#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/36/2223693.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_2223693
loop_
_publ_author_name
'Jing, Lin-Hai'
_publ_section_title
;
 (E)-1-Nitro-4-(2-nitroethenyl)benzene
;
_journal_coeditor_code           CI2942
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2809
_journal_paper_doi               10.1107/S1600536809042561
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C8 H6 N2 O4'
_chemical_formula_moiety         'C8 H6 N2 O4'
_chemical_formula_sum            'C8 H6 N2 O4'
_chemical_formula_weight         194.15
_chemical_name_systematic
;
(E)-1-Nitro-4-(2-nitroethenyl)benzene
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.847(4)
_cell_length_b                   4.9991(11)
_cell_length_c                   20.495(5)
_cell_measurement_reflns_used    5000
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.25
_cell_volume                     1623.6(7)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2004)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2004)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2004)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku AFC10/Saturn724+'
_diffrn_measurement_method       multi-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12157
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.25
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         1921
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0583P)²+0.0124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0896
_reflns_number_gt                1821
_reflns_number_total             1921
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2942.cif
_cod_data_source_block           I
_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               2223693
_cod_database_fobs_code          2223693
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, 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
O O1 0.00934(11) -0.2104(4) 0.37970(9) 0.0256(4) Uani d . 1 . .
O O2 0.03415(11) -0.1404(4) 0.27702(8) 0.0227(4) Uani d . 1 . .
O O3 0.40990(11) 1.2126(4) 0.30965(8) 0.0231(4) Uani d . 1 . .
O O4 0.39197(11) 1.1786(3) 0.41409(8) 0.0227(4) Uani d . 1 . .
N N1 0.04305(12) -0.0847(4) 0.33513(10) 0.0181(4) Uani d . 1 . .
N N2 0.37733(12) 1.1093(4) 0.35767(10) 0.0172(4) Uani d . 1 . .
C C1 0.20144(14) 0.4859(5) 0.32540(12) 0.0201(5) Uani d . 1 . .
C C2 0.24209(16) 0.6078(5) 0.27306(12) 0.0212(5) Uani d . 1 . .
H H2 0.2299 0.5506 0.2299 0.025 Uiso calc R 1 . .
C C3 0.29987(15) 0.8108(5) 0.28293(12) 0.0194(5) Uani d . 1 . .
H H3 0.3273 0.8938 0.2470 0.023 Uiso calc R 1 . .
C C4 0.31691(14) 0.8909(5) 0.34625(11) 0.0170(5) Uani d . 1 . .
C C5 0.27766(15) 0.7755(5) 0.39972(12) 0.0195(5) Uani d . 1 . .
H H5 0.2901 0.8348 0.4427 0.023 Uiso calc R 1 . .
C C6 0.21957(15) 0.5709(5) 0.38928(12) 0.0214(5) Uani d . 1 . .
H H6 0.1922 0.4887 0.4253 0.026 Uiso calc R 1 . .
C C7 0.14131(14) 0.2682(5) 0.31123(13) 0.0200(5) Uani d . 1 . .
H H7 0.1345 0.2178 0.2669 0.024 Uiso calc R 1 . .
C C8 0.09642(15) 0.1380(5) 0.35480(12) 0.0198(5) Uani d . 1 . .
H H8 0.0988 0.1896 0.3994 0.024 Uiso calc R 1 . .
O O5 0.69565(11) 0.3595(4) 0.15876(8) 0.0214(4) Uani d . 1 . .
O O6 0.72313(10) 0.2899(4) 0.05672(9) 0.0234(4) Uani d . 1 . .
O O7 0.33698(11) 1.6608(4) 0.01863(8) 0.0239(4) Uani d . 1 . .
O O8 0.31958(11) 1.7112(3) 0.12274(9) 0.0222(4) Uani d . 1 . .
N N3 0.68809(12) 0.4151(4) 0.10092(10) 0.0167(4) Uani d . 1 . .
N N4 0.35187(12) 1.6000(4) 0.07547(10) 0.0167(4) Uani d . 1 . .
C C9 0.52828(13) 0.9813(5) 0.11027(11) 0.0170(5) Uani d . 1 . .
