#------------------------------------------------------------------------------
#$Date: 2020-06-05 14:28:54 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252912 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157484.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_7157484
loop_
_publ_author_name
'Cui, Hao'
'Li, Ke'
'Wang, Yue'
'Song, Manman'
'Wang, Congcong'
'Wei, Donghui'
'Li, Er-Qing'
'Duan, Zheng'
'Mathey, François'
_publ_section_title
;
 Copper(i)/Ganphos catalysis: enantioselective synthesis of diverse
 spirooxindoles using iminoesters and alkyl substituted
 methyleneindolinones.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3740
_journal_page_last               3746
_journal_paper_doi               10.1039/d0ob00546k
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H23 Cl N2 O3'
_chemical_formula_sum            'C22 H23 Cl N2 O3'
_chemical_formula_weight         398.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc23mtn7
_audit_creation_date             2019-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-24 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.944(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.1998(14)
_cell_length_b                   12.3700(6)
_cell_length_c                   9.5879(6)
_cell_measurement_reflns_used    6811
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0840
_cell_measurement_theta_min      4.1430
_cell_volume                     2487.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_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    -62.00 -37.00   1.00    1.50    --  -33.50 178.00 120.00   25
  2  ω    -47.00  -7.00   1.00    1.50    --  -33.50 -77.00   0.00   40
  3  ω    -85.00 -48.00   1.00    1.50    --  -33.50 -77.00 -30.00   37
  4  ω    -61.00 -36.00   1.00    1.50    --  -33.50 178.00-180.00   25
  5  ω   -105.00 -80.00   1.00    1.50    --  -33.50 178.00-180.00   25
  6  ω     14.00 107.00   1.00    1.50    --   36.47  37.00-150.00   93
  7  ω     74.00 100.00   1.00    1.50    --   36.47 178.00 -90.00   26
  8  ω     51.00 106.00   1.00    1.50    --   36.47  37.00 120.00   55
  9  ω     57.00 104.00   1.00    1.50    --   36.47 178.00   0.00   47
 10  ω     68.00 102.00   1.00    1.50    --   36.47 178.00 120.00   34
 11  ω     62.00 110.00   1.00    1.50    --   36.47 178.00  60.00   48
 12  ω     61.00  96.00   1.00    7.50    --  108.00-111.00 120.00   35
 13  ω     38.00 110.00   1.00    7.50    --  108.00 -94.00  30.00   72
 14  ω     42.00 137.00   1.00    7.50    --  108.00 -77.00-180.00   95
 15  ω     39.00 127.00   1.00    7.50    --  108.00 -30.00  60.00   88
 16  ω     88.00 177.00   1.00    6.00    --  108.00  30.00-120.00   89
 17  ω    152.00 177.00   1.00    6.00    --  108.00  45.00-120.00   25
 18  ω    109.00 135.00   1.00    6.00    --  108.00 111.00  60.00   26
 19  ω     39.00  90.00   1.00    6.00    --  108.00 -77.00 120.00   51
 20  ω     27.00  56.00   1.00    1.00    --   36.47  24.00 -78.00   29
 21  ω    -15.00  19.00   1.00    1.00    --    0.00 -57.00   0.00   34
 22  ω      7.00  32.00   1.00    1.00    --   36.47  19.00 120.00   25
 23  ω     54.00  80.00   1.00    1.00    --   36.47  57.00  30.00   26
 24  ω     41.00  67.00   1.00    1.00    --   36.47  37.00 120.00   26
 25  ω     57.00  82.00   1.00    1.00    --   36.47 178.00 150.00   25
 26  ω     69.00 105.00   1.00    1.00    --   36.47  57.00   0.00   36
 27  ω     76.00 105.00   1.00    1.00    --   36.47  77.00 120.00   29
 28  ω      0.00  31.00   1.00    1.00    --   36.47  91.00  -2.60   31
 29  ω     66.00  92.00   1.00    1.00    --   36.47  19.00 120.00   26
 30  ω     35.00  61.00   1.00    1.00    --   36.47  57.00 150.00   26
 31  ω     32.00  63.00   1.00    1.00    --   36.47  77.00  60.00   31
 32  ω     42.00 100.00   1.00    1.00    --   36.47  77.00  30.00   58
