#------------------------------------------------------------------------------
#$Date: 2021-10-04 02:47:18 +0300 (Mon, 04 Oct 2021) $
#$Revision: 269521 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/48/1564802.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_1564802
loop_
_publ_author_name
'Luo, Xiaowei'
'Cai, Guodi'
'Guo, Yinfeng'
'Gao, Chenghai'
'Huang, Weifeng'
'Zhang, Zhenhua'
'Lu, Humu'
'Liu, Kai'
'Chen, Jianghe'
'Xiong, Xiaofeng'
'Lei, Jinping'
'Zhou, Xuefeng'
'Wang, Junjian'
'Liu, Yonghong'
_publ_section_title
;
 Exploring Marine-Derived Ascochlorins as Novel Human Dihydroorotate
 Dehydrogenase Inhibitors for Treatment of Triple-Negative Breast Cancer.
;
_journal_issue                   18
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              13918
_journal_page_last               13932
_journal_paper_doi               10.1021/acs.jmedchem.1c01402
_journal_volume                  64
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H29 Cl O5'
_chemical_formula_sum            'C23 H29 Cl O5'
_chemical_formula_weight         420.91
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.884(2)
_cell_angle_beta                 100.853(2)
_cell_angle_gamma                93.813(3)
_cell_formula_units_Z            2
_cell_length_a                   6.1316(2)
_cell_length_b                   11.2090(3)
_cell_length_c                   16.0507(3)
_cell_measurement_reflns_used    9364
_cell_measurement_temperature    99.9(8)
_cell_measurement_theta_max      73.4980
_cell_measurement_theta_min      4.7680
_cell_volume                     1080.58(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (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      99.9(8)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -22.00  86.00   0.50    1.80    --    0.00  57.00 -90.00  216
  2  ω     64.00  91.00   0.50    1.80    --   40.00  69.00  91.81   54
  3  ω     14.00  57.00   0.50    1.80    --   40.00  69.00  91.81   86
  4  ω     17.00  49.00   0.50    1.80    --   44.00  72.00 -59.60   64
  5  ω    -34.00  68.00   0.50    6.00    --   48.00 -52.00 112.97  204
  6  ω     32.00  83.00   0.50    6.00    --   56.00  75.00 -35.03  102
  7  ω     31.00  56.00   0.50    6.00    --   56.00  70.00 132.27   50
  8  ω     75.00 117.00   0.50    6.00    --   56.00  73.00  22.13   84
  9  ω     29.00  55.00   0.50    6.00    --   56.00  73.00  22.13   52
 10  ω     32.00  59.00   0.50    6.00    --   56.00  75.00 142.88   54
 11  ω     86.00 115.00   0.50    6.00    --   56.00  75.00 -35.03   58
 12  ω     33.00  58.00   0.50    6.00    --   60.00  74.00  69.46   50
 13  ω     39.00  70.00   0.50    6.00    --   64.00  75.00 -85.91   62
 14  ω     36.00  75.00   0.50    6.00    --   64.00  74.00 171.73   78
 15  ω    103.00 133.00   0.50    6.00    --   64.00  75.00-161.53   60
 16  ω     37.00  74.00   0.50    6.00    --   64.00  75.00-161.53   74
 17  ω     43.00  70.00   0.50    6.00    --   68.00  73.00  79.07   54
 18  ω     42.00  78.00   0.50    6.00    --   68.00  73.00 127.03   72
 19  ω     40.00  80.00   0.50    6.00    --   68.00  75.00-137.52   80
 20  ω     45.00  79.00   0.50    6.00    --   72.00  75.00  19.15   68
 21  ω     94.00 134.00   0.50    6.00    --   80.00  71.00 -61.22   80
 22  ω     54.00  95.00   0.50    6.00    --   80.00  74.00  95.52   82
 23  ω     54.00  83.00   0.50    6.00    --   80.00  71.00 -61.22   58
 24  ω    136.00 169.00   0.50    6.00    --   80.00  74.00  95.52   66
 25  ω    113.00 180.00   0.50    6.00    --   92.00  69.00 -37.62  134
 26  ω     66.00 106.00   0.50    6.00    --   92.00  69.00 -37.62   80
 27  ω     13.00  58.00   0.50    6.00    --   95.20 -82.00 150.00   90
 28  ω      6.00 126.00   0.50    6.00    --   95.20 -82.00   0.00  240
 29  ω     82.00 185.00   0.50    6.00    --   95.20  45.00  90.00  206
 30  ω     73.00 110.00   0.50    6.00    --   95.20  61.00-180.00   74
 31  ω     13.00 100.00   0.50    6.00    --   95.20 -82.00 -90.00  174
