Sulphur ylide-mediated cyclopropanation and subsequent spirocyclopropane rearrangement reactions.
Dai, Qing-Song; Li, Jun-Long; Wang, Qi-Wei; Yang, Si-Lin; Tao, Ying-Mao; He, Mei-Hao; Li, Qing-Zhu; Han, Bo; Zhang, Xiang; Organic & biomolecular chemistry 20 (2022) 3486–3490; doi:10.1039/d2ob00466f

data_7158592
_publ_section_title
;
 Sulphur ylide-mediated cyclopropanation and subsequent spirocyclopropane
 rearrangement reactions.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3486
_journal_page_last               3490
_journal_paper_doi               10.1039/d2ob00466f
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C28 H20 N2 O3 S2'
_chemical_formula_sum            'C28 H20 N2 O3 S2'
_chemical_formula_weight         496.58
_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             2022-03-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-03-04 deposited with the CCDC.	2022-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                112.336(3)
_cell_angle_beta                 91.537(3)
_cell_angle_gamma                112.501(3)
_cell_formula_units_Z            2
_cell_length_a                   11.4722(9)
_cell_length_b                   11.6024(9)
_cell_length_c                   11.8100(11)
_cell_measurement_reflns_used    5926
_cell_measurement_temperature    185(2)
_cell_measurement_theta_max      26.685
_cell_measurement_theta_min      2.442
_cell_volume                     1315.8(2)
_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      185.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_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  0.0948
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29591
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.571
_diffrn_reflns_theta_min         1.962
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1359 before and 0.0795 after correction.
The Ratio of minimum to maximum transmission is 0.8124.
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    1.253
_exptl_crystal_description       plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         6044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0552P)^2^+0.2234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1357
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4037
_reflns_number_total             6044
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00466f2.cif
_cod_data_source_block           mo_ljl_dqs_0304_160k_0m_a
_cod_depositor_comments
'Adding full bibliography for 7158590--7158592.cif.'
_cod_original_cell_volume        1315.76(19)
_cod_database_code               7158592
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.906
_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. Uiso/Uaniso restraints and constraints
Uanis(S2A) = Uanis(S2)
3. Others
 Sof(H15A)=Sof(S2A)=1-FVAR(1)
 Sof(S2)=Sof(H15)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C24(H24)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C15(H15A), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C27(H27), C28(H28), C29(H29), C30(H30),
  C31(H31)
4.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              18633
_shelx_fab_checksum              31878
_olex2_submission_special_instructions 'No special instructions were received'