Annulation of quinone methides with 2-benzylidene dithiolanes: synthesis of spirochroman dithiolanes.
Singh, Surya Pratap; Arora, Shivani; Bhardwaj, Prashant Kumar; Singh, Anand; Organic & biomolecular chemistry 21 (2023) 4962–4966; doi:10.1039/d3ob00583f

data_7159399
_publ_section_title
;
 Annulation of quinone methides with 2-benzylidene dithiolanes: synthesis
 of spirochroman dithiolanes.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4962
_journal_page_last               4966
_journal_paper_doi               10.1039/d3ob00583f
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C32 H35 Cl O3 S2'
_chemical_formula_sum            'C32 H35 Cl O3 S2'
_chemical_formula_weight         567.17
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-06
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2021-12-06 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                61.943(2)
_cell_angle_beta                 71.660(2)
_cell_angle_gamma                74.099(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3448(6)
_cell_length_b                   12.6474(7)
_cell_length_c                   13.0332(8)
_cell_measurement_reflns_used    9663
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.33
_cell_volume                     1412.12(15)
_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      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_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  0.0525
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21388
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.347
_diffrn_reflns_theta_min         2.098
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6153
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0954 before and 0.0663 after correction. The Ratio of minimum to maximum transmission is 0.8251. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear yellowish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         6997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0152P)^2^+1.9230P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5439
_reflns_number_total             6997
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00583f2.cif
_cod_data_source_block           9nova_0m
_cod_database_code               7159399
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.911
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C32(H32), C16(H16), C7(H7), C11(H11), C13(H13), C8(H8), C14(H14),
 C10(H10), C15(H15)
2.d Tetrahedral OH refined with riding coordinates:
 O3(H3)
2.e Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C29(H29A,H29B,H29C), C25(H25A,H25B,
 H25C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              68443
_shelx_hkl_checksum              42990
_olex2_submission_special_instructions 'No special instructions were received'