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#$Date: 2025-08-19 23:06:29 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301812 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/46/4024604.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_4024604
loop_
_publ_author_name
'Carlos Saavedra'
'Rosendo Hernández'
'Alicia Boto'
'Eleuterio Álvarez'
_publ_section_title
;
Catalytic, One-Pot Synthesis of β-Amino Acids from α-Amino Acids.
Preparation of α,β-Peptide Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4655
_journal_page_last               4665
_journal_paper_doi               10.1021/jo9004487
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H30 N2 O4'
_chemical_formula_sum            'C20 H30 N2 O4'
_chemical_formula_weight         362.46
_space_group_IT_number           170
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      170
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   11.7280(10)
_cell_length_b                   11.7280(10)
_cell_length_c                   26.998(5)
_cell_measurement_reflns_used    3311
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.42
_cell_measurement_theta_min      2.51
_cell_volume                     3216.0(7)
_computing_cell_refinement       'SAINT+ v. 7.06 a (Bruker AXS, 2003)'
_computing_data_collection       'APEX-W2K-NT v. 1.0 (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT+ v. 7.06 a (Bruker AXS, 2001)'
_computing_molecular_graphics    'XP, SHELXTL v. 6.10 (Bruker, 2000)'
_computing_publication_material  'XCIF, SHELXTL v. 6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
 Bruker-Nonius X8kappa APEX II CCD area detector'
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            26186
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.47
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.9331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS: Area-Detector Absorption Correction. Bruker-AXS
 within v. 7.06 a (Bruker AXS, 2003); ratio of minimum to maximum
 apparent transmission:  0.557670m
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         2240
_refine_ls_number_restraints     383
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1434
_refine_ls_R_factor_gt           0.0774
_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)+(0.0906P)²+2.6693P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1858
_refine_ls_wR_factor_ref         0.2375
_reflns_number_gt                1336
_reflns_number_total             2240
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9004487_si_003.cif
_cod_data_source_block           71
_cod_database_code               4024604
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'
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 0.7891(7) 0.9286(7) 0.4474(2) 0.101(2) Uani 1 1 d . . .
O3 O 1.5179(6) 1.1613(5) 0.46331(12) 0.0854(12) Uani 1 1 d . . .
O4 O 1.5191(6) 1.0786(6) 0.53731(14) 0.0883(13) Uani 1 1 d . . .
N1 N 0.8461(5) 0.8493(5) 0.3820(2) 0.0685(13) Uani 1 1 d . . .
H1N H 0.9087 0.9034 0.3594 0.082 Uiso 1 1 d R B .
N2 N 1.1037(6) 0.9209(6) 0.4633(2) 0.0712(13) Uani 1 1 d D . .
H2N H 1.0510 0.9448 0.4804 0.085 Uiso 1 1 d R B .
C1 C 0.7951(6) 0.9182(6) 0.4023(3) 0.0641(13) Uani 1 1 d GD A .
C2A C 0.7442(5) 0.9832(6) 0.3725(2) 0.063(4) Uani 0.50 1 d PGDU A 1
C3A C 0.7787(6) 1.0102(7) 0.3228(2) 0.081(4) Uani 0.50 1 d PGU A 1
