##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 1004278'
_chemical_name_systematic
;
N-(4-methylphenyl)-3-nitropyridin-2-amine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H11 N3 O2'
_chemical_formula_sum     'C12 H11 N3 O2'
_chemical_formula_iupac     'C12 H11 N3 O2'
_chemical_formula_weight     229.24
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     11.4079(6)
_cell_length_b     13.1968(8)
_cell_length_c     14.3681(7)
_cell_angle_alpha     90.00
_cell_angle_beta     96.387(5)
_cell_angle_gamma     90.00
_cell_volume     2149.7(2)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4609
_cell_measurement_theta_min     3.0923
_cell_measurement_theta_max     76.3710
_cell_measurement_temperature     100(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.417
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     960
_exptl_absorpt_coefficient_mu     0.824
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Agilent, 2013)'
_exptl_absorpt_correction_T_min     0.20565
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_source     'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator     Mirror
_diffrn_measurement_device_type
                  'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     10.4041
_diffrn_reflns_number     24994
_diffrn_reflns_av_R_equivalents     0.0641
_diffrn_reflns_av_sigmaI/netI     0.0404
_diffrn_reflns_theta_min     3.09
_diffrn_reflns_theta_max     74.96
_diffrn_reflns_theta_full     74.96
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4623
_reflns_number_gt     3633
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0614
_refine_ls_R_factor_gt     0.0426
_refine_ls_wR_factor_gt     0.1080
_refine_ls_wR_factor_ref     0.1236
_refine_ls_goodness_of_fit_ref     1.010
_refine_ls_restrained_S_all     1.009
_refine_ls_number_reflns     4623
_refine_ls_number_parameters     629
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0775P)²+0.0456P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.274
_refine_diff_density_min     -0.268
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
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'
_computing_data_collection     'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement     'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction     'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway,
2001)
and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material     'publCIF (Westrip, 2010)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.1693(2) 0.4996(2) 1.11071(17) 0.0305(6) Uani d . 1 1 . .
    O O2 0.3584(2) 0.4890(2) 1.14982(19) 0.0406(7) Uani d . 1 1 . .
    N N1 0.0806(3) 0.4751(3) 0.9351(2) 0.0244(7) Uani d D 1 1 . .
    H H1N 0.069(3) 0.486(3) 0.9939(11) 0.029 Uiso d D 1 1 . .
    N N2 0.2143(3) 0.4208(3) 0.8357(2) 0.0260(7) Uani d . 1 1 . .
    N N3 0.2712(3) 0.4837(2) 1.0903(2) 0.0278(6) Uani d . 1 1 . .
    C C1 0.1923(3) 0.4515(3) 0.9220(2) 0.0218(7) Uani d . 1 1 . .
    C C2 0.3235(3) 0.3972(3) 0.8216(3) 0.0305(8) Uani d . 1 1 . .
    H H2 0.3364 0.3756 0.7605 0.037 Uiso calc R 1 1 . .
    C C3 0.4211(3) 0.4013(3) 0.8889(3) 0.0321(8) Uani d . 1 1 . .
    H H3 0.4977 0.3834 0.8743 0.039 Uiso calc R 1 1 . .
    C C4 0.4021(3) 0.4322(3) 0.9773(3) 0.0281(8) Uani d . 1 1 . .
    H H4 0.4660 0.4365 1.0256 0.034 Uiso calc R 1 1 . .
    C C5 0.2883(3) 0.4573(3) 0.9954(2) 0.0244(7) Uani d . 1 1 . .
    C C6 -0.0239(3) 0.4736(3) 0.8718(2) 0.0214(7) Uani d . 1 1 . .
    C C7 -0.1293(3) 0.4664(3) 0.9128(2) 0.0250(7) Uani d . 1 1 . .
    H H7 -0.1271 0.4602 0.9789 0.030 Uiso calc R 1 1 . .
    C C8 -0.2366(3) 0.4684(3) 0.8576(2) 0.0245(7) Uani d . 1 1 . .
    H H8 -0.3074 0.4633 0.8864 0.029 Uiso calc R 1 1 . .
    C C9 -0.2432(3) 0.4777(3) 0.7603(3) 0.0242(7) Uani d . 1 1 . .
    C C10 -0.1377(3) 0.4853(3) 0.7207(2) 0.0243(7) Uani d . 1 1 . .
    H H10 -0.1401 0.4916 0.6547 0.029 Uiso calc R 1 1 . .
    C C11 -0.0288(3) 0.4837(3) 0.7750(2) 0.0236(7) Uani d . 1 1 . .
    H H11 0.0419 0.4896 0.7461 0.028 Uiso calc R 1 1 . .
    C C12 -0.3607(3) 0.4781(3) 0.7003(2) 0.0282(7) Uani d . 1 1 . .
    H H12A -0.3549 0.5194 0.6444 0.042 Uiso calc R 1 1 . .
