#------------------------------------------------------------------------------
#$Date: 2023-11-06 08:48:05 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287302 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/01/1570130.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_1570130
loop_
_publ_author_name
'Zhang, Mengchu'
'Zhang, Tianyuan'
'Yu, Sifan'
'Qiu, Huang'
'Yusuf, Abdulla'
'Xu, Xinfang'
'Qian, Yu'
'Hu, Wenhao'
_publ_section_title
;
 Construction of 4-hydroxycoumarin derivatives with adjacent quaternary
 and tertiary stereocenters via ternary catalysis.
;
_journal_issue                   42
_journal_name_full               'Chemical science'
_journal_page_first              11850
_journal_page_last               11857
_journal_paper_doi               10.1039/d3sc03452f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C29 H23 N O4'
_chemical_formula_sum            'C29 H23 N O4'
_chemical_formula_weight         449.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-05-22 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                112.6020(10)
_cell_angle_beta                 91.9090(10)
_cell_angle_gamma                104.2180(10)
_cell_formula_units_Z            2
_cell_length_a                   10.06580(10)
_cell_length_b                   10.9123(2)
_cell_length_c                   11.3400(2)
_cell_measurement_reflns_used    20022
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.5840
_cell_measurement_theta_min      4.2360
_cell_volume                     1103.30(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  26.00   0.50    0.10    --  -46.62  57.00  90.00  178
  2  ω    -44.00 -18.00   0.50    0.10    --    8.00 132.00  90.05   52
  3  ω      5.00  33.00   0.50    0.10    --   36.00  93.00  85.34   56
  4  ω     28.00 125.00   0.50    0.10    --   52.00  77.00  58.53  194
  5  ω     90.00 178.00   0.50    0.80    --  107.00 102.00 137.00  176
  6  ω    113.00 139.00   0.50    0.80    --  107.00  45.00 150.00   52
  7  ω    106.00 132.00   0.50    0.10    --   60.00  74.00 163.69   52
  8  ω     38.00  64.00   0.50    0.10    --   60.00  74.00 163.69   52
  9  ω     34.00 129.00   0.50    0.10    --   56.00  73.00 141.67  190
 10  ω     46.00  72.00   0.50    0.10    --   68.00  75.00   7.91   52
 11  ω     31.00 122.00   0.50    0.10    --   46.62  19.00 -60.00  182
 12  ω     66.00 105.00   0.50    0.80    --  107.00 -77.00   0.00   78
 13  ω     81.00 106.00   0.50    0.80    --  107.00-102.00  34.00   50
 14  ω     77.00 112.00   0.50    0.80    --  107.00-125.00  30.00   70
 15  ω     73.00 105.00   0.50    0.80    --  107.00 -94.00   0.00   64
 16  ω     85.00 112.00   0.50    0.80    --  107.00-125.00 -60.00   54
 17  ω     64.00 112.00   0.50    0.80    --  107.00-125.00 -30.00   96
 18  ω     49.00 112.00   0.50    0.80    --  107.00-125.00   0.00  126
 19  ω     45.00  70.00   0.50    0.80    --  107.00-125.00  30.00   50
 20  ω     35.00  69.00   0.50    0.80    --  107.00 -94.00   0.00   68
 21  ω     38.00  68.00   0.50    0.80    --  107.00 -61.00  30.00   60
 22  ω     35.00  68.00   0.50    0.80    --  107.00 -61.00  90.00   66
 23  ω     35.00  90.00   0.50    0.80    --  107.00 -94.00 150.00  110
 24  ω     74.00 112.00   0.50    0.80    --  107.00-125.00 150.00   76
