#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/52/7215218.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_7215218
loop_
_publ_author_name
'Hayward, John J.'
'Gumbau-Brisa, Roger'
'Alberola, Antonio'
'Clarke, Caroline S.'
'Rawson, Jeremy M.'
'Pilkington, Melanie'
_publ_section_title
;
 An unusual single-crystal-to-single-crystal [2 + 2] photocyclisation
 reaction of a TTF-arylnitrile derivative
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              7268
_journal_paper_doi               10.1039/C4CE00346B
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C12 H6 N2 S4'
_chemical_formula_sum            'C12 H6 N2 S4'
_chemical_formula_weight         306.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 91.393(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9337(4)
_cell_length_b                   11.3951(9)
_cell_length_c                   27.644(2)
_cell_measurement_reflns_used    3915
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.13
_cell_measurement_theta_min      2.84
_cell_volume                     1238.77(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 1.004
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 1.004
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            17919
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 1.004
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         1.787
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.516
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0849
_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)+(0.1541P)²+9.6439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2579
_refine_ls_wR_factor_ref         0.2704
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1908
_reflns_number_total             2213
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ce00346b2.cif
_cod_data_source_block           cmpnd3
_cod_depositor_comments
'Adding full bibliography for 7215216--7215218.cif.'
_cod_database_code               7215218
#BEGIN Tags that were not found in dictionaries:
_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   0.707
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2013-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S1 S 0.8726(6) 0.51388(19) 0.36460(8) 0.0247(6) Uani 1 1 d . .
S2 S 0.5482(6) 0.73625(19) 0.39351(8) 0.0242(6) Uani 1 1 d . .
S3 S 0.5265(6) 0.82194(18) 0.28220(8) 0.0228(6) Uani 1 1 d . .
S4 S 0.8455(6) 0.59905(18) 0.25221(7) 0.0220(6) Uani 1 1 d . .
N1 N 0.8784(19) 0.7402(6) 0.0736(3) 0.0236(16) Uani 1 1 d . .
N2 N 1.276(2) 0.6209(8) -0.0226(3) 0.040(2) Uani 1 1 d . .
C1 C 0.673(3) 0.6382(9) 0.4393(3) 0.032(2) Uani 1 1 d . .
H1 H 0.6429 0.6563 0.4717 0.038 Uiso 1 1 calc R U
C2 C 0.810(3) 0.5377(9) 0.4264(3) 0.032(2) Uani 1 1 d . .
H2 H 0.8714 0.4814 0.4493 0.038 Uiso 1 1 calc R U
C3 C 0.706(2) 0.6501(7) 0.3463(3) 0.0203(17) Uani 1 1 d . .
C4 C 0.692(2) 0.6852(7) 0.2997(3) 0.0179(17) Uani 1 1 d . .
C5 C 0.764(2) 0.7055(7) 0.2067(3) 0.0213(18) Uani 1 1 d . .
C6 C 0.623(2) 0.8052(8) 0.2220(3) 0.0225(18) Uani 1 1 d . .
H6 H 0.5769 0.8656 0.2001 0.027 Uiso 1 1 calc R U
C7 C 0.861(2) 0.6779(7) 0.1573(3) 0.0202(17) Uani 1 1 d . .
C8 C 1.032(2) 0.5755(8) 0.1454(3) 0.0230(18) Uani 1 1 d . .
H8 H 1.0800 0.5196 0.1691 0.028 Uiso 1 1 calc R U
C9 C 1.131(2) 0.5567(8) 0.0980(3) 0.0244(19) Uani 1 1 d . .
H9 H 1.2467 0.4891 0.0893 0.029 Uiso 1 1 calc R U
C10 C 1.051(2) 0.6422(8) 0.0647(3) 0.0237(18) Uani 1 1 d . .
C11 C 0.783(2) 0.7551(8) 0.1191(3) 0.0257(19) Uani 1 1 d . .
H11 H 0.6561 0.8216 0.1260 0.031 Uiso 1 1 calc R U
C12 C 1.176(2) 0.6304(8) 0.0158(3) 0.030(2) Uani 1 1 d . .
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
C2 S1 C3 94.8(4)
C1 S2 C3 94.8(4)
C6 S3 C4 94.5(4)
C4 S4 C5 95.1(4)
C10 N1 C11 116.0(7)
C2 C1 S2 117.9(7)
C2 C1 H1 121.1
S2 C1 H1 121.1
C1 C2 S1 117.8(7)
C1 C2 H2 121.1
S1 C2 H2 121.1
C4 C3 S1 123.0(6)
C4 C3 S2 122.4(7)
S1 C3 S2 114.5(5)
C3 C4 S3 122.3(6)
C3 C4 S4 122.7(6)
S3 C4 S4 115.0(5)
C6 C5 C7 126.7(8)
C6 C5 S4 115.3(7)
C7 C5 S4 118.0(6)
C5 C6 S3 120.0(7)
C5 C6 H6 120.0
S3 C6 H6 120.0
C8 C7 C11 116.4(8)
C8 C7 C5 122.7(8)
C11 C7 C5 120.8(8)
C7 C8 C9 120.0(8)
C7 C8 H8 120.0
C9 C8 H8 120.0
C10 C9 C8 117.2(8)
C10 C9 H9 121.4
C8 C9 H9 121.4
N1 C10 C9 125.4(8)
N1 C10 C12 115.8(8)
C9 C10 C12 118.7(8)
N1 C11 C7 124.8(8)
N1 C11 H11 117.6
C7 C11 H11 117.6
N2 C12 C10 179.5(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.752(9)
S1 C3 1.754(9)
S2 C1 1.749(10)
S2 C3 1.760(8)
S3 C6 1.728(8)
S3 C4 1.753(8)
S4 C4 1.757(8)
S4 C5 1.771(9)
N1 C10 1.332(12)
N1 C11 1.331(11)
N2 C12 1.146(12)
C1 C2 1.319(14)
C1 H1 0.9300
C2 H2 0.9300
C3 C4 1.348(12)
C5 C6 1.337(12)
C5 C7 1.460(12)
C6 H6 0.9300
C7 C8 1.391(12)
C7 C11 1.403(12)
C8 C9 1.392(12)
C8 H8 0.9300
C9 C10 1.373(12)
C9 H9 0.9300
C10 C12 1.457(12)
C11 H11 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198402
