#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/01/1520158.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_1520158
loop_
_publ_author_name
'McDonald, E.'
'Horton, Peter N.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C23H20N2O6
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              595
_journal_year                    2008
_chemical_formula_sum            'C23 H20 N2 O6'
_chemical_formula_weight         420.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 107.4310(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   21.5955(7)
_cell_length_b                   9.5241(3)
_cell_length_c                   30.6167(10)
_cell_measurement_reflns_used    13783
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     6008.0(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            52032
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut Block'
_exptl_crystal_F_000             2640
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     844
_refine_ls_number_reflns         13704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0795
_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)+(0.0218P)²+12.5958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1653
_reflns_number_gt                8793
_reflns_number_total             13704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-595.cif
_cod_data_source_block           2008src0845
_cod_depositor_comments
;
Citation :
McDonald, E and Horton, Peter N. and Hursthouse, Michael B. (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/595)

More at:
http://ecrystals.chem.soton.ac.uk/595/
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1520158
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.96335(13) -0.0167(3) 0.32274(10) 0.0196(6) Uani 1 1 d . . .
C2 C 1.06047(13) -0.0837(3) 0.37608(10) 0.0187(6) Uani 1 1 d . . .
C3 C 1.06589(12) -0.1324(3) 0.33019(9) 0.0175(6) Uani 1 1 d . . .
H3 H 1.0765 -0.2347 0.3304 0.021 Uiso 1 1 calc R . .
C4 C 0.99953(13) -0.0986(3) 0.29559(9) 0.0175(6) Uani 1 1 d . . .
H4 H 0.9756 -0.1839 0.2804 0.021 Uiso 1 1 calc R . .
C5 C 1.01928(13) 0.0018(3) 0.26181(9) 0.0180(6) Uani 1 1 d . . .
C6 C 1.05481(13) -0.0951(3) 0.23670(10) 0.0191(6) Uani 1 1 d . . .
C7 C 1.11213(13) -0.0408(3) 0.31044(9) 0.0180(6) Uani 1 1 d . . .
C8 C 0.96843(13) 0.0996(3) 0.23283(10) 0.0199(6) Uani 1 1 d . . .
C9 C 0.86976(14) 0.1086(3) 0.17284(11) 0.0288(7) Uani 1 1 d . . .
H9A H 0.8459 0.1587 0.1907 0.043 Uiso 1 1 calc R . .
H9B H 0.8400 0.0463 0.1508 0.043 Uiso 1 1 calc R . .
H9C H 0.8886 0.1766 0.1564 0.043 Uiso 1 1 calc R . .
C10 C 1.17691(13) 0.0034(3) 0.34108(10) 0.0233(6) Uani 1 1 d . . .
H10A H 1.1987 0.0620 0.3239 0.035 Uiso 1 1 calc R . .
H10B H 1.2034 -0.0799 0.3526 0.035 Uiso 1 1 calc R . .
H10C H 1.1712 0.0572 0.3669 0.035 Uiso 1 1 calc R . .
C11 C 0.97760(13) 0.0413(3) 0.40489(9) 0.0186(6) Uani 1 1 d . . .
C12 C 0.91406(14) 0.0143(3) 0.40421(11) 0.0236(6) Uani 1 1 d . . .
H12 H 0.8863 -0.0413 0.3806 0.028 Uiso 1 1 calc R . .
C13 C 0.89208(15) 0.0702(3) 0.43866(11) 0.0281(7) Uani 1 1 d . . .
H13 H 0.8483 0.0560 0.4380 0.034 Uiso 1 1 calc R . .
C14 C 0.93356(15) 0.1469(3) 0.47415(11) 0.0276(7) Uani 1 1 d . . .
H14 H 0.9187 0.1810 0.4984 0.033 Uiso 1 1 calc R . .
C15 C 0.99649(15) 0.1734(3) 0.47412(11) 0.0257(7) Uani 1 1 d . . .
H15 H 1.0246 0.2268 0.4982 0.031 Uiso 1 1 calc R . .
C16 C 1.01881(14) 0.1223(3) 0.43887(10) 0.0226(6) Uani 1 1 d . . .
H16 H 1.0616 0.1427 0.4382 0.027 Uiso 1 1 calc R . .
C17 C 1.15578(13) -0.2314(3) 0.26578(10) 0.0203(6) Uani 1 1 d . . .
H17A H 1.1323 -0.2935 0.2402 0.024 Uiso 1 1 calc R . .
H17B H 1.1642 -0.2860 0.2945 0.024 Uiso 1 1 calc R . .
