#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/23/2012318.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_paper_doi               10.1107/S0108270101011556
_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       'ω 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      ?
_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/[σ²(Fo²)+(0.0297P)²+1.4795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .092
_reflns_number_gt                4169
_reflns_number_total             4962
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1068.cif
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' 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      'P 21/c'
_cod_database_code               2012318
_cod_database_fobs_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_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_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_site_symmetry_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) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21135080
