#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/33/2223375.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_2223375
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
'White, Jonathan M.'
_publ_section_title
;
 1,10-Phenanthrolin-1-ium 2-carboxy-4,5-dichlorobenzoate
;
_journal_coeditor_code           FL2261
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2333
_journal_paper_doi               10.1107/S1600536809034448
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H9 N2 +, C8 H3 Cl2 O4 -'
_chemical_formula_moiety         'C12 H9 N2 +, C8 H3 Cl2 O4 -'
_chemical_formula_sum            'C20 H12 Cl2 N2 O4'
_chemical_formula_weight         415.22
_chemical_melting_point_gt       464
_chemical_melting_point_lt       465
_chemical_name_common
'1,10-phenanthrolinium hydrogen 4,5-dichlorophthalate'
_chemical_name_systematic
;
1,10-Phenanthrolin-1-ium 2-carboxy-4,5-dichlorobenzoate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 94.978(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4598(11)
_cell_length_b                   7.3696(12)
_cell_length_c                   18.302(3)
_cell_measurement_reflns_used    3630
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.23
_cell_volume                     868.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5464
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         1.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.187
_refine_ls_abs_structure_details 'Flack (1983), 1564 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3734
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0319
_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)+(0.053P)²+0.0522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0853
_reflns_number_gt                3629
_reflns_number_total             3734
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2261.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2223375
_cod_database_fobs_code          2223375
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1A 0.4667(2) 0.7304(2) 0.14863(8) 0.0192(4) Uani . . 1.000
N N10A 0.4177(2) 0.7715(2) 0.29542(8) 0.0212(4) Uani . . 1.000
C C2A 0.5046(3) 0.7149(3) 0.07881(10) 0.0232(5) Uani . . 1.000
C C3A 0.3645(3) 0.7828(3) 0.02322(10) 0.0277(5) Uani . . 1.000
C C4A 0.1845(3) 0.8641(3) 0.04213(10) 0.0268(5) Uani . . 1.000
C C5A -0.0459(3) 0.9562(3) 0.13825(11) 0.0233(5) Uani . . 1.000
C C6A -0.0804(3) 0.9634(2) 0.20961(11) 0.0246(5) Uani . . 1.000
C C7A 0.0442(3) 0.9113(2) 0.34093(10) 0.0259(6) Uani . . 1.000
C C8A 0.2013(3) 0.8540(3) 0.39058(10) 0.0286(5) Uani . . 1.000
C C9A 0.3857(3) 0.7854(3) 0.36523(10) 0.0253(5) Uani . . 1.000
C C11A 0.2617(3) 0.8274(2) 0.24641(9) 0.0184(4) Uani . . 1.000
C C12A 0.2916(3) 0.8115(2) 0.16952(10) 0.0178(4) Uani . . 1.000
C C13A 0.1421(3) 0.8783(2) 0.11565(10) 0.0207(4) Uani . . 1.000
C C14A 0.0717(3) 0.9002(2) 0.26564(10) 0.0207(5) Uani . . 1.000
Cl Cl4 1.15820(7) 0.37080(8) 0.46649(2) 0.03320(10) Uani . . 1.000
Cl Cl5 1.59276(7) 0.22144(8) 0.42219(2) 0.03160(10) Uani . . 1.000
O O11 1.5052(2) 0.18688(18) 0.14604(7) 0.0251(4) Uani . . 1.000
O O12 1.2404(2) 0.34157(19) 0.09355(7) 0.0265(4) Uani . . 1.000
O O21 0.9277(2) 0.4836(2) 0.12771(7) 0.0271(4) Uani . . 1.000
O O22 0.76248(19) 0.53666(18) 0.22655(7) 0.0254(4) Uani . . 1.000
C C1 1.2820(3) 0.3211(2) 0.22748(9) 0.0179(5) Uani . . 1.000
