#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:38:37 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180347 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/16/7201688.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_7201688
loop_
_publ_author_name
'Burke, Nichola J.'
'Burrows, Andrew D.'
'Mahon, Mary F.'
'Warren, John E.'
_publ_section_title
;
 Isomerism and interpenetration in hydrogen-bonded network structures
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              15
_journal_paper_doi               10.1039/b712678f
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C8 H13 N3 O3 S'
_chemical_formula_weight         231.27
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 94.837(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.2870(6)
_cell_length_b                   19.4830(12)
_cell_length_c                   14.679(2)
_cell_measurement_reflns_used    18347
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.440
_cell_measurement_theta_min      3.780
_cell_volume                     2076.6(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'Denzo & Scalepack (Otwinowski & Minor, 1997)'
_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      170(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_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  0.1151
_diffrn_reflns_av_sigmaI/netI    0.0877
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36141
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.78
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
?
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       0.0052(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0517
_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)+(0.0659P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1236
_reflns_number_gt                2886
_reflns_number_total             4724
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b712678f.txt
_cod_data_source_block           compound_2_h02njb3
_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.

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed
to 'multi-scan' 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/c
_cod_database_code               7201688
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S1 S 1.13376(8) 0.21276(3) 0.00205(4) 0.02322(18) Uani 1 1 d . . .
S2 S -0.57491(9) 0.02083(4) 0.28352(4) 0.0299(2) Uani 1 1 d . . .
O1 O 1.0868(3) 0.24656(9) -0.08449(11) 0.0349(5) Uani 1 1 d . . .
O2 O 1.3294(2) 0.21498(9) 0.02838(12) 0.0316(4) Uani 1 1 d . . .
O3 O 1.0251(2) 0.23730(9) 0.07378(11) 0.0340(5) Uani 1 1 d . . .
O4 O -0.7157(3) 0.07336(12) 0.28181(12) 0.0516(6) Uani 1 1 d . . .
O5 O -0.3980(3) 0.04564(12) 0.32226(12) 0.0495(6) Uani 1 1 d . . .
O6 O -0.6279(3) -0.04209(11) 0.32612(12) 0.0502(6) Uani 1 1 d . . .
N1 N 0.8836(3) 0.23178(12) 0.24844(14) 0.0382(6) Uani 1 1 d . . .
H1A H 0.9187 0.2282 0.3071 0.046 Uiso 1 1 calc R . .
H1B H 0.9658 0.2298 0.2079 0.046 Uiso 1 1 calc R . .
N2 N 0.6602(3) 0.24642(13) 0.13152(14) 0.0413(6) Uani 1 1 d . . .
H2A H 0.5444 0.2528 0.1111 0.050 Uiso 1 1 calc R . .
H2B H 0.7459 0.2442 0.0928 0.050 Uiso 1 1 calc R . .
N3 N 0.5801(3) 0.24316(11) 0.28052(13) 0.0295(5) Uani 1 1 d . . .
N4 N -0.0244(3) 0.08088(11) 0.39078(13) 0.0299(5) Uani 1 1 d . . .
H4B H 0.0871 0.0842 0.3724 0.036 Uiso 1 1 calc R . .
H4A H -0.1199 0.0762 0.3504 0.036 Uiso 1 1 calc R . .
N5 N -0.2203(3) 0.07716(11) 0.50392(13) 0.0300(5) Uani 1 1 d . . .
H5A H -0.3126 0.0721 0.4618 0.036 Uiso 1 1 calc R . .
H5B H -0.2412 0.0784 0.5621 0.036 Uiso 1 1 calc R . .
N6 N 0.0941(3) 0.09014(11) 0.54177(13) 0.0272(5) Uani 1 1 d . . .
C1 C 0.7058(3) 0.24010(14) 0.22096(16) 0.0285(6) Uani 1 1 d . . .
C2 C 0.6243(4) 0.22738(17) 0.37697(17) 0.0447(8) Uani 1 1 d . . .
H2C H 0.6475 0.1780 0.3842 0.067 Uiso 1 1 calc R . .
H2D H 0.5208 0.2405 0.4117 0.067 Uiso 1 1 calc R . .
H2E H 0.7345 0.2530 0.3999 0.067 Uiso 1 1 calc R . .
C3 C 0.3857(4) 0.25263(18) 0.24993(19) 0.0499(8) Uani 1 1 d . . .
H3A H 0.3738 0.2879 0.2022 0.075 Uiso 1 1 calc R . .
H3B H 0.3184 0.2671 0.3017 0.075 Uiso 1 1 calc R . .
H3C H 0.3345 0.2093 0.2253 0.075 Uiso 1 1 calc R . .
C4 C -0.0487(4) 0.08302(12) 0.47965(16) 0.0263(6) Uani 1 1 d . . .
C5 C 0.2798(3) 0.10131(15) 0.51385(18) 0.0346(6) Uani 1 1 d . . .
H5C H 0.3130 0.0634 0.4745 0.052 Uiso 1 1 calc R . .
H5D H 0.3676 0.1033 0.5682 0.052 Uiso 1 1 calc R . .
H5E H 0.2833 0.1447 0.4802 0.052 Uiso 1 1 calc R . .
C6 C 0.0679(4) 0.09601(14) 0.63880(16) 0.0345(6) Uani 1 1 d . . .
H6A H 0.0363 0.1435 0.6529 0.052 Uiso 1 1 calc R . .
