#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/55/4025529.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_4025529
loop_
_publ_author_name
'Alexander F. Pozharskii'
'Alexander V. Degtyarev'
'Valery A. Ozeryanskii'
'Oksana V. Ryabtsova'
'Zoya A. Starikova'
'Gennadii S. Borodkin'
_publ_section_title
;
 1,8,1',8'-Tetrakis(dimethylamino)-2,2'-dinaphthylmethanols: Double In/Out
 Proton Sponges with Low-Barrier Hydrogen-Bond Switching
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4706
_journal_page_last               4715
_journal_paper_doi               10.1021/jo100384s
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C35 H40 N4 O'
_chemical_formula_sum            'C35 H40 N4 O'
_chemical_formula_weight         532.71
_chemical_name_systematic
; 
 ? 
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.0820(10)
_cell_angle_beta                 118.6410(10)
_cell_angle_gamma                102.7560(10)
_cell_formula_units_Z            2
_cell_length_a                   11.9154(5)
_cell_length_b                   11.9676(9)
_cell_length_c                   12.0603(5)
_cell_measurement_reflns_used    5108
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.16
_cell_measurement_theta_min      2.26
_cell_volume                     1418.38(14)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17109
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         7419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0446
_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)+(0.0155P)²+0.7616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0915
_reflns_number_gt                5597
_reflns_number_total             7419
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo100384s_si_002.cif
_cod_data_source_block           fin
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025529
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 0.47281(9) 0.88247(8) 0.00503(9) 0.01685(18) Uani 1 1 d . . .
H1O H 0.5256 0.9361 0.0770 0.020 Uiso 1 1 d R . .
N1 N 0.62561(11) 0.96599(9) 0.26270(10) 0.0178(2) Uani 1 1 d . . .
N2 N 0.76266(11) 1.01831(10) 0.55265(11) 0.0196(2) Uani 1 1 d . . .
N1' N 0.22502(11) 0.70093(9) -0.01336(10) 0.0173(2) Uani 1 1 d . . .
N2' N -0.04715(11) 0.63886(10) -0.22895(11) 0.0187(2) Uani 1 1 d . . .
C1 C 0.58089(12) 0.84834(11) 0.27467(12) 0.0145(2) Uani 1 1 d . . .
C2 C 0.51448(12) 0.75623(11) 0.16019(12) 0.0147(2) Uani 1 1 d . . .
C3 C 0.46518(12) 0.63793(11) 0.16158(12) 0.0163(2) Uani 1 1 d . . .
H3A H 0.4312 0.5760 0.0877 0.020 Uiso 1 1 calc R . .
C4 C 0.46676(12) 0.61321(11) 0.26944(12) 0.0172(2) Uani 1 1 d . . .
H4A H 0.4292 0.5353 0.2666 0.021 Uiso 1 1 calc R . .
C5 C 0.52465(12) 0.70440(11) 0.38539(12) 0.0163(2) Uani 1 1 d . . .
C6 C 0.51387(13) 0.67630(12) 0.49176(13) 0.0200(3) Uani 1 1 d . . .
H6A H 0.4659 0.5994 0.4823 0.024 Uiso 1 1 calc R . .
C7 C 0.57267(14) 0.76021(13) 0.60707(13) 0.0233(3) Uani 1 1 d . . .
H7A H 0.5600 0.7430 0.6742 0.028 Uiso 1 1 calc R . .
C8 C 0.65271(14) 0.87313(12) 0.62320(13) 0.0221(3) Uani 1 1 d . . .
H8A H 0.6982 0.9286 0.7044 0.027 Uiso 1 1 calc R . .
C9 C 0.66686(13) 0.90544(11) 0.52330(12) 0.0180(3) Uani 1 1 d . . .
C10 C 0.59318(12) 0.82331(11) 0.39468(12) 0.0154(2) Uani 1 1 d . . .
C11 C 0.57519(14) 1.05649(12) 0.29754(14) 0.0234(3) Uani 1 1 d . . .
