#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/31/7113194.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_7113194
loop_
_publ_author_name
'Jiang, Jun'
'He, Long'
'Luo, Shi-Wei'
'Cun, Lin-Feng'
'Gong, Liu-Zhu'
_publ_section_title
;
 Enantioselective desymmetrization of prochiral cyclohexanone derivatives
 via the organocatalytic direct Aldol reaction.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              736
_journal_page_last               738
_journal_paper_doi               10.1039/b615043h
_journal_year                    2007
_chemical_formula_sum            'C14 H17 Cl O2'
_chemical_formula_weight         252.73
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   6.748(5)
_cell_length_b                   10.465(5)
_cell_length_c                   19.186(5)
_cell_measurement_reflns_used    6583
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.6354
_cell_measurement_theta_min      2.3003
_cell_volume                     1354.9(12)
_computing_cell_refinement       'CrysAlis RED'
_computing_data_collection       'CrysAlis CCD'
_computing_data_reduction        'CrysAlis RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7351
_diffrn_reflns_theta_full        62.63
_diffrn_reflns_theta_max         62.63
_diffrn_reflns_theta_min         4.61
_exptl_absorpt_coefficient_mu    2.397
_exptl_absorpt_correction_T_max  0.7956
_exptl_absorpt_correction_T_min  0.4628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       0.0135(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0485P)²+0.3620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0928
_reflns_number_gt                1975
_reflns_number_total             2045
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b615043h.txt
_cod_data_source_block           080627-cu
_cod_database_code               7113194
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.89245(12) -0.35461(7) 0.37744(4) 0.0932(3) Uani 1 1 d .
O1 O 0.3020(2) 0.11887(16) 0.49336(8) 0.0652(4) Uani 1 1 d .
H1 H 0.3036 0.0457 0.5087 0.098 Uiso 1 1 calc R
O2 O 0.0282(2) 0.28948(18) 0.39588(9) 0.0739(5) Uani 1 1 d .
C13 C 0.4544(4) 0.2028(2) 0.30994(10) 0.0595(6) Uani 1 1 d .
H13A H 0.5436 0.1316 0.3020 0.071 Uiso 1 1 calc R
H13B H 0.3689 0.2102 0.2695 0.071 Uiso 1 1 calc R
C7 C 0.4445(3) 0.1305(2) 0.43917(10) 0.0528(5) Uani 1 1 d .
H7 H 0.5388 0.1979 0.4517 0.063 Uiso 1 1 calc R
C11 C 0.4407(4) 0.4368(2) 0.33343(14) 0.0712(7) Uani 1 1 d .
H11A H 0.3492 0.4499 0.2951 0.085 Uiso 1 1 calc R
H11B H 0.5193 0.5138 0.3386 0.085 Uiso 1 1 calc R
C12 C 0.5762(4) 0.3249(2) 0.31683(11) 0.0603(6) Uani 1 1 d .
H12 H 0.6675 0.3140 0.3561 0.072 Uiso 1 1 calc R
C5 C 0.7516(4) 0.0112(2) 0.40309(15) 0.0678(7) Uani 1 1 d .
H5 H 0.8138 0.0897 0.3970 0.081 Uiso 1 1 calc R
C8 C 0.3266(3) 0.17373(19) 0.37401(11) 0.0525(5) Uani 1 1 d .
H8 H 0.2336 0.1055 0.3617 0.063 Uiso 1 1 calc R
C4 C 0.5580(3) 0.0076(2) 0.42664(11) 0.0522(5) Uani 1 1 d .
C10 C 0.3235(4) 0.4126(2) 0.40067(14) 0.0653(6) Uani 1 1 d .
H10A H 0.4137 0.4048 0.4398 0.078 Uiso 1 1 calc R
H10B H 0.2345 0.4835 0.4096 0.078 Uiso 1 1 calc R
C3 C 0.4723(4) -0.1106(2) 0.43729(12) 0.0599(6) Uani 1 1 d .
H3 H 0.3430 -0.1152 0.4539 0.072 Uiso 1 1 calc R
C2 C 0.5746(4) -0.2222(2) 0.42372(12) 0.0679(7) Uani 1 1 d .
