#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/24/8102419.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_8102419
loop_
_publ_author_name
'Hui-Ming Huang'
'Shi-Yuan Luo'
'Fang Xiong'
'Bin-Hai Kuang'
'Shao-Hua Li'
'Cheng-Mei Liu'
'Guo-Gang Tu'
_publ_section_title
;
 Crystal structure of
 2-chloro-N-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl]nicotinamide,
 C14H8ClFN4OS
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              201
_journal_volume                  224
_journal_year                    2009
_chemical_formula_moiety         'C14 H8 Cl F N4 O S'
_chemical_formula_sum            'C14 H8 Cl F N4 O S'
_chemical_formula_weight         334.75
_chemical_name_systematic
; 
2-Chloro-N-[5-(4-Fluorophenyl)-1,3,4-thiadiazol-2-yl]-nicotinamide 
;
_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
_audit_update_record
;
2008-12-23 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.137(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.451(4)
_cell_length_b                   19.628(9)
_cell_length_c                   10.519(5)
_cell_measurement_reflns_used    2223
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.98
_cell_measurement_theta_min      2.31
_cell_volume                     1444.3(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8573
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2492
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0387
_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)+(0.0531P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                1599
_reflns_number_total             2492
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2533.cff
_cod_data_source_block           081205
_cod_original_cell_volume        1444.5(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8102419
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 0.00921(9) 0.42092(3) 0.32240(7) 0.0493(2) Uani 1 1 d . . .
Cl1 Cl 0.38361(10) 0.21657(4) 0.64377(8) 0.0725(3) Uani 1 1 d . . .
O1 O 0.2229(2) 0.31053(8) 0.40155(18) 0.0545(5) Uani 1 1 d . . .
N3 N 0.2510(3) 0.51660(10) 0.4187(2) 0.0518(6) Uani 1 1 d . . .
N2 N 0.3933(3) 0.40846(10) 0.4580(2) 0.0465(5) Uani 1 1 d . . .
N1 N 0.7269(3) 0.20368(11) 0.6423(2) 0.0578(6) Uani 1 1 d . . .
F1 F -0.8283(2) 0.57967(11) 0.0674(2) 0.1050(7) Uani 1 1 d . . .
C3 C 0.5583(3) 0.29966(11) 0.5146(2) 0.0418(6) Uani 1 1 d . . .
C6 C 0.3771(3) 0.33880(12) 0.4547(2) 0.0437(6) Uani 1 1 d . . .
C4 C 0.5728(3) 0.24224(12) 0.5948(2) 0.0472(6) Uani 1 1 d . . .
C2 C 0.7185(3) 0.31629(13) 0.4825(3) 0.0526(7) Uani 1 1 d . . .
H2 H 0.7170 0.3543 0.4294 0.063 Uiso 1 1 calc R . .
C8 C -0.0622(4) 0.50570(12) 0.3063(2) 0.0459(6) Uani 1 1 d . . .
N4 N 0.0752(3) 0.54852(11) 0.3609(2) 0.0544(6) Uani 1 1 d . . .
C1 C 0.8791(4) 0.27656(13) 0.5291(3) 0.0590(8) Uani 1 1 d . . .
H1 H 0.9869 0.2868 0.5074 0.071 Uiso 1 1 calc R . .
C7 C 0.2359(3) 0.45032(12) 0.4067(2) 0.0435(6) Uani 1 1 d . . .
C12 C -0.6404(4) 0.56139(19) 0.1257(3) 0.0701(9) Uani 1 1 d . . .
C5 C 0.8774(4) 0.22155(14) 0.6080(3) 0.0621(8) Uani 1 1 d . . .
H5 H 0.9872 0.1950 0.6398 0.074 Uiso 1 1 calc R . .
C11 C -0.5947(4) 0.49440(17) 0.1365(3) 0.0658(8) Uani 1 1 d U . .
H11 H -0.6891 0.4613 0.1053 0.079 Uiso 1 1 calc R . .
C10 C -0.4048(4) 0.47610(14) 0.1950(3) 0.0567(7) Uani 1 1 d U . .
H10 H -0.3710 0.4303 0.2030 0.068 Uiso 1 1 calc R . .
C9 C -0.2646(4) 0.52533(13) 0.2416(2) 0.0486(6) Uani 1 1 d . . .
C14 C -0.3167(4) 0.59407(14) 0.2275(3) 0.0645(8) Uani 1 1 d . . .
H14 H -0.2239 0.6278 0.2572 0.077 Uiso 1 1 calc R . .
C13 C -0.5079(5) 0.61169(16) 0.1688(3) 0.0734(9) Uani 1 1 d . . .
H13 H -0.5448 0.6572 0.1592 0.088 Uiso 1 1 calc R . .
H6 H 0.502(3) 0.4278(11) 0.503(2) 0.052(8) Uiso 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'
F F 0.0171 0.0103 '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'
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
C7 S1 C8 86.69(12) . . ?
C7 N3 N4 111.7(2) . . ?
C6 N2 C7 121.9(2) . . ?
C6 N2 H6 120.3(15) . . ?
C7 N2 H6 117.3(15) . . ?
C4 N1 C5 116.6(2) . . ?
C2 C3 C4 116.4(2) . . ?
C2 C3 C6 120.4(2) . . ?
C4 C3 C6 122.9(2) . . ?
O1 C6 N2 121.6(2) . . ?
O1 C6 C3 122.0(2) . . ?
