#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:20:18 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278981 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/76/1567648.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_1567648
loop_
_publ_author_name
'Guo, Wengang'
'Jiang, Feng'
'Li, Shijia'
'Sun, Jianwei'
_publ_section_title
;
 Organocatalytic asymmetric azidation of sulfoxonium ylides: mild
 synthesis of enantioenriched α-azido ketones bearing a labile tertiary
 stereocenter.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              11648
_journal_page_last               11655
_journal_paper_doi               10.1039/d2sc03552a
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H25 N O3'
_chemical_formula_weight         387.46
_chemical_name_systematic
'tert-Butyl (R)-(1-([1,1'-biphenyl]-4-yl)-2-oxo-2-phenylethyl)carbamate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-02-02 deposited with the CCDC.	2022-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.1980(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.5777(2)
_cell_length_b                   41.8595(7)
_cell_length_c                   10.6059(2)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      140.147
_cell_measurement_theta_min      6.334
_cell_volume                     4249.18(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            39522
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.496
_diffrn_reflns_theta_min         4.607
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1648
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and diethyl ether'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details
; 
 Flack x determined using 5988 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1073
_refine_ls_number_reflns         14813
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0626P)²+0.1763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                13568
_reflns_number_total             14813
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc03552a2.cif
_cod_data_source_block           cu_d8v21695_0m
_cod_depositor_comments          'Adding full bibliography for 1567648.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1567648
_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   0.884
_shelx_estimated_absorpt_t_max   0.923
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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_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
N1 N 0.25734(19) 0.36799(5) 0.6422(2) 0.0543(4) Uani 1 1 d . . . . .
N1A N 0.24773(19) 0.36991(5) 0.1371(2) 0.0545(5) Uani 1 1 d . . . . .
N1B N 0.3264(2) 0.67666(5) 0.2562(2) 0.0605(5) Uani 1 1 d . . . . .
N1C N 0.3458(2) 0.67937(5) 0.7582(2) 0.0567(5) Uani 1 1 d . . . . .
O1 O 0.5517(3) 0.34895(5) 0.6226(3) 0.0941(8) Uani 1 1 d . . . . .
O2 O 0.20271(19) 0.36909(5) 0.82700(19) 0.0691(5) Uani 1 1 d . . . . .
O3 O 0.03785(16) 0.36291(5) 0.60486(18) 0.0659(5) Uani 1 1 d . . . . .
O1A O 0.5419(3) 0.35255(6) 0.1157(3) 0.0928(7) Uani 1 1 d . . . . .
O2A O 0.19309(18) 0.37033(5) 0.32178(19) 0.0676(5) Uani 1 1 d . . . . .
O3A O 0.02835(16) 0.36476(5) 0.09959(18) 0.0628(4) Uani 1 1 d . . . . .
O1B O 0.5409(2) 0.67599(6) 0.5046(2) 0.0849(6) Uani 1 1 d . . . . .
O2B O 0.2587(2) 0.67901(5) 0.0237(2) 0.0723(5) Uani 1 1 d . . . . .
O3B O 0.1603(2) 0.71032(4) 0.13220(19) 0.0694(5) Uani 1 1 d . . . . .
O1C O 0.5472(2) 0.67600(7) 1.0119(2) 0.0877(7) Uani 1 1 d . . . . .
O2C O 0.2641(2) 0.67814(5) 0.52362(19) 0.0715(5) Uani 1 1 d . . . . .
O3C O 0.1722(2) 0.71123(5) 0.63234(18) 0.0680(5) Uani 1 1 d . . . . .
C1 C 0.5083(4) 0.28527(8) 0.6586(4) 0.0796(8) Uani 1 1 d . . . . .
H1D H 0.5596 0.2905 0.6089 0.096 Uiso 1 1 calc R U . . .
C2 C 0.4878(5) 0.25377(8) 0.6803(5) 0.1032(12) Uani 1 1 d . . . . .
H2 H 0.5246 0.2378 0.6445 0.124 Uiso 1 1 calc R U . . .
C3 C 0.4135(5) 0.24565(8) 0.7542(5) 0.1014(12) Uani 1 1 d . . . . .
H3 H 0.4003 0.2243 0.7691 0.122 Uiso 1 1 calc R U . . .
C4 C 0.3582(4) 0.26919(9) 0.8064(4) 0.0955(11) Uani 1 1 d . . . . .
H4 H 0.3073 0.2637 0.8563 0.115 Uiso 1 1 calc R U . . .
C5 C 0.3781(3) 0.30120(7) 0.7847(3) 0.0736(7) Uani 1 1 d . . . . .
H5 H 0.3409 0.3170 0.8205 0.088 Uiso 1 1 calc R U . . .
C6 C 0.4530(3) 0.30946(6) 0.7103(3) 0.0615(6) Uani 1 1 d . . . . .
C7 C 0.4788(2) 0.34324(6) 0.6811(3) 0.0582(6) Uani 1 1 d . . . . .
C8 C 0.4079(2) 0.37088(6) 0.7236(3) 0.0522(5) Uani 1 1 d . . . . .
H8 H 0.4281 0.3681 0.8221 0.063 Uiso 1 1 calc R U . . .
C9 C 0.4647(2) 0.40290(5) 0.7078(2) 0.0509(5) Uani 1 1 d . . . . .
C10 C 0.5548(3) 0.41977(6) 0.8239(3) 0.0612(6) Uani 1 1 d . . . . .
H10 H 0.5800 0.4113 0.9123 0.073 Uiso 1 1 calc R U . . .
C11 C 0.6076(3) 0.44912(7) 0.8097(3) 0.0655(6) Uani 1 1 d . . . . .
H11 H 0.6688 0.4598 0.8893 0.079 Uiso 1 1 calc R U . . .
C12 C 0.5718(2) 0.46321(6) 0.6798(3) 0.0546(5) Uani 1 1 d . . . . .
C13 C 0.4806(3) 0.44616(7) 0.5645(3) 0.0641(6) Uani 1 1 d . . . . .
H13 H 0.4538 0.4548 0.4760 0.077 Uiso 1 1 calc R U . . .
C14 C 0.4286(3) 0.41660(6) 0.5779(3) 0.0639(6) Uani 1 1 d . . . . .
H14 H 0.3683 0.4058 0.4984 0.077 Uiso 1 1 calc R U . . .
C15 C 0.6235(2) 0.49550(6) 0.6643(3) 0.0575(6) Uani 1 1 d . . . . .
C16 C 0.7057(3) 0.51359(7) 0.7789(3) 0.0759(7) Uani 1 1 d . . . . .
H16 H 0.7308 0.5054 0.8679 0.091 Uiso 1 1 calc R U . . .
C17 C 0.7514(4) 0.54378(7) 0.7636(4) 0.0860(9) Uani 1 1 d . . . . .
H17 H 0.8065 0.5554 0.8427 0.103 Uiso 1 1 calc R U . . .
C18 C 0.7173(3) 0.55670(7) 0.6356(4) 0.0763(8) Uani 1 1 d . . . . .
H18 H 0.7489 0.5769 0.6264 0.092 Uiso 1 1 calc R U . . .
C19 C 0.6351(4) 0.53918(8) 0.5199(4) 0.0821(8) Uani 1 1 d . . . . .
H19 H 0.6103 0.5477 0.4315 0.098 Uiso 1 1 calc R U . . .
C20 C 0.5890(3) 0.50892(7) 0.5340(3) 0.0737(7) Uani 1 1 d . . . . .
H20 H 0.5339 0.4974 0.4545 0.088 Uiso 1 1 calc R U . . .
C21 C 0.1682(2) 0.36698(6) 0.7027(3) 0.0531(5) Uani 1 1 d . . . . .
C22 C -0.0813(2) 0.35768(7) 0.6409(3) 0.0594(6) Uani 1 1 d . . . . .