H6B H 0.1818 0.0830 0.6749 0.052 Uiso 1 1 calc R . .
H6C H -0.0321 0.0655 0.6538 0.052 Uiso 1 1 calc R . .
C12 C -0.5664(4) -0.08439(14) 0.04760(17) 0.0332(6) Uani 1 1 d . . .
H12 H -0.5883 -0.1302 0.0275 0.040 Uiso 1 1 calc R . .
C13 C -0.5817(3) -0.06745(15) 0.13645(17) 0.0330(6) Uani 1 1 d . . .
H13 H -0.6160 -0.1016 0.1780 0.040 Uiso 1 1 calc R . .
C14 C -0.5475(3) 0.00022(14) 0.16786(16) 0.0279(6) Uani 1 1 d . . .
C15 C -0.4991(3) 0.05009(15) 0.10905(16) 0.0310(6) Uani 1 1 d . . .
H15 H -0.4767 0.0955 0.1306 0.037 Uiso 1 1 calc R . .
C16 C -0.4820(3) 0.03402(13) 0.01457(16) 0.0273(6) Uani 1 1 d . . .
C17 C 1.0466(4) 0.02795(14) -0.11754(17) 0.0335(6) Uani 1 1 d . . .
H17 H 1.0503 0.0088 -0.1769 0.040 Uiso 1 1 calc R . .
C18 C 1.0841(3) 0.09634(14) -0.10322(16) 0.0302(6) Uani 1 1 d . . .
H18 H 1.1143 0.1245 -0.1526 0.036 Uiso 1 1 calc R . .
C19 C 1.0776(3) 0.12482(13) -0.01502(16) 0.0262(6) Uani 1 1 d . . .
C20 C 1.0361(3) 0.08549(14) 0.05674(17) 0.0309(6) Uani 1 1 d . . .
H20 H 1.0325 0.1056 0.1155 0.037 Uiso 1 1 calc R . .
C21 C 0.9974(3) 0.01368(14) 0.04433(16) 0.0276(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'
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
O2 S1 O1 112.09(11) . . ?
O2 S1 O3 112.48(10) . . ?
O1 S1 O3 112.61(11) . . ?
O2 S1 C19 106.08(11) . . ?
O1 S1 C19 106.32(11) . . ?
O3 S1 C19 106.68(11) . . ?
O6 S2 O5 112.04(13) . . ?
O6 S2 O4 113.13(13) . . ?
O5 S2 O4 112.16(13) . . ?
O6 S2 C14 106.16(12) . . ?
O5 S2 C14 106.47(11) . . ?
O4 S2 C14 106.29(11) . . ?
C1 N3 C2 121.6(2) . . ?
C1 N3 C3 120.7(2) . . ?
C2 N3 C3 117.0(2) . . ?
C4 N6 C6 121.2(2) . . ?
C4 N6 C5 120.8(2) . . ?
C6 N6 C5 117.6(2) . . ?
N3 C1 N2 121.3(2) . . ?
N3 C1 N1 121.1(2) . . ?
N2 C1 N1 117.6(2) . . ?
N4 C4 N6 120.9(2) . . ?
N4 C4 N5 117.7(2) . . ?
N6 C4 N5 121.5(2) . . ?
C13 C12 C16 120.0(3) . 3_455 ?
C12 C13 C14 120.9(2) . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 S2 120.0(2) . . ?
C13 C14 S2 119.56(19) . . ?
C14 C15 C16 120.2(3) . . ?
C12 C16 C16 120.6(3) 3_455 3_455 ?
C12 C16 C15 121.4(2) 3_455 . ?
C16 C16 C15 117.9(3) 3_455 . ?
C18 C17 C21 119.9(2) . 3_755 ?
C17 C18 C19 120.0(2) . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 S1 119.96(19) . . ?
C18 C19 S1 118.91(19) . . ?
C19 C20 C21 120.4(2) . . ?
C17 C21 C21 120.9(3) 3_755 3_755 ?
C17 C21 C20 121.4(2) 3_755 . ?
C21 C21 C20 117.7(3) 3_755 . ?
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 O2 1.4460(17) . ?
S1 O1 1.4460(17) . ?
S1 O3 1.4510(17) . ?
S1 C19 1.774(3) . ?
S2 O6 1.444(2) . ?
S2 O5 1.4476(19) . ?
S2 O4 1.448(2) . ?
S2 C14 1.772(2) . ?
N1 C1 1.335(3) . ?
N2 C1 1.332(3) . ?
N3 C1 1.320(3) . ?
N3 C2 1.458(3) . ?
N3 C3 1.461(3) . ?
N4 C4 1.332(3) . ?
N5 C4 1.334(3) . ?
N6 C4 1.332(3) . ?
N6 C6 1.457(3) . ?
N6 C5 1.463(3) . ?
C12 C13 1.359(3) . ?
C12 C16 1.405(4) 3_455 ?
C13 C14 1.412(4) . ?
C14 C15 1.366(4) . ?
C15 C16 1.437(3) . ?
C16 C12 1.405(4) 3_455 ?
C16 C16 1.411(5) 3_455 ?
C17 C18 1.373(4) . ?
C17 C21 1.405(4) 3_755 ?
C18 C19 1.413(3) . ?
C19 C20 1.357(3) . ?
C20 C21 1.436(4) . ?
C21 C17 1.405(4) 3_755 ?
C21 C21 1.410(5) 3_755 ?
