#------------------------------------------------------------------------------
#$Date: 2024-12-06 17:17:49 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296292 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/38/7133862.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_7133862
loop_
_publ_author_name
'Vijaykumar, Muniyappa'
'Pradhan, Chandini'
'Gonnade, Rajesh G.'
'Punji, Benudhar'
_publ_section_title
;
 Chelation-assisted and steric-controlled selectivity in the Pd-catalyzed
 C-H/C-H oxidative coupling of indoles.
;
_journal_issue                   89
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13028
_journal_page_last               13031
_journal_paper_doi               10.1039/d4cc03835e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C33 H28 N4 O3'
_chemical_formula_sum            'C33 H28 N4 O3'
_chemical_formula_weight         528.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'difference Fourier'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-06-26 deposited with the CCDC.	2024-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.094(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2208(6)
_cell_length_b                   16.2811(8)
_cell_length_c                   13.3170(7)
_cell_measurement_reflns_used    9689
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.21
_cell_volume                     2595.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            65679
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.338
_diffrn_reflns_theta_min         1.819
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         6403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0482
_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)+(0.0427P)²+2.1616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5431
_reflns_number_total             6403
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03835e2.cif
_cod_data_source_block           comp_25
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'direct method' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7133856--7133864.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7133862
_shelx_shelxl_version_number     2018/3
_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   0.991
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_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_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
O1 O 0.24977(10) 0.50957(7) 0.90959(9) 0.0302(3) Uani 1 1 d . . . . .
O2 O 0.43071(11) 0.10056(7) 0.30144(10) 0.0326(3) Uani 1 1 d . . . . .
N1 N 0.40874(10) 0.37660(7) 0.70459(9) 0.0180(2) Uani 1 1 d . . . . .
N2 N 0.56367(10) 0.36058(8) 0.66541(10) 0.0208(2) Uani 1 1 d . . . . .
N3 N 0.27579(9) 0.25854(7) 0.48327(9) 0.0174(2) Uani 1 1 d . . . . .
N4 N 0.20795(10) 0.23679(8) 0.61610(10) 0.0208(2) Uani 1 1 d . . . . .
C1 C 0.32577(11) 0.45068(8) 0.51860(11) 0.0173(3) Uani 1 1 d . . . . .
C2 C 0.26221(12) 0.51931(9) 0.46628(12) 0.0210(3) Uani 1 1 d . . . . .
H2 H 0.248479 0.530414 0.391557 0.025 Uiso 1 1 calc R U . . .
C3 C 0.21813(12) 0.57222(9) 0.51986(13) 0.0236(3) Uani 1 1 d . . . . .
H3 H 0.178016 0.619568 0.482075 0.028 Uiso 1 1 calc R U . . .
C4 C 0.23171(12) 0.55703(9) 0.62689(13) 0.0224(3) Uani 1 1 d . . . . .
H4 H 0.198025 0.591548 0.661601 0.027 Uiso 1 1 calc R U . . .
C5 C 0.29658(11) 0.48928(9) 0.68291(11) 0.0190(3) Uani 1 1 d . . . . .
C6 C 0.34831(11) 0.44004(8) 0.63049(11) 0.0169(3) Uani 1 1 d . . . . .
C7 C 0.38911(12) 0.38432(9) 0.79670(11) 0.0207(3) Uani 1 1 d . . . . .
C8 C 0.32245(12) 0.45097(9) 0.78794(12) 0.0205(3) Uani 1 1 d . . . . .
C9 C 0.30297(12) 0.45734(9) 0.88592(12) 0.0233(3) Uani 1 1 d . . . . .
C10 C 0.36230(14) 0.38413(10) 0.96183(12) 0.0274(3) Uani 1 1 d . . . . .
C11 C 0.42466(14) 0.33774(11) 0.90222(13) 0.0294(3) Uani 1 1 d . . . . .
H11A H 0.506638 0.340196 0.945957 0.035 Uiso 1 1 calc R U . . .
H11B H 0.400963 0.279571 0.888386 0.035 Uiso 1 1 calc R U . . .
C12 C 0.44128(19) 0.41642(13) 1.07487(14) 0.0451(5) Uani 1 1 d . . . . .
H12A H 0.500564 0.448673 1.067893 0.068 Uiso 1 1 calc R U . . .
H12B H 0.474445 0.370164 1.125284 0.068 Uiso 1 1 calc R U . . .
