#------------------------------------------------------------------------------
#$Date: 2024-07-05 17:08:14 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292867 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/15/1571530.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_1571530
loop_
_publ_author_name
'Grzelak, Magdalena'
'Kumar, Dharmendra'
'Kochman, Michał Andrzej'
'Morawiak, Maja'
'Wiosna-Sałyga, Gabriela'
'Kubas, Adam'
'Data, Przemysław'
'Lindner, Marcin'
_publ_section_title
;
 An unprecedented roll-off ratio in high-performing red TADF OLED emitters
 featuring 2,3-indole-annulated naphthalene imide and auxiliary donors.
;
_journal_issue                   22
_journal_name_full               'Chemical science'
_journal_page_first              8404
_journal_page_last               8413
_journal_paper_doi               10.1039/d4sc01391c
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C43 H35 N3 O3, C H2 Cl2'
_chemical_formula_sum            'C44 H37 Cl2 N3 O3'
_chemical_formula_weight         726.66
_chemical_name_common            'JW 156'
_chemical_name_systematic        'MMG 156'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-11
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-02-16 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.5023(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.9323(4)
_cell_length_b                   11.41330(17)
_cell_length_c                   13.3857(2)
_cell_measurement_reflns_used    9456
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.8830
_cell_measurement_theta_min      4.2900
_cell_volume                     3624.96(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 -35.00   0.50    0.20    --    0.00 121.00 -81.00   50
  2  ω    -73.00 -47.00   0.50    0.20    --    0.00 153.00  77.00   52
  3  ω    -12.00  14.00   0.50    0.20    --    0.00  57.00   0.00   52
  4  ω    -15.00  78.00   0.50    0.20    --    0.00  57.00-150.00  186
  5  ω     36.00  62.00   0.50    0.20    --    0.00  57.00   0.00   52
  6  ω   -130.00-105.00   0.50    2.00    --  -54.00-121.00-164.00   50
  7  ω    -99.00 -54.00   0.50    2.00    --  -54.00-153.00  36.00   90
  8  ω   -133.00 -86.00   0.50    2.00    --  -54.00 -99.00-120.00   94
  9  ω   -127.00 -91.00   0.50    2.00    --  -54.00 -99.00 -60.00   72
 10  ω   -138.00 -93.00   0.50    2.00    --  -54.00 -99.00 -90.00   90
 11  ω   -140.00-112.00   0.50    2.00    --  -54.00 -99.00  60.00   56
 12  ω   -140.00 -90.00   0.50    2.00    --  -54.00 -99.00-150.00  100
 13  ω     36.00 110.00   0.50    2.00    --   55.77-121.00-164.00  148
 14  ω     93.00 126.00   0.50    2.00    --   55.77 153.00  77.00   66
 15  ω     35.00 134.00   0.50    2.00    --   55.77  57.00 -90.00  198
 16  ω     83.00 110.00   0.50    5.00    --  111.55-121.00-164.00   54
 17  ω     99.00 167.00   0.50    5.00    --  111.55 121.00 -81.00  136
 18  ω     74.00 132.00   0.50    5.00    --  111.55-153.00  36.00  116
 19  ω     76.00 116.00   0.50    5.00    --  111.55 153.00  77.00   80
 20  ω     77.00 117.00   0.50    5.00    --  111.55  61.00 -90.00   80
 21  ω     85.00 177.00   0.50    5.00    --  111.55  61.00 -30.00  184
 22  ω     83.00 116.00   0.50    5.00    --  111.55 -61.00 150.00   66
 23  ω     80.00 105.00   0.50    5.00    --  111.55 -94.00-150.00   50
 24  ω     77.00 156.00   0.50    5.00    --  111.55  61.00-150.00  158
 25  ω     27.00  69.00   0.50    5.00    --  111.55 -94.00-150.00   84
 26  ω     49.00 102.00   0.50    5.00    --  111.55-111.00  90.00  106
 27  ω    116.00 149.00   0.50    5.00    --  111.55  77.00 -90.00   66
 28  ω     70.00 112.00   0.50    5.00    --  111.55  77.00 -90.00   84
 29  ω    139.00 168.00   0.50    5.00    --  111.55  61.00-120.00   58
 30  ω     70.00 159.00   0.50    5.00    --  111.55  77.00   0.00  178
;
_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      0.0265972000
_diffrn_orient_matrix_UB_12      0.0737324000
_diffrn_orient_matrix_UB_13      0.0902946000
_diffrn_orient_matrix_UB_21      -0.0097377000
_diffrn_orient_matrix_UB_22      0.1120939000
_diffrn_orient_matrix_UB_23      -0.0640214000
_diffrn_orient_matrix_UB_31      -0.0584272000
_diffrn_orient_matrix_UB_32      0.0148552000
_diffrn_orient_matrix_UB_33      0.0349340000
_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  0.0366
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.201
_diffrn_reflns_theta_min         3.726
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.974
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light orange'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/hexane'
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     483
_refine_ls_number_reflns         7095
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0588P)²+1.3822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5724
_reflns_number_total             7095
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc01391c2.cif
_cod_data_source_block           2023_08_10_dt_jw-156_n_auto
_cod_depositor_comments
'Adding full bibliography for 1571528--1571532.cif.'
