##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-Bromo-2,6-dimethylaniline
;
_chemical_name_common     '4-Bromo-2,6-dimethylaniline'
_chemical_formula_moiety     'C8 H10 Br N'
_chemical_formula_sum     'C8 H10 Br N'
_chemical_formula_iupac     'C8 H10 Br N'
_chemical_formula_weight     200.07
_chemical_melting_point     321
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     20.141(4)
_cell_length_b     5.1500(10)
_cell_length_c     17.300(4)
_cell_angle_alpha     90.00
_cell_angle_beta     111.53(3)
_cell_angle_gamma     90.00
_cell_volume     1669.3(7)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     10
_cell_measurement_theta_max     13
_cell_measurement_temperature     294(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.592
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     800
_exptl_absorpt_coefficient_mu     4.849
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.211
_exptl_absorpt_correction_T_max     0.379
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     294(2)
_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     'Enraf--Nonius CAD-4 diffractometer'
_diffrn_measurement_method     'ω/2θ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3392
_diffrn_reflns_av_R_equivalents     0.0400
_diffrn_reflns_av_sigmaI/netI     0.0542
_diffrn_reflns_theta_min     1.09
_diffrn_reflns_theta_max     25.96
_diffrn_reflns_theta_full     25.96
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_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 > 2sigma(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     3268
_reflns_number_gt     1523
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1313
_refine_ls_R_factor_gt     0.0641
_refine_ls_wR_factor_gt     0.1357
_refine_ls_wR_factor_ref     0.1657
_refine_ls_goodness_of_fit_ref     1.055
_refine_ls_restrained_S_all     1.054
_refine_ls_number_reflns     3268
_refine_ls_number_parameters     183
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0500P)²+0.6000P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.237
_refine_diff_density_min     -0.250
_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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 Software (Enraf--Nonius,1985)'
_computing_cell_refinement     'CAD-4 Software'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo,1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXTL (Bruker, 2000)'
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_disorder_assembly
    _atom_site_disorder_group
    Br Br1 0.08550(5) 0.9358(3) 0.10030(5) 0.1246(5) Uani d . 1 . .
    Br Br2 0.43509(5) 0.5936(2) 0.34568(6) 0.1157(4) Uani d . 1 . .
    N N1 0.1751(3) 1.3344(13) 0.4526(4) 0.100(2) Uani d . 1 . .
    H H1A 0.2092 1.4455 0.4708 0.120 Uiso calc R 1 . .
    H H1B 0.1557 1.2726 0.4854 0.120 Uiso calc R 1 . .
    N N2 0.7343(3) 0.1666(14) 0.4436(4) 0.102(2) Uani d . 1 . .
    H H2D 0.7635 0.2300 0.4226 0.123 Uiso calc R 1 . .
    H H2E 0.7482 0.0463 0.4805 0.123 Uiso calc R 1 . .
    C C1 0.2375(4) 1.5677(16) 0.3431(5) 0.103(3) Uani d . 1 . .
    H H1C 0.2540 1.6065 0.2989 0.154 Uiso calc R 1 . .
    H H1D 0.2771 1.5124 0.3912 0.154 Uiso calc R 1 . .
    H H1E 0.2165 1.7202 0.3565 0.154 Uiso calc R 1 . .
    C C2 0.0684(4) 0.9407(18) 0.4006(5) 0.103(3) Uani d . 1 . .
    H H2A 0.0354 0.8059 0.3727 0.154 Uiso calc R 1 . .
    H H2B 0.0437 1.0737 0.4183 0.154 Uiso calc R 1 . .
    H H2C 0.1056 0.8692 0.4482 0.154 Uiso calc R 1 . .
    C C3 0.1002(4) 1.0549(18) 0.3425(5) 0.086(2) Uani d . 1 . .
    C C4 0.0812(4) 0.9643(17) 0.2630(5) 0.090(2) Uani d . 1 . .
    H H4A 0.0475 0.8324 0.2448 0.108 Uiso calc R 1 . .
    C C5 0.1113(4) 1.066(2) 0.2090(5) 0.095(2) Uani d . 1 . .
    C C6 0.1609(4) 1.2610(17) 0.2362(4) 0.086(2) Uani d . 1 . .
