#------------------------------------------------------------------------------
#$Date: 2024-07-05 18:05:24 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292914 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/13/1571375.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_1571375
loop_
_publ_author_name
'Chen, Bin'
'Pan, Bendu'
'He, Xiaobo'
'Jiang, Long'
'Chan, Albert S. C.'
'Qiu, Liqin'
_publ_section_title
;
 Access to chiral dihydrophenanthridines via a
 palladium(0)-catalyzed Suzuki coupling and C-H arylation cascade reaction
 using new chiral-bridged biphenyl bifunctional ligands.
;
_journal_issue                   18
_journal_name_full               'Chemical science'
_journal_page_first              6884
_journal_page_last               6890
_journal_paper_doi               10.1039/d4sc00621f
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H25 N O2, 0.08(H2 O1)'
_chemical_formula_sum            'C25 H25.17 N O2.08'
_chemical_formula_weight         372.96
_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_Hall           'P 31 2"'
_space_group_name_H-M_alt        'P 31 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-11-14 deposited with the CCDC.	2024-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   11.43405(6)
_cell_length_b                   11.43405(6)
_cell_length_c                   25.89293(13)
_cell_measurement_reflns_used    39378
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.0070
_cell_measurement_theta_min      4.4180
_cell_volume                     2931.65(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  27.00   1.00    2.00    --   38.00  90.00-156.35   25
  2  ω    -98.00 -19.00   1.00    2.00    --  -41.94 -38.00-180.00   79
  3  ω   -112.00 -15.00   1.00    2.00    --  -41.94 -57.00 120.00   97
  4  ω   -101.00 -74.00   1.00    2.00    --  -41.94 -57.00 -30.00   27
  5  ω    -67.00 -17.00   1.00    2.00    --  -41.94 -57.00 -30.00   50
  6  ω   -118.00  -6.00   1.00    2.00    --  -41.94 -19.00 -90.00  112
  7  ω      6.00  81.00   1.00    2.00    --   41.94 -99.00   0.00   75
  8  ω     10.00  35.00   1.00    2.00    --   41.94  78.00 -42.18   25
  9  ω     27.00  94.00   1.00    2.00    --   41.94-125.00-150.00   67
 10  ω     14.00  39.00   1.00    2.00    --   46.00  81.00   0.50   25
 11  ω     13.00  38.00   1.00    2.00    --   46.00  82.00-156.35   25
 12  ω     14.00  42.00   1.00    2.00    --   46.00  81.00  55.05   28
 13  ω     13.00  38.00   1.00    2.00    --   46.00  82.00  91.46   25
 14  ω     25.00  54.00   1.00    2.00    --   54.00  71.00-108.66   29
 15  ω     83.00 129.00   1.00    2.00    --   58.00  70.00  18.19   46
 16  ω     28.00  54.00   1.00    2.00    --   58.00  70.00  18.19   26
 17  ω     29.00  54.00   1.00    2.00    --   58.00  71.00 140.60   25
 18  ω    101.00 130.00   1.00    2.00    --   58.00  71.00 140.60   29
 19  ω     37.00  62.00   1.00    2.00    --   66.00  70.00 -47.60   25
 20  ω    108.00 134.00   1.00    2.00    --   66.00  70.00 -47.60   26
 21  ω     37.00  62.00   1.00    2.00    --   66.00  69.00 -72.16   25
 22  ω     36.00  62.00   1.00    2.00    --   66.00  71.00 151.49   26
 23  ω     41.00  70.00   1.00    2.00    --   70.00  69.00-125.01   29
 24  ω     40.00  66.00   1.00    2.00    --   70.00  70.00  92.44   26
 25  ω    105.00 131.00   1.00    2.00    --   70.00  70.00-159.10   26
 26  ω    116.00 142.00   1.00    2.00    --   70.00  70.00  33.06   26
 27  ω     40.00  66.00   1.00    2.00    --   70.00  70.00-159.10   26
 28  ω     43.00  68.00   1.00    2.00    --   70.00  64.00-176.14   25
 29  ω     40.00  66.00   1.00    2.00    --   70.00  70.00  33.06   26
 30  ω     44.00  78.00   1.00    2.00    --   74.00  71.00 121.27   34
 31  ω     94.00 120.00   1.00    2.00    --   74.00  71.00 121.27   26
 32  ω     46.00  74.00   1.00    2.00    --   74.00  64.00 -17.42   28
 33  ω     48.00  74.00   1.00    8.00    --   78.00  70.00  43.71   26
 34  ω    134.00 160.00   1.00    8.00    --   90.00  68.00  41.85   26
 35  ω     60.00  93.00   1.00    8.00    --   90.00  70.00-108.20   33
