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_4134469
_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_formula_moiety         'C15 H13 Cl'
_chemical_formula_sum            'C15 H13 Cl'
_chemical_formula_weight         228.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 94.829(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.636(5)
_cell_length_b                   7.7229(16)
_cell_length_c                   6.3397(11)
_cell_measurement_reflns_used    1239
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      2.77
_cell_volume                     1153.1(4)
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_collection       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'SHELXL-2016/6, Sheldrick, G. M.'
_computing_structure_refinement  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_structure_solution
;

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

;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
'Nonius Kappa CCD with a Bruker Apex II detector'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5898
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.958
_diffrn_reflns_theta_min         2.776
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.52(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2872
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0377P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0888
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2292
_reflns_number_total             2872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c00147_si_001.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4134467--4134469.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4134469
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.875
_shelx_estimated_absorpt_t_max   0.954
_shelx_res_checksum              56815
_shelx_hkl_checksum              45315