#------------------------------------------------------------------------------
#$Date: 2023-10-06 03:48:35 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/95/7159553.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_7159553
loop_
_publ_author_name
'Budnikov, Alexander S.'
'Krylov, Igor B.'
'Lastovko, Andrey V.'
'Dolotov, Roman A.'
'Shevchenko, Mikhail I.'
'Terent'ev, Alexander O.'
_publ_section_title
;
 The diacetyliminoxyl radical in oxidative functionalization of alkenes.
;
_journal_issue                   38
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7758
_journal_page_last               7766
_journal_paper_doi               10.1039/d3ob00925d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C24 H22 N2 O5'
_chemical_formula_sum            'C24 H22 N2 O5'
_chemical_formula_weight         418.43
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-11-28
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-04-04 deposited with the CCDC.	2023-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.950(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6766(3)
_cell_length_b                   15.1780(4)
_cell_length_c                   12.1389(3)
_cell_measurement_reflns_used    15408
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      77.4360
_cell_measurement_theta_min      3.7450
_cell_volume                     2078.53(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00   0.00   0.50    4.11    --  -48.70 103.00 121.00  162
  2  ω     31.00  57.00   0.50    4.11    --   48.70-103.00  18.00   52
  3  ω    -73.00 -48.00   0.50   17.87    --  -86.25 103.00 121.00   50
  4  ω   -120.00 -91.00   0.50   17.87    --  -86.25-103.00  18.00   58
  5  ω     64.00  90.00   0.50   17.87    --  107.75-103.00  18.00   52
  6  ω    135.00 161.00   0.50   17.87    --  107.75 103.00 121.00   52
  7  ω   -116.00 -74.00   0.50    4.11    --  -48.70-125.00 -60.00   84
  8  ω   -115.00 -74.00   0.50    4.11    --  -48.70-125.00-180.00   82
  9  ω    -26.00  25.00   0.50    4.11    --  -48.70  19.00  30.00  102
 10  ω   -107.00 -74.00   0.50    4.11    --  -48.70-125.00 150.00   66
 11  ω   -115.00 -74.00   0.50    4.11    --  -48.70-125.00 120.00   82
 12  ω     77.00 103.00   0.50   17.87    --  107.75 -95.00  30.00   52
 13  ω     76.00 101.00   0.50   17.87    --  107.75-107.00 132.60   50
 14  ω     36.00  61.00   0.50   17.87    --  107.75 -54.00  -3.08   50
 15  ω    116.00 158.00   0.50   17.87    --  107.75  77.00-180.00   84
 16  ω     38.00  65.00   0.50   17.87    --  107.75 -61.00 120.00   54
 17  ω     44.00 105.00   0.50   17.87    --  107.75 -77.00  90.00  122
 18  ω     36.00  70.00   0.50   17.87    --  107.75 -95.00  30.00   68
 19  ω     54.00  79.00   0.50   17.87    --  107.75-144.00  13.18   50
 20  ω     99.00 165.00   0.50   17.87    --  107.75  15.00-180.00  132
 21  ω     37.00  70.00   0.50   17.87    --  107.75 -61.00 -90.00   66
 22  ω    105.00 177.00   0.50   17.87    --  107.75  45.00   0.00  144
 23  ω     38.00  90.00   0.50   17.87    --  107.75 -77.00  30.00  104
 24  ω     39.00  71.00   0.50   17.87    --  107.75 -61.00 -60.00   64
 25  ω     49.00  78.00   0.50   17.87    --  107.75-125.00 120.00   58
