#------------------------------------------------------------------------------
#$Date: 2017-11-15 15:07:08 +0200 (Wed, 15 Nov 2017) $
#$Revision: 203218 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/30/03/2300302.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_2300302
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                 138.055(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   17.356(6)
_cell_length_b                   13.241(3)
_cell_length_c                   16.161(7)
_cell_measurement_temperature    103(2)
_cell_volume                     2482.5(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_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  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21324
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8951
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.595
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         4908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0656P)²+0.8233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1074
_reflns_number_gt                4449
_reflns_number_total             5031
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            wf5065.cif
_cod_data_source_block           103K
_cod_original_cell_volume        2482.3(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2300302
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 C1 0.03957(15) 0.44437(12) 0.86614(15) 0.0169(3) Uani d . 1 . .
H H1B 0.0417 0.4539 0.9260 0.020 Uiso calc R 1 . .
C C2 -0.01100(14) 0.51316(12) 0.78012(14) 0.0149(3) Uani d . 1 . .
H H2A -0.0477 0.5714 0.7727 0.018 Uiso calc R 1 . .
C C3 -0.00538(14) 0.49267(11) 0.70540(14) 0.0137(3) Uani d . 1 . .
C C4 0.04540(15) 0.40228(12) 0.71448(14) 0.0164(3) Uani d . 1 . .
H H4A 0.0449 0.3908 0.6561 0.020 Uiso calc R 1 . .
C C5 0.09246(15) 0.33494(12) 0.80044(15) 0.0167(3) Uani d . 1 . .
H H5A 0.1254 0.2739 0.8070 0.020 Uiso calc R 1 . .
C C6 -0.05019(14) 0.57231(12) 0.61896(14) 0.0144(3) Uani d . 1 . .
C C7 0.35985(15) 0.43912(12) 0.87583(14) 0.0167(3) Uani d . 1 . .
H H7A 0.3597 0.4479 0.9341 0.020 Uiso calc R 1 . .
C C8 0.31124(14) 0.50818(12) 0.79119(14) 0.0150(3) Uani d . 1 . .
H H8A 0.2744 0.5665 0.7834 0.018 Uiso calc R 1 . .
C C9 0.31889(14) 0.48811(12) 0.71766(14) 0.0140(3) Uani d . 1 . .
C C10 0.37074(15) 0.39828(12) 0.72766(14) 0.0163(3) Uani d . 1 . .
H H10A 0.3714 0.3872 0.6701 0.020 Uiso calc R 1 . .
C C11 0.41744(15) 0.33065(12) 0.81353(14) 0.0168(3) Uani d . 1 . .
H H11A 0.4522 0.2703 0.8215 0.020 Uiso calc R 1 . .
C C12 0.27544(14) 0.56836(11) 0.63220(14) 0.0147(3) Uani d . 1 . .
C C13 0.67983(15) 0.43640(12) 0.83007(15) 0.0180(4) Uani d . 1 . .
H H13A 0.6676 0.4402 0.8784 0.022 Uiso calc R 1 . .
C C14 0.63626(15) 0.50668(12) 0.74775(15) 0.0167(3) Uani d . 1 . .
H H14A 0.5913 0.5615 0.7318 0.020 Uiso calc R 1 . .
C CC15 0.66246(14) 0.49249(11) 0.68789(13) 0.0140(3) Uani d . 1 . .
C C16 0.72695(14) 0.40769(12) 0.70835(14) 0.0158(3) Uani d . 1 . .
H H16A 0.7407 0.4018 0.6616 0.019 Uiso calc R 1 . .
C C17 0.76679(15) 0.33871(12) 0.79037(14) 0.0166(3) Uani d . 1 . .
H H17A 0.8087 0.2813 0.8055 0.020 Uiso calc R 1 . .
C C18 0.62149(14) 0.57213(12) 0.60301(13) 0.0148(3) Uani d . 1 . .
N N1 0.09000(12) 0.35862(10) 0.87381(12) 0.0157(3) Uani d . 1 . .
H H1A 0.1233 0.3169 0.9354 0.019 Uiso calc R 1 . .
N N2 0.41173(12) 0.35345(10) 0.88470(12) 0.0160(3) Uani d . 1 . .
H H2B 0.4435 0.3112 0.9454 0.019 Uiso calc R 1 . .
N N3 0.74378(12) 0.35598(10) 0.84910(12) 0.0168(3) Uani d . 1 . .
H H3A 0.7713 0.3124 0.9072 0.020 Uiso calc R 1 . .
Cl Cl3 0.55612(4) 0.80167(3) 0.38250(4) 0.01354(12) Uani d . 1 . .
Cl Cl1 -0.11025(3) 0.80359(3) 0.39994(3) 0.01273(12) Uani d . 1 . .
Cl Cl2 0.22941(3) 0.79584(3) 0.41991(3) 0.01364(12) Uani d . 1 . .