 32  ω    152.00 180.00   0.50    6.00    --   95.20  61.00 150.00   56
 33  ω     72.00 184.00   0.50    6.00    --   95.20  61.00-120.00  224
 34  ω     73.00 145.00   0.50    6.00    --   95.20  61.00 150.00  144
 35  ω     60.00 126.00   0.50    6.00    --   95.20 -82.00  90.00  132
 36  ω     29.00 126.00   0.50    6.00    --   95.20 -82.00 -60.00  194
 37  ω     76.00 122.00   0.50    6.00    --   95.20  61.00  30.00   92
 38  ω    129.00 154.00   0.50    6.00    --   95.20  61.00 120.00   50
 39  ω     75.00 104.00   0.50    6.00    --   95.20  61.00 120.00   58
 40  ω     66.00  92.00   0.50    6.00    --   95.20 -61.00  30.00   52
 41  ω    130.00 184.00   0.50    6.00    --   95.20  70.00   3.66  108
 42  ω     29.00  57.00   0.50    6.00    --   95.20 -61.00  30.00   56
 43  ω     72.00 100.00   0.50    6.00    --   95.20  70.00   3.66   56
 44  ω    129.00 183.00   0.50    6.00    --   95.20  73.00 148.72  108
 45  ω     77.00 183.00   0.50    6.00    --   95.20  60.00 -65.41  212
 46  ω    133.00 158.00   0.50    6.00    --   95.20  74.00-106.58   50
 47  ω     68.00 125.00   0.50    6.00    --   95.20  74.00-106.58  114
 48  ω     69.00  96.00   0.50    6.00    --   95.20  73.00 148.72   54
 49  ω    117.00 167.00   0.50    6.00    --   95.20  61.00  60.00  100
 50  ω     72.00 113.00   0.50    6.00    --   95.20  61.00  60.00   82
 51  ω     67.00 175.00   0.50    6.00    --   95.20  74.00 -18.79  216
 52  ω     72.00 178.00   0.50    6.00    --   95.20  61.00-150.00  212
 53  ω     91.00 118.00   0.50    6.00    --   95.20 -82.00 150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1154991000
_diffrn_orient_matrix_UB_12      0.1182931000
_diffrn_orient_matrix_UB_13      -0.0046259000
_diffrn_orient_matrix_UB_21      0.0476327000
_diffrn_orient_matrix_UB_22      0.0184577000
_diffrn_orient_matrix_UB_23      -0.0899670000
_diffrn_orient_matrix_UB_31      -0.2239761000
_diffrn_orient_matrix_UB_32      -0.0682280000
_diffrn_orient_matrix_UB_33      -0.0379902000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22591
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.306
_diffrn_reflns_theta_min         3.954
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (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    1.294
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 2710 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     537
_refine_ls_number_reflns         8105
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0915P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.868
_reflns_number_gt                6767
_reflns_number_total             8105
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jm1c01402_si_010.cif
_cod_data_source_block           luoxiaowei_lxw_as41_collect2
_cod_database_code               1564802
_shelx_shelxl_version_number     2014/7
_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   0.914
_shelx_estimated_absorpt_t_min   0.712
_reflns_odcompleteness_completeness 99.48
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C16'(H16'), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C9'(H9'A,H9'B), C17'(H17C,H17D), C13'(H13C,H13D), C12(H12A,H12B), C12'(H12C,
 H12D), C17(H17A,H17B), C13(H13A,H13B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C8'(H8'), C10'(H10'), C8(H8), C14'(H14')
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C23(H23A,H23B,H23C), C20(H20A,H20B,H20C), C20'(H20D,H20E,
 H20F), C23'(H23D,H23E,H23F), C7'(H7'A,H7'B,H7'C), C22(H22A,H22B,H22C),
 C21(H21A,H21B,H21C), C21'(H21D,H21E,H21F), C22'(H22D,H22E,H22F)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O3'(H3'), O2'(H2')
;
_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 2.021
_oxdiff_exptl_absorpt_empirical_full_min 0.436
loop_
_space_group_symop_operation_xyz
'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_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 1.14958(19) 0.45853(10) 0.20582(7) 0.0434(3) Uani 1 1 d . . . . .