_cod_original_cell_volume        3624.94(10)
_cod_database_code               1571530
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C44 H37 Cl2 N3 O3'
_chemical_oxdiff_usercomment     '100 K'
_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   0.889
_shelx_estimated_absorpt_t_min   0.749
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1A-C49 \\sim Cl1B-C49
 with sigma of 0.02
 Cl1B-C49 \\sim Cl1A-C49
 with sigma of 0.01
3. Others
 Sof(H49C)=Sof(H49D)=Sof(Cl1B)=1-FVAR(1)
 Sof(H49A)=Sof(H49B)=Sof(Cl1A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C49(H49A,H49B), C49(H49C,H49D)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13), C17(H17), C23(H23),
 C25(H25), C33(H33), C34(H34), C35(H35), C36(H36), C40(H40), C41(H41), C42(H42),
  C43(H43)
4.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C48(H48A,H48B,
 H48C)
;
_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 1.215
_oxdiff_exptl_absorpt_empirical_full_min 0.833
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C2 C 0.21326(7) 0.75443(14) 0.49815(12) 0.0208(3) Uani 1 1 d . . . . .
C3 C 0.26897(7) 0.75606(14) 0.46014(12) 0.0185(3) Uani 1 1 d . . . . .
C4 C 0.30728(7) 0.84182(14) 0.49508(12) 0.0195(3) Uani 1 1 d . . . . .
H4 H 0.297624 0.898832 0.541622 0.023 Uiso 1 1 calc R U . . .
C5 C 0.36054(7) 0.84479(14) 0.46181(12) 0.0192(3) Uani 1 1 d . . . . .
H5 H 0.386689 0.904404 0.485391 0.023 Uiso 1 1 calc R U . . .
C6 C 0.37506(6) 0.76165(14) 0.39514(11) 0.0182(3) Uani 1 1 d . . . . .
H6 H 0.411496 0.763957 0.374291 0.022 Uiso 1 1 calc R U . . .
C7 C 0.33672(6) 0.67277(13) 0.35702(11) 0.0172(3) Uani 1 1 d . . . . .
C8 C 0.34869(6) 0.58499(14) 0.28686(11) 0.0168(3) Uani 1 1 d . . . . .
C9 C 0.39727(7) 0.55627(13) 0.23882(11) 0.0167(3) Uani 1 1 d . . . . .
C10 C 0.45176(6) 0.60343(13) 0.24123(11) 0.0172(3) Uani 1 1 d . . . . .
H10 H 0.462899 0.669741 0.281909 0.021 Uiso 1 1 calc R U . . .
C11 C 0.48880(6) 0.55181(14) 0.18355(12) 0.0179(3) Uani 1 1 d . . . . .
C12 C 0.47341(7) 0.45236(14) 0.12413(12) 0.0194(3) Uani 1 1 d . . . . .
H12 H 0.499782 0.418877 0.085159 0.023 Uiso 1 1 calc R U . . .
C13 C 0.42049(7) 0.40243(14) 0.12148(11) 0.0186(3) Uani 1 1 d . . . . .
H13 H 0.410316 0.334548 0.082208 0.022 Uiso 1 1 calc R U . . .
C14 C 0.38248(7) 0.45550(13) 0.17874(11) 0.0173(3) Uani 1 1 d . . . . .
C16 C 0.30720(7) 0.50123(13) 0.25297(11) 0.0174(3) Uani 1 1 d . . . . .
C17 C 0.25367(7) 0.49996(14) 0.28578(12) 0.0194(3) Uani 1 1 d . . . . .
H17 H 0.226168 0.443333 0.261208 0.023 Uiso 1 1 calc R U . . .