 33  ω     -9.00  16.00   1.00    1.00    --   36.47 108.00  58.07   25
 34  ω     35.00  61.00   1.00    1.00    --   36.47  57.00   0.00   26
 35  ω      9.00  34.00   1.00    1.00    --   36.47  77.00  30.00   25
 36  ω     24.00  50.00   1.00    1.00    --   36.47  57.00 120.00   26
 37  ω     84.00 110.00   1.00    1.00    --   36.47 178.00  90.00   26
 38  ω     14.00  40.00   1.00    1.00    --   36.47  77.00 120.00   26
 39  ω     45.00  71.00   1.00    1.00    --   36.47  57.00 -30.00   26
 40  ω     19.00  44.00   1.00    1.00    --   36.47  57.00-180.00   25
 41  ω     58.00  84.00   1.00    1.00    --   36.47 178.00-120.00   26
 42  ω    130.00 156.00   1.00    6.00    --  108.00  30.00 120.00   26
 43  ω     87.00 143.00   1.00    6.00    --  108.00  30.00  60.00   56
 44  ω     88.00 114.00   1.00    6.00    --  108.00  61.00   0.00   26
 45  ω     88.00 114.00   1.00    6.00    --  108.00  61.00 -30.00   26
 46  ω     79.00 104.00   1.00    6.00    --  108.00  77.00 -60.00   25
 47  ω     83.00 109.00   1.00    6.00    --  108.00  77.00  90.00   26
 48  ω     86.00 112.00   1.00    6.00    --  108.00  30.00 120.00   26
 49  ω     89.00 115.00   1.00    6.00    --  108.00  61.00  60.00   26
 50  ω     79.00 104.00   1.00    6.00    --  108.00  77.00  60.00   25
 51  ω    153.00 178.00   1.00    6.00    --  108.00  30.00 -30.00   25
 52  ω     79.00 104.00   1.00    6.00    --  108.00  77.00   0.00   25
 53  ω     88.00 114.00   1.00    6.00    --  108.00  45.00  90.00   26
 54  ω     88.00 118.00   1.00    6.00    --  108.00  61.00  30.00   30
 55  ω     81.00 106.00   1.00    6.00    --  108.00  74.00  28.64   25
 56  ω     88.00 114.00   1.00    6.00    --  108.00  61.00  90.00   26
 57  ω    129.00 155.00   1.00    6.00    --  108.00  77.00 -30.00   26
 58  ω     82.00 133.00   1.00    6.00    --  108.00  30.00  30.00   51
 59  ω     79.00 104.00   1.00    6.00    --  108.00  77.00 -30.00   25
 60  ω     84.00 123.00   1.00    6.00    --  108.00  30.00   0.00   39
 61  ω     88.00 124.00   1.00    6.00    --  108.00  45.00   0.00   36
 62  ω     87.00 117.00   1.00    6.00    --  108.00  42.00  -9.89   30
 63  ω     88.00 114.00   1.00    6.00    --  108.00  61.00 -60.00   26
 64  ω     79.00 105.00   1.00    6.00    --  108.00  77.00  30.00   26
 65  ω     89.00 137.00   1.00    6.00    --  108.00  45.00 -30.00   48
 66  ω     89.00 132.00   1.00    6.00    --  108.00  45.00  30.00   43
 67  ω     79.00 105.00   1.00    6.00    --  108.00  77.00   5.88   26
 68  ω     83.00 129.00   1.00    6.00    --  108.00  30.00 -30.00   46
 69  ω     83.00 129.00   1.00    6.00    --  108.00  30.00  90.00   46
 70  ω     24.00  50.00   1.00    1.00    --   36.47  57.00 120.00   26
 71  ω     51.00  77.00   1.00    1.00    --   36.47  57.00   0.00   26
 72  ω     41.00  67.00   1.00    1.00    --   36.47  37.00 120.00   26
 73  ω     69.00  95.00   1.00    1.00    --   36.47  57.00  30.00   26
 74  ω     24.00  50.00   1.00    1.00    --   36.47  57.00-180.00   26
 75  ω     84.00 110.00   1.00    6.00    --  108.00  30.00   0.00   26
 76  ω     89.00 115.00   1.00    6.00    --  108.00  45.00 -30.00   26
 77  ω     91.00 117.00   1.00    6.00    --  108.00  61.00  60.00   26
 78  ω     87.00 113.00   1.00    6.00    --  108.00  42.00 110.61   26
 79  ω     85.00 111.00   1.00    6.00    --  108.00  37.00 115.89   26
 80  ω     69.00  95.00   1.00    1.00    --   36.47  57.00  30.00   26
 81  ω     41.00  67.00   1.00    1.00    --   36.47  37.00 120.00   26
 82  ω     24.00  50.00   1.00    1.00    --   36.47  57.00-180.00   26
 83  ω     51.00  77.00   1.00    1.00    --   36.47  57.00   0.00   26
 84  ω     24.00  50.00   1.00    1.00    --   36.47  57.00 120.00   26
 85  ω     91.00 117.00   1.00    6.00    --  108.00  61.00  60.00   26
 86  ω     89.00 115.00   1.00    6.00    --  108.00  45.00 -30.00   26
