#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/16/1501617.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_1501617
loop_
_publ_author_name
'Eric Gagnon'
'Thierry Maris'
'Kenneth E. Maly'
'James D. Wuest'
_publ_section_title
;
 The potential of intermolecular N/O interactions of nitro groups in
 crystal engineering, as revealed by structures of
 hexakis(4-nitrophenyl)benzene
;
_journal_name_full               Tetrahedron
_journal_page_first              6603
_journal_page_last               6613
_journal_paper_doi               10.1016/j.tet.2007.03.101
_journal_volume                  63
_journal_year                    2007
_chemical_formula_moiety         'C42 H24 N6 O12, 7(C4 H8 O2)'
_chemical_formula_sum            'C70 H80 N6 O26'
_chemical_formula_weight         1421.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.10(3)
_cell_angle_beta                 108.37(3)
_cell_angle_gamma                110.42(3)
_cell_formula_units_Z            1
_cell_length_a                   11.533(2)
_cell_length_b                   13.037(3)
_cell_length_c                   14.014(3)
_cell_measurement_reflns_used    1100
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.62
_cell_measurement_theta_min      5.10
_cell_volume                     1703.7(11)
_computing_cell_refinement       'SMART (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.875
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Micro source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6484
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         66.71
_diffrn_reflns_theta_min         3.66
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.897
_exptl_absorpt_correction_T_max  0.9200
_exptl_absorpt_correction_T_min  0.7100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             750
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         5328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0719P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1327
_reflns_number_gt                3740
_reflns_number_total             5328
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            deposit.cif
_cod_data_source_block           jw1177
_cod_original_cell_volume        1703.7(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1501617
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
O10 O 0.10518(19) 0.20903(17) 0.54793(13) 0.0629(5) Uani 1 1 d .
O11 O 0.2144(2) 0.10811(19) 0.54967(16) 0.0786(7) Uani 1 1 d .
O20 O -0.5040(2) -0.36667(17) 0.37373(12) 0.0821(7) Uani 1 1 d .
O21 O -0.4081(2) -0.47485(18) 0.39048(14) 0.0994(9) Uani 1 1 d .
O30 O 0.69553(18) 0.55634(18) 1.18655(18) 0.0855(6) Uani 1 1 d .
O31 O 0.56526(19) 0.63684(15) 1.14825(16) 0.0685(5) Uani 1 1 d .
N10 N 0.14728(17) 0.14688(15) 0.58268(13) 0.0358(4) Uani 1 1 d .
N20 N -0.42380(18) -0.39116(16) 0.42824(13) 0.0398(4) Uani 1 1 d .
N30 N 0.58135(19) 0.55162(16) 1.15356(14) 0.0418(4) Uani 1 1 d .
C1 C 0.02449(19) 0.02910(17) 0.91751(14) 0.0309(4) Uani 1 1 d .
C2 C -0.08546(19) -0.07905(18) 0.88852(14) 0.0304(4) Uani 1 1 d .
C3 C 0.11293(19) 0.11036(17) 1.02841(14) 0.0311(4) Uani 1 1 d .
C10 C 0.1145(2) 0.11547(18) 0.66794(15) 0.0343(4) Uani 1 1 d .
C11 C 0.1701(2) 0.05272(19) 0.71144(15) 0.0370(5) Uani 1 1 d .
H11 H 0.2290 0.0290 0.6878 0.044 Uiso 1 1 calc R
C12 C 0.1378(2) 0.02384(18) 0.79268(15) 0.0347(4) Uani 1 1 d .
H12 H 0.1733 -0.0222 0.8230 0.042 Uiso 1 1 calc R
C13 C 0.05642(19) 0.06086(18) 0.82870(14) 0.0324(4) Uani 1 1 d .
C14 C 0.0054(2) 0.12668(19) 0.78469(16) 0.0404(5) Uani 1 1 d .
H14 H -0.0497 0.1543 0.8106 0.049 Uiso 1 1 calc R
C15 C 0.0336(2) 0.15399(19) 0.70140(15) 0.0392(5) Uani 1 1 d .
H15 H -0.0033 0.1984 0.6695 0.047 Uiso 1 1 calc R
C20 C -0.17954(19) -0.16591(17) 0.76933(14) 0.0299(4) Uani 1 1 d .
C21 C -0.2813(2) -0.14710(19) 0.70641(16) 0.0414(5) Uani 1 1 d .
