#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/17/8101770.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_8101770
loop_
_publ_author_name
'Balalaie, S.'
'Bararjanian, M.'
'Rominger, F.'
_publ_section_title
;
Crystal structure of piperidinium 5-cyano-6-(3-chlorophenyl)-4-oxo-
2-thiopyrimidinate, (C₅H₁₂N)[C₁₁H₅ClN₃OS]
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              269
_journal_page_last               270
_journal_volume                  220
_journal_year                    2005
_chemical_formula_structural     (C5H12N)[C11H5ClN3OS]
_chemical_formula_sum            'C16 H17 Cl N4 O S'
_chemical_formula_weight         348.85
_chemical_name_systematic
;
piperidinium 5-cyano-6-(3-chlorophenyl)-4-oxo-2-thiopyrimidinate
;
_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                100.1750(10)
_cell_angle_beta                 90.1990(10)
_cell_angle_gamma                101.0540(10)
_cell_formula_units_Z            2
_cell_length_a                   7.4861(2)
_cell_length_b                   9.8257(3)
_cell_length_c                   11.6947(2)
_cell_measurement_temperature    200(2)
_cell_volume                     830.36(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      200(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       phi/omega
_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  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8710
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_T_max  0.9714
_exptl_absorpt_correction_T_min  0.9047
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0431P)²+0.2221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                3068
_reflns_number_total             3780
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1519.cff
_cod_data_source_block           sba14
_cod_depositor_comments
;
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8101770
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_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.25516(5) 0.68328(4) 0.77349(3) 0.02889(11) Uani 1 2 i d . . .
Cl1 Cl -0.43365(6) 0.09816(5) 0.90343(4) 0.04368(13) Uani 1 2 i d . . .
C1 C 0.18176(18) 0.53268(15) 0.67785(12) 0.0221(3) Uani 1 2 i d . . .
N2 N 0.01826(15) 0.44956(13) 0.68714(10) 0.0238(3) Uani 1 2 i d . . .
C3 C -0.03511(17) 0.33296(15) 0.60677(12) 0.0211(3) Uani 1 2 i d . . .
C4 C 0.06752(18) 0.29349(15) 0.51164(12) 0.0219(3) Uani 1 2 i d . . .
C5 C 0.24054(18) 0.38103(15) 0.50000(12) 0.0217(3) Uani 1 2 i d . . .
O5 O 0.34530(13) 0.35889(11) 0.41846(8) 0.0256(2) Uani 1 2 i d . . .
N6 N 0.28971(16) 0.49456(13) 0.58751(10) 0.0223(3) Uani 1 2 i d . . .
H6 H 0.395(3) 0.5468(19) 0.5854(15) 0.035(5) Uiso 1 2 i d . . .
C7 C 0.01869(18) 0.16584(16) 0.42876(13) 0.0260(3) Uani 1 2 i d . . .
N7 N -0.01065(19) 0.06511(16) 0.35984(13) 0.0386(3) Uani 1 2 i d . . .
C11 C -0.21390(18) 0.24684(15) 0.62876(12) 0.0224(3) Uani 1 2 i d . . .
C12 C -0.35827(19) 0.20959(15) 0.54694(13) 0.0264(3) Uani 1 2 i d . . .
H12 H -0.3414 0.2302 0.4709 0.032 Uiso 1 2 i calc R . .
C13 C -0.5278(2) 0.14191(17) 0.57731(14) 0.0314(3) Uani 1 2 i d . . .
H13 H -0.6274 0.1191 0.5222 0.038 Uiso 1 2 i calc R . .
C14 C -0.5531(2) 0.10757(17) 0.68648(15) 0.0326(4) Uani 1 2 i d . . .
H14 H -0.6689 0.0614 0.7069 0.039 Uiso 1 2 i calc R . .
C15 C -0.4065(2) 0.14173(16) 0.76540(13) 0.0278(3) Uani 1 2 i d . . .
C16 C -0.23826(19) 0.21198(16) 0.73906(13) 0.0256(3) Uani 1 2 i d . . .
H16 H -0.1402 0.2364 0.7953 0.031 Uiso 1 2 i calc R . .
N31 N 0.20031(19) 0.32582(15) 0.19282(11) 0.0291(3) Uani 1 2 i d . . .
H31A H 0.242(3) 0.318(2) 0.2630(18) 0.046(5) Uiso 1 2 i d . . .
