#------------------------------------------------------------------------------
#$Date: 2021-09-06 13:29:07 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268671 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/32/7243243.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_7243243
loop_
_publ_author_name
'Bereczki, Laura'
'Zodge, Amit'
'Kőrösi, Márton'
'Holczbauer, Tamás'
'De, Sourav'
'Székely, Edit'
'Bombicz, Petra'
_publ_section_title
;
 A bug in enantiomer separation: double salt formation -- diastereomeric
 and double salt structures of 1-cyclohexylethylammonium 2- and
 4-chloromandelate
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              5367
_journal_page_last               5376
_journal_paper_doi               10.1039/D1CE00145K
_journal_volume                  23
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C8 H18 N 1+, C8 H6 Cl O3 1-'
_chemical_formula_sum            'C16 H24 Cl N O3'
_chemical_formula_weight         313.81
_chemical_melting_point          420(1)
_chemical_name_common
;
(S)-(1-cyclohexylethyl)ammonium (R,S)-2-chloromandelate
;
_chemical_name_systematic
;
(S)-(1-cyclohexylethyl)ammonium (R,S)-2-(2-chlorophenyl)-2-hydroxyacetate
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-01-29 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.277(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.6370(2)
_cell_length_b                   25.3851(6)
_cell_length_c                   13.5859(3)
_cell_measurement_reflns_used    24104
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      72.300
_cell_measurement_theta_min      3.255
_cell_volume                     3323.56(13)
_computing_cell_refinement
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_collection
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_reduction
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_molecular_graphics
;
Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.
;
_computing_publication_material
;
C. F. Macrae, J. Appl. Cryst., 41, 466-470, 2008
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
;
  Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.
;
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  RAXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_unetI/netI     0.1044
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25816
_diffrn_reflns_point_group_measured_fraction_full 0.888
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.238
_diffrn_reflns_theta_min         3.253
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    2.113
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
  NUMABS, Numerical Absorption correction Program (T.Higashi, 2011)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   0.992144
_exptl_transmission_factor_min   0.972722
_refine_diff_density_max         1.429
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details
;
 Flack x determined using 2072 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.189(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     835
_refine_ls_number_reflns         25816
_refine_ls_number_restraints     235
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.1070
_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)+(0.1862P)²+5.1105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2808
_refine_ls_wR_factor_ref         0.3010
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.781
_reflns_Friedel_fraction_max     0.779
_reflns_number_gt                19821
_reflns_number_total             25816
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00145k2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7243242--7243247.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7243243
_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_min   0.973
_shelx_estimated_absorpt_t_max   0.992
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
Cl1C Cl 0.7896(4) 0.16510(15) 0.8284(2) 0.0668(12) Uani 1 1 d . . . . .
Cl1D Cl 0.6076(4) 0.16228(15) 0.3279(2) 0.0584(10) Uani 1 1 d . . . . .
Cl1B Cl 0.1069(4) 0.34407(18) 0.9110(3) 0.0725(13) Uani 1 1 d . . . . .
Cl1A Cl 0.3195(5) 0.32761(19) 1.4150(3) 0.0850(15) Uani 1 1 d . . . . .
O2D O 0.7950(9) 0.2266(4) 0.4819(6) 0.046(2) Uani 1 1 d . . . . .
O2A O 0.0635(9) 0.2675(4) 1.2633(6) 0.047(2) Uani 1 1 d . . . . .
O1A O 0.0906(9) 0.2514(3) 1.1025(5) 0.042(2) Uani 1 1 d . . . . .
O1C O 0.5984(9) 0.2483(4) 1.1383(6) 0.046(2) Uani 1 1 d . . . . .
O1D O 0.7616(9) 0.2402(4) 0.6419(7) 0.051(3) Uani 1 1 d . . . . .
O2B O 0.2959(9) 0.2774(4) 0.7616(6) 0.045(2) Uani 1 1 d . . . . .
O1B O 0.2568(9) 0.2567(4) 0.6037(6) 0.049(2) Uani 1 1 d D . . . .
O3A O 0.3448(9) 0.2960(4) 1.1015(6) 0.049(2) Uani 1 1 d . . . . .
H3A H 0.426517 0.288798 1.111769 0.073 Uiso 1 1 calc R U . . .
O2C O 0.5586(9) 0.2265(4) 0.9825(5) 0.043(2) Uani 1 1 d . . . . .
N1A N 0.7752(11) 0.2763(4) 1.2973(7) 0.042(3) Uani 1 1 d . . . . .
