#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/37/2013778.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2013778
loop_
_publ_author_name
'Nygren, Cara'
'Chen, Tianniu'
'Zhong, Sanbao'
'Kaczmarek, Conrad'
'Turner, John F. C.'
'Baker, David C.'
_publ_section_title
;A pair of epimeric
 13-hydroxy-2,3,6,7-tetramethoxy-8b,11,12,12a,13,13a-hexahydro-9H-9a-azacyclopenta[b]triphenylene-10-ones
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o208
_journal_page_last               o210
_journal_paper_doi               10.1107/S0108270104001659
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C24 H27 N O6'
_chemical_formula_moiety         'C24 H27 N O6'
_chemical_formula_sum            'C24 H27 N O6'
_chemical_formula_weight         425.47
_chemical_name_systematic
;
(8bS,13aS,14S,14aR)-8b,9,11,12,13,13a,14,14a-octahydro-14-hydroxy-2,3,6,7-
tetramethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinolin-11-one
;
_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           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.0534(16)
_cell_length_b                   14.9664(18)
_cell_length_c                   21.356(3)
_cell_measurement_reflns_used    8864
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.015
_cell_measurement_theta_min      2.28
_cell_volume                     4172.2(9)
_computing_cell_refinement       'SAINT (Bruker 1997)'
_computing_data_collection       'SMART (Bruker 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 'not measured'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            45934
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.66
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         5663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0549P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0861
_reflns_number_gt                4458
_reflns_number_total             5663
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1452.cif
_cod_data_source_block           III
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        4172.1(9)
_cod_database_code               2013778
_cod_database_fobs_code          2013778
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 -0.38698(16) 0.6461(2) 0.10355(14) 0.0729(8) Uani d . 1 . . C
H1A -0.3781 0.6981 0.1293 0.109 Uiso calc R 1 . . H
H1B -0.4513 0.6183 0.1132 0.109 Uiso calc R 1 . . H
H1C -0.3861 0.6634 0.0603 0.109 Uiso calc R 1 . . H
C2 -0.08087(18) 0.40862(17) 0.14478(11) 0.0581(6) Uani d . 1 . . C
H2A -0.0294 0.4047 0.1128 0.087 Uiso calc R 1 . . H
H2B -0.1106 0.3507 0.1514 0.087 Uiso calc R 1 . . H
H2C -0.0503 0.4292 0.1830 0.087 Uiso calc R 1 . . H
C3 -0.20793(13) 0.61648(16) 0.10554(9) 0.0450(5) Uani d . 1 . . C
C4 -0.12901(15) 0.55531(14) 0.11359(10) 0.0457(5) Uani d . 1 . . C
C5 -0.02846(14) 0.58458(14) 0.10897(9) 0.0410(4) Uani d . 1 . . C
H5 0.0246 0.5445 0.1162 0.049 Uiso calc R 1 . . H
C6 -0.00527(13) 0.67289(13) 0.09364(8) 0.0361(4) Uani d . 1 . . C
C7 0.10248(13) 0.70448(13) 0.08994(8) 0.0338(4) Uani d . 1 . . C
C8 0.18466(13) 0.64392(13) 0.09112(8) 0.0357(4) Uani d . 1 . . C
