#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/73/2017300.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_2017300
loop_
_publ_author_name
'Cobo, Debora'
'Quiroga, Jairo'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 (E)-3-(4-Methylphenyl)-2-(2-thienyl)acrylonitrile has Z'
 = 0.75 in the space group C2/m: fourfold disordered
 molecules lie in channels enclosed by fully ordered molecules
;
_journal_coeditor_code           GG3209
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o444
_journal_page_last               o446
_journal_paper_doi               10.1107/S0108270109029667
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H11 N1 S1'
_chemical_formula_moiety         'C14 H11 N1 S1'
_chemical_formula_sum            'C14 H11 N S'
_chemical_formula_weight         225.31
_chemical_melting_point          380
_chemical_name_systematic
;
(E)-3-(4-Methylphenyl)-2-(2-thienyl)acrylonitrile
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 126.173(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   21.4869(7)
_cell_length_b                   7.0302(3)
_cell_length_c                   14.1810(5)
_cell_measurement_reflns_used    2133
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.56
_cell_volume                     1729.22(12)
_computing_cell_refinement       'DENZO--SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction
'DENZO--SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9286
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.56
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.250
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2133
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.239
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0583
_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/[σ²(Fo²)+(0.0000P)²+5.111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1324
_reflns_number_gt                1956
_reflns_number_total             2133
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3209.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_original_formula_sum        'C14 H11 N1 S1'
_cod_database_code               2017300
_cod_database_fobs_code          2017300
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.30694(5) 0.5000 0.35009(7) 0.0323(2) Uani d SD 1 A 1
C C2 0.21398(17) 0.5000 0.2247(2) 0.0259(7) Uani d SD 1 A 1
C C3 0.16158(18) 0.5000 0.2507(3) 0.0313(8) Uani d SD 1 A 1
H H3 0.1073 0.5000 0.1935 0.038 Uiso calc SR 1 A 1
C C4 0.1983(2) 0.5000 0.3735(3) 0.0380(9) Uani d SD 1 A 1
H H4 0.1711 0.5000 0.4072 0.046 Uiso calc SR 1 A 1
C C5 0.2758(2) 0.5000 0.4366(3) 0.0358(9) Uani d SD 1 A 1
H H5 0.3093 0.5000 0.5195 0.043 Uiso calc SR 1 A 1
C C27 0.19723(17) 0.5000 0.1081(2) 0.0252(7) Uani d SD 1 A 1
C C17 0.25178(17) 0.5000 0.0894(3) 0.0273(7) Uani d SD 1 A 1
H H17 0.3031 0.5000 0.1586 0.033 Uiso calc SR 1 A 1
C C11 0.24579(18) 0.5000 -0.0191(3) 0.0257(7) Uani d SD 1 A 1
C C12 0.17754(19) 0.5000 -0.1321(3) 0.0435(11) Uani d SD 1 A 1
