#------------------------------------------------------------------------------
#$Date: 2020-10-06 11:19:02 +0200 (mar 06 de oct de 2020) $
#$Revision: 257598 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/99/7239951.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_7239951
loop_
_publ_author_name
'Largeron, Martine'
'Deschamps, Patrick'
'Hammad, Karim'
'Fleury, Maurice-Bernard'
_publ_section_title
;
 A dual biomimetic process for the selective aerobic oxidative coupling of
 primary amines using pyrogallol as a precatalyst. Isolation of the [5 +
 2] cycloaddition redox intermediates
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              1894
_journal_page_last               1905
_journal_paper_doi               10.1039/C9GC03992A
_journal_volume                  22
_journal_year                    2020
_chemical_formula_sum            'C33 H27 N O6'
_chemical_formula_weight         533.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-11-12 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                102.027(2)
_cell_angle_beta                 105.432(2)
_cell_angle_gamma                112.595(2)
_cell_formula_units_Z            4
_cell_length_a                   12.6327(6)
_cell_length_b                   15.2434(7)
_cell_length_c                   15.9800(7)
_cell_measurement_reflns_used    9064
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.0
_cell_measurement_theta_min      3.4
_cell_volume                     2566.4(2)
_computing_cell_refinement       'SAINT v8.34 A (Bruker,2013)'
_computing_data_reduction        'SAINT v8.34 A (Bruker,2013)'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick,2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            77250
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.744
_diffrn_reflns_theta_max         66.744
_diffrn_reflns_theta_min         3.061
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  1.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens,1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     743
_refine_ls_number_reflns         9064
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0568P)²+0.8441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1045
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7943
_reflns_number_total             9064
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9gc03992a2.cif
_cod_data_source_block           cu_v830_0m
_cod_depositor_comments
;Adding full bibliography for 7239951--7239953.cif.

 Adding full bibliography for 7239951--7239953.cif.
;
_cod_database_code               7239951
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.824
_shelx_estimated_absorpt_t_max   0.964
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.14813(11) 0.53030(9) 0.30643(8) 0.0173(2) Uani 1 1 d . . . . .
C2 C 0.23688(11) 0.50878(9) 0.36018(8) 0.0177(2) Uani 1 1 d . . . . .
C3 C 0.35067(11) 0.58439(9) 0.42631(8) 0.0190(3) Uani 1 1 d . . . . .
C4 C 0.37927(11) 0.68540(9) 0.44197(8) 0.0190(3) Uani 1 1 d . . . . .
C4A C 0.29410(11) 0.71116(9) 0.38843(8) 0.0179(2) Uani 1 1 d . . . . .
C5 C 0.32932(11) 0.81813(9) 0.40908(8) 0.0178(2) Uani 1 1 d . . . . .
C6 C 0.24471(11) 0.85674(9) 0.35520(8) 0.0188(3) Uani 1 1 d . . . . .
C7 C 0.11829(11) 0.81426(9) 0.36347(8) 0.0205(3) Uani 1 1 d . . . . .
C8 C 0.04334(11) 0.71688(9) 0.31482(8) 0.0206(3) Uani 1 1 d . . . . .
H8 H -0.037488 0.684521 0.315118 0.031 Uiso 1 1 calc R U . . .
C9 C 0.08972(11) 0.65847(9) 0.25874(8) 0.0185(2) Uani 1 1 d . . . . .
H9 H 0.016742 0.594332 0.212031 0.028 Uiso 1 1 calc R U . . .
C9A C 0.17854(11) 0.63110(9) 0.31936(8) 0.0171(2) Uani 1 1 d . . . . .
C10 C 0.15544(11) 0.71997(9) 0.20742(8) 0.0182(2) Uani 1 1 d . . . . .
C12 C 0.02117(11) 0.44137(9) 0.24293(8) 0.0196(3) Uani 1 1 d . . . . .
H12A H -0.008793 0.452412 0.184125 0.029 Uiso 1 1 calc R U . . .
H12B H 0.028472 0.378073 0.228265 0.029 Uiso 1 1 calc R U . . .
C13 C -0.07139(11) 0.43081(9) 0.28929(8) 0.0206(3) Uani 1 1 d . . . . .
C14 C -0.06124(12) 0.39839(10) 0.36494(9) 0.0274(3) Uani 1 1 d . . . . .
