#------------------------------------------------------------------------------
#$Date: 2019-08-01 06:28:16 +0300 (Thu, 01 Aug 2019) $
#$Revision: 217344 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/32/7233293.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_7233293
loop_
_publ_author_name
'Hloušková, Zuzana'
'Klikar, Milan'
'Pytela, Oldřich'
'Almonasy, Numan'
'R°užička, Aleš'
'Jandová, Veronika'
'Bureš, Filip'
_publ_section_title
;
 Structural elaboration of dicyanopyrazine: towards push--pull molecules
 with tailored photoredox activity
;
_journal_issue                   41
_journal_name_full               'RSC Advances'
_journal_page_first              23797
_journal_paper_doi               10.1039/C9RA04731J
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C8 H5 N2 O S2'
_chemical_formula_sum            'C8 H5 N2 O S2'
_chemical_formula_weight         209.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'APEX3 v2016.5-0'
_audit_update_record
;
2019-02-16 deposited with the CCDC.    2019-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.394(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.7934(12)
_cell_length_b                   12.8464(14)
_cell_length_c                   16.339(2)
_cell_measurement_reflns_used    17817
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1809.3(4)
_computing_cell_refinement       'APEX3 v2016.5-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'Platon (Spek, 2009)'
_computing_publication_material  'Platon (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1061
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17327
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.580
_diffrn_reflns_theta_min         2.543
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.544
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_crystal_colour            'fluorescent yellow'
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0468
_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)+(0.0737P)²+1.3810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1302
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1744
_reflns_number_total             2081
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ra04731j2.cif
_cod_data_source_block           12
_cod_database_code               7233293
_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.
;
_exptl_absorpt_special_details
;
The ratio of minimum to maximum
apparent transmission was 0.493
;
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'
'-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_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
S1 S 0.63804(7) 0.63712(4) 0.41273(3) 0.0290(2) Uani 1 1 d . . .
C1 C 0.6060(3) 0.40626(17) 0.39469(15) 0.0269(5) Uani 1 1 d . . .
N1 N 0.5000 0.41007(19) 0.2500 0.0221(5) Uani 1 2 d S T P
O2 O 0.6823(2) 1.03527(13) 0.31167(12) 0.0402(5) Uani 1 1 d . . .
C2 C 0.5530(2) 0.46476(16) 0.31891(13) 0.0212(4) Uani 1 1 d . . .
S2 S 0.71563(7) 0.83370(5) 0.32846(4) 0.0350(2) Uani 1 1 d . . .
N2 N 0.5000 0.62828(18) 0.2500 0.0211(5) Uani 1 2 d S T P
N3 N 0.6472(3) 0.36069(17) 0.45474(15) 0.0409(6) Uani 1 1 d . . .
C3 C 0.5555(2) 0.57440(16) 0.31909(13) 0.0207(4) Uani 1 1 d . . .
C5 C 0.5143(3) 0.83414(18) 0.42215(14) 0.0292(5) Uani 1 1 d . . .
H5 H 0.4466 0.8120 0.4574 0.035 Uiso 1 1 calc R U .
C4 C 0.6068(2) 0.76844(17) 0.38905(13) 0.0237(4) Uani 1 1 d . . .
C7 C 0.6336(3) 0.95030(17) 0.34832(14) 0.0287(5) Uani 1 1 d . . .
C6 C 0.5292(3) 0.93926(18) 0.39853(15) 0.0316(5) Uani 1 1 d . . .
H6 H 0.4726 0.9953 0.4159 0.038 Uiso 1 1 calc R U .
C8 C 0.6384(4) 1.13357(19) 0.34237(18) 0.0458(7) Uani 1 1 d . . .
H8A H 0.6805 1.1904 0.3135 0.069 Uiso 1 1 calc R U .
H8B H 0.6798 1.1384 0.4025 0.069 Uiso 1 1 calc R U .
H8C H 0.5250 1.1388 0.3320 0.069 Uiso 1 1 calc R U .
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
_geom_angle_site_symmetry_1
C4 S1 C3 103.38(10) .
N3 C1 C2 179.5(3) .
C2 N1 C2 116.3(2) 2_655
C7 O2 C8 115.0(2) .
N1 C2 C3 122.16(19) .
N1 C2 C1 116.75(19) .
C3 C2 C1 121.08(19) .
C7 S2 C4 90.81(11) .
C3 N2 C3 117.4(2) 2_655
N2 C3 C2 120.99(19) .
N2 C3 S1 121.30(16) .
C2 C3 S1 117.69(15) .
C4 C5 C6 112.9(2) .
C4 C5 H5 123.6 .
C6 C5 H5 123.6 .
C5 C4 S2 111.77(17) .
C5 C4 S1 126.53(18) .
S2 C4 S1 121.18(13) .
C6 C7 O2 131.6(2) .
C6 C7 S2 112.50(17) .
O2 C7 S2 115.93(18) .
C7 C6 C5 112.0(2) .
C7 C6 H6 124.0 .
C5 C6 H6 124.0 .
O2 C8 H8A 109.5 .
O2 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
O2 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C4 1.740(2) .
S1 C3 1.754(2) .
C1 N3 1.138(3) .
C1 C2 1.445(3) .
N1 C2 1.331(2) 2_655
N1 C2 1.331(2) .
O2 C7 1.354(3) .
O2 C8 1.439(3) .
C2 C3 1.409(3) .
S2 C7 1.721(2) .
S2 C4 1.724(2) .
N2 C3 1.332(2) 2_655
N2 C3 1.332(2) .
C5 C4 1.357(3) .
C5 C6 1.418(3) .
C5 H5 0.9500 .
C7 C6 1.354(4) .
C6 H6 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
