#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:55:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180323 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/37/7153776.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_7153776
loop_
_publ_author_name
'Biet, Thomas'
'Avarvari, Narcis'
_publ_section_title
;
 Tetrathiafulvalene mono- and bis-1,2,3-triazole precursors by click
 chemistry: structural diversity and reactivity.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3167
_journal_page_last               3174
_journal_paper_doi               10.1039/c4ob00148f
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C26 H22 N6 S4'
_chemical_formula_sum            'C26 H22 N6 S4'
_chemical_formula_weight         546.74
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7025(5)
_cell_length_b                   19.621(2)
_cell_length_c                   20.267(3)
_cell_measurement_reflns_used    4058
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.03
_cell_measurement_theta_min      3.71
_cell_volume                     2665.3(5)
_computing_cell_refinement
'Dirax/1sq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  area_detector
_diffrn_measurement_method       CCD
_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  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13973
_diffrn_reflns_theta_full        24.03
_diffrn_reflns_theta_max         24.03
_diffrn_reflns_theta_min         3.71
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            plate
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       orange
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0195P)²+1.3413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                2912
_reflns_number_total             4058
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00148f2.cif
_cod_data_source_block           8
_cod_depositor_comments
;Adding full bibliography for 7153774--7153777.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2665.3(6)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7153776
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
S1 S -0.3361(2) 0.20518(6) 0.65313(7) 0.0626(4) Uani 1 1 d .
S2 S -0.4054(2) 0.34635(6) 0.60975(7) 0.0676(4) Uani 1 1 d .
S3 S 0.03890(17) 0.25106(5) 0.73896(6) 0.0530(3) Uani 1 1 d .
S4 S -0.00930(19) 0.39389(5) 0.69470(6) 0.0578(3) Uani 1 1 d .
N1 N 0.2644(5) 0.28612(17) 0.89445(17) 0.0441(9) Uani 1 1 d .
N2 N 0.4147(6) 0.2624(2) 0.9314(2) 0.0634(11) Uani 1 1 d .
N3 N 0.5639(6) 0.2491(2) 0.8924(2) 0.0703(12) Uani 1 1 d .
N4 N 0.2208(5) 0.49799(17) 0.80000(19) 0.0479(9) Uani 1 1 d .
N5 N 0.3719(7) 0.53499(19) 0.8252(2) 0.0654(12) Uani 1 1 d .
N6 N 0.5318(6) 0.4969(2) 0.8242(2) 0.0719(13) Uani 1 1 d .
C1 C -0.5522(7) 0.2209(2) 0.6064(2) 0.0577(13) Uani 1 1 d .
C2 C -0.5821(7) 0.2844(3) 0.5868(2) 0.0586(13) Uani 1 1 d .
C3 C -0.2595(7) 0.2907(2) 0.6568(2) 0.0497(11) Uani 1 1 d .
C4 C -0.1011(6) 0.3099(2) 0.6921(2) 0.0468(11) Uani 1 1 d .
C5 C 0.1830(6) 0.3132(2) 0.7782(2) 0.0404(11) Uani 1 1 d .
C6 C 0.1628(6) 0.3784(2) 0.7586(2) 0.0405(10) Uani 1 1 d .
C7 C 0.3166(6) 0.2887(2) 0.8305(2) 0.0390(10) Uani 1 1 d .
C8 C 0.5073(7) 0.2640(2) 0.8303(3) 0.0578(12) Uani 1 1 d .
H8 H 0.5861 0.2583 0.7929 0.069 Uiso 1 1 calc R
C9 C 0.2850(6) 0.4344(2) 0.7837(2) 0.0435(11) Uani 1 1 d .
C10 C 0.4838(7) 0.4356(2) 0.7997(2) 0.0604(13) Uani 1 1 d .
H10 H 0.5719 0.3994 0.7943 0.073 Uiso 1 1 calc R
C11 C -0.6795(8) 0.1594(3) 0.5914(3) 0.0876(18) Uani 1 1 d .
H11A H -0.6241 0.1201 0.6128 0.131 Uiso 1 1 calc R
H11B H -0.6827 0.1520 0.5446 0.131 Uiso 1 1 calc R
H11C H -0.8126 0.1670 0.6073 0.131 Uiso 1 1 calc R
C12 C -0.7522(7) 0.3096(3) 0.5439(3) 0.0811(17) Uani 1 1 d .
H12A H -0.7381 0.3577 0.5366 0.122 Uiso 1 1 calc R
H12B H -0.8769 0.3007 0.5656 0.122 Uiso 1 1 calc R
H12C H -0.7494 0.2862 0.5023 0.122 Uiso 1 1 calc R
C13 C 0.0737(7) 0.3038(2) 0.9253(2) 0.0556(12) Uani 1 1 d .
H13A H 0.0593 0.2778 0.9658 0.067 Uiso 1 1 calc R
H13B H -0.0338 0.2907 0.8960 0.067 Uiso 1 1 calc R
C14 C 0.0538(7) 0.3785(2) 0.9411(2) 0.0488(12) Uani 1 1 d .
C15 C 0.2132(8) 0.4191(3) 0.9569(3) 0.0744(16) Uani 1 1 d .
H15 H 0.3414 0.4011 0.9556 0.089 Uiso 1 1 calc R
C16 C 0.1860(10) 0.4864(3) 0.9748(3) 0.0880(19) Uani 1 1 d .
H16 H 0.2956 0.5132 0.9856 0.106 Uiso 1 1 calc R
C17 C 0.0000(12) 0.5134(3) 0.9767(3) 0.0845(17) Uani 1 1 d .