H14 H 0.000315 0.377743 0.384729 0.041 Uiso 1 1 calc R U . . .
C15 C -0.13978(13) 0.39580(11) 0.41190(10) 0.0328(3) Uani 1 1 d . . . . .
H15 H -0.131887 0.373028 0.463139 0.049 Uiso 1 1 calc R U . . .
C16 C -0.22970(13) 0.42626(11) 0.38441(10) 0.0322(3) Uani 1 1 d . . . . .
H16 H -0.282811 0.425310 0.416965 0.048 Uiso 1 1 calc R U . . .
C17 C -0.24102(12) 0.45805(11) 0.30892(10) 0.0310(3) Uani 1 1 d . . . . .
H17 H -0.302078 0.479355 0.289758 0.047 Uiso 1 1 calc R U . . .
C18 C -0.16392(12) 0.45906(10) 0.26100(9) 0.0259(3) Uani 1 1 d . . . . .
H18 H -0.174321 0.479262 0.208263 0.039 Uiso 1 1 calc R U . . .
C19 C 0.09442(12) 0.88618(10) 0.42660(9) 0.0241(3) Uani 1 1 d . . . . .
H19A H 0.089262 0.937605 0.399062 0.036 Uiso 1 1 calc R U . . .
H19B H 0.166482 0.922156 0.486531 0.036 Uiso 1 1 calc R U . . .
C20 C -0.02211(12) 0.83771(10) 0.44534(8) 0.0242(3) Uani 1 1 d . . . . .
C21 C -0.04754(14) 0.75511(11) 0.47516(10) 0.0310(3) Uani 1 1 d . . . . .
H21 H 0.009595 0.728406 0.484402 0.046 Uiso 1 1 calc R U . . .
C22 C -0.15525(15) 0.71100(12) 0.49165(10) 0.0348(3) Uani 1 1 d . . . . .
H22 H -0.172487 0.653221 0.509951 0.052 Uiso 1 1 calc R U . . .
C23 C -0.23722(14) 0.75104(11) 0.48148(9) 0.0326(3) Uani 1 1 d . . . . .
H23 H -0.311122 0.720676 0.492266 0.049 Uiso 1 1 calc R U . . .
C24 C -0.21098(13) 0.83556(11) 0.45549(10) 0.0317(3) Uani 1 1 d . . . . .
H24 H -0.265158 0.865188 0.451043 0.047 Uiso 1 1 calc R U . . .
C25 C -0.10535(12) 0.87742(10) 0.43580(9) 0.0265(3) Uani 1 1 d . . . . .
H25 H -0.089893 0.933848 0.415593 0.040 Uiso 1 1 calc R U . . .
C26 C 0.28923(12) 0.88914(9) 0.21309(9) 0.0217(3) Uani 1 1 d . . . . .
H26A H 0.257011 0.939008 0.213884 0.033 Uiso 1 1 calc R U . . .
H26B H 0.265988 0.850317 0.147467 0.033 Uiso 1 1 calc R U . . .
C27 C 0.42858(12) 0.94586(10) 0.25914(9) 0.0257(3) Uani 1 1 d . . . . .
C28 C 0.49925(15) 0.89524(14) 0.27108(11) 0.0389(4) Uani 1 1 d . . . . .
H28 H 0.457616 0.823275 0.250584 0.058 Uiso 1 1 calc R U . A 1
C29A C 0.6264(6) 0.9445(7) 0.3111(4) 0.0643(17) Uani 0.756(17) 1 d D . P B 1
H29A H 0.671799 0.907885 0.321571 0.096 Uiso 0.756(17) 1 calc R U P B 1
C30A C 0.6862(8) 1.0478(7) 0.3356(6) 0.070(2) Uani 0.756(17) 1 d D . P B 1
H30A H 0.774267 1.083110 0.359179 0.105 Uiso 0.756(17) 1 calc R U P B 1
C31A C 0.6191(8) 1.1007(5) 0.3263(6) 0.063(2) Uani 0.756(17) 1 d D . P B 1
H31A H 0.662373 1.172677 0.347116 0.095 Uiso 0.756(17) 1 calc R U P B 1
C29B C 0.6312(16) 0.9623(10) 0.3072(10) 0.022(3) Uiso 0.244(17) 1 d D . P B 2
H29B H 0.684195 0.931716 0.308312 0.033 Uiso 0.244(17) 1 calc R U P B 2
C30B C 0.687(2) 1.0676(13) 0.3405(17) 0.025(3) Uiso 0.244(17) 1 d D . P B 2
H30B H 0.774333 1.106153 0.373948 0.037 Uiso 0.244(17) 1 calc R U P B 2
C31B C 0.6143(17) 1.1160(13) 0.3245(14) 0.020(3) Uiso 0.244(17) 1 d D . P B 2
H31B H 0.648192 1.187228 0.338340 0.030 Uiso 0.244(17) 1 calc R U P B 2
C32 C 0.48805(14) 1.05127(11) 0.28660(10) 0.0364(4) Uani 1 1 d . . . . .
