#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:37:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178434 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/55/4025553.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_4025553
loop_
_publ_author_name
'Sujeewa Ranatunga'
'Wathsala Liyanage'
'Juan R. Del Valle'
_publ_section_title
;
 Synthesis and Conformational Analysis of Bicyclic Extended Dipeptide
 Surrogates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5113
_journal_page_last               5125
_journal_paper_doi               10.1021/jo1008433
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C23 H31 N3 O7'
_chemical_formula_sum            'C23 H31 N3 O7'
_chemical_formula_weight         461.51
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 106.951(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6123(3)
_cell_length_b                   32.1258(14)
_cell_length_c                   10.7380(5)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    228(2)
_cell_measurement_theta_max      25.14
_cell_measurement_theta_min      2.08
_cell_volume                     2511.90(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      228(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  '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  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            45065
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker,SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chip
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     623
_refine_ls_number_reflns         6325
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0403
_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)+(0.0484P)²+0.1910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                4644
_reflns_number_total             6325
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1008433_si_004.cif
_cod_data_source_block           jd05
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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               4025553
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7136(4) 1.01540(13) 0.2758(3) 0.0647(9) Uani 1 1 d . . .
H1 H 0.7595 1.0069 0.3630 0.078 Uiso 1 1 calc R . .
C2 C 0.8337(5) 1.02999(14) 0.2089(4) 0.0821(12) Uani 1 1 d . . .
H2 H 0.9602 1.0316 0.2519 0.098 Uiso 1 1 calc R . .
C3 C 0.7690(7) 1.04195(11) 0.0822(4) 0.0719(10) Uani 1 1 d . . .
H3 H 0.8506 1.0520 0.0382 0.086 Uiso 1 1 calc R . .
C4 C 0.5869(6) 1.03941(11) 0.0196(3) 0.0662(10) Uani 1 1 d . . .
H4 H 0.5426 1.0471 -0.0685 0.079 Uiso 1 1 calc R . .
C5 C 0.4671(5) 1.02566(9) 0.0847(3) 0.0518(7) Uani 1 1 d . . .
H5 H 0.3408 1.0245 0.0409 0.062 Uiso 1 1 calc R . .
C6 C 0.5295(4) 1.01346(8) 0.2140(3) 0.0413(6) Uani 1 1 d . . .
C7 C 0.3886(4) 1.00294(9) 0.2833(3) 0.0456(6) Uani 1 1 d . . .
H7A H 0.2924 0.9861 0.2241 0.055 Uiso 1 1 calc R . .
H7B H 0.3314 1.0290 0.2988 0.055 Uiso 1 1 calc R . .
C8 C 0.4549(4) 0.97968(8) 0.4130(2) 0.0412(6) Uani 1 1 d . A .
H8 H 0.5693 0.9931 0.4660 0.049 Uiso 1 1 calc R . .
C9 C 0.3101(5) 0.98452(11) 0.4843(3) 0.0622(9) Uani 1 1 d . . .
O1 O 0.257(4) 1.0177(3) 0.508(3) 0.114(8) Uani 0.59(5) 1 d P A 1
O1A O 0.335(3) 1.0090(12) 0.580(3) 0.113(9) Uani 0.41(5) 1 d P A 2
O2 O 0.2086(3) 0.95195(8) 0.4784(2) 0.0641(6) Uani 1 1 d . A .
C10 C 0.0672(6) 0.95315(14) 0.5425(4) 0.0798(11) Uani 1 1 d . . .
H10A H 0.0699 0.9799 0.5851 0.120 Uiso 1 1 calc R A .
H10B H 0.0878 0.9311 0.6068 0.120 Uiso 1 1 calc R . .
H10C H -0.0517 0.9493 0.4787 0.120 Uiso 1 1 calc R . .
N1 N 0.4947(3) 0.93642(6) 0.39515(17) 0.0349(5) Uani 1 1 d . . .
H1N H 0.4618 0.9256 0.3175 0.042 Uiso 1 1 calc R A .
C11 C 0.5823(3) 0.91284(8) 0.4977(2) 0.0323(5) Uani 1 1 d . A .
O3 O 0.6629(3) 0.92793(6) 0.60411(16) 0.0513(5) Uani 1 1 d . . .
C12 C 0.5639(3) 0.86646(8) 0.4782(2) 0.0309(5) Uani 1 1 d . . .
H12 H 0.5492 0.8594 0.3860 0.037 Uiso 1 1 calc R A .
N2 N 0.7215(3) 0.84419(6) 0.56361(16) 0.0293(4) Uani 1 1 d . A .
