#------------------------------------------------------------------------------
#$Date: 2019-11-08 03:23:24 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225045 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/66/7156686.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_7156686
loop_
_publ_author_name
'Khanvilkar, Aditya N.'
'Samanta, Sudeep G.'
'Bedekar, Ashutosh V.'
_publ_section_title
;
 Applications of chiral naphthyloxycyclohexanols in deracemization of
 α-substituted carboxylic acids by dynamic thermodynamic resolution.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2670
_journal_page_last               2683
_journal_paper_doi               10.1039/c8ob02896f
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H21 Cl O3'
_chemical_formula_sum            'C19 H21 Cl O3'
_chemical_formula_weight         332.83
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_update_record
;
2018-07-07 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8657(9)
_cell_length_b                   10.5557(9)
_cell_length_c                   18.970(2)
_cell_measurement_reflns_used    2163
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9400
_cell_measurement_theta_min      4.2630
_cell_volume                     1775.3(3)
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.8623
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11056
_diffrn_reflns_theta_full        29.0891
_diffrn_reflns_theta_max         29.09
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.227
_exptl_crystal_density_diffrn    1.2452
_exptl_crystal_F_000             704.9279
_refine_diff_density_max         0.5736
_refine_diff_density_min         -0.4648
_refine_diff_density_rms         0.0687
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.16(14)
_refine_ls_d_res_high            0.7309
_refine_ls_d_res_low             6.3919
_refine_ls_goodness_of_fit_ref   0.9575
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9575
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0699
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1033P)²+0.6623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2009
_reflns_Friedel_coverage         0.811
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              24
_reflns_limit_l_min              -24
_reflns_number_gt                2615
_reflns_number_total             4101
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8ob02896f2.cif
_cod_data_source_block           exp_973
_cod_depositor_comments
'Adding full bibliography for 7156681--7156686.cif.'
_cod_database_code               7156686
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H4 of C4, H10 of C10, H5 of C5, H12 of C12, H17 of C17, H9 of C9, {H13a,
  H13b} of C13, H6 of C6, {H16a,H16b} of C16, H20 of C20, H7 of C7, {H14a,H14b}
  of C14, {H15a,H15b} of C15
 At 1.5 times of:
  {H22a,H22b,H22c} of C22
2.a Ternary CH refined with riding coordinates:
 C12(H12), C17(H17), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C16(H16a,H16b), C14(H14a,H14b), C15(H15a,H15b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C5(H5), C9(H9), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,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_refinement_flags_posn
Cl21 Cl 0.8526(3) 0.80354(14) 0.42878(8) 0.1441(9) Uani 1.000000 .
C19 C 0.7229(5) 0.5764(4) 0.4138(2) 0.0676(11) Uani 1.000000 .
O18 O 0.7625(2) 0.4605(2) 0.39864(14) 0.0606(7) Uani 1.000000 .
O11 O 0.6027(3) 0.2883(2) 0.47766(12) 0.0590(7) Uani 1.000000 .
O23 O 0.6051(4) 0.6223(3) 0.3990(3) 0.1331(18) Uani 1.000000 .
C1 C 0.7052(4) 0.0948(4) 0.5273(3) 0.0621(10) Uani 1.000000 .
C2 C 0.6411(4) 0.2128(3) 0.53287(18) 0.0515(8) Uani 1.000000 .
C3 C 0.6115(3) 0.2667(3) 0.60018(19) 0.0465(7) Uani 1.000000 .
C4 C 0.5526(4) 0.3899(3) 0.60805(19) 0.0524(8) Uani 1.000000 .
H4 H 0.5280(4) 0.4369(3) 0.56820(19) 0.0629(10) Uiso 1.000000 R
C10 C 0.7401(4) 0.0266(4) 0.5878(3) 0.0699(11) Uani 1.000000 .
H10 H 0.7841(4) -0.0530(4) 0.5836(3) 0.0839(13) Uiso 1.000000 R
C5 C 0.5312(5) 0.4410(4) 0.6730(2) 0.0659(10) Uani 1.000000 .
H5 H 0.4932(5) 0.5228(4) 0.6773(2) 0.0790(12) Uiso 1.000000 R
C12 C 0.6488(4) 0.2558(3) 0.40719(18) 0.0504(8) Uani 1.000000 .
H12 H 0.7503(4) 0.2191(3) 0.40827(18) 0.0605(10) Uiso 1.000000 R
C17 C 0.6512(4) 0.3770(3) 0.36603(17) 0.0473(8) Uani 1.000000 .
H17 H 0.5514(4) 0.4168(3) 0.36790(17) 0.0568(9) Uiso 1.000000 R
C9 C 0.7114(5) 0.0735(4) 0.6523(3) 0.0730(13) Uani 1.000000 .
H9 H 0.7334(5) 0.0247(4) 0.6918(3) 0.0876(15) Uiso 1.000000 R
C8 C 0.6486(4) 0.1957(4) 0.6614(2) 0.0582(9) Uani 1.000000 .
