#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/98/2019887.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_2019887
loop_
_publ_author_name
'Wang, Bi-Qin'
'Yan, Hai-Biao'
'Huang, Zheng-Qing'
'Zhang, Yun-Hua'
'Sun, Jing'
_publ_section_title
;
 Reversible phase transition of 2-carboxypyridinium
 perchlorate--pyridinium-2-carboxylate (1/1)
;
_journal_coeditor_code           KU3149
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229615003691
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C6 H6 N O2 + , Cl O4 - , C6 H5 N O2'
_chemical_formula_moiety         'C6 H6 N O2 +, Cl O4 -, C6 H5 N O2'
_chemical_formula_sum            'C12 H11 Cl N2 O8'
_chemical_formula_weight         346.68
_chemical_name_systematic
;
2-Carboxypyridinium perchlorate--pyridinium-2-carboxylate (1/1)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.18(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.904(4)
_cell_length_b                   11.953(2)
_cell_length_c                   12.018(2)
_cell_measurement_reflns_used    9700
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      3.11
_cell_volume                     2853.0(10)
_computing_cell_refinement
;
RAPID-AUTO (Rigaku, 2000)
;
_computing_data_collection
;
RAPID-AUTO (Rigaku, 2000)
;
_computing_data_reduction
;
RAPID-AUTO (Rigaku, 2000)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAPID'
_diffrn_measurement_method       ω
_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  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13514
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(RAPID-AUTO; Rigaku, 2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.401
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0570
_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)+(0.1057P)²+2.1900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1594
_refine_ls_wR_factor_ref         0.1648
_reflns_number_gt                2854
_reflns_number_total             3245
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ku3149sup1.cif
_cod_data_source_block           223K
_cod_original_cell_volume        2852.8(10)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               2019887
_cod_database_fobs_code          2019887
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
Cl Cl1 0.5000 0.44877(5) 0.7500 0.0351(2) Uani d S 1 2
O O4 0.70447(7) 0.74680(14) 0.33260(13) 0.0420(4) Uani d . 1 1
H H4B 0.7313 0.7326 0.2962 0.063 Uiso calc PR 0.50 1
N N2 0.65780(8) 0.60176(14) 0.55031(14) 0.0357(4) Uani d . 1 1
H H2A 0.6856 0.5463 0.5565 0.043 Uiso calc R 1 1
O O3 0.73367(10) 0.57781(16) 0.40846(16) 0.0589(5) Uani d . 1 1
C C12 0.70224(10) 0.66473(18) 0.39856(16) 0.0359(4) Uani d . 1 1
C C10 0.61344(10) 0.77205(18) 0.46109(17) 0.0375(4) Uani d . 1 1
H H10A 0.6118 0.8292 0.4065 0.045 Uiso calc R 1 1
C C9 0.57293(10) 0.77693(19) 0.53425(19) 0.0420(5) Uani d . 1 1
H H9A 0.5441 0.8383 0.5299 0.050 Uiso calc R 1 1
