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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/59/1555955.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_1555955
loop_
_publ_author_name
'Han, Yixin'
'Breitler, Simon'
'Zheng, Shao-Liang'
'Corey, E. J.'
_publ_section_title
;
 Enantioselective Conversion of Achiral Cyclohexadienones to Chiral
 Cyclohexenones by Desymmetrization.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6172
_journal_page_last               6175
_journal_paper_doi               10.1021/acs.orglett.6b03186
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H15 Cl O'
_chemical_formula_weight         222.70
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7518(2)
_cell_length_b                   8.9722(2)
_cell_length_c                   13.5378(3)
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.6
_cell_measurement_theta_min      2.49
_cell_volume                     1063.03(4)
_computing_cell_refinement       'SAINT 8.35A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT 8.35A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0091
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26362
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.721
_diffrn_reflns_theta_min         5.916
_exptl_absorpt_coefficient_mu    2.906
_exptl_absorpt_correction_T_max  0.8642
_exptl_absorpt_correction_T_min  0.7847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 763 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0201
_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)+(0.0236P)²+0.3953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0523
_refine_ls_wR_factor_ref         0.0524
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                1876
_reflns_number_total             1877
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b03186_si_001.cif
_cod_data_source_block           SB-IV-630
_cod_database_code               1555955
_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_min   0.623
_shelx_estimated_absorpt_t_max   0.722
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
Cl1 Cl 0.70147(5) 0.87314(5) 0.05941(3) 0.02064(13) Uani 1 1 d . .
O1 O 0.42658(15) 0.63677(17) 0.17336(10) 0.0210(3) Uani 1 1 d . .
C1 C 0.6827(2) 0.7829(2) 0.44202(14) 0.0196(4) Uani 1 1 d . .
H1A H 0.6851 0.7547 0.5127 0.024 Uiso 1 1 calc R U
H1B H 0.6527 0.8887 0.4346 0.024 Uiso 1 1 calc R U
C2 C 0.5850(2) 0.6769(2) 0.37909(14) 0.0173(4) Uani 1 1 d . .
H2 H 0.4754 0.6673 0.3990 0.021 Uiso 1 1 calc R U
C3 C 0.6153(2) 0.7484(2) 0.27400(14) 0.0135(4) Uani 1 1 d . .
H3 H 0.5540 0.8422 0.2693 0.016 Uiso 1 1 calc R U
C4 C 0.5617(2) 0.6446(2) 0.19362(13) 0.0137(4) Uani 1 1 d . .
C5 C 0.6761(2) 0.5436(2) 0.14396(14) 0.0153(4) Uani 1 1 d . .
H5A H 0.6366 0.5175 0.0776 0.018 Uiso 1 1 calc R U
H5B H 0.6831 0.4501 0.1825 0.018 Uiso 1 1 calc R U
C6 C 0.8351(2) 0.6063(2) 0.13224(13) 0.0152(4) Uani 1 1 d . .
H6 H 0.9142 0.5321 0.1117 0.018 Uiso 1 1 calc R U
C7 C 0.8932(2) 0.7288(2) 0.20035(14) 0.0145(4) Uani 1 1 d . .
C8 C 0.7880(2) 0.7926(2) 0.27923(13) 0.0132(4) Uani 1 1 d . .
H8 H 0.7945 0.9037 0.2755 0.016 Uiso 1 1 calc R U
C9 C 0.8318(2) 0.7446(2) 0.38736(14) 0.0168(4) Uani 1 1 d . .
H9 H 0.9268 0.7909 0.4148 0.020 Uiso 1 1 calc R U
C10 C 0.8257(2) 0.5761(2) 0.39031(14) 0.0187(4) Uani 1 1 d . .
H10 H 0.9109 0.5110 0.3951 0.022 Uiso 1 1 calc R U
C11 C 0.6797(2) 0.5354(2) 0.38500(13) 0.0194(4) Uani 1 1 d . .
H11 H 0.6417 0.4362 0.3849 0.023 Uiso 1 1 calc R U
C12 C 0.8599(2) 0.7614(2) 0.09300(14) 0.0165(4) Uani 1 1 d . .
H12 H 0.9522 0.7736 0.0502 0.020 Uiso 1 1 calc R U
C13 C 1.0618(2) 0.7266(2) 0.22679(15) 0.0195(4) Uani 1 1 d . .
