#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/80/2228087.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_2228087
loop_
_publ_author_name
'Guo, Ze-Rong'
'Li, Hua-Bo'
'Li, Fang'
_publ_section_title
;
 1,3,5-Trinitro-2,4-bis(2-phenylethenyl)benzene
;
_journal_coeditor_code           WN2408
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2486
_journal_paper_doi               10.1107/S1600536810034732
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H15 N3 O6'
_chemical_formula_moiety         'C22 H15 N3 O6'
_chemical_formula_sum            'C22 H15 N3 O6'
_chemical_formula_weight         417.37
_chemical_name_common            2,4,6-Trinitro-1,3-distyrylbenzene
_chemical_name_systematic
;
1,3,5-Trinitro-2,4-bis(2-phenylethenyl)benzene
;
_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                101.660(3)
_cell_angle_beta                 92.616(3)
_cell_angle_gamma                105.122(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0762(14)
_cell_length_b                   8.6625(17)
_cell_length_c                   16.717(3)
_cell_measurement_reflns_used    1118
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.79
_cell_measurement_theta_min      2.50
_cell_volume                     963.6(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5265
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.577217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0816
_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)+(0.1716P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2075
_refine_ls_wR_factor_ref         0.2359
_reflns_number_gt                2146
_reflns_number_total             3363
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            wn2408.cif
_cod_data_source_block           I
_cod_original_cell_volume        963.5(3)
_cod_database_code               2228087
_cod_database_fobs_code          2228087
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O O1 0.4557(4) 0.2087(3) 0.37673(15) 0.0606(7) Uani d . 1 . .
O O2 0.1502(4) 0.1919(3) 0.34477(15) 0.0629(7) Uani d . 1 . .
O O3 0.0777(6) -0.3754(4) 0.12446(17) 0.1042(13) Uani d . 1 . .
O O4 0.0663(6) -0.5709(4) 0.18422(17) 0.0944(11) Uani d . 1 . .
O O5 0.2954(4) -0.4565(3) 0.47219(15) 0.0599(7) Uani d . 1 . .
O O6 0.1092(4) -0.3227(3) 0.53578(14) 0.0558(7) Uani d . 1 . .
N N1 0.2829(5) 0.1337(3) 0.35892(14) 0.0450(7) Uani d . 1 . .
N N2 0.0966(4) -0.4259(4) 0.18514(18) 0.0576(8) Uani d . 1 . .
N N3 0.2018(4) -0.3561(3) 0.47819(16) 0.0413(6) Uani d . 1 . .
C C1 0.5959(7) 0.1705(4) 0.0976(2) 0.0659(11) Uani d . 1 . .
H H1 0.6973 0.1494 0.1272 0.079 Uiso calc R 1 . .
C C2 0.6401(8) 0.2529(5) 0.0357(2) 0.0796(13) Uani d . 1 . .
H H2 0.7691 0.2860 0.0230 0.096 Uiso calc R 1 . .
C C3 0.4936(11) 0.2845(6) -0.0061(3) 0.0892(16) Uani d . 1 . .
H H3 0.5228 0.3398 -0.0482 0.107 Uiso calc R 1 . .
C C4 0.3043(10) 0.2385(6) 0.0110(3) 0.0914(16) Uani d . 1 . .
H H4 0.2057 0.2629 -0.0187 0.110 Uiso calc R 1 . .
C C5 0.2581(7) 0.1525(5) 0.0745(2) 0.0739(12) Uani d . 1 . .
H H5 0.1289 0.1199 0.0869 0.089 Uiso calc R 1 . .
C C6 0.4058(6) 0.1181(4) 0.11752(19) 0.0533(9) Uani d . 1 . .
C C7 0.3715(6) 0.0306(4) 0.18496(19) 0.0502(9) Uani d . 1 . .
H H7 0.4820 0.0413 0.2202 0.060 Uiso calc R 1 . .
C C8 0.2044(5) -0.0607(4) 0.20150(18) 0.0479(8) Uani d . 1 . .
H H8 0.0901 -0.0756 0.1677 0.057 Uiso calc R 1 . .
C C9 0.1924(4) -0.1401(4) 0.27196(18) 0.0403(7) Uani d . 1 . .
C C10 0.1482(5) -0.3101(4) 0.26559(18) 0.0417(8) Uani d . 1 . .
C C11 0.1561(4) -0.3773(4) 0.33316(18) 0.0413(8) Uani d . 1 . .
H H11 0.1338 -0.4899 0.3271 0.050 Uiso calc R 1 . .
C C12 0.1978(4) -0.2745(3) 0.40967(17) 0.0369(7) Uani d . 1 . .
C C13 0.2335(4) -0.1039(3) 0.42426(17) 0.0352(7) Uani d . 1 . .
C C14 0.2324(4) -0.0458(3) 0.35209(17) 0.0358(7) Uani d . 1 . .
C C15 0.2759(4) -0.0028(3) 0.50832(17) 0.0351(7) Uani d . 1 . .
H H15 0.3253 -0.0496 0.5470 0.042 Uiso calc R 1 . .
