#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:13:44 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180129 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/27/7102718.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_7102718
loop_
_publ_author_name
'Devic, Thomas'
'Batail, Patrick'
'Avarvari, Narcis'
_publ_section_title
;
 [2 + 2]Photocyclization in a single-crystal-to-single-crystal
 transformation of a TTF-amido-pyridine.
;
_journal_issue                   13
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1538
_journal_page_last               1539
_journal_paper_doi               10.1039/b404482g
_journal_year                    2004
_chemical_formula_moiety         '2(C14H10S6N2O), C4H8O'
_chemical_formula_sum            'C32 H28 N4 O3 S12'
_chemical_formula_weight         901.39
_chemical_name_common
;
bis(-3,4-ethylenedithio-4'-(-3-
pyridincarmaboyl)tetrathiafulvalene), tetrahydrofurane solvate.
;
_chemical_name_systematic
;
bis(-3,4-ethylenedithio-4'-(-3-pyridincarmaboyl)tetrathiafulvalene),
tetrahydrofurane solvate.
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   14.3756(13)
_cell_length_b                   11.1605(7)
_cell_length_c                   22.9236(19)
_cell_measurement_reflns_used    6400
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      2.25
_cell_volume                     3677.8(5)
_computing_cell_refinement       'CELL, Stoe-IPDS'
_computing_data_collection       'EXPOSE, Stoe-IPDS'
_computing_data_reduction        'INTEGRATE, Stoe-IPDS'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.66
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  area_detector
_diffrn_measurement_method       'rotation, phi incr. 1'
_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  0.1450
_diffrn_reflns_av_sigmaI/netI    0.3544
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            23684
_diffrn_reflns_theta_full        25.86
_diffrn_reflns_theta_max         25.86
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.802
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.595
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.595
_refine_ls_R_factor_all          0.1690
_refine_ls_R_factor_gt           0.0470
_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)+(0.0201P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                1083
_reflns_number_total             3536
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b404482g.txt
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7102718
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'
'-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 1.08749(13) -0.03585(17) 0.59739(6) 0.0377(5) Uani 1 1 d .
S2 S 1.04465(13) 0.20235(15) 0.55225(7) 0.0404(5) Uani 1 1 d .
S3 S 0.98121(12) 0.02619(16) 0.71862(7) 0.0373(5) Uani 1 1 d .
S4 S 0.94863(13) 0.27140(16) 0.67765(7) 0.0418(5) Uani 1 1 d .
S5 S 0.85253(15) 0.04051(17) 0.81764(7) 0.0507(6) Uani 1 1 d .
S6 S 0.80985(13) 0.33343(16) 0.76722(7) 0.0428(5) Uani 1 1 d .
C1 C 1.0653(4) -0.0369(6) 0.5197(2) 0.0274(16) Uani 1 1 d .
C2 C 1.0345(4) 0.0875(6) 0.4973(3) 0.0334(18) Uani 1 1 d .
H2 H 1.0695 0.1096 0.4622 0.040 Uiso 1 1 calc R
C3 C 1.0326(5) 0.1018(6) 0.6098(3) 0.0350(18) Uani 1 1 d .
C4 C 0.9919(5) 0.1281(6) 0.6613(3) 0.0332(18) Uani 1 1 d .
C5 C 0.8998(5) 0.1116(6) 0.7573(3) 0.0330(17) Uani 1 1 d .
C6 C 0.8845(4) 0.2241(5) 0.7388(3) 0.0320(17) Uani 1 1 d .
C7 C 0.8174(6) 0.1685(7) 0.8594(3) 0.055(2) Uani 1 1 d .
H7A H 0.7853 0.1418 0.8943 0.065 Uiso 1 1 calc R
H7B H 0.8722 0.2127 0.8715 0.065 Uiso 1 1 calc R
C8 C 0.7537(6) 0.2513(7) 0.8249(3) 0.063(2) Uani 1 1 d .
H8A H 0.7257 0.3081 0.8517 0.075 Uiso 1 1 calc R
H8B H 0.7039 0.2039 0.8081 0.075 Uiso 1 1 calc R
O1 O 1.1733(4) -0.1931(5) 0.51878(18) 0.0563(15) Uani 1 1 d .
C9 C 1.1439(5) -0.1061(6) 0.4933(3) 0.0350(18) Uani 1 1 d .
N1 N 1.1770(3) -0.0716(4) 0.4406(2) 0.0312(14) Uani 1 1 d .
H1 H 1.1554 -0.0056 0.4267 0.037 Uiso 1 1 calc R
C10 C 1.2438(5) -0.1328(6) 0.4060(2) 0.0278(17) Uani 1 1 d .
C11 C 1.2786(5) -0.0775(6) 0.3574(3) 0.0371(19) Uani 1 1 d .