    H H6A 0.1803 1.3325 0.1998 0.103 Uiso calc R 1 . .
    C C7 0.1822(4) 1.3524(15) 0.3159(5) 0.079(2) Uani d U 1 . .
    C C8 0.1512(4) 1.2540(18) 0.3696(5) 0.086(2) Uani d U 1 . .
    C C9 0.6901(4) 0.5486(19) 0.3171(5) 0.108(3) Uani d . 1 . .
    H H9A 0.7332 0.6128 0.3586 0.163 Uiso calc R 1 . .
    H H9B 0.6673 0.6858 0.2790 0.163 Uiso calc R 1 . .
    H H9C 0.7013 0.4084 0.2874 0.163 Uiso calc R 1 . .
    C C10 0.6417(4) -0.0549(16) 0.5187(5) 0.101(3) Uani d . 1 . .
    H H10A 0.6562 -0.2025 0.4948 0.152 Uiso calc R 1 . .
    H H10B 0.6024 -0.1023 0.5346 0.152 Uiso calc R 1 . .
    H H10C 0.6810 0.0023 0.5669 0.152 Uiso calc R 1 . .
    C C11 0.6190(4) 0.1636(15) 0.4553(5) 0.083(2) Uani d . 1 . .
    C C12 0.5507(4) 0.2581(19) 0.4319(5) 0.093(2) Uani d . 1 . .
    H H12A 0.5193 0.1906 0.4550 0.112 Uiso calc R 1 . .
    C C13 0.5290(4) 0.4543(18) 0.3736(5) 0.089(2) Uani d . 1 . .
    C C14 0.5726(4) 0.5468(19) 0.3354(5) 0.097(3) Uani d . 1 . .
    H H14A 0.5561 0.6727 0.2942 0.116 Uiso calc R 1 . .
    C C15 0.6406(5) 0.4529(17) 0.3581(5) 0.087(2) Uani d . 1 . .
    C C16 0.6641(4) 0.2596(18) 0.4174(5) 0.087(2) Uani d . 1 . .
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
    Br1 0.1232(8) 0.1683(11) 0.0770(6) -0.0228(7) 0.0304(5) -0.0229(6)
    Br2 0.0927(6) 0.1499(9) 0.0949(7) 0.0165(6) 0.0231(5) 0.0050(7)
    N1 0.096(4) 0.113(6) 0.087(5) -0.010(4) 0.029(4) -0.010(4)
    N2 0.092(4) 0.116(6) 0.095(5) 0.001(4) 0.028(4) -0.003(4)
    C1 0.098(6) 0.088(6) 0.117(7) -0.006(5) 0.033(5) -0.009(6)
    C2 0.093(5) 0.119(7) 0.094(6) -0.004(5) 0.032(5) 0.013(6)
    C3 0.077(4) 0.106(6) 0.070(5) 0.002(5) 0.023(4) 0.006(5)
    C4 0.084(5) 0.091(6) 0.085(5) 0.005(4) 0.020(4) -0.002(5)
    C5 0.092(5) 0.126(7) 0.063(4) -0.007(5) 0.024(4) 0.002(5)
    C6 0.086(5) 0.105(6) 0.065(5) -0.007(5) 0.026(4) 0.008(5)
    C7 0.073(4) 0.085(5) 0.074(4) -0.003(4) 0.021(3) 0.005(4)
    C8 0.082(4) 0.095(5) 0.073(4) 0.007(4) 0.020(4) 0.002(4)
    C9 0.105(6) 0.136(8) 0.083(5) 0.006(6) 0.033(5) 0.000(6)
    C10 0.109(6) 0.091(6) 0.092(6) -0.002(5) 0.023(5) -0.008(5)
    C11 0.080(5) 0.078(6) 0.076(5) -0.009(4) 0.009(4) -0.008(4)
    C12 0.084(5) 0.109(7) 0.077(5) -0.003(5) 0.019(4) 0.002(5)
    C13 0.090(5) 0.104(7) 0.062(4) 0.014(5) 0.013(4) -0.013(5)
    C14 0.095(6) 0.120(7) 0.071(5) 0.001(5) 0.025(4) 0.006(5)
    C15 0.094(5) 0.095(6) 0.071(5) -0.009(5) 0.029(4) -0.010(5)
    C16 0.079(5) 0.104(6) 0.075(5) -0.009(5) 0.023(4) -0.014(5)
_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
    Br1 C5 . 1.880(8) yes
    N1 C8 . 1.399(9) yes
    N1 H1A . 0.8600 ?