H3A H 0.8318 0.9799 0.3077 0.097 Uiso 0.50 1 d PR A 1
C4A C 0.7354(8) 1.0815(9) 0.2953(3) 0.088(4) Uani 0.50 1 d PGU A 1
H4A H 0.7590 1.0999 0.2614 0.105 Uiso 0.50 1 d PR A 1
C5A C 0.6577(7) 1.1257(7) 0.3174(3) 0.070(4) Uani 0.50 1 d PGU A 1
H5A H 0.6281 1.1745 0.2986 0.085 Uiso 0.50 1 d PR A 1
C6A C 0.6232(6) 1.0988(6) 0.3671(3) 0.068(4) Uani 0.50 1 d PGU A 1
H6A H 0.5701 1.1290 0.3822 0.081 Uiso 0.50 1 d PR A 1
C7A C 0.6665(7) 1.0275(7) 0.39460(13) 0.063(4) Uani 0.50 1 d PGU A 1
H7A H 0.6429 1.0091 0.4285 0.076 Uiso 0.50 1 d PR A 1
C2B C 0.7353(5) 0.9740(5) 0.3632(2) 0.050(3) Uani 0.50 1 d PGDU A 2
C3B C 0.7196(8) 0.9433(8) 0.3130(2) 0.069(3) Uani 0.50 1 d PGU A 2
H3B H 0.7522 0.8904 0.2995 0.083 Uiso 0.50 1 d PR A 2
C4B C 0.6562(9) 0.9900(10) 0.28266(18) 0.075(3) Uani 0.50 1 d PGU A 2
H4B H 0.6455 0.9690 0.2484 0.090 Uiso 0.50 1 d PR A 2
C5B C 0.6085(7) 1.0675(9) 0.3025(2) 0.068(3) Uani 0.50 1 d PGU A 2
H5B H 0.5652 1.0994 0.2817 0.082 Uiso 0.50 1 d PR A 2
C6B C 0.6243(5) 1.0982(6) 0.3527(3) 0.061(4) Uani 0.50 1 d PGU A 2
H6B H 0.5917 1.1512 0.3662 0.074 Uiso 0.50 1 d PR A 2
C7B C 0.6876(6) 1.0515(6) 0.3830(2) 0.056(3) Uani 0.50 1 d PGU A 2
H7B H 0.6984 1.0725 0.4173 0.068 Uiso 0.50 1 d PR A 2
C8A C 1.0502(6) 0.8862(7) 0.4151(2) 0.0686(12) Uani 0.50 1 d PDU B 1
O2A O 1.1302(13) 0.9652(14) 0.3847(6) 0.078(5) Uani 0.50 1 d PDU B 1
C8B C 1.0502(6) 0.8862(7) 0.4151(2) 0.0686(17) Uani 0.50 1 d PDU B 2
O2B O 1.1125(13) 0.9092(11) 0.3744(5) 0.052(3) Uani 0.50 1 d PDU B 2
C9A C 0.9070(14) 0.7842(13) 0.4060(9) 0.066(5) Uani 0.50 1 d PDU B 1
H9A H 0.8644 0.7574 0.4393 0.079 Uiso 0.50 1 d PR B 1
C10A C 0.8659(15) 0.6539(15) 0.3782(6) 0.073(3) Uani 0.50 1 d PDU B 1
H10A H 0.7693 0.6052 0.3735 0.088 Uiso 0.50 1 d PR B 1
H10B H 0.9076 0.6745 0.3451 0.088 Uiso 0.50 1 d PR B 1
C11A C 0.9058(14) 0.5654(11) 0.4056(5) 0.068(3) Uani 0.50 1 d PDU B 1
H11A H 1.0007 0.6215 0.4147 0.082 Uiso 0.50 1 d PR B 1
C12A C 0.894(2) 0.4569(14) 0.3722(7) 0.116(6) Uani 0.50 1 d PDU B 1
H12A H 0.9031 0.3903 0.3910 0.174 Uiso 0.50 1 d PR B 1
H12B H 0.9647 0.4968 0.3475 0.174 Uiso 0.50 1 d PR B 1
H12C H 0.8086 0.4154 0.3555 0.174 Uiso 0.50 1 d PR B 1
C13A C 0.8313(19) 0.5114(19) 0.4521(6) 0.105(5) Uani 0.50 1 d PDU B 1
H13A H 0.7378 0.4536 0.4445 0.157 Uiso 0.50 1 d PR B 1
H13B H 0.8418 0.5845 0.4729 0.157 Uiso 0.50 1 d PR B 1
H13C H 0.8649 0.4612 0.4698 0.157 Uiso 0.50 1 d PR B 1
C9B C 0.9084(16) 0.7998(17) 0.4197(10) 0.062(4) Uani 0.50 1 d PDU B 2
H9B H 0.8748 0.7932 0.4542 0.074 Uiso 0.50 1 d PR B 2
C10B C 0.9046(15) 0.6769(13) 0.4025(7) 0.070(4) Uani 0.50 1 d PDU B 2
H10C H 0.9422 0.6929 0.3687 0.084 Uiso 0.50 1 d PR B 2
H10D H 0.9597 0.6554 0.4240 0.084 Uiso 0.50 1 d PR B 2
C11B C 0.7706(14) 0.5627(14) 0.4011(5) 0.081(3) Uani 0.50 1 d PDU B 2
H11B H 0.7108 0.5862 0.3830 0.097 Uiso 0.50 1 d PR B 2
C12B C 0.766(2) 0.4465(13) 0.3772(8) 0.106(6) Uani 0.50 1 d PDU B 2
H12D H 0.8081 0.4730 0.3445 0.159 Uiso 0.50 1 d PR B 2
H12E H 0.6751 0.3750 0.3733 0.159 Uiso 0.50 1 d PR B 2
H12F H 0.8149 0.4162 0.3977 0.159 Uiso 0.50 1 d PR B 2
C13B C 0.719(2) 0.5191(18) 0.4522(7) 0.127(8) Uani 0.50 1 d PDU B 2
H13D H 0.6324 0.4386 0.4511 0.190 Uiso 0.50 1 d PR B 2
H13E H 0.7104 0.5886 0.4691 0.190 Uiso 0.50 1 d PR B 2
H13F H 0.7808 0.5017 0.4704 0.190 Uiso 0.50 1 d PR B 2
C14 C 1.4609(8) 1.0771(7) 0.4937(2) 0.0683(13) Uani 1 1 d . B .