H32 H 0.442498 1.088180 0.278996 0.055 Uiso 1 1 calc R U . B 1
C33 C 0.64918(11) 0.53471(9) 0.81124(8) 0.0176(2) Uani 1 1 d . . . . .
C34 C 0.73782(11) 0.51124(9) 0.86278(8) 0.0179(2) Uani 1 1 d . . . . .
C35 C 0.85524(11) 0.58566(9) 0.92460(8) 0.0190(3) Uani 1 1 d . . . . .
C36 C 0.88778(11) 0.68679(9) 0.93727(8) 0.0193(3) Uani 1 1 d . . . . .
C36A C 0.80251(11) 0.71428(9) 0.88682(8) 0.0178(2) Uani 1 1 d . . . . .
C37 C 0.84140(11) 0.82160(9) 0.90615(8) 0.0182(3) Uani 1 1 d . . . . .
C38 C 0.75750(11) 0.86192(9) 0.85467(8) 0.0178(2) Uani 1 1 d . . . . .
C39 C 0.63650(11) 0.82605(9) 0.87100(8) 0.0197(3) Uani 1 1 d . . . . .
C40 C 0.55609(11) 0.72910(9) 0.82548(8) 0.0197(3) Uani 1 1 d . . . . .
H40 H 0.477683 0.700756 0.830539 0.030 Uiso 1 1 calc R U . . .
C41 C 0.59211(11) 0.66465(9) 0.76529(8) 0.0182(2) Uani 1 1 d . . . . .
H41 H 0.515352 0.601196 0.721704 0.027 Uiso 1 1 calc R U . . .
C41A C 0.68246(11) 0.63554(9) 0.82220(8) 0.0172(2) Uani 1 1 d . . . . .
C42 C 0.65292(11) 0.72065(9) 0.70871(8) 0.0174(2) Uani 1 1 d . . . . .
C44 C 0.52138(11) 0.44723(9) 0.75214(8) 0.0194(3) Uani 1 1 d . . . . .
H44A H 0.529619 0.385496 0.729612 0.029 Uiso 1 1 calc R U . . .
H44B H 0.484861 0.462171 0.697344 0.029 Uiso 1 1 calc R U . . .
C45 C 0.43276(11) 0.42575(9) 0.80281(8) 0.0210(3) Uani 1 1 d . . . . .
C46 C 0.33340(13) 0.32911(11) 0.77138(10) 0.0302(3) Uani 1 1 d . . . . .
H46 H 0.325459 0.277104 0.721723 0.045 Uiso 1 1 calc R U . . .
C47 C 0.24561(13) 0.30719(12) 0.81122(11) 0.0363(3) Uani 1 1 d . . . . .
H47 H 0.177671 0.240936 0.787926 0.054 Uiso 1 1 calc R U . . .
C48 C 0.25643(14) 0.38102(13) 0.88439(10) 0.0358(3) Uani 1 1 d . . . . .
H48 H 0.196321 0.366056 0.911633 0.054 Uiso 1 1 calc R U . . .
C49 C 0.35555(14) 0.47684(12) 0.91754(10) 0.0336(3) Uani 1 1 d . . . . .
H49 H 0.364142 0.528028 0.968274 0.050 Uiso 1 1 calc R U . . .
C50 C 0.44316(13) 0.49908(10) 0.87714(9) 0.0271(3) Uani 1 1 d . . . . .
H50 H 0.511046 0.565403 0.900783 0.041 Uiso 1 1 calc R U . . .
