Enantioselective Vanadium-Catalyzed Oxidative Coupling: Development and Mechanistic Insights.
Kang, Houng; Herling, Madison R.; Niederer, Kyle A.; Lee, Young Eun; Vasu Govardhana Reddy, Peddiahgari; Dey, Sangeeta; Allen, Scott E.; Sung, Paul; Hewitt, Kirsten; Torruellas, Carilyn; Kim, Gina J.; Kozlowski, Marisa C.; The Journal of organic chemistry 83 (2018) 14362–14384; doi:10.1021/acs.joc.8b02083

data_4035677
_publ_section_title
;
 Enantioselective Vanadium-Catalyzed Oxidative Coupling: Development and
 Mechanistic Insights.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14362
_journal_page_last               14384
_journal_paper_doi               10.1021/acs.joc.8b02083
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H22 O2'
_chemical_formula_weight         270.36
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      18
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.2248(16)
_cell_length_b                   21.607(2)
_cell_length_c                   8.7927(8)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    143(1)
_cell_measurement_theta_max      64.39
_cell_measurement_theta_min      3.41
_cell_volume                     3082.5(5)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17988
_diffrn_reflns_theta_full        64.74
_diffrn_reflns_theta_max         64.74
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    0.582
_exptl_absorpt_correction_T_max  0.7525
_exptl_absorpt_correction_T_min  0.6793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         5084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.3428P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0838
_reflns_number_gt                4936
_reflns_number_total             5084
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02083_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
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The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file
'/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/lists/replacement-tags.lst'.

Automatic conversion script
Id: cif_correct_tags 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21 21 2 '
_cod_database_code               4035677