#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/01/7150131.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_7150131
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         'C19 H31 N O2'
_chemical_formula_sum            'C19 H31 N O2'
_chemical_formula_weight         305.46
_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                101.634(3)
_cell_angle_beta                 99.209(4)
_cell_angle_gamma                90.717(4)
_cell_formula_units_Z            4
_cell_length_a                   10.6747(6)
_cell_length_b                   12.0073(3)
_cell_length_c                   15.3190(11)
_cell_measurement_reflns_used    8123
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      1.4
_cell_volume                     1896.34(18)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_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  0.0642
_diffrn_reflns_av_sigmaI/netI    0.0868
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16337
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.070
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         8344
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1544
_refine_ls_R_factor_gt           0.0775
_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)+(0.1368P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2110
_refine_ls_wR_factor_ref         0.2478
_reflns_number_gt                4113
_reflns_number_total             8344
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b419361j-ccdc.txt
_cod_data_source_block           1OH
_cod_original_sg_symbol_Hall     '-P 1         '
_cod_original_sg_symbol_H-M      'P -1         '
_cod_database_code               7150131
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 0.08455(18) 0.29019(19) 0.09565(14) 0.0582(6) Uani 1 1 d . . .
O3 O 0.58302(18) 0.2717(2) 0.09485(15) 0.0598(6) Uani 1 1 d . . .
O11 O 0.03837(17) 0.46164(18) 0.20661(13) 0.0457(5) Uani 1 1 d . . .
H11 H 0.034(3) 0.393(3) 0.161(2) 0.055 Uiso 1 1 d . . .
O31 O 0.52866(18) 0.14395(19) 0.19609(14) 0.0489(5) Uani 1 1 d . . .
H31 H 0.523(3) 0.180(3) 0.149(2) 0.059 Uiso 1 1 d . . .
N1 N 0.2798(2) 0.25429(18) 0.06715(14) 0.0387(6) Uani 1 1 d . . .
H1 H 0.3613 0.2729 0.0845 0.046 Uiso 1 1 calc R . .
N3 N 0.7787(2) 0.28537(19) 0.06375(15) 0.0413(6) Uani 1 1 d . . .
H3 H 0.8588 0.2698 0.0781 0.050 Uiso 1 1 calc R . .
C1 C 0.2013(2) 0.3132(2) 0.11510(17) 0.0357(6) Uani 1 1 d . . .
C3 C 0.6984(2) 0.2520(2) 0.11145(17) 0.0354(6) Uani 1 1 d . . .
C11 C 0.1651(2) 0.4780(2) 0.23518(17) 0.0366(6) Uani 1 1 d . . .
C12 C 0.2515(2) 0.4088(2) 0.19267(16) 0.0338(6) Uani 1 1 d . . .
C13 C 0.3814(2) 0.4292(2) 0.22553(18) 0.0380(6) Uani 1 1 d . . .
H13 H 0.4402 0.3819 0.1973 0.046 Uiso 1 1 calc R . .
C14 C 0.4267(3) 0.5170(2) 0.29843(18) 0.0401(7) Uani 1 1 d . . .
C15 C 0.3374(3) 0.5833(2) 0.33743(18) 0.0426(7) Uani 1 1 d . . .
H15 H 0.3675 0.6438 0.3871 0.051 Uiso 1 1 calc R . .
C16 C 0.2076(3) 0.5682(2) 0.30950(18) 0.0389(6) Uani 1 1 d . . .
C17 C 0.2452(3) 0.1592(2) -0.01349(19) 0.0432(7) Uani 1 1 d . . .
C18 C 0.1955(10) 0.2149(8) -0.0922(4) 0.071(2) Uani 0.712(18) 1 d PU . .
H18A H 0.1185 0.2548 -0.0803 0.086 Uiso 0.712(18) 1 calc PR . .
H18B H 0.1755 0.1563 -0.1477 0.086 Uiso 0.712(18) 1 calc PR . .
H18C H 0.2603 0.2694 -0.0993 0.086 Uiso 0.712(18) 1 calc PR . .