H1A1 H 0.861330 0.275812 1.273939 0.063 Uiso 1 1 calc R U . . .
H1A2 H 0.715957 0.267595 1.249466 0.063 Uiso 1 1 calc R U . . .
H1A3 H 0.768126 0.253215 1.346353 0.063 Uiso 1 1 calc R U . . .
O3B O -0.0016(9) 0.2925(3) 0.6101(6) 0.043(2) Uani 1 1 d . . . . .
H3B H -0.034188 0.262627 0.611149 0.064 Uiso 1 1 calc R U . . .
N1B N 0.5763(11) 0.2725(4) 0.7949(7) 0.040(3) Uani 1 1 d . . . . .
H1B1 H 0.644032 0.260980 0.756129 0.060 Uiso 1 1 calc R U . . .
H1B2 H 0.497466 0.274204 0.760627 0.060 Uiso 1 1 calc R U . . .
H1B3 H 0.565967 0.250539 0.845288 0.060 Uiso 1 1 calc R U . . .
O3D O 0.4980(9) 0.2097(4) 0.6321(5) 0.046(2) Uani 1 1 d D . . . .
H3D H 0.427853 0.226128 0.617071 0.070 Uiso 1 1 calc DR U . . .
O3C O 0.8470(9) 0.1986(4) 1.1405(6) 0.049(3) Uani 1 1 d . . . . .
H3C H 0.928307 0.205963 1.129395 0.074 Uiso 1 1 calc R U . . .
N1C N 0.2695(11) 0.2250(4) 0.9434(7) 0.043(3) Uani 1 1 d . . . . .
H1C1 H 0.353563 0.223613 0.970732 0.065 Uiso 1 1 calc R U . . .
H1C2 H 0.208492 0.236187 0.987636 0.065 Uiso 1 1 calc R U . . .
H1C3 H 0.270767 0.247149 0.892597 0.065 Uiso 1 1 calc R U . . .
N1D N 0.0786(11) 0.2212(4) 0.4533(7) 0.045(3) Uani 1 1 d . . . . .
H1D1 H 0.131982 0.233296 0.501976 0.067 Uiso 1 1 calc R U . . .
H1D2 H -0.009064 0.219654 0.473485 0.067 Uiso 1 1 calc R U . . .
H1D3 H 0.084421 0.242802 0.401862 0.067 Uiso 1 1 calc R U . . .
C1A C 0.1366(14) 0.2702(5) 1.1825(9) 0.043(3) Uani 1 1 d . . . . .
C1D C 0.7228(13) 0.2243(5) 0.5590(8) 0.036(3) Uani 1 1 d . . . . .
C2A C 0.2683(15) 0.2941(6) 1.1943(9) 0.047(4) Uani 1 1 d . . . . .
H2A H 0.322522 0.275445 1.244566 0.057 Uiso 1 1 calc R U . . .
C9C C 0.2296(14) 0.1722(5) 0.9089(8) 0.040(3) Uani 1 1 d . . . . .
H9C H 0.148100 0.176596 0.866302 0.048 Uiso 1 1 calc R U . . .
C1B C 0.2216(14) 0.2778(5) 0.6851(9) 0.038(3) Uani 1 1 d . . . . .
C9A C 0.7425(13) 0.3292(5) 1.3335(9) 0.042(3) Uani 1 1 d . . . . .
H9A H 0.665132 0.325321 1.379441 0.051 Uiso 1 1 calc R U . . .
C11A C 0.6891(14) 0.3644(5) 1.2468(9) 0.046(3) Uani 1 1 d . . . . .
H11A H 0.610618 0.345931 1.216204 0.055 Uiso 1 1 calc R U . . .
C3D C 0.5926(14) 0.1434(5) 0.5262(10) 0.046(4) Uani 1 1 d . . . . .
C1C C 0.6288(15) 0.2262(5) 1.0577(8) 0.044(4) Uani 1 1 d . . . . .
C3B C 0.0933(13) 0.3622(5) 0.7102(9) 0.040(3) Uani 1 1 d . . . . .
C2B C 0.0744(14) 0.3008(5) 0.6937(8) 0.041(3) Uani 1 1 d . . . . .
H2B H 0.026957 0.285191 0.750346 0.049 Uiso 1 1 calc R U . . .
C3A C 0.2450(14) 0.3540(6) 1.2259(10) 0.051(4) Uani 1 1 d . . . . .
C3C C 0.7423(13) 0.1416(5) 1.0193(9) 0.043(3) Uani 1 1 d . . . . .
C2D C 0.5781(13) 0.2011(5) 0.5481(8) 0.042(3) Uani 1 1 d . U . . .
