Kinetic Resolution of Allylic Alcohol with Chiral BINOL-Based Alkoxides: A Combination of Experimental and Theoretical Studies.
Liu, Yidong; Liu, Song; Li, Dongmei; Zhang, Nan; Peng, Lei; Ao, Jun; Song, Choong Eui; Lan, Yu; Yan, Hailong; Journal of the American Chemical Society 141 (2019) 1150–1159; doi:10.1021/jacs.8b12796

data_4133656
_publ_section_title
;
 Kinetic Resolution of Allylic Alcohol with Chiral BINOL-Based Alkoxides:
 A Combination of Experimental and Theoretical Studies.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1150
_journal_page_last               1159
_journal_paper_doi               10.1021/jacs.8b12796
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H13 Cl O2'
_chemical_formula_sum            'C16 H13 Cl O2'
_chemical_formula_weight         272.71
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-08
_audit_creation_method
;
 Olex2 1.2-alpha
 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                68.974(6)
_cell_angle_beta                 75.048(5)
_cell_angle_gamma                71.536(5)
_cell_formula_units_Z            2
_cell_length_a                   6.5896(3)
_cell_length_b                   9.7473(5)
_cell_length_c                   12.2249(8)
_cell_measurement_reflns_used    3312
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1460
_cell_measurement_theta_min      4.4170
_cell_volume                     685.90(7)
_computing_molecular_graphics
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9288
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         3.339
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       Block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1783 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5563
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0469P)^2^+0.0545P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1072
_reflns_Friedel_coverage         0.985
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                4503
_reflns_number_total             5563
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b12796_si_002.cif
_cod_data_source_block           LYD-1950
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4133656
_shelx_shelxl_version_number     2014/7
_oxdiff_exptl_absorpt_empirical_details
;
 Empirical correction (ABSPACK) includes:
 - Absorption correction using spherical harmonics
 - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.465
_oxdiff_exptl_absorpt_empirical_full_min 0.628
_reflns_friedel_fraction
;
 is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_olex2_refinement_description
;
 1. Fixed Uiso
 At 1.2 times of:
 All C(H) groups
 At 1.5 times of:
 All O(H) groups
 2. Restrained distances
 H004-O00C
 2.5 with sigma of 0.02
 3.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00R(H00R)
 3.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C007(H007), C009(H009), C00B(H00B), C00F(H00F), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00N(H00N), C00O(H00O), C00Q(H00Q),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011), C1(H1)
 3.c Idealised tetrahedral OH refined as rotating group:
 O004(H004), O00C(H00C)
;
_olex2_submission_special_instructions 'No special instructions were received'