#------------------------------------------------------------------------------
#$Date: 2017-05-05 08:49:52 +0300 (Fri, 05 May 2017) $
#$Revision: 196234 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/87/2018705.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_2018705
loop_
_publ_author_name
'Vranec, Peter'
'Potočňák, Ivan'
'Repovský, Peter'
_publ_section_title
;
 Low-dimensional compounds containing bioactive ligands. IV. Unusual ionic
 forms of 5-chloroquinolin-8-ol
;
_journal_coeditor_code           FG3281
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m370
_journal_page_last               m376
_journal_paper_doi               10.1107/S0108270112047452
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C2 H10 N2 2+, 2C9 H5 Cl N O -'
_chemical_formula_moiety         'C2 H10 N2 2+, 2(C9 H5 Cl N O -)'
_chemical_formula_sum            'C20 H20 Cl2 N4 O2'
_chemical_formula_weight         419.30
_chemical_name_systematic
;
Ethylenediammonium bis(5-chloroquinolin-8-olate)
;
_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                 96.087(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.8369(5)
_cell_length_b                   6.8335(3)
_cell_length_c                   8.7459(4)
_cell_measurement_reflns_used    3109
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      29.5422
_cell_measurement_theta_min      3.2432
_cell_volume                     941.16(7)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 8.3438
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur (Sapphire2, large Be window)'
_diffrn_measurement_method       'ω scans'
_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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6777
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_T_max  0.241
_exptl_absorpt_correction_T_min  0.106
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis PRO (Oxford Diffraction, 2007), based on expressions derived
by
Clark & Reid (1995)]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.3170
_exptl_crystal_size_mid          0.2999
_exptl_crystal_size_min          0.1798
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.189
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0366
_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)+(0.0437P)²+0.3861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                1610
_reflns_number_total             1953
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fg3281.cif
_cod_data_source_block           III
_cod_depositor_comments
;

2017-04-24
Fixing wrong formula (asymetric unit was indicated instead).
                 miguel
;
_cod_original_formula_sum            'C10 H10 Cl N2 O'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018705
_cod_database_fobs_code          2018705
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_symmetry_multiplicity
Cl Cl1 0.05358(3) 0.72953(8) 0.71628(6) 0.03992(18) Uani d . 1 1
C C1 0.24967(11) 0.1971(3) 0.4904(2) 0.0265(4) Uani d . 1 1
H H1 0.2705 0.0842 0.4434 0.032 Uiso calc R 1 1
C C2 0.16153(11) 0.2106(3) 0.4988(2) 0.0281(4) Uani d . 1 1
