#------------------------------------------------------------------------------
#$Date: 2017-02-13 17:46:56 +0200 (Mon, 13 Feb 2017) $
#$Revision: 192027 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/45/2004577.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2004577
loop_
_publ_author_name
'Beeson, J. C.'
'Czarnik, A. W.'
'Fitzgerald, L. J.'
'Gerkin, R. E.'
_publ_section_title
;
 Hexaazatriphenylenehexacarboxamide Solvate Exhibiting π-Complexation
 in the Solid State
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              724
_journal_page_last               729
_journal_paper_doi               10.1107/S0108270195011036
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C18 H12 N12 O6,2(C2 H6 O1 S1),0.5(H2 O1)'
_chemical_formula_sum            'C22 H25 N12 O8.5 S2'
_chemical_formula_weight         657.63
_chemical_name_common            'hexaazatriphenylenehexacarboxamide solvate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                103.54(3)
_cell_angle_beta                 99.02(5)
_cell_angle_gamma                92.72(4)
_cell_formula_units_Z            2
_cell_length_a                   12.723(4)
_cell_length_b                   13.429(2)
_cell_length_c                   8.737(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      14.9
_cell_measurement_theta_min      14.3
_cell_volume                     1427.8(13)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection       'MSC/AFC Diffractometer Control Software'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1989)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
'TEXSAN (Molecular Structure Corporation, 1989)'
_computing_structure_refinement
'TEXSAN (Molecular Structure Corporation, 1989)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device       AFC5S
_diffrn_measurement_method       ' ω-2θ '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8671
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        '+- 3.9 (av. max. relative intensity)'
_diffrn_standards_interval_count 150
_diffrn_standards_number         6
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type
' empirical,\y-scan, six scans  (North, Phillips \& Mathews, 1968)'
_exptl_crystal_colour            amber
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_meas      1.56
_exptl_crystal_density_method    flotation
_exptl_crystal_description       plate
_exptl_crystal_F_000             682
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.68
_refine_ls_hydrogen_treatment    'see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         4120
_refine_ls_R_factor_obs          0.047
_refine_ls_shift/esd_max         0.02
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=σF⁻²
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.052
_reflns_number_observed          4120
_reflns_number_total             8312
_reflns_observed_criterion       'I > 3\s(I)'
_cod_data_source_file            bk1108.cif
_cod_data_source_block           I
_cod_depositor_comments
;
 Changing the _atom_site_occupancy data item value from '?' to '1'