C15 C 1.3235(7) 0.9607(7) 0.4883(2) 0.0619(12) Uani 1 1 d . . .
C16 C 1.2387(8) 1.0213(7) 0.4729(3) 0.073(2) Uani 1 1 d . B .
H16 H 1.2761 1.0711 0.4414 0.087 Uiso 1 1 d R . .
C17 C 1.2347(13) 1.1152(13) 0.5102(6) 0.159(6) Uani 1 1 d . . .
H17A H 1.1679 1.1376 0.5003 0.238 Uiso 1 1 d R B .
H17B H 1.3211 1.1955 0.5116 0.238 Uiso 1 1 d R . .
H17C H 1.2128 1.0736 0.5430 0.238 Uiso 1 1 d R . .
C18 C 1.3275(8) 0.8771(7) 0.4472(3) 0.074(2) Uani 1 1 d . B .
H18A H 1.3550 0.9284 0.4165 0.111 Uiso 1 1 d R . .
H18B H 1.2396 0.8003 0.4428 0.111 Uiso 1 1 d R . .
H18C H 1.3901 0.8477 0.4554 0.111 Uiso 1 1 d R . .
C19 C 1.2741(11) 0.8778(12) 0.5355(4) 0.119(4) Uani 1 1 d . B .
H19A H 1.1870 0.8012 0.5293 0.179 Uiso 1 1 d R . .
H19B H 1.2678 0.9310 0.5622 0.179 Uiso 1 1 d R . .
H19C H 1.3353 0.8478 0.5453 0.179 Uiso 1 1 d R . .
C20 C 1.6508(9) 1.1895(10) 0.5445(4) 0.102(3) Uani 1 1 d . . .
H20A H 1.7078 1.1922 0.5174 0.153 Uiso 1 1 d R . .
H20B H 1.6861 1.1798 0.5761 0.153 Uiso 1 1 d R . .
H20C H 1.6474 1.2713 0.5447 0.153 Uiso 1 1 d 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C14 O4 C20 115.5(6) . . ?
C1 N1 C9A 128.8(10) . . ?
C1 N1 C9B 113.5(9) . . ?
C1 N1 H1N 107.3 . . ?
C9A N1 H1N 103.2 . . ?
C9B N1 H1N 109.5 . . ?
C8A N2 C16 123.2(5) . . ?
C8A N2 H2N 106.2 . . ?
C16 N2 H2N 107.0 . . ?
O1 C1 N1 122.1(6) . . ?
O1 C1 C2A 116.5(7) . . ?
N1 C1 C2A 121.5(7) . . ?
O1 C1 C2B 124.2(6) . . ?
N1 C1 C2B 113.6(7) . . ?
C3A C2A C7A 120.0 . . ?
C3A C2A C1 120.9(5) . . ?
C7A C2A C1 118.9(5) . . ?
C4A C3A C2A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A H3B 113.1 . . ?
C2A C3A H3B 107.8 . . ?
H3A C3A H3B 45.7 . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C6A C5A C4A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A H5B 121.4 . . ?
C4A C5A H5B 102.0 . . ?
C7A C6A C5A 120.0 . . ?
C7A C6A H6A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C7A C6A H6B 149.3 . . ?
C5A C6A H6B 89.4 . . ?
C6A C7A C2A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C2A C7A H7A 120.0 . . ?
C6A C7A H7B 102.2 . . ?
C2A C7A H7B 114.4 . . ?
H7A C7A H7B 51.4 . . ?
C3B C2B C7B 120.0 . . ?
C3B C2B C1 124.9(5) . . ?
C7B C2B C1 114.9(5) . . ?
C2B C3B C4B 120.0 . . ?