H12C H 0.399884 0.451282 1.104481 0.068 Uiso 1 1 calc R U . . .
C13 C 0.27224(19) 0.32998(12) 0.97173(19) 0.0447(5) Uani 1 1 d . . . . .
H13A H 0.223555 0.307834 0.898639 0.067 Uiso 1 1 calc R U . . .
H13B H 0.227751 0.362865 0.999907 0.067 Uiso 1 1 calc R U . . .
H13C H 0.307769 0.284610 1.022993 0.067 Uiso 1 1 calc R U . . .
C14 C 0.49022(11) 0.32387(9) 0.69445(10) 0.0172(3) Uani 1 1 d . . . . .
C15 C 0.48819(12) 0.24048(9) 0.71483(11) 0.0202(3) Uani 1 1 d . . . . .
H15 H 0.433622 0.217603 0.735438 0.024 Uiso 1 1 calc R U . . .
C16 C 0.56905(12) 0.19188(9) 0.70392(12) 0.0228(3) Uani 1 1 d . . . . .
H16 H 0.571854 0.134563 0.718206 0.027 Uiso 1 1 calc R U . . .
C17 C 0.64543(12) 0.22776(10) 0.67204(12) 0.0240(3) Uani 1 1 d . . . . .
H17 H 0.700957 0.195557 0.663061 0.029 Uiso 1 1 calc R U . . .
C18 C 0.63946(12) 0.31161(10) 0.65343(12) 0.0243(3) Uani 1 1 d . . . . .
H18 H 0.691903 0.335841 0.630930 0.029 Uiso 1 1 calc R U . . .
C19 C 0.36156(11) 0.39258(9) 0.45427(11) 0.0184(3) Uani 1 1 d . . . . .
C20 C 0.42619(12) 0.42187(9) 0.40191(11) 0.0210(3) Uani 1 1 d . . . . .
H20 H 0.438184 0.479339 0.401010 0.025 Uiso 1 1 calc R U . . .
C21 C 0.47395(12) 0.36930(10) 0.35063(12) 0.0234(3) Uani 1 1 d . . . . .
H21 H 0.517882 0.391809 0.316483 0.028 Uiso 1 1 calc R U . . .
C22 C 0.45833(12) 0.28545(10) 0.34883(12) 0.0230(3) Uani 1 1 d . . . . .
H22 H 0.493617 0.249920 0.316830 0.028 Uiso 1 1 calc R U . . .
C23 C 0.38931(11) 0.25401(9) 0.39524(11) 0.0198(3) Uani 1 1 d . . . . .
C24 C 0.33965(11) 0.30780(9) 0.44507(10) 0.0176(3) Uani 1 1 d . . . . .
C25 C 0.28835(12) 0.17768(9) 0.46123(11) 0.0204(3) Uani 1 1 d . . . . .
H25 H 0.255235 0.132447 0.481121 0.024 Uiso 1 1 calc R U . . .
C26 C 0.35554(12) 0.17162(9) 0.40641(12) 0.0215(3) Uani 1 1 d . . . . .
C27 C 0.20125(11) 0.28258(8) 0.53033(11) 0.0168(3) Uani 1 1 d . . . . .
C28 C 0.12707(11) 0.34707(9) 0.48564(11) 0.0194(3) Uani 1 1 d . . . . .
H28 H 0.121925 0.375181 0.421130 0.023 Uiso 1 1 calc R U . . .
C29 C 0.06072(12) 0.36893(9) 0.53870(13) 0.0233(3) Uani 1 1 d . . . . .
H29 H 0.011213 0.414353 0.512980 0.028 Uiso 1 1 calc R U . . .
C30 C 0.06721(13) 0.32401(10) 0.62951(13) 0.0255(3) Uani 1 1 d . . . . .
H30 H 0.023165 0.338257 0.667688 0.031 Uiso 1 1 calc R U . . .
C31 C 0.37944(13) 0.09753(10) 0.36020(13) 0.0262(3) Uani 1 1 d . . . . .
C32 C 0.3367(2) 0.01640(11) 0.38116(18) 0.0435(5) Uani 1 1 d . . . . .
H32A H 0.261699 0.006247 0.322788 0.065 Uiso 1 1 calc R U . . .
H32B H 0.333533 0.018002 0.453351 0.065 Uiso 1 1 calc R U . . .
H32C H 0.386975 -0.027736 0.380953 0.065 Uiso 1 1 calc R U . . .
