#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151603.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_7151603
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         C20H14O22.5C10H9N1
_chemical_formula_sum            'C45 H36.5 N2.5 O2'
_chemical_formula_weight         644.27
_chemical_name_common
;
2,2'-dihydroxyl-1,1'-binaphthyl 6-methylquinoline clathrate
;
_chemical_name_systematic
;
2,2'-dihydroxyl-1,1'-binaphthyl 6-methylquinoline clathrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                94.6520(10)
_cell_angle_beta                 98.0680(10)
_cell_angle_gamma                103.8220(10)
_cell_formula_units_Z            2
_cell_length_a                   8.83960(10)
_cell_length_b                   9.46950(10)
_cell_length_c                   21.6106(3)
_cell_volume                     1726.77(4)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14800
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9776
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.018
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       N/A
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         7905
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0745
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0955P)²+1.5288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2028
_refine_ls_wR_factor_ref         0.2283
_reflns_number_gt                4984
_reflns_number_total             7905
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b314691j.txt
_cod_data_source_block           c_BINAP.2.5(6MeQ)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_original_formula_sum        'C45 H36.50 N2.50 O2'
_cod_database_code               7151603
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6636(2) 0.2596(2) 0.26556(9) 0.0413(5) Uani 1 1 d D . .
C4C C 0.5347(6) 0.0507(5) 0.4094(2) 0.0870(13) Uiso 1 1 d . . .
O2 O 0.5088(2) 0.2359(2) 0.12202(9) 0.0394(5) Uani 1 1 d D . .
C2C C 0.7738(9) -0.0413(8) 0.4191(3) 0.134(2) Uiso 1 1 d . . .
C11 C 0.4683(3) 0.0324(3) 0.17981(11) 0.0264(5) Uani 1 1 d . . .
C1 C 0.4046(3) 0.1189(3) 0.22622(11) 0.0268(5) Uani 1 1 d . . .
C20 C 0.4778(3) -0.1137(3) 0.18681(11) 0.0278(5) Uani 1 1 d . . .
C10 C 0.2387(3) 0.0885(3) 0.22738(11) 0.0264(5) Uani 1 1 d . . .
C9 C 0.1804(3) 0.1784(3) 0.26951(12) 0.0307(5) Uani 1 1 d . . .
N1B N 0.7871(3) 0.3984(3) 0.10118(11) 0.0412(6) Uani 1 1 d D . .
C6C C 0.6200(6) -0.0441(5) 0.5045(2) 0.0853(13) Uiso 1 1 d . . .
C3 C 0.4466(3) 0.3222(3) 0.30792(12) 0.0347(6) Uani 1 1 d . . .
H3 H 0.5169 0.4004 0.3349 0.042 Uiso 1 1 calc R . .
C2 C 0.5054(3) 0.2337(3) 0.26643(12) 0.0296(5) Uani 1 1 d . . .
C19 C 0.5387(3) -0.1919(3) 0.14119(12) 0.0324(6) Uani 1 1 d . . .
N1A N 0.8772(3) 0.5081(3) 0.32917(11) 0.0429(6) Uiso 1 1 d D . .
C3C C 0.6443(11) 0.0231(10) 0.3869(4) 0.080(2) Uiso 0.50 1 d P . .
C8 C 0.1285(3) -0.0263(3) 0.18681(12) 0.0306(5) Uani 1 1 d . . .
H8 H 0.1651 -0.0864 0.1587 0.037 Uiso 1 1 calc R . .
C9B C 0.9771(3) 0.6038(3) 0.07235(12) 0.0320(6) Uani 1 1 d . . .
C7 C -0.0300(3) -0.0520(3) 0.18748(13) 0.0372(6) Uani 1 1 d . . .
H7 H -0.1007 -0.1296 0.1603 0.045 Uiso 1 1 calc R . .
C12 C 0.5207(3) 0.0968(3) 0.12904(12) 0.0313(6) Uani 1 1 d . . .
C10B C 0.8275(3) 0.5027(3) 0.06207(12) 0.0334(6) Uani 1 1 d . . .
C13 C 0.5824(3) 0.0192(3) 0.08418(12) 0.0379(6) Uani 1 1 d . . .
H13 H 0.6182 0.0648 0.0500 0.045 Uiso 1 1 calc R . .
C5 C 0.0146(3) 0.1486(3) 0.26839(13) 0.0407(7) Uani 1 1 d . . .
H5 H -0.0251 0.2075 0.2958 0.049 Uiso 1 1 calc R . .
C18 C 0.4305(3) -0.1855(3) 0.23904(12) 0.0340(6) Uani 1 1 d . . .
H18 H 0.3903 -0.1363 0.2699 0.041 Uiso 1 1 calc R . .
C14 C 0.5903(3) -0.1206(3) 0.09001(13) 0.0394(6) Uani 1 1 d . . .
H14 H 0.6307 -0.1709 0.0596 0.047 Uiso 1 1 calc R . .
