#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:17:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180386 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/55/7205533.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_7205533
loop_
_publ_author_name
'Kurach, Ewa'
'Djurado, David'
'Rimarčik, Jan'
'Kornet, Aleksandra'
'Wlostowski, Marek'
'Lukeš, Vladimir'
'Pécaut, Jacques'
'Zagorska, Malgorzata'
'Pron, Adam'
_publ_section_title
;
 Effect of substituents on redox, spectroscopic and structural
 properties of conjugated diaryltetrazines-a combined experimental and
 theoretical study.
;
_journal_issue                   7
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              2690
_journal_page_last               2700
_journal_paper_doi               10.1039/c0cp01553a
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety
;
'C18H10N4S4'
;
_chemical_formula_sum            'C27 H15 N6 S6'
_chemical_formula_weight         615.81
_chemical_name_systematic
;
3,6-bis(2',2-bi-5-thienyl)-1,2,4,5-tetrazine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.418(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8286(2)
_cell_length_b                   22.7537(9)
_cell_length_c                   19.7775(7)
_cell_measurement_reflns_used    2945
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      28.9411
_cell_measurement_theta_min      3.0920
_cell_volume                     2615.14(17)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector_area_resol_mean 15.9653
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
1 omega -13.00 39.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 17.1550 77.0000 180.0000 0.0000 0.0000 52

2 omega -6.00 43.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 17.1550 45.0000 90.0000 0.0000 0.0000 49

3 omega -54.00 -4.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 17.1550 -45.0000 90.0000 0.0000 0.0000 50

4 omega -9.00 32.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- 17.1550 -56.0000 209.0000 0.0000 0.0000 41

5 omega 4.00 48.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -18.7175 56.0000 171.0000 0.0000 0.0000 44

6 omega -78.00 -37.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
- -18.7175 -77.0000 300.0000 0.0000 0.0000 41

