#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012318.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_2012318
loop_
_publ_author_name
'Batsanov, Andrei S.'
'Perepichka, Igor F.'
'Bryce, Martin R.'
'Howard, Judith A. K.'
_publ_section_title
;
 Cocrystals of 2-(2,4,5,7-tetranitrofluoren-9-ylidene)propanedinitrile
 and 2,4,5,7-tetranitrofluoren-9-one with chlorobenzene
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1299
_journal_page_last               1302
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C16 H4 N6 O8 , C6 H5 Cl'
_chemical_formula_moiety         'C16 H4 N6 O8 , C6 H5 Cl'
_chemical_formula_sum            'C22 H9 Cl N6 O8'
_chemical_formula_weight         520.80
_chemical_name_systematic
;
2-(2,4,5,7-tetranitrofluorene-9-ylidene)propanedinitrile chlorobenzene solvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 118.330(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.823(2)
_cell_length_b                   8.360(6)
_cell_length_c                   17.461(3)
_cell_measurement_reflns_used    512
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      12
_cell_volume                     2161.6(16)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1995)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Siemens SMART 1K CCD area-detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .034
_diffrn_reflns_av_sigmaI/netI    .023
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22991
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.38
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .243
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          .28
_exptl_crystal_size_mid          .22
_exptl_crystal_size_min          .18
_refine_diff_density_max         .30
_refine_diff_density_min         -.54
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         4962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          .050
_refine_ls_R_factor_gt           .038
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0297P)^2^+1.4795P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .092
_reflns_number_gt                4169
_reflns_number_total             4962
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    gg1068.cif
_[local]_cod_data_source_block   I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2012318
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
C1 .23854(11) -.19503(19) .34253(10) .0212(3) Uani d 1 C
H1 .1855(13) -.230(2) .3425(12) .024(5) Uiso d 1 H
C2 .32228(11) -.24500(19) .40781(10) .0221(3) Uani d 1 C
C3 .40327(11) -.18737(19) .41742(10) .0219(3) Uani d 1 C
H3 .4602(13) -.218(2) .4659(12) .024(5) Uiso d 1 H
C4 .40084(10) -.07805(18) .35642(9) .0196(3) Uani d 1 C
C5 .34500(10) .11195(18) .16181(10) .0182(3) Uani d 1 C
C6 .30495(11) .20857(18) .08858(10) .0195(3) Uani d 1 C
H6 .3387(12) .248(2) .0629(12) .023(5) Uiso d 1 H
C7 .21337(11) .23966(18) .05338(9) .0202(3) Uani d 1 C
C8 .15945(11) .17234(19) .08505(10) .0204(3) Uani d 1 C
H8 .0965(13) .193(2) .0568(12) .023(5) Uiso d 1 H
C9 .16176(10) -.01653(18) .20435(9) .0187(3) Uani d 1 C
C10 .23862(10) -.09306(18) .27946(10) .0190(3) Uani d 1 C
C11 .32020(10) -.03994(17) .28250(9) .0179(3) Uani d 1 C
C12 .29654(10) .05363(17) .20241(9) .0174(3) Uani d 1 C
C13 .20180(10) .07749(18) .15932(10) .0184(3) Uani d 1 C
C14 .07282(11) -.03101(19) .18105(10) .0220(3) Uani d 1 C
C15 .03905(11) -.1325(2) .22607(11) .0273(4) Uani d 1 C
C16 .00240(11) .0503(2) .10676(11) .0240(3) Uani d 1 C
N2 .32456(11) -.35946(17) .47329(9) .0282(3) Uani d 1 N
N4 .48503(9) .01231(17) .38111(8) .0229(3) Uani d 1 N
N5 .43829(9) .06086(16) .18837(8) .0196(3) Uani d 1 N