C15 C 0.5484(3) -0.3367(3) 0.14918(14) 0.0423(7) Uani 1 1 d . . .
H15 H 0.5890 -0.3881 0.1192 0.051 Uiso 1 1 calc R . .
C4 C 0.2882(3) 0.2950(3) 0.30907(13) 0.0365(6) Uani 1 1 d . . .
H4 H 0.2508 0.3552 0.3368 0.044 Uiso 1 1 calc R . .
C5B C 1.0084(3) 0.7120(3) 0.03128(13) 0.0395(6) Uani 1 1 d . . .
H5B H 1.1082 0.7791 0.0378 0.047 Uiso 1 1 calc R . .
C10A C 0.9884(3) 0.4971(3) 0.37854(12) 0.0350(6) Uiso 1 1 d . . .
C9A C 1.1292(3) 0.6084(3) 0.39891(13) 0.0384(6) Uani 1 1 d . . .
C17 C 0.4430(3) -0.3254(3) 0.24466(14) 0.0419(7) Uani 1 1 d . . .
H17 H 0.4123 -0.3704 0.2797 0.050 Uiso 1 1 calc R . .
C8B C 0.7148(3) 0.5100(3) 0.01010(13) 0.0396(6) Uani 1 1 d . . .
H8B H 0.6160 0.4414 0.0019 0.048 Uiso 1 1 calc R . .
C16 C 0.5007(4) -0.4031(3) 0.19915(15) 0.0458(7) Uani 1 1 d . . .
H16 H 0.5062 -0.4999 0.2032 0.055 Uiso 1 1 calc R . .
C4B C 1.0884(3) 0.5903(3) 0.12412(13) 0.0402(6) Uani 1 1 d . . .
H4B H 1.1905 0.6535 0.1321 0.048 Uiso 1 1 calc R . .
C6 C -0.0882(3) 0.0372(3) 0.22877(14) 0.0431(7) Uani 1 1 d . . .
H6 H -0.1974 0.0198 0.2289 0.052 Uiso 1 1 calc R . .
C6B C 0.8964(4) 0.7211(3) -0.01789(13) 0.0413(7) Uani 1 1 d . . .
C7B C 0.7492(4) 0.6169(3) -0.02835(14) 0.0436(7) Uani 1 1 d . . .
H7B H 0.6728 0.6210 -0.0626 0.052 Uiso 1 1 calc R . .
C7A C 1.0698(4) 0.3573(4) 0.45904(15) 0.0477(7) Uani 1 1 d . . .
H7A H 1.0495 0.2723 0.4794 0.057 Uiso 1 1 calc R . .
C8A C 0.9613(4) 0.3717(3) 0.41010(14) 0.0444(7) Uani 1 1 d . . .
H8A H 0.8677 0.2972 0.3974 0.053 Uiso 1 1 calc R . .
C5A C 1.2384(3) 0.5888(4) 0.44977(14) 0.0461(7) Uani 1 1 d . . .
H5A H 1.3325 0.6623 0.4632 0.055 Uiso 1 1 calc R . .
C6A C 1.2115(4) 0.4662(4) 0.48001(13) 0.0453(7) Uani 1 1 d . . .
C3B C 1.0461(4) 0.4851(3) 0.16212(14) 0.0469(7) Uani 1 1 d . . .
H3B H 1.1187 0.4747 0.1966 0.056 Uiso 1 1 calc R . .
C2B C 0.8937(4) 0.3926(3) 0.14940(15) 0.0471(7) Uani 1 1 d . . .
H2B H 0.8656 0.3222 0.1768 0.057 Uiso 1 1 calc R . .
C2A C 0.9051(4) 0.6283(4) 0.30121(15) 0.0527(8) Uani 1 1 d . . .
H2A H 0.8293 0.6367 0.2675 0.063 Uiso 1 1 calc R . .
C11A C 1.3268(4) 0.4482(5) 0.53553(16) 0.0654(10) Uani 1 1 d . . .
HA1 H 1.4088 0.5386 0.5477 0.098 Uiso 1 1 calc R . .
HA2 H 1.3742 0.3695 0.5240 0.098 Uiso 1 1 calc R . .
HA3 H 1.2715 0.4248 0.5706 0.098 Uiso 1 1 calc R . .
C4A C 1.1525(4) 0.7334(4) 0.36688(16) 0.0546(8) Uani 1 1 d . . .
H4A H 1.2451 0.8094 0.3788 0.065 Uiso 1 1 calc R . .
C5C C 0.4932(10) 0.0194(9) 0.4717(4) 0.071(2) Uiso 0.50 1 d P . .
C3A C 1.0407(4) 0.7440(4) 0.31865(17) 0.0611(9) Uani 1 1 d . . .
H3A H 1.0542 0.8277 0.2974 0.073 Uiso 1 1 calc R . .
