##############################################################################
#                                                                            #
# 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_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2012-05-07
_journal_date_accepted     2012-05-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      6
_journal_page_first     o1967
_journal_page_last     o1967
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812024348
_journal_coeditor_code     FJ2555
_publ_contact_author_name
;
Marijana Đaković
;
_publ_contact_author_address
;
Laboratory of General and Inorganic Chemistry
Department of Chemistry
Faculty of Science, University of Zagreb
Horvatovac 102a
HR-10 000 Zagreb, Croatia
;
_publ_contact_author_email     mdjakovic@chem.pmf.hr
_publ_contact_author_fax     '00385 1 4606341'
_publ_contact_author_phone     '00385 1 4606356'
_publ_section_title
;
N-(4-Methylbenzyl)-3-nitroaniline
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Đaković, Marijana' .
;
Department of Chemistry
Faculty of Science
University of Zagreb
Horvatovac 102a
HR-10000 Zagreb
Croatia
;
    'Portada, Tomislav' .
;
Department of Organic Chemistry and Biochemistry
Ruđer Bošković Institute
PO Box 180
HR-10000 Zagreb
Croatia
;
    'Klačić, Tin' .
;
5th High School
Klaićeva 1
HR-10000 Zagreb
Croatia
;
data_I
_chemical_name_systematic
;
N-(4-Methylbenzyl)-3-nitroaniline
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H14 N2 O2'
_chemical_formula_sum     'C14 H14 N2 O2'
_chemical_formula_structural     ?
_chemical_formula_iupac     'C14 H14 N2 O2'
_chemical_formula_weight     242.27
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P  21'
_symmetry_space_group_name_Hall     'P  2 yb'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,1/2+y,-z
_cell_length_a     5.1851(4)
_cell_length_b     21.408(2)
_cell_length_c     5.6833(4)
_cell_angle_alpha     90
_cell_angle_beta     98.010(7)
_cell_angle_gamma     90
_cell_volume     624.71(8)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4334
_cell_measurement_theta_min     4.3936
_cell_measurement_theta_max     32.6896
_cell_measurement_temperature     296
_cell_special_details
;
;
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.57
_exptl_crystal_size_mid     0.50
_exptl_crystal_size_min     0.19
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.288
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     256
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2009)
;
_exptl_absorpt_correction_T_min     0.95317
_exptl_absorpt_correction_T_max     0.95783
_exptl_special_details
;
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with a Sapphire-3 CCD area detector
;
_diffrn_measurement_method     'CCD'
_diffrn_detector_area_resol_mean     16.3426
_diffrn_reflns_number     11868
_diffrn_reflns_av_R_equivalents     0.0416
_diffrn_reflns_av_sigmaI/netI     0.0256
_diffrn_reflns_theta_min     4.40
_diffrn_reflns_theta_max     30.00
_diffrn_reflns_theta_full     30.00
