#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:22:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180426 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/95/7209536.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_7209536
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)0.70(C3H8O)0.65
_chemical_formula_sum            'C25.95 H11.2 F4.2 I6 N6 O0.65 P0.7 S12'
_chemical_formula_weight         1665.12
_chemical_name_common            (DIP)3(PF6)0.70(1-PrOH)0.65
_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                   20.0460(8)
_cell_length_b                   20.0460(8)
_cell_length_c                   7.1715(5)
_cell_measurement_reflns_used    8255
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.03
_cell_measurement_theta_min      2.35
_cell_volume                     2495.7(2)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1005
_diffrn_reflns_av_sigmaI/netI    0.0215
_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            50765
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.17
_exptl_absorpt_coefficient_mu    4.297
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1533
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         3.369
_refine_diff_density_min         -1.931
_refine_diff_density_rms         0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.489
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1181
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.482
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0729
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0408P)²+33.9753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1599
_reflns_number_gt                1174
_reflns_number_total             1181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26739j.txt
_cod_data_source_block           m130a1
_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               7209536
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 1.11085(5) 0.35587(5) 0.2500 0.0308(3) Uani 1 2 d S
S1 S 1.08421(18) 0.50267(18) 0.2500 0.0345(8) Uani 1 2 d S
S2 S 0.91418(18) 0.57785(17) 0.2500 0.0318(7) Uani 1 2 d S
C1 C 1.0000 0.5074(9) 0.2500 0.029(3) Uani 1 4 d S
C2 C 1.0000 0.5761(9) 0.2500 0.028(4) Uani 1 4 d S
C3 C 1.0384(7) 0.4017(7) 0.2500 0.028(2) Uani 1 2 d S
C4 C 0.9594(7) 0.6779(8) 0.2500 0.031(3) Uani 1 2 d S
N1 N 0.9196(7) 0.7137(7) 0.2500 0.036(3) Uani 1 2 d S
C5 C 0.9599(8) 0.7901(8) 0.2500 0.042(4) Uani 1 2 d S
H5 H 0.9338 0.8176 0.2500 0.3(2) Uiso 1 2 calc SR
F1 F 0.9264(11) 0.9264(11) 0.050(7) 0.069(11) Uani 0.25 2 d SPDU
P1 P 1.0000 1.0000 0.093(4) 0.057(7) Uani 0.25 6 d SPDU
F2 F 0.9431(15) 0.9431(15) 0.2500 0.085(10) Uani 0.50 4 d SPDU
O1 O 0.704(7) 0.381(5) 0.195(17) 0.18(5) Uani 0.17 1 d PU
C6 C 0.726(4) 0.4395(8) 0.023(6) 0.091(9) Uani 1 1 d U
C7 C 0.6667 0.3333 0.0000 0.20(6) Uani 0.50 6 d SPU
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 95.8(7) . .
C2 S2 C4 94.2(6) . .
C2 C1 S1 122.7(5) . 9_765
C2 C1 S1 122.7(5) . .
S1 C1 S1 114.6(10) 9_765 .
C1 C2 S2 121.0(5) . 9_765
C1 C2 S2 121.0(5) . .
S2 C2 S2 118.0(10) 9_765 .
C3 C3 S1 116.9(4) 9_765 .
C3 C3 I1 127.4(4) 9_765 .
S1 C3 I1 115.7(6) . .
N1 C4 C4 121.7(8) . 9_765
N1 C4 S2 121.4(10) . .
C4 C4 S2 116.8(4) 9_765 .
C4 N1 C5 116.5(12) . .
N1 C5 C5 121.8(8) . 9_765
N1 C5 H5 119.1 . .
C5 C5 H5 119.1 9_765 .
F2 F1 P1 65.2(16) . .
F2 F1 F1 109(3) . 15_655
P1 F1 F1 69.4(8) . 15_655
F2 F1 F1 109(3) . 14_565
P1 F1 F1 69.4(8) . 14_565
F1 F1 F1 102(4) 15_655 14_565
F2 F1 P1 112(2) . 13_775
P1 F1 P1 46(2) . 13_775
F1 F1 P1 51.7(14) 15_655 13_775
F1 F1 P1 51.7(14) 14_565 13_775
P1 P1 F1 78(2) 13_775 .
P1 P1 F1 78(2) 13_775 3_675
F1 P1 F1 116.0(16) . 3_675
P1 P1 F1 78(2) 13_775 2_765
F1 P1 F1 116.0(15) . 2_765
F1 P1 F1 116.0(16) 3_675 2_765
P1 P1 F2 134.7(14) 13_775 3_675
F1 P1 F2 119.4(18) . 3_675
F1 P1 F2 56(2) 3_675 3_675
F1 P1 F2 119.4(18) 2_765 3_675
P1 P1 F2 134.7(14) 13_775 2_765
F1 P1 F2 119.4(18) . 2_765
F1 P1 F2 119.4(19) 3_675 2_765
F1 P1 F2 56(2) 2_765 2_765
F2 P1 F2 76(2) 3_675 2_765
P1 P1 F2 134.7(14) 13_775 .