 87  ω     84.00 110.00   1.00    6.00    --  108.00  30.00   0.00   26
 88  ω     24.00  50.00   1.00    1.00    --   36.47  57.00 120.00   26
 89  ω     69.00  95.00   1.00    1.00    --   36.47  57.00  30.00   26
 90  ω     24.00  50.00   1.00    1.00    --   36.47  57.00-180.00   26
 91  ω     41.00  67.00   1.00    1.00    --   36.47  37.00 120.00   26
 92  ω     51.00  77.00   1.00    1.00    --   36.47  57.00   0.00   26
 93  ω     84.00 110.00   1.00    6.00    --  108.00  30.00   0.00   26
 94  ω     89.00 115.00   1.00    6.00    --  108.00  45.00 -30.00   26
 95  ω     91.00 117.00   1.00    6.00    --  108.00  61.00  60.00   26
 96  ω     86.00 112.00   1.00    6.00    --  108.00  39.00  82.69   26
 97  ω     69.00  95.00   1.00    1.00    --   36.47  57.00  30.00   26
 98  ω     41.00  67.00   1.00    1.00    --   36.47  37.00 120.00   26
 99  ω     24.00  50.00   1.00    1.00    --   36.47  57.00-180.00   26
100  ω     51.00  77.00   1.00    1.00    --   36.47  57.00   0.00   26
101  ω     24.00  50.00   1.00    1.00    --   36.47  57.00 120.00   26
102  ω     91.00 117.00   1.00    6.00    --  108.00  61.00  60.00   26
103  ω     89.00 115.00   1.00    6.00    --  108.00  45.00 -30.00   26
104  ω     84.00 110.00   1.00    6.00    --  108.00  30.00   0.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0401215000
_diffrn_orient_matrix_UB_12      0.0387657000
_diffrn_orient_matrix_UB_13      -0.1755796000
_diffrn_orient_matrix_UB_21      -0.0589977000
_diffrn_orient_matrix_UB_22      0.0085798000
_diffrn_orient_matrix_UB_23      0.0207410000
_diffrn_orient_matrix_UB_31      0.0174342000
_diffrn_orient_matrix_UB_32      0.1180243000
_diffrn_orient_matrix_UB_33      0.0561157000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17070
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         4.217
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.526
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.065
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1510 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4120
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0880P)²+0.1735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1291
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.842
_reflns_Friedel_fraction_max     0.842
_reflns_number_gt                3851
_reflns_number_total             4120
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00546k2.cif
_cod_data_source_block           201909229
_cod_depositor_comments          'Adding full bibliography for 7157484.cif.'
_cod_database_code               7157484
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20O4Cl1
_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   0.875
_shelx_estimated_absorpt_t_min   0.781
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2
 0.87 with sigma of 0.02
 N1-H1A
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7), C16(H16), C17(H17), C18(H18)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15)
3.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
;
_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 1.321
_oxdiff_exptl_absorpt_empirical_full_min 0.882
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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
C1 C 0.13048(15) 0.3235(3) 0.3768(4) 0.0570(7) Uani 1 1 d . . . . .
H1 H 0.1258 0.3277 0.2747 0.068 Uiso 1 1 calc R . . . .
C2 C 0.08820(15) 0.3761(3) 0.4117(5) 0.0648(8) Uani 1 1 d . . . . .
C3 C 0.09403(18) 0.3752(4) 0.5608(5) 0.0769(10) Uani 1 1 d . . . . .
H3 H 0.0653 0.4125 0.5809 0.092 Uiso 1 1 calc R . . . .
C4 C 0.1432(2) 0.3180(5) 0.6795(5) 0.0871(13) Uani 1 1 d . . . . .
H4 H 0.1482 0.3161 0.7822 0.105 Uiso 1 1 calc R . . . .
C5 C 0.18577(17) 0.2625(4) 0.6484(4) 0.0672(8) Uani 1 1 d . . . . .
H5 H 0.2188 0.2233 0.7304 0.081 Uiso 1 1 calc R . . . .
