#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:30:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180302 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151602.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151602
loop_
_publ_author_name
'Caira, Mino R.'
'Paul Chang, Y.'
'Nassimbeni, Luigi R.'
'Su, Hong'
_publ_section_title
;
 Inclusion of quinolines by binaphthol: structures and selectivity.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              655
_journal_page_last               659
_journal_paper_doi               10.1039/b314691j
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         C20H14O22C10H9N1
_chemical_formula_sum            'C40 H32 N2 O2'
_chemical_formula_weight         572.68
_chemical_name_common
;
2,2-dihydroxyl-1,1'-binaphthyl di-2-methylquinoline
;
_chemical_name_systematic
;
2,2-dihydroxyl-1,1'-binaphthyl di-2-methylquinoline
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 99.4430(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.8402(3)
_cell_length_b                   10.5377(2)
_cell_length_c                   9.7304(2)
_cell_volume                     1501.04(5)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       '1.0° φ scans and 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  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6421
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.77
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9808
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(13)
_refine_ls_extinction_coef       N/A
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3420
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0483P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0894
_reflns_number_gt                2538
_reflns_number_total             3420
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b314691j.txt
_cod_data_source_block           c:BINAP.2(2MeQ)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      C2
_cod_database_code               7151602
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.02990(10) 0.38199(13) 0.94511(15) 0.0262(3) Uani 1 1 d . . .
C9 C 0.15976(10) 0.29521(15) 0.84486(15) 0.0308(4) Uani 1 1 d . . .
C10 C 0.10264(10) 0.29297(14) 0.94942(15) 0.0273(3) Uani 1 1 d . . .
N1G N -0.03704(9) 0.77800(13) 0.70216(14) 0.0345(3) Uani 1 1 d D . .
C6 C 0.24610(12) 0.11567(16) 0.95460(17) 0.0412(4) Uani 1 1 d . . .
H6 H 0.2936 0.0563 0.9566 0.049 Uiso 1 1 calc R . .
C10G C -0.10166(11) 0.81723(14) 0.59294(15) 0.0317(4) Uani 1 1 d . . .
C8 C 0.12098(10) 0.19999(14) 1.05536(15) 0.0323(4) Uani 1 1 d . . .
H8 H 0.0851 0.1979 1.1264 0.039 Uiso 1 1 calc R . .
C9G C -0.11418(11) 0.94657(15) 0.55628(16) 0.0347(4) Uani 1 1 d . . .
C3 C 0.07219(12) 0.47177(16) 0.73496(17) 0.0387(4) Uani 1 1 d . . .
H3 H 0.0616 0.5321 0.6629 0.046 Uiso 1 1 calc R . .
C2 C 0.01529(10) 0.46937(14) 0.83824(15) 0.0314(4) Uani 1 1 d . . .
C7 C 0.18955(11) 0.11320(16) 1.05690(18) 0.0396(4) Uani 1 1 d . . .
H7 H 0.1989 0.0512 1.1272 0.047 Uiso 1 1 calc R . .
C5 C 0.23145(10) 0.20511(16) 0.85233(17) 0.0382(4) Uani 1 1 d . . .
H5 H 0.2700 0.2072 0.7847 0.046 Uiso 1 1 calc R . .
C4 C 0.14243(12) 0.38712(16) 0.73895(17) 0.0389(4) Uani 1 1 d . . .
H4 H 0.1798 0.3904 0.6698 0.047 Uiso 1 1 calc R . .
C2G C 0.01663(11) 0.86450(16) 0.77369(16) 0.0356(4) Uani 1 1 d . . .
C4G C -0.05610(12) 1.03531(16) 0.63564(17) 0.0416(4) Uani 1 1 d . . .
H4G H -0.0622 1.1224 0.6152 0.050 Uiso 1 1 calc R . .
C3G C 0.00850(12) 0.99459(16) 0.74141(17) 0.0399(4) Uani 1 1 d . . .
H3G H 0.0479 1.0534 0.7933 0.048 Uiso 1 1 calc R . .
C5G C -0.18249(12) 0.97931(19) 0.44289(17) 0.0459(5) Uani 1 1 d . . .
H5G H -0.1914 1.0650 0.4172 0.055 Uiso 1 1 calc R . .
C8G C -0.15673(12) 0.72530(16) 0.51539(18) 0.0407(4) Uani 1 1 d . . .
