#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/01/7150134.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_7150134
loop_
_publ_author_name
'Kanamori, Daisuke'
'Furukawa, Atsushi'
'Okamura, Taka-aki'
'Yamamoto, Hitoshi'
'Ueyama, Norikazu'
_publ_section_title
;
 Contribution of the intramolecular hydrogen bond to the shift of the
 pKa value and the oxidation potential of phenols and phenolate anions.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1453
_journal_page_last               1459
_journal_paper_doi               10.1039/b419361j
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C16 H24 N2 O3'
_chemical_formula_sum            'C16 H24 N2 O3'
_chemical_formula_weight         292.37
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.46(2)
_cell_angle_beta                 109.07(3)
_cell_angle_gamma                90.81(3)
_cell_formula_units_Z            4
_cell_length_a                   12.233(4)
_cell_length_b                   13.207(4)
_cell_length_c                   11.841(4)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    298
_cell_measurement_theta_max      12.3
_cell_measurement_theta_min      11.0
_cell_volume                     1731.8(11)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.911
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_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  0.0628
_diffrn_reflns_av_sigmaI/netI    0.0940
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5813
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        0.01
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1885
_refine_ls_R_factor_gt           0.0605
_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)+(0.1190P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.2267
_reflns_number_gt                2337
_reflns_number_total             5561
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b419361j-ccdc.txt
_cod_data_source_block           2'OH
_cod_original_cell_volume        1732.0(10)
_cod_original_sg_symbol_Hall     '-P 1         '
_cod_original_sg_symbol_H-M      'P -1         '
_cod_database_code               7150134
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 0.9768(3) 0.4813(2) 0.3498(3) 0.0746(9) Uani 1 1 d . . .
O2 O 0.6137(3) 0.7356(2) 0.0431(3) 0.0777(9) Uani 1 1 d . . .
O3 O 0.5020(3) 0.1646(2) 0.3533(3) 0.0849(10) Uani 1 1 d . . .
O4 O 0.0816(3) -0.2051(2) 0.0587(3) 0.0792(9) Uani 1 1 d . . .
O11 O 0.8268(2) 0.6005(2) 0.3004(2) 0.0603(7) Uani 1 1 d . . .
H11 H 0.8659 0.5631 0.3397 0.072 Uiso 1 1 calc R . .
O31 O 0.3375(3) 0.0337(2) 0.3131(2) 0.0664(8) Uani 1 1 d . . .
H31 H 0.3913 0.0810 0.3519 0.080 Uiso 1 1 calc R . .
N1 N 1.0075(3) 0.3513(2) 0.2008(3) 0.0590(9) Uani 1 1 d . . .
H1 H 0.9875 0.3210 0.1220 0.071 Uiso 1 1 calc R . .
N2 N 0.6430(3) 0.7043(3) 0.2262(3) 0.0670(10) Uani 1 1 d . . .
H2 H 0.6829 0.6709 0.2762 0.080 Uiso 1 1 calc R . .
N3 N 0.5067(3) 0.2364(2) 0.2034(3) 0.0629(9) Uani 1 1 d . . .
H3 H 0.4796 0.2307 0.1249 0.075 Uiso 1 1 calc R . .
N4 N 0.1548(3) -0.1046(3) 0.2576(3) 0.0698(10) Uani 1 1 d . . .
H4 H 0.2054 -0.0526 0.3082 0.084 Uiso 1 1 calc R . .
C1 C 0.9588(3) 0.4378(3) 0.2382(4) 0.0569(10) Uani 1 1 d . . .
C2 C 0.6620(3) 0.6892(3) 0.1199(4) 0.0555(10) Uani 1 1 d . . .
C3 C 0.4685(4) 0.1614(3) 0.2408(4) 0.0587(10) Uani 1 1 d . . .
C4 C 0.1507(4) -0.1321(3) 0.1404(4) 0.0610(11) Uani 1 1 d . . .
C11 C 0.8170(3) 0.5640(3) 0.1801(3) 0.0470(9) Uani 1 1 d . . .
C12 C 0.8824(3) 0.4835(3) 0.1415(3) 0.0489(9) Uani 1 1 d . . .
C13 C 0.8753(4) 0.4525(3) 0.0189(4) 0.0650(11) Uani 1 1 d . . .