H2 H 0.5159 -0.3012 0.4320 0.081 Uiso 1 1 calc R
C9 C 0.2077(3) 0.2918(2) 0.39216(11) 0.0561(5) Uani 1 1 d .
C6 C 0.8544(4) -0.0998(3) 0.38837(16) 0.0764(7) Uani 1 1 d .
H6 H 0.9841 -0.0959 0.3721 0.092 Uiso 1 1 calc R
C14 C 0.6996(5) 0.3499(4) 0.25154(14) 0.0953(10) Uani 1 1 d .
H14A H 0.7724 0.4280 0.2571 0.143 Uiso 1 1 calc R
H14B H 0.6135 0.3568 0.2119 0.143 Uiso 1 1 calc R
H14C H 0.7904 0.2805 0.2446 0.143 Uiso 1 1 calc R
C1 C 0.7643(4) -0.2151(2) 0.39784(13) 0.0653(6) 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'
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
C12 C13 C8 113.58(17)
O1 C7 C4 112.63(17)
O1 C7 C8 105.56(17)
C4 C7 C8 112.27(17)
C12 C11 C10 111.0(2)
C11 C12 C13 109.9(2)
C11 C12 C14 111.6(2)
C13 C12 C14 111.5(2)
C6 C5 C4 121.2(2)
C9 C8 C13 108.72(18)
C9 C8 C7 108.95(17)
C13 C8 C7 114.62(18)
C3 C4 C5 117.9(2)
C3 C4 C7 121.67(19)
C5 C4 C7 120.4(2)
C9 C10 C11 108.5(2)
C4 C3 C2 121.3(2)
C1 C2 C3 119.2(2)
O2 C9 C10 122.2(2)
O2 C9 C8 121.7(2)
C10 C9 C8 115.96(18)
C1 C6 C5 119.5(2)
C6 C1 C2 120.8(2)
C6 C1 Cl1 119.4(2)
C2 C1 Cl1 119.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.742(2)
O1 C7 1.421(3)
O2 C9 1.214(3)
C13 C12 1.526(3)
C13 C8 1.532(3)
C7 C4 1.516(3)
C7 C8 1.549(3)
C11 C12 1.519(3)
C11 C10 1.534(4)
C12 C14 1.527(3)
C5 C6 1.382(4)
C5 C4 1.383(3)
C8 C9 1.514(3)
C4 C3 1.381(3)
C10 C9 1.495(3)
C3 C2 1.381(3)
C2 C1 1.375(4)
C6 C1 1.363(4)
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
C10 C11 C12 C13 58.0(3)
C10 C11 C12 C14 -177.8(2)
C8 C13 C12 C11 -55.4(2)
C8 C13 C12 C14 -179.6(2)
C12 C13 C8 C9 51.0(2)
C12 C13 C8 C7 -71.2(2)
O1 C7 C8 C9 53.4(2)
C4 C7 C8 C9 176.42(17)
O1 C7 C8 C13 175.40(17)
C4 C7 C8 C13 -61.5(2)
C6 C5 C4 C3 2.1(4)
C6 C5 C4 C7 -177.0(2)
O1 C7 C4 C3 31.4(3)
C8 C7 C4 C3 -87.6(2)
O1 C7 C4 C5 -149.5(2)
C8 C7 C4 C5 91.5(3)
C12 C11 C10 C9 -57.6(3)
C5 C4 C3 C2 -1.2(3)
C7 C4 C3 C2 178.0(2)
C4 C3 C2 C1 -1.2(3)
C11 C10 C9 O2 -119.7(2)
C11 C10 C9 C8 56.5(3)
C13 C8 C9 O2 123.5(2)
C7 C8 C9 O2 -111.0(2)
C13 C8 C9 C10 -52.8(2)
C7 C8 C9 C10 72.8(2)
C4 C5 C6 C1 -0.6(4)
C5 C6 C1 C2 -1.9(4)
C5 C6 C1 Cl1 178.6(2)
C3 C2 C1 C6 2.8(4)
C3 C2 C1 Cl1 -177.68(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101442205