H2D H 0.532018 0.218026 0.491988 0.050 Uiso 1 1 calc R U . . .
C2C C 0.7714(13) 0.1977(5) 1.0508(9) 0.041(3) Uani 1 1 d . . . . .
H2C H 0.826887 0.214874 0.999812 0.049 Uiso 1 1 calc R U . . .
C9B C 0.6130(14) 0.3270(5) 0.8333(9) 0.047(4) Uani 1 1 d . . . . .
H9B H 0.560287 0.333308 0.893646 0.056 Uiso 1 1 calc R U . . .
C8C C 0.7013(14) 0.1034(6) 1.0918(10) 0.048(4) Uani 1 1 d . . . . .
H8C H 0.694279 0.113793 1.157197 0.057 Uiso 1 1 calc R U . . .
C4D C 0.6105(14) 0.1224(5) 0.4320(10) 0.048(4) Uani 1 1 d . . . . .
C11C C 0.1856(15) 0.1372(5) 0.9955(10) 0.051(4) Uani 1 1 d . . . . .
H11C H 0.111355 0.156021 1.029759 0.061 Uiso 1 1 calc R U . . .
C9D C 0.1255(14) 0.1683(5) 0.4247(9) 0.048(3) Uani 1 1 d D . . . .
H9D H 0.061422 0.151218 0.378433 0.057 Uiso 1 1 calc R U . A 1
C4B C 0.1065(16) 0.3836(7) 0.8046(11) 0.067(5) Uani 1 1 d . . . . .
C8A C 0.2039(14) 0.3883(6) 1.1619(11) 0.052(4) Uani 1 1 d . . . . .
H8A H 0.196591 0.377371 1.096773 0.063 Uiso 1 1 calc R U . . .
C11B C 0.5695(16) 0.3683(5) 0.7564(10) 0.052(4) Uani 1 1 d . U . . .
H11B H 0.471141 0.362942 0.740865 0.063 Uiso 1 1 calc R U . . .
C13C C 0.2517(18) 0.0956(6) 1.1568(10) 0.064(5) Uani 1 1 d . . . . .
H13A H 0.180000 0.114976 1.191285 0.076 Uiso 1 1 calc R U . . .
H13B H 0.327733 0.089473 1.202415 0.076 Uiso 1 1 calc R U . . .
C4C C 0.7423(14) 0.1225(7) 0.9230(10) 0.053(4) Uani 1 1 d . . . . .
C5D C 0.6319(16) 0.0696(7) 0.4165(12) 0.065(5) Uani 1 1 d . . . . .
H5D H 0.647776 0.056710 0.353439 0.078 Uiso 1 1 calc R U . . .
C10A C 0.8604(15) 0.3508(5) 1.3905(9) 0.047(3) Uani 1 1 d . . . . .
H10A H 0.896001 0.324255 1.434074 0.070 Uiso 1 1 calc R U . . .
H10B H 0.829504 0.380536 1.428269 0.070 Uiso 1 1 calc R U . . .
H10C H 0.932128 0.361790 1.346225 0.070 Uiso 1 1 calc R U . . .
C14C C 0.1919(19) 0.0414(7) 1.1203(11) 0.070(5) Uani 1 1 d . . . . .
H14A H 0.265653 0.020621 1.091228 0.083 Uiso 1 1 calc R U . . .
H14B H 0.155106 0.021892 1.175774 0.083 Uiso 1 1 calc R U . . .
C16C C 0.1223(15) 0.0837(5) 0.9598(9) 0.049(4) Uani 1 1 d . . . . .
H16A H 0.042087 0.090576 0.918360 0.059 Uiso 1 1 calc R U . . .
H16B H 0.190315 0.064947 0.920762 0.059 Uiso 1 1 calc R U . . .
C13A C 0.7468(18) 0.4065(6) 1.0844(11) 0.067(5) Uani 1 1 d . . . . .
H13C H 0.676507 0.387339 1.047649 0.080 Uiso 1 1 calc R U . . .
H13D H 0.822493 0.414235 1.039912 0.080 Uiso 1 1 calc R U . . .
C7D C 0.6120(16) 0.0549(6) 0.5890(12) 0.063(5) Uani 1 1 d . . . . .
H7D H 0.613922 0.031909 0.642242 0.076 Uiso 1 1 calc R U . . .
C8D C 0.5922(15) 0.1070(6) 0.6039(11) 0.054(4) Uani 1 1 d . . . . .
H8D H 0.577814 0.119132 0.667627 0.065 Uiso 1 1 calc R U . . .
