#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:18:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180071 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/17/7051746.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_7051746
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            'C18 H12 Br2 N4 O6 S2'
_chemical_formula_weight         604.26
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.2877(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.78470(10)
_cell_length_b                   9.8956(2)
_cell_length_c                   14.0214(2)
_cell_measurement_temperature    150(2)
_cell_volume                     1073.63(3)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0105
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4719
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    4.015
_exptl_absorpt_correction_T_max  0.7947
_exptl_absorpt_correction_T_min  0.6896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
HKL SCALEPACK (Otwinowski & Minor, 1997)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0212
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0293P)²+0.5749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0547
_refine_ls_wR_factor_ref         0.0557
_reflns_number_gt                2313
_reflns_number_total             2449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b9nj00263d.txt
_cod_data_source_block           NBSac2.Pyz
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7051746
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.10881(2) 0.082276(16) 0.750211(11) 0.02148(7) Uani 1 1 d . . .
S1 S 0.26960(5) 0.05934(4) 0.55610(3) 0.01876(10) Uani 1 1 d . . .
O1S O 0.44433(16) 0.08365(13) 0.59642(9) 0.0256(3) Uani 1 1 d . . .
O2S O 0.21886(19) -0.07812(12) 0.53980(10) 0.0291(3) Uani 1 1 d . . .
O7 O -0.05752(16) 0.31424(13) 0.61697(9) 0.0271(3) Uani 1 1 d . . .
N1 N 0.1338(2) 0.13658(16) 0.62203(10) 0.0269(3) Uani 1 1 d . . .
N2 N 0.44400(18) 0.52537(15) 0.58845(10) 0.0221(3) Uani 1 1 d . . .
C1 C 0.2115(2) 0.16433(16) 0.45671(11) 0.0179(3) Uani 1 1 d . . .
C2 C 0.2729(2) 0.15970(18) 0.36790(12) 0.0228(3) Uani 1 1 d . . .
H2 H 0.3513 0.0940 0.3532 0.027 Uiso 1 1 calc R . .
C3 C 0.2120(2) 0.25796(19) 0.30155(12) 0.0246(4) Uani 1 1 d . . .
H3 H 0.2506 0.2582 0.2411 0.030 Uiso 1 1 calc R . .
C4 C 0.0949(2) 0.35551(19) 0.32399(12) 0.0256(4) Uani 1 1 d . . .
H4 H 0.0566 0.4203 0.2785 0.031 Uiso 1 1 calc R . .
C5 C 0.0337(2) 0.35788(17) 0.41369(12) 0.0221(3) Uani 1 1 d . . .
H5 H -0.0455 0.4229 0.4285 0.027 Uiso 1 1 calc R . .
C6 C 0.0938(2) 0.26092(16) 0.48019(11) 0.0182(3) Uani 1 1 d . . .
C7 C 0.0435(2) 0.24532(16) 0.57886(12) 0.0199(3) Uani 1 1 d . . .
C21 C 0.5183(3) 0.40827(17) 0.57000(13) 0.0248(4) Uani 1 1 d . . .
H21 H 0.5329 0.3425 0.6176 0.030 Uiso 1 1 calc R . .
C22 C 0.5742(2) 0.38260(18) 0.48128(12) 0.0233(3) Uani 1 1 d . . .
H22 H 0.6252 0.2999 0.4702 0.028 Uiso 1 1 calc R . .
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
O2S S1 O1S 117.15(8) . . ?
O2S S1 N1 110.18(9) . . ?
O1S S1 N1 109.66(8) . . ?
O2S S1 C1 113.18(8) . . ?
O1S S1 C1 111.35(8) . . ?
N1 S1 C1 92.58(7) . . ?
C7 N1 S1 115.85(11) . . ?
C7 N1 Br1 122.06(11) . . ?
S1 N1 Br1 122.07(8) . . ?
C22 N2 C21 117.73(15) 3_666 . ?
C2 C1 C6 122.60(15) . . ?
C2 C1 S1 127.59(13) . . ?
C6 C1 S1 109.77(12) . . ?
C1 C2 C3 116.89(16) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C4 C3 C2 121.23(15) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.97(16) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 118.23(16) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C1 120.07(15) . . ?
C5 C6 C7 126.53(15) . . ?
C1 C6 C7 113.39(14) . . ?
O7 C7 N1 124.59(15) . . ?
O7 C7 C6 127.10(15) . . ?
N1 C7 C6 108.31(13) . . ?
N2 C21 C22 121.28(17) . . ?
N2 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
N2 C22 C21 120.99(16) 3_666 . ?
N2 C22 H22 119.5 3_666 . ?
C21 C22 H22 119.5 . . ?
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 1.9062(14) . ?
S1 O2S 1.4279(13) . ?
S1 O1S 1.4350(13) . ?
S1 N1 1.6644(15) . ?
S1 C1 1.7573(16) . ?
O7 C7 1.209(2) . ?
N1 C7 1.387(2) . ?
N2 C22 1.332(2) 3_666 ?
N2 C21 1.333(2) . ?
C1 C2 1.383(2) . ?
C1 C6 1.388(2) . ?
C2 C3 1.393(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.487(2) . ?
C21 C22 1.386(3) . ?
C21 H21 0.9300 . ?
C22 N2 1.332(2) 3_666 ?
C22 H22 0.9300 . ?
