#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/94/2239481.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_2239481
loop_
_publ_author_name
'Jan, Chin Yee'
'Shamsudin, Norzianah Binti Haji'
'Tan, Ai Ling'
'Young, David J.'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 4-Nitrophthalonitrile
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o323
_journal_paper_doi               10.1107/S1600536814003468
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C8 H3 N3 O2'
_chemical_formula_moiety         'C8 H3 N3 O2'
_chemical_formula_sum            'C8 H3 N3 O2'
_chemical_formula_weight         173.13
_chemical_name_common
;
4-Nitrophthalonitrile
;
_chemical_name_systematic
;
4-Nitrobenzene-1,2-dicarbonitrile
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   12.8642(3)
_cell_length_b                   9.2013(2)
_cell_length_c                   13.2578(3)
_cell_measurement_reflns_used    4240
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1427
_cell_measurement_theta_min      3.3308
_cell_volume                     1569.29(6)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0101
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7104
_diffrn_reflns_theta_full        76.34
_diffrn_reflns_theta_max         76.34
_diffrn_reflns_theta_min         6.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.942
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0298
_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)+(0.0522P)²+0.3777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0878
_reflns_number_gt                1556
_reflns_number_total             1638
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wm5005sup1.cif
_cod_data_source_block           I
_cod_database_code               2239481
_cod_database_fobs_code          2239481
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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_occupancy
_atom_site_symmetry_multiplicity
O O1 0.55783(6) 0.56540(8) 0.23140(6) 0.0224(2) Uani d 1 1
O O2 0.41285(6) 0.62811(9) 0.16017(6) 0.0284(2) Uani d 1 1
N N1 0.46305(7) 0.56035(9) 0.22296(6) 0.0185(2) Uani d 1 1
N N2 0.49465(7) 0.20831(10) 0.59515(7) 0.0245(2) Uani d 1 1
N N3 0.20184(7) 0.10850(10) 0.54001(7) 0.0214(2) Uani d 1 1
C C1 0.40488(7) 0.46610(10) 0.29308(7) 0.0159(2) Uani d 1 1
C C2 0.30038(8) 0.44112(11) 0.27448(7) 0.0185(2) Uani d 1 1
C C3 0.24639(7) 0.34933(11) 0.33907(7) 0.0183(2) Uani d 1 1
C C4 0.29752(7) 0.28688(10) 0.42094(7) 0.0158(2) Uani d 1 1
C C5 0.40307(7) 0.31687(10) 0.43884(7) 0.0152(2) Uani d 1 1
C C6 0.45807(7) 0.40675(10) 0.37365(7) 0.0156(2) Uani d 1 1
C C7 0.45469(7) 0.25464(10) 0.52497(7) 0.0176(2) Uani d 1 1
C C8 0.24319(7) 0.18890(10) 0.48760(7) 0.0173(2) Uani d 1 1
H H2 0.2670(11) 0.4827(16) 0.2163(10) 0.027(3) Uiso d 1 1
H H3 0.1745(11) 0.3317(13) 0.3282(9) 0.020(3) Uiso d 1 1
H H6 0.5294(10) 0.4254(13) 0.3839(9) 0.017(3) Uiso d 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0156(4) 0.0246(4) 0.0271(4) -0.0022(3) 0.0032(3) 0.0031(3)
O2 0.0248(4) 0.0300(4) 0.0304(4) -0.0019(3) -0.0029(3) 0.0151(3)
N1 0.0177(4) 0.0174(4) 0.0204(4) -0.0004(3) 0.0013(3) 0.0015(3)
N2 0.0198(4) 0.0303(5) 0.0235(5) 0.0001(3) -0.0016(3) 0.0064(4)
N3 0.0183(4) 0.0241(4) 0.0217(4) -0.0026(3) 0.0008(3) 0.0014(3)
C1 0.0166(5) 0.0145(4) 0.0167(5) 0.0002(3) 0.0030(3) -0.0003(3)
C2 0.0176(5) 0.0204(5) 0.0174(5) 0.0014(3) -0.0017(3) 0.0002(4)
C3 0.0132(5) 0.0219(5) 0.0199(5) -0.0009(3) -0.0010(3) -0.0005(4)
C4 0.0155(4) 0.0152(4) 0.0166(4) -0.0002(3) 0.0021(3) -0.0022(3)
C5 0.0152(4) 0.0144(4) 0.0159(4) 0.0021(3) -0.0001(3) -0.0020(3)
C6 0.0125(4) 0.0153(4) 0.0190(5) 0.0005(3) 0.0006(3) -0.0021(4)
C7 0.0135(4) 0.0185(5) 0.0208(5) -0.0015(3) 0.0019(3) 0.0000(4)
C8 0.0139(4) 0.0196(5) 0.0184(4) 0.0002(3) -0.0014(3) -0.0023(4)
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
O2 N1 O1 124.59(8)
O2 N1 C1 117.40(8)
O1 N1 C1 118.01(8)
C6 C1 C2 123.54(9)
C6 C1 N1 117.94(8)
C2 C1 N1 118.52(9)
C1 C2 C3 118.44(9)
C1 C2 H2 120.7(8)
C3 C2 H2 120.8(8)
C2 C3 C4 119.67(9)
C2 C3 H3 119.8(8)
C4 C3 H3 120.5(8)
C3 C4 C5 120.44(9)
C3 C4 C8 120.41(8)
C5 C4 C8 119.15(8)
C6 C5 C4 120.23(9)
C6 C5 C7 119.68(8)
C4 C5 C7 120.09(8)
C1 C6 C5 117.66(9)
C1 C6 H6 121.4(8)
C5 C6 H6 120.9(8)
N2 C7 C5 178.04(11)
N3 C8 C4 178.30(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2252(12)
O2 N1 1.2243(11)
N1 C1 1.4752(12)
N2 C7 1.1453(13)
N3 C8 1.1459(13)
C1 C6 1.3811(14)
C1 C2 1.3859(14)
C2 C3 1.3889(14)
C2 H2 0.962(14)
C3 C4 1.3932(13)
C3 H3 0.949(13)
C4 C5 1.4057(13)
C4 C8 1.4431(13)
C5 C6 1.3898(13)
C5 C7 1.4397(13)
C6 H6 0.943(13)
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 N3 7_565 0.962(14) 2.621(14) 3.3880(13) 136.9(11)
C3 H3 N2 4_456 0.950(14) 2.554(14) 3.3955(13) 147.8(10)
C6 H6 N3 4_556 0.943(13) 2.457(13) 3.3412(13) 156.1(10)
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
O2 N1 C1 C6 -170.25(9)
O1 N1 C1 C6 9.80(13)
O2 N1 C1 C2 10.12(13)
O1 N1 C1 C2 -169.82(9)
C6 C1 C2 C3 -1.26(15)
N1 C1 C2 C3 178.34(8)
C1 C2 C3 C4 0.91(15)
C2 C3 C4 C5 0.38(14)
C2 C3 C4 C8 -178.71(9)
C3 C4 C5 C6 -1.41(14)
C8 C4 C5 C6 177.69(8)
C3 C4 C5 C7 178.52(9)
C8 C4 C5 C7 -2.37(13)
C2 C1 C6 C5 0.25(14)
N1 C1 C6 C5 -179.36(8)
C4 C5 C6 C1 1.09(14)
C7 C5 C6 C1 -178.85(8)
C6 C5 C7 N2 96(3)
C4 C5 C7 N2 -84(3)
C3 C4 C8 N3 122(3)
C5 C4 C8 N3 -57(4)