 26  ω     86.00 111.00   0.50   17.87    --  107.75-125.00 120.00   50
 27  ω    135.00 163.00   0.50   17.87    --  107.75   0.00-180.00   56
 28  ω     93.00 139.00   0.50   17.87    --  107.75  61.00-150.00   92
 29  ω     38.00  63.00   0.50   17.87    --  107.75 -77.00   0.00   50
 30  ω     67.00  94.00   0.50   17.87    --  107.75 -77.00   0.00   54
 31  ω     58.00 108.00   0.50   17.87    --  107.75-107.00-138.08  100
 32  ω     63.00  97.00   0.50   17.87    --  107.75 -77.00  54.21   68
 33  ω     36.00  80.00   0.50   17.87    --  107.75   0.00-180.00   88
 34  ω     94.00 125.00   0.50   17.87    --  107.75-144.00  13.18   62
 35  ω    104.00 130.00   0.50   17.87    --  107.75  77.00  30.00   52
 36  ω     83.00 114.00   0.50   17.87    --  107.75 -82.00 132.39   62
 37  ω     56.00 107.00   0.50   17.87    --  107.75-125.00  90.00  102
 38  ω     36.00  72.00   0.50   17.87    --  107.75 -77.00-120.00   72
 39  ω     56.00  91.00   0.50   17.87    --  107.75 -95.00  60.00   70
 40  ω     38.00  70.00   0.50   17.87    --  107.75 -61.00  30.00   64
 41  ω     43.00  70.00   0.50   17.87    --  107.75 -77.00-150.00   54
 42  ω     37.00  92.00   0.50   17.87    --  107.75 -77.00 150.00  110
 43  ω     38.00  89.00   0.50   17.87    --  107.75 -95.00 -90.00  102
 44  ω     55.00  81.00   0.50   17.87    --  107.75-125.00-150.00   52
 45  ω    124.00 178.00   0.50   17.87    --  107.75  45.00 -60.00  108
 46  ω    100.00 164.00   0.50   17.87    --  107.75  45.00  90.00  128
 47  ω     40.00  82.00   0.50   17.87    --  107.75 -87.00 -86.11   84
 48  ω     85.00 111.00   0.50   17.87    --  107.75 -87.00 -86.11   52
 49  ω     36.00  69.00   0.50   17.87    --  107.75 -61.00-180.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1019
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25662
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.826
_diffrn_reflns_theta_min         4.686
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4433
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0655
_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)+(0.0741P)²+2.2397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1740
_refine_ls_wR_factor_ref         0.1776
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3958
_reflns_number_total             4433
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00925d3.cif
_cod_data_source_block           la-293
_cod_depositor_comments
'Adding full bibliography for 7159551--7159553.cif.'
_cod_database_code               7159553
_shelx_shelxl_version_number     2017/1
_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_max   0.985
_shelx_estimated_absorpt_t_min   0.913
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1-C8A \\sim C1-C8B
 with sigma of 0.003
 C8A-C9A \\sim C8B-C9B
 with sigma of 0.003
 C8A-C13A \\sim C8B-C13B
 with sigma of 0.003
 C9A-C10A \\sim C9B-C10B
 with sigma of 0.003
 C10A-C11A \\sim C10B-C11B
 with sigma of 0.003
 C11A-C12A \\sim C11B-C12B
 with sigma of 0.003
 C12A-C13A \\sim C12B-C13B
 with sigma of 0.003
 C1-C19A \\sim C1-C19B
 with sigma of 0.003
 O4A-C19A \\sim O4B-C19B
 with sigma of 0.003
 O4A-C20A \\sim O4B-C20B
 with sigma of 0.003
 C20A-C21A \\sim C20B-C21B
 with sigma of 0.003
 C21A-N2A \\sim C21B-N2B