C18 C 1.22047(13) -0.1911(3) 0.25921(10) 0.0199(6) Uani 1 1 d . . .
C19 C 1.27811(14) -0.2342(3) 0.29065(11) 0.0289(7) Uani 1 1 d . . .
H19 H 1.2769 -0.2825 0.3175 0.035 Uiso 1 1 calc R . .
C20 C 1.33766(15) -0.2076(4) 0.28341(13) 0.0374(8) Uani 1 1 d . . .
H20 H 1.3768 -0.2372 0.3053 0.045 Uiso 1 1 calc R . .
C21 C 1.33950(15) -0.1380(3) 0.24436(12) 0.0335(8) Uani 1 1 d . . .
H21 H 1.3800 -0.1206 0.2391 0.040 Uiso 1 1 calc R . .
C22 C 1.28279(16) -0.0937(4) 0.21303(12) 0.0353(8) Uani 1 1 d . . .
H22 H 1.2842 -0.0456 0.1862 0.042 Uiso 1 1 calc R . .
C23 C 1.22346(15) -0.1192(3) 0.22057(11) 0.0306(7) Uani 1 1 d . . .
H23 H 1.1846 -0.0869 0.1990 0.037 Uiso 1 1 calc R . .
N1 N 1.00070(11) -0.0168(2) 0.36910(8) 0.0183(5) Uani 1 1 d . . .
N2 N 1.11373(11) -0.1121(2) 0.26783(8) 0.0187(5) Uani 1 1 d . . .
O1 O 0.91184(9) 0.0414(2) 0.30717(7) 0.0275(5) Uani 1 1 d . . .
O2 O 1.10029(10) -0.1011(2) 0.41293(7) 0.0251(5) Uani 1 1 d . . .
O3 O 1.07191(9) 0.07767(19) 0.29204(6) 0.0192(4) Uani 1 1 d . . .
O4 O 1.03324(9) -0.1516(2) 0.19964(7) 0.0239(5) Uani 1 1 d . . .
O5 O 0.97082(10) 0.2254(2) 0.23599(7) 0.0253(5) Uani 1 1 d . . .
O6 O 0.92145(9) 0.0256(2) 0.20358(7) 0.0236(5) Uani 1 1 d . . .
C31 C 0.37215(13) 0.0138(3) 0.00875(10) 0.0195(6) Uani 1 1 d . . .
C32 C 0.27697(13) 0.0910(3) -0.04437(10) 0.0195(6) Uani 1 1 d . . .
C33 C 0.27213(13) 0.1406(3) 0.00161(9) 0.0179(6) Uani 1 1 d . . .
H33 H 0.2639 0.2439 0.0018 0.022 Uiso 1 1 calc R . .
C34 C 0.33783(13) 0.0994(3) 0.03631(9) 0.0181(6) Uani 1 1 d . . .
H34 H 0.3636 0.1820 0.0520 0.022 Uiso 1 1 calc R . .
C35 C 0.31513(13) 0.0014(3) 0.06945(9) 0.0177(6) Uani 1 1 d . . .
C36 C 0.28138(13) 0.1017(3) 0.09455(10) 0.0189(6) Uani 1 1 d . . .
C37 C 0.22382(13) 0.0546(3) 0.02041(10) 0.0189(6) Uani 1 1 d . . .
C38 C 0.36351(13) -0.1009(3) 0.09858(9) 0.0194(6) Uani 1 1 d . . .
C39 C 0.45988(15) -0.1182(3) 0.16021(11) 0.0301(7) Uani 1 1 d . . .
H39A H 0.4381 -0.1835 0.1755 0.045 Uiso 1 1 calc R . .
H39B H 0.4897 -0.0584 0.1831 0.045 Uiso 1 1 calc R . .
H39C H 0.4844 -0.1715 0.1435 0.045 Uiso 1 1 calc R . .
C40 C 0.15763(13) 0.0178(3) -0.01076(10) 0.0232(6) Uani 1 1 d . . .
H40A H 0.1621 -0.0366 -0.0368 0.035 Uiso 1 1 calc R . .
H40B H 0.1334 0.1042 -0.0219 0.035 Uiso 1 1 calc R . .
H40C H 0.1343 -0.0380 0.0061 0.035 Uiso 1 1 calc R . .
C41 C 0.35801(13) -0.0408(3) -0.07336(9) 0.0183(6) Uani 1 1 d . . .
C42 C 0.31568(14) -0.1157(3) -0.10827(10) 0.0217(6) Uani 1 1 d . . .