C13 C 0.8772(3) 0.84175(8) 0.5295(2) 0.0338(5) Uani 1 1 d . . .
O4 O 0.9023(2) 0.86033(6) 0.43699(15) 0.0409(4) Uani 1 1 d . A .
O5 O 1.0151(2) 0.81829(7) 0.60328(17) 0.0475(5) Uani 1 1 d . A .
C14 C 0.9876(4) 0.79510(10) 0.7119(3) 0.0514(7) Uani 1 1 d . . .
H14A H 1.0131 0.8132 0.7886 0.062 Uiso 1 1 calc R A .
H14B H 1.0737 0.7717 0.7325 0.062 Uiso 1 1 calc R . .
C15 C 0.7942(4) 0.77901(8) 0.6804(2) 0.0368(6) Uani 1 1 d . A .
H15 H 0.7683 0.7619 0.6004 0.044 Uiso 1 1 calc R . .
C16 C 0.6671(3) 0.81604(8) 0.6542(2) 0.0328(5) Uani 1 1 d . . .
H16 H 0.6761 0.8308 0.7367 0.039 Uiso 1 1 calc R A .
C17 C 0.4659(4) 0.80755(9) 0.5820(3) 0.0447(6) Uani 1 1 d . A .
H17A H 0.3973 0.7991 0.6422 0.054 Uiso 1 1 calc R . .
H17B H 0.4539 0.7859 0.5156 0.054 Uiso 1 1 calc R . .
C18 C 0.4002(4) 0.84974(9) 0.5201(3) 0.0447(6) Uani 1 1 d . A .
H18A H 0.3705 0.8685 0.5831 0.054 Uiso 1 1 calc R . .
H18B H 0.2914 0.8465 0.4447 0.054 Uiso 1 1 calc R . .
N3 N 0.7696(3) 0.75328(7) 0.78529(17) 0.0424(5) Uani 1 1 d . . .
H3N H 0.7767 0.7646 0.8602 0.051 Uiso 1 1 calc R A .
C19 C 0.7360(5) 0.71248(9) 0.7683(2) 0.0544(8) Uani 1 1 d . A .
O6 O 0.700(6) 0.6940(5) 0.6648(18) 0.097(5) Uani 0.71(10) 1 d P A 1
O6A O 0.762(10) 0.6952(10) 0.677(4) 0.074(10) Uani 0.29(10) 1 d P A 2
O7 O 0.7253(3) 0.69505(6) 0.88050(15) 0.0523(5) Uani 1 1 d . . .
C20 C 0.6872(5) 0.65023(9) 0.8848(2) 0.0571(9) Uani 1 1 d . A .
C21 C 0.8384(7) 0.62484(12) 0.8577(4) 0.0881(13) Uani 1 1 d . . .
H21A H 0.8291 0.6265 0.7659 0.132 Uiso 1 1 calc R A .
H21B H 0.8268 0.5960 0.8813 0.132 Uiso 1 1 calc R . .
H21C H 0.9566 0.6356 0.9086 0.132 Uiso 1 1 calc R . .
C22 C 0.6866(6) 0.64440(10) 1.0249(3) 0.0618(9) Uani 1 1 d . . .
H22A H 0.8015 0.6545 1.0829 0.093 Uiso 1 1 calc R A .
H22B H 0.6727 0.6151 1.0414 0.093 Uiso 1 1 calc R . .
H22C H 0.5853 0.6599 1.0398 0.093 Uiso 1 1 calc R . .
C23 C 0.4986(7) 0.64032(12) 0.7931(3) 0.0848(13) Uani 1 1 d . . .
H23A H 0.4088 0.6593 0.8097 0.127 Uiso 1 1 calc R A .
H23B H 0.4658 0.6119 0.8073 0.127 Uiso 1 1 calc R . .
H23C H 0.5009 0.6435 0.7038 0.127 Uiso 1 1 calc R . .
C24 C 1.2985(4) 0.78496(12) 1.1727(3) 0.0619(9) Uani 1 1 d . . .
H24 H 1.3056 0.8046 1.2389 0.074 Uiso 1 1 calc R . .
C25 C 1.3950(5) 0.79129(18) 1.0844(5) 0.0940(15) Uani 1 1 d . . .
H25 H 1.4683 0.8152 1.0917 0.113 Uiso 1 1 calc R . .
C26 C 1.3869(6) 0.7641(2) 0.9880(5) 0.107(2) Uani 1 1 d . . .
H26 H 1.4535 0.7690 0.9282 0.128 Uiso 1 1 calc R . .