O O1 -0.11127(10) 0.64368(8) 0.59645(10) 0.0174(3) Uani d . 1 . .
O O2 -0.01290(12) 0.55395(9) 0.57319(11) 0.0218(3) Uani d . 1 . .
H H2 -0.0239 0.6050 0.5345 0.033 Uiso calc R 1 . .
O O3 0.21999(10) 0.64235(8) 0.61429(10) 0.0179(3) Uani d . 1 . .
O O4 0.30740(12) 0.54730(8) 0.58197(11) 0.0210(3) Uani d . 1 . .
H H4 0.2994 0.5987 0.5457 0.031 Uiso calc R 1 . .
O O5 0.54958(10) 0.63833(8) 0.57009(10) 0.0184(3) Uani d . 1 . .
O O6 0.67288(11) 0.55969(9) 0.56980(10) 0.0204(3) Uani d . 1 . .
H H6 0.6591 0.6100 0.5287 0.031 Uiso calc R 1 . .
O O7 -0.19455(11) 0.80848(8) 0.40613(11) 0.0179(3) Uani d . 1 . .
O O8 -0.02732(12) 0.71855(9) 0.46760(11) 0.0230(3) Uani d . 1 . .
O O9 -0.17838(11) 0.79138(9) 0.28243(11) 0.0230(3) Uani d . 1 . .
O O10 -0.03837(12) 0.89499(9) 0.44632(12) 0.0263(3) Uani d . 1 . .
O O11 0.14983(11) 0.80153(9) 0.43163(11) 0.0194(3) Uani d . 1 . .
O O12 0.30829(11) 0.70725(8) 0.48165(11) 0.0198(3) Uani d . 1 . .
O O13 0.15581(12) 0.78773(9) 0.30036(11) 0.0237(3) Uani d . 1 . .
O O14 0.30568(12) 0.88475(9) 0.46859(11) 0.0253(3) Uani d . 1 . .
O O15 0.47374(11) 0.79988(8) 0.39108(11) 0.0186(3) Uani d . 1 . .
O O16 0.65164(11) 0.72593(9) 0.45924(11) 0.0213(3) Uani d . 1 . .
O O17 0.48804(11) 0.78057(10) 0.26604(11) 0.0242(3) Uani d . 1 . .
O O18 0.61393(12) 0.89945(9) 0.41699(12) 0.0275(3) Uani d . 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'
Cl Cl 0.1484 0.1585 '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'
H H 0.0000 0.0000 '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
C2 C1 N1 . . 123.09(14) ?
C2 C1 H1B . . 118.5 ?
N1 C1 H1B . . 118.5 ?
C3 C2 C1 . . 112.56(16) ?
C3 C2 H2A . . 123.7 ?
C1 C2 H2A . . 123.7 ?
C2 C3 C4 . . 122.84(15) ?
C2 C3 C6 . . 112.82(15) ?
C4 C3 C6 . . 124.27(14) ?
C5 C4 C3 . . 122.12(15) ?
C5 C4 H4A . . 118.9 ?
C3 C4 H4A . . 118.9 ?
N1 C5 C4 . . 113.58(16) ?
N1 C5 H5A . . 123.2 ?
C4 C5 H5A . . 123.2 ?
O1 C6 O2 . . 129.62(14) ?
O1 C6 C3 . . 124.44(14) ?
O2 C6 C3 . . 105.94(14) ?
C8 C7 N2 . . 123.03(14) ?
C8 C7 H7A . . 118.5 ?
N2 C7 H7A . . 118.5 ?
C7 C8 C9 . . 112.58(16) ?
C7 C8 H8A . . 123.7 ?
C9 C8 H8A . . 123.7 ?
C8 C9 C10 . . 122.99(15) ?
C8 C9 C12 . . 112.70(15) ?
C10 C9 C12 . . 124.23(14) ?
C11 C10 C9 . . 122.12(15) ?
C11 C10 H10A . . 118.9 ?
C9 C10 H10A . . 118.9 ?
N2 C11 C10 . . 113.35(16) ?
N2 C11 H11A . . 123.3 ?
C10 C11 H11A . . 123.3 ?
O3 C12 O4 . . 129.27(14) ?
O3 C12 C9 . . 124.60(14) ?
O4 C12 C9 . . 106.12(14) ?
C14 C13 N3 . . 121.98(14) ?
C14 C13 H13A . . 119.0 ?
N3 C13 H13A . . 119.0 ?
C13 C14 CC15 . . 112.38(16) ?
C13 C14 H14A . . 123.8 ?
CC15 C14 H14A . . 123.8 ?
C14 CC15 C18 . . 113.03(15) ?
C14 CC15 C16 . . 124.14(14) ?
C18 CC15 C16 . . 122.82(14) ?
C17 C16 CC15 . . 120.86(15) ?
C17 C16 H16A . . 119.6 ?
CC15 C16 H16A . . 119.6 ?
N3 C17 C16 . . 113.66(16) ?
N3 C17 H17A . . 123.2 ?
