#------------------------------------------------------------------------------
#$Date: 2020-02-20 02:09:12 +0200 (Thu, 20 Feb 2020) $
#$Revision: 248297 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/79/4037944.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_4037944
loop_
_publ_author_name
'Navo, Claudio D.'
'Mazo, Nuria'
'Oroz, Paula'
'Gutiérrez-Jiménez, Marta I'
'Marín, Javier'
'Asenjo, Juan'
'Avenoza, Alberto'
'Busto, Jesús H'
'Corzana, Francisco'
'Zurbano, María M'
'Jiménez-Osés, Gonzalo'
'Peregrina, Jesús M'
_publ_section_title
;
 Synthesis of N <sub>β</sub> -Substituted α,β-Diamino
 Acids via Stereoselective N-Michael Additions to a Chiral Bicyclic
 Dehydroalanine.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03020
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C23 H29 N3 O5'
_chemical_formula_sum            'C23 H29 N3 O5'
_chemical_formula_weight         427.49
_chemical_name_common            JA-TFG-1
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-04-27T13:44:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 113.483(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0249(11)
_cell_length_b                   7.4099(6)
_cell_length_c                   13.5550(12)
_cell_measurement_reflns_used    110
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      24.877
_cell_measurement_theta_min      4.03
_cell_measurement_wavelength     0.71076
_cell_volume                     1107.76(17)
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_orient_matrix_UB_11      0.064081
_diffrn_orient_matrix_UB_12      0.095445
_diffrn_orient_matrix_UB_13      0.023953
_diffrn_orient_matrix_UB_21      -0.020141
_diffrn_orient_matrix_UB_22      0.026746
_diffrn_orient_matrix_UB_23      0.063309
_diffrn_orient_matrix_UB_31      0.060902
_diffrn_orient_matrix_UB_32      -0.091582
_diffrn_orient_matrix_UB_33      0.043452
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8516
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         33.497
_diffrn_reflns_theta_min         2.917
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  1
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
	[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            'translucent pale colourless'
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.05
_refine_ls_abs_structure_details
;
 Flack x determined using 3097 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     296
_refine_ls_number_reflns         8516
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0632P)²+0.0389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.97
_reflns_number_gt                7284
_reflns_number_total             8516
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03020_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4037944
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.982
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.10583(8) 0.99060(13) 0.63281(7) 0.01495(18) Uani 1 1 d . . . . .
O2 O 0.18410(9) 1.25894(14) 0.70651(8) 0.01699(19) Uani 1 1 d . . . . .
N1 N 0.27189(9) 0.98889(15) 0.78388(8) 0.01176(18) Uani 1 1 d . . . . .
O5 O 0.15094(10) 0.77468(15) 0.82387(8) 0.0202(2) Uani 1 1 d . . . . .
O3 O 0.23571(10) 0.79368(16) 0.59925(8) 0.0219(2) Uani 1 1 d . . . . .
N2 N 0.26639(11) 1.01059(17) 0.99687(9) 0.0156(2) Uani 1 1 d . . . . .
O4 O 0.50517(10) 1.31334(16) 0.90220(9) 0.0227(2) Uani 1 1 d . . . . .
C1 C 0.23002(11) 0.80210(17) 0.77092(10) 0.0141(2) Uani 1 1 d . . . . .
C4 C 0.15334(12) 0.80717(18) 0.64822(10) 0.0155(2) Uani 1 1 d . . . . .
C3 C 0.18784(11) 1.09596(18) 0.70904(9) 0.0128(2) Uani 1 1 d . . . . .
N3 N 0.45874(11) 1.14193(18) 0.75233(9) 0.0186(2) Uani 1 1 d . . . . .
C5 C 0.32064(12) 1.15297(18) 0.95506(10) 0.0152(2) Uani 1 1 d . . . . .
H5A H 0.3877 1.2122 1.0149 0.018 Uiso 1 1 calc R U . . .
H5B H 0.2591 1.2455 0.9169 0.018 Uiso 1 1 calc R U . . .
C6 C 0.36838(11) 1.06526(18) 0.87797(10) 0.0126(2) Uani 1 1 d . . . . .
C7 C 0.44922(11) 1.18869(18) 0.84430(10) 0.0149(2) Uani 1 1 d . . . . .
C8 C 0.14781(12) 0.9332(2) 1.10357(11) 0.0182(3) Uani 1 1 d . . . . .
C9 C 0.20397(13) 1.0813(2) 1.06130(11) 0.0185(2) Uani 1 1 d . . . . .
H9A H 0.1396 1.1656 1.0169 0.022 Uiso 1 1 calc R U . . .
H9B H 0.2623 1.1501 1.1228 0.022 Uiso 1 1 calc R U . . .