H13A H 1.0933 0.8259 0.2490 0.029 Uiso 1 1 calc R U
H13B H 1.1217 0.6980 0.1686 0.029 Uiso 1 1 calc R U
H13C H 1.0793 0.6543 0.2799 0.029 Uiso 1 1 calc R U
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
C2 C1 C9 93.86(15)
C2 C1 H1A 113.0
C9 C1 H1A 112.9
C2 C1 H1B 113.0
C9 C1 H1B 112.9
H1A C1 H1B 110.4
C11 C2 C1 100.64(16)
C11 C2 C3 107.16(15)
C1 C2 C3 98.90(15)
C11 C2 H2 115.9
C1 C2 H2 115.9
C3 C2 H2 115.9
C4 C3 C8 119.32(15)
C4 C3 C2 110.28(15)
C8 C3 C2 102.92(15)
C4 C3 H3 107.9
C8 C3 H3 107.9
C2 C3 H3 107.9
O1 C4 C3 120.04(17)
O1 C4 C5 120.70(17)
C3 C4 C5 119.13(15)
C4 C5 C6 115.76(16)
C4 C5 H5A 108.3
C6 C5 H5A 108.3
C4 C5 H5B 108.3
C6 C5 H5B 108.3
H5A C5 H5B 107.4
C12 C6 C5 120.98(16)
C12 C6 C7 59.87(12)
C5 C6 C7 120.91(16)
C12 C6 H6 114.7
C5 C6 H6 114.7
C7 C6 H6 114.7
C12 C7 C13 114.65(16)
C12 C7 C8 119.04(16)
C13 C7 C8 115.31(16)
C12 C7 C6 59.51(12)
C13 C7 C6 117.24(16)
C8 C7 C6 119.64(15)
C7 C8 C3 117.23(15)
C7 C8 C9 113.76(15)
C3 C8 C9 102.01(14)
C7 C8 H8 107.8
C3 C8 H8 107.8
C9 C8 H8 107.8
C10 C9 C1 100.37(16)
C10 C9 C8 106.81(15)
C1 C9 C8 100.37(14)
C10 C9 H9 115.7
C1 C9 H9 115.7
C8 C9 H9 115.7
C11 C10 C9 107.87(18)
C11 C10 H10 126.1
C9 C10 H10 126.1
C10 C11 C2 107.28(17)
C10 C11 H11 126.4
C2 C11 H11 126.4
C6 C12 C7 60.62(12)
C6 C12 Cl1 120.08(14)
C7 C12 Cl1 120.52(14)
C6 C12 H12 115.0
C7 C12 H12 115.0
Cl1 C12 H12 115.0
C7 C13 H13A 109.5
C7 C13 H13B 109.5
H13A C13 H13B 109.5
C7 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C12 1.770(2)
O1 C4 1.216(2)
C1 C2 1.536(3)
C1 C9 1.539(3)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C11 1.518(3)
C2 C3 1.583(3)
C2 H2 1.0000
C3 C4 1.507(3)
C3 C8 1.565(2)
C3 H3 1.0000
C4 C5 1.508(3)
C5 C6 1.510(3)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C12 1.505(3)
C6 C7 1.522(3)
C6 H6 1.0000
C7 C12 1.511(3)
C7 C13 1.518(3)
C7 C8 1.522(3)
C8 C9 1.573(3)
C8 H8 1.0000
C9 C10 1.513(3)
C9 H9 1.0000
C10 C11 1.331(3)
C10 H10 0.9500
C11 H11 0.9500
C12 H12 1.0000
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
C9 C1 C2 C11 49.55(16)
C9 C1 C2 C3 -59.92(16)
C11 C2 C3 C4 62.67(19)
C1 C2 C3 C4 166.79(15)
C11 C2 C3 C8 -65.68(17)
C1 C2 C3 C8 38.44(17)
C8 C3 C4 O1 -162.38(17)
C2 C3 C4 O1 78.9(2)
C8 C3 C4 C5 21.8(2)
C2 C3 C4 C5 -96.98(19)
O1 C4 C5 C6 150.26(18)
C3 C4 C5 C6 -33.9(2)
C4 C5 C6 C12 -47.1(2)
C4 C5 C6 C7 24.1(2)
C5 C6 C7 C12 -110.25(19)
C12 C6 C7 C13 -103.95(18)
C5 C6 C7 C13 145.80(18)
C12 C6 C7 C8 108.25(19)
C5 C6 C7 C8 -2.0(3)
C12 C7 C8 C3 58.8(2)
C13 C7 C8 C3 -159.03(17)
C6 C7 C8 C3 -10.6(2)
C12 C7 C8 C9 177.59(16)
C13 C7 C8 C9 -40.2(2)
C6 C7 C8 C9 108.19(19)
C4 C3 C8 C7 1.0(2)
C2 C3 C8 C7 123.42(17)
C4 C3 C8 C9 -123.98(17)
C2 C3 C8 C9 -1.52(16)
C2 C1 C9 C10 -49.65(16)
C2 C1 C9 C8 59.76(16)
C7 C8 C9 C10 -58.9(2)
C3 C8 C9 C10 68.28(18)
C7 C8 C9 C1 -163.19(15)
C3 C8 C9 C1 -35.98(16)
C1 C9 C10 C11 33.3(2)
C8 C9 C10 C11 -70.93(19)
C9 C10 C11 C2 -0.4(2)
C1 C2 C11 C10 -32.8(2)
C3 C2 C11 C10 70.08(19)
C5 C6 C12 C7 110.14(19)
C5 C6 C12 Cl1 -0.2(2)
C7 C6 C12 Cl1 -110.33(16)
C13 C7 C12 C6 108.32(19)
C8 C7 C12 C6 -109.23(18)
C13 C7 C12 Cl1 -142.06(15)
C8 C7 C12 Cl1 0.4(2)
C6 C7 C12 Cl1 109.62(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168305557