C C2 1.0928(3) 0.3971(2) 0.24707(9) 0.0178(4) Uani . . 1.000
C C3 1.0603(3) 0.4092(2) 0.32117(10) 0.0206(5) Uani . . 1.000
C C4 1.2096(3) 0.3536(3) 0.37559(9) 0.0215(5) Uani . . 1.000
C C5 1.3983(3) 0.2862(2) 0.35636(10) 0.0207(5) Uani . . 1.000
C C6 1.4314(3) 0.2693(2) 0.28333(10) 0.0196(4) Uani . . 1.000
C C11 1.3502(3) 0.2788(2) 0.15083(9) 0.0195(5) Uani . . 1.000
C C21 0.9127(3) 0.4764(2) 0.19673(9) 0.0193(4) Uani . . 1.000
H H1A 0.556(3) 0.683(3) 0.1842(12) 0.021(5) Uiso . . 1.000
H H2A 0.62580 0.65840 0.06680 0.0280 Uiso calc R 1.000
H H3A 0.39190 0.77330 -0.02570 0.0330 Uiso calc R 1.000
H H4A 0.09010 0.91030 0.00560 0.0320 Uiso calc R 1.000
H H5A -0.14490 1.00210 0.10310 0.0280 Uiso calc R 1.000
H H6A -0.20540 1.01040 0.22290 0.0300 Uiso calc R 1.000
H H7A -0.07860 0.95670 0.35670 0.0310 Uiso calc R 1.000
H H8A 0.18650 0.86030 0.44060 0.0340 Uiso calc R 1.000
H H9A 0.49080 0.74780 0.39980 0.0300 Uiso calc R 1.000
H H3 0.93520 0.45580 0.33450 0.0250 Uiso calc R 1.000
H H6 1.55700 0.22200 0.27080 0.0230 Uiso calc R 1.000
H H12 1.113(5) 0.400(4) 0.1072(17) 0.035(9) Uiso . . 1.000
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O12 H12 . . . 111(2) no
C2A N1A C12A . . . 122.34(16) no
C9A N10A C11A . . . 116.68(15) no
C12A N1A H1A . . . 117.5(13) no
C2A N1A H1A . . . 120.1(13) no
N1A C2A C3A . . . 120.63(18) no
C2A C3A C4A . . . 118.74(17) no
C3A C4A C13A . . . 120.89(17) no
C6A C5A C13A . . . 120.73(18) no
C5A C6A C14A . . . 121.35(18) no
C8A C7A C14A . . . 118.87(17) no
C7A C8A C9A . . . 119.43(17) no
N10A C9A C8A . . . 123.79(17) no
N10A C11A C14A . . . 124.31(15) no
C12A C11A C14A . . . 117.85(16) no
N10A C11A C12A . . . 117.83(16) no
C11A C12A C13A . . . 120.89(17) no
N1A C12A C11A . . . 119.61(16) no
N1A C12A C13A . . . 119.50(16) no
C5A C13A C12A . . . 118.94(17) no
C4A C13A C5A . . . 123.19(17) no
C4A C13A C12A . . . 117.87(17) no
C6A C14A C7A . . . 122.97(17) no
C7A C14A C11A . . . 116.91(16) no
C6A C14A C11A . . . 120.09(16) no
C3A C2A H2A . . . 120.00 no
N1A C2A H2A . . . 120.00 no
C2A C3A H3A . . . 121.00 no
C4A C3A H3A . . . 121.00 no
C3A C4A H4A . . . 120.00 no
C13A C4A H4A . . . 120.00 no
C6A C5A H5A . . . 120.00 no
C13A C5A H5A . . . 120.00 no
C14A C6A H6A . . . 119.00 no
C5A C6A H6A . . . 119.00 no
C8A C7A H7A . . . 121.00 no
C14A C7A H7A . . . 121.00 no
C9A C8A H8A . . . 120.00 no
C7A C8A H8A . . . 120.00 no
C8A C9A H9A . . . 118.00 no
N10A C9A H9A . . . 118.00 no
C2 C1 C11 . . . 129.18(16) no
C2 C1 C6 . . . 118.60(15) no
C6 C1 C11 . . . 112.19(16) no
C1 C2 C21 . . . 128.55(15) no
C1 C2 C3 . . . 118.51(16) no
C3 C2 C21 . . . 112.92(16) no
C2 C3 C4 . . . 121.74(17) no
Cl4 C4 C5 . . . 121.05(14) no
C3 C4 C5 . . . 119.63(16) no
Cl4 C4 C3 . . . 119.32(15) no
C4 C5 C6 . . . 119.44(17) no
Cl5 C5 C4 . . . 121.47(14) no
Cl5 C5 C6 . . . 119.09(15) no
C1 C6 C5 . . . 122.00(17) no
O11 C11 C1 . . . 118.72(15) no
O12 C11 C1 . . . 118.97(15) no
O11 C11 O12 . . . 122.32(16) no
O22 C21 C2 . . . 117.04(15) no
O21 C21 O22 . . . 123.49(17) no
O21 C21 C2 . . . 119.41(16) no
C2 C3 H3 . . . 119.00 no
C4 C3 H3 . . . 119.00 no
C1 C6 H6 . . . 119.00 no
C5 C6 H6 . . . 119.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl4 C4 . . 1.7291(17) no
Cl5 C5 . . 1.7305(19) no
O11 C11 . . 1.218(2) no
O12 C11 . . 1.299(2) no
O21 C21 . . 1.276(2) no
O22 C21 . . 1.236(2) no
O12 H12 . . 0.98(3) no
N1A C12A . . 1.363(2) no
