#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/39/4023944.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_4023944
loop_
_publ_author_name
'Martin Juhl'
'Rune Monrad'
'Inger Søtofte'
'David Tanner'
_publ_section_title
;
 Toward the Synthesis of Norzoanthamine: Complete Fragment Assembly
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4644
_journal_page_last               4654
_journal_paper_doi               10.1021/jo070165r
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C47 H54 N2 O13'
_chemical_formula_weight         854.92
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8902(5)
_cell_length_b                   15.6556(12)
_cell_length_c                   40.494(3)
_cell_measurement_reflns_used    22324
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      59.82
_cell_measurement_theta_min      3.03
_cell_volume                     4368.2(6)
_computing_cell_refinement       'SAINT (Bruker AXS,1998)'
_computing_data_collection       'SMART (Bruker AXS,1998)'
_computing_data_reduction        'SAINT (Bruker AXS,1998)'
_computing_molecular_graphics    'SHELXTL,ver.6.12 (Sheldrick,2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXTL,ver.6.12 (Sheldrick,2001)'
_computing_structure_solution    'SHELXTL,ver.6.12 (Sheldrick,2001)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1123
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            22324
_diffrn_reflns_theta_full        59.82
_diffrn_reflns_theta_max         59.82
_diffrn_reflns_theta_min         3.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1816
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       0.0036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.203
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         3478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.203
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0758
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1152P)²+1.5865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1800
_refine_ls_wR_factor_ref         0.2139
_reflns_number_gt                2571
_reflns_number_total             3478
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070165rsi20070209_105650.cif
_cod_data_source_block           mju85c
_cod_database_code               4023944
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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 0.8572(13) 0.6916(5) 0.1926(2) 0.040(2) Uani 1 1 d . . .
C2 C 0.7573(13) 0.7754(5) 0.1979(2) 0.046(2) Uani 1 1 d . . .
H21 H 0.8108 0.8031 0.2176 0.069 Uiso 1 1 calc R . .
H22 H 0.6180 0.7658 0.2010 0.069 Uiso 1 1 calc R . .
H23 H 0.7779 0.8122 0.1786 0.069 Uiso 1 1 calc R . .
C3 C 0.9965(13) 0.6631(5) 0.2123(2) 0.045(2) Uani 1 1 d . . .
H3 H 1.0332 0.6979 0.2305 0.054 Uiso 1 1 calc R . .
C4 C 1.1007(12) 0.5790(5) 0.2078(2) 0.040(2) Uani 1 1 d . . .
H4 H 1.0583 0.5386 0.2256 0.048 Uiso 1 1 calc R . .
O1 O 1.3097(8) 0.5918(4) 0.21034(13) 0.0484(16) Uani 1 1 d . . .
C5 C 1.3906(14) 0.5698(6) 0.2414(2) 0.056(3) Uani 1 1 d . . .
H51 H 1.3501 0.5111 0.2473 0.067 Uiso 1 1 calc R . .
H52 H 1.5339 0.5705 0.2397 0.067 Uiso 1 1 calc R . .
O2 O 1.3320(9) 0.6264(4) 0.26650(15) 0.0548(17) Uani 1 1 d . . .
C6 C 1.4185(15) 0.7098(6) 0.2640(2) 0.062(3) Uani 1 1 d . . .
H61 H 1.5602 0.7043 0.2641 0.092 Uiso 1 1 calc R . .
H62 H 1.3774 0.7449 0.2827 0.092 Uiso 1 1 calc R . .
H63 H 1.3769 0.7370 0.2433 0.092 Uiso 1 1 calc R . .
C7 C 1.0612(12) 0.5385(5) 0.17420(19) 0.038(2) Uani 1 1 d . . .
H7 H 1.1478 0.5665 0.1576 0.046 Uiso 1 1 calc R . .
C8 C 0.8522(11) 0.5483(5) 0.16251(19) 0.0322(19) Uani 1 1 d . . .
H8 H 0.7686 0.5161 0.1784 0.039 Uiso 1 1 calc R . .
C9 C 0.7853(13) 0.6418(4) 0.1634(2) 0.040(2) Uani 1 1 d . . .
H91 H 0.8302 0.6704 0.1429 0.048 Uiso 1 1 calc R . .
H92 H 0.6417 0.6431 0.1633 0.048 Uiso 1 1 calc R . .
C10 C 1.1139(13) 0.4432(5) 0.1757(2) 0.040(2) Uani 1 1 d . . .
H101 H 1.2544 0.4381 0.1804 0.048 Uiso 1 1 calc R . .
H102 H 1.0429 0.4168 0.1943 0.048 Uiso 1 1 calc R . .
