#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:22:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180426 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/95/7209539.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_7209539
loop_
_publ_author_name
'Imakubo, Tatsuro'
'Murayama, Ryosuke'
_publ_section_title
;
 Solvent dependence of crystal morphology, donor/anion ratio and
 electrical conductivity in a series of hexagonal supramolecular organic
 conductors based on diiodo(pyrazino)tetrathiafulvalene (DIP)
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              3072
_journal_paper_doi               10.1039/c2ce26739j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         (C8H2N2I2S4)3(PF6)0.62(C4H8O2)0.49
_chemical_formula_sum            'C25.96 H9.92 F3.72 I6 N6 O0.98 P0.62 S12'
_chemical_formula_weight         1657.63
_chemical_name_common            (DIP)3(PF6)0.62(AcOEt)0.49
_chemical_name_systematic
;
?
;
_space_group_IT_number           193
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  '-P 6c 2'
_symmetry_space_group_name_H-M   'P 63/m c m'
_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                120.00
_cell_formula_units_Z            2
_cell_length_a                   20.0593(13)
_cell_length_b                   20.0593(13)
_cell_length_c                   7.1695(9)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.23
_cell_measurement_theta_min      2.34
_cell_volume                     2498.3(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  '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  0.1259
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            50752
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.17
_exptl_absorpt_coefficient_mu    4.291
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rot
_exptl_crystal_F_000             1530
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.409
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.469
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1181
_refine_ls_number_restraints     116
_refine_ls_restrained_S_all      1.427
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0442P)²+7.2281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1198
_reflns_number_gt                1138
_reflns_number_total             1181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26739j.txt
_cod_data_source_block           m1361
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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_sg_symbol_H-M      P6(3)/mcm
_cod_database_code               7209539
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'-y, -x, -z'
'-x+y, y, -z'
'x, x-y, -z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'x, y, -z-1/2'
'-y, x-y, -z-1/2'
'-x+y, -x, -z-1/2'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'y, x, z'
'x-y, -y, z'
'-x, -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
I1 I 1.11088(3) 0.35586(3) 0.2500 0.0334(2) Uani 1 2 d SU
S1 S 1.08447(12) 0.50269(11) 0.2500 0.0368(5) Uani 1 2 d SU
S2 S 0.91419(11) 0.57779(11) 0.2500 0.0337(4) Uani 1 2 d SU
N1 N 0.9193(4) 0.7134(4) 0.2500 0.0381(16) Uani 1 2 d SU
C1 C 1.0000 0.5077(6) 0.2500 0.031(2) Uani 1 4 d SU
C2 C 1.0000 0.5752(6) 0.2500 0.030(2) Uani 1 4 d SU
C3 C 1.0379(5) 0.4012(4) 0.2500 0.0301(15) Uani 1 2 d SU
C4 C 0.9596(4) 0.6775(4) 0.2500 0.0295(16) Uani 1 2 d SU
C5 C 0.9606(5) 0.7909(5) 0.2500 0.046(2) Uani 1 2 d SU
H5 H 0.9346 0.8185 0.2500 0.056 Uiso 1 2 calc SR
P1 P 1.0000 1.0000 0.057(3) 0.052(5) Uani 0.25 6 d SPDU
F1 F 0.9252(8) 0.9252(8) 0.056(5) 0.078(8) Uani 0.25 2 d SPDU
F2 F 0.9347(13) 0.9347(13) 0.2500 0.102(8) Uani 0.50 4 d SPU
C6 C 0.714(6) 0.408(6) 0.223(7) 0.09(3) Uani 0.08 1 d PDU
C7 C 0.728(2) 0.4412(5) 0.023(4) 0.088(5) Uani 1 1 d DU
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 S1 C3 95.5(4) . .
C4 S2 C2 94.4(4) . .
C4 N1 C5 116.0(7) . .
C2 C1 S1 122.8(3) . 9_765
C2 C1 S1 122.8(3) . .
S1 C1 S1 114.3(6) 9_765 .
C1 C2 S2 121.5(3) . 9_765
C1 C2 S2 121.5(3) . .
S2 C2 S2 117.1(6) 9_765 .
C3 C3 S1 117.3(3) 9_765 .
C3 C3 I1 127.7(2) 9_765 .
S1 C3 I1 115.0(4) . .
N1 C4 C4 121.9(5) . 9_765
N1 C4 S2 121.1(6) . .
C4 C4 S2 117.0(2) 9_765 .
N1 C5 C5 122.1(5) . 9_765
N1 C5 H5 119.0 . .
C5 C5 H5 119.0 9_765 .
P1 P1 F1 89.6(15) 13_775 .
