#------------------------------------------------------------------------------
#$Date: 2024-04-05 01:26:09 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/28/7132818.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_7132818
loop_
_publ_author_name
'Campbell, Aaron D. G.'
'Roper, Natalie J.'
'Waddell, Paul G.'
'Wills, Corinne'
'Dixon, Casey M.'
'Denton, Ross M.'
'Ermanis, Kristaps'
'Armstrong, Roly J.'
_publ_section_title
;
 Synthesis, structure and stereodynamics of atropisomeric
 N-chloroamides.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3818
_journal_page_last               3821
_journal_paper_doi               10.1039/d4cc00268g
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C13 H18 Cl N O'
_chemical_formula_sum            'C13 H18 Cl N O'
_chemical_formula_weight         239.746
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-01-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-11-13 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                93.580(2)
_cell_angle_beta                 96.362(2)
_cell_angle_gamma                93.083(2)
_cell_formula_units_Z            2
_cell_length_a                   6.66649(19)
_cell_length_b                   9.4285(3)
_cell_length_c                   10.2117(3)
_cell_measurement_reflns_used    7636
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.8840
_cell_measurement_theta_min      4.3590
_cell_volume                     635.47(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9295
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     58.00  90.00   0.50    0.05    --   48.76 156.00 -20.00   64
  2  ω      0.00  25.00   0.50    0.05    --   38.00  97.00  91.24   50
  3  ω    -44.00 -14.00   0.50    0.05    --   10.00 128.00  93.35   60
  4  ω    -33.00  -8.00   0.50    0.05    --   14.00 116.00  24.95   50
  5  ω     15.00  40.00   0.50    0.05    --   50.00  91.00 118.39   50
  6  ω     15.00  40.00   0.50    0.05    --   50.00  92.00  57.26   50
  7  ω    -26.00  -1.00   0.50    0.05    --   18.00 108.00-135.02   50
  8  ω      8.00  37.00   0.50    0.05    --   42.00  90.00-100.38   58
  9  ω     16.00  41.00   0.50    0.05    --   50.00  90.00-114.30   50
 10  ω     24.00  90.00   0.50    0.05    --   48.76  77.00   0.00  132
 11  ω     44.00  69.00   0.50    0.05    --   70.00  76.00-108.70   50
 12  ω     70.00 113.00   0.50    0.05    --   96.11  77.00  30.00   86
 13  ω     33.00  60.00   0.50    0.05    --   58.00  76.00  91.53   54
 14  ω     33.00  59.00   0.50    0.05    --   58.00  75.00 147.44   52
 15  ω     32.00  70.00   0.50    0.05    --   54.00  77.00 174.11   76
 16  ω     87.00 112.00   0.50    0.05    --   54.00  77.00 174.11   50
 17  ω     82.00 107.00   0.50    0.05    --   96.11 156.00 -20.00   50
 18  ω    103.00 128.00   0.50    0.05    --  108.00 120.00-176.00   50
 19  ω     21.00  49.00   0.50    0.05    --   96.11 -45.00-180.00   56
 20  ω     35.00  67.00   0.50    0.05    --  108.00 -61.00-120.00   64
 21  ω     19.00  51.00   0.50    0.05    --   96.11 -45.00 -30.00   64
 22  ω     34.00  69.00   0.50    0.05    --  108.00 -61.00 120.00   70
 23  ω     39.00 106.00   0.50    0.05    --  108.00 -95.00 120.00  134
 24  ω     70.00 109.00   0.50    0.05    --  108.00-120.00  99.00   78
 25  ω     28.00 105.00   0.50    0.05    --   96.11 -95.00 -30.00  154
 26  ω     43.00  95.00   0.50    0.05    --  108.00 -95.00 -90.00  104
 27  ω     62.00  87.00   0.50    0.05    --  108.00-156.00 -57.00   50
 28  ω     57.00  82.00   0.50    0.05    --   96.11-156.00 -57.00   50
