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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
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#                                                                            #
# 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 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     'manual editing of SHELXL-97 .cif file'
_journal_date_recd_electronic     2005-06-23
_journal_date_accepted     2005-06-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      8
_journal_page_first     o2379
_journal_page_last     o2381
_journal_paper_category     EO
_publ_contact_author_name     'Rafal Kruszynski'
_publ_contact_author_address
;Institute of General and Ecological Chemistry
 Technical University of \/L\'od\'z
 ul. \.Zeromskiego 116
 90-924 \/L\'od\'z
 Poland
;
_publ_contact_author_email     kruszyna@p.lodz.pl
_publ_contact_author_fax     '(48-42) 631 31 03'
_publ_contact_author_phone     '(48-42) 631 31 37'
_publ_section_title
;
Stacking and N---H...O interactions in 2,3-dimethyl-6-nitroaniline
;
loop_
    _publ_author_name
    _publ_author_address
    'Kruszynski, Rafal'
;Institute of General and Ecological Chemistry
 Technical University of \/L\'od\'z
 ul. \.Zeromskiego 116
 90-924 \/L\'od\'z
 Poland
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2,3-dimethyl-6-nitroaniline
;
_chemical_name_common
;
6-nitro-2,3-xylidine
;
_chemical_formula_moiety     'C8 H10 N2 O2'
_chemical_formula_sum     'C8 H10 N2 O2'
_chemical_formula_iupac     'C8 H10 N2 O2'
_chemical_formula_weight     166.18
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     14.4439(11)
_cell_length_b     8.6837(6)
_cell_length_c     14.0031(10)
_cell_angle_alpha     90.00
_cell_angle_beta     111.251(9)
_cell_angle_gamma     90.00
_cell_volume     1636.9(2)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     5030
_cell_measurement_theta_min     2
_cell_measurement_theta_max     25
_cell_measurement_temperature     291.0(3)
_exptl_crystal_description     prism
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.481
_exptl_crystal_size_mid     0.402
_exptl_crystal_size_min     0.253
_exptl_crystal_density_diffrn     1.349
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     704
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details
;
(X-RED; Stoe & Cie, 1999)
;
_exptl_absorpt_correction_T_min     0.941
_exptl_absorpt_correction_T_max     0.991
_exptl_special_details
;
;
_diffrn_ambient_temperature     291.0(3)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Kuma KM-4 CCD'
_diffrn_measurement_method     \w
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9090
_diffrn_reflns_av_R_equivalents     0.0346
_diffrn_reflns_av_sigmaI/netI     0.0175
_diffrn_reflns_theta_min     2.79
_diffrn_reflns_theta_max     25.33
_diffrn_reflns_theta_full     25.33
_diffrn_measured_fraction_theta_max     0.465
_diffrn_measured_fraction_theta_full     0.465
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     21
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     14.66
_diffrn_standards_decay_%     9.7
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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     1492
_reflns_number_gt     1297
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0639
_refine_ls_R_factor_gt     0.0540
_refine_ls_wR_factor_gt     0.1530
_refine_ls_wR_factor_ref     0.1634
_refine_ls_goodness_of_fit_ref     1.167
_refine_ls_restrained_S_all     1.167
_refine_ls_number_reflns     1492
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'w = 1/[\s^2^(Fo^2^)+(0.0975P)^2^+0.2133P] where P = (Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     direct
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.210
_refine_diff_density_min     -0.185
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection
;
CrysAlis CCD (UNIL IC & Kuma, 2000)
;
_computing_cell_refinement
;
CrysAlis RED (UNIL IC & Kuma, 2000)
;
_computing_data_reduction     'CrysAlis RED'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
MERCURY (Version 1.4; Bruno <i>et al.</i>, 2002)
;