 for all fully occupied atom sites.

 Antanas Vaitkus,
 2017-02-13

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w=\s~F~^-2^' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w=\s~F~^-2^'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1428(2)
_cod_original_formula_sum        'C22 H25 N12 O8.50 S2'
_cod_database_code               2004577
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_type_symbol
O(1) 1 .4726(2) -0.37310(10) .5706(2) .0439(6) Uij O
O(2) .530(10) .2250(10) -0.4290(10) .391(2) .092(4) Uij O
O(2A) .470(10) .2410(10) -0.4180(10) .452(2) .056(3) Uij O
O(3) 1 .0863(2) .1969(2) .6908(3) .0591(7) Uij O
O(4) 1 .1168(2) .3328(2) .4705(3) .0555(7) Uij O
O(5) 1 .6829(2) .1369(2) -.0145(2) .0422(6) Uij O
O(6) 1 .8109(2) .0302(2) .2043(2) .0506(6) Uij O
N(1) 1 .4567(2) -0.21230(10) .3475(2) .0264(5) Uij N
N(2) 1 .2570(2) -0.1651(2) .4258(3) .0374(6) Uij N
N(3) 1 .1965(2) .03110(10) .4568(2) .0257(5) Uij N
N(4) 1 .3228(2) .17790(10) .3702(2) .0279(5) Uij N
N(5) 1 .4970(2) .1206(2) .2323(2) .0279(5) Uij N
N(6) 1 .5731(2) -.07150(10) .2317(2) .0272(5) Uij N
N(7) 1 .4634(2) -0.4434(2) .3065(3) .0454(8) Uij N
N(8) .530(10) .1633(4) -0.2891(4) .5897(7) .056(2) Uij N
N(8A) .470(10) .1083(5) -0.3329(4) .3940(10) .095(3) Uij N
N(9) 1 -.0183(2) .1105(2) .4623(4) .0473(8) Uij N
N(10) 1 .2774(2) .3722(2) .4109(4) .0525(9) Uij N
N(11) 1 .6091(3) .2646(2) .1395(4) .0546(9) Uij N
N(12) 1 .7318(2) -0.1114(2) .0189(3) .0467(8) Uij N
C(1) 1 .4193(2) -0.1207(2) .3414(3) .0235(6) Uij C
C(2) 1 .3216(2) -.0951(2) .3887(3) .0247(6) Uij C
C(3) 1 .2876(2) .0079(2) .4000(3) .0234(6) Uij C
C(4) 1 .3502(2) .0806(2) .3564(3) .0234(6) Uij C
C(5) 1 .4460(2) .0516(2) .2918(3) .0234(6) Uij C
C(6) 1 .4820(2) -.0457(2) .2872(3) .0233(6) Uij C
C(7) 1 .3950(2) -0.2778(2) .3940(3) .0287(6) Uij C
C(8) 1 .2925(2) -0.2555(2) .4250(4) .0406(8) Uij C
C(9) 1 .1712(2) .1272(2) .4734(3) .0258(6) Uij C
C(10) 1 .2349(2) .2012(2) .4286(3) .0270(6) Uij C
C(11) 1 .5842(2) .0944(2) .1744(3) .0272(6) Uij C
C(12) 1 .6244(2) -.0017(2) .1782(3) .0265(6) Uij C
C(13) 1 .4458(2) -0.3719(2) .4294(3) .0324(7) Uij C
C(14) .530(10) .2265(8) -0.3282(7) .4880(10) .040(2) Uij C
C(14A) .470(10) .2069(9) -0.3487(9) .4070(10) .050(3) Uij C
C(15) 1 .0746(2) .1504(2) .5529(3) .0333(7) Uij C
C(16) 1 .2040(2) .3096(2) .4390(3) .0361(7) Uij C
C(17) 1 .6319(2) .1685(2) .0921(3) .0315(7) Uij C
C(18) 1 .7322(2) -.0267(2) .1332(3) .0336(7) Uij C
H(1) 1 .491(3) -0.496(2) .323(4) .055(10) Uij H
H(2) 1 .440(3) -0.441(2) .204(4) .060(10) Uij H
H(3) .530(10) .1048 -0.3314 .6037 .0673 Uij H
H(4) .530(10) .1745 -0.2191 .6460 .0673 Uij H
H(3A) .470(10) .0555 -0.3885 .3754 .1115 Uij H
H(4A) .470(10) .0880 -0.2642 .4101 .1115 Uij H
H(5) 1 -.021(3) .079(3) .363(4) .070(10) Uij H
H(6) 1 -.077(3) .116(3) .506(4) .080(10) Uij H
H(7) 1 .343(3) .351(2) .393(4) .070(10) Uij H
H(8) 1 .266(2) .433(2) .416(3) .052(9) Uij H
H(9) 1 .580(3) .285(3) .228(4) .080(10) Uij H
H(10) 1 .632(3) .314(3) .101(4) .070(10) Uij H
H(11) 1 .799(3) -0.130(3) -.011(4) .100(10) Uij H