C C10 0.51094(15) 1.0658(5) 0.04660(12) 0.0203(5) Uani d . 1 . .
H H10 0.5396 0.9851 0.0110 0.024 Uiso calc R 1 . .
C C11 0.45240(14) 1.2658(5) 0.03503(12) 0.0204(5) Uani d . 1 . .
H H11 0.4398 1.3216 -0.0082 0.024 Uiso calc R 1 . .
C C12 0.41275(14) 1.3822(5) 0.08803(11) 0.0167(5) Uani d . 1 . .
C C13 0.42840(15) 1.3075(5) 0.15165(12) 0.0184(5) Uani d . 1 . .
H H13 0.4004 1.3928 0.1870 0.022 Uiso calc R 1 . .
C C14 0.48642(15) 1.1037(5) 0.16264(12) 0.0173(5) Uani d . 1 . .
H H14 0.4978 1.0470 0.2060 0.021 Uiso calc R 1 . .
C C15 0.58824(14) 0.7649(5) 0.12470(12) 0.0175(5) Uani d . 1 . .
H H15 0.5946 0.7135 0.1691 0.021 Uiso calc R 1 . .
C C16 0.63421(15) 0.6356(5) 0.08075(11) 0.0191(5) Uani d . 1 . .
H H16 0.6320 0.6871 0.0362 0.023 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 0.0000 '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 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 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
O2 N1 O1 . . 123.6(2) ?
O2 N1 C8 . . 120.5(2) ?
O1 N1 C8 . . 115.9(2) ?
O3 N2 O4 . . 123.9(2) ?
O3 N2 C4 . . 117.33(19) ?
O4 N2 C4 . . 118.79(19) ?
C2 C1 C6 . . 119.4(2) ?
C2 C1 C7 . . 118.0(2) ?
C6 C1 C7 . . 122.6(2) ?
C3 C2 C1 . . 121.0(2) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C2 C3 C4 . . 118.6(2) ?
C2 C3 H3 . . 120.7 ?
C4 C3 H3 . . 120.7 ?
C3 C4 C5 . . 122.2(2) ?
C3 C4 N2 . . 119.4(2) ?
C5 C4 N2 . . 118.4(2) ?
C4 C5 C6 . . 118.7(2) ?
C4 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
C5 C6 C1 . . 120.0(2) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
C8 C7 C1 . . 125.5(2) ?
C8 C7 H7 . . 117.2 ?
C1 C7 H7 . . 117.2 ?
C7 C8 N1 . . 120.3(2) ?
C7 C8 H8 . . 119.8 ?
N1 C8 H8 . . 119.8 ?
O5 N3 O6 . . 123.5(2) ?
O5 N3 C16 . . 120.3(2) ?
O6 N3 C16 . . 116.11(19) ?
O7 N4 O8 . . 123.8(2) ?
O7 N4 C12 . . 118.28(19) ?
O8 N4 C12 . . 117.89(19) ?
C10 C9 C14 . . 119.3(2) ?
C10 C9 C15 . . 122.5(2) ?
C14 C9 C15 . . 118.2(2) ?
C11 C10 C9 . . 120.6(2) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C12 C11 C10 . . 118.3(2) ?
C12 C11 H11 . . 120.9 ?
C10 C11 H11 . . 120.9 ?
C13 C12 C11 . . 123.2(2) ?
C13 C12 N4 . . 118.8(2) ?
C11 C12 N4 . . 118.0(2) ?
C12 C13 C14 . . 118.1(2) ?
C12 C13 H13 . . 121.0 ?
C14 C13 H13 . . 121.0 ?
C13 C14 C9 . . 120.6(2) ?
C13 C14 H14 . . 119.7 ?
C9 C14 H14 . . 119.7 ?
C16 C15 C9 . . 125.2(2) ?
C16 C15 H15 . . 117.4 ?
C9 C15 H15 . . 117.4 ?
C15 C16 N3 . . 119.9(2) ?
C15 C16 H16 . . 120.0 ?
N3 C16 H16 . . 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 . 1.231(3) ?
O2 N1 . 1.231(3) ?
O3 N2 . 1.225(3) ?
