#------------------------------------------------------------------------------
#$Date: 2024-02-04 12:58:20 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289313 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/06/1570631.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1570631
loop_
_publ_author_name
'Obieta, Maria'
'Urgoitia, Garazi'
'Herrero, María Teresa'
'SanMartin, Raul'
_publ_section_title
;
 Efficient iron-catalyzed direct acylation of amines with carboxylic acids
 and esters under oxygenated conditions
;
_journal_issue                   2
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              478
_journal_page_last               488
_journal_paper_doi               10.1039/D3CY01429K
_journal_volume                  14
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H19 N O2'
_chemical_formula_sum            'C17 H19 N O2'
_chemical_formula_weight         269.33
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-07-13T13:43:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-08-23 deposited with the CCDC.	2023-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.144(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.40420(10)
_cell_length_b                   22.6075(4)
_cell_length_c                   23.7568(4)
_cell_measurement_reflns_used    26127
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      73.278
_cell_measurement_theta_min      2.639
_cell_volume                     2890.81(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00 -84.00   0.50    3.00    --  -36.99-148.00 139.00   50
  2  ω    -85.00 -27.00   0.50    3.00    --  -36.99 125.00  22.00  116
  3  ω    -64.00 -39.00   0.50    3.00    --  -36.99 148.00-172.00   50
  4  ω     56.00  81.00   0.50    3.00    --   36.99-148.00 139.00   50
  5  ω     41.00  94.00   0.50    3.00    --   36.99-125.00 -55.00  106
  6  ω    102.00 129.00   0.50   12.00    --  111.20 125.00  22.00   54
  7  ω     99.00 124.00   0.50   12.00    --  111.20 148.00-172.00   50
  8  ω     66.00 129.00   0.50   12.00    --  111.20-148.00 139.00  126
  9  ω     72.00 108.00   0.50   12.00    --  111.20-125.00 -55.00   72
 10  ω    -63.00   0.00   0.50    3.00    --  -36.99 -77.00-150.00  126
 11  ω   -114.00 -60.00   0.50    3.00    --  -36.99 -57.00  30.00  108
 12  ω   -111.00  52.00   0.50    3.00    --  -36.99  19.00 -30.00  326
 13  ω   -113.00 -11.00   0.50    3.00    --  -36.99 -57.00 120.00  204
 14  ω    -78.00 -42.00   0.50    3.00    --  -36.99-178.00  60.00   72
 15  ω   -124.00 -93.00   0.50    3.00    --  -36.99-178.00  60.00   62
 16  ω   -110.00 -74.00   0.50    3.00    --  -36.99 -77.00-150.00   72
 17  ω    -46.00 -12.00   0.50    3.00    --   36.99 -38.00  90.00   68
 18  ω     22.00  51.00   0.50    3.00    --   36.99 -38.00  90.00   58
 19  ω    100.00 125.00   0.50    3.00    --   36.99-178.00 -90.00   50
 20  ω     75.00 123.00   0.50    3.00    --   36.99 178.00 150.00   96
 21  ω     63.00  89.00   0.50    3.00    --   36.99-178.00 -90.00   52
 22  ω     53.00  79.00   0.50   12.00    --  111.20-112.00  30.00   52
 23  ω     66.00  92.00   0.50   12.00    --  111.20 178.00 -60.00   52
 24  ω     43.00  70.00   0.50   12.00    --  111.20 -61.00  90.00   54
 25  ω     64.00 146.00   0.50   12.00    --  111.20 178.00 150.00  164
 26  ω     67.00 112.00   0.50   12.00    --  111.20 178.00-120.00   90
 27  ω     30.00  55.00   0.50   12.00    --  111.20 -45.00  60.00   50
 28  ω     43.00  69.00   0.50   12.00    --  111.20-112.00 -60.00   52
 29  ω     27.00 176.00   0.50   12.00    --  111.20  15.00 -60.00  298
 30  ω     84.00 137.00   0.50   12.00    --  111.20  45.00-180.00  106
 31  ω     79.00 106.00   0.50   12.00    --  111.20-112.00 -60.00   54
 32  ω     75.00 103.00   0.50   12.00    --  111.20 -45.00 -60.00   56
 33  ω    112.00 153.00   0.50   12.00    --  111.20 112.00  60.00   82
 34  ω     38.00 102.00   0.50   12.00    --  111.20 -95.00 120.00  128
 35  ω     34.00  71.00   0.50   12.00    --  111.20 -45.00 -60.00   74
 36  ω     85.00 142.00   0.50   12.00    --  111.20 -61.00-180.00  114
 37  ω    105.00 172.00   0.50   12.00    --  111.20  61.00-120.00  134
 38  ω    104.00 144.00   0.50   12.00    --  111.20 178.00 -60.00   80
 39  ω     35.00 149.00   0.50   12.00    --  111.20 -77.00-120.00  228
 40  ω     42.00  75.00   0.50   12.00    --  111.20 -61.00-180.00   66
 41  ω     81.00 107.00   0.50   12.00    --  111.20 -61.00  90.00   52
 42  ω     82.00 137.00   0.50   12.00    --  111.20 -45.00  60.00  110
 43  ω    137.00 176.00   0.50   12.00    --  111.20  61.00 120.00   78
 44  ω    103.00 129.00   0.50   12.00    --  111.20 112.00 -60.00   52
 45  ω     82.00 134.00   0.50   12.00    --  111.20  61.00 120.00  104
 46  ω    -84.00 -43.00   0.50    3.00    --  -36.99 178.00-120.00   82
 47  ω     89.00 114.00   0.50    3.00    --   36.99  57.00  30.00   50
 48  ω     65.00  90.00   0.50    3.00    --   36.99 178.00  30.00   50
 49  ω     29.00  55.00   0.50    3.00    --   36.99  57.00  30.00   52
 50  ω    105.00 131.00   0.50   12.00    --  111.20  61.00   0.00   52
 51  ω    112.00 138.00   0.50   12.00    --  111.20 112.00  30.00   52
 52  ω    131.00 161.00   0.50   12.00    --  111.20 112.00 120.00   60
 53  ω    153.00 178.00   0.50   12.00    --  111.20  61.00   0.00   50
 54  ω     93.00 119.00   0.50   12.00    --  111.20  77.00 -60.00   52
 55  ω   -116.00   1.00   0.50    3.00    --  -36.99 -77.00-120.00  234
 56  ω   -116.00   1.00   0.50    3.00    --  -36.99 -77.00  90.00  234
 57  ω   -126.00 -41.00   0.50    3.00    --  -36.99-178.00 -90.00  170
 58  ω   -116.00   1.00   0.50    3.00    --  -36.99 -77.00   0.00  234
 59  ω   -116.00   1.00   0.50    3.00    --  -36.99 -77.00 120.00  234
 60  ω   -116.00   1.00   0.50    3.00    --  -36.99 -77.00  60.00  234
 61  ω   -114.00  -7.00   0.50    3.00    --  -36.99 -57.00-120.00  214
 62  ω   -116.00   1.00   0.50    3.00    --  -36.99 -77.00 -60.00  234
 63  ω   -120.00   1.00   0.50    3.00    --  -36.99 -38.00   0.00  242
 64  ω   -116.00   1.00   0.50    3.00    --  -36.99 -77.00 -30.00  234
 65  ω   -120.00   1.00   0.50    3.00    --  -36.99 -38.00  60.00  242
 66  ω   -116.00   1.00   0.50    3.00    --  -36.99 -77.00  30.00  234
 67  ω     63.00 125.00   0.50    3.00    --   36.99 178.00  60.00  124
 68  ω     63.00 125.00   0.50    3.00    --   36.99 178.00-120.00  124
 69  ω     59.00 178.00   0.50   12.00    --  111.20  30.00  60.00  238
 70  ω     59.00 115.00   0.50   12.00    --  111.20  30.00 -60.00  112
 71  ω     79.00 178.00   0.50   12.00    --  111.20  61.00 150.00  198
 72  ω     59.00 178.00   0.50   12.00    --  111.20  30.00   0.00  238
 73  ω     59.00 178.00   0.50   12.00    --  111.20  30.00 120.00  238
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0088143
_diffrn_orient_matrix_UB_12      -0.0650537
_diffrn_orient_matrix_UB_13      0.0190709
_diffrn_orient_matrix_UB_21      0.0346755
_diffrn_orient_matrix_UB_22      0.019849
_diffrn_orient_matrix_UB_23      0.0622701
_diffrn_orient_matrix_UB_31      -0.2838119
_diffrn_orient_matrix_UB_32      0.0044287
_diffrn_orient_matrix_UB_33      0.0011155
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_av_unetI/netI     0.0928
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            51265
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.994
_diffrn_reflns_theta_min         2.703
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
        model based on expressions derived by R.C. Clark & J.S. Reid.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.592
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 The Friedel pair coverage of the experiment is almost complete 
 (99%). Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON
 (Spek, 2009). The resulting value was y=-0.02(10)
;
_refine_ls_abs_structure_Flack   0.03(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     807
_refine_ls_number_reflns         10736
_refine_ls_number_restraints     98
_refine_ls_restrained_S_all      1.13
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0996P)²+0.2720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1633
_refine_ls_wR_factor_ref         0.1738
_reflns_Friedel_coverage         0.939
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                9216
_reflns_number_total             10736
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cy01429k2.cif
_cod_data_source_block           b20230143_o342m2remducu
_cod_depositor_comments
'Adding full bibliography for 1570630--1570631.cif.'