    H H12B -0.4211 0.5066 0.7362 0.042 Uiso calc R 1 1 . .
    H H12C -0.3823 0.4086 0.6816 0.042 Uiso calc R 1 1 . .
    O O3 0.5598(2) 0.6453(2) 1.07113(18) 0.0350(6) Uani d . 1 1 . .
    O O4 0.7456(3) 0.6690(2) 1.1166(2) 0.0416(7) Uani d . 1 1 . .
    N N4 0.4768(3) 0.6770(2) 0.8954(2) 0.0246(6) Uani d D 1 1 . .
    H H4N 0.465(4) 0.666(3) 0.9539(12) 0.030 Uiso d D 1 1 . .
    N N5 0.6142(3) 0.7310(3) 0.7993(2) 0.0301(7) Uani d . 1 1 . .
    N N6 0.6613(3) 0.6682(2) 1.0544(2) 0.0303(7) Uani d . 1 1 . .
    C C13 0.5895(3) 0.7002(3) 0.8844(3) 0.0252(8) Uani d . 1 1 . .
    C C14 0.7248(3) 0.7557(3) 0.7875(3) 0.0326(8) Uani d . 1 1 . .
    H H14 0.7406 0.7770 0.7270 0.039 Uiso calc R 1 1 . .
    C C15 0.8189(3) 0.7523(3) 0.8582(3) 0.0357(10) Uani d . 1 1 . .
    H H15 0.8962 0.7713 0.8463 0.043 Uiso calc R 1 1 . .
    C C16 0.7964(3) 0.7208(3) 0.9452(3) 0.0327(9) Uani d . 1 1 . .
    H H16 0.8587 0.7161 0.9947 0.039 Uiso calc R 1 1 . .
    C C17 0.6822(3) 0.6959(3) 0.9604(3) 0.0263(8) Uani d . 1 1 . .
    C C18 0.3730(3) 0.6821(3) 0.8309(3) 0.0223(7) Uani d . 1 1 . .
    C C19 0.2680(3) 0.6955(3) 0.8700(2) 0.0229(7) Uani d . 1 1 . .
    H H19 0.2691 0.7027 0.9359 0.027 Uiso calc R 1 1 . .
    C C20 0.1620(3) 0.6984(3) 0.8131(2) 0.0241(7) Uani d . 1 1 . .
    H H20 0.0909 0.7065 0.8409 0.029 Uiso calc R 1 1 . .
    C C21 0.1568(3) 0.6898(3) 0.7160(2) 0.0230(7) Uani d . 1 1 . .
    C C22 0.2628(3) 0.6757(3) 0.6785(2) 0.0237(7) Uani d . 1 1 . .
    H H22 0.2616 0.6689 0.6125 0.028 Uiso calc R 1 1 . .
    C C23 0.3706(3) 0.6712(3) 0.7341(2) 0.0233(7) Uani d . 1 1 . .
    H H23 0.4416 0.6608 0.7065 0.028 Uiso calc R 1 1 . .
    C C24 0.0417(3) 0.6970(3) 0.6543(2) 0.0268(7) Uani d . 1 1 . .
    H H24A 0.0370 0.6424 0.6078 0.040 Uiso calc R 1 1 . .
    H H24B 0.0368 0.7627 0.6223 0.040 Uiso calc R 1 1 . .
    H H24C -0.0238 0.6906 0.6927 0.040 Uiso calc R 1 1 . .
    O O5 0.8659(2) 0.4620(2) 0.14411(17) 0.0357(6) Uani d . 1 1 . .
    O O6 0.6805(2) 0.4394(2) 0.09688(17) 0.0326(6) Uani d . 1 1 . .
    N N7 0.9406(3) 0.4660(2) 0.3234(2) 0.0250(6) Uani d D 1 1 . .
    H H7N 0.953(4) 0.478(3) 0.2651(12) 0.030 Uiso d D 1 1 . .
    N N8 0.7985(2) 0.4312(2) 0.42218(19) 0.0242(6) Uani d . 1 1 . .
    N N9 0.7626(3) 0.4480(2) 0.1605(2) 0.0266(6) Uani d . 1 1 . .
    C C25 0.8268(3) 0.4458(3) 0.3342(2) 0.0217(7) Uani d . 1 1 . .
    C C26 0.6856(3) 0.4129(3) 0.4340(3) 0.0277(7) Uani d . 1 1 . .
    H H26 0.6671 0.4017 0.4960 0.033 Uiso calc R 1 1 . .
    C C27 0.5933(3) 0.4092(3) 0.3618(3) 0.0278(8) Uani d . 1 1 . .
    H H27 0.5143 0.3984 0.3744 0.033 Uiso calc R 1 1 . .
    C C28 0.6209(3) 0.4218(3) 0.2718(3) 0.0263(8) Uani d . 1 1 . .