P1 P1 F1 89.6(15) 13_775 3_675
F1 P1 F1 120.00(6) . 3_675
P1 P1 F1 89.6(15) 13_775 2_765
F1 P1 F1 120.00(4) . 2_765
F1 P1 F1 120.00(7) 3_675 2_765
P1 P1 F1 61.5(11) 13_775 15_655
F1 P1 F1 63.7(10) . 15_655
F1 P1 F1 151.1(14) 3_675 15_655
F1 P1 F1 63.7(10) 2_765 15_655
P1 P1 F1 61.5(11) 13_775 14_565
F1 P1 F1 63.7(10) . 14_565
F1 P1 F1 63.7(10) 3_675 14_565
F1 P1 F1 151.1(14) 2_765 14_565
F1 P1 F1 99.1(14) 15_655 14_565
P1 P1 F1 61.5(11) 13_775 13_775
F1 P1 F1 151.1(14) . 13_775
F1 P1 F1 63.7(10) 3_675 13_775
F1 P1 F1 63.7(10) 2_765 13_775
F1 P1 F1 99.1(14) 15_655 13_775
F1 P1 F1 99.1(14) 14_565 13_775
P1 P1 F2 136.5(7) 13_775 3_675
F1 P1 F2 110.4(13) . 3_675
F1 P1 F2 46.9(14) 3_675 3_675
F1 P1 F2 110.4(13) 2_765 3_675
F1 P1 F2 162.0(15) 15_655 3_675
F1 P1 F2 92.5(9) 14_565 3_675
F1 P1 F2 92.5(9) 13_775 3_675
P1 P1 F2 136.5(7) 13_775 2_765
F1 P1 F2 110.4(13) . 2_765
F1 P1 F2 110.4(13) 3_675 2_765
F1 P1 F2 46.9(14) 2_765 2_765
F1 P1 F2 92.5(9) 15_655 2_765
F1 P1 F2 162.0(15) 14_565 2_765
F1 P1 F2 92.5(9) 13_775 2_765
F2 P1 F2 73.2(11) 3_675 2_765
P1 P1 F2 136.5(7) 13_775 .
F1 P1 F2 46.9(14) . .
F1 P1 F2 110.4(13) 3_675 .
F1 P1 F2 110.4(13) 2_765 .
F1 P1 F2 92.5(9) 15_655 .
F1 P1 F2 92.5(9) 14_565 .
F1 P1 F2 162.0(15) 13_775 .
F2 P1 F2 73.2(11) 3_675 .
F2 P1 F2 73.2(11) 2_765 .
F2 F1 P1 81.8(19) . .
F2 F1 P1 110.7(17) . 13_775
P1 F1 P1 28.9(14) . 13_775
F2 F1 F1 114(2) . 15_655
P1 F1 F1 64.1(4) . 15_655
P1 F1 F1 52.2(8) 13_775 15_655
F2 F1 F1 114(2) . 14_565
P1 F1 F1 64.1(4) . 14_565
P1 F1 F1 52.2(8) 13_775 14_565
F1 F1 F1 100(2) 15_655 14_565
F1 F2 F1 164(3) . 16_556
F1 F2 P1 144.3(19) . 16_556
F1 F2 P1 51.3(10) 16_556 16_556
F1 F2 P1 51.3(10) . .
F1 F2 P1 144.3(19) 16_556 .
P1 F2 P1 93.0(14) 16_556 .
C6 C6 C7 158(4) 16_556 .
C6 C6 C7 159(4) 16_556 11_655
C7 C6 C7 9(2) . 11_655
C6 C6 C7 18(3) 16_556 16_556
C7 C6 C7 140(7) . 16_556
C7 C6 C7 143(6) 11_655 16_556
C7 C7 C6 137(10) 11_655 .
C7 C7 C6 34(9) 11_655 11_655
C6 C7 C6 139(8) . 11_655
C7 C7 C6 138(10) 11_655 16_556
C6 C7 C6 4.4(17) . 16_556
C6 C7 C6 144(6) 11_655 16_556
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C3 2.075(7) .
S1 C1 1.746(6) .
S1 C3 1.765(8) .
S2 C4 1.734(8) .
S2 C2 1.747(6) .
N1 C4 1.322(10) .
N1 C5 1.347(12) .
C1 C2 1.356(15) .
C1 S1 1.746(6) 9_765
C2 S2 1.747(6) 9_765
C3 C3 1.316(16) 9_765
C4 C4 1.405(15) 9_765
C5 C5 1.371(19) 9_765
C5 H5 0.9300 .
P1 P1 0.82(4) 13_775
P1 F1 1.500(17) .
P1 F1 1.500(16) 3_675
P1 F1 1.500(17) 2_765
P1 F1 1.71(2) 15_655
P1 F1 1.71(2) 14_565
P1 F1 1.71(2) 13_775
P1 F2 1.90(2) 3_675
P1 F2 1.90(2) 2_765
P1 F2 1.90(2) .
F1 F2 1.40(3) .
F1 P1 1.71(2) 13_775
F1 F1 1.70(3) 15_655
F1 F1 1.70(3) 14_565
F2 F1 1.40(3) 16_556
F2 P1 1.90(2) 16_556
C6 C6 0.39(11) 16_556
C6 C7 1.54(2) .
C6 C7 1.88(5) 11_655
C6 C7 1.91(9) 16_556
C7 C7 0.43(5) 11_655
C7 C6 1.88(5) 11_655
C7 C6 1.91(9) 16_556