O4 N2 . 1.229(3) ?
N1 C8 . 1.455(3) ?
N2 C4 . 1.471(3) ?
C1 C2 . 1.392(3) ?
C1 C6 . 1.406(3) ?
C1 C7 . 1.476(3) ?
C2 C3 . 1.382(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.385(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.386(3) ?
C5 C6 . 1.392(4) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 C8 . 1.314(4) ?
C7 H7 . 0.95 ?
C8 H8 . 0.95 ?
O5 N3 . 1.223(3) ?
O6 N3 . 1.233(3) ?
O7 N4 . 1.227(3) ?
O8 N4 . 1.229(3) ?
N3 C16 . 1.455(3) ?
N4 C12 . 1.477(3) ?
C9 C10 . 1.399(3) ?
C9 C14 . 1.402(3) ?
C9 C15 . 1.470(3) ?
C10 C11 . 1.385(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.383(3) ?
C11 H11 . 0.95 ?
C12 C13 . 1.379(3) ?
C13 C14 . 1.391(3) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
C15 C16 . 1.327(3) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
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
C2 H2 O5 4_455 0.95 2.57 3.389(3) 144
C5 H5 O6 2_665 0.95 2.43 3.234(3) 143
C6 H6 O7 3_535 0.95 2.56 3.469(3) 160
C7 H7 O5 4_455 0.95 2.45 3.304(3) 150
C10 H10 O4 2_674 0.95 2.41 3.352(3) 174
C11 H11 O1 3_564 0.95 2.44 3.243(3) 142
C14 H14 O2 4 0.95 2.57 3.381(3) 144
C15 H15 O2 4 0.95 2.44 3.296(3) 150
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 . . . . 0.0(4) ?
C7 C1 C2 C3 . . . . -179.2(2) ?
C1 C2 C3 C4 . . . . 0.2(4) ?
C2 C3 C4 C5 . . . . -0.4(4) ?
C2 C3 C4 N2 . . . . -179.1(2) ?
O3 N2 C4 C3 . . . . 0.4(3) ?
O4 N2 C4 C3 . . . . -180.0(2) ?
O3 N2 C4 C5 . . . . -178.4(2) ?
O4 N2 C4 C5 . . . . 1.2(3) ?
C3 C4 C5 C6 . . . . 0.4(4) ?
N2 C4 C5 C6 . . . . 179.2(2) ?
C4 C5 C6 C1 . . . . -0.3(4) ?
C2 C1 C6 C5 . . . . 0.1(4) ?
C7 C1 C6 C5 . . . . 179.3(2) ?
C2 C1 C7 C8 . . . . -178.2(2) ?
C6 C1 C7 C8 . . . . 2.6(4) ?
C1 C7 C8 N1 . . . . -176.1(2) ?
O2 N1 C8 C7 . . . . -5.7(3) ?
O1 N1 C8 C7 . . . . 173.6(2) ?
C14 C9 C10 C11 . . . . -0.8(4) ?
C15 C9 C10 C11 . . . . 178.3(2) ?
C9 C10 C11 C12 . . . . 1.0(4) ?
C10 C11 C12 C13 . . . . -0.4(4) ?
C10 C11 C12 N4 . . . . 178.6(2) ?
O7 N4 C12 C13 . . . . -178.4(2) ?
O8 N4 C12 C13 . . . . 2.2(3) ?
O7 N4 C12 C11 . . . . 2.6(3) ?
O8 N4 C12 C11 . . . . -176.8(2) ?
C11 C12 C13 C14 . . . . -0.5(4) ?
N4 C12 C13 C14 . . . . -179.5(2) ?
C12 C13 C14 C9 . . . . 0.8(3) ?
C10 C9 C14 C13 . . . . -0.2(3) ?
C15 C9 C14 C13 . . . . -179.3(2) ?
C10 C9 C15 C16 . . . . 2.9(4) ?
C14 C9 C15 C16 . . . . -178.0(2) ?
C9 C15 C16 N3 . . . . -176.7(2) ?
O5 N3 C16 C15 . . . . -4.9(3) ?
O6 N3 C16 C15 . . . . 173.9(2) ?