_cod_database_code               1570631
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O -0.1556(6) 0.33358(13) 0.55948(14) 0.0444(7) Uani 1 1 d . . . . .
O2A O 0.3213(6) 0.25085(12) 0.50359(12) 0.0391(7) Uani 1 1 d . . . . .
N1A N 0.2644(7) 0.34136(14) 0.57655(14) 0.0344(8) Uani 1 1 d . . . . .
H1A H 0.408515 0.323561 0.575022 0.041 Uiso 1 1 calc R . . . .
C1A C 0.0534(8) 0.31355(16) 0.55588(17) 0.0332(9) Uani 1 1 d . . . . .
C2A C 0.0930(8) 0.25349(16) 0.52771(17) 0.0338(8) Uani 1 1 d . . . . .
H2A H -0.044021 0.247323 0.497092 0.041 Uiso 1 1 calc R . . . .
C3A C 0.0845(8) 0.20373(16) 0.57024(16) 0.0337(9) Uani 1 1 d . . . . .
C4A C -0.1074(8) 0.20138(19) 0.60593(18) 0.0388(9) Uani 1 1 d . . . . .
H4A H -0.23569 0.230238 0.602877 0.047 Uiso 1 1 calc R . . . .
C5A C -0.1091(10) 0.1566(2) 0.6459(2) 0.0456(11) Uani 1 1 d . . . . .
H5A H -0.237765 0.155473 0.670592 0.055 Uiso 1 1 calc R . . . .
C6A C 0.0731(10) 0.1136(2) 0.6502(2) 0.0452(11) Uani 1 1 d . . . . .
H6A H 0.06899 0.082957 0.677507 0.054 Uiso 1 1 calc R . . . .
C7A C 0.2611(9) 0.11550(19) 0.6146(2) 0.0430(10) Uani 1 1 d . . . . .
H7A H 0.388334 0.086387 0.617697 0.052 Uiso 1 1 calc R . . . .
C8A C 0.2646(9) 0.16003(18) 0.57427(18) 0.0376(9) Uani 1 1 d . . . . .
H8A H 0.391991 0.160431 0.549201 0.045 Uiso 1 1 calc R . . . .
C9A C 0.2566(8) 0.40067(17) 0.60143(17) 0.0348(9) Uani 1 1 d . . . . .
H9A H 0.104919 0.403274 0.622523 0.042 Uiso 1 1 calc R . . . .
C10A C 0.2385(8) 0.44821(17) 0.55608(17) 0.0340(9) Uani 1 1 d . . . . .
C11A C 0.4141(9) 0.45133(18) 0.51662(19) 0.0383(9) Uani 1 1 d . . . . .
H11A H 0.544257 0.423013 0.517561 0.046 Uiso 1 1 calc R . . . .
C12A C 0.3996(9) 0.49543(19) 0.47611(19) 0.0423(10) Uani 1 1 d . . . . .
H12A H 0.520623 0.497202 0.449518 0.051 Uiso 1 1 calc R . . . .
C13A C 0.2118(9) 0.53685(19) 0.47385(19) 0.0411(10) Uani 1 1 d . . . . .
H13A H 0.203487 0.567138 0.446022 0.049 Uiso 1 1 calc R . . . .
C14A C 0.0351(9) 0.53384(19) 0.51265(19) 0.0398(10) Uani 1 1 d . . . . .
H14A H -0.095905 0.56195 0.511382 0.048 Uiso 1 1 calc R . . . .
C15A C 0.0504(9) 0.48956(18) 0.55340(18) 0.0370(9) Uani 1 1 d . . . . .
H15A H -0.071077 0.487766 0.579888 0.044 Uiso 1 1 calc R . . . .
C16A C 0.4840(10) 0.4093(2) 0.6437(2) 0.0469(11) Uani 1 1 d . . . . .
H16G H 0.47916 0.380656 0.674568 0.07 Uiso 1 1 calc GR . . . .
H16H H 0.483336 0.449518 0.659078 0.07 Uiso 1 1 calc GR . . . .
H16I H 0.635402 0.403231 0.624621 0.07 Uiso 1 1 calc GR . . . .
C17A C 0.3197(11) 0.2847(2) 0.45235(18) 0.0489(12) Uani 1 1 d . . . . .
H17D H 0.19729 0.267936 0.4238 0.073 Uiso 1 1 calc GR . . . .
H17E H 0.484926 0.283321 0.438417 0.073 Uiso 1 1 calc GR . . . .
H17F H 0.275929 0.325797 0.459879 0.073 Uiso 1 1 calc GR . . . .
O1B O 0.2209(6) 0.32886(14) 0.31786(13) 0.0419(7) Uani 1 1 d . . . . .
O2B O 0.6911(7) 0.25511(14) 0.25303(14) 0.0485(8) Uani 1 1 d . . . . .
N1B N 0.6397(8) 0.34055(15) 0.32690(16) 0.0406(9) Uani 1 1 d . . . . .
H1B H 0.784378 0.324322 0.322114 0.049 Uiso 1 1 calc R . . . .
C1B C 0.4314(9) 0.31192(18) 0.30986(17) 0.0388(10) Uani 1 1 d . . . . .
C2B C 0.4724(9) 0.25188(17) 0.27991(17) 0.0355(9) Uani 1 1 d . . . . .
H2B H 0.33053 0.245278 0.250577 0.043 Uiso 1 1 calc R . . . .
C3B C 0.4748(8) 0.20216(16) 0.32267(16) 0.0318(8) Uani 1 1 d . . . . .
C4B C 0.6787(9) 0.19625(18) 0.36307(18) 0.0380(9) Uani 1 1 d . . . . .
H4B H 0.816611 0.222215 0.362335 0.046 Uiso 1 1 calc R . . . .
C5B C 0.6799(10) 0.15274(19) 0.40400(19) 0.0427(10) Uani 1 1 d . . . . .
H5B H 0.818325 0.149255 0.431403 0.051 Uiso 1 1 calc R . . . .
C6B C 0.4822(10) 0.11433(19) 0.40549(19) 0.0440(11) Uani 1 1 d . . . . .