H11A H 0.4842 1.0200 0.2754 0.035 Uiso 1 1 calc R . .
H11B H 0.5769 1.1151 0.2502 0.035 Uiso 1 1 calc R . .
H11C H 0.6313 1.0940 0.3900 0.035 Uiso 1 1 calc R . .
C12 C 0.76437(14) 1.01391(13) 0.29374(14) 0.0258(3) Uani 1 1 d . . .
H12A H 0.7920 0.9506 0.2688 0.039 Uiso 1 1 calc R . .
H12B H 0.8230 1.0505 0.3862 0.039 Uiso 1 1 calc R . .
H12C H 0.7692 1.0720 0.2466 0.039 Uiso 1 1 calc R . .
C13 C 0.89793(14) 1.00850(14) 0.60417(15) 0.0288(3) Uani 1 1 d . . .
H13A H 0.8947 0.9444 0.5452 0.043 Uiso 1 1 calc R . .
H13B H 0.9296 0.9931 0.6886 0.043 Uiso 1 1 calc R . .
H13C H 0.9582 1.0815 0.6125 0.043 Uiso 1 1 calc R . .
C14 C 0.76537(17) 1.11564(13) 0.64133(15) 0.0308(3) Uani 1 1 d . . .
H14A H 0.6761 1.1212 0.6063 0.046 Uiso 1 1 calc R . .
H14B H 0.8254 1.1890 0.6500 0.046 Uiso 1 1 calc R . .
H14C H 0.7964 1.1005 0.7258 0.046 Uiso 1 1 calc R . .
C1' C 0.24369(12) 0.65390(11) -0.11451(12) 0.0149(2) Uani 1 1 d . . .
C2' C 0.37462(12) 0.67787(11) -0.09244(12) 0.0155(2) Uani 1 1 d . . .
C3' C 0.39463(13) 0.61265(11) -0.18361(12) 0.0180(3) Uani 1 1 d . . .
H3'A H 0.4795 0.6335 -0.1738 0.022 Uiso 1 1 calc R . .
C4' C 0.29229(13) 0.51960(12) -0.28587(12) 0.0192(3) Uani 1 1 d . . .
H4'A H 0.3104 0.4738 -0.3395 0.023 Uiso 1 1 calc R . .
C5' C 0.15993(13) 0.49224(11) -0.31094(12) 0.0176(2) Uani 1 1 d . . .
C6' C 0.05614(14) 0.39098(12) -0.41223(13) 0.0215(3) Uani 1 1 d . . .
H6'A H 0.0766 0.3406 -0.4597 0.026 Uiso 1 1 calc R . .
C7' C -0.07261(14) 0.36724(12) -0.44012(13) 0.0238(3) Uani 1 1 d . . .
H7'A H -0.1388 0.2976 -0.5019 0.029 Uiso 1 1 calc R . .
C8' C -0.10618(14) 0.44797(12) -0.37563(13) 0.0221(3) Uani 1 1 d . . .
H8'A H -0.1957 0.4327 -0.3989 0.026 Uiso 1 1 calc R . .
C9' C -0.00963(13) 0.54916(11) -0.27880(12) 0.0172(2) Uani 1 1 d . . .
C10' C 0.13152(12) 0.56748(11) -0.23285(12) 0.0157(2) Uani 1 1 d . . .
C11' C 0.23009(15) 0.82225(12) 0.02271(15) 0.0262(3) Uani 1 1 d . . .
H11D H 0.2775 0.8713 -0.0087 0.039 Uiso 1 1 calc R . .
H11E H 0.2762 0.8502 0.1164 0.039 Uiso 1 1 calc R . .
H11F H 0.1399 0.8260 -0.0156 0.039 Uiso 1 1 calc R . .
C12' C 0.15499(14) 0.62039(13) 0.03035(13) 0.0217(3) Uani 1 1 d . . .
H12D H 0.1548 0.5414 0.0035 0.033 Uiso 1 1 calc R . .
H12E H 0.0637 0.6212 -0.0077 0.033 Uiso 1 1 calc R . .
