#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:18:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180071 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/17/7051747.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7051747
loop_
_publ_author_name
'Dolenc, Darko'
'Modec, Barbara'
_publ_section_title
;
 EDA Complexes of N-halosaccharins with N- and O-donor ligands
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2344
_journal_paper_doi               10.1039/b9nj00263d
_journal_volume                  33
_journal_year                    2009
_chemical_formula_sum            'C7 H4 Br N O3 S'
_chemical_formula_weight         262.08
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.1549(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.7944(2)
_cell_length_b                   28.4335(7)
_cell_length_c                   8.6973(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1730.15(8)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7625
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    4.962
_exptl_absorpt_correction_T_max  0.6637
_exptl_absorpt_correction_T_min  0.5647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
HKL SCALEPACK (Otwinowski & Minor, 1997)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.012
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0320P)²+1.3738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0795
_reflns_number_gt                3070
_reflns_number_total             3955
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b9nj00263d.txt
_cod_data_source_block           NBSac
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               7051747
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.75510(5) 0.151189(11) 0.37061(4) 0.04250(10) Uani 1 1 d . . .
S1 S 0.76216(11) 0.15744(3) 0.02338(9) 0.03493(17) Uani 1 1 d . . .
O11S O 0.9341(3) 0.13346(9) 0.0563(3) 0.0516(6) Uani 1 1 d . . .
O12S O 0.5896(3) 0.13099(8) -0.0470(3) 0.0491(5) Uani 1 1 d . . .
O71 O 0.7413(4) 0.25830(8) 0.2950(3) 0.0515(6) Uani 1 1 d . . .
N1 N 0.7836(4) 0.18561(9) 0.2032(3) 0.0407(6) Uani 1 1 d . . .
C11 C 0.7418(4) 0.21093(10) -0.0823(4) 0.0329(6) Uani 1 1 d . . .
C12 C 0.7267(4) 0.21666(12) -0.2458(4) 0.0427(7) Uani 1 1 d . . .
H12 H 0.7281 0.1911 -0.3120 0.051 Uiso 1 1 calc R . .
C13 C 0.7095(5) 0.26235(13) -0.3061(4) 0.0489(8) Uani 1 1 d . . .
H13 H 0.6970 0.2676 -0.4162 0.059 Uiso 1 1 calc R . .
C14 C 0.7104(5) 0.30016(13) -0.2075(4) 0.0511(8) Uani 1 1 d . . .
H14 H 0.6996 0.3304 -0.2516 0.061 Uiso 1 1 calc R . .
C15 C 0.7273(4) 0.29397(11) -0.0425(4) 0.0432(7) Uani 1 1 d . . .
H15 H 0.7284 0.3196 0.0243 0.052 Uiso 1 1 calc R . .
C16 C 0.7424(4) 0.24852(10) 0.0192(4) 0.0335(6) Uani 1 1 d . . .
C17 C 0.7563(4) 0.23410(11) 0.1884(4) 0.0361(6) Uani 1 1 d . . .
Br2 Br 0.30066(5) 0.148528(11) -0.56978(4) 0.04370(10) Uani 1 1 d . . .
S2 S 0.22716(10) 0.05827(3) -0.41155(10) 0.03960(18) Uani 1 1 d . . .
O21S O 0.1660(3) 0.08166(9) -0.3002(3) 0.0561(6) Uani 1 1 d . . .
O22S O 0.0867(3) 0.04078(9) -0.5703(3) 0.0538(6) Uani 1 1 d . . .
O72 O 0.6957(3) 0.10114(8) -0.3897(3) 0.0474(5) Uani 1 1 d . . .
N2 N 0.3803(3) 0.09323(9) -0.4505(3) 0.0441(6) Uani 1 1 d . . .
C21 C 0.4111(4) 0.01779(10) -0.3000(4) 0.0362(6) Uani 1 1 d . . .
C22 C 0.3966(5) -0.02383(12) -0.2258(4) 0.0473(8) Uani 1 1 d . . .
H22 H 0.2804 -0.0343 -0.2327 0.057 Uiso 1 1 calc R . .
