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_7131220
_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 H23 N O4'
_chemical_formula_sum            'C27 H23 N O4'
_chemical_formula_weight         425.46
_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             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                71.0100(10)
_cell_angle_beta                 73.2780(10)
_cell_angle_gamma                75.2040(10)
_cell_formula_units_Z            2
_cell_length_a                   8.7528(2)
_cell_length_b                   10.3009(2)
_cell_length_c                   13.3655(2)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      68.38
_cell_measurement_theta_min      5.02
_cell_volume                     1073.74(4)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0362
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18612
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.375
_diffrn_reflns_theta_min         3.588
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6936
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0857 before and 0.0465 after correction.
The Ratio of minimum to maximum transmission is 0.9210.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.031
_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     290
_refine_ls_number_reflns         3853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0345P)^2^+0.2899P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3572
_reflns_number_total             3853
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06744g2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7131220--7131221.cif.'
_cod_database_code               7131220
_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:
 C5(H5), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C26(H26), C25(H25), C17(H17), C24(H24), C12(H12), C21(H21), C8(H8),
 C18(H18), C20(H20), C9(H9), C19(H19), C11(H11), C10(H10)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              5788
_shelx_hkl_checksum              55312
_olex2_submission_special_instructions 'No special instructions were received'