#------------------------------------------------------------------------------
#$Date: 2020-08-06 16:44:15 +0200 (Thu 06 de Aug de 2020) $
#$Revision: 255097 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/75/7157542.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_7157542
loop_
_publ_author_name
'Nguyen, Tuan K.'
'Titov, Gleb D.'
'Khoroshilova, Olesya V.'
'Kinzhalov, Mikhail A.'
'Rostovskii, Nikolai V.'
_publ_section_title
;
 Light-induced one-pot synthesis of pyrimidine derivatives from vinyl
 azides.
;
_journal_issue                   26
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4971
_journal_page_last               4982
_journal_paper_doi               10.1039/d0ob00693a
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H14 Cl4 N2 O4'
_chemical_formula_sum            'C20 H14 Cl4 N2 O4'
_chemical_formula_weight         488.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2020-03-31 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.7710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.82480(10)
_cell_length_b                   16.44070(10)
_cell_length_c                   12.04070(10)
_cell_measurement_reflns_used    19869
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.2600
_cell_measurement_theta_min      3.8950
_cell_volume                     2016.53(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00   6.00   0.50    0.40    --   38.95 -54.00-138.00   52
  2  ω     29.00  64.00   0.50    0.40    --   38.95  54.00   6.00   70
  3  ω     67.00 102.00   0.50    0.40    --   38.95  54.00   6.00   70
  4  ω     80.00 141.00   0.50    0.90    --  100.00  54.00   6.00  122
  5  ω     70.00 118.00   0.50    0.90    --  100.00 -54.00-138.00   96
  6  ω     42.00  68.00   0.50    0.90    --  100.00 -54.00-138.00   52
  7  ω     -7.00  21.00   0.50    0.40    --  -38.95  32.00 120.00   56
  8  ω    -46.00 -20.00   0.50    0.40    --  -38.95  32.00 120.00   52
  9  ω    -72.00 -46.00   0.50    0.40    --  -38.95 -21.00-120.00   52
 10  ω    -46.00 -21.00   0.50    0.40    --  -38.95 -54.00-138.00   50
 11  ω    -80.00 -54.00   0.50    0.40    --  -38.95 -54.00-138.00   52
 12  ω    -56.00  25.00   0.50    0.40    --  -38.95  43.00-180.00  162
 13  ω   -107.00 -79.00   0.50    0.40    --  -38.95 -21.00-120.00   56
 14  ω    -34.00  -8.00   0.50    0.40    --  -38.95  54.00   6.00   52
 15  ω     23.00  49.00   0.50    0.40    --   38.95  21.00  90.00   52
 16  ω     76.00 106.00   0.50    0.40    --   38.95  21.00 -30.00   60
 17  ω     32.00 100.00   0.50    0.40    --   38.95  65.00  30.00  136
 18  ω     24.00  72.00   0.50    0.40    --   38.95  21.00 -30.00   96
 19  ω     22.00  49.00   0.50    0.40    --   38.95 -54.00-138.00   54
 20  ω     76.00 102.00   0.50    0.40    --   38.95  21.00  90.00   52
 21  ω    -17.00  53.00   0.50    0.40    --   38.95 -43.00  90.00  140
 22  ω     35.00  61.00   0.50    0.40    --   38.95  32.00   0.00   52
 23  ω     31.00  80.00   0.50    0.90    --  100.00-111.00 -90.00   98
 24  ω    130.00 156.00   0.50    0.90    --  100.00   7.00 -30.00   52
 25  ω     78.00 124.00   0.50    0.90    --  100.00 -69.00   0.00   92
 26  ω     84.00 155.00   0.50    0.90    --  100.00 133.00-120.00  142
 27  ω     94.00 119.00   0.50    0.90    --  100.00 -22.00  90.00   50
 28  ω     61.00  93.00   0.50    0.90    --  100.00   7.00 -30.00   64
 29  ω     63.00  89.00   0.50    0.90    --  100.00 -22.00  90.00   52
 30  ω     83.00 114.00   0.50    0.90    --  100.00 -30.00-180.00   62
 31  ω     46.00 116.00   0.50    0.90    --  100.00 -45.00  90.00  140