C11B C 0.9265(5) 0.8380(4) -0.06157(17) 0.0643(10) Uani 1 1 d . . .
HB1 H 0.8609 0.9050 -0.0554 0.096 Uiso 1 1 calc R . .
HB2 H 0.9012 0.7924 -0.1049 0.096 Uiso 1 1 calc R . .
HB3 H 1.0369 0.8915 -0.0525 0.096 Uiso 1 1 calc R . .
N1C N 0.7312(11) -0.0649(10) 0.4851(4) 0.103(3) Uiso 0.50 1 d P . .
C7C C 0.6575(13) -0.0107(12) 0.4420(5) 0.099(3) Uiso 0.50 1 d P . .
C8C C 0.4310(12) 0.0771(11) 0.4290(5) 0.086(3) Uiso 0.50 1 d P . .
H2 H 0.605(2) 0.289(4) 0.1090(17) 0.086(13) Uiso 1 1 d D . .
H1 H 0.721(3) 0.350(3) 0.2916(16) 0.084(13) 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 O1 H1 111.3(19) . . ?
C8C C4C C3C 178.3(9) . . ?
C8C C4C C7C 127.0(8) . . ?
C3C C4C C7C 54.7(6) . . ?
C8C C4C C5C 54.7(6) . . ?
C3C C4C C5C 126.9(7) . . ?
C7C C4C C5C 72.3(6) . . ?
C12 O2 H2 108(2) . . ?
C7C C2C C3C 52.1(6) . . ?
C7C C2C N1C 52.5(6) . . ?
C3C C2C N1C 104.6(7) . . ?
C12 C11 C20 119.1(2) . . ?
C12 C11 C1 118.9(2) . . ?
C20 C11 C1 122.0(2) . . ?
C2 C1 C10 119.2(2) . . ?
C2 C1 C11 120.0(2) . . ?
C10 C1 C11 120.7(2) . . ?
C11 C20 C19 119.9(2) . . ?
C11 C20 C18 122.2(2) . . ?
C19 C20 C18 117.9(2) . . ?
C8 C10 C9 118.3(2) . . ?
C8 C10 C1 122.2(2) . . ?
C9 C10 C1 119.5(2) . . ?
C4 C9 C5 122.6(2) . . ?
C4 C9 C10 118.9(2) . . ?
C5 C9 C10 118.4(2) . . ?
C2B N1B C10B 117.9(2) . . ?
N1C C6C C5C 176.6(8) . 2_656 ?
N1C C6C C7C 56.1(6) . . ?
C5C C6C C7C 126.5(7) 2_656 . ?
N1C C6C C5C 127.3(7) . . ?
C5C C6C C5C 55.4(6) 2_656 . ?
C7C C6C C5C 71.2(6) . . ?
N1C C6C C8C 127.7(7) . 2_656 ?
C5C C6C C8C 49.8(5) 2_656 2_656 ?
C7C C6C C8C 176.2(7) . 2_656 ?
C5C C6C C8C 105.1(6) . 2_656 ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
O1 C2 C1 118.5(2) . . ?
O1 C2 C3 120.6(2) . . ?
C1 C2 C3 120.8(2) . . ?
C14 C19 C15 122.3(2) . . ?
C14 C19 C20 118.5(2) . . ?
C15 C19 C20 119.1(2) . . ?
C2A N1A C10A 117.6(3) . . ?
C4C C3C C7C 73.1(8) . . ?
C4C C3C C2C 126.9(8) . . ?
C7C C3C C2C 53.8(6) . . ?
C7 C8 C10 121.5(2) . . ?
C7 C8 H8 119.2 . . ?
C10 C8 H8 119.2 . . ?
C10B C9B C5B 119.1(2) . . ?
C10B C9B C4B 117.3(2) . . ?
C5B C9B C4B 123.6(3) . . ?
C8 C7 C6 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
O2 C12 C11 118.8(2) . . ?
O2 C12 C13 120.4(2) . . ?
C11 C12 C13 120.8(2) . . ?
N1B C10B C8B 118.6(2) . . ?
N1B C10B C9B 122.3(2) . . ?
C8B C10B C9B 119.1(2) . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C6 C5 C9 121.8(3) . . ?
C6 C5 H5 119.1 . . ?
C9 C5 H5 119.1 . . ?
C17 C18 C20 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C20 C18 H18 119.7 . . ?
C13 C14 C19 121.1(2) . . ?
C13 C14 H14 119.5 . . ?
C19 C14 H14 119.5 . . ?
C16 C15 C19 121.7(3) . . ?
C16 C15 H15 119.2 . . ?
C19 C15 H15 119.2 . . ?
C3 C4 C9 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C9 C4 H4 119.5 . . ?
C6B C5B C9B 121.3(3) . . ?
C6B C5B H5B 119.3 . . ?
C9B C5B H5B 119.3 . . ?
N1A C10A C8A 119.1(3) . . ?
N1A C10A C9A 122.1(2) . . ?