C6 C 0.17976(12) 0.2647(2) 0.4978(3) 0.0472(6) Uani 1 1 d . . . . .
C7 C 0.22752(13) 0.2028(2) 0.4709(3) 0.0448(6) Uani 1 1 d . . . . .
H7 H 0.2402 0.1403 0.5434 0.054 Uiso 1 1 calc R . . . .
C8 C 0.29180(12) 0.2650(2) 0.5154(3) 0.0425(5) Uani 1 1 d . . . . .
C9 C 0.28357(13) 0.3877(3) 0.5046(3) 0.0473(6) Uani 1 1 d . . . . .
C10 C 0.34050(12) 0.2485(2) 0.6900(3) 0.0454(6) Uani 1 1 d . . . . .
C11 C 0.35587(13) 0.3484(3) 0.7660(3) 0.0525(7) Uani 1 1 d . . . . .
C12 C 0.39905(19) 0.3579(4) 0.9287(4) 0.0740(10) Uani 1 1 d . . . . .
H12 H 0.4090 0.4252 0.9789 0.089 Uiso 1 1 calc R . . . .
C13 C 0.42676(18) 0.2653(5) 1.0140(4) 0.0822(12) Uani 1 1 d . . . . .
H13 H 0.4566 0.2705 1.1230 0.099 Uiso 1 1 calc R . . . .
C14 C 0.41148(17) 0.1650(4) 0.9424(4) 0.0769(11) Uani 1 1 d . . . . .
H14 H 0.4306 0.1035 1.0034 0.092 Uiso 1 1 calc R . . . .
C15 C 0.36753(15) 0.1556(3) 0.7791(4) 0.0589(8) Uani 1 1 d . . . . .
H15 H 0.3565 0.0879 0.7304 0.071 Uiso 1 1 calc R . . . .
C16 C 0.30690(14) 0.2242(2) 0.3827(3) 0.0491(6) Uani 1 1 d . . . . .
H16 H 0.2937 0.2817 0.3021 0.059 Uiso 1 1 calc R . . . .
C17 C 0.26049(15) 0.1300(3) 0.3029(3) 0.0514(6) Uani 1 1 d . . . . .
H17 H 0.2790 0.0633 0.3637 0.062 Uiso 1 1 calc R . . . .
C18 C 0.37762(18) 0.2009(3) 0.4412(4) 0.0646(8) Uani 1 1 d . . . . .
H18 H 0.3931 0.1480 0.5288 0.078 Uiso 1 1 calc R . . . .
C19 C 0.41735(19) 0.3044(4) 0.5061(6) 0.0849(12) Uani 1 1 d . . . . .
H19A H 0.3991 0.3604 0.4266 0.127 Uiso 1 1 calc GR . . . .
H19B H 0.4603 0.2906 0.5301 0.127 Uiso 1 1 calc GR . . . .
H19C H 0.4176 0.3268 0.6023 0.127 Uiso 1 1 calc GR . . . .
C20 C 0.3861(2) 0.1534(4) 0.3051(6) 0.0866(12) Uani 1 1 d . . . . .
H20A H 0.3663 0.0835 0.2761 0.130 Uiso 1 1 calc GR . . . .
H20B H 0.4307 0.1466 0.3409 0.130 Uiso 1 1 calc GR . . . .
H20C H 0.3664 0.2004 0.2133 0.130 Uiso 1 1 calc GR . . . .
C21 C 0.24098(19) 0.1130(3) 0.1266(4) 0.0675(9) Uani 1 1 d . . . . .
C22 C 0.2308(5) -0.0137(7) -0.0670(7) 0.165(4) Uani 1 1 d . . . . .
H22A H 0.1880 0.0095 -0.1396 0.248 Uiso 1 1 calc GR . . . .
H22B H 0.2342 -0.0901 -0.0788 0.248 Uiso 1 1 calc GR . . . .
H22C H 0.2597 0.0239 -0.0912 0.248 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.02496(5) 0.44943(12) 0.25850(18) 0.1034(5) Uani 1 1 d . . . . .
N1 N 0.32214(13) 0.4295(2) 0.6539(3) 0.0547(6) Uani 1 1 d D . . . .
H1A H 0.3230(16) 0.495(2) 0.675(4) 0.050(9) Uiso 1 1 d D . . . .
N2 N 0.20300(12) 0.1585(2) 0.3094(3) 0.0498(5) Uani 1 1 d D . . . .