H6B H 0.484616 0.084338 0.433544 0.053 Uiso 1 1 calc R . . . .
C7B C 0.2806(9) 0.1199(2) 0.3657(2) 0.0467(11) Uani 1 1 d . . . . .
H7B H 0.143821 0.093625 0.366486 0.056 Uiso 1 1 calc R . . . .
C8B C 0.2767(10) 0.16398(19) 0.32449(19) 0.0416(10) Uani 1 1 d . . . . .
H8B H 0.136744 0.167678 0.297516 0.05 Uiso 1 1 calc R . . . .
C9B C 0.6306(9) 0.39897(17) 0.35361(17) 0.0366(9) Uani 1 1 d . . . . .
H9B H 0.475768 0.401265 0.373608 0.044 Uiso 1 1 calc R . . . .
C10B C 0.6203(8) 0.44729(16) 0.30907(17) 0.0335(9) Uani 1 1 d . . . . .
C11B C 0.8019(9) 0.44966(18) 0.27066(18) 0.0373(9) Uani 1 1 d . . . . .
H11B H 0.93451 0.421924 0.273162 0.045 Uiso 1 1 calc R . . . .
C12B C 0.7872(10) 0.4926(2) 0.22909(19) 0.0434(10) Uani 1 1 d . . . . .
H12B H 0.909643 0.493977 0.202807 0.052 Uiso 1 1 calc R . . . .
C13B C 0.5965(9) 0.53348(19) 0.2253(2) 0.0436(10) Uani 1 1 d . . . . .
H13B H 0.587516 0.562591 0.196365 0.052 Uiso 1 1 calc R . . . .
C14B C 0.4181(9) 0.53205(19) 0.2638(2) 0.0426(10) Uani 1 1 d . . . . .
H14B H 0.287824 0.560384 0.261672 0.051 Uiso 1 1 calc R . . . .
C15B C 0.4321(9) 0.48860(17) 0.30559(18) 0.0369(9) Uani 1 1 d . . . . .
H15B H 0.3102 0.48745 0.332014 0.044 Uiso 1 1 calc R . . . .
C16B C 0.8575(10) 0.4052(2) 0.3982(2) 0.0482(11) Uani 1 1 d . . . . .
H16J H 0.857701 0.444767 0.415071 0.072 Uiso 1 1 calc GR . . . .
H16K H 1.011123 0.399404 0.379912 0.072 Uiso 1 1 calc GR . . . .
H16L H 0.846775 0.375353 0.427819 0.072 Uiso 1 1 calc GR . . . .
C17B C 0.7006(12) 0.2112(2) 0.2118(2) 0.0540(13) Uani 1 1 d . . . . .
H17G H 0.566743 0.217669 0.181739 0.081 Uiso 1 1 calc GR . . . .
H17H H 0.680356 0.172288 0.228892 0.081 Uiso 1 1 calc GR . . . .
H17I H 0.861314 0.212968 0.195727 0.081 Uiso 1 1 calc GR . . . .
O1C O 0.5056(6) 0.17505(13) 0.05647(14) 0.0425(7) Uani 1 1 d . . . . .
O2C O -0.0273(6) 0.26267(14) 0.01029(12) 0.0422(7) Uani 1 1 d . . . . .
N1C N 0.0943(7) 0.15910(14) 0.06340(14) 0.0353(8) Uani 1 1 d . . . . .
H1C H -0.056129 0.174027 0.05725 0.042 Uiso 1 1 calc R . . . .
C1C C 0.2897(8) 0.19183(17) 0.05119(16) 0.0340(9) Uani 1 1 d . . . . .
C2C C 0.2264(8) 0.25539(17) 0.03124(17) 0.0330(8) Uani 1 1 d . . . . .
H2C H 0.334355 0.266271 0.000781 0.04 Uiso 1 1 calc R . . . .
C3C C 0.2767(8) 0.29767(16) 0.08007(16) 0.0319(8) Uani 1 1 d . . . . .
C4C C 0.4821(9) 0.33386(18) 0.08490(19) 0.0397(10) Uani 1 1 d . . . . .
H4C H 0.598935 0.332012 0.057356 0.048 Uiso 1 1 calc R . . . .
C5C C 0.5195(10) 0.3730(2) 0.1298(2) 0.0468(11) Uani 1 1 d . . . . .
H5C H 0.660224 0.398397 0.132406 0.056 Uiso 1 1 calc R . . . .
C6C C 0.3535(10) 0.3755(2) 0.17070(19) 0.0467(11) Uani 1 1 d . . . . .
H6C H 0.380167 0.40245 0.201312 0.056 Uiso 1 1 calc R . . . .
C7C C 0.1496(9) 0.3389(2) 0.16705(18) 0.0429(10) Uani 1 1 d . . . . .
H7C H 0.036271 0.34 0.195385 0.051 Uiso 1 1 calc R . . . .
C8C C 0.1102(9) 0.30017(18) 0.12173(17) 0.0367(9) Uani 1 1 d . . . . .
H8C H -0.031567 0.275129 0.119011 0.044 Uiso 1 1 calc R . . . .
C9C C 0.1241(9) 0.09912(16) 0.08672(17) 0.0351(9) Uani 1 1 d . . . . .
H9C H 0.303589 0.093584 0.099934 0.042 Uiso 1 1 calc R . . . .
C10C C 0.0541(8) 0.05222(17) 0.04248(17) 0.0340(9) Uani 1 1 d . . . . .
C11C C 0.2137(10) 0.0055(2) 0.0353(2) 0.0464(11) Uani 1 1 d . . . . .
H11C H 0.367245 0.003179 0.057971 0.056 Uiso 1 1 calc R . . . .
C12C C 0.1519(12) -0.0380(2) -0.0047(2) 0.0550(13) Uani 1 1 d . . . . .
H12C H 0.263507 -0.069711 -0.009281 0.066 Uiso 1 1 calc R . . . .
C13C C -0.0716(11) -0.0353(2) -0.0381(2) 0.0542(13) Uani 1 1 d . . . . .
H13C H -0.113947 -0.065083 -0.065485 0.065 Uiso 1 1 calc R . . . .
C14C C -0.2310(10) 0.0107(2) -0.0311(2) 0.0517(12) Uani 1 1 d . . . . .
H14C H -0.383518 0.012942 -0.054282 0.062 Uiso 1 1 calc R . . . .
C15C C -0.1731(9) 0.0539(2) 0.0091(2) 0.0417(10) Uani 1 1 d . . . . .
H15C H -0.287837 0.084892 0.014089 0.05 Uiso 1 1 calc R . . . .
C16C C -0.0246(10) 0.0929(2) 0.13784(18) 0.0451(11) Uani 1 1 d . . . . .
H16M H 0.045677 0.118952 0.168154 0.068 Uiso 1 1 calc GR . . . .
H16N H -0.017362 0.051811 0.151008 0.068 Uiso 1 1 calc GR . . . .
H16O H -0.197904 0.103963 0.127286 0.068 Uiso 1 1 calc GR . . . .
C17C C -0.0813(13) 0.2428(3) -0.0446(2) 0.0624(15) Uani 1 1 d . . . . .
H17J H 0.014403 0.265666 -0.07015 0.094 Uiso 1 1 calc GR . . . .
H17K H -0.259195 0.247745 -0.055617 0.094 Uiso 1 1 calc GR . . . .
H17L H -0.037314 0.20084 -0.046816 0.094 Uiso 1 1 calc GR . . . .