_computing_publication_material     SHELXL97
loop_
    _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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    C1 0.38107(12) 0.80506(19) 0.07627(12) 0.0371(4) Uani d . 1 . . C
    C2 0.38012(12) 0.81245(18) -0.02559(12) 0.0353(4) Uani d . 1 . . C
    C3 0.37547(12) 0.67001(18) -0.07882(13) 0.0368(4) Uani d . 1 . . C
    C4 0.36957(12) 0.53156(18) -0.03186(13) 0.0396(5) Uani d . 1 . . C
    C5 0.37129(14) 0.5295(2) 0.06996(15) 0.0482(5) Uani d . 1 . . C
    H5 0.3684 0.4360 0.1012 0.058 Uiso calc R 1 . . H
    C6 0.37709(14) 0.6637(2) 0.12263(14) 0.0456(5) Uani d . 1 . . C
    H6 0.3784 0.6612 0.1895 0.055 Uiso calc R 1 . . H
    N1 0.38383(11) 0.94163(18) 0.13640(12) 0.0474(4) Uani d . 1 . . N
    O1 0.38809(11) 1.07134(16) 0.10086(12) 0.0652(5) Uani d . 1 . . O
    O2 0.38082(12) 0.92551(18) 0.22332(11) 0.0677(5) Uani d . 1 . . O
    N2 0.38212(11) 0.94697(17) -0.07443(12) 0.0498(5) Uani d . 1 . . N
    H2A 0.38409(12) 1.0347(18) -0.0432(6) 0.060 Uiso calc R 1 . . H
    H2B 0.38142(12) 0.94573(17) -0.1371(12) 0.060 Uiso calc R 1 . . H
    C7 0.37622(17) 0.6753(2) -0.18646(14) 0.0559(6) Uani d . 1 . . C
    H7A 0.3853 0.5732 -0.2078 0.084 Uiso calc R 1 . . H
    H7B 0.4296 0.7401 -0.1878 0.084 Uiso calc R 1 . . H
    H7C 0.3142 0.7161 -0.2321 0.084 Uiso calc R 1 . . H
    C8 0.36032(16) 0.3797(2) -0.08706(16) 0.0564(5) Uani d . 1 . . C
    H8A 0.4199 0.3605 -0.1006 0.085 Uiso calc R 1 . . H
    H8B 0.3046 0.3834 -0.1506 0.085 Uiso calc R 1 . . H
    H8C 0.3507 0.2985 -0.0451 0.085 Uiso calc R 1 . . H
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0406(9) 0.0395(9) 0.0331(9) 0.0016(6) 0.0155(7) -0.0038(7)
    C2 0.0363(8) 0.0362(9) 0.0343(9) 0.0034(6) 0.0140(7) 0.0012(6)
    C3 0.0407(9) 0.0373(9) 0.0321(8) 0.0057(6) 0.0127(7) -0.0013(6)
    C4 0.0426(9) 0.0360(10) 0.0390(10) 0.0036(6) 0.0133(7) 0.0002(7)
    C5 0.0619(11) 0.0401(10) 0.0458(11) 0.0038(8) 0.0233(9) 0.0096(8)
    C6 0.0589(11) 0.0495(11) 0.0329(9) 0.0040(8) 0.0220(8) 0.0037(7)
    N1 0.0513(9) 0.0498(9) 0.0440(9) -0.0005(7) 0.0205(7) -0.0127(7)
    O1 0.0947(11) 0.0398(8) 0.0712(10) -0.0049(7) 0.0422(8) -0.0119(6)
    O2 0.0944(12) 0.0747(10) 0.0433(8) -0.0013(8) 0.0362(8) -0.0161(7)
    N2 0.0736(11) 0.0372(8) 0.0461(9) -0.0008(7) 0.0305(8) 0.0031(6)
    C7 0.0828(15) 0.0515(11) 0.0369(10) 0.0074(9) 0.0259(10) 0.0006(8)
    C8 0.0697(12) 0.0383(10) 0.0610(12) 0.0036(9) 0.0234(10) -0.0059(9)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    C1 C6 . 1.399(2) ?
    C1 C2 . 1.423(2) ?
    C1 N1 . 1.447(2) ?
    C2 N2 . 1.359(2) ?
    C2 C3 . 1.433(2) ?
    C3 C4 . 1.388(2) ?
    C3 C7 . 1.512(2) ?
    C4 C5 . 1.417(3) ?
    C4 C8 . 1.510(2) ?
    C5 C6 . 1.365(2) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    N1 O2 . 1.241(2) ?
    N1 O1 . 1.242(2) ?
    N2 H2A . 0.8742 ?
    N2 H2B . 0.8742 ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
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
    C6 C1 C2 . . 121.16(14) ?
    C6 C1 N1 . . 116.49(15) ?
    C2 C1 N1 . . 122.33(15) ?
    N2 C2 C1 . . 123.29(14) ?
    N2 C2 C3 . . 119.06(14) ?
    C1 C2 C3 . . 117.65(14) ?
    C4 C3 C2 . . 120.05(15) ?
    C4 C3 C7 . . 121.51(15) ?
    C2 C3 C7 . . 118.44(14) ?
    C3 C4 C5 . . 120.38(15) ?
    C3 C4 C8 . . 121.56(16) ?
    C5 C4 C8 . . 118.06(15) ?
    C6 C5 C4 . . 120.56(15) ?
    C6 C5 H5 . . 119.7 ?
    C4 C5 H5 . . 119.7 ?
    C5 C6 C1 . . 120.18(16) ?
    C5 C6 H6 . . 119.9 ?
    C1 C6 H6 . . 119.9 ?
    O2 N1 O1 . . 121.30(15) ?
    O2 N1 C1 . . 118.35(15) ?
    O1 N1 C1 . . 120.34(15) ?
    C2 N2 H2A . . 120.0 ?
    C2 N2 H2B . . 120.0 ?
    H2A N2 H2B . . 120.0 ?
    C3 C7 H7A . . 109.5 ?
    C3 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C3 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    C4 C8 H8A . . 109.5 ?
    C4 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C4 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
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
    N2 H2A O1 . 0.87 2.02 2.654(2) 128
    N2 H2B O2 6_575 0.87 2.25 3.035(2) 150
    C6 H6 O2 . 0.93 2.34 2.665(2) 100