;
_diffrn_measurement_device_type  'κ-geometry diffractometer'
_diffrn_measurement_method       omega-scan
_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  0.0530
_diffrn_reflns_av_sigmaI/netI    0.1064
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10794
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.555
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'long plate'
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.820
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         3751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.820
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0183P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0555
_refine_ls_wR_factor_ref         0.0607
_reflns_number_gt                2146
_reflns_number_total             3751
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CP01553A.TXT
_cod_data_source_block           echo15
_cod_database_code               7205533
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.61889(17) 0.70709(4) 0.46733(4) 0.0371(3) Uani 1 1 d . . .
S2 S 0.58196(16) 0.61437(4) 0.65916(4) 0.0257(3) Uani 1 1 d . . .
S3 S 0.81396(15) 0.44308(4) 0.96561(4) 0.0260(3) Uani 1 1 d . . .
S4 S 1.08829(17) 0.33217(4) 1.13226(4) 0.0328(3) Uani 1 1 d . . .
N1 N 0.7113(5) 0.53837(12) 0.77937(13) 0.0243(7) Uani 1 1 d . . .
N2 N 1.0553(5) 0.50113(12) 0.73633(13) 0.0239(7) Uani 1 1 d . . .
N3 N 1.1011(5) 0.47111(12) 0.79249(14) 0.0248(7) Uani 1 1 d . . .
N4 N 0.7572(5) 0.50818(13) 0.83551(13) 0.0254(8) Uani 1 1 d . . .
C1 C 0.3888(6) 0.75295(15) 0.45573(17) 0.0328(10) Uani 1 1 d . . .
H1 H 0.3641 0.7786 0.4193 0.039 Uiso 1 1 calc R . .
C2 C 0.2472(6) 0.74748(16) 0.50576(17) 0.0340(10) Uani 1 1 d . . .
H2 H 0.1134 0.7694 0.5078 0.041 Uiso 1 1 calc R . .
C3 C 0.3207(6) 0.70536(14) 0.55467(16) 0.0257(9) Uani 1 1 d . . .
H3 H 0.2406 0.6965 0.5923 0.031 Uiso 1 1 calc R . .
C4 C 0.5209(6) 0.67891(15) 0.54127(15) 0.0218(9) Uani 1 1 d . . .
C5 C 0.6573(6) 0.63559(14) 0.57961(16) 0.0238(9) Uani 1 1 d . . .
C6 C 0.8509(6) 0.60717(15) 0.56386(16) 0.0278(9) Uani 1 1 d . . .
H6 H 0.9163 0.6123 0.5228 0.033 Uiso 1 1 calc R . .
C7 C 0.9430(6) 0.56964(14) 0.61475(16) 0.0237(9) Uani 1 1 d . . .
H7 H 1.0758 0.5476 0.6112 0.028 Uiso 1 1 calc R . .
C8 C 0.8172(6) 0.56876(14) 0.67048(16) 0.0203(9) Uani 1 1 d . . .
C9 C 0.8607(6) 0.53492(14) 0.73165(16) 0.0203(9) Uani 1 1 d . . .
C10 C 0.9508(6) 0.47681(14) 0.84146(16) 0.0205(9) Uani 1 1 d . . .
C11 C 1.0074(6) 0.44557(14) 0.90400(15) 0.0201(9) Uani 1 1 d . . .
C12 C 1.2022(6) 0.41465(15) 0.92365(17) 0.0278(9) Uani 1 1 d . . .
H12 H 1.3255 0.4106 0.8968 0.033 Uiso 1 1 calc R . .
C13 C 1.1975(6) 0.38979(15) 0.98813(16) 0.0280(10) Uani 1 1 d . . .
H13 H 1.3176 0.3676 1.0085 0.034 Uiso 1 1 calc R . .
C14 C 0.9994(6) 0.40123(14) 1.01820(16) 0.0211(9) Uani 1 1 d . . .
C15 C 0.9289(6) 0.38375(13) 1.08346(15) 0.0196(8) Uani 1 1 d . . .
C16 C 0.7398(6) 0.40257(13) 1.11616(15) 0.0186(9) Uani 1 1 d . . .
H16 H 0.6328 0.4300 1.0986 0.022 Uiso 1 1 calc R . .
C17 C 0.7316(6) 0.37454(14) 1.17968(16) 0.0275(10) Uani 1 1 d . . .
H17 H 0.6168 0.3821 1.2086 0.033 Uiso 1 1 calc R . .
C18 C 0.9027(6) 0.33603(16) 1.19507(15) 0.0294(10) Uani 1 1 d . . .
H18 H 0.9183 0.3142 1.2349 0.035 Uiso 1 1 calc R . .
S21 S 0.09572(19) 0.69288(4) 0.18182(4) 0.0444(3) Uani 1 1 d . . .
S22 S 0.14545(16) 0.61020(4) 0.38163(4) 0.0270(3) Uani 1 1 d . . .
N21 N 0.3079(5) 0.53430(12) 0.49860(14) 0.0236(7) Uani 1 1 d . . .
N22 N 0.6369(5) 0.49814(13) 0.44788(13) 0.0251(8) Uani 1 1 d . . .