H8 0.1711 0.5829 0.0917 0.043 Uiso calc R 1 . . H
C9 0.28480(13) 0.67271(13) 0.09138(8) 0.0335(4) Uani d . 1 . . C
C10 0.35058(15) 0.52462(14) 0.10445(10) 0.0468(5) Uani d . 1 . . C
H10A 0.3115 0.5169 0.1421 0.070 Uiso calc R 1 . . H
H10B 0.4149 0.4941 0.1084 0.070 Uiso calc R 1 . . H
H10C 0.3132 0.5004 0.0696 0.070 Uiso calc R 1 . . H
C11 0.30628(13) 0.76456(13) 0.08704(8) 0.0351(4) Uani d . 1 . . C
C12 0.43643(15) 0.87549(15) 0.07236(11) 0.0503(5) Uani d . 1 . . C
H12A 0.4059 0.8924 0.0332 0.075 Uiso calc R 1 . . H
H12B 0.5096 0.8799 0.0691 0.075 Uiso calc R 1 . . H
H12C 0.4125 0.9146 0.1049 0.075 Uiso calc R 1 . . H
C13 0.22633(14) 0.82430(13) 0.08444(8) 0.0368(4) Uani d . 1 . . C
H13 0.2404 0.8851 0.0813 0.044 Uiso calc R 1 . . H
C14 0.12380(13) 0.79549(13) 0.08639(8) 0.0346(4) Uani d . 1 . . C
C15 0.03773(13) 0.86356(13) 0.08722(8) 0.0364(4) Uani d . 1 . . C
H15 0.0598 0.9136 0.0609 0.044 Uiso calc R 1 . . H
C16 -0.05984(13) 0.82460(14) 0.05676(8) 0.0379(4) Uani d . 1 . . C
H16 -0.0439 0.8168 0.0122 0.046 Uiso calc R 1 . . H
C17 -0.08515(13) 0.73258(14) 0.08162(8) 0.0374(4) Uani d . 1 . . C
C18 -0.18580(14) 0.70331(15) 0.08866(9) 0.0429(4) Uani d . 1 . . C
H18 -0.2393 0.7432 0.0818 0.051 Uiso calc R 1 . . H
C19 0.01858(13) 0.90181(13) 0.15334(9) 0.0377(4) Uani d . 1 . . C
H19 0.0796 0.9352 0.1663 0.045 Uiso calc R 1 . . H
C20 -0.07248(15) 0.96574(14) 0.15272(10) 0.0440(5) Uani d . 1 . . C
H20 -0.0539 1.0194 0.1290 0.053 Uiso calc R 1 . . H
C21 -0.14634(15) 0.89314(15) 0.05988(9) 0.0439(5) Uani d . 1 . . C
H21A -0.1301 0.9435 0.0330 0.053 Uiso calc R 1 . . H
H21B -0.2093 0.8663 0.0448 0.053 Uiso calc R 1 . . H
C22 -0.11493(17) 0.99393(18) 0.21682(11) 0.0600(6) Uani d . 1 . . C
H22A -0.0661 0.9805 0.2498 0.072 Uiso calc R 1 . . H
H22B -0.1296 1.0575 0.2175 0.072 Uiso calc R 1 . . H
C23 -0.2124(2) 0.94022(18) 0.22547(11) 0.0631(6) Uani d . 1 . . C
H23A -0.2008 0.8906 0.2538 0.076 Uiso calc R 1 . . H
H23B -0.2665 0.9775 0.2423 0.076 Uiso calc R 1 . . H
C24 -0.24051(16) 0.90671(15) 0.16120(10) 0.0503(5) Uani d . 1 . . C
C25 0.12520(18) 0.6868(2) 0.44443(15) 0.0762(8) Uani d . 1 . . C
H25A 0.1520 0.7465 0.4456 0.114 Uiso calc R 1 . . H
H25B 0.0614 0.6847 0.4668 0.114 Uiso calc R 1 . . H
H25C 0.1141 0.6693 0.4017 0.114 Uiso calc R 1 . . H
C26 0.3180(2) 0.66777(19) 0.58921(12) 0.0718(7) Uani d . 1 . . C
H26A 0.3681 0.7144 0.5853 0.108 Uiso calc R 1 . . H
H26B 0.3104 0.6521 0.6325 0.108 Uiso calc R 1 . . H
H26C 0.2536 0.6883 0.5731 0.108 Uiso calc R 1 . . H
C27 0.29411(15) 0.62605(14) 0.44984(10) 0.0460(5) Uani d . 1 . . C
C28 0.37175(15) 0.60827(14) 0.49247(10) 0.0438(5) Uani d . 1 . . C
C29 0.47152(15) 0.60509(14) 0.47247(9) 0.0424(4) Uani d . 1 . . C
H29 0.5228 0.5941 0.5017 0.051 Uiso calc R 1 . . H
C30 0.49892(14) 0.61766(13) 0.41009(9) 0.0386(4) Uani d . 1 . . C
C31 0.60741(14) 0.61966(13) 0.38919(9) 0.0379(4) Uani d . 1 . . C
C32 0.68862(15) 0.59450(14) 0.42873(9) 0.0413(4) Uani d . 1 . . C
H32 0.6739 0.5725 0.4684 0.050 Uiso calc R 1 . . H
