Diastereoselective spirocyclopropanation of (<i>E</i>)-2-ylidene-3-cyclohexenones and sulfur ylides.
Li, Zheng-Yan; Zheng, Xing; Ma, Yi-Na; Yuan, Mingwei; Zhang, Yin; Jiang, Lin; Yuan, Minglong; Organic & biomolecular chemistry 23 (2025) 9592–9596; doi:10.1039/d5ob01383f

data_7160791
_publ_section_title
;
 Diastereoselective spirocyclopropanation of
 (<i>E</i>)-2-ylidene-3-cyclohexenones and sulfur ylides.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9592
_journal_page_last               9596
_journal_paper_doi               10.1039/d5ob01383f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C19 H16 O2 S'
_chemical_formula_sum            'C19 H16 O2 S'
_chemical_formula_weight         308.38
_chemical_name_systematic
(1R,2S,3S)-1-phenyl-2-(thiophene-2-carbonyl)spiro[2.5]oct-7-en-4-one
_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_update_record
;
2025-07-16 deposited with the CCDC.	2025-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.3039(2)
_cell_length_b                   7.84730(10)
_cell_length_c                   37.4016(6)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      68.1199
_cell_measurement_theta_min      2.3626
_cell_volume                     3024.21(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            17332
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         2.36
_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus
_exptl_absorpt_coefficient_mu    1.930
_exptl_absorpt_correction_T_max  0.73
_exptl_absorpt_correction_T_min  0.35
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1296
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.600
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0934P)^2^+1.8484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1529
_reflns_number_gt                2531
_reflns_number_total             2769
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01383f2.cif
_cod_data_source_block           md_jl3
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7160791.cif.
;
_cod_database_code               7160791
_shelx_res_checksum              68101