C18 C 0.24251(7) 0.58330(14) 0.35447(12) 0.0188(3) Uani 1 1 d . . . . .
C19 C 0.18665(7) 0.57995(14) 0.39083(12) 0.0209(3) Uani 1 1 d . . . . .
C20 C 0.28273(7) 0.67086(14) 0.39072(11) 0.0177(3) Uani 1 1 d . . . . .
C21 C 0.11969(7) 0.66461(15) 0.49172(12) 0.0211(3) Uani 1 1 d . . . . .
C22 C 0.10956(7) 0.59683(15) 0.57390(13) 0.0238(3) Uani 1 1 d . . . . .
C23 C 0.05488(8) 0.59396(16) 0.59825(13) 0.0261(4) Uani 1 1 d . . . . .
H23 H 0.047006 0.547440 0.653583 0.031 Uiso 1 1 calc R U . . .
C24 C 0.01129(7) 0.65719(16) 0.54403(14) 0.0281(4) Uani 1 1 d . . . . .
C25 C 0.02329(8) 0.72320(17) 0.46251(14) 0.0300(4) Uani 1 1 d . . . . .
H25 H -0.006139 0.766481 0.424766 0.036 Uiso 1 1 calc R U . . .
C26 C 0.07727(8) 0.72786(16) 0.43435(13) 0.0265(4) Uani 1 1 d . . . . .
C27 C 0.15615(8) 0.52869(18) 0.63456(15) 0.0330(4) Uani 1 1 d . . . . .
H27A H 0.175769 0.480983 0.589180 0.049 Uiso 1 1 calc R U . . .
H27B H 0.140112 0.477547 0.682295 0.049 Uiso 1 1 calc R U . . .
H27C H 0.182880 0.583238 0.671667 0.049 Uiso 1 1 calc R U . . .
C28 C -0.04732(8) 0.65461(19) 0.57440(17) 0.0377(5) Uani 1 1 d . . . . .
H28A H -0.056245 0.574779 0.594132 0.057 Uiso 1 1 calc R U . . .
H28B H -0.074635 0.679572 0.517401 0.057 Uiso 1 1 calc R U . . .
H28C H -0.049091 0.707821 0.631361 0.057 Uiso 1 1 calc R U . . .
C29 C 0.08923(9) 0.8007(2) 0.34565(16) 0.0378(5) Uani 1 1 d . . . . .
H29A H 0.112594 0.868044 0.369653 0.057 Uiso 1 1 calc R U . . .
H29B H 0.053625 0.828383 0.308731 0.057 Uiso 1 1 calc R U . . .
H29C H 0.109241 0.752914 0.300887 0.057 Uiso 1 1 calc R U . . .
C32 C 0.55444(7) 0.69615(13) 0.12693(11) 0.0167(3) Uani 1 1 d . . . . .
C33 C 0.51099(7) 0.75773(14) 0.07015(11) 0.0189(3) Uani 1 1 d . . . . .
H33 H 0.473033 0.733596 0.070568 0.023 Uiso 1 1 calc R U . . .
C34 C 0.52286(7) 0.85459(14) 0.01268(12) 0.0220(3) Uani 1 1 d . . . . .
H34 H 0.492921 0.895209 -0.026253 0.026 Uiso 1 1 calc R U . . .
C35 C 0.57783(7) 0.89194(14) 0.01192(12) 0.0228(3) Uani 1 1 d . . . . .
H35 H 0.585640 0.958806 -0.026187 0.027 Uiso 1 1 calc R U . . .
C36 C 0.62163(7) 0.83038(14) 0.06769(12) 0.0203(3) Uani 1 1 d . . . . .
H36 H 0.659534 0.854894 0.067336 0.024 Uiso 1 1 calc R U . . .
C37 C 0.60984(7) 0.73375(14) 0.12341(11) 0.0174(3) Uani 1 1 d . . . . .
C39 C 0.64546(7) 0.57431(14) 0.22595(12) 0.0196(3) Uani 1 1 d . . . . .
C40 C 0.69203(7) 0.51315(16) 0.26980(13) 0.0250(4) Uani 1 1 d . . . . .
H40 H 0.728836 0.539981 0.262365 0.030 Uiso 1 1 calc R U . . .
C41 C 0.68500(8) 0.41224(16) 0.32486(14) 0.0277(4) Uani 1 1 d . . . . .
