#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006962.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2006962
loop_
_publ_author_name
'Alarc\`on, R.'
'Cox, O.'
'Rivera, L. A.'
'Huang, S. D.'
_publ_section_title
;
 <i>erythro</i>-1-(Benzothiazol-2-yl)-1,2-dibromo-2-(2-chloro-5-nitrophenyl)ethane
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              68
_journal_page_last               69
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C15 H9 Br2 Cl N2 O2 S'
_chemical_formula_sum            'C15 H9 Br2 Cl N2 O2 S'
_chemical_formula_weight         476.57
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 104.51(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.557(4)
_cell_length_b                   14.518(5)
_cell_length_c                   11.094(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295.0(10)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      12
_cell_volume                     1646.1(10)
_computing_cell_refinement       'CAD-4-PC Software'
_computing_data_collection       'CAD-4-PC Software (Enraf-Nonius, 1992)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1985, 1992)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      295.2
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3202
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.237
_exptl_absorpt_correction_T_max  0.069
_exptl_absorpt_correction_T_min  0.046
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '\y scan (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.923
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             928.00
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.51
_refine_diff_density_max         1.41
_refine_diff_density_min         -0.69
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.905
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2300
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.053
_refine_ls_shift/esd_max         0.0034
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme
'sigma; w = 1/[\s^2^~c~(F~o~) + (p^3^/4F~o~^2^)], with p = 0.03'
_refine_ls_wR_factor_obs         0.061
_reflns_number_observed          2300
_reflns_number_total             3187
_reflns_observed_criterion       I>2.5\s(I)
_[local]_cod_data_source_file    sx1024.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_original_cell_volume        1646.1(9)
_cod_database_code               2006962
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,1/2+y,1/2-z'
'   -x,   -y,   -z'
'   +x,1/2-y,1/2+z'
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
Br(1) 0.0553(4) 0.0689(4) 0.0540(4) 0.0068(3) 0.0149(3) 0.0211(3)
Br(2) 0.0550(4) 0.0865(5) 0.0462(4) 0.0012(3) 0.0184(3) 0.0243(3)
Cl 0.0711(10) 0.0402(8) 0.0690(10) 0.0027(7) 0.0219(8) -0.0160(7)
S 0.0553(8) 0.0454(8) 0.0700(10) -0.0048(7) 0.0319(8) -0.0059(7)
O(1) 0.079(3) 0.094(4) 0.090(4) 0.006(3) 0.062(3) 0.001(3)
O(2) 0.074(3) 0.056(3) 0.066(3) 0.010(2) 0.029(2) -0.013(2)
N(1) 0.047(3) 0.054(3) 0.062(3) -0.008(2) 0.026(2) -0.014(2)
N(2) 0.052(3) 0.061(3) 0.046(3) 0.008(2) 0.023(2) 0.003(2)
C(1) 0.045(3) 0.045(3) 0.053(3) -0.002(2) 0.021(3) -0.005(3)
C(2) 0.044(3) 0.061(4) 0.040(3) -0.001(3) 0.014(2) 0.000(3)
C(3) 0.065(4) 0.075(4) 0.064(4) -0.020(3) 0.026(3) 0.003(3)
C(4) 0.059(4) 0.131(7) 0.057(4) -0.035(4) 0.027(3) -0.012(4)
C(5) 0.055(4) 0.151(7) 0.050(4) -0.026(4) 0.031(3) -0.027(4)
C(6) 0.048(3) 0.096(5) 0.052(4) -0.006(3) 0.020(3) -0.025(3)
C(7) 0.038(3) 0.068(4) 0.041(3) -0.006(3) 0.012(2) -0.005(3)
C(8) 0.053(3) 0.041(3) 0.050(3) 0.001(3) 0.024(3) -0.002(2)
C(9) 0.051(3) 0.040(3) 0.055(3) 0.001(2) 0.023(3) -0.005(3)
C(10) 0.042(3) 0.032(3) 0.039(3) 0.001(2) 0.016(2) 0.000(2)
C(11) 0.049(3) 0.035(3) 0.034(3) 0.003(2) 0.011(2) -0.002(2)
C(12) 0.054(3) 0.033(3) 0.065(4) -0.012(2) 0.014(3) 0.003(3)