H21 H -0.2964 -0.0827 0.7397 0.050 Uiso 1 1 calc R
C22 C -0.3631(2) -0.2217(2) 0.59382(16) 0.0429(5) Uani 1 1 d .
H22 H -0.4333 -0.2086 0.5498 0.051 Uiso 1 1 calc R
C23 C -0.3398(2) -0.31332(18) 0.54901(15) 0.0333(4) Uani 1 1 d .
C24 C -0.2396(2) -0.3351(2) 0.60905(16) 0.0413(5) Uani 1 1 d .
H24 H -0.2257 -0.4002 0.5755 0.050 Uiso 1 1 calc R
C25 C -0.1581(2) -0.25850(18) 0.72150(15) 0.0353(5) Uani 1 1 d .
H25 H -0.0870 -0.2711 0.7650 0.042 Uiso 1 1 calc R
C30 C 0.2334(2) 0.22506(18) 1.05863(14) 0.0323(4) Uani 1 1 d .
C31 C 0.3601(2) 0.2307(2) 1.08398(16) 0.0419(5) Uani 1 1 d .
H31 H 0.3704 0.1607 1.0805 0.050 Uiso 1 1 calc R
C32 C 0.4759(2) 0.3397(2) 1.11533(17) 0.0467(5) Uani 1 1 d .
H32 H 0.5648 0.3443 1.1351 0.056 Uiso 1 1 calc R
C33 C 0.4598(2) 0.4378(2) 1.11723(16) 0.0393(5) Uani 1 1 d .
C34 C 0.3346(2) 0.4342(2) 1.08947(17) 0.0426(5) Uani 1 1 d .
H34 H 0.3241 0.5034 1.0897 0.051 Uiso 1 1 calc R
C35 C 0.2224(2) 0.32716(19) 1.06080(16) 0.0402(5) Uani 1 1 d .
H35 H 0.1341 0.3239 1.0418 0.048 Uiso 1 1 calc R
O40 O 0.37169(19) 0.96719(16) 0.06921(16) 0.0683(5) Uani 1 1 d .
O43 O 0.30547(18) 0.73386(15) 0.05723(15) 0.0667(5) Uani 1 1 d .
C41 C 0.4650(3) 0.9148(3) 0.0721(2) 0.0696(8) Uani 1 1 d .
H41A H 0.4512 0.8755 -0.0042 0.084 Uiso 1 1 calc R
H41B H 0.5618 0.9801 0.1161 0.084 Uiso 1 1 calc R
C42 C 0.4439(3) 0.8290(3) 0.1182(2) 0.0651(7) Uani 1 1 d .
H42A H 0.4633 0.8689 0.1960 0.078 Uiso 1 1 calc R
H42B H 0.5089 0.7956 0.1174 0.078 Uiso 1 1 calc R
C44 C 0.2147(3) 0.7859(3) 0.0573(2) 0.0689(7) Uani 1 1 d .
H44A H 0.1175 0.7211 0.0161 0.083 Uiso 1 1 calc R
H44B H 0.2326 0.8275 0.1344 0.083 Uiso 1 1 calc R
C45 C 0.2330(3) 0.8699(3) 0.0082(2) 0.0616(7) Uani 1 1 d .
H45A H 0.1666 0.9019 0.0074 0.074 Uiso 1 1 calc R
H45B H 0.2141 0.8287 -0.0693 0.074 Uiso 1 1 calc R
O50 O 0.8312(2) 0.39670(19) 0.46528(17) 0.0839(6) Uani 1 1 d .
C51 C 0.6873(4) 0.3040(3) 0.4044(3) 0.0910(10) Uani 1 1 d .
H51A H 0.6256 0.3415 0.3946 0.109 Uiso 1 1 calc R
H51B H 0.6656 0.2548 0.4456 0.109 Uiso 1 1 calc R
C52 C 0.6660(3) 0.2280(3) 0.2962(3) 0.0849(9) Uani 1 1 d .
H52A H 0.5675 0.1664 0.2521 0.102 Uiso 1 1 calc R
H52B H 0.6884 0.2782 0.2560 0.102 Uiso 1 1 calc R
O53 O 0.7509(2) 0.1695(2) 0.30741(16) 0.1012(9) Uani 1 1 d .
