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_4134467
_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 unk
_chemical_formula_moiety         'C19 H21 N O'
_chemical_formula_sum            'C19 H21 N O'
_chemical_formula_weight         279.37
_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_date             2019-08-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.162(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2036(9)
_cell_length_b                   8.1137(11)
_cell_length_c                   15.041(3)
_cell_measurement_reflns_used    2465
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.72
_cell_volume                     752.7(2)
_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      100.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1579
_diffrn_reflns_point_group_measured_fraction_full 0.537
_diffrn_reflns_point_group_measured_fraction_max 0.535
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.963
_diffrn_reflns_theta_min         2.856
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 12644 reflections, Rint = 0.0566
 (4374 with I > 3sig(I), Rint = 0.0423)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       prism
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1579
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0597P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                1253
_reflns_number_total             1579
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c00147_si_003.cif
_cod_data_source_block           xb-7-95
_cod_depositor_comments
'Adding full bibliography for 4134467--4134469.cif.'
_cod_database_code               4134467
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.84727
 0.15273
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_shelx_res_checksum              52064
_shelx_hkl_checksum              75151
_olex2_submission_special_instructions 'No special instructions were received'