C33 C 0.13963(13) 0.25774(10) 0.66320(12) 0.0245(3) Uani 1 1 d . . . . .
H33 H 0.141109 0.225219 0.723037 0.029 Uiso 1 1 calc R U . . .
O3 O 0.52818(11) -0.02863(8) 0.22628(11) 0.0338(3) Uani 1 1 d . . . . .
H3A H 0.490(2) 0.0148(15) 0.245(2) 0.051 Uiso 1 1 d . U . . .
H3B H 0.597(2) -0.0286(15) 0.280(2) 0.051 Uiso 1 1 d . U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C6 107.04(11) . . ?
C7 N1 C14 125.43(12) . . ?
C6 N1 C14 126.67(11) . . ?
C14 N2 C18 116.21(13) . . ?
C25 N3 C24 108.88(11) . . ?
C25 N3 C27 121.63(12) . . ?
C24 N3 C27 129.34(12) . . ?
C27 N4 C33 116.35(13) . . ?
C2 C1 C6 116.23(13) . . ?
C2 C1 C19 119.68(12) . . ?
C6 C1 C19 124.05(12) . . ?
C3 C2 C1 122.25(13) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C4 C3 C2 121.20(13) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 118.19(13) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C4 C5 C6 119.84(13) . . ?
C4 C5 C8 134.44(13) . . ?
C6 C5 C8 105.63(12) . . ?
C1 C6 C5 121.69(12) . . ?
C1 C6 N1 129.29(12) . . ?
C5 C6 N1 108.47(11) . . ?
N1 C7 C8 110.92(12) . . ?
N1 C7 C11 134.35(13) . . ?
C8 C7 C11 114.72(13) . . ?
C7 C8 C5 107.82(12) . . ?
C7 C8 C9 109.64(13) . . ?
C5 C8 C9 142.54(14) . . ?
O1 C9 C8 128.79(14) . . ?
O1 C9 C10 123.65(13) . . ?
C8 C9 C10 107.56(12) . . ?
C12 C10 C13 110.32(16) . . ?
C12 C10 C9 109.08(14) . . ?
C13 C10 C9 107.63(14) . . ?
C12 C10 C11 112.51(15) . . ?
C13 C10 C11 111.29(14) . . ?
C9 C10 C11 105.77(12) . . ?
C7 C11 C10 102.15(12) . . ?
C7 C11 H11A 111.3 . . ?
C10 C11 H11A 111.3 . . ?
C7 C11 H11B 111.3 . . ?
C10 C11 H11B 111.3 . . ?
H11A C11 H11B 109.2 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 125.02(13) . . ?
N2 C14 N1 115.50(12) . . ?
C15 C14 N1 119.47(12) . . ?
C16 C15 C14 117.29(13) . . ?
C16 C15 H15 121.4 . . ?
C14 C15 H15 121.4 . . ?
C17 C16 C15 119.21(14) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 118.62(14) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
N2 C18 C17 123.62(14) . . ?
N2 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
C20 C19 C24 116.05(13) . . ?
C20 C19 C1 118.94(13) . . ?
C24 C19 C1 124.95(12) . . ?
C19 C20 C21 122.18(14) . . ?
C19 C20 H20 118.9 . . ?
C21 C20 H20 118.9 . . ?
C22 C21 C20 121.19(13) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 118.40(14) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C22 C23 C24 119.97(13) . . ?
C22 C23 C26 132.47(13) . . ?
C24 C23 C26 107.55(12) . . ?
C19 C24 N3 131.43(12) . . ?
C19 C24 C23 121.91(13) . . ?
N3 C24 C23 106.58(12) . . ?
C26 C25 N3 110.29(13) . . ?
C26 C25 H25 124.9 . . ?
N3 C25 H25 124.9 . . ?
C25 C26 C23 106.67(13) . . ?
C25 C26 C31 126.38(14) . . ?
C23 C26 C31 126.74(13) . . ?
N4 C27 C28 124.62(13) . . ?
N4 C27 N3 114.50(12) . . ?
C28 C27 N3 120.86(12) . . ?
C29 C28 C27 117.44(13) . . ?
C29 C28 H28 121.3 . . ?
C27 C28 H28 121.3 . . ?
C30 C29 C28 119.44(14) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C29 C30 C33 118.21(14) . . ?
C29 C30 H30 120.9 . . ?
C33 C30 H30 120.9 . . ?
O2 C31 C26 120.88(15) . . ?