 32  ω     32.00  63.00   0.50    0.90    --  100.00 -30.00-180.00   62
 33  ω     83.00 110.00   0.50    0.90    --  100.00 -45.00   0.00   54
 34  ω    108.00 156.00   0.50    0.90    --  100.00  93.00  60.00   96
 35  ω     78.00 125.00   0.50    0.90    --  100.00  61.00 150.00   94
 36  ω     31.00  75.00   0.50    0.90    --  100.00 -30.00  30.00   88
 37  ω     84.00 125.00   0.50    0.90    --  100.00 111.00  60.00   82
 38  ω     61.00 104.00   0.50    0.90    --  100.00 -61.00   0.00   86
 39  ω    107.00 133.00   0.50    0.90    --  100.00  30.00  90.00   52
 40  ω    101.00 157.00   0.50    0.90    --  100.00  93.00-150.00  112
 41  ω     86.00 134.00   0.50    0.90    --  100.00 111.00 -90.00   96
 42  ω     86.00 152.00   0.50    0.90    --  100.00  53.00 -30.00  132
 43  ω     93.00 147.00   0.50    0.90    --  100.00  93.00 -30.00  108
 44  ω     40.00  66.00   0.50    0.90    --  100.00 -54.00-138.00   52
 45  ω    -77.00 -25.00   0.50    0.40    --  -38.95 -32.00  90.00  104
 46  ω     18.00  56.00   0.50    0.40    --   38.95  65.00 120.00   76
 47  ω     82.00 108.00   0.50    0.40    --   38.95  32.00-150.00   52
 48  ω     61.00 101.00   0.50    0.40    --   38.95  65.00 120.00   80
 49  ω     21.00  90.00   0.50    0.40    --   38.95  65.00 150.00  138
 50  ω     15.00  59.00   0.50    0.40    --   38.95 -11.00-150.00   88
 51  ω    -27.00   6.00   0.50    0.40    --   38.95 -11.00-150.00   66
 52  ω     -3.00  48.00   0.50    0.40    --   38.95 -32.00 120.00  102
 53  ω     31.00  57.00   0.50    0.40    --   38.95  65.00  90.00   52
 54  ω     63.00  97.00   0.50    0.40    --   38.95  65.00  90.00   68
 55  ω     86.00 114.00   0.50    0.90    --  100.00  53.00 -60.00   56
 56  ω     76.00 101.00   0.50    0.90    --  100.00  69.00 120.00   50
 57  ω     78.00 110.00   0.50    0.90    --  100.00  61.00 120.00   64
 58  ω    106.00 153.00   0.50    0.90    --  100.00  93.00   0.00   94
 59  ω    114.00 157.00   0.50    0.90    --  100.00  67.00  99.99   86
 60  ω    121.00 154.00   0.50    0.90    --  100.00  69.00  30.00   66
 61  ω    132.00 157.00   0.50    0.90    --  100.00  69.00  60.00   50
 62  ω     93.00 119.00   0.50    0.90    --  100.00  69.00  30.00   52
 63  ω     84.00 110.00   0.50    0.90    --  100.00  45.00 150.00   52
 64  ω    110.00 136.00   0.50    0.90    --  100.00 133.00 120.00   52
 65  ω    118.00 157.00   0.50    0.90    --  100.00 133.00 150.00   78
 66  ω     76.00 102.00   0.50    0.90    --  100.00  67.00  99.99   52
 67  ω    113.00 149.00   0.50    0.90    --  100.00  77.00 120.00   72
 68  ω     80.00 121.00   0.50    0.90    --  100.00  53.00 150.00   82
 69  ω    127.00 153.00   0.50    0.90    --  100.00  53.00 150.00   52
 70  ω     75.00 108.00   0.50    0.90    --  100.00-111.00-120.00   66
 71  ω    132.00 157.00   0.50    0.90    --  100.00  69.00  90.00   50
 72  ω    120.00 146.00   0.50    0.90    --  100.00  61.00 120.00   52
 73  ω     76.00 112.00   0.50    0.90    --  100.00  69.00  60.00   72
 74  ω     36.00  61.00   0.50    0.90    --  100.00-133.00  30.00   50
 75  ω     80.00 120.00   0.50    0.90    --  100.00  53.00-180.00   80
 76  ω     86.00 115.00   0.50    0.90    --  100.00  61.00-150.00   58
 77  ω     80.00 106.00   0.50    0.90    --  100.00  53.00  90.00   52
 78  ω     76.00 105.00   0.50    0.90    --  100.00  69.00  90.00   58
 79  ω     83.00 109.00   0.50    0.90    --  100.00  45.00  90.00   52
 80  ω    132.00 157.00   0.50    0.90    --  100.00  61.00-150.00   50
 81  ω     78.00 107.00   0.50    0.90    --  100.00  61.00  90.00   58
