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_7156686
_publ_section_title
;
 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 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       '\w 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/[\s^2^(Fo^2^)+(0.1033P)^2^+0.6623P] where P=(Fo^2^+2Fc^2^)/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)
;