#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:28:39 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179724 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/24/7002455.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_7002455
loop_
_publ_author_name
'Howard, Ruth H.'
'Alonso-Moreno, Carlos'
'Broomfield, Lewis M.'
'Hughes, David L.'
'Wright, Joseph A.'
'Bochmann, Manfred'
_publ_section_title
;
 Synthesis and structures of complexes with axially chiral
 isoquinolinyl-naphtholate ligands
;
_journal_issue                   40
_journal_name_full               'Dalton Transactions'
_journal_page_first              8667
_journal_page_last               8682
_journal_paper_doi               10.1039/b907982c
_journal_year                    2009
_chemical_formula_moiety         'C27 H29 N O'
_chemical_formula_structural     L(H)-H
_chemical_formula_sum            'C27 H29 N O'
_chemical_formula_weight         383.51
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 105.175(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.228(3)
_cell_length_b                   11.794(2)
_cell_length_c                   25.429(5)
_cell_measurement_temperature    295(1)
_cell_volume                     4697.2(15)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p20 beta
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p20 beta
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p20 beta
;
_computing_molecular_graphics    'ORTEP (Johnson, 1971)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      295(1)
_diffrn_detector_area_resol_mean 16.0050
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 3/CCD'
_diffrn_measurement_method       'Thin slice φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1458
_diffrn_reflns_av_sigmaI/netI    0.1379
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29252
_diffrn_reflns_theta_full        20.00
_diffrn_reflns_theta_max         20.00
_diffrn_reflns_theta_min         3.55
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         4361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1743
_refine_ls_R_factor_gt           0.0750
_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)+(0.0197P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                2295
_reflns_number_total             4361
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b907982c.txt
_cod_data_source_block           L(H)-H
_cod_original_cell_volume        4697.1(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7002455
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.4238(3) 0.3594(5) 0.2099(2) 0.0448(16) Uani 1 1 d . A .
C2 C 0.4176(3) 0.2580(5) 0.1824(2) 0.0511(17) Uani 1 1 d . . .
O2 O 0.3514(3) 0.1845(3) 0.18245(16) 0.0623(13) Uani 1 1 d . . .
C3 C 0.4792(3) 0.2218(5) 0.1548(2) 0.0494(17) Uani 1 1 d . . .
C31 C 0.4728(4) 0.1062(5) 0.1252(3) 0.0658(19) Uani 1 1 d . . .
C32 C 0.3889(4) 0.0990(4) 0.0796(3) 0.097(2) Uani 1 1 d . . .
H32A H 0.3413 0.1092 0.0950 0.146 Uiso 1 1 calc R . .
H32B H 0.3849 0.0261 0.0623 0.146 Uiso 1 1 calc R . .
H32C H 0.3882 0.1573 0.0531 0.146 Uiso 1 1 calc R . .
C33 C 0.5474(3) 0.0882(4) 0.0994(3) 0.103(2) Uani 1 1 d . . .
H33A H 0.6003 0.0905 0.1272 0.155 Uiso 1 1 calc R . .
H33B H 0.5470 0.1469 0.0732 0.155 Uiso 1 1 calc R . .
H33C H 0.5416 0.0157 0.0816 0.155 Uiso 1 1 calc R . .
C34 C 0.4769(3) 0.0108(5) 0.1678(3) 0.097(2) Uani 1 1 d . . .
H34A H 0.5299 0.0157 0.1954 0.145 Uiso 1 1 calc R . .
H34B H 0.4729 -0.0617 0.1501 0.145 Uiso 1 1 calc R . .
H34C H 0.4303 0.0194 0.1842 0.145 Uiso 1 1 calc R . .
C4 C 0.5447(3) 0.2965(5) 0.1561(2) 0.0511(16) Uani 1 1 d . . .
H4 H 0.5858 0.2761 0.1383 0.061 Uiso 1 1 calc R . .
C5 C 0.6216(3) 0.4782(5) 0.1824(2) 0.0521(17) Uani 1 1 d . . .
H5 H 0.6618 0.4556 0.1644 0.063 Uiso 1 1 calc R . .
C6 C 0.6305(3) 0.5820(5) 0.2071(2) 0.0476(16) Uani 1 1 d . A .
C61 C 0.7022(4) 0.6659(5) 0.2068(3) 0.070(2) Uani 1 1 d . . .
