#------------------------------------------------------------------------------
#$Date: 2022-03-08 03:32:48 +0200 (Tue, 08 Mar 2022) $
#$Revision: 273519 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158558.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_7158558
loop_
_publ_author_name
'Yan, Jiahang'
'Zhang, Wenting'
'He, Qiaoqiao'
'Hou, Jun'
'Zeng, Hongxin'
'Wei, Hongbo'
'Xie, Weiqing'
_publ_section_title
;
 Enantioselective direct vinylogous Michael addition for constructing
 enantioenriched γ,γ-dialkyl substituted butyrolactams and
 octahydroindoles
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00112H
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H24 Cl N O4'
_chemical_formula_sum            'C20 H24 Cl N O4'
_chemical_formula_weight         377.85
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-18 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.1400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.41290(10)
_cell_length_b                   6.44320(10)
_cell_length_c                   24.3361(3)
_cell_measurement_reflns_used    22661
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      74.0840
_cell_measurement_theta_min      3.6780
_cell_volume                     1909.70(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  23.00   1.00    1.00    --    0.00 -57.00   4.00   52
  2  ω     -8.00  30.00   1.00    1.00    --    0.00  57.00 146.00   38
  3  ω     72.00 101.00   1.00    1.00    --   95.80  57.00 146.00   29
  4  ω     22.00 104.00   1.00    1.00    --   95.80 -57.00   4.00   82
  5  ω     46.00  87.00   1.00    1.00    --    0.00  57.00-120.00   41
  6  ω    -18.00  24.00   1.00    1.00    --    0.00 -19.00  60.00   42
  7  ω     38.00  72.00   1.00    1.00    --    0.00  37.00  30.00   34
  8  ω     17.00  89.00   1.00    1.00    --    0.00  37.00-180.00   72
  9  ω    -23.00  40.00   1.00    1.00    --    0.00  57.00-120.00   63
 10  ω    -22.00  17.00   1.00    1.00    --    0.00  19.00 150.00   39
 11  ω    -83.00  12.00   1.00    1.00    --    0.00 -37.00-180.00   95
 12  ω    -10.00  25.00   1.00    1.00    --    0.00  37.00  30.00   35
 13  ω     59.00  85.00   1.00    1.00    --    0.00  19.00 150.00   26
 14  ω    -30.00  54.00   1.00    1.00    --    0.00  77.00 -30.00   84
 15  ω    -88.00 -29.00   1.00    1.00    --    0.00 -19.00  60.00   59
 16  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 17  ω     75.00 104.00   1.00    1.00    --   95.80  45.00 120.00   29
 18  ω     65.00  93.00   1.00    1.00    --   95.80  77.00-120.00   28
 19  ω     60.00 128.00   1.00    1.00    --   95.80 -82.00   0.00   68
 20  ω    104.00 130.00   1.00    1.00    --   95.80  45.00-120.00   26
 21  ω     68.00 128.00   1.00    1.00    --   95.80 -82.00-150.00   60
 22  ω     63.00 122.00   1.00    1.00    --   95.80  82.00  60.00   59
 23  ω    150.00 182.00   1.00    1.00    --   95.80  82.00 150.00   32
 24  ω     75.00 100.00   1.00    1.00    --   95.80  45.00-120.00   25
 25  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 26  ω     63.00  98.00   1.00    1.00    --   95.80  82.00-150.00   35
 27  ω    105.00 184.00   1.00    1.00    --   95.80  82.00-150.00   79
 28  ω     71.00 183.00   1.00    1.00    --   95.80  61.00  30.00  112
 29  ω     73.00  99.00   1.00    1.00    --   95.80  61.00 -60.00   26
 30  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 31  ω     75.00 185.00   1.00    1.00    --   95.80  45.00 -60.00  110
 32  ω     70.00  95.00   1.00    1.00    --   95.80  62.00-137.57   25
 33  ω    140.00 181.00   1.00    1.00    --   95.80  62.00-137.57   41
 34  ω     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 35  ω      6.00 127.00   1.00    1.00    --   95.80 -82.00 150.00  121
 36  ω    126.00 152.00   1.00    1.00    --   95.80  77.00 -60.00   26
 37  ω     34.00  59.00   1.00    1.00    --   95.80 -82.00-150.00   25
 38  ω     75.00 165.00   1.00    1.00    --   95.80  45.00 -90.00   90
 39  ω    132.00 177.00   1.00    1.00    --   95.80  79.00  45.99   45
 40  ω     75.00 156.00   1.00    1.00    --   95.80  45.00-180.00   81
 41  ω     63.00  96.00   1.00    1.00    --   95.80  82.00-180.00   33