C C16 0.2545(4) 0.1434(4) 0.53706(17) 0.0390(7) Uani d . 1 . .
H H16 0.2098 0.1960 0.4999 0.047 Uiso calc R 1 . .
C C17 0.2962(4) 0.2302(3) 0.62389(17) 0.0367(7) Uani d . 1 . .
C C18 0.3403(5) 0.3997(4) 0.6440(2) 0.0480(8) Uani d . 1 . .
H H18 0.3405 0.4570 0.6026 0.058 Uiso calc R 1 . .
C C19 0.3838(6) 0.4843(4) 0.7246(2) 0.0557(9) Uani d . 1 . .
H H19 0.4147 0.5982 0.7372 0.067 Uiso calc R 1 . .
C C20 0.3820(5) 0.4014(4) 0.7870(2) 0.0559(9) Uani d . 1 . .
H H20 0.4124 0.4589 0.8414 0.067 Uiso calc R 1 . .
C C21 0.3350(5) 0.2343(4) 0.76815(19) 0.0519(9) Uani d . 1 . .
H H21 0.3313 0.1781 0.8102 0.062 Uiso calc R 1 . .
C C22 0.2930(5) 0.1474(4) 0.68758(18) 0.0433(8) Uani d . 1 . .
H H22 0.2624 0.0335 0.6757 0.052 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
O2 N1 O1 . . 126.0(3) ?
O2 N1 C14 . . 117.4(3) ?
O1 N1 C14 . . 116.5(3) ?
O3 N2 O4 . . 122.9(3) ?
O3 N2 C10 . . 119.5(3) ?
O4 N2 C10 . . 117.5(3) ?
O5 N3 O6 . . 124.5(3) ?
O5 N3 C12 . . 116.7(3) ?
O6 N3 C12 . . 118.8(2) ?
C2 C1 C6 . . 122.2(4) ?
C2 C1 H1 . . 118.9 ?
C6 C1 H1 . . 118.9 ?
C3 C2 C1 . . 118.7(5) ?
C3 C2 H2 . . 120.7 ?
C1 C2 H2 . . 120.7 ?
C2 C3 C4 . . 122.1(5) ?
C2 C3 H3 . . 118.9 ?
C4 C3 H3 . . 118.9 ?
C3 C4 C5 . . 119.3(5) ?
C3 C4 H4 . . 120.3 ?
C5 C4 H4 . . 120.3 ?
C6 C5 C4 . . 119.4(5) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C5 C6 C1 . . 118.3(4) ?
C5 C6 C7 . . 123.0(4) ?
C1 C6 C7 . . 118.6(3) ?
C8 C7 C6 . . 128.2(3) ?
C8 C7 H7 . . 115.9 ?
C6 C7 H7 . . 115.9 ?
C7 C8 C9 . . 122.1(3) ?
C7 C8 H8 . . 118.9 ?
C9 C8 H8 . . 118.9 ?
C14 C9 C10 . . 114.8(3) ?
C14 C9 C8 . . 120.5(3) ?
C10 C9 C8 . . 124.7(3) ?
C11 C10 C9 . . 122.3(3) ?
C11 C10 N2 . . 116.5(3) ?
C9 C10 N2 . . 121.2(3) ?
C12 C11 C10 . . 118.6(3) ?
C12 C11 H11 . . 120.7 ?
C10 C11 H11 . . 120.7 ?
C11 C12 C13 . . 124.4(3) ?
C11 C12 N3 . . 115.1(3) ?
C13 C12 N3 . . 120.5(2) ?
C14 C13 C12 . . 113.1(3) ?
C14 C13 C15 . . 126.0(3) ?
C12 C13 C15 . . 120.9(3) ?
C9 C14 C13 . . 126.6(3) ?
C9 C14 N1 . . 114.9(3) ?
C13 C14 N1 . . 118.4(2) ?
C16 C15 C13 . . 129.8(3) ?
C16 C15 H15 . . 115.1 ?
C13 C15 H15 . . 115.1 ?
C15 C16 C17 . . 124.7(3) ?
C15 C16 H16 . . 117.7 ?
C17 C16 H16 . . 117.7 ?
C18 C17 C22 . . 118.3(3) ?
C18 C17 C16 . . 119.5(3) ?
C22 C17 C16 . . 122.2(3) ?
C19 C18 C17 . . 120.8(3) ?
C19 C18 H18 . . 119.6 ?
C17 C18 H18 . . 119.6 ?
C18 C19 C20 . . 120.4(3) ?
C18 C19 H19 . . 119.8 ?
C20 C19 H19 . . 119.8 ?
C21 C20 C19 . . 119.4(3) ?
C21 C20 H20 . . 120.3 ?
C19 C20 H20 . . 120.3 ?
C20 C21 C22 . . 120.9(3) ?
C20 C21 H21 . . 119.5 ?
C22 C21 H21 . . 119.5 ?
C21 C22 C17 . . 120.1(3) ?
C21 C22 H22 . . 120.0 ?
C17 C22 H22 . . 120.0 ?
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
O1 N1 . 1.217(3) ?
