#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/09/7150920.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_7150920
loop_
_publ_author_name
'Karapetyan, Vahuni'
'Mkrtchyan, Satenik'
'Schmidt, Andreas'
'Gütlein, Jörg-Peter'
'Villinger, Alexander'
'Reinke, Helmut'
'Jiao, Haijun'
'Fischer, Christine'
'Langer, Peter'
_publ_section_title
;
 Synthesis of 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes by
 cyclization of 1,3-bis(silyl enol ethers) with quinazolines
;
_journal_issue                   16
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              2961
_journal_page_last               2968
_journal_paper_doi               10.1039/b803141j
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C20 H24 N2 O7'
_chemical_formula_sum            'C20 H24 N2 O7'
_chemical_formula_weight         404.41
_chemical_melting_point          424
_chemical_name_common
;
11-Hydroxy-4-isopropyl-8,13-diaza-
tricyclo(7.3.1.0$2,7!)trideca-2(7),3,5,10-tetraene-8,10,13-
tricarboxylic acid trimethyl ester
;
_chemical_name_systematic
;
11-Hydroxy-4-isopropyl-8,13-diaza-tricyclo[7.3.1.0^2,7^]trideca-
2(7),3,5,10-tetraene-8,10,13-tricarboxylic acid trimethyl ester
;
_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                102.5480(10)
_cell_angle_beta                 102.9830(10)
_cell_angle_gamma                90.4220(10)
_cell_formula_units_Z            4
_cell_length_a                   9.4794(5)
_cell_length_b                   12.6941(6)
_cell_length_c                   16.9496(9)
_cell_measurement_reflns_used    5165
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.69
_cell_measurement_theta_min      2.53
_cell_volume                     1936.59(17)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23764
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9741
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         11025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0494
_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)+(0.0634P)²+0.2808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1334
_reflns_number_gt                7531
_reflns_number_total             11025
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b803141j.txt
_cod_data_source_block           kv4(5q)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P-1 '
_cod_database_code               7150920
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 0.67670(12) 0.75018(10) 0.44512(7) 0.0312(3) Uani 1 1 d . . .
H1A H 0.6620 0.8137 0.4397 0.047 Uiso 1 1 calc R . .
O2 O 0.21706(13) 0.57477(11) 0.06694(7) 0.0352(3) Uani 1 1 d . . .
O3 O 0.12133(12) 0.67514(10) 0.16662(7) 0.0297(3) Uani 1 1 d . . .
O4 O 0.54070(13) 0.90027(10) 0.38447(8) 0.0356(3) Uani 1 1 d . . .
O5 O 0.33398(12) 0.85084(9) 0.28654(7) 0.0297(3) Uani 1 1 d . . .
O6 O 0.26850(13) 0.43258(10) 0.40028(7) 0.0315(3) Uani 1 1 d . . .
O7 O 0.13750(12) 0.57273(10) 0.36942(7) 0.0301(3) Uani 1 1 d . . .
N1 N 0.33575(13) 0.53645(10) 0.31984(8) 0.0219(3) Uani 1 1 d . . .
N2 N 0.33976(13) 0.60894(10) 0.20349(7) 0.0197(2) Uani 1 1 d . . .
C1 C 0.32953(16) 0.63714(12) 0.29108(8) 0.0195(3) Uani 1 1 d . . .
H1 H 0.2350 0.6699 0.2949 0.023 Uiso 1 1 calc R . .
C2 C 0.45362(16) 0.71579(12) 0.34383(8) 0.0206(3) Uani 1 1 d . . .
C3 C 0.56744(16) 0.68311(13) 0.39521(9) 0.0231(3) Uani 1 1 d . . .
C4 C 0.58279(17) 0.56813(13) 0.40177(9) 0.0248(3) Uani 1 1 d . . .
H4A H 0.5597 0.5587 0.4540 0.030 Uiso 1 1 calc R . .