H42 H 0.2724 -0.1321 -0.1081 0.026 Uiso 1 1 calc R . .
C43 C 0.33720(15) -0.1672(3) -0.14383(10) 0.0241(6) Uani 1 1 d . . .
H43 H 0.3081 -0.2161 -0.1686 0.029 Uiso 1 1 calc R . .
C44 C 0.40109(15) -0.1468(3) -0.14283(11) 0.0259(7) Uani 1 1 d . . .
H44 H 0.4158 -0.1819 -0.1670 0.031 Uiso 1 1 calc R . .
C45 C 0.44386(15) -0.0754(3) -0.10673(11) 0.0276(7) Uani 1 1 d . . .
H45 H 0.4879 -0.0641 -0.1058 0.033 Uiso 1 1 calc R . .
C46 C 0.42224(14) -0.0207(3) -0.07198(10) 0.0246(6) Uani 1 1 d . . .
H46 H 0.4510 0.0300 -0.0475 0.029 Uiso 1 1 calc R . .
C47 C 0.18119(14) 0.2417(3) 0.06727(10) 0.0218(6) Uani 1 1 d . . .
H47A H 0.1647 0.2885 0.0371 0.026 Uiso 1 1 calc R . .
H47B H 0.2069 0.3115 0.0893 0.026 Uiso 1 1 calc R . .
C48 C 0.12386(13) 0.1966(3) 0.08279(10) 0.0206(6) Uani 1 1 d . . .
C49 C 0.07193(15) 0.2883(4) 0.07609(11) 0.0322(7) Uani 1 1 d . . .
H49 H 0.0723 0.3755 0.0611 0.039 Uiso 1 1 calc R . .
C50 C 0.01946(16) 0.2530(4) 0.09123(13) 0.0439(10) Uani 1 1 d . . .
H50 H -0.0164 0.3153 0.0859 0.053 Uiso 1 1 calc R . .
C51 C 0.01900(16) 0.1281(4) 0.11392(13) 0.0432(10) Uani 1 1 d . . .
H51 H -0.0168 0.1046 0.1245 0.052 Uiso 1 1 calc R . .
C52 C 0.07088(16) 0.0378(4) 0.12110(12) 0.0358(8) Uani 1 1 d . . .
H52 H 0.0711 -0.0478 0.1371 0.043 Uiso 1 1 calc R . .
C53 C 0.12291(14) 0.0705(3) 0.10519(10) 0.0260(7) Uani 1 1 d . . .
H53 H 0.1580 0.0064 0.1097 0.031 Uiso 1 1 calc R . .
N31 N 0.33577(11) 0.0190(2) -0.03728(8) 0.0183(5) Uani 1 1 d . . .
N32 N 0.22381(11) 0.1267(2) 0.06337(8) 0.0189(5) Uani 1 1 d . . .
O31 O 0.42226(9) -0.0497(2) 0.02448(7) 0.0269(5) Uani 1 1 d . . .
O32 O 0.23797(9) 0.1122(2) -0.08136(7) 0.0244(5) Uani 1 1 d . . .
O33 O 0.26104(9) -0.06841(19) 0.03856(6) 0.0184(4) Uani 1 1 d . . .
O34 O 0.30283(10) 0.1524(2) 0.13270(7) 0.0233(4) Uani 1 1 d . . .
O35 O 0.35734(10) -0.2258(2) 0.09582(7) 0.0252(5) Uani 1 1 d . . .
O36 O 0.41153(9) -0.0309(2) 0.12816(7) 0.0233(4) Uani 1 1 d . . .
C61 C 0.79173(13) 0.5056(3) 0.15625(10) 0.0194(6) Uani 1 1 d . . .
C62 C 0.88618(13) 0.5857(3) 0.20959(10) 0.0187(6) Uani 1 1 d . . .
C63 C 0.89154(13) 0.6307(3) 0.16330(9) 0.0180(6) Uani 1 1 d . . .
H63 H 0.9005 0.7335 0.1622 0.022 Uiso 1 1 calc R . .
C64 C 0.82663(13) 0.5889(3) 0.12860(9) 0.0181(6) Uani 1 1 d . . .
H64 H 0.8011 0.6709 0.1122 0.022 Uiso 1 1 calc R . .
C65 C 0.84933(13) 0.4877(3) 0.09635(9) 0.0170(6) Uani 1 1 d . . .
C66 C 0.88497(13) 0.5827(3) 0.07112(9) 0.0169(5) Uani 1 1 d . . .
