#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:07:59 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180376 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/45/7204523.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_7204523
loop_
_publ_author_name
'Butler, Richard N.'
'Smyth, Georgina M.'
'McArdle, Patrick'
'Cunningham, Desmond'
_publ_section_title
;
 A new tricyclic ring and a nitrogen???sulfur analogue of the
 tri-pentagon bowl: cycloaddition reactions of the unstablised
 1,3,4-thiadiazolium-3-methanide 1,3-dipole: steric influences on the
 endo-effect: substituted pyrrolo[2,1-b]-1,3,4-thiadiazole systems:
 azolium 1,3-dipoles
;
_journal_issue                   24
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2851
_journal_paper_doi               10.1039/b208544p
_journal_year                    2002
_chemical_formula_sum            'C13 H11 N3 O2 S'
_chemical_formula_weight         273.31
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                117.58(2)
_cell_angle_beta                 99.770(10)
_cell_angle_gamma                99.90(2)
_cell_formula_units_Z            4
_cell_length_a                   10.537(2)
_cell_length_b                   11.710(4)
_cell_length_c                   12.259(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      12
_cell_volume                     1265.8(6)
_computing_cell_refinement       'XDS (W.Kabsch, 2000)'
_computing_data_collection       'Marresearch MarControl software'
_computing_data_reduction        'XDS (W.Kabsch, 2000)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.920
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Marresearch image plate'
_diffrn_measurement_method       '180 mm image plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5814
_diffrn_reflns_theta_full        21.21
_diffrn_reflns_theta_max         21.21
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.9553
_exptl_absorpt_correction_T_min  0.8933
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.043(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0368
_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)+(0.0471P)²+0.3996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0902
_reflns_number_gt                2388
_reflns_number_total             2577
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b208544p.txt
_cod_data_source_block           gs2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_cell_volume        1265.8(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204523
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
S1 S 0.17392(7) 0.23795(7) 0.73934(7) 0.0604(3) Uani 1 1 d . . .
S101 S 0.44452(7) 0.78300(8) 0.69422(7) 0.0647(3) Uani 1 1 d . . .
N2 N -0.18959(17) 0.22866(17) 0.60633(18) 0.0364(5) Uani 1 1 d . . .
O2 O -0.21279(17) 0.41815(17) 0.60292(18) 0.0551(5) Uani 1 1 d . . .
N4 N 0.15612(18) 0.40273(18) 0.65664(18) 0.0386(5) Uani 1 1 d . . .
O1 O -0.13384(18) 0.03697(18) 0.5687(2) 0.0677(6) Uani 1 1 d . . .
N3 N 0.1280(2) 0.4602(2) 0.77626(19) 0.0475(5) Uani 1 1 d . . .
C7A C 0.1321(2) 0.2569(2) 0.6005(2) 0.0421(6) Uani 1 1 d . . .
H7A H 0.1945 0.2276 0.5495 0.055 Uiso 1 1 calc R . .
N102 N 0.77737(17) 0.69997(17) 0.78274(16) 0.0322(5) Uani 1 1 d . . .
O101 O 0.68571(15) 0.67031(16) 0.58466(15) 0.0474(5) Uani 1 1 d . . .
O102 O 0.81561(19) 0.67428(19) 0.95867(18) 0.0652(6) Uani 1 1 d . . .
N103 N 0.5279(2) 0.8160(2) 0.9204(2) 0.0550(6) Uani 1 1 d . . .
N104 N 0.4490(2) 0.6823(2) 0.84236(19) 0.0498(6) Uani 1 1 d . . .
C2 C 0.1404(2) 0.3894(3) 0.8277(3) 0.0535(7) Uani 1 1 d . . .
H2 H 0.1318 0.4174 0.9098 0.070 Uiso 1 1 calc R . .
C5 C 0.0691(2) 0.4212(2) 0.5642(2) 0.0385(6) Uani 1 1 d . . .
H5A H 0.1122 0.4207 0.5001 0.050 Uiso 1 1 calc R . .
H5B H 0.0481 0.5059 0.6068 0.050 Uiso 1 1 calc R . .
C6 C -0.0584(2) 0.3030(2) 0.5019(2) 0.0358(6) Uani 1 1 d . . .
H6 H -0.0978 0.2768 0.4124 0.047 Uiso 1 1 calc R . .
C7 C -0.0153(2) 0.1884(2) 0.5102(2) 0.0385(6) Uani 1 1 d . . .
H7 H -0.0180 0.1171 0.4251 0.050 Uiso 1 1 calc R . .
C8 C -0.1154(2) 0.1378(2) 0.5630(2) 0.0415(6) Uani 1 1 d . . .