C27 C 1.2802(7) 0.7289(2) 0.9774(4) 0.0949(16) Uani 1 1 d . . .
H27 H 1.2750 0.7095 0.9107 0.114 Uiso 1 1 calc R . .
C28 C 1.1805(5) 0.72189(12) 1.0648(3) 0.0622(9) Uani 1 1 d . . .
H28 H 1.1057 0.6982 1.0564 0.075 Uiso 1 1 calc R . .
C29 C 1.1915(4) 0.74999(9) 1.1643(2) 0.0433(6) Uani 1 1 d . . .
C30 C 1.0809(4) 0.74337(9) 1.2577(3) 0.0473(7) Uani 1 1 d . . .
H30A H 1.1457 0.7560 1.3416 0.057 Uiso 1 1 calc R . .
H30B H 1.0709 0.7134 1.2717 0.057 Uiso 1 1 calc R . .
C31 C 0.8868(4) 0.76205(7) 1.2095(2) 0.0351(6) Uani 1 1 d . . .
H31 H 0.8280 0.7519 1.1199 0.042 Uiso 1 1 calc R . .
C32 C 0.7725(4) 0.74800(8) 1.2952(2) 0.0358(6) Uani 1 1 d . . .
O8 O 0.7232(3) 0.76941(6) 1.36975(17) 0.0494(5) Uani 1 1 d . . .
O9 O 0.7371(3) 0.70735(6) 1.27879(18) 0.0522(5) Uani 1 1 d . . .
C33 C 0.6296(5) 0.68902(10) 1.3551(3) 0.0589(9) Uani 1 1 d . . .
H33A H 0.6957 0.6914 1.4469 0.088 Uiso 1 1 calc R . .
H33B H 0.6079 0.6599 1.3322 0.088 Uiso 1 1 calc R . .
H33C H 0.5130 0.7034 1.3376 0.088 Uiso 1 1 calc R . .
N4 N 0.8904(3) 0.80706(6) 1.20713(17) 0.0335(5) Uani 1 1 d . . .
H4N H 0.9059 0.8204 1.2801 0.040 Uiso 1 1 calc R . .
C34 C 0.8711(3) 0.82917(8) 1.09857(19) 0.0311(5) Uani 1 1 d . . .
O10 O 0.8510(3) 0.81330(6) 0.99094(14) 0.0437(4) Uani 1 1 d . . .
C35 C 0.8636(4) 0.87612(8) 1.1129(2) 0.0351(6) Uani 1 1 d . . .
H35 H 0.9060 0.8843 1.2058 0.042 Uiso 1 1 calc R . .
N5 N 0.9726(3) 0.89699(6) 1.03900(16) 0.0301(4) Uani 1 1 d . . .
C36 C 1.1547(3) 0.90098(8) 1.0918(2) 0.0356(6) Uani 1 1 d . . .
O11 O 1.2406(3) 0.88532(6) 1.19476(17) 0.0516(5) Uani 1 1 d . . .
O12 O 1.2489(2) 0.92364(6) 1.02699(17) 0.0442(5) Uani 1 1 d . . .
C37 C 1.1499(4) 0.94202(9) 0.9033(2) 0.0406(6) Uani 1 1 d . . .
H37A H 1.1282 0.9210 0.8344 0.049 Uiso 1 1 calc R . .
H37B H 1.2229 0.9645 0.8816 0.049 Uiso 1 1 calc R . .
C38 C 0.9692(3) 0.95897(7) 0.9117(2) 0.0312(5) Uani 1 1 d . . .
H38 H 0.9931 0.9774 0.9888 0.037 Uiso 1 1 calc R . .
C39 C 0.8558(3) 0.92248(8) 0.9319(2) 0.0339(5) Uani 1 1 d . . .
H39 H 0.8175 0.9056 0.8513 0.041 Uiso 1 1 calc R . .
C40 C 0.6905(4) 0.93153(10) 0.9786(3) 0.0551(8) Uani 1 1 d . . .
H40A H 0.5816 0.9372 0.9052 0.066 Uiso 1 1 calc R . .
H40B H 0.7134 0.9554 1.0380 0.066 Uiso 1 1 calc R . .
C41 C 0.6671(4) 0.89173(10) 1.0487(3) 0.0553(8) Uani 1 1 d . . .
H41A H 0.5963 0.8711 0.9870 0.066 Uiso 1 1 calc R . .
H41B H 0.6040 0.8974 1.1145 0.066 Uiso 1 1 calc R . .
N6 N 0.8745(3) 0.98288(7) 0.79707(17) 0.0394(5) Uani 1 1 d . . .