C23 C -0.1967(3) 0.34761(9) 0.5014(3) 0.0746(8) Uani 1 1 d . . . . .
H23A H -0.2099 0.3639 0.4333 0.112 Uiso 1 1 calc R U . . .
H23B H -0.2820 0.3446 0.5112 0.112 Uiso 1 1 calc R U . . .
H23C H -0.1709 0.3280 0.4717 0.112 Uiso 1 1 calc R U . . .
C24 C -0.0508(3) 0.33072(7) 0.7439(3) 0.0687(7) Uani 1 1 d . . . . .
H24A H -0.0094 0.3132 0.7163 0.103 Uiso 1 1 calc R U . . .
H24B H -0.1362 0.3238 0.7463 0.103 Uiso 1 1 calc R U . . .
H24C H 0.0127 0.3380 0.8348 0.103 Uiso 1 1 calc R U . . .
C25 C -0.1152(4) 0.38844(8) 0.6931(4) 0.0811(9) Uani 1 1 d . . . . .
H25A H -0.0385 0.3943 0.7792 0.122 Uiso 1 1 calc R U . . .
H25B H -0.1978 0.3856 0.7081 0.122 Uiso 1 1 calc R U . . .
H25C H -0.1308 0.4050 0.6253 0.122 Uiso 1 1 calc R U . . .
C1A C 0.5055(4) 0.28861(8) 0.1554(4) 0.0843(9) Uani 1 1 d . . . . .
H1E H 0.5559 0.2941 0.1050 0.101 Uiso 1 1 calc R U . . .
C2A C 0.4879(5) 0.25703(9) 0.1785(5) 0.1091(13) Uani 1 1 d . . . . .
H2A H 0.5257 0.2413 0.1430 0.131 Uiso 1 1 calc R U . . .
C3A C 0.4149(5) 0.24858(9) 0.2535(5) 0.1079(13) Uani 1 1 d . . . . .
H3A H 0.4032 0.2271 0.2689 0.130 Uiso 1 1 calc R U . . .
C4A C 0.3591(4) 0.27178(10) 0.3058(4) 0.0981(11) Uani 1 1 d . . . . .
H4A H 0.3099 0.2660 0.3570 0.118 Uiso 1 1 calc R U . . .
C5A C 0.3754(3) 0.30379(8) 0.2829(3) 0.0759(7) Uani 1 1 d . . . . .
H5A H 0.3371 0.3194 0.3187 0.091 Uiso 1 1 calc R U . . .
C6A C 0.4489(3) 0.31264(7) 0.2067(3) 0.0641(6) Uani 1 1 d . . . . .
C7A C 0.4708(2) 0.34637(6) 0.1758(3) 0.0594(6) Uani 1 1 d . . . . .
C8A C 0.3980(2) 0.37346(6) 0.2183(3) 0.0546(5) Uani 1 1 d . . . . .
H8A H 0.4185 0.3705 0.3168 0.066 Uiso 1 1 calc R U . . .
C9A C 0.4534(2) 0.40586(6) 0.2028(3) 0.0537(5) Uani 1 1 d . . . . .
C10A C 0.5722(3) 0.41781(7) 0.3107(3) 0.0643(6) Uani 1 1 d . . . . .
H10A H 0.6131 0.4066 0.3941 0.077 Uiso 1 1 calc R U . . .
C11A C 0.6308(3) 0.44633(7) 0.2958(3) 0.0666(6) Uani 1 1 d . . . . .
H11A H 0.7122 0.4535 0.3689 0.080 Uiso 1 1 calc R U . . .
C12A C 0.5719(3) 0.46437(6) 0.1757(3) 0.0586(6) Uani 1 1 d . . . . .
C13A C 0.4502(3) 0.45259(7) 0.0702(3) 0.0760(8) Uani 1 1 d . . . . .
H13A H 0.4064 0.4644 -0.0114 0.091 Uiso 1 1 calc R U . . .
C14A C 0.3923(3) 0.42401(7) 0.0829(3) 0.0750(8) Uani 1 1 d . . . . .
H14A H 0.3109 0.4168 0.0097 0.090 Uiso 1 1 calc R U . . .
C15A C 0.6351(3) 0.49477(6) 0.1578(3) 0.0615(6) Uani 1 1 d . . . . .
C16A C 0.7779(3) 0.49954(8) 0.2192(4) 0.0876(9) Uani 1 1 d . . . . .
H16A H 0.8365 0.4836 0.2749 0.105 Uiso 1 1 calc R U . . .
C17A C 0.8348(4) 0.52795(10) 0.1985(5) 0.1021(11) Uani 1 1 d . . . . .
H17A H 0.9312 0.5308 0.2411 0.123 Uiso 1 1 calc R U . . .
C18A C 0.7526(4) 0.55154(8) 0.1175(4) 0.0857(9) Uani 1 1 d . . . . .
H18A H 0.7919 0.5705 0.1054 0.103 Uiso 1 1 calc R U . . .
C19A C 0.6123(4) 0.54714(8) 0.0541(4) 0.0860(9) Uani 1 1 d . . . . .
H19A H 0.5549 0.5631 -0.0023 0.103 Uiso 1 1 calc R U . . .
C20A C 0.5540(3) 0.51899(7) 0.0731(4) 0.0792(8) Uani 1 1 d . . . . .
H20A H 0.4576 0.5163 0.0277 0.095 Uiso 1 1 calc R U . . .
C21A C 0.1587(2) 0.36851(6) 0.1975(2) 0.0517(5) Uani 1 1 d . . . . .
C22A C -0.0902(2) 0.35924(7) 0.1361(3) 0.0585(6) Uani 1 1 d . . . . .
C23A C -0.2072(3) 0.35022(10) -0.0044(3) 0.0784(8) Uani 1 1 d . . . . .
H23D H -0.2222 0.3674 -0.0693 0.118 Uiso 1 1 calc R U . . .
H23E H -0.2915 0.3463 0.0064 0.118 Uiso 1 1 calc R U . . .
H23F H -0.1815 0.3313 -0.0389 0.118 Uiso 1 1 calc R U . . .
C24A C -0.1220(3) 0.38943(8) 0.1935(4) 0.0799(8) Uani 1 1 d . . . . .
H24D H -0.0453 0.3945 0.2809 0.120 Uiso 1 1 calc R U . . .
H24E H -0.2052 0.3865 0.2074 0.120 Uiso 1 1 calc R U . . .
H24F H -0.1357 0.4066 0.1290 0.120 Uiso 1 1 calc R U . . .
C25A C -0.0605(3) 0.33151(7) 0.2352(3) 0.0722(7) Uani 1 1 d . . . . .
H25D H -0.0220 0.3142 0.2036 0.108 Uiso 1 1 calc R U . . .
H25E H -0.1457 0.3247 0.2386 0.108 Uiso 1 1 calc R U . . .
H25F H 0.0052 0.3380 0.3266 0.108 Uiso 1 1 calc R U . . .
C1B C 0.8103(3) 0.65564(8) 0.5652(3) 0.0765(8) Uani 1 1 d . . . . .
H1F H 0.7985 0.6716 0.6204 0.092 Uiso 1 1 calc R U . . .
C2B C 0.9420(3) 0.64389(10) 0.5974(4) 0.0901(10) Uani 1 1 d . . . . .
H2B H 1.0182 0.6521 0.6733 0.108 Uiso 1 1 calc R U . . .
C3B C 0.9619(3) 0.62029(9) 0.5192(3) 0.0842(9) Uani 1 1 d . . . . .
H3B H 1.0511 0.6125 0.5412 0.101 Uiso 1 1 calc R U . . .
C4B C 0.8494(4) 0.60819(9) 0.4084(3) 0.0883(9) Uani 1 1 d . . . . .
H4B H 0.8621 0.5918 0.3558 0.106 Uiso 1 1 calc R U . . .