 42  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 43  ω     77.00 103.00   1.00    1.00    --   95.80  45.00 150.00   26
 44  ω    134.00 178.00   1.00    1.00    --   95.80  45.00 150.00   44
 45  ω     69.00  95.00   1.00    1.00    --   95.80  79.00  45.99   26
 46  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 47  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -90.00   25
 48  ω     63.00  88.00   1.00    1.00    --   95.80  82.00   0.00   25
 49  ω     65.00  92.00   1.00    1.00    --   95.80  77.00  90.00   27
 50  ω    111.00 183.00   1.00    1.00    --   95.80  77.00  90.00   72
 51  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 52  ω     83.00 115.00   1.00    1.00    --   95.80 -82.00 -60.00   32
 53  ω     43.00  79.00   1.00    1.00    --   95.80 -82.00 -60.00   36
 54  ω     74.00 184.00   1.00    1.00    --   95.80  51.00  58.33  110
 55  ω     71.00 175.00   1.00    1.00    --   95.80  61.00   0.00  104
 56  ω     70.00  96.00   1.00    1.00    --   95.80  64.00-174.64   26
 57  ω    126.00 151.00   1.00    1.00    --   95.80  77.00-180.00   25
 58  ω     70.00  96.00   1.00    1.00    --   95.80  62.00 121.44   26
 59  ω    159.00 184.00   1.00    1.00    --   95.80  62.00 121.44   25
 60  ω    148.00 184.00   1.00    1.00    --   95.80  52.00 -25.40   36
 61  ω     73.00  99.00   1.00    1.00    --   95.80  52.00 -25.40   26
 62  ω     74.00 100.00   1.00    1.00    --   95.80  61.00  60.00   26
 63  ω     68.00  94.00   1.00    1.00    --   95.80  70.00 -26.29   26
 64  ω     88.00 113.00   1.00    1.00    --   95.80 -82.00  60.00   25
 65  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 66  ω    125.00 164.00   1.00    1.00    --   95.80  45.00 120.00   39
 67  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 68  ω    148.00 173.00   1.00    1.00    --   95.80  75.00  -4.79   25
 69  ω     67.00  92.00   1.00    1.00    --   95.80  75.00  -4.79   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0836107000
_diffrn_orient_matrix_UB_12      0.1638191000
_diffrn_orient_matrix_UB_13      0.0111638000
_diffrn_orient_matrix_UB_21      0.0906574000
_diffrn_orient_matrix_UB_22      0.1088486000
_diffrn_orient_matrix_UB_23      0.0423496000
_diffrn_orient_matrix_UB_31      0.0281004000
_diffrn_orient_matrix_UB_32      0.1359916000
_diffrn_orient_matrix_UB_33      -0.0473700000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            42350
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.060
_diffrn_reflns_theta_max         67.060
_diffrn_reflns_theta_min         3.629
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.978
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 2812 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(5)
_refine_ls_extinction_coef       0.0011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         6817
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0299
_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+0.1130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6431
_reflns_number_total             6817
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00112h2.cif
_cod_data_source_block           exp_2460
_cod_database_code               7158558
_shelx_shelxl_version_number     2017/1
_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   0.670
_shelx_estimated_absorpt_t_min   0.536
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C25(H25), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C22(H22A,H22B), C23(H23A,H23B),
 C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C19(H19), C35(H35), C36(H36), C38(H38), C39(H39)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C20(H20A,H20B,
 H20C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C40(H40A,
 H40B,H40C)
;
_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 1.452
_oxdiff_exptl_absorpt_empirical_full_min 0.566
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
Cl1 Cl 1.00569(6) 0.40903(13) 0.55228(4) 0.0716(3) Uani 1 1 d . . . . .
O1 O 0.36329(12) 0.9110(3) 0.77333(6) 0.0376(4) Uani 1 1 d . . . . .
O2 O 0.25273(12) 0.8866(3) 0.68833(6) 0.0385(4) Uani 1 1 d . . . . .
O3 O 0.57832(12) 0.8593(3) 0.77045(6) 0.0365(4) Uani 1 1 d . . . . .
O4 O 0.49104(13) 0.4272(3) 0.51174(6) 0.0392(4) Uani 1 1 d . . . . .