C16 C17 H17A . . 123.2 ?
O5 C18 O6 . . 130.54(14) ?
O5 C18 CC15 . . 122.79(14) ?
O6 C18 CC15 . . 106.67(14) ?
C5 N1 C1 . . 125.72(14) ?
C5 N1 H1A . . 117.1 ?
C1 N1 H1A . . 117.1 ?
C11 N2 C7 . . 125.87(14) ?
C11 N2 H2B . . 117.1 ?
C7 N2 H2B . . 117.1 ?
C17 N3 C13 . . 126.93(14) ?
C17 N3 H3A . . 116.5 ?
C13 N3 H3A . . 116.5 ?
O17 Cl3 O18 . . 111.42(8) ?
O17 Cl3 O16 . . 107.95(8) ?
O18 Cl3 O16 . . 104.67(8) ?
O17 Cl3 O15 . . 102.80(8) ?
O18 Cl3 O15 . . 113.45(7) ?
O16 Cl3 O15 . . 116.57(7) ?
O9 Cl1 O10 . . 110.46(8) ?
O9 Cl1 O8 . . 108.20(8) ?
O10 Cl1 O8 . . 104.92(8) ?
O9 Cl1 O7 . . 102.96(9) ?
O10 Cl1 O7 . . 114.60(7) ?
O8 Cl1 O7 . . 115.62(7) ?
O13 Cl2 O14 . . 110.76(8) ?
O13 Cl2 O12 . . 109.09(7) ?
O14 Cl2 O12 . . 104.86(8) ?
O13 Cl2 O11 . . 101.99(9) ?
O14 Cl2 O11 . . 115.24(7) ?
O12 Cl2 O11 . . 114.90(7) ?
C6 O2 H2 . . 109.5 ?
C12 O4 H4 . . 109.5 ?
C18 O6 H6 . . 109.5 ?
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
C1 C2 . 1.310(2) ?
C1 N1 . 1.382(2) ?
C1 H1B . 0.9500 ?
C2 C3 . 1.310(2) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.428(2) ?
C3 C6 . 1.433(2) ?
C4 C5 . 1.305(2) ?
C4 H4A . 0.9500 ?
C5 N1 . 1.257(2) ?
C5 H5A . 0.9500 ?
C6 O1 . 1.255(2) ?
C6 O2 . 1.318(2) ?
C7 C8 . 1.305(2) ?
C7 N2 . 1.388(2) ?
C7 H7A . 0.9500 ?
C8 C9 . 1.317(2) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.426(2) ?
C9 C12 . 1.434(2) ?
C10 C11 . 1.308(2) ?
C10 H10A . 0.9500 ?
C11 N2 . 1.262(2) ?
C11 H11A . 0.9500 ?
C12 O3 . 1.247(2) ?
C12 O4 . 1.309(2) ?
C13 C14 . 1.308(2) ?
C13 N3 . 1.397(2) ?
C13 H13A . 0.9500 ?
C14 CC15 . 1.354(2) ?
C14 H14A . 0.9500 ?
CC15 C18 . 1.431(2) ?
CC15 C16 . 1.439(2) ?
C16 C17 . 1.306(2) ?
C16 H16A . 0.9500 ?
C17 N3 . 1.295(2) ?
C17 H17A . 0.9500 ?
C18 O5 . 1.273(2) ?
C18 O6 . 1.350(2) ?
N1 H1A . 0.8800 ?
N2 H2B . 0.8800 ?
N3 H3A . 0.8800 ?
Cl3 O17 . 1.3070(13) ?
Cl3 O18 . 1.4702(13) ?
Cl3 O16 . 1.4946(13) ?
Cl3 O15 . 1.5358(13) ?
Cl1 O9 . 1.3001(14) ?
Cl1 O10 . 1.4805(13) ?
Cl1 O8 . 1.4812(13) ?
Cl1 O7 . 1.5403(13) ?
Cl2 O13 . 1.3056(14) ?
Cl2 O14 . 1.4859(13) ?
Cl2 O12 . 1.4878(12) ?
Cl2 O11 . 1.5293(13) ?
O2 H2 . 0.8400 ?
O4 H4 . 0.8400 ?
O6 H6 . 0.8400 ?
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 H1A O7 2_546 0.88 1.84 2.604(2) 144.0
N1 H1A O1 2_546 0.88 2.33 2.8641(18) 119.5
N2 H2B O15 2_646 0.88 1.85 2.621(2) 145.2
N2 H2B O5 2_646 0.88 2.32 2.8928(18) 123.2
N3 H3A O11 2_646 0.88 1.84 2.599(2) 143.5
N3 H3A O3 2_646 0.88 2.30 2.8624(18) 121.7
O2 H2 O8 . 0.84 1.83 2.6625(17) 172.4
O4 H4 O12 . 0.84 1.84 2.6742(17) 169.9
O6 H6 O16 . 0.84 1.85 2.6821(17) 171.4