C11 C 1.0694(12) 0.3936(5) 0.14471(19) 0.0339(19) Uani 1 1 d . . .
H11 H 1.1702 0.4046 0.1275 0.041 Uiso 1 1 calc R . .
C12 C 0.8649(12) 0.4082(5) 0.13060(19) 0.035(2) Uani 1 1 d . . .
H12 H 0.7714 0.3851 0.1472 0.042 Uiso 1 1 calc R . .
C13 C 0.8262(11) 0.5058(5) 0.12818(18) 0.0291(18) Uani 1 1 d . . .
C14 C 0.9634(12) 0.5471(5) 0.10232(18) 0.036(2) Uani 1 1 d . . .
H141 H 1.0984 0.5402 0.1095 0.055 Uiso 1 1 calc R . .
H142 H 0.9331 0.6080 0.1002 0.055 Uiso 1 1 calc R . .
H143 H 0.9453 0.5190 0.0809 0.055 Uiso 1 1 calc R . .
C15 C 0.6110(11) 0.5156(5) 0.11766(18) 0.0330(19) Uani 1 1 d . . .
H151 H 0.5810 0.5772 0.1155 0.040 Uiso 1 1 calc R . .
H152 H 0.5275 0.4922 0.1354 0.040 Uiso 1 1 calc R . .
C16 C 0.5588(12) 0.4704(4) 0.08474(18) 0.0316(18) Uani 1 1 d . . .
H16 H 0.4195 0.4530 0.0865 0.038 Uiso 1 1 calc R . .
C17 C 0.5714(12) 0.5350(5) 0.05663(19) 0.037(2) Uani 1 1 d . . .
O3 O 0.7102(9) 0.5343(3) 0.03658(13) 0.0427(15) Uani 1 1 d . . .
C18 C 0.4123(13) 0.5984(5) 0.0530(2) 0.047(2) Uani 1 1 d . . .
H181 H 0.4599 0.6482 0.0408 0.071 Uiso 1 1 calc R . .
H182 H 0.3681 0.6165 0.0749 0.071 Uiso 1 1 calc R . .
H183 H 0.3039 0.5724 0.0410 0.071 Uiso 1 1 calc R . .
C19 C 0.6732(12) 0.3902(5) 0.07811(18) 0.0323(19) Uani 1 1 d . . .
C20 C 0.8206(11) 0.3633(4) 0.09799(18) 0.0277(18) Uani 1 1 d . . .
C21 C 1.2462(13) 0.2625(5) 0.15557(19) 0.037(2) Uani 1 1 d . . .
O4 O 1.0732(8) 0.3027(3) 0.15510(12) 0.0390(14) Uani 1 1 d . . .
O5 O 1.3970(9) 0.2957(4) 0.14576(15) 0.0477(16) Uani 1 1 d . . .
C22 C 1.2337(12) 0.1757(5) 0.16929(19) 0.0332(19) Uani 1 1 d . . .
C23 C 1.3909(13) 0.1227(5) 0.1655(2) 0.043(2) Uani 1 1 d . . .
H231 H 1.5018 0.1418 0.1537 0.052 Uiso 1 1 calc R . .
C24 C 1.3871(13) 0.0402(6) 0.1792(2) 0.045(2) Uani 1 1 d . . .
H24 H 1.4942 0.0026 0.1765 0.054 Uiso 1 1 calc R . .
C25 C 1.2262(13) 0.0150(5) 0.1965(2) 0.041(2) Uani 1 1 d . . .
N1 N 1.2237(14) -0.0697(5) 0.2121(2) 0.058(2) Uani 1 1 d . . .
O6 O 1.0974(11) -0.0860(4) 0.23257(18) 0.068(2) Uani 1 1 d . . .
O7 O 1.3465(13) -0.1213(5) 0.2034(2) 0.094(3) Uani 1 1 d . . .
C26 C 1.0642(13) 0.0664(5) 0.20036(19) 0.044(2) Uani 1 1 d . . .
H26 H 0.9548 0.0469 0.2125 0.053 Uiso 1 1 calc R . .
C27 C 1.0654(13) 0.1476(5) 0.18611(19) 0.041(2) Uani 1 1 d . . .
H27 H 0.9546 0.1835 0.1877 0.050 Uiso 1 1 calc R . .
C28 C 0.9294(12) 0.2831(5) 0.0892(2) 0.037(2) Uani 1 1 d . . .
H281 H 1.0632 0.2865 0.0980 0.045 Uiso 1 1 calc R . .
H282 H 0.9376 0.2779 0.0648 0.045 Uiso 1 1 calc R . .