C51 C 0.62153(12) 0.90209(10) 0.93720(9) 0.0239(3) Uani 1 1 d . . . . .
H51A H 0.614226 0.953007 0.909671 0.036 Uiso 1 1 calc R U . . .
H51B H 0.696558 0.937942 0.995236 0.036 Uiso 1 1 calc R U . . .
C52 C 0.50883(13) 0.85323(10) 0.95959(9) 0.0250(3) Uani 1 1 d . . . . .
C53 C 0.50732(14) 0.79294(11) 1.01416(10) 0.0316(3) Uani 1 1 d . . . . .
H53 H 0.578861 0.785161 1.039527 0.047 Uiso 1 1 calc R U . . .
C54 C 0.40177(15) 0.74385(12) 1.03193(10) 0.0389(4) Uani 1 1 d . . . . .
H54 H 0.401632 0.703050 1.069496 0.058 Uiso 1 1 calc R U . . .
C55 C 0.29725(15) 0.75458(13) 0.99483(11) 0.0420(4) Uani 1 1 d . . . . .
H55 H 0.224635 0.720200 1.005876 0.063 Uiso 1 1 calc R U . . .
C56 C 0.29881(16) 0.81509(14) 0.94199(12) 0.0452(4) Uani 1 1 d . . . . .
H56 H 0.227467 0.823366 0.917333 0.068 Uiso 1 1 calc R U . . .
C57 C 0.40416(15) 0.86440(12) 0.92426(11) 0.0359(3) Uani 1 1 d . . . . .
H57 H 0.404156 0.906092 0.887590 0.054 Uiso 1 1 calc R U . . .
C58 C 0.79714(12) 0.88337(9) 0.70883(8) 0.0211(3) Uani 1 1 d . . . . .
H58A H 0.784896 0.944512 0.717607 0.032 Uiso 1 1 calc R U . . .
H58B H 0.761739 0.845288 0.641451 0.032 Uiso 1 1 calc R U . . .
C59 C 0.93424(12) 0.91587(10) 0.74626(8) 0.0217(3) Uani 1 1 d . . . . .
C60 C 0.97661(13) 0.84402(10) 0.73834(9) 0.0277(3) Uani 1 1 d . . . . .
H60 H 0.918566 0.774037 0.709344 0.042 Uiso 1 1 calc R U . . .
C61 C 1.10239(13) 0.87328(12) 0.77223(10) 0.0335(3) Uani 1 1 d . . . . .
H61 H 1.130254 0.823475 0.766050 0.050 Uiso 1 1 calc R U . . .
C62 C 1.18782(13) 0.97515(12) 0.81519(10) 0.0330(3) Uani 1 1 d . . . . .
H62 H 1.274213 0.995371 0.839047 0.049 Uiso 1 1 calc R U . . .
C63 C 1.14656(14) 1.04692(11) 0.82307(10) 0.0351(3) Uani 1 1 d . . . . .
H63 H 1.204849 1.116829 0.852315 0.053 Uiso 1 1 calc R U . . .
C64 C 1.02058(13) 1.01778(10) 0.78861(10) 0.0290(3) Uani 1 1 d . . . . .
H64 H 0.993128 1.067867 0.793999 0.044 Uiso 1 1 calc R U . . .
N11 N 0.22801(9) 0.81868(7) 0.25586(7) 0.0189(2) Uani 1 1 d . . . . .
N43 N 0.72922(9) 0.81954(7) 0.75364(7) 0.0179(2) Uani 1 1 d . . . . .
O1 O 0.30369(8) 0.96154(6) 0.38824(6) 0.02094(19) Uani 1 1 d . . . . .
H1 H 0.376616 0.983244 0.425620 0.046(2) Uiso 1 1 calc R U . . .
O2 O 0.42913(8) 0.88612(6) 0.47064(6) 0.02218(19) Uani 1 1 d . . . . .
O3 O 0.49028(8) 0.75423(7) 0.50943(6) 0.0250(2) Uani 1 1 d . . . . .
H3 H 0.498007 0.812819 0.516282 0.046(2) Uiso 1 1 calc R U . . .
O4 O 0.42723(8) 0.55284(7) 0.47304(6) 0.0251(2) Uani 1 1 d . . . . .
H4 H 0.488048 0.602783 0.517168 0.046(2) Uiso 1 1 calc R U . . .
