#------------------------------------------------------------------------------
#$Date: 2020-10-27 07:30:32 +0200 (Tue, 27 Oct 2020) $
#$Revision: 258611 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038923.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4038923
loop_
_publ_author_name
'Vogt, Astrid'
'Henne, Florian'
'Wetzel, Christoph'
'Mena-Osteritz, Elena'
'Bäuerle, Peter'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -19.00  31.00   1.00    4.00    --   -9.42 -99.00-150.00   50
  2  ω    -18.00  43.00   1.00    4.00    --   11.14 -99.00-150.00   61
  3  ω    -84.00  14.00   1.00    4.00    --   -9.42 -38.00 -60.00   98
  4  ω    -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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0274P)²+0.5639P] where P=(Fo²+2Fc²)/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 > 2σ(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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.01198(4) 0.08310(10) 0.85819(3) 0.02440(15) Uani 1 1 d . . . . .
O1 O -0.14000(12) 0.7115(3) 0.50124(7) 0.0276(3) Uani 1 1 d . . . . .
O2 O -0.25272(11) 0.8559(3) 0.59846(7) 0.0227(3) Uani 1 1 d . . . . .
N3 N -0.00874(13) 0.3407(3) 0.62758(9) 0.0198(3) Uani 1 1 d . . . . .
H3 H 0.019398 0.331148 0.580181 0.024 Uiso 1 1 calc R . . . .
C1 C -0.16444(15) 0.6987(4) 0.57392(10) 0.0193(4) Uani 1 1 d . . . . .
C2 C -0.12499(15) 0.4693(4) 0.72554(10) 0.0186(4) Uani 1 1 d . . . . .
H2 H -0.184017 0.557088 0.751612 0.022 Uiso 1 1 calc R . . . .
C3 C -0.10393(15) 0.5127(4) 0.64231(10) 0.0181(3) Uani 1 1 d . . . . .
C4 C 0.03277(15) 0.1889(4) 0.70107(10) 0.0191(4) Uani 1 1 d . . . . .
C5 C 0.12548(17) -0.0855(4) 0.81369(11) 0.0254(4) Uani 1 1 d . . . . .
H5 H 0.181089 -0.213547 0.844599 0.030 Uiso 1 1 calc R . . . .
C6 C -0.03834(16) 0.2649(4) 0.76216(10) 0.0183(3) Uani 1 1 d . . . . .
C7 C 0.12599(16) -0.0141(4) 0.73001(11) 0.0231(4) Uani 1 1 d . . . . .
H7 H 0.179647 -0.087713 0.696571 0.028 Uiso 1 1 calc R . . . .
C8 C -0.32004(17) 1.0390(4) 0.53214(11) 0.0255(4) Uani 1 1 d . . . . .
H8A H -0.373303 0.925682 0.490079 0.038 Uiso 1 1 calc GR . . . .
H8B H -0.263271 1.141183 0.504175 0.038 Uiso 1 1 calc GR . . . .
H8C H -0.368243 1.171749 0.558115 0.038 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S1 C5 90.79(8) . . ?
C1 O2 C8 115.28(12) . . ?
C4 N3 C3 108.16(13) . . ?
O1 C1 O2 122.90(15) . . ?
O1 C1 C3 124.69(16) . . ?
O2 C1 C3 112.41(14) . . ?
C3 C2 C6 105.33(14) . . ?
N3 C3 C1 119.38(14) . . ?
N3 C3 C2 109.90(14) . . ?
C2 C3 C1 130.72(16) . . ?
N3 C4 C6 107.69(15) . . ?
N3 C4 C7 137.30(16) . . ?
C6 C4 C7 115.01(15) . . ?
C7 C5 S1 114.26(14) . . ?
C2 C6 S1 141.14(13) . . ?
C4 C6 S1 109.93(13) . . ?
C4 C6 C2 108.91(14) . . ?
C5 C7 C4 110.00(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C5 1.7389(19) . ?
S1 C6 1.7316(17) . ?
O1 C1 1.2224(19) . ?
O2 C1 1.338(2) . ?
O2 C8 1.445(2) . ?
N3 C3 1.382(2) . ?
N3 C4 1.361(2) . ?
C1 C3 1.448(2) . ?
C2 C3 1.385(2) . ?
C2 C6 1.402(2) . ?
C4 C6 1.397(2) . ?
C4 C7 1.416(2) . ?
C5 C7 1.357(2) . ?
