Synthesis and characterization of S,N-heterotetracenes
Vogt, Astrid; Henne, Florian; Wetzel, Christoph; Mena-Osteritz, Elena; Bäuerle, Peter; Beilstein Journal of Organic Chemistry 16 (2020) 2636–2644; doi:10.3762/bjoc.16.214

data_4038923
_publ_section_title
;
 Synthesis and characterization of S,N-heterotetracenes
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              2636
_journal_page_last               2644
_journal_paper_doi               10.3762/bjoc.16.214
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         'C8 H7 N O2 S'
_chemical_formula_sum            'C8 H7 N O2 S'
_chemical_formula_weight         181.21
_chemical_name_systematic        Methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-07-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.785(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0745(8)
_cell_length_b                   4.6972(3)
_cell_length_c                   15.6995(9)
_cell_measurement_reflns_used    2730
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.6210
_cell_measurement_theta_min      4.0400
_cell_volume                     802.25(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.882
_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    -19.00  31.00   1.00    4.00    --   -9.42 -99.00-150.00   50
  2  \w    -18.00  43.00   1.00    4.00    --   11.14 -99.00-150.00   61
  3  \w    -84.00  14.00   1.00    4.00    --   -9.42 -38.00 -60.00   98
  4  \w    -89.00   3.00   1.00    4.00    --   -9.42 -19.00  30.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0570733000
_diffrn_orient_matrix_UB_12      -0.0532312000
_diffrn_orient_matrix_UB_13      0.0224853000
_diffrn_orient_matrix_UB_21      -0.0313620000
_diffrn_orient_matrix_UB_22      -0.0850494000
_diffrn_orient_matrix_UB_23      0.0262333000
_diffrn_orient_matrix_UB_31      -0.0032484000
_diffrn_orient_matrix_UB_32      -0.1128332000
_diffrn_orient_matrix_UB_33      -0.0303495000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6335
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.464
_diffrn_reflns_theta_min         3.746
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.355
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_preparation       'Chloroform solution'
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0049(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0274P)^2^+0.5639P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1601
_reflns_number_total             1974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-16-214-S2.cif
_cod_data_source_block           fhe18048
_cod_original_cell_volume        802.26(9)
_cod_database_code               4038923
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C8 H7 N O2 S'
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C5(H5), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_olex2_date_sample_data_collection 2018-08-22
_olex2_submission_original_sample_id 'Met-Thienopyrrole-carboxylate '
_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 1.208
_oxdiff_exptl_absorpt_empirical_full_min 0.801