O2 C31 C32 120.13(14) . . ?
C26 C31 C32 118.94(14) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N4 C33 C30 123.76(14) . . ?
N4 C33 H33 118.1 . . ?
C30 C33 H33 118.1 . . ?
H3A O3 H3B 105(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.2270(18) . ?
O2 C31 1.2345(18) . ?
N1 C7 1.3631(17) . ?
N1 C6 1.4178(17) . ?
N1 C14 1.4280(17) . ?
N2 C14 1.3298(18) . ?
N2 C18 1.3418(19) . ?
N3 C25 1.3741(18) . ?
N3 C24 1.4068(17) . ?
N3 C27 1.4286(17) . ?
N4 C27 1.3350(18) . ?
N4 C33 1.3438(19) . ?
C1 C2 1.3942(19) . ?
C1 C6 1.4008(18) . ?
C1 C19 1.4821(19) . ?
C2 C3 1.394(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.4152(19) . ?
C5 C8 1.4340(19) . ?
C7 C8 1.371(2) . ?
C7 C11 1.487(2) . ?
C8 C9 1.4369(19) . ?
C9 C10 1.544(2) . ?
C10 C12 1.516(2) . ?
C10 C13 1.532(3) . ?
C10 C11 1.560(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3870(19) . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.3961(19) . ?
C19 C24 1.405(2) . ?
C20 C21 1.401(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.398(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.4170(19) . ?
C23 C26 1.441(2) . ?
C25 C26 1.372(2) . ?
C25 H25 0.9500 . ?
C26 C31 1.449(2) . ?
C27 C28 1.3869(19) . ?
C28 C29 1.386(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.384(2) . ?
C29 H29 0.9500 . ?
C30 C33 1.385(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.509(2) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33 0.9500 . ?
O3 H3A 0.96(3) . ?
O3 H3B 0.89(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C25 H25 O1 0.95 2.49 3.3822(19) 156.2 2_546 yes
C28 H28 O3 0.95 2.63 3.3704(19) 134.6 2 yes
C32 H32B O1 0.98 2.50 3.433(2) 158.2 2_546 yes
O3 H3A O2 0.96(3) 1.90(3) 2.8602(17) 172(2) . yes
O3 H3B O1 0.89(3) 2.05(3) 2.9278(18) 171(2) 4_665 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -3.4(2) . . . . ?
C19 C1 C2 C3 174.40(13) . . . . ?
C1 C2 C3 C4 -2.7(2) . . . . ?
C2 C3 C4 C5 3.5(2) . . . . ?
C3 C4 C5 C6 1.7(2) . . . . ?
C3 C4 C5 C8 -174.50(15) . . . . ?
C2 C1 C6 C5 8.64(19) . . . . ?
C19 C1 C6 C5 -169.03(13) . . . . ?
C2 C1 C6 N1 179.19(13) . . . . ?
C19 C1 C6 N1 1.5(2) . . . . ?
C4 C5 C6 C1 -8.0(2) . . . . ?
C8 C5 C6 C1 169.15(12) . . . . ?
C4 C5 C6 N1 179.70(12) . . . . ?
C8 C5 C6 N1 -3.15(15) . . . . ?
C7 N1 C6 C1 -168.25(14) . . . . ?
C14 N1 C6 C1 22.0(2) . . . . ?
C7 N1 C6 C5 3.28(15) . . . . ?
C14 N1 C6 C5 -166.50(12) . . . . ?
C6 N1 C7 C8 -2.10(16) . . . . ?
C14 N1 C7 C8 167.84(13) . . . . ?
C6 N1 C7 C11 178.73(17) . . . . ?
C14 N1 C7 C11 -11.3(3) . . . . ?
N1 C7 C8 C5 0.12(17) . . . . ?
C11 C7 C8 C5 179.47(13) . . . . ?
N1 C7 C8 C9 179.81(12) . . . . ?
C11 C7 C8 C9 -0.84(19) . . . . ?
C4 C5 C8 C7 178.43(15) . . . . ?
C6 C5 C8 C7 1.89(16) . . . . ?
C4 C5 C8 C9 -1.1(3) . . . . ?
C6 C5 C8 C9 -177.63(19) . . . . ?
C7 C8 C9 O1 178.29(16) . . . . ?
C5 C8 C9 O1 -2.2(3) . . . . ?
C7 C8 C9 C10 -1.83(17) . . . . ?