C5B C 0.7161(3) 0.62012(8) 0.3733(3) 0.0759(7) Uani 1 1 d . . . . .
H5B H 0.6407 0.6119 0.2965 0.091 Uiso 1 1 calc R U . . .
C6B C 0.6945(3) 0.64403(6) 0.4513(3) 0.0582(6) Uani 1 1 d . . . . .
C7B C 0.5558(3) 0.65870(6) 0.4204(3) 0.0587(6) Uani 1 1 d . . . . .
C8B C 0.4324(3) 0.65255(6) 0.2782(3) 0.0548(5) Uani 1 1 d . . . . .
H8B H 0.4662 0.6553 0.2059 0.066 Uiso 1 1 calc R U . . .
C9B C 0.3735(2) 0.61883(6) 0.2652(2) 0.0529(5) Uani 1 1 d . . . . .
C10B C 0.3116(3) 0.60795(6) 0.3484(3) 0.0575(5) Uani 1 1 d . . . . .
H10B H 0.3090 0.6211 0.4178 0.069 Uiso 1 1 calc R U . . .
C11B C 0.2534(3) 0.57770(7) 0.3301(3) 0.0637(6) Uani 1 1 d . . . . .
H11B H 0.2119 0.5709 0.3872 0.076 Uiso 1 1 calc R U . . .
C12B C 0.2561(3) 0.55725(6) 0.2275(3) 0.0640(6) Uani 1 1 d . . . . .
C13B C 0.3167(3) 0.56870(7) 0.1435(3) 0.0724(7) Uani 1 1 d . . . . .
H13B H 0.3181 0.5558 0.0728 0.087 Uiso 1 1 calc R U . . .
C14B C 0.3749(3) 0.59884(6) 0.1624(3) 0.0650(6) Uani 1 1 d . . . . .
H14B H 0.4158 0.6058 0.1051 0.078 Uiso 1 1 calc R U . . .
C15B C 0.1958(3) 0.52448(7) 0.2044(4) 0.0749(8) Uani 1 1 d . . . . .
C16B C 0.2035(3) 0.50555(8) 0.3139(4) 0.0916(10) Uani 1 1 d . . . . .
H16B H 0.2439 0.5137 0.4040 0.110 Uiso 1 1 calc R U . . .
C17B C 0.1518(4) 0.47457(10) 0.2918(6) 0.1155(15) Uani 1 1 d . . . . .
H17B H 0.1572 0.4622 0.3667 0.139 Uiso 1 1 calc R U . . .
C18B C 0.0931(5) 0.46229(10) 0.1600(7) 0.1262(18) Uani 1 1 d . . . . .
H18B H 0.0617 0.4413 0.1458 0.151 Uiso 1 1 calc R U . . .
C19B C 0.0800(5) 0.48084(10) 0.0480(6) 0.1250(16) Uani 1 1 d . . . . .
H19B H 0.0365 0.4728 -0.0421 0.150 Uiso 1 1 calc R U . . .
C20B C 0.1324(4) 0.51173(9) 0.0709(4) 0.0997(11) Uani 1 1 d . . . . .
H20B H 0.1249 0.5242 -0.0047 0.120 Uiso 1 1 calc R U . . .
C21B C 0.2489(3) 0.68794(6) 0.1275(3) 0.0554(5) Uani 1 1 d . . . . .
C22B C 0.0813(4) 0.73007(7) 0.0082(3) 0.0730(8) Uani 1 1 d . . . . .
C23B C 0.0030(7) 0.75257(12) 0.0597(4) 0.140(2) Uani 1 1 d . . . . .
H23G H -0.0645 0.7408 0.0794 0.209 Uiso 1 1 calc R U . . .
H23H H -0.0439 0.7684 -0.0104 0.209 Uiso 1 1 calc R U . . .
H23I H 0.0675 0.7629 0.1432 0.209 Uiso 1 1 calc R U . . .
C24B C 0.1833(5) 0.74771(9) -0.0332(4) 0.1068(13) Uani 1 1 d . . . . .
H24G H 0.2495 0.7591 0.0458 0.160 Uiso 1 1 calc R U . . .
H24H H 0.1331 0.7625 -0.1067 0.160 Uiso 1 1 calc R U . . .
H24I H 0.2318 0.7326 -0.0650 0.160 Uiso 1 1 calc R U . . .
C25B C -0.0187(4) 0.70958(9) -0.1099(4) 0.0909(10) Uani 1 1 d . . . . .
H25G H 0.0336 0.6951 -0.1398 0.136 Uiso 1 1 calc R U . . .
H25H H -0.0756 0.7230 -0.1865 0.136 Uiso 1 1 calc R U . . .
H25I H -0.0772 0.6976 -0.0784 0.136 Uiso 1 1 calc R U . . .
C1C C 0.8109(3) 0.64931(7) 1.1002(3) 0.0689(7) Uani 1 1 d . . . . .
H1G H 0.7861 0.6582 1.1669 0.083 Uiso 1 1 calc R U . . .
C2C C 0.9442(3) 0.63799(9) 1.1391(3) 0.0805(8) Uani 1 1 d . . . . .
H2C H 1.0086 0.6392 1.2319 0.097 Uiso 1 1 calc R U . . .
C3C C 0.9833(3) 0.62495(7) 1.0430(3) 0.0749(8) Uani 1 1 d . . . . .
H3C H 1.0734 0.6171 1.0704 0.090 Uiso 1 1 calc R U . . .
C4C C 0.8884(3) 0.62348(7) 0.9056(3) 0.0711(7) Uani 1 1 d . . . . .
H4C H 0.9149 0.6149 0.8396 0.085 Uiso 1 1 calc R U . . .
C5C C 0.7535(3) 0.63476(7) 0.8647(3) 0.0628(6) Uani 1 1 d . . . . .
H5C H 0.6901 0.6337 0.7715 0.075 Uiso 1 1 calc R U . . .
C6C C 0.7123(2) 0.64764(6) 0.9619(3) 0.0538(5) Uani 1 1 d . . . . .
C7C C 0.5704(3) 0.66097(6) 0.9268(3) 0.0557(5) Uani 1 1 d . . . . .
C8C C 0.4512(2) 0.65517(5) 0.7811(2) 0.0504(5) Uani 1 1 d . . . . .
H8C H 0.4882 0.6578 0.7113 0.060 Uiso 1 1 calc R U . . .
C9C C 0.3930(2) 0.62134(5) 0.7699(2) 0.0473(5) Uani 1 1 d . . . . .
C10C C 0.4332(2) 0.59712(6) 0.7059(3) 0.0557(5) Uani 1 1 d . . . . .
H10C H 0.5009 0.6012 0.6739 0.067 Uiso 1 1 calc R U . . .
C11C C 0.3747(2) 0.56694(6) 0.6884(3) 0.0572(5) Uani 1 1 d . . . . .
H11C H 0.4055 0.5510 0.6473 0.069 Uiso 1 1 calc R U . . .
C12C C 0.2704(2) 0.56022(6) 0.7317(2) 0.0511(5) Uani 1 1 d . . . . .
C13C C 0.2323(3) 0.58464(6) 0.7977(3) 0.0591(6) Uani 1 1 d . . . . .
H13C H 0.1640 0.5808 0.8291 0.071 Uiso 1 1 calc R U . . .
C14C C 0.2933(2) 0.61444(6) 0.8175(3) 0.0558(5) Uani 1 1 d . . . . .
H14C H 0.2669 0.6301 0.8636 0.067 Uiso 1 1 calc R U . . .
C15C C 0.2009(3) 0.52864(6) 0.7052(3) 0.0565(5) Uani 1 1 d . . . . .
C16C C 0.2743(3) 0.50069(6) 0.7137(3) 0.0703(7) Uani 1 1 d . . . . .
H16C H 0.3696 0.5018 0.7377 0.084 Uiso 1 1 calc R U . . .
