#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006337.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_2006337
loop_
_publ_author_name
'Velikova, V.'
'Angelova, O.'
'Petrova, R.'
'Kossev, K.'
_publ_contact_author
;
     Dr Olyana Angelova
     Bulgarian Academy of Sciences
     Central Laboratory of Mineralogy and Crystalography
     Rakovski str. 92
     1000 Sofia
     BULGARIA
;
_publ_section_title
;
 <i>N</i>-(2-Pyridinium)urea Perchlorate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              971
_journal_page_last               973
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C6 H8 N3 O +, Cl O4 -'
_chemical_formula_structural     '(C5 N H5) NH C (N H2) O (Cl O4)'
_chemical_formula_sum            'C6 H7 Cl N3 O5'
_chemical_formula_weight         237.60
_chemical_name_systematic        'N-(2-pyridinium)urea perchlorate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_type_scat_source
'International Tables for Crystallography (Vol. C)'
_audit_creation_method
'from SDP files using KAPPA (Macicek, 1992. Unpublished)'
_cell_angle_alpha                90
_cell_angle_beta                 100.14(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.946(2)
_cell_length_b                   16.441(4)
_cell_length_c                   9.582(2)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    292
_cell_measurement_theta_max      21.08
_cell_measurement_theta_min      19.93
_cell_volume                     922.1(4)
_computing_data_collection       'CAD-4 (Enraf-Nonius, 1988)'
_computing_data_reduction        'SDP/PDP (Enraf-Nonius, 1985)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'KAPPA (Mac\'i\<cek, 1992)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      292
_diffrn_measurement_device       'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  'graphite (perpendicular mode)'
_diffrn_radiation_source         '2kW fine focus Philips tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4848
_diffrn_reflns_reduction_process
'F~obs~ = ( I~raw~/LP )^1/2^, where LP = Lorentz-polarization correction'
_diffrn_reflns_theta_max         28.0
_diffrn_reflns_theta_min         0.0
_diffrn_standards_decay_%        1.4
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.42
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_method    none
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.248
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   0.948
_refine_ls_goodness_of_fit_obs   1.042
_refine_ls_hydrogen_treatment    'H-atom positional parameters refined'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.948
_refine_ls_restrained_S_obs      1.042
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_obs          0.0363
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0353P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.0824
_refine_ls_wR_factor_obs         0.0737
_reflns_number_observed          1392
_reflns_number_total             2025
_reflns_observed_criterion       >2\s(I)
_[local]_cod_data_source_file    sk1081.cif
_[local]_cod_data_source_block   LRSA0241
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_original_cell_volume        922.1(8)
_cod_database_code               2006337
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
1/2+x,1/2-y,1/2+z
-x,-y,-z
1/2-x,1/2+y,1/2-z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl 0.0392(3) 0.0250(2) 0.0508(3) -0.0003(2) 0.0015(2) 0.0016(2)
O11 0.0792(13) 0.0336(9) 0.0815(13) 0.0131(9) 0.0218(10) -0.0024(9)
O12 0.0578(11) 0.0456(10) 0.0692(12) -0.0105(8) -0.0112(9) -0.0051(8)
O13 0.1041(16) 0.0438(10) 0.0822(13) -0.0096(9) 0.0502(12) -0.0107(10)
O14 0.0540(11) 0.0592(12) 0.0951(15) -0.0147(10) -0.0247(10) 0.0223(10)