H13 H 0.9184 0.3992 -0.0066 0.078 Uiso 1 1 calc R . .
C14 C 0.8059(4) 0.4980(3) -0.0680(4) 0.0690(12) Uani 1 1 d . . .
H14 H 0.8028 0.4769 -0.1505 0.083 Uiso 1 1 calc R . .
C15 C 0.7410(4) 0.5762(3) -0.0277(4) 0.0649(12) Uani 1 1 d . . .
H15 H 0.6945 0.6078 -0.0852 0.078 Uiso 1 1 calc R . .
C16 C 0.7423(3) 0.6091(3) 0.0929(3) 0.0487(9) Uani 1 1 d . . .
C17 C 1.0946(4) 0.3040(3) 0.2871(4) 0.0680(12) Uani 1 1 d . . .
C18 C 1.0369(4) 0.2598(4) 0.3620(5) 0.0879(15) Uani 1 1 d . . .
H18A H 0.9727 0.2083 0.3063 0.106 Uiso 1 1 calc R . .
H18B H 1.0090 0.3161 0.4119 0.106 Uiso 1 1 calc R . .
H18C H 1.0923 0.2270 0.4154 0.106 Uiso 1 1 calc R . .
C19 C 1.1964(4) 0.3849(4) 0.3729(5) 0.0964(17) Uani 1 1 d . . .
H19A H 1.1699 0.4409 0.4247 0.116 Uiso 1 1 calc R . .
H19B H 1.2307 0.4135 0.3241 0.116 Uiso 1 1 calc R . .
H19C H 1.2534 0.3519 0.4245 0.116 Uiso 1 1 calc R . .
C20 C 1.1345(5) 0.2144(4) 0.2040(5) 0.112(2) Uani 1 1 d . . .
H20A H 1.0690 0.1636 0.1503 0.135 Uiso 1 1 calc R . .
H20B H 1.1914 0.1808 0.2550 0.135 Uiso 1 1 calc R . .
H20C H 1.1683 0.2422 0.1544 0.135 Uiso 1 1 calc R . .
C21 C 0.5613(4) 0.7719(4) 0.2693(4) 0.0771(13) Uani 1 1 d . . .
C22 C 0.4415(5) 0.7437(5) 0.1779(6) 0.123(2) Uani 1 1 d . . .
H22A H 0.4396 0.7561 0.1010 0.147 Uiso 1 1 calc R . .
H22B H 0.3895 0.7863 0.2103 0.147 Uiso 1 1 calc R . .
H22C H 0.4176 0.6704 0.1630 0.147 Uiso 1 1 calc R . .
C23 C 0.5997(6) 0.8859(4) 0.2891(6) 0.132(2) Uani 1 1 d . . .
H23A H 0.6769 0.9048 0.3493 0.159 Uiso 1 1 calc R . .
H23B H 0.5473 0.9298 0.3190 0.159 Uiso 1 1 calc R . .
H23C H 0.5993 0.8959 0.2116 0.159 Uiso 1 1 calc R . .
C24 C 0.5643(6) 0.7537(6) 0.3894(6) 0.172(4) Uani 1 1 d . . .
H24A H 0.6421 0.7720 0.4485 0.207 Uiso 1 1 calc R . .
H24B H 0.5401 0.6806 0.3754 0.207 Uiso 1 1 calc R . .
H24C H 0.5127 0.7969 0.4217 0.207 Uiso 1 1 calc R . .
C31 C 0.3175(3) 0.0132(3) 0.1895(3) 0.0499(9) Uani 1 1 d . . .
C32 C 0.3824(3) 0.0735(3) 0.1474(4) 0.0534(10) Uani 1 1 d . . .
C33 C 0.3641(4) 0.0469(3) 0.0215(4) 0.0704(12) Uani 1 1 d . . .
H33 H 0.4080 0.0851 -0.0074 0.085 Uiso 1 1 calc R . .
C34 C 0.2827(5) -0.0344(3) -0.0627(4) 0.0826(15) Uani 1 1 d . . .
H34 H 0.2716 -0.0514 -0.1474 0.099 Uiso 1 1 calc R . .
C35 C 0.2176(4) -0.0904(3) -0.0184(4) 0.0730(13) Uani 1 1 d . . .