C8A C10A C9A 118.8(3) . . ?
C4A C9A C5A 123.6(3) . . ?
C4A C9A C10A 117.6(3) . . ?
C5A C9A C10A 118.8(3) . . ?
C18 C17 C16 121.4(3) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C7B C8B C10B 120.0(3) . . ?
C7B C8B H8B 120.0 . . ?
C10B C8B H8B 120.0 . . ?
C15 C16 C17 119.3(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C3B C4B C9B 119.4(3) . . ?
C3B C4B H4B 120.3 . . ?
C9B C4B H4B 120.3 . . ?
C5 C6 C7 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C5B C6B C7B 118.7(3) . . ?
C5B C6B C11B 122.1(3) . . ?
C7B C6B C11B 119.2(3) . . ?
C8B C7B C6B 121.7(3) . . ?
C8B C7B H7B 119.2 . . ?
C6B C7B H7B 119.2 . . ?
C8A C7A C6A 121.9(3) . . ?
C8A C7A H7A 119.1 . . ?
C6A C7A H7A 119.1 . . ?
C7A C8A C10A 120.5(3) . . ?
C7A C8A H8A 119.8 . . ?
C10A C8A H8A 119.8 . . ?
C6A C5A C9A 122.0(3) . . ?
C6A C5A H5A 119.0 . . ?
C9A C5A H5A 119.0 . . ?
C5A C6A C7A 118.0(3) . . ?
C5A C6A C11A 121.6(3) . . ?
C7A C6A C11A 120.3(3) . . ?
C4B C3B C2B 119.3(3) . . ?
C4B C3B H3B 120.4 . . ?
C2B C3B H3B 120.4 . . ?
N1B C2B C3B 123.7(3) . . ?
N1B C2B H2B 118.1 . . ?
C3B C2B H2B 118.1 . . ?
N1A C2A C3A 124.0(3) . . ?
N1A C2A H2A 118.0 . . ?
C3A C2A H2A 118.0 . . ?
C6A C11A HA1 109.5 . . ?
C6A C11A HA2 109.5 . . ?
HA1 C11A HA2 109.5 . . ?
C6A C11A HA3 109.5 . . ?
HA1 C11A HA3 109.5 . . ?
HA2 C11A HA3 109.5 . . ?
C3A C4A C9A 119.8(3) . . ?
C3A C4A H4A 120.1 . . ?
C9A C4A H4A 120.1 . . ?
C8C C5C C6C 80.0(7) . 2_656 ?
C8C C5C C5C 152.4(12) . 2_656 ?
C6C C5C C5C 72.7(7) 2_656 2_656 ?
C8C C5C C4C 48.3(5) . . ?
C6C C5C C4C 128.3(7) 2_656 . ?
C5C C5C C4C 158.9(11) 2_656 . ?
C8C C5C C6C 155.2(9) . . ?
C6C C5C C6C 124.6(6) 2_656 . ?
C5C C5C C6C 51.9(6) 2_656 . ?
C4C C5C C6C 107.1(6) . . ?
C8C C5C C7C 101.9(8) . . ?
C6C C5C C7C 177.1(8) 2_656 . ?
C5C C5C C7C 105.3(9) 2_656 . ?
C4C C5C C7C 53.6(5) . . ?
C6C C5C C7C 53.4(5) . . ?
C4A C3A C2A 118.9(3) . . ?
C4A C3A H3A 120.5 . . ?
C2A C3A H3A 120.5 . . ?
C6B C11B HB1 109.5 . . ?
C6B C11B HB2 109.5 . . ?
HB1 C11B HB2 109.5 . . ?
C6B C11B HB3 109.5 . . ?
HB1 C11B HB3 109.5 . . ?
HB2 C11B HB3 109.5 . . ?
C6C N1C C7C 74.1(8) . . ?
C6C N1C C2C 127.1(8) . . ?
C7C N1C C2C 53.1(6) . . ?
C3C C7C N1C 148.5(12) . . ?
C3C C7C C2C 74.1(8) . . ?
N1C C7C C2C 74.4(8) . . ?
C3C C7C C4C 52.2(6) . . ?
N1C C7C C4C 159.2(11) . . ?
C2C C7C C4C 126.4(10) . . ?
C3C C7C C6C 161.2(11) . . ?
N1C C7C C6C 49.8(6) . . ?
C2C C7C C6C 124.1(9) . . ?
C4C C7C C6C 109.4(8) . . ?
C3C C7C C5C 106.1(9) . . ?
N1C C7C C5C 105.2(9) . . ?
C2C C7C C5C 176.4(10) . . ?
C4C C7C C5C 54.0(5) . . ?
C6C C7C C5C 55.4(5) . . ?
C4C C8C C5C 77.0(8) . . ?
C4C C8C C6C 127.2(8) . 2_656 ?
C5C C8C C6C 50.3(6) . 2_656 ?
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
O1 C2 1.364(3) . ?