 36  ω     61.00  94.00   1.00    8.00    --   90.00  68.00  41.85   33
 37  ω     64.00  90.00   1.00    8.00    --   90.00  56.00   9.55   26
 38  ω    102.00 161.00   1.00    8.00    --   90.00  69.00-139.78   59
 39  ω     61.00  89.00   1.00    8.00    --   90.00  69.00-139.78   28
 40  ω     62.00  93.00   1.00    8.00    --   90.00  62.00 -48.57   31
 41  ω     70.00  96.00   1.00    8.00    --   94.00  46.00  -3.66   26
 42  ω     66.00  97.00   1.00    8.00    --   94.00  61.00 103.15   31
 43  ω     67.00 101.00   1.00    8.00    --   94.00  57.00 167.09   34
 44  ω    146.00 172.00   1.00    8.00    --  106.00  65.00 -22.41   26
 45  ω     78.00 125.00   1.00    8.00    --  106.00  65.00 -22.41   47
 46  ω     33.00 104.00   1.00    8.00    --  111.00 -94.00 -60.00   71
 47  ω     83.00 175.00   1.00    8.00    --  111.00  61.00  90.00   92
 48  ω     42.00 107.00   1.00    8.00    --  111.00-111.00 150.00   65
 49  ω     84.00 171.00   1.00    8.00    --  111.00  61.00  30.00   87
 50  ω    143.00 171.00   1.00    8.00    --  111.00  61.00   0.00   28
 51  ω     84.00 140.00   1.00    8.00    --  111.00  61.00   0.00   56
 52  ω    115.00 172.00   1.00    8.00    --  111.00  61.00-150.00   57
 53  ω     83.00 112.00   1.00    8.00    --  111.00  61.00-150.00   29
 54  ω     83.00 156.00   1.00    8.00    --  111.00  61.00-180.00   73
 55  ω     47.00  74.00   1.00    8.00    --  111.00 -94.00 -30.00   27
 56  ω     83.00 154.00   1.00    8.00    --  111.00  61.00 -60.00   71
 57  ω    141.00 176.00   1.00    8.00    --  111.00  61.00 120.00   35
 58  ω     83.00 135.00   1.00    8.00    --  111.00  61.00 120.00   52
 59  ω     44.00 109.00   1.00    8.00    --  111.00-111.00 -90.00   65
 60  ω     41.00 109.00   1.00    8.00    --  111.00-111.00  90.00   68
 61  ω     84.00 112.00   1.00    8.00    --  111.00  61.00-120.00   28
 62  ω    115.00 166.00   1.00    8.00    --  111.00  61.00-120.00   51
 63  ω     83.00 163.00   1.00    8.00    --  111.00  61.00  60.00   80
 64  ω     39.00  75.00   1.00    8.00    --  111.00-111.00  60.00   36
 65  ω    109.00 177.00   1.00    8.00    --  111.00 111.00 -60.00   68
 66  ω     45.00  82.00   1.00    8.00    --  111.00-111.00 120.00   37
 67  ω     83.00 172.00   1.00    8.00    --  111.00  61.00 150.00   89
 68  ω     48.00 109.00   1.00    8.00    --  111.00-111.00  30.00   61
 69  ω     83.00 178.00   1.00    8.00    --  111.00  61.00 -90.00   95
 70  ω     83.00 108.00   1.00    8.00    --  111.00-111.00-180.00   25
 71  ω     44.00  73.00   1.00    8.00    --  111.00-111.00-180.00   29
 72  ω     50.00 103.00   1.00    8.00    --  111.00-111.00-120.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0103759000
_diffrn_orient_matrix_UB_12      0.1063135000
_diffrn_orient_matrix_UB_13      -0.0391012000
_diffrn_orient_matrix_UB_21      -0.0262009000
_diffrn_orient_matrix_UB_22      -0.0994663000
_diffrn_orient_matrix_UB_23      -0.0445660000
_diffrn_orient_matrix_UB_31      -0.1530016000
_diffrn_orient_matrix_UB_32      -0.0548344000
_diffrn_orient_matrix_UB_33      0.0049746000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            57622
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.125
_diffrn_reflns_theta_min         4.465
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
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    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             1193
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1666 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_coef       0.00057(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0272
_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)+(0.0513P)²+0.2475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0733
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                3934
_reflns_number_total             3980
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc00621f2.cif
_cod_data_source_block           a23101302aqlq
_cod_depositor_comments          'Adding full bibliography for 1571375.cif.'
