#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:07:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180376 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/45/7204524.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_7204524
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            'C20 H17 N3 O2 S'
_chemical_formula_weight         363.43
_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                 99.75(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.524(2)
_cell_length_b                   11.088(3)
_cell_length_c                   12.935(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      12
_cell_volume                     1770.3(6)
_computing_cell_refinement       'Nonius CAD4 software'
_computing_data_collection       'Nonius CAD4 software'
_computing_data_reduction        'XCAD (P.McArdle, 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      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  '4-circle diffractometer'
_diffrn_measurement_method       'scintillation counter'
_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  0.0228
_diffrn_reflns_av_sigmaI/netI    0.1239
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2370
_diffrn_reflns_theta_full        21.98
_diffrn_reflns_theta_max         21.98
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.203
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0422
_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=3D1/[σ²(Fo²)+(0.0429P)²+0.0000P] where P=3D(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                1072
_reflns_number_total             2164
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b208544p.txt
_cod_data_source_block           gs1
_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 '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_H-M      P21/a
_cod_database_code               7204524
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
S1 S 0.07701(9) 0.02494(10) 0.17684(9) 0.0440(4) Uani 1 1 d . . .
O1 O -0.0623(2) -0.0080(3) 0.3710(2) 0.0592(9) Uani 1 1 d . . .
O2 O 0.2418(3) -0.2334(3) 0.4570(2) 0.0683(11) Uani 1 1 d . . .
N2 N 0.0768(3) -0.1441(3) 0.4041(3) 0.0438(10) Uani 1 1 d . . .
N4 N 0.2695(3) 0.0415(3) 0.2934(3) 0.0383(9) Uani 1 1 d . . .
N3 N 0.2678(3) -0.0676(3) 0.2376(3) 0.0392(9) Uani 1 1 d . . .
C7A C 0.1587(3) 0.0938(4) 0.2930(3) 0.0352(11) Uani 1 1 d . . .
C2 C 0.1788(4) -0.0848(4) 0.1744(3) 0.0379(11) Uani 1 1 d . . .
C5 C 0.3174(3) 0.0225(4) 0.4040(3) 0.0443(12) Uani 1 1 d . . .
H5A H 0.3513 0.0958 0.4345 0.058 Uiso 1 1 calc R . .
H5B H 0.3714 -0.0411 0.4106 0.058 Uiso 1 1 calc R . .
C6 C 0.2230(3) -0.0133(4) 0.4574(3) 0.0402(12) Uani 1 1 d . . .
H6 H 0.2378 0.0067 0.5323 0.052 Uiso 1 1 calc R . .
C7 C 0.1263(3) 0.0577(4) 0.4010(3) 0.0378(12) Uani 1 1 d . . .
H7 H 0.1122 0.1291 0.4412 0.049 Uiso 1 1 calc R . .
C8 C 0.0338(4) -0.0293(4) 0.3902(3) 0.0418(11) Uani 1 1 d . . .
C9 C 0.1877(4) -0.1430(5) 0.4407(3) 0.0449(12) Uani 1 1 d . . .
C10 C 0.0120(4) -0.2534(4) 0.3836(4) 0.0697(15) Uani 1 1 d . . .
H10A H 0.0581 -0.3197 0.3727 0.098 Uiso 1 1 calc R . .
H10B H -0.0418 -0.2421 0.3220 0.098 Uiso 1 1 calc R . .
H10C H -0.0230 -0.2704 0.4425 0.098 Uiso 1 1 calc R . .
C11 C 0.1614(4) -0.1877(4) 0.1023(3) 0.0403(12) Uani 1 1 d . . .
C12 C 0.0593(4) -0.2180(4) 0.0523(4) 0.0554(14) Uani 1 1 d . . .
H12 H 0.0004 -0.1711 0.0625 0.072 Uiso 1 1 calc R . .
C13 C 0.0431(4) -0.3174(5) -0.0133(4) 0.0685(16) Uani 1 1 d . . .
H13 H -0.0265 -0.3380 -0.0457 0.089 Uiso 1 1 calc R . .
C14 C 0.1293(5) -0.3851(5) -0.0304(4) 0.0678(16) Uani 1 1 d . . .
H14 H 0.1189 -0.4512 -0.0751 0.088 Uiso 1 1 calc R . .
C15 C 0.2317(5) -0.3548(5) 0.0190(4) 0.0664(15) Uani 1 1 d . . .
H15 H 0.2903 -0.4014 0.0076 0.086 Uiso 1 1 calc R . .
C16 C 0.2492(4) -0.2565(4) 0.0851(4) 0.0592(14) Uani 1 1 d . . .
H16 H 0.3190 -0.2366 0.1177 0.077 Uiso 1 1 calc R . .