C12A C 0.7995(16) 0.3724(6) 1.1664(9) 0.058(4) Uani 1 1 d . . . . .
H12A H 0.881236 0.388565 1.195447 0.070 Uiso 1 1 calc R U . . .
H12B H 0.826452 0.338412 1.140091 0.070 Uiso 1 1 calc R U . . .
C4A C 0.2630(16) 0.3701(7) 1.3191(11) 0.066(5) Uani 1 1 d . . . . .
C7B C 0.1066(16) 0.4485(6) 0.6464(12) 0.062(5) Uani 1 1 d . . . . .
H7B H 0.109287 0.471274 0.592814 0.074 Uiso 1 1 calc R U . . .
C16B C 0.5854(19) 0.4223(6) 0.8013(11) 0.065(4) Uani 1 1 d . U . . .
H16C H 0.529734 0.424196 0.860476 0.078 Uiso 1 1 calc R U . . .
H16D H 0.681628 0.427458 0.820255 0.078 Uiso 1 1 calc R U . . .
C16A C 0.6350(15) 0.4181(5) 1.2836(10) 0.050(4) Uani 1 1 d . . . . .
H16I H 0.563657 0.412493 1.332588 0.059 Uiso 1 1 calc R U . . .
H16J H 0.710350 0.437455 1.314416 0.059 Uiso 1 1 calc R U . . .
C7C C 0.6731(16) 0.0535(7) 1.0679(12) 0.065(5) Uani 1 1 d . . . . .
H7C H 0.657875 0.029126 1.117791 0.078 Uiso 1 1 calc R U . . .
C14A C 0.6842(18) 0.4587(5) 1.1217(11) 0.060(4) Uani 1 1 d . . . . .
H14C H 0.757795 0.480336 1.149168 0.072 Uiso 1 1 calc R U . . .
H14D H 0.644237 0.477668 1.066339 0.072 Uiso 1 1 calc R U . . .
C6C C 0.6660(17) 0.0377(6) 0.9736(12) 0.062(4) Uani 1 1 d . . . . .
H6C H 0.636598 0.003868 0.957515 0.074 Uiso 1 1 calc R U . . .
C8B C 0.0921(16) 0.3941(6) 0.6329(12) 0.061(5) Uani 1 1 d . . . . .
H8B H 0.081724 0.380309 0.569813 0.074 Uiso 1 1 calc R U . . .
C10D C 0.2683(15) 0.1735(6) 0.3840(11) 0.060(4) Uani 1 1 d . . . . .
H10D H 0.270389 0.201715 0.337108 0.090 Uiso 1 1 calc R U . . .
H10E H 0.294166 0.141159 0.352286 0.090 Uiso 1 1 calc R U . . .
H10F H 0.332414 0.180824 0.436595 0.090 Uiso 1 1 calc R U . . .
C6D C 0.6293(18) 0.0362(7) 0.4959(15) 0.080(6) Uani 1 1 d . . . . .
H6D H 0.639524 0.000180 0.485932 0.096 Uiso 1 1 calc R U . . .
C15A C 0.5748(16) 0.4508(6) 1.1980(10) 0.061(4) Uani 1 1 d . . . . .
H15A H 0.495894 0.432618 1.169275 0.073 Uiso 1 1 calc R U . . .
H15B H 0.543297 0.484699 1.222231 0.073 Uiso 1 1 calc R U . . .
C12C C 0.3016(16) 0.1272(6) 1.0722(9) 0.054(4) Uani 1 1 d . . . . .
H12C H 0.377779 0.108817 1.040899 0.065 Uiso 1 1 calc R U . . .
H12D H 0.336453 0.160742 1.096048 0.065 Uiso 1 1 calc R U . . .
C5B C 0.124(2) 0.4372(7) 0.8214(15) 0.083(6) Uani 1 1 d . . . . .
H5B H 0.139128 0.451048 0.883848 0.100 Uiso 1 1 calc R U . . .
C7A C 0.1701(16) 0.4395(7) 1.1824(14) 0.071(5) Uani 1 1 d . . . . .
H7A H 0.140504 0.462103 1.132606 0.086 Uiso 1 1 calc R U . . .
C10C C 0.3452(15) 0.1501(6) 0.8453(9) 0.058(4) Uani 1 1 d . . . . .
H10G H 0.376008 0.176719 0.800209 0.087 Uiso 1 1 calc R U . . .
H10H H 0.311136 0.120299 0.809142 0.087 Uiso 1 1 calc R U . . .