C10 C 0.33122(13) 0.6651(2) 0.80663(11) 0.0204(3) Uani 1 1 d . . . . .
H10A H 0.3846 0.687 0.7689 0.031 Uiso 1 1 calc R U . . .
H10B H 0.3779 0.676 0.8844 0.031 Uiso 1 1 calc R U . . .
H10C H 0.2969 0.5434 0.7898 0.031 Uiso 1 1 calc R U . . .
C11 C 0.44772(13) 1.2686(2) 0.58237(11) 0.0191(3) Uani 1 1 d . . . . .
C12 C 0.04796(14) 0.6784(2) 0.60673(12) 0.0245(3) Uani 1 1 d . . . . .
H12A H -0.0045 0.6976 0.6456 0.037 Uiso 1 1 calc R U . . .
H12B H 0.0016 0.6996 0.5298 0.037 Uiso 1 1 calc R U . . .
H12C H 0.0782 0.554 0.6179 0.037 Uiso 1 1 calc R U . . .
C13 C 0.52222(13) 1.2502(3) 0.70129(12) 0.0246(3) Uani 1 1 d . . . . .
H13A H 0.6008 1.1926 0.713 0.03 Uiso 1 1 calc R U . . .
H13B H 0.5391 1.3715 0.7347 0.03 Uiso 1 1 calc R U . . .
C14 C 0.16686(14) 0.7509(2) 1.09195(12) 0.0226(3) Uani 1 1 d . . . . .
H14 H 0.2156 0.7152 1.0548 0.027 Uiso 1 1 calc R U . . .
C15 C 0.33184(14) 1.3438(2) 0.54491(13) 0.0244(3) Uani 1 1 d . . . . .
H15 H 0.2995 1.3836 0.5947 0.029 Uiso 1 1 calc R U . . .
C16 C 0.11505(15) 0.6196(3) 1.13442(13) 0.0276(3) Uani 1 1 d . . . . .
H16 H 0.1281 0.4953 1.1255 0.033 Uiso 1 1 calc R U . . .
C17 C 0.07371(15) 0.9831(2) 1.15679(13) 0.0260(3) Uani 1 1 d . . . . .
H17 H 0.0581 1.1071 1.1636 0.031 Uiso 1 1 calc R U . . .
C18 C 0.04443(15) 0.6706(3) 1.18967(13) 0.0287(3) Uani 1 1 d . . . . .
H18 H 0.011 0.5817 1.2204 0.034 Uiso 1 1 calc R U . . .
C19 C 0.02308(16) 0.8525(3) 1.19955(14) 0.0311(4) Uani 1 1 d . . . . .
H19 H -0.0266 0.8878 1.2359 0.037 Uiso 1 1 calc R U . . .
C20 C 0.26354(17) 1.3608(3) 0.43537(15) 0.0343(4) Uani 1 1 d . . . . .
H20 H 0.1848 1.4125 0.4105 0.041 Uiso 1 1 calc R U . . .
C21 C 0.18652(19) 0.8258(3) 0.48533(13) 0.0351(4) Uani 1 1 d . . . . .
H21A H 0.2509 0.8133 0.4587 0.053 Uiso 1 1 calc R U . . .
H21B H 0.1222 0.738 0.4491 0.053 Uiso 1 1 calc R U . . .
H21C H 0.1529 0.9482 0.4705 0.053 Uiso 1 1 calc R U . . .
C22 C 0.4923(2) 1.2090(3) 0.50828(15) 0.0330(4) Uani 1 1 d . . . . .
H22 H 0.5701 1.1545 0.5325 0.04 Uiso 1 1 calc R U . . .
C23 C 0.3093(2) 1.3032(3) 0.36281(15) 0.0454(5) Uani 1 1 d . . . . .
H23 H 0.2621 1.3148 0.2878 0.054 Uiso 1 1 calc R U . . .
C24 C 0.4235(3) 1.2286(3) 0.39846(17) 0.0486(6) Uani 1 1 d . . . . .
H24 H 0.4555 1.1905 0.3481 0.058 Uiso 1 1 calc R U . . .
H2 H 0.3264(19) 0.941(3) 1.0396(16) 0.019(5) Uiso 1 1 d . . . . .
H6 H 0.4193(18) 0.974(3) 0.9122(16) 0.015(4) Uiso 1 1 d . . . . .
H3 H 0.4148(19) 1.053(3) 0.7180(17) 0.020(5) Uiso 1 1 d . . . . .
H5 H 0.185(2) 0.848(3) 0.8866(18) 0.025(5) 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 0 '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 0.006 '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
C3 O1 C4 107.66(9) . . ?