C5 C8 C9 C10 177.69(19) . . . . ?
O1 C9 C10 C12 -55.3(2) . . . . ?
C8 C9 C10 C12 124.84(15) . . . . ?
O1 C9 C10 C13 64.4(2) . . . . ?
C8 C9 C10 C13 -115.46(15) . . . . ?
O1 C9 C10 C11 -176.52(15) . . . . ?
C8 C9 C10 C11 3.59(17) . . . . ?
N1 C7 C11 C10 -177.83(16) . . . . ?
C8 C7 C11 C10 3.02(18) . . . . ?
C12 C10 C11 C7 -122.81(16) . . . . ?
C13 C10 C11 C7 112.79(16) . . . . ?
C9 C10 C11 C7 -3.81(16) . . . . ?
C18 N2 C14 C15 1.3(2) . . . . ?
C18 N2 C14 N1 -178.75(12) . . . . ?
C7 N1 C14 N2 -124.06(15) . . . . ?
C6 N1 C14 N2 43.92(18) . . . . ?
C7 N1 C14 C15 55.87(19) . . . . ?
C6 N1 C14 C15 -136.15(14) . . . . ?
N2 C14 C15 C16 -0.1(2) . . . . ?
N1 C14 C15 C16 -179.98(12) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C15 C16 C17 C18 0.8(2) . . . . ?
C14 N2 C18 C17 -1.5(2) . . . . ?
C16 C17 C18 N2 0.5(2) . . . . ?
C2 C1 C19 C20 58.60(18) . . . . ?
C6 C1 C19 C20 -123.80(14) . . . . ?
C2 C1 C19 C24 -124.36(15) . . . . ?
C6 C1 C19 C24 53.2(2) . . . . ?
C24 C19 C20 C21 -4.88(19) . . . . ?
C1 C19 C20 C21 172.43(13) . . . . ?
C19 C20 C21 C22 0.5(2) . . . . ?
C20 C21 C22 C23 2.8(2) . . . . ?
C21 C22 C23 C24 -1.6(2) . . . . ?
C21 C22 C23 C26 179.65(15) . . . . ?
C20 C19 C24 N3 -177.59(13) . . . . ?
C1 C19 C24 N3 5.3(2) . . . . ?
C20 C19 C24 C23 6.08(19) . . . . ?
C1 C19 C24 C23 -171.04(12) . . . . ?
C25 N3 C24 C19 -174.89(14) . . . . ?
C27 N3 C24 C19 9.6(2) . . . . ?
C25 N3 C24 C23 1.85(14) . . . . ?
C27 N3 C24 C23 -173.63(12) . . . . ?
C22 C23 C24 C19 -3.0(2) . . . . ?
C26 C23 C24 C19 176.03(12) . . . . ?
C22 C23 C24 N3 179.86(12) . . . . ?
C26 C23 C24 N3 -1.09(14) . . . . ?
C24 N3 C25 C26 -1.95(16) . . . . ?
C27 N3 C25 C26 173.95(12) . . . . ?
N3 C25 C26 C23 1.23(16) . . . . ?
N3 C25 C26 C31 -173.78(14) . . . . ?
C22 C23 C26 C25 178.83(15) . . . . ?
C24 C23 C26 C25 -0.05(15) . . . . ?
C22 C23 C26 C31 -6.2(3) . . . . ?
C24 C23 C26 C31 174.93(14) . . . . ?
C33 N4 C27 C28 -2.3(2) . . . . ?
C33 N4 C27 N3 179.60(12) . . . . ?
C25 N3 C27 N4 45.83(17) . . . . ?
C24 N3 C27 N4 -139.19(13) . . . . ?
C25 N3 C27 C28 -132.33(14) . . . . ?
C24 N3 C27 C28 42.65(19) . . . . ?
N4 C27 C28 C29 4.7(2) . . . . ?
N3 C27 C28 C29 -177.37(12) . . . . ?
C27 C28 C29 C30 -2.9(2) . . . . ?
C28 C29 C30 C33 -0.7(2) . . . . ?
C25 C26 C31 O2 171.59(15) . . . . ?
C23 C26 C31 O2 -2.4(2) . . . . ?
C25 C26 C31 C32 -6.0(2) . . . . ?
C23 C26 C31 C32 179.97(16) . . . . ?
C27 N4 C33 C30 -1.8(2) . . . . ?
C29 C30 C33 N4 3.3(2) . . . . ?
