Construction of sulfur-substituted methylenecyclobutanes via thioaromatization of [1.1.1]propellane with sulfenamides
Hong, Jun; Wu, Tianbao; Yu, Zhihao; Zhu, Yu; Tang, Daijun; Wang, Minyan; Jiang, Xinpeng; Green Chemistry 28 (2026) 3226–3231; doi:10.1039/D5GC05901A

data_7251603
_publ_section_title
;
 Construction of sulfur-substituted methylenecyclobutanes via
 thioaromatization of [1.1.1]propellane with sulfenamides
;
_journal_issue                   7
_journal_name_full               'Green Chemistry'
_journal_page_first              3226
_journal_page_last               3231
_journal_paper_doi               10.1039/D5GC05901A
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C17 H16 Br N S'
_chemical_formula_sum            'C17 H16 Br N S'
_chemical_formula_weight         346.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-01
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-07-05 deposited with the CCDC.	2026-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.2640(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4027(4)
_cell_length_b                   12.8347(5)
_cell_length_c                   13.5644(5)
_cell_measurement_reflns_used    7654
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.697
_cell_measurement_theta_min      4.231
_cell_volume                     1554.50(11)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14153
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.798
_diffrn_reflns_theta_min         4.230
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    3.146
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1601 before and 0.0704 after correction.
The Ratio of minimum to maximum transmission is 0.8972.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0339P)^2^+0.7755P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3253
_reflns_number_total             3532
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc05901a2.cif
_cod_data_source_block           240625_hj_3_150_0m
_cod_database_code               7251603
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.884
_shelx_estimated_absorpt_t_min   0.834
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Rotating group:
 N1(H1A,H1B)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
;
_olex2_submission_special_instructions 'No special instructions were received'