H8G H -0.1484 0.6390 0.5383 0.049 Uiso 1 1 calc R . .
C7G C -0.22244(13) 0.7607(2) 0.40680(18) 0.0507(5) Uani 1 1 d . . .
H7G H -0.2592 0.6985 0.3560 0.061 Uiso 1 1 calc R . .
C6G C -0.23547(13) 0.8886(2) 0.37049(19) 0.0530(5) Uani 1 1 d . . .
H6G H -0.2810 0.9119 0.2958 0.064 Uiso 1 1 calc R . .
O1 O -0.05579(8) 0.55148(10) 0.83261(12) 0.0426(3) Uani 1 1 d D . .
C11G C 0.08802(13) 0.81799(19) 0.89020(18) 0.0495(5) Uani 1 1 d . . .
H11A H 0.0729 0.7326 0.9160 0.074 Uiso 1 1 calc R . .
H11B H 0.0902 0.8737 0.9700 0.074 Uiso 1 1 calc R . .
H11C H 0.1471 0.8175 0.8599 0.074 Uiso 1 1 calc R . .
H1 H -0.0476(14) 0.6240(11) 0.7739(18) 0.064(6) Uiso 1 1 d D . .
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
_geom_angle_publ_flag
C2 C1 C10 119.09(13) . . ?
C2 C1 C1 119.99(12) . 2_557 ?
C10 C1 C1 120.92(12) . 2_557 ?
C4 C9 C5 122.93(14) . . ?
C4 C9 C10 118.36(14) . . ?
C5 C9 C10 118.71(14) . . ?
C8 C10 C1 122.08(13) . . ?
C8 C10 C9 117.69(13) . . ?
C1 C10 C9 120.23(13) . . ?
C2G N1G C10G 118.76(14) . . ?
C5 C6 C7 119.26(15) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
N1G C10G C8G 118.62(14) . . ?
N1G C10G C9G 122.12(14) . . ?
C8G C10G C9G 119.25(14) . . ?
C7 C8 C10 121.67(15) . . ?
C7 C8 H8 119.2 . . ?
C10 C8 H8 119.2 . . ?
C4G C9G C5G 124.08(15) . . ?
C4G C9G C10G 117.21(14) . . ?
C5G C9G C10G 118.70(16) . . ?
C4 C3 C2 120.60(15) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O1 C2 C1 118.73(13) . . ?
O1 C2 C3 120.65(13) . . ?
C1 C2 C3 120.60(14) . . ?
C8 C7 C6 120.71(16) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C6 C5 C9 121.94(15) . . ?
C6 C5 H5 119.0 . . ?
C9 C5 H5 119.0 . . ?
C3 C4 C9 121.11(15) . . ?
C3 C4 H4 119.4 . . ?
C9 C4 H4 119.4 . . ?
N1G C2G C3G 121.94(15) . . ?
N1G C2G C11G 117.35(16) . . ?
C3G C2G C11G 120.71(17) . . ?
C3G C4G C9G 119.83(15) . . ?
C3G C4G H4G 120.1 . . ?
C9G C4G H4G 120.1 . . ?
C4G C3G C2G 120.12(16) . . ?
C4G C3G H3G 119.9 . . ?
C2G C3G H3G 119.9 . . ?
C6G C5G C9G 120.86(17) . . ?
C6G C5G H5G 119.6 . . ?
C9G C5G H5G 119.6 . . ?
C7G C8G C10G 120.35(17) . . ?
C7G C8G H8G 119.8 . . ?
C10G C8G H8G 119.8 . . ?
C8G C7G C6G 120.66(18) . . ?
C8G C7G H7G 119.7 . . ?
C6G C7G H7G 119.7 . . ?
C5G C6G C7G 120.18(17) . . ?
C5G C6G H6G 119.9 . . ?
C7G C6G H6G 119.9 . . ?
C2 O1 H1 110.6(12) . . ?
C2G C11G H11A 109.5 . . ?
C2G C11G H11B 109.5 . . ?
H11A C11G H11B 109.5 . . ?
C2G C11G H11C 109.5 . . ?
H11A C11G H11C 109.5 . . ?
H11B C11G H11C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(2) . ?
C1 C10 1.4254(19) . ?
C1 C1 1.497(3) 2_557 ?
C9 C4 1.407(2) . ?
C9 C5 1.419(2) . ?
C9 C10 1.4273(19) . ?