_cod_database_code               1571375
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C25H25.2NO2.1
_chemical_oxdiff_usercomment     371
_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.
;
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.912
_diffrn_oxdiff_digest_frames
;
0147483cd1f0d7435140473481e48cb6a5032715934
;
_diffrn_oxdiff_digest_hkl
;
01ddb8f28627720fd303f5a17c6f2f3bd68c49
;
_reflns_odcompleteness_completeness 99.96
_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, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O3) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
3. Others
 Fixed Sof: O3(0.08333) H3a(0.08333) H3b(0.08333)
4.a Riding coordinates:
 O3(H3a,H3b)
4.b Ternary CH refined with riding coordinates:
 C1(H1)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C17(H17),
 C19(H19)
4.d Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C22(H22a,H22b,H22c), C23(H23a,H23b,H23c), C24(H24a,H24b,
 H24c), C25(H25a,H25b,H25c)
;
_olex2_date_sample_data_collection 2023-10-13
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.408
_oxdiff_exptl_absorpt_empirical_full_min 0.743
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'
'y, x, -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
O1 O -0.66748(11) -0.83516(12) -0.72861(4) 0.0322(2) Uani 1 1 d . . . . .
O2 O -0.57633(11) -0.62049(12) -0.75640(4) 0.0322(3) Uani 1 1 d . . . . .
N1 N -0.44540(12) -0.68441(12) -0.71419(4) 0.0216(2) Uani 1 1 d . . . . .
C1 C -0.42158(13) -0.79047(13) -0.69301(5) 0.0203(3) Uani 1 1 d . . . . .
H1 H -0.4985 -0.8794 -0.7044 0.024 Uiso 1 1 calc R . . . .
C2 C -0.29458(13) -0.77554(13) -0.71757(5) 0.0201(3) Uani 1 1 d . . . . .
C3 C -0.28838(14) -0.89141(14) -0.72828(5) 0.0230(3) Uani 1 1 d . . . . .
H3 H -0.3622 -0.9774 -0.7194 0.028 Uiso 1 1 calc R . . . .
C4 C -0.17502(15) -0.88257(14) -0.75192(5) 0.0241(3) Uani 1 1 d . . . . .
C5 C -0.07118(14) -0.75473(14) -0.76553(5) 0.0228(3) Uani 1 1 d . . . . .
H5 H 0.0053 -0.7479 -0.7828 0.027 Uiso 1 1 calc R . . . .
C6 C -0.07316(14) -0.63626(14) -0.75519(5) 0.0213(3) Uani 1 1 d . . . . .
C7 C -0.18731(13) -0.64613(13) -0.72967(5) 0.0195(2) Uani 1 1 d . . . . .
C8 C -0.20365(14) -0.52946(13) -0.71555(4) 0.0202(3) Uani 1 1 d . . . . .
C9 C -0.33588(14) -0.54995(14) -0.70971(5) 0.0212(3) Uani 1 1 d . . . . .
C10 C -0.35575(15) -0.44302(15) -0.69646(5) 0.0254(3) Uani 1 1 d . . . . .
H10 H -0.4449 -0.4584 -0.6923 0.030 Uiso 1 1 calc R . . . .