H35 H 0.1631 -0.1459 -0.0750 0.088 Uiso 1 1 calc R . .
C36 C 0.2303(3) -0.0672(3) 0.1059(4) 0.0548(10) Uani 1 1 d . . .
C37 C 0.5919(4) 0.3295(3) 0.2847(4) 0.0679(12) Uani 1 1 d . . .
C38 C 0.5415(5) 0.3981(4) 0.3730(5) 0.112(2) Uani 1 1 d . . .
H38A H 0.4703 0.4200 0.3267 0.134 Uiso 1 1 calc R . .
H38B H 0.5958 0.4592 0.4242 0.134 Uiso 1 1 calc R . .
H38C H 0.5258 0.3591 0.4249 0.134 Uiso 1 1 calc R . .
C39 C 0.7042(5) 0.2931(5) 0.3521(6) 0.125(2) Uani 1 1 d . . .
H39A H 0.7346 0.2504 0.2924 0.150 Uiso 1 1 calc R . .
H39B H 0.6903 0.2522 0.4030 0.150 Uiso 1 1 calc R . .
H39C H 0.7595 0.3534 0.4039 0.150 Uiso 1 1 calc R . .
C40 C 0.6125(6) 0.3886(5) 0.1996(5) 0.137(3) Uani 1 1 d . . .
H40A H 0.6464 0.3446 0.1442 0.165 Uiso 1 1 calc R . .
H40B H 0.6644 0.4517 0.2485 0.165 Uiso 1 1 calc R . .
H40C H 0.5397 0.4070 0.1519 0.165 Uiso 1 1 calc R . .
C41 C 0.0820(4) -0.1533(4) 0.3108(5) 0.0807(14) Uani 1 1 d . . .
C42 C -0.0441(5) -0.1422(6) 0.2513(6) 0.129(2) Uani 1 1 d . . .
H42A H -0.0544 -0.0687 0.2624 0.155 Uiso 1 1 calc R . .
H42B H -0.0894 -0.1720 0.2895 0.155 Uiso 1 1 calc R . .
H42C H -0.0692 -0.1787 0.1638 0.155 Uiso 1 1 calc R . .
C43 C 0.1014(6) -0.2685(4) 0.2978(5) 0.1053(18) Uani 1 1 d . . .
H43A H 0.1824 -0.2735 0.3374 0.126 Uiso 1 1 calc R . .
H43B H 0.0776 -0.3070 0.2110 0.126 Uiso 1 1 calc R . .
H43C H 0.0564 -0.2979 0.3368 0.126 Uiso 1 1 calc R . .
C44 C 0.1249(5) -0.0922(4) 0.4498(5) 0.117(2) Uani 1 1 d . . .
H44A H 0.2054 -0.1006 0.4870 0.141 Uiso 1 1 calc R . .
H44B H 0.0797 -0.1191 0.4904 0.141 Uiso 1 1 calc R . .
H44C H 0.1164 -0.0186 0.4590 0.141 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
C11 O11 H11 109.5 . . ?
C31 O31 H31 109.5 . . ?
C1 N1 C17 124.0(3) . . ?
C1 N1 H1 118.0 . . ?
C17 N1 H1 118.0 . . ?
C2 N2 C21 127.5(3) . . ?
C2 N2 H2 116.2 . . ?
C21 N2 H2 116.2 . . ?
C3 N3 C37 125.8(4) . . ?
C3 N3 H3 117.1 . . ?
C37 N3 H3 117.1 . . ?
C4 N4 C41 127.0(4) . . ?
C4 N4 H4 116.5 . . ?
C41 N4 H4 116.5 . . ?
O1 C1 N1 121.7(4) . . ?
O1 C1 C12 119.8(3) . . ?
N1 C1 C12 118.5(4) . . ?
O2 C2 N2 122.3(4) . . ?
O2 C2 C16 120.3(4) . . ?
N2 C2 C16 117.4(3) . . ?
O3 C3 N3 121.1(4) . . ?
O3 C3 C32 119.6(4) . . ?
N3 C3 C32 119.2(4) . . ?
O4 C4 N4 122.7(4) . . ?
O4 C4 C36 119.6(4) . . ?
N4 C4 C36 117.6(4) . . ?
O11 C11 C16 119.0(3) . . ?