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -30
_diffrn_reflns_limit_k_max     30
_diffrn_reflns_limit_l_min     -7
_diffrn_reflns_limit_l_max     7
_diffrn_reflns_reduction_process
;
;
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
Refinement on F² for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The observed criterion of F² > σ(F²)
is used only for calculating -R-factor-obs 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     1856
_reflns_number_gt     1373
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0638
_refine_ls_R_factor_gt     0.0459
_refine_ls_wR_factor_gt     0.1097
_refine_ls_wR_factor_ref     0.1165
_refine_ls_goodness_of_fit_ref     1.034
_refine_ls_restrained_S_all     1.034
_refine_ls_number_reflns     1856
_refine_ls_number_parameters     167
_refine_ls_number_restraints     1
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0688P)²]         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     0.162
_refine_diff_density_min     -0.112
_refine_ls_extinction_method     'none'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    O O 0.0106 0.0060 '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'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    O O1 0.0400(4) 0.59135(11) 0.2460(4) 0.0814(8) Uani . . 1.000
    O O2 0.1836(4) 0.49767(11) 0.2911(3) 0.0688(7) Uani . . 1.000
    N N1 0.8389(4) 0.47827(11) -0.2730(5) 0.0645(8) Uani . . 1.000
    N N2 0.1802(4) 0.54885(10) 0.1976(3) 0.0525(7) Uani . . 1.000
    C C1 0.6686(4) 0.52300(11) -0.2149(4) 0.0455(6) Uani . . 1.000
    C C2 0.5065(4) 0.51224(10) -0.0402(4) 0.0417(6) Uani . . 1.000
    C C3 0.3489(4) 0.56021(10) 0.0150(4) 0.0434(6) Uani . . 1.000
    C C4 0.3374(5) 0.61797(11) -0.0925(5) 0.0564(8) Uani . . 1.000
    C C5 0.4936(5) 0.62762(13) -0.2656(5) 0.0627(9) Uani . . 1.000
    C C6 0.6563(5) 0.58119(12) -0.3245(4) 0.0558(8) Uani . . 1.000
    C C7 0.8676(5) 0.41780(13) -0.1683(5) 0.0619(8) Uani . . 1.000
    C C8 0.6482(4) 0.37253(11) -0.2473(4) 0.0511(7) Uani . . 1.000
    C C9 0.5891(6) 0.32463(15) -0.1024(5) 0.0703(10) Uani . . 1.000
    C C10 0.3929(7) 0.28214(14) -0.1763(6) 0.0747(11) Uani . . 1.000
    C C11 0.2506(6) 0.28531(12) -0.3980(5) 0.0628(9) Uani . . 1.000
    C C12 0.3078(6) 0.33344(14) -0.5412(5) 0.0669(9) Uani . . 1.000
    C C13 0.5021(6) 0.37587(13) -0.4681(5) 0.0608(8) Uani . . 1.000
    C C14 0.0335(7) 0.23991(16) -0.4795(9) 0.0912(13) Uani . . 1.000
    H H1N 0.913(6) 0.4885(14) -0.376(5) 0.061(8) Uiso . . 1.000
    H H2 0.50580 0.47380 0.03580 0.0500 Uiso calc R 1.000
    H H4 0.22830 0.64920 -0.04980 0.0680 Uiso calc R 1.000
    H H5 0.48930 0.66590 -0.34350 0.0750 Uiso calc R 1.000
    H H6 0.76130 0.58890 -0.44120 0.0670 Uiso calc R 1.000
    H H7A 0.88320 0.42240 0.00290 0.0740 Uiso calc R 1.000
    H H7B 1.02900 0.39970 -0.20470 0.0740 Uiso calc R 1.000
    H H9 0.68320 0.32070 0.04860 0.0840 Uiso calc R 1.000
    H H10 0.35690 0.25070 -0.07280 0.0890 Uiso calc R 1.000
    H H12 0.21290 0.33750 -0.69180 0.0800 Uiso calc R 1.000