C17C C 0.2090(4) 0.47140(7) 0.6874(4) 0.0860(9) Uani 1 1 d . . . . .
H17C H 0.2605 0.4529 0.6947 0.103 Uiso 1 1 calc R U . . .
C18C C 0.0689(4) 0.46937(8) 0.6506(5) 0.0977(11) Uani 1 1 d . . . . .
H18C H 0.0248 0.4496 0.6326 0.117 Uiso 1 1 calc R U . . .
C19C C -0.0065(4) 0.49664(9) 0.6404(5) 0.1064(13) Uani 1 1 d . . . . .
H19C H -0.1020 0.4953 0.6151 0.128 Uiso 1 1 calc R U . . .
C20C C 0.0585(3) 0.52604(7) 0.6676(4) 0.0838(9) Uani 1 1 d . . . . .
H20C H 0.0063 0.5444 0.6606 0.101 Uiso 1 1 calc R U . . .
C21C C 0.2605(3) 0.68862(6) 0.6281(3) 0.0548(5) Uani 1 1 d . . . . .
C22C C 0.0934(4) 0.73090(8) 0.5076(3) 0.0781(8) Uani 1 1 d . . . . .
C23C C 0.1953(5) 0.74835(9) 0.4662(4) 0.0993(12) Uani 1 1 d . . . . .
H23J H 0.2610 0.7599 0.5449 0.149 Uiso 1 1 calc R U . . .
H23K H 0.1451 0.7630 0.3919 0.149 Uiso 1 1 calc R U . . .
H23L H 0.2443 0.7332 0.4355 0.149 Uiso 1 1 calc R U . . .
C24C C 0.0142(7) 0.75343(13) 0.5603(4) 0.137(2) Uani 1 1 d . . . . .
H24J H -0.0533 0.7416 0.5795 0.206 Uiso 1 1 calc R U . . .
H24K H -0.0328 0.7693 0.4907 0.206 Uiso 1 1 calc R U . . .
H24L H 0.0786 0.7637 0.6441 0.206 Uiso 1 1 calc R U . . .
C25C C -0.0086(4) 0.71019(10) 0.3889(4) 0.0913(10) Uani 1 1 d . . . . .
H25J H 0.0430 0.6958 0.3579 0.137 Uiso 1 1 calc R U . . .
H25K H -0.0666 0.7236 0.3129 0.137 Uiso 1 1 calc R U . . .
H25L H -0.0661 0.6982 0.4215 0.137 Uiso 1 1 calc R U . . .
H1A H 0.212(3) 0.3684(6) 0.045(3) 0.052(7) Uiso 1 1 d . . . . .
H1 H 0.221(3) 0.3667(7) 0.551(3) 0.065(8) Uiso 1 1 d . . . . .
H1C H 0.333(3) 0.6857(8) 0.829(4) 0.072(9) Uiso 1 1 d . . . . .
H1B H 0.315(3) 0.6835(8) 0.324(4) 0.073(9) Uiso 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 0.0091 '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 0.0180 '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
C21 N1 C8 122.0(2) . . ?
C21 N1 H1 117(2) . . ?
C8 N1 H1 121(2) . . ?
C21A N1A C8A 122.1(2) . . ?
C21A N1A H1A 117.6(17) . . ?
C8A N1A H1A 120.3(17) . . ?
C21B N1B C8B 120.2(2) . . ?
C21B N1B H1B 121(2) . . ?
C8B N1B H1B 119(2) . . ?
C21C N1C C8C 120.4(2) . . ?
C21C N1C H1C 121(2) . . ?
C8C N1C H1C 118(2) . . ?
C21 O3 C22 121.88(19) . . ?
C21A O3A C22A 121.64(18) . . ?
C21B O3B C22B 119.8(2) . . ?
C21C O3C C22C 119.8(2) . . ?
C2 C1 C6 120.7(4) . . ?
C2 C1 H1D 119.7 . . ?
C6 C1 H1D 119.7 . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 123.7(3) . . ?
C1 C6 C7 117.4(3) . . ?
O1 C7 C6 120.6(2) . . ?
O1 C7 C8 120.0(2) . . ?
C6 C7 C8 119.4(2) . . ?
N1 C8 C9 113.3(2) . . ?
N1 C8 C7 107.97(19) . . ?
C9 C8 C7 111.49(18) . . ?
N1 C8 H8 108.0 . . ?
C9 C8 H8 108.0 . . ?
C7 C8 H8 108.0 . . ?
C10 C9 C14 117.8(2) . . ?
C10 C9 C8 120.6(2) . . ?
C14 C9 C8 121.6(2) . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 122.0(2) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C13 C12 C11 116.6(2) . . ?
C13 C12 C15 121.2(2) . . ?
C11 C12 C15 122.2(2) . . ?
C14 C13 C12 121.7(2) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C9 121.1(2) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C16 C15 C20 117.0(3) . . ?
C16 C15 C12 121.5(2) . . ?
C20 C15 C12 121.5(2) . . ?
C15 C16 C17 121.1(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 121.4(3) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 118.5(3) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
C18 C19 C20 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
O2 C21 O3 126.0(2) . . ?
O2 C21 N1 124.5(2) . . ?
O3 C21 N1 109.5(2) . . ?
O3 C22 C25 109.3(2) . . ?
O3 C22 C24 110.8(2) . . ?
C25 C22 C24 112.6(2) . . ?
O3 C22 C23 102.04(19) . . ?
C25 C22 C23 112.1(3) . . ?
C24 C22 C23 109.4(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C2A C1A C6A 120.8(4) . . ?
C2A C1A H1E 119.6 . . ?
C6A C1A H1E 119.6 . . ?
C3A C2A C1A 120.3(4) . . ?
C3A C2A H2A 119.8 . . ?
C1A C2A H2A 119.8 . . ?
C4A C3A C2A 119.9(4) . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 120.5(4) . . ?
C3A C4A H4A 119.8 . . ?
C5A C4A H4A 119.8 . . ?
C4A C5A C6A 120.2(4) . . ?
C4A C5A H5A 119.9 . . ?
C6A C5A H5A 119.9 . . ?
C5A C6A C1A 118.3(3) . . ?
C5A C6A C7A 124.0(3) . . ?
C1A C6A C7A 117.7(3) . . ?
O1A C7A C6A 120.8(2) . . ?
O1A C7A C8A 120.0(3) . . ?
C6A C7A C8A 119.2(2) . . ?
N1A C8A C9A 113.7(2) . . ?
N1A C8A C7A 107.87(19) . . ?
C9A C8A C7A 111.27(19) . . ?
N1A C8A H8A 107.9 . . ?
C9A C8A H8A 107.9 . . ?
C7A C8A H8A 107.9 . . ?
C14A C9A C10A 117.8(2) . . ?
C14A C9A C8A 122.8(2) . . ?
C10A C9A C8A 119.4(2) . . ?
C9A C10A C11A 120.7(3) . . ?
C9A C10A H10A 119.7 . . ?
C11A C10A H10A 119.7 . . ?
C12A C11A C10A 121.9(2) . . ?
C12A C11A H11A 119.0 . . ?
C10A C11A H11A 119.0 . . ?
C11A C12A C13A 116.7(2) . . ?
C11A C12A C15A 122.4(2) . . ?
C13A C12A C15A 121.0(3) . . ?
C14A C13A C12A 121.9(3) . . ?
C14A C13A H13A 119.0 . . ?
C12A C13A H13A 119.0 . . ?
C13A C14A C9A 120.9(3) . . ?
C13A C14A H14A 119.5 . . ?
C9A C14A H14A 119.5 . . ?
C16A C15A C20A 116.8(3) . . ?
C16A C15A C12A 121.6(3) . . ?
C20A C15A C12A 121.5(2) . . ?
C15A C16A C17A 120.6(3) . . ?