H6N H 0.7906 0.9711 0.7340 0.047 Uiso 1 1 calc R . .
C42 C 0.9168(4) 1.02318(8) 0.7887(2) 0.0372(6) Uani 1 1 d . . .
O13 O 1.0362(3) 1.04128(6) 0.87054(16) 0.0464(5) Uani 1 1 d . . .
O14 O 0.8080(3) 1.03975(6) 0.67830(16) 0.0516(5) Uani 1 1 d . . .
C43 C 0.8165(5) 1.08517(9) 0.6545(3) 0.0584(9) Uani 1 1 d . . .
C44 C 0.6560(7) 1.09091(12) 0.5315(4) 0.1014(17) Uani 1 1 d . . .
H44A H 0.6351 1.1204 0.5136 0.152 Uiso 1 1 calc R . .
H44B H 0.5465 1.0784 0.5440 0.152 Uiso 1 1 calc R . .
H44C H 0.6846 1.0776 0.4587 0.152 Uiso 1 1 calc R . .
C45 C 0.7792(6) 1.10947(11) 0.7646(3) 0.0689(10) Uani 1 1 d . . .
H45A H 0.8805 1.1057 0.8431 0.103 Uiso 1 1 calc R . .
H45B H 0.6666 1.0995 0.7793 0.103 Uiso 1 1 calc R . .
H45C H 0.7665 1.1388 0.7420 0.103 Uiso 1 1 calc R . .
C46 C 1.0003(7) 1.09560(13) 0.6355(4) 0.0873(13) Uani 1 1 d . . .
H46A H 1.0959 1.0923 0.7173 0.131 Uiso 1 1 calc R . .
H46B H 0.9990 1.1242 0.6059 0.131 Uiso 1 1 calc R . .
H46C H 1.0240 1.0771 0.5709 0.131 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 0.0000 '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
C6 C1 C2 119.9(3) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 C7 123.1(3) . . ?
C5 C6 C7 118.1(3) . . ?
C6 C7 C8 117.7(2) . . ?
C6 C7 H7A 107.9 . . ?
C8 C7 H7A 107.9 . . ?
C6 C7 H7B 107.9 . . ?
C8 C7 H7B 107.9 . . ?
H7A C7 H7B 107.2 . . ?
N1 C8 C9 112.0(2) . . ?
N1 C8 C7 112.0(2) . . ?
C9 C8 C7 108.2(2) . . ?
N1 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
C7 C8 H8 108.1 . . ?
O1 C9 O2 119.9(11) . . ?
O1A C9 O2 119.4(14) . . ?
O1 C9 C8 122.7(5) . . ?
O1A C9 C8 120.9(8) . . ?
O2 C9 C8 113.8(3) . . ?
C9 O2 C10 118.4(3) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 N1 C8 120.43(19) . . ?
C11 N1 H1N 119.8 . . ?
C8 N1 H1N 119.8 . . ?
O3 C11 N1 122.3(2) . . ?
O3 C11 C12 121.4(2) . . ?
N1 C11 C12 116.12(18) . . ?
N2 C12 C11 111.71(18) . . ?
N2 C12 C18 103.34(18) . . ?
C11 C12 C18 110.8(2) . . ?
N2 C12 H12 110.3 . . ?
C11 C12 H12 110.3 . . ?
C18 C12 H12 110.3 . . ?
C13 N2 C12 118.97(18) . . ?
C13 N2 C16 125.8(2) . . ?
C12 N2 C16 112.15(18) . . ?
O4 C13 N2 123.7(2) . . ?
O4 C13 O5 118.2(2) . . ?
N2 C13 O5 118.1(2) . . ?
C13 O5 C14 119.4(2) . . ?
O5 C14 C15 110.9(2) . . ?
O5 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
O5 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N3 C15 C14 111.2(2) . . ?
N3 C15 C16 111.9(2) . . ?
C14 C15 C16 107.7(2) . . ?
N3 C15 H15 108.7 . . ?
C14 C15 H15 108.7 . . ?
C16 C15 H15 108.7 . . ?
N2 C16 C15 108.66(19) . . ?
N2 C16 C17 102.00(17) . . ?
C15 C16 C17 116.6(2) . . ?
N2 C16 H16 109.7 . . ?
C15 C16 H16 109.7 . . ?
C17 C16 H16 109.7 . . ?
C16 C17 C18 102.4(2) . . ?
C16 C17 H17A 111.3 . . ?
C18 C17 H17A 111.3 . . ?
C16 C17 H17B 111.3 . . ?
C18 C17 H17B 111.3 . . ?