N7 .17001(9) .34439(17) -.02414(8) .0244(3) Uani d 1 N
N15 .00956(11) -.2142(2) .25905(11) .0405(4) Uani d 1 N
N16 -.05422(10) .1107(2) .04664(10) .0330(3) Uani d 1 N
O1 .25449(10) -.38247(17) .47685(9) .0404(3) Uani d 1 O
O2 .39689(9) -.42598(17) .51972(9) .0421(3) Uani d 1 O
O3 .55675(8) -.04650(15) .43572(8) .0301(3) Uani d 1 O
O4 .47786(8) .14739(14) .35047(8) .0297(3) Uani d 1 O
O5 .46121(8) -.07217(14) .22242(8) .0263(3) Uani d 1 O
O6 .48590(7) .14971(14) .17174(7) .0256(3) Uani d 1 O
O7 .21897(9) .41470(16) -.04710(8) .0321(3) Uani d 1 O
O8 .08731(8) .35537(18) -.06039(8) .0380(3) Uani d 1 O
Cl .24376(4) .32680(6) .33292(3) .04034(13) Uani d 1 Cl
C21 .23139(12) .4516(2) .24742(11) .0272(4) Uani d 1 C
C22 .30763(12) .4980(2) .24204(11) .0272(4) Uani d 1 C
H22 .3672(14) .463(3) .2850(13) .035(5) Uiso d 1 H
C23 .29692(12) .5967(2) .17370(12) .0286(4) Uani d 1 C
H23 .3485(14) .631(3) .1685(13) .037(6) Uiso d 1 H
C24 .21124(13) .6465(2) .11179(12) .0297(4) Uani d 1 C
H24 .2054(15) .714(3) .0660(15) .044(6) Uiso d 1 H
C25 .13567(12) .5974(2) .11843(12) .0309(4) Uani d 1 C
H25 .0760(15) .629(3) .0760(14) .039(6) Uiso d 1 H
C26 .14494(12) .4998(2) .18646(12) .0302(4) Uani d 1 C
H26 .0942(14) .468(3) .1921(13) .036(5) Uiso d 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 .0255(8) .0198(7) .0222(7) .0001(6) .0146(7) -.0014(6)
C2 .0326(9) .0182(7) .0170(7) .0019(6) .0130(7) .0000(6)
C3 .0262(8) .0195(7) .0171(7) .0033(6) .0079(6) -.0021(6)
C4 .0208(7) .0192(7) .0182(7) .0009(6) .0088(6) -.0037(6)
C5 .0183(7) .0164(7) .0198(7) -.0004(6) .0089(6) -.0031(6)
C6 .0224(8) .0180(7) .0198(7) -.0022(6) .0114(6) -.0014(6)
C7 .0248(8) .0184(7) .0154(7) .0012(6) .0079(6) .0000(6)
C8 .0192(8) .0203(7) .0196(7) .0010(6) .0076(6) -.0013(6)
C9 .0215(8) .0165(7) .0189(7) .0017(6) .0102(6) -.0009(6)
C10 .0214(7) .0171(7) .0191(7) .0021(6) .0101(6) -.0023(6)
C11 .0218(8) .0152(7) .0170(7) .0023(6) .0094(6) -.0024(5)
C12 .0197(7) .0151(7) .0170(7) .0001(6) .0084(6) -.0031(5)
C13 .0196(7) .0171(7) .0194(7) .0008(6) .0100(6) -.0019(6)
C14 .0222(8) .0239(8) .0222(7) .0008(6) .0123(6) -.0018(6)
C15 .0207(8) .0341(9) .0278(8) .0016(7) .0121(7) .0012(7)
C16 .0200(8) .0282(8) .0273(8) -.0002(7) .0141(7) -.0017(7)
N2 .0400(9) .0235(7) .0214(7) .0015(6) .0149(6) .0022(6)
N4 .0219(7) .0250(7) .0193(6) -.0006(5) .0078(5) -.0056(5)
N5 .0188(6) .0211(6) .0185(6) -.0005(5) .0086(5) -.0026(5)
N7 .0272(7) .0253(7) .0193(6) .0025(6) .0098(6) .0028(5)
N15 .0294(8) .0530(11) .0433(9) -.0012(8) .0208(8) .0118(8)
N16 .0235(7) .0416(9) .0314(8) .0052(7) .0110(6) .0041(7)
O1 .0506(8) .0397(8) .0462(8) .0086(7) .0355(7) .0155(6)
O2 .0388(8) .0428(8) .0315(7) .0016(6) .0060(6) .0177(6)
O3 .0196(6) .0343(7) .0264(6) .0038(5) .0028(5) -.0046(5)
O4 .0301(6) .0249(6) .0291(6) -.0057(5) .0101(5) -.0011(5)
O5 .0276(6) .0224(6) .0316(6) .0072(5) .0164(5) .0056(5)
O6 .0207(6) .0271(6) .0299(6) -.0045(5) .0128(5) .0006(5)
O7 .0359(7) .0346(7) .0297(6) .0012(6) .0188(6) .0104(5)
O8 .0254(7) .0503(8) .0308(7) .0065(6) .0072(5) .0146(6)
Cl .0638(3) .0312(2) .0334(2) -.0042(2) .0291(2) -.00185(19)
C21 .0376(10) .0209(8) .0265(8) -.0018(7) .0180(7) -.0042(6)
C22 .0250(9) .0242(8) .0298(9) .0002(7) .0108(7) -.0061(7)
C23 .0284(9) .0263(9) .0363(9) -.0027(7) .0197(8) -.0041(7)
C24 .0352(10) .0239(8) .0309(9) .0022(7) .0165(8) -.0012(7)
C25 .0249(9) .0292(9) .0353(9) .0046(7) .0116(8) -.0049(8)
C26 .0286(9) .0281(9) .0399(10) -.0043(7) .0211(8) -.0084(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .1585 '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_publ_flag
C2 C1 C10 116.82(15) ?
C2 C1 H1 119.9(11) ?
C10 C1 H1 123.3(11) ?
C3 C2 C1 123.58(15) ?