H41 H 0.716933 0.369420 0.354669 0.033 Uiso 1 1 calc R U . . .
C42 C 0.63127(7) 0.37450(15) 0.33604(12) 0.0236(3) Uani 1 1 d . . . . .
H42 H 0.626374 0.306521 0.374917 0.028 Uiso 1 1 calc R U . . .
C43 C 0.58442(7) 0.43529(14) 0.29082(11) 0.0193(3) Uani 1 1 d . . . . .
H43 H 0.547715 0.408206 0.298663 0.023 Uiso 1 1 calc R U . . .
C44 C 0.59071(7) 0.53566(14) 0.23402(11) 0.0176(3) Uani 1 1 d . . . . .
C45 C 0.29636(7) 0.32615(14) 0.13662(12) 0.0195(3) Uani 1 1 d . . . . .
H45A H 0.270352 0.294147 0.181542 0.023 Uiso 1 1 calc R U . . .
H45B H 0.323162 0.263249 0.124535 0.023 Uiso 1 1 calc R U . . .
C46 C 0.26243(7) 0.36002(14) 0.03653(12) 0.0208(3) Uani 1 1 d . . . . .
H46A H 0.288594 0.382980 -0.011547 0.025 Uiso 1 1 calc R U . . .
H46B H 0.238527 0.428617 0.046866 0.025 Uiso 1 1 calc R U . . .
C47 C 0.22499(7) 0.25934(15) -0.00859(13) 0.0253(4) Uani 1 1 d . . . . .
H47A H 0.248629 0.189101 -0.014347 0.030 Uiso 1 1 calc R U . . .
H47B H 0.197165 0.240072 0.037525 0.030 Uiso 1 1 calc R U . . .
C48 C 0.19383(8) 0.28922(18) -0.11207(14) 0.0326(4) Uani 1 1 d . . . . .
H48A H 0.221182 0.303565 -0.159156 0.049 Uiso 1 1 calc R U . . .
H48B H 0.170925 0.359639 -0.107079 0.049 Uiso 1 1 calc R U . . .
H48C H 0.169332 0.223673 -0.136529 0.049 Uiso 1 1 calc R U . . .
N1 N 0.17576(6) 0.66576(12) 0.46077(10) 0.0204(3) Uani 1 1 d . . . . .
N15 N 0.32790(6) 0.42378(12) 0.18784(10) 0.0182(3) Uani 1 1 d . . . . .
N31 N 0.54459(6) 0.59882(12) 0.18619(10) 0.0193(3) Uani 1 1 d . . . . .
O30 O 0.20001(5) 0.82512(11) 0.55903(10) 0.0290(3) Uani 1 1 d . . . . .
O38 O 0.65588(5) 0.67582(10) 0.17444(9) 0.0230(3) Uani 1 1 d . . . . .
O47 O 0.15119(5) 0.50727(11) 0.36255(10) 0.0280(3) Uani 1 1 d . . . . .
C49 C 0.08815(10) 0.5516(2) 0.13635(19) 0.0460(5) Uani 1 1 d D . . . .
H49A H 0.111775 0.578107 0.198477 0.055 Uiso 0.65(3) 1 calc R U P A 1
H49B H 0.091606 0.610464 0.083193 0.055 Uiso 0.65(3) 1 calc R U P A 1
H49C H 0.113036 0.549081 0.201487 0.055 Uiso 0.35(3) 1 calc R U P A 2
H49D H 0.094881 0.626800 0.103070 0.055 Uiso 0.35(3) 1 calc R U P A 2
Cl1A Cl 0.11410(14) 0.4171(6) 0.0989(10) 0.0725(15) Uani 0.65(3) 1 d D . P A 1
Cl1B Cl 0.1055(6) 0.4365(7) 0.0608(11) 0.0638(19) Uani 0.35(3) 1 d D . P A 2
Cl50 Cl 0.01827(3) 0.54570(6) 0.15884(7) 0.0701(2) Uani 1 1 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'
Cl Cl 0.3639 0.7018 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-10 5 -1 0.0410
-11 -3 6 0.0421
14 -3 -2 0.0320
-7 6 -3 0.0422
1 4 7 0.0654
-15 0 2 0.0303
15 1 0 0.0242
-5 -4 -7 0.0594
-14 -2 -2 0.0427
8 4 -6 0.0676
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
N1 C2 C3 116.59(14) . . ?
O30 C2 C3 122.94(15) . . ?
O30 C2 N1 120.46(15) . . ?
