#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/57/2015747.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_2015747
loop_
_publ_author_name
'Gagnon, Eric'
'Maly, Kenneth E.'
'Maris, Thierry'
'Wuest, James D.'
_publ_section_title
;
 A new pseudopolymorph of hexakis(4-cyanophenyl)benzene
;
_journal_coeditor_code           GZ3032
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o4
_journal_page_last               o6
_journal_paper_doi               10.1107/S0108270106046452
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C48 H24 N6 , 2C H2 Cl2'
_chemical_formula_moiety         'C48 H24 N6 , 2C H2 Cl2'
_chemical_formula_sum            'C50 H28 Cl4 N6'
_chemical_formula_weight         854.58
_chemical_name_common            hexakis(4-cyanophenyl)benzene
_chemical_name_systematic
;
4,4',4'',4''',4'''',4'''''-benzenehexaylhexabenzonitrile dichloromethane
disolvate
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0921(3)
_cell_length_b                   19.3442(3)
_cell_length_c                   20.1742(4)
_cell_measurement_reflns_used    17112
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      67.21
_cell_measurement_theta_min      4.42
_cell_volume                     4328.73(16)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material
'enCIFer (Allen et al.,  2004) and publCIF (Westrip, 2006)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker SMART 6000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_av_sigmaI/netI    0.018
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            57445
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         4.38
_diffrn_standards_decay_%        0.30
_diffrn_standards_interval_time  1440
_diffrn_standards_number         151
_exptl_absorpt_coefficient_mu    2.819
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.281
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3865
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.119P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1382
_reflns_number_gt                3494
_reflns_number_total             3865
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gz3032.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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               2015747
_cod_database_fobs_code          2015747
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_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
C C1 0.0000 0.54553(6) 0.2500 0.0295(3) Uani d S 1 . .
N N1 0.0000 0.88565(7) 0.2500 0.0705(5) Uani d S 1 . .
C C2 0.06316(8) 0.51073(5) 0.19855(4) 0.0289(2) Uani d . 1 . .
N N2 0.37714(12) 0.67215(6) -0.05659(6) 0.0651(4) Uani d . 1 . .
C C3 0.06362(8) 0.44098(5) 0.19866(5) 0.0307(2) Uani d . 1 . .
N N3 0.38402(16) 0.26434(11) -0.04262(11) 0.1071(7) Uani d . 1 . .
C C4 0.0000 0.40677(7) 0.2500 0.0312(3) Uani d S 1 . .
N N4 0.0000 0.06745(7) 0.2500 0.0586(4) Uani d S 1 . .
C C5 0.0000 0.61995(6) 0.2500 0.0309(3) Uani d S 1 . .
C C6 -0.05247(10) 0.65481(5) 0.19553(5) 0.0372(3) Uani d . 1 . .
H H6 -0.0871 0.6296 0.1599 0.045 Uiso calc R 1 . .
C C7 -0.05239(11) 0.72363(5) 0.19524(6) 0.0434(3) Uani d . 1 . .
H H7 -0.0864 0.7489 0.1594 0.052 Uiso calc R 1 . .
C C8 0.0000 0.75784(7) 0.2500 0.0431(4) Uani d S 1 . .
C C9 0.0000 0.82943(8) 0.2500 0.0509(4) Uani d S 1 . .
C C10 0.12990(9) 0.54787(5) 0.14348(5) 0.0316(2) Uani d . 1 . .
C C11 0.23002(10) 0.58647(5) 0.15963(5) 0.0398(3) Uani d . 1 . .
H H11 0.2560 0.5903 0.2044 0.048 Uiso calc R 1 . .
C C12 0.29244(11) 0.61985(6) 0.10888(6) 0.0454(3) Uani d . 1 . .
H H12 0.3608 0.6471 0.1200 0.054 Uiso calc R 1 . .
C C13 0.25731(10) 0.61477(5) 0.03955(6) 0.0412(3) Uani d . 1 . .
C C14 0.15595(11) 0.57602(6) 0.02361(5) 0.0424(3) Uani d . 1 . .
H H14 0.1298 0.5720 -0.0211 0.051 Uiso calc R 1 . .
C C15 0.09324(10) 0.54306(6) 0.07492(5) 0.0390(3) Uani d . 1 . .
H H15 0.0239 0.5165 0.0642 0.047 Uiso calc R 1 . .
C C16 0.32203(12) 0.64664(6) -0.01203(6) 0.0493(3) Uani d . 1 . .
C C17 0.13343(9) 0.40327(5) 0.14529(5) 0.0333(2) Uani d . 1 . .
C C18 0.25865(10) 0.40777(5) 0.14290(6) 0.0396(3) Uani d . 1 . .
H H18 0.3001 0.4358 0.1742 0.048 Uiso calc R 1 . .
C C19 0.32396(10) 0.37149(6) 0.09494(6) 0.0495(3) Uani d . 1 . .