Cl1' Cl -0.0665(2) 0.50272(11) 0.79791(8) 0.0459(3) Uani 1 1 d . . . . .
O5' O 0.2317(6) 0.1289(3) 0.9616(2) 0.0386(8) Uani 1 1 d . . . . .
O2 O 1.0677(6) 0.7394(3) 0.5058(2) 0.0404(8) Uani 1 1 d . . . . .
H2 H 0.9556 0.7172 0.5239 0.061 Uiso 1 1 calc GR . . . .
O3 O 1.4433(6) 0.6633(3) 0.2850(2) 0.0379(8) Uani 1 1 d . . . . .
H3 H 1.4393 0.6163 0.2450 0.057 Uiso 1 1 calc GR . . . .
O3' O -0.3738(6) 0.3042(3) 0.7133(2) 0.0389(8) Uani 1 1 d . . . . .
H3' H -0.3640 0.3461 0.7564 0.058 Uiso 1 1 calc GR . . . .
O1' O 0.3216(6) 0.3778(3) 0.4700(2) 0.0380(8) Uani 1 1 d . . . . .
O4 O 0.5869(6) 0.5877(3) 0.1356(2) 0.0440(9) Uani 1 1 d . . . . .
O2' O -0.0244(6) 0.2453(3) 0.4828(2) 0.0386(8) Uani 1 1 d . . . . .
H2' H 0.0881 0.2672 0.4649 0.058 Uiso 1 1 calc GR . . . .
O1 O 0.7281(6) 0.6055(3) 0.5212(2) 0.0435(9) Uani 1 1 d . . . . .
O5 O 0.8971(7) 0.8034(3) 0.0415(2) 0.0450(9) Uani 1 1 d . . . . .
O4' O 0.5509(7) 0.3475(4) 0.8754(2) 0.0498(10) Uani 1 1 d . . . . .
C9' C -0.3754(8) 0.1762(4) 0.5624(3) 0.0342(10) Uani 1 1 d . . . . .
H9'A H -0.5157 0.1902 0.5791 0.041 Uiso 1 1 calc R . . . .
H9'B H -0.3996 0.1739 0.5008 0.041 Uiso 1 1 calc R . . . .
C4' C -0.2068(8) 0.3387(4) 0.6722(3) 0.0327(11) Uani 1 1 d . . . . .
C5 C 1.1161(8) 0.5358(4) 0.2967(3) 0.0333(11) Uani 1 1 d . . . . .
C2' C -0.0303(8) 0.3081(4) 0.5549(3) 0.0323(10) Uani 1 1 d . . . . .
C3' C -0.2049(8) 0.2768(4) 0.5967(3) 0.0320(10) Uani 1 1 d . . . . .
C15 C 1.0815(9) 0.9472(4) 0.1497(3) 0.0355(11) Uani 1 1 d . . . . .
C6' C 0.1273(9) 0.4650(4) 0.6613(3) 0.0346(11) Uani 1 1 d . . . . .
C1' C 0.1349(8) 0.4021(4) 0.5852(3) 0.0330(11) Uani 1 1 d . . . . .
C10 C 1.3143(8) 0.9239(4) 0.3918(3) 0.0342(10) Uani 1 1 d . . . . .
H10 H 1.1658 0.9313 0.3949 0.041 Uiso 1 1 calc R . . . .
C11 C 1.4191(8) 1.0147(4) 0.3592(3) 0.0349(10) Uani 1 1 d . . . . .
C3 C 1.2560(8) 0.7029(4) 0.3955(3) 0.0315(10) Uani 1 1 d . . . . .
C19 C 0.7634(9) 0.6913(5) 0.0307(3) 0.0379(11) Uani 1 1 d . . . . .
C14 C 1.0662(9) 1.0502(4) 0.1885(3) 0.0409(11) Uani 1 1 d . . . . .