N1 N 0.43400(13) 0.8598(2) 0.69364(6) 0.0232(3) Uani 1 1 d . . . . .
C1 C 0.41745(15) 0.8528(3) 0.63107(7) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.33841(16) 0.6775(3) 0.60684(8) 0.0282(4) Uani 1 1 d . . . . .
H2A H 0.350067 0.558740 0.631788 0.034 Uiso 1 1 calc R . . . .
H2B H 0.263269 0.723954 0.604248 0.034 Uiso 1 1 calc R . . . .
C3 C 0.35615(16) 0.6129(3) 0.54888(8) 0.0315(5) Uani 1 1 d . . . . .
H3A H 0.302992 0.506706 0.534108 0.038 Uiso 1 1 calc R . . . .
H3B H 0.343085 0.731649 0.523984 0.038 Uiso 1 1 calc R . . . .
C4 C 0.46927(16) 0.5313(3) 0.54938(8) 0.0271(4) Uani 1 1 d . . . . .
C5 C 0.55528(15) 0.5885(3) 0.60118(7) 0.0241(4) Uani 1 1 d . . . . .
H5 H 0.544672 0.494365 0.631301 0.029 Uiso 1 1 calc R . . . .
C6 C 0.53639(16) 0.8115(3) 0.62082(8) 0.0246(4) Uani 1 1 d . . . . .
H6 H 0.551494 0.909256 0.592402 0.029 Uiso 1 1 calc R . . . .
C7 C 0.61285(15) 0.8612(3) 0.67625(8) 0.0285(4) Uani 1 1 d . . . . .
H7A H 0.670751 0.758277 0.684456 0.034 Uiso 1 1 calc R . . . .
H7B H 0.646186 0.996629 0.674509 0.034 Uiso 1 1 calc R . . . .
C8 C 0.54385(16) 0.8589(3) 0.72061(7) 0.0252(4) Uani 1 1 d . . . . .
C9 C 0.34979(16) 0.8886(3) 0.72369(8) 0.0267(4) Uani 1 1 d . . . . .
C10 C 0.15042(18) 0.9283(4) 0.70846(10) 0.0413(5) Uani 1 1 d . . . . .
C11 C 0.1337(2) 0.7703(6) 0.75118(12) 0.0660(8) Uani 1 1 d . . . . .
H11A H 0.141899 0.633555 0.736874 0.099 Uiso 1 1 calc GR . . . .
H11B H 0.061258 0.785071 0.759122 0.099 Uiso 1 1 calc GR . . . .
H11C H 0.187129 0.791022 0.784911 0.099 Uiso 1 1 calc GR . . . .
C12 C 0.1533(2) 1.1465(5) 0.72989(19) 0.0961(14) Uani 1 1 d . . . . .
H12A H 0.203736 1.155218 0.765098 0.144 Uiso 1 1 calc GR . . . .
H12B H 0.081312 1.186135 0.734896 0.144 Uiso 1 1 calc GR . . . .
H12C H 0.176857 1.238088 0.703396 0.144 Uiso 1 1 calc GR . . . .
C13 C 0.0647(2) 0.8996(8) 0.65607(14) 0.0884(14) Uani 1 1 d . . . . .
H13A H 0.077350 0.997171 0.628178 0.133 Uiso 1 1 calc GR . . . .
H13B H -0.006840 0.922465 0.664415 0.133 Uiso 1 1 calc GR . . . .
H13C H 0.069013 0.760958 0.642223 0.133 Uiso 1 1 calc GR . . . .
C14 C 0.67006(16) 0.5496(3) 0.59035(7) 0.0266(4) Uani 1 1 d . . . . .
C15 C 0.71502(19) 0.3519(3) 0.59828(9) 0.0356(5) Uani 1 1 d . . . . .
H15 H 0.675405 0.247353 0.611714 0.043 Uiso 1 1 calc R . . . .
C16 C 0.8178(2) 0.3066(4) 0.58663(10) 0.0434(6) Uani 1 1 d . . . . .
H16 H 0.846934 0.173579 0.592399 0.052 Uiso 1 1 calc R . . . .
C17 C 0.87566(19) 0.4612(4) 0.56647(10) 0.0418(6) Uani 1 1 d . . . . .
C18 C 0.83342(19) 0.6604(4) 0.55784(11) 0.0448(6) Uani 1 1 d . . . . .
H18 H 0.873494 0.764366 0.544447 0.054 Uiso 1 1 calc R . . . .