H(12) 1 .669(3) -0.144(2) -.022(4) .060(10) Uij H
S(1) .620(10) .9814(2) .1865(2) .0982(2) .0555(6) Uij S
O(7) .620(10) 1.0850(8) .1560(7) .1360(10) .067(2) Uij O
C(19) 1 .9237(3) .1095(4) -.0883(4) .0850(10) Uij C
C(20) .620(10) .9770(10) .3017(7) .0280(10) .210(7) Uij C
S(1A) .380(10) 1.0049(3) .2246(3) .0473(6) .0730(10) Uij S
O(7A) .380(10) 1.1000(10) .2000(10) .103(2) .097(5) Uij O
C(20A) .380(10) .9154(8) .2668(8) .1700(10) .078(4) Uij C
S(2) .730(10) .2936(2) .46230(10) .8657(3) .0781(7) Uij S
O(8) .730(10) .3624(7) .5534(3) .9875(5) .085(2) Uij O
C(21) .730(10) .3370(10) .3530(10) .923(2) .171(6) Uij C
C(22) .730(10) .1687(10) .4505(10) .945(2) .184(6) Uij C
S(2A) .270(10) .2650(10) .4770(9) .954(3) .200(6) Uij S
O(8A) .270(10) .3371 .5564 .9881 .111(9) Uij O
C(21A) .270(10) .328(2) .356(2) .884(4) .092(8) Uij C
C(22A) .270(10) .182(4) .473(3) .826(5) .25(2) Uij C
O(9) .5 .9765(4) .4779(3) .3976(6) .073(2) Uij O
H(17) .50(10) .9476 .5053 .4885 .1077 Uij H
H(18) .50(10) 1.0368 .4372 .4287 .1077 Uij H
H(19A) .62 .9716 .1108 -0.1615 .1037 Uij H
H(19B) .62 .8591 .1365 -0.1251 .1037 Uij H
H(19C) .62 .9091 .0418 -0.0804 .1037 Uij H
H(20A) .62 1.0463 .3263 .0237 .2535 Uij H
H(20B) .62 .9335 .2871 -0.0747 .2535 Uij H
H(20C) .62 .9457 .3520 .1001 .2535 Uij H
H(19AA) .38 .8517 .1257 -0.1105 .1037 Uij H
H(19AB) .38 .9512 .0921 -0.1853 .1037 Uij H
H(19AC) .38 .9269 .0544 -0.0386 .1037 Uij H
H(20AA) .38 .9527 .3071 .2692 .0953 Uij H
H(20AB) .38 .8676 .3069 .1211 .0953 Uij H
H(20AC) .38 .8765 .2091 .1863 .0953 Uij H
H(21A) .73 .4126 .3638 .9560 .2072 Uij H
H(21B) .73 .3041 .3447 1.0092 .2072 Uij H
H(21C) .73 .3191 .2962 .8353 .2072 Uij H
H(22A) .73 .1221 .3959 .8763 .2218 Uij H
H(22B) .73 .1357 .5130 .9553 .2218 Uij H
H(22C) .73 .1851 .4366 1.0487 .2218 Uij H
H(21AA) .27 .3700 .3651 .8055 .1155 Uij H
H(21AB) .27 .2728 .3019 .8341 .1155 Uij H
H(21AC) .27 .3709 .3390 .9696 .1155 Uij H
H(22AA) .27 .1440 .5329 .8493 .2974 Uij H
H(22AB) .27 .2097 .4695 .7317 .2974 Uij H
H(22AC) .27 .1336 .4138 .8133 .2974 Uij H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0 0 'Stewart, Davidson \& Simpson (1965)'
C .002 .002 'Cromer \& Waber (1974)'
O .008 .006 'Cromer \& Waber (1974)'
N .004 .003 'Cromer \& Waber (1974)'
S .110 .124 'Cromer \& Waber (1974)'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 1 2
0 -4 2
2 -1 0
-8 5 1
7 -6 0
1 -9 3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(1) N(1) C(7) 116.9(2) yes
C(2) N(2) C(8) 117.1(2) yes
C(3) N(3) C(9) 117.0(2) yes
C(4) N(4) C(10) 117.3(2) yes
C(5) N(5) C(11) 117.7(2) yes
C(6) N(6) C(12) 117.1(2) yes
N(1) C(1) C(2) 121.1(2) yes
N(1) C(1) C(6) 119.8(2) yes
C(2) C(1) C(6) 119.1(2) yes
N(2) C(2) C(1) 120.9(2) yes
N(2) C(2) C(3) 118.2(2) yes
C(1) C(2) C(3) 120.9(2) yes
N(3) C(3) C(2) 118.8(2) yes
N(3) C(3) C(4) 121.6(2) yes
C(2) C(3) C(4) 119.6(2) yes
N(4) C(4) C(3) 121.2(2) yes
N(4) C(4) C(5) 119.1(2) yes
C(3) C(4) C(5) 119.7(2) yes
N(5) C(5) C(4) 117.7(2) yes
N(5) C(5) C(6) 121.2(2) yes
C(4) C(5) C(6) 121.0(2) yes
N(6) C(6) C(1) 119.8(2) yes
