#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/79/2227901.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_2227901
loop_
_publ_author_name
'Prasath, R.'
'Bhavana, P.'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 N,N'-Bis[(E)-(3-methyl-2-thienyl)methylidene]ethane-1,2-diamine
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2884
_journal_paper_doi               10.1107/S1600536810041632
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H16 N2 S2'
_chemical_formula_moiety         'C14 H16 N2 S2'
_chemical_formula_sum            'C14 H16 N2 S2'
_chemical_formula_weight         276.41
_chemical_name_systematic
;
N,N'-Bis[(E)-(3-methyl-2-thienyl)methylidene]ethane-
1,2-diamine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.7600(10)
_cell_angle_beta                 91.6530(10)
_cell_angle_gamma                106.0660(10)
_cell_formula_units_Z            2
_cell_length_a                   8.7610(6)
_cell_length_b                   8.9502(6)
_cell_length_c                   8.9853(6)
_cell_measurement_reflns_used    4410
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      4.3
_cell_volume                     675.61(8)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_av_sigmaI/netI    0.026
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6435
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.3
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.10
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.10
_refine_ls_R_factor_all          0.035
_refine_ls_R_factor_gt           0.031
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0508P)²+0.4238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.095
_refine_ls_wR_factor_ref         0.100
_reflns_number_gt                2822
_reflns_number_total             3089
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2279.cif
_cod_data_source_block           I
_cod_database_code               2227901
_cod_database_fobs_code          2227901
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.47805(4) 0.72178(4) 0.45069(4) 0.01583(12) Uani d . 1 . .
N N1 0.48699(16) 0.93243(16) 0.19349(14) 0.0171(3) Uani d . 1 . .
C C1 0.47949(19) 1.03494(19) 0.07326(17) 0.0170(3) Uani d . 1 . .
H H1A 0.5554 1.1387 0.0968 0.020 Uiso calc R 1 . .
H H1B 0.3712 1.0483 0.0637 0.020 Uiso calc R 1 . .
C C2 0.59455(18) 0.98652(18) 0.29593(17) 0.0151(3) Uani d . 1 . .
H H2 0.6641 1.0881 0.2890 0.018 Uiso calc R 1 . .
C C3 0.61453(18) 0.89825(18) 0.42300(17) 0.0147(3) Uani d . 1 . .
C C4 0.73245(18) 0.93799(18) 0.53428(17) 0.0157(3) Uani d . 1 . .
C C5 0.7128(2) 0.82044(19) 0.63988(17) 0.0174(3) Uani d . 1 . .
H H5 0.7844 0.8264 0.7228 0.021 Uiso calc R 1 . .
C C6 0.5808(2) 0.69924(19) 0.60906(17) 0.0180(3) Uani d . 1 . .
H H6 0.5493 0.6120 0.6686 0.022 Uiso calc R 1 . .
C C7 0.8608(2) 1.0898(2) 0.5493(2) 0.0223(3) Uani d . 1 . .
H H7A 0.8213 1.1682 0.6035 0.033 Uiso calc R 1 . .
H H7B 0.8913 1.1247 0.4500 0.033 Uiso calc R 1 . .
H H7C 0.9535 1.0756 0.6043 0.033 Uiso calc R 1 . .
S S2 0.08033(5) 0.56857(5) 0.69562(4) 0.01757(12) Uani d . 1 . .
N N2 0.01928(16) 0.80946(15) 0.92178(15) 0.0166(3) Uani d . 1 . .
C C8 -0.0229(2) 0.91842(18) 1.02823(18) 0.0179(3) Uani d . 1 . .
H H8A 0.0328 0.9189 1.1257 0.021 Uiso calc R 1 . .
H H8B -0.1388 0.8846 1.0427 0.021 Uiso calc R 1 . .
C C9 0.09982(18) 0.72358(18) 0.97335(17) 0.0151(3) Uani d . 1 . .
H H9 0.1320 0.7369 1.0761 0.018 Uiso calc R 1 . .
C C10 0.14457(18) 0.60595(17) 0.88127(17) 0.0138(3) Uani d . 1 . .
C C11 0.23606(18) 0.51136(18) 0.92386(17) 0.0147(3) Uani d . 1 . .
C C12 0.25375(19) 0.40900(18) 0.80306(18) 0.0177(3) Uani d . 1 . .
H H12 0.3134 0.3356 0.8116 0.021 Uiso calc R 1 . .
C C13 0.1767(2) 0.42700(19) 0.67441(19) 0.0196(3) Uani d . 1 . .
H H13 0.1764 0.3680 0.5836 0.023 Uiso calc R 1 . .
C C14 0.30760(19) 0.5131(2) 1.07776(18) 0.0191(3) Uani d . 1 . .
H H14A 0.3663 0.6200 1.1108 0.029 Uiso calc R 1 . .
H H14B 0.3803 0.4473 1.0766 0.029 Uiso calc R 1 . .
H H14C 0.2229 0.4731 1.1464 0.029 Uiso calc R 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'
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
C6 S1 C3 . . 91.47(8) ?
