Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes.
Xu, Bin; Troian-Gautier, Ludovic; Dykstra, Ryan; Martin, Robert T.; Gutierrez, Osvaldo; Tambar, Uttam K.; Journal of the American Chemical Society 142 (2020) 6206–6215; doi:10.1021/jacs.0c00147

data_4134468
_publ_section_title
;
 Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to
 Cyclopropanes.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6206
_journal_page_last               6215
_journal_paper_doi               10.1021/jacs.0c00147
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H9 Cl S'
_chemical_formula_sum            'C11 H9 Cl S'
_chemical_formula_weight         208.69
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 109.178(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3530(4)
_cell_length_b                   5.8263(2)
_cell_length_c                   10.6780(4)
_cell_measurement_reflns_used    4327
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      2.00
_cell_volume                     490.83(4)
_computing_cell_refinement
'CrysAlisPro V 1.171.39.46, Agilent Technologies'
_computing_data_collection       'CrystalClear 1.40 (Rigaku Inc., 2008)'
_computing_data_reduction
'CrysAlisPro V 1.171.39.46, Agilent Technologies'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_structure_solution
;

Sheldrick. G. M.  (2015) SHELXT. Acta Cryst. A71, 3-8.

;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku AFC-12 with a Saturn 724+ CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6202
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.380
_diffrn_reflns_theta_min         2.019
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       plates
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.856
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.  The bulk sample was racemic.  The 
crystal is a racemic twin.
;
_refine_ls_abs_structure_Flack   0.44(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1963
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0830P)^2^+0.3225P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1237
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1885
_reflns_number_total             1963
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c00147_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4134467--4134469.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4134468
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.918
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              67363
_shelx_hkl_checksum              4874