Unusual Oxidative Dimerization in the 3-Aminothieno[2,3-b]pyridine-2-carboxamide Series
Stroganova, Tatyana A.; Vasilin, Vladimir K.; Dotsenko, Victor V.; Aksenov, Nicolai A.; Morozov, Pavel G.; Vassiliev, Pavel M.; Volynkin, Vitaly A.; Krapivin, Gennady D.; ACS Omega  (2021) –; doi:10.1021/acsomega.1c00341

data_4518745
_publ_section_title
;
 Unusual Oxidative Dimerization in the
 3-Aminothieno[2,3-b]pyridine-2-carboxamide Series
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.1c00341
_journal_year                    2021
_chemical_formula_moiety         'C36 H36 N6 O4 S2, 2(C2 D6 O S)'
_chemical_formula_sum            'C40 H36 D12 N6 O6 S4'
_chemical_formula_weight         849.16
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                75.757(2)
_cell_angle_beta                 83.114(2)
_cell_angle_gamma                66.615(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0531(3)
_cell_length_b                   12.6868(3)
_cell_length_c                   16.6049(5)
_cell_measurement_reflns_used    16779
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8970
_cell_measurement_theta_min      4.1860
_cell_volume                     2070.87(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -84.00  18.00   1.00    1.50    --  -41.60 101.00 140.00  102
  2  \w    101.00 178.00   1.00    6.00    --  112.00 101.00 140.00   77
  3  \w     32.00 112.00   1.00    6.00    --  112.00-101.00  35.00   80
  4  \w   -114.00 -13.00   1.00    1.50    --  -41.60 -57.00   0.00  101
  5  \w      4.00  84.00   1.00    1.50    --   41.60-101.00  35.00   80
  6  \w      5.00  33.00   1.00    1.50    --   42.00  89.00  50.89   28
  7  \w     12.00  40.00   1.00    1.50    --   46.00  83.00 -85.95   28
  8  \w     11.00  38.00   1.00    1.50    --   46.00  84.00 164.28   27
  9  \w     15.00 120.00   1.00    1.50    --   46.00  72.00 -54.74  105
 10  \w     20.00  46.00   1.00    1.50    --   54.00  81.00-122.69   26
 11  \w     60.00 159.00   1.00    6.00    --   86.00  45.00-124.54   99
 12  \w     79.00 178.00   1.00    6.00    --  112.00  77.00-180.00   99
 13  \w     84.00 178.00   1.00    6.00    --  112.00  30.00  30.00   94
 14  \w     36.00 116.00   1.00    6.00    --  112.00-111.00   0.00   80
 15  \w     86.00 178.00   1.00    6.00    --  112.00  45.00 120.00   92
 16  \w     83.00 178.00   1.00    6.00    --  112.00  61.00 -60.00   95
 17  \w     30.00 109.00   1.00    6.00    --  112.00 -95.00  60.00   79
 18  \w    100.00 178.00   1.00    6.00    --  112.00 111.00  60.00   78
 19  \w     36.00 116.00   1.00    6.00    --  112.00-111.00 -60.00   80
 20  \w     57.00 151.00   1.00    6.00    --  112.00 178.00-150.00   94
 21  \w     57.00 151.00   1.00    6.00    --  112.00 178.00 -30.00   94
 22  \w     30.00 109.00   1.00    6.00    --  112.00 -95.00-150.00   79
 23  \w     30.00 109.00   1.00    6.00    --  112.00 -95.00 -90.00   79
 24  \w    100.00 178.00   1.00    6.00    --  112.00 111.00 -60.00   78
 25  \w     36.00 116.00   1.00    6.00    --  112.00-111.00-180.00   80
 26  \w     86.00 178.00   1.00    6.00    --  112.00  45.00-120.00   92
 27  \w     30.00 109.00   1.00    6.00    --  112.00 -95.00-120.00   79
 28  \w     36.00 116.00   1.00    6.00    --  112.00-111.00  90.00   80
 29  \w     57.00 151.00   1.00    6.00    --  112.00 178.00-180.00   94
 30  \w     36.00 116.00   1.00    6.00    --  112.00-111.00  30.00   80
 31  \w    153.00 178.00   1.00    6.00    --  112.00 111.00 -90.00   25
 32  \w     70.00 114.00   1.00    6.00    --  112.00-111.00-150.00   44
 33  \w     39.00 138.00   1.00    6.00    --  112.00 -45.00  30.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0212356000
_diffrn_orient_matrix_UB_12      -0.1288714000
_diffrn_orient_matrix_UB_13      0.0044903000
_diffrn_orient_matrix_UB_21      -0.0498957000
_diffrn_orient_matrix_UB_22      -0.0119045000
_diffrn_orient_matrix_UB_23      0.0911946000
_diffrn_orient_matrix_UB_31      -0.1418901000
_diffrn_orient_matrix_UB_32      0.0403066000
_diffrn_orient_matrix_UB_33      -0.0288343000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30796
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.494
_diffrn_reflns_theta_min         3.889
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.547
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       irregular
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.236
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     531
_refine_ls_number_reflns         8458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0681P)^2^+2.0654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1363
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7911
_reflns_number_total             8458
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c00341_si_002.cif
_cod_data_source_block           anna_10182017_sta5712_3
_cod_database_code               4518745
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C35(H35A,H35B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18), C27(H27), C28(H28), C11(H11), C21(H21), C3(H3), C22(H22),
 C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C32(H32A,H32B,H32C), C39(D39A,D39B,D39C), C40(D40A,D40B,
 D40C), C30(H30A,H30B,H30C), C36(H36A,H36B,H36C), C37(D37A,D37B,D37C), C31(H31A,
 H31B,H31C), C34(H34A,H34B,H34C), C38(D38A,D38B,D38C)
;
_shelx_res_checksum              95807
_shelx_hkl_checksum              61812
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.458
_oxdiff_exptl_absorpt_empirical_full_min 0.482