C2 N1 C1 . . 116.35(13) ?
N1 C1 C1 . 2_675 109.83(16) ?
N1 C1 H1A . . 109.7 ?
C1 C1 H1A 2_675 . 109.7 ?
N1 C1 H1B . . 109.7 ?
C1 C1 H1B 2_675 . 109.7 ?
H1A C1 H1B . . 108.2 ?
N1 C2 C3 . . 122.28(14) ?
N1 C2 H2 . . 118.9 ?
C3 C2 H2 . . 118.9 ?
C4 C3 C2 . . 127.93(14) ?
C4 C3 S1 . . 111.67(12) ?
C2 C3 S1 . . 120.39(12) ?
C3 C4 C5 . . 111.63(14) ?
C3 C4 C7 . . 124.67(14) ?
C5 C4 C7 . . 123.60(14) ?
C6 C5 C4 . . 112.87(14) ?
C6 C5 H5 . . 123.6 ?
C4 C5 H5 . . 123.6 ?
C5 C6 S1 . . 112.33(12) ?
C5 C6 H6 . . 123.8 ?
S1 C6 H6 . . 123.8 ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C13 S2 C10 . . 91.55(8) ?
C9 N2 C8 . . 116.78(14) ?
N2 C8 C8 . 2_577 110.34(17) ?
N2 C8 H8A . . 109.6 ?
C8 C8 H8A 2_577 . 109.6 ?
N2 C8 H8B . . 109.6 ?
C8 C8 H8B 2_577 . 109.6 ?
H8A C8 H8B . . 108.1 ?
N2 C9 C10 . . 122.61(14) ?
N2 C9 H9 . . 118.7 ?
C10 C9 H9 . . 118.7 ?
C11 C10 C9 . . 127.42(14) ?
C11 C10 S2 . . 111.68(12) ?
C9 C10 S2 . . 120.89(11) ?
C10 C11 C12 . . 111.52(14) ?
C10 C11 C14 . . 124.84(14) ?
C12 C11 C14 . . 123.64(14) ?
C13 C12 C11 . . 113.24(14) ?
C13 C12 H12 . . 123.4 ?
C11 C12 H12 . . 123.4 ?
C12 C13 S2 . . 112.00(12) ?
C12 C13 H13 . . 124.0 ?
S2 C13 H13 . . 124.0 ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
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 C6 . 1.7119(16) ?
S1 C3 . 1.7309(16) ?
N1 C2 . 1.274(2) ?
N1 C1 . 1.4621(19) ?
C1 C1 2_675 1.525(3) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C3 . 1.453(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.377(2) ?
C4 C5 . 1.429(2) ?
C4 C7 . 1.502(2) ?
C5 C6 . 1.360(2) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
S2 C13 . 1.7125(17) ?
S2 C10 . 1.7318(16) ?
N2 C9 . 1.272(2) ?
N2 C8 . 1.460(2) ?
C8 C8 2_577 1.520(3) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.453(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.377(2) ?
C11 C12 . 1.426(2) ?
C11 C14 . 1.499(2) ?
C12 C13 . 1.361(2) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
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
C13 H13 Cg1 2_666 0.95 2.89 3.6179(19) 134
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
C2 N1 C1 C1 . . . 2_675 114.66(18) ?
C1 N1 C2 C3 . . . . 179.26(14) ?
N1 C2 C3 C4 . . . . 174.57(16) ?
N1 C2 C3 S1 . . . . -6.9(2) ?
C6 S1 C3 C4 . . . . -1.13(13) ?
C6 S1 C3 C2 . . . . -179.90(13) ?
C2 C3 C4 C5 . . . . -179.55(15) ?
S1 C3 C4 C5 . . . . 1.80(17) ?
C2 C3 C4 C7 . . . . 3.9(3) ?
S1 C3 C4 C7 . . . . -174.74(13) ?
C3 C4 C5 C6 . . . . -1.7(2) ?
C7 C4 C5 C6 . . . . 174.86(15) ?
C4 C5 C6 S1 . . . . 0.86(18) ?
C3 S1 C6 C5 . . . . 0.14(13) ?
C9 N2 C8 C8 . . . 2_577 128.94(18) ?
C8 N2 C9 C10 . . . . 177.52(14) ?
N2 C9 C10 C11 . . . . 177.29(16) ?
N2 C9 C10 S2 . . . . -3.6(2) ?
C13 S2 C10 C11 . . . . -0.31(12) ?
C13 S2 C10 C9 . . . . -179.53(13) ?
C9 C10 C11 C12 . . . . 179.52(15) ?
S2 C10 C11 C12 . . . . 0.36(17) ?
C9 C10 C11 C14 . . . . 0.1(3) ?
S2 C10 C11 C14 . . . . -179.05(12) ?
C10 C11 C12 C13 . . . . -0.2(2) ?
C14 C11 C12 C13 . . . . 179.18(14) ?
C11 C12 C13 S2 . . . . 0.01(18) ?
C10 S2 C13 C12 . . . . 0.17(13) ?
