#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/84/1508450.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_1508450
loop_
_publ_author_name
'Lieffrig, Julien'
'Jeannin, Olivier'
'Shin, Kyoung-Soon'
'Auban-Senzier, Pascale'
'Fourmigue, Marc'
_publ_section_title
;
 Halogen Bonding Interactions in DDQ Charge Transfer Salts with Iodinated
 TTFs
;
_journal_issue                   2
_journal_name_full               Crystals
_journal_page_first              327
_journal_page_last               337
_journal_paper_doi               10.3390/cryst2020327
_journal_volume                  2
_journal_year                    2012
_chemical_formula_moiety         'C8 H5 I S6, C8 Cl2 N2 O2'
_chemical_formula_sum            'C16 H5 Cl2 I N2 O2 S6'
_chemical_formula_weight         647.38
_chemical_name_common            'EDT-TTF-I, DDQ'
_chemical_name_systematic
; 
3-iodo-3',4'-ethylenedithio-tetrathiafulvalene,
dichlorodicyanobenzoquinone  
;
_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                62.1690(10)
_cell_angle_beta                 76.2820(10)
_cell_angle_gamma                78.6150(10)
_cell_formula_units_Z            2
_cell_length_a                   7.0227(2)
_cell_length_b                   12.6760(3)
_cell_length_c                   13.1732(3)
_cell_measurement_reflns_used    6635
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.06
_cell_volume                     1002.31(4)
_computing_cell_refinement       'Bruker SMART, 2006'
_computing_data_collection       'Bruker SMART, 2006'
_computing_data_reduction        'Bruker SAINT, 2006'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14723
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    2.508
_exptl_absorpt_correction_T_max  0.860
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.942
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4566
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0341
_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)+(0.0405P)²+3.4283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                3871
_reflns_number_total             4566
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file
C16H5Cl2IN2O2S6_P-1_EDTIDDQ_crystals-02-00327-s001_DC188.cif
_cod_data_source_block           EDTI-DDQ_chateigner_1508450
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1508450
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
I001 I -0.15422(4) 1.07095(3) 0.85497(2) 0.02409(10) Uani 1 1 d .
S1 S 0.13000(15) 0.95044(10) 0.69348(9) 0.0208(2) Uani 1 1 d .
S2 S 0.50402(16) 0.95804(10) 0.74718(9) 0.0206(2) Uani 1 1 d .
S3 S 0.35102(15) 0.82162(10) 0.53243(9) 0.0193(2) Uani 1 1 d .
S4 S 0.72788(15) 0.82145(10) 0.58938(9) 0.0190(2) Uani 1 1 d .
S5 S 0.50886(16) 0.69272(11) 0.38850(10) 0.0236(2) Uani 1 1 d .
S6 S 0.96625(15) 0.69606(11) 0.45605(10) 0.0219(2) Uani 1 1 d .
C1 C 0.1220(6) 1.0131(4) 0.7867(4) 0.0199(9) Uani 1 1 d .
C2 C 0.2949(7) 1.0180(4) 0.8100(4) 0.0220(9) Uani 1 1 d .
H2 H 0.3021 1.0521 0.8578 0.026 Uiso 1 1 calc R
C3 C 0.3814(6) 0.9202(4) 0.6716(3) 0.0175(8) Uani 1 1 d .
C4 C 0.4790(6) 0.8653(4) 0.6010(3) 0.0167(8) Uani 1 1 d .
C5 C 0.5556(6) 0.7540(4) 0.4732(4) 0.0175(8) Uani 1 1 d .
C6 C 0.7316(6) 0.7548(4) 0.4991(3) 0.0168(8) Uani 1 1 d .
C7 C 0.7273(6) 0.5891(4) 0.3951(4) 0.0229(9) Uani 1 1 d .
H7A H 0.7226 0.5263 0.4742 0.027 Uiso 1 1 calc R
H7B H 0.7268 0.5518 0.3454 0.027 Uiso 1 1 calc R
C8 C 0.9153(7) 0.6448(5) 0.3589(4) 0.0281(10) Uani 1 1 d .