H14 H 0.9226 1.0721 0.1886 0.049 Uiso 1 1 calc R . . . .
C17' C 0.2670(9) 0.1862(5) 0.8255(3) 0.0379(11) Uani 1 1 d . . . . .
H17C H 0.3510 0.1270 0.8033 0.045 Uiso 1 1 calc R . . . .
H17D H 0.1897 0.2304 0.7788 0.045 Uiso 1 1 calc R . . . .
C6 C 0.9420(9) 0.5046(4) 0.3373(3) 0.0343(11) Uani 1 1 d . . . . .
C16' C 0.1042(8) 0.1276(5) 0.8761(3) 0.0360(10) Uani 1 1 d . . . . .
H16' H -0.0218 0.1774 0.8745 0.043 Uiso 1 1 calc R . . . .
C1 C 0.9256(8) 0.5742(4) 0.4096(3) 0.0347(11) Uani 1 1 d . . . . .
C18 C 0.7121(9) 0.6689(5) 0.1192(3) 0.0364(11) Uani 1 1 d . . . . .
C4 C 1.2730(8) 0.6328(4) 0.3256(3) 0.0322(10) Uani 1 1 d . . . . .
C2 C 1.0810(8) 0.6719(4) 0.4373(3) 0.0335(10) Uani 1 1 d . . . . .
C13' C -0.2918(9) -0.1357(5) 0.7623(3) 0.0427(11) Uani 1 1 d . . . . .
H13C H -0.4392 -0.1498 0.7756 0.051 Uiso 1 1 calc R . . . .
H13D H -0.2034 -0.2004 0.7852 0.051 Uiso 1 1 calc R . . . .
C8' C 0.3067(8) 0.4311(4) 0.5366(3) 0.0360(11) Uani 1 1 d . . . . .
H8' H 0.4121 0.4935 0.5566 0.043 Uiso 1 1 calc R . . . .
C7 C 0.7770(10) 0.4003(5) 0.3027(4) 0.0432(13) Uani 1 1 d . . . . .
H7A H 0.6889 0.4213 0.2497 0.065 Uiso 1 1 calc GR . . . .
H7B H 0.6815 0.3822 0.3425 0.065 Uiso 1 1 calc GR . . . .
H7C H 0.8564 0.3316 0.2941 0.065 Uiso 1 1 calc GR . . . .
C19' C 0.3746(9) 0.2363(5) 0.9767(3) 0.0410(12) Uani 1 1 d . . . . .
C23 C 1.6588(9) 1.0178(5) 0.3508(3) 0.0424(12) Uani 1 1 d . . . . .
H23A H 1.7498 1.0565 0.4003 0.064 Uiso 1 1 calc GR . . . .
H23B H 1.6788 1.0614 0.3015 0.064 Uiso 1 1 calc GR . . . .
H23C H 1.7013 0.9376 0.3453 0.064 Uiso 1 1 calc GR . . . .
C15' C 0.0186(8) 0.0024(5) 0.8483(3) 0.0373(11) Uani 1 1 d . . . . .
C10' C -0.2985(8) 0.0584(4) 0.5952(3) 0.0327(10) Uani 1 1 d . . . . .
H10' H -0.1521 0.0435 0.5932 0.039 Uiso 1 1 calc R . . . .
C12 C 1.2975(10) 1.1246(4) 0.3291(3) 0.0411(11) Uani 1 1 d . . . . .
H12A H 1.3860 1.1954 0.3545 0.049 Uiso 1 1 calc R . . . .
H12B H 1.1573 1.1217 0.3490 0.049 Uiso 1 1 calc R . . . .
C5' C -0.0451(9) 0.4314(4) 0.7028(3) 0.0355(11) Uani 1 1 d . . . . .
C12' C -0.3102(9) -0.1350(5) 0.6652(3) 0.0401(11) Uani 1 1 d . . . . .
H12C H -0.1624 -0.1359 0.6519 0.048 Uiso 1 1 calc R . . . .
H12D H -0.3959 -0.2068 0.6401 0.048 Uiso 1 1 calc R . . . .
C20 C 0.9062(10) 0.5970(5) 0.0050(4) 0.0487(13) Uani 1 1 d . . . . .