N2 C6 C3 116.3(2) . . ?
N1 C4 C3 124.8(2) . . ?
N1 C4 Cl1 114.22(19) . . ?
C3 C4 Cl1 121.00(19) . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
N4 C8 C9 124.1(2) . . ?
N4 C8 S1 114.15(19) . . ?
C9 C8 S1 121.66(19) . . ?
C8 N4 N3 112.6(2) . . ?
C5 C1 C2 118.6(3) . . ?
C5 C1 H1 120.7 . . ?
C2 C1 H1 120.7 . . ?
N3 C7 N2 121.4(2) . . ?
N3 C7 S1 114.92(18) . . ?
N2 C7 S1 123.69(18) . . ?
C11 C12 C13 123.0(3) . . ?
C11 C12 F1 118.8(3) . . ?
C13 C12 F1 118.2(3) . . ?
N1 C5 C1 123.8(2) . . ?
N1 C5 H5 118.1 . . ?
C1 C5 H5 118.1 . . ?
C12 C11 C10 118.7(3) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C9 C14 119.3(2) . . ?
C10 C9 C8 120.5(2) . . ?
C14 C9 C8 120.2(2) . . ?
C13 C14 C9 119.5(3) . . ?
C13 C14 H14 120.2 . . ?
C9 C14 H14 120.2 . . ?
C12 C13 C14 119.0(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
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 C7 1.715(2) . ?
S1 C8 1.738(2) . ?
Cl1 C4 1.734(3) . ?
O1 C6 1.224(3) . ?
N3 C7 1.308(3) . ?
N3 N4 1.389(3) . ?
N2 C6 1.372(3) . ?
N2 C7 1.380(3) . ?
N2 H6 0.87(2) . ?
N1 C4 1.321(3) . ?
N1 C5 1.338(3) . ?
F1 C12 1.369(3) . ?
C3 C2 1.387(3) . ?
C3 C4 1.389(3) . ?
C3 C6 1.492(3) . ?
C2 C1 1.369(3) . ?
C2 H2 0.9300 . ?
C8 N4 1.296(3) . ?
C8 C9 1.476(3) . ?
C1 C5 1.365(3) . ?
C1 H1 0.9300 . ?
C12 C11 1.353(4) . ?
C12 C13 1.359(4) . ?
C5 H5 0.9300 . ?
C11 C10 1.382(4) . ?
C11 H11 0.9300 . ?
C10 C9 1.383(4) . ?
C10 H10 0.9300 . ?
C9 C14 1.398(4) . ?
C14 C13 1.387(4) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H6 N3 0.87(2) 2.05(2) 2.916(3) 170(2) 3_666
C1 H1 O1 0.93 2.43 3.343(3) 167.8 1_655
C10 H10 S1 0.93 2.68 3.105(3) 108.6 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 C6 O1 2.7(4) . . . . ?
C7 N2 C6 C3 -179.6(2) . . . . ?
C2 C3 C6 O1 130.8(3) . . . . ?
C4 C3 C6 O1 -43.7(4) . . . . ?
C2 C3 C6 N2 -46.9(3) . . . . ?
C4 C3 C6 N2 138.6(2) . . . . ?
C5 N1 C4 C3 -1.0(4) . . . . ?
C5 N1 C4 Cl1 -179.7(2) . . . . ?
C2 C3 C4 N1 0.7(4) . . . . ?
C6 C3 C4 N1 175.4(2) . . . . ?
C2 C3 C4 Cl1 179.21(19) . . . . ?
C6 C3 C4 Cl1 -6.0(4) . . . . ?
C4 C3 C2 C1 0.3(4) . . . . ?
C6 C3 C2 C1 -174.6(2) . . . . ?
C7 S1 C8 N4 -0.4(2) . . . . ?
C7 S1 C8 C9 -177.4(2) . . . . ?
C9 C8 N4 N3 177.9(2) . . . . ?
S1 C8 N4 N3 1.0(3) . . . . ?
C7 N3 N4 C8 -1.3(3) . . . . ?
C3 C2 C1 C5 -0.8(4) . . . . ?
N4 N3 C7 N2 -179.5(2) . . . . ?
N4 N3 C7 S1 1.0(3) . . . . ?
C6 N2 C7 N3 175.2(2) . . . . ?
C6 N2 C7 S1 -5.4(3) . . . . ?
C8 S1 C7 N3 -0.4(2) . . . . ?
C8 S1 C7 N2 -179.9(2) . . . . ?
C4 N1 C5 C1 0.5(4) . . . . ?
C2 C1 C5 N1 0.4(5) . . . . ?
C13 C12 C11 C10 0.5(5) . . . . ?
F1 C12 C11 C10 179.7(2) . . . . ?
C12 C11 C10 C9 0.1(4) . . . . ?
C11 C10 C9 C14 -0.8(4) . . . . ?
C11 C10 C9 C8 178.9(2) . . . . ?
N4 C8 C9 C10 -175.0(2) . . . . ?
S1 C8 C9 C10 1.8(4) . . . . ?
N4 C8 C9 C14 4.7(4) . . . . ?
S1 C8 C9 C14 -178.5(2) . . . . ?
C10 C9 C14 C13 0.9(4) . . . . ?
C8 C9 C14 C13 -178.8(3) . . . . ?
C11 C12 C13 C14 -0.4(5) . . . . ?
F1 C12 C13 C14 -179.6(3) . . . . ?
C9 C14 C13 C12 -0.3(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653959