 25  ω     34.00 112.00   0.50    0.80    --  107.00-125.00 120.00  156
 26  ω     36.00  62.00   0.50    0.80    --  107.00-125.00 150.00   52
 27  ω     -9.00  83.00   0.50    0.10    --   46.62-102.00  34.00  184
 28  ω     41.00  69.00   0.50    0.80    --  107.00 -61.00 -90.00   56
 29  ω     40.00  79.00   0.50    0.80    --  107.00 -94.00-120.00   78
 30  ω     81.00 110.00   0.50    0.80    --  107.00-125.00-150.00   58
 31  ω     78.00 105.00   0.50    0.80    --  107.00 -94.00-180.00   54
 32  ω     70.00 106.00   0.50    0.80    --  107.00 -77.00-180.00   72
 33  ω     54.00  79.00   0.50    0.80    --  107.00-125.00-150.00   50
 34  ω     37.00  64.00   0.50    0.80    --  107.00 -77.00-180.00   54
 35  ω     36.00  71.00   0.50    0.80    --  107.00 -61.00-180.00   70
 36  ω     34.00  59.00   0.50    0.80    --  107.00 -94.00-180.00   50
 37  ω     37.00  70.00   0.50    0.80    --  107.00 -61.00-120.00   66
 38  ω     36.00  63.00   0.50    0.80    --  107.00-125.00 -60.00   54
 39  ω     94.00 178.00   0.50    0.80    --  107.00  45.00 -60.00  168
 40  ω     31.00 125.00   0.50    0.10    --   52.00  70.00  33.88  188
 41  ω     31.00 129.00   0.50    0.10    --   56.00  80.00-108.52  196
 42  ω     37.00  63.00   0.50    0.10    --   60.00  75.00-121.64   52
 43  ω     33.00  58.00   0.50    0.10    --   56.00  75.00-139.50   50
 44  ω     28.00 125.00   0.50    0.10    --   52.00  77.00-157.06  194
 45  ω     23.00 120.00   0.50    0.10    --   46.62  77.00   0.00  194
 46  ω     27.00 125.00   0.50    0.10    --   52.00  79.00 -63.29  196
 47  ω     36.00  62.00   0.50    0.10    --   60.00  78.00 135.63   52
 48  ω    -17.00  27.00   0.50    0.10    --   16.00  97.00  -1.14   88
 49  ω      4.00  33.00   0.50    0.10    --   36.00  94.00-151.81   58
 50  ω    -66.00 -41.00   0.50    0.10    --  -64.00 -75.00 -47.29   50
 51  ω    -37.00 -10.00   0.50    0.10    --  -40.00 -90.00 -91.46   54
 52  ω    -63.00 -35.00   0.50    0.10    --  -60.00 -80.00 -59.05   56
 53  ω    -71.00 -45.00   0.50    0.10    --  -68.00 -75.00-166.58   52
 54  ω    -84.00 -58.00   0.50    0.80    --  -80.00 -72.00-123.10   52
 55  ω    -83.00 -58.00   0.50    0.80    --  -80.00 -73.00 -73.37   50
 56  ω    -88.00 -58.00   0.50    0.80    --  -80.00 -73.00 -86.07   60
 57  ω    -90.00 -64.00   0.50    0.80    --  -80.00 -60.00-121.97   52
 58  ω    -89.00 -63.00   0.50    0.80    --  -84.00 -73.00-163.23   52
 59  ω    -94.00 -68.00   0.50    0.80    --  -84.00 -61.00-167.36   52
 60  ω    -93.00 -67.00   0.50    0.80    --  -88.00 -71.00-174.39   52
 61  ω   -106.00 -77.00   0.50    0.80    -- -100.00 -79.00-130.44   58
 62  ω   -106.00 -76.00   0.50    0.80    -- -100.00 -77.00-120.00   60
 63  ω   -104.00 -77.00   0.50    0.80    -- -100.00 -75.00 -72.26   54
 64  ω    -94.00 -69.00   0.50    0.80    --  -92.00 -74.00 -45.47   50
 65  ω    -92.00 -58.00   0.50    0.80    --  -80.00 -73.00 -20.55   68
 66  ω    -80.00 -54.00   0.50    0.80    --  -76.00 -72.00  24.43   52
 67  ω    -62.00 -36.00   0.50    0.10    --  -60.00 -78.00  57.84   52
 68  ω    -74.00 -49.00   0.50    0.10    --  -68.00 -64.00 144.90   50
 69  ω    -71.00 -45.00   0.50    0.10    --  -68.00 -74.00 131.48   52
 70  ω    -87.00 -52.00   0.50    0.80    --  -76.00 -76.00  66.19   70