H H2 0.1244 0.1098 0.4581 0.034 Uiso calc R 1 1
C C3 0.13066(10) 0.3702(3) 0.5661(2) 0.0271(4) Uani d . 1 1
H H3 0.0714 0.3818 0.5733 0.032 Uiso calc R 1 1
C C4 0.18667(10) 0.5197(2) 0.62566(18) 0.0209(4) Uani d . 1 1
C C5 0.16087(10) 0.6923(3) 0.6970(2) 0.0249(4) Uani d . 1 1
C C6 0.21846(11) 0.8303(3) 0.75126(19) 0.0248(4) Uani d . 1 1
H H6 0.1998 0.9451 0.7989 0.030 Uiso calc R 1 1
C C7 0.30545(10) 0.8038(2) 0.73709(19) 0.0224(4) Uani d . 1 1
H H7 0.3444 0.9017 0.7765 0.027 Uiso calc R 1 1
C C8 0.33615(10) 0.6403(2) 0.66789(17) 0.0188(3) Uani d . 1 1
C C9 0.27492(9) 0.4934(2) 0.61074(18) 0.0189(3) Uani d . 1 1
C C11 0.53688(10) 0.5689(2) 0.9921(2) 0.0208(4) Uani d . 1 1
O O1 0.41795(6) 0.61455(16) 0.65317(12) 0.0202(3) Uani d . 1 1
N N1 0.30504(8) 0.3310(2) 0.54356(16) 0.0219(3) Uani d . 1 1
N N2 0.50427(9) 0.7520(2) 0.91811(17) 0.0183(3) Uani d . 1 1
H H11B 0.5767(11) 0.512(3) 0.925(2) 0.024(5) Uiso d . 1 1
H H2N2 0.4685(12) 0.801(3) 0.980(2) 0.020(5) Uiso d . 1 1
H H11A 0.5664(11) 0.601(3) 1.092(2) 0.023(5) Uiso d . 1 1
H H1N2 0.4779(14) 0.722(3) 0.825(3) 0.036(6) Uiso d . 1 1
H H3N2 0.5461(14) 0.839(3) 0.907(2) 0.037(6) Uiso d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
C C 0.0033 0.0016 '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
N1 C1 C2 . . 124.21(16)
N1 C1 H1 . . 117.9
C2 C1 H1 . . 117.9
C3 C2 C1 . . 118.73(16)
C3 C2 H2 . . 120.6
C1 C2 H2 . . 120.6
C2 C3 C4 . . 119.99(16)
C2 C3 H3 . . 120.0
C4 C3 H3 . . 120.0
C5 C4 C3 . . 124.40(15)
C5 C4 C9 . . 118.45(15)
C3 C4 C9 . . 117.15(15)
C6 C5 C4 . . 121.12(15)
C6 C5 Cl1 . . 119.26(14)
C4 C5 Cl1 . . 119.63(13)
C5 C6 C7 . . 120.38(16)
C5 C6 H6 . . 119.8
C7 C6 H6 . . 119.8
C8 C7 C6 . . 122.35(15)
C8 C7 H7 . . 118.8
C6 C7 H7 . . 118.8
O1 C8 C7 . . 122.80(14)
O1 C8 C9 . . 119.96(14)
C7 C8 C9 . . 117.23(14)
N1 C9 C4 . . 122.10(14)
N1 C9 C8 . . 117.43(14)
C4 C9 C8 . . 120.47(15)
N2 C11 C11 . 3_667 109.19(16)
N2 C11 H11B . . 107.0(11)
C11 C11 H11B 3_667 . 110.9(11)
N2 C11 H11A . . 108.4(11)
C11 C11 H11A 3_667 . 110.9(11)
H11B C11 H11A . . 110.3(14)
C1 N1 C9 . . 117.81(14)
C11 N2 H2N2 . . 105.8(12)
C11 N2 H1N2 . . 107.9(13)
H2N2 N2 H1N2 . . 111.8(18)
C11 N2 H3N2 . . 112.2(13)
H2N2 N2 H3N2 . . 110.0(18)
H1N2 N2 H3N2 . . 109.2(18)
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 C5 . 1.7437(17) yes
C1 N1 . 1.317(2) yes
C1 C2 . 1.409(2) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.355(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.416(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.414(2) ?
C4 C9 . 1.429(2) ?
C5 C6 . 1.362(3) ?
C6 C7 . 1.408(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.383(2) ?
C7 H7 . 0.9500 ?
C8 O1 . 1.3272(18) yes
C8 C9 . 1.447(2) ?
C9 N1 . 1.365(2) yes
C11 N2 . 1.477(2) ?
C11 C11 3_667 1.518(3) ?
C11 H11B . 0.983(19) ?
C11 H11A . 0.974(18) ?
N2 H2N2 . 0.89(2) ?
N2 H1N2 . 0.90(2) ?
N2 H3N2 . 0.90(2) ?
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 H2N2 O1 4_576 0.89(2) 1.88(2) 2.7427(18) 163.6(16)
N2 H1N2 O1 . 0.90(2) 1.84(2) 2.7292(18) 168.7(19)
N2 H3N2 O1 2_656 0.90(2) 2.05(2) 2.8646(18) 149.0(18)
N2 H3N2 N1 2_656 0.90(2) 2.35(2) 3.051(2) 134.3(17)