H H12 0.1294 0.5000 -0.1432 0.052 Uiso calc SR 1 A 1
C C13 0.1790(2) 0.5000 -0.2279(3) 0.0455(11) Uani d SD 1 A 1
H H13 0.1316 0.5000 -0.3039 0.055 Uiso calc SR 1 A 1
C C14 0.24721(19) 0.5000 -0.2170(3) 0.0324(8) Uani d SD 1 A 1
C C15 0.31524(19) 0.5000 -0.1049(3) 0.0322(8) Uani d SD 1 A 1
H H15 0.3631 0.5000 -0.0947 0.039 Uiso calc SR 1 A 1
C C16 0.31497(17) 0.5000 -0.0074(3) 0.0255(7) Uani d SD 1 A 1
H H16 0.3625 0.5000 0.0684 0.031 Uiso calc SR 1 A 1
C C18 0.2474(2) 0.5000 -0.3233(3) 0.0381(9) Uani d SD 1 A 1
H H18A 0.1972 0.4569 -0.3915 0.057 Uiso calc PR 0.50 A 1
H H18B 0.2878 0.4140 -0.3102 0.057 Uiso calc PR 0.50 A 1
H H18C 0.2575 0.6291 -0.3373 0.057 Uiso calc PR 0.50 A 1
C C271 0.11614(18) 0.5000 0.0151(3) 0.0314(8) Uani d SD 1 A 1
N N271 0.05107(17) 0.5000 -0.0555(3) 0.0515(11) Uani d SD 1 A 1
S S31 0.0188(7) 0.1891(8) 0.2699(7) 0.0305(11) Uani d PD 0.25 B -2
C C32 0.0177(5) -0.0379(9) 0.3137(6) 0.026(4) Uani d PD 0.25 B -2
C C33 0.020(3) -0.1710(12) 0.245(3) 0.021(5) Uani d PD 0.25 B -2
H H33 0.0169 -0.3044 0.2515 0.025 Uiso calc PR 0.25 B -2
C C34 0.029(2) -0.0840(18) 0.162(2) 0.035(12) Uani d PD 0.25 B -2
H H34 0.0385 -0.1530 0.1143 0.042 Uiso calc PR 0.25 B -2
C C35 0.0224(18) 0.1071(16) 0.1599(18) 0.026(7) Uani d PD 0.25 B -2
H H35 0.0201 0.1866 0.1037 0.031 Uiso calc PR 0.25 B -2
C C57 0.0115(12) -0.0765(10) 0.4099(13) 0.022(4) Uani d PD 0.25 B -2
C C47 0.0020(13) 0.0582(11) 0.4675(14) 0.022(3) Uani d PD 0.25 B -2
H H47 -0.0011 0.1838 0.4404 0.026 Uiso calc PR 0.25 B -2
C C41 -0.0045(16) 0.0463(12) 0.5647(16) 0.019(4) Uani d PD 0.25 B -2
C C42 0.0010(13) -0.1193(13) 0.6233(13) 0.040(5) Uani d PD 0.25 B -2
H H42 0.0091 -0.2379 0.6001 0.048 Uiso calc PR 0.25 B -2
C C43 -0.0052(9) -0.1126(15) 0.7147(11) 0.043(5) Uiso d PD 0.25 B -2
H H43 0.0013 -0.2265 0.7556 0.052 Uiso calc PR 0.25 B -2
C C44 -0.0203(5) 0.0545(15) 0.7484(6) 0.030(4) Uani d PD 0.25 B -2
C C45 -0.0253(14) 0.2199(15) 0.6910(14) 0.033(4) Uani d PD 0.25 B -2
H H45 -0.0355 0.3372 0.7127 0.040 Uiso calc PR 0.25 B -2
C C46 -0.0156(7) 0.2173(11) 0.6027(8) 0.031(3) Uani d PD 0.25 B -2
H H46 -0.0166 0.3335 0.5675 0.037 Uiso calc PR 0.25 B -2
C C48 -0.032(3) 0.057(2) 0.844(3) 0.033(9) Uani d PD 0.25 B -2
H H48A -0.0256 -0.0724 0.8743 0.049 Uiso calc PR 0.25 B -2
H H48B -0.0840 0.1026 0.8115 0.049 Uiso calc PR 0.25 B -2
H H48C 0.0062 0.1412 0.9068 0.049 Uiso calc PR 0.25 B -2
C C571 0.0167(6) -0.2760(9) 0.4359(8) 0.025(2) Uani d PD 0.25 B -2
N N571 0.0212(5) -0.4358(9) 0.4533(7) 0.043(2) Uani d PD 0.25 B -2
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 S1 C2 . . 91.97(16) ?
C3 C2 C27 . . 127.3(3) ?
C3 C2 S1 . . 111.0(2) ?
C27 C2 S1 . . 121.8(2) ?
C2 C3 C4 . . 112.1(3) ?
C2 C3 H3 . . 123.9 ?
C4 C3 H3 . . 123.9 ?
C5 C4 C3 . . 112.8(3) ?
C5 C4 H4 . . 123.6 ?
C3 C4 H4 . . 123.6 ?
C4 C5 S1 . . 112.2(2) ?
C4 C5 H5 . . 123.9 ?
S1 C5 H5 . . 123.9 ?
C17 C27 C271 . . 123.0(3) ?
C17 C27 C2 . . 123.9(3) ?