C33 0.78939(14) 0.60151(13) 0.41027(9) 0.0410(4) Uani d . 1 . . C
C34 0.8546(2) 0.5721(3) 0.51190(12) 0.0870(10) Uani d . 1 . . C
H34A 0.8167 0.6224 0.5275 0.130 Uiso calc R 1 . . H
H34B 0.9190 0.5682 0.5334 0.130 Uiso calc R 1 . . H
H34C 0.8161 0.5184 0.5189 0.130 Uiso calc R 1 . . H
C35 0.81271(14) 0.63127(14) 0.34954(10) 0.0421(4) Uani d . 1 . . C
C36 0.93900(18) 0.6768(2) 0.27640(13) 0.0731(8) Uani d . 1 . . C
H36A 0.9139 0.6402 0.2428 0.110 Uiso calc R 1 . . H
H36B 1.0120 0.6827 0.2729 0.110 Uiso calc R 1 . . H
H36C 0.9079 0.7349 0.2741 0.110 Uiso calc R 1 . . H
C37 0.73366(15) 0.65526(14) 0.31023(9) 0.0444(5) Uani d . 1 . . C
H37 0.7486 0.6746 0.2699 0.053 Uiso calc R 1 . . H
C38 0.63171(14) 0.65119(14) 0.32969(8) 0.0412(4) Uani d . 1 . . C
C39 0.54856(14) 0.68634(15) 0.28707(9) 0.0455(5) Uani d . 1 . . C
H39 0.5706 0.6741 0.2441 0.055 Uiso calc R 1 . . H
C40 0.44783(14) 0.63474(14) 0.29714(9) 0.0419(4) Uani d . 1 . . C
H40 0.4616 0.5728 0.2849 0.050 Uiso calc R 1 . . H
C41 0.41947(14) 0.63212(13) 0.36641(9) 0.0385(4) Uani d . 1 . . C
C42 0.31890(15) 0.63767(14) 0.38729(10) 0.0455(5) Uani d . 1 . . C
H42 0.2670 0.6495 0.3586 0.055 Uiso calc R 1 . . H
C43 0.53451(16) 0.78797(15) 0.29227(10) 0.0498(5) Uani d . 1 . . C
H43 0.5988 0.8156 0.2787 0.060 Uiso calc R 1 . . H
C44 0.45112(16) 0.81881(16) 0.24687(11) 0.0523(5) Uani d . 1 . . C
H44 0.4756 0.8111 0.2038 0.063 Uiso calc R 1 . . H
C45 0.36677(16) 0.66932(14) 0.25197(10) 0.0469(5) Uani d . 1 . . C
H45A 0.3847 0.6522 0.2096 0.056 Uiso calc R 1 . . H
H45B 0.3011 0.6426 0.2620 0.056 Uiso calc R 1 . . H
C46 0.4113(2) 0.91385(18) 0.25493(15) 0.0728(8) Uani d . 1 . . C
H46A 0.4259 0.9358 0.2968 0.087 Uiso calc R 1 . . H
H46B 0.4429 0.9536 0.2247 0.087 Uiso calc R 1 . . H
C47 0.29618(18) 0.90797(16) 0.24401(12) 0.0595(6) Uani d . 1 . . C
H47A 0.2593 0.9432 0.2748 0.071 Uiso calc R 1 . . H
H47B 0.2786 0.9293 0.2025 0.071 Uiso calc R 1 . . H
C48 0.27091(16) 0.81063(15) 0.25066(9) 0.0458(5) Uani d . 1 . . C
N1 -0.16062(12) 0.92395(12) 0.12327(7) 0.0421(4) Uani d . 1 . . N
N2 0.35887(12) 0.76510(12) 0.25583(7) 0.0439(4) Uani d . 1 . . N
O1 -0.30562(11) 0.58452(12) 0.11522(8) 0.0637(5) Uani d . 1 . . O
O2 -0.15729(11) 0.46877(11) 0.12600(9) 0.0654(5) Uani d . 1 . . O
O3 0.36857(9) 0.61711(9) 0.09430(6) 0.0390(3) Uani d . 1 . . O
O4 0.40874(9) 0.78597(9) 0.08694(7) 0.0435(3) Uani d . 1 . . O
O5 -0.00081(10) 0.83453(9) 0.19847(6) 0.0439(3) Uani d . 1 . . O
H5A 0.0536 0.8174 0.2135 0.050 Uiso calc . 1 . . H
O6 -0.32067(13) 0.87013(14) 0.14628(10) 0.0756(5) Uani d . 1 . . O
O7 0.19539(11) 0.62821(13) 0.47251(8) 0.0686(5) Uani d . 1 . . O
O8 0.35066(11) 0.59153(10) 0.55475(7) 0.0510(4) Uani d . 1 . . O
O9 0.87204(10) 0.58299(12) 0.44724(7) 0.0546(4) Uani d . 1 . . O
O10 0.91417(10) 0.63643(11) 0.33464(7) 0.0543(4) Uani d . 1 . . O
O11 0.51549(13) 0.81767(11) 0.35438(7) 0.0601(4) Uani d . 1 . . O
H11 0.4692 0.7879 0.3698 0.050 Uiso calc . 1 . . H
O12 0.18543(11) 0.77607(11) 0.25114(7) 0.0575(4) Uani d . 1 . . O
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_publ_flag
O1 C1 H1A 109.5 ?