O5 O 0.20917(8) 0.41083(6) 0.34746(6) 0.02086(19) Uani 1 1 d . . . . .
H5 H 0.273939 0.407467 0.373577 0.046(2) Uiso 1 1 calc R U . . .
O6 O 0.14137(8) 0.67874(6) 0.12688(6) 0.02062(19) Uani 1 1 d . . . . .
O7 O 0.82117(8) 0.96668(6) 0.88440(6) 0.01961(19) Uani 1 1 d . . . . .
H7 H 0.893617 0.987196 0.922014 0.046(2) Uiso 1 1 calc R U . . .
O8 O 0.94366(8) 0.88821(6) 0.96550(6) 0.0237(2) Uani 1 1 d . . . . .
O9 O 1.00308(8) 0.75424(7) 0.99974(6) 0.0265(2) Uani 1 1 d . . . . .
H9A H 1.013510 0.813402 1.005770 0.046(2) Uiso 1 1 calc R U . . .
O10 O 0.93237(8) 0.55343(7) 0.96949(6) 0.0252(2) Uani 1 1 d . . . . .
H10 H 0.994144 0.603139 1.013161 0.046(2) Uiso 1 1 calc R U . . .
O11 O 0.70525(8) 0.41283(6) 0.85138(6) 0.02167(19) Uani 1 1 d . . . . .
H11 H 0.768547 0.407323 0.876990 0.046(2) Uiso 1 1 calc R U . . .
O12 O 0.63351(8) 0.67519(6) 0.62789(6) 0.02012(19) 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 0.0181 0.0096 '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 0.0189 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C9A C1 C2 118.05(11) . . ?
C9A C1 C12 124.10(11) . . ?
C2 C1 C12 117.69(10) . . ?
O5 C2 C3 118.89(11) . . ?
O5 C2 C1 118.71(10) . . ?
C3 C2 C1 122.39(11) . . ?
O4 C3 C2 116.17(11) . . ?
O4 C3 C4 124.19(11) . . ?
C2 C3 C4 119.63(11) . . ?
O3 C4 C3 115.91(11) . . ?
O3 C4 C4A 123.91(11) . . ?
C3 C4 C4A 120.18(11) . . ?
C4 C4A C9A 118.66(11) . . ?
C4 C4A C5 117.30(11) . . ?
C9A C4A C5 124.02(11) . . ?
O2 C5 C4A 122.78(11) . . ?
O2 C5 C6 114.71(10) . . ?
C4A C5 C6 122.51(10) . . ?
O1 C6 N11 109.47(9) . . ?
O1 C6 C7 111.17(10) . . ?
N11 C6 C7 109.66(10) . . ?
O1 C6 C5 109.49(9) . . ?
N11 C6 C5 106.16(9) . . ?
C7 C6 C5 110.76(10) . . ?
C8 C7 C19 127.69(12) . . ?
C8 C7 C6 115.23(11) . . ?
C19 C7 C6 117.07(10) . . ?
C7 C8 C9 118.27(11) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C8 C9 C9A 111.84(10) . . ?
C8 C9 C10 110.52(10) . . ?
C9A C9 C10 108.96(10) . . ?
C8 C9 H9 108.5 . . ?
C9A C9 H9 108.5 . . ?
C10 C9 H9 108.5 . . ?
C1 C9A C4A 121.01(11) . . ?
C1 C9A C9 120.23(10) . . ?
C4A C9A C9 118.76(10) . . ?
O6 C10 N11 123.99(11) . . ?
O6 C10 C9 120.96(11) . . ?
N11 C10 C9 115.05(10) . . ?
C13 C12 C1 110.42(10) . . ?
C13 C12 H12A 109.6 . . ?
C1 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C1 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C18 118.17(12) . . ?
C14 C13 C12 120.68(11) . . ?
C18 C13 C12 121.03(11) . . ?
C15 C14 C13 120.95(13) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 120.37(13) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.12(13) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.55(13) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 120.80(13) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C7 C19 C20 115.36(11) . . ?
C7 C19 H19A 108.4 . . ?
C20 C19 H19A 108.4 . . ?
C7 C19 H19B 108.4 . . ?
C20 C19 H19B 108.4 . . ?
H19A C19 H19B 107.5 . . ?
C21 C20 C25 118.05(13) . . ?