O1D O 1.1187(17) 0.8347(5) 0.1875(4) 0.061(2) Uani 0.508(10) 1 d . U P A 2
O1E O 1.1404(16) 0.8000(5) 0.1913(3) 0.052(2) Uani 0.492(10) 1 d . U P A 1
O2D O 0.5520(16) 0.8954(3) 0.1293(3) 0.055(2) Uani 0.508(10) 1 d . U P A 2
O2E O 0.5864(14) 0.7407(3) 0.2423(4) 0.045(2) Uani 0.492(10) 1 d . U P A 1
N1D N 0.7283(19) 0.8095(4) 0.2047(4) 0.042(2) Uani 0.508(10) 1 d . U P A 2
H1D H 0.572376 0.821044 0.203767 0.05 Uiso 0.508(10) 1 calc R . P A 2
N1E N 0.738(2) 0.8308(5) 0.1807(5) 0.043(2) Uani 0.492(10) 1 d D U P A 1
C0AA C 0.9191(19) 0.7934(4) 0.1972(3) 0.039(2) Uani 0.492(10) 1 d . U P A 1
C1D C 0.892(2) 0.8454(4) 0.1841(4) 0.042(3) Uani 0.508(10) 1 d . U P A 2
C2D C 0.791(4) 0.8881(7) 0.1544(9) 0.040(4) Uani 0.508(10) 1 d . U P A 2
H2D H 0.90835 0.899359 0.125869 0.048 Uiso 0.508(10) 1 calc R . P A 2
C2E C 0.824(4) 0.7353(8) 0.2254(10) 0.041(4) Uani 0.492(10) 1 d . U P A 1
H2E H 0.944054 0.7216 0.257166 0.05 Uiso 0.492(10) 1 calc R . P A 1
C3D C 0.7722(10) 0.9454(2) 0.1977(2) 0.0495(12) Uani 1 1 d . . . . .
C4D C 0.9669(11) 0.9544(2) 0.2397(2) 0.0528(13) Uani 1 1 d . . . . .
H4D H 1.106803 0.928761 0.241995 0.063 Uiso 1 1 calc R . . . .
C5D C 0.9569(11) 1.0006(2) 0.2781(2) 0.0544(13) Uani 1 1 d . . . . .
H5D H 1.090029 1.006224 0.3065 0.065 Uiso 1 1 calc R . . . .
C6D C 0.7563(11) 1.0383(2) 0.2753(2) 0.0561(13) Uani 1 1 d . . . . .
H6D H 0.751233 1.07002 0.301342 0.067 Uiso 1 1 calc R . . . .
C7D C 0.5621(11) 1.0295(3) 0.2341(2) 0.0576(13) Uani 1 1 d . . . . .
H7D H 0.422179 1.055134 0.232116 0.069 Uiso 1 1 calc R . . . .
C8D C 0.5709(11) 0.9835(2) 0.1957(2) 0.0566(13) Uani 1 1 d . . . . .
H8D H 0.436586 0.978025 0.167576 0.068 Uiso 1 1 calc R . . . .
C9D C 0.794(5) 0.7533(7) 0.2284(11) 0.050(5) Uani 0.508(10) 1 d . U P A 2
H9D H 0.963307 0.75741 0.248731 0.061 Uiso 0.508(10) 1 calc R . P A 2
C9E C 0.796(5) 0.9041(8) 0.1571(11) 0.046(5) Uani 0.492(10) 1 d . U P A 1
H9E H 0.973765 0.905014 0.148619 0.055 Uiso 0.492(10) 1 calc R . P A 1
H1E H 0.577(5) 0.829(6) 0.183(5) 0.055 Uiso 0.492(10) 1 d DR . P A 1
C10D C 0.8073(10) 0.6964(3) 0.1825(2) 0.0532(13) Uani 1 1 d . . . . .
C11D C 0.6048(10) 0.6907(2) 0.1422(2) 0.0512(12) Uani 1 1 d . . . . .
H11D H 0.467927 0.716996 0.142814 0.061 Uiso 1 1 calc R . . . .
C12D C 0.6017(11) 0.6470(3) 0.1012(2) 0.0561(13) Uani 1 1 d . . . . .
H12D H 0.462922 0.643396 0.07391 0.067 Uiso 1 1 calc R . . . .
C13D C 0.8015(11) 0.6084(3) 0.1000(3) 0.0606(14) Uani 1 1 d . . . . .
H13D H 0.799503 0.57846 0.071926 0.073 Uiso 1 1 calc R . . . .
C14D C 1.0040(12) 0.6137(3) 0.1401(3) 0.0655(16) Uani 1 1 d . . . . .
H14D H 1.140812 0.5874 0.139477 0.079 Uiso 1 1 calc R . . . .
C15D C 1.0055(11) 0.6578(3) 0.1811(2) 0.0663(17) Uani 1 1 d . . . . .
H15D H 1.144164 0.661467 0.208419 0.08 Uiso 1 1 calc R . . . .
C16D C 0.607(2) 0.7375(6) 0.2750(6) 0.051(3) Uani 0.508(10) 1 d . U P A 2
H16A H 0.436212 0.736073 0.257092 0.076 Uiso 0.508(10) 1 calc GR . P A 2
H16B H 0.618515 0.767904 0.304562 0.076 Uiso 0.508(10) 1 calc GR . P A 2
H16C H 0.650863 0.698948 0.291877 0.076 Uiso 0.508(10) 1 calc GR . P A 2
C16E C 0.633(3) 0.8928(6) 0.0974(6) 0.062(3) Uani 0.492(10) 1 d . U P A 1
H16D H 0.456533 0.891874 0.103537 0.094 Uiso 0.492(10) 1 calc GR . P A 1
H16E H 0.681464 0.854991 0.0815 0.094 Uiso 0.492(10) 1 calc GR . P A 1
H16F H 0.663997 0.924868 0.071127 0.094 Uiso 0.492(10) 1 calc GR . P A 1
C17D C 0.557(3) 0.8602(6) 0.0788(5) 0.067(4) Uani 0.508(10) 1 d . U P A 2
H17A H 0.675636 0.877304 0.054533 0.101 Uiso 0.508(10) 1 calc GR . P A 2
H17B H 0.390799 0.859747 0.058419 0.101 Uiso 0.508(10) 1 calc GR . P A 2
H17C H 0.606921 0.819703 0.089059 0.101 Uiso 0.508(10) 1 calc GR . P A 2
C19E C 0.591(3) 0.7669(6) 0.2954(5) 0.057(3) Uani 0.492(10) 1 d . U P A 1
H19A H 0.716616 0.79834 0.298481 0.086 Uiso 0.492(10) 1 calc GR . P A 1
H19B H 0.632734 0.737065 0.324636 0.086 Uiso 0.492(10) 1 calc GR . P A 1
H19C H 0.42769 0.783817 0.300446 0.086 Uiso 0.492(10) 1 calc GR . P A 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -7 -1 0.0494
4 -1 -2 0.2927
0 7 1 0.0551
-4 1 1 0.2903
0 -2 15 0.0561
4 -1 -1 0.2915
0 2 -15 0.0437
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A O2A C17A 112.6(3) . . ?
C1A N1A H1A 119.5 . . ?
C1A N1A C9A 121.1(3) . . ?
C9A N1A H1A 119.5 . . ?
O1A C1A N1A 123.6(4) . . ?
O1A C1A C2A 121.4(4) . . ?
N1A C1A C2A 115.0(4) . . ?
O2A C2A C1A 112.1(3) . . ?
O2A C2A H2A 108.5 . . ?
O2A C2A C3A 108.7(3) . . ?
C1A C2A H2A 108.5 . . ?
C3A C2A C1A 110.6(3) . . ?
C3A C2A H2A 108.5 . . ?
C4A C3A C2A 120.1(4) . . ?
C8A C3A C2A 120.9(4) . . ?
C8A C3A C4A 119.1(4) . . ?
C3A C4A H4A 120.2 . . ?
C5A C4A C3A 119.5(4) . . ?