C62 C 0.7676(6) 0.6190(7) 0.1804(5) 0.103(5) Uani 0.769(11) 1 d P A 1
H62A H 0.7399 0.5946 0.1440 0.154 Uiso 0.769(11) 1 calc PR A 1
H62B H 0.7960 0.5558 0.2012 0.154 Uiso 0.769(11) 1 calc PR A 1
H62C H 0.8087 0.6768 0.1790 0.154 Uiso 0.769(11) 1 calc PR A 1
C63 C 0.7432(8) 0.7097(14) 0.2624(5) 0.172(8) Uani 0.769(11) 1 d P A 1
H63A H 0.7002 0.7384 0.2785 0.258 Uiso 0.769(11) 1 calc PR A 1
H63B H 0.7822 0.7695 0.2600 0.258 Uiso 0.769(11) 1 calc PR A 1
H63C H 0.7738 0.6494 0.2845 0.258 Uiso 0.769(11) 1 calc PR A 1
C64 C 0.6598(6) 0.7664(9) 0.1678(7) 0.173(8) Uani 0.769(11) 1 d P A 1
H64A H 0.6160 0.8010 0.1814 0.260 Uiso 0.769(11) 1 calc PR A 1
H64B H 0.6352 0.7374 0.1318 0.260 Uiso 0.769(11) 1 calc PR A 1
H64C H 0.7025 0.8219 0.1664 0.260 Uiso 0.769(11) 1 calc PR A 1
C65 C 0.701(2) 0.775(3) 0.2342(18) 0.067(11) Uiso 0.231(11) 1 d P A 2
H65A H 0.7475 0.8208 0.2301 0.100 Uiso 0.231(11) 1 calc PR A 2
H65B H 0.7060 0.7619 0.2722 0.100 Uiso 0.231(11) 1 calc PR A 2
H65C H 0.6478 0.8128 0.2182 0.100 Uiso 0.231(11) 1 calc PR A 2
C66 C 0.710(2) 0.677(3) 0.1522(14) 0.102(14) Uiso 0.231(11) 1 d P A 2
H66A H 0.7013 0.6041 0.1345 0.153 Uiso 0.231(11) 1 calc PR A 2
H66B H 0.7667 0.7033 0.1531 0.153 Uiso 0.231(11) 1 calc PR A 2
H66C H 0.6688 0.7296 0.1324 0.153 Uiso 0.231(11) 1 calc PR A 2
C67 C 0.7936(14) 0.595(2) 0.2431(13) 0.069(11) Uiso 0.231(11) 1 d P A 2
H67A H 0.7954 0.5211 0.2277 0.104 Uiso 0.231(11) 1 calc PR A 2
H67B H 0.7924 0.5878 0.2805 0.104 Uiso 0.231(11) 1 calc PR A 2
H67C H 0.8432 0.6373 0.2411 0.104 Uiso 0.231(11) 1 calc PR A 2
C7 C 0.5679(3) 0.6122(4) 0.2339(2) 0.0545(17) Uani 1 1 d . . .
H7 H 0.5720 0.6826 0.2509 0.065 Uiso 1 1 calc R A .
C8 C 0.5018(3) 0.5432(5) 0.2361(2) 0.0510(16) Uani 1 1 d . A .
H8 H 0.4628 0.5668 0.2549 0.061 Uiso 1 1 calc R . .
C9 C 0.4915(3) 0.4352(5) 0.2100(2) 0.0421(15) Uani 1 1 d . . .
C10 C 0.5535(3) 0.4036(4) 0.1832(2) 0.0418(15) Uani 1 1 d . A .
C11 C 0.3654(3) 0.3884(5) 0.2448(3) 0.0435(16) Uani 1 1 d . . .
N12 N 0.3043(3) 0.4631(4) 0.2257(2) 0.0519(13) Uani 1 1 d . A .
C13 C 0.2552(3) 0.4987(4) 0.2589(3) 0.0595(19) Uani 1 1 d . . .
H13 H 0.2127 0.5519 0.2454 0.071 Uiso 1 1 calc R A .
C14 C 0.2654(4) 0.4605(5) 0.3103(3) 0.070(2) Uani 1 1 d . A .
H14 H 0.2305 0.4875 0.3313 0.084 Uiso 1 1 calc R . .
C15 C 0.3433(5) 0.3355(6) 0.3849(3) 0.097(2) Uani 1 1 d . A .
H15 H 0.3102 0.3605 0.4075 0.116 Uiso 1 1 calc R . .
C16 C 0.4041(6) 0.2573(7) 0.4035(4) 0.131(3) Uani 1 1 d . . .
H16 H 0.4121 0.2281 0.4384 0.157 Uiso 1 1 calc R . .
C17 C 0.4563(5) 0.2187(6) 0.3702(4) 0.116(3) Uani 1 1 d . A .
H17 H 0.4990 0.1655 0.3836 0.139 Uiso 1 1 calc R . .
C18 C 0.4439(4) 0.2598(5) 0.3185(3) 0.086(2) Uani 1 1 d . . .
H18 H 0.4779 0.2340 0.2967 0.103 Uiso 1 1 calc R A .
C19 C 0.3803(4) 0.3405(5) 0.2980(3) 0.0524(17) Uani 1 1 d . A .
C20 C 0.3285(4) 0.3805(5) 0.3319(3) 0.0595(18) Uani 1 1 d . . .