H12F H 0.2001 0.6452 0.1242 0.033 Uiso 1 1 calc R . .
C13' C -0.02385(16) 0.74703(12) -0.26973(15) 0.0274(3) Uani 1 1 d . . .
H13D H 0.0660 0.7710 -0.2541 0.041 Uiso 1 1 calc R . .
H13E H -0.0342 0.8091 -0.2204 0.041 Uiso 1 1 calc R . .
H13F H -0.0880 0.7323 -0.3615 0.041 Uiso 1 1 calc R . .
C14' C -0.18284(14) 0.60191(14) -0.25161(15) 0.0272(3) Uani 1 1 d . . .
H14D H -0.1973 0.5307 -0.2243 0.041 Uiso 1 1 calc R . .
H14E H -0.2476 0.5868 -0.3433 0.041 Uiso 1 1 calc R . .
H14F H -0.1932 0.6638 -0.2022 0.041 Uiso 1 1 calc R . .
C15 C 0.49760(12) 0.77423(11) 0.02807(12) 0.0143(2) Uani 1 1 d . . .
C16 C 0.63144(12) 0.77570(11) 0.03566(12) 0.0159(2) Uani 1 1 d . . .
C17 C 0.68661(13) 0.85815(12) -0.01170(13) 0.0196(3) Uani 1 1 d . . .
H17A H 0.6417 0.9104 -0.0488 0.023 Uiso 1 1 calc R . .
C18 C 0.80793(14) 0.86327(13) -0.00411(13) 0.0238(3) Uani 1 1 d . . .
H18A H 0.8434 0.9188 -0.0362 0.029 Uiso 1 1 calc R . .
C19 C 0.87634(14) 0.78616(13) 0.05097(13) 0.0235(3) Uani 1 1 d . . .
H19A H 0.9574 0.7896 0.0559 0.028 Uiso 1 1 calc R . .
C20 C 0.82266(14) 0.70381(12) 0.09865(13) 0.0222(3) Uani 1 1 d . . .
H20A H 0.8681 0.6519 0.1359 0.027 Uiso 1 1 calc R . .
C21 C 0.70165(13) 0.69858(12) 0.09098(13) 0.0193(3) Uani 1 1 d . . .
H21A H 0.6666 0.6429 0.1231 0.023 Uiso 1 1 calc R . .
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
C15 O1 H1O 107.2 . . ?
C1 N1 C11 118.41(10) . . ?
C1 N1 C12 118.84(11) . . ?
C11 N1 C12 113.17(11) . . ?
C9 N2 C13 110.56(11) . . ?
C9 N2 C14 114.29(11) . . ?
C13 N2 C14 110.31(12) . . ?
C1' N1' C11' 124.67(11) . . ?
C1' N1' C12' 119.08(10) . . ?
C11' N1' C12' 113.25(11) . . ?
C9' N2' C14' 115.77(11) . . ?
C9' N2' C13' 113.17(10) . . ?
C14' N2' C13' 110.02(11) . . ?
C2 C1 N1 116.01(10) . . ?
C2 C1 C10 119.77(11) . . ?
N1 C1 C10 124.08(11) . . ?
C1 C2 C3 120.22(11) . . ?
C1 C2 C15 123.39(11) . . ?
C3 C2 C15 116.28(11) . . ?
C4 C3 C2 120.99(12) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 120.79(12) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C4 C5 C6 118.87(12) . . ?
C4 C5 C10 120.05(11) . . ?
C6 C5 C10 121.09(12) . . ?
C7 C6 C5 120.87(12) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C6 C7 C8 118.87(12) . . ?
C6 C7 H7A 120.6 . . ?
C8 C7 H7A 120.6 . . ?
C9 C8 C7 122.63(13) . . ?
C9 C8 H8A 118.7 . . ?
C7 C8 H8A 118.7 . . ?
C8 C9 N2 118.72(12) . . ?
C8 C9 C10 120.06(12) . . ?