C67 C 0.94049(13) 0.5390(3) 0.14634(9) 0.0178(6) Uani 1 1 d . . .
C68 C 0.80027(13) 0.3863(3) 0.06730(9) 0.0185(6) Uani 1 1 d . . .
C69 C 0.70277(14) 0.3729(3) 0.00647(11) 0.0283(7) Uani 1 1 d . . .
H69A H 0.7236 0.3057 -0.0089 0.043 Uiso 1 1 calc R . .
H69B H 0.6735 0.4338 -0.0164 0.043 Uiso 1 1 calc R . .
H69C H 0.6779 0.3218 0.0234 0.043 Uiso 1 1 calc R . .
C70 C 1.00450(13) 0.5020(3) 0.17966(10) 0.0217(6) Uani 1 1 d . . .
H70A H 0.9975 0.4435 0.2041 0.033 Uiso 1 1 calc R . .
H70B H 1.0274 0.5881 0.1929 0.033 Uiso 1 1 calc R . .
H70C H 1.0306 0.4501 0.1638 0.033 Uiso 1 1 calc R . .
C71 C 0.80666(13) 0.4497(3) 0.23853(10) 0.0203(6) Uani 1 1 d . . .
C72 C 0.85017(14) 0.3740(3) 0.27299(10) 0.0216(6) Uani 1 1 d . . .
H72 H 0.8935 0.3597 0.2725 0.026 Uiso 1 1 calc R . .
C73 C 0.82939(15) 0.3193(3) 0.30833(11) 0.0256(7) Uani 1 1 d . . .
H73 H 0.8589 0.2690 0.3325 0.031 Uiso 1 1 calc R . .
C74 C 0.76557(15) 0.3378(3) 0.30840(11) 0.0268(7) Uani 1 1 d . . .
H74 H 0.7517 0.3010 0.3327 0.032 Uiso 1 1 calc R . .
C75 C 0.72217(15) 0.4102(3) 0.27282(11) 0.0274(7) Uani 1 1 d . . .
H75 H 0.6782 0.4198 0.2723 0.033 Uiso 1 1 calc R . .
C76 C 0.74265(14) 0.4687(3) 0.23793(10) 0.0236(6) Uani 1 1 d . . .
H76 H 0.7134 0.5207 0.2141 0.028 Uiso 1 1 calc R . .
C77 C 0.98478(13) 0.7241(3) 0.10007(10) 0.0197(6) Uani 1 1 d . . .
H77A H 0.9990 0.7715 0.1302 0.024 Uiso 1 1 calc R . .
H77B H 0.9585 0.7921 0.0776 0.024 Uiso 1 1 calc R . .
C78 C 1.04420(14) 0.6864(3) 0.08616(10) 0.0221(6) Uani 1 1 d . . .
C79 C 1.04052(17) 0.6800(4) 0.04016(12) 0.0360(8) Uani 1 1 d . . .
H79 H 0.9999 0.6929 0.0174 0.043 Uiso 1 1 calc R . .
C80 C 1.0959(2) 0.6549(4) 0.02722(15) 0.0530(11) Uani 1 1 d . . .
H80 H 1.0930 0.6498 -0.0043 0.064 Uiso 1 1 calc R . .
C81 C 1.1547(2) 0.6373(4) 0.05980(18) 0.0598(13) Uani 1 1 d . . .
H81 H 1.1925 0.6205 0.0508 0.072 Uiso 1 1 calc R . .
C82 C 1.15922(18) 0.6440(5) 0.10530(17) 0.0564(12) Uani 1 1 d . . .
H82 H 1.2001 0.6325 0.1278 0.068 Uiso 1 1 calc R . .
C83 C 1.10382(15) 0.6676(4) 0.11841(13) 0.0379(8) Uani 1 1 d . . .
H83 H 1.1070 0.6708 0.1500 0.045 Uiso 1 1 calc R . .
N61 N 0.82776(11) 0.5113(2) 0.20224(8) 0.0186(5) Uani 1 1 d . . .
N62 N 0.94346(10) 0.6043(2) 0.10312(8) 0.0171(5) Uani 1 1 d . . .
O61 O 0.74157(9) 0.4423(2) 0.14086(7) 0.0269(5) Uani 1 1 d . . .
O62 O 0.92473(9) 0.6092(2) 0.24644(7) 0.0251(5) Uani 1 1 d . . .
O63 O 0.90209(9) 0.41673(19) 0.12852(6) 0.0177(4) Uani 1 1 d . . .