C19 C 0.1481(9) 0.0744(7) -0.0009(6) 0.069(2) Uani 0.712(18) 1 d PU . .
H19A H 0.0692 0.1124 0.0084 0.083 Uiso 0.712(18) 1 calc PR . .
H19B H 0.1806 0.0424 0.0519 0.083 Uiso 0.712(18) 1 calc PR . .
H19C H 0.1314 0.0131 -0.0548 0.083 Uiso 0.712(18) 1 calc PR . .
C20 C 0.3675(8) 0.0987(7) -0.0283(6) 0.062(2) Uani 0.712(18) 1 d PU . .
H20A H 0.4318 0.1537 -0.0357 0.075 Uiso 0.712(18) 1 calc PR . .
H20B H 0.3503 0.0383 -0.0828 0.075 Uiso 0.712(18) 1 calc PR . .
H20C H 0.3990 0.0655 0.0240 0.075 Uiso 0.712(18) 1 calc PR . .
C21 C 0.5706(3) 0.5371(3) 0.3334(2) 0.0490(8) Uani 1 1 d . . .
C22 C 0.6265(4) 0.4329(4) 0.3565(4) 0.1059(18) Uani 1 1 d . . .
H22A H 0.6067 0.3697 0.3042 0.127 Uiso 1 1 calc R . .
H22B H 0.5910 0.4145 0.4074 0.127 Uiso 1 1 calc R . .
H22C H 0.7189 0.4453 0.3734 0.127 Uiso 1 1 calc R . .
C23 C 0.6340(4) 0.5691(6) 0.2581(3) 0.117(2) Uani 1 1 d . . .
H23A H 0.5979 0.6385 0.2422 0.140 Uiso 1 1 calc R . .
H23B H 0.6189 0.5069 0.2047 0.140 Uiso 1 1 calc R . .
H23C H 0.7256 0.5824 0.2791 0.140 Uiso 1 1 calc R . .
C24 C 0.5995(4) 0.6349(4) 0.4158(3) 0.115(2) Uani 1 1 d . . .
H24A H 0.5654 0.7049 0.3999 0.138 Uiso 1 1 calc R . .
H24B H 0.6916 0.6456 0.4353 0.138 Uiso 1 1 calc R . .
H24C H 0.5600 0.6168 0.4650 0.138 Uiso 1 1 calc R . .
C25 C 0.1129(3) 0.6438(3) 0.3569(2) 0.0516(8) Uani 1 1 d . . .
C26 C 0.1810(4) 0.7368(3) 0.4328(2) 0.0725(11) Uani 1 1 d . . .
H26A H 0.1183 0.7833 0.4616 0.087 Uiso 1 1 calc R . .
H26B H 0.2351 0.7849 0.4081 0.087 Uiso 1 1 calc R . .
H26C H 0.2336 0.7020 0.4777 0.087 Uiso 1 1 calc R . .
C27 C 0.0305(3) 0.7020(3) 0.2896(2) 0.0659(10) Uani 1 1 d . . .
H27A H -0.0296 0.7496 0.3206 0.079 Uiso 1 1 calc R . .
H27B H -0.0165 0.6441 0.2405 0.079 Uiso 1 1 calc R . .
H27C H 0.0848 0.7497 0.2646 0.079 Uiso 1 1 calc R . .
C28 C 0.0300(4) 0.5709(3) 0.3981(2) 0.0696(10) Uani 1 1 d . . .
H28A H -0.0307 0.6188 0.4282 0.084 Uiso 1 1 calc R . .
H28B H 0.0838 0.5361 0.4423 0.084 Uiso 1 1 calc R . .
H28C H -0.0163 0.5111 0.3503 0.084 Uiso 1 1 calc R . .
C31 C 0.6552(2) 0.1393(2) 0.22476(17) 0.0348(6) Uani 1 1 d . . .
C32 C 0.7445(2) 0.1909(2) 0.18552(17) 0.0339(6) Uani 1 1 d . . .