    H H28 0.5610 0.4184 0.2204 0.032 Uiso calc R 1 1 . .
    C C29 0.7366(3) 0.4392(3) 0.2567(2) 0.0241(7) Uani d . 1 1 . .
    C C30 1.0440(3) 0.4666(3) 0.3872(2) 0.0220(7) Uani d . 1 1 . .
    C C31 1.1492(3) 0.4748(3) 0.3470(2) 0.0232(7) Uani d . 1 1 . .
    H H31 1.1472 0.4801 0.2809 0.028 Uiso calc R 1 1 . .
    C C32 1.2568(3) 0.4754(3) 0.4023(2) 0.0256(7) Uani d . 1 1 . .
    H H32 1.3273 0.4825 0.3734 0.031 Uiso calc R 1 1 . .
    C C33 1.2639(3) 0.4659(3) 0.4994(2) 0.0225(7) Uani d . 1 1 . .
    C C34 1.1585(3) 0.4584(3) 0.5390(2) 0.0250(7) Uani d . 1 1 . .
    H H34 1.1610 0.4528 0.6051 0.030 Uiso calc R 1 1 . .
    C C35 1.0491(3) 0.4589(3) 0.4846(2) 0.0234(7) Uani d . 1 1 . .
    H H35 0.9784 0.4540 0.5136 0.028 Uiso calc R 1 1 . .
    C C36 1.3811(3) 0.4627(3) 0.5588(2) 0.0269(7) Uani d . 1 1 . .
    H H36A 1.3743 0.4966 0.6187 0.040 Uiso calc R 1 1 . .
    H H36B 1.4405 0.4974 0.5261 0.040 Uiso calc R 1 1 . .
    H H36C 1.4048 0.3920 0.5703 0.040 Uiso calc R 1 1 . .
    O O7 0.2612(2) 0.7100(2) 0.10311(17) 0.0298(6) Uani d . 1 1 . .
    O O8 0.0735(2) 0.7151(2) 0.05973(17) 0.0349(6) Uani d . 1 1 . .
    N N10 0.3413(3) 0.7031(2) 0.2823(2) 0.0218(6) Uani d D 1 1 . .
    H H10N 0.358(3) 0.695(3) 0.2239(12) 0.026 Uiso d D 1 1 . .
    N N11 0.2005(3) 0.7369(3) 0.3827(2) 0.0261(7) Uani d . 1 1 . .
    N N12 0.1578(2) 0.7149(2) 0.12156(19) 0.0247(6) Uani d . 1 1 . .
    C C37 0.2271(3) 0.7206(3) 0.2953(2) 0.0229(7) Uani d . 1 1 . .
    C C38 0.0884(3) 0.7487(3) 0.3965(2) 0.0283(8) Uani d . 1 1 . .
    H H38 0.0712 0.7591 0.4590 0.034 Uiso calc R 1 1 . .
    C C39 -0.0058(3) 0.7470(3) 0.3266(3) 0.0300(8) Uani d . 1 1 . .
    H H39 -0.0846 0.7546 0.3411 0.036 Uiso calc R 1 1 . .
    C C40 0.0185(3) 0.7339(3) 0.2358(2) 0.0266(7) Uani d . 1 1 . .
    H H40 -0.0432 0.7328 0.1857 0.032 Uiso calc R 1 1 . .
    C C41 0.1350(3) 0.7223(3) 0.2190(2) 0.0239(7) Uani d . 1 1 . .
    C C42 0.4438(3) 0.6970(3) 0.3468(2) 0.0223(7) Uani d . 1 1 . .
    C C43 0.5494(3) 0.6836(3) 0.3066(2) 0.0243(7) Uani d . 1 1 . .
    H H43 0.5474 0.6785 0.2404 0.029 Uiso calc R 1 1 . .
    C C44 0.6560(3) 0.6777(3) 0.3620(2) 0.0252(7) Uani d . 1 1 . .
    H H44 0.7264 0.6688 0.3334 0.030 Uiso calc R 1 1 . .
    C C45 0.6625(3) 0.6846(3) 0.4598(3) 0.0238(8) Uani d . 1 1 . .
    C C46 0.5573(3) 0.6970(3) 0.4987(2) 0.0239(7) Uani d . 1 1 . .
    H H46 0.5595 0.7013 0.5649 0.029 Uiso calc R 1 1 . .
    C C47 0.4485(3) 0.7033(3) 0.4441(2) 0.0259(7) Uani d . 1 1 . .
    H H47 0.3781 0.7117 0.4729 0.031 Uiso calc R 1 1 . .
    C C48 0.7799(3) 0.6812(3) 0.5197(3) 0.0293(8) Uani d . 1 1 . .
    H H48A 0.7675 0.6639 0.5842 0.044 Uiso calc R 1 1 . .