H H19 0.4094 0.3746 0.0942 0.059 Uiso calc R 1 . .
C C20 0.26421(12) 0.33033(7) 0.04765(7) 0.0535(3) Uani d . 1 . .
C C21 0.13814(12) 0.32596(6) 0.05053(6) 0.0493(3) Uani d . 1 . .
H H21 0.0961 0.2986 0.0190 0.059 Uiso calc R 1 . .
C C22 0.07419(10) 0.36141(5) 0.09914(6) 0.0392(3) Uani d . 1 . .
H H22 -0.0111 0.3571 0.1010 0.047 Uiso calc R 1 . .
C C23 0.32914(15) 0.29406(8) -0.00100(9) 0.0743(5) Uani d . 1 . .
C C24 0.0000 0.33275(7) 0.2500 0.0334(3) Uani d S 1 . .
C C25 -0.10428(10) 0.29803(5) 0.23224(6) 0.0409(3) Uani d . 1 . .
H H25 -0.1750 0.3230 0.2207 0.049 Uiso calc R 1 . .
C C26 -0.10419(10) 0.22943(5) 0.23159(7) 0.0446(3) Uani d . 1 . .
H H26 -0.1741 0.2044 0.2188 0.054 Uiso calc R 1 . .
C C27 0.0000 0.19525(7) 0.2500 0.0403(4) Uani d S 1 . .
C C28 0.0000 0.12432(8) 0.2500 0.0442(4) Uani d S 1 . .
C C29 0.6145(6) 0.4921(2) 0.1182(4) 0.0666(7) Uani d PDU 0.5312(11) A 1
H H29A 0.6001 0.4598 0.0810 0.080 Uiso calc PR 0.5312(11) A 1
H H29B 0.5464 0.4881 0.1497 0.080 Uiso calc PR 0.5312(11) A 1
Cl Cl1 0.7509(7) 0.4705(3) 0.1586(4) 0.0848(8) Uani d PDU 0.5312(11) A 1
Cl Cl2 0.62378(12) 0.57770(7) 0.08797(6) 0.1118(3) Uani d PDU 0.5312(11) A 1
C C30 0.6042(7) 0.4850(4) 0.1294(3) 0.0666(7) Uani d PDU 0.4688(11) A 2
H H30A 0.5789 0.4362 0.1252 0.080 Uiso calc PR 0.4688(11) A 2
H H30B 0.5519 0.5076 0.1627 0.080 Uiso calc PR 0.4688(11) A 2
Cl Cl3 0.7561(8) 0.4891(3) 0.1554(5) 0.0848(8) Uani d PDU 0.4688(11) A 2
Cl Cl4 0.58793(15) 0.52710(7) 0.05219(7) 0.1118(3) Uani d PDU 0.4688(11) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0000 '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 0.0311 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C2 3 . 123.49(11) n
C2 C1 C5 3 . 118.25(6) n
C2 C1 C5 . . 118.26(6) n
C3 C2 C1 . . 118.30(8) n
C3 C2 C10 . . 118.24(8) n
C1 C2 C10 . . 123.46(8) n
C2 C3 C4 . . 117.79(9) n
C2 C3 C17 . . 118.87(8) n
C4 C3 C17 . . 123.33(8) n
C3 C4 C3 3 . 124.32(12) n
C3 C4 C24 3 . 117.84(6) n
C3 C4 C24 . . 117.84(6) n
C6 C5 C6 3 . 123.06(12) n
C6 C5 C1 3 . 118.47(6) n
C6 C5 C1 . . 118.47(6) n
C7 C6 C5 . . 118.67(10) n
C7 C6 H6 . . 120.7 ?
C5 C6 H6 . . 120.7 ?
C6 C7 C8 . . 117.73(10) n
C6 C7 H7 . . 121.1 ?
C8 C7 H7 . . 121.1 ?
C9 C8 C7 . 3 117.94(6) n
C9 C8 C7 . . 117.93(6) n
C7 C8 C7 3 . 124.13(13) n
N1 C9 C8 . . 180.0000(10) n
C11 C10 C15 . . 119.24(9) n
C11 C10 C2 . . 118.50(9) n
C15 C10 C2 . . 122.25(8) n
C10 C11 C12 . . 118.53(10) n
C10 C11 H11 . . 120.7 ?
C12 C11 H11 . . 120.7 ?
C11 C12 C13 . . 122.78(10) n
C11 C12 H12 . . 118.6 ?
C13 C12 H12 . . 118.6 ?
C14 C13 C16 . . 118.58(11) n
C14 C13 C12 . . 118.41(10) n
C16 C13 C12 . . 123.01(10) n
C13 C14 C15 . . 118.45(10) n
C13 C14 H14 . . 120.8 ?
C15 C14 H14 . . 120.8 ?
C14 C15 C10 . . 122.58(10) n
C14 C15 H15 . . 118.7 ?
C10 C15 H15 . . 118.7 ?