 with sigma of 0.003
 C19A-N2A \\sim N2B-C19B
 with sigma of 0.003
 C20A-C22A \\sim C20B-C22B
 with sigma of 0.003
 O5A-C23A \\sim O5B-C23B
 with sigma of 0.003
 C21A-C23A \\sim C21B-C23B
 with sigma of 0.003
 C23A-C24A \\sim C23B-C24B
 with sigma of 0.003
3. Uiso/Uaniso restraints and constraints
Uanis(C19A) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(C8A) = Uanis(C8B)
Uanis(C9A) = Uanis(C9B)
Uanis(C10A) = Uanis(C10B)
Uanis(C11A) = Uanis(C11B)
Uanis(C12A) = Uanis(C12B)
Uanis(C13A) = Uanis(C13B)
Uanis(C19A) = Uanis(C19B)
Uanis(N2A) = Uanis(O4B)
Uanis(O4A) = Uanis(N2B)
Uanis(C20A) = Uanis(C20B)
Uanis(C21A) = Uanis(C21B)
Uanis(C24A) = Uanis(C22B)
Uanis(C24B) = Uanis(C22A)
Uanis(C23A) = Uanis(C23B)
Uanis(O5A) = Uanis(O5B)
4. Others
 Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=
 Sof(H12B)=Sof(C13B)=Sof(H13B)=1-FVAR(1)
 Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=
 Sof(H12A)=Sof(C13A)=Sof(H13A)=FVAR(1)
 Sof(O4B)=Sof(O5B)=Sof(N2B)=Sof(C19B)=Sof(C20B)=Sof(C21B)=Sof(C22B)=Sof(H22D)=
 Sof(H22E)=Sof(H22F)=Sof(C23B)=Sof(C24B)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(2)
 Sof(O4A)=Sof(O5A)=Sof(N2A)=Sof(C19A)=Sof(C20A)=Sof(C21A)=Sof(C22A)=Sof(H22A)=
 Sof(H22B)=Sof(H22C)=Sof(C23A)=Sof(C24A)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9A(H9A), C9B(H9B), C10A(H10A),
 C10B(H10B), C11A(H11A), C11B(H11B), C12A(H12A), C12B(H12B), C13A(H13A),
 C13B(H13B)
5.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C22A(H22A,H22B,H22C), C22B(H22D,
 H22E,H22F), C24A(H24A,H24B,H24C), C24B(H24D,H24E,H24F)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
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 0.45324(12) 0.59889(9) 0.65277(13) 0.0274(3) Uani 1 1 d . . . . .
O2 O 0.49920(16) 0.87768(11) 0.53792(17) 0.0426(4) Uani 1 1 d . . . . .
O3 O 0.64777(15) 0.74889(13) 0.76524(14) 0.0399(4) Uani 1 1 d . . . . .
O4A O 0.2712(2) 0.5124(2) 0.4737(3) 0.0252(6) Uani 0.5796(18) 1 d D . P A 1
O4B O 0.1611(4) 0.6055(3) 0.6052(3) 0.0254(7) Uani 0.4204(18) 1 d D . P A 2
O5A O -0.0638(2) 0.6135(2) 0.2939(2) 0.0350(6) Uani 0.5796(18) 1 d D . P A 1
O5B O -0.0340(3) 0.5757(3) 0.2661(4) 0.0350(6) Uani 0.4204(18) 1 d D . P A 2
N1 N 0.39927(16) 0.67944(11) 0.61240(15) 0.0261(4) Uani 1 1 d . . . . .
N2A N 0.1580(4) 0.5864(3) 0.5620(3) 0.0254(7) Uani 0.5796(18) 1 d D . P A 1
N2B N 0.2317(4) 0.5231(5) 0.4847(5) 0.0252(6) Uani 0.4204(18) 1 d D . P A 2
C1 C 0.36338(17) 0.54108(13) 0.67802(17) 0.0244(4) Uani 1 1 d D . . . .
C2 C 0.41379(18) 0.44725(13) 0.68209(16) 0.0257(4) Uani 1 1 d . . . . .
C3 C 0.52030(19) 0.42955(15) 0.65476(19) 0.0318(5) Uani 1 1 d . . . . .
H3 H 0.562661 0.475757 0.630104 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5645(2) 0.34373(17) 0.6637(2) 0.0393(6) Uani 1 1 d . . . . .
H4 H 0.637737 0.331826 0.646266 0.047 Uiso 1 1 calc R U . . .
C5 C 0.5026(3) 0.27601(16) 0.6978(2) 0.0428(6) Uani 1 1 d . . . . .
H5 H 0.533456 0.217764 0.704378 0.051 Uiso 1 1 calc R U . . .
C6 C 0.3951(3) 0.29337(15) 0.7225(2) 0.0384(6) Uani 1 1 d . . . . .
H6 H 0.351616 0.246599 0.744407 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3510(2) 0.37837(15) 0.71534(18) 0.0315(5) Uani 1 1 d . . . . .
H7 H 0.277750 0.389846 0.733097 0.038 Uiso 1 1 calc R U . . .