H4B H 0.6841 0.5488 0.4029 0.030 Uiso 1 1 calc R . .
C5 C 0.48001(16) 0.49393(12) 0.32752(9) 0.0215(3) Uani 1 1 d . . .
H5 H 0.4763 0.4191 0.3372 0.026 Uiso 1 1 calc R . .
C6 C 0.52876(15) 0.49135(12) 0.24790(8) 0.0196(3) Uani 1 1 d . . .
C7 C 0.46117(15) 0.54754(12) 0.18883(8) 0.0191(3) Uani 1 1 d . . .
C8 C 0.22446(16) 0.61542(13) 0.13925(9) 0.0228(3) Uani 1 1 d . . .
C9 C 0.00381(19) 0.69555(18) 0.10202(12) 0.0404(5) Uani 1 1 d . . .
H9A H 0.0426 0.7330 0.0659 0.061 Uiso 1 1 calc R . .
H9B H -0.0649 0.7407 0.1272 0.061 Uiso 1 1 calc R . .
H9C H -0.0459 0.6268 0.0691 0.061 Uiso 1 1 calc R . .
C10 C 0.44945(17) 0.82974(13) 0.34121(9) 0.0240(3) Uani 1 1 d . . .
C11 C 0.3216(2) 0.96341(15) 0.28240(13) 0.0391(4) Uani 1 1 d . . .
H11A H 0.3061 1.0056 0.3352 0.059 Uiso 1 1 calc R . .
H11B H 0.2394 0.9697 0.2372 0.059 Uiso 1 1 calc R . .
H11C H 0.4110 0.9910 0.2720 0.059 Uiso 1 1 calc R . .
C12 C 0.51852(16) 0.54666(12) 0.11965(9) 0.0212(3) Uani 1 1 d . . .
H12 H 0.4759 0.5871 0.0803 0.025 Uiso 1 1 calc R . .
C13 C 0.63741(16) 0.48703(13) 0.10813(9) 0.0232(3) Uani 1 1 d . . .
H13 H 0.6744 0.4865 0.0604 0.028 Uiso 1 1 calc R . .
C14 C 0.70381(16) 0.42763(12) 0.16545(9) 0.0229(3) Uani 1 1 d . . .
C15 C 0.64882(16) 0.43279(12) 0.23522(9) 0.0222(3) Uani 1 1 d . . .
H15 H 0.6944 0.3951 0.2759 0.027 Uiso 1 1 calc R . .
C16 C 0.83165(17) 0.35987(14) 0.15341(10) 0.0275(3) Uani 1 1 d . . .
H16 H 0.8608 0.3271 0.2028 0.033 Uiso 1 1 calc R . .
C17 C 0.96167(19) 0.42960(16) 0.15112(13) 0.0400(4) Uani 1 1 d . . .
H17A H 0.9395 0.4585 0.1009 0.060 Uiso 1 1 calc R . .
H17B H 1.0461 0.3856 0.1507 0.060 Uiso 1 1 calc R . .
H17C H 0.9829 0.4895 0.2003 0.060 Uiso 1 1 calc R . .
C18 C 0.7931(2) 0.26730(14) 0.07677(11) 0.0349(4) Uani 1 1 d . . .
H18A H 0.7129 0.2214 0.0811 0.052 Uiso 1 1 calc R . .
H18B H 0.8777 0.2243 0.0729 0.052 Uiso 1 1 calc R . .
H18C H 0.7639 0.2967 0.0270 0.052 Uiso 1 1 calc R . .
C19 C 0.24850(17) 0.50829(13) 0.36678(9) 0.0231(3) Uani 1 1 d . . .
C20 C 0.0428(2) 0.54983(17) 0.42044(12) 0.0386(4) Uani 1 1 d . . .
H20A H -0.0140 0.4816 0.3931 0.058 Uiso 1 1 calc R . .
H20B H -0.0229 0.6085 0.4280 0.058 Uiso 1 1 calc R . .
