##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2,4,6-Trichloroaniline
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H4 Cl3 N'
_chemical_formula_sum     'C6 H4 Cl3 N'
_chemical_formula_iupac     'C6 H4 Cl3 N'
_chemical_formula_weight     196.45
_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     13.1933(9)
_cell_length_b     3.7913(3)
_cell_length_c     15.7740(10)
_cell_angle_alpha     90.00
_cell_angle_beta     111.546(8)
_cell_angle_gamma     90.00
_cell_volume     733.88(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2998
_cell_measurement_theta_min     2.763
_cell_measurement_theta_max     26.451
_cell_measurement_temperature     100(2)
_exptl_crystal_description     Needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.06
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.778
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     392
_exptl_absorpt_coefficient_mu     1.158
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(CrysAlis RED; Oxford Diffraction, 2006)'
_exptl_absorpt_correction_T_min     0.6544
_exptl_absorpt_correction_T_max     0.9551
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_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 single-crystal X-ray diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω and φ
;
_diffrn_detector_area_resol_mean     8.4012
_diffrn_reflns_number     6014
_diffrn_reflns_av_R_equivalents     0.0196
_diffrn_reflns_av_sigmaI/netI     0.0283
_diffrn_reflns_theta_min     2.52
_diffrn_reflns_theta_max     26.37
_diffrn_reflns_theta_full     26.37
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -3
_diffrn_reflns_limit_k_max     4
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_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     2640
_reflns_number_gt     2394
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0281
_refine_ls_R_factor_gt     0.0223
_refine_ls_wR_factor_gt     0.0494
_refine_ls_wR_factor_ref     0.0516
_refine_ls_goodness_of_fit_ref     1.057
_refine_ls_restrained_S_all     1.057
_refine_ls_number_reflns     2640
_refine_ls_number_parameters     205
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     refxyz
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0308P)²+0.0195P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.314
_refine_diff_density_min     -0.200
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 909 Friedel pairs'
_refine_ls_abs_structure_Flack     0.05(6)
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis RED
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997)
;
_computing_publication_material     'SHELXL97'
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
    C C1 -0.17763(17) 0.1364(8) -0.48017(15) 0.0136(5) Uani d . 1 . .
    C C2 -0.15064(17) 0.1814(7) -0.38618(15) 0.0136(5) Uani d . 1 . .
    C C3 -0.21934(19) 0.0893(7) -0.34146(16) 0.0161(5) Uani d . 1 . .
    H H3 -0.1964(19) 0.127(8) -0.2782(16) 0.019 Uiso d . 1 . .
    C C4 -0.32004(18) -0.0566(7) -0.39203(16) 0.0145(5) Uani d . 1 . .
    C C5 -0.35067(17) -0.1116(8) -0.48459(15) 0.0139(5) Uani d . 1 . .
    H H5 -0.4162(19) -0.201(7) -0.5161(16) 0.017 Uiso d . 1 . .
    C C6 -0.27979(18) -0.0155(7) -0.52667(14) 0.0145(5) Uani d . 1 . .
    C C7 0.18568(16) -0.1233(8) -0.04221(14) 0.0123(5) Uani d . 1 . .
    C C8 0.26254(17) -0.2849(7) -0.07128(14) 0.0137(5) Uani d . 1 . .
    C C9 0.36317(17) -0.4004(8) -0.01229(14) 0.0130(5) Uani d . 1 . .
    H H9 0.4118(18) -0.505(7) -0.0361(15) 0.016 Uiso d . 1 . .
    C C10 0.38899(16) -0.3535(7) 0.08034(14) 0.0129(5) Uani d . 1 . .
    C C11 0.31648(17) -0.1988(7) 0.11387(15) 0.0124(5) Uani d . 1 . .
    H H11 0.3328(18) -0.175(7) 0.1782(16) 0.015 Uiso d . 1 . .
    C C12 0.21624(17) -0.0889(7) 0.05230(15) 0.0127(5) Uani d . 1 . .