C29 C 0.8282(12) 0.2045(4) 0.1033(2) 0.039(2) Uani 1 1 d . . .
H291 H 0.7917 0.2146 0.1266 0.047 Uiso 1 1 calc R . .
H292 H 0.7090 0.1918 0.0906 0.047 Uiso 1 1 calc R . .
O8 O 0.9647(8) 0.1329(3) 0.10100(13) 0.0364(14) Uani 1 1 d . . .
C30 C 0.8968(13) 0.0583(5) 0.1126(2) 0.036(2) Uani 1 1 d . . .
O9 O 0.7330(9) 0.0508(3) 0.12306(16) 0.0505(16) Uani 1 1 d . . .
C31 C 1.0407(12) -0.0114(5) 0.11254(19) 0.037(2) Uani 1 1 d . . .
C32 C 1.2317(12) -0.0015(5) 0.10189(19) 0.036(2) Uani 1 1 d . . .
H32 H 1.2743 0.0525 0.0940 0.044 Uiso 1 1 calc R . .
C33 C 1.3604(12) -0.0697(5) 0.10261(18) 0.037(2) Uani 1 1 d . . .
H33 H 1.4896 -0.0644 0.0947 0.044 Uiso 1 1 calc R . .
C34 C 1.2908(12) -0.1458(5) 0.1155(2) 0.038(2) Uani 1 1 d . . .
N2 N 1.4218(12) -0.2200(5) 0.11627(18) 0.0484(19) Uani 1 1 d . . .
O10 O 1.5955(10) -0.2089(4) 0.10820(16) 0.0579(18) Uani 1 1 d . . .
O11 O 1.3562(9) -0.2896(4) 0.12505(17) 0.0586(18) Uani 1 1 d . . .
C35 C 1.1050(12) -0.1585(5) 0.1267(2) 0.044(2) Uani 1 1 d . . .
H35 H 1.0641 -0.2123 0.1351 0.053 Uiso 1 1 calc R . .
C36 C 0.9801(13) -0.0894(5) 0.1254(2) 0.045(2) Uani 1 1 d . . .
H36 H 0.8511 -0.0954 0.1333 0.054 Uiso 1 1 calc R . .
C37 C 0.6009(12) 0.3405(5) 0.04815(19) 0.0350(19) Uani 1 1 d . . .
H371 H 0.6965 0.2956 0.0424 0.042 Uiso 1 1 calc R . .
H372 H 0.5896 0.3796 0.0290 0.042 Uiso 1 1 calc R . .
C38 C 0.4029(11) 0.2988(5) 0.0549(2) 0.035(2) Uani 1 1 d . . .
H381 H 0.4027 0.2743 0.0774 0.042 Uiso 1 1 calc R . .
H382 H 0.3004 0.3431 0.0539 0.042 Uiso 1 1 calc R . .
C39 C 0.3567(12) 0.2291(4) 0.0302(2) 0.039(2) Uani 1 1 d . . .
H391 H 0.2216 0.2090 0.0332 0.046 Uiso 1 1 calc R . .
H392 H 0.3707 0.2510 0.0074 0.046 Uiso 1 1 calc R . .
O12 O 0.4901(8) 0.1602(3) 0.03573(13) 0.0401(14) Uani 1 1 d . . .
C40 C 0.4685(13) 0.0940(5) 0.0116(2) 0.041(2) Uani 1 1 d . . .
H401 H 0.4996 0.1165 -0.0106 0.050 Uiso 1 1 calc R . .
H402 H 0.3327 0.0734 0.0115 0.050 Uiso 1 1 calc R . .
C41 C 0.6033(12) 0.0216(5) 0.02003(19) 0.036(2) Uani 1 1 d . . .
C42 C 0.8030(12) 0.0377(5) 0.0248(2) 0.038(2) Uani 1 1 d . . .
H42 H 0.8511 0.0944 0.0234 0.046 Uiso 1 1 calc R . .
C43 C 0.9285(14) -0.0288(5) 0.03163(19) 0.043(2) Uani 1 1 d . . .
H43 H 1.0625 -0.0172 0.0349 0.051 Uiso 1 1 calc R . .
C44 C 0.8612(13) -0.1124(6) 0.0338(2) 0.043(2) Uani 1 1 d . . .
O13 O 0.9991(10) -0.1734(4) 0.04017(15) 0.0559(18) Uani 1 1 d . . .
C45 C 0.9326(16) -0.2588(5) 0.0438(3) 0.066(3) Uani 1 1 d . . .
H451 H 0.8200 -0.2598 0.0586 0.099 Uiso 1 1 calc R . .
H452 H 1.0366 -0.2940 0.0532 0.099 Uiso 1 1 calc R . .
