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###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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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# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2,2,2-Tribromo-N-(2-chlorophenyl)acetamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H5 Br3 Cl N O'
_chemical_formula_sum     'C8 H5 Br3 Cl N O'
_chemical_formula_iupac     'C8 H5 Br3 Cl N O'
_chemical_formula_weight     406.31
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
_symmetry_space_group_name_HALL     'P 2c -2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    '-x+1/2, y+1/2, z+1/2'
    'x+1/2, -y+1/2, z'
_cell_length_a     9.1947(6)
_cell_length_b     12.9645(7)
_cell_length_c     9.5213(6)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1134.98(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3507
_cell_measurement_theta_min     2.66
_cell_measurement_theta_max     27.82
_cell_measurement_temperature     299(2)
_exptl_crystal_description     rod
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.34
_exptl_crystal_density_diffrn     2.378
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     760
_exptl_absorpt_coefficient_mu     10.864
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_absorpt_correction_T_min     0.0978
_exptl_absorpt_correction_T_max     0.1195
_exptl_special_details
;
CrysAlis RED (Oxford Diffraction, 2009)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature     299(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
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω and φ scans.
;
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4524
_diffrn_reflns_av_R_equivalents     0.0221
_diffrn_reflns_av_sigmaI/netI     0.0195
_diffrn_reflns_theta_min     2.65
_diffrn_reflns_theta_max     26.37
_diffrn_reflns_theta_full     26.37
_diffrn_measured_fraction_theta_max     0.984
_diffrn_measured_fraction_theta_full     0.984
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     6
_diffrn_standards_number     0
_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 >
σ(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     1645
_reflns_number_gt     1491
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0321
_refine_ls_R_factor_gt     0.0271
_refine_ls_wR_factor_gt     0.0640
_refine_ls_wR_factor_ref     0.0655
_refine_ls_goodness_of_fit_ref     1.067
_refine_ls_restrained_S_all     1.066
_refine_ls_number_reflns     1645
_refine_ls_number_parameters     131
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0357P)²+1.2795P] 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     0.004
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.767
_refine_diff_density_min     -0.560
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0072(5)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983), 416 Friedel pairs'
_refine_ls_abs_structure_Flack     0.049(18)
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'
    'Br' 'Br' -0.2901 2.4595
                         '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'
    '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 (Oxford Diffraction, 2009)
;
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 0.56049(8) 0.28366(5) 1.15778(8) 0.0510(2) Uani d . 1 . .
    Br Br2 0.43394(7) 0.06152(5) 1.19542(7) 0.0483(2) Uani d . 1 . .
    Br Br3 0.70743(6) 0.09279(5) 1.00260(9) 0.0474(2) Uani d . 1 . .
    Cl Cl1 0.5017(2) 0.46215(12) 0.7770(2) 0.0536(5) Uani d . 1 . .
    O O1 0.3140(5) 0.1287(4) 0.9233(5) 0.0521(13) Uani d . 1 . .
    N N1 0.4832(5) 0.2390(4) 0.8407(6) 0.0366(12) Uani d D 1 . .
    H H1N 0.554(5) 0.277(4) 0.866(9) 0.044 Uiso d D 1 . .
    C C1 0.4101(6) 0.2689(4) 0.7164(7) 0.0311(12) Uani d . 1 . .
    C C2 0.4114(6) 0.3709(4) 0.6763(7) 0.0360(14) Uani d . 1 . .
    C C3 0.3435(8) 0.4026(5) 0.5526(7) 0.0475(17) Uani d . 1 . .
    H H3 0.3476 0.4712 0.5244 0.057 Uiso calc R 1 . .
    C C4 0.2701(8) 0.3305(6) 0.4724(8) 0.0573(19) Uani d . 1 . .
    H H4 0.2235 0.3506 0.3901 0.069 Uiso calc R 1 . .
    C C5 0.2660(9) 0.2308(6) 0.5136(9) 0.063(2) Uani d . 1 . .
    H H5 0.2152 0.1829 0.4598 0.076 Uiso calc R 1 . .
    C C6 0.3362(8) 0.1987(5) 0.6347(7) 0.0471(17) Uani d . 1 . .
    H H6 0.3335 0.1296 0.6607 0.057 Uiso calc R 1 . .
    C C7 0.4282(6) 0.1716(4) 0.9346(6) 0.0278(12) Uani d . 1 . .
    C C8 0.5253(6) 0.1542(4) 1.0638(7) 0.0288(12) 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 0.0744(5) 0.0373(3) 0.0411(4) -0.0059(3) -0.0169(4) -0.0036(3)
    Br2 0.0476(4) 0.0509(4) 0.0464(4) -0.0058(3) 0.0000(3) 0.0248(3)
    Br3 0.0328(3) 0.0471(4) 0.0623(5) 0.0097(3) 0.0018(3) 0.0139(4)
    Cl1 0.0620(10) 0.0384(8) 0.0604(12) -0.0142(8) -0.0155(9) 0.0153(8)
    O1 0.047(3) 0.067(3) 0.043(3) -0.025(2) -0.009(2) 0.011(3)
    N1 0.040(3) 0.035(3) 0.035(3) -0.007(2) -0.008(2) 0.013(3)
    C1 0.035(3) 0.032(3) 0.026(3) 0.008(2) 0.000(2) 0.004(2)
    C2 0.032(3) 0.036(3) 0.040(4) 0.004(2) 0.004(3) 0.004(3)
    C3 0.057(4) 0.052(4) 0.033(4) 0.018(3) 0.004(3) 0.018(3)
    C4 0.074(5) 0.070(5) 0.028(4) 0.010(4) -0.017(4) 0.012(4)
    C5 0.092(5) 0.065(5) 0.033(4) 0.011(4) -0.020(4) -0.016(4)
    C6 0.068(4) 0.039(3) 0.034(4) 0.011(3) -0.005(4) -0.002(3)
    C7 0.028(3) 0.027(3) 0.029(3) 0.002(2) 0.000(2) 0.000(2)
    C8 0.032(3) 0.027(3) 0.027(3) 0.001(2) -0.001(2) 0.008(2)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'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
    Br1 C8 . 1.929(6) ?