 82  ω     43.00  94.00   0.50    0.90    --  100.00 -93.00  60.00  102
 83  ω     79.00 104.00   0.50    0.90    --  100.00  61.00  60.00   50
 84  ω     82.00 130.00   0.50    0.90    --  100.00 -86.00-180.00   96
 85  ω     76.00 101.00   0.50    0.90    --  100.00  69.00 150.00   50
 86  ω     26.00  51.00   0.50    0.90    --  100.00 -93.00 -30.00   50
 87  ω    108.00 140.00   0.50    0.90    --  100.00 111.00  30.00   64
 88  ω     83.00 109.00   0.50    0.90    --  100.00  77.00  60.00   52
 89  ω     83.00 108.00   0.50    0.90    --  100.00  77.00  90.00   50
 90  ω     83.00 109.00   0.50    0.90    --  100.00  77.00 120.00   52
 91  ω    130.00 156.00   0.50    0.90    --  100.00  53.00 -60.00   52
 92  ω    106.00 131.00   0.50    0.90    --  100.00  22.00 -60.00   50
 93  ω     82.00 108.00   0.50    0.90    --  100.00-111.00-180.00   52
 94  ω     37.00  65.00   0.50    0.90    --  100.00-111.00   0.00   56
 95  ω     86.00 120.00   0.50    0.90    --  100.00  37.00  60.00   68
 96  ω     80.00 110.00   0.50    0.90    --  100.00  53.00 120.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1369845000
_diffrn_orient_matrix_UB_12      -0.0247362000
_diffrn_orient_matrix_UB_13      0.0841085000
_diffrn_orient_matrix_UB_21      0.0640861000
_diffrn_orient_matrix_UB_22      0.0555530000
_diffrn_orient_matrix_UB_23      -0.0680923000
_diffrn_orient_matrix_UB_31      -0.0024101000
_diffrn_orient_matrix_UB_32      0.0712990000
_diffrn_orient_matrix_UB_33      0.0822795000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25202
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.448
_diffrn_reflns_theta_min         3.901
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 3387 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         7584
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0233
_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)+(0.0340P)²+0.0377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0585
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                7401
_reflns_number_total             7584
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00693a2.cif
_cod_data_source_block           15289_htk-02
_cod_depositor_comments
'Adding full bibliography for 7157540--7157542.cif.'
_cod_database_code               7157542
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H14 Cl4 N2 O4'
_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 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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.a Ternary CH refined with riding coordinates:
 C2(H2A), C2A(H2AB)
2.b Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C16(H16), C15(H15), C15A(H15A), C10A(H10A), C13(H13), C7(H7),
 C10(H10), C9(H9), C13A(H13A), C9A(H9A), C16A(H16A)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F), C20A(H20D,
 H20E,H20F)
;
_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 2.314
_oxdiff_exptl_absorpt_empirical_full_min 0.853
loop_
_space_group_symop_operation_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
Cl3 Cl 0.77991(6) 0.46437(4) 0.32231(5) 0.01716(13) Uani 1 1 d . . . . .
Cl2A Cl 0.00367(6) 0.31701(4) 0.31563(6) 0.02028(14) Uani 1 1 d . . . . .
Cl1 Cl 1.19783(6) 0.67109(4) 1.02248(6) 0.02126(14) Uani 1 1 d . . . . .
Cl2 Cl 0.97906(6) 0.57293(4) 0.57482(6) 0.02133(14) Uani 1 1 d . . . . .
Cl3A Cl 0.44331(6) 0.56415(4) 0.96937(6) 0.02088(14) Uani 1 1 d . . . . .
Cl1A Cl 0.24837(6) 0.42868(4) 0.75234(5) 0.02075(14) Uani 1 1 d . . . . .
Cl4 Cl 0.70510(7) 0.73016(4) 0.05012(6) 0.02208(14) Uani 1 1 d . . . . .
Cl4A Cl 0.46509(7) 0.29822(5) 1.23328(6) 0.02363(15) Uani 1 1 d . . . . .