O64 O 0.86480(9) 0.6327(2) 0.03298(7) 0.0232(4) Uani 1 1 d . . .
O65 O 0.80567(10) 0.2607(2) 0.06953(7) 0.0256(5) Uani 1 1 d . . .
O66 O 0.75229(9) 0.4582(2) 0.03823(7) 0.0215(4) Uani 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 0.0000 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
O1 C1 N1 125.6(3) . .
O1 C1 C4 125.8(3) . .
N1 C1 C4 108.6(2) . .
O2 C2 N1 124.9(3) . .
O2 C2 C3 126.3(2) . .
N1 C2 C3 108.8(2) . .
C2 C3 C4 105.0(2) . .
C2 C3 C7 114.8(2) . .
C4 C3 C7 100.8(2) . .
C2 C3 H3 111.8 . .
C4 C3 H3 111.8 . .
C7 C3 H3 111.8 . .
C1 C4 C3 104.9(2) . .
C1 C4 C5 109.7(2) . .
C3 C4 C5 101.6(2) . .
C1 C4 H4 113.3 . .
C3 C4 H4 113.3 . .
C5 C4 H4 113.3 . .
O3 C5 C8 111.5(2) . .
O3 C5 C6 102.0(2) . .
C8 C5 C6 117.3(2) . .
O3 C5 C4 101.7(2) . .
C8 C5 C4 118.2(2) . .
C6 C5 C4 103.8(2) . .
O4 C6 N2 128.5(3) . .
O4 C6 C5 128.4(2) . .
N2 C6 C5 102.9(2) . .
O3 C7 N2 100.7(2) . .
O3 C7 C10 111.6(2) . .
N2 C7 C10 114.7(2) . .
O3 C7 C3 102.0(2) . .
N2 C7 C3 105.6(2) . .
C10 C7 C3 119.8(2) . .
O5 C8 O6 125.9(3) . .
O5 C8 C5 124.2(3) . .
O6 C8 C5 109.9(2) . .
O6 C9 H9A 109.5 . .
O6 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
O6 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C7 C10 H10A 109.5 . .
C7 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C7 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C16 C11 C12 121.6(3) . .
C16 C11 N1 119.6(2) . .
C12 C11 N1 118.8(3) . .
C13 C12 C11 118.6(3) . .
C13 C12 H12 120.7 . .
C11 C12 H12 120.7 . .
C12 C13 C14 120.6(3) . .
C12 C13 H13 119.7 . .
C14 C13 H13 119.7 . .
C15 C14 C13 119.9(3) . .
C15 C14 H14 120.0 . .
C13 C14 H14 120.0 . .
C14 C15 C16 120.3(3) . .
C14 C15 H15 119.9 . .
C16 C15 H15 119.9 . .
C11 C16 C15 118.9(3) . .
C11 C16 H16 120.6 . .
C15 C16 H16 120.6 . .
N2 C17 C18 114.5(2) . .
N2 C17 H17A 108.6 . .
C18 C17 H17A 108.6 . .
N2 C17 H17B 108.6 . .
C18 C17 H17B 108.6 . .
H17A C17 H17B 107.6 . .
C23 C18 C19 118.5(3) . .
C23 C18 C17 121.2(3) . .
C19 C18 C17 120.2(3) . .
C18 C19 C20 121.0(3) . .
C18 C19 H19 119.5 . .
C20 C19 H19 119.5 . .
C21 C20 C19 119.6(3) . .
C21 C20 H20 120.2 . .
C19 C20 H20 120.2 . .
C22 C21 C20 120.1(3) . .
C22 C21 H21 120.0 . .
C20 C21 H21 120.0 . .
C21 C22 C23 120.2(3) . .
C21 C22 H22 119.9 . .
C23 C22 H22 119.9 . .
C18 C23 C22 120.6(3) . .
C18 C23 H23 119.7 . .
C22 C23 H23 119.7 . .
C2 N1 C1 112.3(2) . .
C2 N1 C11 124.9(2) . .
C1 N1 C11 122.8(2) . .
C6 N2 C17 121.7(2) . .
C6 N2 C7 107.5(2) . .
C17 N2 C7 124.8(2) . .
C5 O3 C7 97.31(19) . .
C8 O6 C9 115.3(2) . .
O31 C31 N31 126.0(3) . .
O31 C31 C34 125.2(3) . .
N31 C31 C34 108.8(2) . .
O32 C32 N31 124.8(3) . .
O32 C32 C33 126.5(2) . .
N31 C32 C33 108.6(2) . .
C32 C33 C34 104.7(2) . .