H31B H 0.092(3) 0.345(2) 0.2054(16) 0.039(5) Uiso 1 2 i d . . .
C32 C 0.1849(3) 0.19484(18) 0.10511(15) 0.0393(4) Uani 1 2 i d . . .
H32A H 0.1028 0.1164 0.1324 0.047 Uiso 1 2 i calc R . .
H32B H 0.3062 0.1694 0.0940 0.047 Uiso 1 2 i calc R . .
C33 C 0.1094(3) 0.2181(2) -0.00982(15) 0.0460(5) Uani 1 2 i d . . .
H33A H 0.1080 0.1331 -0.0699 0.055 Uiso 1 2 i calc R . .
H33B H -0.0177 0.2318 -0.0003 0.055 Uiso 1 2 i calc R . .
C34 C 0.2229(2) 0.3460(2) -0.05018(14) 0.0398(4) Uani 1 2 i d . . .
H34A H 0.3448 0.3266 -0.0711 0.048 Uiso 1 2 i calc R . .
H34B H 0.1633 0.3636 -0.1203 0.048 Uiso 1 2 i calc R . .
C35 C 0.2434(2) 0.47475(19) 0.04400(14) 0.0368(4) Uani 1 2 i d . . .
H35A H 0.1231 0.5010 0.0580 0.044 Uiso 1 2 i calc R . .
H35B H 0.3252 0.5545 0.0183 0.044 Uiso 1 2 i calc R . .
C36 C 0.3207(2) 0.44814(17) 0.15582(14) 0.0311(3) Uani 1 2 i d . . .
H36A H 0.4447 0.4282 0.1438 0.037 Uiso 1 2 i calc R . .
H36B H 0.3293 0.5329 0.2171 0.037 Uiso 1 2 i 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'
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
N2 C1 N6 119.29(13) . . ?
N2 C1 S1 121.46(11) . . ?
N6 C1 S1 119.24(10) . . ?
C3 N2 C1 118.84(12) . . ?
N2 C3 C4 123.55(12) . . ?
N2 C3 C11 113.97(11) . . ?
C4 C3 C11 122.47(13) . . ?
C3 C4 C7 124.56(12) . . ?
C3 C4 C5 118.31(13) . . ?
C7 C4 C5 116.97(12) . . ?
O5 C5 N6 120.06(12) . . ?
O5 C5 C4 124.94(13) . . ?
N6 C5 C4 114.99(12) . . ?
C5 N6 C1 124.88(12) . . ?
N7 C7 C4 176.05(15) . . ?
C12 C11 C16 119.83(13) . . ?
C12 C11 C3 122.43(13) . . ?
C16 C11 C3 117.58(12) . . ?
C11 C12 C13 119.55(14) . . ?
C14 C13 C12 120.89(14) . . ?
C13 C14 C15 118.65(14) . . ?
C16 C15 C14 121.85(14) . . ?
C16 C15 Cl1 118.45(12) . . ?
C14 C15 Cl1 119.69(11) . . ?
C15 C16 C11 119.18(14) . . ?
C32 N31 C36 112.24(12) . . ?
N31 C32 C33 109.33(15) . . ?
C34 C33 C32 111.68(14) . . ?
C35 C34 C33 110.78(14) . . ?
C34 C35 C36 111.13(14) . . ?
N31 C36 C35 109.39(13) . . ?
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 C1 1.6858(15) . ?
Cl1 C15 1.7445(15) . ?
C1 N2 1.3513(18) . ?
C1 N6 1.3754(18) . ?
N2 C3 1.3405(18) . ?
C3 C4 1.3951(19) . ?
C3 C11 1.4895(18) . ?
C4 C7 1.428(2) . ?
C4 C5 1.4323(18) . ?
C5 O5 1.2526(16) . ?
C5 N6 1.3652(18) . ?
C7 N7 1.145(2) . ?
C11 C12 1.391(2) . ?
C11 C16 1.396(2) . ?
C12 C13 1.394(2) . ?
C13 C14 1.382(2) . ?
C14 C15 1.383(2) . ?
C15 C16 1.379(2) . ?
N31 C32 1.482(2) . ?
N31 C36 1.489(2) . ?
C32 C33 1.527(3) . ?
C33 C34 1.526(3) . ?
C34 C35 1.507(3) . ?
C35 C36 1.512(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17239418