H20C H 0.1012 0.5438 0.4747 0.058 Uiso 1 1 calc R . .
O8 O 1.16269(14) 0.03351(11) 0.45878(7) 0.0359(3) Uani 1 1 d . . .
H8 H 1.1533 -0.0337 0.4535 0.054 Uiso 1 1 calc R . .
O9 O 0.71361(13) -0.03914(11) 0.07048(7) 0.0369(3) Uani 1 1 d . . .
O10 O 0.61576(12) -0.07818(10) 0.17087(7) 0.0312(3) Uani 1 1 d . . .
O11 O 1.03930(14) -0.15894(10) 0.39806(8) 0.0383(3) Uani 1 1 d . . .
O12 O 0.84528(13) -0.17774(9) 0.29071(7) 0.0309(3) Uani 1 1 d . . .
O13 O 0.75279(14) 0.30474(9) 0.39910(7) 0.0331(3) Uani 1 1 d . . .
O14 O 0.63379(14) 0.14191(10) 0.37620(8) 0.0364(3) Uani 1 1 d . . .
N3 N 0.82273(14) 0.15512(10) 0.31922(8) 0.0217(3) Uani 1 1 d . . .
N4 N 0.83481(13) 0.01114(10) 0.20735(7) 0.0205(3) Uani 1 1 d . . .
C21 C 0.82252(16) 0.03734(12) 0.29464(9) 0.0208(3) Uani 1 1 d . . .
H21 H 0.7288 0.0046 0.2985 0.025 Uiso 1 1 calc R . .
C22 C 0.94762(17) -0.00363(13) 0.35125(9) 0.0237(3) Uani 1 1 d . . .
C23 C 1.05520(17) 0.06488(13) 0.40394(9) 0.0252(3) Uani 1 1 d . . .
C24 C 1.06695(17) 0.18250(13) 0.40510(9) 0.0255(3) Uani 1 1 d . . .
H24A H 1.1683 0.2046 0.4072 0.031 Uiso 1 1 calc R . .
H24B H 1.0398 0.2250 0.4552 0.031 Uiso 1 1 calc R . .
C25 C 0.96636(16) 0.20502(12) 0.32708(9) 0.0215(3) Uani 1 1 d . . .
H25 H 0.9596 0.2849 0.3333 0.026 Uiso 1 1 calc R . .
C26 C 1.02036(16) 0.15849(12) 0.24977(9) 0.0200(3) Uani 1 1 d . . .
C27 C 0.95503(15) 0.06542(12) 0.19180(9) 0.0199(3) Uani 1 1 d . . .
C28 C 0.71993(16) -0.03524(13) 0.14312(10) 0.0245(3) Uani 1 1 d . . .
C29 C 0.4979(2) -0.13747(17) 0.10593(12) 0.0431(5) Uani 1 1 d . . .
H29A H 0.4501 -0.0887 0.0720 0.065 Uiso 1 1 calc R . .
H29B H 0.4276 -0.1670 0.1311 0.065 Uiso 1 1 calc R . .
H29C H 0.5364 -0.1967 0.0708 0.065 Uiso 1 1 calc R . .
C30 C 0.95002(17) -0.11872(13) 0.35031(10) 0.0263(3) Uani 1 1 d . . .
C31 C 0.8427(2) -0.29326(14) 0.28328(13) 0.0379(4) Uani 1 1 d . . .
H31A H 0.9366 -0.3198 0.2754 0.057 Uiso 1 1 calc R . .
H31B H 0.7659 -0.3285 0.2354 0.057 Uiso 1 1 calc R . .
H31C H 0.8240 -0.3099 0.3339 0.057 Uiso 1 1 calc R . .
C32 C 1.01310(16) 0.02579(12) 0.12297(9) 0.0220(3) Uani 1 1 d . . .
H32 H 0.9708 -0.0384 0.0840 0.026 Uiso 1 1 calc R . .
C33 C 1.13197(16) 0.07947(13) 0.11110(9) 0.0237(3) Uani 1 1 d . . .