C19 C 0.73053(17) 0.7023(4) 0.56950(9) 0.0364(5) Uani 1 1 d . . . . .
H19 H 0.701387 0.835152 0.563250 0.044 Uiso 1 1 calc R . . . .
C20 C 0.37897(18) 1.0655(3) 0.60671(8) 0.0332(5) Uani 1 1 d . . . . .
H20A H 0.306338 1.092775 0.613067 0.050 Uiso 1 1 calc GR . . . .
H20B H 0.378240 1.066179 0.567188 0.050 Uiso 1 1 calc GR . . . .
H20C H 0.428239 1.170889 0.624603 0.050 Uiso 1 1 calc GR . . . .
Cl2 Cl -0.00353(5) -0.04573(13) 0.94762(3) 0.0633(2) Uani 1 1 d . . . . .
O5 O 0.42285(12) 0.3847(2) 0.73063(5) 0.0329(3) Uani 1 1 d . . . . .
O6 O 0.50739(13) -0.0478(3) 0.98485(6) 0.0413(4) Uani 1 1 d . . . . .
O7 O 0.75015(11) 0.4035(2) 0.80878(6) 0.0315(3) Uani 1 1 d . . . . .
O8 O 0.63873(11) 0.3327(3) 0.72553(5) 0.0316(3) Uani 1 1 d . . . . .
N2 N 0.56978(12) 0.3728(2) 0.80607(6) 0.0223(3) Uani 1 1 d . . . . .
C21 C 0.58879(15) 0.3853(3) 0.86882(7) 0.0237(4) Uani 1 1 d . . . . .
C22 C 0.66661(16) 0.2121(3) 0.89539(8) 0.0286(4) Uani 1 1 d . . . . .
H22A H 0.657256 0.091735 0.870974 0.034 Uiso 1 1 calc R . . . .
H22B H 0.741981 0.258936 0.899383 0.034 Uiso 1 1 calc R . . . .
C23 C 0.64412(16) 0.1509(3) 0.95268(8) 0.0315(5) Uani 1 1 d . . . . .
H23A H 0.697309 0.047347 0.969234 0.038 Uiso 1 1 calc R . . . .
H23B H 0.653585 0.271679 0.976941 0.038 Uiso 1 1 calc R . . . .
C24 C 0.53062(16) 0.0658(3) 0.94948(7) 0.0272(4) Uani 1 1 d . . . . .
C25 C 0.44626(15) 0.1315(3) 0.89780(7) 0.0248(4) Uani 1 1 d . . . . .
H25 H 0.456151 0.039906 0.867015 0.030 Uiso 1 1 calc R . . . .
C26 C 0.47002(15) 0.3552(3) 0.88046(7) 0.0246(4) Uani 1 1 d . . . . .
H26 H 0.459135 0.450992 0.910194 0.030 Uiso 1 1 calc R . . . .
C27 C 0.39474(16) 0.4192(3) 0.82583(8) 0.0309(5) Uani 1 1 d . . . . .
H27A H 0.329103 0.333942 0.818980 0.037 Uiso 1 1 calc R . . . .
H27B H 0.373142 0.563373 0.827522 0.037 Uiso 1 1 calc R . . . .
C28 C 0.45947(15) 0.3884(3) 0.78029(7) 0.0244(4) Uani 1 1 d . . . . .
C29 C 0.65299(15) 0.3664(3) 0.77495(8) 0.0240(4) Uani 1 1 d . . . . .
C30 C 0.85382(16) 0.3603(4) 0.78997(10) 0.0363(5) Uani 1 1 d . . . . .
C31 C 0.9387(2) 0.4233(6) 0.84078(11) 0.0556(7) Uani 1 1 d . . . . .
H31A H 0.929988 0.567716 0.848571 0.083 Uiso 1 1 calc GR . . . .
H31B H 1.010989 0.400026 0.833418 0.083 Uiso 1 1 calc GR . . . .
H31C H 0.928879 0.341987 0.872495 0.083 Uiso 1 1 calc GR . . . .
C32 C 0.8592(2) 0.1305(4) 0.77800(13) 0.0565(7) Uani 1 1 d . . . . .
H32A H 0.843058 0.053040 0.809117 0.085 Uiso 1 1 calc GR . . . .
H32B H 0.931558 0.095706 0.772447 0.085 Uiso 1 1 calc GR . . . .
