#------------------------------------------------------------------------------
#$Date: 2018-09-22 05:14:24 +0300 (Sat, 22 Sep 2018) $
#$Revision: 211114 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/26/2242644.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2242644
loop_
_publ_author_name
'Gibbons, Dáire'
'Emandi, Ganapathi'
'Senge, Mathias O.'
_publ_section_title
;
 Crystal structure and synthesis of
 3-(1H-pyrrol-2-yl)-1-(thiophen-2-yl)propanone
;
_journal_coeditor_code           TX2008
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1463
_journal_page_last               1466
_journal_paper_doi               10.1107/S2056989018012331
_journal_volume                  74
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C11 H9 N O S'
_chemical_formula_moiety         'C11 H9 N O S'
_chemical_formula_sum            'C11 H9 N O S'
_chemical_formula_weight         203.25
_chemical_name_systematic
;
3-(1H-Pyrrol-2-yl)-1-(thiophen-2-yl)propanone
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1559(3)
_cell_length_b                   3.92580(10)
_cell_length_c                   21.6293(6)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.65
_cell_volume                     947.27(4)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEXII area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEXII area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         1.883
_diffrn_source                   'standard sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triangular
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.167
_refine_ls_abs_structure_details
;
Flack x determined using 956 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2159
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0321
_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)+(0.0533P)²+0.3056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                2070
_reflns_number_total             2159
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2008sup1.cif
_cod_data_source_block           I
_cod_database_code               2242644
_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.
;
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.979
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.4383(3) 0.3593(7) 0.30581(13) 0.0220(6) Uani d 1
H H1 0.4090 0.2839 0.2669 0.026 Uiso calc 1
C C2 0.5545(3) 0.3241(7) 0.32434(13) 0.0199(5) Uani d 1
H H2 0.6149 0.2208 0.2997 0.024 Uiso calc 1
C C3 0.5754(2) 0.4580(6) 0.38425(12) 0.0146(5) Uani d 1
H H3 0.6510 0.4546 0.4045 0.018 Uiso calc 1
C C4 0.4712(2) 0.5956(7) 0.40983(12) 0.0154(5) Uani d 1
C C5 0.4521(2) 0.7623(7) 0.46958(11) 0.0158(5) Uani d 1
C C6 0.5566(2) 0.7940(7) 0.51008(13) 0.0167(5) Uani d 1
H H6 0.6303 0.6917 0.4983 0.020 Uiso calc 1
C C7 0.5498(2) 0.9663(7) 0.56396(12) 0.0166(5) Uani d 1
H H7 0.4753 1.0719 0.5733 0.020 Uiso calc 1
C C8 0.6436(2) 1.0055(7) 0.60829(13) 0.0160(5) Uani d 1
C C9 0.6393(2) 1.1517(7) 0.66686(12) 0.0183(5) Uani d 1
H H9 0.5713 1.2570 0.6852 0.022 Uiso calc 1
C C10 0.7529(3) 1.1168(7) 0.69428(12) 0.0195(5) Uani d 1
H H10 0.7758 1.1928 0.7343 0.023 Uiso calc 1
C C11 0.8247(2) 0.9509(7) 0.65194(13) 0.0182(6) Uani d 1
H H11 0.9065 0.8924 0.6579 0.022 Uiso calc 1
N N1 0.7588(2) 0.8850(6) 0.60020(11) 0.0179(5) Uani d 1
H H1A 0.787(3) 0.791(9) 0.5687(16) 0.019(8) Uiso d 1
O O1 0.35144(16) 0.8661(6) 0.48409(9) 0.0199(4) Uani d 1
S S1 0.35151(5) 0.55340(15) 0.36015(3) 0.01928(17) Uani d 1
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
C2 C1 H1 123.7
C2 C1 S1 112.5(2)
S1 C1 H1 123.7
C1 C2 H2 123.6
C1 C2 C3 112.8(3)
C3 C2 H2 123.6
C2 C3 H3 124.2
C4 C3 C2 111.6(2)
C4 C3 H3 124.2
C3 C4 C5 130.0(2)
C3 C4 S1 111.2(2)
C5 C4 S1 118.77(19)
C6 C5 C4 116.8(2)
O1 C5 C4 120.2(2)
O1 C5 C6 122.9(2)
C5 C6 H6 119.5
C7 C6 C5 121.0(2)
C7 C6 H6 119.5
C6 C7 H7 116.8
C6 C7 C8 126.4(3)
C8 C7 H7 116.8
C9 C8 C7 129.1(2)
N1 C8 C7 124.1(2)
N1 C8 C9 106.8(2)
C8 C9 H9 125.9
C8 C9 C10 108.2(2)
C10 C9 H9 125.9
C9 C10 H10 126.6
C11 C10 C9 106.8(2)
C11 C10 H10 126.6
C10 C11 H11 125.6
N1 C11 C10 108.7(2)
N1 C11 H11 125.6
C8 N1 H1A 127(2)
C11 N1 C8 109.4(2)
C11 N1 H1A 124(2)
C1 S1 C4 91.90(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 H1 0.9500
C1 C2 1.364(4)
C1 S1 1.702(3)
C2 H2 0.9500
C2 C3 1.418(4)
C3 H3 0.9500
C3 C4 1.397(4)
C4 C5 1.464(3)
C4 S1 1.722(3)
C5 C6 1.463(3)
C5 O1 1.236(3)
C6 H6 0.9500
C6 C7 1.350(4)
C7 H7 0.9500
C7 C8 1.428(4)
C8 C9 1.392(4)
C8 N1 1.381(3)
C9 H9 0.9500
C9 C10 1.406(4)
C10 H10 0.9500
C10 C11 1.380(4)
C11 H11 0.9500
C11 N1 1.364(4)
N1 H1A 0.84(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O1 3_565 0.84(4) 2.06(4) 2.889(3) 171(3)
C6 H6 O1 3_565 0.95 2.50 3.396(3) 158
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C1 C2 C3 C4 -0.2(3)
C2 C1 S1 C4 0.4(2)
C2 C3 C4 C5 -179.2(2)
C2 C3 C4 S1 0.5(3)
C3 C4 C5 C6 0.0(4)
C3 C4 C5 O1 -179.5(3)
C3 C4 S1 C1 -0.5(2)
C4 C5 C6 C7 175.0(2)
C5 C4 S1 C1 179.2(2)
C5 C6 C7 C8 177.7(2)
C6 C7 C8 C9 -173.4(3)
C6 C7 C8 N1 3.8(4)
C7 C8 C9 C10 177.3(3)
C7 C8 N1 C11 -177.4(3)
C8 C9 C10 C11 0.2(3)
C9 C8 N1 C11 0.3(3)
C9 C10 C11 N1 0.0(3)
C10 C11 N1 C8 -0.2(3)
N1 C8 C9 C10 -0.3(3)
O1 C5 C6 C7 -5.6(4)
S1 C1 C2 C3 -0.2(3)
S1 C4 C5 C6 -179.67(19)
S1 C4 C5 O1 0.9(3)

_cod_database_fobs_code 2242644
