#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:22:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180426 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/95/7209537.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_7209537
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)0.63(C3H8O)0.92
_chemical_formula_sum            'C26.76 H13.36 F3.78 I6 N6 O0.92 P0.63 S12'
_chemical_formula_weight         1671.20
_chemical_name_common            (DIP)3(PF6)0.63(2-PrOH)0.92
_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                   20.0545(8)
_cell_length_b                   20.0545(8)
_cell_length_c                   7.1733(5)
_cell_measurement_reflns_used    5599
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.35
_cell_volume                     2498.5(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0143
_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            50730
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.17
_exptl_absorpt_coefficient_mu    4.294
_exptl_absorpt_correction_T_max  0.9190
_exptl_absorpt_correction_T_min  0.4805
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'SADABS; Sheldrick 1996'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.420
_refine_diff_density_min         -1.013
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.287
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1181
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.346
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0487
_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)+(0.0365P)²+18.5943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                1170
_reflns_number_total             1181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26739j.txt
_cod_data_source_block           m149_sad
_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               7209537
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 0.11099(3) 0.35588(3) 0.2500 0.0345(2) Uani 1 2 d S
S1 S 0.08438(13) 0.50260(12) 0.2500 0.0376(5) Uani 1 2 d S
S2 S -0.08583(12) 0.57777(12) 0.2500 0.0349(5) Uani 1 2 d S
N1 N -0.0803(4) 0.7136(4) 0.2500 0.0384(18) Uani 1 2 d S
C1 C 0.0000 0.5071(6) 0.2500 0.030(2) Uani 1 4 d S
C2 C 0.0000 0.5756(6) 0.2500 0.030(2) Uani 1 4 d S
C3 C 0.0383(5) 0.4020(5) 0.2500 0.0314(17) Uani 1 2 d S
C4 C -0.0403(5) 0.6778(5) 0.2500 0.0314(17) Uani 1 2 d S
C5 C -0.0392(6) 0.7908(6) 0.2500 0.048(3) Uani 1 2 d S
H5 H -0.0651 0.8184 0.2500 0.13(7) Uiso 1 2 calc SR
P1 P 1.0000 0.0000 0.087(3) 0.061(6) Uani 0.25 6 d SPDU
F1 F 0.9425(11) -0.0575(11) 0.2500 0.100(8) Uani 0.50 4 d SPDU
F2 F 1.0000 0.0714(9) 0.045(5) 0.073(8) Uani 0.25 2 d SPDU
C6 C 0.7077(19) 0.4303(8) 0.965(4) 0.184(11) Uani 1 1 d DU
C7 C 0.6667 0.3333 1.0000 0.18(4) Uani 0.50 6 d SPDU
C8 C 0.700(9) 0.370(5) 0.7500 0.18(4) Uani 0.33 2 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 95.4(4) . .
C4 S2 C2 94.2(4) . .
C4 N1 C5 116.0(8) . .
C2 C1 S1 122.6(3) . 9
C2 C1 S1 122.6(3) . .
S1 C1 S1 114.8(7) 9 .
C1 C2 S2 121.2(3) . .
C1 C2 S2 121.2(3) . 9
S2 C2 S2 117.5(7) . 9
C3 C3 S1 117.2(3) 9 .
C3 C3 I1 127.4(2) 9 .
S1 C3 I1 115.4(4) . .
N1 C4 C4 121.8(5) . 9
N1 C4 S2 121.1(6) . .
C4 C4 S2 117.0(3) 9 .
N1 C5 C5 122.2(5) . 9
N1 C5 H5 118.9 . .
C5 C5 H5 118.9 9 .
P1 P1 F2 78.0(18) 13_755 2_645
P1 P1 F2 78.0(18) 13_755 .
F2 P1 F2 115.8(12) 2_645 .
P1 P1 F2 78.0(18) 13_755 3_765
F2 P1 F2 115.8(12) 2_645 3_765
F2 P1 F2 115.8(12) . 3_765
P1 P1 F1 135.4(10) 13_755 3_765
F2 P1 F1 119.4(14) 2_645 3_765
F2 P1 F1 57.3(15) . 3_765
F2 P1 F1 119.4(14) 3_765 3_765
P1 P1 F1 135.4(10) 13_755 .
F2 P1 F1 57.3(15) 2_645 .
F2 P1 F1 119.4(14) . .
F2 P1 F1 119.4(14) 3_765 .
F1 P1 F1 74.9(15) 3_765 .
