#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/43/2204379.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_2204379
loop_
_publ_author_name
'Hiroyuki Ishida'
_publ_section_title
;
 1,2,3,4-Tetrahydroquinolinium hydrogen chloranilate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1674
_journal_page_last               o1676
_journal_paper_doi               10.1107/S1600536804021531
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C9 H12 N 1+, C6 H Cl2 O4 1-'
_chemical_formula_moiety         'C9 H12 N 1+, C6 H Cl2 O4 1-'
_chemical_formula_sum            'C15 H13 Cl2 N O4'
_chemical_formula_weight         342.16
_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
_cell_angle_alpha                90
_cell_angle_beta                 108.79(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.840(8)
_cell_length_b                   7.0633(10)
_cell_length_c                   17.107(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      11.5
_cell_volume                     2955.9(14)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1990)
;
_computing_data_reduction
'TEXSAN for Windows (Molecular Structure Corporation, 1997-1999)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Rigaku AFC-5R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.015
_diffrn_reflns_av_sigmaI/netI    0.032
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3771
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        0.16
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.456
_exptl_absorpt_correction_T_max  0.872
_exptl_absorpt_correction_T_min  0.783
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.61
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.067
_refine_ls_R_factor_gt           0.042
_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)+(0.067P)²+1.1P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.110
_refine_ls_wR_factor_ref         0.121
_reflns_number_gt                2498
_reflns_number_total             3395
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6000.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2204379
_cod_database_fobs_code          2204379
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,   +y,1/2-z'
'   -x,   -y,   -z'
'   +x,   -y,1/2+z'
'1/2+x,1/2+y,   +z'
1/2-x,1/2+y,1/2-z
'1/2-x,1/2-y,   -z'
1/2+x,1/2-y,1/2+z
loop_
_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_type_symbol
Cl1 0.34526(2) 0.40579(10) 0.52845(3) 0.04241(17) Uani d . 1 Cl
Cl2 0.58195(2) 0.16961(9) 0.52962(4) 0.04317(17) Uani d . 1 Cl
O1 0.44826(6) 0.3578(2) 0.67302(8) 0.0364(4) Uani d . 1 O
O2 0.38233(6) 0.3434(3) 0.38271(9) 0.0426(4) Uani d . 1 O
