Diastereoselective cyclopropanation of α,β-unsaturated carbonyl compounds with vinyl sulfoxonium ylides.
Deshwal, Shalu; Gopalakrishnan, Dinesh Kumar; Purohit, Alok; Karmakar, Tarak; Vaitla, Janakiram; Organic & biomolecular chemistry 22 (2024) 6294–6307; doi:10.1039/d4ob00677a

data_7160044
_publ_section_title
;
 Diastereoselective cyclopropanation of &#x3b1;,&#x3b2;-unsaturated
 carbonyl compounds with vinyl sulfoxonium ylides.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6294
_journal_page_last               6307
_journal_paper_doi               10.1039/d4ob00677a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C30 H26 O6'
_chemical_formula_sum            'C30 H26 O6'
_chemical_formula_weight         482.51
_chemical_name_systematic        trans-cyclopropane
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2jvgb6
_audit_creation_date             2024-04-17
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-04-17 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                71.649(2)
_cell_angle_beta                 79.384(3)
_cell_angle_gamma                83.229(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6562(6)
_cell_length_b                   11.0892(6)
_cell_length_c                   13.6698(9)
_cell_measurement_reflns_used    7936
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      25.29
_cell_measurement_theta_min      2.40
_cell_volume                     1221.60(14)
_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)'
_diffrn_ambient_temperature      299.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0931
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            54112
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.444
_diffrn_reflns_theta_min         1.939
_diffrn_source_current           1.41
_diffrn_source_power             0.0705
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7216
_exptl_absorpt_correction_T_min  0.6780
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1160 before and 0.0935 after correction.
The Ratio of minimum to maximum transmission is 0.9396.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_preparation       'Crystallised in methanol'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5015
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      0.865
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0800P)^2^+0.5825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1551
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3573
_reflns_number_total             5015
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00677a2.cif
_cod_data_source_block           cp_ome_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160044--7160045.cif.'
_cod_database_code               7160044
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.979
_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. Rigid body (RIGU) restrains
 O01, C22, C12, C21, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22)=Sof(H22A)=Sof(H22B)=1-FVAR(1)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C007(H007), C00E(H00E)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C22(H22A,H22B)
4.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00V(H00V), C00W(H00W), C00X(H00X),
 C00Y(H00Y)
4.d Idealised Me refined as rotating group:
 C00T(H00A,H00B,H00C), C00U(H00D,H00F,H00G), C12(H12A,H12B,H12C), C21(H21A,
 H21B,H21C)
;
_shelx_res_checksum              21739
_olex2_submission_original_sample_id trans_cyclopropane
_olex2_submission_special_instructions 'No special instructions were received'