C15A C16A H16A 119.7 . . ?
C17A C16A H16A 119.7 . . ?
C18A C17A C16A 121.3(3) . . ?
C18A C17A H17A 119.4 . . ?
C16A C17A H17A 119.4 . . ?
C17A C18A C19A 119.1(3) . . ?
C17A C18A H18A 120.4 . . ?
C19A C18A H18A 120.4 . . ?
C18A C19A C20A 120.4(3) . . ?
C18A C19A H19A 119.8 . . ?
C20A C19A H19A 119.8 . . ?
C19A C20A C15A 121.8(3) . . ?
C19A C20A H20A 119.1 . . ?
C15A C20A H20A 119.1 . . ?
O2A C21A O3A 125.8(2) . . ?
O2A C21A N1A 124.6(2) . . ?
O3A C21A N1A 109.58(19) . . ?
O3A C22A C24A 109.6(2) . . ?
O3A C22A C25A 110.8(2) . . ?
C24A C22A C25A 112.4(2) . . ?
O3A C22A C23A 102.03(19) . . ?
C24A C22A C23A 112.1(3) . . ?
C25A C22A C23A 109.4(2) . . ?
C22A C23A H23D 109.5 . . ?
C22A C23A H23E 109.5 . . ?
H23D C23A H23E 109.5 . . ?
C22A C23A H23F 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
C22A C24A H24D 109.5 . . ?
C22A C24A H24E 109.5 . . ?
H24D C24A H24E 109.5 . . ?
C22A C24A H24F 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
C22A C25A H25D 109.5 . . ?
C22A C25A H25E 109.5 . . ?
H25D C25A H25E 109.5 . . ?
C22A C25A H25F 109.5 . . ?
H25D C25A H25F 109.5 . . ?
H25E C25A H25F 109.5 . . ?
C2B C1B C6B 120.9(3) . . ?
C2B C1B H1F 119.5 . . ?
C6B C1B H1F 119.5 . . ?
C3B C2B C1B 120.7(3) . . ?
C3B C2B H2B 119.6 . . ?
C1B C2B H2B 119.6 . . ?
C2B C3B C4B 119.3(3) . . ?
C2B C3B H3B 120.4 . . ?
C4B C3B H3B 120.4 . . ?
C3B C4B C5B 120.7(3) . . ?
C3B C4B H4B 119.7 . . ?
C5B C4B H4B 119.7 . . ?
C6B C5B C4B 120.6(3) . . ?
C6B C5B H5B 119.7 . . ?
C4B C5B H5B 119.7 . . ?
C5B C6B C1B 117.8(3) . . ?
C5B C6B C7B 124.4(2) . . ?
C1B C6B C7B 117.8(3) . . ?
O1B C7B C6B 120.5(2) . . ?
O1B C7B C8B 120.0(2) . . ?
C6B C7B C8B 119.4(2) . . ?
N1B C8B C9B 111.7(2) . . ?
N1B C8B C7B 108.4(2) . . ?
C9B C8B C7B 112.74(19) . . ?
N1B C8B H8B 107.9 . . ?
C9B C8B H8B 107.9 . . ?
C7B C8B H8B 107.9 . . ?
C14B C9B C10B 118.2(2) . . ?
C14B C9B C8B 119.4(2) . . ?
C10B C9B C8B 122.3(2) . . ?
C9B C10B C11B 121.1(2) . . ?
C9B C10B H10B 119.5 . . ?
C11B C10B H10B 119.5 . . ?
C10B C11B C12B 121.0(2) . . ?
C10B C11B H11B 119.5 . . ?
C12B C11B H11B 119.5 . . ?
C13B C12B C11B 117.3(3) . . ?
C13B C12B C15B 119.7(3) . . ?
C11B C12B C15B 123.0(3) . . ?
C14B C13B C12B 121.5(3) . . ?
C14B C13B H13B 119.2 . . ?
C12B C13B H13B 119.2 . . ?
C9B C14B C13B 121.0(2) . . ?
C9B C14B H14B 119.5 . . ?
C13B C14B H14B 119.5 . . ?
C16B C15B C20B 117.8(3) . . ?
C16B C15B C12B 121.5(3) . . ?
C20B C15B C12B 120.6(3) . . ?
C15B C16B C17B 121.1(4) . . ?
C15B C16B H16B 119.4 . . ?
C17B C16B H16B 119.4 . . ?
C18B C17B C16B 119.9(4) . . ?
C18B C17B H17B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C17B C18B C19B 120.4(4) . . ?
C17B C18B H18B 119.8 . . ?
C19B C18B H18B 119.8 . . ?
C18B C19B C20B 119.3(5) . . ?
C18B C19B H19B 120.3 . . ?
C20B C19B H19B 120.3 . . ?
C19B C20B C15B 121.3(4) . . ?
C19B C20B H20B 119.3 . . ?
C15B C20B H20B 119.3 . . ?
O2B C21B O3B 125.6(2) . . ?
O2B C21B N1B 124.4(2) . . ?
O3B C21B N1B 109.9(2) . . ?
O3B C22B C23B 102.6(2) . . ?
O3B C22B C25B 110.5(2) . . ?
C23B C22B C25B 110.9(4) . . ?
O3B C22B C24B 109.1(3) . . ?
C23B C22B C24B 111.7(4) . . ?
C25B C22B C24B 111.6(3) . . ?
C22B C23B H23G 109.5 . . ?
C22B C23B H23H 109.5 . . ?
H23G C23B H23H 109.5 . . ?
C22B C23B H23I 109.5 . . ?
H23G C23B H23I 109.5 . . ?
H23H C23B H23I 109.5 . . ?
C22B C24B H24G 109.5 . . ?
C22B C24B H24H 109.5 . . ?
H24G C24B H24H 109.5 . . ?
C22B C24B H24I 109.5 . . ?
H24G C24B H24I 109.5 . . ?
H24H C24B H24I 109.5 . . ?
C22B C25B H25G 109.5 . . ?
C22B C25B H25H 109.5 . . ?
H25G C25B H25H 109.5 . . ?
C22B C25B H25I 109.5 . . ?
H25G C25B H25I 109.5 . . ?
H25H C25B H25I 109.5 . . ?
C2C C1C C6C 120.7(3) . . ?
C2C C1C H1G 119.6 . . ?
C6C C1C H1G 119.6 . . ?
C3C C2C C1C 120.8(3) . . ?
C3C C2C H2C 119.6 . . ?
C1C C2C H2C 119.6 . . ?
C2C C3C C4C 119.5(3) . . ?
C2C C3C H3C 120.2 . . ?
C4C C3C H3C 120.3 . . ?
C3C C4C C5C 120.4(3) . . ?
C3C C4C H4C 119.8 . . ?
C5C C4C H4C 119.8 . . ?
C4C C5C C6C 120.5(3) . . ?
C4C C5C H5C 119.8 . . ?
C6C C5C H5C 119.8 . . ?
C5C C6C C1C 118.1(2) . . ?
C5C C6C C7C 124.1(2) . . ?
C1C C6C C7C 117.7(2) . . ?
O1C C7C C6C 120.8(2) . . ?
O1C C7C C8C 119.4(2) . . ?
C6C C7C C8C 119.8(2) . . ?
N1C C8C C9C 112.25(18) . . ?
N1C C8C C7C 107.50(19) . . ?
C9C C8C C7C 110.75(18) . . ?
N1C C8C H8C 108.8 . . ?
C9C C8C H8C 108.8 . . ?
C7C C8C H8C 108.8 . . ?
C14C C9C C10C 117.9(2) . . ?
C14C C9C C8C 120.7(2) . . ?
C10C C9C C8C 121.3(2) . . ?
C11C C10C C9C 121.4(2) . . ?
C11C C10C H10C 119.3 . . ?
C9C C10C H10C 119.3 . . ?
C10C C11C C12C 120.8(2) . . ?