    H H13 0.53540 0.40770 -0.57100 0.0730 Uiso calc R 1.000
    H H14A -0.04300 0.25020 -0.63840 0.1370 Uiso calc R 1.000
    H H14B -0.09690 0.24240 -0.37530 0.1370 Uiso calc R 1.000
    H H14C 0.10230 0.19820 -0.47650 0.1370 Uiso calc R 1.000
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 N2 . . 1.220(3) no
    O2 N2 . . 1.217(3) no
    N1 C1 . . 1.374(3) no
    N1 C7 . . 1.424(4) no
    N2 C3 . . 1.468(3) no
    N1 H1N . . 0.78(3) no
    C1 C6 . . 1.390(3) no
    C1 C2 . . 1.406(3) no
    C2 C3 . . 1.376(3) no
    C3 C4 . . 1.377(3) no
    C4 C5 . . 1.374(4) no
    C5 C6 . . 1.375(4) no
    C7 C8 . . 1.514(4) no
    C8 C13 . . 1.374(4) no
    C8 C9 . . 1.376(4) no
    C9 C10 . . 1.386(5) no
    C10 C11 . . 1.370(4) no
    C11 C14 . . 1.510(5) no
    C11 C12 . . 1.371(4) no
    C12 C13 . . 1.377(4) no
    C2 H2 . . 0.9300 no
    C4 H4 . . 0.9300 no
    C5 H5 . . 0.9300 no
    C6 H6 . . 0.9300 no
    C7 H7A . . 0.9700 no
    C7 H7B . . 0.9700 no
    C9 H9 . . 0.9300 no
    C10 H10 . . 0.9300 no
    C12 H12 . . 0.9300 no
    C13 H13 . . 0.9300 no
    C14 H14A . . 0.9600 no
    C14 H14B . . 0.9600 no
    C14 H14C . . 0.9600 no
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    O1 C1 3.362(3) . 1_455 no
    O1 C6 3.364(3) . 1_456 no
    O2 C7 3.352(3) . 1_455 no
    O2 C13 3.282(4) . 1_556 no
    O1 H14C 2.7900 . 2_555 no
    O1 H4 2.4000 . . no
    O1 H6 2.4400 . 1_456 no
    O2 H1N 2.52(3) . 1_456 no
    O2 H2 2.4200 . . no
    O2 H7A 2.6400 . 1_455 no
    O2 H13 2.6900 . 1_556 no
    N1 C3 3.398(3) . 1_655 no
    N2 C1 3.333(3) . 1_455 no
    N1 H13 2.6200 . . no
    C1 O1 3.362(3) . 1_655 no
    C1 N2 3.333(3) . 1_655 no
    C1 C13 3.520(4) . . no
    C2 C8 3.333(3) . . no
    C3 N1 3.398(3) . 1_455 no
    C6 O1 3.364(3) . 1_654 no
    C7 O2 3.352(3) . 1_655 no
    C8 C2 3.333(3) . . no
    C13 C1 3.520(4) . . no
    C13 O2 3.282(4) . 1_554 no
    C2 H7A 2.7300 . . no
    C6 H14C 3.0800 . 2_654 no
    C7 H2 2.6300 . . no
    C8 H2 2.8600 . . no
    C9 H14B 2.9800 . 1_655 no
    C11 H7B 2.9800 . 1_455 no
    C12 H7B 2.9200 . 1_455 no
    C13 H7B 3.0900 . 1_455 no
    H1N O2 2.52(3) . 1_654 no
    H1N H6 2.3000 . . no
    H2 O2 2.4200 . . no
    H2 C7 2.6300 . . no
    H2 C8 2.8600 . . no
    H2 H7A 2.2800 . . no
    H4 O1 2.4000 . . no
    H5 H14C 2.5700 . 2_654 no
    H6 O1 2.4400 . 1_654 no
    H6 H1N 2.3000 . . no
    H6 H14C 2.5100 . 2_654 no
    H7A O2 2.6400 . 1_655 no
    H7A C2 2.7300 . . no
    H7A H2 2.2800 . . no
    H7A H9 2.4400 . . no
    H7B C11 2.9800 . 1_655 no
    H7B C12 2.9200 . 1_655 no
    H7B C13 3.0900 . 1_655 no
    H9 H7A 2.4400 . . no
    H9 H14A 2.6000 . 1_656 no
    H12 H14A 2.3400 . . no
    H13 O2 2.6900 . 1_554 no
    H13 N1 2.6200 . . no
    H14A H9 2.6000 . 1_454 no
    H14A H12 2.3400 . . no
    H14B C9 2.9800 . 1_455 no
    H14C O1 2.7900 . 2_545 no
    H14C C6 3.0800 . 2_644 no
    H14C H5 2.5700 . 2_644 no
    H14C H6 2.5100 . 2_644 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 N1 C7 . . . 124.5(2) no
