Synthesis, crystal structure and conformational analysis of an unexpected [1,5]dithiocine product of aminopyridine and thiovanillin
Mambourg, Kalina; Bodart, Laurie; Tumanov, Nikolay; Lanners, Steve; Wouters, Johan; Acta Crystallographica Section C Structural Chemistry 76 (2020) –; doi:10.1107/S2053229620000996

data_2021975
_publ_section_title
;
 Synthesis, crystal structure and conformational analysis of an unexpected
 [1,5]dithiocine product of aminopyridine and thiovanillin
;
_journal_coeditor_code           EP3003
_journal_issue                   3
_journal_name_full
'Acta Crystallographica Section C Structural Chemistry'
_journal_paper_doi               10.1107/S2053229620000996
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C21 H18 N2 O2 S2, 0.463C H4 O'
_chemical_formula_moiety         'C21 H18 N2 O2 S2, 0.463(C H4 O)'
_chemical_formula_sum            'C21.46 H19.85 N2 O2.46 S2'
_chemical_formula_weight         409.34
_chemical_name_systematic
'4,10-Dimethoxy-13-(pyridin-3-yl)-6<i>H</i>,12<i>H</i>-6,12-epiminodibenzo[<i>b</i>,<i>f</i>][1,5]dithiocine methanol 0.463-solvate'
_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
_atom_sites_solution_secondary   dual
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                84.662(2)
_cell_angle_beta                 73.498(2)
_cell_angle_gamma                68.886(2)
_cell_formula_units_Z            8
_cell_length_a                   14.7387(4)
_cell_length_b                   16.6445(3)
_cell_length_c                   17.8970(4)
_cell_measurement_reflns_used    18138
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      67.0
_cell_measurement_theta_min      2.8
_cell_volume                     3926.80(17)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2020)
;
_computing_publication_material
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b),
OLEX2 (Dolomanov <i>et al.</i>, 2009) and
ShelXle (H\"ubschle <i>et al.</i>, 2011)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 5.1856
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Xcalibur Ruby Gemini Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33207
_diffrn_reflns_theta_full        67.122
_diffrn_reflns_theta_max         67.122
_diffrn_reflns_theta_min         2.575
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.644
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_correction_T_min  0.414
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis PRO (Rigaku OD, 2018), based on expressions derived by
Clark & Reid (1995)]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1715
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.339
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1184
_refine_ls_number_reflns         13626
_refine_ls_number_restraints     838
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0560P)^2^+0.8423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                12152
_reflns_number_total             13626
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ep3003sup1.cif
_cod_data_source_block           I
_cod_database_code               2021975
_shelx_estimated_absorpt_t_min   0.376
_shelx_estimated_absorpt_t_max   0.857
_shelx_hkl_checksum              57457
_shelx_res_checksum              72250
_cod_database_fobs_code 2021975