C5A C4A H4A 120.2 . . ?
C4A C5A H5A 119.5 . . ?
C6A C5A C4A 121.1(4) . . ?
C6A C5A H5A 119.4 . . ?
C5A C6A H6A 120.3 . . ?
C7A C6A C5A 119.4(4) . . ?
C7A C6A H6A 120.3 . . ?
C6A C7A H7A 120 . . ?
C6A C7A C8A 120.1(4) . . ?
C8A C7A H7A 120 . . ?
C3A C8A C7A 120.7(4) . . ?
C3A C8A H8A 119.6 . . ?
C7A C8A H8A 119.6 . . ?
N1A C9A H9A 108.1 . . ?
N1A C9A C10A 111.3(3) . . ?
N1A C9A C16A 109.3(4) . . ?
C10A C9A H9A 108.1 . . ?
C10A C9A C16A 111.9(4) . . ?
C16A C9A H9A 108.1 . . ?
C11A C10A C9A 120.5(4) . . ?
C15A C10A C9A 120.9(4) . . ?
C15A C10A C11A 118.6(4) . . ?
C10A C11A H11A 119.8 . . ?
C12A C11A C10A 120.3(4) . . ?
C12A C11A H11A 119.8 . . ?
C11A C12A H12A 119.6 . . ?
C13A C12A C11A 120.8(4) . . ?
C13A C12A H12A 119.6 . . ?
C12A C13A H13A 120.4 . . ?
C12A C13A C14A 119.3(4) . . ?
C14A C13A H13A 120.4 . . ?
C13A C14A H14A 120.1 . . ?
C13A C14A C15A 119.8(4) . . ?
C15A C14A H14A 120.1 . . ?
C10A C15A C14A 121.2(4) . . ?
C10A C15A H15A 119.4 . . ?
C14A C15A H15A 119.4 . . ?
C9A C16A H16G 109.5 . . ?
C9A C16A H16H 109.5 . . ?
C9A C16A H16I 109.5 . . ?
H16G C16A H16H 109.5 . . ?
H16G C16A H16I 109.5 . . ?
H16H C16A H16I 109.5 . . ?
O2A C17A H17D 109.5 . . ?
O2A C17A H17E 109.5 . . ?
O2A C17A H17F 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C2B O2B C17B 111.7(4) . . ?
C1B N1B H1B 119.7 . . ?
C1B N1B C9B 120.6(4) . . ?
C9B N1B H1B 119.7 . . ?
O1B C1B N1B 124.8(4) . . ?
O1B C1B C2B 120.9(4) . . ?
N1B C1B C2B 114.3(4) . . ?
O2B C2B C1B 108.9(3) . . ?
O2B C2B H2B 108.5 . . ?
O2B C2B C3B 112.9(4) . . ?
C1B C2B H2B 108.5 . . ?
C3B C2B C1B 109.5(3) . . ?
C3B C2B H2B 108.5 . . ?
C4B C3B C2B 119.3(4) . . ?
C8B C3B C2B 121.7(4) . . ?
C8B C3B C4B 118.9(4) . . ?
C3B C4B H4B 119.9 . . ?
C5B C4B C3B 120.2(4) . . ?
C5B C4B H4B 119.9 . . ?
C4B C5B H5B 119.6 . . ?
C6B C5B C4B 120.7(4) . . ?
C6B C5B H5B 119.6 . . ?
C5B C6B H6B 120.3 . . ?
C5B C6B C7B 119.3(4) . . ?
C7B C6B H6B 120.3 . . ?
C6B C7B H7B 119.8 . . ?
C6B C7B C8B 120.4(4) . . ?
C8B C7B H7B 119.8 . . ?
C3B C8B C7B 120.4(5) . . ?
C3B C8B H8B 119.8 . . ?
C7B C8B H8B 119.8 . . ?
N1B C9B H9B 108.3 . . ?
N1B C9B C10B 110.3(3) . . ?
N1B C9B C16B 108.7(4) . . ?
C10B C9B H9B 108.3 . . ?
C10B C9B C16B 112.8(4) . . ?
C16B C9B H9B 108.3 . . ?
C11B C10B C9B 119.9(4) . . ?
C15B C10B C9B 120.7(4) . . ?
C15B C10B C11B 119.5(4) . . ?
C10B C11B H11B 120.2 . . ?
C12B C11B C10B 119.6(4) . . ?
C12B C11B H11B 120.2 . . ?
C11B C12B H12B 119.6 . . ?
C11B C12B C13B 120.7(4) . . ?
C13B C12B H12B 119.6 . . ?
C12B C13B H13B 120 . . ?
C12B C13B C14B 120.0(4) . . ?
C14B C13B H13B 120 . . ?
C13B C14B H14B 120.3 . . ?
C13B C14B C15B 119.3(4) . . ?
C15B C14B H14B 120.3 . . ?
C10B C15B C14B 120.8(4) . . ?
C10B C15B H15B 119.6 . . ?
C14B C15B H15B 119.6 . . ?
C9B C16B H16J 109.5 . . ?
C9B C16B H16K 109.5 . . ?
C9B C16B H16L 109.5 . . ?
H16J C16B H16K 109.5 . . ?
H16J C16B H16L 109.5 . . ?
H16K C16B H16L 109.5 . . ?
O2B C17B H17G 109.5 . . ?
O2B C17B H17H 109.5 . . ?
O2B C17B H17I 109.5 . . ?
H17G C17B H17H 109.5 . . ?
H17G C17B H17I 109.5 . . ?
H17H C17B H17I 109.5 . . ?
C17C O2C C2C 114.0(4) . . ?
C1C N1C H1C 119 . . ?
C1C N1C C9C 121.9(4) . . ?
C9C N1C H1C 119 . . ?
O1C C1C N1C 124.7(4) . . ?
O1C C1C C2C 120.3(4) . . ?
N1C C1C C2C 115.0(4) . . ?
O2C C2C C1C 113.3(3) . . ?
O2C C2C H2C 108.9 . . ?
O2C C2C C3C 107.3(3) . . ?
C1C C2C H2C 108.9 . . ?
C3C C2C C1C 109.5(3) . . ?
C3C C2C H2C 108.9 . . ?
C4C C3C C2C 122.0(3) . . ?
C4C C3C C8C 118.9(4) . . ?
C8C C3C C2C 119.1(4) . . ?
C3C C4C H4C 119.8 . . ?
C3C C4C C5C 120.3(4) . . ?
C5C C4C H4C 119.8 . . ?
C4C C5C H5C 119.8 . . ?
C6C C5C C4C 120.5(5) . . ?
C6C C5C H5C 119.8 . . ?
C5C C6C H6C 120 . . ?
C7C C6C C5C 119.9(4) . . ?
C7C C6C H6C 120 . . ?
C6C C7C H7C 120.2 . . ?
C6C C7C C8C 119.6(4) . . ?
C8C C7C H7C 120.2 . . ?
C3C C8C H8C 119.6 . . ?
C7C C8C C3C 120.7(4) . . ?
C7C C8C H8C 119.6 . . ?
N1C C9C H9C 107.7 . . ?
N1C C9C C10C 111.8(3) . . ?
N1C C9C C16C 109.8(3) . . ?
C10C C9C H9C 107.7 . . ?
C10C C9C C16C 111.8(4) . . ?
C16C C9C H9C 107.7 . . ?
C11C C10C C9C 120.0(4) . . ?
C11C C10C C15C 118.3(4) . . ?
C15C C10C C9C 121.7(4) . . ?
C10C C11C H11C 119.6 . . ?
C10C C11C C12C 120.8(5) . . ?
C12C C11C H11C 119.6 . . ?
C11C C12C H12C 119.8 . . ?
C13C C12C C11C 120.3(5) . . ?
C13C C12C H12C 119.8 . . ?