O1 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
O1 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
O2 C2 H2A 109.5 ?
O2 C2 H2B 109.5 ?
H2A C2 H2B 109.5 ?
O2 C2 H2C 109.5 ?
H2A C2 H2C 109.5 ?
H2B C2 H2C 109.5 ?
O1 C3 C18 124.08(19) ?
O1 C3 C4 116.05(19) ?
C18 C3 C4 119.87(17) ?
O2 C4 C5 124.48(19) ?
O2 C4 C3 116.52(17) ?
C5 C4 C3 119.00(19) ?
C4 C5 C6 121.41(18) ?
C4 C5 H5 119.3 ?
C6 C5 H5 119.3 ?
C5 C6 C17 119.16(16) ?
C5 C6 C7 121.28(16) yes
C17 C6 C7 119.56(17) ?
C14 C7 C8 118.67(16) ?
C14 C7 C6 120.22(16) ?
C8 C7 C6 121.10(16) yes
C9 C8 C7 121.55(17) ?
C9 C8 H8 119.2 ?
C7 C8 H8 119.2 ?
O3 C9 C8 124.46(17) ?
O3 C9 C11 115.84(15) ?
C8 C9 C11 119.68(16) ?
O3 C10 H10A 109.5 ?
O3 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
O3 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
O4 C11 C13 125.90(17) ?
O4 C11 C9 114.95(16) ?
C13 C11 C9 119.14(16) ?
O4 C12 H12A 109.5 ?
O4 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
O4 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
C11 C13 C14 121.43(17) ?
C11 C13 H13 119.3 ?
C14 C13 H13 119.3 ?
C7 C14 C13 119.45(16) ?
C7 C14 C15 120.56(15) ?
C13 C14 C15 119.95(16) ?
C14 C15 C19 112.30(14) ?
C14 C15 C16 110.63(15) yes
C19 C15 C16 113.06(14) ?
C14 C15 H15 106.8 ?
C19 C15 H15 106.8 ?
C16 C15 H15 106.8 ?
C17 C16 C21 115.78(15) yes
C17 C16 C15 112.09(15) yes
C21 C16 C15 109.74(16) ?
C17 C16 H16 106.2 ?
C21 C16 H16 106.2 ?
C15 C16 H16 106.2 ?
C18 C17 C6 118.88(18) yes
C18 C17 C16 122.02(17) ?
C6 C17 C16 118.93(15) ?
C3 C18 C17 121.47(19) ?
C3 C18 H18 119.3 ?
C17 C18 H18 119.3 ?
O5 C19 C20 108.21(15) yes
O5 C19 C15 112.80(15) yes
C20 C19 C15 110.52(15) ?
O5 C19 H19 108.4 ?
C20 C19 H19 108.4 ?
C15 C19 H19 108.4 ?
N1 C20 C19 110.53(16) ?
N1 C20 C22 102.61(16) ?
C19 C20 C22 116.46(17) ?
N1 C20 H20 109.0 ?
C19 C20 H20 109.0 ?
C22 C20 H20 109.0 ?
N1 C21 C16 110.56(14) ?
N1 C21 H21A 109.5 ?
C16 C21 H21A 109.5 ?
N1 C21 H21B 109.5 ?
C16 C21 H21B 109.5 ?
H21A C21 H21B 108.1 ?
C23 C22 C20 105.41(18) ?
C23 C22 H22A 110.7 ?
C20 C22 H22A 110.7 ?
C23 C22 H22B 110.7 ?
C20 C22 H22B 110.7 ?
H22A C22 H22B 108.8 ?
C24 C23 C22 105.67(19) ?
C24 C23 H23A 110.6 ?
C22 C23 H23A 110.6 ?
C24 C23 H23B 110.6 ?
C22 C23 H23B 110.6 ?
H23A C23 H23B 108.7 ?
O6 C24 N1 126.3(2) ?
O6 C24 C23 126.5(2) ?
N1 C24 C23 107.19(19) ?
O7 C25 H25A 109.5 ?
O7 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
O7 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
O8 C26 H26A 109.5 ?
O8 C26 H26B 109.5 ?
H26A C26 H26B 109.5 ?
O8 C26 H26C 109.5 ?
H26A C26 H26C 109.5 ?