O3 0.48340(6) 0.2510(3) 0.38367(9) 0.0466(4) Uani d . 1 O
O4 0.54607(6) 0.2552(3) 0.67284(9) 0.0399(4) Uani d . 1 O
N 0.38474(7) 0.3619(3) 0.22434(11) 0.0335(4) Uani d . 1 N
C1 0.45193(8) 0.3308(3) 0.60226(12) 0.0278(4) Uani d . 1 C
C2 0.40986(8) 0.3482(3) 0.52748(12) 0.0286(4) Uani d . 1 C
C3 0.41800(8) 0.3235(3) 0.45046(12) 0.0299(4) Uani d . 1 C
C4 0.47592(8) 0.2676(3) 0.45027(12) 0.0301(4) Uani d . 1 C
C5 0.51810(8) 0.2407(3) 0.52868(12) 0.0291(4) Uani d . 1 C
C6 0.50741(8) 0.2727(3) 0.59976(12) 0.0282(4) Uani d . 1 C
C7 0.40313(11) 0.1878(4) 0.19134(17) 0.0561(7) Uani d . 1 C
C8 0.36387(13) 0.0326(4) 0.1829(2) 0.0631(8) Uani d . 1 C
C9 0.30810(12) 0.0842(4) 0.12204(18) 0.0564(7) Uani d . 1 C
C10 0.23445(10) 0.3256(4) 0.11574(17) 0.0528(7) Uani d . 1 C
C11 0.21712(11) 0.4965(5) 0.13567(18) 0.0569(7) Uani d . 1 C
C12 0.25393(11) 0.6201(4) 0.18672(18) 0.0504(6) Uani d . 1 C
C13 0.30855(10) 0.5727(3) 0.21646(14) 0.0398(5) Uani d . 1 C
C14 0.32553(8) 0.4019(3) 0.19319(11) 0.0289(4) Uani d . 1 C
C15 0.28928(9) 0.2732(3) 0.14344(13) 0.0371(5) Uani d . 1 C
H1 0.5346(15) 0.280(6) 0.715(3) 0.119(15) Uiso d . 1 H
H2 0.3949(10) 0.352(4) 0.2786(17) 0.042(7) Uiso d . 1 H
H3 0.4019(11) 0.463(4) 0.2127(17) 0.047(7) Uiso d . 1 H
H4 0.4069 0.2153 0.1379 0.084 Uiso calc R 1 H
H5 0.4386 0.1494 0.2283 0.084 Uiso calc R 1 H
H6 0.3775 -0.0804 0.1639 0.095 Uiso calc R 1 H
H7 0.3601 0.0051 0.2364 0.095 Uiso calc R 1 H
H8 0.3104 0.0889 0.0666 0.085 Uiso calc R 1 H
H9 0.2817 -0.0124 0.1232 0.085 Uiso calc R 1 H
H10 0.2088 0.2420 0.0827 0.063 Uiso calc R 1 H
H11 0.1804 0.5292 0.1147 0.068 Uiso calc R 1 H
H12 0.2420 0.7351 0.2011 0.060 Uiso calc R 1 H
H13 0.3337 0.6543 0.2517 0.048 Uiso calc R 1 H
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 0 -4
-2 -2 -1
-4 -2 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 O4 H1 114(3)
C14 N C7 116.10(18)
C14 N H2 108.6(16)
C7 N H2 107.9(17)
C14 N H3 107.3(17)
C7 N H3 109.3(17)
H2 N H3 107(2)
O1 C1 C2 126.28(18)
O1 C1 C6 115.86(17)
C2 C1 C6 117.86(17)
C1 C2 C3 122.69(18)
C1 C2 Cl1 118.97(15)
C3 C2 Cl1 118.33(15)
O2 C3 C2 124.88(19)
O2 C3 C4 117.18(17)
C2 C3 C4 117.94(16)
O3 C4 C5 123.76(19)
O3 C4 C3 118.02(18)
C5 C4 C3 118.21(16)
C6 C5 C4 120.19(18)
C6 C5 Cl2 120.97(16)
C4 C5 Cl2 118.84(14)
O4 C6 C5 121.40(18)
O4 C6 C1 115.61(17)
C5 C6 C1 122.99(17)
C8 C7 N 111.0(2)
C8 C7 H4 109.4
N C7 H4 109.4
C8 C7 H5 109.4
N C7 H5 109.4
H4 C7 H5 108.0
C7 C8 C9 111.0(3)
C7 C8 H6 109.4
C9 C8 H6 109.4
C7 C8 H7 109.4
C9 C8 H7 109.4
H6 C8 H7 108.0
C15 C9 C8 110.7(2)
C15 C9 H8 109.5
C8 C9 H8 109.5
C15 C9 H9 109.5
C8 C9 H9 109.5
H8 C9 H9 108.1