C33 C 0.8735(2) 0.1845(2) 0.21771(17) 0.0359(6) Uani 1 1 d . . .
H33 H 0.9342 0.2190 0.1912 0.043 Uiso 1 1 calc R . .
C34 C 0.9155(2) 0.1293(2) 0.28722(17) 0.0368(6) Uani 1 1 d . . .
C35 C 0.8240(3) 0.0789(2) 0.32360(17) 0.0396(7) Uani 1 1 d . . .
H35 H 0.8518 0.0399 0.3708 0.048 Uiso 1 1 calc R . .
C36 C 0.6941(3) 0.0823(2) 0.29522(17) 0.0369(6) Uani 1 1 d . . .
C37 C 0.7483(3) 0.3466(3) -0.01181(18) 0.0436(7) Uani 1 1 d . . .
C38 C 0.6578(13) 0.4415(10) 0.0078(8) 0.081(3) Uani 0.564(16) 1 d PU . .
H38A H 0.5766 0.4092 0.0156 0.097 Uiso 0.564(16) 1 calc PR . .
H38B H 0.6439 0.4810 -0.0428 0.097 Uiso 0.564(16) 1 calc PR . .
H38C H 0.6945 0.4956 0.0632 0.097 Uiso 0.564(16) 1 calc PR . .
C39 C 0.6919(15) 0.2544(12) -0.0928(7) 0.092(4) Uani 0.564(16) 1 d PU . .
H39A H 0.6130 0.2218 -0.0813 0.111 Uiso 0.564(16) 1 calc PR . .
H39B H 0.7527 0.1944 -0.1026 0.111 Uiso 0.564(16) 1 calc PR . .
H39C H 0.6739 0.2876 -0.1467 0.111 Uiso 0.564(16) 1 calc PR . .
C40 C 0.8696(10) 0.4002(12) -0.0236(9) 0.075(3) Uani 0.564(16) 1 d PU . .
H40A H 0.9226 0.4268 0.0356 0.090 Uiso 0.564(16) 1 calc PR . .
H40B H 0.8510 0.4649 -0.0529 0.090 Uiso 0.564(16) 1 calc PR . .
H40C H 0.9148 0.3441 -0.0613 0.090 Uiso 0.564(16) 1 calc PR . .
C41 C 1.0580(3) 0.1244(3) 0.32225(19) 0.0449(7) Uani 1 1 d . . .
C42 C 1.1191(4) 0.0616(5) 0.2468(3) 0.122(2) Uani 1 1 d . . .
H42A H 1.0812 -0.0160 0.2269 0.146 Uiso 1 1 calc R . .
H42B H 1.2104 0.0585 0.2679 0.146 Uiso 1 1 calc R . .
H42C H 1.1059 0.1010 0.1962 0.146 Uiso 1 1 calc R . .
C43 C 1.1148(4) 0.2434(4) 0.3547(3) 0.0941(15) Uani 1 1 d . . .
H43A H 1.0745 0.2827 0.4047 0.113 Uiso 1 1 calc R . .
H43B H 1.1009 0.2844 0.3051 0.113 Uiso 1 1 calc R . .
H43C H 1.2063 0.2407 0.3755 0.113 Uiso 1 1 calc R . .
C44 C 1.0836(4) 0.0638(4) 0.4001(3) 0.0983(15) Uani 1 1 d . . .
H44A H 1.0435 0.1033 0.4502 0.118 Uiso 1 1 calc R . .
H44B H 1.1754 0.0633 0.4201 0.118 Uiso 1 1 calc R . .
H44C H 1.0484 -0.0148 0.3805 0.118 Uiso 1 1 calc R . .
C45 C 0.5954(3) 0.0271(3) 0.33848(19) 0.0486(8) Uani 1 1 d . . .
C46 C 0.6603(4) -0.0305(3) 0.4133(2) 0.0637(10) Uani 1 1 d . . .
H46A H 0.5956 -0.0651 0.4395 0.076 Uiso 1 1 calc R . .
