#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:30:06 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180224 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/10/7111035.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7111035
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
'White, Jonathan M.'
_publ_section_title
;
 Molecular recognition involving Kemp’s triacid: selectivity
 towards the 8-substituted quinoline system as seen in the cocrystalline
 adducts with 8-aminoquinoline and 8-hydroxyquinoline
;
_journal_issue                   23
_journal_name_full               'Chemical Communications'
_journal_page_first              2349
_journal_paper_doi               10.1039/b004945j
_journal_year                    2000
_chemical_formula_moiety         '(C12 H18 O6)2 (C9 H8 N2)'
_chemical_formula_sum            'C33 H44 N2 O12'
_chemical_formula_weight         660.70
_chemical_name_common
;
Kemp's triacid: 8-aminoquinoline (2:1)     
;
_chemical_name_systematic
;
bis(cis-cis-1,3,5-trimethylcyclohexane-1,3,5-tricarboxylic acid)
(8-aminoquinoline)
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.161(6)
_cell_angle_beta                 74.331(8)
_cell_angle_gamma                70.170(10)
_cell_formula_units_Z            2
_cell_length_a                   8.3968(9)
_cell_length_b                   8.7615(8)
_cell_length_c                   12.3337(9)
_cell_measurement_temperature    293(2)
_cell_volume                     810.87(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius CAD 4 '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3063
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.103
_exptl_crystal_colour            'pale brown '
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         2851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0412
_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)+(0.0585P)²+0.2342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                2254
_reflns_number_total             2851
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b004945jsup1.cif
_cod_data_source_block           Compound_1
_cod_original_cell_volume        810.87(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7111035
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O -0.0569(2) -0.01256(19) 0.65559(12) 0.0608(4) Uani 1 1 d .
O2 O 0.0208(2) 0.17341(18) 0.51268(11) 0.0609(4) Uani 1 1 d .
O3 O 0.31947(18) 0.30402(18) 0.44415(11) 0.0582(4) Uani 1 1 d .
O4 O 0.51991(19) 0.17297(19) 0.54695(12) 0.0628(4) Uani 1 1 d .
O5 O 0.50282(19) -0.14710(18) 0.73338(12) 0.0583(4) Uani 1 1 d .
O6 O 0.29603(18) -0.0508(2) 0.63555(12) 0.0645(4) Uani 1 1 d .
C1 C -0.0201(2) 0.2198(2) 0.70440(15) 0.0442(4) Uani 1 1 d .
C2 C 0.0571(2) 0.3640(2) 0.65325(17) 0.0458(5) Uani 1 1 d .
C3 C 0.2516(2) 0.3331(2) 0.64248(14) 0.0415(4) Uani 1 1 d .
C4 C 0.3074(3) 0.2306(2) 0.75256(15) 0.0432(4) Uani 1 1 d .
C5 C 0.2539(2) 0.0711(2) 0.79771(14) 0.0402(4) Uani 1 1 d .
C6 C 0.0576(2) 0.1129(2) 0.80773(15) 0.0441(4) Uani 1 1 d .
C7 C -0.0106(2) 0.1222(2) 0.61486(16) 0.0457(4) Uani 1 1 d .
C8 C 0.3647(2) 0.2636(2) 0.53626(15) 0.0414(4) Uani 1 1 d .
C9 C 0.3549(2) -0.0508(2) 0.71691(14) 0.0396(4) Uani 1 1 d .
C10 C -0.2173(3) 0.2930(4) 0.7488(2) 0.0643(6) Uani 1 1 d .
C11 C 0.2851(3) 0.5019(3) 0.6237(2) 0.0566(5) Uani 1 1 d .
C12 C 0.2960(3) -0.0006(3) 0.91648(16) 0.0528(5) Uani 1 1 d .
N1 N 0.1298(4) 0.6251(3) 0.8968(2) 0.0768(7) Uani 0.50 1 d P
C13 C 0.1298(4) 0.6251(3) 0.8968(2) 0.0768(7) Uani 0.50 1 d P
C14 C 0.2843(4) 0.5524(4) 0.9226(3) 0.0810(8) Uani 1 1 d .