H20A H 0.9582 0.6208 -0.0455 0.073 Uiso 1 1 calc GR . . . .
H20B H 0.8195 0.5220 -0.0058 0.073 Uiso 1 1 calc GR . . . .
H20C H 1.0314 0.5886 0.0499 0.073 Uiso 1 1 calc GR . . . .
C8 C 0.7488(9) 0.5482(5) 0.4575(4) 0.0390(12) Uani 1 1 d . . . . .
H8 H 0.6455 0.4843 0.4388 0.047 Uiso 1 1 calc R . . . .
C14' C -0.1866(9) -0.0195(5) 0.8031(3) 0.0413(11) Uani 1 1 d . . . . .
H14' H -0.2750 0.0452 0.7960 0.050 Uiso 1 1 calc R . . . .
C17 C 0.8321(9) 0.7672(4) 0.1778(3) 0.0375(11) Uani 1 1 d . . . . .
H17A H 0.9702 0.7417 0.2102 0.045 Uiso 1 1 calc R . . . .
H17B H 0.7403 0.7935 0.2167 0.045 Uiso 1 1 calc R . . . .
C20' C 0.5884(10) 0.2089(7) 1.0353(4) 0.0583(16) Uani 1 1 d . . . . .
H20D H 0.5554 0.1819 1.0884 0.087 Uiso 1 1 calc GR . . . .
H20E H 0.6874 0.2799 1.0451 0.087 Uiso 1 1 calc GR . . . .
H20F H 0.6579 0.1475 1.0096 0.087 Uiso 1 1 calc GR . . . .
C16 C 0.8763(9) 0.8662(4) 0.1177(3) 0.0378(11) Uani 1 1 d . . . . .
H16 H 0.7468 0.9143 0.1059 0.045 Uiso 1 1 calc R . . . .
C11' C -0.4191(8) -0.0275(4) 0.6271(3) 0.0350(10) Uani 1 1 d . . . . .
C13 C 1.2504(10) 1.1360(5) 0.2323(3) 0.0465(12) Uani 1 1 d . . . . .
H13A H 1.2120 1.2169 0.2187 0.056 Uiso 1 1 calc R . . . .
H13B H 1.3847 1.1223 0.2109 0.056 Uiso 1 1 calc R . . . .
C18' C 0.4150(9) 0.2681(5) 0.8890(3) 0.0390(11) Uani 1 1 d . . . . .
C23' C -0.6608(9) -0.0210(5) 0.6313(3) 0.0420(12) Uani 1 1 d . . . . .
H23D H -0.7081 0.0559 0.6130 0.063 Uiso 1 1 calc GR . . . .
H23E H -0.6808 -0.0322 0.6887 0.063 Uiso 1 1 calc GR . . . .
H23F H -0.7478 -0.0825 0.5950 0.063 Uiso 1 1 calc GR . . . .
C7' C 0.2957(10) 0.5664(5) 0.6964(4) 0.0448(13) Uani 1 1 d . . . . .
H7'A H 0.4362 0.5526 0.6811 0.067 Uiso 1 1 calc GR . . . .
H7'B H 0.3130 0.5707 0.7571 0.067 Uiso 1 1 calc GR . . . .
H7'C H 0.2450 0.6403 0.6732 0.067 Uiso 1 1 calc GR . . . .
C22 C 1.2970(9) 0.8996(5) 0.1395(4) 0.0486(13) Uani 1 1 d . . . . .
H22A H 1.3191 0.9111 0.0825 0.073 Uiso 1 1 calc GR . . . .
H22B H 1.2936 0.8158 0.1511 0.073 Uiso 1 1 calc GR . . . .
H22C H 1.4168 0.9413 0.1785 0.073 Uiso 1 1 calc GR . . . .
C9 C 1.4143(8) 0.8106(4) 0.4243(3) 0.0343(10) Uani 1 1 d . . . . .
H9A H 1.4496 0.8149 0.4858 0.041 Uiso 1 1 calc R . . . .
H9B H 1.5516 0.8024 0.4037 0.041 Uiso 1 1 calc R . . . .
C21 C 0.5507(10) 0.7005(6) -0.0331(4) 0.0512(14) Uani 1 1 d . . . . .