C4 C3 C2 118.57(14) . . ?
C4 C3 C20 120.60(14) . . ?
C20 C3 C2 120.83(14) . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.99(14) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.32(14) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.33(14) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C8 124.27(14) . . ?
C6 C7 C20 117.94(14) . . ?
C20 C7 C8 117.78(14) . . ?
C7 C8 C9 134.22(14) . . ?
C16 C8 C7 119.62(14) . . ?
C16 C8 C9 106.15(13) . . ?
C10 C9 C8 134.71(15) . . ?
C10 C9 C14 118.95(14) . . ?
C14 C9 C8 106.33(13) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 118.98(14) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C12 121.35(14) . . ?
C10 C11 N31 119.32(14) . . ?
C12 C11 N31 119.31(14) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.16(14) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 121.1 . . ?
C12 C13 C14 117.71(15) . . ?
C14 C13 H13 121.1 . . ?
C13 C14 C9 121.84(14) . . ?
N15 C14 C9 109.39(13) . . ?
N15 C14 C13 128.77(15) . . ?
C17 C16 C8 122.55(14) . . ?
N15 C16 C8 110.01(13) . . ?
N15 C16 C17 127.42(14) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 C16 117.79(14) . . ?
C18 C17 H17 121.1 . . ?
C17 C18 C19 117.69(14) . . ?
C17 C18 C20 122.07(15) . . ?
C20 C18 C19 120.24(14) . . ?
N1 C19 C18 117.09(14) . . ?
O47 C19 C18 122.71(15) . . ?
O47 C19 N1 120.20(14) . . ?
C3 C20 C7 119.81(14) . . ?
C3 C20 C18 120.02(14) . . ?
C7 C20 C18 120.17(14) . . ?
C22 C21 C26 122.31(15) . . ?
C22 C21 N1 119.50(15) . . ?
C26 C21 N1 118.13(15) . . ?
C21 C22 C27 121.31(15) . . ?
C23 C22 C21 117.72(16) . . ?
C23 C22 C27 120.97(16) . . ?
C22 C23 H23 119.0 . . ?
C22 C23 C24 122.01(16) . . ?
C24 C23 H23 119.0 . . ?
C23 C24 C28 120.57(17) . . ?
C25 C24 C23 118.28(16) . . ?
C25 C24 C28 121.15(18) . . ?
C24 C25 H25 119.1 . . ?
C24 C25 C26 121.89(17) . . ?
C26 C25 H25 119.1 . . ?
C21 C26 C25 117.79(16) . . ?
C21 C26 C29 121.39(16) . . ?
C25 C26 C29 120.82(17) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C33 C32 C37 117.96(14) . . ?
C33 C32 N31 122.60(14) . . ?
C37 C32 N31 119.44(14) . . ?
C32 C33 H33 119.7 . . ?
C32 C33 C34 120.53(15) . . ?
C34 C33 H33 119.7 . . ?
C33 C34 H34 119.7 . . ?
C35 C34 C33 120.63(15) . . ?
C35 C34 H34 119.7 . . ?
C34 C35 H35 120.3 . . ?
C34 C35 C36 119.31(15) . . ?
C36 C35 H35 120.3 . . ?
C35 C36 H36 120.0 . . ?
C37 C36 C35 119.94(15) . . ?
C37 C36 H36 120.0 . . ?
C36 C37 C32 121.61(15) . . ?
C36 C37 O38 116.22(14) . . ?
O38 C37 C32 122.17(14) . . ?
C40 C39 C44 121.32(15) . . ?
C40 C39 O38 116.52(15) . . ?
O38 C39 C44 122.16(14) . . ?
C39 C40 H40 120.1 . . ?
C39 C40 C41 119.88(16) . . ?
C41 C40 H40 120.1 . . ?
C40 C41 H41 120.2 . . ?
C42 C41 C40 119.63(16) . . ?
C42 C41 H41 120.2 . . ?
C41 C42 H42 119.8 . . ?
C41 C42 C43 120.44(15) . . ?
C43 C42 H42 119.8 . . ?
C42 C43 H43 119.7 . . ?
C42 C43 C44 120.66(15) . . ?
C44 C43 H43 119.7 . . ?
C39 C44 N31 119.47(14) . . ?
C43 C44 C39 118.03(15) . . ?
C43 C44 N31 122.50(14) . . ?
H45A C45 H45B 107.7 . . ?
C46 C45 H45A 108.8 . . ?