H2 H 0.1824(15) 0.207(2) 0.241(4) 0.049(8) Uiso 1 1 d D . . . .
O1 O 0.24940(11) 0.43953(19) 0.3835(3) 0.0594(5) Uani 1 1 d . . . . .
O2 O 0.2205(2) 0.1819(3) 0.0280(3) 0.1012(11) Uani 1 1 d . . . . .
O3 O 0.2468(2) 0.0099(3) 0.0975(4) 0.0989(11) 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_
_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
C2 C1 H1 120.8 . . ?
C6 C1 H1 120.8 . . ?
C6 C1 C2 118.4(3) . . ?
C1 C2 Cl1 118.8(3) . . ?
C3 C2 C1 123.1(3) . . ?
C3 C2 Cl1 118.2(3) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.0(3) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 122.4(2) . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 C7 118.6(3) . . ?
C6 C7 H7 105.9 . . ?
C6 C7 C8 115.9(2) . . ?
C8 C7 H7 105.9 . . ?
N2 C7 C6 115.5(2) . . ?
N2 C7 H7 105.9 . . ?
N2 C7 C8 106.9(2) . . ?
C9 C8 C7 112.7(2) . . ?
C9 C8 C16 109.8(2) . . ?
C10 C8 C7 110.5(2) . . ?
C10 C8 C9 102.3(2) . . ?
C10 C8 C16 119.2(2) . . ?
C16 C8 C7 102.6(2) . . ?
N1 C9 C8 108.0(2) . . ?
O1 C9 C8 126.2(3) . . ?
O1 C9 N1 125.8(3) . . ?
C11 C10 C8 108.6(2) . . ?
C15 C10 C8 131.7(3) . . ?
C15 C10 C11 119.6(3) . . ?
C10 C11 N1 109.6(2) . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 N1 128.9(3) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 118.0(4) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.7(3) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.1(4) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 119.0(4) . . ?
C10 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C8 C16 H16 106.8 . . ?
C17 C16 C8 103.9(2) . . ?
C17 C16 H16 106.8 . . ?
C17 C16 C18 116.4(3) . . ?
C18 C16 C8 115.5(2) . . ?
C18 C16 H16 106.8 . . ?
C16 C17 H17 109.8 . . ?
C21 C17 C16 113.7(3) . . ?
C21 C17 H17 109.8 . . ?
N2 C17 C16 105.7(2) . . ?
N2 C17 H17 109.8 . . ?
N2 C17 C21 107.7(3) . . ?
C16 C18 H18 108.4 . . ?
C19 C18 C16 110.5(3) . . ?
C19 C18 H18 108.4 . . ?
C19 C18 C20 110.0(3) . . ?
C20 C18 C16 110.9(3) . . ?
C20 C18 H18 108.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 C17 124.1(4) . . ?
O2 C21 O3 124.8(3) . . ?
O3 C21 C17 111.0(3) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
C9 N1 C11 111.5(3) . . ?
C9 N1 H1A 123(2) . . ?
C11 N1 H1A 125(2) . . ?
C7 N2 C17 104.1(2) . . ?
C7 N2 H2 109(2) . . ?
C17 N2 H2 110(2) . . ?
C21 O3 C22 115.0(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
C1 H1 0.9300 . ?
C1 C2 1.386(5) . ?
C1 C6 1.384(4) . ?
C2 C3 1.365(6) . ?
C2 Cl1 1.754(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.363(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(4) . ?
C6 C7 1.512(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.592(4) . ?
C7 N2 1.461(4) . ?
C8 C9 1.527(4) . ?
C8 C10 1.504(4) . ?
C8 C16 1.572(3) . ?
C9 N1 1.362(4) . ?
C9 O1 1.219(4) . ?
C10 C11 1.388(4) . ?
C10 C15 1.386(4) . ?
C11 C12 1.383(4) . ?
C11 N1 1.397(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.391(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9800 . ?
C16 C17 1.532(4) . ?
C16 C18 1.539(4) . ?
C17 H17 0.9800 . ?
C17 C21 1.526(4) . ?
C17 N2 1.466(4) . ?
C18 H18 0.9800 . ?
C18 C19 1.533(6) . ?
C18 C20 1.535(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O2 1.182(5) . ?
C21 O3 1.328(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 O3 1.453(6) . ?
N1 H1A 0.84(2) . ?
N2 H2 0.84(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N2 0.84(2) 2.14(3) 2.955(4) 164(3) 4_556
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
C1 C2 C3 C4 -1.3(6) . . . . ?