H11 H 1.2585 -0.0010 0.3474 0.045 Uiso 1 1 calc R
C12 C 1.3432(5) -0.1353(6) 0.3236(3) 0.046(2) Uani 1 1 d .
H12 H 1.3658 -0.0998 0.2897 0.055 Uiso 1 1 calc R
C13 C 1.3737(4) -0.2452(7) 0.3403(3) 0.0402(19) Uani 1 1 d .
H13 H 1.4206 -0.2816 0.3187 0.048 Uiso 1 1 calc R
N2 N 1.3397(4) -0.3031(5) 0.3863(2) 0.0372(15) Uani 1 1 d .
C14 C 1.2735(3) -0.2464(4) 0.42027(18) 0.0339(18) Uani 1 1 d .
H14 H 1.2490 -0.2850 0.4528 0.041 Uiso 1 1 calc R
C15 C 0.5045(3) 0.0390(4) 0.54829(18) 0.088(3) Uiso 1 1 d R
C16 C 0.4199(3) 0.0085(4) 0.50439(18) 0.115(4) Uiso 1 1 d R
O2 O 0.5783(3) 0.0845(4) 0.52447(18) 0.251(11) Uiso 0.50 1 d PR
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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
C3 S1 C1 95.0(3) . .
C3 S2 C2 93.6(3) . .
C4 S3 C5 94.9(3) . .
C4 S4 C6 94.8(3) . .
C5 S5 C7 99.9(3) . .
C6 S6 C8 101.1(3) . .
C9 C1 C2 123.1(5) . .
C9 C1 C2 113.5(5) . 5_756
C2 C1 C2 88.8(5) . 5_756
C9 C1 S1 105.6(4) . .
C2 C1 S1 111.9(4) . .
C2 C1 S1 113.7(4) 5_756 .
C1 C2 C1 91.2(5) . 5_756
C1 C2 S2 112.5(4) . .
C1 C2 S2 119.8(4) 5_756 .
C4 C3 S2 124.4(5) . .
C4 C3 S1 122.0(5) . .
S2 C3 S1 113.4(4) . .
C3 C4 S3 123.7(5) . .
C3 C4 S4 122.6(5) . .
S3 C4 S4 113.6(4) . .
C6 C5 S5 128.0(5) . .
C6 C5 S3 117.3(5) . .
S5 C5 S3 114.6(4) . .
C5 C6 S6 129.4(5) . .
C5 C6 S4 116.5(5) . .
S6 C6 S4 114.1(3) . .
C8 C7 S5 112.1(5) . .
C7 C8 S6 114.9(5) . .
O1 C9 N1 122.5(6) . .
O1 C9 C1 118.8(6) . .
N1 C9 C1 118.6(6) . .
C9 N1 C10 126.8(5) . .
C11 C10 C14 119.8(6) . .
C11 C10 N1 119.0(6) . .
C14 C10 N1 121.2(5) . .
C10 C11 C12 119.7(7) . .
C13 C12 C11 118.9(7) . .
N2 C13 C12 123.0(6) . .
C13 N2 C14 118.5(5) . .
C10 C14 N2 120.0(5) . .
O2 C15 C16 115.9 . .
O2 C15 C16 45.9(3) . 5_656
C16 C15 C16 88.5(3) . 5_656
O2 C16 C15 119.8(4) 5_656 .
O2 C16 C15 49.1(3) 5_656 5_656
C15 C16 C15 91.5(3) . 5_656
C16 O2 C15 85.0(5) 5_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C3 1.750(7) .
S1 C1 1.809(6) .
S2 C3 1.742(7) .
S2 C2 1.803(6) .
S3 C4 1.745(7) .
S3 C5 1.750(6) .
S4 C4 1.757(7) .
S4 C6 1.759(6) .
S5 C5 1.733(6) .
S5 C7 1.792(7) .
S6 C6 1.750(6) .
S6 C8 1.800(7) .
C1 C9 1.497(8) .
C1 C2 1.545(8) .
C1 C2 1.591(8) 5_756
C2 C1 1.591(8) 5_756
C3 C4 1.348(7) .
C5 C6 1.344(8) .
C7 C8 1.522(10) .
O1 C9 1.209(7) .
C9 N1 1.353(7) .
N1 C10 1.422(7) .
C10 C11 1.368(8) .
C10 C14 1.377(7) .
C11 C12 1.372(8) .
C12 C13 1.358(9) .
C13 N2 1.330(7) .
N2 C14 1.383(6) .
C15 O2 1.2972 .
C15 C16 1.6148 .
C15 C16 1.709(9) 5_656
C16 O2 1.231(9) 5_656
C16 C15 1.709(9) 5_656
O2 C16 1.231(9) 5_656