H33 H 1.1691 0.0521 0.0635 0.028 Uiso 1 1 calc R . .
C34 C 1.19817(16) 0.17333(13) 0.16811(9) 0.0234(3) Uani 1 1 d . . .
C35 C 1.14143(16) 0.20992(12) 0.23722(9) 0.0229(3) Uani 1 1 d . . .
H35 H 1.1866 0.2722 0.2774 0.027 Uiso 1 1 calc R . .
C36 C 1.32824(17) 0.23350(13) 0.15676(10) 0.0281(3) Uani 1 1 d . . .
H36 H 1.3559 0.2972 0.2048 0.034 Uiso 1 1 calc R . .
C37 C 1.4580(2) 0.16271(18) 0.15807(15) 0.0463(5) Uani 1 1 d . . .
H37A H 1.4765 0.1340 0.2084 0.069 Uiso 1 1 calc R . .
H37B H 1.5437 0.2061 0.1577 0.069 Uiso 1 1 calc R . .
H37C H 1.4370 0.1027 0.1090 0.069 Uiso 1 1 calc R . .
C38 C 1.2958(2) 0.27598(15) 0.07733(11) 0.0353(4) Uani 1 1 d . . .
H38A H 1.2684 0.2151 0.0291 0.053 Uiso 1 1 calc R . .
H38B H 1.3823 0.3157 0.0737 0.053 Uiso 1 1 calc R . .
H38C H 1.2159 0.3244 0.0782 0.053 Uiso 1 1 calc R . .
C39 C 0.73778(17) 0.20864(13) 0.36827(9) 0.0248(3) Uani 1 1 d . . .
C40 C 0.5414(3) 0.19077(19) 0.42959(15) 0.0564(6) Uani 1 1 d . . .
H40A H 0.6014 0.2334 0.4818 0.085 Uiso 1 1 calc R . .
H40B H 0.4841 0.1340 0.4414 0.085 Uiso 1 1 calc R . .
H40C H 0.4762 0.2380 0.4018 0.085 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1A 109.5 . . ?
C8 O3 C9 114.84(13) . . ?
C10 O5 C11 115.63(13) . . ?
C19 O7 C20 114.73(13) . . ?
C19 N1 C1 124.46(12) . . ?
C19 N1 C5 118.47(12) . . ?
C1 N1 C5 111.67(12) . . ?
C8 N2 C7 121.11(12) . . ?
C8 N2 C1 122.12(12) . . ?
C7 N2 C1 114.67(11) . . ?
N1 C1 N2 106.85(11) . . ?
N1 C1 C2 110.01(12) . . ?
N2 C1 C2 111.05(12) . . ?
N1 C1 H1 109.6 . . ?
N2 C1 H1 109.6 . . ?
C2 C1 H1 109.6 . . ?
C3 C2 C10 118.83(14) . . ?
C3 C2 C1 121.50(13) . . ?
C10 C2 C1 119.65(13) . . ?
O1 C3 C2 123.63(14) . . ?
O1 C3 C4 113.37(13) . . ?
C2 C3 C4 123.00(14) . . ?
C3 C4 C5 109.77(12) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 C6 108.95(12) . . ?
N1 C5 C4 107.90(12) . . ?
C6 C5 C4 111.03(12) . . ?
N1 C5 H5 109.6 . . ?
C6 C5 H5 109.6 . . ?
C4 C5 H5 109.6 . . ?
C15 C6 C7 119.41(13) . . ?
C15 C6 C5 117.94(13) . . ?
C7 C6 C5 122.61(13) . . ?
C6 C7 C12 119.06(13) . . ?
C6 C7 N2 118.75(12) . . ?
C12 C7 N2 122.10(13) . . ?
O2 C8 O3 123.75(14) . . ?
O2 C8 N2 124.71(14) . . ?
O3 C8 N2 111.52(12) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 O5 122.58(15) . . ?