H17A C17 H17B 109.2 . . ?
C17 C18 C12 104.3(2) . . ?
C17 C18 H18A 110.9 . . ?
C12 C18 H18A 110.9 . . ?
C17 C18 H18B 110.9 . . ?
C12 C18 H18B 110.9 . . ?
H18A C18 H18B 108.9 . . ?
C19 N3 C15 121.0(2) . . ?
C19 N3 H3N 119.5 . . ?
C15 N3 H3N 119.5 . . ?
O6A C19 N3 120(2) . . ?
O6 C19 N3 125.9(7) . . ?
O6A C19 O7 127.5(17) . . ?
O6 C19 O7 123.6(9) . . ?
N3 C19 O7 110.1(2) . . ?
C19 O7 C20 119.8(2) . . ?
O7 C20 C21 110.8(3) . . ?
O7 C20 C22 102.1(2) . . ?
C21 C20 C22 110.3(3) . . ?
O7 C20 C23 110.0(3) . . ?
C21 C20 C23 113.1(3) . . ?
C22 C20 C23 110.0(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C29 120.1(4) . . ?
C25 C24 H24 119.9 . . ?
C29 C24 H24 119.9 . . ?
C26 C25 C24 121.5(5) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C25 C26 C27 119.4(4) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C26 C27 C28 120.2(4) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C29 C28 C27 119.7(4) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C24 C29 C28 119.0(3) . . ?
C24 C29 C30 120.6(3) . . ?
C28 C29 C30 120.3(3) . . ?
C29 C30 C31 113.0(2) . . ?
C29 C30 H30A 109.0 . . ?
C31 C30 H30A 109.0 . . ?
C29 C30 H30B 109.0 . . ?
C31 C30 H30B 109.0 . . ?
H30A C30 H30B 107.8 . . ?
N4 C31 C32 109.1(2) . . ?
N4 C31 C30 112.0(2) . . ?
C32 C31 C30 110.2(2) . . ?
N4 C31 H31 108.5 . . ?
C32 C31 H31 108.5 . . ?
C30 C31 H31 108.5 . . ?
O8 C32 O9 124.1(2) . . ?
O8 C32 C31 125.9(2) . . ?
O9 C32 C31 110.1(2) . . ?
C32 O9 C33 116.8(2) . . ?
O9 C33 H33A 109.5 . . ?
O9 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O9 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C34 N4 C31 123.28(18) . . ?
C34 N4 H4N 118.4 . . ?
C31 N4 H4N 118.4 . . ?
O10 C34 N4 123.4(2) . . ?
O10 C34 C35 120.56(19) . . ?
N4 C34 C35 115.93(19) . . ?
N5 C35 C34 110.8(2) . . ?
N5 C35 C41 103.78(19) . . ?
C34 C35 C41 109.8(2) . . ?
N5 C35 H35 110.8 . . ?
C34 C35 H35 110.8 . . ?
C41 C35 H35 110.8 . . ?
C36 N5 C35 119.51(19) . . ?
C36 N5 C39 126.0(2) . . ?
C35 N5 C39 111.54(19) . . ?
O11 C36 N5 124.0(2) . . ?
O11 C36 O12 117.8(2) . . ?
N5 C36 O12 118.20(19) . . ?
C36 O12 C37 118.74(19) . . ?
O12 C37 C38 109.37(19) . . ?
O12 C37 H37A 109.8 . . ?
C38 C37 H37A 109.8 . . ?
O12 C37 H37B 109.8 . . ?
C38 C37 H37B 109.8 . . ?
H37A C37 H37B 108.2 . . ?
N6 C38 C37 112.09(19) . . ?
N6 C38 C39 111.69(18) . . ?
C37 C38 C39 107.4(2) . . ?
N6 C38 H38 108.5 . . ?
C37 C38 H38 108.5 . . ?
C39 C38 H38 108.5 . . ?
N5 C39 C38 107.61(18) . . ?
N5 C39 C40 102.6(2) . . ?
C38 C39 C40 117.7(2) . . ?
N5 C39 H39 109.5 . . ?
C38 C39 H39 109.5 . . ?
C40 C39 H39 109.5 . . ?
C39 C40 C41 103.4(2) . . ?
C39 C40 H40A 111.1 . . ?
C41 C40 H40A 111.1 . . ?
C39 C40 H40B 111.1 . . ?
C41 C40 H40B 111.1 . . ?
H40A C40 H40B 109.1 . . ?
C40 C41 C35 104.9(2) . . ?
C40 C41 H41A 110.8 . . ?