H10I H 0.421295 0.139422 0.886541 0.087 Uiso 1 1 calc R U . . .
C6B C 0.1166(18) 0.4674(7) 0.7408(17) 0.088(7) Uani 1 1 d . . . . .
H6B H 0.118595 0.503698 0.749323 0.105 Uiso 1 1 calc R U . . .
C5C C 0.7028(18) 0.0723(7) 0.9027(12) 0.069(5) Uani 1 1 d . . . . .
H5C H 0.700942 0.061306 0.837380 0.082 Uiso 1 1 calc R U . . .
C5A C 0.235(2) 0.4207(8) 1.3493(14) 0.092(7) Uani 1 1 d . . . . .
H5A H 0.251933 0.430999 1.413989 0.111 Uiso 1 1 calc R U . . .
C15C C 0.0797(15) 0.0500(6) 1.0460(10) 0.057(4) Uani 1 1 d . . . . .
H15C H 0.001455 0.066585 1.078258 0.068 Uiso 1 1 calc R U . . .
H15D H 0.048938 0.016095 1.021437 0.068 Uiso 1 1 calc R U . . .
C14B C 0.6305(19) 0.4626(6) 0.6375(11) 0.073(5) Uani 1 1 d D U . . .
H14I H 0.607852 0.491585 0.593786 0.087 Uiso 1 1 calc R U . B 3
H14J H 0.728653 0.464293 0.653363 0.087 Uiso 1 1 calc R U . B 3
C15B C 0.5425(17) 0.4659(6) 0.7329(11) 0.066(4) Uani 1 1 d D U . . .
H15E H 0.556974 0.499741 0.764567 0.079 Uiso 1 1 calc R U . . .
H15F H 0.444773 0.462604 0.716793 0.079 Uiso 1 1 calc R U . . .
C12B C 0.650(2) 0.3646(6) 0.6621(11) 0.085(6) Uani 1 1 d D U . . .
H12E H 0.636273 0.330288 0.632326 0.102 Uiso 1 1 calc R U . C 3
H12F H 0.748233 0.369209 0.675300 0.102 Uiso 1 1 calc R U . C 3
C6A C 0.1809(18) 0.4570(7) 1.2788(15) 0.075(6) Uani 1 1 d . . . . .
H6A H 0.153893 0.490852 1.296768 0.091 Uiso 1 1 calc R U . . .
C10B C 0.7575(14) 0.3255(6) 0.8579(9) 0.053(4) Uani 1 1 d . . . . .
H10J H 0.811247 0.323809 0.798719 0.080 Uiso 1 1 calc R U . . .
H10K H 0.776288 0.295005 0.897611 0.080 Uiso 1 1 calc R U . . .
H10L H 0.781872 0.356694 0.894039 0.080 Uiso 1 1 calc R U . . .
C11D C 0.157(3) 0.1338(10) 0.5151(18) 0.039(6) Uani 0.502(19) 1 d D U P D 1
H11D H 0.247999 0.149061 0.530200 0.047 Uiso 0.502(19) 1 calc R U P D 1
C12D C 0.105(5) 0.1385(13) 0.605(2) 0.076(11) Uani 0.502(19) 1 d D U P D 1
H12G H 0.045386 0.169398 0.602941 0.091 Uiso 0.502(19) 1 calc R U P D 1
H12H H 0.182369 0.147689 0.647387 0.091 Uiso 0.502(19) 1 calc R U P D 1
C16D C 0.206(3) 0.0792(9) 0.499(2) 0.048(8) Uani 0.502(19) 1 d D U P D 1
H16E H 0.294769 0.080823 0.465236 0.058 Uiso 0.502(19) 1 calc R U P D 1
H16F H 0.141147 0.061710 0.454892 0.058 Uiso 0.502(19) 1 calc R U P D 1
C13D C 0.019(5) 0.0951(18) 0.665(3) 0.062(12) Uani 0.502(19) 1 d D U P D 1
H13E H -0.078830 0.096937 0.647031 0.075 Uiso 0.502(19) 1 calc R U P D 1
H13F H 0.027610 0.101125 0.734952 0.075 Uiso 0.502(19) 1 calc R U P D 1
C14D C 0.082(4) 0.0376(19) 0.636(3) 0.060(11) Uani 0.502(19) 1 d D U P D 1
H14E H 0.087244 0.015566 0.694228 0.072 Uiso 0.502(19) 1 calc R U P D 1
H14F H 0.021410 0.020374 0.588492 0.072 Uiso 0.502(19) 1 calc R U P D 1
C15D C 0.224(3) 0.0447(12) 0.593(2) 0.068(10) Uani 0.502(19) 1 d D U P D 1
