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_7132854
_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 H14 O2'
_chemical_formula_sum            'C21 H14 O2'
_chemical_formula_weight         298.32
_chemical_name_systematic        'Naphthylidene butenolide'
_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   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2hnqgc
_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                90
_cell_angle_beta                 98.770(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1483(7)
_cell_length_b                   18.7780(15)
_cell_length_c                   9.9744(8)
_cell_measurement_reflns_used    6652
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      2.33
_cell_volume                     1508.3(2)
_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      298.00
_diffrn_measured_fraction_theta_full 0.999
_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  0.1039
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            47156
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.169
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6884
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1464 before and 0.0716 after correction.
The Ratio of minimum to maximum transmission is 0.9232.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_preparation       'As mentioned in 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         0.141
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.018(2)
_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   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0585
_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^)+(0.0520P)^2^+0.1853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1262
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1793
_reflns_number_total             2951
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00450g2.cif
_cod_data_source_block           021223_a512_0m_a
_cod_depositor_comments
'Adding full bibliography for 7132854--7132855.cif.'
_cod_database_code               7132854
_shelx_shelxl_version_number     2019/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C008(H008), C009(H009), C00C(H00C), C00D(H00D), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N)
;
_shelx_res_checksum              87726
_shelx_hkl_checksum              78392
_olex2_submission_original_sample_id 'Naphthylidene butenolide'
_olex2_submission_special_instructions 'No special instructions were received'