C10 C8 1.416(2) . ?
N1G C2G 1.330(2) . ?
N1G C10G 1.373(2) . ?
C6 C5 1.362(2) . ?
C6 C7 1.404(2) . ?
C6 H6 0.9400 . ?
C10G C8G 1.405(2) . ?
C10G C9G 1.413(2) . ?
C8 C7 1.366(2) . ?
C8 H8 0.9400 . ?
C9G C4G 1.413(2) . ?
C9G C5G 1.413(2) . ?
C3 C4 1.368(2) . ?
C3 C2 1.415(2) . ?
C3 H3 0.9400 . ?
C2 O1 1.3585(19) . ?
C7 H7 0.9400 . ?
C5 H5 0.9400 . ?
C4 H4 0.9400 . ?
C2G C3G 1.407(3) . ?
C2G C11G 1.501(2) . ?
C4G C3G 1.356(2) . ?
C4G H4G 0.9400 . ?
C3G H3G 0.9400 . ?
C5G C6G 1.359(3) . ?
C5G H5G 0.9400 . ?
C8G C7G 1.367(3) . ?
C8G H8G 0.9400 . ?
C7G C6G 1.398(3) . ?
C7G H7G 0.9400 . ?
C6G H6G 0.9400 . ?
O1 H1 0.974(7) . ?
C11G H11A 0.9700 . ?
C11G H11B 0.9700 . ?
C11G H11C 0.9700 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1G 0.974(14) 1.784(13) 2.7390(17) 166.2(15) .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C10 C8 -179.43(14) . . . . ?
C1 C1 C10 C8 0.9(2) 2_557 . . . ?
C2 C1 C10 C9 0.43(19) . . . . ?
C1 C1 C10 C9 -179.24(14) 2_557 . . . ?
C4 C9 C10 C8 -179.95(14) . . . . ?
C5 C9 C10 C8 -0.07(19) . . . . ?
C4 C9 C10 C1 0.2(2) . . . . ?
C5 C9 C10 C1 -179.94(13) . . . . ?
C2G N1G C10G C8G 178.43(15) . . . . ?
C2G N1G C10G C9G -1.4(2) . . . . ?
C1 C10 C8 C7 178.49(14) . . . . ?
C9 C10 C8 C7 -1.4(2) . . . . ?
N1G C10G C9G C4G 1.0(2) . . . . ?
C8G C10G C9G C4G -178.86(14) . . . . ?
N1G C10G C9G C5G -179.68(14) . . . . ?
C8G C10G C9G C5G 0.5(2) . . . . ?
C10 C1 C2 O1 178.12(13) . . . . ?
C1 C1 C2 O1 -2.2(2) 2_557 . . . ?
C10 C1 C2 C3 -0.7(2) . . . . ?
C1 C1 C2 C3 179.00(14) 2_557 . . . ?
C4 C3 C2 O1 -178.48(15) . . . . ?
C4 C3 C2 C1 0.3(2) . . . . ?
C10 C8 C7 C6 1.7(2) . . . . ?
C5 C6 C7 C8 -0.6(2) . . . . ?
C7 C6 C5 C9 -0.8(2) . . . . ?
C4 C9 C5 C6 -178.96(15) . . . . ?
C10 C9 C5 C6 1.2(2) . . . . ?
C2 C3 C4 C9 0.4(2) . . . . ?
C5 C9 C4 C3 179.55(15) . . . . ?
C10 C9 C4 C3 -0.6(2) . . . . ?
C10G N1G C2G C3G 0.6(2) . . . . ?
C10G N1G C2G C11G -178.55(14) . . . . ?
C5G C9G C4G C3G -178.98(15) . . . . ?
C10G C9G C4G C3G 0.3(2) . . . . ?
C9G C4G C3G C2G -1.1(2) . . . . ?
N1G C2G C3G C4G 0.7(3) . . . . ?
C11G C2G C3G C4G 179.80(15) . . . . ?
C4G C9G C5G C6G 179.49(16) . . . . ?
C10G C9G C5G C6G 0.2(2) . . . . ?
N1G C10G C8G C7G 179.33(15) . . . . ?
C9G C10G C8G C7G -0.8(2) . . . . ?
C10G C8G C7G C6G 0.5(3) . . . . ?
C9G C5G C6G C7G -0.5(3) . . . . ?
C8G C7G C6G C5G 0.2(3) . . . . ?