O1 H1 0.968(9) . ?
C4C C8C 1.133(10) . ?
C4C C3C 1.216(10) . ?
C4C C7C 1.471(12) . ?
C4C C5C 1.478(9) . ?
O2 C12 1.365(3) . ?
O2 H2 0.969(8) . ?
C2C C7C 1.284(12) . ?
C2C C3C 1.531(11) . ?
C2C N1C 1.546(11) . ?
C11 C12 1.381(3) . ?
C11 C20 1.424(3) . ?
C11 C1 1.497(3) . ?
C1 C2 1.377(3) . ?
C1 C10 1.430(3) . ?
C20 C19 1.425(3) . ?
C20 C18 1.426(4) . ?
C10 C8 1.414(3) . ?
C10 C9 1.426(3) . ?
C9 C4 1.405(4) . ?
C9 C5 1.421(4) . ?
N1B C2B 1.317(4) . ?
N1B C10B 1.367(3) . ?
C6C N1C 1.173(9) . ?
C6C C5C 1.248(9) 2_656 ?
C6C C7C 1.476(12) . ?
C6C C5C 1.514(10) . ?
C6C C8C 1.598(11) 2_656 ?
C3 C4 1.365(4) . ?
C3 C2 1.412(4) . ?
C3 H3 0.9400 . ?
C19 C14 1.415(4) . ?
C19 C15 1.417(4) . ?
N1A C2A 1.319(4) . ?
N1A C10A 1.374(4) . ?
C3C C7C 1.255(13) . ?
C8 C7 1.366(3) . ?
C8 H8 0.9400 . ?
C9B C10B 1.412(4) . ?
C9B C5B 1.413(4) . ?
C9B C4B 1.418(4) . ?
C7 C6 1.410(4) . ?
C7 H7 0.9400 . ?
C12 C13 1.415(4) . ?
C10B C8B 1.411(4) . ?
C13 C14 1.357(4) . ?
C13 H13 0.9400 . ?
C5 C6 1.359(4) . ?
C5 H5 0.9400 . ?
C18 C17 1.370(4) . ?
C18 H18 0.9400 . ?
C14 H14 0.9400 . ?
C15 C16 1.361(4) . ?
C15 H15 0.9400 . ?
C4 H4 0.9400 . ?
C5B C6B 1.371(4) . ?
C5B H5B 0.9400 . ?
C10A C8A 1.405(4) . ?
C10A C9A 1.414(4) . ?
C9A C4A 1.407(4) . ?
C9A C5A 1.413(4) . ?
C17 C16 1.404(4) . ?
C17 H17 0.9400 . ?
C8B C7B 1.367(4) . ?
C8B H8B 0.9400 . ?
C16 H16 0.9400 . ?
C4B C3B 1.359(4) . ?
C4B H4B 0.9400 . ?
C6 H6 0.9400 . ?
C6B C7B 1.408(4) . ?
C6B C11B 1.512(4) . ?
C7B H7B 0.9400 . ?
C7A C8A 1.363(4) . ?
C7A C6A 1.409(5) . ?
C7A H7A 0.9400 . ?
C8A H8A 0.9400 . ?
C5A C6A 1.365(4) . ?
C5A H5A 0.9400 . ?
C6A C11A 1.510(4) . ?
C3B C2B 1.397(4) . ?
C3B H3B 0.9400 . ?
C2B H2B 0.9400 . ?
C2A C3A 1.399(5) . ?
C2A H2A 0.9400 . ?
C11A HA1 0.9700 . ?
C11A HA2 0.9700 . ?
C11A HA3 0.9700 . ?
C4A C3A 1.360(5) . ?
C4A H4A 0.9400 . ?
C5C C8C 1.239(12) . ?
C5C C6C 1.248(9) 2_656 ?
C5C C5C 1.304(16) 2_656 ?
C5C C7C 1.741(14) . ?
C3A H3A 0.9400 . ?
C11B HB1 0.9700 . ?
C11B HB2 0.9700 . ?
C11B HB3 0.9700 . ?
N1C C7C 1.274(13) . ?
C8C C6C 1.598(11) 2_656 ?
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 N1A 0.97(3) 1.82(3) 2.760(3) 163(3) .
O2 H2 N1B 0.97(3) 1.73(3) 2.690(3) 169(3) .
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
C12 C11 C1 C2 -71.2(3) . . . . ?
C20 C11 C1 C2 108.2(3) . . . . ?
C12 C11 C1 C10 105.8(3) . . . . ?
C20 C11 C1 C10 -74.9(3) . . . . ?
C12 C11 C20 C19 -0.9(3) . . . . ?
C1 C11 C20 C19 179.7(2) . . . . ?
C12 C11 C20 C18 178.1(2) . . . . ?
C1 C11 C20 C18 -1.3(3) . . . . ?
C2 C1 C10 C8 179.1(2) . . . . ?
C11 C1 C10 C8 2.2(4) . . . . ?