 71  ω    -85.00 -59.00   0.50    0.80    --  -80.00 -73.00  97.69   52
 72  ω    -85.00 -59.00   0.50    0.80    --  -80.00 -69.00  76.60   52
 73  ω    -88.00 -62.00   0.50    0.80    --  -84.00 -73.00  61.83   52
 74  ω    -91.00 -61.00   0.50    0.80    --  -80.00 -64.00 122.42   60
 75  ω    -88.00 -62.00   0.50    0.80    --  -84.00 -72.00 109.72   52
 76  ω    -91.00 -65.00   0.50    0.80    --  -88.00 -74.00  59.20   52
 77  ω    -84.00 -58.00   0.50    0.80    --  -80.00 -74.00   9.87   52
 78  ω    -97.00 -65.00   0.50    0.80    --  -84.00 -65.00 -55.19   64
 79  ω   -106.00 -79.00   0.50    0.80    --  -96.00 -60.00 -11.27   54
 80  ω   -107.00 -79.00   0.50    0.80    -- -100.00 -73.00 -53.25   56
 81  ω   -112.00 -83.00   0.50    0.80    -- -100.00 -77.00 -30.00   58
 82  ω   -125.00 -80.00   0.50    0.80    -- -100.00 -68.00 -90.41   90
 83  ω   -124.00 -82.00   0.50    0.80    -- -100.00 -71.00-146.41   84
 84  ω   -125.00 -78.00   0.50    0.80    -- -100.00 -74.00-113.15   94
 85  ω   -119.00 -74.00   0.50    0.10    --  -46.62-125.00-180.00   90
 86  ω   -137.00-112.00   0.50    0.10    --  -64.00 -75.00 -47.29   50
 87  ω   -119.00 -23.00   0.50    0.10    --  -46.62 -77.00  30.00  192
 88  ω    -92.00 -66.00   0.50    0.80    --  -88.00 -75.00 132.52   52
 89  ω   -101.00 -66.00   0.50    0.80    --  -84.00 -65.00 140.28   70
 90  ω   -108.00 -76.00   0.50    0.80    -- -100.00 -77.00  60.00   64
 91  ω   -105.00 -77.00   0.50    0.80    -- -100.00 -74.00  71.34   56
 92  ω   -108.00 -82.00   0.50    0.80    -- -100.00 -65.00 112.08   52
 93  ω   -112.00 -77.00   0.50    0.80    -- -100.00 -74.00 160.32   70
 94  ω   -111.00 -79.00   0.50    0.80    -- -100.00 -72.00  99.44   64
 95  ω   -110.00 -78.00   0.50    0.80    -- -100.00 -78.00 137.21   64
 96  ω   -119.00 -23.00   0.50    0.10    --  -46.62 -77.00  90.00  192
 97  ω   -116.00 -76.00   0.50    0.80    -- -100.00 -78.00  -5.10   80
 98  ω   -131.00 -74.00   0.50    0.80    --  -92.00 -64.00  17.55  114
 99  ω   -127.00 -80.00   0.50    0.80    -- -100.00 -72.00 108.96   94
100  ω   -136.00 -78.00   0.50    0.80    -- -100.00 -76.00 142.81  116
101  ω   -146.00-120.00   0.50    0.80    --  -76.00 -72.00  24.43   52
102  ω   -145.00 -80.00   0.50    0.80    -- -100.00 -68.00  -5.44  130
103  ω   -145.00-119.00   0.50    0.80    --  -80.00 -64.00 122.42   52
104  ω   -142.00-116.00   0.50    0.80    -- -100.00 -72.00  99.44   52
105  ω   -145.00 -77.00   0.50    0.80    -- -100.00 -77.00  30.00  136
106  ω   -140.00-114.00   0.50    0.80    -- -100.00 -54.00  15.05   52
107  ω   -153.00-127.00   0.50    0.80    --  -96.00 -60.00 -11.27   52
108  ω   -157.00-113.00   0.50    0.80    -- -100.00 -75.00 -72.26   88
109  ω   -168.00-142.00   0.50    0.80    -- -100.00 -79.00-130.44   52
110  ω   -156.00 -78.00   0.50    0.80    -- -100.00 -72.00-168.47  156
111  ω   -163.00-138.00   0.50    0.80    -- -100.00 -73.00 -53.25   50
112  ω   -165.00-139.00   0.50    0.80    -- -100.00 -77.00 -30.00   52
113  ω   -170.00-144.00   0.50    0.80    -- -100.00 -68.00 -90.41   52
114  ω   -173.00-131.00   0.50    0.80    -- -100.00 -74.00-113.15   84
115  ω   -173.00-140.00   0.50    0.80    -- -100.00 -77.00-120.00   66