C15 C 0.3084(4) 0.4193(4) 1.0115(3) 0.0815(8) Uani 1 1 d .
C16 C -0.0074(3) 0.5666(3) 0.9553(2) 0.0698(7) Uani 1 1 d .
C17 C -0.1756(4) 0.6404(3) 0.9270(2) 0.0743(7) Uani 1 1 d .
N2 N -0.1798(8) 0.7522(6) 0.8507(4) 0.0653(12) Uani 0.50 1 d P
H1 H -0.049(4) -0.069(4) 0.591(3) 0.114(10) Uiso 1 1 d .
H2A H 0.000(3) 0.445(3) 0.7038(17) 0.055(6) Uiso 1 1 d .
H2B H 0.025(3) 0.413(2) 0.5814(18) 0.055(6) Uiso 1 1 d .
H4A H 0.432(3) 0.206(2) 0.7462(16) 0.050(5) Uiso 1 1 d .
H4B H 0.252(2) 0.299(2) 0.8133(17) 0.051(5) Uiso 1 1 d .
H4 H 0.593(4) 0.124(4) 0.470(3) 0.130(11) Uiso 1 1 d .
H5 H 0.564(4) -0.205(4) 0.670(3) 0.125(11) Uiso 1 1 d .
H6A H 0.024(2) 0.011(3) 0.8310(17) 0.054(5) Uiso 1 1 d .
H6B H 0.007(3) 0.177(2) 0.8727(18) 0.054(5) Uiso 1 1 d .
H10A H -0.232(3) 0.363(3) 0.809(2) 0.076(7) Uiso 1 1 d .
H10B H -0.272(3) 0.205(3) 0.786(2) 0.082(8) Uiso 1 1 d .
H10C H -0.276(4) 0.367(4) 0.689(2) 0.092(9) Uiso 1 1 d .
H11A H 0.249(3) 0.572(3) 0.556(2) 0.080(7) Uiso 1 1 d .
H11B H 0.408(3) 0.487(3) 0.6163(18) 0.066(7) Uiso 1 1 d .
H11C H 0.217(3) 0.560(3) 0.690(2) 0.077(7) Uiso 1 1 d .
H12A H 0.420(3) -0.018(3) 0.9144(19) 0.069(7) Uiso 1 1 d .
H12B H 0.230(3) 0.076(3) 0.9703(18) 0.061(6) Uiso 1 1 d .
H12C H 0.270(3) -0.103(3) 0.9485(19) 0.067(7) Uiso 1 1 d .
H13 H 0.086(7) 0.737(7) 0.823(4) 0.084(15) Uiso 0.50 1 d P
H14 H 0.393(4) 0.593(4) 0.875(3) 0.116(10) Uiso 1 1 d .
H15 H 0.420(4) 0.375(4) 1.025(2) 0.101(10) Uiso 1 1 d .
H16 H -0.106(5) 0.771(4) 0.821(3) 0.020(11) Uiso 0.50 1 d P
H17 H -0.251(6) 0.773(6) 0.838(4) 0.037(15) Uiso 0.50 1 d P
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C7 O1 H1 110.2(17) . .
C8 O4 H4 111.5(18) . .
C9 O5 H5 111(2) . .
C7 C1 C2 112.54(15) . .
C7 C1 C6 113.80(15) . .
C2 C1 C6 110.99(15) . .
C7 C1 C10 103.81(16) . .
C2 C1 C10 107.81(17) . .
C6 C1 C10 107.33(16) . .
C3 C2 C1 118.85(15) . .
C3 C2 H2A 105.0(12) . .
C1 C2 H2A 106.4(12) . .
C3 C2 H2B 110.4(12) . .
C1 C2 H2B 108.4(13) . .
H2A C2 H2B 107.0(17) . .
C8 C3 C4 112.96(15) . .
C8 C3 C2 114.27(15) . .
C4 C3 C2 110.19(15) . .
C8 C3 C11 102.24(15) . .
C4 C3 C11 108.57(16) . .
C2 C3 C11 108.08(16) . .
C3 C4 C5 116.26(14) . .
C3 C4 H4A 111.4(11) . .
C5 C4 H4A 109.6(12) . .