C1A C 0.6939(3) 0.1619(5) 0.5828(2) 0.0476(17) Uani 1 1 d . . .
C2A C 0.7434(3) 0.0687(5) 0.5787(3) 0.0486(16) Uani 1 1 d . . .
O2A O 0.7558(2) -0.0156(3) 0.6169(2) 0.0614(14) Uani 1 1 d . . .
C3A C 0.7805(3) 0.0526(5) 0.5335(2) 0.0460(16) Uani 1 1 d . . .
C31A C 0.8358(4) -0.0512(5) 0.5295(3) 0.0547(17) Uani 1 1 d . . .
C32A C 0.9160(4) -0.0502(4) 0.5771(2) 0.084(2) Uani 1 1 d . . .
H32D H 0.9507 -0.1148 0.5746 0.126 Uiso 1 1 calc R . .
H32E H 0.8999 -0.0530 0.6108 0.126 Uiso 1 1 calc R . .
H32F H 0.9478 0.0180 0.5758 0.126 Uiso 1 1 calc R . .
C33A C 0.7866(3) -0.1622(4) 0.5302(2) 0.091(2) Uani 1 1 d . . .
H33D H 0.8226 -0.2255 0.5276 0.137 Uiso 1 1 calc R . .
H33E H 0.7368 -0.1633 0.4999 0.137 Uiso 1 1 calc R . .
H33F H 0.7697 -0.1672 0.5636 0.137 Uiso 1 1 calc R . .
C34A C 0.8652(3) -0.0498(4) 0.4766(2) 0.086(2) Uani 1 1 d . . .
H34D H 0.8996 -0.1155 0.4754 0.129 Uiso 1 1 calc R . .
H34E H 0.8981 0.0174 0.4756 0.129 Uiso 1 1 calc R . .
H34F H 0.8161 -0.0504 0.4457 0.129 Uiso 1 1 calc R . .
C4A C 0.7642(3) 0.1357(5) 0.4946(2) 0.0498(17) Uani 1 1 d . . .
H4A H 0.7869 0.1273 0.4648 0.060 Uiso 1 1 calc R . .
C5A C 0.7019(3) 0.3204(5) 0.4567(2) 0.0575(17) Uani 1 1 d . . .
H5A H 0.7256 0.3109 0.4274 0.069 Uiso 1 1 calc R . .
C6A C 0.6558(3) 0.4181(5) 0.4588(3) 0.0531(17) Uani 1 1 d . . .
C61A C 0.6442(4) 0.5131(5) 0.4163(3) 0.070(2) Uani 1 1 d . . .
C62A C 0.6755(4) 0.4784(5) 0.3670(3) 0.141(3) Uani 1 1 d . . .
H62D H 0.6663 0.5396 0.3413 0.211 Uiso 1 1 calc R . .
H62E H 0.6445 0.4128 0.3502 0.211 Uiso 1 1 calc R . .
H62F H 0.7353 0.4609 0.3786 0.211 Uiso 1 1 calc R . .
C63A C 0.6950(5) 0.6133(6) 0.4427(3) 0.207(5) Uani 1 1 d . . .
H63D H 0.6879 0.6744 0.4169 0.310 Uiso 1 1 calc R . .
H63E H 0.7543 0.5930 0.4546 0.310 Uiso 1 1 calc R . .
H63F H 0.6754 0.6368 0.4735 0.310 Uiso 1 1 calc R . .
C64A C 0.5508(4) 0.5441(5) 0.3954(3) 0.142(3) Uani 1 1 d . . .
H64D H 0.5447 0.6038 0.3690 0.213 Uiso 1 1 calc R . .
H64E H 0.5294 0.5692 0.4252 0.213 Uiso 1 1 calc R . .
H64F H 0.5191 0.4789 0.3787 0.213 Uiso 1 1 calc R . .
C7A C 0.6217(3) 0.4286(5) 0.5047(3) 0.0636(18) Uani 1 1 d . . .
H7A H 0.5908 0.4934 0.5080 0.076 Uiso 1 1 calc R . .
C8A C 0.6327(3) 0.3470(5) 0.5443(2) 0.0572(17) Uani 1 1 d . . .
H8A H 0.6088 0.3575 0.5734 0.069 Uiso 1 1 calc R . .
C9A C 0.6795(3) 0.2474(5) 0.5418(3) 0.0459(16) Uani 1 1 d . . .
C10A C 0.7150(3) 0.2334(5) 0.4970(2) 0.0459(16) Uani 1 1 d . . .
C11A C 0.6496(4) 0.1706(4) 0.6275(3) 0.0411(15) Uani 1 1 d . . .
N12A N 0.6928(3) 0.2247(4) 0.6721(2) 0.0491(14) Uani 1 1 d . . .
C13A C 0.6545(4) 0.2336(4) 0.7142(3) 0.0555(17) Uani 1 1 d . . .