O4 C10 C2 124.49(14) . . ?
O5 C10 C2 112.92(13) . . ?
O5 C11 H11A 109.5 . . ?
O5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C7 120.36(13) . . ?
C13 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C12 C13 C14 121.30(14) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 117.48(13) . . ?
C15 C14 C16 120.16(14) . . ?
C13 C14 C16 122.36(13) . . ?
C14 C15 C6 122.31(14) . . ?
C14 C15 H15 118.8 . . ?
C6 C15 H15 118.8 . . ?
C14 C16 C18 112.49(14) . . ?
C14 C16 C17 111.28(14) . . ?
C18 C16 C17 110.96(14) . . ?
C14 C16 H16 107.3 . . ?
C18 C16 H16 107.3 . . ?
C17 C16 H16 107.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O6 C19 O7 124.78(14) . . ?
O6 C19 N1 123.56(14) . . ?
O7 C19 N1 111.65(13) . . ?
O7 C20 H20A 109.5 . . ?
O7 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O7 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C23 O8 H8 109.5 . . ?
C28 O10 C29 114.45(13) . . ?
C30 O12 C31 116.64(14) . . ?
C39 O14 C40 115.42(14) . . ?
C39 N3 C21 123.88(13) . . ?
C39 N3 C25 117.49(12) . . ?
C21 N3 C25 110.87(11) . . ?
C28 N4 C27 120.70(12) . . ?
C28 N4 C21 121.97(12) . . ?
C27 N4 C21 114.76(11) . . ?
N3 C21 N4 106.55(12) . . ?
N3 C21 C22 110.11(12) . . ?
N4 C21 C22 111.82(12) . . ?
N3 C21 H21 109.4 . . ?
N4 C21 H21 109.4 . . ?
C22 C21 H21 109.4 . . ?
C23 C22 C30 119.26(14) . . ?
C23 C22 C21 121.38(14) . . ?
C30 C22 C21 119.35(13) . . ?
O8 C23 C22 123.51(15) . . ?
O8 C23 C24 113.58(13) . . ?
C22 C23 C24 122.89(14) . . ?
C23 C24 C25 109.71(12) . . ?
C23 C24 H24A 109.7 . . ?
C25 C24 H24A 109.7 . . ?
C23 C24 H24B 109.7 . . ?
C25 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
N3 C25 C26 109.34(11) . . ?
N3 C25 C24 107.81(12) . . ?
C26 C25 C24 111.60(12) . . ?
N3 C25 H25 109.4 . . ?
C26 C25 H25 109.4 . . ?
C24 C25 H25 109.4 . . ?
C35 C26 C27 119.18(13) . . ?
C35 C26 C25 118.33(13) . . ?
C27 C26 C25 122.48(13) . . ?
C32 C27 C26 119.22(13) . . ?
C32 C27 N4 122.24(13) . . ?
C26 C27 N4 118.47(12) . . ?
O9 C28 O10 123.69(14) . . ?
O9 C28 N4 124.73(15) . . ?
O10 C28 N4 111.57(13) . . ?
O10 C29 H29A 109.5 . . ?
O10 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O10 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O11 C30 O12 122.58(15) . . ?
O11 C30 C22 124.53(15) . . ?
O12 C30 C22 112.89(13) . . ?
O12 C31 H31A 109.5 . . ?
O12 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O12 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C27 120.51(13) . . ?
C33 C32 H32 119.7 . . ?
C27 C32 H32 119.7 . . ?
C32 C33 C34 121.10(14) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C35 C34 C33 117.60(14) . . ?
C35 C34 C36 120.17(14) . . ?
C33 C34 C36 122.22(14) . . ?
C34 C35 C26 122.36(14) . . ?
C34 C35 H35 118.8 . . ?
C26 C35 H35 118.8 . . ?
C34 C36 C38 112.73(14) . . ?
C34 C36 C37 111.09(14) . . ?
C38 C36 C37 109.85(15) . . ?