C10C C11C H11C 119.6 . . ?
C12C C11C H11C 119.6 . . ?
C13C C12C C11C 117.2(2) . . ?
C13C C12C C15C 121.7(2) . . ?
C11C C12C C15C 121.1(2) . . ?
C14C C13C C12C 121.6(2) . . ?
C14C C13C H13C 119.2 . . ?
C12C C13C H13C 119.2 . . ?
C13C C14C C9C 121.0(2) . . ?
C13C C14C H14C 119.5 . . ?
C9C C14C H14C 119.5 . . ?
C16C C15C C20C 117.5(3) . . ?
C16C C15C C12C 121.5(2) . . ?
C20C C15C C12C 121.0(2) . . ?
C17C C16C C15C 121.4(3) . . ?
C17C C16C H16C 119.3 . . ?
C15C C16C H16C 119.3 . . ?
C18C C17C C16C 120.2(3) . . ?
C18C C17C H17C 119.9 . . ?
C16C C17C H17C 119.9 . . ?
C17C C18C C19C 119.7(3) . . ?
C17C C18C H18C 120.2 . . ?
C19C C18C H18C 120.2 . . ?
C18C C19C C20C 120.4(3) . . ?
C18C C19C H19C 119.8 . . ?
C20C C19C H19C 119.8 . . ?
C19C C20C C15C 120.9(3) . . ?
C19C C20C H20C 119.6 . . ?
C15C C20C H20C 119.6 . . ?
O2C C21C O3C 125.5(2) . . ?
O2C C21C N1C 124.6(2) . . ?
O3C C21C N1C 109.9(2) . . ?
O3C C22C C23C 109.2(3) . . ?
O3C C22C C24C 101.9(2) . . ?
C23C C22C C24C 112.3(4) . . ?
O3C C22C C25C 110.6(3) . . ?
C23C C22C C25C 112.0(3) . . ?
C24C C22C C25C 110.4(4) . . ?
C22C C23C H23J 109.5 . . ?
C22C C23C H23K 109.5 . . ?
H23J C23C H23K 109.5 . . ?
C22C C23C H23L 109.5 . . ?
H23J C23C H23L 109.5 . . ?
H23K C23C H23L 109.5 . . ?
C22C C24C H24J 109.5 . . ?
C22C C24C H24K 109.5 . . ?
H24J C24C H24K 109.5 . . ?
C22C C24C H24L 109.5 . . ?
H24J C24C H24L 109.5 . . ?
H24K C24C H24L 109.5 . . ?
C22C C25C H25J 109.5 . . ?
C22C C25C H25K 109.5 . . ?
H25J C25C H25K 109.5 . . ?
C22C C25C H25L 109.5 . . ?
H25J C25C H25L 109.5 . . ?
H25K C25C H25L 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
N1 C21 1.348(3) . ?
N1 C8 1.458(3) . ?
N1 H1 0.88(3) . ?
N1A C21A 1.347(3) . ?
N1A C8A 1.458(3) . ?
N1A H1A 0.89(3) . ?
N1B C21B 1.344(3) . ?
N1B C8B 1.452(3) . ?
N1B H1B 0.83(4) . ?
N1C C21C 1.345(3) . ?
N1C C8C 1.448(3) . ?
N1C H1C 0.87(4) . ?
O1 C7 1.201(3) . ?
O2 C21 1.212(3) . ?
O3 C21 1.337(3) . ?
O3 C22 1.480(2) . ?
O1A C7A 1.203(3) . ?
O2A C21A 1.212(3) . ?
O3A C21A 1.336(3) . ?
O3A C22A 1.480(2) . ?
O1B C7B 1.211(3) . ?
O2B C21B 1.208(3) . ?
O3B C21B 1.342(3) . ?
O3B C22B 1.475(3) . ?
O1C C7C 1.207(3) . ?
O2C C21C 1.207(3) . ?
O3C C21C 1.344(3) . ?
O3C C22C 1.478(3) . ?
C1 C2 1.372(5) . ?
C1 C6 1.393(4) . ?
C1 H1D 0.9300 . ?
C2 C3 1.369(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.497(4) . ?
C7 C8 1.547(3) . ?
C8 C9 1.507(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.387(3) . ?
C9 C14 1.388(4) . ?
C10 C11 1.384(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(4) . ?
C12 C15 1.493(3) . ?
C13 C14 1.386(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.381(4) . ?
C15 C20 1.390(4) . ?
C16 C17 1.387(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.360(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.388(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C22 C25 1.504(4) . ?
C22 C24 1.508(4) . ?
C22 C23 1.523(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C1A C2A 1.371(6) . ?
C1A C6A 1.394(4) . ?
C1A H1E 0.9300 . ?
C2A C3A 1.371(7) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.370(7) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.385(5) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.389(4) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.490(4) . ?
C7A C8A 1.542(3) . ?
C8A C9A 1.514(3) . ?
C8A H8A 0.9800 . ?
C9A C14A 1.383(4) . ?
C9A C10A 1.384(3) . ?
C10A C11A 1.385(4) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.380(4) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.388(4) . ?
C12A C15A 1.486(4) . ?
C13A C14A 1.376(4) . ?
C13A H13A 0.9300 . ?
C14A H14A 0.9300 . ?
C15A C16A 1.382(4) . ?
C15A C20A 1.384(4) . ?
C16A C17A 1.392(5) . ?
C16A H16A 0.9300 . ?
C17A C18A 1.354(5) . ?
C17A H17A 0.9300 . ?
C18A C19A 1.357(5) . ?
C18A H18A 0.9300 . ?
C19A C20A 1.384(4) . ?
C19A H19A 0.9300 . ?
C20A H20A 0.9300 . ?
C22A C24A 1.502(4) . ?
C22A C25A 1.506(4) . ?
C22A C23A 1.525(4) . ?
C23A H23D 0.9600 . ?
C23A H23E 0.9600 . ?
C23A H23F 0.9600 . ?
C24A H24D 0.9600 . ?
C24A H24E 0.9600 . ?
C24A H24F 0.9600 . ?
C25A H25D 0.9600 . ?
C25A H25E 0.9600 . ?
C25A H25F 0.9600 . ?
C1B C2B 1.376(5) . ?
C1B C6B 1.391(4) . ?
C1B H1F 0.9300 . ?
C2B C3B 1.362(5) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.365(5) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.389(4) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.378(4) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.492(4) . ?
C7B C8B 1.539(3) . ?
C8B C9B 1.526(3) . ?
C8B H8B 0.9800 . ?
C9B C14B 1.379(3) . ?
C9B C10B 1.380(3) . ?
C10B C11B 1.385(4) . ?
C10B H10B 0.9300 . ?
C11B C12B 1.394(4) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.386(4) . ?
C12B C15B 1.488(4) . ?
C13B C14B 1.381(4) . ?
C13B H13B 0.9300 . ?
C14B H14B 0.9300 . ?
C15B C16B 1.379(5) . ?
C15B C20B 1.390(5) . ?
C16B C17B 1.388(5) . ?
C16B H16B 0.9300 . ?
C17B C18B 1.366(7) . ?
C17B H17B 0.9300 . ?
C18B C19B 1.376(7) . ?
C18B H18B 0.9300 . ?
C19B C20B 1.387(5) . ?
C19B H19B 0.9300 . ?
C20B H20B 0.9300 . ?
C22B C23B 1.502(5) . ?
C22B C25B 1.515(5) . ?
C22B C24B 1.519(6) . ?
C23B H23G 0.9600 . ?
C23B H23H 0.9600 . ?
C23B H23I 0.9600 . ?
C24B H24G 0.9600 . ?
C24B H24H 0.9600 . ?
C24B H24I 0.9600 . ?
C25B H25G 0.9600 . ?
C25B H25H 0.9600 . ?
C25B H25I 0.9600 . ?