H13A H 0.6841 0.2710 0.7457 0.067 Uiso 1 1 calc R . .
C14A C 0.5759(4) 0.1910(4) 0.7125(3) 0.0567(18) Uani 1 1 d . . .
H14A H 0.5537 0.1968 0.7426 0.068 Uiso 1 1 calc R . .
C15A C 0.4449(4) 0.0959(5) 0.6583(3) 0.070(2) Uani 1 1 d . . .
H15A H 0.4200 0.0994 0.6873 0.083 Uiso 1 1 calc R . .
C16A C 0.4014(4) 0.0507(5) 0.6104(4) 0.082(2) Uani 1 1 d . . .
H16A H 0.3463 0.0239 0.6069 0.098 Uiso 1 1 calc R . .
C17A C 0.4365(4) 0.0429(5) 0.5656(3) 0.078(2) Uani 1 1 d . . .
H17A H 0.4049 0.0123 0.5328 0.093 Uiso 1 1 calc R . .
C18A C 0.5180(4) 0.0810(5) 0.5709(3) 0.0635(18) Uani 1 1 d . . .
H18A H 0.5422 0.0752 0.5416 0.076 Uiso 1 1 calc R . .
C19A C 0.5653(4) 0.1289(4) 0.6202(3) 0.0476(16) Uani 1 1 d . . .
C20A C 0.5290(4) 0.1383(4) 0.6646(3) 0.0484(16) Uani 1 1 d . . .
H2A H 0.771(4) 0.001(4) 0.655(3) 0.10(3) Uiso 1 1 d . . .
H2 H 0.296(4) 0.218(4) 0.179(2) 0.10(2) Uiso 1 1 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 C9 120.2(5) . . ?
C2 C1 C11 121.7(5) . . ?
C9 C1 C11 117.8(5) . . ?
C1 C2 O2 119.9(5) . . ?
C1 C2 C3 122.8(5) . . ?
O2 C2 C3 117.2(6) . . ?
C2 O2 H2 117(3) . . ?
C4 C3 C2 115.6(5) . . ?
C4 C3 C31 122.0(5) . . ?
C2 C3 C31 122.4(5) . . ?
C33 C31 C32 108.1(6) . . ?
C33 C31 C3 111.7(5) . . ?
C32 C31 C3 110.3(4) . . ?
C33 C31 C34 107.7(5) . . ?
C32 C31 C34 110.7(5) . . ?
C3 C31 C34 108.3(5) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C3 C4 C10 123.9(5) . . ?
C3 C4 H4 118.1 . . ?
C10 C4 H4 118.1 . . ?
C6 C5 C10 122.6(5) . . ?
C6 C5 H5 118.7 . . ?
C10 C5 H5 118.7 . . ?
C5 C6 C7 116.5(5) . . ?
C5 C6 C61 124.5(6) . . ?
C7 C6 C61 119.0(6) . . ?
C66 C61 C65 114(2) . . ?
C66 C61 C63 139.2(15) . . ?
C65 C61 C63 45.8(14) . . ?
C66 C61 C62 49.0(15) . . ?
C65 C61 C62 129.6(14) . . ?
C63 C61 C62 111.1(9) . . ?
C66 C61 C6 109.0(14) . . ?
C65 C61 C6 117.2(14) . . ?
C63 C61 C6 111.8(7) . . ?
C62 C61 C6 113.1(6) . . ?
C66 C61 C64 57.5(15) . . ?
C65 C61 C64 65.4(13) . . ?
C63 C61 C64 110.4(9) . . ?
C62 C61 C64 103.7(7) . . ?
C6 C61 C64 106.4(7) . . ?
C66 C61 C67 105.9(19) . . ?
C65 C61 C67 106.6(18) . . ?
C63 C61 C67 63.6(11) . . ?
C62 C61 C67 57.2(10) . . ?
C6 C61 C67 103.3(9) . . ?
C64 C61 C67 149.5(9) . . ?
C61 C62 H62A 109.5 . . ?
C61 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C61 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C61 C63 H63A 109.5 . . ?
C61 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C61 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
C61 C64 H64A 109.5 . . ?
C61 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
C61 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C61 C65 H65A 109.5 . . ?
C61 C65 H65B 109.5 . . ?
H65A C65 H65B 109.5 . . ?
C61 C65 H65C 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
C61 C66 H66A 109.5 . . ?
C61 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
C61 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
C61 C67 H67A 109.5 . . ?
C61 C67 H67B 109.5 . . ?
H67A C67 H67B 109.5 . . ?
C61 C67 H67C 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C8 C7 C6 123.0(5) . . ?
C8 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?
C7 C8 C9 120.8(5) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C1 119.1(5) . . ?
C10 C9 C8 116.9(5) . . ?
C1 C9 C8 124.1(5) . . ?
C9 C10 C5 120.1(5) . . ?