C35 C41 H41A 110.8 . . ?
C40 C41 H41B 110.8 . . ?
C35 C41 H41B 110.8 . . ?
H41A C41 H41B 108.8 . . ?
C42 N6 C38 119.83(19) . . ?
C42 N6 H6N 120.1 . . ?
C38 N6 H6N 120.1 . . ?
O13 C42 O14 126.1(2) . . ?
O13 C42 N6 123.9(2) . . ?
O14 C42 N6 110.1(2) . . ?
C42 O14 C43 119.7(2) . . ?
O14 C43 C46 109.3(3) . . ?
O14 C43 C45 110.2(2) . . ?
C46 C43 C45 112.6(3) . . ?
O14 C43 C44 101.7(2) . . ?
C46 C43 C44 113.3(3) . . ?
C45 C43 C44 109.2(3) . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C43 C45 H45A 109.5 . . ?
C43 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C43 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 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
C1 C6 1.366(4) . ?
C1 C2 1.397(5) . ?
C1 H1 0.9400 . ?
C2 C3 1.361(6) . ?
C2 H2 0.9400 . ?
C3 C4 1.355(6) . ?
C3 H3 0.9400 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.510(4) . ?
C7 C8 1.531(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 N1 1.447(3) . ?
C8 C9 1.522(4) . ?
C8 H8 0.9900 . ?
C9 O1 1.195(9) . ?
C9 O1A 1.262(11) . ?
C9 O2 1.291(4) . ?
O2 C10 1.438(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
N1 C11 1.343(3) . ?
N1 H1N 0.8700 . ?
C11 O3 1.228(3) . ?
C11 C12 1.505(3) . ?
C12 N2 1.467(3) . ?
C12 C18 1.540(4) . ?
C12 H12 0.9900 . ?
N2 C13 1.341(3) . ?
N2 C16 1.472(3) . ?
C13 O4 1.221(3) . ?
C13 O5 1.346(3) . ?
O5 C14 1.449(3) . ?
C14 C15 1.503(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 N3 1.452(3) . ?
C15 C16 1.507(4) . ?
C15 H15 0.9900 . ?
C16 C17 1.527(4) . ?
C16 H16 0.9900 . ?
C17 C18 1.528(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
N3 C19 1.338(4) . ?
N3 H3N 0.8700 . ?
C19 O6A 1.20(3) . ?
C19 O6 1.220(16) . ?
C19 O7 1.352(3) . ?
O7 C20 1.472(3) . ?
C20 C21 1.507(6) . ?
C20 C22 1.517(4) . ?
C20 C23 1.519(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C24 C25 1.373(6) . ?
C24 C29 1.375(5) . ?
C24 H24 0.9400 . ?
C25 C26 1.342(8) . ?
C25 H25 0.9400 . ?
C26 C27 1.378(8) . ?
C26 H26 0.9400 . ?
C27 C28 1.386(6) . ?
C27 H27 0.9400 . ?
C28 C29 1.383(4) . ?
C28 H28 0.9400 . ?
C29 C30 1.501(4) . ?
C30 C31 1.538(4) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C31 N4 1.446(3) . ?
C31 C32 1.508(3) . ?
C31 H31 0.9900 . ?
C32 O8 1.196(3) . ?
C32 O9 1.334(3) . ?
O9 C33 1.442(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 H33C 0.9700 . ?
N4 C34 1.336(3) . ?
N4 H4N 0.8700 . ?
C34 O10 1.231(3) . ?
C34 C35 1.519(3) . ?
C35 N5 1.467(3) . ?
C35 C41 1.537(4) . ?
C35 H35 0.9900 . ?
N5 C36 1.342(3) . ?
N5 C39 1.479(3) . ?
C36 O11 1.217(3) . ?
C36 O12 1.349(3) . ?
O12 C37 1.448(3) . ?
C37 C38 1.507(4) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C38 N6 1.452(3) . ?
C38 C39 1.508(3) . ?
C38 H38 0.9900 . ?
C39 C40 1.512(4) . ?
C39 H39 0.9900 . ?
C40 C41 1.521(4) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
N6 C42 1.343(3) . ?
N6 H6N 0.8700 . ?
C42 O13 1.213(3) . ?
C42 O14 1.342(3) . ?
O14 C43 1.486(3) . ?
C43 C46 1.509(6) . ?
C43 C45 1.511(5) . ?
C43 C44 1.526(5) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C44 H44C 0.9700 . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C45 H45C 0.9700 . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C46 H46C 0.9700 . ?
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
C46 H46A O13 0.97 2.46 3.015(4) 116.3 .