N2 C9 C10 121.08(11) . . ?
C5 C10 C9 115.63(11) . . ?
C5 C10 C1 117.28(11) . . ?
C9 C10 C1 127.10(11) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2' C1' N1' 119.76(11) . . ?
C2' C1' C10' 119.46(11) . . ?
N1' C1' C10' 120.14(11) . . ?
C1' C2' C3' 119.10(12) . . ?
C1' C2' C15 122.02(11) . . ?
C3' C2' C15 118.87(11) . . ?
C4' C3' C2' 121.59(12) . . ?
C4' C3' H3'A 119.2 . . ?
C2' C3' H3'A 119.2 . . ?
C3' C4' C5' 120.82(12) . . ?
C3' C4' H4'A 119.6 . . ?
C5' C4' H4'A 119.6 . . ?
C4' C5' C6' 120.33(12) . . ?
C4' C5' C10' 119.12(12) . . ?
C6' C5' C10' 120.55(12) . . ?
C7' C6' C5' 120.40(13) . . ?
C7' C6' H6'A 119.8 . . ?
C5' C6' H6'A 119.8 . . ?
C6' C7' C8' 120.02(13) . . ?
C6' C7' H7'A 120.0 . . ?
C8' C7' H7'A 120.0 . . ?
C9' C8' C7' 121.67(13) . . ?
C9' C8' H8'A 119.2 . . ?
C7' C8' H8'A 119.2 . . ?
C8' C9' N2' 120.95(12) . . ?
C8' C9' C10' 119.41(12) . . ?
N2' C9' C10' 119.54(11) . . ?
C5' C10' C1' 118.44(11) . . ?
C5' C10' C9' 116.52(11) . . ?
C1' C10' C9' 125.03(11) . . ?
N1' C11' H11D 109.5 . . ?
N1' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
N1' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
N1' C12' H12D 109.5 . . ?
N1' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
N1' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
N2' C13' H13D 109.5 . . ?
N2' C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
N2' C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
N2' C14' H14D 109.5 . . ?
N2' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
N2' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
O1 C15 C2' 103.73(9) . . ?
O1 C15 C16 109.01(9) . . ?
C2' C15 C16 111.76(10) . . ?
O1 C15 C2 112.93(10) . . ?
C2' C15 C2 112.83(10) . . ?
C16 C15 C2 106.63(9) . . ?
C17 C16 C21 118.08(12) . . ?
C17 C16 C15 119.43(11) . . ?
C21 C16 C15 122.48(11) . . ?
C18 C17 C16 120.86(12) . . ?
C18 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?
C19 C18 C17 120.40(12) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C18 C19 C20 119.33(12) . . ?
C18 C19 H19A 120.3 . . ?
C20 C19 H19A 120.3 . . ?
C21 C20 C19 120.30(13) . . ?
C21 C20 H20A 119.9 . . ?
C19 C20 H20A 119.9 . . ?
C20 C21 C16 121.04(12) . . ?
C20 C21 H21A 119.5 . . ?
C16 C21 H21A 119.5 . . ?
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
O1 C15 1.4219(14) . ?
O1 H1O 0.8500 . ?
N1 C1 1.4422(15) . ?
N1 C11 1.4587(17) . ?
N1 C12 1.4621(17) . ?
N2 C9 1.4376(16) . ?
N2 C13 1.4625(18) . ?
N2 C14 1.4646(18) . ?
N1' C1' 1.4144(16) . ?
N1' C11' 1.4427(17) . ?
N1' C12' 1.4475(16) . ?
N2' C9' 1.4227(17) . ?
N2' C14' 1.4544(17) . ?
N2' C13' 1.4574(17) . ?
C1 C2 1.3927(17) . ?
C1 C10 1.4591(17) . ?
C2 C3 1.4134(17) . ?
C2 C15 1.5565(16) . ?
C3 C4 1.3615(17) . ?
C3 H3A 0.9300 . ?
C4 C5 1.4103(18) . ?
C4 H4A 0.9300 . ?