O2 N1 . 1.211(3) ?
O3 N2 . 1.199(4) ?
O4 N2 . 1.214(4) ?
O5 N3 . 1.216(3) ?
O6 N3 . 1.218(3) ?
N1 C14 . 1.481(4) ?
N2 C10 . 1.472(4) ?
N3 C12 . 1.465(4) ?
C1 C2 . 1.376(5) ?
C1 C6 . 1.382(5) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.341(7) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.356(7) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.420(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.370(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.476(5) ?
C7 C8 . 1.315(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.475(4) ?
C8 H8 . 0.9300 ?
C9 C14 . 1.394(4) ?
C9 C10 . 1.404(4) ?
C10 C11 . 1.376(4) ?
C11 C12 . 1.372(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.401(4) ?
C13 C14 . 1.398(4) ?
C13 C15 . 1.469(4) ?
C15 C16 . 1.311(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.471(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.385(4) ?
C17 C22 . 1.397(4) ?
C18 C19 . 1.376(4) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.379(5) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.364(5) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.381(4) ?
C21 H21 . 0.9300 ?
C22 H22 . 0.9300 ?
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
C16 H16 O2 . 0.93 2.60 3.398(4) 144
C16 H16 N1 . 0.93 2.42 2.980(4) 119
C18 H18 O5 1_565 0.93 2.48 3.387(4) 166
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.7(6) ?
C1 C2 C3 C4 . . . . 0.2(7) ?
C2 C3 C4 C5 . . . . -0.6(7) ?
C3 C4 C5 C6 . . . . 0.1(6) ?
C4 C5 C6 C1 . . . . 0.7(5) ?
C4 C5 C6 C7 . . . . 179.5(4) ?
C2 C1 C6 C5 . . . . -1.1(5) ?
C2 C1 C6 C7 . . . . -180.0(3) ?
C5 C6 C7 C8 . . . . 18.2(5) ?
C1 C6 C7 C8 . . . . -163.0(4) ?
C6 C7 C8 C9 . . . . -179.5(3) ?
C7 C8 C9 C14 . . . . 65.4(4) ?
C7 C8 C9 C10 . . . . -112.4(4) ?
C14 C9 C10 C11 . . . . -3.9(4) ?
C8 C9 C10 C11 . . . . 174.0(3) ?
C14 C9 C10 N2 . . . . 178.0(3) ?
C8 C9 C10 N2 . . . . -4.0(5) ?
O3 N2 C10 C11 . . . . 176.3(3) ?
O4 N2 C10 C11 . . . . -0.5(5) ?
O3 N2 C10 C9 . . . . -5.6(5) ?
O4 N2 C10 C9 . . . . 177.7(3) ?
C9 C10 C11 C12 . . . . 3.8(5) ?
N2 C10 C11 C12 . . . . -178.1(3) ?
C10 C11 C12 C13 . . . . -0.1(5) ?
C10 C11 C12 N3 . . . . 179.5(3) ?
O5 N3 C12 C11 . . . . 47.8(4) ?
O6 N3 C12 C11 . . . . -130.5(3) ?
O5 N3 C12 C13 . . . . -132.5(3) ?
O6 N3 C12 C13 . . . . 49.1(4) ?
C11 C12 C13 C14 . . . . -3.0(4) ?
N3 C12 C13 C14 . . . . 177.4(2) ?
C11 C12 C13 C15 . . . . 179.6(3) ?
N3 C12 C13 C15 . . . . 0.0(4) ?
C10 C9 C14 C13 . . . . 0.4(5) ?
C8 C9 C14 C13 . . . . -177.6(3) ?
C10 C9 C14 N1 . . . . 178.9(3) ?
C8 C9 C14 N1 . . . . 0.8(4) ?
C12 C13 C14 C9 . . . . 2.8(4) ?
C15 C13 C14 C9 . . . . -179.9(3) ?
C12 C13 C14 N1 . . . . -175.6(2) ?
C15 C13 C14 N1 . . . . 1.7(4) ?
O2 N1 C14 C9 . . . . 74.1(3) ?
O1 N1 C14 C9 . . . . -104.5(3) ?
O2 N1 C14 C13 . . . . -107.4(3) ?
O1 N1 C14 C13 . . . . 74.1(3) ?
C14 C13 C15 C16 . . . . 26.2(5) ?
C12 C13 C15 C16 . . . . -156.8(3) ?
C13 C15 C16 C17 . . . . 177.8(3) ?
C15 C16 C17 C18 . . . . 156.0(3) ?
C15 C16 C17 C22 . . . . -24.0(5) ?
C22 C17 C18 C19 . . . . 1.4(5) ?
C16 C17 C18 C19 . . . . -178.7(3) ?
C17 C18 C19 C20 . . . . -0.8(5) ?
C18 C19 C20 C21 . . . . -0.5(6) ?
C19 C20 C21 C22 . . . . 1.2(5) ?
C20 C21 C22 C17 . . . . -0.6(5) ?
C18 C17 C22 C21 . . . . -0.7(5) ?
C16 C17 C22 C21 . . . . 179.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4530538
