#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/58/2235867.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2235867
loop_
_publ_author_name
'Katzsch, Felix'
'Weber, Edwin'
_publ_section_title
;
 Redetermination of tetramethyl
 tetrathiafulvalene-2,3,6,7-tetracarboxylate
;
_journal_coeditor_code           IM2387
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2354
_journal_page_last               o2355
_journal_paper_doi               10.1107/S1600536812029534
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H12 O8 S4'
_chemical_formula_moiety         'C14 H12 O8 S4'
_chemical_formula_sum            'C14 H12 O8 S4'
_chemical_formula_weight         436.48
_chemical_name_systematic
;
Tetramethyl tetrathiafulvalene-2,3,6,7-tetracarboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.2210(10)
_cell_angle_beta                 99.2550(10)
_cell_angle_gamma                99.3280(10)
_cell_formula_units_Z            1
_cell_length_a                   6.8666(2)
_cell_length_b                   7.8783(2)
_cell_length_c                   8.4335(2)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      45.31
_cell_measurement_theta_min      2.50
_cell_volume                     434.53(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0120
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10884
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  0.9169
_exptl_absorpt_correction_T_min  0.7046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0206
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0273P)²+0.2220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0540
_refine_ls_wR_factor_ref         0.0545
_reflns_number_gt                1471
_reflns_number_total             1534
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2387.cif
_cod_data_source_block           I
_cod_database_code               2235867
_cod_database_fobs_code          2235867
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.30978(5) 0.63798(4) 1.10656(4) 0.01479(11) Uani d . 1 1
S S2 0.06589(5) 0.56717(4) 0.76932(4) 0.01637(11) Uani d . 1 1
O O1 0.69629(14) 0.93615(13) 0.94082(12) 0.0194(2) Uani d . 1 1
O O2 0.72198(13) 0.79160(12) 1.14884(11) 0.0167(2) Uani d . 1 1
O O3 0.27914(16) 0.78034(15) 0.55357(13) 0.0265(3) Uani d . 1 1
O O4 0.56544(14) 0.69314(13) 0.64417(11) 0.0181(2) Uani d . 1 1
C C1 0.0779(2) 0.54255(17) 0.97428(16) 0.0140(3) Uani d . 1 1
C C2 0.4249(2) 0.71176(17) 0.95464(16) 0.0131(3) Uani d . 1 1
C C3 0.31610(19) 0.67605(17) 0.80137(16) 0.0138(3) Uani d . 1 1
C C4 0.62881(19) 0.82552(17) 1.00955(16) 0.0138(3) Uani d . 1 1
C C5 0.9200(2) 0.90095(19) 1.21844(18) 0.0196(3) Uani d . 1 1
H H5A 1.0006 0.8996 1.1353 0.029 Uiso calc R 1 1
H H5B 0.9840 0.8560 1.3075 0.029 Uiso calc R 1 1
H H5C 0.9061 1.0194 1.2584 0.029 Uiso calc R 1 1
C C6 0.3832(2) 0.72501(17) 0.65299(16) 0.0153(3) Uani d . 1 1
C C7 0.6552(2) 0.7573(2) 0.51653(17) 0.0226(3) Uani d . 1 1
H H7A 0.5790 0.6946 0.4108 0.034 Uiso calc R 1 1
H H7B 0.7911 0.7391 0.5270 0.034 Uiso calc R 1 1
H H7C 0.6548 0.8805 0.5272 0.034 Uiso calc R 1 1
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'
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_site_symmetry_1
_geom_angle
C2 S1 C1 . 94.90(6)
C3 S2 C1 . 94.65(6)
C4 O2 C5 . 115.25(10)
C6 O4 C7 . 115.57(11)
C1 C1 S1 2_567 122.42(14)
C1 C1 S2 2_567 122.68(14)
S1 C1 S2 . 114.90(7)
C3 C2 C4 . 125.13(12)
C3 C2 S1 . 117.68(10)
C4 C2 S1 . 116.86(10)
C2 C3 C6 . 126.96(12)
C2 C3 S2 . 117.78(10)
C6 C3 S2 . 115.23(10)
O1 C4 O2 . 125.14(12)
O1 C4 C2 . 124.48(12)
O2 C4 C2 . 110.33(11)
O2 C5 H5A . 109.5
O2 C5 H5B . 109.5
H5A C5 H5B . 109.5
O2 C5 H5C . 109.5
H5A C5 H5C . 109.5
H5B C5 H5C . 109.5
O3 C6 O4 . 125.74(12)
O3 C6 C3 . 122.87(12)
O4 C6 C3 . 111.34(11)
O4 C7 H7A . 109.5
O4 C7 H7B . 109.5
H7A C7 H7B . 109.5
O4 C7 H7C . 109.5
H7A C7 H7C . 109.5
H7B C7 H7C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C2 . 1.7452(13)
S1 C1 . 1.7570(13)
S2 C3 . 1.7468(13)
S2 C1 . 1.7636(13)
O1 C4 . 1.2022(16)
O2 C4 . 1.3363(16)
O2 C5 . 1.4559(16)
O3 C6 . 1.2007(17)
O4 C6 . 1.3263(16)
O4 C7 . 1.4487(16)
C1 C1 2_567 1.343(3)
C2 C3 . 1.3419(19)
C2 C4 . 1.4882(18)
C3 C6 . 1.4921(18)
C5 H5A . 0.9600
C5 H5B . 0.9600
C5 H5C . 0.9600
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C7 H7A S1 1_554 0.96 2.83 3.735(2) 157.7
C5 H5A O1 2_777 0.96 2.50 3.324(2) 143.3
C5 H5C O3 2_677 0.96 2.65 3.481(2) 144.9
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_4
_geom_torsion
C2 S1 C1 C1 2_567 178.58(16)
C2 S1 C1 S2 . -1.44(8)
C3 S2 C1 C1 2_567 -177.53(16)
C3 S2 C1 S1 . 2.49(8)
C1 S1 C2 C3 . -0.67(11)
C1 S1 C2 C4 . 173.05(10)
C4 C2 C3 C6 . 7.2(2)
S1 C2 C3 C6 . -179.69(10)
C4 C2 C3 S2 . -170.52(10)
S1 C2 C3 S2 . 2.63(15)
C1 S2 C3 C2 . -3.06(11)
C1 S2 C3 C6 . 178.99(10)
C5 O2 C4 O1 . 0.21(18)
C5 O2 C4 C2 . -177.38(10)
C3 C2 C4 O1 . 22.1(2)
S1 C2 C4 O1 . -151.10(11)
C3 C2 C4 O2 . -160.29(12)
S1 C2 C4 O2 . 26.51(14)
C7 O4 C6 O3 . 10.1(2)
C7 O4 C6 C3 . -172.26(11)
C2 C3 C6 O3 . -137.60(15)
S2 C3 C6 O3 . 40.13(17)
C2 C3 C6 O4 . 44.73(18)
S2 C3 C6 O4 . -137.54(10)