C12C C13C H13C 120.3 . . ?
C14C C13C C12C 119.3(5) . . ?
C14C C13C H13C 120.3 . . ?
C13C C14C H14C 119.5 . . ?
C13C C14C C15C 120.9(5) . . ?
C15C C14C H14C 119.5 . . ?
C10C C15C H15C 119.8 . . ?
C14C C15C C10C 120.3(4) . . ?
C14C C15C H15C 119.8 . . ?
C9C C16C H16M 109.5 . . ?
C9C C16C H16N 109.5 . . ?
C9C C16C H16O 109.5 . . ?
H16M C16C H16N 109.5 . . ?
H16M C16C H16O 109.5 . . ?
H16N C16C H16O 109.5 . . ?
O2C C17C H17J 109.5 . . ?
O2C C17C H17K 109.5 . . ?
O2C C17C H17L 109.5 . . ?
H17J C17C H17K 109.5 . . ?
H17J C17C H17L 109.5 . . ?
H17K C17C H17L 109.5 . . ?
C2D O2D C17D 102.0(12) . . ?
C2E O2E C19E 110.9(13) . . ?
C1D N1D H1D 118.6 . . ?
C1D N1D C9D 122.7(14) . . ?
C9D N1D H1D 118.6 . . ?
C0AA N1E C9E 122.6(13) . . ?
C0AA N1E H1E 131(9) . . ?
C9E N1E H1E 106(9) . . ?
O1E C0AA N1E 126.2(10) . . ?
O1E C0AA C2E 120.5(12) . . ?
N1E C0AA C2E 113.3(12) . . ?
O1D C1D N1D 122.9(10) . . ?
O1D C1D C2D 123.2(15) . . ?
C2D C1D N1D 113.4(15) . . ?
O2D C2D H2D 107.5 . . ?
O2D C2D C3D 93.8(12) . . ?
C1D C2D O2D 131.1(17) . . ?
C1D C2D H2D 107.5 . . ?
C1D C2D C3D 107.0(14) . . ?
C3D C2D H2D 107.5 . . ?
O2E C2E C0AA 113.3(13) . . ?
O2E C2E H2E 111.4 . . ?
C0AA C2E H2E 111.4 . . ?
C10D C2E O2E 106.0(16) . . ?
C10D C2E C0AA 103.0(14) . . ?
C10D C2E H2E 111.4 . . ?
C4D C3D C2D 118.0(9) . . ?
C8D C3D C2D 123.8(9) . . ?
C8D C3D C4D 118.2(5) . . ?
C9E C3D C4D 119.6(12) . . ?
C9E C3D C8D 121.8(12) . . ?
C3D C4D H4D 119.8 . . ?
C5D C4D C3D 120.4(5) . . ?
C5D C4D H4D 119.8 . . ?
C4D C5D H5D 119.7 . . ?
C6D C5D C4D 120.7(6) . . ?
C6D C5D H5D 119.7 . . ?
C5D C6D H6D 120.3 . . ?
C5D C6D C7D 119.4(5) . . ?
C7D C6D H6D 120.3 . . ?
C6D C7D H7D 119.9 . . ?
C6D C7D C8D 120.2(5) . . ?
C8D C7D H7D 119.9 . . ?
C3D C8D C7D 121.2(6) . . ?
C3D C8D H8D 119.4 . . ?
C7D C8D H8D 119.4 . . ?
N1D C9D H9D 107 . . ?
N1D C9D C10D 116.7(18) . . ?
N1D C9D C16D 108.7(16) . . ?
C10D C9D H9D 107 . . ?
C16D C9D H9D 107 . . ?
C16D C9D C10D 110.0(14) . . ?
N1E C9E H9E 106.4 . . ?
C3D C9E N1E 112.6(16) . . ?
C3D C9E H9E 106.4 . . ?
C3D C9E C16E 130.7(18) . . ?
C16E C9E N1E 91.9(11) . . ?
C16E C9E H9E 106.4 . . ?
C2E C10D C11D 125.2(11) . . ?
C2E C10D C15D 115.5(11) . . ?
C11D C10D C9D 115.9(10) . . ?
C15D C10D C9D 124.9(10) . . ?
C15D C10D C11D 119.2(6) . . ?
C10D C11D H11D 119.8 . . ?
C12D C11D C10D 120.5(5) . . ?
C12D C11D H11D 119.8 . . ?
C11D C12D H12D 120 . . ?
C11D C12D C13D 120.1(6) . . ?
C13D C12D H12D 120 . . ?
C12D C13D H13D 120.1 . . ?
C14D C13D C12D 119.8(6) . . ?
C14D C13D H13D 120.1 . . ?
C13D C14D H14D 120.2 . . ?
C13D C14D C15D 119.7(6) . . ?
C15D C14D H14D 120.2 . . ?
C10D C15D C14D 120.7(6) . . ?
C10D C15D H15D 119.6 . . ?
C14D C15D H15D 119.6 . . ?
C9D C16D H16A 109.5 . . ?
C9D C16D H16B 109.5 . . ?
C9D C16D H16C 109.5 . . ?
H16A C16D H16B 109.5 . . ?
H16A C16D H16C 109.5 . . ?
H16B C16D H16C 109.5 . . ?
C9E C16E H16D 109.5 . . ?
C9E C16E H16E 109.5 . . ?
C9E C16E H16F 109.5 . . ?
H16D C16E H16E 109.5 . . ?
H16D C16E H16F 109.5 . . ?
H16E C16E H16F 109.5 . . ?
O2D C17D H17A 109.5 . . ?
O2D C17D H17B 109.5 . . ?
O2D C17D H17C 109.5 . . ?
H17A C17D H17B 109.5 . . ?
H17A C17D H17C 109.5 . . ?
H17B C17D H17C 109.5 . . ?
O2E C19E H19A 109.5 . . ?
O2E C19E H19B 109.5 . . ?
O2E C19E H19C 109.5 . . ?
H19A C19E H19B 109.5 . . ?
H19A C19E H19C 109.5 . . ?
H19B C19E H19C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.227(5) . ?
O2A C2A 1.408(5) . ?
O2A C17A 1.437(5) . ?
N1A H1A 0.88 . ?
N1A C1A 1.355(6) . ?
N1A C9A 1.468(5) . ?
C1A C2A 1.537(5) . ?
C2A H2A 1 . ?
C2A C3A 1.516(5) . ?
C3A C4A 1.398(6) . ?
C3A C8A 1.384(6) . ?
C4A H4A 0.95 . ?
C4A C5A 1.389(6) . ?
C5A H5A 0.95 . ?
C5A C6A 1.381(7) . ?
C6A H6A 0.95 . ?
C6A C7A 1.380(7) . ?
C7A H7A 0.95 . ?
C7A C8A 1.392(6) . ?
C8A H8A 0.95 . ?
C9A H9A 1 . ?
C9A C10A 1.519(6) . ?
C9A C16A 1.529(7) . ?
C10A C11A 1.394(6) . ?
C10A C15A 1.378(6) . ?
C11A H11A 0.95 . ?
C11A C12A 1.383(6) . ?
C12A H12A 0.95 . ?
C12A C13A 1.378(7) . ?
C13A H13A 0.95 . ?
C13A C14A 1.387(6) . ?
C14A H14A 0.95 . ?
C14A C15A 1.390(6) . ?
C15A H15A 0.95 . ?
C16A H16G 0.98 . ?
C16A H16H 0.98 . ?
C16A H16I 0.98 . ?
C17A H17D 0.98 . ?
C17A H17E 0.98 . ?
C17A H17F 0.98 . ?
O1B C1B 1.231(6) . ?
O2B C2B 1.395(5) . ?
O2B C17B 1.399(6) . ?
N1B H1B 0.88 . ?