C45 H45A O13 0.97 2.36 2.937(4) 117.4 .
C33 H33A O6 0.97 2.33 3.215(16) 150.9 1_556
C31 H31 O10 0.99 2.44 2.814(3) 101.5 .
C30 H30B O9 0.98 2.57 2.930(4) 101.5 .
C23 H23C O6 0.97 2.34 2.91(3) 116.7 .
C21 H21A O6 0.97 2.49 3.01(2) 113.2 .
C15 H15 O8 0.99 2.41 3.235(3) 140.3 1_554
C15 H15 O6 0.99 2.39 2.818(17) 105.0 .
C10 H10A O1 0.97 2.21 2.613(16) 103.8 .
C7 H7B O1 0.98 2.50 2.911(16) 104.9 .
C5 H5 O13 0.94 2.56 3.450(4) 158.7 1_454
N6 H6N O3 0.87 2.01 2.839(3) 159.8 .
N4 H4N O4 0.87 2.12 2.983(3) 169.0 1_556
N3 H3N O10 0.87 2.07 2.860(3) 151.0 .
N1 H1N O11 0.87 2.23 2.939(3) 139.2 1_454
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
C6 C1 C2 C3 -0.6(6) . . . . ?
C1 C2 C3 C4 -0.5(6) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
C2 C1 C6 C5 0.9(5) . . . . ?
C2 C1 C6 C7 -172.6(3) . . . . ?
C4 C5 C6 C1 0.0(5) . . . . ?
C4 C5 C6 C7 173.8(3) . . . . ?
C1 C6 C7 C8 -21.0(4) . . . . ?
C5 C6 C7 C8 165.5(3) . . . . ?
C6 C7 C8 N1 -73.7(3) . . . . ?
C6 C7 C8 C9 162.3(3) . . . . ?
N1 C8 C9 O1 -180(2) . . . . ?
C7 C8 C9 O1 -56(2) . . . . ?
N1 C8 C9 O1A 132(3) . . . . ?
C7 C8 C9 O1A -105(3) . . . . ?
N1 C8 C9 O2 -21.3(4) . . . . ?
C7 C8 C9 O2 102.7(3) . . . . ?
O1 C9 O2 C10 -21.1(19) . . . . ?
O1A C9 O2 C10 27(2) . . . . ?
C8 C9 O2 C10 -180.0(3) . . . . ?
C9 C8 N1 C11 -69.0(3) . . . . ?
C7 C8 N1 C11 169.1(2) . . . . ?
C8 N1 C11 O3 -14.5(4) . . . . ?
C8 N1 C11 C12 160.8(2) . . . . ?
O3 C11 C12 N2 -31.3(3) . . . . ?
N1 C11 C12 N2 153.3(2) . . . . ?
O3 C11 C12 C18 83.4(3) . . . . ?
N1 C11 C12 C18 -92.0(2) . . . . ?
C11 C12 N2 C13 -80.3(3) . . . . ?
C18 C12 N2 C13 160.6(2) . . . . ?
C11 C12 N2 C16 118.4(2) . . . . ?
C18 C12 N2 C16 -0.8(2) . . . . ?
C12 N2 C13 O4 7.1(4) . . . . ?
C16 N2 C13 O4 165.7(2) . . . . ?
C12 N2 C13 O5 -174.5(2) . . . . ?
C16 N2 C13 O5 -16.0(3) . . . . ?
O4 C13 O5 C14 -178.5(2) . . . . ?
N2 C13 O5 C14 3.0(3) . . . . ?
C13 O5 C14 C15 35.8(3) . . . . ?
O5 C14 C15 N3 176.0(2) . . . . ?
O5 C14 C15 C16 -61.1(3) . . . . ?
C13 N2 C16 C15 -11.7(3) . . . . ?
C12 N2 C16 C15 148.09(19) . . . . ?
C13 N2 C16 C17 -135.5(2) . . . . ?
C12 N2 C16 C17 24.3(2) . . . . ?
N3 C15 C16 N2 170.37(18) . . . . ?
C14 C15 C16 N2 47.9(2) . . . . ?
N3 C15 C16 C17 -75.1(3) . . . . ?
C14 C15 C16 C17 162.4(2) . . . . ?
N2 C16 C17 C18 -37.6(3) . . . . ?
C15 C16 C17 C18 -155.8(2) . . . . ?
C16 C17 C18 C12 38.1(3) . . . . ?
N2 C12 C18 C17 -23.3(3) . . . . ?
C11 C12 C18 C17 -143.1(2) . . . . ?
