#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/34/7103426.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_7103426
loop_
_publ_author_name
'Bacon, Catherine E'
'Eisler, Dana J'
'Melen, Rebecca L'
'Rawson, Jeremy M'
_publ_section_title
;
 Formation of N-bridgehead 1,2,5-thiadiazolium and selenadiazolium
 rings through an intramolecular cyclisation reaction.
;
_journal_issue                   40
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4924
_journal_page_last               4926
_journal_paper_doi               10.1039/b809987a
_journal_year                    2008
_chemical_formula_moiety         'C11 H10 Cl N3 O S'
_chemical_formula_sum            'C11 H10 Cl N3 O S'
_chemical_formula_weight         267.73
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 111.0242(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.1059(6)
_cell_length_b                   4.9368(2)
_cell_length_c                   20.7418(6)
_cell_measurement_reflns_used    7515
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2304.07(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick 1997)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9748
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.498
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2635
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0285P)²+3.3848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0884
_reflns_number_gt                1982
_reflns_number_total             2635
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b809987a.txt
_cod_data_source_block           jr0708a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_Hall     -C2yc
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7103426
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
N1 N 0.52316(8) 0.2492(4) 0.45092(8) 0.0249(4) Uani 1 1 d . . .
S1 S 0.58043(2) 0.44545(12) 0.48516(3) 0.02534(15) Uani 1 1 d . . .
N2 N 0.61813(7) 0.3066(4) 0.43642(8) 0.0222(4) Uani 1 1 d . . .
C1 C 0.67375(9) 0.3733(5) 0.43889(11) 0.0262(5) Uani 1 1 d . . .
H1A H 0.6959 0.5120 0.4689 0.031 Uiso 1 1 calc R . .
C2 C 0.69691(10) 0.2360(5) 0.39709(11) 0.0299(5) Uani 1 1 d . . .
H2A H 0.7356 0.2790 0.3981 0.036 Uiso 1 1 calc R . .
C3 C 0.66407(10) 0.0326(5) 0.35282(11) 0.0307(5) Uani 1 1 d . . .
H3A H 0.6805 -0.0611 0.3238 0.037 Uiso 1 1 calc R . .
C4 C 0.60821(9) -0.0316(5) 0.35120(11) 0.0270(5) Uani 1 1 d . . .
H4A H 0.5857 -0.1687 0.3209 0.032 Uiso 1 1 calc R . .
C5 C 0.58480(9) 0.1059(4) 0.39436(10) 0.0223(4) Uani 1 1 d . . .
C6 C 0.52880(9) 0.0804(4) 0.40480(10) 0.0221(4) Uani 1 1 d . . .
C7 C 0.47992(9) -0.1075(4) 0.36796(10) 0.0223(5) Uani 1 1 d . . .
C8 C 0.42549(9) -0.0862(5) 0.37597(10) 0.0260(5) Uani 1 1 d . . .
H8A H 0.4189 0.0500 0.4048 0.031 Uiso 1 1 calc R . .
C9 C 0.38091(9) -0.2664(5) 0.34132(11) 0.0289(5) Uani 1 1 d . . .
H9A H 0.3433 -0.2570 0.3463 0.035 Uiso 1 1 calc R . .
C10 C 0.39191(9) -0.4609(5) 0.29928(11) 0.0280(5) Uani 1 1 d . . .
H10A H 0.3620 -0.5866 0.2745 0.034 Uiso 1 1 calc R . .
C11 C 0.44753(9) -0.4671(5) 0.29431(11) 0.0272(5) Uani 1 1 d . . .
H11A H 0.4549 -0.6008 0.2654 0.033 Uiso 1 1 calc R . .
N3 N 0.49180(7) -0.2959(4) 0.32775(8) 0.0244(4) Uani 1 1 d . . .
O1 O 0.76072(8) 0.7421(4) 0.28243(9) 0.0401(4) Uani 1 1 d D . .
H1C H 0.7538(14) 0.587(3) 0.2643(15) 0.066(10) Uiso 1 1 d D . .
H1B H 0.7773(12) 0.716(7) 0.3255(6) 0.065(10) Uiso 1 1 d D . .
Cl1 Cl 0.68040(2) 0.83197(12) 0.55615(3) 0.03117(16) 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'
S S 0.1246 0.1234 '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'
Cl Cl 0.1484 0.1585 '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
C6 N1 S1 113.76(14) . . ?
N1 S1 N2 92.89(9) . . ?
C1 N2 C5 122.79(18) . . ?
C1 N2 S1 126.83(15) . . ?
C5 N2 S1 110.36(13) . . ?
N2 C1 C2 118.4(2) . . ?
N2 C1 H1A 120.8 . . ?
C2 C1 H1A 120.8 . . ?
C1 C2 C3 120.6(2) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
N2 C5 C4 118.69(18) . . ?
N2 C5 C6 109.42(17) . . ?
C4 C5 C6 131.89(19) . . ?
N1 C6 C5 113.57(18) . . ?
N1 C6 C7 120.21(18) . . ?
C5 C6 C7 126.20(18) . . ?
N3 C7 C8 123.23(19) . . ?
N3 C7 C6 116.48(18) . . ?
C8 C7 C6 120.29(19) . . ?
C9 C8 C7 118.8(2) . . ?
C9 C8 H8A 120.6 . . ?
C7 C8 H8A 120.6 . . ?
C8 C9 C10 119.0(2) . . ?
C8 C9 H9A 120.5 . . ?
C10 C9 H9A 120.5 . . ?
C11 C10 C9 118.2(2) . . ?
C11 C10 H10A 120.9 . . ?
C9 C10 H10A 120.9 . . ?
N3 C11 C10 124.1(2) . . ?
N3 C11 H11A 118.0 . . ?
C10 C11 H11A 118.0 . . ?
C11 N3 C7 116.63(18) . . ?
H1C O1 H1B 106(3) . . ?
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
N1 C6 1.312(3) . ?
N1 S1 1.6266(18) . ?
S1 N2 1.7253(18) . ?
N2 C1 1.364(3) . ?
N2 C5 1.373(3) . ?
C1 C2 1.368(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.399(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.372(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.394(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.447(3) . ?
C6 C7 1.479(3) . ?
C7 N3 1.347(3) . ?
C7 C8 1.384(3) . ?
C8 C9 1.381(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.382(3) . ?
C10 H10A 0.9500 . ?
C11 N3 1.343(3) . ?
C11 H11A 0.9500 . ?
O1 H1C 0.843(10) . ?
O1 H1B 0.847(10) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653060