C8A C 0.3549(7) 0.5637(11) 0.7980(5) 0.0230(14) Uani 0.630(15) 1 d D . P A 1
C8B C 0.3330(11) 0.569(2) 0.7878(10) 0.0230(14) Uani 0.370(15) 1 d D . P A 2
C9A C 0.4585(7) 0.5920(7) 0.8764(6) 0.0281(12) Uani 0.630(15) 1 d D . P A 1
H9A H 0.530104 0.599278 0.853920 0.034 Uiso 0.630(15) 1 calc R U P A 1
C9B C 0.4275(11) 0.5901(13) 0.8813(10) 0.0281(12) Uani 0.370(15) 1 d D . P A 2
H9B H 0.504203 0.596068 0.868892 0.034 Uiso 0.370(15) 1 calc R U P A 2
C10A C 0.4546(8) 0.6092(6) 0.9872(5) 0.0369(15) Uani 0.630(15) 1 d D . P A 1
H10A H 0.524703 0.627044 1.041692 0.044 Uiso 0.630(15) 1 calc R U P A 1
C10B C 0.4157(13) 0.6025(12) 0.9907(10) 0.0369(15) Uani 0.370(15) 1 d D . P A 2
H10B H 0.483125 0.616241 1.051009 0.044 Uiso 0.370(15) 1 calc R U P A 2
C11A C 0.3506(10) 0.6007(5) 1.0199(7) 0.0375(17) Uani 0.630(15) 1 d D . P A 1
H11A H 0.350325 0.611529 1.096904 0.045 Uiso 0.630(15) 1 calc R U P A 1
C11B C 0.3059(13) 0.5950(10) 1.0118(14) 0.0375(17) Uani 0.370(15) 1 d D . P A 2
H11B H 0.293860 0.608642 1.084424 0.045 Uiso 0.370(15) 1 calc R U P A 2
C12A C 0.2467(10) 0.5768(9) 0.9417(8) 0.043(2) Uani 0.630(15) 1 d D . P A 1
H12A H 0.174535 0.573105 0.963884 0.051 Uiso 0.630(15) 1 calc R U P A 1
C12B C 0.2138(16) 0.5668(16) 0.9227(15) 0.043(2) Uani 0.370(15) 1 d D . P A 2
H12B H 0.138623 0.556722 0.937056 0.051 Uiso 0.370(15) 1 calc R U P A 2
C13A C 0.2493(9) 0.5581(14) 0.8303(9) 0.0335(15) Uani 0.630(15) 1 d D . P A 1
H13A H 0.178494 0.541334 0.775931 0.040 Uiso 0.630(15) 1 calc R U P A 1
C13B C 0.2256(16) 0.552(3) 0.8131(18) 0.0335(15) Uani 0.370(15) 1 d D . P A 2
H13B H 0.160196 0.530864 0.755417 0.040 Uiso 0.370(15) 1 calc R U P A 2
C14 C 0.47573(18) 0.74008(14) 0.61438(17) 0.0255(4) Uani 1 1 d . . . . .
C15 C 0.4287(2) 0.82521(14) 0.55668(18) 0.0289(4) Uani 1 1 d . . . . .
C16 C 0.2974(2) 0.83851(16) 0.5211(2) 0.0352(5) Uani 1 1 d . . . . .
H16A H 0.279758 0.898020 0.490014 0.053 Uiso 1 1 calc R U . . .
H16B H 0.264818 0.831156 0.587292 0.053 Uiso 1 1 calc R U . . .
H16C H 0.261489 0.795069 0.462631 0.053 Uiso 1 1 calc R U . . .
C17 C 0.60854(19) 0.73125(14) 0.66509(18) 0.0275(4) Uani 1 1 d . . . . .
C18 C 0.6812(2) 0.70325(16) 0.5880(2) 0.0344(5) Uani 1 1 d . . . . .
H18A H 0.764938 0.702251 0.630118 0.052 Uiso 1 1 calc R U . . .
H18B H 0.669950 0.744757 0.524310 0.052 Uiso 1 1 calc R U . . .
H18C H 0.656728 0.644174 0.558615 0.052 Uiso 1 1 calc R U . . .