H46B H 0.7125 0.0264 0.4604 0.076 Uiso 1 1 calc R . .
H46C H 0.7143 -0.0896 0.3877 0.076 Uiso 1 1 calc R . .
C47 C 0.5121(3) 0.1184(3) 0.3817(2) 0.0608(9) Uani 1 1 d . . .
H47A H 0.4493 0.0827 0.4089 0.073 Uiso 1 1 calc R . .
H47B H 0.4681 0.1562 0.3353 0.073 Uiso 1 1 calc R . .
H47C H 0.5655 0.1747 0.4285 0.073 Uiso 1 1 calc R . .
C48 C 0.5123(3) -0.0647(3) 0.2678(2) 0.0643(10) Uani 1 1 d . . .
H48A H 0.4502 -0.0986 0.2967 0.077 Uiso 1 1 calc R . .
H48B H 0.5661 -0.1239 0.2421 0.077 Uiso 1 1 calc R . .
H48C H 0.4676 -0.0301 0.2197 0.077 Uiso 1 1 calc R . .
C51 C 0.134(3) 0.1794(17) -0.0826(13) 0.079(6) Uani 0.288(18) 1 d PU . .
H51A H 0.0701 0.2207 -0.0515 0.094 Uiso 0.288(18) 1 calc PR . .
H51B H 0.0970 0.1061 -0.1184 0.094 Uiso 0.288(18) 1 calc PR . .
H51C H 0.1640 0.2244 -0.1226 0.094 Uiso 0.288(18) 1 calc PR . .
C52 C 0.210(3) 0.0523(18) 0.0235(15) 0.079(6) Uani 0.288(18) 1 d PU . .
H52A H 0.1269 0.0613 0.0429 0.095 Uiso 0.288(18) 1 calc PR . .
H52B H 0.2745 0.0449 0.0750 0.095 Uiso 0.288(18) 1 calc PR . .
H52C H 0.2066 -0.0161 -0.0243 0.095 Uiso 0.288(18) 1 calc PR . .
C53 C 0.355(2) 0.136(2) -0.0607(16) 0.076(6) Uani 0.288(18) 1 d PU . .
H53A H 0.3683 0.1977 -0.0922 0.091 Uiso 0.288(18) 1 calc PR . .
H53B H 0.3397 0.0637 -0.1045 0.091 Uiso 0.288(18) 1 calc PR . .
H53C H 0.4316 0.1318 -0.0165 0.091 Uiso 0.288(18) 1 calc PR . .
C54 C 0.7360(17) 0.4684(9) 0.0302(8) 0.076(4) Uani 0.436(16) 1 d PU . .
H54A H 0.6547 0.4773 0.0523 0.091 Uiso 0.436(16) 1 calc PR . .
H54B H 0.7392 0.5153 -0.0150 0.091 Uiso 0.436(16) 1 calc PR . .
H54C H 0.8058 0.4927 0.0808 0.091 Uiso 0.436(16) 1 calc PR . .
C55 C 0.6352(15) 0.2993(14) -0.0815(10) 0.080(5) Uani 0.436(16) 1 d PU . .
H55A H 0.5702 0.2705 -0.0522 0.096 Uiso 0.436(16) 1 calc PR . .
H55B H 0.6609 0.2371 -0.1262 0.096 Uiso 0.436(16) 1 calc PR . .
H55C H 0.6006 0.3595 -0.1118 0.096 Uiso 0.436(16) 1 calc PR . .
C56 C 0.8637(14) 0.3401(16) -0.0605(10) 0.075(4) Uani 0.436(16) 1 d PU . .
H56A H 0.8600 0.2668 -0.1030 0.090 Uiso 0.436(16) 1 calc PR . .
H56B H 0.9418 0.3472 -0.0160 0.090 Uiso 0.436(16) 1 calc PR . .
H56C H 0.8630 0.4020 -0.0935 0.090 Uiso 0.436(16) 1 calc PR . .
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'
O O 0.0106 0.0060 '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'
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 101.4(18) . . ?