C2 C1 C10 C9 0.7(3) . . . . ?
C11 C1 C10 C9 -176.2(2) . . . . ?
C8 C10 C9 C4 -178.5(2) . . . . ?
C1 C10 C9 C4 -0.1(3) . . . . ?
C8 C10 C9 C5 -0.3(3) . . . . ?
C1 C10 C9 C5 178.1(2) . . . . ?
C10 C1 C2 O1 178.8(2) . . . . ?
C11 C1 C2 O1 -4.2(3) . . . . ?
C10 C1 C2 C3 -0.9(4) . . . . ?
C11 C1 C2 C3 176.1(2) . . . . ?
C4 C3 C2 O1 -179.3(2) . . . . ?
C4 C3 C2 C1 0.3(4) . . . . ?
C11 C20 C19 C14 0.8(3) . . . . ?
C18 C20 C19 C14 -178.3(2) . . . . ?
C11 C20 C19 C15 179.5(2) . . . . ?
C18 C20 C19 C15 0.5(3) . . . . ?
C8C C4C C3C C7C -172(30) . . . . ?
C5C C4C C3C C7C -4.9(10) . . . . ?
C8C C4C C3C C2C -172(30) . . . . ?
C7C C4C C3C C2C 0.3(8) . . . . ?
C5C C4C C3C C2C -4.6(14) . . . . ?
C7C C2C C3C C4C -0.4(10) . . . . ?
N1C C2C C3C C4C 1.0(12) . . . . ?
N1C C2C C3C C7C 1.3(9) . . . . ?
C9 C10 C8 C7 -0.1(4) . . . . ?
C1 C10 C8 C7 -178.5(2) . . . . ?
C10 C8 C7 C6 0.5(4) . . . . ?
C20 C11 C12 O2 178.9(2) . . . . ?
C1 C11 C12 O2 -1.7(3) . . . . ?
C20 C11 C12 C13 0.3(4) . . . . ?
C1 C11 C12 C13 179.7(2) . . . . ?
C2B N1B C10B C8B 179.8(3) . . . . ?
C2B N1B C10B C9B -0.9(4) . . . . ?
C5B C9B C10B N1B -177.7(2) . . . . ?
C4B C9B C10B N1B 2.3(4) . . . . ?
C5B C9B C10B C8B 1.7(4) . . . . ?
C4B C9B C10B C8B -178.4(2) . . . . ?
O2 C12 C13 C14 -178.1(2) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C4 C9 C5 C6 178.5(3) . . . . ?
C10 C9 C5 C6 0.4(4) . . . . ?
C11 C20 C18 C17 -179.2(2) . . . . ?
C19 C20 C18 C17 -0.2(4) . . . . ?
C12 C13 C14 C19 -0.6(4) . . . . ?
C15 C19 C14 C13 -178.7(3) . . . . ?
C20 C19 C14 C13 0.0(4) . . . . ?
C14 C19 C15 C16 179.0(3) . . . . ?
C20 C19 C15 C16 0.3(4) . . . . ?
C2 C3 C4 C9 0.4(4) . . . . ?
C5 C9 C4 C3 -178.6(3) . . . . ?
C10 C9 C4 C3 -0.5(4) . . . . ?
C10B C9B C5B C6B 0.4(4) . . . . ?
C4B C9B C5B C6B -179.5(3) . . . . ?
C2A N1A C10A C8A 178.9(3) . . . . ?
C2A N1A C10A C9A -0.7(4) . . . . ?
N1A C10A C9A C4A 0.3(4) . . . . ?
C8A C10A C9A C4A -179.3(3) . . . . ?
N1A C10A C9A C5A -179.6(3) . . . . ?
C8A C10A C9A C5A 0.7(4) . . . . ?
C20 C18 C17 C16 -0.7(4) . . . . ?
N1B C10B C8B C7B 177.3(2) . . . . ?
C9B C10B C8B C7B -2.1(4) . . . . ?
C19 C15 C16 C17 -1.2(4) . . . . ?
C18 C17 C16 C15 1.5(4) . . . . ?
C10B C9B C4B C3B -1.8(4) . . . . ?
C5B C9B C4B C3B 178.2(3) . . . . ?
C9 C5 C6 C7 0.1(4) . . . . ?
C8 C7 C6 C5 -0.5(4) . . . . ?
C9B C5B C6B C7B -2.0(4) . . . . ?
C9B C5B C6B C11B 178.8(3) . . . . ?
C10B C8B C7B C6B 0.5(4) . . . . ?
C5B C6B C7B C8B 1.6(4) . . . . ?
C11B C6B C7B C8B -179.2(3) . . . . ?
C6A C7A C8A C10A 0.3(4) . . . . ?
N1A C10A C8A C7A 179.7(3) . . . . ?
C9A C10A C8A C7A -0.6(4) . . . . ?
C4A C9A C5A C6A 179.6(3) . . . . ?
