#------------------------------------------------------------------------------
#$Date: 2015-09-26 05:42:51 +0300 (Sat, 26 Sep 2015) $
#$Revision: 158402 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/11/2241155.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_2241155
loop_
_publ_author_name
'Saphu, Watcharin'
'Chainok, Kittipong'
_publ_section_title
;
 Crystal structure of 4-nitro-N-[(pyridin-2-yl)methylidene]aniline
;
_journal_coeditor_code           TK5383
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o760
_journal_paper_doi               10.1107/S2056989015016928
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C12 H9 N3 O2'
_chemical_formula_moiety         'C12 H9 N3 O2'
_chemical_formula_sum            'C12 H9 N3 O2'
_chemical_formula_weight         227.22
_chemical_name_systematic
;
4-Nitro-N-[(pyridin-2-yl)methylidene]aniline
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.57(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8573(8)
_cell_length_b                   20.334(4)
_cell_length_c                   13.629(3)
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.000
_cell_measurement_theta_min      3.357
_cell_volume                     1068.9(4)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010) and enCIFer (Allen et al.,  2004)
;
_computing_structure_refinement
;
SHELXL2015 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4963
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.766
_diffrn_reflns_theta_min         3.357
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.1347
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0721P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1455
_reflns_number_gt                1389
_reflns_number_total             2729
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5383sup1.cif
_cod_data_source_block           I
_cod_database_code               2241155
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_occupancy
O O1 1.1083(5) 0.13951(9) 0.12132(11) 0.0956(6) Uani d 1
O O2 0.8270(5) 0.22866(8) 0.14401(10) 0.0803(5) Uani d 1
N N1 0.7398(4) 0.15745(8) 0.80644(11) 0.0590(5) Uani d 1
N N2 0.7157(4) 0.09779(7) 0.56225(11) 0.0514(4) Uani d 1
N N3 0.9470(5) 0.17696(9) 0.17367(11) 0.0593(5) Uani d 1
C C1 0.6529(6) 0.14026(10) 0.89705(15) 0.0665(6) Uani d 1
H H1 0.7013 0.1697 0.9476 0.080 Uiso calc 1
C C2 0.4961(6) 0.08178(10) 0.92062(15) 0.0649(6) Uani d 1
H H2 0.4409 0.0721 0.9853 0.078 Uiso calc 1
C C3 0.4229(5) 0.03823(10) 0.84726(14) 0.0608(5) Uani d 1
H H3 0.3171 -0.0018 0.8611 0.073 Uiso calc 1
C C4 0.5083(5) 0.05437(9) 0.75229(13) 0.0515(5) Uani d 1
H H4 0.4605 0.0256 0.7008 0.062 Uiso calc 1
C C5 0.6660(5) 0.11411(8) 0.73519(12) 0.0460(4) Uani d 1