H453 H 0.8954 -0.2816 0.0222 0.099 Uiso 1 1 calc R . .
C46 C 0.6664(13) -0.1295(5) 0.0289(2) 0.042(2) Uani 1 1 d . . .
H46 H 0.6193 -0.1864 0.0301 0.051 Uiso 1 1 calc R . .
C47 C 0.5401(13) -0.0622(5) 0.0221(2) 0.042(2) Uani 1 1 d . . .
H47 H 0.4064 -0.0742 0.0187 0.050 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 0.0181 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 0.0311 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 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
C3 C1 C9 122.7(8) . . ?
C3 C1 C2 122.6(8) . . ?
C9 C1 C2 114.7(7) . . ?
C1 C2 H21 109.5 . . ?
C1 C2 H22 109.5 . . ?
H21 C2 H22 109.5 . . ?
C1 C2 H23 109.5 . . ?
H21 C2 H23 109.5 . . ?
H22 C2 H23 109.5 . . ?
C1 C3 C4 124.3(8) . . ?
C1 C3 H3 117.9 . . ?
C4 C3 H3 117.9 . . ?
O1 C4 C3 110.0(7) . . ?
O1 C4 C7 107.2(7) . . ?
C3 C4 C7 112.7(7) . . ?
O1 C4 H4 109.0 . . ?
C3 C4 H4 109.0 . . ?
C7 C4 H4 109.0 . . ?
C5 O1 C4 114.6(7) . . ?
O2 C5 O1 112.1(7) . . ?
O2 C5 H51 109.2 . . ?
O1 C5 H51 109.2 . . ?
O2 C5 H52 109.2 . . ?
O1 C5 H52 109.2 . . ?
H51 C5 H52 107.9 . . ?
C5 O2 C6 113.6(7) . . ?
O2 C6 H61 109.5 . . ?
O2 C6 H62 109.5 . . ?
H61 C6 H62 109.5 . . ?
O2 C6 H63 109.5 . . ?
H61 C6 H63 109.5 . . ?
H62 C6 H63 109.5 . . ?
C8 C7 C4 113.8(7) . . ?
C8 C7 C10 109.5(7) . . ?
C4 C7 C10 109.1(6) . . ?
C8 C7 H7 108.1 . . ?
C4 C7 H7 108.1 . . ?
C10 C7 H7 108.1 . . ?
C7 C8 C9 112.0(7) . . ?
C7 C8 C13 110.1(6) . . ?
C9 C8 C13 113.2(6) . . ?
C7 C8 H8 107.1 . . ?
C9 C8 H8 107.1 . . ?
C13 C8 H8 107.1 . . ?
C1 C9 C8 114.4(7) . . ?
C1 C9 H91 108.6 . . ?
C8 C9 H91 108.7 . . ?
C1 C9 H92 108.7 . . ?
C8 C9 H92 108.7 . . ?
H91 C9 H92 107.6 . . ?
C11 C10 C7 114.8(6) . . ?
C11 C10 H101 108.6 . . ?
C7 C10 H101 108.6 . . ?
C11 C10 H102 108.6 . . ?
C7 C10 H102 108.6 . . ?
H101 C10 H102 107.5 . . ?
O4 C11 C10 104.8(6) . . ?
O4 C11 C12 105.3(6) . . ?
C10 C11 C12 114.8(7) . . ?
O4 C11 H11 110.6 . . ?
C10 C11 H11 110.6 . . ?
C12 C11 H11 110.6 . . ?
C20 C12 C11 115.9(6) . . ?
C20 C12 C13 111.3(6) . . ?
C11 C12 C13 109.1(6) . . ?
C20 C12 H12 106.7 . . ?
C11 C12 H12 106.7 . . ?
C13 C12 H12 106.7 . . ?
C15 C13 C14 110.9(6) . . ?
C15 C13 C8 108.3(6) . . ?
C14 C13 C8 110.8(6) . . ?
C15 C13 C12 106.2(6) . . ?
C14 C13 C12 110.3(6) . . ?
C8 C13 C12 110.2(6) . . ?
C13 C14 H141 109.5 . . ?
C13 C14 H142 109.5 . . ?
H141 C14 H142 109.5 . . ?
C13 C14 H143 109.5 . . ?
H141 C14 H143 109.5 . . ?
H142 C14 H143 109.5 . . ?
C13 C15 C16 114.4(6) . . ?
C13 C15 H151 108.7 . . ?
C16 C15 H151 108.7 . . ?
C13 C15 H152 108.7 . . ?
C16 C15 H152 108.7 . . ?
H151 C15 H152 107.6 . . ?
