#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/24/2232440.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_2232440
loop_
_publ_author_name
'Stilinović, Vladimir'
'Portada, Tomislav'
_publ_section_title
;
 N-Benzyl-3-nitroaniline
;
_journal_coeditor_code           RK2302
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3013
_journal_paper_doi               10.1107/S1600536811042632
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H12 N2 O2'
_chemical_formula_moiety         'C13 H12 N2 O2'
_chemical_formula_sum            'C13 H12 N2 O2'
_chemical_formula_weight         228.25
_chemical_name_systematic
;
N-benzyl-3-nitroaniline
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 97.334(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.3359(2)
_cell_length_b                   19.2285(6)
_cell_length_c                   5.6017(2)
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      54.0
_cell_measurement_theta_min      4.6
_cell_volume                     570.04(3)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection
'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997), POV-Ray (Cason et al.,
2002) and
Mercury (Macrae et al., 2006)
;
_computing_publication_material
;
WinGX (Farrugia, 1999), PLATON (Spek, 2009) and
PARST
(Nardelli, 1995)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method       'φ and 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  0.0173
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7072
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         3.82
_diffrn_standards_number         27
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.231
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1280
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0615P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0808
_reflns_number_gt                1093
_reflns_number_total             1280
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2302.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2232440
_cod_database_fobs_code          2232440
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
H H1 0.844(5) 0.2074(13) 0.076(5) 0.063(6) Uiso d . 1
C C3 0.2527(3) 0.28407(9) 0.4595(3) 0.0412(4) Uani d . 1
C C2 0.4146(3) 0.23191(9) 0.4090(3) 0.0423(4) Uani d . 1
H H2 0.4181 0.1896 0.4896 0.051 Uiso calc R 1
C C1 0.5737(3) 0.24414(9) 0.2335(3) 0.0454(4) Uani d . 1
N N2 0.0876(3) 0.27154(8) 0.6441(3) 0.0489(4) Uani d . 1
C C6 0.5584(3) 0.30889(10) 0.1187(4) 0.0516(4) Uani d . 1
H H6 0.6626 0.318 0.0013 0.062 Uiso calc R 1
C C4 0.2364(4) 0.34794(9) 0.3472(4) 0.0528(5) Uani d . 1
H H4 0.1244 0.382 0.3858 0.063 Uiso calc R 1
N N1 0.7446(4) 0.19560(9) 0.1759(4) 0.0663(5) Uani d . 1
O O2 -0.0522(3) 0.31801(9) 0.6928(3) 0.0763(5) Uani d . 1
O O1 0.0942(3) 0.21462(8) 0.7433(3) 0.0645(4) Uani d . 1
C C5 0.3954(4) 0.35886(10) 0.1740(4) 0.0579(5) Uani d . 1
H H5 0.3905 0.4013 0.0939 0.069 Uiso calc R 1
C C8 0.5655(3) 0.07735(9) 0.2164(3) 0.0496(4) Uani d D 1
C C7 0.7768(4) 0.12849(11) 0.2881(5) 0.0616(5) Uani d . 1
H H7A 0.7937 0.1347 0.4612 0.074 Uiso calc R 1
H H7B 0.9335 0.1085 0.2492 0.074 Uiso calc R 1
C C11 0.1852(4) -0.01992(12) 0.0930(5) 0.0705(6) Uani d U 1
H H11 0.0576 -0.0523 0.0518 0.085 Uiso calc R 1
C C13 0.4114(4) 0.08153(12) -0.0021(3) 0.0666(6) Uani d D 1
H H13 0.4348 0.1172 -0.1093 0.08 Uiso calc R 1
C C10 0.3354(5) -0.02457(12) 0.3060(5) 0.0739(6) Uani d . 1
H H10 0.3118 -0.0606 0.4115 0.089 Uiso calc R 1
C C9 0.5222(4) 0.02354(12) 0.3673(4) 0.0651(5) Uani d . 1
H H9 0.6224 0.0197 0.5152 0.078 Uiso calc R 1
C C12 0.2233(5) 0.03297(16) -0.0607(4) 0.0764(6) Uani d U 1
H H12 0.1207 0.0363 -0.2075 0.092 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
C2 C3 C4 124.08(15)
C2 C3 N2 118.44(14)
C4 C3 N2 117.48(15)
C3 C2 C1 118.37(15)
C3 C2 H2 120.8
C1 C2 H2 120.8
N1 C1 C2 122.14(17)
N1 C1 C6 119.94(16)
C2 C1 C6 117.90(16)
O2 N2 O1 122.47(15)
O2 N2 C3 118.66(16)
O1 N2 C3 118.87(14)
C5 C6 C1 121.74(16)
C5 C6 H6 119.1
C1 C6 H6 119.1
C3 C4 C5 116.54(16)
C3 C4 H4 121.7
C5 C4 H4 121.7
C1 N1 C7 123.70(18)
C1 N1 H1 117.6(17)
C7 N1 H1 118.6(17)
C6 C5 C4 121.36(17)
C6 C5 H5 119.3
C4 C5 H5 119.3
C9 C8 C13 117.32(18)
C9 C8 C7 120.31(17)
C13 C8 C7 122.36(19)
N1 C7 C8 115.13(19)
N1 C7 H7A 108.5
C8 C7 H7A 108.5
N1 C7 H7B 108.5
C8 C7 H7B 108.5
H7A C7 H7B 107.5
C10 C11 C12 119.1(2)
C10 C11 H11 120.4
C12 C11 H11 120.4
C12 C13 C8 120.2(2)
C12 C13 H13 119.9
C8 C13 H13 119.9
C11 C10 C9 120.4(2)
C11 C10 H10 119.8
C9 C10 H10 119.8
C10 C9 C8 121.9(2)
C10 C9 H9 119.1
C8 C9 H9 119.1
C11 C12 C13 121.1(2)
C11 C12 H12 119.4
C13 C12 H12 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C3 C2 1.376(2)
C3 C4 1.378(2)
C3 N2 1.461(2)
C2 C1 1.398(2)
C2 H2 0.93
C1 N1 1.372(2)
C1 C6 1.399(3)
N2 O2 1.217(2)
N2 O1 1.226(2)
C6 C5 1.358(3)
C6 H6 0.93
C4 C5 1.384(3)
C4 H4 0.93
N1 C7 1.436(3)
N1 H1 0.85(3)
C5 H5 0.93
C8 C9 1.374(3)
C8 C13 1.3868(17)
C8 C7 1.511(3)
C7 H7A 0.97
C7 H7B 0.97
C11 C10 1.353(4)
C11 C12 1.364(4)
C11 H11 0.93
C13 C12 1.379(4)
C13 H13 0.93
C10 C9 1.371(3)
C10 H10 0.93
C9 H9 0.93
C12 H12 0.93
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
N1 H1 O1 1_654 0.84(2) 2.44(2) 3.263(2) 166(2)
C6 H6 O2 1_654 0.93 2.446 3.364(2) 169
C13 H13 O1 1_554 0.93 2.670 3.293(2) 125
C7 H7A O1 1_655 0.97 2.605 3.318(2) 130
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 594377