    H H48B 0.8181 0.7477 0.5188 0.044 Uiso calc R 1 1 . .
    H H48C 0.8303 0.6299 0.4950 0.044 Uiso calc R 1 1 . .
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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 N3 . 1.249(4) ?
    O2 N3 . 1.239(4) ?
    N1 C1 . 1.345(4) ?
    N1 C6 . 1.416(4) ?
    N1 H1N . 0.882(10) ?
    N2 C2 . 1.322(5) ?
    N2 C1 . 1.353(5) ?
    N3 C5 . 1.442(4) ?
    C1 C5 . 1.435(5) ?
    C2 C3 . 1.393(5) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.374(5) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.392(4) ?
    C4 H4 . 0.9500 ?
    C6 C11 . 1.393(5) ?
    C6 C7 . 1.400(5) ?
    C7 C8 . 1.384(5) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.397(5) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.391(5) ?
    C9 C12 . 1.510(4) ?
    C10 C11 . 1.392(5) ?
    C10 H10 . 0.9500 ?
    C11 H11 . 0.9500 ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    O3 N6 . 1.245(4) ?
    O4 N6 . 1.238(4) ?
    N4 C13 . 1.347(5) ?
    N4 C18 . 1.421(4) ?
    N4 H4N . 0.880(10) ?
    N5 C14 . 1.331(5) ?
    N5 C13 . 1.349(5) ?
    N6 C17 . 1.445(5) ?
    C13 C17 . 1.434(5) ?
    C14 C15 . 1.394(6) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.368(6) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.385(5) ?
    C16 H16 . 0.9500 ?
    C18 C19 . 1.390(5) ?
    C18 C23 . 1.396(5) ?
    C19 C20 . 1.383(5) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.395(5) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.390(5) ?
    C21 C24 . 1.503(4) ?
    C22 C23 . 1.391(5) ?
    C22 H22 . 0.9500 ?
    C23 H23 . 0.9500 ?
    C24 H24A . 0.9800 ?
    C24 H24B . 0.9800 ?
    C24 H24C . 0.9800 ?
    O5 N9 . 1.241(4) ?
    O6 N9 . 1.239(4) ?
    N7 C25 . 1.351(4) ?
    N7 C30 . 1.411(4) ?
    N7 H7N . 0.880(10) ?
    N8 C26 . 1.339(4) ?
    N8 C25 . 1.353(4) ?
    N9 C29 . 1.450(4) ?
    C25 C29 . 1.433(5) ?
    C26 C27 . 1.394(5) ?
    C26 H26 . 0.9500 ?
    C27 C28 . 1.375(5) ?
    C27 H27 . 0.9500 ?
    C28 C29 . 1.380(5) ?
    C28 H28 . 0.9500 ?
    C30 C31 . 1.393(4) ?
    C30 C35 . 1.397(5) ?
    C31 C32 . 1.386(5) ?
    C31 H31 . 0.9500 ?
    C32 C33 . 1.393(5) ?
    C32 H32 . 0.9500 ?
    C33 C34 . 1.390(4) ?
    C33 C36 . 1.505(4) ?
    C34 C35 . 1.398(4) ?
    C34 H34 . 0.9500 ?
    C35 H35 . 0.9500 ?
    C36 H36A . 0.9800 ?
    C36 H36B . 0.9800 ?
    C36 H36C . 0.9800 ?
    O7 N12 . 1.240(4) ?
    O8 N12 . 1.234(4) ?
    N10 C37 . 1.356(4) ?
    N10 C42 . 1.412(4) ?
    N10 H10N . 0.888(10) ?
    N11 C38 . 1.325(4) ?
    N11 C37 . 1.343(4) ?
    N12 C41 . 1.455(4) ?
    C37 C41 . 1.432(5) ?
    C38 C39 . 1.387(5) ?
    C38 H38 . 0.9500 ?
    C39 C40 . 1.375(5) ?
    C39 H39 . 0.9500 ?
    C40 C41 . 1.385(5) ?
    C40 H40 . 0.9500 ?
    C42 C47 . 1.395(5) ?
    C42 C43 . 1.405(5) ?
    C43 C44 . 1.380(5) ?
    C43 H43 . 0.9500 ?
    C44 C45 . 1.402(5) ?
    C44 H44 . 0.9500 ?
    C45 C46 . 1.388(5) ?
    C45 C48 . 1.510(4) ?
    C46 C47 . 1.396(5) ?
    C46 H46 . 0.9500 ?
    C47 H47 . 0.9500 ?
    C48 H48A . 0.9800 ?
    C48 H48B . 0.9800 ?
    C48 H48C . 0.9800 ?
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
    C1 N1 C6 . . 130.5(3) ?
    C1 N1 H1N . . 115(3) ?
    C6 N1 H1N . . 114(3) ?
    C2 N2 C1 . . 119.0(3) ?