O3A O 0.87425(19) 0.39077(12) 0.64542(16) 0.0178(4) Uani 1 1 d . . . . .
O4 O 0.31914(19) 0.71459(12) 0.53452(17) 0.0170(4) Uani 1 1 d . . . . .
O3 O 0.34142(19) 0.61153(12) 0.66256(17) 0.0178(4) Uani 1 1 d . . . . .
O4A O 0.88550(19) 0.28613(12) 0.76952(17) 0.0195(4) Uani 1 1 d . . . . .
O2 O 0.23209(18) 0.56183(13) 0.39381(17) 0.0187(4) Uani 1 1 d . . . . .
O1A O 0.8938(2) 0.50421(13) 1.02732(17) 0.0215(4) Uani 1 1 d . . . . .
O1 O 0.32953(19) 0.50158(13) 0.27740(17) 0.0212(4) Uani 1 1 d . . . . .
O2A O 0.98366(19) 0.42991(14) 0.91708(17) 0.0218(4) Uani 1 1 d . . . . .
N1A N 0.6117(2) 0.36403(14) 0.6889(2) 0.0159(5) Uani 1 1 d . . . . .
N2 N 0.6931(2) 0.53805(14) 0.5428(2) 0.0143(4) Uani 1 1 d . . . . .
N2A N 0.5259(2) 0.47524(14) 0.7592(2) 0.0152(4) Uani 1 1 d . . . . .
N1 N 0.6009(2) 0.64305(14) 0.61938(19) 0.0152(4) Uani 1 1 d . . . . .
C5 C 0.8305(3) 0.61725(16) 0.7118(2) 0.0151(5) Uani 1 1 d . . . . .
C17A C 0.8824(3) 0.46376(17) 0.9402(2) 0.0164(5) Uani 1 1 d . . . . .
C19A C 0.8406(3) 0.35694(16) 0.7202(2) 0.0150(5) Uani 1 1 d . . . . .
C1 C 0.7028(3) 0.59941(16) 0.6187(2) 0.0139(5) Uani 1 1 d . . . . .
C19 C 0.3711(3) 0.64540(16) 0.5861(2) 0.0140(5) Uani 1 1 d . . . . .
C4 C 0.4804(3) 0.61564(16) 0.5447(2) 0.0145(5) Uani 1 1 d . . . . .
C2 C 0.5848(2) 0.53703(16) 0.4289(2) 0.0145(5) Uani 1 1 d . . . . .
H2A H 0.5710 0.4796 0.4000 0.017 Uiso 1 1 calc R . . . .
C5A C 0.3821(3) 0.38916(16) 0.6014(2) 0.0151(5) Uani 1 1 d . . . . .
C7A C 0.1435(3) 0.37489(17) 0.5323(2) 0.0172(5) Uani 1 1 d . . . . .
H7A H 0.0620 0.3816 0.5447 0.021 Uiso 1 1 calc R . . . .
C16 C 0.5650(3) 0.66518(17) 0.3034(2) 0.0159(5) Uani 1 1 d . . . . .
H16 H 0.5072 0.6872 0.3399 0.019 Uiso 1 1 calc R . . . .
C15 C 0.5933(3) 0.71066(17) 0.2181(2) 0.0176(5) Uani 1 1 d . . . . .
H15 H 0.5558 0.7630 0.1964 0.021 Uiso 1 1 calc R . . . .
C15A C 0.6058(3) 0.31423(18) 1.0878(2) 0.0180(5) Uani 1 1 d . . . . .
H15A H 0.6379 0.2610 1.1120 0.022 Uiso 1 1 calc R . . . .
C20 C 0.2210(3) 0.74943(17) 0.5780(2) 0.0189(6) Uani 1 1 d . . . . .
H20A H 0.1906 0.8014 0.5383 0.028 Uiso 1 1 calc GR . . . .
H20B H 0.2596 0.7585 0.6633 0.028 Uiso 1 1 calc GR . . . .
H20C H 0.1466 0.7120 0.5618 0.028 Uiso 1 1 calc GR . . . .
C1A C 0.5121(3) 0.41006(16) 0.6889(2) 0.0148(5) Uani 1 1 d . . . . .
C10A C 0.3815(3) 0.35493(16) 0.4948(2) 0.0172(5) Uani 1 1 d . . . . .