P1 P1 F1 135.4(10) 13_755 2_645
F2 P1 F1 119.4(14) 2_645 2_645
F2 P1 F1 119.4(14) . 2_645
F2 P1 F1 57.3(15) 3_765 2_645
F1 P1 F1 74.9(15) 3_765 2_645
F1 P1 F1 74.9(15) . 2_645
P1 P1 F2 56.5(12) 13_755 15_545
F2 P1 F2 58.5(10) 2_645 15_545
F2 P1 F2 58.5(10) . 15_545
F2 P1 F2 134.5(18) 3_765 15_545
F1 P1 F2 95.7(9) 3_765 15_545
F1 P1 F2 95.7(9) . 15_545
F1 P1 F2 168.1(19) 2_645 15_545
P1 P1 F2 56.5(12) 13_755 13_755
F2 P1 F2 58.5(10) 2_645 13_755
F2 P1 F2 134.5(18) . 13_755
F2 P1 F2 58.5(10) 3_765 13_755
F1 P1 F2 168.1(19) 3_765 13_755
F1 P1 F2 95.7(9) . 13_755
F1 P1 F2 95.7(9) 2_645 13_755
F2 P1 F2 92.5(17) 15_545 13_755
P1 P1 F2 56.5(12) 13_755 14_665
F2 P1 F2 134.5(18) 2_645 14_665
F2 P1 F2 58.5(10) . 14_665
F2 P1 F2 58.5(10) 3_765 14_665
F1 P1 F2 95.7(9) 3_765 14_665
F1 P1 F2 168.1(19) . 14_665
F1 P1 F2 95.7(9) 2_645 14_665
F2 P1 F2 92.5(17) 15_545 14_665
F2 P1 F2 92.5(17) 13_755 14_665
P1 P1 P1 180.0 13_755 16_556
F2 P1 P1 102.0(18) 2_645 16_556
F2 P1 P1 102.0(18) . 16_556
F2 P1 P1 102.0(18) 3_765 16_556
F1 P1 P1 44.6(10) 3_765 16_556
F1 P1 P1 44.6(10) . 16_556
F1 P1 P1 44.6(10) 2_645 16_556
F2 P1 P1 123.5(12) 15_545 16_556
F2 P1 P1 123.5(12) 13_755 16_556
F2 P1 P1 123.5(12) 14_665 16_556
F2 F1 F2 159(2) 2_645 17_646
F2 F1 P1 146(2) 2_645 16_556
F2 F1 P1 55.3(9) 17_646 16_556
F2 F1 P1 55.3(9) 2_645 .
F2 F1 P1 146(2) 17_646 .
P1 F1 P1 90.8(19) 16_556 .
P1 F2 F1 67.3(14) . 3_765
P1 F2 F2 68.8(6) . 15_545
F1 F2 F2 109(2) 3_765 15_545
P1 F2 F2 68.8(6) . 14_665
F1 F2 F2 109(2) 3_765 14_665
F2 F2 F2 104(3) 15_545 14_665
P1 F2 P1 45.5(18) . 13_755
F1 F2 P1 112.8(18) 3_765 13_755
F2 F2 P1 52.6(11) 15_545 13_755
F2 F2 P1 52.6(11) 14_665 13_755
C6 C6 C7 80.2(10) 11_657 .
C6 C6 C8 125(8) 11_657 .
C7 C6 C8 64(2) . .
C6 C7 C6 19.7(19) 3_665 12_557
C6 C7 C6 117.9(5) 3_665 2_655
C6 C7 C6 111(2) 12_557 2_655
C6 C7 C6 131(2) 3_665 10_667
C6 C7 C6 117.9(5) 12_557 10_667
C6 C7 C6 19.7(19) 2_655 10_667
C6 C7 C6 111(2) 3_665 11_657
C6 C7 C6 117.9(5) 12_557 11_657
C6 C7 C6 131(2) 2_655 11_657
C6 C7 C6 117.9(5) 10_667 11_657
C6 C7 C6 117.9(5) 3_665 .
C6 C7 C6 131(2) 12_557 .
C6 C7 C6 117.9(5) 2_655 .
C6 C7 C6 111(2) 10_667 .
C6 C7 C6 19.7(19) 11_657 .
C6 C7 C8 63(3) 3_665 3_665
C6 C7 C8 78(2) 12_557 3_665
C6 C7 C8 82(7) 2_655 3_665
C6 C7 C8 102(6) 10_667 3_665
C6 C7 C8 114(6) 11_657 3_665
C6 C7 C8 100(5) . 3_665
C6 C7 C8 78(2) 3_665 21_556
C6 C7 C8 63(3) 12_557 21_556
C6 C7 C8 114(6) 2_655 21_556
C6 C7 C8 100(5) 10_667 21_556
C6 C7 C8 82(7) 11_657 21_556
C6 C7 C8 102(6) . 21_556
C8 C7 C8 141(5) 3_665 21_556
C6 C7 C8 100(5) 3_665 2_655
C6 C7 C8 114(5) 12_557 2_655
C6 C7 C8 63(3) 2_655 2_655
C6 C7 C8 78(2) 10_667 2_655
C6 C7 C8 102(6) 11_657 2_655
C6 C7 C8 82(7) . 2_655
C8 C7 C8 37(4) 3_665 2_655
C8 C7 C8 176(10) 21_556 2_655
C6 C7 C8 82(7) 3_665 .
