B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-catalyzed cyclopropanation of 3-alkenyl-oxindoles with diazomethanes.
Xiao, Lei; Jin, Lvnan; Zhao, Yunbo; Guo, Jing; Stephan, Douglas W.; Chemical communications (Cambridge, England) 59 (2023) 1833–1836; doi:10.1039/d2cc06744g

data_7131221
_publ_section_title
;
 B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-catalyzed cyclopropanation of
 3-alkenyl-oxindoles with diazomethanes.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1833
_journal_page_last               1836
_journal_paper_doi               10.1039/d2cc06744g
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C27 H22 Br N O5'
_chemical_formula_sum            'C27 H22 Br N O5'
_chemical_formula_weight         520.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-12-10
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-10 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2115(3)
_cell_length_b                   14.3699(3)
_cell_length_c                   24.8145(5)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      3.56
_cell_volume                     4710.98(17)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            36413
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.562
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.706
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6383
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1224 before and 0.0578 after correction.
The Ratio of minimum to maximum transmission is 0.8476.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       block
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0397P)^2^+1.5452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0764
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3775
_reflns_number_total             4300
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06744g2.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 7131220--7131221.cif.'
_cod_database_code               7131221
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C26(H26), C27(H27), C9(H9), C24(H24), C5(H5), C12(H12), C10(H10),
 C4(H4), C1(H1), C11(H11), C3(H3), C2(H2)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              56038
_shelx_hkl_checksum              8076
_olex2_submission_special_instructions 'No special instructions were received'