H10A H 0.4626 0.3475 0.4818 0.021 Uiso 1 1 calc R . . . .
C13 C 0.7359(3) 0.60234(17) 0.1969(2) 0.0160(5) Uani 1 1 d . . . . .
H13 H 0.7944 0.5809 0.1607 0.019 Uiso 1 1 calc R . . . .
C7 C 1.0696(3) 0.62117(17) 0.7988(3) 0.0180(5) Uani 1 1 d . . . . .
H7 H 1.1535 0.6107 0.7931 0.022 Uiso 1 1 calc R . . . .
C10 C 0.8249(3) 0.65176(16) 0.8168(2) 0.0164(5) Uani 1 1 d . . . . .
H10 H 0.7416 0.6631 0.8233 0.020 Uiso 1 1 calc R . . . .
C3A C 0.7543(3) 0.44370(16) 0.8512(2) 0.0147(5) Uani 1 1 d . . . . .
C12 C 0.7059(2) 0.55906(16) 0.2837(2) 0.0143(5) Uani 1 1 d . . . . .
C3 C 0.4628(3) 0.56485(17) 0.4521(2) 0.0147(5) Uani 1 1 d . . . . .
C11A C 0.5982(3) 0.43432(17) 0.9675(2) 0.0147(5) Uani 1 1 d . . . . .
C9 C 0.9370(3) 0.66972(18) 0.9109(2) 0.0182(5) Uani 1 1 d . . . . .
H9 H 0.9310 0.6933 0.9810 0.022 Uiso 1 1 calc R . . . .
C11 C 0.6185(3) 0.58834(16) 0.3373(2) 0.0146(5) Uani 1 1 d . . . . .
C13A C 0.4693(3) 0.42860(19) 1.0990(2) 0.0179(5) Uani 1 1 d . . . . .
H13A H 0.4104 0.4535 1.1318 0.021 Uiso 1 1 calc R . . . .
C6 C 0.9561(3) 0.60504(17) 0.7045(2) 0.0160(5) Uani 1 1 d . . . . .
C9A C 0.2665(3) 0.33148(17) 0.4077(2) 0.0181(6) Uani 1 1 d . . . . .
H9A H 0.2682 0.3081 0.3361 0.022 Uiso 1 1 calc R . . . .
C12A C 0.5092(3) 0.46826(17) 1.0154(2) 0.0163(5) Uani 1 1 d . . . . .
C4A C 0.7337(3) 0.39063(16) 0.7612(2) 0.0151(5) Uani 1 1 d . . . . .
C2A C 0.6351(3) 0.47848(16) 0.8723(2) 0.0147(5) Uani 1 1 d . . . . .
H2AB H 0.6530 0.5368 0.8960 0.018 Uiso 1 1 calc R . . . .
C8 C 1.0581(3) 0.65269(16) 0.9011(2) 0.0172(5) Uani 1 1 d . . . . .
C14 C 0.6777(3) 0.67779(17) 0.1649(2) 0.0164(5) Uani 1 1 d . . . . .
C17 C 0.3375(3) 0.53895(16) 0.3659(2) 0.0152(5) Uani 1 1 d . . . . .
C16A C 0.6456(3) 0.35692(17) 1.0056(2) 0.0170(5) Uani 1 1 d . . . . .
H16A H 0.7067 0.3325 0.9748 0.020 Uiso 1 1 calc R . . . .
C6A C 0.2604(3) 0.39675(16) 0.6185(2) 0.0157(5) Uani 1 1 d . . . . .
C8A C 0.1488(3) 0.34280(16) 0.4272(2) 0.0168(5) Uani 1 1 d . . . . .
C18 C 0.1072(3) 0.54193(18) 0.3060(3) 0.0206(6) Uani 1 1 d . . . . .
H18A H 0.0980 0.5711 0.2327 0.031 Uiso 1 1 calc GR . . . .
H18B H 0.0361 0.5580 0.3347 0.031 Uiso 1 1 calc GR . . . .
H18C H 0.1026 0.4832 0.2912 0.031 Uiso 1 1 calc GR . . . .
C14A C 0.5186(3) 0.35109(18) 1.1332(2) 0.0181(5) Uani 1 1 d . . . . .