C34 C36 H36 107.7 . . ?
C38 C36 H36 107.7 . . ?
C37 C36 H36 107.7 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O13 C39 O14 124.49(14) . . ?
O13 C39 N3 124.02(15) . . ?
O14 C39 N3 111.48(13) . . ?
O14 C40 H40A 109.5 . . ?
O14 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O14 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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 C3 1.3393(18) . ?
O1 H1A 0.8400 . ?
O2 C8 1.2081(18) . ?
O3 C8 1.3445(18) . ?
O3 C9 1.4444(19) . ?
O4 C10 1.2271(19) . ?
O5 C10 1.3360(19) . ?
O5 C11 1.450(2) . ?
O6 C19 1.2138(19) . ?
O7 C19 1.3403(19) . ?
O7 C20 1.4464(19) . ?
N1 C19 1.3637(19) . ?
N1 C1 1.4607(19) . ?
N1 C5 1.4629(19) . ?
N2 C8 1.3756(18) . ?
N2 C7 1.4322(18) . ?
N2 C1 1.4751(17) . ?
C1 C2 1.517(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.355(2) . ?
C2 C10 1.457(2) . ?
C3 C4 1.493(2) . ?
C4 C5 1.530(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.516(2) . ?
C5 H5 1.0000 . ?
C6 C15 1.395(2) . ?
C6 C7 1.397(2) . ?
C7 C12 1.397(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(2) . ?
C14 C16 1.517(2) . ?
C15 H15 0.9500 . ?
C16 C18 1.523(2) . ?
C16 C17 1.525(3) . ?
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 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O8 C23 1.3424(19) . ?
O8 H8 0.8400 . ?
O9 C28 1.2092(19) . ?
O10 C28 1.3436(19) . ?
O10 C29 1.450(2) . ?
O11 C30 1.229(2) . ?
O12 C30 1.333(2) . ?
O12 C31 1.444(2) . ?
O13 C39 1.2119(19) . ?
O14 C39 1.343(2) . ?
O14 C40 1.446(2) . ?
N3 C39 1.3656(19) . ?
N3 C21 1.4621(19) . ?
N3 C25 1.4635(19) . ?
N4 C28 1.3774(19) . ?
N4 C27 1.4302(19) . ?
N4 C21 1.4755(18) . ?
C21 C22 1.521(2) . ?
C21 H21 1.0000 . ?
C22 C23 1.354(2) . ?
C22 C30 1.458(2) . ?
C23 C24 1.492(2) . ?
C24 C25 1.530(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.5157(19) . ?
C25 H25 1.0000 . ?
C26 C35 1.396(2) . ?
C26 C27 1.399(2) . ?
C27 C32 1.398(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.387(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.401(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.388(2) . ?
C34 C36 1.516(2) . ?
C35 H35 0.9500 . ?
C36 C38 1.526(2) . ?
C36 C37 1.528(2) . ?
C36 H36 1.0000 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 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
O1 H1A O4 0.84 1.84 2.5769(17) 145.5 .
O8 H8 O11 0.84 1.86 2.5923(18) 145.3 .
O1 H1A O8 0.84 2.59 3.0645(17) 117.1 2_766
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
C19 N1 C1 N2 -136.53(14) . . . . ?
C5 N1 C1 N2 69.98(14) . . . . ?
C19 N1 C1 C2 102.83(16) . . . . ?
C5 N1 C1 C2 -50.66(15) . . . . ?
C8 N2 C1 N1 110.79(15) . . . . ?
C7 N2 C1 N1 -52.88(15) . . . . ?
C8 N2 C1 C2 -129.24(14) . . . . ?
C7 N2 C1 C2 67.09(15) . . . . ?
N1 C1 C2 C3 14.01(18) . . . . ?
N2 C1 C2 C3 -104.07(15) . . . . ?
N1 C1 C2 C10 -164.38(12) . . . . ?
N2 C1 C2 C10 77.54(16) . . . . ?