H8A H 0.9134 0.7125 0.2827 0.034 Uiso 1 1 calc R
H8B H 1.0231 0.5868 0.3506 0.034 Uiso 1 1 calc R
Cl1 Cl 0.87206(15) 0.31981(9) 0.94407(9) 0.0214(2) Uani 1 1 d .
Cl2 Cl 1.01446(14) 0.57522(10) 0.75927(9) 0.0208(2) Uani 1 1 d .
O1 O 0.5864(4) 0.3319(3) 1.1421(2) 0.0189(6) Uani 1 1 d .
O2 O 0.8462(4) 0.7638(3) 0.8322(2) 0.0192(6) Uani 1 1 d .
N2 N 0.5585(6) 0.8260(4) 1.0622(4) 0.0295(9) Uani 1 1 d .
N1 N 0.4013(6) 0.5089(3) 1.2935(3) 0.0238(8) Uani 1 1 d .
C9 C 0.6508(6) 0.4299(4) 1.0734(3) 0.0146(8) Uani 1 1 d .
C10 C 0.7895(6) 0.4477(4) 0.9640(3) 0.0151(8) Uani 1 1 d .
C11 C 0.8522(5) 0.5564(4) 0.8864(3) 0.0151(8) Uani 1 1 d .
C12 C 0.7885(6) 0.6654(4) 0.9034(3) 0.0146(8) Uani 1 1 d .
C13 C 0.6617(6) 0.6461(4) 1.0146(3) 0.0142(8) Uani 1 1 d .
C14 C 0.6044(6) 0.7477(4) 1.0395(4) 0.0188(9) Uani 1 1 d .
C15 C 0.5983(6) 0.5354(4) 1.0940(3) 0.0139(8) Uani 1 1 d .
C16 C 0.4845(6) 0.5189(4) 1.2063(4) 0.0170(8) 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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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 95.3(2)
C4 S3 C5 95.8(2)
C4 S4 C6 95.3(2)
C5 S5 C7 99.4(2)
C6 S6 C8 101.4(2)
C2 C1 S1 116.7(3)
C2 C1 I001 125.9(3)
S1 C1 I001 117.4(2)
C1 C2 S2 117.1(3)
C1 C2 H2 121.4
S2 C2 H2 121.4
C4 C3 S1 122.2(3)
C4 C3 S2 122.4(3)
S1 C3 S2 115.4(2)
C3 C4 S4 122.7(3)
C3 C4 S3 121.2(3)
S4 C4 S3 115.7(2)
C6 C5 S3 116.2(3)
C6 C5 S5 128.2(3)
S3 C5 S5 115.6(2)
C5 C6 S4 116.9(3)
C5 C6 S6 129.2(3)
S4 C6 S6 113.9(2)
C8 C7 S5 114.2(3)
C8 C7 H7A 108.7
S5 C7 H7A 108.7
C8 C7 H7B 108.7
S5 C7 H7B 108.7
H7A C7 H7B 107.6
C7 C8 S6 115.8(3)
C7 C8 H8A 108.3
S6 C8 H8A 108.3
C7 C8 H8B 108.3
S6 C8 H8B 108.3
H8A C8 H8B 107.4
O1 C9 C15 123.0(4)
O1 C9 C10 122.5(4)
C15 C9 C10 114.5(3)
C11 C10 C9 122.3(4)
C11 C10 Cl1 122.3(3)
C9 C10 Cl1 115.4(3)
C10 C11 C12 123.2(4)
C10 C11 Cl2 121.6(3)
C12 C11 Cl2 115.3(3)
O2 C12 C13 122.9(4)
O2 C12 C11 122.6(4)
C13 C12 C11 114.4(3)
C15 C13 C14 120.5(4)
C15 C13 C12 122.5(4)
C14 C13 C12 117.0(4)
N2 C14 C13 178.3(5)
C13 C15 C16 120.3(4)
C13 C15 C9 122.9(4)
C16 C15 C9 116.6(4)