    N1 H1B . 0.8600 ?
    C1 C7 . 1.520(10) ?
    C1 H1C . 0.9600 ?
    C1 H1D . 0.9600 ?
    C1 H1E . 0.9600 ?
    C2 C3 . 1.497(10) ?
    C2 H2A . 0.9600 ?
    C2 H2B . 0.9600 ?
    C2 H2C . 0.9600 ?
    C3 C4 . 1.367(10) ?
    C3 C8 . 1.405(11) ?
    C4 C5 . 1.390(11) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.374(11) ?
    C6 C7 . 1.369(10) ?
    C6 H6A . 0.9300 ?
    C7 C8 . 1.390(10) ?
    Br2 C13 . 1.913(8) yes
    N2 C16 . 1.403(9) yes
    N2 H2D . 0.8600 ?
    N2 H2E . 0.8600 ?
    C9 C15 . 1.503(11) ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 C11 . 1.520(10) ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 C12 . 1.373(10) ?
    C11 C16 . 1.391(10) ?
    C12 C13 . 1.380(11) ?
    C12 H12A . 0.9300 ?
    C13 C14 . 1.363(11) ?
    C14 C15 . 1.368(10) ?
    C14 H14A . 0.9300 ?
    C15 C16 . 1.382(11) ?
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
    C8 N1 H1A . . 120.0 ?
    C8 N1 H1B . . 120.0 ?
    H1A N1 H1B . . 120.0 ?
    C7 C1 H1C . . 109.5 ?
    C7 C1 H1D . . 109.5 ?
    H1C C1 H1D . . 109.5 ?
    C7 C1 H1E . . 109.5 ?
    H1C C1 H1E . . 109.5 ?
    H1D C1 H1E . . 109.5 ?
    C3 C2 H2A . . 109.5 ?
    C3 C2 H2B . . 109.5 ?
    H2A C2 H2B . . 109.5 ?
    C3 C2 H2C . . 109.5 ?
    H2A C2 H2C . . 109.5 ?
    H2B C2 H2C . . 109.5 ?
    C4 C3 C8 . . 119.0(7) ?
    C4 C3 C2 . . 120.7(8) ?
    C8 C3 C2 . . 120.3(7) ?
    C3 C4 C5 . . 121.2(8) ?
    C3 C4 H4A . . 119.4 ?
    C5 C4 H4A . . 119.4 ?
    C6 C5 C4 . . 119.1(8) ?
    C6 C5 Br1 . . 120.2(6) yes
    C4 C5 Br1 . . 120.7(7) yes
    C7 C6 C5 . . 121.1(7) ?
    C7 C6 H6A . . 119.5 ?
    C5 C6 H6A . . 119.5 ?
    C6 C7 C8 . . 119.8(7) ?
    C6 C7 C1 . . 119.1(7) ?
    C8 C7 C1 . . 121.1(7) ?
    C7 C8 N1 . . 120.6(8) yes
    C7 C8 C3 . . 119.7(7) ?
    N1 C8 C3 . . 119.5(7) yes
    C16 N2 H2D . . 120.0 ?
    C16 N2 H2E . . 120.0 ?
    H2D N2 H2E . . 120.0 ?
    C15 C9 H9A . . 109.5 ?
    C15 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C15 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C11 C10 H10A . . 109.5 ?
    C11 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C11 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C12 C11 C16 . . 119.4(8) ?
    C12 C11 C10 . . 118.6(8) ?
    C16 C11 C10 . . 121.8(8) ?
    C11 C12 C13 . . 119.3(8) ?
    C11 C12 H12A . . 120.4 ?
    C13 C12 H12A . . 120.4 ?
    C14 C13 C12 . . 121.5(8) ?
    C14 C13 Br2 . . 119.9(7) yes
    C12 C13 Br2 . . 118.5(7) yes
    C13 C14 C15 . . 119.5(8) ?
    C13 C14 H14A . . 120.3 ?
    C15 C14 H14A . . 120.3 ?