    O2 N3 O1 . . 121.7(3) ?
    O2 N3 C5 . . 119.0(3) ?
    O1 N3 C5 . . 119.3(3) ?
    N1 C1 N2 . . 118.1(3) ?
    N1 C1 C5 . . 122.8(3) ?
    N2 C1 C5 . . 119.0(3) ?
    N2 C2 C3 . . 125.4(4) ?
    N2 C2 H2 . . 117.3 ?
    C3 C2 H2 . . 117.3 ?
    C4 C3 C2 . . 117.2(3) ?
    C4 C3 H3 . . 121.4 ?
    C2 C3 H3 . . 121.4 ?
    C3 C4 C5 . . 119.3(3) ?
    C3 C4 H4 . . 120.3 ?
    C5 C4 H4 . . 120.3 ?
    C4 C5 C1 . . 120.1(3) ?
    C4 C5 N3 . . 117.4(3) ?
    C1 C5 N3 . . 122.4(3) ?
    C11 C6 C7 . . 119.1(3) ?
    C11 C6 N1 . . 125.2(3) ?
    C7 C6 N1 . . 115.6(3) ?
    C8 C7 C6 . . 120.3(3) ?
    C8 C7 H7 . . 119.9 ?
    C6 C7 H7 . . 119.9 ?
    C7 C8 C9 . . 121.4(3) ?
    C7 C8 H8 . . 119.3 ?
    C9 C8 H8 . . 119.3 ?
    C10 C9 C8 . . 117.6(3) ?
    C10 C9 C12 . . 121.3(3) ?
    C8 C9 C12 . . 121.1(3) ?
    C9 C10 C11 . . 122.0(3) ?
    C9 C10 H10 . . 119.0 ?
    C11 C10 H10 . . 119.0 ?
    C10 C11 C6 . . 119.7(3) ?
    C10 C11 H11 . . 120.2 ?
    C6 C11 H11 . . 120.2 ?
    C9 C12 H12A . . 109.5 ?
    C9 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C9 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C13 N4 C18 . . 130.5(3) ?
    C13 N4 H4N . . 113(3) ?
    C18 N4 H4N . . 115(3) ?
    C14 N5 C13 . . 119.1(3) ?
    O4 N6 O3 . . 121.8(3) ?
    O4 N6 C17 . . 118.5(3) ?
    O3 N6 C17 . . 119.7(3) ?
    N4 C13 N5 . . 118.2(3) ?
    N4 C13 C17 . . 122.4(3) ?
    N5 C13 C17 . . 119.4(3) ?
    N5 C14 C15 . . 124.3(4) ?
    N5 C14 H14 . . 117.9 ?
    C15 C14 H14 . . 117.9 ?
    C16 C15 C14 . . 117.9(4) ?
    C16 C15 H15 . . 121.1 ?
    C14 C15 H15 . . 121.1 ?
    C15 C16 C17 . . 119.4(4) ?
    C15 C16 H16 . . 120.3 ?
    C17 C16 H16 . . 120.3 ?
    C16 C17 C13 . . 119.9(4) ?
    C16 C17 N6 . . 117.6(3) ?
    C13 C17 N6 . . 122.4(3) ?
    C19 C18 C23 . . 119.6(3) ?
    C19 C18 N4 . . 115.8(3) ?
    C23 C18 N4 . . 124.6(3) ?
    C20 C19 C18 . . 120.0(3) ?
    C20 C19 H19 . . 120.0 ?
    C18 C19 H19 . . 120.0 ?
    C19 C20 C21 . . 121.8(3) ?
    C19 C20 H20 . . 119.1 ?
    C21 C20 H20 . . 119.1 ?
    C22 C21 C20 . . 117.2(3) ?
    C22 C21 C24 . . 121.4(3) ?
    C20 C21 C24 . . 121.4(3) ?
    C21 C22 C23 . . 122.3(3) ?
    C21 C22 H22 . . 118.9 ?
    C23 C22 H22 . . 118.9 ?
    C22 C23 C18 . . 119.1(3) ?
    C22 C23 H23 . . 120.4 ?
    C18 C23 H23 . . 120.4 ?
    C21 C24 H24A . . 109.5 ?
    C21 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C21 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    C25 N7 C30 . . 132.1(3) ?
    C25 N7 H7N . . 114(3) ?
    C30 N7 H7N . . 114(3) ?
    C26 N8 C25 . . 118.5(3) ?
    O6 N9 O5 . . 122.0(3) ?
    O6 N9 C29 . . 118.6(3) ?
    O5 N9 C29 . . 119.5(3) ?
    N7 C25 N8 . . 118.0(3) ?
    N7 C25 C29 . . 122.6(3) ?
    N8 C25 C29 . . 119.4(3) ?
    N8 C26 C27 . . 124.7(3) ?
    N8 C26 H26 . . 117.7 ?
