#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:26:20 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179449 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/46/4334624.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_4334624
loop_
_publ_author_name
'Flavia Pop'
'François Riobé'
'Sabine Seifert'
'Thomas Cauchy'
'Jie Ding'
'Nathalie Dupont'
'Andreas Hauser'
'Marius Koch'
'Narcis Avarvari'
_publ_section_title
;
 Tetrathiafulvalene-1,3,5-triazines as (Multi)Donor-Acceptor Systems with
 Tunable Charge Transfer: Structural, Photophysical, and Theoretical
 Investigations
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5023
_journal_page_last               5034
_journal_paper_doi               10.1021/ic3027336
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C11 H7 Cl2 N3 S6'
_chemical_formula_sum            'C11 H7 Cl2 N3 S6'
_chemical_formula_weight         444.46
_chemical_name_common            TTF(SMe)2-dichloro-1,3,5-triazine
_chemical_name_systematic
;
 ?
;
_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                90.000(5)
_cell_angle_beta                 94.935(7)
_cell_angle_gamma                90.000(7)
_cell_formula_units_Z            4
_cell_length_a                   7.0913(5)
_cell_length_b                   15.9784(15)
_cell_length_c                   15.2724(12)
_cell_measurement_reflns_used    22558
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.51
_cell_measurement_theta_min      3.33
_cell_volume                     1724.1(2)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega 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  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22558
_diffrn_reflns_theta_full        26.51
_diffrn_reflns_theta_max         26.51
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    1.099
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0551
_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)+(0.0134P)²+5.0296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1168
_reflns_number_gt                2306
_reflns_number_total             3510
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic3027336_si_002_2.cif
_cod_data_source_block           3b
_cod_database_code               4334624
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
S1 S 0.26288(19) 0.47670(7) 0.54286(8) 0.0396(3) Uani 1 1 d .
S2 S 0.2084(2) 0.49474(8) 0.34913(8) 0.0464(3) Uani 1 1 d .
S3 S 0.2519(2) 0.27366(7) 0.52079(8) 0.0436(3) Uani 1 1 d .
S4 S 0.19126(19) 0.29263(8) 0.32827(8) 0.0427(3) Uani 1 1 d .
S5 S 0.2115(3) 0.08488(8) 0.51007(10) 0.0651(5) Uani 1 1 d .
S6 S 0.1107(2) 0.11171(9) 0.29444(9) 0.0586(4) Uani 1 1 d .
Cl1 Cl 0.3445(3) 0.68168(10) 0.80703(9) 0.0709(5) Uani 1 1 d .
Cl2 Cl 0.2973(2) 0.88602(8) 0.54407(10) 0.0653(4) Uani 1 1 d .
N1 N 0.2960(5) 0.6309(2) 0.6448(2) 0.0396(9) Uani 1 1 d .
N2 N 0.3147(6) 0.7772(2) 0.6707(3) 0.0476(11) Uani 1 1 d .
N3 N 0.2671(6) 0.7260(2) 0.5244(3) 0.0429(10) Uani 1 1 d .
C1 C 0.2499(6) 0.5779(3) 0.4986(3) 0.0352(11) Uani 1 1 d .
C2 C 0.2252(7) 0.5850(3) 0.4106(3) 0.0439(12) Uani 1 1 d .
H2 H 0.2174 0.6373 0.3837 0.053 Uiso 1 1 calc R
C3 C 0.2300(7) 0.4266(3) 0.4402(3) 0.0369(11) Uani 1 1 d .
C4 C 0.2223(6) 0.3425(3) 0.4309(3) 0.0339(10) Uani 1 1 d .
C5 C 0.2016(7) 0.1823(3) 0.4584(3) 0.0393(11) Uani 1 1 d .
C6 C 0.1735(7) 0.1912(3) 0.3709(3) 0.0389(11) Uani 1 1 d .
C7 C 0.1283(10) 0.1045(4) 0.6144(4) 0.077(2) Uani 1 1 d .
H7A H 0.1282 0.0533 0.6473 0.115 Uiso 1 1 calc R
H7B H 0.0020 0.1265 0.6067 0.115 Uiso 1 1 calc R
H7C H 0.2098 0.1444 0.6458 0.115 Uiso 1 1 calc R
C8 C 0.3295(10) 0.0622(5) 0.2815(5) 0.093(2) Uani 1 1 d .
H8A H 0.3102 0.0169 0.2404 0.140 Uiso 1 1 calc R
H8B H 0.3812 0.0407 0.3372 0.140 Uiso 1 1 calc R
H8C H 0.4158 0.1020 0.2600 0.140 Uiso 1 1 calc R
C9 C 0.2702(6) 0.6480(3) 0.5581(3) 0.0355(11) Uani 1 1 d .
C10 C 0.3143(7) 0.6981(3) 0.6949(3) 0.0419(12) Uani 1 1 d .
C11 C 0.2917(7) 0.7854(3) 0.5839(3) 0.0428(12) 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'
Cl Cl 0.1484 0.1585 '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
C1 S1 C3 94.5(2)
C2 S2 C3 95.2(2)
C4 S3 C5 95.2(2)
C4 S4 C6 95.5(2)
C5 S5 C7 104.2(3)
C6 S6 C8 102.9(3)
C10 N1 C9 113.8(4)
C10 N2 C11 111.8(4)
C11 N3 C9 114.0(4)
C2 C1 C9 124.2(4)
C2 C1 S1 117.5(3)
C9 C1 S1 118.3(3)
C1 C2 S2 118.1(4)
C4 C3 S1 123.2(3)
C4 C3 S2 122.1(3)
S1 C3 S2 114.7(3)
C3 C4 S4 123.1(3)
C3 C4 S3 122.6(3)
S4 C4 S3 114.3(2)
C6 C5 S5 122.8(4)
C6 C5 S3 117.2(3)
S5 C5 S3 119.7(3)
C5 C6 S4 117.3(3)
C5 C6 S6 126.4(4)
S4 C6 S6 116.3(3)
N3 C9 N1 123.9(4)
N3 C9 C1 118.7(4)
N1 C9 C1 117.4(4)
N2 C10 N1 128.4(4)
N2 C10 Cl1 114.9(4)
N1 C10 Cl1 116.7(4)
N3 C11 N2 128.1(4)
N3 C11 Cl2 115.8(4)
N2 C11 Cl2 116.1(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.752(4)
S1 C3 1.759(5)
S2 C2 1.719(5)
S2 C3 1.763(5)
S3 C4 1.758(4)
S3 C5 1.763(5)
S4 C4 1.755(4)
S4 C6 1.755(5)
S5 C5 1.744(5)
S5 C7 1.775(6)
S6 C6 1.757(5)
S6 C8 1.768(7)
Cl1 C10 1.727(5)
Cl2 C11 1.721(5)
N1 C10 1.318(6)
N1 C9 1.350(6)
N2 C10 1.317(6)
N2 C11 1.328(6)
N3 C11 1.315(6)
N3 C9 1.349(6)
C1 C2 1.346(6)
C1 C9 1.441(6)
C3 C4 1.352(6)
C5 C6 1.341(6)