C9 C10 C4 118.4(5) . . ?
C5 C10 C4 121.4(5) . . ?
N12 C11 C19 122.5(5) . . ?
N12 C11 C1 117.7(6) . . ?
C19 C11 C1 119.7(5) . . ?
C11 N12 C13 118.6(5) . . ?
C14 C13 N12 123.4(6) . . ?
C14 C13 H13 118.3 . . ?
N12 C13 H13 118.3 . . ?
C13 C14 C20 119.9(6) . . ?
C13 C14 H14 120.1 . . ?
C20 C14 H14 120.1 . . ?
C16 C15 C20 121.3(7) . . ?
C16 C15 H15 119.3 . . ?
C20 C15 H15 119.3 . . ?
C15 C16 C17 120.6(8) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.9(7) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.6(7) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C11 123.2(6) . . ?
C18 C19 C20 119.4(6) . . ?
C11 C19 C20 117.4(6) . . ?
C14 C20 C15 123.7(7) . . ?
C14 C20 C19 118.1(6) . . ?
C15 C20 C19 118.2(6) . . ?
C2A C1A C9A 119.6(6) . . ?
C2A C1A C11A 121.0(6) . . ?
C9A C1A C11A 119.2(5) . . ?
O2A C2A C1A 120.3(6) . . ?
O2A C2A C3A 117.1(6) . . ?
C1A C2A C3A 122.5(6) . . ?
C2A O2A H2A 122(3) . . ?
C4A C3A C2A 116.1(5) . . ?
C4A C3A C31A 121.9(6) . . ?
C2A C3A C31A 122.0(6) . . ?
C32A C31A C33A 109.6(5) . . ?
C32A C31A C3A 109.4(5) . . ?
C33A C31A C3A 111.3(5) . . ?
C32A C31A C34A 107.4(5) . . ?
C33A C31A C34A 107.5(5) . . ?
C3A C31A C34A 111.6(5) . . ?
C31A C32A H32D 109.5 . . ?
C31A C32A H32E 109.5 . . ?
H32D C32A H32E 109.5 . . ?
C31A C32A H32F 109.5 . . ?
H32D C32A H32F 109.5 . . ?
H32E C32A H32F 109.5 . . ?
C31A C33A H33D 109.5 . . ?
C31A C33A H33E 109.5 . . ?
H33D C33A H33E 109.5 . . ?
C31A C33A H33F 109.5 . . ?
H33D C33A H33F 109.5 . . ?
H33E C33A H33F 109.5 . . ?
C31A C34A H34D 109.5 . . ?
C31A C34A H34E 109.5 . . ?
H34D C34A H34E 109.5 . . ?
C31A C34A H34F 109.5 . . ?
H34D C34A H34F 109.5 . . ?
H34E C34A H34F 109.5 . . ?
C3A C4A C10A 123.9(5) . . ?
C3A C4A H4A 118.0 . . ?
C10A C4A H4A 118.0 . . ?
C6A C5A C10A 123.5(5) . . ?
C6A C5A H5A 118.3 . . ?
C10A C5A H5A 118.3 . . ?
C5A C6A C7A 115.8(6) . . ?
C5A C6A C61A 123.2(6) . . ?
C7A C6A C61A 120.9(6) . . ?
C63A C61A C64A 110.5(6) . . ?
C63A C61A C62A 108.6(6) . . ?
C64A C61A C62A 107.1(6) . . ?
C63A C61A C6A 108.0(6) . . ?
C64A C61A C6A 110.5(5) . . ?
C62A C61A C6A 112.2(5) . . ?
C61A C62A H62D 109.5 . . ?
C61A C62A H62E 109.5 . . ?
H62D C62A H62E 109.5 . . ?
C61A C62A H62F 109.5 . . ?
H62D C62A H62F 109.5 . . ?
H62E C62A H62F 109.5 . . ?
C61A C63A H63D 109.5 . . ?
C61A C63A H63E 109.5 . . ?
H63D C63A H63E 109.5 . . ?
C61A C63A H63F 109.5 . . ?
H63D C63A H63F 109.5 . . ?
H63E C63A H63F 109.5 . . ?
C61A C64A H64D 109.5 . . ?
C61A C64A H64E 109.5 . . ?
H64D C64A H64E 109.5 . . ?
C61A C64A H64F 109.5 . . ?
H64D C64A H64F 109.5 . . ?
H64E C64A H64F 109.5 . . ?
C8A C7A C6A 122.5(5) . . ?
C8A C7A H7A 118.7 . . ?
C6A C7A H7A 118.7 . . ?
C7A C8A C9A 121.4(6) . . ?
C7A C8A H8A 119.3 . . ?
C9A C8A H8A 119.3 . . ?
C8A C9A C10A 118.2(6) . . ?
C8A C9A C1A 122.9(6) . . ?
C10A C9A C1A 118.9(5) . . ?