    C27 C26 H26 . . 117.7 ?
    C28 C27 C26 . . 117.6(3) ?
    C28 C27 H27 . . 121.2 ?
    C26 C27 H27 . . 121.2 ?
    C27 C28 C29 . . 119.4(3) ?
    C27 C28 H28 . . 120.3 ?
    C29 C28 H28 . . 120.3 ?
    C28 C29 C25 . . 120.3(3) ?
    C28 C29 N9 . . 117.6(3) ?
    C25 C29 N9 . . 122.0(3) ?
    C31 C30 C35 . . 118.6(3) ?
    C31 C30 N7 . . 115.3(3) ?
    C35 C30 N7 . . 126.1(3) ?
    C32 C31 C30 . . 120.8(3) ?
    C32 C31 H31 . . 119.6 ?
    C30 C31 H31 . . 119.6 ?
    C31 C32 C33 . . 121.5(3) ?
    C31 C32 H32 . . 119.3 ?
    C33 C32 H32 . . 119.3 ?
    C34 C33 C32 . . 117.4(3) ?
    C34 C33 C36 . . 121.3(3) ?
    C32 C33 C36 . . 121.3(3) ?
    C33 C34 C35 . . 122.0(3) ?
    C33 C34 H34 . . 119.0 ?
    C35 C34 H34 . . 119.0 ?
    C30 C35 C34 . . 119.7(3) ?
    C30 C35 H35 . . 120.2 ?
    C34 C35 H35 . . 120.2 ?
    C33 C36 H36A . . 109.5 ?
    C33 C36 H36B . . 109.5 ?
    H36A C36 H36B . . 109.5 ?
    C33 C36 H36C . . 109.5 ?
    H36A C36 H36C . . 109.5 ?
    H36B C36 H36C . . 109.5 ?
    C37 N10 C42 . . 131.1(3) ?
    C37 N10 H10N . . 118(3) ?
    C42 N10 H10N . . 111(3) ?
    C38 N11 C37 . . 118.8(3) ?
    O8 N12 O7 . . 122.0(3) ?
    O8 N12 C41 . . 119.0(3) ?
    O7 N12 C41 . . 119.0(3) ?
    N11 C37 N10 . . 118.5(3) ?
    N11 C37 C41 . . 119.4(3) ?
    N10 C37 C41 . . 122.1(3) ?
    N11 C38 C39 . . 124.9(3) ?
    N11 C38 H38 . . 117.5 ?
    C39 C38 H38 . . 117.5 ?
    C40 C39 C38 . . 117.9(3) ?
    C40 C39 H39 . . 121.1 ?
    C38 C39 H39 . . 121.1 ?
    C39 C40 C41 . . 118.6(3) ?
    C39 C40 H40 . . 120.7 ?
    C41 C40 H40 . . 120.7 ?
    C40 C41 C37 . . 120.3(3) ?
    C40 C41 N12 . . 116.9(3) ?
    C37 C41 N12 . . 122.7(3) ?
    C47 C42 C43 . . 118.8(3) ?
    C47 C42 N10 . . 126.3(3) ?
    C43 C42 N10 . . 115.0(3) ?
    C44 C43 C42 . . 120.7(3) ?
    C44 C43 H43 . . 119.7 ?
    C42 C43 H43 . . 119.7 ?
    C43 C44 C45 . . 121.3(3) ?
    C43 C44 H44 . . 119.3 ?
    C45 C44 H44 . . 119.3 ?
    C46 C45 C44 . . 117.3(3) ?
    C46 C45 C48 . . 121.7(3) ?
    C44 C45 C48 . . 120.9(3) ?
    C45 C46 C47 . . 122.4(3) ?
    C45 C46 H46 . . 118.8 ?
    C47 C46 H46 . . 118.8 ?
    C46 C47 C42 . . 119.5(3) ?
    C46 C47 H47 . . 120.2 ?
    C42 C47 H47 . . 120.2 ?
    C45 C48 H48A . . 109.5 ?
    C45 C48 H48B . . 109.5 ?
    H48A C48 H48B . . 109.5 ?
    C45 C48 H48C . . 109.5 ?
    H48A C48 H48C . . 109.5 ?
    H48B C48 H48C . . 109.5 ?
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 N1 C1 N2 . . . . 0.1(6) ?
    C6 N1 C1 C5 . . . . -179.8(3) ?
    C2 N2 C1 N1 . . . . -179.9(3) ?
    C2 N2 C1 C5 . . . . -0.1(5) ?
    C1 N2 C2 C3 . . . . -0.2(6) ?
    N2 C2 C3 C4 . . . . 0.2(6) ?
    C2 C3 C4 C5 . . . . 0.2(6) ?
    C3 C4 C5 C1 . . . . -0.5(6) ?
    C3 C4 C5 N3 . . . . 176.5(3) ?
