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_7156681
_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 Br O3'
_chemical_formula_sum            'C19 H21 Br O3'
_chemical_formula_weight         377.28
_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                 95.420(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6654(18)
_cell_length_b                   5.3717(12)
_cell_length_c                   17.065(3)
_cell_measurement_reflns_used    4403
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9870
_cell_measurement_theta_min      3.4620
_cell_volume                     882.0(3)
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.6863
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4672
_diffrn_reflns_theta_full        28.9436
_diffrn_reflns_theta_max         28.94
_diffrn_reflns_theta_min         3.60
_exptl_absorpt_coefficient_mu    2.342
_exptl_crystal_density_diffrn    1.4205
_exptl_crystal_F_000             388.0
_refine_diff_density_max         0.7902
_refine_diff_density_min         -0.6905
_refine_diff_density_rms         0.1387
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.07(2)
_refine_ls_d_res_high            0.7343
_refine_ls_d_res_low             5.6628
_refine_ls_goodness_of_fit_ref   1.0588
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0588
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0709
_refine_ls_shift/su_max          0.0549
_refine_ls_shift/su_mean         0.0017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0967P)^2^+0.4416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2044
_reflns_Friedel_coverage         0.466
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              6
_reflns_limit_k_min              -7
_reflns_limit_l_max              23
_reflns_limit_l_min              -22
_reflns_number_gt                1931
_reflns_number_total             4672
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8ob02896f2.cif
_cod_data_source_block           exp_1059
_cod_depositor_comments
'Adding full bibliography for 7156681--7156686.cif.'
_cod_database_code               7156681
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H12 of C12, H6 of C6, {H15a,H15b} of C15, {H14a,H14b} of C14, H13 of C13,
  H7 of C7, H10 of C10, H5 of C5, H4 of C4, {H17a,H17b} of C17, H20 of C20,
  {H16a,H16b} of C16, H9 of C9, H2 of C2
 At 1.5 times of:
  {H18a,H18b,H18c} of C18
2.a Ternary CH refined with riding coordinates:
 C20(H20), C13(H13), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C16(H16a,H16b), C14(H14a,H14b), C15(H15a,H15b)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c)
;