C C11 0.65560(9) 0.68213(17) 0.47070(15) 0.0325(4) Uani d . 1 1
C C8 0.57523(10) 0.6918(2) 0.61269(18) 0.0411(5) Uani d . 1 1
H H8A 0.5472 0.6938 0.6605 0.049 Uiso calc R 1 1
C C7 0.61898(10) 0.60360(18) 0.62039(18) 0.0394(4) Uani d . 1 1
H H7A 0.6215 0.5454 0.6742 0.047 Uiso calc R 1 1
Cl Cl2 0.5000 0.96787(7) 0.7500 0.0520(2) Uani d S 1 2
O O1 0.77749(7) 0.73989(13) 0.20873(12) 0.0400(3) Uani d . 1 1
H H1C 0.7499 0.7277 0.2442 0.060 Uiso calc PR 0.50 1
O O2 0.74865(9) 0.56814(14) 0.13636(14) 0.0485(4) Uani d . 1 1
N N1 0.82078(8) 0.59328(14) -0.01206(15) 0.0368(4) Uani d . 1 1
H H1A 0.7960 0.5348 -0.0124 0.044 Uiso calc R 1 1
C C5 0.82236(9) 0.67533(16) 0.06529(15) 0.0317(4) Uani d . 1 1
C C6 0.77878(9) 0.65715(16) 0.14345(15) 0.0333(4) Uani d . 1 1
C C2 0.89779(10) 0.77548(19) -0.01224(18) 0.0395(5) Uani d . 1 1
H H2B 0.9244 0.8389 -0.0123 0.047 Uiso calc R 1 1
C C4 0.85552(11) 0.59724(19) -0.08847(19) 0.0421(5) Uani d . 1 1
H H4A 0.8528 0.5379 -0.1411 0.051 Uiso calc R 1 1
C C3 0.89544(10) 0.68894(19) -0.08961(18) 0.0407(5) Uani d . 1 1
H H3A 0.9206 0.6924 -0.1421 0.049 Uiso calc R 1 1
C C1 0.86075(9) 0.76884(18) 0.06592(16) 0.0362(4) Uani d . 1 1
H H1B 0.8620 0.8277 0.1185 0.043 Uiso calc R 1 1
O O10 0.53517(13) 0.3813(2) 0.6925(2) 0.0849(7) Uani d . 1 1
O O9 0.45293(12) 0.5178(2) 0.6689(2) 0.0809(7) Uani d . 1 1
O O5 0.5000 0.8505(3) 0.7500 0.0840(10) Uani d S 1 2
O O7 0.4720(5) 1.0047(10) 0.6389(9) 0.173(6) Uani d P 0.50 1
O O6 0.5756(2) 0.9917(4) 0.7706(5) 0.0813(14) Uani d P 0.50 1
O O8 0.4912(7) 1.0098(9) 0.8470(12) 0.197(7) Uani d P 0.50 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'
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
O10 Cl1 O10 2_656 . 110.2(2) y
O10 Cl1 O9 2_656 . 108.32(15) y
O10 Cl1 O9 . . 110.68(16) ?
O10 Cl1 O9 2_656 2_656 110.68(16) ?
O10 Cl1 O9 . 2_656 108.32(15) ?
O9 Cl1 O9 . 2_656 108.6(2) y
C12 O4 H4B . . 109.5 ?
C7 N2 C11 . . 122.81(18) ?
C7 N2 H2A . . 118.6 ?
C11 N2 H2A . . 118.6 ?
O3 C12 O4 . . 126.65(19) ?
O3 C12 C11 . . 119.25(18) ?
O4 C12 C11 . . 114.10(18) ?
C11 C10 C9 . . 118.59(19) ?
C11 C10 H10A . . 120.7 ?
C9 C10 H10A . . 120.7 ?
C8 C9 C10 . . 120.0(2) ?
C8 C9 H9A . . 120.0 ?
C10 C9 H9A . . 120.0 ?
N2 C11 C10 . . 119.83(18) ?
N2 C11 C12 . . 115.17(17) ?
C10 C11 C12 . . 124.99(18) ?
C9 C8 C7 . . 119.41(19) ?
C9 C8 H8A . . 120.3 ?
C7 C8 H8A . . 120.3 ?
N2 C7 C8 . . 119.29(19) ?
N2 C7 H7A . . 120.4 ?
C8 C7 H7A . . 120.4 ?
O8 Cl2 O8 . 2_656 135.8(11) ?
O8 Cl2 O7 . 2_656 31.7(7) ?
O8 Cl2 O7 2_656 2_656 127.3(7) ?
O8 Cl2 O7 . . 127.3(7) y
O8 Cl2 O7 2_656 . 31.7(7) ?
O7 Cl2 O7 2_656 . 142.0(12) ?
O8 Cl2 O5 . . 112.1(5) y
O8 Cl2 O5 2_656 . 112.1(5) ?
O7 Cl2 O5 2_656 . 109.0(6) ?
O7 Cl2 O5 . . 109.0(6) y
O8 Cl2 O6 . . 101.7(6) y
O8 Cl2 O6 2_656 . 70.0(6) ?
O7 Cl2 O6 2_656 . 71.2(5) ?
O7 Cl2 O6 . . 101.7(5) y
O5 Cl2 O6 . . 100.6(2) y
O8 Cl2 O6 . 2_656 70.0(6) ?
O8 Cl2 O6 2_656 2_656 101.7(6) ?
O7 Cl2 O6 2_656 2_656 101.7(5) ?