O11 C11 C12 120.7(3) . . ?
C16 C11 C12 120.3(3) . . ?
C13 C12 C11 119.0(3) . . ?
C13 C12 C1 123.2(3) . . ?
C11 C12 C1 117.7(3) . . ?
C12 C13 C14 122.0(4) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C13 C14 C15 117.8(4) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C16 C15 C14 123.0(4) . . ?
C16 C15 H15 118.5 . . ?
C14 C15 H15 118.5 . . ?
C15 C16 C11 117.8(3) . . ?
C15 C16 C2 116.7(3) . . ?
C11 C16 C2 125.5(3) . . ?
N1 C17 C19 110.8(3) . . ?
N1 C17 C18 109.6(3) . . ?
C19 C17 C18 110.5(4) . . ?
N1 C17 C20 105.7(4) . . ?
C19 C17 C20 110.4(4) . . ?
C18 C17 C20 109.7(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C22 111.3(4) . . ?
N2 C21 C24 106.5(4) . . ?
C22 C21 C24 109.7(5) . . ?
N2 C21 C23 109.7(4) . . ?
C22 C21 C23 109.2(5) . . ?
C24 C21 C23 110.5(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O31 C31 C36 118.8(3) . . ?
O31 C31 C32 119.8(3) . . ?
C36 C31 C32 121.4(4) . . ?
C33 C32 C31 118.2(4) . . ?
C33 C32 C3 123.4(4) . . ?
C31 C32 C3 118.4(3) . . ?
C34 C33 C32 121.9(4) . . ?
C34 C33 H33 119.0 . . ?
C32 C33 H33 119.0 . . ?
C33 C34 C35 118.4(4) . . ?
C33 C34 H34 120.8 . . ?
C35 C34 H34 120.8 . . ?
C36 C35 C34 122.7(4) . . ?
C36 C35 H35 118.6 . . ?
C34 C35 H35 118.6 . . ?
C35 C36 C31 117.2(4) . . ?
C35 C36 C4 117.1(4) . . ?
C31 C36 C4 125.7(4) . . ?
N3 C37 C38 109.5(4) . . ?
N3 C37 C39 109.6(4) . . ?
C38 C37 C39 111.9(4) . . ?
N3 C37 C40 106.3(4) . . ?
C38 C37 C40 109.8(5) . . ?
C39 C37 C40 109.5(5) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
N4 C41 C42 111.0(5) . . ?
N4 C41 C43 110.7(4) . . ?
C42 C41 C43 111.0(5) . . ?
N4 C41 C44 105.0(4) . . ?
C42 C41 C44 110.3(5) . . ?
C43 C41 C44 108.8(5) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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
O1 C1 1.235(4) . ?
O2 C2 1.228(4) . ?
O3 C3 1.247(4) . ?
O4 C4 1.234(4) . ?
O11 C11 1.341(4) . ?
O11 H11 0.8200 . ?
O31 C31 1.352(4) . ?
O31 H31 0.8200 . ?
N1 C1 1.334(5) . ?
N1 C17 1.489(5) . ?
N1 H1 0.8600 . ?
N2 C2 1.317(5) . ?
N2 C21 1.474(5) . ?
N2 H2 0.8600 . ?
N3 C3 1.323(5) . ?
N3 C37 1.484(5) . ?
N3 H3 0.8600 . ?
N4 C4 1.321(5) . ?
N4 C41 1.473(5) . ?
N4 H4 0.8600 . ?
C1 C12 1.494(5) . ?
C2 C16 1.497(5) . ?
C3 C32 1.483(5) . ?
C4 C36 1.508(5) . ?
C11 C16 1.408(5) . ?
C11 C12 1.408(5) . ?
C12 C13 1.373(5) . ?
C13 C14 1.383(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(5) . ?
C15 H15 0.9300 . ?
C17 C19 1.512(6) . ?
C17 C18 1.516(6) . ?
C17 C20 1.522(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.480(7) . ?
C21 C24 1.494(7) . ?
C21 C23 1.504(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C31 C36 1.401(5) . ?
C31 C32 1.402(5) . ?
C32 C33 1.377(5) . ?
C33 C34 1.375(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.385(6) . ?
C34 H34 0.9300 . ?
C35 C36 1.376(5) . ?