C6 C7 C8 102(6) 12_557 .
C6 C7 C8 100(5) 2_655 .
C6 C7 C8 114(5) 10_667 .
C6 C7 C8 78(2) 11_657 .
C6 C7 C8 63(3) . .
C8 C7 C8 37(4) 3_665 .
C8 C7 C8 145(10) 21_556 .
C8 C7 C8 37(4) 2_655 .
C6 C7 C8 102(6) 3_665 19_666
C6 C7 C8 82(7) 12_557 19_666
C6 C7 C8 78(2) 2_655 19_666
C6 C7 C8 63(3) 10_667 19_666
C6 C7 C8 100(5) 11_657 19_666
C6 C7 C8 114(5) . 19_666
C8 C7 C8 145(10) 3_665 19_666
C8 C7 C8 37(4) 21_556 19_666
C8 C7 C8 141(5) 2_655 19_666
C8 C7 C8 176(10) . 19_666
C6 C7 C8 114(5) 3_665 20_656
C6 C7 C8 100(5) 12_557 20_656
C6 C7 C8 102(6) 2_655 20_656
C6 C7 C8 82(7) 10_667 20_656
C6 C7 C8 63(3) 11_657 20_656
C6 C7 C8 78(2) . 20_656
C8 C7 C8 176(10) 3_665 20_656
C8 C7 C8 37(4) 21_556 20_656
C8 C7 C8 145(10) 2_655 20_656
C8 C7 C8 141(5) . 20_656
C8 C7 C8 37(4) 19_666 20_656
C8 C8 C8 60.00(2) 2_655 3_665
C8 C8 C6 97(10) 2_655 .
C8 C8 C6 124(3) 3_665 .
C8 C8 C6 97(10) 2_655 16_557
C8 C8 C6 124(3) 3_665 16_557
C6 C8 C6 107(7) . 16_557
C8 C8 C7 71.5(18) 2_655 16_557
C8 C8 C7 71.5(18) 3_665 16_557
C6 C8 C7 154(10) . 16_557
C6 C8 C7 52.9(15) 16_557 16_557
C8 C8 C7 71.5(18) 2_655 .
C8 C8 C7 71.5(18) 3_665 .
C6 C8 C7 52.9(15) . .
C6 C8 C7 154(10) 16_557 .
C7 C8 C7 137(4) 16_557 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C3 2.080(8) .
S1 C1 1.740(7) .
S1 C3 1.750(9) .
S2 C4 1.739(9) .
S2 C2 1.744(6) .
N1 C4 1.319(11) .
N1 C5 1.341(12) .
C1 C2 1.373(16) .
C1 S1 1.740(7) 9
C2 S2 1.744(6) 9
C3 C3 1.331(17) 9
C4 C4 1.400(16) 9
C5 C5 1.36(2) 9
C5 H5 0.9300 .
P1 P1 1.25(5) 13_755
P1 F2 1.463(17) 2_645
P1 F2 1.463(17) .
P1 F2 1.463(17) 3_765
P1 F1 1.641(17) 3_765
P1 F1 1.641(17) .
P1 F1 1.641(17) 2_645
P1 F2 1.72(3) 15_545
P1 F2 1.72(3) 13_755
P1 F2 1.72(3) 14_665
P1 P1 2.34(5) 16_556
F1 F2 1.50(4) 2_645
F1 F2 1.50(4) 17_646
F1 P1 1.641(17) 16_556
F2 F1 1.50(4) 3_765
F2 F2 1.57(4) 15_545
F2 F2 1.57(4) 14_665
F2 P1 1.72(3) 13_755
C6 C6 0.58(6) 11_657
C6 C7 1.709(11) .
C6 C8 1.91(9) .
C7 C6 1.709(11) 3_665
C7 C6 1.709(11) 12_557
C7 C6 1.709(11) 2_655
C7 C6 1.709(11) 10_667
C7 C6 1.709(11) 11_657
C7 C8 1.93(3) 3_665
C7 C8 1.93(3) 21_556
C7 C8 1.93(3) 2_655
C7 C8 1.93(3) .
C7 C8 1.93(3) 19_666
C7 C8 1.93(3) 20_656
C8 C8 1.22(13) 2_655
C8 C8 1.22(13) 3_665
C8 C6 1.91(9) 16_557
C8 C7 1.93(3) 16_557