C21 C -0.1554(7) 0.73123(16) 0.1724(2) 0.0462(12) Uani 1 1 d . . .
H21 H -0.2046 0.7516 0.1332 0.055 Uiso 1 1 calc R . .
C22 C -0.2755(7) 0.72885(16) 0.2281(2) 0.0456(12) Uani 1 1 d . . .
H22 H -0.4157 0.7477 0.2316 0.055 Uiso 1 1 calc R . .
C23 C -0.1638(6) 0.69450(14) 0.28023(16) 0.0251(9) Uani 1 1 d . . .
H23 H -0.2227 0.6882 0.3220 0.030 Uiso 1 1 calc R . .
C24 C 0.0400(6) 0.67150(15) 0.26270(15) 0.0261(9) Uani 1 1 d . . .
C25 C 0.1974(6) 0.63191(14) 0.30052(15) 0.0215(9) Uani 1 1 d . . .
C26 C 0.3893(6) 0.60568(15) 0.28046(16) 0.0241(9) Uani 1 1 d . . .
H26 H 0.4432 0.6118 0.2380 0.029 Uiso 1 1 calc R . .
C27 C 0.4999(6) 0.56848(14) 0.32923(16) 0.0218(9) Uani 1 1 d . . .
H27 H 0.6336 0.5476 0.3228 0.026 Uiso 1 1 calc R . .
C28 C 0.3871(6) 0.56672(13) 0.38750(16) 0.0203(9) Uani 1 1 d . . .
C29 C 0.4468(6) 0.53154(15) 0.44678(16) 0.0204(9) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 91.90(18) . . ?
C8 S2 C5 91.78(17) . . ?
C11 S3 C14 91.76(17) . . ?
C18 S4 C15 91.59(17) . . ?
N4 N1 C9 117.7(3) . . ?
N3 N2 C9 117.6(3) . . ?
N2 N3 C10 116.9(3) . . ?
N1 N4 C10 118.0(3) . . ?
C2 C1 S1 111.5(3) . . ?
C1 C2 C3 113.5(4) . . ?
C4 C3 C2 112.9(3) . . ?
C3 C4 C5 130.3(3) . . ?
C3 C4 S1 110.2(2) . . ?
C5 C4 S1 119.4(3) . . ?
C6 C5 C4 129.7(3) . . ?
C6 C5 S2 110.4(3) . . ?
C4 C5 S2 119.9(3) . . ?
C5 C6 C7 114.0(3) . . ?
C8 C7 C6 112.9(3) . . ?
C7 C8 C9 127.8(3) . . ?
C7 C8 S2 110.9(3) . . ?
C9 C8 S2 121.3(3) . . ?
N1 C9 N2 124.6(3) . . ?
N1 C9 C8 118.7(3) . . ?
N2 C9 C8 116.7(3) . . ?
N4 C10 N3 125.1(3) . . ?
N4 C10 C11 118.4(3) . . ?
N3 C10 C11 116.5(3) . . ?
C12 C11 C10 128.9(3) . . ?
C12 C11 S3 110.9(3) . . ?
C10 C11 S3 120.2(3) . . ?
C11 C12 C13 113.2(3) . . ?
C14 C13 C12 113.4(3) . . ?
C13 C14 C15 130.4(3) . . ?
C13 C14 S3 110.7(2) . . ?
C15 C14 S3 118.9(3) . . ?
C16 C15 C14 128.6(3) . . ?
C16 C15 S4 111.0(2) . . ?
C14 C15 S4 120.4(3) . . ?
C15 C16 C17 110.9(3) . . ?
C18 C17 C16 114.8(3) . . ?
C17 C18 S4 111.6(3) . . ?
C21 S21 C24 91.4(2) . . ?
C28 S22 C25 91.49(17) . . ?
N22 N21 C29 117.4(3) 3_666 . ?
N21 N22 C29 118.9(3) 3_666 . ?
C22 C21 S21 112.7(3) . . ?
C21 C22 C23 112.3(4) . . ?
C24 C23 C22 112.8(3) . . ?
C23 C24 C25 129.3(3) . . ?
C23 C24 S21 110.9(2) . . ?
C25 C24 S21 119.7(3) . . ?
C26 C25 C24 128.8(3) . . ?
C26 C25 S22 110.7(2) . . ?
C24 C25 S22 120.5(3) . . ?
C25 C26 C27 114.3(3) . . ?
C28 C27 C26 111.8(3) . . ?
C27 C28 C29 126.8(3) . . ?
C27 C28 S22 111.7(3) . . ?
C29 C28 S22 121.4(3) . . ?
N22 C29 N21 123.7(3) . . ?
N22 C29 C28 118.4(3) . . ?
N21 C29 C28 117.9(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.701(4) . ?
S1 C4 1.733(3) . ?
S2 C8 1.720(3) . ?
S2 C5 1.734(3) . ?
S3 C11 1.724(3) . ?
S3 C14 1.727(3) . ?
S4 C18 1.711(3) . ?
S4 C15 1.742(3) . ?
N1 N4 1.316(3) . ?
N1 C9 1.335(4) . ?
N2 N3 1.314(3) . ?
N2 C9 1.367(4) . ?
N3 C10 1.361(4) . ?
N4 C10 1.333(4) . ?
C1 C2 1.342(4) . ?
C2 C3 1.405(4) . ?
C3 C4 1.357(4) . ?
C4 C5 1.444(4) . ?
C5 C6 1.357(4) . ?
C6 C7 1.395(4) . ?
C7 C8 1.370(4) . ?
C8 C9 1.440(4) . ?
C10 C11 1.443(4) . ?
C11 C12 1.367(4) . ?
C12 C13 1.397(4) . ?
C13 C14 1.364(4) . ?
C14 C15 1.440(4) . ?
C15 C16 1.388(4) . ?
C16 C17 1.413(4) . ?
C17 C18 1.345(4) . ?
S21 C21 1.702(4) . ?
S21 C24 1.727(3) . ?
S22 C28 1.718(3) . ?
S22 C25 1.727(3) . ?
N21 N22 1.310(3) 3_666 ?
N21 C29 1.356(4) . ?
N22 N21 1.310(3) 3_666 ?
N22 C29 1.342(4) . ?
C21 C22 1.350(5) . ?
C22 C23 1.413(4) . ?
C23 C24 1.367(4) . ?
C24 C25 1.452(4) . ?
C25 C26 1.354(4) . ?
C26 C27 1.402(4) . ?
C27 C28 1.371(4) . ?
C28 C29 1.440(4) . ?