C11 C -0.24654(17) -0.31462(15) -0.68931(6) 0.0293(3) Uani 1 1 d . . . . .
H11 H -0.2609 -0.2416 -0.6815 0.035 Uiso 1 1 calc R . . . .
C12 C -0.11609(17) -0.29247(15) -0.69354(6) 0.0305(3) Uani 1 1 d . . . . .
H12 H -0.0410 -0.2047 -0.6880 0.037 Uiso 1 1 calc R . . . .
C13 C -0.09572(15) -0.39911(14) -0.70589(5) 0.0257(3) Uani 1 1 d . . . . .
H13 H -0.0060 -0.3833 -0.7079 0.031 Uiso 1 1 calc R . . . .
C14 C -0.42329(14) -0.78888(13) -0.63390(5) 0.0210(3) Uani 1 1 d . . . . .
C15 C -0.54727(14) -0.83718(14) -0.60916(5) 0.0236(3) Uani 1 1 d . . . . .
H15 H -0.6276 -0.8726 -0.6291 0.028 Uiso 1 1 calc R . . . .
C16 C -0.55499(16) -0.83417(14) -0.55542(6) 0.0265(3) Uani 1 1 d . . . . .
C17 C -0.43690(17) -0.78556(15) -0.52681(5) 0.0281(3) Uani 1 1 d . . . . .
H17 H -0.4415 -0.7844 -0.4902 0.034 Uiso 1 1 calc R . . . .
C18 C -0.31179(16) -0.73846(15) -0.55061(5) 0.0265(3) Uani 1 1 d . . . . .
C19 C -0.30613(14) -0.73958(14) -0.60449(5) 0.0230(3) Uani 1 1 d . . . . .
H19 H -0.2214 -0.7063 -0.6212 0.028 Uiso 1 1 calc R . . . .
C20 C -0.57200(14) -0.72240(15) -0.73256(5) 0.0240(3) Uani 1 1 d . . . . .
C21 C -0.16267(18) -1.00576(16) -0.76173(7) 0.0356(3) Uani 1 1 d . . . . .
H21A H -0.1041 -1.0115 -0.7355 0.053 Uiso 1 1 calc GR . . . .
H21B H -0.1236 -0.9992 -0.7960 0.053 Uiso 1 1 calc GR . . . .
H21C H -0.2523 -1.0867 -0.7601 0.053 Uiso 1 1 calc GR . . . .
C22 C 0.04800(14) -0.50584(15) -0.77229(5) 0.0255(3) Uani 1 1 d . . . . .
H22A H 0.1083 -0.4632 -0.7428 0.038 Uiso 1 1 calc GR . . . .
H22B H 0.0182 -0.4450 -0.7858 0.038 Uiso 1 1 calc GR . . . .
H22C H 0.0963 -0.5246 -0.7994 0.038 Uiso 1 1 calc GR . . . .
C23 C -0.68920(17) -0.88058(17) -0.52926(6) 0.0342(3) Uani 1 1 d . . . . .
H23A H -0.7561 -0.9692 -0.5428 0.051 Uiso 1 1 calc GR . . . .
H23B H -0.7192 -0.8153 -0.5360 0.051 Uiso 1 1 calc GR . . . .
H23C H -0.6794 -0.8873 -0.4920 0.051 Uiso 1 1 calc GR . . . .
C24 C -0.18564(18) -0.6891(2) -0.51843(6) 0.0369(4) Uani 1 1 d . . . . .
H24A H -0.1060 -0.6379 -0.5403 0.055 Uiso 1 1 calc GR . . . .
H24B H -0.1834 -0.7665 -0.5033 0.055 Uiso 1 1 calc GR . . . .
H24C H -0.1856 -0.6306 -0.4907 0.055 Uiso 1 1 calc GR . . . .
C25 C -0.70726(18) -0.6498(2) -0.77415(7) 0.0419(4) Uani 1 1 d . . . . .
H25A H -0.7334 -0.5904 -0.7566 0.063 Uiso 1 1 calc GR . . . .
H25B H -0.7735 -0.7442 -0.7665 0.063 Uiso 1 1 calc GR . . . .