    N1 C1 C5 C4 . . . . -179.7(3) ?
    N2 C1 C5 C4 . . . . 0.4(5) ?
    N1 C1 C5 N3 . . . . 3.5(6) ?
    N2 C1 C5 N3 . . . . -176.4(3) ?
    O2 N3 C5 C4 . . . . 4.3(5) ?
    O1 N3 C5 C4 . . . . -175.0(3) ?
    O2 N3 C5 C1 . . . . -178.8(3) ?
    O1 N3 C5 C1 . . . . 1.9(5) ?
    C1 N1 C6 C11 . . . . -25.8(7) ?
    C1 N1 C6 C7 . . . . 157.6(4) ?
    C11 C6 C7 C8 . . . . 0.6(6) ?
    N1 C6 C7 C8 . . . . 177.5(3) ?
    C6 C7 C8 C9 . . . . -0.2(6) ?
    C7 C8 C9 C10 . . . . -0.1(5) ?
    C7 C8 C9 C12 . . . . 179.0(3) ?
    C8 C9 C10 C11 . . . . 0.0(5) ?
    C12 C9 C10 C11 . . . . -179.2(3) ?
    C9 C10 C11 C6 . . . . 0.5(6) ?
    C7 C6 C11 C10 . . . . -0.8(5) ?
    N1 C6 C11 C10 . . . . -177.3(3) ?
    C18 N4 C13 N5 . . . . -2.2(6) ?
    C18 N4 C13 C17 . . . . 176.0(3) ?
    C14 N5 C13 N4 . . . . 179.0(3) ?
    C14 N5 C13 C17 . . . . 0.7(6) ?
    C13 N5 C14 C15 . . . . -0.2(6) ?
    N5 C14 C15 C16 . . . . 0.5(6) ?
    C14 C15 C16 C17 . . . . -1.4(6) ?
    C15 C16 C17 C13 . . . . 1.9(6) ?
    C15 C16 C17 N6 . . . . -176.8(4) ?
    N4 C13 C17 C16 . . . . -179.8(3) ?
    N5 C13 C17 C16 . . . . -1.6(6) ?
    N4 C13 C17 N6 . . . . -1.2(6) ?
    N5 C13 C17 N6 . . . . 177.0(3) ?
    O4 N6 C17 C16 . . . . 0.6(5) ?
    O3 N6 C17 C16 . . . . 179.9(3) ?
    O4 N6 C17 C13 . . . . -178.0(3) ?
    O3 N6 C17 C13 . . . . 1.3(5) ?
    C13 N4 C18 C19 . . . . -153.3(4) ?
    C13 N4 C18 C23 . . . . 29.0(6) ?
    C23 C18 C19 C20 . . . . -0.3(6) ?
    N4 C18 C19 C20 . . . . -178.1(3) ?
    C18 C19 C20 C21 . . . . -1.0(6) ?
    C19 C20 C21 C22 . . . . 1.5(5) ?
    C19 C20 C21 C24 . . . . -177.6(3) ?
    C20 C21 C22 C23 . . . . -0.6(5) ?
    C24 C21 C22 C23 . . . . 178.5(3) ?
    C21 C22 C23 C18 . . . . -0.6(5) ?
    C19 C18 C23 C22 . . . . 1.1(5) ?
    N4 C18 C23 C22 . . . . 178.7(3) ?
    C30 N7 C25 N8 . . . . 6.6(6) ?
    C30 N7 C25 C29 . . . . -173.1(3) ?
    C26 N8 C25 N7 . . . . 178.8(3) ?
    C26 N8 C25 C29 . . . . -1.4(5) ?
    C25 N8 C26 C27 . . . . -1.0(6) ?
    N8 C26 C27 C28 . . . . 2.3(6) ?
    C26 C27 C28 C29 . . . . -1.3(6) ?
    C27 C28 C29 C25 . . . . -1.0(6) ?
    C27 C28 C29 N9 . . . . 177.6(4) ?
    N7 C25 C29 C28 . . . . -177.9(4) ?
    N8 C25 C29 C28 . . . . 2.4(6) ?
    N7 C25 C29 N9 . . . . 3.7(6) ?
    N8 C25 C29 N9 . . . . -176.1(3) ?
    O6 N9 C29 C28 . . . . 0.0(5) ?
    O5 N9 C29 C28 . . . . -178.8(4) ?
    O6 N9 C29 C25 . . . . 178.5(3) ?
    O5 N9 C29 C25 . . . . -0.3(5) ?
    C25 N7 C30 C31 . . . . 169.7(4) ?
    C25 N7 C30 C35 . . . . -9.7(6) ?
    C35 C30 C31 C32 . . . . 0.0(5) ?
    N7 C30 C31 C32 . . . . -179.5(3) ?
    C30 C31 C32 C33 . . . . 1.3(6) ?