C1C C2C 1.374(4) . ?
C1C C6C 1.394(4) . ?
C1C H1G 0.9300 . ?
C2C C3C 1.366(5) . ?
C2C H2C 0.9300 . ?
C3C C4C 1.375(4) . ?
C3C H3C 0.9300 . ?
C4C C5C 1.386(4) . ?
C4C H4C 0.9300 . ?
C5C C6C 1.387(4) . ?
C5C H5C 0.9300 . ?
C6C C7C 1.493(3) . ?
C7C C8C 1.542(3) . ?
C8C C9C 1.529(3) . ?
C8C H8C 0.9800 . ?
C9C C14C 1.379(3) . ?
C9C C10C 1.384(3) . ?
C10C C11C 1.384(3) . ?
C10C H10C 0.9300 . ?
C11C C12C 1.392(3) . ?
C11C H11C 0.9300 . ?
C12C C13C 1.392(3) . ?
C12C C15C 1.480(3) . ?
C13C C14C 1.379(4) . ?
C13C H13C 0.9300 . ?
C14C H14C 0.9300 . ?
C15C C16C 1.385(4) . ?
C15C C20C 1.389(4) . ?
C16C C17C 1.376(4) . ?
C16C H16C 0.9300 . ?
C17C C18C 1.365(5) . ?
C17C H17C 0.9300 . ?
C18C C19C 1.370(5) . ?
C18C H18C 0.9300 . ?
C19C C20C 1.379(4) . ?
C19C H19C 0.9300 . ?
C20C H20C 0.9300 . ?
C22C C23C 1.514(6) . ?
C22C C24C 1.517(5) . ?
C22C C25C 1.531(5) . ?
C23C H23J 0.9600 . ?
C23C H23K 0.9600 . ?
C23C H23L 0.9600 . ?
C24C H24J 0.9600 . ?
C24C H24K 0.9600 . ?
C24C H24L 0.9600 . ?
C25C H25J 0.9600 . ?
C25C H25K 0.9600 . ?
C25C H25L 0.9600 . ?
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
N1B H1B O2C 0.83(4) 2.41(4) 3.174(3) 154(3) .
N1C H1C O2B 0.87(4) 2.51(4) 3.314(3) 155(3) 1_556
N1 H1 O2A 0.88(3) 2.32(3) 3.171(3) 162(3) .
N1A H1A O2 0.89(3) 2.27(3) 3.116(3) 159(2) 1_554
C25C H25J O2C 0.96 2.37 2.941(4) 117.9 .
C23C H23L O2C 0.96 2.46 3.027(4) 117.5 .
C8C H8C O1B 0.98 2.60 3.554(3) 165.8 .
C25B H25G O2B 0.96 2.37 2.952(4) 118.6 .
C24B H24I O2B 0.96 2.40 2.977(4) 118.0 .
C25A H25F O2A 0.96 2.42 2.929(3) 112.6 .
C24A H24D O2A 0.96 2.58 3.120(4) 116.2 .
C23A H23E O1A 0.96 2.50 3.399(3) 155.7 1_455
C25 H25A O2 0.96 2.60 3.148(4) 116.2 .
C24 H24C O2 0.96 2.43 2.921(3) 111.8 .
C23 H23B O1 0.96 2.51 3.415(3) 157.1 1_455
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 -0.5(6) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 C1 -0.4(5) . . . . ?
C4 C5 C6 C7 179.5(3) . . . . ?
C2 C1 C6 C5 0.5(5) . . . . ?
C2 C1 C6 C7 -179.4(3) . . . . ?
C5 C6 C7 O1 175.7(3) . . . . ?
C1 C6 C7 O1 -4.4(4) . . . . ?
C5 C6 C7 C8 -5.8(4) . . . . ?
C1 C6 C7 C8 174.1(2) . . . . ?
C21 N1 C8 C9 -109.9(3) . . . . ?
C21 N1 C8 C7 126.2(2) . . . . ?
O1 C7 C8 N1 114.0(3) . . . . ?
C6 C7 C8 N1 -64.5(3) . . . . ?
O1 C7 C8 C9 -11.0(4) . . . . ?
C6 C7 C8 C9 170.5(2) . . . . ?
N1 C8 C9 C10 132.2(2) . . . . ?
C7 C8 C9 C10 -105.8(3) . . . . ?
N1 C8 C9 C14 -47.3(3) . . . . ?
C7 C8 C9 C14 74.7(3) . . . . ?
C14 C9 C10 C11 -0.7(4) . . . . ?
C8 C9 C10 C11 179.7(2) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C10 C11 C12 C15 177.3(2) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C15 C12 C13 C14 -178.0(2) . . . . ?
C12 C13 C14 C9 0.6(4) . . . . ?
C10 C9 C14 C13 0.0(4) . . . . ?
C8 C9 C14 C13 179.5(2) . . . . ?
C13 C12 C15 C16 175.1(3) . . . . ?
C11 C12 C15 C16 -2.4(4) . . . . ?
C13 C12 C15 C20 -3.7(4) . . . . ?
C11 C12 C15 C20 178.7(3) . . . . ?
C20 C15 C16 C17 0.0(4) . . . . ?
C12 C15 C16 C17 -178.9(3) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C18 C19 C20 C15 0.3(5) . . . . ?
C16 C15 C20 C19 -0.1(4) . . . . ?
C12 C15 C20 C19 178.8(3) . . . . ?
C22 O3 C21 O2 -5.3(4) . . . . ?
C22 O3 C21 N1 173.8(2) . . . . ?
C8 N1 C21 O2 1.8(4) . . . . ?
C8 N1 C21 O3 -177.3(2) . . . . ?
C21 O3 C22 C25 72.5(3) . . . . ?
C21 O3 C22 C24 -52.2(3) . . . . ?
C21 O3 C22 C23 -168.6(2) . . . . ?
C6A C1A C2A C3A -0.5(7) . . . . ?
C1A C2A C3A C4A 0.0(7) . . . . ?
C2A C3A C4A C5A 0.3(7) . . . . ?
C3A C4A C5A C6A -0.1(6) . . . . ?
C4A C5A C6A C1A -0.4(5) . . . . ?
C4A C5A C6A C7A 179.5(3) . . . . ?
C2A C1A C6A C5A 0.7(5) . . . . ?
C2A C1A C6A C7A -179.2(3) . . . . ?
C5A C6A C7A O1A 175.9(3) . . . . ?
C1A C6A C7A O1A -4.3(4) . . . . ?
C5A C6A C7A C8A -5.7(4) . . . . ?
C1A C6A C7A C8A 174.2(3) . . . . ?
C21A N1A C8A C9A -109.4(3) . . . . ?
C21A N1A C8A C7A 126.7(2) . . . . ?
O1A C7A C8A N1A 113.3(3) . . . . ?
C6A C7A C8A N1A -65.1(3) . . . . ?
O1A C7A C8A C9A -12.1(4) . . . . ?
C6A C7A C8A C9A 169.5(2) . . . . ?
N1A C8A C9A C14A -29.5(3) . . . . ?
C7A C8A C9A C14A 92.5(3) . . . . ?
N1A C8A C9A C10A 152.3(2) . . . . ?
C7A C8A C9A C10A -85.7(3) . . . . ?
C14A C9A C10A C11A -2.8(4) . . . . ?
C8A C9A C10A C11A 175.5(2) . . . . ?
C9A C10A C11A C12A 1.9(4) . . . . ?
C10A C11A C12A C13A 0.3(4) . . . . ?
C10A C11A C12A C15A -179.1(2) . . . . ?
C11A C12A C13A C14A -1.5(5) . . . . ?
C15A C12A C13A C14A 178.0(3) . . . . ?
C12A C13A C14A C9A 0.4(5) . . . . ?
C10A C9A C14A C13A 1.7(4) . . . . ?
C8A C9A C14A C13A -176.5(3) . . . . ?