H15G H 0.263906 0.010774 0.576122 0.082 Uiso 0.502(19) 1 calc R U P D 1
H15H H 0.284877 0.062030 0.639849 0.082 Uiso 0.502(19) 1 calc R U P D 1
C15E C 0.044(4) 0.0340(12) 0.533(2) 0.076(9) Uani 0.498(19) 1 d D U P D 2
H15I H 0.051622 -0.001312 0.506387 0.091 Uiso 0.498(19) 1 calc R U P D 2
H15J H -0.053316 0.042093 0.542420 0.091 Uiso 0.498(19) 1 calc R U P D 2
C16E C 0.109(4) 0.0732(10) 0.464(2) 0.060(8) Uani 0.498(19) 1 d D U P D 2
H16G H 0.208474 0.067801 0.462098 0.072 Uiso 0.498(19) 1 calc R U P D 2
H16H H 0.072298 0.068082 0.398053 0.072 Uiso 0.498(19) 1 calc R U P D 2
C11E C 0.079(4) 0.1278(10) 0.497(2) 0.051(8) Uani 0.498(19) 1 d D U P D 2
H11E H 0.163383 0.130306 0.537211 0.061 Uiso 0.498(19) 1 calc R U P D 2
C12E C -0.003(4) 0.1236(13) 0.575(2) 0.056(8) Uani 0.498(19) 1 d D U P D 2
H12I H -0.088981 0.107186 0.553674 0.067 Uiso 0.498(19) 1 calc R U P D 2
H12J H -0.025318 0.158871 0.597183 0.067 Uiso 0.498(19) 1 calc R U P D 2
C13E C 0.057(5) 0.0917(18) 0.664(4) 0.067(12) Uani 0.498(19) 1 d D U P D 2
H13G H -0.017649 0.084697 0.710153 0.081 Uiso 0.498(19) 1 calc R U P D 2
H13H H 0.126120 0.112779 0.697530 0.081 Uiso 0.498(19) 1 calc R U P D 2
C14E C 0.123(5) 0.0381(19) 0.631(3) 0.066(11) Uani 0.498(19) 1 d D U P D 2
H14G H 0.222843 0.040613 0.622403 0.079 Uiso 0.498(19) 1 calc R U P D 2
H14H H 0.101553 0.009401 0.675781 0.079 Uiso 0.498(19) 1 calc R U P D 2
C13B C 0.596(7) 0.4101(11) 0.589(2) 0.086(12) Uani 0.72(13) 1 d D U P E 3
H13I H 0.641474 0.407337 0.525439 0.104 Uiso 0.72(13) 1 calc R U P E 3
H13J H 0.496338 0.407014 0.578331 0.104 Uiso 0.72(13) 1 calc R U P E 3
C13F C 0.65(2) 0.417(3) 0.601(9) 0.092(19) Uani 0.28(13) 1 d D U P E 4
H13K H 0.738036 0.418607 0.567182 0.110 Uiso 0.28(13) 1 calc R U P E 4
H13L H 0.579252 0.412873 0.550051 0.110 Uiso 0.28(13) 1 calc R U P E 4
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'
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'
Cl Cl 0.3639 0.7018 '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
O1A C1A O2A 120.9(12) . . ?
O1A C1A C2A 124.7(11) . . ?
O2A C1A C2A 114.4(12) . . ?
O1D C1D O2D 124.6(12) . . ?
O1D C1D C2D 118.8(9) . . ?
O2D C1D C2D 116.6(10) . . ?
C1A C2A O3A 111.8(11) . . ?
C1A C2A C3A 108.2(11) . . ?
O3A C2A C3A 105.8(10) . . ?
N1C C9C C10C 109.1(10) . . ?
N1C C9C C11C 110.9(9) . . ?
C10C C9C C11C 115.3(11) . . ?
O2B C1B O1B 123.9(12) . . ?
O2B C1B C2B 117.5(10) . . ?
O1B C1B C2B 118.3(12) . . ?
N1A C9A C10A 110.6(11) . . ?
N1A C9A C11A 109.9(10) . . ?
C10A C9A C11A 115.6(11) . . ?
C12A C11A C16A 110.3(11) . . ?
C12A C11A C9A 112.5(11) . . ?
C16A C11A C9A 111.8(10) . . ?
C4D C3D C8D 116.1(13) . . ?
C4D C3D C2D 124.4(11) . . ?
C8D C3D C2D 119.5(12) . . ?