C31 O31 H31 105(2) . . ?
C1 N1 C17 127.0(2) . . ?
C1 N1 H1 116.5 . . ?
C17 N1 H1 116.5 . . ?
C3 N3 C37 126.9(2) . . ?
C3 N3 H3 116.5 . . ?
C37 N3 H3 116.5 . . ?
O1 C1 N1 120.2(2) . . ?
O1 C1 C12 119.5(2) . . ?
N1 C1 C12 120.3(2) . . ?
O3 C3 N3 119.9(2) . . ?
O3 C3 C32 119.8(2) . . ?
N3 C3 C32 120.3(2) . . ?
O11 C11 C12 121.4(2) . . ?
O11 C11 C16 117.6(2) . . ?
C12 C11 C16 121.0(2) . . ?
C13 C12 C11 118.9(2) . . ?
C13 C12 C1 122.3(2) . . ?
C11 C12 C1 118.8(2) . . ?
C14 C13 C12 121.8(3) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15 C14 C13 117.0(2) . . ?
C15 C14 C21 122.5(2) . . ?
C13 C14 C21 120.6(3) . . ?
C14 C15 C16 124.8(2) . . ?
C14 C15 H15 117.6 . . ?
C16 C15 H15 117.6 . . ?
C15 C16 C11 116.6(3) . . ?
C15 C16 C25 122.3(2) . . ?
C11 C16 C25 121.1(2) . . ?
C53 C17 N1 109.7(8) . . ?
N1 C17 C19 113.1(3) . . ?
C53 C17 C51 107.3(10) . . ?
N1 C17 C51 115.5(7) . . ?
N1 C17 C18 106.1(4) . . ?
C19 C17 C18 111.0(4) . . ?
N1 C17 C20 106.6(3) . . ?
C19 C17 C20 108.9(4) . . ?
C18 C17 C20 111.0(4) . . ?
C53 C17 C52 109.8(11) . . ?
N1 C17 C52 106.4(8) . . ?
C51 C17 C52 108.2(9) . . ?
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 . . ?
C22 C21 C24 109.3(3) . . ?
C22 C21 C23 108.7(4) . . ?
C24 C21 C23 107.7(4) . . ?
C22 C21 C14 110.7(3) . . ?
C24 C21 C14 112.0(3) . . ?
C23 C21 C14 108.3(3) . . ?
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 . . ?
C26 C25 C28 107.8(3) . . ?
C26 C25 C27 107.5(3) . . ?
C28 C25 C27 110.4(3) . . ?
C26 C25 C16 111.4(3) . . ?
C28 C25 C16 109.3(3) . . ?
C27 C25 C16 110.3(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O31 C31 C36 118.1(2) . . ?
O31 C31 C32 120.9(2) . . ?
C36 C31 C32 121.0(2) . . ?
C33 C32 C31 118.8(2) . . ?
C33 C32 C3 122.1(2) . . ?
C31 C32 C3 119.1(2) . . ?
C34 C33 C32 121.8(2) . . ?
C34 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?
C33 C34 C35 117.4(2) . . ?
C33 C34 C41 120.9(2) . . ?
C35 C34 C41 121.7(2) . . ?
C34 C35 C36 124.0(2) . . ?
C34 C35 H35 118.0 . . ?
C36 C35 H35 118.0 . . ?
C35 C36 C31 117.0(2) . . ?
C35 C36 C45 122.4(2) . . ?
C31 C36 C45 120.6(2) . . ?
N3 C37 C54 106.7(5) . . ?
N3 C37 C40 107.3(4) . . ?
N3 C37 C55 115.7(5) . . ?
C54 C37 C55 112.3(7) . . ?
N3 C37 C38 112.8(4) . . ?
C40 C37 C38 107.2(6) . . ?
N3 C37 C39 104.5(6) . . ?
C40 C37 C39 112.9(7) . . ?
C38 C37 C39 112.1(6) . . ?
N3 C37 C56 107.2(5) . . ?
C54 C37 C56 107.6(7) . . ?