C11 C10 C15 121.9(2)
C11 C10 H10 119.0
C15 C10 H10 119.0
C10 C11 C12 120.2(2)
C10 C11 H11 119.9
C12 C11 H11 119.9
C11 C12 C13 119.8(2)
C11 C12 H12 120.1
C13 C12 H12 120.1
C12 C13 C14 119.1(2)
C12 C13 H13 120.4
C14 C13 H13 120.4
C15 C14 C13 122.3(2)
C15 C14 N 120.94(19)
C13 C14 N 116.74(19)
C14 C15 C10 116.6(2)
C14 C15 C9 121.6(2)
C10 C15 C9 121.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.723(2)
Cl2 C5 1.720(2)
O1 C1 1.259(2)
O2 C3 1.235(2)
O3 C4 1.221(2)
O4 C6 1.331(2)
O4 H1 0.88(4)
N C14 1.476(3)
N C7 1.493(3)
N H2 0.88(3)
N H3 0.89(3)
C1 C2 1.392(3)
C1 C6 1.505(3)
C2 C3 1.411(3)
C3 C4 1.549(3)
C4 C5 1.443(3)
C5 C6 1.350(3)
C7 C8 1.469(4)
C8 C9 1.525(4)
C9 C15 1.506(4)
C10 C11 1.368(4)
C10 C15 1.391(3)
C11 C12 1.376(4)
C12 C13 1.378(4)
C13 C14 1.385(3)
C14 C15 1.383(3)
C7 H4 0.97
C7 H5 0.97
C8 H6 0.97
C8 H7 0.97
C9 H8 0.97
C9 H9 0.97
C10 H10 0.93
C11 H11 0.93
C12 H12 0.93
C13 H13 0.93
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 O4 2.693(2) 2_656 no
O1 N 2.883(3) 4_565 no
O1 O1 3.090(2) 2_656 no
O2 N 2.733(2) . no
O2 C14 3.126(3) . no
O2 C13 3.295(3) . no
O3 N 3.173(3) . no
O3 C7 3.306(3) . no
O3 C1 3.364(3) 3_666 no
O3 C6 3.378(3) 3_666 no
C3 C5 3.457(3) 3_666 no
C4 C6 3.420(3) 3_666 no
C4 C5 3.490(3) 3_666 no
C5 C5 3.579(3) 3_656 no
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
_geom_hbond_publ_flag
O4 H1 O1 . 0.88(5) 2.18(4) 2.630(2) 111(4) yes
O4 H1 O1 2_656 0.88(5) 1.90(5) 2.693(2) 148(4) yes
N H2 O2 . 0.88(3) 1.91(3) 2.733(2) 154(3) yes
N H2 O3 . 0.88(3) 2.51(3) 3.173(3) 132(2) yes
N H3 O1 4_564 0.90(3) 2.01(3) 2.883(3) 166(3) yes
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
O1 C1 C2 C3 177.1(2)
C6 C1 C2 C3 -3.4(3)
O1 C1 C2 Cl1 -1.9(3)
C6 C1 C2 Cl1 177.59(15)
C1 C2 C3 O2 -177.6(2)
Cl1 C2 C3 O2 1.4(3)
C1 C2 C3 C4 2.3(3)
Cl1 C2 C3 C4 -178.72(15)
O2 C3 C4 O3 1.8(3)
C2 C3 C4 O3 -178.1(2)
O2 C3 C4 C5 -179.1(2)
C2 C3 C4 C5 1.0(3)
O3 C4 C5 C6 176.0(2)
C3 C4 C5 C6 -3.1(3)
O3 C4 C5 Cl2 -3.4(3)
C3 C4 C5 Cl2 177.50(15)
C4 C5 C6 O4 -177.7(2)
Cl2 C5 C6 O4 1.7(3)
C4 C5 C6 C1 2.0(3)
Cl2 C5 C6 C1 -178.58(16)
O1 C1 C6 O4 0.6(3)
C2 C1 C6 O4 -179.01(19)
O1 C1 C6 C5 -179.2(2)
C2 C1 C6 C5 1.2(3)
C14 N C7 C8 -38.9(3)
N C7 C8 C9 61.7(3)
C7 C8 C9 C15 -51.3(3)
C15 C10 C11 C12 -2.2(4)
C10 C11 C12 C13 1.3(4)
C11 C12 C13 C14 1.0(4)
C12 C13 C14 C15 -2.5(3)
C12 C13 C14 N 177.7(2)
C7 N C14 C15 6.7(3)
C7 N C14 C13 -173.5(2)
C13 C14 C15 C10 1.6(3)
N C14 C15 C10 -178.6(2)
C13 C14 C15 C9 -177.1(2)
N C14 C15 C9 2.7(3)
C11 C10 C15 C14 0.8(4)
C11 C10 C15 C9 179.4(3)
C8 C9 C15 C14 19.3(4)
C8 C9 C15 C10 -159.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654766
2 PubChem 139067057