H26B C26 H26C 109.5 ?
O7 C27 C42 123.68(19) ?
O7 C27 C28 117.22(19) ?
C42 C27 C28 119.07(18) ?
C29 C28 O8 118.87(19) ?
C29 C28 C27 119.72(19) ?
O8 C28 C27 121.39(18) ?
C28 C29 C30 122.50(18) ?
C28 C29 H29 118.7 ?
C30 C29 H29 118.7 ?
C29 C30 C41 117.66(17) ?
C29 C30 C31 122.36(17) ?
C41 C30 C31 119.93(17) ?
C38 C31 C32 117.84(17) ?
C38 C31 C30 119.89(17) ?
C32 C31 C30 122.20(17) ?
C33 C32 C31 121.85(18) ?
C33 C32 H32 119.1 ?
C31 C32 H32 119.1 ?
O9 C33 C32 125.01(18) ?
O9 C33 C35 115.28(16) ?
C32 C33 C35 119.70(17) ?
O9 C34 H34A 109.5 ?
O9 C34 H34B 109.5 ?
H34A C34 H34B 109.5 ?
O9 C34 H34C 109.5 ?
H34A C34 H34C 109.5 ?
H34B C34 H34C 109.5 ?
O10 C35 C37 124.76(18) ?
O10 C35 C33 116.34(17) ?
C37 C35 C33 118.88(17) ?
O10 C36 H36A 109.5 ?
O10 C36 H36B 109.5 ?
H36A C36 H36B 109.5 ?
O10 C36 H36C 109.5 ?
H36A C36 H36C 109.5 ?
H36B C36 H36C 109.5 ?
C35 C37 C38 121.42(17) ?
C35 C37 H37 119.3 ?
C38 C37 H37 119.3 ?
C31 C38 C37 120.26(17) ?
C31 C38 C39 120.27(17) ?
C37 C38 C39 119.38(17) ?
C38 C39 C43 112.76(17) ?
C38 C39 C40 110.77(17) ?
C43 C39 C40 112.62(17) ?
C38 C39 H39 106.7 ?
C43 C39 H39 106.7 ?
C40 C39 H39 106.7 ?
C45 C40 C41 117.04(16) ?
C45 C40 C39 109.54(17) ?
C41 C40 C39 110.83(15) ?
C45 C40 H40 106.2 ?
C41 C40 H40 106.2 ?
C39 C40 H40 106.2 ?
C42 C41 C30 119.44(18) ?
C42 C41 C40 122.62(17) ?
C30 C41 C40 117.80(16) ?
C27 C42 C41 121.52(18) ?
C27 C42 H42 119.2 ?
C41 C42 H42 119.2 ?
O11 C43 C44 111.91(19) ?
O11 C43 C39 113.46(16) ?
C44 C43 C39 109.76(18) ?
O11 C43 H43 107.1 ?
C44 C43 H43 107.1 ?
C39 C43 H43 107.1 ?
N2 C44 C46 102.59(18) ?
N2 C44 C43 109.74(17) ?
C46 C44 C43 116.9(2) ?
N2 C44 H44 109.1 ?
C46 C44 H44 109.1 ?
C43 C44 H44 109.1 ?
N2 C45 C40 110.61(17) ?
N2 C45 H45A 109.5 ?
C40 C45 H45A 109.5 ?
N2 C45 H45B 109.5 ?
C40 C45 H45B 109.5 ?
H45A C45 H45B 108.1 ?
C47 C46 C44 105.4(2) ?
C47 C46 H46A 110.7 ?
C44 C46 H46A 110.7 ?
C47 C46 H46B 110.7 ?
C44 C46 H46B 110.7 ?
H46A C46 H46B 108.8 ?
C48 C47 C46 105.0(2) ?
C48 C47 H47A 110.8 ?
C46 C47 H47A 110.8 ?
C48 C47 H47B 110.8 ?
C46 C47 H47B 110.8 ?
H47A C47 H47B 108.8 ?
O12 C48 N2 124.3(2) ?
O12 C48 C47 127.5(2) ?
N2 C48 C47 108.25(19) ?
C24 N1 C21 127.16(18) ?
C24 N1 C20 115.83(17) ?
C21 N1 C20 116.21(16) ?
C48 N2 C45 124.27(18) ?
C48 N2 C44 114.58(18) ?
C45 N2 C44 118.79(18) ?
C3 O1 C1 115.97(19) ?
C4 O2 C2 118.02(16) ?
C9 O3 C10 117.70(14) ?
C11 O4 C12 117.84(16) ?