N2 C16 C13 . . 178.37(12) n
C18 C17 C22 . . 118.81(10) n
C18 C17 C3 . . 120.32(9) n
C22 C17 C3 . . 120.83(9) n
C17 C18 C19 . . 120.64(10) n
C17 C18 H18 . . 119.7 ?
C19 C18 H18 . . 119.7 ?
C18 C19 C20 . . 120.59(11) n
C18 C19 H19 . . 119.7 ?
C20 C19 H19 . . 119.7 ?
C21 C20 C23 . . 120.66(13) n
C21 C20 C19 . . 118.39(11) n
C23 C20 C19 . . 120.95(12) n
C22 C21 C20 . . 120.53(11) n
C22 C21 H21 . . 119.7 ?
C20 C21 H21 . . 119.7 ?
C21 C22 C17 . . 121.03(10) n
C21 C22 H22 . . 119.5 ?
C17 C22 H22 . . 119.5 ?
N3 C23 C20 . . 179.0(2) n
C25 C24 C25 3 . 121.97(13) n
C25 C24 C4 3 . 119.02(6) ?
C25 C24 C4 . . 119.02(6) ?
C26 C25 C24 . . 119.14(10) n
C26 C25 H25 . . 120.4 ?
C24 C25 H25 . . 120.4 ?
C25 C26 C27 . . 118.44(10) n
C25 C26 H26 . . 120.8 ?
C27 C26 H26 . . 120.8 ?
C28 C27 C26 . . 118.57(7) n
C28 C27 C26 . 3 118.57(7) n
C26 C27 C26 . 3 122.86(13) n
N4 C28 C27 . . 180.0 n
Cl2 C29 Cl1 . . 109.3(3) n
Cl2 C29 H29A . . 109.8 ?
Cl1 C29 H29A . . 109.8 ?
Cl2 C29 H29B . . 109.8 ?
Cl1 C29 H29B . . 109.8 ?
H29A C29 H29B . . 108.3 ?
Cl4 C30 Cl3 . . 109.8(4) n
Cl4 C30 H30A . . 109.7 ?
Cl3 C30 H30A . . 109.7 ?
Cl4 C30 H30B . . 109.7 ?
Cl3 C30 H30B . . 109.7 ?
H30A C30 H30B . . 108.2 ?
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 3 1.4217(11) n
C1 C2 . 1.4217(11) n
C1 C5 . 1.4397(17) n
N1 C9 . 1.088(2) n
C2 C3 . 1.3493(13) n
C2 C10 . 1.5161(13) n
N2 C16 . 1.1939(17) n
C3 C4 . 1.4173(11) n
C3 C17 . 1.5136(13) n
N3 C23 . 1.186(2) n
C4 C3 3 1.4173(11) n
C4 C24 . 1.4318(18) n
N4 C28 . 1.100(2) n
C5 C6 3 1.4144(12) n
C5 C6 . 1.4145(12) n
C6 C7 . 1.3314(14) n
C6 H6 . 0.9500 ?
C7 C8 . 1.4128(14) n
C7 H7 . 0.9500 ?
C8 C9 . 1.385(2) n
C8 C7 3 1.4128(14) n
C10 C11 . 1.3773(15) n
C10 C15 . 1.4447(15) n
C11 C12 . 1.3945(16) n
C11 H11 . 0.9500 ?
C12 C13 . 1.4553(18) n
C12 H12 . 0.9500 ?
C13 C14 . 1.3891(16) n
C13 C16 . 1.4065(17) n
C14 C15 . 1.4007(16) n
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C17 C18 . 1.3925(15) n
C17 C22 . 1.3980(14) n
C18 C19 . 1.3977(15) n
C18 H18 . 0.9500 ?
C19 C20 . 1.4083(18) n
C19 H19 . 0.9500 ?
C20 C21 . 1.4021(19) n
C20 C23 . 1.4051(19) n
C21 C22 . 1.3910(16) n
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
C24 C25 3 1.3847(12) n
C24 C25 . 1.3848(12) n
C25 C26 . 1.3271(14) n
C25 H25 . 0.9500 ?
C26 C27 . 1.3823(13) n
C26 H26 . 0.9500 ?
C27 C28 . 1.3721(19) n
C27 C26 3 1.3824(14) n
C29 Cl2 . 1.768(3) n
C29 Cl1 . 1.768(2) n
C29 H29A . 0.9900 ?
C29 H29B . 0.9900 ?
C30 Cl4 . 1.766(3) n
C30 Cl3 . 1.767(3) n
C30 H30A . 0.9900 ?
C30 H30B . 0.9900 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C19 H19 N2 5_665 0.95 2.65 3.5076(17) 151
C7 H7 N2 4_465 0.95 2.61 3.5355(16) 165
C21 H21 N3 4_455 0.95 2.69 3.320(2) 124
C29 H29B N4 6_666 0.99 2.59 3.288(9) 127