F1 P1 F2 56(2) . .
F1 P1 F2 119.4(18) 3_675 .
F1 P1 F2 119.4(18) 2_765 .
F2 P1 F2 76(2) 3_675 .
F2 P1 F2 76(2) 2_765 .
P1 P1 F1 55.2(15) 13_775 14_565
F1 P1 F1 58.8(14) . 14_565
F1 P1 F1 58.8(14) 3_675 14_565
F1 P1 F1 134(2) 2_765 14_565
F2 P1 F1 96.3(11) 3_675 14_565
F2 P1 F1 170(3) 2_765 14_565
F2 P1 F1 96.3(11) . 14_565
P1 P1 F1 55.2(15) 13_775 15_655
F1 P1 F1 58.8(14) . 15_655
F1 P1 F1 134(2) 3_675 15_655
F1 P1 F1 58.8(14) 2_765 15_655
F2 P1 F1 170(3) 3_675 15_655
F2 P1 F1 96.3(11) 2_765 15_655
F2 P1 F1 96.3(11) . 15_655
F1 P1 F1 91(2) 14_565 15_655
P1 P1 F1 55.2(15) 13_775 13_775
F1 P1 F1 134(2) . 13_775
F1 P1 F1 58.8(14) 3_675 13_775
F1 P1 F1 58.8(14) 2_765 13_775
F2 P1 F1 96.3(11) 3_675 13_775
F2 P1 F1 96.3(11) 2_765 13_775
F2 P1 F1 170(3) . 13_775
F1 P1 F1 91(2) 14_565 13_775
F1 P1 F1 91(2) 15_655 13_775
P1 P1 P1 180.00(4) 13_775 16_556
F1 P1 P1 102(2) . 16_556
F1 P1 P1 102(2) 3_675 16_556
F1 P1 P1 102(2) 2_765 16_556
F2 P1 P1 45.3(14) 3_675 16_556
F2 P1 P1 45.3(14) 2_765 16_556
F2 P1 P1 45.3(14) . 16_556
F1 P1 P1 124.8(15) 14_565 16_556
F1 P1 P1 124.8(15) 15_655 16_556
F1 P1 P1 124.8(15) 13_775 16_556
F1 F2 F1 154(3) . 16_556
F1 F2 P1 148(3) . 16_556
F1 F2 P1 58.5(11) 16_556 16_556
F1 F2 P1 58.5(11) . .
F1 F2 P1 148(3) 16_556 .
P1 F2 P1 89(3) 16_556 .
O1 O1 O1 90.00(4) 16_556 3_665
O1 O1 O1 90.00(11) 16_556 2_655
O1 O1 O1 60.00(4) 3_665 2_655
O1 O1 O1 63(8) 16_556 18_666
O1 O1 O1 27(8) 3_665 18_666
O1 O1 O1 64(2) 2_655 18_666
O1 O1 O1 63(8) 16_556 17_656
O1 O1 O1 64(2) 3_665 17_656
O1 O1 O1 27(8) 2_655 17_656
O1 O1 O1 53(4) 18_666 17_656
O1 O1 C6 140(4) 16_556 .
O1 O1 C6 130(5) 3_665 .
O1 O1 C6 110(10) 2_655 .
O1 O1 C6 157(10) 18_666 .
O1 O1 C6 131(10) 17_656 .
O1 O1 C7 148(3) 16_556 .
O1 O1 C7 63(2) 3_665 .
O1 O1 C7 63(2) 2_655 .
O1 O1 C7 89(7) 18_666 .
O1 O1 C7 89(7) 17_656 .
C6 O1 C7 69(5) . .
C6 C6 O1 133(10) 11_655 .
C6 C6 C7 83.8(13) 11_655 .
O1 C6 C7 56(4) . .
O1 C7 O1 119(6) 12 3_665
O1 C7 O1 133(9) 12 .
O1 C7 O1 55(5) 3_665 .