C46 C45 H45B 108.8 . . ?
N15 C45 H45A 108.8 . . ?
N15 C45 H45B 108.8 . . ?
N15 C45 C46 113.68(13) . . ?
C45 C46 H46A 109.2 . . ?
C45 C46 H46B 109.2 . . ?
C45 C46 C47 111.94(14) . . ?
H46A C46 H46B 107.9 . . ?
C47 C46 H46A 109.2 . . ?
C47 C46 H46B 109.2 . . ?
C46 C47 H47A 109.1 . . ?
C46 C47 H47B 109.1 . . ?
H47A C47 H47B 107.8 . . ?
C48 C47 C46 112.47(15) . . ?
C48 C47 H47A 109.1 . . ?
C48 C47 H47B 109.1 . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C2 N1 C19 125.22(13) . . ?
C2 N1 C21 118.45(13) . . ?
C19 N1 C21 116.25(13) . . ?
C14 N15 C16 108.12(13) . . ?
C14 N15 C45 126.56(13) . . ?
C16 N15 C45 125.31(13) . . ?
C32 N31 C11 120.44(13) . . ?
C44 N31 C11 119.59(13) . . ?
C44 N31 C32 119.03(13) . . ?
C37 O38 C39 117.42(12) . . ?
H49A C49 H49B 107.7 . . ?
H49C C49 H49D 107.9 . . ?
Cl1A C49 H49A 108.8 . . ?
Cl1A C49 H49B 108.8 . . ?
Cl1B C49 H49C 109.1 . . ?
Cl1B C49 H49D 109.1 . . ?
Cl50 C49 H49A 108.8 . . ?
Cl50 C49 H49B 108.8 . . ?
Cl50 C49 H49C 109.1 . . ?
Cl50 C49 H49D 109.1 . . ?
Cl50 C49 Cl1A 113.6(2) . . ?
Cl50 C49 Cl1B 112.3(4) . . ?
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
C2 C3 1.488(2) . ?
C2 N1 1.401(2) . ?
C2 O30 1.218(2) . ?
C3 C4 1.381(2) . ?
C3 C20 1.413(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.404(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.417(2) . ?
C7 C8 1.428(2) . ?
C7 C20 1.423(2) . ?
C8 C9 1.438(2) . ?
C8 C16 1.410(2) . ?
C9 C10 1.407(2) . ?
C9 C14 1.422(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(2) . ?
C11 C12 1.407(2) . ?
C11 N31 1.435(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.401(2) . ?
C14 N15 1.376(2) . ?
C16 C17 1.408(2) . ?
C16 N15 1.378(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.373(2) . ?
C18 C19 1.482(2) . ?
C18 C20 1.428(2) . ?
C19 N1 1.403(2) . ?
C19 O47 1.212(2) . ?
C21 C22 1.392(2) . ?
C21 C26 1.392(2) . ?
C21 N1 1.455(2) . ?
C22 C23 1.390(2) . ?
C22 C27 1.507(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.392(3) . ?
C24 C25 1.387(3) . ?
C24 C28 1.511(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.393(2) . ?
C26 C29 1.507(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C32 C33 1.395(2) . ?
C32 C37 1.400(2) . ?
C32 N31 1.403(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.397(2) . ?
C34 H34 0.9500 . ?
C34 C35 1.384(2) . ?
C35 H35 0.9500 . ?
C35 C36 1.395(2) . ?
C36 H36 0.9500 . ?
C36 C37 1.381(2) . ?
C37 O38 1.3861(19) . ?
C39 C40 1.379(2) . ?
C39 C44 1.400(2) . ?
C39 O38 1.3873(19) . ?
C40 H40 0.9500 . ?
C40 C41 1.389(2) . ?
C41 H41 0.9500 . ?
C41 C42 1.383(2) . ?
C42 H42 0.9500 . ?
C42 C43 1.388(2) . ?
C43 H43 0.9500 . ?
C43 C44 1.394(2) . ?
C44 N31 1.401(2) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C45 C46 1.523(2) . ?
C45 N15 1.465(2) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C46 C47 1.532(2) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C47 C48 1.524(2) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C49 H49C 0.9900 . ?
C49 H49D 0.9900 . ?
C49 Cl1A 1.754(4) . ?
C49 Cl1B 1.741(5) . ?
C49 Cl50 1.739(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
C2 C3 C4 C5 179.08(14) . . . . ?
C2 C3 C20 C7 -178.71(14) . . . . ?