H21A H 0.4639 0.7593 -0.0134 0.077 Uiso 1 1 calc GR . . . .
H21B H 0.4671 0.6243 -0.0399 0.077 Uiso 1 1 calc GR . . . .
H21C H 0.5859 0.7237 -0.0867 0.077 Uiso 1 1 calc GR . . . .
C21' C 0.2551(11) 0.3349(5) 1.0117(4) 0.0526(14) Uani 1 1 d . . . . .
H21D H 0.1311 0.3550 0.9695 0.079 Uiso 1 1 calc GR . . . .
H21E H 0.3563 0.4044 1.0265 0.079 Uiso 1 1 calc GR . . . .
H21F H 0.2025 0.3077 1.0613 0.079 Uiso 1 1 calc GR . . . .
C22' C 0.1793(9) -0.0941(5) 0.8721(4) 0.0468(12) Uani 1 1 d . . . . .
H22D H 0.3293 -0.0591 0.8812 0.070 Uiso 1 1 calc GR . . . .
H22E H 0.1582 -0.1534 0.8269 0.070 Uiso 1 1 calc GR . . . .
H22F H 0.1521 -0.1309 0.9231 0.070 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'
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' O5' C16' 109.3(4) . . ?
C2 O2 H2 109.5 . . ?
C4 O3 H3 109.5 . . ?
C4' O3' H3' 109.5 . . ?
C2' O2' H2' 109.5 . . ?
C16 O5 C19 111.4(4) . . ?
H9'A C9' H9'B 108.1 . . ?
C3' C9' H9'A 109.5 . . ?
C3' C9' H9'B 109.5 . . ?
C10' C9' H9'A 109.5 . . ?
C10' C9' H9'B 109.5 . . ?
C10' C9' C3' 110.7(4) . . ?
O3' C4' C3' 115.9(5) . . ?
O3' C4' C5' 122.9(4) . . ?
C3' C4' C5' 121.2(4) . . ?
C6 C5 Cl1 121.2(4) . . ?
C6 C5 C4 122.2(4) . . ?
C4 C5 Cl1 116.6(4) . . ?
O2' C2' C3' 116.9(5) . . ?
O2' C2' C1' 120.7(4) . . ?
C3' C2' C1' 122.4(4) . . ?
C4' C3' C9' 122.5(4) . . ?
C4' C3' C2' 116.9(5) . . ?
C2' C3' C9' 120.5(4) . . ?
C14 C15 C16 120.3(4) . . ?
C14 C15 C22 123.8(5) . . ?
C22 C15 C16 115.8(4) . . ?
C1' C6' C7' 122.2(5) . . ?
C5' C6' C1' 117.2(5) . . ?
C5' C6' C7' 120.6(5) . . ?
C2' C1' C8' 118.9(4) . . ?
C6' C1' C2' 119.6(4) . . ?
C6' C1' C8' 121.5(5) . . ?
C11 C10 H10 117.0 . . ?
C11 C10 C9 126.0(4) . . ?
C9 C10 H10 117.0 . . ?
C10 C11 C23 123.8(4) . . ?
C10 C11 C12 120.4(4) . . ?
C23 C11 C12 115.7(4) . . ?
C4 C3 C2 117.2(5) . . ?
C4 C3 C9 121.9(4) . . ?
C2 C3 C9 120.9(4) . . ?
O5 C19 C18 103.7(4) . . ?
O5 C19 C20 107.3(4) . . ?
O5 C19 C21 111.4(4) . . ?
C20 C19 C18 111.2(4) . . ?
C21 C19 C18 110.5(4) . . ?
C21 C19 C20 112.4(5) . . ?
C15 C14 H14 115.9 . . ?
C15 C14 C13 128.2(5) . . ?
C13 C14 H14 115.9 . . ?
H17C C17' H17D 109.0 . . ?
C16' C17' H17C 111.1 . . ?
C16' C17' H17D 111.1 . . ?
C18' C17' H17C 111.1 . . ?
C18' C17' H17D 111.1 . . ?
C18' C17' C16' 103.5(4) . . ?
C5 C6 C1 117.1(5) . . ?
C5 C6 C7 119.8(5) . . ?
C1 C6 C7 123.1(5) . . ?
O5' C16' C17' 103.4(4) . . ?