116  ω   -170.00 -76.00   0.50    0.80    -- -100.00 -77.00-150.00  188
117  ω   -169.00 -77.00   0.50    0.80    -- -100.00 -76.00 -24.66  184
118  ω   -164.00-138.00   0.50    0.80    -- -100.00 -77.00  60.00   52
119  ω   -173.00 -86.00   0.50    0.80    -- -100.00-102.00  34.00  174
120  ω   -167.00 -81.00   0.50    0.80    -- -100.00 -65.00 172.23  172
121  ω   -173.00-124.00   0.50    0.80    -- -100.00 -65.00 112.08   98
122  ω   -173.00 -81.00   0.50    0.80    -- -100.00 -72.00  91.04  184
123  ω   -171.00-132.00   0.50    0.80    -- -100.00 -74.00 160.32   78
124  ω   -173.00-126.00   0.50    0.80    -- -100.00 -78.00 137.21   94
125  ω   -173.00 -76.00   0.50    0.80    -- -100.00 -77.00  53.55  194
126  ω   -169.00 -79.00   0.50    0.80    -- -100.00 -72.00-103.46  180
127  ω   -162.00-130.00   0.50    0.80    -- -100.00 -15.00 -90.00   64
128  ω   -172.00-100.00   0.50    0.80    -- -100.00 -49.00  59.98  144
129  ω    -82.00  13.00   0.50    0.10    --  -46.62 102.00 137.00  190
130  ω   -106.00 -27.00   0.50    0.80    -- -100.00 102.00 137.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1589974000
_diffrn_orient_matrix_UB_12      -0.0350506000
_diffrn_orient_matrix_UB_13      -0.0105728000
_diffrn_orient_matrix_UB_21      -0.0126448000
_diffrn_orient_matrix_UB_22      -0.0989613000
_diffrn_orient_matrix_UB_23      -0.1425815000
_diffrn_orient_matrix_UB_31      -0.0024419000
_diffrn_orient_matrix_UB_32      -0.1198068000
_diffrn_orient_matrix_UB_33      0.0407790000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            44222
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.040
_diffrn_reflns_theta_min         4.267
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4553
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0987P)²+0.2025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3918
_reflns_number_total             4553
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc03452f2.cif
_cod_data_source_block           zhangmch_210427_3
_cod_depositor_comments
'Adding full bibliography for 1570130--1570133.cif.'
_cod_database_code               1570130
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C3-H3
 0.91 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C16(H16), C20(H20), C24(H24), C11(H11), C19(H19), C18(H18), C26(H26),
 C17(H17), C8(H8), C27(H27), C10(H10), C9(H9)
3.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C31(H31A,H31B,H31C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.773
_oxdiff_exptl_absorpt_empirical_full_min 0.619
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O14 O 0.73232(9) 0.48855(10) 0.18687(9) 0.0238(2) Uani 1 1 d . . . . .
O6 O 0.57140(10) 0.18747(11) 0.31826(10) 0.0297(3) Uani 1 1 d . . . . .
O30 O 1.01698(10) 0.73028(11) 0.69430(9) 0.0295(3) Uani 1 1 d . . . . .
O34 O 0.73210(11) 0.28898(11) 0.48947(10) 0.0312(3) Uani 1 1 d . . . . .
N29 N 0.93181(12) 0.88427(13) 0.64434(11) 0.0272(3) Uani 1 1 d . . . . .
C4 C 0.72892(14) 0.41127(14) 0.35679(13) 0.0234(3) Uani 1 1 d . . . . .
C13 C 0.67811(13) 0.39752(14) 0.23922(13) 0.0230(3) Uani 1 1 d . . . . .
C12 C 0.56125(14) 0.28376(14) 0.15970(13) 0.0253(3) Uani 1 1 d . . . . .
C3 C 0.84478(13) 0.53493(14) 0.44043(13) 0.0229(3) Uani 1 1 d D . . . .
C5 C 0.68197(14) 0.29719(15) 0.39569(14) 0.0262(3) Uani 1 1 d . . . . .