C4A C10A C9A 119.0(6) . . ?
C4A C10A C5A 122.4(6) . . ?
C9A C10A C5A 118.6(5) . . ?
N12A C11A C19A 123.7(5) . . ?
N12A C11A C1A 115.3(5) . . ?
C19A C11A C1A 120.9(6) . . ?
C11A N12A C13A 117.0(5) . . ?
C14A C13A N12A 123.9(5) . . ?
C14A C13A H13A 118.0 . . ?
N12A C13A H13A 118.0 . . ?
C13A C14A C20A 118.9(6) . . ?
C13A C14A H14A 120.5 . . ?
C20A C14A H14A 120.5 . . ?
C16A C15A C20A 120.1(6) . . ?
C16A C15A H15A 120.0 . . ?
C20A C15A H15A 120.0 . . ?
C15A C16A C17A 122.1(6) . . ?
C15A C16A H16A 119.0 . . ?
C17A C16A H16A 119.0 . . ?
C18A C17A C16A 119.0(6) . . ?
C18A C17A H17A 120.5 . . ?
C16A C17A H17A 120.5 . . ?
C17A C18A C19A 120.5(6) . . ?
C17A C18A H18A 119.8 . . ?
C19A C18A H18A 119.8 . . ?
C18A C19A C20A 120.1(6) . . ?
C18A C19A C11A 122.7(6) . . ?
C20A C19A C11A 117.2(6) . . ?
C14A C20A C19A 119.0(6) . . ?
C14A C20A C15A 122.7(7) . . ?
C19A C20A C15A 118.2(6) . . ?
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 1.376(6) . ?
C1 C9 1.416(6) . ?
C1 C11 1.498(6) . ?
C2 O2 1.380(5) . ?
C2 C3 1.429(6) . ?
O2 H2 0.96(5) . ?
C3 C4 1.376(6) . ?
C3 C31 1.547(6) . ?
C31 C33 1.536(6) . ?
C31 C32 1.542(6) . ?
C31 C34 1.552(7) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C4 C10 1.428(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(6) . ?
C5 C10 1.416(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.409(6) . ?
C6 C61 1.530(7) . ?
C61 C66 1.43(3) . ?
C61 C65 1.46(3) . ?
C61 C63 1.488(11) . ?
C61 C62 1.503(9) . ?
C61 C64 1.583(11) . ?
C61 C67 1.74(2) . ?
C62 H62A 0.9600 . ?
C62 H62B 0.9600 . ?
C62 H62C 0.9600 . ?
C63 H63A 0.9600 . ?
C63 H63B 0.9600 . ?
C63 H63C 0.9600 . ?
C64 H64A 0.9600 . ?
C64 H64B 0.9600 . ?
C64 H64C 0.9600 . ?
C65 H65A 0.9600 . ?
C65 H65B 0.9600 . ?
C65 H65C 0.9600 . ?
C66 H66A 0.9600 . ?
C66 H66B 0.9600 . ?
C66 H66C 0.9600 . ?
C67 H67A 0.9600 . ?
C67 H67B 0.9600 . ?
C67 H67C 0.9600 . ?
C7 C8 1.359(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.426(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.404(6) . ?
C11 N12 1.320(5) . ?
C11 C19 1.426(7) . ?
N12 C13 1.370(6) . ?
C13 C14 1.351(7) . ?
C13 H13 0.9300 . ?
C14 C20 1.394(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.344(8) . ?
C15 C20 1.408(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.420(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.401(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.434(7) . ?
C1A C2A 1.382(6) . ?
C1A C9A 1.426(6) . ?
C1A C11A 1.499(6) . ?
C2A O2A 1.367(6) . ?
C2A C3A 1.444(6) . ?
O2A H2A 0.96(6) . ?
C3A C4A 1.367(6) . ?
C3A C31A 1.538(6) . ?
C31A C32A 1.528(6) . ?
C31A C33A 1.536(6) . ?
C31A C34A 1.540(6) . ?
C32A H32D 0.9600 . ?
C32A H32E 0.9600 . ?
C32A H32F 0.9600 . ?
C33A H33D 0.9600 . ?
C33A H33E 0.9600 . ?
C33A H33F 0.9600 . ?
C34A H34D 0.9600 . ?
C34A H34E 0.9600 . ?
C34A H34F 0.9600 . ?
C4A C10A 1.413(6) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.382(6) . ?
C5A C10A 1.427(6) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.422(6) . ?
C6A C61A 1.534(7) . ?
C61A C63A 1.496(7) . ?
C61A C64A 1.515(7) . ?
C61A C62A 1.525(7) . ?
C62A H62D 0.9600 . ?
C62A H62E 0.9600 . ?
C62A H62F 0.9600 . ?
C63A H63D 0.9600 . ?
C63A H63E 0.9600 . ?
C63A H63F 0.9600 . ?
C64A H64D 0.9600 . ?