O5' C16' H16' 109.3 . . ?
O5' C16' C15' 109.9(4) . . ?
C17' C16' H16' 109.3 . . ?
C15' C16' C17' 115.4(4) . . ?
C15' C16' H16' 109.3 . . ?
C6 C1 C8 121.5(5) . . ?
C2 C1 C6 120.4(4) . . ?
C2 C1 C8 118.1(5) . . ?
O4 C18 C19 124.5(5) . . ?
O4 C18 C17 127.6(5) . . ?
C17 C18 C19 107.8(4) . . ?
O3 C4 C5 121.8(4) . . ?
O3 C4 C3 117.0(5) . . ?
C3 C4 C5 121.1(4) . . ?
O2 C2 C3 116.8(4) . . ?
O2 C2 C1 121.3(4) . . ?
C3 C2 C1 122.0(4) . . ?
H13C C13' H13D 108.0 . . ?
C12' C13' H13C 109.4 . . ?
C12' C13' H13D 109.4 . . ?
C14' C13' H13C 109.4 . . ?
C14' C13' H13D 109.4 . . ?
C14' C13' C12' 111.3(4) . . ?
O1' C8' C1' 123.9(5) . . ?
O1' C8' H8' 118.1 . . ?
C1' C8' H8' 118.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O5' C19' C20' 108.5(4) . . ?
O5' C19' C18' 103.6(4) . . ?
O5' C19' C21' 110.0(4) . . ?
C20' C19' C18' 111.5(4) . . ?
C20' C19' C21' 113.1(5) . . ?
C18' C19' C21' 109.7(4) . . ?
C11 C23 H23A 109.5 . . ?
C11 C23 H23B 109.5 . . ?
C11 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C16' C15' C22' 116.3(4) . . ?
C14' C15' C16' 120.3(4) . . ?
C14' C15' C22' 123.3(5) . . ?
C9' C10' H10' 116.6 . . ?
C11' C10' C9' 126.7(4) . . ?
C11' C10' H10' 116.6 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C11 C12 C13 113.7(4) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C4' C5' Cl1' 116.8(4) . . ?
C6' C5' Cl1' 120.5(4) . . ?
C6' C5' C4' 122.7(4) . . ?
C13' C12' H12C 109.2 . . ?
C13' C12' H12D 109.2 . . ?
H12C C12' H12D 107.9 . . ?
C11' C12' C13' 112.0(4) . . ?
C11' C12' H12C 109.2 . . ?
C11' C12' H12D 109.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C8 C1 124.0(5) . . ?
O1 C8 H8 118.0 . . ?
C1 C8 H8 118.0 . . ?
C13' C14' H14' 116.1 . . ?
C15' C14' C13' 127.9(5) . . ?
C15' C14' H14' 116.1 . . ?
C18 C17 H17A 111.1 . . ?
C18 C17 H17B 111.1 . . ?
C18 C17 C16 103.3(4) . . ?
H17A C17 H17B 109.1 . . ?
C16 C17 H17A 111.1 . . ?
C16 C17 H17B 111.1 . . ?
C19' C20' H20D 109.5 . . ?
C19' C20' H20E 109.5 . . ?
C19' C20' H20F 109.5 . . ?
H20D C20' H20E 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
O5 C16 C15 110.5(4) . . ?
O5 C16 C17 104.1(4) . . ?
O5 C16 H16 109.2 . . ?
C15 C16 C17 114.5(4) . . ?
C15 C16 H16 109.2 . . ?
C17 C16 H16 109.2 . . ?
C10' C11' C12' 119.9(4) . . ?
C10' C11' C23' 123.8(4) . . ?
C12' C11' C23' 116.2(4) . . ?
C14 C13 C12 113.0(4) . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
O4' C18' C17' 127.5(5) . . ?
O4' C18' C19' 124.2(5) . . ?
C17' C18' C19' 108.4(5) . . ?
C11' C23' H23D 109.5 . . ?
C11' C23' H23E 109.5 . . ?
C11' C23' H23F 109.5 . . ?
H23D C23' H23E 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 109.5 . . ?
C6' C7' H7'A 109.5 . . ?
C6' C7' H7'B 109.5 . . ?
C6' C7' H7'C 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
C15 C22 H22A 109.5 . . ?