C19 C16 C17 112.9(6) . . ?
C19 C16 C15 114.3(6) . . ?
C17 C16 C15 109.0(6) . . ?
C19 C16 H16 106.7 . . ?
C17 C16 H16 106.7 . . ?
C15 C16 H16 106.7 . . ?
O3 C17 C18 120.3(7) . . ?
O3 C17 C16 121.4(7) . . ?
C18 C17 C16 118.3(7) . . ?
C17 C18 H181 109.5 . . ?
C17 C18 H182 109.5 . . ?
H181 C18 H182 109.5 . . ?
C17 C18 H183 109.5 . . ?
H181 C18 H183 109.5 . . ?
H182 C18 H183 109.5 . . ?
C20 C19 C16 122.9(7) . . ?
C20 C19 C37 123.7(7) . . ?
C16 C19 C37 113.3(7) . . ?
C19 C20 C28 119.3(7) . . ?
C19 C20 C12 121.2(7) . . ?
C28 C20 C12 119.3(6) . . ?
O5 C21 O4 123.1(7) . . ?
O5 C21 C22 124.2(7) . . ?
O4 C21 C22 112.7(7) . . ?
C21 O4 C11 117.9(6) . . ?
C23 C22 C27 120.9(7) . . ?
C23 C22 C21 118.0(7) . . ?
C27 C22 C21 121.1(7) . . ?
C22 C23 C24 119.8(8) . . ?
C22 C23 H231 120.1 . . ?
C24 C23 H231 120.1 . . ?
C25 C24 C23 118.7(8) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C24 C25 C26 122.9(7) . . ?
C24 C25 N1 119.3(8) . . ?
C26 C25 N1 117.7(8) . . ?
O7 N1 O6 123.3(8) . . ?
O7 N1 C25 117.6(9) . . ?
O6 N1 C25 119.1(8) . . ?
C25 C26 C27 118.5(8) . . ?
C25 C26 H26 120.7 . . ?
C27 C26 H26 120.7 . . ?
C26 C27 C22 119.1(8) . . ?
C26 C27 H27 120.4 . . ?
C22 C27 H27 120.4 . . ?
C20 C28 C29 110.8(6) . . ?
C20 C28 H281 109.5 . . ?
C29 C28 H281 109.5 . . ?
C20 C28 H282 109.5 . . ?
C29 C28 H282 109.5 . . ?
H281 C28 H282 108.1 . . ?
O8 C29 C28 107.4(6) . . ?
O8 C29 H291 110.2 . . ?
C28 C29 H291 110.2 . . ?
O8 C29 H292 110.2 . . ?
C28 C29 H292 110.2 . . ?
H291 C29 H292 108.5 . . ?
C30 O8 C29 114.8(6) . . ?
O9 C30 O8 122.0(7) . . ?
O9 C30 C31 123.9(7) . . ?
O8 C30 C31 114.1(7) . . ?
C36 C31 C32 119.8(7) . . ?
C36 C31 C30 116.5(7) . . ?
C32 C31 C30 123.7(7) . . ?
C33 C32 C31 120.8(7) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C34 C33 C32 116.6(7) . . ?
C34 C33 H33 121.7 . . ?
C32 C33 H33 121.7 . . ?
C35 C34 C33 124.8(7) . . ?
C35 C34 N2 116.8(8) . . ?
C33 C34 N2 118.3(8) . . ?
O11 N2 O10 123.3(7) . . ?
O11 N2 C34 118.6(8) . . ?
O10 N2 C34 118.1(8) . . ?
C34 C35 C36 117.0(8) . . ?
C34 C35 H35 121.5 . . ?
C36 C35 H35 121.5 . . ?
C35 C36 C31 120.9(8) . . ?
C35 C36 H36 119.5 . . ?
C31 C36 H36 119.5 . . ?
C19 C37 C38 111.5(7) . . ?
C19 C37 H371 109.3 . . ?
C38 C37 H371 109.3 . . ?
C19 C37 H372 109.3 . . ?
C38 C37 H372 109.3 . . ?
H371 C37 H372 108.0 . . ?
C39 C38 C37 112.1(7) . . ?
C39 C38 H381 109.2 . . ?
C37 C38 H381 109.2 . . ?
C39 C38 H382 109.2 . . ?
C37 C38 H382 109.2 . . ?
H381 C38 H382 107.9 . . ?
O12 C39 C38 107.7(6) . . ?
O12 C39 H391 110.2 . . ?
C38 C39 H391 110.2 . . ?
O12 C39 H392 110.2 . . ?
C38 C39 H392 110.2 . . ?
H391 C39 H392 108.5 . . ?
C40 O12 C39 111.8(6) . . ?