C2 C 0.92568(13) 0.59175(14) 0.35464(13) 0.0230(3) Uani 1 1 d . . . . .
H2 H 1.018013 0.642430 0.383544 0.028 Uiso 1 1 calc R U . . .
C23 C 0.73640(14) 0.74101(15) 0.50186(13) 0.0237(3) Uani 1 1 d . . . . .
C1 C 0.86921(13) 0.57172(14) 0.23884(13) 0.0227(3) Uani 1 1 d . . . . .
C16 C 0.85315(15) 0.63829(15) 0.05209(13) 0.0267(3) Uani 1 1 d . . . . .
H16 H 0.757171 0.613189 0.046432 0.032 Uiso 1 1 calc R U . . .
C20 C 1.07789(14) 0.66603(14) 0.15510(13) 0.0250(3) Uani 1 1 d . . . . .
H20 H 1.133044 0.659575 0.218701 0.030 Uiso 1 1 calc R U . . .
C7 C 0.50951(14) 0.18266(15) 0.20620(14) 0.0271(3) Uani 1 1 d . . . . .
C24 C 0.62045(14) 0.71008(15) 0.41615(13) 0.0252(3) Uani 1 1 d . . . . .
H24 H 0.565731 0.619138 0.374624 0.030 Uiso 1 1 calc R U . . .
C21 C 0.92967(14) 0.75642(15) 0.63737(13) 0.0249(3) Uani 1 1 d . . . . .
C25 C 0.58446(14) 0.81523(16) 0.39118(13) 0.0277(3) Uani 1 1 d . . . . .
C15 C 0.93373(14) 0.62619(14) 0.14772(13) 0.0227(3) Uani 1 1 d . . . . .
C22 C 0.79826(13) 0.65105(14) 0.54757(13) 0.0232(3) Uani 1 1 d . . . . .
C11 C 0.49516(15) 0.27128(16) 0.04339(14) 0.0283(3) Uani 1 1 d . . . . .
H11 H 0.528584 0.337425 0.010797 0.034 Uiso 1 1 calc R U . . .
C19 C 1.13903(15) 0.71506(15) 0.06819(14) 0.0279(3) Uani 1 1 d . . . . .
H19 H 1.235004 0.741745 0.074141 0.034 Uiso 1 1 calc R U . . .
C18 C 1.05814(16) 0.72463(15) -0.02765(14) 0.0292(3) Uani 1 1 d . . . . .
H18 H 1.099448 0.755745 -0.086937 0.035 Uiso 1 1 calc R U . . .
C26 C 0.66703(16) 0.95070(16) 0.45631(15) 0.0305(3) Uani 1 1 d . . . . .
H26 H 0.643204 1.020917 0.440961 0.037 Uiso 1 1 calc R U . . .
C28 C 0.81770(14) 0.87786(15) 0.56431(13) 0.0259(3) Uani 1 1 d . . . . .
C17 C 0.91547(16) 0.68749(15) -0.03432(14) 0.0292(3) Uani 1 1 d . . . . .
H17 H 0.860965 0.695601 -0.097276 0.035 Uiso 1 1 calc R U . . .
C8 C 0.39307(15) 0.07287(16) 0.14078(16) 0.0330(3) Uani 1 1 d . . . . .
H8 H 0.358492 0.007041 0.173467 0.040 Uiso 1 1 calc R U . . .
C27 C 0.78459(16) 0.98437(16) 0.54403(15) 0.0307(3) Uani 1 1 d . . . . .
H27 H 0.838649 1.075362 0.587244 0.037 Uiso 1 1 calc R U . . .
C32 C 0.70468(14) 0.59282(15) 0.62939(13) 0.0262(3) Uani 1 1 d . . . . .
H32A H 0.618704 0.532387 0.576924 0.039 Uiso 1 1 calc R U . . .
H32B H 0.686907 0.667631 0.700279 0.039 Uiso 1 1 calc R U . . .
H32C H 0.750072 0.542122 0.661990 0.039 Uiso 1 1 calc R U . . .
C10 C 0.38067(16) 0.16133(17) -0.02314(16) 0.0343(4) Uani 1 1 d . . . . .