C3 N1 C6 121.43(11) . . ?
C3 N1 C1 110.12(10) . . ?
C6 N1 C1 126.24(10) . . ?
C1 O5 H5 103.3(13) . . ?
C4 O3 C21 115.62(12) . . ?
C9 N2 C5 112.80(11) . . ?
C9 N2 H2 107.2(13) . . ?
C5 N2 H2 107.3(14) . . ?
O5 C1 N1 110.14(11) . . ?
O5 C1 C10 111.08(11) . . ?
N1 C1 C10 113.83(11) . . ?
O5 C1 C4 108.38(10) . . ?
N1 C1 C4 97.79(10) . . ?
C10 C1 C4 114.84(11) . . ?
O3 C4 O1 108.06(11) . . ?
O3 C4 C12 115.30(12) . . ?
O1 C4 C12 108.33(11) . . ?
O3 C4 C1 106.08(10) . . ?
O1 C4 C1 102.03(10) . . ?
C12 C4 C1 116.01(12) . . ?
O2 C3 O1 123.12(12) . . ?
O2 C3 N1 127.60(12) . . ?
O1 C3 N1 109.27(11) . . ?
C7 N3 C13 123.59(13) . . ?
C7 N3 H3 116.1(14) . . ?
C13 N3 H3 119.4(14) . . ?
N2 C5 C6 107.76(11) . . ?
N2 C5 H5A 110.2 . . ?
C6 C5 H5A 110.2 . . ?
N2 C5 H5B 110.2 . . ?
C6 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
N1 C6 C5 112.37(10) . . ?
N1 C6 C7 110.53(10) . . ?
C5 C6 C7 114.03(11) . . ?
N1 C6 H6 107.4(13) . . ?
C5 C6 H6 109.2(13) . . ?
C7 C6 H6 102.6(13) . . ?
O4 C7 N3 124.15(13) . . ?
O4 C7 C6 120.75(12) . . ?
N3 C7 C6 114.96(11) . . ?
C14 C8 C17 118.83(14) . . ?
C14 C8 C9 122.86(13) . . ?
C17 C8 C9 118.32(14) . . ?
N2 C9 C8 112.33(12) . . ?
N2 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
N2 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C22 C11 C15 118.82(15) . . ?
C22 C11 C13 120.68(15) . . ?
C15 C11 C13 120.50(14) . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C11 110.92(12) . . ?
N3 C13 H13A 109.5 . . ?
C11 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 108 . . ?
C8 C14 C16 120.64(15) . . ?
C8 C14 H14 119.7 . . ?
C16 C14 H14 119.7 . . ?
C20 C15 C11 120.36(16) . . ?
C20 C15 H15 119.8 . . ?
C11 C15 H15 119.8 . . ?
C18 C16 C14 120.07(17) . . ?
C18 C16 H16 120 . . ?
C14 C16 H16 120 . . ?
C19 C17 C8 120.41(17) . . ?
C19 C17 H17 119.8 . . ?
C8 C17 H17 119.8 . . ?
C19 C18 C16 119.48(15) . . ?
C19 C18 H18 120.3 . . ?
C16 C18 H18 120.3 . . ?
C17 C19 C18 120.54(15) . . ?
C17 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C23 C20 C15 120.24(18) . . ?
C23 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 C22 C24 120.36(19) . . ?
C11 C22 H22 119.8 . . ?
C24 C22 H22 119.8 . . ?
C20 C23 C24 120.12(17) . . ?
C20 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C22 120.07(19) . . ?
C23 C24 H24 120 . . ?
C22 C24 H24 120 . . ?
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 C3 1.3556(15) . ?
O1 C4 1.4568(16) . ?
O2 C3 1.2085(17) . ?
N1 C3 1.3649(16) . ?
N1 C6 1.4538(16) . ?
N1 C1 1.4593(16) . ?
O5 C1 1.4159(16) . ?
O5 H5 0.95(2) . ?
O3 C4 1.3984(17) . ?
O3 C21 1.4364(18) . ?
N2 C9 1.4571(17) . ?
N2 C5 1.4678(17) . ?
N2 H2 0.89(2) . ?
O4 C7 1.2252(17) . ?
C1 C10 1.5086(19) . ?
C1 C4 1.5478(18) . ?
C4 C12 1.5050(19) . ?
N3 C7 1.3421(18) . ?
N3 C13 1.4580(18) . ?
N3 H3 0.86(2) . ?
C5 C6 1.5238(18) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.5308(18) . ?
C6 H6 0.91(2) . ?
C8 C14 1.389(2) . ?
C8 C17 1.401(2) . ?
C8 C9 1.515(2) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 C22 1.385(2) . ?
C11 C15 1.395(2) . ?