C19A C 0.2586(6) 0.5506(9) 0.5743(6) 0.0214(13) Uani 0.5796(18) 1 d D U P A 1
C19B C 0.2470(9) 0.5478(13) 0.5871(9) 0.0214(13) Uani 0.4204(18) 1 d D . P A 2
C20A C 0.1701(3) 0.5345(2) 0.3920(3) 0.0252(6) Uani 0.5796(18) 1 d D . P A 1
C20B C 0.0797(4) 0.6085(3) 0.5012(4) 0.0252(6) Uani 0.4204(18) 1 d D . P A 2
C21A C 0.0990(4) 0.5793(4) 0.4461(3) 0.0221(11) Uani 0.5796(18) 1 d D . P A 1
C21B C 0.1219(6) 0.5589(6) 0.4269(4) 0.0221(11) Uani 0.4204(18) 1 d D . P A 2
C22A C 0.1600(5) 0.5056(5) 0.2731(4) 0.0379(12) Uani 0.5796(18) 1 d D . P A 1
H22A H 0.181924 0.554448 0.229728 0.057 Uiso 0.5796(18) 1 calc R U P A 1
H22B H 0.078226 0.487695 0.237556 0.057 Uiso 0.5796(18) 1 calc R U P A 1
H22C H 0.213381 0.455727 0.273435 0.057 Uiso 0.5796(18) 1 calc R U P A 1
C22B C -0.0286(6) 0.6616(7) 0.4952(9) 0.0377(11) Uani 0.4204(18) 1 d D . P A 2
H22D H -0.097293 0.622355 0.484160 0.057 Uiso 0.4204(18) 1 calc R U P A 2
H22E H -0.040835 0.702868 0.431141 0.057 Uiso 0.4204(18) 1 calc R U P A 2
H22F H -0.019186 0.694605 0.566393 0.057 Uiso 0.4204(18) 1 calc R U P A 2
C23A C -0.0164(3) 0.6196(2) 0.3956(3) 0.0277(6) Uani 0.5796(18) 1 d D . P A 1
C23B C 0.0650(4) 0.5457(3) 0.3059(4) 0.0277(6) Uani 0.4204(18) 1 d D . P A 2
C24A C -0.0717(4) 0.6671(5) 0.4757(6) 0.0377(11) Uani 0.5796(18) 1 d D . P A 1
H24A H -0.101558 0.624334 0.522032 0.057 Uiso 0.5796(18) 1 calc R U P A 1
H24B H -0.137527 0.703247 0.432314 0.057 Uiso 0.5796(18) 1 calc R U P A 1
H24C H -0.012514 0.705064 0.525603 0.057 Uiso 0.5796(18) 1 calc R U P A 1
C24B C 0.1318(8) 0.4979(8) 0.2359(6) 0.0379(12) Uani 0.4204(18) 1 d D . P A 2
H24D H 0.206373 0.528763 0.239418 0.057 Uiso 0.4204(18) 1 calc R U P A 2
H24E H 0.084284 0.495361 0.156565 0.057 Uiso 0.4204(18) 1 calc R U P A 2
H24F H 0.148958 0.437857 0.265340 0.057 Uiso 0.4204(18) 1 calc R U P A 2
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 -1 0.0340
1 -1 1 0.0773
1 1 1 0.0217
-1 -1 -1 0.0324
0 -1 1 0.0748
1 0 -1 0.0248
-1 0 1 0.0095
0 -1 0 0.0650
0 1 0 0.0512
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
N1 O1 C1 108.32(14) . . ?
C20A O4A C19A 105.4(3) . . ?
C20B O4B C19B 103.5(4) . . ?
C14 N1 O1 111.83(16) . . ?
C19A N2A C21A 106.6(5) . . ?
C19B N2B C21B 104.8(5) . . ?
O1 C1 C2 105.88(16) . . ?
O1 C1 C8A 107.0(5) . . ?
O1 C1 C8B 111.0(9) . . ?
O1 C1 C19A 103.8(5) . . ?
O1 C1 C19B 111.4(8) . . ?
C8A C1 C2 107.3(7) . . ?
C8B C1 C2 113.8(12) . . ?
C19A C1 C2 109.5(5) . . ?
C19A C1 C8A 122.2(6) . . ?