H17 H -0.0192 0.5584 0.9899 0.101 Uiso 1 1 calc R
C18 C -0.1581(10) 0.4741(4) 0.9592(3) 0.095(2) Uani 1 1 d .
H18 H -0.2854 0.4929 0.9593 0.114 Uiso 1 1 calc R
C19 C -0.1343(8) 0.4071(3) 0.9414(3) 0.0762(16) Uani 1 1 d .
H19 H -0.2446 0.3811 0.9295 0.091 Uiso 1 1 calc R
C20 C 0.0287(7) 0.5307(2) 0.7923(2) 0.0572(13) Uani 1 1 d .
H20A H 0.0152 0.5661 0.8254 0.069 Uiso 1 1 calc R
H20B H -0.0757 0.4974 0.7999 0.069 Uiso 1 1 calc R
C21 C 0.0001(8) 0.56198(19) 0.7248(2) 0.0527(12) Uani 1 1 d .
C22 C 0.1580(8) 0.5832(3) 0.6863(3) 0.0710(15) Uani 1 1 d .
H22 H 0.2878 0.5775 0.7015 0.085 Uiso 1 1 calc R
C23 C 0.1254(11) 0.6127(3) 0.6260(3) 0.092(2) Uani 1 1 d .
H23 H 0.2333 0.6274 0.6009 0.111 Uiso 1 1 calc R
C24 C -0.0630(12) 0.6207(3) 0.6027(3) 0.0864(18) Uani 1 1 d .
H24 H -0.0837 0.6400 0.5613 0.104 Uiso 1 1 calc R
C25 C -0.2199(10) 0.6008(3) 0.6393(4) 0.099(2) Uani 1 1 d .
H25 H -0.3490 0.6066 0.6234 0.119 Uiso 1 1 calc R
C26 C -0.1891(9) 0.5716(3) 0.7009(3) 0.0843(18) Uani 1 1 d .
H26 H -0.2981 0.5583 0.7263 0.101 Uiso 1 1 calc R
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
C3 S1 C1 95.5(2)
C3 S2 C2 95.1(2)
C5 S3 C4 94.8(2)
C4 S4 C6 95.1(2)
N2 N1 C7 110.9(3)
N2 N1 C13 120.0(4)
C7 N1 C13 129.1(4)
N3 N2 N1 107.9(4)
N2 N3 C8 108.0(4)
N5 N4 C9 110.4(3)
N5 N4 C20 118.1(3)
C9 N4 C20 131.5(4)
N6 N5 N4 107.6(3)
N5 N6 C10 108.8(4)
C2 C1 C11 127.4(5)
C2 C1 S1 116.9(4)
C11 C1 S1 115.7(4)
C1 C2 C12 126.4(5)
C1 C2 S2 118.0(4)
C12 C2 S2 115.7(4)
C4 C3 S2 124.1(3)
C4 C3 S1 121.7(3)
S2 C3 S1 114.2(2)
C3 C4 S4 123.9(3)
C3 C4 S3 121.8(3)
S4 C4 S3 114.3(2)
C6 C5 C7 125.8(4)
C6 C5 S3 118.2(3)
C7 C5 S3 116.0(3)
C5 C6 C9 123.8(4)
C5 C6 S4 116.5(3)
C9 C6 S4 119.5(3)
N1 C7 C8 103.5(4)
N1 C7 C5 123.3(4)
C8 C7 C5 133.1(4)
N3 C8 C7 109.6(4)
N4 C9 C10 103.5(4)
N4 C9 C6 126.6(4)
C10 C9 C6 129.7(4)
N6 C10 C9 109.7(4)
N1 C13 C14 113.5(4)
C15 C14 C19 118.4(4)
C15 C14 C13 123.1(4)
C19 C14 C13 118.5(4)
C14 C15 C16 120.9(5)
C17 C16 C15 120.2(5)
C16 C17 C18 119.2(5)
C17 C18 C19 121.5(6)
C18 C19 C14 119.8(5)
N4 C20 C21 113.0(4)
C26 C21 C22 118.0(5)
C26 C21 C20 119.5(5)
C22 C21 C20 122.5(5)
C23 C22 C21 120.7(6)
C24 C23 C22 120.5(6)
C25 C24 C23 120.1(6)
C24 C25 C26 120.0(6)
C21 C26 C25 120.7(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C3 1.756(4)
S1 C1 1.758(5)
S2 C3 1.749(4)
S2 C2 1.760(5)
S3 C5 1.747(4)
S3 C4 1.764(4)
S4 C4 1.760(4)
S4 C6 1.761(4)
N1 N2 1.339(5)
N1 C7 1.343(5)
N1 C13 1.465(5)
N2 N3 1.301(5)
N3 C8 1.348(6)
N4 N5 1.346(5)
N4 C9 1.360(5)
N4 C20 1.447(5)
N5 N6 1.307(5)
N6 C10 1.340(5)
C1 C2 1.322(6)
C1 C11 1.509(6)
C2 C12 1.517(6)
C3 C4 1.334(5)
C5 C6 1.347(5)
C5 C7 1.468(5)
C6 C9 1.461(5)
C7 C8 1.367(6)
C9 C10 1.372(6)
C13 C14 1.506(6)
C14 C15 1.370(6)
C14 C19 1.380(6)
C15 C16 1.381(7)
C16 C17 1.355(8)
C17 C18 1.359(8)
C18 C19 1.372(7)
C20 C21 1.512(6)
C21 C26 1.370(7)
C21 C22 1.378(7)
C22 C23 1.370(7)
C23 C24 1.358(8)
C24 C25 1.346(8)
C25 C26 1.390(8)