O12 C40 C41 109.1(6) . . ?
O12 C40 H401 109.9 . . ?
C41 C40 H401 109.9 . . ?
O12 C40 H402 109.9 . . ?
C41 C40 H402 109.9 . . ?
H401 C40 H402 108.3 . . ?
C47 C41 C42 117.9(8) . . ?
C47 C41 C40 122.2(8) . . ?
C42 C41 C40 119.9(7) . . ?
C43 C42 C41 120.2(8) . . ?
C43 C42 H42 119.9 . . ?
C41 C42 H42 119.9 . . ?
C42 C43 C44 120.9(8) . . ?
C42 C43 H43 119.6 . . ?
C44 C43 H43 119.6 . . ?
O13 C44 C46 124.4(8) . . ?
O13 C44 C43 115.9(8) . . ?
C46 C44 C43 119.7(8) . . ?
C44 O13 C45 116.9(8) . . ?
O13 C45 H451 109.5 . . ?
O13 C45 H452 109.5 . . ?
H451 C45 H452 109.5 . . ?
O13 C45 H453 109.5 . . ?
H451 C45 H453 109.5 . . ?
H452 C45 H453 109.5 . . ?
C44 C46 C47 119.3(8) . . ?
C44 C46 H46 120.4 . . ?
C47 C46 H46 120.4 . . ?
C41 C47 C46 122.1(9) . . ?
C41 C47 H47 119.0 . . ?
C46 C47 H47 119.0 . . ?
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 C3 1.328(11) . ?
C1 C9 1.500(11) . ?
C1 C2 1.498(11) . ?
C2 H21 0.9800 . ?
C2 H22 0.9800 . ?
C2 H23 0.9800 . ?
C3 C4 1.511(12) . ?
C3 H3 0.9500 . ?
C4 O1 1.458(10) . ?
C4 C7 1.527(11) . ?
C4 H4 1.0000 . ?
O1 C5 1.418(9) . ?
C5 O2 1.407(10) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
O2 C6 1.440(10) . ?
C6 H61 0.9800 . ?
C6 H62 0.9800 . ?
C6 H63 0.9800 . ?
C7 C8 1.523(10) . ?
C7 C10 1.535(11) . ?
C7 H7 1.0000 . ?
C8 C9 1.534(10) . ?
C8 C13 1.552(10) . ?
C8 H8 1.0000 . ?
C9 H91 0.9900 . ?
C9 H92 0.9900 . ?
C10 C11 1.506(10) . ?
C10 H101 0.9900 . ?
C10 H102 0.9900 . ?
C11 O4 1.484(9) . ?
C11 C12 1.537(10) . ?
C11 H11 1.0000 . ?
C12 C20 1.527(10) . ?
C12 C13 1.555(10) . ?
C12 H12 1.0000 . ?
C13 C15 1.550(10) . ?
C13 C14 1.552(10) . ?
C14 H141 0.9800 . ?
C14 H142 0.9800 . ?
C14 H143 0.9800 . ?
C15 C16 1.551(10) . ?
C15 H151 0.9900 . ?
C15 H152 0.9900 . ?
C16 C19 1.506(10) . ?
C16 C17 1.526(10) . ?
C16 H16 1.0000 . ?
C17 O3 1.255(9) . ?
C17 C18 1.487(10) . ?
C18 H181 0.9800 . ?
C18 H182 0.9800 . ?
C18 H183 0.9800 . ?
C19 C20 1.363(10) . ?
C19 C37 1.526(10) . ?
C20 C28 1.506(10) . ?
C21 O5 1.228(10) . ?
C21 O4 1.349(9) . ?
C21 C22 1.471(10) . ?
C22 C23 1.373(11) . ?
C22 C27 1.415(11) . ?
C23 C24 1.407(11) . ?
C23 H231 0.9500 . ?
C24 C25 1.369(12) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(11) . ?
C25 N1 1.471(10) . ?
N1 O7 1.222(10) . ?
N1 O6 1.228(10) . ?
C26 C27 1.396(11) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.526(10) . ?
C28 H281 0.9900 . ?
C28 H282 0.9900 . ?
C29 O8 1.465(8) . ?
C29 H291 0.9900 . ?
C29 H292 0.9900 . ?
O8 C30 1.345(9) . ?
C30 O9 1.210(9) . ?
C30 C31 1.474(11) . ?
C31 C36 1.392(11) . ?
C31 C32 1.393(12) . ?
C32 C33 1.388(11) . ?
C32 H32 0.9500 . ?
C33 C34 1.388(11) . ?
C33 H33 0.9500 . ?
C34 C35 1.372(12) . ?