O2C C1C O1C 126.2(13) . . ?
O2C C1C C2C 116.0(10) . . ?
O1C C1C C2C 117.8(12) . . ?
C8B C3B C4B 119.5(14) . . ?
C8B C3B C2B 119.2(12) . . ?
C4B C3B C2B 121.3(13) . . ?
O3B C2B C1B 111.7(10) . . ?
O3B C2B C3B 109.3(11) . . ?
C1B C2B C3B 106.1(10) . . ?
C8A C3A C4A 117.9(16) . . ?
C8A C3A C2A 120.3(14) . . ?
C4A C3A C2A 121.8(14) . . ?
C4C C3C C8C 114.1(13) . . ?
C4C C3C C2C 126.3(13) . . ?
C8C C3C C2C 119.5(11) . . ?
O3D C2D C3D 111.5(10) . . ?
O3D C2D C1D 111.7(10) . . ?
C3D C2D C1D 108.1(10) . . ?
O3C C2C C3C 110.7(11) . . ?
O3C C2C C1C 113.0(10) . . ?
C3C C2C C1C 107.0(10) . . ?
C10B C9B N1B 106.3(11) . . ?
C10B C9B C11B 116.0(11) . . ?
N1B C9B C11B 109.0(11) . . ?
C7C C8C C3C 122.0(13) . . ?
C5D C4D C3D 122.1(14) . . ?
C5D C4D Cl1D 116.4(12) . . ?
C3D C4D Cl1D 121.5(10) . . ?
C9C C11C C12C 114.2(12) . . ?
C9C C11C C16C 112.0(11) . . ?
C12C C11C C16C 110.3(11) . . ?
N1D C9D C10D 107.7(11) . . ?
N1D C9D C11E 111.0(12) . . ?
C10D C9D C11E 125.9(17) . . ?
N1D C9D C11D 111.7(13) . . ?
C10D C9D C11D 99.6(15) . . ?
C5B C4B C3B 122.7(17) . . ?
C5B C4B Cl1B 115.1(13) . . ?
C3B C4B Cl1B 122.2(13) . . ?
C3A C8A C7A 125.2(17) . . ?
C12B C11B C16B 110.5(13) . . ?
C12B C11B C9B 113.3(12) . . ?
C16B C11B C9B 108.6(12) . . ?
C12C C13C C14C 110.4(12) . . ?
C5C C4C C3C 121.1(14) . . ?
C5C C4C Cl1C 120.4(12) . . ?
C3C C4C Cl1C 118.5(13) . . ?
C6D C5D C4D 118.6(15) . . ?
C15C C14C C13C 110.3(13) . . ?
C15C C16C C11C 111.0(11) . . ?
C12A C13A C14A 112.6(12) . . ?
C8D C7D C6D 119.9(16) . . ?
C7D C8D C3D 122.0(14) . . ?
C13A C12A C11A 111.7(13) . . ?
C3A C4A C5A 122.9(19) . . ?
C3A C4A Cl1A 123.1(13) . . ?
C5A C4A Cl1A 114.1(14) . . ?
C6B C7B C8B 118.3(16) . . ?
C15B C16B C11B 113.1(13) . . ?
C15A C16A C11A 111.0(11) . . ?
C8C C7C C6C 121.6(15) . . ?
C15A C14A C13A 112.9(12) . . ?
C7C C6C C5C 118.2(16) . . ?
C3B C8B C7B 119.8(16) . . ?
C7D C6D C5D 121.2(16) . . ?
C14A C15A C16A 109.4(13) . . ?
C13C C12C C11C 112.0(13) . . ?
C6B C5B C4B 114.9(17) . . ?
C8A C7A C6A 118.6(18) . . ?
C5B C6B C7B 124.7(17) . . ?
C6C C5C C4C 122.6(15) . . ?
C4A C5A C6A 118.3(18) . . ?
C14C C15C C16C 114.2(13) . . ?
C13F C14B C15B 117(5) . . ?
C13B C14B C15B 107(2) . . ?
C16B C15B C14B 109.0(13) . . ?
C11B C12B C13F 113(5) . . ?
C11B C12B C13B 108(2) . . ?
C7A C6A C5A 116.9(16) . . ?
C12D C11D C16D 110(2) . . ?
C12D C11D C9D 127(2) . . ?
C16D C11D C9D 118(2) . . ?
C11D C12D C13D 127(3) . . ?
C11D C16D C15D 116(2) . . ?
C12D C13D C14D 108(3) . . ?
C15D C14D C13D 109(3) . . ?