C271 C27 C2 . . 113.1(3) ?
C27 C17 C11 . . 131.3(3) ?
C27 C17 H17 . . 114.4 ?
C11 C17 H17 . . 114.4 ?
C12 C11 C16 . . 117.4(3) ?
C12 C11 C17 . . 126.0(3) ?
C16 C11 C17 . . 116.6(3) ?
C13 C12 C11 . . 120.8(3) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C12 C13 C14 . . 122.0(3) ?
C12 C13 H13 . . 119.0 ?
C14 C13 H13 . . 119.0 ?
C13 C14 C15 . . 117.4(3) ?
C13 C14 C18 . . 121.1(3) ?
C15 C14 C18 . . 121.5(3) ?
C14 C15 C16 . . 121.4(3) ?
C14 C15 H15 . . 119.3 ?
C16 C15 H15 . . 119.3 ?
C15 C16 C11 . . 120.8(3) ?
C15 C16 H16 . . 119.6 ?
C11 C16 H16 . . 119.6 ?
N271 C271 C27 . . 177.1(3) ?
C35 S31 C32 . . 91.9(2) ?
C33 C32 C57 . . 126.6(5) ?
C33 C32 S31 . . 111.1(3) ?
C57 C32 S31 . . 122.2(4) ?
C32 C33 C34 . . 111.8(4) ?
C32 C33 H33 . . 124.1 ?
C34 C33 H33 . . 123.0 ?
C35 C34 C33 . . 112.6(5) ?
C35 C34 H34 . . 123.7 ?
C33 C34 H34 . . 123.7 ?
C34 C35 S31 . . 112.0(4) ?
C34 C35 H35 . . 124.0 ?
S31 C35 H35 . . 124.0 ?
C47 C57 C571 . . 123.3(4) ?
C47 C57 C32 . . 124.3(4) ?
C571 C57 C32 . . 112.4(4) ?
C57 C47 C41 . . 131.6(5) ?
C57 C47 H47 . . 114.2 ?
C41 C47 H47 . . 114.2 ?
C46 C41 C42 . . 117.6(4) ?
C46 C41 C47 . . 116.6(5) ?
C42 C41 C47 . . 125.9(5) ?
C43 C42 C41 . . 120.7(5) ?
C43 C42 H42 . . 119.6 ?
C41 C42 H42 . . 119.6 ?
C42 C43 C44 . . 121.9(5) ?
C42 C43 H43 . . 119.0 ?
C44 C43 H43 . . 119.0 ?
C43 C44 C45 . . 117.6(4) ?
C43 C44 C48 . . 121.1(5) ?
C45 C44 C48 . . 121.3(5) ?
C46 C45 C44 . . 121.3(5) ?
C46 C45 H45 . . 119.4 ?
C44 C45 H45 . . 119.4 ?
C45 C46 C41 . . 120.8(4) ?
C45 C46 H46 . . 119.6 ?
C41 C46 H46 . . 119.6 ?
C44 C48 H48A . . 109.5 ?
C44 C48 H48B . . 109.5 ?
H48A C48 H48B . . 109.5 ?
C44 C48 H48C . . 109.5 ?
H48A C48 H48C . . 109.5 ?
H48B C48 H48C . . 109.5 ?
N571 C571 C57 . . 177.3(9) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C5 . 1.708(3) ?
S1 C2 . 1.720(3) ?
C2 C3 . 1.376(4) ?
C2 C27 . 1.470(4) ?
C3 C4 . 1.426(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.348(5) ?
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C27 C17 . 1.346(4) ?
C27 C271 . 1.436(4) y
C17 C11 . 1.467(4) ?
C17 H17 . 0.9500 ?
C11 C12 . 1.395(4) ?
C11 C16 . 1.395(4) ?
C12 C13 . 1.377(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.379(5) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.385(4) ?
C14 C18 . 1.512(4) ?
C15 C16 . 1.387(4) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C271 N271 . 1.142(4) y
S31 C35 . 1.708(6) ?
S31 C32 . 1.717(5) ?
C32 C33 . 1.378(6) ?
C32 C57 . 1.473(5) ?
C33 C34 . 1.426(6) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.350(7) ?