C2 C3 C20 C18 1.4(2) . . . . ?
C3 C2 N1 C19 -0.3(2) . . . . ?
C3 C2 N1 C21 -176.74(14) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C3 C20 C7 0.5(2) . . . . ?
C4 C3 C20 C18 -179.42(15) . . . . ?
C4 C5 C6 C7 1.2(2) . . . . ?
C5 C6 C7 C8 179.13(14) . . . . ?
C5 C6 C7 C20 -0.8(2) . . . . ?
C6 C7 C8 C9 2.2(3) . . . . ?
C6 C7 C8 C16 -179.34(14) . . . . ?
C6 C7 C20 C3 0.0(2) . . . . ?
C6 C7 C20 C18 179.87(14) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C7 C8 C9 C14 178.20(16) . . . . ?
C7 C8 C16 C17 -0.1(2) . . . . ?
C7 C8 C16 N15 -178.67(13) . . . . ?
C8 C7 C20 C3 -179.97(14) . . . . ?
C8 C7 C20 C18 -0.1(2) . . . . ?
C8 C9 C10 C11 179.99(16) . . . . ?
C8 C9 C14 C13 -179.43(14) . . . . ?
C8 C9 C14 N15 0.52(17) . . . . ?
C8 C16 C17 C18 -0.9(2) . . . . ?
C8 C16 N15 C14 0.12(17) . . . . ?
C8 C16 N15 C45 -179.01(14) . . . . ?
C9 C8 C16 C17 178.75(14) . . . . ?
C9 C8 C16 N15 0.20(17) . . . . ?
C9 C10 C11 C12 -1.1(2) . . . . ?
C9 C10 C11 N31 -179.52(13) . . . . ?
C9 C14 N15 C16 -0.41(17) . . . . ?
C9 C14 N15 C45 178.72(14) . . . . ?
C10 C9 C14 C13 -0.4(2) . . . . ?
C10 C9 C14 N15 179.54(13) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C10 C11 N31 C32 -82.19(19) . . . . ?
C10 C11 N31 C44 109.01(17) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
C12 C11 N31 C32 99.35(17) . . . . ?
C12 C11 N31 C44 -69.45(19) . . . . ?
C12 C13 C14 C9 -0.8(2) . . . . ?
C12 C13 C14 N15 179.30(15) . . . . ?
C13 C14 N15 C16 179.54(15) . . . . ?
C13 C14 N15 C45 -1.3(3) . . . . ?
C14 C9 C10 C11 1.3(2) . . . . ?
C16 C8 C9 C10 -179.23(16) . . . . ?
C16 C8 C9 C14 -0.43(16) . . . . ?
C16 C17 C18 C19 -178.50(14) . . . . ?
C16 C17 C18 C20 1.4(2) . . . . ?
C17 C16 N15 C14 -178.33(15) . . . . ?
C17 C16 N15 C45 2.5(3) . . . . ?
C17 C18 C19 N1 -179.83(14) . . . . ?
C17 C18 C19 O47 0.1(2) . . . . ?
C17 C18 C20 C3 178.92(15) . . . . ?
C17 C18 C20 C7 -1.0(2) . . . . ?
C18 C19 N1 C2 0.5(2) . . . . ?
C18 C19 N1 C21 177.03(14) . . . . ?
C19 C18 C20 C3 -1.1(2) . . . . ?
C19 C18 C20 C7 178.94(14) . . . . ?
C20 C3 C4 C5 -0.1(2) . . . . ?
C20 C7 C8 C9 -177.91(16) . . . . ?
C20 C7 C8 C16 0.6(2) . . . . ?
C20 C18 C19 N1 0.2(2) . . . . ?
C20 C18 C19 O47 -179.81(16) . . . . ?
C21 C22 C23 C24 -0.8(3) . . . . ?
C22 C21 C26 C25 1.0(3) . . . . ?
C22 C21 C26 C29 -179.99(18) . . . . ?
C22 C21 N1 C2 -94.07(19) . . . . ?
C22 C21 N1 C19 89.15(19) . . . . ?
C22 C23 C24 C25 1.0(3) . . . . ?
C22 C23 C24 C28 -178.32(17) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
C24 C25 C26 C21 -0.7(3) . . . . ?
C24 C25 C26 C29 -179.77(18) . . . . ?
C26 C21 C22 C23 -0.2(3) . . . . ?
C26 C21 C22 C27 179.72(17) . . . . ?