C10A C9A C5A C6A -0.5(4) . . . . ?
C9A C5A C6A C7A 0.1(4) . . . . ?
C9A C5A C6A C11A -178.2(3) . . . . ?
C8A C7A C6A C5A 0.0(4) . . . . ?
C8A C7A C6A C11A 178.3(3) . . . . ?
C9B C4B C3B C2B -0.1(4) . . . . ?
C10B N1B C2B C3B -1.2(4) . . . . ?
C4B C3B C2B N1B 1.7(5) . . . . ?
C10A N1A C2A C3A 0.3(5) . . . . ?
C5A C9A C4A C3A -179.5(3) . . . . ?
C10A C9A C4A C3A 0.6(5) . . . . ?
C3C C4C C5C C8C -179.6(11) . . . . ?
C7C C4C C5C C8C 176.3(9) . . . . ?
C8C C4C C5C C6C 0.9(9) . . . 2_656 ?
C3C C4C C5C C6C -178.6(9) . . . 2_656 ?
C7C C4C C5C C6C 177.2(10) . . . 2_656 ?
C8C C4C C5C C5C -171(3) . . . 2_656 ?
C3C C4C C5C C5C 9(3) . . . 2_656 ?
C7C C4C C5C C5C 5(3) . . . 2_656 ?
C8C C4C C5C C6C -176.5(10) . . . . ?
C3C C4C C5C C6C 4.0(10) . . . . ?
C7C C4C C5C C6C -0.2(6) . . . . ?
C8C C4C C5C C7C -176.3(9) . . . . ?
C3C C4C C5C C7C 4.2(9) . . . . ?
N1C C6C C5C C8C -6(2) . . . . ?
C5C C6C C5C C8C 171(3) 2_656 . . . ?
C7C C6C C5C C8C -6(2) . . . . ?
C8C C6C C5C C8C 174.2(18) 2_656 . . . ?
N1C C6C C5C C6C -177.3(10) . . . 2_656 ?
C5C C6C C5C C6C 0.000(1) 2_656 . . 2_656 ?
C7C C6C C5C C6C -177.3(10) . . . 2_656 ?
C8C C6C C5C C6C 3.0(9) 2_656 . . 2_656 ?
N1C C6C C5C C5C -177.3(10) . . . 2_656 ?
C7C C6C C5C C5C -177.3(10) . . . 2_656 ?
C8C C6C C5C C5C 3.0(9) 2_656 . . 2_656 ?
N1C C6C C5C C4C 0.2(11) . . . . ?
C5C C6C C5C C4C 177.5(12) 2_656 . . . ?
C7C C6C C5C C4C 0.2(6) . . . . ?
C8C C6C C5C C4C -179.5(6) 2_656 . . . ?
N1C C6C C5C C7C 0.0(9) . . . . ?
C5C C6C C5C C7C 177.3(10) 2_656 . . . ?
C8C C6C C5C C7C -179.8(7) 2_656 . . . ?
C9A C4A C3A C2A -1.0(5) . . . . ?
N1A C2A C3A C4A 0.6(6) . . . . ?
C5C C6C N1C C7C -140(13) 2_656 . . . ?
C5C C6C N1C C7C 0.0(10) . . . . ?
C8C C6C N1C C7C 179.7(9) 2_656 . . . ?
C5C C6C N1C C2C -144(13) 2_656 . . . ?
C7C C6C N1C C2C -3.7(8) . . . . ?
C5C C6C N1C C2C -3.7(14) . . . . ?
C8C C6C N1C C2C 176.0(7) 2_656 . . . ?
C7C C2C N1C C6C 4.5(10) . . . . ?
C3C C2C N1C C6C 3.2(12) . . . . ?
C3C C2C N1C C7C -1.3(9) . . . . ?
C4C C3C C7C N1C 177(2) . . . . ?
C2C C3C C7C N1C -3.0(19) . . . . ?
C4C C3C C7C C2C 179.7(8) . . . . ?
C2C C3C C7C C4C -179.7(8) . . . . ?
C4C C3C C7C C6C 13(3) . . . . ?
C2C C3C C7C C6C -167(4) . . . . ?
C4C C3C C7C C5C 3.5(7) . . . . ?
C2C C3C C7C C5C -176.2(10) . . . . ?
C6C N1C C7C C3C -173(2) . . . . ?
C2C N1C C7C C3C 3.0(19) . . . . ?
C6C N1C C7C C2C -176.3(8) . . . . ?
C6C N1C C7C C4C -1(3) . . . . ?
C2C N1C C7C C4C 176(3) . . . . ?
C2C N1C C7C C6C 176.3(8) . . . . ?
C6C N1C C7C C5C 0.0(7) . . . . ?
C2C N1C C7C C5C 176.3(10) . . . . ?
N1C C2C C7C C3C -178.4(10) . . . . ?
C3C C2C C7C N1C 178.4(10) . . . . ?