C2B C3B H3A 92.6 . . ?
C4B C3B H3A 120.5 . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
H3A C3B H3B 56.4 . . ?
C5B C4B C3B 120.0 . . ?
C5B C4B H4A 89.9 . . ?
C3B C4B H4A 103.0 . . ?
C5B C4B H4B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
H4A C4B H4B 77.1 . . ?
C6B C5B C4B 120.0 . . ?
C6B C5B H5A 83.0 . . ?
C4B C5B H5A 138.1 . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
H5A C5B H5B 51.5 . . ?
C5B C6B C7B 120.0 . . ?
C5B C6B H6A 135.6 . . ?
C7B C6B H6A 101.4 . . ?
C5B C6B H6B 120.0 . . ?
C7B C6B H6B 120.0 . . ?
C6B C7B C2B 120.0 . . ?
C6B C7B H7A 120.2 . . ?
C2B C7B H7A 108.9 . . ?
C6B C7B H7B 120.0 . . ?
C2B C7B H7B 120.0 . . ?
O2A C8A N2 109.5(10) . . ?
O2A C8A C9A 127.2(13) . . ?
N2 C8A C9A 122.3(10) . . ?
N1 C9A C8A 107.7(12) . . ?
N1 C9A C10A 108.3(15) . . ?
C8A C9A C10A 122.2(14) . . ?
N1 C9A H9A 105.7 . . ?
C8A C9A H9A 106.5 . . ?
C10A C9A H9A 105.4 . . ?
N1 C9A H9B 99.2 . . ?
C8A C9A H9B 91.4 . . ?
C10A C9A H9B 125.0 . . ?
C11A C10A C9A 112.8(16) . . ?
C11A C10A H10A 108.8 . . ?
C9A C10A H10A 109.5 . . ?
C11A C10A H10B 108.8 . . ?
C9A C10A H10B 109.0 . . ?
H10A C10A H10B 107.8 . . ?
C11A C10A H10C 84.9 . . ?
C9A C10A H10C 83.6 . . ?
H10A C10A H10C 154.1 . . ?
H10B C10A H10C 46.2 . . ?
C11A C10A H11B 106.6 . . ?
C9A C10A H11B 99.7 . . ?
H10B C10A H11B 119.9 . . ?
H10C C10A H11B 165.4 . . ?
C13A C11A C12A 111.2(14) . . ?
C13A C11A C10A 112.7(13) . . ?
C12A C11A C10A 110.9(12) . . ?
C13A C11A H11A 107.3 . . ?
C12A C11A H11A 107.6 . . ?
C10A C11A H11A 106.8 . . ?
C13A C11A H10D 87.6 . . ?
C12A C11A H10D 152.7 . . ?
C10A C11A H10D 77.2 . . ?
H11A C11A H10D 46.1 . . ?
C13A C11A H12F 72.9 . . ?
C10A C11A H12F 115.6 . . ?
H11A C11A H12F 133.7 . . ?
H10D C11A H12F 159.6 . . ?
C11A C12A H12A 111.2 . . ?
C11A C12A H12B 107.8 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.3 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11A C12A H12D 88.3 . . ?
H12A C12A H12D 141.9 . . ?
H12B C12A H12D 93.9 . . ?
C11A C12A H12F 71.4 . . ?
H12A C12A H12F 74.0 . . ?
H12B C12A H12F 176.4 . . ?
H12C C12A H12F 67.9 . . ?
H12D C12A H12F 82.6 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 108.8 . . ?
H13A C13A H13B 109.5 . . ?
C11A C13A H13C 110.0 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C11A C13A H13F 153.3 . . ?
H13A C13A H13F 59.8 . . ?
H13B C13A H13F 59.3 . . ?
H13C C13A H13F 96.7 . . ?
C10B C9B N1 111.7(17) . . ?
C10B C9B H9A 84.2 . . ?
N1 C9B H9A 115.5 . . ?
C10B C9B H9B 113.2 . . ?
N1 C9B H9B 114.0 . . ?
C11B C10B C9B 112.9(13) . . ?
C9B C10B H10A 101.8 . . ?
C11B C10B H10B 88.9 . . ?
C9B C10B H10B 109.7 . . ?
H10A C10B H10B 61.4 . . ?
C11B C10B H10C 108.7 . . ?
C9B C10B H10C 108.0 . . ?
H10A C10B H10C 83.0 . . ?
C11B C10B H10D 108.7 . . ?