C32 C33 C37 114.6(2) . .
C34 C33 C37 101.0(2) . .
C32 C33 H33 111.9 . .
C34 C33 H33 111.9 . .
C37 C33 H33 111.9 . .
C31 C34 C33 104.8(2) . .
C31 C34 C35 109.9(2) . .
C33 C34 C35 101.3(2) . .
C31 C34 H34 113.3 . .
C33 C34 H34 113.3 . .
C35 C34 H34 113.3 . .
O33 C35 C38 112.0(2) . .
O33 C35 C36 101.8(2) . .
C38 C35 C36 116.9(2) . .
O33 C35 C34 101.6(2) . .
C38 C35 C34 118.3(2) . .
C36 C35 C34 103.9(2) . .
O34 C36 N32 128.0(3) . .
O34 C36 C35 128.5(3) . .
N32 C36 C35 103.4(2) . .
O33 C37 N32 100.6(2) . .
O33 C37 C40 111.8(2) . .
N32 C37 C40 114.7(2) . .
O33 C37 C33 102.2(2) . .
N32 C37 C33 105.1(2) . .
C40 C37 C33 120.0(2) . .
O35 C38 O36 126.3(3) . .
O35 C38 C35 123.8(3) . .
O36 C38 C35 109.8(2) . .
O36 C39 H39A 109.5 . .
O36 C39 H39B 109.5 . .
H39A C39 H39B 109.5 . .
O36 C39 H39C 109.5 . .
H39A C39 H39C 109.5 . .
H39B C39 H39C 109.5 . .
C37 C40 H40A 109.5 . .
C37 C40 H40B 109.5 . .
H40A C40 H40B 109.5 . .
C37 C40 H40C 109.5 . .
H40A C40 H40C 109.5 . .
H40B C40 H40C 109.5 . .
C42 C41 C46 121.3(3) . .
C42 C41 N31 120.1(2) . .
C46 C41 N31 118.7(2) . .
C41 C42 C43 119.2(3) . .
C41 C42 H42 120.4 . .
C43 C42 H42 120.4 . .
C44 C43 C42 119.8(3) . .
C44 C43 H43 120.1 . .
C42 C43 H43 120.1 . .
C43 C44 C45 120.5(3) . .
C43 C44 H44 119.7 . .
C45 C44 H44 119.7 . .
C46 C45 C44 119.9(3) . .
C46 C45 H45 120.0 . .
C44 C45 H45 120.0 . .
C45 C46 C41 119.2(3) . .
C45 C46 H46 120.4 . .
C41 C46 H46 120.4 . .
N32 C47 C48 114.1(2) . .
N32 C47 H47A 108.7 . .
C48 C47 H47A 108.7 . .
N32 C47 H47B 108.7 . .
C48 C47 H47B 108.7 . .
H47A C47 H47B 107.6 . .
C53 C48 C49 119.2(3) . .
C53 C48 C47 122.4(3) . .
C49 C48 C47 118.4(3) . .
C48 C49 C50 120.2(3) . .
C48 C49 H49 119.9 . .
C50 C49 H49 119.9 . .
C51 C50 C49 120.5(3) . .
C51 C50 H50 119.8 . .
C49 C50 H50 119.8 . .
C52 C51 C50 119.4(3) . .
C52 C51 H51 120.3 . .
C50 C51 H51 120.3 . .
C51 C52 C53 120.6(3) . .
C51 C52 H52 119.7 . .
C53 C52 H52 119.7 . .
C48 C53 C52 120.1(3) . .
C48 C53 H53 119.9 . .
C52 C53 H53 119.9 . .
C31 N31 C32 112.6(2) . .
C31 N31 C41 122.9(2) . .
C32 N31 C41 124.5(2) . .
C36 N32 C47 123.2(2) . .
C36 N32 C37 107.6(2) . .
C47 N32 C37 126.0(2) . .
C35 O33 C37 97.39(19) . .
C38 O36 C39 115.2(2) . .
O61 C61 N61 125.4(3) . .
O61 C61 C64 125.6(3) . .
N61 C61 C64 108.9(2) . .
O62 C62 N61 125.4(3) . .
O62 C62 C63 126.6(2) . .
N61 C62 C63 108.0(2) . .
C62 C63 C64 105.3(2) . .
C62 C63 C67 113.4(2) . .
C64 C63 C67 101.1(2) . .
C62 C63 H63 112.1 . .
C64 C63 H63 112.1 . .
C67 C63 H63 112.1 . .
C61 C64 C63 104.7(2) . .