H32C H 0.806507 0.097032 0.744857 0.085 Uiso 1 1 calc GR . . . .
C33 C 0.86479(18) 0.4946(4) 0.74052(9) 0.0456(6) Uani 1 1 d . . . . .
H33A H 0.814008 0.448165 0.707961 0.068 Uiso 1 1 calc GR . . . .
H33B H 0.938325 0.484841 0.733801 0.068 Uiso 1 1 calc GR . . . .
H33C H 0.848999 0.636219 0.748342 0.068 Uiso 1 1 calc GR . . . .
C34 C 0.33101(16) 0.0956(3) 0.90795(7) 0.0264(4) Uani 1 1 d . . . . .
C35 C 0.27224(17) 0.2474(4) 0.93021(9) 0.0355(5) Uani 1 1 d . . . . .
H35 H 0.302248 0.379359 0.937065 0.043 Uiso 1 1 calc R . . . .
C36 C 0.16955(19) 0.2057(4) 0.94240(10) 0.0429(6) Uani 1 1 d . . . . .
H36 H 0.130715 0.308922 0.956915 0.051 Uiso 1 1 calc R . . . .
C37 C 0.12587(18) 0.0085(4) 0.93264(9) 0.0394(5) Uani 1 1 d . . . . .
C38 C 0.1818(2) -0.1440(4) 0.91081(11) 0.0454(6) Uani 1 1 d . . . . .
H38 H 0.151570 -0.275725 0.904051 0.055 Uiso 1 1 calc R . . . .
C39 C 0.28415(19) -0.0995(3) 0.89888(10) 0.0393(5) Uani 1 1 d . . . . .
H39 H 0.322401 -0.203655 0.884388 0.047 Uiso 1 1 calc R . . . .
C40 C 0.62988(18) 0.6005(3) 0.88946(8) 0.0323(5) Uani 1 1 d . . . . .
H40A H 0.700673 0.624715 0.880312 0.048 Uiso 1 1 calc GR . . . .
H40B H 0.635620 0.608159 0.929314 0.048 Uiso 1 1 calc GR . . . .
H40C H 0.579148 0.703900 0.871706 0.048 Uiso 1 1 calc GR . . . .
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
C9 O2 C10 120.78(16) . . ?
C8 N1 C1 114.08(15) . . ?
C8 N1 C9 121.07(15) . . ?
C9 N1 C1 124.47(15) . . ?
N1 C1 C2 111.37(15) . . ?
N1 C1 C6 102.63(14) . . ?
N1 C1 C20 109.73(15) . . ?
C2 C1 C6 111.43(15) . . ?
C20 C1 C2 112.38(16) . . ?
C20 C1 C6 108.85(15) . . ?
C3 C2 C1 111.06(16) . . ?
C4 C3 C2 112.99(15) . . ?
O4 C4 C3 122.40(17) . . ?
O4 C4 C5 122.38(18) . . ?
C3 C4 C5 115.22(16) . . ?
C4 C5 C6 110.79(16) . . ?
C14 C5 C4 110.23(15) . . ?
C14 C5 C6 114.23(16) . . ?
C5 C6 C1 114.26(15) . . ?
C7 C6 C1 105.54(15) . . ?
C7 C6 C5 111.28(16) . . ?
C8 C7 C6 106.83(15) . . ?
O3 C8 N1 126.74(18) . . ?
O3 C8 C7 125.60(18) . . ?
N1 C8 C7 107.65(15) . . ?
O1 C9 O2 125.71(19) . . ?
O1 C9 N1 124.82(18) . . ?
O2 C9 N1 109.47(16) . . ?
O2 C10 C11 110.6(2) . . ?
O2 C10 C12 108.8(2) . . ?
O2 C10 C13 102.1(2) . . ?
C11 C10 C13 109.5(3) . . ?
C12 C10 C11 113.2(3) . . ?
C12 C10 C13 112.1(3) . . ?
C15 C14 C5 119.50(18) . . ?
C15 C14 C19 117.94(19) . . ?
C19 C14 C5 122.45(18) . . ?
C14 C15 C16 121.6(2) . . ?
C17 C16 C15 118.9(2) . . ?
C16 C17 Cl1 119.8(2) . . ?
C16 C17 C18 121.1(2) . . ?
C18 C17 Cl1 119.0(2) . . ?
C17 C18 C19 119.0(2) . . ?
C18 C19 C14 121.3(2) . . ?
C29 O7 C30 120.69(15) . . ?