N1 C16 C15 177.2(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I001 C1 2.082(4)
S1 C3 1.715(4)
S1 C1 1.733(4)
S2 C3 1.725(5)
S2 C2 1.728(4)
S3 C4 1.726(4)
S3 C5 1.736(4)
S4 C4 1.720(4)
S4 C6 1.744(4)
S5 C5 1.745(4)
S5 C7 1.802(4)
S6 C6 1.749(4)
S6 C8 1.810(5)
C1 C2 1.340(6)
C2 H2 0.9300
C3 C4 1.391(6)
C5 C6 1.361(6)
C7 C8 1.492(7)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9700
C8 H8B 0.9700
Cl1 C10 1.728(4)
Cl2 C11 1.729(4)
O1 C9 1.243(5)
O2 C12 1.235(5)
N2 C14 1.132(6)
N1 C16 1.119(6)
C9 C15 1.447(6)
C9 C10 1.481(6)
C10 C11 1.360(6)
C11 C12 1.469(6)
C12 C13 1.459(5)
C13 C15 1.385(6)
C13 C14 1.434(6)
C15 C16 1.445(6)
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
C3 S1 C1 C2 0.0(4)
C3 S1 C1 I001 -178.8(2)
S1 C1 C2 S2 -1.5(5)
I001 C1 C2 S2 177.2(2)
C3 S2 C2 C1 2.1(4)
C1 S1 C3 C4 179.4(4)
C1 S1 C3 S2 1.4(3)
C2 S2 C3 C4 -180.0(4)
C2 S2 C3 S1 -2.1(3)
S1 C3 C4 S4 -173.6(2)
S2 C3 C4 S4 4.2(5)
S1 C3 C4 S3 -1.1(5)
S2 C3 C4 S3 176.6(2)
C6 S4 C4 C3 176.1(4)
C6 S4 C4 S3 3.2(3)
C5 S3 C4 C3 -175.8(3)
C5 S3 C4 S4 -2.9(3)
C4 S3 C5 C6 1.2(4)
C4 S3 C5 S5 -179.1(2)
C7 S5 C5 C6 20.5(4)
C7 S5 C5 S3 -159.1(3)
S3 C5 C6 S4 0.8(5)
S5 C5 C6 S4 -178.7(2)
S3 C5 C6 S6 179.9(3)
S5 C5 C6 S6 0.3(6)
C4 S4 C6 C5 -2.4(4)
C4 S4 C6 S6 178.3(2)
C8 S6 C6 C5 4.3(5)
C8 S6 C6 S4 -176.6(2)
C5 S5 C7 C8 -53.9(4)
S5 C7 C8 S6 69.0(4)
C6 S6 C8 C7 -38.7(4)
O1 C9 C10 C11 176.8(4)
C15 C9 C10 C11 -3.8(5)
O1 C9 C10 Cl1 -5.2(5)
C15 C9 C10 Cl1 174.3(3)
C9 C10 C11 C12 -0.2(6)
Cl1 C10 C11 C12 -178.1(3)
C9 C10 C11 Cl2 179.9(3)
Cl1 C10 C11 Cl2 2.0(5)
C10 C11 C12 O2 -179.9(4)
Cl2 C11 C12 O2 0.0(5)
C10 C11 C12 C13 3.9(5)
Cl2 C11 C12 C13 -176.3(3)
O2 C12 C13 C15 -179.8(4)
C11 C12 C13 C15 -3.5(5)
O2 C12 C13 C14 -0.1(6)
C11 C12 C13 C14 176.2(3)
C15 C13 C14 N2 24(15)
C12 C13 C14 N2 -156(15)
C14 C13 C15 C16 -4.1(6)
C12 C13 C15 C16 175.6(4)
C14 C13 C15 C9 179.8(4)
C12 C13 C15 C9 -0.5(6)
O1 C9 C15 C13 -176.5(4)
C10 C9 C15 C13 4.1(5)
O1 C9 C15 C16 7.3(6)
C10 C9 C15 C16 -172.1(3)
C13 C15 C16 N1 -42(10)
C9 C15 C16 N1 134(9)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 30652003 ChemSpider