C9B C10B H10D 110.7 . . ?
H10A C10B H10D 139.8 . . ?
H10B C10B H10D 123.9 . . ?
H10C C10B H10D 107.7 . . ?
C10B C11B C12B 112.2(14) . . ?
C10B C11B C13B 110.8(13) . . ?
C12B C11B C13B 105.4(16) . . ?
C10B C11B H10A 79.9 . . ?
C12B C11B H10A 98.4 . . ?
C13B C11B H10A 146.9 . . ?
C10B C11B H11B 109.9 . . ?
C12B C11B H11B 109.5 . . ?
C13B C11B H11B 108.9 . . ?
C11B C12B H12C 146.6 . . ?
C11B C12B H12D 108.5 . . ?
H12C C12B H12D 45.1 . . ?
C11B C12B H12E 110.8 . . ?
H12C C12B H12E 99.3 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.2 . . ?
H12C C12B H12F 72.4 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11B C13B H13A 81.3 . . ?
C11B C13B H13B 92.8 . . ?
H13A C13B H13B 86.0 . . ?
C11B C13B H13D 110.4 . . ?
H13A C13B H13D 75.8 . . ?
H13B C13B H13D 147.5 . . ?
C11B C13B H13E 109.7 . . ?
H13A C13B H13E 163.9 . . ?
H13B C13B H13E 81.9 . . ?
H13D C13B H13E 109.5 . . ?
C11B C13B H13F 108.3 . . ?
H13A C13B H13F 54.9 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
O3 C14 O4 121.0(7) . . ?
O3 C14 C15 125.5(7) . . ?
O4 C14 C15 113.5(6) . . ?
C18 C15 C14 107.2(6) . . ?
C18 C15 C19 109.1(7) . . ?
C14 C15 C19 112.7(7) . . ?
C18 C15 C16 110.0(6) . . ?
C14 C15 C16 104.6(6) . . ?
C19 C15 C16 113.0(7) . . ?
N2 C16 C17 107.0(7) . . ?
N2 C16 C15 111.6(6) . . ?
C17 C16 C15 114.7(9) . . ?
N2 C16 H16 107.7 . . ?
C17 C16 H16 107.9 . . ?
C15 C16 H16 107.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.6 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.4 . . ?
C15 C18 H18B 109.3 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.7 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.2 . . ?
C15 C19 H19B 109.4 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.8 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.6 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.4 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 1.229(9) . ?
O3 C14 1.199(8) . ?
O4 C14 1.356(9) . ?
O4 C20 1.451(10) . ?
N1 C1 1.340(9) . ?
N1 C9A 1.44(3) . ?
N1 C9B 1.53(3) . ?
N1 H1N 0.9200 . ?
N2 C8A 1.412(8) . ?
N2 C16 1.447(10) . ?
N2 H2N 0.9200 . ?
C1 C2A 1.429(7) . ?
C1 C2B 1.580(7) . ?
C2A C3A 1.3900 . ?
C2A C7A 1.3900 . ?
C3A C4A 1.3900 . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3900 . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9500 . ?
C6A C7A 1.3900 . ?
C6A H6A 0.9500 . ?
C6A H6B 0.8615 . ?
C7A H7A 0.9500 . ?
C2B C3B 1.3900 . ?
C2B C7B 1.3901 . ?
C3B C4B 1.3901 . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3900 . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3899 . ?
C5B H5B 0.9500 . ?
C6B C7B 1.3900 . ?
C6B H6B 0.9500 . ?
C7B H7B 0.9500 . ?
C8A O2A 1.244(13) . ?
C8A C9A 1.517(15) . ?
C9A C10A 1.547(16) . ?
C9A H9A 1.0000 . ?
C10A C11A 1.525(14) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10A H10C 0.8163 . ?
C11A C13A 1.480(16) . ?
C11A C12A 1.508(15) . ?
C11A H11A 1.0000 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C9B C10B 1.494(16) . ?
C9B H9B 1.0000 . ?
C10B C11B 1.469(16) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B C12B 1.486(16) . ?
C11B C13B 1.494(16) . ?
C11B H11B 1.0000 . ?
C12B H12C 0.9503 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14 C15 1.511(11) . ?
C15 C18 1.495(10) . ?
C15 C19 1.531(10) . ?
C15 C16 1.541(10) . ?
C16 C17 1.511(12) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
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 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O2B 0.92 2.39 2.846(16) 110.5 .
N1 H1N O2A 0.92 2.42 2.903(18) 112.8 .