C21 C20 C19 121.68(12) . . ?
C25 C20 C19 120.24(12) . . ?
C22 C21 C20 121.07(14) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C21 120.14(14) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 119.56(13) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C23 C24 C25 120.20(14) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 120.89(13) . . ?
C20 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
N11 C26 C27 114.84(10) . . ?
N11 C26 H26A 108.6 . . ?
C27 C26 H26A 108.6 . . ?
N11 C26 H26B 108.6 . . ?
C27 C26 H26B 108.6 . . ?
H26A C26 H26B 107.5 . . ?
C28 C27 C32 119.38(14) . . ?
C28 C27 C26 121.44(13) . . ?
C32 C27 C26 119.11(13) . . ?
C27 C28 C29B 113.0(5) . . ?
C27 C28 C29A 122.9(4) . . ?
C27 C28 H28 118.5 . . ?
C29A C28 H28 118.5 . . ?
C30A C29A C28 118.3(6) . . ?
C30A C29A H29A 120.9 . . ?
C28 C29A H29A 120.9 . . ?
C31A C30A C29A 120.3(7) . . ?
C31A C30A H30A 119.8 . . ?
C29A C30A H30A 119.8 . . ?
C30A C31A C32 122.0(6) . . ?
C30A C31A H31A 119.0 . . ?
C32 C31A H31A 119.0 . . ?
C30B C29B C28 125.6(14) . . ?
C30B C29B H29B 117.2 . . ?
C28 C29B H29B 117.2 . . ?
C31B C30B C29B 119.4(18) . . ?
C31B C30B H30B 120.3 . . ?
C29B C30B H30B 120.3 . . ?
C30B C31B C32 114.0(16) . . ?
C30B C31B H31B 123.0 . . ?
C32 C31B H31B 123.0 . . ?
C31B C32 C27 127.8(6) . . ?
C31A C32 C27 117.0(4) . . ?
C31A C32 H32 121.5 . . ?
C27 C32 H32 121.5 . . ?
C41A C33 C34 118.43(11) . . ?
C41A C33 C44 124.68(11) . . ?
C34 C33 C44 116.78(11) . . ?
O11 C34 C35 119.62(11) . . ?
O11 C34 C33 118.21(11) . . ?
C35 C34 C33 122.17(11) . . ?
O10 C35 C34 116.60(11) . . ?
O10 C35 C36 123.89(11) . . ?
C34 C35 C36 119.51(11) . . ?
O9 C36 C35 115.59(11) . . ?
O9 C36 C36A 123.89(11) . . ?
C35 C36 C36A 120.52(11) . . ?
C36 C36A C41A 118.73(11) . . ?
C36 C36A C37 117.41(11) . . ?
C41A C36A C37 123.84(11) . . ?
O8 C37 C36A 122.48(11) . . ?
O8 C37 C38 114.93(10) . . ?
C36A C37 C38 122.58(10) . . ?
O7 C38 N43 109.05(9) . . ?
O7 C38 C39 111.27(10) . . ?
N43 C38 C39 109.37(9) . . ?
O7 C38 C37 109.55(9) . . ?
N43 C38 C37 107.35(9) . . ?
C39 C38 C37 110.15(10) . . ?
C40 C39 C51 126.89(12) . . ?
C40 C39 C38 115.24(11) . . ?
C51 C39 C38 117.85(10) . . ?
C39 C40 C41 118.30(11) . . ?
C39 C40 H40 120.8 . . ?
C41 C40 H40 120.8 . . ?
C40 C41 C42 110.69(10) . . ?
C40 C41 C41A 112.13(10) . . ?
C42 C41 C41A 108.13(10) . . ?
C40 C41 H41 108.6 . . ?
C42 C41 H41 108.6 . . ?
C41A C41 H41 108.6 . . ?
C33 C41A C36A 120.61(11) . . ?
C33 C41A C41 120.53(10) . . ?
C36A C41A C41 118.86(10) . . ?
O12 C42 N43 123.88(11) . . ?
O12 C42 C41 121.13(11) . . ?
N43 C42 C41 114.96(10) . . ?
C33 C44 C45 113.77(10) . . ?
C33 C44 H44A 108.8 . . ?
C45 C44 H44A 108.8 . . ?
C33 C44 H44B 108.8 . . ?