O1 0.0337(8) 0.0318(8) 0.0606(10) -0.0117(7) -0.0035(7) 0.0012(6)
C1 0.0302(11) 0.0323(11) 0.0364(11) -0.0030(9) 0.0027(9) -0.0009(9)
C2 0.0299(10) 0.0286(10) 0.0330(10) 0.0014(8) 0.0073(9) -0.0010(8)
C3 0.0367(12) 0.0288(10) 0.0423(12) -0.0018(10) 0.0045(10) -0.0050(10)
C4 0.0377(13) 0.0434(13) 0.0432(13) -0.0034(10) 0.0015(10) -0.0129(10)
C5 0.0327(12) 0.0484(13) 0.0373(12) 0.0058(10) -0.0013(10) -0.0017(10)
C6 0.0376(12) 0.0346(12) 0.0432(13) 0.0062(10) 0.0063(10) 0.0048(10)
N1 0.0324(10) 0.0279(9) 0.0412(10) -0.0021(8) 0.0021(8) -0.0024(7)
N2 0.0324(9) 0.0245(8) 0.0482(10) -0.0029(9) -0.0012(8) -0.0003(8)
N3 0.0383(11) 0.0366(11) 0.0523(12) -0.0038(9) -0.0079(9) 0.0010(9)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
Cl 0.08102(9) 0.35132(3) 0.65718(6) 0.0391(2) Uani
O11 0.1051(3) 0.42645(10) 0.5888(2) 0.0638(5) Uani
O12 -0.0529(3) 0.29663(10) 0.5599(2) 0.0602(5) Uani
O13 -0.0294(4) 0.36465(11) 0.7756(2) 0.0726(6) Uani
O14 0.2993(3) 0.31530(11) 0.7035(2) 0.0740(6) Uani
O1 0.2783(2) 0.01546(9) 0.5730(2) 0.0435(4) Uani
C1 0.2339(3) 0.08835(12) 0.5742(2) 0.0334(5) Uani
C2 0.5984(3) 0.12384(12) 0.7240(2) 0.0303(4) Uani
C3 0.7436(4) 0.18389(13) 0.7927(2) 0.0363(5) Uani
C4 0.9528(4) 0.16201(14) 0.8655(2) 0.0421(6) Uani
C5 1.0236(4) 0.08155(14) 0.8702(2) 0.0404(5) Uani
C6 0.8790(4) 0.02434(14) 0.8029(2) 0.0386(5) Uani
N1 0.6709(3) 0.04660(10) 0.7325(2) 0.0344(4) Uani
N2 0.3884(3) 0.14281(10) 0.6483(2) 0.0360(4) Uani
N3 0.0407(3) 0.12092(13) 0.5071(2) 0.0443(5) Uani
H3 0.696(4) 0.2346(14) 0.790(2) 0.051 Uiso
H4 1.046(4) 0.2014(14) 0.915(2) 0.051 Uiso
H5 1.156(4) 0.0651(14) 0.917(2) 0.051 Uiso
H6 0.914(4) -0.0305(15) 0.802(2) 0.051 Uiso
HN31 -0.052(4) 0.0870(15) 0.468(2) 0.051 Uiso
HN32 0.014(4) 0.1689(15) 0.508(3) 0.051 Uiso
HN1 0.576(4) 0.0122(14) 0.689(2) 0.051 Uiso
HN2 0.352(4) 0.1885(14) 0.655(3) 0.051 Uiso
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
Cl 0.1485 0.1585
O 0.0106 0.0060
N 0.0061 0.0033
C 0.0033 0.0016
H 0.0000 0.0000
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O11 Cl O13 1 1 109.43(11) yes
O11 Cl O14 1 1 110.22(12) yes
O13 Cl O14 1 1 109.76(13) yes
O11 Cl O12 1 1 109.63(11) yes
O13 Cl O12 1 1 109.51(11) yes
O14 Cl O12 1 1 108.28(11) yes
O1 C1 N3 1 1 124.0(2) yes
O1 C1 N2 1 1 120.7(2) yes
N3 C1 N2 1 1 115.3(2) yes
N1 C2 N2 1 1 120.2(2) yes
N1 C2 C3 1 1 118.4(2) no
N2 C2 C3 1 1 121.4(2) yes
C4 C3 C2 1 1 119.1(2) yes
C4 C3 H3 1 1 121.9(16) no
C2 C3 H3 1 1 119.0(15) no
C3 C4 C5 1 1 120.9(2) no
C3 C4 H4 1 1 119.1(14) no
C5 C4 H4 1 1 119.9(14) no
C6 C5 C4 1 1 118.8(2) no
C6 C5 H5 1 1 117.7(16) no
C4 C5 H5 1 1 123.5(16) no
N1 C6 C5 1 1 119.8(2) no
N1 C6 H6 1 1 116.4(14) no
C5 C6 H6 1 1 123.8(14) no
C2 N1 C6 1 1 122.9(2) yes
C2 N1 HN1 1 1 114.9(16) no
C6 N1 HN1 1 1 122.1(16) no
C2 N2 C1 1 1 125.9(2) yes
C2 N2 HN2 1 1 114.3(18) no
C1 N2 HN2 1 1 119.5(18) no
C1 N3 HN31 1 1 113.6(11) no
C1 N3 HN32 1 1 123.2(11) no
HN31 N3 HN32 1 1 123.(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl O11 1 1.417(2) yes
Cl O13 1 1.425(2) yes
Cl O14 1 1.425(2) yes
Cl O12 1 1.432(2) yes
O1 C1 1 1.228(2) yes
C1 N3 1 1.326(3) yes
C1 N2 1 1.386(2) yes
C2 N1 1 1.339(2) yes
C2 N2 1 1.366(3) yes
C2 C3 1 1.397(3) yes
C3 C4 1 1.363(3) yes
C3 H3 1 0.88(2) no
C4 C5 1 1.387(3) yes
C4 H4 1 0.93(2) no
C5 C6 1 1.359(3) yes
C5 H5 1 0.88(2) no
C6 N1 1 1.351(3) yes
C6 H6 1 0.92(2) no
N1 HN1 1 0.85(2) no
N2 HN2 1 0.79(2) no
N3 HN31 1 0.83(2) no
N3 HN32 1 0.80(2) no
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_publ_flag
N1 C2 C3 C4 0.0(3) no
N2 C2 C3 C4 -179.2(2) no
C2 C3 C4 C5 0.9(3) no
C3 C4 C5 C6 -1.1(3) no
C4 C5 C6 N1 0.3(3) no
N2 C2 N1 C6 178.3(2) no
C3 C2 N1 C6 -0.9(3) no
C5 C6 N1 C2 0.7(3) no
N1 C2 N2 C1 -0.6(3) no
C3 C2 N2 C1 178.6(2) no
O1 C1 N2 C2 0.6(3) no
N3 C1 N2 C2 -179.4(2) no