N2 H2N O2A 0.92 2.25 2.768(15) 115.4 5_565
N2 H2N O2B 0.92 2.36 2.901(15) 117.2 5_565
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
C9A N1 C1 O1 -3.8(12) . . . . ?
C9B N1 C1 O1 -6.5(11) . . . . ?
C9A N1 C1 C2A 176.5(9) . . . . ?
C9B N1 C1 C2A 173.8(8) . . . . ?
C9A N1 C1 C2B -179.5(8) . . . . ?
C9B N1 C1 C2B 177.8(8) . . . . ?
O1 C1 C2A C3A 161.4(6) . . . . ?
N1 C1 C2A C3A -18.8(8) . . . . ?
C2B C1 C2A C3A -44.3(2) . . . . ?
O1 C1 C2A C7A -14.2(8) . . . . ?
N1 C1 C2A C7A 165.6(5) . . . . ?
C2B C1 C2A C7A 140.1(6) . . . . ?
C7A C2A C3A C4A 0.0 . . . . ?
C1 C2A C3A C4A -175.6(6) . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C5A C6A C7A 0.0 . . . . ?
C5A C6A C7A C2A 0.0 . . . . ?
C3A C2A C7A C6A 0.0 . . . . ?
C1 C2A C7A C6A 175.7(6) . . . . ?
O1 C1 C2B C3B -167.7(7) . . . . ?
N1 C1 C2B C3B 7.9(8) . . . . ?
C2A C1 C2B C3B 164.35(12) . . . . ?
O1 C1 C2B C7B 7.4(9) . . . . ?
N1 C1 C2B C7B -176.9(5) . . . . ?
C2A C1 C2B C7B -20.5(6) . . . . ?
C7B C2B C3B C4B 0.0 . . . . ?
C1 C2B C3B C4B 174.9(6) . . . . ?
C2B C3B C4B C5B 0.0 . . . . ?
C3B C4B C5B C6B 0.0 . . . . ?
C4B C5B C6B C7B 0.0 . . . . ?
C5B C6B C7B C2B 0.0 . . . . ?
C3B C2B C7B C6B 0.0 . . . . ?
C1 C2B C7B C6B -175.4(5) . . . . ?
C16 N2 C8A O2A -8.5(13) . . . . ?
C16 N2 C8A C9A -177.7(11) . . . . ?
C1 N1 C9A C8A -83.8(13) . . . . ?
C9B N1 C9A C8A -75(4) . . . . ?
C1 N1 C9A C10A 142.3(11) . . . . ?
C9B N1 C9A C10A 152(5) . . . . ?
O2A C8A C9A N1 -50(2) . . . . ?
N2 C8A C9A N1 117.2(13) . . . . ?
O2A C8A C9A C10A 76(2) . . . . ?
N2 C8A C9A C10A -116.7(16) . . . . ?
N1 C9A C10A C11A -170.3(13) . . . . ?
C8A C9A C10A C11A 64(2) . . . . ?
C9A C10A C11A C13A 68.4(18) . . . . ?
C9A C10A C11A C12A -166.2(14) . . . . ?
C1 N1 C9B C10B 152.4(11) . . . . ?
C9A N1 C9B C10B -20(3) . . . . ?
N1 C9B C10B C11B -68.6(19) . . . . ?
C9B C10B C11B C12B 171.8(18) . . . . ?
C9B C10B C11B C13B -71(2) . . . . ?
C20 O4 C14 O3 1.7(11) . . . . ?
C20 O4 C14 C15 -179.4(7) . . . . ?
O3 C14 C15 C18 65.1(9) . . . . ?
O4 C14 C15 C18 -113.7(7) . . . . ?
O3 C14 C15 C19 -174.8(9) . . . . ?
O4 C14 C15 C19 6.3(10) . . . . ?
O3 C14 C15 C16 -51.7(9) . . . . ?
O4 C14 C15 C16 129.5(6) . . . . ?
C8A N2 C16 C17 128.1(9) . . . . ?
C8A N2 C16 C15 -105.6(7) . . . . ?
C18 C15 C16 N2 61.9(7) . . . . ?
C14 C15 C16 N2 176.8(5) . . . . ?
C19 C15 C16 N2 -60.2(9) . . . . ?
C18 C15 C16 C17 -176.2(8) . . . . ?
C14 C15 C16 C17 -61.3(8) . . . . ?
C19 C15 C16 C17 61.7(10) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 15941892