C3 C4 H4B 107.4(11) . .
C5 C4 H4B 105.7(11) . .
H4A C4 H4B 105.7(16) . .
C9 C5 C12 109.67(15) . .
C9 C5 C6 111.57(15) . .
C12 C5 C6 108.97(15) . .
C9 C5 C4 108.89(14) . .
C12 C5 C4 108.83(16) . .
C6 C5 C4 108.87(15) . .
C5 C6 C1 118.01(15) . .
C5 C6 H6A 109.1(11) . .
C1 C6 H6A 110.5(12) . .
C5 C6 H6B 103.3(11) . .
C1 C6 H6B 107.2(11) . .
H6A C6 H6B 108.1(16) . .
O2 C7 O1 122.16(18) . .
O2 C7 C1 122.53(17) . .
O1 C7 C1 114.92(16) . .
O3 C8 O4 122.33(17) . .
O3 C8 C3 122.48(16) . .
O4 C8 C3 114.76(16) . .
O6 C9 O5 122.06(16) . .
O6 C9 C5 119.54(16) . .
O5 C9 C5 118.35(15) . .
C1 C10 H10A 107.3(14) . .
C1 C10 H10B 110.9(15) . .
H10A C10 H10B 108(2) . .
C1 C10 H10C 112.5(16) . .
H10A C10 H10C 107(2) . .
H10B C10 H10C 111(2) . .
C3 C11 H11A 111.5(15) . .
C3 C11 H11B 110.4(14) . .
H11A C11 H11B 109(2) . .
C3 C11 H11C 109.8(14) . .
H11A C11 H11C 107(2) . .
H11B C11 H11C 109.5(19) . .
C5 C12 H12A 110.9(13) . .
C5 C12 H12B 110.8(12) . .
H12A C12 H12B 105.6(18) . .
C5 C12 H12C 113.2(14) . .
H12A C12 H12C 108.8(19) . .
H12B C12 H12C 107.2(18) . .
C14 N1 C16 120.0(3) . .
C14 N1 H13 130(2) . .
C16 N1 H13 110(2) . .
C14 C13 C16 120.0(3) . .
C14 C13 H13 130(2) . .
C16 C13 H13 110(2) . .
C13 C14 N1 0.0(2) . .
C13 C14 C15 120.6(3) . .
N1 C14 C15 120.6(3) . .
C13 C14 H14 120.7(18) . .
N1 C14 H14 120.7(18) . .
C15 C14 H14 118.7(17) . .
C17 C15 C14 121.2(3) 2_567 .
C17 C15 H15 123.1(19) 2_567 .
C14 C15 H15 115.6(19) . .
C13 C16 N1 0.0(3) . .
C13 C16 C16 122.5(3) . 2_567
N1 C16 C16 122.5(3) . 2_567
C13 C16 C17 121.2(3) . .
N1 C16 C17 121.2(3) . .
C16 C16 C17 116.4(3) 2_567 .
N2 C17 C15 127.6(4) . 2_567
N2 C17 C16 113.2(4) . .
C15 C17 C16 119.3(3) 2_567 .
N2 C17 H17 23.2(16) . .
C15 C17 H17 104.6(18) 2_567 .
C16 C17 H17 136.1(18) . .
C17 N2 H16 120(3) . .
C17 N2 H17 108(4) . .
H16 N2 H17 130(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.312(2) .
O1 H1 1.01(3) .
O2 C7 1.220(2) .
O3 C8 1.229(2) .
O4 C8 1.299(2) .
O4 H4 1.08(4) .
O5 C9 1.281(2) .
O5 H5 0.96(4) .
O6 C9 1.232(2) .
C1 C7 1.522(3) .
C1 C2 1.539(3) .
C1 C6 1.546(3) .
C1 C10 1.552(3) .
C2 C3 1.535(3) .
C2 H2A 0.97(2) .
C2 H2B 0.95(2) .
C3 C8 1.519(2) .
C3 C4 1.531(2) .
C3 C11 1.551(3) .
C4 C5 1.544(2) .
C4 H4A 0.97(2) .
C4 H4B 0.99(2) .
C5 C9 1.514(2) .