N(6) C(6) C(5) 121.0(2) yes
C(1) C(6) C(5) 119.2(2) yes
N(1) C(7) C(8) 121.4(2) yes
N(1) C(7) C(13) 116.3(2) yes
C(8) C(7) C(13) 122.0(2) yes
N(2) C(8) C(7) 122.0(2) yes
N(2) C(8) C(14) 116.6(4) yes
N(2) C(8) C(14A) 117.4(5) yes
C(7) C(8) C(14) 120.4(4) yes
C(7) C(8) C(14A) 118.0(5) yes
N(3) C(9) C(10) 121.4(2) yes
N(3) C(9) C(15) 114.2(2) yes
C(10) C(9) C(15) 124.3(2) yes
N(4) C(10) C(9) 121.5(2) yes
N(4) C(10) C(16) 116.5(2) yes
C(9) C(10) C(16) 121.9(2) yes
N(5) C(11) C(12) 121.1(2) yes
N(5) C(11) C(17) 116.1(2) yes
C(12 C(11) C(17) 122.6(2) yes
N(6) C(12) C(11) 121.7(2) yes
N(6) C(12) C(18) 116.6(2) yes
C(11) C(12) C(18) 121.6(2) yes
O(1) C(13) N(7) 124.9(2) yes
O(1) C(13) C(7) 117.7(2) yes
N(7) C(13) C(7) 117.3(2) yes
O(2) C(14) N(8) 130.0(10) yes
O(2) C(14) C(8) 108.4(10) yes
N(8) C(14) C(8) 118.6(7) yes
O(2A) C(14A) N(8A) 122.0(10) yes
O(2A) C(14A) C(8) 114.0(10) yes
N(8A) C(14A) C(8) 119.0(9) yes
O(3) C(15) N(9) 125.1(3) yes
O(3) C(15) C(9) 120.0(3) yes
N(9) C(15) C(9) 114.8(3) yes
O(4) C(16) N(10) 125.4(2) yes
O(4) C(16) C(10) 120.3(2) yes
N(10) C(16) C(10) 114.4(2) yes
O(5) C(17) N(11) 125.0(3) yes
O(5) C(17) C(11) 120.2(2) yes
N(11) C(17) C(11) 114.7(2) yes
O(6) C(18) N(12) 125.6(3) yes
O(6) C(18) C(12) 118.6(2) yes
N(12) C(18) C(12) 115.8(2) yes
O(7) S(1) C(19) 107.4(4) yes
O(7) S(1) C(20) 114.8(6) yes
C(19) S(1) C(20) 92.7(4) yes
C(19) S(1) C(20A) 115.3(4) yes
C(19) S(1A) O(7A) 110.6(8) yes
C(19) S(1A) C(20A) 99.4(4) yes
O(8) S(2) C(21) 104.7(6) yes
O(8) S(2) C(22) 105.0(6) yes
C(21) S(2) C(22) 91.5(7) yes
O(8A) S(2A) C(21A) 109.0(10) yes
O(8A) S(2A) C(22A) 115(2) yes
C(21A) S(2A) C(22A) 102(2) yes
H(17) O(9) H(18) 108 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(13) 1.231(3) yes
O(2) C(14) 1.41(2) yes
O(2A) C(14A) 1.17(2) yes
O(3) C(15) 1.202(3) yes
O(4) C(16) 1.221(3) yes
O(5) C(17) 1.225(3) yes
O(6) C(18) 1.219(3) yes
N(1) C(1) 1.349(3) yes
N(1) C(7) 1.325(3) yes
N(2) C(2) 1.347(3) yes
N(2) C(8) 1.313(3) yes
N(3) C(3) 1.352(3) yes
N(3) C(9) 1.326(3) yes
N(4) C(4) 1.351(3) yes
N(4) C(10) 1.321(3) yes
N(5) C(5) 1.351(3) yes
N(5) C(11) 1.319(3) yes
N(6) C(6) 1.353(3) yes
N(6) C(12) 1.331(3) yes
N(7) C(13) 1.318(3) yes
N(8) C(14) 1.320(10) yes
N(8A) C(14A) 1.270(10) yes
N(9) C(15) 1.326(4) yes
N(10) C(16) 1.317(4) yes
N(11) C(17) 1.322(3) yes
N(12) C(18) 1.324(4) yes
C(1) C(2) 1.403(3) yes
C(1) C(6) 1.463(3) yes
C(2) C(3) 1.455(3) yes
C(3) C(4) 1.389(3) yes
C(4) C(5) 1.453(3) yes
C(5) C(6) 1.399(3) yes
C(7) C(8) 1.406(3) yes
C(7) C(13) 1.519(3) yes
C(8) C(14) 1.512(10) yes
C(8) C(14A) 1.580(10) yes
C(9) C(10) 1.415(3) yes
C(9) C(15) 1.515(3) yes
C(10) C(16) 1.512(3) yes
C(11) C(12) 1.416(3) yes
C(11) C(17) 1.513(3) yes
C(12) C(18) 1.516(3) yes
S(1) O(7) 1.411(10) yes
S(1) C(19) 1.740(4) yes
S(1) C(20) 1.790(10) yes
C(19) S(1A) 1.862(5) yes
S(1A) O(7A) 1.32(2) yes
S(1A) C(20A) 1.710(10) yes
S(2) O(8) 1.548(5) yes
S(2) C(21) 1.740(10) yes
S(2) C(22) 1.840(10) yes
S(2A) O(8A) 1.322(9) yes
S(2A) C(21A) 1.86(3) yes
S(2A) C(22A) 1.40(4) yes
O(9) H(17) 0.93 no
O(9) H(18) 1.00 no