C34 N2 1.471(10) . ?
N2 O11 1.232(9) . ?
N2 O10 1.253(9) . ?
C35 C36 1.383(11) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.537(11) . ?
C37 H371 0.9900 . ?
C37 H372 0.9900 . ?
C38 C39 1.514(11) . ?
C38 H381 0.9900 . ?
C38 H382 0.9900 . ?
C39 O12 1.435(8) . ?
C39 H391 0.9900 . ?
C39 H392 0.9900 . ?
O12 C40 1.431(9) . ?
C40 C41 1.505(11) . ?
C40 H401 0.9900 . ?
C40 H402 0.9900 . ?
C41 C47 1.384(11) . ?
C41 C42 1.412(12) . ?
C42 C43 1.381(11) . ?
C42 H42 0.9500 . ?
C43 C44 1.392(12) . ?
C43 H43 0.9500 . ?
C44 O13 1.372(10) . ?
C44 C46 1.383(13) . ?
O13 C45 1.421(10) . ?
C45 H451 0.9800 . ?
C45 H452 0.9800 . ?
C45 H453 0.9800 . ?
C46 C47 1.394(11) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
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
C9 C1 C3 C4 0.8(13) . . . . ?
C2 C1 C3 C4 180.0(8) . . . . ?
C1 C3 C4 O1 131.9(9) . . . . ?
C1 C3 C4 C7 12.4(12) . . . . ?
C3 C4 O1 C5 100.0(8) . . . . ?
C7 C4 O1 C5 -137.2(7) . . . . ?
C4 O1 C5 O2 -68.9(10) . . . . ?
O1 C5 O2 C6 -71.4(10) . . . . ?
O1 C4 C7 C8 -160.2(7) . . . . ?
C3 C4 C7 C8 -39.1(10) . . . . ?
O1 C4 C7 C10 77.2(8) . . . . ?
C3 C4 C7 C10 -161.7(7) . . . . ?
C4 C7 C8 C9 52.8(9) . . . . ?
C10 C7 C8 C9 175.1(6) . . . . ?
C4 C7 C8 C13 179.7(6) . . . . ?
C10 C7 C8 C13 -58.0(8) . . . . ?
C3 C1 C9 C8 12.8(12) . . . . ?
C2 C1 C9 C8 -166.4(7) . . . . ?
C7 C8 C9 C1 -38.7(10) . . . . ?
C13 C8 C9 C1 -163.9(7) . . . . ?
C8 C7 C10 C11 50.9(10) . . . . ?
C4 C7 C10 C11 176.1(7) . . . . ?
C7 C10 C11 O4 -162.9(7) . . . . ?
C7 C10 C11 C12 -48.0(10) . . . . ?
O4 C11 C12 C20 -69.2(8) . . . . ?
C10 C11 C12 C20 176.1(6) . . . . ?
O4 C11 C12 C13 164.2(6) . . . . ?
C10 C11 C12 C13 49.6(9) . . . . ?
C7 C8 C13 C15 178.7(7) . . . . ?
C9 C8 C13 C15 -55.1(9) . . . . ?
C7 C8 C13 C14 -59.4(8) . . . . ?
C9 C8 C13 C14 66.8(8) . . . . ?
C7 C8 C13 C12 63.0(8) . . . . ?
C9 C8 C13 C12 -170.8(7) . . . . ?
C20 C12 C13 C15 57.2(8) . . . . ?
C11 C12 C13 C15 -173.7(6) . . . . ?
C20 C12 C13 C14 -63.0(8) . . . . ?
C11 C12 C13 C14 66.1(8) . . . . ?
C20 C12 C13 C8 174.3(6) . . . . ?
C11 C12 C13 C8 -56.6(8) . . . . ?
C14 C13 C15 C16 62.3(8) . . . . ?
C8 C13 C15 C16 -175.9(6) . . . . ?
C12 C13 C15 C16 -57.5(8) . . . . ?
C13 C15 C16 C19 32.0(9) . . . . ?
C13 C15 C16 C17 -95.4(8) . . . . ?
C19 C16 C17 O3 -22.8(11) . . . . ?
C15 C16 C17 O3 105.4(8) . . . . ?
C19 C16 C17 C18 156.0(7) . . . . ?
C15 C16 C17 C18 -75.8(9) . . . . ?
C17 C16 C19 C20 120.5(8) . . . . ?
C15 C16 C19 C20 -4.9(10) . . . . ?
C17 C16 C19 C37 -62.5(9) . . . . ?
C15 C16 C19 C37 172.1(6) . . . . ?
C16 C19 C20 C28 -179.0(7) . . . . ?
