Phosphine-catalysed intermolecular cyclopropanation reaction between benzyl bromides and activated alkenes
Zhang, Jie; Song, Xue; Chen, Zhi-Chao; Du, Wei; Chen, Ying-Chun; New Journal of Chemistry 46 (2022) 16382–16386; doi:10.1039/D2NJ03417D

data_7061694
_publ_section_title
;
 Phosphine-catalysed intermolecular cyclopropanation reaction between
 benzyl bromides and activated alkenes
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16382
_journal_page_last               16386
_journal_paper_doi               10.1039/D2NJ03417D
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C23 H16 Cl N O'
_chemical_formula_sum            'C23 H16 Cl N O'
_chemical_formula_weight         357.82
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-06-10 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                65.607(6)
_cell_angle_beta                 80.571(5)
_cell_angle_gamma                89.902(5)
_cell_formula_units_Z            4
_cell_length_a                   6.1239(8)
_cell_length_b                   17.725(3)
_cell_length_c                   18.644(3)
_cell_measurement_reflns_used    7659
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.429
_cell_measurement_theta_min      2.304
_cell_volume                     1813.3(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1189
_diffrn_reflns_av_unetI/netI     0.1077
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28020
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.092
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1944 before and 0.1125 after correction.
The Ratio of minimum to maximum transmission is 0.3378.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0797
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1376P)^2^+0.2638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2013
_refine_ls_wR_factor_ref         0.2226
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4704
_reflns_number_total             6349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj03417d2.cif
_cod_data_source_block           3v
_cod_depositor_comments          'Adding full bibliography for 7061694.cif.'
_cod_database_code               7061694
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.926
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C18(H18), C28(H28), C39(H39)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C24(H24), C25(H25),
  C26(H26), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37),
 C41(H41), C43(H43), C44(H44), C45(H45), C46(H46)
;
_shelx_res_checksum              545
_olex2_submission_special_instructions 'No special instructions were received'