C19 O5 H5A 109.5 ?
C27 O7 C25 118.41(19) ?
C28 O8 C26 114.35(17) ?
C33 O9 C34 117.53(17) ?
C35 O10 C36 116.73(17) ?
C43 O11 H11 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.428(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 O2 . 1.402(3) ?
C2 H2A . 0.9600 ?
C2 H2B . 0.9600 ?
C2 H2C . 0.9600 ?
C3 O1 . 1.378(2) ?
C3 C18 . 1.379(3) ?
C3 C4 . 1.389(3) ?
C4 O2 . 1.373(3) ?
C4 C5 . 1.387(3) ?
C5 C6 . 1.395(3) ?
C5 H5 . 0.9300 ?
C6 C17 . 1.397(3) ?
C6 C7 . 1.486(2) ?
C7 C14 . 1.392(3) ?
C7 C8 . 1.405(2) ?
C8 C9 . 1.376(2) ?
C8 H8 . 0.9300 ?
C9 O3 . 1.375(2) ?
C9 C11 . 1.406(3) ?
C10 O3 . 1.421(2) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 O4 . 1.375(2) ?
C11 C13 . 1.375(3) ?
C12 O4 . 1.422(3) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.407(2) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.517(2) ?
C15 C19 . 1.544(3) yes
C15 C16 . 1.544(3) ?
C15 H15 . 0.9800 ?
C16 C17 . 1.512(3) ?
C16 C21 . 1.527(3) ?
C16 H16 . 0.9800 ?
C17 C18 . 1.393(3) ?
C18 H18 . 0.9300 ?
C19 O5 . 1.417(2) yes
C19 C20 . 1.526(3) yes
C19 H19 . 0.9800 ?
C20 N1 . 1.453(2) ?
C20 C22 . 1.536(3) ?
C20 H20 . 0.9800 ?
C21 N1 . 1.442(2) ?
C21 H21A . 0.9700 ?
C21 H21B . 0.9700 ?
C22 C23 . 1.516(4) ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
C23 C24 . 1.507(3) ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
C24 O6 . 1.223(3) ?
C24 N1 . 1.345(3) ?
C25 O7 . 1.403(3) ?
C25 H25A . 0.9600 ?
C25 H25B . 0.9600 ?
C25 H25C . 0.9600 ?
C26 O8 . 1.423(3) ?
C26 H26A . 0.9600 ?
C26 H26B . 0.9600 ?
C26 H26C . 0.9600 ?
C27 O7 . 1.377(2) ?
C27 C42 . 1.385(3) ?
C27 C28 . 1.388(3) ?
C28 C29 . 1.371(3) ?
C28 O8 . 1.381(2) ?
C29 C30 . 1.392(3) ?
C29 H29 . 0.9300 ?
C30 C41 . 1.412(3) ?
C30 C31 . 1.485(3) ?
C31 C38 . 1.392(3) ?
C31 C32 . 1.407(3) ?
C32 C33 . 1.377(3) ?
C32 H32 . 0.9300 ?
C33 O9 . 1.365(2) ?
C33 C35 . 1.405(3) ?
C34 O9 . 1.409(3) ?
C34 H34A . 0.9600 ?
C34 H34B . 0.9600 ?
C34 H34C . 0.9600 ?
C35 O10 . 1.364(2) ?
C35 C37 . 1.378(3) ?
C36 O10 . 1.420(3) ?
C36 H36A . 0.9600 ?
C36 H36B . 0.9600 ?
C36 H36C . 0.9600 ?
C37 C38 . 1.395(3) ?
C37 H37 . 0.9300 ?
C38 C39 . 1.511(3) ?
C39 C43 . 1.536(3) ?
C39 C40 . 1.540(3) ?
C39 H39 . 0.9800 ?
C40 C45 . 1.523(3) ?
C40 C41 . 1.525(3) ?
C40 H40 . 0.9800 ?
C41 C42 . 1.389(3) ?
C42 H42 . 0.9300 ?
C43 O11 . 1.421(3) ?
C43 C44 . 1.529(3) ?
C43 H43 . 0.9800 ?
C44 N2 . 1.460(3) ?
C44 C46 . 1.524(4) ?
C44 H44 . 0.9800 ?
C45 N2 . 1.440(3) ?
C45 H45A . 0.9700 ?
C45 H45B . 0.9700 ?
C46 C47 . 1.524(3) ?
C46 H46A . 0.9700 ?
C46 H46B . 0.9700 ?
C47 C48 . 1.500(3) ?
C47 H47A . 0.9700 ?
