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_7156682
_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 unk
_chemical_formula_moiety         'C26 H26 O5'
_chemical_formula_sum            'C26 H26 O5'
_chemical_formula_weight         418.49
_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                   8.2235(6)
_cell_length_b                   15.8364(13)
_cell_length_c                   17.2177(13)
_cell_measurement_reflns_used    2163
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9400
_cell_measurement_theta_min      4.2630
_cell_volume                     2242.3(3)
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.8669
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13939
_diffrn_reflns_theta_full        28.9593
_diffrn_reflns_theta_max         28.96
_diffrn_reflns_theta_min         3.50
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_density_diffrn    1.2396
_exptl_crystal_F_000             888.4921
_refine_diff_density_max         0.2894
_refine_diff_density_min         -0.3311
_refine_diff_density_rms         0.0821
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.1(11)
_refine_ls_d_res_high            0.7339
_refine_ls_d_res_low             5.8279
_refine_ls_goodness_of_fit_ref   1.0707
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    46
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0707
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0637P)^2^+0.0510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1265
_reflns_Friedel_coverage         0.821
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              19
_reflns_limit_k_min              -19
_reflns_limit_l_max              23
_reflns_limit_l_min              -22
_reflns_number_gt                3857
_reflns_number_total             5147
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8ob02896f2.cif
_cod_data_source_block           exp_1012
_cod_depositor_comments
'Adding full bibliography for 7156681--7156686.cif.'
_cod_database_code               7156682
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H29 of C29, H8 of C8, H30 of C30, H7 of C7, H6 of C6, {H15a,H15b} of C15,
  {H16a,H16b} of C16, H9 of C9, H27 of C27, H31 of C31, H2 of C2, H3 of C3, H28
  of C28, H4 of C4, H12 of C12, H13 of C13, H20 of C20, {H17a,H17b} of C17,
  {H14a,H14b} of C14
 At 1.5 times of:
  {H24a,H24b,H24c} of C24
2.a Ternary CH refined with riding coordinates:
 C12(H12), C13(H13), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C14(H14a,H14b), C15(H15a,H15b), C16(H16a,H16b)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C27(H27), C31(H31), C2(H2), C3(H3), C28(H28), C4(H4), C29(H29),
 C8(H8), C30(H30), C7(H7), C6(H6)
2.d Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c)
;