C10 C2 C3 O1 0.9(2) . . . . ?
C1 C2 C3 O1 -177.49(13) . . . . ?
C10 C2 C3 C4 -179.28(13) . . . . ?
C1 C2 C3 C4 2.3(2) . . . . ?
O1 C3 C4 C5 -164.25(12) . . . . ?
C2 C3 C4 C5 15.9(2) . . . . ?
C19 N1 C5 C6 154.87(13) . . . . ?
C1 N1 C5 C6 -49.88(15) . . . . ?
C19 N1 C5 C4 -84.50(16) . . . . ?
C1 N1 C5 C4 70.76(14) . . . . ?
C3 C4 C5 N1 -49.92(16) . . . . ?
C3 C4 C5 C6 69.40(16) . . . . ?
N1 C5 C6 C15 -166.69(13) . . . . ?
C4 C5 C6 C15 74.61(17) . . . . ?
N1 C5 C6 C7 15.29(19) . . . . ?
C4 C5 C6 C7 -103.41(16) . . . . ?
C15 C6 C7 C12 -2.1(2) . . . . ?
C5 C6 C7 C12 175.89(13) . . . . ?
C15 C6 C7 N2 -178.83(13) . . . . ?
C5 C6 C7 N2 -0.8(2) . . . . ?
C8 N2 C7 C6 -143.67(14) . . . . ?
C1 N2 C7 C6 20.18(18) . . . . ?
C8 N2 C7 C12 39.7(2) . . . . ?
C1 N2 C7 C12 -156.44(13) . . . . ?
C9 O3 C8 O2 -5.0(2) . . . . ?
C9 O3 C8 N2 173.62(14) . . . . ?
C7 N2 C8 O2 -2.6(2) . . . . ?
C1 N2 C8 O2 -165.23(15) . . . . ?
C7 N2 C8 O3 178.84(12) . . . . ?
C1 N2 C8 O3 16.2(2) . . . . ?
C11 O5 C10 O4 -1.0(2) . . . . ?
C11 O5 C10 C2 178.55(13) . . . . ?
C3 C2 C10 O4 -2.2(2) . . . . ?
C1 C2 C10 O4 176.23(14) . . . . ?
C3 C2 C10 O5 178.25(13) . . . . ?
C1 C2 C10 O5 -3.32(19) . . . . ?
C6 C7 C12 C13 2.6(2) . . . . ?
N2 C7 C12 C13 179.27(13) . . . . ?
C7 C12 C13 C14 -0.8(2) . . . . ?
C12 C13 C14 C15 -1.6(2) . . . . ?
C12 C13 C14 C16 178.62(14) . . . . ?
C13 C14 C15 C6 2.2(2) . . . . ?
C16 C14 C15 C6 -178.05(14) . . . . ?
C7 C6 C15 C14 -0.3(2) . . . . ?
C5 C6 C15 C14 -178.43(14) . . . . ?
C15 C14 C16 C18 116.67(17) . . . . ?
C13 C14 C16 C18 -63.6(2) . . . . ?
C15 C14 C16 C17 -118.10(17) . . . . ?
C13 C14 C16 C17 61.6(2) . . . . ?
C20 O7 C19 O6 3.4(2) . . . . ?
C20 O7 C19 N1 -178.06(13) . . . . ?
C1 N1 C19 O6 -168.82(14) . . . . ?
C5 N1 C19 O6 -17.0(2) . . . . ?
C1 N1 C19 O7 12.6(2) . . . . ?
C5 N1 C19 O7 164.45(13) . . . . ?
C39 N3 C21 N4 140.84(14) . . . . ?
C25 N3 C21 N4 -70.84(14) . . . . ?
C39 N3 C21 C22 -97.71(16) . . . . ?
C25 N3 C21 C22 50.61(15) . . . . ?
C28 N4 C21 N3 -108.18(15) . . . . ?
C27 N4 C21 N3 53.75(15) . . . . ?