C64A H64E 0.9600 . ?
C64A H64F 0.9600 . ?
C7A C8A 1.369(6) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.409(6) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.414(7) . ?
C11A N12A 1.330(6) . ?
C11A C19A 1.418(6) . ?
N12A C13A 1.374(6) . ?
C13A C14A 1.361(6) . ?
C13A H13A 0.9300 . ?
C14A C20A 1.401(6) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.349(7) . ?
C15A C20A 1.422(6) . ?
C15A H15A 0.9300 . ?
C16A C17A 1.405(7) . ?
C16A H16A 0.9300 . ?
C17A C18A 1.370(6) . ?
C17A H17A 0.9300 . ?
C18A C19A 1.405(6) . ?
C18A H18A 0.9300 . ?
C19A C20A 1.409(6) . ?
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
C9 C1 C2 O2 -179.9(5) . . . . ?
C11 C1 C2 O2 6.2(8) . . . . ?
C9 C1 C2 C3 2.3(8) . . . . ?
C11 C1 C2 C3 -171.5(5) . . . . ?
C1 C2 C3 C4 -1.5(8) . . . . ?
O2 C2 C3 C4 -179.3(5) . . . . ?
C1 C2 C3 C31 178.5(5) . . . . ?
O2 C2 C3 C31 0.7(8) . . . . ?
C4 C3 C31 C33 0.5(8) . . . . ?
C2 C3 C31 C33 -179.5(5) . . . . ?
C4 C3 C31 C32 -119.8(6) . . . . ?
C2 C3 C31 C32 60.2(7) . . . . ?
C4 C3 C31 C34 119.0(6) . . . . ?
C2 C3 C31 C34 -61.1(7) . . . . ?
C2 C3 C4 C10 0.5(8) . . . . ?
C31 C3 C4 C10 -179.6(5) . . . . ?
C10 C5 C6 C7 0.0(8) . . . . ?
C10 C5 C6 C61 -179.2(6) . . . . ?
C5 C6 C61 C66 48(2) . . . . ?
C7 C6 C61 C66 -132(2) . . . . ?
C5 C6 C61 C65 178.5(19) . . . . ?
C7 C6 C61 C65 -1(2) . . . . ?
C5 C6 C61 C63 -131.3(10) . . . . ?
C7 C6 C61 C63 49.6(11) . . . . ?
C5 C6 C61 C62 -5.0(11) . . . . ?
C7 C6 C61 C62 175.8(7) . . . . ?
C5 C6 C61 C64 108.2(9) . . . . ?
C7 C6 C61 C64 -71.0(10) . . . . ?
C5 C6 C61 C67 -64.7(14) . . . . ?
C7 C6 C61 C67 116.2(12) . . . . ?
C5 C6 C7 C8 0.5(8) . . . . ?
C61 C6 C7 C8 179.7(6) . . . . ?
C6 C7 C8 C9 -1.1(8) . . . . ?
C2 C1 C9 C10 -2.0(8) . . . . ?
C11 C1 C9 C10 172.0(5) . . . . ?
C2 C1 C9 C8 178.4(5) . . . . ?
C11 C1 C9 C8 -7.6(8) . . . . ?
C7 C8 C9 C10 1.2(7) . . . . ?
C7 C8 C9 C1 -179.1(5) . . . . ?
C1 C9 C10 C5 179.6(5) . . . . ?
C8 C9 C10 C5 -0.8(7) . . . . ?
C1 C9 C10 C4 1.0(7) . . . . ?
C8 C9 C10 C4 -179.4(5) . . . . ?
C6 C5 C10 C9 0.2(8) . . . . ?
C6 C5 C10 C4 178.7(5) . . . . ?
C3 C4 C10 C9 -0.3(8) . . . . ?
C3 C4 C10 C5 -178.8(5) . . . . ?
C2 C1 C11 N12 -105.5(6) . . . . ?
C9 C1 C11 N12 80.5(6) . . . . ?
C2 C1 C11 C19 78.1(7) . . . . ?
C9 C1 C11 C19 -95.9(6) . . . . ?
C19 C11 N12 C13 2.2(8) . . . . ?
C1 C11 N12 C13 -174.1(4) . . . . ?
C11 N12 C13 C14 -0.6(8) . . . . ?
N12 C13 C14 C20 -0.2(9) . . . . ?
C20 C15 C16 C17 0.9(13) . . . . ?
C15 C16 C17 C18 -1.1(13) . . . . ?
C16 C17 C18 C19 0.4(12) . . . . ?
C17 C18 C19 C11 178.6(6) . . . . ?
C17 C18 C19 C20 0.4(10) . . . . ?
N12 C11 C19 C18 178.9(5) . . . . ?
C1 C11 C19 C18 -4.9(8) . . . . ?
N12 C11 C19 C20 -2.9(8) . . . . ?
C1 C11 C19 C20 173.3(5) . . . . ?