C5 C12 1.534(2) .
C5 C6 1.539(3) .
C6 H6A 0.98(2) .
C6 H6B 1.01(2) .
C10 H10A 1.02(3) .
C10 H10B 0.99(3) .
C10 H10C 0.98(3) .
C11 H11A 0.97(3) .
C11 H11B 0.98(2) .
C11 H11C 1.00(3) .
C12 H12A 1.00(2) .
C12 H12B 0.98(2) .
C12 H12C 0.96(2) .
N1 C14 1.325(4) .
N1 C16 1.373(3) .
N1 H13 1.19(5) .
C13 C14 1.325(4) .
C13 C16 1.373(3) .
C13 H13 1.19(5) .
C14 C15 1.397(4) .
C14 H14 1.07(3) .
C15 C17 1.357(4) 2_567
C15 H15 0.93(3) .
C16 C16 1.397(5) 2_567
C16 C17 1.440(4) .
C17 N2 1.183(5) .
C17 C15 1.357(4) 2_567
C17 H17 1.49(4) .
N2 H16 0.68(3) .
N2 H17 0.62(4) .
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_site_symmetry_1
_geom_torsion_site_symmetry_4
C7 C1 C2 C3 -87.9(2) . .
C6 C1 C2 C3 40.9(2) . .
C10 C1 C2 C3 158.20(18) . .
C1 C2 C3 C8 83.5(2) . .
C1 C2 C3 C4 -44.9(2) . .
C1 C2 C3 C11 -163.43(17) . .
C8 C3 C4 C5 -78.1(2) . .
C2 C3 C4 C5 51.1(2) . .
C11 C3 C4 C5 169.25(16) . .
C3 C4 C5 C9 69.0(2) . .
C3 C4 C5 C12 -171.50(16) . .
C3 C4 C5 C6 -52.8(2) . .
C9 C5 C6 C1 -71.4(2) . .
C12 C5 C6 C1 167.34(16) . .
C4 C5 C6 C1 48.8(2) . .
C7 C1 C6 C5 85.0(2) . .
C2 C1 C6 C5 -43.2(2) . .
C10 C1 C6 C5 -160.73(18) . .
C2 C1 C7 O2 -14.3(3) . .
C6 C1 C7 O2 -141.69(19) . .
C10 C1 C7 O2 102.0(2) . .
C2 C1 C7 O1 172.77(16) . .
C6 C1 C7 O1 45.4(2) . .
C10 C1 C7 O1 -70.9(2) . .
C4 C3 C8 O3 162.88(17) . .
C2 C3 C8 O3 35.9(2) . .
C11 C3 C8 O3 -80.6(2) . .
C4 C3 C8 O4 -24.5(2) . .
C2 C3 C8 O4 -151.50(16) . .
C11 C3 C8 O4 92.00(19) . .
C12 C5 C9 O6 151.86(19) . .
C6 C5 C9 O6 31.0(2) . .
C4 C5 C9 O6 -89.2(2) . .
C12 C5 C9 O5 -30.7(2) . .
C6 C5 C9 O5 -151.53(16) . .
C4 C5 C9 O5 88.29(18) . .
C16 C13 C14 N1 0(100) . .
C16 C13 C14 C15 -2.0(4) . .
C16 N1 C14 C13 0(100) . .
C16 N1 C14 C15 -2.0(4) . .
C13 C14 C15 C17 0.8(4) . 2_567
N1 C14 C15 C17 0.8(4) . 2_567
C14 C13 C16 N1 0(100) . .
C14 C13 C16 C16 1.6(4) . 2_567
C14 C13 C16 C17 -178.3(2) . .
C14 N1 C16 C13 0(100) . .
C14 N1 C16 C16 1.6(4) . 2_567
C14 N1 C16 C17 -178.3(2) . .
C13 C16 C17 N2 0.0(4) . .
N1 C16 C17 N2 0.0(4) . .
C16 C16 C17 N2 -179.9(3) 2_567 .
C13 C16 C17 C15 -178.8(2) . 2_567
N1 C16 C17 C15 -178.8(2) . 2_567
C16 C16 C17 C15 1.3(4) 2_567 2_567