    C31 C32 C33 C34 . . . . -1.7(5) ?
    C31 C32 C33 C36 . . . . 177.7(3) ?
    C32 C33 C34 C35 . . . . 0.9(5) ?
    C36 C33 C34 C35 . . . . -178.5(3) ?
    C31 C30 C35 C34 . . . . -0.8(5) ?
    N7 C30 C35 C34 . . . . 178.7(3) ?
    C33 C34 C35 C30 . . . . 0.3(5) ?
    C38 N11 C37 N10 . . . . -176.4(4) ?
    C38 N11 C37 C41 . . . . 3.6(6) ?
    C42 N10 C37 N11 . . . . 0.9(6) ?
    C42 N10 C37 C41 . . . . -179.1(4) ?
    C37 N11 C38 C39 . . . . -1.0(6) ?
    N11 C38 C39 C40 . . . . -1.2(6) ?
    C38 C39 C40 C41 . . . . 0.6(6) ?
    C39 C40 C41 C37 . . . . 2.1(6) ?
    C39 C40 C41 N12 . . . . -176.3(3) ?
    N11 C37 C41 C40 . . . . -4.2(6) ?
    N10 C37 C41 C40 . . . . 175.8(3) ?
    N11 C37 C41 N12 . . . . 174.0(3) ?
    N10 C37 C41 N12 . . . . -6.0(6) ?
    O8 N12 C41 C40 . . . . -2.9(5) ?
    O7 N12 C41 C40 . . . . 176.1(3) ?
    O8 N12 C41 C37 . . . . 178.8(3) ?
    O7 N12 C41 C37 . . . . -2.1(5) ?
    C37 N10 C42 C47 . . . . 3.7(7) ?
    C37 N10 C42 C43 . . . . -176.3(4) ?
    C47 C42 C43 C44 . . . . -0.7(6) ?
    N10 C42 C43 C44 . . . . 179.3(3) ?
    C42 C43 C44 C45 . . . . 0.2(6) ?
    C43 C44 C45 C46 . . . . 0.4(5) ?
    C43 C44 C45 C48 . . . . -178.2(3) ?
    C44 C45 C46 C47 . . . . -0.5(5) ?
    C48 C45 C46 C47 . . . . 178.0(3) ?
    C45 C46 C47 C42 . . . . 0.0(6) ?
    C43 C42 C47 C46 . . . . 0.6(5) ?
    N10 C42 C47 C46 . . . . -179.3(4) ?
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 H1N O1 . 0.881(19) 1.93(2) 2.632(4) 135(3)
    N4 H4N O3 . 0.88(2) 1.92(3) 2.630(4) 137(4)
    N7 H7N O5 . 0.88(2) 1.92(3) 2.622(4) 136(4)
    N10 H10N O7 . 0.89(2) 1.96(2) 2.636(4) 132(3)
    C31 H31 O1 1_654 0.95 2.50 3.444(4) 173
    C28 H28 O2 1_554 0.95 2.59 3.414(4) 145
    C4 H4 O6 1_556 0.95 2.55 3.440(4) 157
    C7 H7 O5 1_456 0.95 2.38 3.331(4) 174
    C43 H43 O3 1_554 0.95 2.49 3.436(4) 172
    C40 H40 O4 1_454 0.95 2.64 3.489(5) 149
    C19 H19 O7 1_556 0.95 2.42 3.364(4) 176
    C16 H16 O8 1_656 0.95 2.52 3.398(4) 153
    N3 O3 Cg(N5,C13--C17) 2_647 1.239(4) 3.551(3) 3.449(3) 75.19(17)
    N6 O4 Cg(N2,C1--C5) 2_657 1.238(4) 3.463(3) 3.469(3) 79.99(18)
    C36 H36C Cg(C42--C47) 2_746 0.98 2.72 3.698(4) 174
    C48 H48B Cg(C30--C35) 2_756 0.98 2.95 3.868(4) 156
data_global
_journal_date_recd_electronic     2014-05-12
_journal_date_accepted     2014-05-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      8
_journal_page_first     58
_journal_page_last     61
_journal_paper_category     GO
_journal_paper_doi     10.1107/S1600536814012227
_journal_coeditor_code     HB0011
_publ_contact_author_name     'Edward R.T. Tiekink'
_publ_contact_author_address
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email
;
edward.tiekink@gmail.com
;
_publ_contact_author_fax     ' +60 3 7967 4193 '
_publ_contact_author_phone     ' +60 3 7967 6775 '
_publ_section_title
;
Crystal structure of a new monoclinic polymorph of
N-(4-methylphenyl)-3-nitropyridin-2-amine
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Aina Mardia Akhmad Aznan ' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    ' Abdullah, Zanariah '
;
 Additional correspondence author, e-mail: zana@um.edu.my.
;
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Vannajan Sanghiran Lee' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_section_synopsis     .