C17 C 0.1568(3) 0.2304(4) 0.2777(3) 0.0364(11) Uani 1 1 d . . .
C18 C 0.2397(4) 0.2886(4) 0.2392(3) 0.0493(13) Uani 1 1 d . . .
H18 H 0.2991 0.2448 0.2256 0.064 Uiso 1 1 calc R . .
C19 C 0.2345(4) 0.4113(4) 0.2211(4) 0.0559(14) Uani 1 1 d . . .
H19 H 0.2910 0.4505 0.1968 0.073 Uiso 1 1 calc R . .
C20 C 0.1463(5) 0.4749(4) 0.2390(4) 0.0605(14) Uani 1 1 d . . .
H20 H 0.1431 0.5575 0.2266 0.079 Uiso 1 1 calc R . .
C21 C 0.0615(4) 0.4184(5) 0.2754(4) 0.0584(14) Uani 1 1 d . . .
H21 H 0.0012 0.4622 0.2868 0.076 Uiso 1 1 calc R . .
C22 C 0.0679(3) 0.2955(4) 0.2945(3) 0.0476(13) Uani 1 1 d . . .
H22 H 0.0113 0.2565 0.3189 0.062 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'
O O 0.0106 0.0060 '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'
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 89.8(2) . . ?
C8 N2 C9 112.4(4) . . ?
C8 N2 C10 123.4(4) . . ?
C9 N2 C10 124.3(4) . . ?
N3 N4 C5 110.1(3) . . ?
N3 N4 C7A 113.3(3) . . ?
C5 N4 C7A 106.5(3) . . ?
C2 N3 N4 113.1(3) . . ?
N4 C7A C17 112.2(3) . . ?
N4 C7A C7 106.0(3) . . ?
C17 C7A C7 111.6(3) . . ?
N4 C7A S1 103.2(2) . . ?
C17 C7A S1 108.2(3) . . ?
C7 C7A S1 115.4(3) . . ?
N3 C2 C11 122.8(4) . . ?
N3 C2 S1 116.0(3) . . ?
C11 C2 S1 121.1(3) . . ?
N4 C5 C6 105.0(3) . . ?
C9 C6 C5 114.6(4) . . ?
C9 C6 C7 103.5(3) . . ?
C5 C6 C7 105.3(3) . . ?
C8 C7 C6 104.6(3) . . ?
C8 C7 C7A 113.2(3) . . ?
C6 C7 C7A 104.7(3) . . ?
O1 C8 N2 124.0(4) . . ?
O1 C8 C7 128.4(4) . . ?
N2 C8 C7 107.7(4) . . ?
O2 C9 N2 123.4(5) . . ?
O2 C9 C6 128.6(4) . . ?
N2 C9 C6 108.0(4) . . ?
C12 C11 C16 119.4(4) . . ?
C12 C11 C2 121.1(4) . . ?
C16 C11 C2 119.6(4) . . ?
C11 C12 C13 120.7(5) . . ?
C14 C13 C12 120.0(5) . . ?
C13 C14 C15 119.5(5) . . ?
C14 C15 C16 121.3(5) . . ?
C15 C16 C11 119.1(5) . . ?
C22 C17 C18 119.3(4) . . ?
C22 C17 C7A 119.7(4) . . ?
C18 C17 C7A 120.8(4) . . ?
C19 C18 C17 120.2(4) . . ?
C20 C19 C18 119.9(5) . . ?
C19 C20 C21 121.0(5) . . ?
C20 C21 C22 118.8(5) . . ?
C17 C22 C21 120.8(4) . . ?
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 1.766(4) . ?
S1 C7A 1.835(4) . ?
O1 C8 1.210(4) . ?
O2 C9 1.209(5) . ?
N2 C8 1.382(5) . ?
N2 C9 1.390(5) . ?
N2 C10 1.457(5) . ?
N4 N3 1.407(4) . ?
N4 C5 1.469(5) . ?
N4 C7A 1.503(5) . ?
N3 C2 1.280(5) . ?
C7A C17 1.527(5) . ?
C7A C7 1.571(5) . ?
C2 C11 1.467(5) . ?
C5 C6 1.520(5) . ?
C6 C9 1.508(6) . ?
C6 C7 1.523(5) . ?
C7 C8 1.496(6) . ?
C11 C12 1.373(5) . ?
C11 C16 1.387(6) . ?
C12 C13 1.385(6) . ?
C13 C14 1.363(6) . ?
C14 C15 1.373(6) . ?
C15 C16 1.380(6) . ?
C17 C22 1.375(5) . ?
C17 C18 1.384(5) . ?
C18 C19 1.380(5) . ?
C19 C20 1.363(6) . ?
C20 C21 1.382(6) . ?
C21 C22 1.385(6) . ?