    N N1 -0.10582(16) 0.2177(6) -0.52298(15) 0.0183(5) Uani d . 1 . .
    H H1A -0.058(2) 0.357(9) -0.4968(17) 0.022 Uiso d . 1 . .
    H H1B -0.138(2) 0.262(7) -0.5786(17) 0.022 Uiso d . 1 . .
    N N2 0.08434(16) -0.0177(6) -0.10248(14) 0.0167(5) Uani d . 1 . .
    H H2A 0.077(2) 0.014(8) -0.1578(18) 0.020 Uiso d . 1 . .
    H H2B 0.0519(19) 0.132(8) -0.0836(16) 0.020 Uiso d . 1 . .
    Cl Cl1 -0.02316(4) 0.36022(18) -0.32306(4) 0.01969(14) Uani d . 1 . .
    Cl Cl2 -0.40873(4) -0.17199(18) -0.33787(4) 0.01946(15) Uani d . 1 . .
    Cl Cl3 -0.31863(5) -0.09196(19) -0.64317(4) 0.02145(16) Uani d . 1 . .
    Cl Cl4 0.22936(4) -0.34462(19) -0.18807(3) 0.01808(15) Uani d . 1 . .
    Cl Cl5 0.51505(4) -0.49705(17) 0.15626(4) 0.01731(15) Uani d . 1 . .
    Cl Cl6 0.12272(4) 0.09515(17) 0.09410(4) 0.01712(15) 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
    C1 0.0135(10) 0.0103(14) 0.0163(11) 0.0037(11) 0.0047(9) 0.0008(10)
    C2 0.0108(10) 0.0084(14) 0.0167(11) -0.0006(11) -0.0007(9) 0.0011(10)
    C3 0.0191(11) 0.0136(15) 0.0128(11) 0.0024(11) 0.0027(9) 0.0003(11)
    C4 0.0155(11) 0.0084(15) 0.0228(12) 0.0008(11) 0.0105(10) 0.0019(10)
    C5 0.0109(10) 0.0118(15) 0.0165(11) -0.0002(12) 0.0020(9) 0.0004(11)
    C6 0.0173(11) 0.0131(15) 0.0100(10) 0.0032(11) 0.0014(9) -0.0015(10)
    C7 0.0127(10) 0.0080(13) 0.0165(11) -0.0026(11) 0.0059(9) 0.0025(10)
    C8 0.0162(11) 0.0142(15) 0.0117(10) -0.0056(11) 0.0061(9) -0.0018(10)
    C9 0.0132(10) 0.0106(14) 0.0178(11) -0.0026(11) 0.0087(9) -0.0017(10)
    C10 0.0091(10) 0.0115(14) 0.0162(11) 0.0002(11) 0.0024(9) 0.0027(11)
    C11 0.0144(11) 0.0091(15) 0.0132(11) -0.0030(10) 0.0047(9) -0.0001(10)
    C12 0.0135(10) 0.0093(15) 0.0194(11) -0.0017(11) 0.0109(9) -0.0009(10)
    N1 0.0165(10) 0.0214(15) 0.0166(10) -0.0027(10) 0.0056(9) -0.0021(10)
    N2 0.0134(10) 0.0205(14) 0.0165(10) 0.0031(10) 0.0060(8) 0.0023(10)
    Cl1 0.0148(3) 0.0204(4) 0.0189(3) -0.0034(3) 0.0004(2) 0.0003(3)
    Cl2 0.0201(3) 0.0214(4) 0.0196(3) -0.0022(3) 0.0105(2) 0.0010(3)
    Cl3 0.0260(3) 0.0255(4) 0.0116(3) -0.0037(3) 0.0056(2) -0.0032(3)
    Cl4 0.0162(3) 0.0254(4) 0.0120(3) -0.0030(3) 0.0044(2) -0.0027(3)
    Cl5 0.0130(3) 0.0201(4) 0.0163(3) 0.0027(3) 0.0025(2) 0.0003(2)
    Cl6 0.0166(3) 0.0168(4) 0.0220(3) 0.0013(3) 0.0119(2) -0.0020(3)
_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 N1 . 1.385(3) ?