C13 C14 C20 C15 -179.6(6) . . . . ?
C13 C14 C20 C19 -0.6(9) . . . . ?
C16 C15 C20 C14 179.0(7) . . . . ?
C16 C15 C20 C19 0.0(11) . . . . ?
C18 C19 C20 C14 -179.7(6) . . . . ?
C11 C19 C20 C14 2.0(8) . . . . ?
C18 C19 C20 C15 -0.7(9) . . . . ?
C11 C19 C20 C15 -178.9(6) . . . . ?
C9A C1A C2A O2A -178.0(5) . . . . ?
C11A C1A C2A O2A -2.7(8) . . . . ?
C9A C1A C2A C3A -1.2(8) . . . . ?
C11A C1A C2A C3A 174.1(5) . . . . ?
O2A C2A C3A C4A 177.2(5) . . . . ?
C1A C2A C3A C4A 0.3(8) . . . . ?
O2A C2A C3A C31A -3.4(8) . . . . ?
C1A C2A C3A C31A 179.7(5) . . . . ?
C4A C3A C31A C32A 116.3(6) . . . . ?
C2A C3A C31A C32A -63.0(6) . . . . ?
C4A C3A C31A C33A -122.4(6) . . . . ?
C2A C3A C31A C33A 58.2(7) . . . . ?
C4A C3A C31A C34A -2.3(7) . . . . ?
C2A C3A C31A C34A 178.3(5) . . . . ?
C2A C3A C4A C10A 0.5(8) . . . . ?
C31A C3A C4A C10A -178.9(5) . . . . ?
C10A C5A C6A C7A 0.6(8) . . . . ?
C10A C5A C6A C61A 178.0(5) . . . . ?
C5A C6A C61A C63A -109.6(7) . . . . ?
C7A C6A C61A C63A 67.7(8) . . . . ?
C5A C6A C61A C64A 129.5(6) . . . . ?
C7A C6A C61A C64A -53.2(8) . . . . ?
C5A C6A C61A C62A 10.0(8) . . . . ?
C7A C6A C61A C62A -172.7(6) . . . . ?
C5A C6A C7A C8A -0.7(9) . . . . ?
C61A C6A C7A C8A -178.2(5) . . . . ?
C6A C7A C8A C9A 0.5(9) . . . . ?
C7A C8A C9A C10A -0.2(8) . . . . ?
C7A C8A C9A C1A 178.5(5) . . . . ?
C2A C1A C9A C8A -177.3(5) . . . . ?
C11A C1A C9A C8A 7.3(8) . . . . ?
C2A C1A C9A C10A 1.3(8) . . . . ?
C11A C1A C9A C10A -174.1(5) . . . . ?
C3A C4A C10A C9A -0.4(8) . . . . ?
C3A C4A C10A C5A 177.6(5) . . . . ?
C8A C9A C10A C4A 178.2(5) . . . . ?
C1A C9A C10A C4A -0.5(8) . . . . ?
C8A C9A C10A C5A 0.1(7) . . . . ?
C1A C9A C10A C5A -178.6(5) . . . . ?
C6A C5A C10A C4A -178.3(5) . . . . ?
C6A C5A C10A C9A -0.3(8) . . . . ?
C2A C1A C11A N12A 92.8(6) . . . . ?
C9A C1A C11A N12A -91.9(6) . . . . ?
C2A C1A C11A C19A -90.7(7) . . . . ?
C9A C1A C11A C19A 84.6(7) . . . . ?
C19A C11A N12A C13A 4.1(8) . . . . ?
C1A C11A N12A C13A -179.5(4) . . . . ?
C11A N12A C13A C14A -0.2(8) . . . . ?
N12A C13A C14A C20A -2.4(8) . . . . ?
C20A C15A C16A C17A 0.5(10) . . . . ?
C15A C16A C17A C18A 0.8(10) . . . . ?
C16A C17A C18A C19A -1.0(9) . . . . ?
C17A C18A C19A C20A -0.1(8) . . . . ?
C17A C18A C19A C11A -179.4(5) . . . . ?
N12A C11A C19A C18A 174.2(5) . . . . ?
C1A C11A C19A C18A -2.0(8) . . . . ?
N12A C11A C19A C20A -5.1(8) . . . . ?
C1A C11A C19A C20A 178.7(5) . . . . ?
C13A C14A C20A C19A 1.3(8) . . . . ?
C13A C14A C20A C15A -177.1(5) . . . . ?
C18A C19A C20A C14A -177.1(5) . . . . ?
C11A C19A C20A C14A 2.2(7) . . . . ?
C18A C19A C20A C15A 1.4(8) . . . . ?
C11A C19A C20A C15A -179.3(5) . . . . ?
C16A C15A C20A C14A 176.9(6) . . . . ?
C16A C15A C20A C19A -1.6(9) . . . . ?