C13 C 0.5406(4) 0.1633(4) 0.3730(2) 0.0663(10) Uani 1.000000 .
H13a H 0.5414(4) 0.0841(4) 0.3989(2) 0.0795(12) Uiso 1.000000 R
H13b H 0.4391(4) 0.1975(4) 0.3747(2) 0.0795(12) Uiso 1.000000 R
C6 C 0.5659(5) 0.3714(5) 0.7333(2) 0.0739(12) Uani 1.000000 .
H6 H 0.5500(5) 0.4067(5) 0.7776(2) 0.0887(14) Uiso 1.000000 R
C16 C 0.6956(5) 0.3551(4) 0.2900(2) 0.0675(11) Uani 1.000000 .
H16a H 0.6932(5) 0.4349(4) 0.2647(2) 0.0810(13) Uiso 1.000000 R
H16b H 0.7977(5) 0.3224(4) 0.2881(2) 0.0810(13) Uiso 1.000000 R
C20 C 0.8505(5) 0.6413(4) 0.4538(3) 0.0771(12) Uani 1.000000 .
H20 H 0.9467(5) 0.6021(4) 0.4406(3) 0.0925(15) Uiso 1.000000 R
C7 C 0.6224(5) 0.2531(5) 0.7278(2) 0.0733(12) Uani 1.000000 .
H7 H 0.6447(5) 0.2081(5) 0.7686(2) 0.0880(15) Uiso 1.000000 R
C14 C 0.5851(5) 0.1388(5) 0.2965(3) 0.0850(14) Uani 1.000000 .
H14a H 0.6838(5) 0.0992(5) 0.2949(3) 0.1020(17) Uiso 1.000000 R
H14b H 0.5131(5) 0.0814(5) 0.2750(3) 0.1020(17) Uiso 1.000000 R
C15 C 0.5890(6) 0.2619(5) 0.2553(3) 0.0860(15) Uani 1.000000 .
H15a H 0.4884(6) 0.2979(5) 0.2533(3) 0.1032(18) Uiso 1.000000 R
H15b H 0.6220(6) 0.2454(5) 0.2074(3) 0.1032(18) Uiso 1.000000 R
C22 C 0.8311(7) 0.6331(6) 0.5319(3) 0.1080(19) Uani 1.000000 .
H22a H 0.919(2) 0.667(4) 0.5547(3) 0.162(3) Uiso 1.000000 GR
H22b H 0.744(3) 0.681(3) 0.5457(4) 0.162(3) Uiso 1.000000 GR
H22c H 0.818(5) 0.5461(7) 0.5453(4) 0.162(3) Uiso 1.000000 GR
H1 H 0.733(4) 0.062(3) 0.485(2) 0.050(10) Uiso 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 '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'
C 0.00347 0.00161 '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 0.01158 0.00611 '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 0.14873 0.16029 '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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O23 C19 O18 124.5(4)
C20 C19 O18 109.4(4)
C20 C19 O23 126.1(4)
C17 O18 C19 118.6(3)
C12 O11 C2 120.3(2)
C10 C1 C2 119.9(4)
C1 C2 O11 125.2(3)
C3 C2 O11 114.3(3)
C3 C2 C1 120.5(3)
C4 C3 C2 122.2(3)
C8 C3 C2 118.7(3)
C8 C3 C4 119.1(3)
C5 C4 C3 121.0(4)
C9 C10 C1 121.3(4)
C6 C5 C4 120.2(4)
C17 C12 O11 106.5(2)
C13 C12 O11 111.8(3)
C13 C12 C17 109.6(3)
C12 C17 O18 107.7(3)
C16 C17 O18 108.7(3)
C16 C17 C12 111.7(3)
C8 C9 C10 121.4(4)
C9 C8 C3 118.2(4)
C7 C8 C3 117.6(4)
C7 C8 C9 124.2(4)
C14 C13 C12 110.7(3)
C7 C6 C5 120.4(4)
C15 C16 C17 110.6(3)
C19 C20 Cl21 107.9(3)
C22 C20 Cl21 108.8(4)
C22 C20 C19 112.4(4)
C6 C7 C8 121.7(4)
C15 C14 C13 110.5(4)
C14 C15 C16 110.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl21 C20 1.777(5)
C19 O18 1.306(4)
C19 O23 1.185(5)
C19 C20 1.523(6)
O18 C17 1.461(4)
O11 C2 1.359(4)
O11 C12 1.439(4)
C1 C2 1.373(5)
C1 C10 1.389(6)
C2 C3 1.422(5)
C3 C4 1.409(5)
C3 C8 1.420(5)
C4 C5 1.359(5)
C10 C9 1.344(6)
C5 C6 1.394(6)
C12 C17 1.499(5)
C12 C13 1.514(5)
C17 C16 1.512(5)
C9 C8 1.415(6)
C8 C7 1.417(6)
C13 C14 1.527(7)
C6 C7 1.350(7)
C16 C15 1.515(6)
C20 C22 1.494(7)
C14 C15 1.516(8)