C55 C37 C56 107.1(8) . . ?
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 . . ?
C42 C41 C43 110.7(4) . . ?
C42 C41 C44 108.2(3) . . ?
C43 C41 C44 107.7(3) . . ?
C42 C41 C34 108.4(2) . . ?
C43 C41 C34 109.2(3) . . ?
C44 C41 C34 112.6(3) . . ?
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 . . ?
C46 C45 C47 107.4(3) . . ?
C46 C45 C48 107.4(3) . . ?
C47 C45 C48 110.1(3) . . ?
C46 C45 C36 111.1(3) . . ?
C47 C45 C36 109.9(2) . . ?
C48 C45 C36 110.8(2) . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C17 C51 H51A 109.5 . . ?
C17 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C17 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C17 C52 H52A 109.5 . . ?
C17 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C17 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C17 C53 H53A 109.5 . . ?
C17 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C17 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C37 C54 H54A 109.5 . . ?
C37 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C37 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C37 C55 H55A 109.5 . . ?
C37 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C37 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C37 C56 H56A 109.5 . . ?
C37 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C37 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 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 1.248(3) . ?
O3 C3 1.253(3) . ?
O11 C11 1.353(3) . ?
O11 H11 0.96(3) . ?
O31 C31 1.357(3) . ?
O31 H31 0.90(3) . ?
N1 C1 1.321(3) . ?
N1 C17 1.497(3) . ?
N1 H1 0.8800 . ?
N3 C3 1.319(3) . ?
N3 C37 1.488(3) . ?
N3 H3 0.8800 . ?
C1 C12 1.499(3) . ?
C3 C32 1.494(4) . ?
C11 C12 1.400(4) . ?
C11 C16 1.414(4) . ?
C12 C13 1.398(4) . ?
C13 C14 1.390(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(4) . ?
C14 C21 1.543(4) . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?
C16 C25 1.538(4) . ?
C17 C53 1.48(2) . ?
C17 C19 1.505(8) . ?
C17 C51 1.513(19) . ?
C17 C18 1.520(7) . ?
C17 C20 1.529(8) . ?
C17 C52 1.57(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.475(5) . ?
C21 C24 1.528(5) . ?
C21 C23 1.536(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.521(4) . ?
C25 C28 1.526(5) . ?
C25 C27 1.530(5) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C31 C36 1.403(4) . ?
C31 C32 1.405(4) . ?
C32 C33 1.395(3) . ?
C33 C34 1.384(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.388(4) . ?
C34 C41 1.536(4) . ?
C35 C36 1.388(4) . ?
C35 H35 0.9500 . ?
C36 C45 1.540(4) . ?
C37 C54 1.490(12) . ?
C37 C40 1.491(10) . ?
C37 C55 1.498(12) . ?
C37 C38 1.518(9) . ?
C37 C39 1.523(11) . ?
C37 C56 1.533(13) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 C42 1.494(5) . ?
C41 C43 1.501(5) . ?
C41 C44 1.509(5) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 C46 1.532(4) . ?
C45 C47 1.534(5) . ?
C45 C48 1.536(4) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
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 1.4(4) . . . . ?
C17 N1 C1 C12 -178.1(2) . . . . ?
C37 N3 C3 O3 -0.3(4) . . . . ?
C37 N3 C3 C32 179.9(2) . . . . ?
O11 C11 C12 C13 -179.6(2) . . . . ?
C16 C11 C12 C13 0.7(4) . . . . ?
O11 C11 C12 C1 -1.3(4) . . . . ?
C16 C11 C12 C1 179.1(2) . . . . ?
O1 C1 C12 C13 171.3(3) . . . . ?
N1 C1 C12 C13 -9.3(4) . . . . ?
O1 C1 C12 C11 -7.0(4) . . . . ?
N1 C1 C12 C11 172.5(2) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C1 C12 C13 C14 -179.0(3) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C12 C13 C14 C21 179.7(3) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C21 C14 C15 C16 -179.2(3) . . . . ?