H10 H 0.337779 0.152875 -0.100896 0.041 Uiso 1 1 calc R U . . .
C9 C 0.32937(16) 0.06299(17) 0.02625(17) 0.0361(4) Uani 1 1 d . . . . .
H9 H 0.251355 -0.010169 -0.018329 0.043 Uiso 1 1 calc R U . . .
C33 C 0.45760(16) 0.78164(18) 0.29853(15) 0.0329(3) Uani 1 1 d . . . . .
H33A H 0.448774 0.695528 0.226568 0.049 Uiso 1 1 calc R U . . .
H33B H 0.465622 0.853786 0.268322 0.049 Uiso 1 1 calc R U . . .
H33C H 0.377284 0.774130 0.341456 0.049 Uiso 1 1 calc R U . . .
C31 C 1.03582(16) 1.00991(17) 0.72626(16) 0.0351(4) Uani 1 1 d . . . . .
H31A H 0.995403 1.064229 0.795985 0.053 Uiso 1 1 calc R U . . .
H31B H 1.070834 1.061904 0.676727 0.053 Uiso 1 1 calc R U . . .
H31C H 1.110280 0.987035 0.760471 0.053 Uiso 1 1 calc R U . . .
H3 H 0.8993(16) 0.5045(17) 0.4849(15) 0.029(4) Uiso 1 1 d D . . . .
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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_
_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
C13 O14 C1 116.14(10) . . ?
C7 O6 C5 121.99(11) . . ?
C21 N29 C28 111.13(12) . . ?
C21 N29 C31 123.97(12) . . ?
C28 N29 C31 124.88(13) . . ?
C13 C4 C3 120.78(12) . . ?
C13 C4 C5 119.24(13) . . ?
C5 C4 C3 119.57(12) . . ?
O14 C13 C12 115.07(12) . . ?
C4 C13 O14 122.91(12) . . ?
C4 C13 C12 122.01(13) . . ?
C7 C12 C13 116.59(13) . . ?
C7 C12 C11 118.72(13) . . ?
C11 C12 C13 124.66(13) . . ?
C4 C3 C2 108.25(11) . . ?
C4 C3 C22 114.80(11) . . ?
C4 C3 H3 106.9(11) . . ?
C2 C3 C22 110.49(11) . . ?
C2 C3 H3 111.2(11) . . ?
C22 C3 H3 105.1(11) . . ?
O6 C5 C4 117.69(12) . . ?
O34 C5 O6 116.75(13) . . ?
O34 C5 C4 125.55(14) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 C3 121.97(12) . . ?
C1 C2 H2 119.0 . . ?
C24 C23 C22 131.73(13) . . ?
C24 C23 C28 119.51(13) . . ?
C28 C23 C22 108.76(12) . . ?
O14 C1 C15 110.86(11) . . ?
C2 C1 O14 121.39(12) . . ?
C2 C1 C15 127.74(12) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C17 C16 C15 120.40(13) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C15 120.38(13) . . ?
O6 C7 C12 121.53(13) . . ?
O6 C7 C8 117.22(13) . . ?
C8 C7 C12 121.26(14) . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.35(14) . . ?
C25 C24 H24 119.8 . . ?
O30 C21 N29 125.52(13) . . ?
O30 C21 C22 125.88(13) . . ?
N29 C21 C22 108.60(12) . . ?
C24 C25 C33 120.33(14) . . ?
C26 C25 C24 118.56(13) . . ?
C26 C25 C33 121.09(13) . . ?
C16 C15 C1 121.14(12) . . ?
C16 C15 C20 118.70(13) . . ?
C20 C15 C1 120.15(12) . . ?
C23 C22 C3 115.62(11) . . ?
C23 C22 C21 101.81(11) . . ?
C23 C22 C32 111.72(11) . . ?
C21 C22 C3 107.51(10) . . ?
C32 C22 C3 111.45(11) . . ?
C32 C22 C21 107.93(11) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.34(14) . . ?
C10 C11 H11 119.8 . . ?
C20 C19 H19 119.8 . . ?
C20 C19 C18 120.49(13) . . ?
C18 C19 H19 119.8 . . ?
C19 C18 H18 120.3 . . ?
C17 C18 C19 119.47(13) . . ?
C17 C18 H18 120.3 . . ?