C3C C2C C7C C4C 0.3(8) . . . . ?
N1C C2C C7C C4C -178.1(15) . . . . ?
C3C C2C C7C C6C 175.0(14) . . . . ?
N1C C2C C7C C6C -3.4(8) . . . . ?
C3C C2C C7C C5C 95(16) . . . . ?
N1C C2C C7C C5C -84(16) . . . . ?
C8C C4C C7C C3C 179.7(11) . . . . ?
C5C C4C C7C C3C 175.9(9) . . . . ?
C8C C4C C7C N1C 5(3) . . . . ?
C3C C4C C7C N1C -175(3) . . . . ?
C5C C4C C7C N1C 1(3) . . . . ?
C8C C4C C7C C2C 179.4(10) . . . . ?
C3C C4C C7C C2C -0.4(10) . . . . ?
C5C C4C C7C C2C 175.5(12) . . . . ?
C8C C4C C7C C6C 4.1(13) . . . . ?
C3C C4C C7C C6C -175.7(11) . . . . ?
C5C C4C C7C C6C 0.2(7) . . . . ?
C8C C4C C7C C5C 3.8(10) . . . . ?
C3C C4C C7C C5C -175.9(9) . . . . ?
N1C C6C C7C C3C 169(4) . . . . ?
C5C C6C C7C C3C -14(4) 2_656 . . . ?
C5C C6C C7C C3C -11(3) . . . . ?
C8C C6C C7C C3C -7(13) 2_656 . . . ?
C5C C6C C7C N1C 177.2(10) 2_656 . . . ?
C5C C6C C7C N1C -180.0(9) . . . . ?
C8C C6C C7C N1C -176(10) 2_656 . . . ?
N1C C6C C7C C2C 4.3(10) . . . . ?
C5C C6C C7C C2C -178.4(9) 2_656 . . . ?
C5C C6C C7C C2C -175.7(12) . . . . ?
C8C C6C C7C C2C -172(10) 2_656 . . . ?
N1C C6C C7C C4C 179.8(11) . . . . ?
C5C C6C C7C C4C -3.0(12) 2_656 . . . ?
C5C C6C C7C C4C -0.2(7) . . . . ?
C8C C6C C7C C4C 3(11) 2_656 . . . ?
N1C C6C C7C C5C 180.0(9) . . . . ?
C5C C6C C7C C5C -2.8(10) 2_656 . . . ?
C8C C6C C7C C5C 4(11) 2_656 . . . ?
C8C C5C C7C C3C -6.2(11) . . . . ?
C6C C5C C7C C3C -134(16) 2_656 . . . ?
C5C C5C C7C C3C 178.6(11) 2_656 . . . ?
C4C C5C C7C C3C -3.4(7) . . . . ?
C6C C5C C7C C3C 176.4(11) . . . . ?
C8C C5C C7C N1C 177.4(10) . . . . ?
C6C C5C C7C N1C 49(16) 2_656 . . . ?
C5C C5C C7C N1C 2.2(13) 2_656 . . . ?
C4C C5C C7C N1C -179.7(11) . . . . ?
C6C C5C C7C N1C 0.0(7) . . . . ?
C8C C5C C7C C2C -100(16) . . . . ?
C6C C5C C7C C2C 132(17) 2_656 . . . ?
C5C C5C C7C C2C 85(16) 2_656 . . . ?
C4C C5C C7C C2C -97(16) . . . . ?
C6C C5C C7C C2C 83(16) . . . . ?
C8C C5C C7C C4C -2.9(7) . . . . ?
C6C C5C C7C C4C -131(16) 2_656 . . . ?
C5C C5C C7C C4C -178.0(11) 2_656 . . . ?
C6C C5C C7C C4C 179.8(8) . . . . ?
C8C C5C C7C C6C 177.4(9) . . . . ?
C6C C5C C7C C6C 49(16) 2_656 . . . ?
C5C C5C C7C C6C 2.2(8) 2_656 . . . ?
C4C C5C C7C C6C -179.8(8) . . . . ?
C3C C4C C8C C5C 168(30) . . . . ?
C7C C4C C8C C5C -4.5(11) . . . . ?
C3C C4C C8C C6C 167(30) . . . 2_656 ?
C7C C4C C8C C6C -5.2(15) . . . 2_656 ?
C5C C4C C8C C6C -0.7(7) . . . 2_656 ?
C6C C5C C8C C4C -179.3(7) 2_656 . . . ?
C5C C5C C8C C4C 173(3) 2_656 . . . ?
C6C C5C C8C C4C 8(2) . . . . ?
C7C C5C C8C C4C 3.1(8) . . . . ?
C5C C5C C8C C6C -8(2) 2_656 . . 2_656 ?
C4C C5C C8C C6C 179.3(7) . . . 2_656 ?
C6C C5C C8C C6C -173(2) . . . 2_656 ?
C7C C5C C8C C6C -177.6(8) . . . 2_656 ?