C19B C1 C2 110.5(7) . . ?
C19B C1 C8B 104.5(8) . . ?
C3 C2 C1 121.94(19) . . ?
C3 C2 C7 119.5(2) . . ?
C7 C2 C1 118.55(19) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
C9A C8A C1 117.4(5) . . ?
C13A C8A C1 122.5(6) . . ?
C13A C8A C9A 120.1(4) . . ?
C9B C8B C1 117.3(9) . . ?
C13B C8B C1 124.6(13) . . ?
C13B C8B C9B 115.5(11) . . ?
C8A C9A H9A 120.7 . . ?
C10A C9A C8A 118.6(4) . . ?
C10A C9A H9A 120.7 . . ?
C8B C9B H9B 118.1 . . ?
C10B C9B C8B 123.8(9) . . ?
C10B C9B H9B 118.1 . . ?
C9A C10A H10A 119.5 . . ?
C11A C10A C9A 121.1(5) . . ?
C11A C10A H10A 119.5 . . ?
C9B C10B H10B 120.1 . . ?
C11B C10B C9B 119.8(12) . . ?
C11B C10B H10B 120.1 . . ?
C10A C11A H11A 119.7 . . ?
C10A C11A C12A 120.6(7) . . ?
C12A C11A H11A 119.7 . . ?
C10B C11B H11B 121.5 . . ?
C10B C11B C12B 117.0(15) . . ?
C12B C11B H11B 121.5 . . ?
C11A C12A H12A 120.5 . . ?
C11A C12A C13A 119.1(8) . . ?
C13A C12A H12A 120.5 . . ?
C11B C12B H12B 118.3 . . ?
C11B C12B C13B 123.3(18) . . ?
C13B C12B H12B 118.3 . . ?
C8A C13A C12A 120.4(7) . . ?
C8A C13A H13A 119.8 . . ?
C12A C13A H13A 119.8 . . ?
C8B C13B C12B 120.0(15) . . ?
C8B C13B H13B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
N1 C14 C15 116.11(18) . . ?
N1 C14 C17 125.38(19) . . ?
C15 C14 C17 118.45(18) . . ?
O2 C15 C14 117.9(2) . . ?
O2 C15 C16 123.7(2) . . ?
C16 C15 C14 118.33(19) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 C14 117.9(2) . . ?
O3 C17 C18 124.6(2) . . ?
C18 C17 C14 117.47(18) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4A C19A C1 116.2(6) . . ?
N2A C19A O4A 112.3(3) . . ?
N2A C19A C1 131.4(8) . . ?
O4B C19B C1 118.4(8) . . ?
N2B C19B O4B 114.6(5) . . ?
N2B C19B C1 124.5(9) . . ?
O4A C20A C22A 117.9(4) . . ?
C21A C20A O4A 106.9(3) . . ?
C21A C20A C22A 135.2(3) . . ?
O4B C20B C22B 116.3(5) . . ?
C21B C20B O4B 107.9(4) . . ?
C21B C20B C22B 135.8(6) . . ?
N2A C21A C23A 123.3(3) . . ?
C20A C21A N2A 108.5(3) . . ?
C20A C21A C23A 128.0(3) . . ?
N2B C21B C23B 124.7(4) . . ?
C20B C21B N2B 108.8(4) . . ?
C20B C21B C23B 126.4(4) . . ?
C20A C22A H22A 109.5 . . ?
C20A C22A H22B 109.5 . . ?
C20A C22A H22C 109.5 . . ?
H22A C22A H22B 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C20B C22B H22D 109.5 . . ?
C20B C22B H22E 109.5 . . ?
C20B C22B H22F 109.5 . . ?
H22D C22B H22E 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
O5A C23A C21A 121.4(3) . . ?
O5A C23A C24A 122.6(4) . . ?
C21A C23A C24A 116.0(3) . . ?
O5B C23B C21B 119.0(4) . . ?
O5B C23B C24B 122.7(5) . . ?
C21B C23B C24B 118.2(4) . . ?
C23A C24A H24A 109.5 . . ?
C23A C24A H24B 109.5 . . ?
C23A C24A H24C 109.5 . . ?