C54 C 0.8928(3) 0.2600(3) 0.3682(2) 0.0722(8) Uani 1 1 d .
H54A H 0.9155 0.3084 0.3267 0.087 Uiso 1 1 calc R
H54B H 0.9533 0.2213 0.3780 0.087 Uiso 1 1 calc R
C55 C 0.9178(3) 0.3392(3) 0.4777(2) 0.0703(8) Uani 1 1 d .
H55A H 0.8980 0.2910 0.5201 0.084 Uiso 1 1 calc R
H55B H 1.0163 0.4013 0.5197 0.084 Uiso 1 1 calc R
O60 O 0.0939(3) 0.6669(2) 0.2159(2) 0.0944(8) Uani 1 1 d .
O63 O 0.0301(2) 0.43436(17) 0.20380(15) 0.0835(7) Uani 1 1 d .
C61 C -0.0403(3) 0.5712(3) 0.1492(3) 0.0791(9) Uani 1 1 d .
H61A H -0.0511 0.5329 0.0738 0.095 Uiso 1 1 calc R
H61B H -0.1082 0.6021 0.1438 0.095 Uiso 1 1 calc R
C62 C -0.0690(3) 0.4783(3) 0.1967(2) 0.0743(8) Uani 1 1 d .
H62A H -0.0616 0.5152 0.2711 0.089 Uiso 1 1 calc R
H62B H -0.1640 0.4109 0.1486 0.089 Uiso 1 1 calc R
C64 C 0.1665(3) 0.5297(3) 0.2704(2) 0.0641(7) Uani 1 1 d .
H64A H 0.2333 0.4978 0.2737 0.077 Uiso 1 1 calc R
H64B H 0.1793 0.5675 0.3466 0.077 Uiso 1 1 calc R
C65 C 0.1944(3) 0.6223(3) 0.2244(2) 0.0668(7) Uani 1 1 d .
H65A H 0.2891 0.6899 0.2733 0.080 Uiso 1 1 calc R
H65B H 0.1884 0.5862 0.1504 0.080 Uiso 1 1 calc R
O70 O 0.5485(2) -0.0092(2) 0.60213(14) 0.0835(7) Uani 1 1 d .
C71 C 0.6431(3) 0.0404(3) 0.5601(2) 0.0690(8) Uani 1 1 d .
H71A H 0.7209 0.0217 0.5832 0.083 Uiso 1 1 calc R
H71B H 0.6814 0.1291 0.5903 0.083 Uiso 1 1 calc R
C72 C 0.4337(3) 0.0136(3) 0.5660(2) 0.0629(7) Uani 1 1 d .
H72A H 0.4669 0.1016 0.5958 0.075 Uiso 1 1 calc R
H72B H 0.3692 -0.0214 0.5951 0.075 Uiso 1 1 calc R
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 0.0091 '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 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O11 N10 O10 122.59(16) . .
O11 N10 C10 118.09(15) . .
O10 N10 C10 119.32(15) . .
O21 N20 O20 122.84(18) . .
O21 N20 C23 118.33(17) . .
O20 N20 C23 118.82(16) . .
O31 N30 O30 122.5(2) . .
O31 N30 C33 118.79(19) . .
O30 N30 C33 118.72(18) . .
C2 C1 C3 121.66(17) . .
C2 C1 C13 120.02(17) . .
C3 C1 C13 118.27(18) . .
C1 C2 C3 120.07(17) . 2_557
C1 C2 C20 121.31(16) . .
C3 C2 C20 118.61(18) 2_557 .
C1 C3 C2 118.26(19) . 2_557
C1 C3 C30 121.10(16) . .
C2 C3 C30 120.62(16) 2_557 .
C15 C10 C11 123.06(18) . .
C15 C10 N10 118.27(16) . .
C11 C10 N10 118.64(16) . .
C10 C11 C12 117.82(18) . .
C13 C12 C11 120.97(18) . .
C12 C13 C14 119.33(18) . .
C12 C13 C1 119.71(16) . .
C14 C13 C1 120.96(16) . .
C13 C14 C15 120.58(18) . .
C10 C15 C14 118.21(18) . .
C25 C20 C21 119.66(18) . .
C25 C20 C2 120.36(16) . .
C21 C20 C2 119.82(16) . .
C20 C21 C22 120.63(18) . .
C23 C22 C21 118.24(18) . .
C22 C23 C24 122.82(19) . .