H25C H -0.7042 -0.6348 -0.8115 0.063 Uiso 1 1 calc GR . . . .
O3 O 0.106(2) 0.000(4) -0.6721(10) 0.026(3) Uani 0.0833 1 d . U P A -1
H3A H 0.1858 0.0407 -0.6859 0.040 Uiso 0.0833 1 d R . P A -1
H3B H 0.0987 -0.0624 -0.6511 0.040 Uiso 0.0833 1 d R . 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 0.0000 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
C20 O2 C25 115.56(13) . . ?
C9 N1 C1 115.72(11) . . ?
C20 N1 C1 117.91(12) . . ?
C20 N1 C9 126.18(12) . . ?
N1 C1 C2 108.18(10) . . ?
N1 C1 C14 110.68(10) . . ?
C2 C1 C14 115.83(11) . . ?
C3 C2 C1 118.64(12) . . ?
C3 C2 C7 121.69(12) . . ?
C7 C2 C1 119.66(11) . . ?
C2 C3 C4 120.57(12) . . ?
C3 C4 C5 117.56(12) . . ?
C3 C4 C21 121.75(13) . . ?
C5 C4 C21 120.67(13) . . ?
C4 C5 C6 123.58(13) . . ?
C5 C6 C7 118.36(13) . . ?
C5 C6 C22 116.87(12) . . ?
C7 C6 C22 124.76(13) . . ?
C2 C7 C6 118.17(12) . . ?
C2 C7 C8 117.12(12) . . ?
C6 C7 C8 124.70(12) . . ?
C9 C8 C7 118.79(12) . . ?
C13 C8 C7 124.08(13) . . ?
C13 C8 C9 117.11(12) . . ?
C8 C9 N1 117.40(11) . . ?
C10 C9 N1 121.81(13) . . ?
C10 C9 C8 120.64(13) . . ?
C11 C10 C9 120.47(14) . . ?
C10 C11 C12 120.05(14) . . ?
C11 C12 C13 119.68(15) . . ?
C12 C13 C8 121.97(14) . . ?
C15 C14 C1 118.13(12) . . ?
C19 C14 C1 122.44(12) . . ?
C19 C14 C15 119.42(12) . . ?
C14 C15 C16 120.85(14) . . ?
C15 C16 C23 120.27(14) . . ?
C17 C16 C15 118.73(13) . . ?
C17 C16 C23 120.99(13) . . ?
C16 C17 C18 121.52(13) . . ?
C17 C18 C19 118.75(13) . . ?
C17 C18 C24 120.27(13) . . ?
C19 C18 C24 120.97(13) . . ?
C14 C19 C18 120.70(12) . . ?
O1 C20 O2 124.09(13) . . ?
O1 C20 N1 123.81(13) . . ?
O2 C20 N1 112.09(12) . . ?
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
O1 C20 1.2071(19) . ?
O2 C20 1.3412(18) . ?
O2 C25 1.4362(19) . ?
N1 C1 1.4751(16) . ?
N1 C9 1.4213(18) . ?
N1 C20 1.3717(18) . ?
C1 C2 1.5146(18) . ?
C1 C14 1.5310(17) . ?
C2 C3 1.3896(19) . ?
C2 C7 1.4062(18) . ?
C3 C4 1.3906(19) . ?
C4 C5 1.391(2) . ?
C4 C21 1.5057(19) . ?
C5 C6 1.392(2) . ?
C6 C7 1.4162(19) . ?
C6 C22 1.5077(19) . ?
C7 C8 1.4824(18) . ?
C8 C9 1.4175(19) . ?
C8 C13 1.403(2) . ?
C9 C10 1.3936(19) . ?
C10 C11 1.384(2) . ?
C11 C12 1.387(2) . ?
C12 C13 1.388(2) . ?
C14 C15 1.3937(19) . ?
C14 C19 1.3918(19) . ?
C15 C16 1.396(2) . ?
C16 C17 1.389(2) . ?
C16 C23 1.510(2) . ?
C17 C18 1.395(2) . ?
C18 C19 1.3969(19) . ?
C18 C24 1.510(2) . ?
