#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/03/2220394.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_2220394
loop_
_publ_author_name
'Zaheer, Muhammad'
'Akhter, Zareen'
'Bolte, Michael'
'Siddiqi, Humaira M.'
_publ_section_title
;
 N-(3-Nitrobenzylidene)aniline
;
_journal_coeditor_code           ZL2143
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2381
_journal_page_last               o2382
_journal_paper_doi               10.1107/S1600536808036970
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H10 N2 O2'
_chemical_formula_moiety         'C13 H10 N2 O2'
_chemical_formula_sum            'C13 H10 N2 O2'
_chemical_formula_weight         226.23
_chemical_name_systematic
;
N-(3-Nitrobenzylidene)aniline
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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            4
_cell_length_a                   7.3177(6)
_cell_length_b                   12.1022(11)
_cell_length_c                   12.4672(12)
_cell_measurement_reflns_used    7899
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      3.7
_cell_volume                     1104.10(17)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_device_type  'Stoe IPDSII two-circle'
_diffrn_measurement_method       ω
_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  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9868
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.51
_diffrn_reflns_theta_min         3.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.46
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0343
_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)+(0.0638P)²+0.081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0931
_reflns_number_gt                1421
_reflns_number_total             1585
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2143.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               2220394
_cod_database_fobs_code          2220394
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
N N1 0.85150(17) 0.74236(10) 0.59232(10) 0.0265(3) Uani d . 1
N N2 0.9518(2) 0.83182(11) 0.11436(10) 0.0339(3) Uani d . 1
O O1 0.9459(2) 0.90457(11) 0.04548(10) 0.0507(4) Uani d . 1
O O2 0.9936(2) 0.73588(10) 0.09536(9) 0.0525(4) Uani d . 1
C C1 0.9027(2) 0.72475(11) 0.49536(12) 0.0255(3) Uani d . 1
H H1 0.9530 0.6549 0.4771 0.031 Uiso calc R 1
C C2 0.8855(2) 0.81012(11) 0.41137(12) 0.0239(3) Uani d . 1
C C3 0.9276(2) 0.78262(11) 0.30530(11) 0.0243(3) Uani d . 1
H H3 0.9685 0.7104 0.2876 0.029 Uiso calc R 1
C C4 0.9088(2) 0.86252(12) 0.22632(11) 0.0262(3) Uani d . 1
C C5 0.8499(2) 0.96943(12) 0.24807(12) 0.0296(3) Uani d . 1
H H5 0.8383 1.0225 0.1924 0.036 Uiso calc R 1
C C6 0.8086(2) 0.99625(12) 0.35358(13) 0.0314(4) Uani d . 1
H H6 0.7678 1.0687 0.3705 0.038 Uiso calc R 1
C C7 0.8262(2) 0.91791(12) 0.43499(12) 0.0277(3) Uani d . 1
H H7 0.7979 0.9375 0.5069 0.033 Uiso calc R 1