C1 C6 C7 C8 94.0(3) . . . . ?
C1 C6 C7 N2 -32.1(4) . . . . ?
C2 C1 C6 C5 -1.4(5) . . . . ?
C2 C1 C6 C7 178.8(3) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 0.6(7) . . . . ?
C4 C5 C6 C1 0.2(6) . . . . ?
C4 C5 C6 C7 -180.0(4) . . . . ?
C5 C6 C7 C8 -85.8(3) . . . . ?
C5 C6 C7 N2 148.1(3) . . . . ?
C6 C1 C2 C3 2.0(6) . . . . ?
C6 C1 C2 Cl1 -179.2(2) . . . . ?
C6 C7 C8 C9 -26.0(3) . . . . ?
C6 C7 C8 C10 87.8(3) . . . . ?
C6 C7 C8 C16 -144.1(2) . . . . ?
C6 C7 N2 C17 165.2(2) . . . . ?
C7 C8 C9 N1 118.0(2) . . . . ?
C7 C8 C9 O1 -63.1(3) . . . . ?
C7 C8 C10 C11 -119.0(2) . . . . ?
C7 C8 C10 C15 57.9(4) . . . . ?
C7 C8 C16 C17 -11.2(2) . . . . ?
C7 C8 C16 C18 -139.9(3) . . . . ?
C8 C7 N2 C17 34.5(3) . . . . ?
C8 C9 N1 C11 -0.1(3) . . . . ?
C8 C10 C11 C12 179.0(3) . . . . ?
C8 C10 C11 N1 -1.4(3) . . . . ?
C8 C10 C15 C14 -178.9(3) . . . . ?
C8 C16 C17 C21 150.8(3) . . . . ?
C8 C16 C17 N2 32.8(3) . . . . ?
C8 C16 C18 C19 -62.1(4) . . . . ?
C8 C16 C18 C20 175.6(3) . . . . ?
C9 C8 C10 C11 1.3(3) . . . . ?
C9 C8 C10 C15 178.1(3) . . . . ?
C9 C8 C16 C17 -131.2(2) . . . . ?
C9 C8 C16 C18 100.0(3) . . . . ?
C10 C8 C9 N1 -0.7(3) . . . . ?
C10 C8 C9 O1 178.1(3) . . . . ?
C10 C8 C16 C17 111.3(3) . . . . ?
C10 C8 C16 C18 -17.5(4) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C10 C11 N1 C9 1.0(3) . . . . ?
C11 C10 C15 C14 -2.3(4) . . . . ?
C11 C12 C13 C14 -1.5(6) . . . . ?
C12 C11 N1 C9 -179.5(3) . . . . ?
C12 C13 C14 C15 0.8(6) . . . . ?
C13 C14 C15 C10 1.1(5) . . . . ?
C15 C10 C11 C12 1.7(4) . . . . ?
C15 C10 C11 N1 -178.7(3) . . . . ?
C16 C8 C9 N1 -128.2(2) . . . . ?
C16 C8 C9 O1 50.6(3) . . . . ?
C16 C8 C10 C11 122.6(3) . . . . ?
C16 C8 C10 C15 -60.5(4) . . . . ?
C16 C17 C21 O2 -52.2(5) . . . . ?
C16 C17 C21 O3 131.2(3) . . . . ?
C16 C17 N2 C7 -42.4(3) . . . . ?
C17 C16 C18 C19 175.6(3) . . . . ?
C17 C16 C18 C20 53.3(4) . . . . ?
C17 C21 O3 C22 -178.5(6) . . . . ?
C18 C16 C17 C21 -81.0(3) . . . . ?
C18 C16 C17 N2 161.0(2) . . . . ?
C21 C17 N2 C7 -164.4(3) . . . . ?
Cl1 C2 C3 C4 179.9(4) . . . . ?
N1 C11 C12 C13 -179.3(3) . . . . ?
N2 C7 C8 C9 104.3(2) . . . . ?
N2 C7 C8 C10 -141.9(2) . . . . ?
N2 C7 C8 C16 -13.8(3) . . . . ?
N2 C17 C21 O2 64.6(5) . . . . ?
N2 C17 C21 O3 -112.0(4) . . . . ?
O1 C9 N1 C11 -179.0(3) . . . . ?
O2 C21 O3 C22 4.9(8) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.154 -0.402 316.3 62.3 ?
2 0.500 0.654 0.694 316.3 62.3 ?
