Applications of chiral naphthyloxycyclohexanols in deracemization of α-substituted carboxylic acids by dynamic thermodynamic resolution.
Khanvilkar, Aditya N.; Samanta, Sudeep G.; Bedekar, Ashutosh V.; Organic & biomolecular chemistry 17 (2019) 2670–2683; doi:10.1039/c8ob02896f

data_7156683
_publ_section_title
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 Applications of chiral naphthyloxycyclohexanols in deracemization of
 \a-substituted carboxylic acids by dynamic thermodynamic resolution.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; 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 ad
_chemical_formula_moiety         'C19 H21 Cl O3'
_chemical_formula_sum            'C19 H21 Cl O3'
_chemical_formula_weight         332.83
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_update_record
;
2018-07-07 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.047(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3718(9)
_cell_length_b                   5.8521(4)
_cell_length_c                   16.3645(14)
_cell_measurement_reflns_used    2163
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9400
_cell_measurement_theta_min      4.2630
_cell_volume                     862.54(13)
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.8516
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10572
_diffrn_reflns_theta_full        29.2402
_diffrn_reflns_theta_max         29.24
_diffrn_reflns_theta_min         3.71
_exptl_absorpt_coefficient_mu    0.234
_exptl_crystal_density_diffrn    1.2814
_exptl_crystal_F_000             352.4639
_refine_diff_density_max         0.4185
_refine_diff_density_min         -0.4811
_refine_diff_density_rms         0.0647
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.00(14)
_refine_ls_d_res_high            0.7275
_refine_ls_d_res_low             5.4847
_refine_ls_goodness_of_fit_ref   1.0266
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0266
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.2557P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1482
_reflns_Friedel_coverage         0.785
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              22
_reflns_limit_l_min              -21
_reflns_number_gt                3022
_reflns_number_total             3982
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8ob02896f2.cif
_cod_data_source_block           exp_1016
_cod_depositor_comments
'Adding full bibliography for 7156681--7156686.cif.'
_cod_database_code               7156683
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H13a,H13b} of C13, {H15a,H15b} of C15, {H14a,H14b} of C14, H2 of C2, H12
  of C12, H3 of C3, H5 of C5, H10 of C10, H8 of C8, H6 of C6, H20 of C20, H17
  of C17, H7 of C7, {H16a,H16b} of C16
 At 1.5 times of:
  {H22a,H22b,H22c} of C22
2.a Ternary CH refined with riding coordinates:
 C12(H12), C20(H20), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C13(H13a,H13b), C15(H15a,H15b), C14(H14a,H14b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C10(H10), C8(H8), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c)
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