 29  ω     53.00  78.00   0.50    0.05    --   48.76-156.00 -57.00   50
 30  ω     50.00  96.00   0.50    0.05    --   48.76-120.00  99.00   92
 31  ω     17.00  47.00   0.50    0.05    --   48.76-120.00  99.00   60
 32  ω   -130.00-105.00   0.50    0.05    --  -92.01-156.00 -57.00   50
 33  ω    -83.00 -53.00   0.50    0.05    --  -49.76-156.00 -57.00   60
 34  ω   -121.00 -96.00   0.50    0.05    --  -92.01-120.00  99.00   50
 35  ω   -152.00-126.00   0.50    0.05    --  -92.01 -61.00   0.00   52
 36  ω    -93.00 -65.00   0.50    0.05    --  -92.01 -77.00-150.00   56
 37  ω    -53.00 -26.00   0.50    0.05    --  -49.76 -77.00-120.00   54
 38  ω    -49.00 -23.00   0.50    0.05    --  -49.76 -77.00 -60.00   52
 39  ω   -146.00-103.00   0.50    0.05    --  -92.01 -77.00-150.00   86
 40  ω   -109.00 -68.00   0.50    0.05    --  -92.01 -77.00 -90.00   82
 41  ω   -141.00 -70.00   0.50    0.05    --  -92.01 -77.00  90.00  142
 42  ω   -156.00 -65.00   0.50    0.05    --  -92.01 -77.00 120.00  182
 43  ω    -60.00 -35.00   0.50    0.05    --  -62.00 -77.00 154.17   50
 44  ω    -73.00 -48.00   0.50    0.05    --  -74.00 -76.00 118.28   50
 45  ω   -114.00 -88.00   0.50    0.05    --  -62.00 -77.00 154.17   52
 46  ω    -69.00 -44.00   0.50    0.05    --  -70.00 -76.00  33.99   50
 47  ω    -89.00 -53.00   0.50    0.05    --  -78.00 -76.00 -44.95   72
 48  ω    -74.00 -48.00   0.50    0.05    --  -74.00 -76.00 -87.50   52
 49  ω   -145.00 -99.00   0.50    0.05    --  -78.00 -76.00 -44.95   92
 50  ω   -148.00-112.00   0.50    0.05    --  -92.01 -77.00 -90.00   72
 51  ω    -70.00 -45.00   0.50    0.05    --  -70.00 -74.00-176.61   50
 52  ω    -63.00 -37.00   0.50    0.05    --  -62.00 -73.00 -92.56   52
 53  ω    -79.00 -52.00   0.50    0.05    --  -78.00 -75.00  13.71   54
 54  ω   -100.00 -65.00   0.50    0.05    --  -90.00 -73.00 -45.61   70
 55  ω   -145.00-106.00   0.50    0.05    --  -78.00 -75.00  13.71   78
 56  ω   -158.00-118.00   0.50    0.05    --  -90.00 -73.00 -45.61   80
 57  ω   -163.00-137.00   0.50    0.05    --  -99.00 -73.00-155.54   52
 58  ω   -102.00 -74.00   0.50    0.05    --  -99.00 -73.00-155.54   56
 59  ω    -73.00 -47.00   0.50    0.05    --  -70.00 -72.00 -31.01   52
 60  ω   -113.00 -75.00   0.50    0.05    --  -99.00 -71.00 -72.31   76
 61  ω   -154.00-116.00   0.50    0.05    --  -90.00 -71.00 -25.17   76
 62  ω   -166.00-126.00   0.50    0.05    --  -99.00 -71.00 -72.31   80
 63  ω   -103.00 -66.00   0.50    0.05    --  -90.00 -71.00 -25.17   74
 64  ω   -145.00 -76.00   0.50    0.05    --  -99.00 -70.00-131.59  138
 65  ω    -96.00 -54.00   0.50    0.05    --  -78.00 -71.00  59.40   84
 66  ω    -88.00 -55.00   0.50    0.05    --  -78.00 -69.00  71.80   66
 67  ω    -93.00 -57.00   0.50    0.05    --  -78.00 -70.00  99.66   72
 68  ω    -95.00 -66.00   0.50    0.05    --  -90.00 -71.00 132.93   58
 69  ω    -77.00 -51.00   0.50    0.05    --  -74.00 -69.00 167.34   52
 70  ω   -161.00 -69.00   0.50    0.05    --  -90.00 -67.00 168.96  184
 71  ω   -158.00 -64.00   0.50    0.05    --  -86.00 -69.00  31.60  188
 72  ω    -94.00 -65.00   0.50    0.05    --  -86.00 -63.00 139.73   58
 73  ω   -156.00-112.00   0.50    0.05    --  -86.00 -63.00 139.73   88
 74  ω    -92.00 -67.00   0.50    0.05    --  -90.00 -69.00  48.86   50
 75  ω    -94.00 -69.00   0.50    0.05    --  -90.00 -66.00 -11.62   50
 76  ω    -98.00 -73.00   0.50    0.05    --  -92.01 -61.00   0.00   50
 77  ω    -88.00 -62.00   0.50    0.05    --  -82.00 -66.00-128.43   52
 78  ω   -100.00 -67.00   0.50    0.05    --  -92.01  77.00-180.00   66