    Br2 C8 . 1.929(6) ?
    Br3 C8 . 1.944(6) ?
    Cl1 C2 . 1.735(7) ?
    O1 C7 . 1.193(6) ?
    N1 C7 . 1.349(7) ?
    N1 C1 . 1.415(8) ?
    N1 H1N . 0.85(3) ?
    C1 C6 . 1.377(9) ?
    C1 C2 . 1.376(8) ?
    C2 C3 . 1.395(9) ?
    C3 C4 . 1.383(10) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.351(11) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.385(10) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.537(8) ?
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
    C7 N1 C1 . . 123.6(5) ?
    C7 N1 H1N . . 118(6) ?
    C1 N1 H1N . . 116(5) ?
    C6 C1 C2 . . 118.8(6) ?
    C6 C1 N1 . . 121.7(5) ?
    C2 C1 N1 . . 119.4(6) ?
    C1 C2 C3 . . 120.9(6) ?
    C1 C2 Cl1 . . 120.4(5) ?
    C3 C2 Cl1 . . 118.7(5) ?
    C4 C3 C2 . . 119.0(6) ?
    C4 C3 H3 . . 120.5 ?
    C2 C3 H3 . . 120.5 ?
    C5 C4 C3 . . 120.0(6) ?
    C5 C4 H4 . . 120.0 ?
    C3 C4 H4 . . 120.0 ?
    C4 C5 C6 . . 121.1(7) ?
    C4 C5 H5 . . 119.5 ?
    C6 C5 H5 . . 119.5 ?
    C1 C6 C5 . . 120.1(6) ?
    C1 C6 H6 . . 119.9 ?
    C5 C6 H6 . . 119.9 ?
    O1 C7 N1 . . 124.9(6) ?
    O1 C7 C8 . . 121.0(5) ?
    N1 C7 C8 . . 114.1(4) ?
    C7 C8 Br1 . . 110.0(4) ?
    C7 C8 Br2 . . 111.0(4) ?
    Br1 C8 Br2 . . 108.3(3) ?
    C7 C8 Br3 . . 108.7(4) ?
    Br1 C8 Br3 . . 110.5(3) ?
    Br2 C8 Br3 . . 108.3(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
    C7 N1 C1 C6 . . . . -41.6(9) ?
    C7 N1 C1 C2 . . . . 137.9(6) ?
    C6 C1 C2 C3 . . . . -2.1(9) ?
    N1 C1 C2 C3 . . . . 178.4(6) ?
    C6 C1 C2 Cl1 . . . . 179.4(5) ?
    N1 C1 C2 Cl1 . . . . -0.1(8) ?
    C1 C2 C3 C4 . . . . 2.2(10) ?
    Cl1 C2 C3 C4 . . . . -179.4(5) ?
    C2 C3 C4 C5 . . . . -0.7(11) ?
    C3 C4 C5 C6 . . . . -0.9(12) ?
    C2 C1 C6 C5 . . . . 0.6(10) ?
    N1 C1 C6 C5 . . . . -179.9(6) ?
    C4 C5 C6 C1 . . . . 0.9(12) ?
    C1 N1 C7 O1 . . . . 1.1(9) ?
    C1 N1 C7 C8 . . . . -177.9(5) ?
    O1 C7 C8 Br1 . . . . -121.3(5) ?
    N1 C7 C8 Br1 . . . . 57.7(6) ?
    O1 C7 C8 Br2 . . . . -1.5(7) ?
    N1 C7 C8 Br2 . . . . 177.5(4) ?
    O1 C7 C8 Br3 . . . . 117.5(5) ?
    N1 C7 C8 Br3 . . . . -63.4(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
    N1 H1N Br1 . 0.85(3) 2.78(8) 3.155(6) 109(6)
    N1 H1N Cl1 . 0.85(3) 2.59(7) 2.961(5) 107(5)
data_global
_journal_date_recd_electronic     2010-01-10
_journal_date_accepted     2010-01-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      2
_journal_page_first     o386
_journal_page_last     o386
_journal_paper_category     QO
_journal_coeditor_code     BT5167
_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
;
2,2,2-Tribromo-N-(2-chlorophenyl)acetamide
;
loop_
    _publ_author_name
    _publ_author_address
    'B. Thimme Gowda'
; Department of Chemistry
  Mangalore University
  Mangalagangotri 574 199
  Mangalore, India
;
    'Sabine Foro'
; Institute of Materials Science
  Darmstadt University of Technology
  Petersenstrasse 23
  D-64287 Darmstadt, Germany
;
    'P. A. Suchetan'
; Department of Chemistry
  Mangalore University
  Mangalagangotri 574 199
  Mangalore, India
;
    'Hartmut Fuess'
; Institute of Materials Science
  Darmstadt University of Technology
  Petersenstrasse 23
  D-64287 Darmstadt, Germany
;