C61 C64 C65 109.5(2) . .
C63 C64 C65 101.7(2) . .
C61 C64 H64 113.4 . .
C63 C64 H64 113.4 . .
C65 C64 H64 113.4 . .
O63 C65 C68 112.1(2) . .
O63 C65 C66 102.0(2) . .
C68 C65 C66 116.7(2) . .
O63 C65 C64 101.1(2) . .
C68 C65 C64 118.0(2) . .
C66 C65 C64 104.7(2) . .
O64 C66 N62 128.3(3) . .
O64 C66 C65 128.7(2) . .
N62 C66 C65 102.9(2) . .
O63 C67 N62 100.1(2) . .
O63 C67 C70 112.2(2) . .
N62 C67 C70 115.5(2) . .
O63 C67 C63 101.9(2) . .
N62 C67 C63 106.0(2) . .
C70 C67 C63 118.8(2) . .
O65 C68 O66 126.2(3) . .
O65 C68 C65 124.3(3) . .
O66 C68 C65 109.4(2) . .
O66 C69 H69A 109.5 . .
O66 C69 H69B 109.5 . .
H69A C69 H69B 109.5 . .
O66 C69 H69C 109.5 . .
H69A C69 H69C 109.5 . .
H69B C69 H69C 109.5 . .
C67 C70 H70A 109.5 . .
C67 C70 H70B 109.5 . .
H70A C70 H70B 109.5 . .
C67 C70 H70C 109.5 . .
H70A C70 H70C 109.5 . .
H70B C70 H70C 109.5 . .
C72 C71 C76 121.5(3) . .
C72 C71 N61 119.9(2) . .
C76 C71 N61 118.6(3) . .
C71 C72 C73 118.9(3) . .
C71 C72 H72 120.5 . .
C73 C72 H72 120.5 . .
C74 C73 C72 120.3(3) . .
C74 C73 H73 119.8 . .
C72 C73 H73 119.8 . .
C75 C74 C73 119.9(3) . .
C75 C74 H74 120.1 . .
C73 C74 H74 120.1 . .
C74 C75 C76 120.4(3) . .
C74 C75 H75 119.8 . .
C76 C75 H75 119.8 . .
C71 C76 C75 118.9(3) . .
C71 C76 H76 120.6 . .
C75 C76 H76 120.6 . .
N62 C77 C78 114.6(2) . .
N62 C77 H77A 108.6 . .
C78 C77 H77A 108.6 . .
N62 C77 H77B 108.6 . .
C78 C77 H77B 108.6 . .
H77A C77 H77B 107.6 . .
C83 C78 C79 118.6(3) . .
C83 C78 C77 121.2(3) . .
C79 C78 C77 120.1(3) . .
C78 C79 C80 120.3(4) . .
C78 C79 H79 119.8 . .
C80 C79 H79 119.8 . .
C81 C80 C79 120.2(4) . .
C81 C80 H80 119.9 . .
C79 C80 H80 119.9 . .
C82 C81 C80 120.2(3) . .
C82 C81 H81 119.9 . .
C80 C81 H81 119.9 . .
C81 C82 C83 119.8(4) . .
C81 C82 H82 120.1 . .
C83 C82 H82 120.1 . .
C78 C83 C82 120.9(4) . .
C78 C83 H83 119.5 . .
C82 C83 H83 119.5 . .
C61 N61 C62 112.6(2) . .
C61 N61 C71 123.6(2) . .
C62 N61 C71 123.8(2) . .
C66 N62 C77 121.4(2) . .
C66 N62 C67 107.5(2) . .
C77 N62 C67 125.0(2) . .
C65 O63 C67 97.37(19) . .
C68 O66 C69 115.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.205(3) .
C1 N1 1.407(3) .
C1 C4 1.516(4) .
C2 O2 1.208(3) .
C2 N1 1.397(3) .
C2 C3 1.517(4) .
C3 C4 1.539(4) .
C3 C7 1.576(4) .
C3 H3 1.0000 .
C4 C5 1.559(4) .
C4 H4 1.0000 .
C5 O3 1.428(3) .
C5 C8 1.509(4) .
C5 C6 1.544(4) .
C6 O4 1.215(3) .
C6 N2 1.352(3) .
C7 O3 1.433(3) .
C7 N2 1.480(3) .
C7 C10 1.493(4) .
C8 O5 1.202(3) .
C8 O6 1.336(3) .
C9 O6 1.459(3) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C16 1.384(4) .
C11 C12 1.390(4) .