    C14 C15 C16 . . 120.1(8) ?
    C14 C15 C9 . . 121.1(8) ?
    C16 C15 C9 . . 118.8(8) ?
    C15 C16 C11 . . 120.1(8) ?
    C15 C16 N2 . . 121.0(8) yes
    C11 C16 N2 . . 118.9(8) yes
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
    C8 C3 C4 C5 . . . . 0.0(12) ?
    C2 C3 C4 C5 . . . . -178.9(8) ?
    C3 C4 C5 C6 . . . . -0.2(13) ?
    C3 C4 C5 Br1 . . . . 179.1(6) ?
    C4 C5 C6 C7 . . . . 1.6(13) ?
    Br1 C5 C6 C7 . . . . -177.8(6) ?
    C5 C6 C7 C8 . . . . -2.6(12) ?
    C5 C6 C7 C1 . . . . 179.6(8) ?
    C6 C7 C8 N1 . . . . 176.4(7) ?
    C1 C7 C8 N1 . . . . -5.9(12) ?
    C6 C7 C8 C3 . . . . 2.3(12) ?
    C1 C7 C8 C3 . . . . -180.0(7) ?
    C4 C3 C8 C7 . . . . -1.0(12) ?
    C2 C3 C8 C7 . . . . 177.8(7) ?
    C4 C3 C8 N1 . . . . -175.1(7) ?
    C2 C3 C8 N1 . . . . 3.7(12) ?
    C16 C11 C12 C13 . . . . -2.7(12) ?
    C10 C11 C12 C13 . . . . -179.3(7) ?
    C11 C12 C13 C14 . . . . 3.7(13) ?
    C11 C12 C13 Br2 . . . . -177.2(6) ?
    C12 C13 C14 C15 . . . . -3.4(13) ?
    Br2 C13 C14 C15 . . . . 177.5(6) ?
    C13 C14 C15 C16 . . . . 2.2(13) ?
    C13 C14 C15 C9 . . . . 179.6(8) ?
    C14 C15 C16 C11 . . . . -1.2(12) ?
    C9 C15 C16 C11 . . . . -178.7(7) ?
    C14 C15 C16 N2 . . . . -177.9(7) ?
    C9 C15 C16 N2 . . . . 4.6(12) ?
    C12 C11 C16 C15 . . . . 1.5(12) ?
    C10 C11 C16 C15 . . . . 178.0(7) ?
    C12 C11 C16 N2 . . . . 178.2(7) ?
    C10 C11 C16 N2 . . . . -5.3(11) ?
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 H1A N2 3_676 0.86 2.50 3.279(10) 151.00 yes
    N2 H2E N1 3_666 0.86 2.50 3.287(10) 152.00 yes
data_global
_journal_date_recd_electronic     2007-11-29
_journal_date_accepted     2007-11-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o220
_journal_page_last     o220
_journal_paper_category     QO
_journal_coeditor_code     HK2405
_publ_contact_author_name     'Professor Hong-Jun Zhu'
_publ_contact_author_address
;
'Hong-Jun Zhu'
Department of Applied Chemistry
College of Science
Nanjing University of Technology
Nanjing 210009
P.R. China
;
_publ_contact_author_email     zhuhj@njut.edu.cn
_publ_contact_author_fax     '86-25-83369345'
_publ_contact_author_phone     '86-25-83587449'
_publ_section_title
;
4-Bromo-2,6-dimethylaniline
;
loop_
    _publ_author_name
    _publ_author_address
    'Rui Liu'
;
Department of Applied Chemistry,
College of Science,
Nanjing University of Technology,
Nanjing 210009
People's Republic of China
;
    'Yu-Hao Li'
;
Department of Applied Chemistry,
College of Science,
Nanjing University of Technology,
Nanjing 210009
People's Republic of China
;
    'Wei Luo'
;
Department of Applied Chemistry,
College of Science,
Nanjing University of Technology,
Nanjing 210009
People's Republic of China
;
    'Shan Liu'
;
Department of Applied Chemistry,
College of Science,
Nanjing University of Technology,
Nanjing 210009
People's Republic of China
;
    'Hong-Jun Zhu'
;
Department of Applied Chemistry,
College of Science,
Nanjing University of Technology,
Nanjing 210009
People's Republic of China
;