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
N1 C1 C2 C3 -144.47(11) . . . . ?
N1 C1 C2 C7 34.57(16) . . . . ?
N1 C1 C14 C15 73.15(15) . . . . ?
N1 C1 C14 C19 -105.95(14) . . . . ?
N1 C9 C10 C11 176.04(13) . . . . ?
C1 N1 C9 C8 36.33(16) . . . . ?
C1 N1 C9 C10 -139.15(12) . . . . ?
C1 N1 C20 O1 6.26(19) . . . . ?
C1 N1 C20 O2 -172.33(11) . . . . ?
C1 C2 C3 C4 178.48(12) . . . . ?
C1 C2 C7 C6 -176.57(11) . . . . ?
C1 C2 C7 C8 2.23(17) . . . . ?
C1 C14 C15 C16 -177.82(12) . . . . ?
C1 C14 C19 C18 179.27(12) . . . . ?
C2 C1 C14 C15 -163.27(12) . . . . ?
C2 C1 C14 C19 17.63(18) . . . . ?
C2 C3 C4 C5 -1.78(19) . . . . ?
C2 C3 C4 C21 177.08(13) . . . . ?
C2 C7 C8 C9 -23.70(16) . . . . ?
C2 C7 C8 C13 154.26(13) . . . . ?
C3 C2 C7 C6 2.43(18) . . . . ?
C3 C2 C7 C8 -178.77(11) . . . . ?
C3 C4 C5 C6 2.3(2) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C4 C5 C6 C22 179.66(12) . . . . ?
C5 C6 C7 C2 -1.96(18) . . . . ?
C5 C6 C7 C8 179.34(12) . . . . ?
C6 C7 C8 C9 155.02(12) . . . . ?
C6 C7 C8 C13 -27.02(19) . . . . ?
C7 C2 C3 C4 -0.54(19) . . . . ?
C7 C8 C9 N1 4.45(17) . . . . ?
C7 C8 C9 C10 179.98(11) . . . . ?
C7 C8 C13 C12 179.00(12) . . . . ?
C8 C9 C10 C11 0.71(19) . . . . ?
C9 N1 C1 C2 -54.29(14) . . . . ?
C9 N1 C1 C14 73.59(14) . . . . ?
C9 N1 C20 O1 -168.48(13) . . . . ?
C9 N1 C20 O2 12.93(18) . . . . ?
C9 C8 C13 C12 -3.0(2) . . . . ?
C9 C10 C11 C12 -2.3(2) . . . . ?
C10 C11 C12 C13 1.2(2) . . . . ?
C11 C12 C13 C8 1.5(2) . . . . ?
C13 C8 C9 N1 -173.65(11) . . . . ?
C13 C8 C9 C10 1.88(18) . . . . ?
C14 C1 C2 C3 90.65(14) . . . . ?
C14 C1 C2 C7 -90.31(14) . . . . ?
C14 C15 C16 C17 -1.8(2) . . . . ?
C14 C15 C16 C23 177.03(13) . . . . ?
C15 C14 C19 C18 0.2(2) . . . . ?
C15 C16 C17 C18 0.9(2) . . . . ?
C16 C17 C18 C19 0.6(2) . . . . ?
C16 C17 C18 C24 -178.68(14) . . . . ?
C17 C18 C19 C14 -1.1(2) . . . . ?
C19 C14 C15 C16 1.3(2) . . . . ?
C20 N1 C1 C2 130.43(12) . . . . ?
C20 N1 C1 C14 -101.69(13) . . . . ?
C20 N1 C9 C8 -148.83(12) . . . . ?
C20 N1 C9 C10 35.69(19) . . . . ?
C21 C4 C5 C6 -176.61(13) . . . . ?
C22 C6 C7 C2 178.01(12) . . . . ?
C22 C6 C7 C8 -0.7(2) . . . . ?
C23 C16 C17 C18 -177.96(13) . . . . ?
C24 C18 C19 C14 178.13(14) . . . . ?
C25 O2 C20 O1 4.9(2) . . . . ?
C25 O2 C20 N1 -176.52(13) . . . . ?