C C11 0.86161(19) 0.65339(11) 0.66706(11) 0.0239(3) Uani d . 1
C C12 0.9017(2) 0.67860(12) 0.77429(12) 0.0291(3) Uani d . 1
H H12 0.9229 0.7531 0.7947 0.035 Uiso calc R 1
C C13 0.9105(2) 0.59535(14) 0.85102(12) 0.0337(4) Uani d . 1
H H13 0.9399 0.6130 0.9232 0.040 Uiso calc R 1
C C14 0.8763(2) 0.48619(13) 0.82226(13) 0.0332(4) Uani d . 1
H H14 0.8832 0.4292 0.8745 0.040 Uiso calc R 1
C C15 0.8317(2) 0.46086(12) 0.71627(13) 0.0308(3) Uani d . 1
H H15 0.8062 0.3866 0.6968 0.037 Uiso calc R 1
C C16 0.8244(2) 0.54339(12) 0.63890(12) 0.0261(3) Uani d . 1
H H16 0.7942 0.5253 0.5669 0.031 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
C1 N1 C11 118.36(12)
O2 N2 O1 123.54(14)
O2 N2 C4 118.32(12)
O1 N2 C4 118.14(13)
N1 C1 C2 121.80(13)
N1 C1 H1 119.1
C2 C1 H1 119.1
C3 C2 C7 119.15(12)
C3 C2 C1 119.04(12)
C7 C2 C1 121.81(13)
C4 C3 C2 118.92(13)
C4 C3 H3 120.5
C2 C3 H3 120.5
C3 C4 C5 122.76(14)
C3 C4 N2 118.30(13)
C5 C4 N2 118.94(12)
C6 C5 C4 118.03(13)
C6 C5 H5 121.0
C4 C5 H5 121.0
C5 C6 C7 120.69(14)
C5 C6 H6 119.7
C7 C6 H6 119.7
C6 C7 C2 120.45(14)
C6 C7 H7 119.8
C2 C7 H7 119.8
C12 C11 C16 119.04(13)
C12 C11 N1 118.00(12)
C16 C11 N1 122.88(13)
C13 C12 C11 120.52(14)
C13 C12 H12 119.7
C11 C12 H12 119.7
C12 C13 C14 120.15(14)
C12 C13 H13 119.9
C14 C13 H13 119.9
C13 C14 C15 119.65(14)
C13 C14 H14 120.2
C15 C14 H14 120.2
C16 C15 C14 120.57(14)
C16 C15 H15 119.7
C14 C15 H15 119.7
C15 C16 C11 120.04(13)
C15 C16 H16 120.0
C11 C16 H16 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.283(2)
N1 C11 1.4258(18)
N2 O2 1.2237(18)
N2 O1 1.2306(17)
N2 C4 1.4783(19)
C1 C2 1.476(2)
C1 H1 0.9500
C2 C3 1.398(2)
C2 C7 1.4060(19)
C3 C4 1.3869(19)
C3 H3 0.9500
C4 C5 1.390(2)
C5 C6 1.388(2)
C5 H5 0.9500
C6 C7 1.395(2)
C6 H6 0.9500
C7 H7 0.9500
C11 C12 1.402(2)
C11 C16 1.4034(19)
C12 C13 1.391(2)
C12 H12 0.9500
C13 C14 1.391(2)
C13 H13 0.9500
C14 C15 1.395(2)
C14 H14 0.9500
C15 C16 1.390(2)
C15 H15 0.9500
C16 H16 0.9500
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
C6 H6 O1 2_675 0.95 2.70 3.261(2) 118.1
C6 H6 O2 4_755 0.95 2.71 3.303(2) 121.5
C7 H7 O1 2_675 0.95 2.66 3.237(2) 119.8
C13 H13 O2 1_556 0.95 2.64 3.541(2) 158.6
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
C11 N1 C1 C2 175.97(13)
N1 C1 C2 C3 -174.08(15)
N1 C1 C2 C7 5.3(2)
C7 C2 C3 C4 -0.3(2)
C1 C2 C3 C4 179.08(12)
C2 C3 C4 C5 0.1(2)
C2 C3 C4 N2 -179.28(15)
O2 N2 C4 C3 3.5(2)
O1 N2 C4 C3 -175.59(15)
O2 N2 C4 C5 -175.94(16)
O1 N2 C4 C5 5.0(2)
C3 C4 C5 C6 0.0(2)
N2 C4 C5 C6 179.38(14)
C4 C5 C6 C7 0.1(2)
C5 C6 C7 C2 -0.3(2)
C3 C2 C7 C6 0.4(2)
C1 C2 C7 C6 -179.00(14)
C1 N1 C11 C12 146.81(14)
C1 N1 C11 C16 -36.5(2)
C16 C11 C12 C13 2.1(2)
N1 C11 C12 C13 179.00(13)
C11 C12 C13 C14 -1.1(2)
C12 C13 C14 C15 -0.5(2)
C13 C14 C15 C16 1.1(2)
C14 C15 C16 C11 -0.1(2)
C12 C11 C16 C15 -1.5(2)
N1 C11 C16 C15 -178.20(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 256764