C37 C19 C20 C28 4.3(11) . . . . ?
C16 C19 C20 C12 6.7(11) . . . . ?
C37 C19 C20 C12 -170.1(7) . . . . ?
C11 C12 C20 C19 -159.8(7) . . . . ?
C13 C12 C20 C19 -34.4(10) . . . . ?
C11 C12 C20 C28 25.9(10) . . . . ?
C13 C12 C20 C28 151.3(7) . . . . ?
O5 C21 O4 C11 -5.0(11) . . . . ?
C22 C21 O4 C11 174.5(6) . . . . ?
C10 C11 O4 C21 -85.3(8) . . . . ?
C12 C11 O4 C21 153.2(6) . . . . ?
O5 C21 C22 C23 -12.4(12) . . . . ?
O4 C21 C22 C23 168.1(7) . . . . ?
O5 C21 C22 C27 167.2(8) . . . . ?
O4 C21 C22 C27 -12.3(10) . . . . ?
C27 C22 C23 C24 -1.6(12) . . . . ?
C21 C22 C23 C24 178.0(7) . . . . ?
C22 C23 C24 C25 -0.9(12) . . . . ?
C23 C24 C25 C26 1.8(13) . . . . ?
C23 C24 C25 N1 -177.4(7) . . . . ?
C24 C25 N1 O7 -15.3(13) . . . . ?
C26 C25 N1 O7 165.5(9) . . . . ?
C24 C25 N1 O6 166.4(9) . . . . ?
C26 C25 N1 O6 -12.8(12) . . . . ?
C24 C25 C26 C27 -0.2(13) . . . . ?
N1 C25 C26 C27 179.0(7) . . . . ?
C25 C26 C27 C22 -2.3(12) . . . . ?
C23 C22 C27 C26 3.2(12) . . . . ?
C21 C22 C27 C26 -176.4(7) . . . . ?
C19 C20 C28 C29 -87.0(9) . . . . ?
C12 C20 C28 C29 87.4(9) . . . . ?
C20 C28 C29 O8 -166.1(6) . . . . ?
C28 C29 O8 C30 179.9(7) . . . . ?
C29 O8 C30 O9 2.5(11) . . . . ?
C29 O8 C30 C31 -175.5(6) . . . . ?
O9 C30 C31 C36 0.0(12) . . . . ?
O8 C30 C31 C36 177.9(7) . . . . ?
O9 C30 C31 C32 -177.0(8) . . . . ?
O8 C30 C31 C32 1.0(11) . . . . ?
C36 C31 C32 C33 2.8(12) . . . . ?
C30 C31 C32 C33 179.6(7) . . . . ?
C31 C32 C33 C34 -2.4(11) . . . . ?
C32 C33 C34 C35 1.6(13) . . . . ?
C32 C33 C34 N2 179.1(7) . . . . ?
C35 C34 N2 O11 3.9(11) . . . . ?
C33 C34 N2 O11 -173.9(8) . . . . ?
C35 C34 N2 O10 -175.5(8) . . . . ?
C33 C34 N2 O10 6.8(11) . . . . ?
C33 C34 C35 C36 -1.0(13) . . . . ?
N2 C34 C35 C36 -178.6(7) . . . . ?
C34 C35 C36 C31 1.2(13) . . . . ?
C32 C31 C36 C35 -2.2(13) . . . . ?
C30 C31 C36 C35 -179.2(8) . . . . ?
C20 C19 C37 C38 106.7(9) . . . . ?
C16 C19 C37 C38 -70.3(8) . . . . ?
C19 C37 C38 C39 -162.9(7) . . . . ?
C37 C38 C39 O12 67.6(8) . . . . ?
C38 C39 O12 C40 -175.0(7) . . . . ?
C39 O12 C40 C41 -176.6(6) . . . . ?
O12 C40 C41 C47 129.0(8) . . . . ?
O12 C40 C41 C42 -53.5(10) . . . . ?
C47 C41 C42 C43 -0.6(12) . . . . ?
C40 C41 C42 C43 -178.2(7) . . . . ?
C41 C42 C43 C44 0.1(12) . . . . ?
C42 C43 C44 O13 179.0(7) . . . . ?
C42 C43 C44 C46 0.5(13) . . . . ?
C46 C44 O13 C45 -4.0(12) . . . . ?
C43 C44 O13 C45 177.6(8) . . . . ?
O13 C44 C46 C47 -179.0(7) . . . . ?
C43 C44 C46 C47 -0.6(13) . . . . ?
C42 C41 C47 C46 0.5(12) . . . . ?
C40 C41 C47 C46 178.1(8) . . . . ?
C44 C46 C47 C41 0.1(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20563729