C5 C6 1.4215(17) . ?
C5 C10 1.4367(17) . ?
C6 C7 1.358(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.4007(19) . ?
C7 H7A 0.9300 . ?
C8 C9 1.3822(18) . ?
C8 H8A 0.9300 . ?
C9 C10 1.4423(18) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C1' C2' 1.4045(17) . ?
C1' C10' 1.4456(17) . ?
C2' C3' 1.4132(17) . ?
C2' C15 1.5453(17) . ?
C3' C4' 1.3668(18) . ?
C3' H3'A 0.9300 . ?
C4' C5' 1.4058(18) . ?
C4' H4'A 0.9300 . ?
C5' C6' 1.4196(18) . ?
C5' C10' 1.4294(17) . ?
C6' C7' 1.355(2) . ?
C6' H6'A 0.9300 . ?
C7' C8' 1.408(2) . ?
C7' H7'A 0.9300 . ?
C8' C9' 1.3791(18) . ?
C8' H8'A 0.9300 . ?
C9' C10' 1.4483(17) . ?
C11' H11D 0.9600 . ?
C11' H11E 0.9600 . ?
C11' H11F 0.9600 . ?
C12' H12D 0.9600 . ?
C12' H12E 0.9600 . ?
C12' H12F 0.9600 . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 0.9600 . ?
C14' H14D 0.9600 . ?
C14' H14E 0.9600 . ?
C14' H14F 0.9600 . ?
C15 C16 1.5489(17) . ?
C16 C17 1.3944(17) . ?
C16 C21 1.3981(17) . ?
C17 C18 1.3908(18) . ?
C17 H17A 0.9300 . ?
C18 C19 1.386(2) . ?
C18 H18A 0.9300 . ?
C19 C20 1.3875(19) . ?
C19 H19A 0.9300 . ?
C20 C21 1.3865(18) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
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
C11 N1 C1 C2 121.06(12) . . . . ?
C12 N1 C1 C2 -94.99(14) . . . . ?
C11 N1 C1 C10 -54.61(16) . . . . ?
C12 N1 C1 C10 89.34(15) . . . . ?
N1 C1 C2 C3 -179.13(11) . . . . ?
C10 C1 C2 C3 -3.26(17) . . . . ?
N1 C1 C2 C15 4.71(17) . . . . ?
C10 C1 C2 C15 -179.42(11) . . . . ?
C1 C2 C3 C4 7.98(18) . . . . ?
C15 C2 C3 C4 -175.59(11) . . . . ?
C2 C3 C4 C5 -3.61(19) . . . . ?
C3 C4 C5 C6 174.68(12) . . . . ?
C3 C4 C5 C10 -5.36(18) . . . . ?
C4 C5 C6 C7 177.37(12) . . . . ?
C10 C5 C6 C7 -2.58(19) . . . . ?
C5 C6 C7 C8 -4.6(2) . . . . ?
C6 C7 C8 C9 4.6(2) . . . . ?
C7 C8 C9 N2 -173.13(12) . . . . ?
C7 C8 C9 C10 2.7(2) . . . . ?
C13 N2 C9 C8 84.36(15) . . . . ?
C14 N2 C9 C8 -40.80(17) . . . . ?
C13 N2 C9 C10 -91.40(14) . . . . ?
C14 N2 C9 C10 143.43(12) . . . . ?
C4 C5 C10 C9 -170.57(11) . . . . ?
C6 C5 C10 C9 9.38(17) . . . . ?
C4 C5 C10 C1 9.64(17) . . . . ?
C6 C5 C10 C1 -170.41(11) . . . . ?
C8 C9 C10 C5 -9.35(17) . . . . ?
N2 C9 C10 C5 166.36(11) . . . . ?
C8 C9 C10 C1 170.43(12) . . . . ?
N2 C9 C10 C1 -13.87(19) . . . . ?
C2 C1 C10 C5 -5.33(17) . . . . ?
N1 C1 C10 C5 170.18(11) . . . . ?