C9 C -0.1612(2) 0.3285(2) 0.5756(2) 0.0360(6) Uani 1 1 d . . .
C10 C -0.2868(2) 0.2166(2) 0.6722(2) 0.0398(6) Uani 1 1 d . . .
C11 C -0.4208(3) 0.1738(3) 0.6097(3) 0.0534(7) Uani 1 1 d . . .
H11 H -0.4489 0.1555 0.5257 0.069 Uiso 1 1 calc R . .
C12 C -0.5146(3) 0.1578(3) 0.6717(3) 0.0662(8) Uani 1 1 d . . .
H12 H -0.6059 0.1284 0.6294 0.086 Uiso 1 1 calc R . .
C13 C -0.4732(3) 0.1850(3) 0.7945(3) 0.0720(9) Uani 1 1 d . . .
H13 H -0.5364 0.1727 0.8355 0.094 Uiso 1 1 calc R . .
C14 C -0.3404(4) 0.2301(4) 0.8578(3) 0.0835(10) Uani 1 1 d . . .
H14 H -0.3131 0.2509 0.9427 0.109 Uiso 1 1 calc R . .
C15 C -0.2449(3) 0.2453(3) 0.7965(3) 0.0684(8) Uani 1 1 d . . .
H15 H -0.1537 0.2746 0.8393 0.089 Uiso 1 1 calc R . .
C102 C 0.5274(3) 0.8762(3) 0.8573(3) 0.0601(8) Uani 1 1 d . . .
H102 H 0.5702 0.9677 0.8972 0.078 Uiso 1 1 calc R . .
C105 C 0.5046(3) 0.5911(3) 0.8718(3) 0.0548(7) Uani 1 1 d . . .
H10A H 0.4339 0.5121 0.8488 0.071 Uiso 1 1 calc R . .
H10B H 0.5508 0.6353 0.9626 0.071 Uiso 1 1 calc R . .
C106 C 0.6032(2) 0.5520(2) 0.7920(2) 0.0429(6) Uani 1 1 d . . .
H106 H 0.6049 0.4596 0.7652 0.056 Uiso 1 1 calc R . .
C107 C 0.5535(2) 0.5658(2) 0.6754(2) 0.0393(6) Uani 1 1 d . . .
H107 H 0.5184 0.4774 0.5969 0.051 Uiso 1 1 calc R . .
C108 C 0.6750(2) 0.6492(2) 0.6703(2) 0.0341(6) Uani 1 1 d . . .
C109 C 0.7428(2) 0.6471(2) 0.8577(2) 0.0403(6) Uani 1 1 d . . .
C110 C 0.9063(2) 0.7870(2) 0.8112(2) 0.0333(6) Uani 1 1 d . . .
C111 C 0.9145(2) 0.9076(2) 0.8150(2) 0.0452(6) Uani 1 1 d . . .
H111 H 0.8370 0.9323 0.7997 0.059 Uiso 1 1 calc R . .
C112 C 1.0386(3) 0.9908(3) 0.8419(2) 0.0619(8) Uani 1 1 d . . .
H112 H 1.0452 1.0725 0.8449 0.081 Uiso 1 1 calc R . .
C113 C 1.1528(3) 0.9545(4) 0.8643(3) 0.0704(9) Uani 1 1 d . . .
H113 H 1.2365 1.0115 0.8827 0.092 Uiso 1 1 calc R . .
C114 C 1.1437(3) 0.8339(3) 0.8597(2) 0.0629(8) Uani 1 1 d . . .
H114 H 1.2213 0.8092 0.8745 0.082 Uiso 1 1 calc R . .
C115 C 1.0201(2) 0.7493(3) 0.8334(2) 0.0459(6) Uani 1 1 d . . .
H115 H 1.0138 0.6678 0.8308 0.060 Uiso 1 1 calc R . .
C207 C 0.4391(2) 0.6346(3) 0.7059(2) 0.0486(7) Uani 1 1 d . . .
H207 H 0.3518 0.5677 0.6527 0.063 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'
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
C2 S1 C7A 87.81(12) . . ?
C102 S101 C207 87.31(13) . . ?
C9 N2 C8 112.39(18) . . ?
C9 N2 C10 124.60(19) . . ?
C8 N2 C10 122.99(18) . . ?
N3 N4 C5 111.47(17) . . ?
N3 N4 C7A 110.85(16) . . ?
C5 N4 C7A 106.30(17) . . ?
C2 N3 N4 110.9(2) . . ?
N4 C7A C7 107.07(17) . . ?