H24A C24A H24B 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
C23B C24B H24D 109.5 . . ?
C23B C24B H24E 109.5 . . ?
C23B C24B H24F 109.5 . . ?
H24D C24B H24E 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 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
O1 N1 1.405(2) . ?
O1 C1 1.460(2) . ?
O2 C15 1.209(3) . ?
O3 C17 1.213(3) . ?
O4A C19A 1.393(11) . ?
O4A C20A 1.373(4) . ?
O4B C19B 1.390(12) . ?
O4B C20B 1.371(4) . ?
O5A C23A 1.219(4) . ?
O5B C23B 1.220(4) . ?
N1 C14 1.278(3) . ?
N2A C19A 1.268(9) . ?
N2A C21A 1.403(4) . ?
N2B C19B 1.266(10) . ?
N2B C21B 1.403(4) . ?
C1 C2 1.537(3) . ?
C1 C8A 1.525(3) . ?
C1 C8B 1.525(4) . ?
C1 C19A 1.519(3) . ?
C1 C19B 1.517(3) . ?
C2 C3 1.394(3) . ?
C2 C7 1.395(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C7 H7 0.9500 . ?
C8A C9A 1.400(4) . ?
C8A C13A 1.389(4) . ?
C8B C9B 1.401(5) . ?
C8B C13B 1.389(5) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.382(4) . ?
C9B H9B 0.9500 . ?
C9B C10B 1.383(5) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.376(6) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.376(6) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.382(6) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.382(6) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.390(4) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.390(4) . ?
C13A H13A 0.9500 . ?
C13B H13B 0.9500 . ?
C14 C15 1.505(3) . ?
C14 C17 1.520(3) . ?
C15 C16 1.495(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.478(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20A C21A 1.365(5) . ?
C20A C22A 1.484(5) . ?
C20B C21B 1.361(5) . ?
C20B C22B 1.485(6) . ?
C21A C23A 1.462(4) . ?
C21B C23B 1.462(4) . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
C23A C24A 1.485(7) . ?
C23B C24B 1.483(7) . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
C24A H24C 0.9800 . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?
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
O1 N1 C14 C15 171.08(16) . . . . ?
O1 N1 C14 C17 -6.1(3) . . . . ?
O1 C1 C2 C3 -5.2(2) . . . . ?
O1 C1 C2 C7 174.12(17) . . . . ?
O1 C1 C8A C9A -32.2(14) . . . . ?
O1 C1 C8A C13A 147.1(16) . . . . ?
O1 C1 C8B C9B -45(3) . . . . ?
O1 C1 C8B C13B 154(3) . . . . ?
O1 C1 C19A O4A 71.0(10) . . . . ?
O1 C1 C19A N2A -110.4(13) . . . . ?
O1 C1 C19B O4B -94.8(14) . . . . ?
O1 C1 C19B N2B 66.3(19) . . . . ?
O4A C20A C21A N2A 1.2(6) . . . . ?
O4A C20A C21A C23A 177.4(5) . . . . ?
O4B C20B C21B N2B 0.4(10) . . . . ?
O4B C20B C21B C23B -178.4(8) . . . . ?
N1 O1 C1 C2 161.41(15) . . . . ?
N1 O1 C1 C8A -84.4(6) . . . . ?
N1 O1 C1 C8B -74.6(11) . . . . ?
N1 O1 C1 C19A 46.1(5) . . . . ?
N1 O1 C1 C19B 41.3(6) . . . . ?
N1 C14 C15 O2 -166.5(2) . . . . ?
N1 C14 C15 C16 10.8(3) . . . . ?
N1 C14 C17 O3 -89.0(3) . . . . ?
N1 C14 C17 C18 92.1(3) . . . . ?
N2A C21A C23A O5A 178.4(5) . . . . ?
N2A C21A C23A C24A -2.2(8) . . . . ?
N2B C21B C23B O5B 175.7(8) . . . . ?
N2B C21B C23B C24B -5.8(13) . . . . ?
C1 O1 N1 C14 164.32(17) . . . . ?
C1 C2 C3 C4 177.68(19) . . . . ?
C1 C2 C7 C6 -178.51(19) . . . . ?
