data_fhe18048
_audit_creation_date               2020-07-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2016/6'
loop_
  _audit_author_name
  _audit_author_email
  _audit_author_address
 'Vogt, A.' astrid.vogt@uni-ulm.de
;

Ulm University
Institute of Organic Chemistry II and Advanced Materials
Albert-Einstein-Allee 11
Ulm
89081
Germany
;
 'Henne, F.' florian.henne@uni-ulm.de
;

Ulm University
Institute of Organic Chemistry II and Advanced Materials
Albert-Einstein-Allee 11
Ulm
89081
Germany
;
 'Mena-Osteritz, E.' elena.mena-osteritz@uni-ulm.de
;

Ulm University
Institute of Organic Chemistry II and Advanced Materials
Albert-Einstein-Allee 11
Ulm
89081
Germany
;
 'Baeuerle, P.' peter.baeuerle@uni-ulm.de
;

Ulm University
Institute of Organic Chemistry II and Advanced Materials
Albert-Einstein-Allee 11
Ulm
89081
Germany
;

_audit_contact_author_address
;
Ulm University
Institute of Organic Chemistry II and Advanced Materials
Albert-Einstein-Allee 11
Ulm
89081
Germany
;
_audit_contact_author_email        peter.baeuerle@uni-ulm.de
_audit_contact_author_name         'Baeuerle, P.'
_audit_contact_author_phone        ''
_publ_contact_author_id_orcid      ''
_publ_requested_journal            'Beilstein J.Org.Chem.'
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          Methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate
_chemical_formula_moiety           'C8 H7 N O2 S'
_chemical_formula_sum              'C8 H7 N O2 S'
_chemical_formula_weight           181.21
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C8 H7 N O2 S'
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'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
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'

_cell_length_a                     11.0745(8)
_cell_length_b                     4.6972(3)
_cell_length_c                     15.6995(9)
_cell_angle_alpha                  90
_cell_angle_beta                   100.785(6)
_cell_angle_gamma                  90
_cell_volume                       802.26(9)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      2730
_cell_measurement_temperature      150.00(10)
_cell_measurement_theta_max        28.6210
_cell_measurement_theta_min        4.0400
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_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_absorpt_special_details     ?
_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_density_meas        ?
_exptl_crystal_density_method      ?
_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
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_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_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_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  1601
_reflns_number_total               1974
_reflns_odcompleteness_completeness  99.73
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       26.32
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_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)'
_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_R_factor_all            0.0513
_refine_ls_R_factor_gt             0.0367
_refine_ls_restrained_S_all        1.032
_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
_refine_special_details            ?
_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)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       direct
_atom_sites_solution_secondary     ?
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 . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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) . ?

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) . . ?


_database_code_depnum_ccdc_archive  ?
_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