C C6 0.7641(5) 0.13469(8) 0.63552(13) 0.0488(5) Uani d 1
H H6 0.8641 0.1758 0.6265 0.059 Uiso calc 1
C C7 0.7881(5) 0.12104(8) 0.46689(12) 0.0453(4) Uani d 1
C C8 0.9466(5) 0.07832(8) 0.40174(13) 0.0508(5) Uani d 1
H H8 1.0149 0.0367 0.4228 0.061 Uiso calc 1
C C9 1.0034(5) 0.09701(9) 0.30649(13) 0.0506(5) Uani d 1
H H9 1.1141 0.0688 0.2632 0.061 Uiso calc 1
C C10 0.8940(5) 0.15815(8) 0.27591(12) 0.0459(5) Uani d 1
C C11 0.7340(5) 0.20177(8) 0.33848(13) 0.0489(5) Uani d 1
H H11 0.6609 0.2428 0.3163 0.059 Uiso calc 1
C C12 0.6854(5) 0.18309(8) 0.43442(13) 0.0494(5) Uani d 1
H H12 0.5828 0.2122 0.4780 0.059 Uiso calc 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 C5 116.52(17)
C6 N2 C7 119.98(15)
O1 N3 C10 118.14(17)
O2 N3 O1 122.71(16)
O2 N3 C10 119.14(17)
N1 C1 H1 118.0
N1 C1 C2 124.10(19)
C2 C1 H1 118.0
C1 C2 H2 120.7
C3 C2 C1 118.63(19)
C3 C2 H2 120.7
C2 C3 H3 120.5
C2 C3 C4 118.98(19)
C4 C3 H3 120.5
C3 C4 H4 120.7
C3 C4 C5 118.57(17)
C5 C4 H4 120.7
N1 C5 C4 123.20(17)
N1 C5 C6 115.24(16)
C4 C5 C6 121.55(16)
N2 C6 C5 121.55(16)
N2 C6 H6 119.2
C5 C6 H6 119.2
C8 C7 N2 118.10(15)
C8 C7 C12 119.28(16)
C12 C7 N2 122.47(16)
C7 C8 H8 119.8
C9 C8 C7 120.47(16)
C9 C8 H8 119.8
C8 C9 H9 120.5
C8 C9 C10 119.04(16)
C10 C9 H9 120.5
C9 C10 N3 118.69(16)
C9 C10 C11 122.07(16)
C11 C10 N3 119.24(16)
C10 C11 H11 120.8
C12 C11 C10 118.40(15)
C12 C11 H11 120.8
C7 C12 H12 119.6
C11 C12 C7 120.71(16)
C11 C12 H12 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N3 1.219(2)
O2 N3 1.216(2)
N1 C1 1.330(3)
N1 C5 1.340(2)
N2 C6 1.262(2)
N2 C7 1.413(2)
N3 C10 1.461(2)
C1 H1 0.9300
C1 C2 1.374(3)
C2 H2 0.9300
C2 C3 1.363(3)
C3 H3 0.9300
C3 C4 1.378(3)
C4 H4 0.9300
C4 C5 1.380(3)
C5 C6 1.474(3)
C6 H6 0.9300
C7 C8 1.388(2)
C7 C12 1.393(2)
C8 H8 0.9300
C8 C9 1.372(3)
C9 H9 0.9300
C9 C10 1.376(2)
C10 C11 1.380(2)
C11 H11 0.9300
C11 C12 1.376(3)
C12 H12 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
C1 H1 O1 1_556 0.93 2.89 3.510(3) 125
C2 H2 O1 1_456 0.93 2.65 3.343(3) 132
C6 H6 O2 4_666 0.93 2.65 3.527(2) 158
C11 H11 N1 4_565 0.93 2.60 3.465(2) 155
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
O1 N3 C10 C9 -5.2(3)
O1 N3 C10 C11 175.38(18)
O2 N3 C10 C9 174.23(18)
O2 N3 C10 C11 -5.2(3)
N1 C1 C2 C3 -0.1(3)
N1 C5 C6 N2 178.44(17)
N2 C7 C8 C9 175.98(17)
N2 C7 C12 C11 -174.32(16)
N3 C10 C11 C12 179.77(15)
C1 N1 C5 C4 0.0(3)
C1 N1 C5 C6 179.76(17)
C1 C2 C3 C4 -0.1(3)
C2 C3 C4 C5 0.2(3)
C3 C4 C5 N1 -0.2(3)
C3 C4 C5 C6 -179.92(17)
C4 C5 C6 N2 -1.8(3)
C5 N1 C1 C2 0.1(3)
C6 N2 C7 C8 139.41(19)
C6 N2 C7 C12 -45.1(3)
C7 N2 C6 C5 175.13(15)
C7 C8 C9 C10 -1.4(3)
C8 C7 C12 C11 1.1(3)
C8 C9 C10 N3 -178.34(16)
C8 C9 C10 C11 1.1(3)
C9 C10 C11 C12 0.3(3)
C10 C11 C12 C7 -1.5(3)
C12 C7 C8 C9 0.3(3)

_cod_database_fobs_code 2241155
