Phosphine catalyzed [3+2] cyclization/Michael addition of allenoate with CS<sub>2</sub> to form 2-thineyl vinyl sulfide.
Fei, Weihong; Xu, Ping; Hou, Jie; Yao, Weijun; Chemical communications (Cambridge, England) 56 (2020) 11669–11672; doi:10.1039/d0cc05070a

data_7127108
_publ_section_title
;
 Phosphine catalyzed [3+2] cyclization/Michael addition of allenoate with
 CS<sub>2</sub> to form 2-thineyl vinyl sulfide.
;
_journal_issue                   78
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11669
_journal_page_last               11672
_journal_paper_doi               10.1039/d0cc05070a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C25 H24 O4 S2'
_chemical_formula_sum            'C25 H24 O4 S2'
_chemical_formula_weight         452.56
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-24 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.154(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.917(3)
_cell_length_b                   7.526(3)
_cell_length_c                   28.688(11)
_cell_measurement_reflns_used    9848
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.06
_cell_measurement_theta_min      2.71
_cell_volume                     2320.1(14)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_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  0.0330
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            38600
_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         30.548
_diffrn_reflns_theta_min         2.576
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0972 before and 0.0465 after correction.
The Ratio of minimum to maximum transmission is 0.9073.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.664
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         7096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0655P)^2^+0.7782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5515
_reflns_number_total             7096
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05070a2.cif
_cod_data_source_block           190429_fx023_0m
_cod_depositor_comments          'Adding full bibliography for 7127108.cif.'
_cod_database_code               7127108
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.847
_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:
 C20(H20A,H20B), C22(H22A,H22B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              26455
_shelx_hkl_checksum              4842
_olex2_submission_special_instructions 'No special instructions were received'