N4 C7A S1 103.40(15) . . ?
C7 C7A S1 118.30(15) . . ?
C109 N102 C108 111.82(18) . . ?
C109 N102 C110 124.48(18) . . ?
C108 N102 C110 123.50(17) . . ?
C102 N103 N104 110.5(2) . . ?
N103 N104 C105 112.6(2) . . ?
N103 N104 C207 111.11(19) . . ?
C105 N104 C207 106.0(2) . . ?
N3 C2 S1 117.5(2) . . ?
N4 C5 C6 105.73(17) . . ?
C9 C6 C7 104.52(17) . . ?
C9 C6 C5 113.4(2) . . ?
C7 C6 C5 105.88(18) . . ?
C8 C7 C6 104.73(18) . . ?
C8 C7 C7A 115.22(19) . . ?
C6 C7 C7A 103.93(17) . . ?
O1 C8 N2 123.0(2) . . ?
O1 C8 C7 128.6(2) . . ?
N2 C8 C7 108.42(18) . . ?
O2 C9 N2 124.6(2) . . ?
O2 C9 C6 126.9(2) . . ?
N2 C9 C6 108.53(19) . . ?
C11 C10 C15 120.3(2) . . ?
C11 C10 N2 119.8(2) . . ?
C15 C10 N2 119.9(2) . . ?
C10 C11 C12 119.8(3) . . ?
C13 C12 C11 119.9(3) . . ?
C14 C13 C12 120.5(3) . . ?
C13 C14 C15 120.4(3) . . ?
C10 C15 C14 119.1(3) . . ?
N103 C102 S101 118.0(2) . . ?
N104 C105 C106 105.86(19) . . ?
C109 C106 C107 104.56(18) . . ?
C109 C106 C105 113.7(2) . . ?
C107 C106 C105 106.1(2) . . ?
C108 C107 C106 104.83(18) . . ?
C108 C107 C207 115.05(19) . . ?
C106 C107 C207 103.99(18) . . ?
O101 C108 N102 124.2(2) . . ?
O101 C108 C107 127.2(2) . . ?
N102 C108 C107 108.68(18) . . ?
O102 C109 N102 124.2(2) . . ?
O102 C109 C106 126.7(2) . . ?
N102 C109 C106 109.1(2) . . ?
C115 C110 C111 121.0(2) . . ?
C115 C110 N102 119.8(2) . . ?
C111 C110 N102 119.2(2) . . ?
C112 C111 C110 119.1(2) . . ?
C113 C112 C111 120.5(3) . . ?
C112 C113 C114 120.0(3) . . ?
C113 C114 C115 120.3(3) . . ?
C110 C115 C114 119.1(3) . . ?
N104 C207 C107 106.78(19) . . ?
N104 C207 S101 103.52(17) . . ?
C107 C207 S101 118.61(16) . . ?
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
S1 C2 1.735(3) . ?
S1 C7A 1.808(2) . ?
S101 C102 1.735(3) . ?
S101 C207 1.801(3) . ?
N2 C9 1.387(3) . ?
N2 C8 1.389(3) . ?
N2 C10 1.435(3) . ?
O2 C9 1.201(3) . ?
N4 N3 1.412(3) . ?
N4 C5 1.454(3) . ?
N4 C7A 1.469(3) . ?
O1 C8 1.200(3) . ?
N3 C2 1.262(3) . ?
C7A C7 1.564(3) . ?
N102 C109 1.386(3) . ?
N102 C108 1.390(3) . ?
N102 C110 1.429(3) . ?
O101 C108 1.203(3) . ?
O102 C109 1.205(3) . ?
N103 C102 1.265(3) . ?
N103 N104 1.397(3) . ?
N104 C105 1.454(3) . ?
N104 C207 1.475(3) . ?
C5 C6 1.529(3) . ?
C6 C9 1.508(3) . ?
C6 C7 1.528(3) . ?
C7 C8 1.502(3) . ?
C10 C11 1.366(3) . ?
C10 C15 1.370(4) . ?
C11 C12 1.383(4) . ?
C12 C13 1.358(4) . ?
C13 C14 1.355(4) . ?
C14 C15 1.388(4) . ?
C105 C106 1.529(4) . ?
C106 C109 1.502(3) . ?
C106 C107 1.526(3) . ?
C107 C108 1.500(3) . ?
C107 C207 1.565(3) . ?
C110 C115 1.375(3) . ?
C110 C111 1.377(3) . ?
C111 C112 1.374(4) . ?
C112 C113 1.370(4) . ?
C113 C114 1.373(4) . ?
C114 C115 1.378(4) . ?