 79  ω    -63.00 -36.00   0.50    0.05    --  -92.01  77.00-180.00   54
 80  ω   -100.00 -50.00   0.50    0.05    --  -92.01 120.00-176.00  100
 81  ω    -68.00 -42.00   0.50    0.05    --  -49.76 120.00-176.00   52
 82  ω    -89.00 -64.00   0.50    0.05    --  -92.01 156.00 -20.00   50
 83  ω    -62.00 -24.00   0.50    0.05    --  -92.01  77.00  30.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1383649000
_diffrn_orient_matrix_UB_12      -0.0496893000
_diffrn_orient_matrix_UB_13      0.1171478000
_diffrn_orient_matrix_UB_21      0.1490456000
_diffrn_orient_matrix_UB_22      -0.0508641000
_diffrn_orient_matrix_UB_23      -0.0953809000
_diffrn_orient_matrix_UB_31      0.1136246000
_diffrn_orient_matrix_UB_32      0.1478062000
_diffrn_orient_matrix_UB_33      0.0181983000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.9987
_diffrn_reflns_Laue_measured_fraction_max 0.9295
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13900
_diffrn_reflns_point_group_measured_fraction_full 0.9987
_diffrn_reflns_point_group_measured_fraction_max 0.9295
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         77.60
_diffrn_reflns_theta_min         4.37
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.486
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             257.434
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.2271
_refine_diff_density_min         -0.2115
_refine_diff_density_rms         0.0370
_refine_ls_d_res_high            0.7893
_refine_ls_d_res_low             10.1247
_refine_ls_extinction_coef       0.0044(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0393
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0393
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0397P)²+0.1645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0812
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2334
_reflns_number_total             2505
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4cc00268g3.cif
_cod_data_source_block           rja230008_fa
_cod_depositor_comments
'Adding full bibliography for 7132810--7132818.cif.'
_cod_database_code               7132818
_chemical_oxdiff_formula         'C13 H18 Cl1 N1 O1'
_diffrn_oxdiff_digest_frames
;
0100b4ee7ff8f213440eb12b4ed1310cce05902c7be
;
_diffrn_oxdiff_digest_hkl
;
01de8c1636134dc45f8b1aeeae182e5593917a
;
_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 Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C3(H3a,H3b,H3c), C11(H11a,H11b,H11c), C13(H13a,H13b,H13c)
;
_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 1.572
_oxdiff_exptl_absorpt_empirical_full_min 0.671
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-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_refinement_flags_posn
Cl1 Cl -0.26171(4) 0.76762(4) 0.81072(3) 0.03805(13) Uani 1.000000 .
O1 O -0.05049(14) 0.84249(10) 1.06388(9) 0.0339(2) Uani 1.000000 .
N1 N -0.00357(15) 0.77150(12) 0.85334(11) 0.0290(2) Uani 1.000000 .
C1 C 0.06419(18) 0.82666(13) 0.98024(12) 0.0270(3) Uani 1.000000 .
C9 C 0.1269(2) 0.91309(15) 0.68977(13) 0.0338(3) Uani 1.000000 .
H9 H 0.0616(2) 0.99058(15) 0.72685(13) 0.0405(4) Uiso 1.000000 R
C6 C 0.3160(2) 0.68724(15) 0.58574(13) 0.0329(3) Uani 1.000000 .
H6 H 0.3850(2) 0.61130(15) 0.54937(13) 0.0395(4) Uiso 1.000000 R
C2 C 0.28985(19) 0.86436(14) 1.00611(13) 0.0299(3) Uani 1.000000 .
H2a H 0.36067(19) 0.80310(14) 0.94619(13) 0.0359(3) Uiso 1.000000 R
H2b H 0.31706(19) 0.96448(14) 0.98600(13) 0.0359(3) Uiso 1.000000 R
C5 C 0.20200(18) 0.66113(13) 0.68992(12) 0.0264(3) Uani 1.000000 .