C(13) 0.051(3) 0.052(3) 0.055(3) -0.005(3) 0.023(3) 0.005(3)
C(14) 0.048(3) 0.039(3) 0.033(3) 0.002(2) 0.017(2) 0.004(2)
C(15) 0.051(3) 0.032(3) 0.047(3) -0.003(2) 0.021(2) -0.002(2)
loop_
_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
Br(1) 0.19134(6) 0.20827(4) 0.02298(6) 0.0592(2) Uij
Br(2) 0.41745(6) 0.08456(5) 0.39943(6) 0.0616(2) Uij
Cl 0.4561(2) 0.36839(10) 0.31000(10) 0.0594(5) Uij
S 0.07300(10) -0.01450(10) 0.19120(10) 0.0540(4) Uij
O(1) 0.7961(5) 0.1210(3) 0.0089(4) 0.080(2) Uij
O(2) 0.6657(4) 0.0162(3) 0.0419(4) 0.0630(10) Uij
N(1) 0.0842(4) 0.1504(3) 0.2815(4) 0.0520(10) Uij
N(2) 0.7072(5) 0.0952(3) 0.0511(4) 0.0510(10) Uij
C(1) 0.1378(5) 0.0953(4) 0.2154(5) 0.046(2) Uij
C(2) -0.0320(5) 0.0119(4) 0.2812(5) 0.047(2) Uij
C(3) -0.1244(7) -0.0421(5) 0.3131(6) 0.066(2) Uij
C(4) -0.1989(7) -0.0055(6) 0.3863(6) 0.080(2) Uij
C(5) -0.1832(6) 0.0842(6) 0.4245(6) 0.082(3) Uij
C(6) -0.0912(6) 0.1425(5) 0.3921(5) 0.064(2) Uij
C(7) -0.0143(5) 0.1045(4) 0.3193(5) 0.049(2) Uij
C(8) 0.2500(5) 0.1226(4) 0.1640(5) 0.046(2) Uij
C(9) 0.3548(5) 0.1708(4) 0.2554(5) 0.047(2) Uij
C(10) 0.4735(5) 0.1991(3) 0.2126(5) 0.0370(10) Uij
C(11) 0.5286(5) 0.2855(3) 0.2365(4) 0.0390(10) Uij
C(12) 0.6412(6) 0.3099(3) 0.2027(5) 0.051(2) Uij
C(13) 0.7021(5) 0.2474(4) 0.1421(5) 0.051(2) Uij
C(14) 0.6459(5) 0.1623(3) 0.1181(4) 0.0390(10) Uij
C(15) 0.5353(5) 0.1370(3) 0.1518(5) 0.0420(10) Uij
H(1) -0.1365 -0.1042 0.2846 0.0797 Uij
H(2) -0.2620 -0.0427 0.4108 0.0959 Uij
H(3) -0.2368 0.1083 0.4750 0.0983 Uij
H(4) -0.0820 0.2051 0.4190 0.0766 Uij
H(5) 0.2859 0.0688 0.1352 0.0556 Uij
H(6) 0.3183 0.2241 0.2845 0.0562 Uij
H(7) 0.6766 0.3700 0.2215 0.0612 Uij
H(8) 0.7798 0.2626 0.1177 0.0607 Uij
H(9) 0.5011 0.0766 0.1335 0.0502 Uij
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0.000 0.000 'International Tables'
C 0.003 0.002 'International Tables'
N 0.006 0.003 'International Tables'
O 0.011 0.006 'International Tables'
S 0.125 0.123 'International Tables'
Cl 0.148 0.159 'International Tables'
Br -0.290 2.459 'International Tables'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 2 7
-1 7 -3
1 8 -3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(1) S C(2) 89.5(3) yes
C(1) N(1) C(7) 109.9(4) yes
O(1) N(2) O(2) 123.6(5) no
O(1) N(2) C(14) 118.3(5) no
O(2) N(2) C(14) 118.0(4) no
S C(1) N(1) 116.2(4) yes
S C(1) C(8) 120.4(4) yes
N(1) C(1) C(8) 123.3(5) yes
S C(2) C(3) 129.2(5) yes
S C(2) C(7) 109.4(4) yes
C(3) C(2) C(7) 121.4(5) no
C(2) C(3) C(4) 119.0(6) no
C(3) C(4) C(5) 120.7(6) no
C(4) C(5) C(6) 122.2(6) no
C(5) C(6) C(7) 116.9(6) no
N(1) C(7) C(2) 114.9(5) yes
N(1) C(7) C(6) 125.2(5) yes
C(2) C(7) C(6) 119.9(5) no
Br(1) C(8) C(1) 110.4(4) yes
Br(1) C(8) C(9) 106.2(4) yes
C(1) C(8) C(9) 113.2(5) yes
Br(2) C(9) C(8) 107.0(4) yes
Br(2) C(9) C(10) 106.7(4) yes
C(8) C(9) C(10) 117.0(5) yes
C(9) C(10) C(11) 122.2(5) yes
C(9) C(10) C(15) 120.5(4) yes
C(11) C(10) C(15) 117.3(5) no
Cl C(11) C(10) 120.4(4) no
Cl C(11) C(12) 117.5(4) no
C(10) C(11) C(12) 122.1(5) no
C(11) C(12) C(13) 120.1(5) no
C(12) C(13) C(14) 117.2(5) no
N(2) C(14) C(13) 118.2(5) no
N(2) C(14) C(15) 118.5(4) no
C(13) C(14) C(15) 123.3(5) no
C(10) C(15) C(14) 120.0(4) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br(1) C(8) 1.972(5) yes
Br(2) C(9) 2.007(6) yes
Cl C(11) 1.736(5) yes
S C(1) 1.729(5) yes
S C(2) 1.711(5) yes
O(1) N(2) 1.209(6) no
O(2) N(2) 1.223(6) no
N(1) C(1) 1.306(7) yes
N(1) C(7) 1.385(7) yes
N(2) C(14) 1.470(6) no
C(1) C(8) 1.492(7) yes
C(2) C(3) 1.366(8) no
C(2) C(7) 1.408(8) no
C(3) C(4) 1.371(9) no
C(4) C(5) 1.370(10) no
C(5) C(6) 1.401(9) no
C(6) C(7) 1.395(8) no
C(8) C(9) 1.476(8) yes
C(9) C(10) 1.504(7) yes
C(10) C(11) 1.380(7) no
C(10) C(15) 1.383(7) no
C(11) C(12) 1.379(7) no
C(12) C(13) 1.380(8) no
C(13) C(14) 1.368(7) no
C(14) C(15) 1.362(7) no