#------------------------------------------------------------------------------
#$Date: 2015-11-18 02:56:00 +0100 (Wed 18 de Nov de 2015) $
#$Revision: 170374 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/02/2020299.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2020299
loop_
_publ_author_name
'Burnett, Marianne E.'
'Johnston, Hannah M.'
'Green, Kayla N.'
_publ_section_title
;
 Structural characterization of the aquaporin inhibitor
 2-nicotinamido-1,3,4-thiadiazole
;
_journal_coeditor_code           YP3101
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229615021130
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C8 H6 N4 O S'
_chemical_formula_moiety         'C8 H6 N4 O S'
_chemical_formula_sum            'C8 H6 N4 O S'
_chemical_formula_weight         206.23
_chemical_melting_point          555
_chemical_name_common            TGN-020
_chemical_name_systematic
;
2-Nicotinamido-1,3,4,-thiadiazole
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2015.09.07 svn.r3215 for OlexSys, GUI svn.r3563)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.7097(3)
_cell_length_b                   9.5406(10)
_cell_length_c                   22.841(2)
_cell_measurement_reflns_used    3955
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.57
_cell_volume                     808.41(13)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
olex2.solve (Bourhis et al.,  2015)
;
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.645
_diffrn_reflns_theta_min         3.423
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.818
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.215
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.369
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.44(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1693
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0323P)²+0.3974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0799
_reflns_number_gt                1396
_reflns_number_total             1693
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yp3101sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        808.42(13)
_cod_database_code               2020299
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.754
_shelx_estimated_absorpt_t_max   0.926
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
S S1 0.8507(3) 0.56853(10) 0.14786(4) 0.0107(2) Uani d 1
O O1 1.0560(7) 0.3558(2) 0.08312(10) 0.0143(7) Uani d 1
N N1 1.0574(9) -0.1352(3) 0.11801(13) 0.0143(8) Uani d 1
N N2 0.7859(8) 0.2846(3) 0.16649(12) 0.0102(8) Uani d 1
H H2 0.7121 0.2135 0.1879 0.012 Uiso calc 1
N N3 0.5688(9) 0.4430(3) 0.23599(12) 0.0125(8) Uani d 1
N N4 0.5409(9) 0.5855(3) 0.24700(12) 0.0125(7) Uani d 1
C C1 1.1945(11) -0.1529(4) 0.06461(16) 0.0130(9) Uani d 1
H H1 1.2571 -0.2453 0.0529 0.016 Uiso calc 1
C C2 1.2508(10) -0.0461(4) 0.02543(16) 0.0141(9) Uani d 1
H H2A 1.3439 -0.0647 -0.0125 0.017 Uiso calc 1
C C3 1.1696(10) 0.0884(4) 0.04241(14) 0.0110(8) Uani d 1
H H3 1.2075 0.1648 0.0165 0.013 Uiso calc 1
C C4 0.9767(10) -0.0040(4) 0.13376(16) 0.0125(9) Uani d 1
H H4 0.8765 0.0112 0.1715 0.015 Uiso calc 1
C C5 1.0317(10) 0.1108(3) 0.09784(15) 0.0102(9) Uani d 1
C C6 0.9599(10) 0.2590(4) 0.11461(15) 0.0098(9) Uani d 1
C C7 0.7235(10) 0.4201(4) 0.18599(14) 0.0112(8) Uani d 1
C C8 0.6743(11) 0.6606(4) 0.20526(14) 0.0119(8) Uani d 1
H H8 0.6743 0.7601 0.2064 0.014 Uiso calc 1
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
C8 S1 C7 85.98(18)
C1 N1 C4 116.8(3)
C6 N2 H2 119.3
C6 N2 C7 121.5(3)
C7 N2 H2 119.3
C7 N3 N4 111.0(3)
C8 N4 N3 112.4(3)
N1 C1 H1 118.0
N1 C1 C2 124.1(3)
C2 C1 H1 118.0
C1 C2 H2A 120.8
C1 C2 C3 118.4(3)
C3 C2 H2A 120.8
C2 C3 H3 120.5
C2 C3 C5 119.0(3)
C5 C3 H3 120.5
N1 C4 H4 118.4
N1 C4 C5 123.3(3)
C5 C4 H4 118.4
C3 C5 C4 118.4(3)
C3 C5 C6 116.7(3)
C4 C5 C6 125.0(3)
O1 C6 N2 120.7(3)
O1 C6 C5 120.9(3)
N2 C6 C5 118.4(3)
N2 C7 S1 123.8(3)
N3 C7 S1 115.3(3)
N3 C7 N2 120.9(3)
S1 C8 H8 122.3
N4 C8 S1 115.4(3)
N4 C8 H8 122.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.728(4)
S1 C8 1.708(4)
O1 C6 1.224(4)
N1 C1 1.332(5)
N1 C4 1.336(4)
N2 H2 0.8800
N2 C6 1.371(4)
N2 C7 1.387(4)
N3 N4 1.386(4)
N3 C7 1.297(4)
N4 C8 1.291(5)
C1 H1 0.9500
C1 C2 1.373(5)
C2 H2A 0.9500
C2 C3 1.374(5)
C3 H3 0.9500
C3 C5 1.382(5)
C4 H4 0.9500
C4 C5 1.384(5)
C5 C6 1.489(5)
C8 H8 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2 N4 3_645 0.88 2.14 2.997(4) 164.1
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1 C1 C2 C3 1.6(6)
N1 C4 C5 C3 1.5(6)
N1 C4 C5 C6 -177.3(4)
N3 N4 C8 S1 -0.2(4)
N4 N3 C7 S1 0.2(4)
N4 N3 C7 N2 178.8(3)
C1 N1 C4 C5 -0.6(6)
C1 C2 C3 C5 -0.6(5)
C2 C3 C5 C4 -0.9(5)
C2 C3 C5 C6 178.0(3)
C3 C5 C6 O1 -7.8(5)
C3 C5 C6 N2 172.8(3)
C4 N1 C1 C2 -1.0(6)
C4 C5 C6 O1 171.1(4)
C4 C5 C6 N2 -8.4(5)
C6 N2 C7 S1 0.6(5)
C6 N2 C7 N3 -177.8(3)
C7 S1 C8 N4 0.3(3)
C7 N2 C6 O1 -2.2(5)
C7 N2 C6 C5 177.3(3)
C7 N3 N4 C8 0.0(4)
C8 S1 C7 N2 -178.8(3)
C8 S1 C7 N3 -0.3(3)

_cod_database_fobs_code 2020299
