#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2223375.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_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 '\f and \w'
_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/[\s^2^(Fo^2^)+(0.053P)^2^+0.0522P] where P=(Fo^2^+2Fc^2^)/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>2\s(I)
_[local]_cod_data_source_file fl2261.cif
_[local]_cod_data_source_block I
_[local]_cod_cif_authors_sg_H-M 'P 21'
_cod_database_code 2223375
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1A 0.0167(6) 0.0212(7) 0.0195(7) -0.0015(6) 0.0013(5) 0.0001(6)
N10A 0.0217(7) 0.0224(7) 0.0193(7) 0.0012(6) 0.0005(6) -0.0004(6)
C2A 0.0222(8) 0.0261(8) 0.0222(8) -0.0047(8) 0.0078(7) -0.0028(7)
C3A 0.0292(10) 0.0360(10) 0.0182(8) -0.0077(8) 0.0036(7) 0.0005(7)
C4A 0.0268(9) 0.0298(9) 0.0230(8) -0.0069(8) -0.0029(7) 0.0060(8)
C5A 0.0176(8) 0.0211(8) 0.0302(9) -0.0004(7) -0.0040(7) 0.0041(7)
C6A 0.0164(8) 0.0202(9) 0.0375(10) 0.0014(7) 0.0033(7) -0.0017(8)
C7A 0.0242(9) 0.0253(10) 0.0295(10) 0.0011(8) 0.0104(7) -0.0027(7)
C8A 0.0358(10) 0.0308(10) 0.0203(8) 0.0001(9) 0.0096(7) -0.0023(8)
C9A 0.0295(9) 0.0263(9) 0.0197(8) 0.0025(8) -0.0007(7) 0.0020(7)
C11A 0.0182(8) 0.0164(7) 0.0207(8) -0.0009(6) 0.0026(6) 0.0009(6)
C12A 0.0163(7) 0.0166(7) 0.0204(8) -0.0040(6) 0.0005(6) 0.0001(6)
C13A 0.0186(7) 0.0188(7) 0.0241(8) -0.0039(7) -0.0020(6) 0.0027(7)
C14A 0.0195(8) 0.0181(8) 0.0248(8) -0.0031(7) 0.0039(6) -0.0021(7)
Cl4 0.0291(2) 0.0541(3) 0.0169(2) 0.0014(2) 0.0045(2) -0.0034(2)
Cl5 0.0251(2) 0.0463(3) 0.0221(2) 0.0067(2) -0.0046(2) -0.0001(2)
O11 0.0227(6) 0.0297(7) 0.0236(6) 0.0044(6) 0.0058(5) -0.0029(5)
O12 0.0260(6) 0.0354(7) 0.0187(6) 0.0056(6) 0.0052(5) 0.0018(5)
O21 0.0264(7) 0.0343(7) 0.0204(6) 0.0068(6) 0.0009(5) 0.0030(5)
O22 0.0200(6) 0.0284(7) 0.0277(7) 0.0044(5) 0.0023(5) 0.0012(5)
C1 0.0189(8) 0.0157(8) 0.0192(8) -0.0027(6) 0.0029(6) 0.0006(6)
C2 0.0188(8) 0.0149(7) 0.0197(8) -0.0012(6) 0.0024(6) 0.0007(6)
C3 0.0189(8) 0.0215(9) 0.0215(8) -0.0012(7) 0.0032(7) -0.0034(6)
C4 0.0229(8) 0.0263(9) 0.0161(7) -0.0035(7) 0.0057(6) -0.0019(7)
C5 0.0188(8) 0.0231(8) 0.0196(8) -0.0005(7) -0.0019(6) 0.0019(7)
C6 0.0155(7) 0.0207(8) 0.0229(8) 0.0010(6) 0.0040(6) -0.0014(7)
C11 0.0202(8) 0.0197(8) 0.0192(8) -0.0041(7) 0.0055(6) -0.0012(6)
C21 0.0168(7) 0.0173(8) 0.0233(8) -0.0023(6) -0.0005(6) -0.0004(6)
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
_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_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
_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