C34 H34 . 0.9500 ?
C35 H35 . 0.9500 ?
C57 C47 . 1.342(5) ?
C57 C571 . 1.438(5) ?
C47 C41 . 1.468(5) ?
C47 H47 . 0.9500 ?
C41 C46 . 1.395(6) ?
C41 C42 . 1.395(6) ?
C42 C43 . 1.378(6) ?
C42 H42 . 0.9500 ?
C43 C44 . 1.379(6) ?
C43 H43 . 0.9500 ?
C44 C45 . 1.387(6) ?
C44 C48 . 1.511(6) ?
C45 C46 . 1.386(6) ?
C45 H45 . 0.9500 ?
C46 H46 . 0.9500 ?
C48 H48A . 0.9800 ?
C48 H48B . 0.9800 ?
C48 H48C . 0.9800 ?
C571 N571 . 1.141(6) ?
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
_geom_hbond_publ_flag
C3 H3 N271 2_555 0.95 2.76 3.689(6) 171 y
C12 H12 N271 . 0.95 2.62 3.471(7) 150 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 S1 C2 C3 . . . . 0.0 ?
C5 S1 C2 C27 . . . . 180.0 ?
C27 C2 C3 C4 . . . . 180.0 ?
S1 C2 C3 C4 . . . . 0.0 ?
C2 C3 C4 C5 . . . . 0.0 ?
C3 C4 C5 S1 . . . . 0.0 ?
C2 S1 C5 C4 . . . . 0.0 ?
C3 C2 C27 C17 . . . . 180.0 ?
S1 C2 C27 C17 . . . . 0.0 ?
C3 C2 C27 C271 . . . . 0.0 ?
S1 C2 C27 C271 . . . . 180.0 ?
C271 C27 C17 C11 . . . . 0.0 ?
C2 C27 C17 C11 . . . . 180.0 ?
C27 C17 C11 C12 . . . . 0.0 ?
C27 C17 C11 C16 . . . . 180.0 ?
C16 C11 C12 C13 . . . . 0.0 ?
C17 C11 C12 C13 . . . . 180.0 ?
C11 C12 C13 C14 . . . . 0.0 ?
C12 C13 C14 C15 . . . . 0.0 ?
C12 C13 C14 C18 . . . . 180.0 ?
C13 C14 C15 C16 . . . . 0.0 ?
C18 C14 C15 C16 . . . . 180.0 ?
C14 C15 C16 C11 . . . . 0.0 ?
C12 C11 C16 C15 . . . . 0.0 ?
C17 C11 C16 C15 . . . . 180.0 ?
C35 S31 C32 C33 . . . . 0.2(19) ?
C35 S31 C32 C57 . . . . -177.5(16) ?
C57 C32 C33 C34 . . . . -178(2) ?
S31 C32 C33 C34 . . . . 4(3) ?
C32 C33 C34 C35 . . . . -8(5) ?
C33 C34 C35 S31 . . . . 8(5) ?
C32 S31 C35 C34 . . . . -5(3) ?
C33 C32 C57 C47 . . . . -174(3) ?
S31 C32 C57 C47 . . . . 4(3) y
C33 C32 C57 C571 . . . . 6(3) ?
S31 C32 C57 C571 . . . . -176.3(11) ?
C571 C57 C47 C41 . . . . 1(4) ?
C32 C57 C47 C41 . . . . -179.3(11) y
C57 C47 C41 C46 . . . . -179(3) ?
C57 C47 C41 C42 . . . . 3(4) y
C46 C41 C42 C43 . . . . 1(4) ?
C47 C41 C42 C43 . . . . 179.2(16) ?
C41 C42 C43 C44 . . . . 3(3) ?
C42 C43 C44 C45 . . . . -3(2) ?
C42 C43 C44 C48 . . . . 176(2) ?
C43 C44 C45 C46 . . . . 0(3) ?
C48 C44 C45 C46 . . . . -179(2) ?
C44 C45 C46 C41 . . . . 3(3) ?
C42 C41 C46 C45 . . . . -4(3) ?
C47 C41 C46 C45 . . . . 177.6(17) ?