C11 N1 1.443(3) .
C12 C13 1.386(4) .
C12 H12 0.9500 .
C13 C14 1.391(4) .
C13 H13 0.9500 .
C14 C15 1.383(4) .
C14 H14 0.9500 .
C15 C16 1.395(4) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 N2 1.468(3) .
C17 C18 1.519(4) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C23 1.386(4) .
C18 C19 1.388(4) .
C19 C20 1.392(4) .
C19 H19 0.9500 .
C20 C21 1.378(5) .
C20 H20 0.9500 .
C21 C22 1.376(5) .
C21 H21 0.9500 .
C22 C23 1.389(4) .
C22 H22 0.9500 .
C23 H23 0.9500 .
C31 O31 1.207(3) .
C31 N31 1.394(4) .
C31 C34 1.517(4) .
C32 O32 1.209(3) .
C32 N31 1.402(3) .
C32 C33 1.518(4) .
C33 C34 1.547(4) .
C33 C37 1.565(4) .
C33 H33 1.0000 .
C34 C35 1.562(4) .
C34 H34 1.0000 .
C35 O33 1.428(3) .
C35 C38 1.509(4) .
C35 C36 1.540(4) .
C36 O34 1.220(3) .
C36 N32 1.342(4) .
C37 O33 1.435(3) .
C37 N32 1.484(3) .
C37 C40 1.503(4) .
C38 O35 1.197(3) .
C38 O36 1.333(3) .
C39 O36 1.460(3) .
C39 H39A 0.9800 .
C39 H39B 0.9800 .
C39 H39C 0.9800 .
C40 H40A 0.9800 .
C40 H40B 0.9800 .
C40 H40C 0.9800 .
C41 C42 1.379(4) .
C41 C46 1.388(4) .
C41 N31 1.447(3) .
C42 C43 1.394(4) .
C42 H42 0.9500 .
C43 C44 1.385(4) .
C43 H43 0.9500 .
C44 C45 1.388(4) .
C44 H44 0.9500 .
C45 C46 1.385(4) .
C45 H45 0.9500 .
C46 H46 0.9500 .
C47 N32 1.458(3) .
C47 C48 1.515(4) .
C47 H47A 0.9900 .
C47 H47B 0.9900 .
C48 C53 1.386(4) .
C48 C49 1.387(4) .
C49 C50 1.388(5) .
C49 H49 0.9500 .
C50 C51 1.379(6) .
C50 H50 0.9500 .
C51 C52 1.377(5) .
C51 H51 0.9500 .
C52 C53 1.387(4) .
C52 H52 0.9500 .
C53 H53 0.9500 .
C61 O61 1.206(3) .
C61 N61 1.391(4) .
C61 C64 1.515(4) .
C62 O62 1.206(3) .
C62 N61 1.405(3) .
C62 C63 1.518(4) .
C63 C64 1.536(4) .
C63 C67 1.574(4) .
C63 H63 1.0000 .
C64 C65 1.560(4) .
C64 H64 1.0000 .
C65 O63 1.432(3) .
C65 C68 1.510(4) .
C65 C66 1.538(4) .
C66 O64 1.215(3) .
C66 N62 1.363(3) .
C67 O63 1.439(3) .
C67 N62 1.481(3) .
C67 C70 1.494(4) .
C68 O65 1.201(3) .
C68 O66 1.335(3) .
C69 O66 1.458(3) .
C69 H69A 0.9800 .
C69 H69B 0.9800 .
C69 H69C 0.9800 .
C70 H70A 0.9800 .
C70 H70B 0.9800 .
C70 H70C 0.9800 .
C71 C72 1.387(4) .
C71 C76 1.389(4) .
C71 N61 1.445(3) .
C72 C73 1.391(4) .
C72 H72 0.9500 .
C73 C74 1.390(4) .
C73 H73 0.9500 .
C74 C75 1.389(4) .
C74 H74 0.9500 .
C75 C76 1.389(4) .
C75 H75 0.9500 .
C76 H76 0.9500 .
C77 N62 1.469(3) .
C77 C78 1.511(4) .
C77 H77A 0.9900 .
C77 H77B 0.9900 .
C78 C83 1.380(4) .
C78 C79 1.388(4) .
C79 C80 1.389(5) .
C79 H79 0.9500 .
C80 C81 1.370(6) .
C80 H80 0.9500 .
C81 C82 1.368(6) .
C81 H81 0.9500 .
C82 C83 1.390(5) .
C82 H82 0.9500 .
C83 H83 0.9500 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139045413