C45 C44 H44B 108.8 . . ?
H44A C44 H44B 107.7 . . ?
C50 C45 C46 117.74(12) . . ?
C50 C45 C44 123.33(11) . . ?
C46 C45 C44 118.88(12) . . ?
C47 C46 C45 121.23(14) . . ?
C47 C46 H46 119.4 . . ?
C45 C46 H46 119.4 . . ?
C48 C47 C46 120.39(13) . . ?
C48 C47 H47 119.8 . . ?
C46 C47 H47 119.8 . . ?
C47 C48 C49 119.20(13) . . ?
C47 C48 H48 120.4 . . ?
C49 C48 H48 120.4 . . ?
C48 C49 C50 120.44(14) . . ?
C48 C49 H49 119.8 . . ?
C50 C49 H49 119.8 . . ?
C45 C50 C49 120.99(13) . . ?
C45 C50 H50 119.5 . . ?
C49 C50 H50 119.5 . . ?
C39 C51 C52 112.29(11) . . ?
C39 C51 H51A 109.1 . . ?
C52 C51 H51A 109.1 . . ?
C39 C51 H51B 109.1 . . ?
C52 C51 H51B 109.1 . . ?
H51A C51 H51B 107.9 . . ?
C57 C52 C53 118.73(13) . . ?
C57 C52 C51 121.17(13) . . ?
C53 C52 C51 120.07(13) . . ?
C52 C53 C54 120.56(15) . . ?
C52 C53 H53 119.7 . . ?
C54 C53 H53 119.7 . . ?
C55 C54 C53 119.94(15) . . ?
C55 C54 H54 120.0 . . ?
C53 C54 H54 120.0 . . ?
C56 C55 C54 119.74(14) . . ?
C56 C55 H55 120.1 . . ?
C54 C55 H55 120.1 . . ?
C55 C56 C57 120.47(16) . . ?
C55 C56 H56 119.8 . . ?
C57 C56 H56 119.8 . . ?
C52 C57 C56 120.55(15) . . ?
C52 C57 H57 119.7 . . ?
C56 C57 H57 119.7 . . ?
N43 C58 C59 113.23(10) . . ?
N43 C58 H58A 108.9 . . ?
C59 C58 H58A 108.9 . . ?
N43 C58 H58B 108.9 . . ?
C59 C58 H58B 108.9 . . ?
H58A C58 H58B 107.7 . . ?
C64 C59 C60 118.75(12) . . ?
C64 C59 C58 120.86(12) . . ?
C60 C59 C58 120.38(11) . . ?
C61 C60 C59 120.73(13) . . ?
C61 C60 H60 119.6 . . ?
C59 C60 H60 119.6 . . ?
C60 C61 C62 120.09(14) . . ?
C60 C61 H61 120.0 . . ?
C62 C61 H61 120.0 . . ?
C63 C62 C61 119.54(13) . . ?
C63 C62 H62 120.2 . . ?
C61 C62 H62 120.2 . . ?
C62 C63 C64 120.45(13) . . ?
C62 C63 H63 119.8 . . ?
C64 C63 H63 119.8 . . ?
C63 C64 C59 120.44(13) . . ?
C63 C64 H64 119.8 . . ?
C59 C64 H64 119.8 . . ?
C10 N11 C26 121.24(10) . . ?
C10 N11 C6 118.27(10) . . ?
C26 N11 C6 120.48(9) . . ?
C42 N43 C58 121.29(10) . . ?
C42 N43 C38 118.29(10) . . ?
C58 N43 C38 119.94(9) . . ?
C6 O1 H1 109.5 . . ?
C4 O3 H3 109.5 . . ?
C3 O4 H4 109.5 . . ?
C2 O5 H5 109.5 . . ?
C38 O7 H7 109.5 . . ?
C36 O9 H9A 109.5 . . ?
C35 O10 H10 109.5 . . ?
C34 O11 H11 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C9A 1.3867(17) . ?
C1 C2 1.4107(17) . ?
C1 C12 1.5263(16) . ?
C2 O5 1.3518(15) . ?
C2 C3 1.3865(17) . ?
C3 O4 1.3591(15) . ?
C3 C4 1.3884(18) . ?
C4 O3 1.3501(15) . ?
C4 C4A 1.4208(17) . ?
C4A C9A 1.4321(17) . ?