C47 H47B . 0.9700 ?
C48 O12 . 1.230(2) ?
C48 N2 . 1.340(3) ?
O5 H5A . 0.8200 ?
O11 H11 . 0.8200 ?
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_publ_flag
O5 H5A O12 0.82 2.00 2.818(2) 179 yes
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_publ_flag
O1 C3 C4 O2 4.3(3) ?
C18 C3 C4 O2 -175.51(19) ?
O1 C3 C4 C5 -175.43(18) ?
C18 C3 C4 C5 4.7(3) ?
O2 C4 C5 C6 177.29(19) ?
C3 C4 C5 C6 -3.0(3) ?
C4 C5 C6 C17 -1.1(3) ?
C4 C5 C6 C7 178.79(18) ?
C5 C6 C7 C14 -167.79(17) ?
C17 C6 C7 C14 12.2(3) ?
C5 C6 C7 C8 11.0(3) yes
C17 C6 C7 C8 -169.06(17) ?
C14 C7 C8 C9 2.6(3) ?
C6 C7 C8 C9 -176.18(16) ?
C7 C8 C9 O3 178.07(16) ?
C7 C8 C9 C11 -3.4(3) ?
O3 C9 C11 O4 -0.6(2) ?
C8 C9 C11 O4 -179.25(16) ?
O3 C9 C11 C13 -179.48(15) ?
C8 C9 C11 C13 1.9(3) ?
O4 C11 C13 C14 -178.37(17) ?
C9 C11 C13 C14 0.4(3) ?
C8 C7 C14 C13 -0.3(3) ?
C6 C7 C14 C13 178.47(16) ?
C8 C7 C14 C15 -177.91(16) ?
C6 C7 C14 C15 0.9(3) ?
C11 C13 C14 C7 -1.1(3) ?
C11 C13 C14 C15 176.47(16) ?
C7 C14 C15 C19 96.3(2) ?
C13 C14 C15 C19 -81.2(2) ?
C7 C14 C15 C16 -31.0(2) ?
C13 C14 C15 C16 151.40(16) ?
C14 C15 C16 C17 48.18(19) yes
C19 C15 C16 C17 -78.76(19) ?
C14 C15 C16 C21 178.29(14) ?
C19 C15 C16 C21 51.3(2) ?
C5 C6 C17 C18 3.5(3) ?
C7 C6 C17 C18 -176.48(16) ?
C5 C6 C17 C16 -171.99(16) ?
C7 C6 C17 C16 8.1(2) ?
C21 C16 C17 C18 19.1(2) ?
C15 C16 C17 C18 146.05(17) ?
C21 C16 C17 C6 -165.57(16) ?
C15 C16 C17 C6 -38.6(2) ?
O1 C3 C18 C17 177.75(19) ?
C4 C3 C18 C17 -2.4(3) ?
C6 C17 C18 C3 -1.7(3) ?
C16 C17 C18 C3 173.59(17) ?
C14 C15 C19 O5 -55.40(19) ?
C16 C15 C19 O5 70.65(19) ?
C14 C15 C19 C20 -176.68(15) ?
C16 C15 C19 C20 -50.6(2) ?
O5 C19 C20 N1 -72.83(19) ?
C15 C19 C20 N1 51.1(2) ?
O5 C19 C20 C22 43.7(2) ?
C15 C19 C20 C22 167.68(18) ?
C17 C16 C21 N1 74.9(2) ?
C15 C16 C21 N1 -53.2(2) ?
N1 C20 C22 C23 17.3(2) ?
C19 C20 C22 C23 -103.5(2) ?
C20 C22 C23 C24 -17.1(2) ?
C22 C23 C24 O6 -170.2(2) ?
C22 C23 C24 N1 10.2(2) ?
O7 C27 C28 C29 179.8(2) ?
C42 C27 C28 C29 1.9(3) ?
O7 C27 C28 O8 1.4(3) ?
C42 C27 C28 O8 -176.58(19) ?
O8 C28 C29 C30 177.43(18) ?
C27 C28 C29 C30 -1.1(3) ?
C28 C29 C30 C41 -1.5(3) ?
C28 C29 C30 C31 176.20(19) ?
C29 C30 C31 C38 -166.16(19) ?
C41 C30 C31 C38 11.4(3) ?
C29 C30 C31 C32 10.7(3) ?
C41 C30 C31 C32 -171.65(19) ?
C38 C31 C32 C33 0.9(3) ?
C30 C31 C32 C33 -176.11(19) ?
C31 C32 C33 O9 176.3(2) ?