C25 C26 H26 119.0 . . ?
C25 C26 C27 122.00(14) . . ?
C27 C26 H26 119.0 . . ?
C23 C28 N29 109.58(12) . . ?
C27 C28 N29 128.52(14) . . ?
C27 C28 C23 121.90(13) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.54(13) . . ?
C18 C17 H17 119.7 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.93(15) . . ?
C9 C8 H8 120.5 . . ?
C26 C27 H27 121.2 . . ?
C28 C27 C26 117.67(14) . . ?
C28 C27 H27 121.2 . . ?
C22 C32 H32A 109.5 . . ?
C22 C32 H32B 109.5 . . ?
C22 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C11 C10 H10 120.0 . . ?
C11 C10 C9 119.95(15) . . ?
C9 C10 H10 120.0 . . ?
C8 C9 C10 120.79(14) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C25 C33 H33A 109.5 . . ?
C25 C33 H33B 109.5 . . ?
C25 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N29 C31 H31A 109.5 . . ?
N29 C31 H31B 109.5 . . ?
N29 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
O14 C13 1.3584(17) . ?
O14 C1 1.4107(16) . ?
O6 C5 1.3840(18) . ?
O6 C7 1.3731(18) . ?
O30 C21 1.2237(17) . ?
O34 C5 1.2055(18) . ?
N29 C21 1.3614(19) . ?
N29 C28 1.4107(18) . ?
N29 C31 1.4456(19) . ?
C4 C13 1.351(2) . ?
C4 C3 1.5000(19) . ?
C4 C5 1.454(2) . ?
C13 C12 1.446(2) . ?
C12 C7 1.396(2) . ?
C12 C11 1.400(2) . ?
C3 C2 1.5042(19) . ?
C3 C22 1.5643(18) . ?
C3 H3 0.930(9) . ?
C2 H2 0.9300 . ?
C2 C1 1.3281(19) . ?
C23 C24 1.3782(19) . ?
C23 C22 1.5133(19) . ?
C23 C28 1.396(2) . ?
C1 C15 1.4732(19) . ?
C16 H16 0.9300 . ?
C16 C15 1.3983(19) . ?
C16 C17 1.386(2) . ?
C20 H20 0.9300 . ?
C20 C15 1.3985(19) . ?
C20 C19 1.386(2) . ?
C7 C8 1.389(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.405(2) . ?
C21 C22 1.5401(19) . ?
C25 C26 1.392(2) . ?
C25 C33 1.501(2) . ?
C22 C32 1.5392(19) . ?
C11 H11 0.9300 . ?
C11 C10 1.380(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.388(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.384(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.397(2) . ?
C28 C27 1.380(2) . ?
C17 H17 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.383(2) . ?
C27 H27 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C9 1.393(2) . ?
C9 H9 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
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
O14 C13 C12 C7 175.33(11) . . . . ?
O14 C13 C12 C11 -6.85(19) . . . . ?
O14 C1 C15 C16 23.22(17) . . . . ?
O14 C1 C15 C20 -156.32(12) . . . . ?
O6 C7 C8 C9 -178.79(13) . . . . ?
O30 C21 C22 C3 -55.43(17) . . . . ?
O30 C21 C22 C23 -177.38(13) . . . . ?
O30 C21 C22 C32 64.91(16) . . . . ?
N29 C21 C22 C3 125.35(12) . . . . ?
N29 C21 C22 C23 3.40(13) . . . . ?
N29 C21 C22 C32 -114.31(12) . . . . ?
N29 C28 C27 C26 178.12(13) . . . . ?
C4 C13 C12 C7 -4.63(19) . . . . ?
C4 C13 C12 C11 173.18(13) . . . . ?
C4 C3 C2 C1 25.13(17) . . . . ?
C4 C3 C22 C23 -76.66(15) . . . . ?
C4 C3 C22 C21 170.43(11) . . . . ?
C4 C3 C22 C32 52.34(15) . . . . ?
C13 O14 C1 C2 -20.11(17) . . . . ?
C13 O14 C1 C15 159.06(11) . . . . ?
C13 C4 C3 C2 -25.02(16) . . . . ?
C13 C4 C3 C22 98.93(14) . . . . ?
C13 C4 C5 O6 -9.70(18) . . . . ?