C12 C 0.2840(2) 0.50618(15) 0.88167(13) 0.0364(3) Uani 1.000000 .
H12a H 0.4254(5) 0.5423(10) 0.8862(3) 0.0546(5) Uiso 1.000000 GR
H12b H 0.2135(10) 0.5657(9) 0.94168(19) 0.0546(5) Uiso 1.000000 GR
H12c H 0.2785(14) 0.4079(2) 0.9077(4) 0.0546(5) Uiso 1.000000 GR
C4 C 0.11181(18) 0.78057(14) 0.74174(12) 0.0271(3) Uani 1.000000 .
C7 C 0.3327(2) 0.81908(16) 0.53323(13) 0.0376(3) Uani 1.000000 .
H7 H 0.4107(2) 0.83124(16) 0.46186(13) 0.0452(4) Uiso 1.000000 R
C3 C 0.3736(2) 0.84575(16) 1.14814(14) 0.0385(3) Uani 1.000000 .
H3a H 0.5168(5) 0.8787(11) 1.1621(3) 0.0577(5) Uiso 1.000000 GR
H3b H 0.2983(11) 0.9016(9) 1.20809(14) 0.0577(5) Uiso 1.000000 GR
H3c H 0.3597(15) 0.7449(2) 1.1658(3) 0.0577(5) Uiso 1.000000 GR
C10 C 0.18154(19) 0.51045(14) 0.74007(12) 0.0295(3) Uani 1.000000 .
C11 C 0.2821(3) 0.40145(17) 0.65410(16) 0.0490(4) Uani 1.000000 .
H11a H 0.2220(13) 0.4017(10) 0.5621(3) 0.0736(6) Uiso 1.000000 GR
H11b H 0.4274(4) 0.4269(8) 0.6599(10) 0.0736(6) Uiso 1.000000 GR
H11c H 0.2608(17) 0.3063(3) 0.6856(8) 0.0736(6) Uiso 1.000000 GR
C8 C 0.2367(2) 0.93246(16) 0.58409(14) 0.0380(3) Uani 1.000000 .
H8 H 0.2457(2) 1.02236(16) 0.54731(14) 0.0456(4) Uiso 1.000000 R
C13 C -0.0415(2) 0.45855(15) 0.73510(16) 0.0409(3) Uani 1.000000 .
H13a H -0.1049(5) 0.5139(8) 0.8020(7) 0.0613(5) Uiso 1.000000 GR
H13b H -0.1115(4) 0.4711(11) 0.6474(4) 0.0613(5) Uiso 1.000000 GR
H13c H -0.0506(2) 0.3576(3) 0.7527(11) 0.0613(5) Uiso 1.000000 GR
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0112
0 0 -1 0.0462
0 -1 0 0.0760
1 0 0 0.0865
-1 0 0 0.0835
0 1 0 0.1070
1 1 0 0.0851
1 -1 0 0.1049
0 -1 1 0.0495
0 1 -1 0.0905
1 2 0 0.0867
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
C1 N1 Cl1 115.43(8) . . ?
C4 N1 Cl1 113.64(8) . . ?
C4 N1 C1 124.39(10) . . ?
N1 C1 O1 121.71(11) . . ?
C2 C1 O1 123.22(11) . . ?
C2 C1 N1 115.06(10) . . ?
C4 C9 H9 119.90(8) . . ?
C8 C9 H9 119.90(8) . . ?
C8 C9 C4 120.21(13) . . ?
C5 C6 H6 118.52(8) . . ?
C7 C6 H6 118.52(8) . . ?
C7 C6 C5 122.96(13) . . ?
H2a C2 C1 109.13(7) . . ?
H2b C2 C1 109.13(7) . . ?
H2b C2 H2a 107.9 . . ?
C3 C2 C1 112.35(11) . . ?
C3 C2 H2a 109.13(8) . . ?
C3 C2 H2b 109.13(7) . . ?
C4 C5 C6 114.90(12) . . ?
C10 C5 C6 120.57(11) . . ?
C10 C5 C4 124.53(11) . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
C10 C12 H12a 109.5 . . ?
C10 C12 H12b 109.5 . . ?
C10 C12 H12c 109.5 . . ?
C9 C4 N1 116.11(11) . . ?
C5 C4 N1 121.25(11) . . ?