C15 C22 H22B 109.5 . . ?
C15 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C9 C3 111.0(4) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C3 C9 H9A 109.4 . . ?
C3 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19' C21' H21D 109.5 . . ?
C19' C21' H21E 109.5 . . ?
C19' C21' H21F 109.5 . . ?
H21D C21' H21E 109.5 . . ?
H21D C21' H21F 109.5 . . ?
H21E C21' H21F 109.5 . . ?
C15' C22' H22D 109.5 . . ?
C15' C22' H22E 109.5 . . ?
C15' C22' H22F 109.5 . . ?
H22D C22' H22E 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 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 C5 1.737(5) . ?
Cl1' C5' 1.743(5) . ?
O5' C16' 1.446(5) . ?
O5' C19' 1.431(7) . ?
O2 H2 0.8200 . ?
O2 C2 1.343(6) . ?
O3 H3 0.8200 . ?
O3 C4 1.358(6) . ?
O3' H3' 0.8200 . ?
O3' C4' 1.357(6) . ?
O1' C8' 1.239(6) . ?
O4 C18 1.215(6) . ?
O2' H2' 0.8200 . ?
O2' C2' 1.352(6) . ?
O1 C8 1.229(7) . ?
O5 C19 1.443(7) . ?
O5 C16 1.432(6) . ?
O4' C18' 1.229(6) . ?
C9' H9'A 0.9700 . ?
C9' H9'B 0.9700 . ?
C9' C3' 1.508(7) . ?
C9' C10' 1.501(6) . ?
C4' C3' 1.390(7) . ?
C4' C5' 1.402(7) . ?
C5 C6 1.380(7) . ?
C5 C4 1.415(7) . ?
C2' C3' 1.396(7) . ?
C2' C1' 1.425(7) . ?
C15 C14 1.321(7) . ?
C15 C16 1.504(8) . ?
C15 C22 1.493(7) . ?
C6' C1' 1.411(7) . ?
C6' C5' 1.386(7) . ?
C6' C7' 1.510(8) . ?
C1' C8' 1.448(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.334(7) . ?
C10 C9 1.505(6) . ?
C11 C23 1.499(7) . ?
C11 C12 1.521(7) . ?
C3 C4 1.384(7) . ?
C3 C2 1.397(7) . ?
C3 C9 1.507(7) . ?
C19 C18 1.532(7) . ?
C19 C20 1.517(7) . ?
C19 C21 1.510(7) . ?
C14 H14 0.9300 . ?
C14 C13 1.493(8) . ?
C17' H17C 0.9700 . ?
C17' H17D 0.9700 . ?
C17' C16' 1.523(7) . ?
C17' C18' 1.488(8) . ?
C6 C1 1.412(7) . ?
C6 C7 1.519(8) . ?
C16' H16' 0.9800 . ?
C16' C15' 1.496(8) . ?
C1 C2 1.411(7) . ?
C1 C8 1.460(7) . ?
C18 C17 1.497(8) . ?
C13' H13C 0.9700 . ?
C13' H13D 0.9700 . ?
C13' C12' 1.542(7) . ?
C13' C14' 1.498(8) . ?
C8' H8' 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C19' C20' 1.515(7) . ?
C19' C18' 1.519(7) . ?
C19' C21' 1.523(8) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C15' C14' 1.334(7) . ?
C15' C22' 1.516(7) . ?
C10' H10' 0.9300 . ?
C10' C11' 1.342(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.535(7) . ?
C12' H12C 0.9700 . ?
C12' H12D 0.9700 . ?
C12' C11' 1.499(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C8 H8 0.9300 . ?
C14' H14' 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C16 1.525(7) . ?
C20' H20D 0.9600 . ?
C20' H20E 0.9600 . ?
C20' H20F 0.9600 . ?
C16 H16 0.9800 . ?
C11' C23' 1.502(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C23' H23D 0.9600 . ?
C23' H23E 0.9600 . ?
C23' H23F 0.9600 . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21' H21D 0.9600 . ?
C21' H21E 0.9600 . ?
C21' H21F 0.9600 . ?
C22' H22D 0.9600 . ?
C22' H22E 0.9600 . ?
C22' H22F 0.9600 . ?