C22 C23 N20 118.57(17) . .
C24 C23 N20 118.57(17) . .
C23 C24 C25 117.93(18) . .
C20 C25 C24 120.70(17) . .
C31 C30 C35 118.0(2) . .
C31 C30 C3 119.59(18) . .
C35 C30 C3 122.43(18) . .
C30 C31 C32 120.12(19) . .
C33 C32 C31 119.6(2) . .
C32 C33 C34 121.7(2) . .
C32 C33 N30 119.16(19) . .
C34 C33 N30 119.15(19) . .
C33 C34 C35 118.1(2) . .
C30 C35 C34 122.53(19) . .
C45 O40 C41 107.37(19) . .
C42 O43 C44 107.85(19) . .
C42 C41 O40 112.7(2) . .
C41 C42 O43 110.7(2) . .
C45 C44 O43 111.9(2) . .
C44 C45 O40 110.2(2) . .
C55 O50 C51 108.6(2) . .
O50 C51 C52 108.1(3) . .
O53 C52 C51 111.5(3) . .
C54 O53 C52 108.4(2) . .
O53 C54 C55 109.8(2) . .
O50 C55 C54 110.6(2) . .
C61 O60 C65 109.9(2) . .
C64 O63 C62 110.76(19) . .
O60 C61 C62 110.8(3) . .
O63 C62 C61 108.7(2) . .
O63 C64 C65 110.5(2) . .
O60 C65 C64 109.9(2) . .
C72 O70 C71 110.19(19) . .
O70 C71 C72 109.2(2) . 2_656
O70 C72 C71 111.3(2) . 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O10 N10 1.209(2) .
O11 N10 1.202(2) .
O20 N20 1.195(2) .
O21 N20 1.183(2) .
O30 N30 1.223(2) .
O31 N30 1.205(2) .
N10 C10 1.474(2) .
N20 C23 1.490(2) .
N30 C33 1.459(3) .
C1 C2 1.374(3) .
C1 C3 1.402(2) .
C1 C13 1.520(2) .
C2 C3 1.419(2) 2_557
C2 C20 1.505(3) .
C3 C2 1.419(2) 2_557
C3 C30 1.481(3) .
C10 C15 1.350(3) .
C10 C11 1.353(2) .
C11 C12 1.404(2) .
C12 C13 1.363(2) .
C13 C14 1.365(3) .
C14 C15 1.404(3) .
C20 C25 1.363(2) .
C20 C21 1.370(2) .
C21 C22 1.395(3) .
C22 C23 1.354(3) .
C23 C24 1.365(2) .
C24 C25 1.398(3) .
C30 C31 1.360(3) .
C30 C35 1.374(3) .
C31 C32 1.405(3) .
C32 C33 1.350(3) .
C33 C34 1.352(3) .
C34 C35 1.378(3) .
O40 C45 1.433(3) .
O40 C41 1.458(3) .
O43 C42 1.422(3) .
O43 C44 1.433(3) .
C41 C42 1.421(4) .
C44 C45 1.429(4) .
O50 C55 1.439(3) .
O50 C51 1.453(4) .
C51 C52 1.469(4) .
C52 O53 1.431(3) .
O53 C54 1.430(4) .
C54 C55 1.481(4) .
O60 C61 1.399(4) .
O60 C65 1.454(3) .
O63 C64 1.412(3) .
O63 C62 1.436(3) .
C61 C62 1.517(4) .
C64 C65 1.497(4) .
O70 C72 1.424(3) .
O70 C71 1.438(3) .
C71 C72 1.527(3) 2_656
C72 C71 1.527(3) 2_656
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C25 H25 O63 0.95 2.54 3.342(2) 142.8 2_556
C31 H31 O40 0.95 2.49 3.438(3) 173.9 1_546
C42 H42B O31 0.99 2.47 3.322(3) 143.3 1_554
C51 H51A O21 0.99 2.57 3.454(4) 149.0 1_665
C54 H54A O50 0.99 3.57 3.941(4) 104.7 2_766
C54 H54B O10 0.99 2.56 3.302(3) 132.1 1_655
C61 H61B O30 0.99 2.44 3.200(4) 133.5 1_454
C62 H62B O43 0.99 2.57 3.353(4) 136.2 2_565
C64 H64A O20 0.99 2.56 3.208(3) 122.8 1_665