C31 C32 C33 C35 -2.5(3) ?
O9 C33 C35 O10 1.2(3) ?
C32 C33 C35 O10 -179.95(19) ?
O9 C33 C35 C37 -177.09(19) ?
C32 C33 C35 C37 1.8(3) ?
O10 C35 C37 C38 -177.6(2) ?
C33 C35 C37 C38 0.5(3) ?
C32 C31 C38 C37 1.4(3) ?
C30 C31 C38 C37 178.49(19) ?
C32 C31 C38 C39 -174.95(19) ?
C30 C31 C38 C39 2.1(3) ?
C35 C37 C38 C31 -2.1(3) ?
C35 C37 C38 C39 174.29(19) ?
C31 C38 C39 C43 93.4(2) ?
C37 C38 C39 C43 -83.0(2) ?
C31 C38 C39 C40 -33.8(3) ?
C37 C38 C39 C40 149.73(19) ?
C38 C39 C40 C45 -177.94(16) ?
C43 C39 C40 C45 54.7(2) ?
C38 C39 C40 C41 51.4(2) ?
C43 C39 C40 C41 -75.9(2) ?
C29 C30 C41 C42 3.2(3) ?
C31 C30 C41 C42 -174.55(18) ?
C29 C30 C41 C40 -172.81(18) ?
C31 C30 C41 C40 9.5(3) ?
C45 C40 C41 C42 16.6(3) ?
C39 C40 C41 C42 143.2(2) ?
C45 C40 C41 C30 -167.56(18) ?
C39 C40 C41 C30 -41.0(2) ?
O7 C27 C42 C41 -177.9(2) ?
C28 C27 C42 C41 -0.1(3) ?
C30 C41 C42 C27 -2.4(3) ?
C40 C41 C42 C27 173.34(19) ?
C38 C39 C43 O11 -55.3(2) ?
C40 C39 C43 O11 71.0(2) ?
C38 C39 C43 C44 178.70(16) ?
C40 C39 C43 C44 -55.0(2) ?
O11 C43 C44 N2 -75.4(2) ?
C39 C43 C44 N2 51.5(2) ?
O11 C43 C44 C46 40.8(3) ?
C39 C43 C44 C46 167.73(19) ?
C41 C40 C45 N2 75.6(2) ?
C39 C40 C45 N2 -51.6(2) ?
N2 C44 C46 C47 -20.2(3) ?
C43 C44 C46 C47 -140.3(2) ?
C44 C46 C47 C48 17.4(3) ?
C46 C47 C48 O12 172.9(2) ?
C46 C47 C48 N2 -7.4(3) ?
O6 C24 N1 C21 -8.9(4) ?
C23 C24 N1 C21 170.71(19) ?
O6 C24 N1 C20 -178.1(2) ?
C23 C24 N1 C20 1.4(2) ?
C16 C21 N1 C24 -110.3(2) ?
C16 C21 N1 C20 59.0(2) ?
C19 C20 N1 C24 112.71(19) ?
C22 C20 N1 C24 -12.1(2) ?
C19 C20 N1 C21 -57.8(2) ?
C22 C20 N1 C21 177.37(17) ?
O12 C48 N2 C45 11.0(3) ?
C47 C48 N2 C45 -168.61(18) ?
O12 C48 N2 C44 173.31(19) ?
C47 C48 N2 C44 -6.3(2) ?
C40 C45 N2 C48 -143.59(19) ?
C40 C45 N2 C44 54.8(2) ?
C46 C44 N2 C48 17.1(2) ?
C43 C44 N2 C48 142.10(19) ?
C46 C44 N2 C45 -179.54(19) ?
C43 C44 N2 C45 -54.6(3) ?
C18 C3 O1 C1 3.2(3) ?
C4 C3 O1 C1 -176.6(2) ?
C5 C4 O2 C2 10.3(3) ?
C3 C4 O2 C2 -169.4(2) ?
C8 C9 O3 C10 -7.0(3) ?
C11 C9 O3 C10 174.39(15) ?
C13 C11 O4 C12 -11.4(3) ?
C9 C11 O4 C12 169.84(16) ?
C42 C27 O7 C25 -34.7(3) ?
C28 C27 O7 C25 147.5(2) ?
C29 C28 O8 C26 110.1(2) ?
C27 C28 O8 C26 -71.4(3) ?
C32 C33 O9 C34 -12.5(3) ?
C35 C33 O9 C34 166.3(2) ?
C37 C35 O10 C36 5.8(3) ?
C33 C35 O10 C36 -172.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652382