C14 C15 N3 C19 -113.4(3) . . . . ?
C16 C15 N3 C19 126.2(3) . . . . ?
C15 N3 C19 O6A 15(3) . . . . ?
C15 N3 C19 O6 -10(3) . . . . ?
C15 N3 C19 O7 177.7(3) . . . . ?
O6A C19 O7 C20 -20(4) . . . . ?
O6 C19 O7 C20 7(3) . . . . ?
N3 C19 O7 C20 179.4(3) . . . . ?
C19 O7 C20 C21 62.7(4) . . . . ?
C19 O7 C20 C22 -179.8(3) . . . . ?
C19 O7 C20 C23 -63.0(4) . . . . ?
C29 C24 C25 C26 0.5(6) . . . . ?
C24 C25 C26 C27 -0.3(6) . . . . ?
C25 C26 C27 C28 0.7(6) . . . . ?
C26 C27 C28 C29 -1.3(5) . . . . ?
C25 C24 C29 C28 -1.1(5) . . . . ?
C25 C24 C29 C30 -178.1(3) . . . . ?
C27 C28 C29 C24 1.5(4) . . . . ?
C27 C28 C29 C30 178.5(3) . . . . ?
C24 C29 C30 C31 89.8(3) . . . . ?
C28 C29 C30 C31 -87.2(3) . . . . ?
C29 C30 C31 N4 -68.2(3) . . . . ?
C29 C30 C31 C32 170.1(2) . . . . ?
N4 C31 C32 O8 -13.8(3) . . . . ?
C30 C31 C32 O8 109.5(3) . . . . ?
N4 C31 C32 O9 167.8(2) . . . . ?
C30 C31 C32 O9 -68.8(3) . . . . ?
O8 C32 O9 C33 1.2(4) . . . . ?
C31 C32 O9 C33 179.6(2) . . . . ?
C32 C31 N4 C34 -136.8(2) . . . . ?
C30 C31 N4 C34 100.9(3) . . . . ?
C31 N4 C34 O10 -1.0(4) . . . . ?
C31 N4 C34 C35 175.4(2) . . . . ?
O10 C34 C35 N5 -45.5(3) . . . . ?
N4 C34 C35 N5 137.9(2) . . . . ?
O10 C34 C35 C41 68.5(3) . . . . ?
N4 C34 C35 C41 -108.0(2) . . . . ?
C34 C35 N5 C36 -82.8(3) . . . . ?
C41 C35 N5 C36 159.4(2) . . . . ?
C34 C35 N5 C39 115.4(2) . . . . ?
C41 C35 N5 C39 -2.4(3) . . . . ?
C35 N5 C36 O11 6.2(4) . . . . ?
C39 N5 C36 O11 165.2(2) . . . . ?
C35 N5 C36 O12 -173.9(2) . . . . ?
C39 N5 C36 O12 -15.0(4) . . . . ?
O11 C36 O12 C37 179.0(2) . . . . ?
N5 C36 O12 C37 -0.8(3) . . . . ?
C36 O12 C37 C38 40.6(3) . . . . ?
O12 C37 C38 N6 172.0(2) . . . . ?
O12 C37 C38 C39 -65.0(2) . . . . ?
C36 N5 C39 C38 -11.5(3) . . . . ?
C35 N5 C39 C38 148.9(2) . . . . ?
C36 N5 C39 C40 -136.2(3) . . . . ?
C35 N5 C39 C40 24.2(3) . . . . ?
N6 C38 C39 N5 172.35(19) . . . . ?
C37 C38 C39 N5 49.1(2) . . . . ?
N6 C38 C39 C40 -72.5(3) . . . . ?
C37 C38 C39 C40 164.2(2) . . . . ?
N5 C39 C40 C41 -35.8(3) . . . . ?
C38 C39 C40 C41 -153.6(2) . . . . ?
C39 C40 C41 C35 35.2(3) . . . . ?
N5 C35 C41 C40 -20.4(3) . . . . ?
C34 C35 C41 C40 -138.8(2) . . . . ?
C37 C38 N6 C42 -84.0(3) . . . . ?
C39 C38 N6 C42 155.4(2) . . . . ?
C38 N6 C42 O13 2.6(4) . . . . ?
C38 N6 C42 O14 -177.2(2) . . . . ?
O13 C42 O14 C43 -6.1(4) . . . . ?
N6 C42 O14 C43 173.7(3) . . . . ?
C42 O14 C43 C46 67.5(3) . . . . ?
C42 O14 C43 C45 -56.7(4) . . . . ?
C42 O14 C43 C44 -172.4(3) . . . . ?