C35 H35 0.9300 . ?
C37 C38 1.491(6) . ?
C37 C39 1.504(7) . ?
C37 C40 1.505(6) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C42 1.500(7) . ?
C41 C43 1.518(7) . ?
C41 C44 1.533(7) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
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
C17 N1 C1 O1 -5.4(6) . . . . ?
C17 N1 C1 C12 173.6(3) . . . . ?
C21 N2 C2 O2 2.9(7) . . . . ?
C21 N2 C2 C16 -174.8(4) . . . . ?
C37 N3 C3 O3 1.1(6) . . . . ?
C37 N3 C3 C32 179.7(4) . . . . ?
C41 N4 C4 O4 0.3(7) . . . . ?
C41 N4 C4 C36 177.2(4) . . . . ?
O11 C11 C12 C13 -176.2(3) . . . . ?
C16 C11 C12 C13 2.3(5) . . . . ?
O11 C11 C12 C1 2.3(5) . . . . ?
C16 C11 C12 C1 -179.2(3) . . . . ?
O1 C1 C12 C13 167.4(4) . . . . ?
N1 C1 C12 C13 -11.6(6) . . . . ?
O1 C1 C12 C11 -11.0(5) . . . . ?
N1 C1 C12 C11 170.0(3) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C1 C12 C13 C14 -178.3(4) . . . . ?
C12 C13 C14 C15 -1.0(6) . . . . ?
C13 C14 C15 C16 -0.5(7) . . . . ?
C14 C15 C16 C11 2.8(6) . . . . ?
C14 C15 C16 C2 -176.2(4) . . . . ?
O11 C11 C16 C15 174.9(3) . . . . ?
C12 C11 C16 C15 -3.7(5) . . . . ?
O11 C11 C16 C2 -6.2(5) . . . . ?
C12 C11 C16 C2 175.3(3) . . . . ?
O2 C2 C16 C15 -12.3(5) . . . . ?
N2 C2 C16 C15 165.5(4) . . . . ?
O2 C2 C16 C11 168.8(4) . . . . ?
N2 C2 C16 C11 -13.5(5) . . . . ?
C1 N1 C17 C19 -54.8(5) . . . . ?
C1 N1 C17 C18 67.5(5) . . . . ?
C1 N1 C17 C20 -174.4(4) . . . . ?
C2 N2 C21 C22 55.3(6) . . . . ?
C2 N2 C21 C24 174.7(5) . . . . ?
C2 N2 C21 C23 -65.7(6) . . . . ?
O31 C31 C32 C33 176.6(3) . . . . ?
C36 C31 C32 C33 -4.4(6) . . . . ?
O31 C31 C32 C3 -2.4(5) . . . . ?
C36 C31 C32 C3 176.5(3) . . . . ?
O3 C3 C32 C33 -161.7(4) . . . . ?
N3 C3 C32 C33 19.7(6) . . . . ?
O3 C3 C32 C31 17.3(6) . . . . ?
N3 C3 C32 C31 -161.3(4) . . . . ?
C31 C32 C33 C34 1.7(6) . . . . ?
C3 C32 C33 C34 -179.3(4) . . . . ?
C32 C33 C34 C35 0.2(7) . . . . ?
C33 C34 C35 C36 0.7(7) . . . . ?
C34 C35 C36 C31 -3.3(6) . . . . ?
C34 C35 C36 C4 177.8(4) . . . . ?
O31 C31 C36 C35 -175.9(3) . . . . ?
C32 C31 C36 C35 5.2(5) . . . . ?
O31 C31 C36 C4 2.9(6) . . . . ?
C32 C31 C36 C4 -176.0(3) . . . . ?
O4 C4 C36 C35 2.9(6) . . . . ?
N4 C4 C36 C35 -174.1(4) . . . . ?
O4 C4 C36 C31 -175.8(4) . . . . ?
N4 C4 C36 C31 7.2(6) . . . . ?
C3 N3 C37 C38 -64.3(6) . . . . ?
C3 N3 C37 C39 58.8(6) . . . . ?
C3 N3 C37 C40 177.1(4) . . . . ?
C4 N4 C41 C42 -61.9(6) . . . . ?
C4 N4 C41 C43 61.8(6) . . . . ?
C4 N4 C41 C44 179.0(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9521803