N1B C1B 1.330(6) . ?
N1B C9B 1.468(5) . ?
C1B C2B 1.557(6) . ?
C2B H2B 1 . ?
C2B C3B 1.514(5) . ?
C3B C4B 1.401(6) . ?
C3B C8B 1.379(6) . ?
C4B H4B 0.95 . ?
C4B C5B 1.383(6) . ?
C5B H5B 0.95 . ?
C5B C6B 1.380(7) . ?
C6B H6B 0.95 . ?
C6B C7B 1.382(7) . ?
C7B H7B 0.95 . ?
C7B C8B 1.396(6) . ?
C8B H8B 0.95 . ?
C9B H9B 1 . ?
C9B C10B 1.518(5) . ?
C9B C16B 1.554(7) . ?
C10B C11B 1.400(6) . ?
C10B C15B 1.378(6) . ?
C11B H11B 0.95 . ?
C11B C12B 1.382(6) . ?
C12B H12B 0.95 . ?
C12B C13B 1.382(7) . ?
C13B H13B 0.95 . ?
C13B C14B 1.387(6) . ?
C14B H14B 0.95 . ?
C14B C15B 1.394(6) . ?
C15B H15B 0.95 . ?
C16B H16J 0.98 . ?
C16B H16K 0.98 . ?
C16B H16L 0.98 . ?
C17B H17G 0.98 . ?
C17B H17H 0.98 . ?
C17B H17I 0.98 . ?
O1C C1C 1.222(5) . ?
O2C C2C 1.426(5) . ?
O2C C17C 1.385(6) . ?
N1C H1C 0.88 . ?
N1C C1C 1.343(5) . ?
N1C C9C 1.468(5) . ?
C1C C2C 1.542(5) . ?
C2C H2C 1 . ?
C2C C3C 1.509(6) . ?
C3C C4C 1.375(6) . ?
C3C C8C 1.397(5) . ?
C4C H4C 0.95 . ?
C4C C5C 1.387(7) . ?
C5C H5C 0.95 . ?
C5C C6C 1.382(7) . ?
C6C H6C 0.95 . ?
C6C C7C 1.375(7) . ?
C7C H7C 0.95 . ?
C7C C8C 1.389(6) . ?
C8C H8C 0.95 . ?
C9C H9C 1 . ?
C9C C10C 1.517(6) . ?
C9C C16C 1.522(5) . ?
C10C C11C 1.384(6) . ?
C10C C15C 1.401(7) . ?
C11C H11C 0.95 . ?
C11C C12C 1.386(7) . ?
C12C H12C 0.95 . ?
C12C C13C 1.386(8) . ?
C13C H13C 0.95 . ?
C13C C14C 1.370(8) . ?
C14C H14C 0.95 . ?
C14C C15C 1.383(7) . ?
C15C H15C 0.95 . ?
C16C H16M 0.98 . ?
C16C H16N 0.98 . ?
C16C H16O 0.98 . ?
C17C H17J 0.98 . ?
C17C H17K 0.98 . ?
C17C H17L 0.98 . ?
O1D C1D 1.243(16) . ?
O1E C0AA 1.225(13) . ?
O2D C2D 1.39(2) . ?
O2D C17D 1.441(13) . ?
O2E C2E 1.38(3) . ?
O2E C19E 1.393(14) . ?
N1D H1D 0.88 . ?
N1D C1D 1.327(15) . ?
N1D C9D 1.42(2) . ?
N1E C0AA 1.327(15) . ?
N1E C9E 1.78(2) . ?
N1E H1E 0.880(15) . ?
C0AA C2E 1.58(2) . ?
C1D C2D 1.29(2) . ?
C2D H2D 1 . ?
C2D C3D 1.66(2) . ?
C2E H2E 1 . ?
C2E C10D 1.34(2) . ?
C3D C4D 1.398(8) . ?
C3D C8D 1.385(8) . ?
C3D C9E 1.36(2) . ?
C4D H4D 0.95 . ?
C4D C5D 1.392(8) . ?
C5D H5D 0.95 . ?
C5D C6D 1.376(8) . ?
C6D H6D 0.95 . ?
C6D C7D 1.383(9) . ?
C7D H7D 0.95 . ?
C7D C8D 1.387(8) . ?
C8D H8D 0.95 . ?
C9D H9D 1 . ?
C9D C10D 1.69(2) . ?
C9D C16D 1.61(3) . ?
C9E H9E 1 . ?
C9E C16E 1.62(3) . ?
C10D C11D 1.393(7) . ?
C10D C15D 1.383(9) . ?
C11D H11D 0.95 . ?
C11D C12D 1.386(8) . ?
C12D H12D 0.95 . ?
C12D C13D 1.390(9) . ?
C13D H13D 0.95 . ?
C13D C14D 1.389(9) . ?
C14D H14D 0.95 . ?
C14D C15D 1.394(10) . ?
C15D H15D 0.95 . ?
C16D H16A 0.98 . ?
C16D H16B 0.98 . ?
C16D H16C 0.98 . ?
C16E H16D 0.98 . ?
C16E H16E 0.98 . ?
C16E H16F 0.98 . ?
C17D H17A 0.98 . ?
C17D H17B 0.98 . ?
C17D H17C 0.98 . ?
C19E H19A 0.98 . ?
C19E H19B 0.98 . ?
C19E H19C 0.98 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C1A C2A O2A 151.4(4) . . . . ?
O1A C1A C2A C3A -87.2(5) . . . . ?
O2A C2A C3A C4A 171.0(4) . . . . ?
O2A C2A C3A C8A -9.2(5) . . . . ?
N1A C1A C2A O2A -29.4(5) . . . . ?
N1A C1A C2A C3A 92.0(4) . . . . ?
N1A C9A C10A C11A -55.4(5) . . . . ?
N1A C9A C10A C15A 125.3(4) . . . . ?
C1A N1A C9A C10A -81.7(5) . . . . ?
C1A N1A C9A C16A 154.2(4) . . . . ?
C1A C2A C3A C4A 47.6(5) . . . . ?
C1A C2A C3A C8A -132.7(4) . . . . ?
C2A C3A C4A C5A -178.1(4) . . . . ?
C2A C3A C8A C7A 177.8(4) . . . . ?
C3A C4A C5A C6A -1.2(7) . . . . ?
C4A C3A C8A C7A -2.4(6) . . . . ?
C4A C5A C6A C7A 0.6(7) . . . . ?
C5A C6A C7A C8A -0.8(7) . . . . ?
C6A C7A C8A C3A 1.8(7) . . . . ?
C8A C3A C4A C5A 2.2(6) . . . . ?
C9A N1A C1A O1A -4.7(6) . . . . ?
C9A N1A C1A C2A 176.2(3) . . . . ?
C9A C10A C11A C12A -178.7(4) . . . . ?
C9A C10A C15A C14A 178.8(4) . . . . ?
C10A C11A C12A C13A -0.2(7) . . . . ?
C11A C10A C15A C14A -0.4(6) . . . . ?
C11A C12A C13A C14A -0.3(7) . . . . ?
C12A C13A C14A C15A 0.4(6) . . . . ?
C13A C14A C15A C10A -0.1(6) . . . . ?
C15A C10A C11A C12A 0.6(6) . . . . ?
C16A C9A C10A C11A 67.2(5) . . . . ?
C16A C9A C10A C15A -112.0(4) . . . . ?
C17A O2A C2A C1A -74.0(4) . . . . ?
C17A O2A C2A C3A 163.5(3) . . . . ?
O1B C1B C2B O2B 152.5(4) . . . . ?
O1B C1B C2B C3B -83.5(5) . . . . ?
O2B C2B C3B C4B 49.8(5) . . . . ?
O2B C2B C3B C8B -133.0(4) . . . . ?