    C1 C6 . 1.400(3) ?
    C1 C2 . 1.402(3) ?
    C2 C3 . 1.382(3) ?
    C2 Cl1 . 1.746(2) ?
    C3 C4 . 1.389(3) ?
    C3 H3 . 0.94(2) ?
    C4 C5 . 1.380(3) ?
    C4 Cl2 . 1.739(2) ?
    C5 C6 . 1.380(3) ?
    C5 H5 . 0.89(2) ?
    C6 Cl3 . 1.741(2) ?
    C7 N2 . 1.385(3) ?
    C7 C8 . 1.398(3) ?
    C7 C12 . 1.400(3) ?
    C8 C9 . 1.383(3) ?
    C8 Cl4 . 1.745(2) ?
    C9 C10 . 1.385(3) ?
    C9 H9 . 0.94(2) ?
    C10 C11 . 1.382(3) ?
    C10 Cl5 . 1.742(2) ?
    C11 C12 . 1.386(3) ?
    C11 H11 . 0.96(2) ?
    C12 Cl6 . 1.744(2) ?
    N1 H1A . 0.81(3) ?
    N1 H1B . 0.84(2) ?
    N2 H2A . 0.85(3) ?
    N2 H2B . 0.83(3) ?
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
    N1 C1 C6 . . 122.4(2) ?
    N1 C1 C2 . . 122.3(2) ?
    C6 C1 C2 . . 115.2(2) ?
    C3 C2 C1 . . 123.3(2) ?
    C3 C2 Cl1 . . 118.81(17) ?
    C1 C2 Cl1 . . 117.87(18) ?
    C2 C3 C4 . . 118.4(2) ?
    C2 C3 H3 . . 119.1(15) ?
    C4 C3 H3 . . 122.4(15) ?
    C5 C4 C3 . . 121.0(2) ?
    C5 C4 Cl2 . . 119.55(18) ?
    C3 C4 Cl2 . . 119.49(17) ?
    C6 C5 C4 . . 118.8(2) ?
    C6 C5 H5 . . 121.5(15) ?
    C4 C5 H5 . . 119.6(15) ?
    C5 C6 C1 . . 123.3(2) ?
    C5 C6 Cl3 . . 118.36(17) ?
    C1 C6 Cl3 . . 118.35(17) ?
    N2 C7 C8 . . 122.3(2) ?
    N2 C7 C12 . . 122.1(2) ?
    C8 C7 C12 . . 115.46(19) ?
    C9 C8 C7 . . 123.41(19) ?
    C9 C8 Cl4 . . 118.41(17) ?
    C7 C8 Cl4 . . 118.17(16) ?
    C8 C9 C10 . . 118.2(2) ?
    C8 C9 H9 . . 119.4(14) ?
    C10 C9 H9 . . 122.4(14) ?
    C11 C10 C9 . . 121.4(2) ?
    C11 C10 Cl5 . . 119.34(16) ?
    C9 C10 Cl5 . . 119.23(17) ?
    C10 C11 C12 . . 118.41(19) ?
    C10 C11 H11 . . 121.7(14) ?
    C12 C11 H11 . . 119.8(14) ?
    C11 C12 C7 . . 123.1(2) ?
    C11 C12 Cl6 . . 118.73(17) ?
    C7 C12 Cl6 . . 118.21(16) ?
    C1 N1 H1A . . 116.0(18) ?
    C1 N1 H1B . . 112.1(17) ?
    H1A N1 H1B . . 114(3) ?
    C7 N2 H2A . . 117.7(17) ?
    C7 N2 H2B . . 116.6(17) ?
    H2A N2 H2B . . 113(3) ?
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
    N1 C1 C2 C3 . . . . -177.4(3) ?