C26 C21 N1 C2 88.88(19) . . . . ?
C26 C21 N1 C19 -87.90(19) . . . . ?
C27 C22 C23 C24 179.27(17) . . . . ?
C28 C24 C25 C26 179.08(18) . . . . ?
C32 C33 C34 C35 -0.7(2) . . . . ?
C32 C37 O38 C39 3.2(2) . . . . ?
C33 C32 C37 C36 1.5(2) . . . . ?
C33 C32 C37 O38 -177.74(14) . . . . ?
C33 C32 N31 C11 5.6(2) . . . . ?
C33 C32 N31 C44 174.51(14) . . . . ?
C33 C34 C35 C36 1.3(2) . . . . ?
C34 C35 C36 C37 -0.4(2) . . . . ?
C35 C36 C37 C32 -1.0(2) . . . . ?
C35 C36 C37 O38 178.33(14) . . . . ?
C36 C37 O38 C39 -176.12(14) . . . . ?
C37 C32 C33 C34 -0.7(2) . . . . ?
C37 C32 N31 C11 -174.02(14) . . . . ?
C37 C32 N31 C44 -5.2(2) . . . . ?
C39 C40 C41 C42 -0.6(3) . . . . ?
C39 C44 N31 C11 172.20(14) . . . . ?
C39 C44 N31 C32 3.2(2) . . . . ?
C40 C39 C44 C43 2.2(2) . . . . ?
C40 C39 C44 N31 -178.41(15) . . . . ?
C40 C39 O38 C37 175.23(14) . . . . ?
C40 C41 C42 C43 1.4(3) . . . . ?
C41 C42 C43 C44 -0.4(2) . . . . ?
C42 C43 C44 C39 -1.3(2) . . . . ?
C42 C43 C44 N31 179.26(15) . . . . ?
C43 C44 N31 C11 -8.4(2) . . . . ?
C43 C44 N31 C32 -177.37(14) . . . . ?
C44 C39 C40 C41 -1.2(3) . . . . ?
C44 C39 O38 C37 -5.2(2) . . . . ?
C45 C46 C47 C48 -176.12(14) . . . . ?
C46 C45 N15 C14 -91.50(18) . . . . ?
C46 C45 N15 C16 87.48(18) . . . . ?
N1 C2 C3 C4 -179.90(14) . . . . ?
N1 C2 C3 C20 -0.7(2) . . . . ?
N1 C21 C22 C23 -177.17(15) . . . . ?
N1 C21 C22 C27 2.8(2) . . . . ?
N1 C21 C26 C25 177.92(15) . . . . ?
N1 C21 C26 C29 -3.0(3) . . . . ?
N15 C16 C17 C18 177.40(15) . . . . ?
N15 C45 C46 C47 -173.53(13) . . . . ?
N31 C11 C12 C13 178.33(14) . . . . ?
N31 C32 C33 C34 179.64(14) . . . . ?
N31 C32 C37 C36 -178.78(14) . . . . ?
N31 C32 C37 O38 1.9(2) . . . . ?
O30 C2 C3 C4 -0.3(2) . . . . ?
O30 C2 C3 C20 178.93(16) . . . . ?
O30 C2 N1 C19 -179.90(16) . . . . ?
O30 C2 N1 C21 3.6(2) . . . . ?
O38 C39 C40 C41 178.35(15) . . . . ?
O38 C39 C44 C43 -177.38(14) . . . . ?
O38 C39 C44 N31 2.0(2) . . . . ?
O47 C19 N1 C2 -179.47(16) . . . . ?
O47 C19 N1 C21 -2.9(2) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-10.1817 5.3544 -1.1470 0.0204 0.7728 0.6344
-11.3842 -2.9359 5.5954 -0.0140 -0.5765 0.8170
14.2720 -2.8035 -2.0165 -0.0092 -0.3241 -0.9460
-6.7069 6.0835 -2.7262 0.0240 0.9218 0.3870
1.4087 3.9695 7.1291 0.9739 -0.0252 0.2257
-15.4795 -0.2759 1.7756 -0.2717 0.0061 0.9624
15.2248 1.1723 -0.0812 0.4840 -0.0116 -0.8750
-4.5016 -3.9050 -6.5533 -0.9994 0.0257 -0.0239
-13.9766 -2.1067 -1.8302 -0.6923 0.0171 0.7214
8.0942 4.4577 -5.8054 0.0198 0.7925 -0.6095