C2 C1 C10 C9 174.90(12) . . . . ?
N1 C1 C10 C9 -9.59(19) . . . . ?
C11' N1' C1' C2' 78.08(16) . . . . ?
C12' N1' C1' C2' -122.89(13) . . . . ?
C11' N1' C1' C10' -111.11(14) . . . . ?
C12' N1' C1' C10' 47.92(16) . . . . ?
N1' C1' C2' C3' 167.85(11) . . . . ?
C10' C1' C2' C3' -3.03(17) . . . . ?
N1' C1' C2' C15 -12.66(17) . . . . ?
C10' C1' C2' C15 176.47(10) . . . . ?
C1' C2' C3' C4' -6.18(18) . . . . ?
C15 C2' C3' C4' 174.31(11) . . . . ?
C2' C3' C4' C5' 5.85(19) . . . . ?
C3' C4' C5' C6' -176.03(12) . . . . ?
C3' C4' C5' C10' 3.77(18) . . . . ?
C4' C5' C6' C7' -177.25(12) . . . . ?
C10' C5' C6' C7' 2.95(19) . . . . ?
C5' C6' C7' C8' 5.0(2) . . . . ?
C6' C7' C8' C9' -3.3(2) . . . . ?
C7' C8' C9' N2' 170.12(12) . . . . ?
C7' C8' C9' C10' -6.18(19) . . . . ?
C14' N2' C9' C8' 19.71(17) . . . . ?
C13' N2' C9' C8' -108.62(14) . . . . ?
C14' N2' C9' C10' -163.99(11) . . . . ?
C13' N2' C9' C10' 67.68(15) . . . . ?
C4' C5' C10' C1' -12.63(17) . . . . ?
C6' C5' C10' C1' 167.18(11) . . . . ?
C4' C5' C10' C9' 168.26(11) . . . . ?
C6' C5' C10' C9' -11.93(17) . . . . ?
C2' C1' C10' C5' 12.25(17) . . . . ?
N1' C1' C10' C5' -158.58(11) . . . . ?
C2' C1' C10' C9' -168.72(11) . . . . ?
N1' C1' C10' C9' 20.44(18) . . . . ?
C8' C9' C10' C5' 13.42(17) . . . . ?
N2' C9' C10' C5' -162.94(11) . . . . ?
C8' C9' C10' C1' -165.62(12) . . . . ?
N2' C9' C10' C1' 18.02(18) . . . . ?
C1' C2' C15 O1 -67.51(13) . . . . ?
C3' C2' C15 O1 111.99(11) . . . . ?
C1' C2' C15 C16 175.20(11) . . . . ?
C3' C2' C15 C16 -5.31(15) . . . . ?
C1' C2' C15 C2 55.04(15) . . . . ?
C3' C2' C15 C2 -125.47(11) . . . . ?
C1 C2 C15 O1 -38.07(16) . . . . ?
C3 C2 C15 O1 145.63(11) . . . . ?
C1 C2 C15 C2' -155.30(11) . . . . ?
C3 C2 C15 C2' 28.40(14) . . . . ?
C1 C2 C15 C16 81.64(13) . . . . ?
C3 C2 C15 C16 -94.67(12) . . . . ?
O1 C15 C16 C17 -16.17(15) . . . . ?
C2' C15 C16 C17 97.90(13) . . . . ?
C2 C15 C16 C17 -138.37(12) . . . . ?
O1 C15 C16 C21 162.52(11) . . . . ?
C2' C15 C16 C21 -83.42(14) . . . . ?
C2 C15 C16 C21 40.31(15) . . . . ?
C21 C16 C17 C18 0.05(19) . . . . ?
C15 C16 C17 C18 178.79(12) . . . . ?
C16 C17 C18 C19 0.0(2) . . . . ?
C17 C18 C19 C20 -0.1(2) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C19 C20 C21 C16 -0.1(2) . . . . ?
C17 C16 C21 C20 0.02(19) . . . . ?
C15 C16 C21 C20 -178.68(12) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659237