C18A C 1.1104(3) 0.4375(2) 1.0078(3) 0.0252(6) Uani 1 1 d . . . . .
H18D H 1.1766 0.4100 0.9824 0.038 Uiso 1 1 calc GR . . . .
H18E H 1.1076 0.4125 1.0808 0.038 Uiso 1 1 calc GR . . . .
H18F H 1.1331 0.4952 1.0218 0.038 Uiso 1 1 calc GR . . . .
C20A C 0.9879(3) 0.25019(19) 0.7332(3) 0.0243(6) Uani 1 1 d . . . . .
H20D H 0.9506 0.2321 0.6510 0.036 Uiso 1 1 calc GR . . . .
H20E H 1.0257 0.2035 0.7838 0.036 Uiso 1 1 calc GR . . . .
H20F H 1.0566 0.2907 0.7401 0.036 Uiso 1 1 calc GR . . . .
H2 H 0.755(4) 0.507(3) 0.554(3) 0.027(10) Uiso 1 1 d . . . . .
H2AA H 0.465(4) 0.507(2) 0.749(3) 0.025(10) Uiso 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_
_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
C19 O4 C20 114.6(2) . . ?
C19A O4A C20A 115.2(2) . . ?
C17 O2 C18 114.6(2) . . ?
C17A O2A C18A 116.3(2) . . ?
C1A N1A C4A 115.2(2) . . ?
C1 N2 C2 119.8(2) . . ?
C1A N2A C2A 119.7(2) . . ?
C1 N1 C4 115.1(2) . . ?
C10 C5 C1 116.5(2) . . ?
C10 C5 C6 116.8(3) . . ?
C6 C5 C1 126.7(2) . . ?
O1A C17A O2A 123.9(2) . . ?
O1A C17A C3A 123.1(3) . . ?
O2A C17A C3A 113.0(2) . . ?
O3A C19A O4A 125.4(3) . . ?
O3A C19A C4A 122.0(2) . . ?
O4A C19A C4A 112.5(2) . . ?
N2 C1 C5 120.1(2) . . ?
N1 C1 N2 122.8(2) . . ?
N1 C1 C5 117.0(2) . . ?
O4 C19 C4 112.2(2) . . ?
O3 C19 O4 124.9(2) . . ?
O3 C19 C4 122.8(2) . . ?
N1 C4 C19 110.5(2) . . ?
C3 C4 N1 125.0(2) . . ?
C3 C4 C19 124.3(2) . . ?
N2 C2 C3 107.2(2) . . ?
N2 C2 C11 110.9(2) . . ?
C3 C2 C11 113.8(2) . . ?
C10A C5A C1A 117.0(2) . . ?
C10A C5A C6A 117.1(2) . . ?
C6A C5A C1A 125.8(2) . . ?
C6A C7A C8A 118.2(2) . . ?
C15 C16 C11 122.2(2) . . ?
C16 C15 C14 118.4(3) . . ?
C14A C15A C16A 118.5(3) . . ?
N1A C1A N2A 122.8(2) . . ?
N1A C1A C5A 116.5(2) . . ?
N2A C1A C5A 120.6(2) . . ?
C9A C10A C5A 122.1(3) . . ?
C14 C13 C12 117.8(2) . . ?
C8 C7 C6 118.7(3) . . ?
C9 C10 C5 122.1(3) . . ?
C17A C3A C2A 116.1(2) . . ?
C4A C3A C17A 126.0(2) . . ?
C4A C3A C2A 117.5(2) . . ?
C13 C12 Cl3 117.1(2) . . ?
C13 C12 C11 122.5(3) . . ?
C11 C12 Cl3 120.4(2) . . ?
C4 C3 C2 116.8(2) . . ?
C4 C3 C17 126.9(2) . . ?
C17 C3 C2 116.1(2) . . ?
C12A C11A C2A 121.0(2) . . ?
C16A C11A C12A 117.3(2) . . ?
C16A C11A C2A 121.6(2) . . ?
C10 C9 C8 118.7(3) . . ?
C16 C11 C2 122.4(2) . . ?
C16 C11 C12 117.1(2) . . ?
C12 C11 C2 120.5(2) . . ?
C12A C13A C14A 117.7(2) . . ?
C5 C6 Cl2 122.2(2) . . ?
C7 C6 Cl2 115.9(2) . . ?