    C6 C1 C2 C3 . . . . -0.9(4) ?
    N1 C1 C2 Cl1 . . . . 2.1(4) ?
    C6 C1 C2 Cl1 . . . . 178.57(19) ?
    C1 C2 C3 C4 . . . . 0.3(4) ?
    Cl1 C2 C3 C4 . . . . -179.3(2) ?
    C2 C3 C4 C5 . . . . 0.6(4) ?
    C2 C3 C4 Cl2 . . . . -179.5(2) ?
    C3 C4 C5 C6 . . . . -0.7(4) ?
    Cl2 C4 C5 C6 . . . . 179.4(2) ?
    C4 C5 C6 C1 . . . . -0.1(4) ?
    C4 C5 C6 Cl3 . . . . 179.1(2) ?
    N1 C1 C6 C5 . . . . 177.3(3) ?
    C2 C1 C6 C5 . . . . 0.8(4) ?
    N1 C1 C6 Cl3 . . . . -1.9(4) ?
    C2 C1 C6 Cl3 . . . . -178.4(2) ?
    N2 C7 C8 C9 . . . . -178.4(3) ?
    C12 C7 C8 C9 . . . . -1.0(4) ?
    N2 C7 C8 Cl4 . . . . 1.5(4) ?
    C12 C7 C8 Cl4 . . . . 178.84(19) ?
    C7 C8 C9 C10 . . . . 0.0(4) ?
    Cl4 C8 C9 C10 . . . . -179.8(2) ?
    C8 C9 C10 C11 . . . . 0.6(4) ?
    C8 C9 C10 Cl5 . . . . 179.9(2) ?
    C9 C10 C11 C12 . . . . -0.2(4) ?
    Cl5 C10 C11 C12 . . . . -179.51(19) ?
    C10 C11 C12 C7 . . . . -0.8(4) ?
    C10 C11 C12 Cl6 . . . . 178.2(2) ?
    N2 C7 C12 C11 . . . . 178.8(2) ?
    C8 C7 C12 C11 . . . . 1.4(4) ?
    N2 C7 C12 Cl6 . . . . -0.3(4) ?
    C8 C7 C12 Cl6 . . . . -177.7(2) ?
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 H1A N1 2_554 0.81(3) 2.48(3) 3.229(3) 155(2)
    N1 H1A Cl1 . 0.81(3) 2.61(3) 2.983(2) 110(2)
    N1 H1B Cl3 . 0.84(3) 2.60(3) 2.991(2) 110(2)
    N2 H2A Cl1 . 0.85(3) 2.78(3) 3.542(2) 150(2)
    N2 H2B Cl6 2 0.83(3) 2.85(3) 3.626(2) 156(2)
data_global
_journal_date_recd_electronic     2007-06-23
_journal_date_accepted     2007-06-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      7
_journal_page_first     o3347
_journal_page_last     o3347
_journal_paper_category     QO
_journal_coeditor_code     BT2410
_publ_contact_author_name     'Prof. B. Thimme Gowda'
_publ_contact_author_address
;
  Department of Chemistry
  Mangalore University
  Mangalagangotri-574 199
  Mangalore, INDIA
;
_publ_contact_author_email     gowdabt@yahoo.com
_publ_contact_author_fax     '91 824 2287367'
_publ_contact_author_phone     '91 824 2287262'
_publ_section_title
;
2,4,6-Trichloroaniline
;
loop_
    _publ_author_name
    _publ_author_address
    'B. Thimme Gowda'
; Department of Chemistry
  Mangalore University
  Mangalagangotri 574 199
  Mangalore, India
;
    'Ingrid Svoboda'
; Institute of Materials Science
  Darmstadt University of Technology
  Petersenstrasse 23
  D-64287 Darmstadt,
  Germany
;
    'Hartmut Fuess '
; Institute of Materials Science
  Darmstadt University of Technology
  Petersenstrasse 23
  D-64287 Darmstadt,
  Germany
;