C14 C15 C16 C11 -0.3(4) . . . . ?
C14 C15 C16 C25 178.9(3) . . . . ?
O11 C11 C16 C15 -180.0(2) . . . . ?
C12 C11 C16 C15 -0.3(4) . . . . ?
O11 C11 C16 C25 0.8(4) . . . . ?
C12 C11 C16 C25 -179.5(3) . . . . ?
C1 N1 C17 C53 165.8(13) . . . . ?
C1 N1 C17 C19 -45.1(6) . . . . ?
C1 N1 C17 C51 44.5(14) . . . . ?
C1 N1 C17 C18 76.7(5) . . . . ?
C1 N1 C17 C20 -164.8(5) . . . . ?
C1 N1 C17 C52 -75.6(12) . . . . ?
C15 C14 C21 C22 123.9(4) . . . . ?
C13 C14 C21 C22 -55.7(4) . . . . ?
C15 C14 C21 C24 1.5(5) . . . . ?
C13 C14 C21 C24 -178.0(3) . . . . ?
C15 C14 C21 C23 -117.1(4) . . . . ?
C13 C14 C21 C23 63.4(4) . . . . ?
C15 C16 C25 C26 2.5(4) . . . . ?
C11 C16 C25 C26 -178.3(3) . . . . ?
C15 C16 C25 C28 -116.5(3) . . . . ?
C11 C16 C25 C28 62.6(4) . . . . ?
C15 C16 C25 C27 121.9(3) . . . . ?
C11 C16 C25 C27 -59.0(4) . . . . ?
O31 C31 C32 C33 179.6(2) . . . . ?
C36 C31 C32 C33 0.1(4) . . . . ?
O31 C31 C32 C3 0.2(4) . . . . ?
C36 C31 C32 C3 -179.2(2) . . . . ?
O3 C3 C32 C33 -168.3(3) . . . . ?
N3 C3 C32 C33 11.5(4) . . . . ?
O3 C3 C32 C31 11.1(4) . . . . ?
N3 C3 C32 C31 -169.2(2) . . . . ?
C31 C32 C33 C34 -0.3(4) . . . . ?
C3 C32 C33 C34 179.0(2) . . . . ?
C32 C33 C34 C35 0.6(4) . . . . ?
C32 C33 C34 C41 -179.3(2) . . . . ?
C33 C34 C35 C36 -0.9(4) . . . . ?
C41 C34 C35 C36 179.1(2) . . . . ?
C34 C35 C36 C31 0.7(4) . . . . ?
C34 C35 C36 C45 -178.9(2) . . . . ?
O31 C31 C36 C35 -179.8(2) . . . . ?
C32 C31 C36 C35 -0.3(4) . . . . ?
O31 C31 C36 C45 -0.1(4) . . . . ?
C32 C31 C36 C45 179.3(2) . . . . ?
C3 N3 C37 C54 78.9(8) . . . . ?
C3 N3 C37 C40 161.1(7) . . . . ?
C3 N3 C37 C55 -46.7(10) . . . . ?
C3 N3 C37 C38 43.3(7) . . . . ?
C3 N3 C37 C39 -78.7(7) . . . . ?
C3 N3 C37 C56 -166.1(8) . . . . ?
C33 C34 C41 C42 -62.2(4) . . . . ?
C35 C34 C41 C42 117.8(4) . . . . ?
C33 C34 C41 C43 58.5(4) . . . . ?
C35 C34 C41 C43 -121.5(3) . . . . ?
C33 C34 C41 C44 178.1(3) . . . . ?
C35 C34 C41 C44 -1.9(4) . . . . ?
C35 C36 C45 C46 -0.7(4) . . . . ?
C31 C36 C45 C46 179.7(3) . . . . ?
C35 C36 C45 C47 118.1(3) . . . . ?
C31 C36 C45 C47 -61.6(3) . . . . ?
C35 C36 C45 C48 -120.0(3) . . . . ?
C31 C36 C45 C48 60.3(4) . . . . ?
