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#$Date: 2017-11-15 15:07:08 +0200 (Wed, 15 Nov 2017) $
#$Revision: 203218 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/30/03/2300301.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_2300301
loop_
_publ_author_name
'Ye, Heng-Yun'
'Cai, Hong-Ling'
'Ge, Jia-Zeng'
'Xiong, Ren-Gen'
_publ_section_title
;
 Reversible structural phase transition of pyridinium-4-carboxylic acid
 perchlorate
;
_journal_coden_ASTM              JACGAR
_journal_issue                   5
_journal_name_full               'Journal of Applied Crystallography'
_journal_page_first              1031
_journal_page_last               1035
_journal_paper_doi               10.1107/S0021889810024039
_journal_volume                  43
_journal_year                    2010
_chemical_formula_sum            'C6 H6 Cl N O6'
_chemical_formula_weight         223.57
_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                 137.919(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5046(11)
_cell_length_b                   13.574(3)
_cell_length_c                   17.423(5)
_cell_measurement_temperature    298(2)
_cell_volume                     872.5(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8786
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8771
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.425
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     79
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0585
_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)+(0.0796P)²+0.7580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1699
_reflns_number_gt                1484
_reflns_number_total             1998
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            wf5065.cif
_cod_data_source_block           298K
_cod_original_cell_volume        872.5(3)
_cod_original_sg_symbol_H-M      'p 21/c'
_cod_database_code               2300301
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_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C5 0.2160(10) 0.3410(2) 0.7842(3) 0.0523(8) Uani d . 1 . .
H H5A 0.3117 0.2816 0.7893 0.063 Uiso calc R 1 . .
C C4 0.0989(9) 0.4103(2) 0.7055(3) 0.0480(8) Uani d . 1 . .
H H4A 0.1167 0.3988 0.6572 0.058 Uiso calc R 1 . .
C C3 -0.0461(8) 0.4974(2) 0.6984(2) 0.0401(7) Uani d . 1 . .
C C2 -0.0763(9) 0.5125(2) 0.7695(3) 0.0474(8) Uani d . 1 . .
H H2A -0.1809 0.5699 0.7639 0.057 Uiso calc R 1 . .
C C1 0.0498(10) 0.4418(3) 0.8481(3) 0.0545(9) Uani d . 1 . .
H H1A 0.0366 0.4513 0.8978 0.065 Uiso calc R 1 . .
C C6 -0.1607(9) 0.5780(2) 0.6177(3) 0.0464(8) Uani d . 1 . .
N N1 0.1921(8) 0.3590(2) 0.8532(2) 0.0511(7) Uani d . 1 . .
H H1B 0.2719 0.3154 0.9034 0.061 Uiso calc R 1 . .
O O1 -0.3160(7) 0.65041(17) 0.6028(2) 0.0586(7) Uani d . 1 . .
O O2 -0.0688(9) 0.55910(19) 0.5681(2) 0.0689(8) Uani d . 1 . .
H H2 -0.1127 0.6072 0.5310 0.103 Uiso calc R 1 . .
Cl Cl1 -0.270(4) 0.8025(10) 0.4111(13) 0.0433(8) Uani d PD 0.33 A 1
O O3 -0.501(7) 0.811(2) 0.423(3) 0.0679(17) Uani d PD 0.33 A 1
O O4 -0.074(5) 0.7089(8) 0.4593(10) 0.0651(16) Uani d PD 0.33 A 1
O O5 -0.490(6) 0.8058(11) 0.2891(11) 0.072(2) Uani d PD 0.33 A 1
O O6 -0.013(3) 0.8843(11) 0.4694(11) 0.083(2) Uani d PD 0.33 A 1
Cl Cl1B -0.297(4) 0.8018(10) 0.4105(12) 0.0433(8) Uani d PD 0.33 B 2
O O3B -0.535(6) 0.8071(19) 0.418(2) 0.0679(17) Uani d PD 0.33 B 2
O O4B -0.030(4) 0.7313(9) 0.4892(9) 0.0651(16) Uani d PD 0.33 B 2
O O5B -0.494(5) 0.7760(10) 0.2991(13) 0.072(2) Uani d PD 0.33 B 2
O O6B -0.130(3) 0.8937(11) 0.4410(13) 0.083(2) Uani d PD 0.33 B 2
Cl Cl1A -0.319(4) 0.7909(9) 0.4047(13) 0.0433(8) Uani d PD 0.33 C 3
O O3A -0.557(7) 0.8203(16) 0.410(3) 0.0679(17) Uani d PD 0.33 C 3
O O4A -0.305(3) 0.6847(6) 0.4062(7) 0.0651(16) Uani d PD 0.33 C 3
O O5A -0.464(8) 0.8233(14) 0.2987(13) 0.072(2) Uani d PD 0.33 C 3
O O6A 0.030(3) 0.8306(8) 0.4991(9) 0.083(2) Uani d PD 0.33 C 3
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C5 C4 . . 119.5(3) ?
