Carbene-mediated stereoselective olefination of vinyl sulfoxonium ylides with diazo compounds and acetals.
Gopalakrishnan, Dinesh Kumar; Bhardwaj, Srashti; Kumar, Sandeep; Karmakar, Tarak; Vaitla, Janakiram; Chemical communications (Cambridge, England) 60 (2024) 3846–3849; doi:10.1039/d4cc00450g

data_7132855
_publ_section_title
;
 Carbene-mediated stereoselective olefination of vinyl sulfoxonium ylides
 with diazo compounds and acetals.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3846
_journal_page_last               3849
_journal_paper_doi               10.1039/d4cc00450g
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C21 H18 O4'
_chemical_formula_sum            'C21 H18 O4'
_chemical_formula_weight         334.35
_chemical_name_systematic        Dienoate
_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.cc2hnqkg
_audit_creation_date             2023-12-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-12 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                91.975(4)
_cell_angle_beta                 93.296(4)
_cell_angle_gamma                108.179(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4870(10)
_cell_length_b                   10.1115(12)
_cell_length_c                   10.5324(11)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.73
_cell_measurement_theta_min      2.53
_cell_volume                     856.01(17)
_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      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_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  0.0448
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            42554
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.304
_diffrn_reflns_theta_min         2.123
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6962
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0782 before and 0.0568 after correction.
The Ratio of minimum to maximum transmission is 0.9327.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dull whiteish white'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_preparation       'As mentioned in the paper'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         6039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0508
_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^)+(0.0858P)^2^+0.1571P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1675
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4272
_reflns_number_total             6039
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00450g2.cif
_cod_data_source_block           121223_6mem_1_0m_a
_cod_depositor_comments
'Adding full bibliography for 7132854--7132855.cif.'
_cod_database_code               7132855
_shelx_shelxl_version_number     2019/1
_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 Secondary CH2 refined with riding coordinates:
 C00E(H00B,H00C), C00O(H00E,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N)
2.c Idealised Me refined as rotating group:
 C00P(H00O,H00P,H00Q)
;
_shelx_res_checksum              47481
_shelx_hkl_checksum              27557
_olex2_submission_original_sample_id Dienoate
_olex2_submission_special_instructions 'No special instructions were received'