C11 C13 1.506(2) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C16 1.397(2) . ?
C14 H14 0.95 . ?
C15 C20 1.387(2) . ?
C15 H15 0.95 . ?
C16 C18 1.390(2) . ?
C16 H16 0.95 . ?
C17 C19 1.387(2) . ?
C17 H17 0.95 . ?
C18 C19 1.389(3) . ?
C18 H18 0.95 . ?
C19 H19 0.95 . ?
C20 C23 1.372(3) . ?
C20 H20 0.95 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 C24 1.393(3) . ?
C22 H22 0.95 . ?
C23 C24 1.377(4) . ?
C23 H23 0.95 . ?
C24 H24 0.95 . ?
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
C3 N1 C1 O5 -83.07(12) . . . . ?
C6 N1 C1 O5 80.12(14) . . . . ?
C3 N1 C1 C10 151.43(11) . . . . ?
C6 N1 C1 C10 -45.38(17) . . . . ?
C3 N1 C1 C4 29.83(13) . . . . ?
C6 N1 C1 C4 -166.98(12) . . . . ?
C21 O3 C4 O1 -61.20(16) . . . . ?
C21 O3 C4 C12 60.13(18) . . . . ?
C21 O3 C4 C1 -169.99(14) . . . . ?
C3 O1 C4 O3 -81.83(12) . . . . ?
C3 O1 C4 C12 152.61(11) . . . . ?
C3 O1 C4 C1 29.73(13) . . . . ?
O5 C1 C4 O3 -167.10(11) . . . . ?
N1 C1 C4 O3 78.59(12) . . . . ?
C10 C1 C4 O3 -42.25(15) . . . . ?
O5 C1 C4 O1 79.86(12) . . . . ?
N1 C1 C4 O1 -34.45(12) . . . . ?
C10 C1 C4 O1 -155.29(11) . . . . ?
O5 C1 C4 C12 -37.63(15) . . . . ?
N1 C1 C4 C12 -151.94(12) . . . . ?
C10 C1 C4 C12 87.21(16) . . . . ?
C4 O1 C3 O2 167.34(13) . . . . ?
C4 O1 C3 N1 -11.63(14) . . . . ?
C6 N1 C3 O2 3.7(2) . . . . ?
C1 N1 C3 O2 167.87(13) . . . . ?
C6 N1 C3 O1 -177.35(10) . . . . ?
C1 N1 C3 O1 -13.21(14) . . . . ?
C9 N2 C5 C6 -172.79(11) . . . . ?
C3 N1 C6 C5 67.15(15) . . . . ?
C1 N1 C6 C5 -94.29(14) . . . . ?
C3 N1 C6 C7 -61.48(15) . . . . ?
C1 N1 C6 C7 137.08(13) . . . . ?
N2 C5 C6 N1 64.49(13) . . . . ?
N2 C5 C6 C7 -168.74(10) . . . . ?
C13 N3 C7 O4 -9.9(2) . . . . ?
C13 N3 C7 C6 174.30(12) . . . . ?
N1 C6 C7 O4 153.26(13) . . . . ?
C5 C6 C7 O4 25.54(18) . . . . ?
N1 C6 C7 N3 -30.74(16) . . . . ?
C5 C6 C7 N3 -158.47(11) . . . . ?
C5 N2 C9 C8 179.71(11) . . . . ?
C14 C8 C9 N2 7.04(19) . . . . ?
C17 C8 C9 N2 -173.08(12) . . . . ?
C7 N3 C13 C11 -133.82(15) . . . . ?
C22 C11 C13 N3 -120.96(17) . . . . ?
C15 C11 C13 N3 58.2(2) . . . . ?
C17 C8 C14 C16 -1.2(2) . . . . ?
C9 C8 C14 C16 178.62(13) . . . . ?
C22 C11 C15 C20 -1.0(2) . . . . ?
C13 C11 C15 C20 179.90(16) . . . . ?
C8 C14 C16 C18 -0.5(2) . . . . ?
C14 C8 C17 C19 1.7(2) . . . . ?
C9 C8 C17 C19 -178.17(14) . . . . ?
C14 C16 C18 C19 1.8(2) . . . . ?
C8 C17 C19 C18 -0.4(3) . . . . ?
C16 C18 C19 C17 -1.4(3) . . . . ?
C11 C15 C20 C23 0.2(3) . . . . ?
C15 C11 C22 C24 1.7(3) . . . . ?
C13 C11 C22 C24 -179.14(19) . . . . ?
C15 C20 C23 C24 -0.2(3) . . . . ?
C20 C23 C24 C22 1.0(4) . . . . ?
C11 C22 C24 C23 -1.7(3) . . . . ?