O7 Cl2 O6 . 2_656 71.2(5) ?
O5 Cl2 O6 . 2_656 100.6(2) ?
O6 Cl2 O6 . 2_656 158.8(4) ?
C6 O1 H1C . . 109.5 ?
C4 N1 C5 . . 123.18(18) ?
C4 N1 H1A . . 118.4 ?
C5 N1 H1A . . 118.4 ?
N1 C5 C1 . . 119.03(17) ?
N1 C5 C6 . . 115.74(17) ?
C1 C5 C6 . . 125.20(18) ?
O2 C6 O1 . . 127.62(18) ?
O2 C6 C5 . . 118.49(17) ?
O1 C6 C5 . . 113.88(16) ?
C3 C2 C1 . . 120.03(19) ?
C3 C2 H2B . . 120.0 ?
C1 C2 H2B . . 120.0 ?
N1 C4 C3 . . 119.6(2) ?
N1 C4 H4A . . 120.2 ?
C3 C4 H4A . . 120.2 ?
C4 C3 C2 . . 118.85(19) ?
C4 C3 H3A . . 120.6 ?
C2 C3 H3A . . 120.6 ?
C5 C1 C2 . . 119.26(19) ?
C5 C1 H1B . . 120.4 ?
C2 C1 H1B . . 120.4 ?
O8 O7 Cl2 2_656 . 72.6(10) ?
O8 O7 O6 2_656 2_656 129.8(16) ?
Cl2 O7 O6 . 2_656 59.8(5) ?
Cl2 O6 O8 . 2_656 48.9(3) ?
Cl2 O6 O7 . 2_656 49.0(2) ?
O8 O6 O7 2_656 2_656 91.5(4) ?
O7 O8 Cl2 2_656 . 75.7(10) ?
O7 O8 O6 2_656 2_656 136.5(14) ?
Cl2 O8 O6 . 2_656 61.1(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
Cl1 O10 2_656 1.4087(19) ?
Cl1 O10 . 1.4087(19) y
Cl1 O9 . 1.414(2) y
Cl1 O9 2_656 1.414(2) ?
O4 C12 . 1.271(3) ?
O4 H4B . 0.8300 ?
N2 C7 . 1.340(3) ?
N2 C11 . 1.346(3) ?
N2 H2A . 0.8700 ?
O3 C12 . 1.215(3) ?
C12 C11 . 1.508(3) ?
C10 C11 . 1.372(3) ?
C10 C9 . 1.399(3) ?
C10 H10A . 0.9400 ?
C9 C8 . 1.378(3) ?
C9 H9A . 0.9400 ?
C8 C7 . 1.380(3) ?
C8 H8A . 0.9400 ?
C7 H7A . 0.9400 ?
Cl2 O8 . 1.333(7) y
Cl2 O8 2_656 1.333(7) ?
Cl2 O7 2_656 1.353(7) ?
Cl2 O7 . 1.353(7) y
Cl2 O5 . 1.403(3) y
Cl2 O6 . 1.548(4) y
Cl2 O6 2_656 1.548(4) ?
O1 C6 . 1.268(2) ?
O1 H1C . 0.8300 ?
O2 C6 . 1.226(2) ?
N1 C4 . 1.338(3) ?
N1 C5 . 1.345(3) ?
N1 H1A . 0.8700 ?
C5 C1 . 1.375(3) ?
C5 C6 . 1.514(2) ?
C2 C3 . 1.381(3) ?
C2 C1 . 1.394(3) ?
C2 H2B . 0.9400 ?
C4 C3 . 1.380(3) ?
C4 H4A . 0.9400 ?
C3 H3A . 0.9400 ?
C1 H1B . 0.9400 ?
O7 O8 2_656 0.735(15) ?
O7 O6 2_656 1.696(13) ?
O6 O8 2_656 1.663(15) ?
O6 O7 2_656 1.696(13) ?
O8 O7 2_656 0.735(15) ?
O8 O6 2_656 1.663(15) ?
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
N2 H2A O2 6_566 0.87 1.93 2.752(2) 156.3
N1 H1A O3 6_565 0.87 1.91 2.706(2) 152.0
O4 H4B O1 . 0.83 1.64 2.444(2) 163.6
O1 H1C O4 . 0.83 1.65 2.444(2) 160.0