C13 C4 C5 O34 169.50(13) . . . . ?
C13 C12 C7 O6 -3.42(19) . . . . ?
C13 C12 C7 C8 176.58(12) . . . . ?
C13 C12 C11 C10 -177.41(13) . . . . ?
C12 C7 C8 C9 1.2(2) . . . . ?
C12 C11 C10 C9 0.8(2) . . . . ?
C3 C4 C13 O14 3.77(19) . . . . ?
C3 C4 C13 C12 -176.27(11) . . . . ?
C3 C4 C5 O6 177.61(11) . . . . ?
C3 C4 C5 O34 -3.2(2) . . . . ?
C3 C2 C1 O14 -4.0(2) . . . . ?
C3 C2 C1 C15 176.98(12) . . . . ?
C5 O6 C7 C12 4.60(19) . . . . ?
C5 O6 C7 C8 -175.41(12) . . . . ?
C5 C4 C13 O14 -168.83(11) . . . . ?
C5 C4 C13 C12 11.13(19) . . . . ?
C5 C4 C3 C2 147.56(12) . . . . ?
C5 C4 C3 C22 -88.50(15) . . . . ?
C2 C3 C22 C23 46.09(15) . . . . ?
C2 C3 C22 C21 -66.82(14) . . . . ?
C2 C3 C22 C32 175.10(11) . . . . ?
C2 C1 C15 C16 -157.67(14) . . . . ?
C2 C1 C15 C20 22.8(2) . . . . ?
C23 C24 C25 C26 -1.0(2) . . . . ?
C23 C24 C25 C33 -179.57(12) . . . . ?
C23 C28 C27 C26 -1.1(2) . . . . ?
C1 O14 C13 C4 20.21(17) . . . . ?
C1 O14 C13 C12 -159.76(11) . . . . ?
C20 C19 C18 C17 1.4(2) . . . . ?
C7 O6 C5 O34 -177.33(12) . . . . ?
C7 O6 C5 C4 1.94(18) . . . . ?
C7 C12 C11 C10 0.4(2) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C24 C23 C22 C3 61.38(19) . . . . ?
C24 C23 C22 C21 177.56(14) . . . . ?
C24 C23 C22 C32 -67.50(18) . . . . ?
C24 C23 C28 N29 -178.55(12) . . . . ?
C24 C23 C28 C27 0.8(2) . . . . ?
C24 C25 C26 C27 0.7(2) . . . . ?
C21 N29 C28 C23 0.09(16) . . . . ?
C21 N29 C28 C27 -179.19(14) . . . . ?
C25 C26 C27 C28 0.3(2) . . . . ?
C15 C16 C17 C18 0.3(2) . . . . ?
C15 C20 C19 C18 -0.3(2) . . . . ?
C22 C3 C2 C1 -101.37(15) . . . . ?
C22 C23 C24 C25 179.33(13) . . . . ?
C22 C23 C28 N29 2.21(15) . . . . ?
C22 C23 C28 C27 -178.45(13) . . . . ?
C11 C12 C7 O6 178.63(12) . . . . ?
C11 C12 C7 C8 -1.4(2) . . . . ?
C11 C10 C9 C8 -0.9(2) . . . . ?
C19 C20 C15 C1 178.87(12) . . . . ?
C19 C20 C15 C16 -0.7(2) . . . . ?
C19 C18 C17 C16 -1.4(2) . . . . ?
C28 N29 C21 O30 178.46(13) . . . . ?
C28 N29 C21 C22 -2.31(15) . . . . ?
C28 C23 C24 C25 0.3(2) . . . . ?
C28 C23 C22 C3 -119.51(13) . . . . ?
C28 C23 C22 C21 -3.33(13) . . . . ?
C28 C23 C22 C32 111.61(13) . . . . ?
C17 C16 C15 C1 -178.86(12) . . . . ?
C17 C16 C15 C20 0.7(2) . . . . ?
C33 C25 C26 C27 179.25(13) . . . . ?
C31 N29 C21 O30 -3.2(2) . . . . ?
C31 N29 C21 C22 176.04(12) . . . . ?
C31 N29 C28 C23 -178.24(13) . . . . ?
C31 N29 C28 C27 2.5(2) . . . . ?