C11A C12A C15A C16A 32.1(4) . . . . ?
C13A C12A C15A C16A -147.3(3) . . . . ?
C11A C12A C15A C20A -151.3(3) . . . . ?
C13A C12A C15A C20A 29.3(4) . . . . ?
C20A C15A C16A C17A 1.8(5) . . . . ?
C12A C15A C16A C17A 178.6(3) . . . . ?
C15A C16A C17A C18A -0.4(6) . . . . ?
C16A C17A C18A C19A -0.8(6) . . . . ?
C17A C18A C19A C20A 0.5(6) . . . . ?
C18A C19A C20A C15A 0.9(5) . . . . ?
C16A C15A C20A C19A -2.1(5) . . . . ?
C12A C15A C20A C19A -178.9(3) . . . . ?
C22A O3A C21A O2A -6.0(4) . . . . ?
C22A O3A C21A N1A 173.8(2) . . . . ?
C8A N1A C21A O2A 0.8(4) . . . . ?
C8A N1A C21A O3A -179.1(2) . . . . ?
C21A O3A C22A C24A 71.5(3) . . . . ?
C21A O3A C22A C25A -53.2(3) . . . . ?
C21A O3A C22A C23A -169.6(2) . . . . ?
C6B C1B C2B C3B -0.8(5) . . . . ?
C1B C2B C3B C4B -0.3(6) . . . . ?
C2B C3B C4B C5B 1.3(6) . . . . ?
C3B C4B C5B C6B -1.1(5) . . . . ?
C4B C5B C6B C1B 0.1(4) . . . . ?
C4B C5B C6B C7B 178.9(3) . . . . ?
C2B C1B C6B C5B 0.9(5) . . . . ?
C2B C1B C6B C7B -178.1(3) . . . . ?
C5B C6B C7B O1B 168.6(3) . . . . ?
C1B C6B C7B O1B -12.5(4) . . . . ?
C5B C6B C7B C8B -13.4(4) . . . . ?
C1B C6B C7B C8B 165.5(2) . . . . ?
C21B N1B C8B C9B -89.9(3) . . . . ?
C21B N1B C8B C7B 145.3(2) . . . . ?
O1B C7B C8B N1B 16.0(3) . . . . ?
C6B C7B C8B N1B -162.0(2) . . . . ?
O1B C7B C8B C9B -108.2(3) . . . . ?
C6B C7B C8B C9B 73.8(3) . . . . ?
N1B C8B C9B C14B 118.1(3) . . . . ?
C7B C8B C9B C14B -119.5(3) . . . . ?
N1B C8B C9B C10B -58.5(3) . . . . ?
C7B C8B C9B C10B 63.9(3) . . . . ?
C14B C9B C10B C11B 0.5(4) . . . . ?
C8B C9B C10B C11B 177.1(2) . . . . ?
C9B C10B C11B C12B 0.3(4) . . . . ?
C10B C11B C12B C13B -1.2(4) . . . . ?
C10B C11B C12B C15B 179.6(2) . . . . ?
C11B C12B C13B C14B 1.5(4) . . . . ?
C15B C12B C13B C14B -179.4(3) . . . . ?
C10B C9B C14B C13B -0.3(4) . . . . ?
C8B C9B C14B C13B -177.0(2) . . . . ?
C12B C13B C14B C9B -0.7(5) . . . . ?
C13B C12B C15B C16B 144.6(3) . . . . ?
C11B C12B C15B C16B -36.3(4) . . . . ?
C13B C12B C15B C20B -34.0(4) . . . . ?
C11B C12B C15B C20B 145.1(3) . . . . ?
C20B C15B C16B C17B 1.2(5) . . . . ?
C12B C15B C16B C17B -177.5(3) . . . . ?
C15B C16B C17B C18B 0.4(6) . . . . ?
C16B C17B C18B C19B -2.4(7) . . . . ?
C17B C18B C19B C20B 2.7(8) . . . . ?
C18B C19B C20B C15B -1.0(7) . . . . ?
C16B C15B C20B C19B -0.9(6) . . . . ?
C12B C15B C20B C19B 177.8(4) . . . . ?
C22B O3B C21B O2B -10.4(4) . . . . ?
C22B O3B C21B N1B 169.6(2) . . . . ?
C8B N1B C21B O2B 1.3(4) . . . . ?
C8B N1B C21B O3B -178.7(2) . . . . ?
C21B O3B C22B C23B -177.0(4) . . . . ?
C21B O3B C22B C25B 64.6(4) . . . . ?
C21B O3B C22B C24B -58.5(4) . . . . ?
C6C C1C C2C C3C 0.3(5) . . . . ?
C1C C2C C3C C4C 0.7(5) . . . . ?
C2C C3C C4C C5C -0.8(5) . . . . ?
C3C C4C C5C C6C -0.1(4) . . . . ?
C4C C5C C6C C1C 1.0(4) . . . . ?
C4C C5C C6C C7C 178.7(2) . . . . ?
C2C C1C C6C C5C -1.1(4) . . . . ?
C2C C1C C6C C7C -178.9(3) . . . . ?
C5C C6C C7C O1C -169.0(3) . . . . ?
C1C C6C C7C O1C 8.6(4) . . . . ?
C5C C6C C7C C8C 11.7(4) . . . . ?
C1C C6C C7C C8C -170.6(2) . . . . ?
C21C N1C C8C C9C -84.5(3) . . . . ?
C21C N1C C8C C7C 153.5(2) . . . . ?
O1C C7C C8C N1C 21.4(3) . . . . ?
C6C C7C C8C N1C -159.4(2) . . . . ?
O1C C7C C8C C9C -101.6(3) . . . . ?
C6C C7C C8C C9C 77.7(3) . . . . ?
N1C C8C C9C C14C -36.5(3) . . . . ?
C7C C8C C9C C14C 83.7(2) . . . . ?
N1C C8C C9C C10C 140.3(2) . . . . ?
C7C C8C C9C C10C -99.5(3) . . . . ?
C14C C9C C10C C11C 0.7(3) . . . . ?
C8C C9C C10C C11C -176.2(2) . . . . ?
C9C C10C C11C C12C 1.7(4) . . . . ?
C10C C11C C12C C13C -2.5(4) . . . . ?
C10C C11C C12C C15C 176.0(2) . . . . ?
C11C C12C C13C C14C 1.1(4) . . . . ?
C15C C12C C13C C14C -177.4(2) . . . . ?
C12C C13C C14C C9C 1.3(4) . . . . ?
C10C C9C C14C C13C -2.1(3) . . . . ?
C8C C9C C14C C13C 174.8(2) . . . . ?
C13C C12C C15C C16C -144.0(3) . . . . ?
C11C C12C C15C C16C 37.5(4) . . . . ?
C13C C12C C15C C20C 37.5(4) . . . . ?
C11C C12C C15C C20C -141.0(3) . . . . ?
C20C C15C C16C C17C -0.7(5) . . . . ?
C12C C15C C16C C17C -179.2(3) . . . . ?
C15C C16C C17C C18C 0.7(5) . . . . ?
C16C C17C C18C C19C -0.2(6) . . . . ?
C17C C18C C19C C20C -0.2(7) . . . . ?
C18C C19C C20C C15C 0.2(7) . . . . ?
C16C C15C C20C C19C 0.2(5) . . . . ?
C12C C15C C20C C19C 178.8(3) . . . . ?
C22C O3C C21C O2C -15.2(4) . . . . ?
C22C O3C C21C N1C 164.5(3) . . . . ?
C8C N1C C21C O2C -0.1(4) . . . . ?
C8C N1C C21C O3C -179.8(2) . . . . ?
C21C O3C C22C C23C -58.8(4) . . . . ?
C21C O3C C22C C24C -177.7(4) . . . . ?
C21C O3C C22C C25C 64.9(4) . . . . ?