C14D C15D C16D 107(3) . . ?
C16E C15E C14E 107(3) . . ?
C11E C16E C15E 110(2) . . ?
C12E C11E C16E 107(2) . . ?
C12E C11E C9D 140(2) . . ?
C16E C11E C9D 112.2(18) . . ?
C11E C12E C13E 116(3) . . ?
C12E C13E C14E 112(4) . . ?
C15E C14E C13E 96(4) . . ?
C14B C13B C12B 107(3) . . ?
C14B C13F C12B 124(8) . . ?
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
Cl1C C4C 1.743(15) . ?
Cl1D C4D 1.740(14) . ?
Cl1B C4B 1.759(18) . ?
Cl1A C4A 1.776(19) . ?
O2D C1D 1.261(12) . ?
O2A C1A 1.310(13) . ?
O1A C1A 1.265(15) . ?
O1C C1C 1.266(13) . ?
O1D C1D 1.252(13) . ?
O2B C1B 1.260(14) . ?
O1B C1B 1.277(12) . ?
O3A C2A 1.464(13) . ?
O2C C1C 1.222(15) . ?
N1A C9A 1.465(15) . ?
O3B C2B 1.364(14) . ?
N1B C9B 1.518(16) . ?
O3D C2D 1.398(11) . ?
O3C C2C 1.417(15) . ?
N1C C9C 1.469(15) . ?
N1D C9D 1.470(16) . ?
C1A C2A 1.415(19) . ?
C1D C2D 1.521(17) . ?
C2A C3A 1.597(19) . ?
C9C C10C 1.520(15) . ?
C9C C11C 1.536(16) . ?
C1B C2B 1.538(17) . ?
C9A C10A 1.478(18) . ?
C9A C11A 1.564(17) . ?
C11A C12A 1.542(16) . ?
C11A C16A 1.546(18) . ?
C3D C4D 1.397(17) . ?
C3D C8D 1.402(17) . ?
C3D C2D 1.501(18) . ?
C1C C2C 1.556(19) . ?
C3B C8B 1.325(18) . ?
C3B C4B 1.399(18) . ?
C3B C2B 1.587(18) . ?
C3A C8A 1.291(18) . ?
C3A C4A 1.341(19) . ?
C3C C4C 1.396(17) . ?
C3C C8C 1.438(17) . ?
C3C C2C 1.513(17) . ?
C9B C10B 1.431(18) . ?
C9B C11B 1.538(18) . ?
C8C C7C 1.33(2) . ?
C4D C5D 1.37(2) . ?
C11C C12C 1.55(2) . ?
C11C C16C 1.564(18) . ?
C9D C10D 1.492(18) . ?
C9D C11E 1.50(2) . ?
C9D C11D 1.54(2) . ?
C4B C5B 1.39(2) . ?
C8A C7A 1.37(2) . ?
C11B C12B 1.503(18) . ?
C11B C16B 1.507(19) . ?
C13C C12C 1.483(18) . ?
C13C C14C 1.57(2) . ?
C4C C5C 1.36(2) . ?
C5D C6D 1.37(2) . ?
C14C C15C 1.49(2) . ?
C16C C15C 1.509(16) . ?
C13A C12A 1.50(2) . ?
C13A C14A 1.54(2) . ?
C7D C8D 1.351(19) . ?
C7D C6D 1.36(2) . ?
C4A C5A 1.37(2) . ?
C7B C6B 1.37(2) . ?
C7B C8B 1.401(19) . ?
C16B C15B 1.50(2) . ?
C16A C15A 1.539(19) . ?
C7C C6C 1.34(2) . ?
C14A C15A 1.496(19) . ?
C6C C5C 1.35(2) . ?
C5B C6B 1.34(2) . ?
C7A C6A 1.39(2) . ?
C5A C6A 1.43(3) . ?
C14B C13F 1.27(11) . ?
C14B C13B 1.53(4) . ?
C14B C15B 1.554(18) . ?
C12B C13F 1.57(4) . ?
C12B C13B 1.61(3) . ?
C11D C12D 1.33(3) . ?
C11D C16D 1.48(3) . ?
C12D C13D 1.60(4) . ?
C16D C15D 1.56(3) . ?
C13D C14D 1.63(3) . ?
C14D C15D 1.50(3) . ?
C15E C16E 1.50(3) . ?
C15E C14E 1.54(4) . ?
C16E C11E 1.49(3) . ?
C11E C12E 1.32(3) . ?
C12E C13E 1.57(4) . ?
C13E C14E 1.57(3) . ?