C28 N2 C21 113.65(15) . . ?
C29 N2 C21 124.52(15) . . ?
C29 N2 C28 121.56(15) . . ?
N2 C21 C22 110.60(15) . . ?
N2 C21 C26 102.06(14) . . ?
N2 C21 C40 111.08(15) . . ?
C22 C21 C26 111.82(15) . . ?
C40 C21 C22 112.24(16) . . ?
C40 C21 C26 108.59(16) . . ?
C23 C22 C21 111.19(16) . . ?
C24 C23 C22 112.51(16) . . ?
O6 C24 C23 122.43(17) . . ?
O6 C24 C25 122.25(18) . . ?
C23 C24 C25 115.32(16) . . ?
C24 C25 C26 110.21(16) . . ?
C34 C25 C24 109.92(15) . . ?
C34 C25 C26 115.00(16) . . ?
C25 C26 C21 113.61(15) . . ?
C27 C26 C21 104.38(14) . . ?
C27 C26 C25 111.86(16) . . ?
C28 C27 C26 106.39(15) . . ?
O5 C28 N2 126.59(18) . . ?
O5 C28 C27 126.15(18) . . ?
N2 C28 C27 107.22(15) . . ?
O7 C29 N2 109.46(15) . . ?
O8 C29 O7 125.93(18) . . ?
O8 C29 N2 124.61(17) . . ?
O7 C30 C31 101.95(18) . . ?
O7 C30 C32 108.58(18) . . ?
O7 C30 C33 110.98(18) . . ?
C32 C30 C31 111.7(2) . . ?
C33 C30 C31 109.9(2) . . ?
C33 C30 C32 113.2(2) . . ?
C35 C34 C25 122.57(18) . . ?
C39 C34 C25 119.56(19) . . ?
C39 C34 C35 117.69(19) . . ?
C36 C35 C34 121.2(2) . . ?
C37 C36 C35 119.1(2) . . ?
C36 C37 Cl2 119.50(19) . . ?
C38 C37 Cl2 119.53(19) . . ?
C38 C37 C36 121.0(2) . . ?
C37 C38 C39 119.2(2) . . ?
C34 C39 C38 121.9(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
Cl1 C17 1.747(2) . ?
O1 C9 1.196(2) . ?
O2 C9 1.338(2) . ?
O2 C10 1.472(2) . ?
O3 C8 1.206(2) . ?
O4 C4 1.208(2) . ?
N1 C1 1.497(2) . ?
N1 C8 1.394(2) . ?
N1 C9 1.399(2) . ?
C1 C2 1.537(3) . ?
C1 C6 1.567(3) . ?
C1 C20 1.533(3) . ?
C2 C3 1.527(3) . ?
C3 C4 1.497(3) . ?
C4 C5 1.531(2) . ?
C5 C6 1.546(3) . ?
C5 C14 1.519(3) . ?
C6 C7 1.526(2) . ?
C7 C8 1.502(3) . ?
C10 C11 1.498(4) . ?
C10 C12 1.498(4) . ?
C10 C13 1.506(4) . ?
C14 C15 1.389(3) . ?
C14 C19 1.392(3) . ?
C15 C16 1.391(3) . ?
C16 C17 1.373(4) . ?
C17 C18 1.387(4) . ?
C18 C19 1.387(3) . ?
Cl2 C37 1.750(2) . ?
O5 C28 1.206(2) . ?
O6 C24 1.207(2) . ?
O7 C29 1.344(2) . ?
O7 C30 1.473(2) . ?
O8 C29 1.201(2) . ?
N2 C21 1.502(2) . ?
N2 C28 1.395(2) . ?
N2 C29 1.394(2) . ?
C21 C22 1.535(3) . ?
C21 C26 1.566(3) . ?
C21 C40 1.529(3) . ?
C22 C23 1.526(3) . ?
C23 C24 1.500(3) . ?
C24 C25 1.533(2) . ?
C25 C26 1.546(3) . ?
C25 C34 1.516(3) . ?
C26 C27 1.526(3) . ?
C27 C28 1.502(3) . ?
C30 C31 1.517(3) . ?
C30 C32 1.513(3) . ?
C30 C33 1.510(3) . ?
C34 C35 1.391(3) . ?
C34 C39 1.385(3) . ?
C35 C36 1.390(3) . ?
C36 C37 1.384(4) . ?
C37 C38 1.368(4) . ?
C38 C39 1.387(3) . ?