    O1 N2 O2 . . . 123.1(2) no
    O1 N2 C3 . . . 117.9(2) no
    O2 N2 C3 . . . 119.0(2) no
    C7 N1 H1N . . . 123(2) no
    C1 N1 H1N . . . 113(2) no
    N1 C1 C6 . . . 120.5(2) no
    C2 C1 C6 . . . 117.9(2) no
    N1 C1 C2 . . . 121.5(2) no
    C1 C2 C3 . . . 118.1(2) no
    N2 C3 C4 . . . 118.0(2) no
    N2 C3 C2 . . . 117.97(19) no
    C2 C3 C4 . . . 124.0(2) no
    C3 C4 C5 . . . 117.3(2) no
    C4 C5 C6 . . . 120.6(2) no
    C1 C6 C5 . . . 122.0(2) no
    N1 C7 C8 . . . 115.3(2) no
    C9 C8 C13 . . . 116.4(2) no
    C7 C8 C9 . . . 121.4(2) no
    C7 C8 C13 . . . 122.2(2) no
    C8 C9 C10 . . . 121.5(3) no
    C9 C10 C11 . . . 121.7(3) no
    C10 C11 C14 . . . 122.2(3) no
    C10 C11 C12 . . . 116.7(3) no
    C12 C11 C14 . . . 121.0(3) no
    C11 C12 C13 . . . 121.8(3) no
    C8 C13 C12 . . . 121.9(3) no
    C1 C2 H2 . . . 121.00 no
    C3 C2 H2 . . . 121.00 no
    C3 C4 H4 . . . 121.00 no
    C5 C4 H4 . . . 121.00 no
    C4 C5 H5 . . . 120.00 no
    C6 C5 H5 . . . 120.00 no
    C1 C6 H6 . . . 119.00 no
    C5 C6 H6 . . . 119.00 no
    N1 C7 H7A . . . 108.00 no
    N1 C7 H7B . . . 108.00 no
    C8 C7 H7A . . . 108.00 no
    C8 C7 H7B . . . 108.00 no
    H7A C7 H7B . . . 107.00 no
    C8 C9 H9 . . . 119.00 no
    C10 C9 H9 . . . 119.00 no
    C9 C10 H10 . . . 119.00 no
    C11 C10 H10 . . . 119.00 no
    C11 C12 H12 . . . 119.00 no
    C13 C12 H12 . . . 119.00 no
    C8 C13 H13 . . . 119.00 no
    C12 C13 H13 . . . 119.00 no
    C11 C14 H14A . . . 109.00 no
    C11 C14 H14B . . . 110.00 no
    C11 C14 H14C . . . 109.00 no
    H14A C14 H14B . . . 109.00 no
    H14A C14 H14C . . . 109.00 no
    H14B C14 H14C . . . 109.00 no
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
    C7 N1 C1 C2 . . . . 0.7(4) no
    C7 N1 C1 C6 . . . . 179.2(2) no
    C1 N1 C7 C8 . . . . 73.9(3) no
    O1 N2 C3 C2 . . . . -179.8(2) no
    O1 N2 C3 C4 . . . . -0.6(3) no
    O2 N2 C3 C2 . . . . -0.8(3) no
    O2 N2 C3 C4 . . . . 178.5(2) no
    N1 C1 C2 C3 . . . . 177.4(2) no
    C6 C1 C2 C3 . . . . -1.1(3) no
    N1 C1 C6 C5 . . . . -178.1(2) no
    C2 C1 C6 C5 . . . . 0.5(4) no
    C1 C2 C3 N2 . . . . -179.93(19) no
    C1 C2 C3 C4 . . . . 0.9(3) no
    N2 C3 C4 C5 . . . . -179.1(2) no
    C2 C3 C4 C5 . . . . 0.1(4) no
    C3 C4 C5 C6 . . . . -0.9(4) no
    C4 C5 C6 C1 . . . . 0.6(4) no
    N1 C7 C8 C9 . . . . -152.7(3) no
    N1 C7 C8 C13 . . . . 29.0(4) no
    C7 C8 C13 C12 . . . . 178.1(3) no
    C7 C8 C9 C10 . . . . -178.3(3) no
    C13 C8 C9 C10 . . . . 0.1(4) no
    C9 C8 C13 C12 . . . . -0.3(4) no
    C8 C9 C10 C11 . . . . 0.8(5) no
    C9 C10 C11 C12 . . . . -1.5(5) no
    C9 C10 C11 C14 . . . . -179.0(3) no
    C10 C11 C12 C13 . . . . 1.3(5) no
    C14 C11 C12 C13 . . . . 178.9(3) no
    C11 C12 C13 C8 . . . . -0.4(5) no
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
    _geom_hbond_publ_flag
    N1 H1N O2 1_654 0.78(3) 2.52(3) 3.277(3) 168(3) yes
    C6 H6 O1 1_654 0.93 2.44 3.364(3) 171 yes
    C7 H7A O2 1_655 0.97 2.64 3.352(3) 130 yes
    C13 H13 O2 1_554 0.93 2.69 3.282(4) 122 yes