C28 N4 C21 C22 131.46(15) . . . . ?
C27 N4 C21 C22 -66.61(16) . . . . ?
N3 C21 C22 C23 -12.0(2) . . . . ?
N4 C21 C22 C23 106.27(16) . . . . ?
N3 C21 C22 C30 166.48(13) . . . . ?
N4 C21 C22 C30 -75.27(17) . . . . ?
C30 C22 C23 O8 -2.9(2) . . . . ?
C21 C22 C23 O8 175.57(14) . . . . ?
C30 C22 C23 C24 175.75(14) . . . . ?
C21 C22 C23 C24 -5.8(2) . . . . ?
O8 C23 C24 C25 165.10(13) . . . . ?
C22 C23 C24 C25 -13.7(2) . . . . ?
C39 N3 C25 C26 -159.73(13) . . . . ?
C21 N3 C25 C26 49.72(15) . . . . ?
C39 N3 C25 C24 78.77(16) . . . . ?
C21 N3 C25 C24 -71.78(14) . . . . ?
C23 C24 C25 N3 50.13(16) . . . . ?
C23 C24 C25 C26 -69.95(16) . . . . ?
N3 C25 C26 C35 167.48(13) . . . . ?
C24 C25 C26 C35 -73.34(17) . . . . ?
N3 C25 C26 C27 -13.65(19) . . . . ?
C24 C25 C26 C27 105.53(16) . . . . ?
C35 C26 C27 C32 0.4(2) . . . . ?
C25 C26 C27 C32 -178.46(13) . . . . ?
C35 C26 C27 N4 177.43(13) . . . . ?
C25 C26 C27 N4 -1.4(2) . . . . ?
C28 N4 C27 C32 -40.1(2) . . . . ?
C21 N4 C27 C32 157.68(13) . . . . ?
C28 N4 C27 C26 142.93(14) . . . . ?
C21 N4 C27 C26 -19.25(18) . . . . ?
C29 O10 C28 O9 4.3(2) . . . . ?
C29 O10 C28 N4 -174.35(14) . . . . ?
C27 N4 C28 O9 3.9(2) . . . . ?
C21 N4 C28 O9 164.74(15) . . . . ?
C27 N4 C28 O10 -177.46(12) . . . . ?
C21 N4 C28 O10 -16.6(2) . . . . ?
C31 O12 C30 O11 -1.3(2) . . . . ?
C31 O12 C30 C22 177.82(13) . . . . ?
C23 C22 C30 O11 4.6(2) . . . . ?
C21 C22 C30 O11 -173.88(15) . . . . ?
C23 C22 C30 O12 -174.43(14) . . . . ?
C21 C22 C30 O12 7.1(2) . . . . ?
C26 C27 C32 C33 -1.6(2) . . . . ?
N4 C27 C32 C33 -178.48(14) . . . . ?
C27 C32 C33 C34 1.0(2) . . . . ?
C32 C33 C34 C35 0.6(2) . . . . ?
C32 C33 C34 C36 179.91(14) . . . . ?
C33 C34 C35 C26 -1.9(2) . . . . ?
C36 C34 C35 C26 178.87(14) . . . . ?
C27 C26 C35 C34 1.3(2) . . . . ?
C25 C26 C35 C34 -179.75(14) . . . . ?
C35 C34 C36 C38 -119.40(16) . . . . ?
C33 C34 C36 C38 61.4(2) . . . . ?
C35 C34 C36 C37 116.81(17) . . . . ?
C33 C34 C36 C37 -62.4(2) . . . . ?
C40 O14 C39 O13 -3.6(3) . . . . ?
C40 O14 C39 N3 177.91(16) . . . . ?
C21 N3 C39 O13 168.31(14) . . . . ?
C25 N3 C39 O13 21.9(2) . . . . ?
C21 N3 C39 O14 -13.2(2) . . . . ?
C25 N3 C39 O14 -159.62(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352769