C23 C 0.5633(5) -0.04938(12) -0.1403(4) 0.0532(9) Uani 1 1 d . . .
H23 H 0.5588 -0.0776 -0.0881 0.064 Uiso 1 1 calc R . .
C24 C 0.7355(5) -0.03415(12) -0.1305(4) 0.0521(9) Uani 1 1 d . . .
H24 H 0.8445 -0.0523 -0.0731 0.063 Uiso 1 1 calc R . .
C25 C 0.7486(4) 0.00816(12) -0.2057(4) 0.0451(7) Uani 1 1 d . . .
H25 H 0.8647 0.0186 -0.1991 0.054 Uiso 1 1 calc R . .
C26 C 0.5839(4) 0.03393(10) -0.2898(4) 0.0351(6) Uani 1 1 d . . .
C27 C 0.5691(4) 0.07935(11) -0.3787(3) 0.0360(6) Uani 1 1 d . . .
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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11S S1 O12S 117.62(15) . . ?
O11S S1 N1 109.94(14) . . ?
O12S S1 N1 109.64(13) . . ?
O11S S1 C11 112.56(14) . . ?
O12S S1 C11 112.60(14) . . ?
N1 S1 C11 91.33(13) . . ?
C17 N1 S1 115.63(19) . . ?
C17 N1 Br1 122.08(19) . . ?
S1 N1 Br1 118.60(15) . . ?
C12 C11 C16 122.6(3) . . ?
C12 C11 S1 126.1(2) . . ?
C16 C11 S1 111.2(2) . . ?
C11 C12 C13 116.7(3) . . ?
C11 C12 H12 121.6 . . ?
C13 C12 H12 121.6 . . ?
C14 C13 C12 121.6(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 121.1(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 118.1(3) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C15 C16 C11 119.8(3) . . ?
C15 C16 C17 126.8(3) . . ?
C11 C16 C17 113.4(2) . . ?
O71 C17 N1 124.0(3) . . ?
O71 C17 C16 128.1(3) . . ?
N1 C17 C16 107.9(2) . . ?
O21S S2 O22S 118.71(15) . . ?
O21S S2 N2 109.81(15) . . ?
O22S S2 N2 108.61(14) . . ?
O21S S2 C21 111.57(14) . . ?
O22S S2 C21 113.47(15) . . ?
N2 S2 C21 91.10(13) . . ?
C27 N2 S2 116.5(2) . . ?
C27 N2 Br2 121.9(2) . . ?
S2 N2 Br2 121.46(14) . . ?
C22 C21 C26 122.2(3) . . ?
C22 C21 S2 127.3(2) . . ?
C26 C21 S2 110.5(2) . . ?
C21 C22 C23 116.8(3) . . ?
C21 C22 H22 121.6 . . ?
C23 C22 H22 121.6 . . ?
C24 C23 C22 121.8(3) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C23 C24 C25 120.9(3) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 117.7(3) . . ?
C26 C25 H25 121.1 . . ?
C24 C25 H25 121.1 . . ?
C25 C26 C21 120.6(3) . . ?
C25 C26 C27 125.5(3) . . ?
C21 C26 C27 113.8(3) . . ?
O72 C27 N2 124.4(3) . . ?
O72 C27 C26 127.7(3) . . ?
N2 C27 C26 107.9(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 N1 1.847(2) . ?
S1 O11S 1.416(2) . ?
S1 O12S 1.422(2) . ?
S1 N1 1.699(2) . ?
S1 C11 1.748(3) . ?
O71 C17 1.201(3) . ?
N1 C17 1.393(4) . ?
C11 C12 1.384(4) . ?
C11 C16 1.385(4) . ?
C12 C13 1.385(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.393(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.485(4) . ?
Br2 N2 1.835(3) . ?
S2 O21S 1.419(2) . ?
S2 O22S 1.421(2) . ?
S2 N2 1.699(3) . ?
S2 C21 1.759(3) . ?
O72 C27 1.203(3) . ?
N2 C27 1.379(4) . ?
C21 C22 1.376(4) . ?
C21 C26 1.388(4) . ?
C22 C23 1.384(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.377(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.394(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.375(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.483(4) . ?
