Bronsted acid-catalyzed chemodivergent reactions of ortho-mercaptobenzyl alcohols with 3-alkyl-2-vinylindoles and styrenes: [5+2] cyclization versus hydroxysulfenylation
Jia-Jia Zhao; Man Tang; Hong-Hao Zhang; Meng-Meng Xu; Feng Shi; Chem.Commun. 52 (2016) 5953–; doi:

data_7119041
_publ_section_title
;
 Bronsted acid-catalyzed chemodivergent reactions of ortho-mercaptobenzyl
 alcohols with 3-alkyl-2-vinylindoles and styrenes: [5+2] cyclization
 versus hydroxysulfenylation
;
_journal_name_full               Chem.Commun.
_journal_page_first              5953
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C26 H25 N O S'
_chemical_formula_sum            'C26 H25 N O S'
_chemical_formula_weight         399.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-01-27 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                64.811(14)
_cell_angle_beta                 88.065(15)
_cell_angle_gamma                80.753(17)
_cell_formula_units_Z            2
_cell_length_a                   8.280(7)
_cell_length_b                   11.804(10)
_cell_length_c                   12.324(10)
_cell_measurement_reflns_used    1821
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.15
_cell_measurement_theta_min      2.49
_cell_volume                     1075.0(16)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10942
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.700
_diffrn_reflns_theta_min         1.827
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0476 before and 0.0372 after correction.
The Ratio of minimum to maximum transmission is 0.8654.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         6542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0619P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1454
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3435
_reflns_number_total             6542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc00920d2.cif
_cod_data_source_block           mo_dm15515_0m
_cod_original_cell_volume        1075.0(15)
_cod_database_code               7119041
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              59537
_shelx_hkl_checksum              76072
_olex2_submission_special_instructions 'No special instructions were received'