O1 C7 O1 55(5) 12 10_665
O1 C7 O1 133(9) 3_665 10_665
O1 C7 O1 168(10) . 10_665
O1 C7 O1 55(5) 12 11_655
O1 C7 O1 168(10) 3_665 11_655
O1 C7 O1 119(6) . 11_655
O1 C7 O1 55(5) 10_665 11_655
O1 C7 O1 168(10) 12 2_655
O1 C7 O1 55(5) 3_665 2_655
O1 C7 O1 55(5) . 2_655
O1 C7 O1 119(7) 10_665 2_655
O1 C7 O1 133(9) 11_655 2_655
O1 C7 C6 54(3) 12 12
O1 C7 C6 65(4) 3_665 12
O1 C7 C6 99(6) . 12
O1 C7 C6 94(6) 10_665 12
O1 C7 C6 107(5) 11_655 12
O1 C7 C6 119(5) 2_655 12
O1 C7 C6 65(4) 12 3_665
O1 C7 C6 54(3) 3_665 3_665
O1 C7 C6 94(6) . 3_665
O1 C7 C6 99(6) 10_665 3_665
O1 C7 C6 119(5) 11_655 3_665
O1 C7 C6 107(5) 2_655 3_665
C6 C7 C6 12(3) 12 3_665
O1 C7 C6 99(6) 12 .
O1 C7 C6 107(5) 3_665 .
O1 C7 C6 54(3) . .
O1 C7 C6 119(5) 10_665 .
O1 C7 C6 65(4) 11_655 .
O1 C7 C6 94(6) 2_655 .
C6 C7 C6 113(5) 12 .
C6 C7 C6 119.2(4) 3_665 .
O1 C7 C6 107(5) 12 10_665
O1 C7 C6 99(6) 3_665 10_665
O1 C7 C6 119(5) . 10_665
O1 C7 C6 54(3) 10_665 10_665
O1 C7 C6 94(6) 11_655 10_665
O1 C7 C6 65(4) 2_655 10_665
C6 C7 C6 119.2(4) 12 10_665
C6 C7 C6 113(5) 3_665 10_665
C6 C7 C6 127(4) . 10_665
O1 C7 C6 94(6) 12 11_655
O1 C7 C6 119(5) 3_665 11_655
O1 C7 C6 65(4) . 11_655
O1 C7 C6 107(5) 10_665 11_655
O1 C7 C6 54(3) 11_655 11_655
O1 C7 C6 99(6) 2_655 11_655
C6 C7 C6 119.2(4) 12 11_655
C6 C7 C6 127(4) 3_665 11_655
C6 C7 C6 12(3) . 11_655
C6 C7 C6 119.2(4) 10_665 11_655
O1 C7 C6 119(5) 12 2_655
O1 C7 C6 94(6) 3_665 2_655
O1 C7 C6 107(5) . 2_655
O1 C7 C6 65(4) 10_665 2_655
O1 C7 C6 99(6) 11_655 2_655
O1 C7 C6 54(3) 2_655 2_655
C6 C7 C6 127(4) 12 2_655
C6 C7 C6 119.2(4) 3_665 2_655
C6 C7 C6 119.2(4) . 2_655
C6 C7 C6 12(3) 10_665 2_655
C6 C7 C6 113(5) 11_655 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C3 2.070(12) .
S1 C1 1.738(10) .
S1 C3 1.756(13) .
S2 C2 1.738(10) .
S2 C4 1.739(14) .
C1 C2 1.38(2) .
C1 S1 1.738(10) 9_765
C2 S2 1.738(10) 9_765
C3 C3 1.33(2) 9_765
C4 N1 1.313(16) .
C4 C4 1.41(2) 9_765
N1 C5 1.327(17) .
C5 C5 1.39(3) 9_765
C5 H5 0.9300 .
F1 F2 1.47(5) .
F1 P1 1.507(19) .
F1 F1 1.64(5) 15_655
F1 F1 1.64(5) 14_565
F1 P1 1.80(4) 13_775
P1 P1 1.33(6) 13_775
P1 F1 1.507(19) 3_675
P1 F1 1.507(19) 2_765
P1 F2 1.604(18) 3_675
P1 F2 1.604(18) 2_765
P1 F2 1.604(18) .
P1 F1 1.80(4) 14_565
P1 F1 1.80(4) 15_655
P1 F1 1.80(4) 13_775
P1 P1 2.26(6) 16_556
F2 F1 1.47(5) 16_556
F2 P1 1.604(18) 16_556
O1 O1 0.8(2) 16_556
O1 O1 1.52(13) 3_665
O1 O1 1.52(14) 2_655
O1 O1 1.71(15) 18_666
O1 O1 1.71(15) 17_656
O1 C6 1.60(11) .
O1 C7 1.65(11) .
C6 C6 0.40(8) 11_655
C6 C7 1.854(13) .
C7 O1 1.65(11) 12
C7 O1 1.65(11) 3_665
C7 O1 1.65(11) 10_665
C7 O1 1.65(11) 11_655
C7 O1 1.65(11) 2_655
C7 C6 1.854(13) 12
C7 C6 1.854(13) 3_665
C7 C6 1.854(13) 10_665
C7 C6 1.854(13) 11_655
C7 C6 1.854(13) 2_655