C5 C4 C9 122.64(12) . . ?
H7 C7 C6 119.83(8) . . ?
C8 C7 C6 120.34(13) . . ?
C8 C7 H7 119.83(8) . . ?
H3a C3 C2 109.5 . . ?
H3b C3 C2 109.5 . . ?
H3b C3 H3a 109.5 . . ?
H3c C3 C2 109.5 . . ?
H3c C3 H3a 109.5 . . ?
H3c C3 H3b 109.5 . . ?
C12 C10 C5 111.54(10) . . ?
C11 C10 C5 111.38(11) . . ?
C11 C10 C12 106.79(11) . . ?
C13 C10 C5 111.01(10) . . ?
C13 C10 C12 109.06(11) . . ?
C13 C10 C11 106.86(12) . . ?
H11a C11 C10 109.5 . . ?
H11b C11 C10 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C10 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
C7 C8 C9 118.88(13) . . ?
H8 C8 C9 120.56(8) . . ?
H8 C8 C7 120.56(8) . . ?
H13a C13 C10 109.5 . . ?
H13b C13 C10 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C10 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
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 N1 1.7255(10) . ?
O1 C1 1.2154(15) . ?
N1 C1 1.3838(17) . ?
N1 C4 1.4481(15) . ?
C1 C2 1.5172(17) . ?
C9 H9 0.9500 . ?
C9 C4 1.3907(18) . ?
C9 C8 1.3854(19) . ?
C6 H6 0.9500 . ?
C6 C5 1.4007(17) . ?
C6 C7 1.388(2) . ?
C2 H2a 0.9900 . ?
C2 H2b 0.9900 . ?
C2 C3 1.5196(18) . ?
C5 C4 1.4066(17) . ?
C5 C10 1.5443(17) . ?
C12 H12a 0.9800 . ?
C12 H12b 0.9800 . ?
C12 H12c 0.9800 . ?
C12 C10 1.5330(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(2) . ?
C3 H3a 0.9800 . ?
C3 H3b 0.9800 . ?
C3 H3c 0.9800 . ?
C10 C11 1.5389(19) . ?
C10 C13 1.5346(19) . ?
C11 H11a 0.9800 . ?
C11 H11b 0.9800 . ?
C11 H11c 0.9800 . ?
C8 H8 0.9500 . ?
C13 H13a 0.9800 . ?
C13 H13b 0.9800 . ?
C13 H13c 0.9800 . ?
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
Cl1 N1 C1 O1 15.03(10) . . . . ?
Cl1 N1 C1 C2 -165.29(9) . . . . ?
Cl1 N1 C4 C9 75.68(10) . . . . ?
Cl1 N1 C4 C5 -104.16(9) . . . . ?
O1 C1 N1 C4 164.73(11) . . . . ?
O1 C1 C2 C3 31.01(14) . . . . ?
N1 C1 C2 C3 -148.67(11) . . . . ?
N1 C4 C9 C8 179.08(11) . . . . ?
N1 C4 C5 C6 -177.38(11) . . . . ?
N1 C4 C5 C10 2.73(14) . . . . ?
C9 C4 C5 C6 2.79(14) . . . . ?
C9 C4 C5 C10 -177.10(11) . . . . ?
C9 C8 C7 C6 1.19(16) . . . . ?
C6 C5 C10 C12 114.09(12) . . . . ?
C6 C5 C10 C11 -5.12(14) . . . . ?
C6 C5 C10 C13 -124.06(13) . . . . ?
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
-0.0000 0.0000 1.0000 0.1171 -0.0954 0.0182
0.0000 -0.0000 -1.0000 -0.1171 0.0954 -0.0182
-0.0000 -1.0000 0.0000 0.0497 0.0509 -0.1478
1.0000 0.0000 -0.0000 0.1384 0.1490 0.1136
-1.0000 -0.0000 0.0000 -0.1384 -0.1490 -0.1136
0.0000 1.0000 -0.0000 -0.0497 -0.0509 0.1478
1.0000 1.0000 -0.0000 0.0887 0.0982 0.2614
1.0000 -1.0000 0.0000 0.1881 0.1999 -0.0342
-0.0000 -1.0000 1.0000 0.1668 -0.0445 -0.1296
0.0000 1.0000 -1.0000 -0.1668 0.0445 0.1296
1.0000 2.0000 -0.0000 0.0390 0.0473 0.4092