C7 C6 C5 121.9(3) . . ?
C10A C9A C8A 118.6(3) . . ?
C11A C12A Cl3A 119.8(2) . . ?
C13A C12A Cl3A 117.5(2) . . ?
C13A C12A C11A 122.7(3) . . ?
N1A C4A C19A 110.7(2) . . ?
C3A C4A N1A 124.9(2) . . ?
C3A C4A C19A 124.3(2) . . ?
N2A C2A C3A 107.2(2) . . ?
N2A C2A C11A 110.3(2) . . ?
C3A C2A C11A 113.8(2) . . ?
C7 C8 Cl1 120.0(2) . . ?
C7 C8 C9 121.7(3) . . ?
C9 C8 Cl1 118.2(2) . . ?
C15 C14 Cl4 119.3(2) . . ?
C13 C14 Cl4 118.7(2) . . ?
C13 C14 C15 121.9(3) . . ?
O2 C17 C3 113.7(2) . . ?
O1 C17 O2 123.3(3) . . ?
O1 C17 C3 123.0(2) . . ?
C11A C16A C15A 121.8(3) . . ?
C5A C6A Cl1A 122.0(2) . . ?
C7A C6A Cl1A 115.9(2) . . ?
C7A C6A C5A 122.0(2) . . ?
C7A C8A Cl2A 119.4(2) . . ?
C9A C8A Cl2A 118.6(2) . . ?
C9A C8A C7A 122.0(3) . . ?
C15A C14A Cl4A 119.2(2) . . ?
C15A C14A C13A 122.0(3) . . ?
C13A C14A Cl4A 118.7(2) . . ?
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
Cl3 C12 1.741(3) . ?
Cl2A C8A 1.739(3) . ?
Cl1 C8 1.738(3) . ?
Cl2 C6 1.744(3) . ?
Cl3A C12A 1.742(3) . ?
Cl1A C6A 1.741(3) . ?
Cl4 C14 1.738(3) . ?
Cl4A C14A 1.736(3) . ?
O3A C19A 1.215(3) . ?
O4 C19 1.326(3) . ?
O4 C20 1.451(3) . ?
O3 C19 1.209(3) . ?
O4A C19A 1.323(3) . ?
O4A C20A 1.448(3) . ?
O2 C17 1.347(3) . ?
O2 C18 1.444(3) . ?
O1A C17A 1.213(4) . ?
O1 C17 1.208(4) . ?
O2A C17A 1.340(3) . ?
O2A C18A 1.441(3) . ?
N1A C1A 1.317(4) . ?
N1A C4A 1.384(4) . ?
N2 C1 1.341(4) . ?
N2 C2 1.473(3) . ?
N2A C1A 1.342(4) . ?
N2A C2A 1.471(3) . ?
N1 C1 1.318(4) . ?
N1 C4 1.385(4) . ?
C5 C1 1.485(4) . ?
C5 C10 1.405(4) . ?
C5 C6 1.407(4) . ?
C17A C3A 1.475(4) . ?
C19A C4A 1.508(4) . ?
C19 C4 1.512(4) . ?
C4 C3 1.354(4) . ?
C2 C3 1.510(4) . ?
C2 C11 1.528(4) . ?
C5A C1A 1.485(4) . ?
C5A C10A 1.399(4) . ?
C5A C6A 1.406(4) . ?
C7A C6A 1.386(4) . ?
C7A C8A 1.390(4) . ?
C16 C15 1.386(4) . ?
C16 C11 1.392(4) . ?
C15 C14 1.390(4) . ?
C15A C16A 1.395(4) . ?
C15A C14A 1.381(4) . ?
C10A C9A 1.384(4) . ?
C13 C12 1.390(4) . ?
C13 C14 1.386(4) . ?
C7 C6 1.387(4) . ?
C7 C8 1.380(4) . ?
C10 C9 1.383(4) . ?
C3A C4A 1.350(4) . ?
C3A C2A 1.509(3) . ?
C12 C11 1.398(4) . ?
C3 C17 1.465(4) . ?
C11A C12A 1.396(4) . ?
C11A C2A 1.520(4) . ?
C11A C16A 1.390(4) . ?
C9 C8 1.384(4) . ?
C13A C12A 1.385(4) . ?
C13A C14A 1.389(4) . ?
C9A C8A 1.384(4) . ?