N1A C2A . . 1.327(2) no
N10A C11A . . 1.354(2) no
N10A C9A . . 1.316(2) no
N1A H1A . . 0.90(2) no
C2A C3A . . 1.395(3) no
C3A C4A . . 1.379(3) no
C4A C13A . . 1.400(3) no
C5A C6A . . 1.345(3) no
C5A C13A . . 1.436(3) no
C6A C14A . . 1.435(3) no
C7A C14A . . 1.407(3) no
C7A C8A . . 1.369(3) no
C8A C9A . . 1.409(3) no
C11A C12A . . 1.442(2) no
C11A C14A . . 1.412(3) no
C12A C13A . . 1.408(3) no
C2A H2A . . 0.9300 no
C3A H3A . . 0.9300 no
C4A H4A . . 0.9300 no
C5A H5A . . 0.9300 no
C6A H6A . . 0.9300 no
C7A H7A . . 0.9300 no
C8A H8A . . 0.9300 no
C9A H9A . . 0.9300 no
C1 C2 . . 1.419(3) no
C1 C11 . . 1.538(2) no
C1 C6 . . 1.397(3) no
C2 C21 . . 1.536(3) no
C2 C3 . . 1.393(2) no
C3 C4 . . 1.387(3) no
C4 C5 . . 1.390(3) no
C5 C6 . . 1.377(3) no
C3 H3 . . 0.9300 no
C6 H6 . . 0.9300 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
N1A H1A O22 . 0.90(2) 1.83(2) 2.6926(19) 158(2) yes
N1A H1A N10A . 0.90(2) 2.38(2) 2.749(2) 104.3(15) yes
O12 H12 O21 . 0.98(3) 1.43(3) 2.4054(19) 179(4) yes
C2A H2A O21 . 0.93 2.52 3.279(2) 140 yes
C3 H3 O22 . 0.93 2.26 2.647(2) 104 yes
C3A H3A O11 2_755 0.93 2.44 3.355(2) 168 yes
C4A H4A O21 2_655 0.93 2.49 3.252(2) 139 yes
C6 H6 O11 . 0.93 2.29 2.668(2) 103 yes
C6A H6A O11 1_365 0.93 2.59 3.270(2) 130 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12A N1A C2A C3A . . . . 0.2(3) no
C2A N1A C12A C11A . . . . -178.71(17) no
C2A N1A C12A C13A . . . . 1.4(3) no
C11A N10A C9A C8A . . . . 0.0(3) no
C9A N10A C11A C12A . . . . -179.22(16) no
C9A N10A C11A C14A . . . . 0.8(2) no
N1A C2A C3A C4A . . . . -0.9(3) no
C2A C3A C4A C13A . . . . -0.1(3) no
C3A C4A C13A C5A . . . . -177.89(19) no
C3A C4A C13A C12A . . . . 1.7(3) no
C13A C5A C6A C14A . . . . 2.4(3) no
C6A C5A C13A C4A . . . . 178.76(18) no
C6A C5A C13A C12A . . . . -0.8(3) no
C5A C6A C14A C7A . . . . 177.74(17) no
C5A C6A C14A C11A . . . . -0.5(2) no
C14A C7A C8A C9A . . . . -0.1(3) no
C8A C7A C14A C6A . . . . -177.47(17) no
C8A C7A C14A C11A . . . . 0.8(2) no
C7A C8A C9A N10A . . . . -0.3(3) no
N10A C11A C12A N1A . . . . 4.5(2) no
N10A C11A C12A C13A . . . . -175.62(15) no
C14A C11A C12A N1A . . . . -175.47(15) no
C14A C11A C12A C13A . . . . 4.4(2) no
N10A C11A C14A C6A . . . . 177.13(15) no
N10A C11A C14A C7A . . . . -1.2(2) no
C12A C11A C14A C6A . . . . -2.9(2) no
C12A C11A C14A C7A . . . . 178.83(14) no
N1A C12A C13A C4A . . . . -2.4(2) no
N1A C12A C13A C5A . . . . 177.27(16) no
C11A C12A C13A C4A . . . . 177.79(16) no
C11A C12A C13A C5A . . . . -2.6(2) no
C6 C1 C2 C3 . . . . -2.9(2) no
C6 C1 C2 C21 . . . . 175.21(15) no
C11 C1 C2 C3 . . . . 174.90(15) no
C11 C1 C2 C21 . . . . -7.0(3) no
C2 C1 C6 C5 . . . . 1.5(2) no
C11 C1 C6 C5 . . . . -176.68(14) no
C2 C1 C11 O11 . . . . -168.30(16) no
C2 C1 C11 O12 . . . . 11.4(3) no
C6 C1 C11 O11 . . . . 9.6(2) no
C6 C1 C11 O12 . . . . -170.67(15) no
C1 C2 C3 C4 . . . . 1.7(2) no
C21 C2 C3 C4 . . . . -176.64(16) no
C1 C2 C21 O21 . . . . -2.2(3) no
C1 C2 C21 O22 . . . . -179.53(16) no
C3 C2 C21 O21 . . . . 175.96(15) no
C3 C2 C21 O22 . . . . -1.4(2) no
C2 C3 C4 Cl4 . . . . -179.50(14) no
C2 C3 C4 C5 . . . . 0.9(3) no
Cl4 C4 C5 Cl5 . . . . -1.6(2) no
Cl4 C4 C5 C6 . . . . 178.04(14) no
C3 C4 C5 Cl5 . . . . 178.02(14) no
C3 C4 C5 C6 . . . . -2.4(3) no
Cl5 C5 C6 C1 . . . . -179.20(12) no
C4 C5 C6 C1 . . . . 1.2(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655882