N1 C5 H5A . . 120.3 ?
C4 C5 H5A . . 120.3 ?
C5 C4 C3 . . 119.4(3) ?
C5 C4 H4A . . 120.3 ?
C3 C4 H4A . . 120.3 ?
C4 C3 C2 . . 119.5(3) ?
C4 C3 C6 . . 121.5(3) ?
C2 C3 C6 . . 119.0(3) ?
C1 C2 C3 . . 119.0(3) ?
C1 C2 H2A . . 120.5 ?
C3 C2 H2A . . 120.5 ?
N1 C1 C2 . . 119.6(3) ?
N1 C1 H1A . . 120.2 ?
C2 C1 H1A . . 120.2 ?
O1 C6 O2 . . 125.5(3) ?
O1 C6 C3 . . 122.5(3) ?
O2 C6 C3 . . 112.0(3) ?
C5 N1 C1 . . 123.0(3) ?
C5 N1 H1B . . 118.5 ?
C1 N1 H1B . . 118.5 ?
C6 O2 H2 . . 109.5 ?
O3 Cl1 O6 . . 110.0(10) ?
O3 Cl1 O4 . . 109.9(10) ?
O6 Cl1 O4 . . 109.9(9) ?
O3 Cl1 O5 . . 109.9(10) ?
O6 Cl1 O5 . . 108.4(9) ?
O4 Cl1 O5 . . 108.8(9) ?
O5B Cl1B O6B . . 111.5(10) ?
O5B Cl1B O4B . . 111.0(10) ?
O6B Cl1B O4B . . 108.8(9) ?
O5B Cl1B O3B . . 109.0(10) ?
O6B Cl1B O3B . . 108.1(10) ?
O4B Cl1B O3B . . 108.4(10) ?
O6A Cl1A O3A . . 109.8(10) ?
O6A Cl1A O5A . . 110.9(10) ?
O3A Cl1A O5A . . 109.6(10) ?
O6A Cl1A O4A . . 110.5(9) ?
O3A Cl1A O4A . . 108.4(10) ?
O5A Cl1A O4A . . 107.5(9) ?
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
C5 N1 . 1.325(4) ?
C5 C4 . 1.367(5) ?
C5 H5A . 0.9300 ?
C4 C3 . 1.380(4) ?
C4 H4A . 0.9300 ?
C3 C2 . 1.383(4) ?
C3 C6 . 1.501(4) ?
C2 C1 . 1.367(5) ?
C2 H2A . 0.9300 ?
C1 N1 . 1.335(4) ?
C1 H1A . 0.9300 ?
C6 O1 . 1.198(4) ?
C6 O2 . 1.310(4) ?
N1 H1B . 0.8600 ?
O2 H2 . 0.8200 ?
Cl1 O3 . 1.442(13) ?
Cl1 O6 . 1.460(13) ?
Cl1 O4 . 1.462(13) ?
Cl1 O5 . 1.471(13) ?
Cl1B O5B . 1.393(15) ?
Cl1B O6B . 1.398(14) ?
Cl1B O4B . 1.401(14) ?
Cl1B O3B . 1.411(15) ?
Cl1A O6A . 1.414(12) ?
Cl1A O3A . 1.432(12) ?
Cl1A O5A . 1.434(12) ?
Cl1A O4A . 1.443(12) ?
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
N1 H1B O3 2_546 0.86 2.25 2.94(3) 137.8
N1 H1B O1 2_546 0.86 2.26 2.880(4) 128.6
N1 H1B O3A 2_546 0.86 2.34 3.01(4) 134.9
O2 H2 O4A . 0.82 1.88 2.666(8) 160.3
O2 H2 O4 . 0.82 1.98 2.767(13) 161.6