N1B C1B C2B O2B -29.7(5) . . . . ?
N1B C1B C2B C3B 94.2(4) . . . . ?
N1B C9B C10B C11B -54.5(5) . . . . ?
N1B C9B C10B C15B 124.8(4) . . . . ?
C1B N1B C9B C10B -88.9(5) . . . . ?
C1B N1B C9B C16B 146.9(4) . . . . ?
C1B C2B C3B C4B -71.8(5) . . . . ?
C1B C2B C3B C8B 105.4(5) . . . . ?
C2B C3B C4B C5B 177.2(4) . . . . ?
C2B C3B C8B C7B -177.6(4) . . . . ?
C3B C4B C5B C6B 0.5(6) . . . . ?
C4B C3B C8B C7B -0.4(6) . . . . ?
C4B C5B C6B C7B -0.5(7) . . . . ?
C5B C6B C7B C8B 0.0(7) . . . . ?
C6B C7B C8B C3B 0.5(7) . . . . ?
C8B C3B C4B C5B 0.0(6) . . . . ?
C9B N1B C1B O1B -5.0(6) . . . . ?
C9B N1B C1B C2B 177.3(3) . . . . ?
C9B C10B C11B C12B 177.9(4) . . . . ?
C9B C10B C15B C14B -178.2(4) . . . . ?
C10B C11B C12B C13B 0.6(7) . . . . ?
C11B C10B C15B C14B 1.0(6) . . . . ?
C11B C12B C13B C14B 0.5(7) . . . . ?
C12B C13B C14B C15B -0.8(7) . . . . ?
C13B C14B C15B C10B 0.0(7) . . . . ?
C15B C10B C11B C12B -1.3(6) . . . . ?
C16B C9B C10B C11B 67.3(5) . . . . ?
C16B C9B C10B C15B -113.4(4) . . . . ?
C17B O2B C2B C1B -161.6(4) . . . . ?
C17B O2B C2B C3B 76.6(5) . . . . ?
O1C C1C C2C O2C 161.3(4) . . . . ?
O1C C1C C2C C3C -79.0(5) . . . . ?
O2C C2C C3C C4C -132.5(4) . . . . ?
O2C C2C C3C C8C 47.6(4) . . . . ?
N1C C1C C2C O2C -20.7(5) . . . . ?
N1C C1C C2C C3C 98.9(4) . . . . ?
N1C C9C C10C C11C 130.4(4) . . . . ?
N1C C9C C10C C15C -51.2(5) . . . . ?
C1C N1C C9C C10C -104.0(4) . . . . ?
C1C N1C C9C C16C 131.2(4) . . . . ?
C1C C2C C3C C4C 104.2(4) . . . . ?
C1C C2C C3C C8C -75.7(5) . . . . ?
C2C C3C C4C C5C 178.7(4) . . . . ?
C2C C3C C8C C7C -179.5(4) . . . . ?
C3C C4C C5C C6C 1.2(7) . . . . ?
C4C C3C C8C C7C 0.5(6) . . . . ?
C4C C5C C6C C7C 0.0(7) . . . . ?
C5C C6C C7C C8C -0.9(7) . . . . ?
C6C C7C C8C C3C 0.6(7) . . . . ?
C8C C3C C4C C5C -1.4(6) . . . . ?
C9C N1C C1C O1C 2.2(6) . . . . ?
C9C N1C C1C C2C -175.6(3) . . . . ?
C9C C10C C11C C12C 179.6(4) . . . . ?
C9C C10C C15C C14C 179.6(4) . . . . ?
C10C C11C C12C C13C -0.2(8) . . . . ?
C11C C10C C15C C14C -1.9(6) . . . . ?
C11C C12C C13C C14C 0.0(8) . . . . ?
C12C C13C C14C C15C -0.8(8) . . . . ?
C13C C14C C15C C10C 1.8(7) . . . . ?
C15C C10C C11C C12C 1.1(6) . . . . ?
C16C C9C C10C C11C -106.0(5) . . . . ?
C16C C9C C10C C15C 72.4(5) . . . . ?
C17C O2C C2C C1C -79.6(5) . . . . ?
C17C O2C C2C C3C 159.4(4) . . . . ?
O1D C1D C2D O2D 154.2(18) . . . . ?
O1D C1D C2D C3D -94.8(16) . . . . ?
O1E C0AA C2E O2E 164.1(12) . . . . ?
O1E C0AA C2E C10D -81.8(17) . . . . ?
O2D C2D C3D C4D 172.4(7) . . . . ?
O2D C2D C3D C8D -5.5(15) . . . . ?
O2E C2E C10D C11D 35.0(18) . . . . ?
O2E C2E C10D C15D -141.9(10) . . . . ?
N1D C1D C2D O2D -18(3) . . . . ?
N1D C1D C2D C3D 93.3(14) . . . . ?
N1D C9D C10D C11D -48(2) . . . . ?
N1D C9D C10D C15D 129.2(15) . . . . ?
N1E C0AA C2E O2E -17.1(19) . . . . ?
N1E C0AA C2E C10D 97.0(14) . . . . ?
C0AA N1E C9E C3D -100.1(18) . . . . ?
C0AA N1E C9E C16E 123.8(13) . . . . ?
C0AA C2E C10D C11D -84.3(15) . . . . ?
C0AA C2E C10D C15D 98.8(12) . . . . ?
C1D N1D C9D C10D -84(2) . . . . ?
C1D N1D C9D C16D 151.5(13) . . . . ?
C1D C2D C3D C4D 37.2(18) . . . . ?
C1D C2D C3D C8D -140.7(12) . . . . ?
C2D C3D C4D C5D -178.2(9) . . . . ?
C2D C3D C8D C7D 178.1(9) . . . . ?
C2E C10D C11D C12D -176.8(12) . . . . ?
C2E C10D C15D C14D 177.1(11) . . . . ?
C3D C4D C5D C6D -0.2(7) . . . . ?
C4D C3D C8D C7D 0.2(7) . . . . ?
C4D C3D C9E N1E 80.2(18) . . . . ?
C4D C3D C9E C16E -165.9(17) . . . . ?
C4D C5D C6D C7D 0.6(7) . . . . ?
C5D C6D C7D C8D -0.6(7) . . . . ?
C6D C7D C8D C3D 0.2(7) . . . . ?
C8D C3D C4D C5D -0.2(7) . . . . ?
C8D C3D C9E N1E -106.7(14) . . . . ?
C8D C3D C9E C16E 7(3) . . . . ?
C9D N1D C1D O1D -5.5(19) . . . . ?
C9D N1D C1D C2D 166.5(17) . . . . ?
C9D C10D C11D C12D 177.4(10) . . . . ?
C9D C10D C15D C14D -177.2(11) . . . . ?
C9E N1E C0AA O1E -10.7(17) . . . . ?
C9E N1E C0AA C2E 170.6(14) . . . . ?
C9E C3D C4D C5D 173.2(12) . . . . ?
C9E C3D C8D C7D -173.0(12) . . . . ?
C10D C11D C12D C13D 0.0(7) . . . . ?
C11D C10D C15D C14D -0.1(7) . . . . ?
C11D C12D C13D C14D 0.1(8) . . . . ?
C12D C13D C14D C15D -0.1(8) . . . . ?
C13D C14D C15D C10D 0.1(8) . . . . ?
C15D C10D C11D C12D 0.0(7) . . . . ?
C16D C9D C10D C11D 76.3(14) . . . . ?
C16D C9D C10D C15D -106.5(15) . . . . ?
C17D O2D C2D C1D -80(2) . . . . ?
C17D O2D C2D C3D 163.9(9) . . . . ?
C19E O2E C2E C0AA -83.9(17) . . . . ?
C19E O2E C2E C10D 163.9(11) . . . . ?