C3 C2 N2 118.10(14) ?
C1 C2 N2 118.24(15) ?
C2 C3 C4 117.97(15) ?
C2 C3 H3 121.7(11) ?
C4 C3 H3 120.3(11) ?
C3 C4 N4 115.93(14) yes
C11 C4 N4 122.00(14) yes
C3 C4 C11 121.43(15) yes
C6 C5 N5 115.98(13) yes
C12 C5 N5 122.00(13) yes
C6 C5 C12 121.71(14) yes
C7 C6 C5 118.01(14) ?
C7 C6 H6 121.5(11) ?
C5 C6 H6 120.5(11) ?
C6 C7 C8 123.18(14) ?
C6 C7 N7 118.55(14) ?
C8 C7 N7 118.22(14) ?
C7 C8 C13 117.39(14) ?
C7 C8 H8 119.9(11) ?
C13 C8 H8 122.7(11) ?
C14 C9 C10 127.04(14) ?
C14 C9 C13 127.07(14) ?
C10 C9 C13 105.88(13) ?
C1 C10 C11 121.70(14) ?
C1 C10 C9 129.54(14) ?
C11 C10 C9 108.69(13) ?
C4 C11 C10 117.50(14) ?
C4 C11 C12 134.53(14) ?
C10 C11 C12 107.93(13) ?
C5 C12 C13 117.48(13) ?
C5 C12 C11 134.62(14) ?
C13 C12 C11 107.82(13) ?
C8 C13 C12 121.59(14) ?
C8 C13 C9 129.48(14) ?
C12 C13 C9 108.89(13) ?
C9 C14 C15 123.50(15) ?
C9 C14 C16 123.00(15) ?
C15 C14 C16 113.47(14) ?
N15 C15 C14 177.56(19) ?
N16 C16 C14 178.05(19) ?
O1 N2 O2 124.80(15) ?
O1 N2 C2 117.96(14) ?
O2 N2 C2 117.24(15) ?
O4 N4 O3 124.14(14) ?
O4 N4 C4 117.36(13) ?
O3 N4 C4 118.25(14) ?
O6 N5 O5 124.85(13) ?
O6 N5 C5 117.94(13) ?
O5 N5 C5 117.12(13) ?
O7 N7 O8 124.68(14) ?
O7 N7 C7 117.85(13) ?
O8 N7 C7 117.46(14) ?
C22 C21 C26 122.09(16) yes
C22 C21 Cl 119.06(14) ?
C26 C21 Cl 118.85(14) ?
C21 C22 C23 118.53(16) ?
C21 C22 H22 120.9(12) ?
C23 C22 H22 120.6(12) ?
C22 C23 C24 120.55(17) ?
C22 C23 H23 120.3(13) ?
C24 C23 H23 119.2(13) ?
C25 C24 C23 119.78(17) ?
C25 C24 H24 120.9(13) ?
C23 C24 H24 119.3(13) ?
C26 C25 C24 120.58(17) ?
C26 C25 H25 118.4(13) ?
C24 C25 H25 121.1(13) ?
C25 C26 C21 118.47(17) ?
C25 C26 H26 121.1(13) ?
C21 C26 H26 120.4(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.391(2) yes
C1 C10 1.393(2) yes
C1 H1 .940(19) ?
C2 C3 1.378(2) yes
C2 N2 1.477(2) yes
C3 C4 1.389(2) yes
C3 H3 .964(19) ?
C4 N4 1.478(2) yes
C4 C11 1.395(2) yes
C5 C6 1.387(2) yes
C5 C12 1.398(2) yes
C5 N5 1.4730(19) yes
C6 C7 1.386(2) yes
C6 H6 .935(19) ?
C7 N7 1.481(2) yes
C7 C8 1.386(2) yes
C8 C13 1.393(2) yes
C8 H8 .949(19) ?
C9 C10 1.480(2) yes
C9 C13 1.481(2) yes
C9 C14 1.357(2) yes
C10 C11 1.419(2) yes
C11 C12 1.482(2) yes
C12 C13 1.417(2) yes
C14 C15 1.444(2) yes
C14 C16 1.446(2) yes
C15 N15 1.147(2) yes
C16 N16 1.147(2) yes
N2 O1 1.225(2) ?
N2 O2 1.229(2) ?
N4 O4 1.231(2) ?
N4 O3 1.2307(17) ?
N5 O6 1.2241(17) ?
N5 O5 1.2334(19) ?
N7 O7 1.2240(18) ?
N7 O8 1.2284(18) ?
Cl C21 1.7508(18) yes
C21 C22 1.385(2) ?
C21 C26 1.394(3) ?
C22 C23 1.390(3) ?
C22 H22 .97(2) ?
C23 C24 1.393(3) ?
C23 H23 .96(2) ?
C24 C25 1.392(3) ?
C24 H24 .94(2) ?
C25 C26 1.387(3) ?
C25 H25 .96(2) ?
C26 H26 .94(2) ?