C4A C5 1.4511(17) . ?
C5 O2 1.2420(15) . ?
C5 C6 1.5605(17) . ?
C6 O1 1.3822(14) . ?
C6 N11 1.4982(15) . ?
C6 C7 1.5299(17) . ?
C7 C8 1.3235(18) . ?
C7 C19 1.5053(18) . ?
C8 C9 1.5123(17) . ?
C8 H8 0.9500 . ?
C9 C9A 1.5234(17) . ?
C9 C10 1.5249(17) . ?
C9 H9 1.0000 . ?
C10 O6 1.2403(15) . ?
C10 N11 1.3345(16) . ?
C12 C13 1.5193(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.3918(19) . ?
C13 C18 1.3939(18) . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.5145(18) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.391(2) . ?
C20 C25 1.3920(19) . ?
C21 C22 1.391(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 N11 1.4724(16) . ?
C26 C27 1.5046(18) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.389(2) . ?
C27 C32 1.394(2) . ?
C28 C29B 1.445(17) . ?
C28 C29A 1.370(7) . ?
C28 H28 0.9500 . ?
C29A C30A 1.369(7) . ?
C29A H29A 0.9500 . ?
C30A C31A 1.378(7) . ?
C30A H30A 0.9500 . ?
C31A C32 1.412(9) . ?
C31A H31A 0.9500 . ?
C29B C30B 1.391(13) . ?
C29B H29B 0.9500 . ?
C30B C31B 1.390(12) . ?
C30B H30B 0.9500 . ?
C31B C32 1.383(19) . ?
C31B H31B 0.9500 . ?
C32 H32 0.9500 . ?
C33 C41A 1.3865(17) . ?
C33 C34 1.4141(17) . ?
C33 C44 1.5120(16) . ?
C34 O11 1.3509(15) . ?
C34 C35 1.3868(18) . ?
C35 O10 1.3594(15) . ?
C35 C36 1.3874(18) . ?
C36 O9 1.3502(15) . ?
C36 C36A 1.4183(17) . ?
C36A C41A 1.4346(17) . ?
C36A C37 1.4505(17) . ?
C37 O8 1.2402(15) . ?
C37 C38 1.5572(17) . ?
C38 O7 1.3843(14) . ?
C38 N43 1.4941(15) . ?
C38 C39 1.5274(17) . ?
C39 C40 1.3230(18) . ?
C39 C51 1.5040(17) . ?
C40 C41 1.5100(17) . ?
C40 H40 0.9500 . ?
C41 C42 1.5245(17) . ?
C41 C41A 1.5268(17) . ?
C41 H41 1.0000 . ?
C42 O12 1.2394(15) . ?
C42 N43 1.3345(16) . ?
C44 C45 1.5255(18) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C50 1.3886(19) . ?
C45 C46 1.3904(18) . ?
C46 C47 1.388(2) . ?
C46 H46 0.9500 . ?
C47 C48 1.379(2) . ?
C47 H47 0.9500 . ?
C48 C49 1.379(2) . ?
C48 H48 0.9500 . ?
C49 C50 1.393(2) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C51 C52 1.5091(18) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 C57 1.383(2) . ?
C52 C53 1.391(2) . ?
C53 C54 1.394(2) . ?
C53 H53 0.9500 . ?
C54 C55 1.382(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.373(3) . ?
C55 H55 0.9500 . ?
C56 C57 1.392(2) . ?
C56 H56 0.9500 . ?
C57 H57 0.9500 . ?
C58 N43 1.4736(16) . ?
C58 C59 1.5062(18) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C59 C64 1.3885(19) . ?
C59 C60 1.3895(19) . ?
C60 C61 1.383(2) . ?
C60 H60 0.9500 . ?
C61 C62 1.386(2) . ?
C61 H61 0.9500 . ?
C62 C63 1.379(2) . ?
C62 H62 0.9500 . ?
C63 C64 1.386(2) . ?
C63 H63 0.9500 . ?
C64 H64 0.9500 . ?
O1 H1 0.8400 . ?
O3 H3 0.8400 . ?
O4 H4 0.8400 . ?
O5 H5 0.8400 . ?
O7 H7 0.8400 . ?
O9 H9A 0.8400 . ?
O10 H10 0.8400 . ?
O11 H11 0.8400 . ?