C1 C8A C9A C10A -177.1(10) . . . . ?
C1 C8A C13A C12A 178.0(15) . . . . ?
C1 C8B C9B C10B -169.1(19) . . . . ?
C1 C8B C13B C12B 169(3) . . . . ?
C2 C1 C8A C9A 81.1(13) . . . . ?
C2 C1 C8A C13A -99.6(16) . . . . ?
C2 C1 C8B C9B 75(3) . . . . ?
C2 C1 C8B C13B -86(3) . . . . ?
C2 C1 C19A O4A -41.7(11) . . . . ?
C2 C1 C19A N2A 136.9(13) . . . . ?
C2 C1 C19B O4B 147.8(12) . . . . ?
C2 C1 C19B N2B -51(2) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C2 C7 C6 0.9(3) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C7 -1.3(4) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C7 C2 C3 C4 -1.7(3) . . . . ?
C8A C1 C2 C3 -119.2(4) . . . . ?
C8A C1 C2 C7 60.1(4) . . . . ?
C8A C1 C19A O4A -168.3(10) . . . . ?
C8A C1 C19A N2A 10.3(19) . . . . ?
C8A C9A C10A C11A -1.5(16) . . . . ?
C8B C1 C2 C3 -127.4(6) . . . . ?
C8B C1 C2 C7 52.0(6) . . . . ?
C8B C1 C19B O4B 25(2) . . . . ?
C8B C1 C19B N2B -174(2) . . . . ?
C8B C9B C10B C11B 0(3) . . . . ?
C9A C8A C13A C12A -3(3) . . . . ?
C9A C10A C11A C12A -1.5(15) . . . . ?
C9B C8B C13B C12B 7(5) . . . . ?
C9B C10B C11B C12B 6(3) . . . . ?
C10A C11A C12A C13A 2(2) . . . . ?
C10B C11B C12B C13B -5(4) . . . . ?
C11A C12A C13A C8A 0(3) . . . . ?
C11B C12B C13B C8B -2(5) . . . . ?
C13A C8A C9A C10A 4(2) . . . . ?
C13B C8B C9B C10B -6(4) . . . . ?
C15 C14 C17 O3 93.8(2) . . . . ?
C15 C14 C17 C18 -85.1(2) . . . . ?
C17 C14 C15 O2 10.9(3) . . . . ?
C17 C14 C15 C16 -171.76(19) . . . . ?
C19A O4A C20A C21A -3.5(8) . . . . ?
C19A O4A C20A C22A 177.6(7) . . . . ?
C19A N2A C21A C20A 1.9(9) . . . . ?
C19A N2A C21A C23A -174.6(8) . . . . ?
C19A C1 C2 C3 106.1(5) . . . . ?
C19A C1 C2 C7 -74.6(5) . . . . ?
C19A C1 C8A C9A -151.3(11) . . . . ?
C19A C1 C8A C13A 28(2) . . . . ?
C19B O4B C20B C21B -3.4(11) . . . . ?
C19B O4B C20B C22B 176.3(11) . . . . ?
C19B N2B C21B C20B 3.1(14) . . . . ?
C19B N2B C21B C23B -178.1(12) . . . . ?
C19B C1 C2 C3 115.5(7) . . . . ?
C19B C1 C2 C7 -65.2(7) . . . . ?
C19B C1 C8B C9B -165(2) . . . . ?
C19B C1 C8B C13B 34(4) . . . . ?
C20A O4A C19A N2A 5.0(12) . . . . ?
C20A O4A C19A C1 -176.1(8) . . . . ?
C20A C21A C23A O5A 2.7(9) . . . . ?
C20A C21A C23A C24A -177.9(6) . . . . ?
C20B O4B C19B N2B 5.9(17) . . . . ?
C20B O4B C19B C1 168.8(12) . . . . ?
C20B C21B C23B O5B -5.8(13) . . . . ?
C20B C21B C23B C24B 172.8(10) . . . . ?
C21A N2A C19A O4A -4.3(12) . . . . ?
C21A N2A C19A C1 177.1(11) . . . . ?
C21B N2B C19B O4B -5.6(18) . . . . ?
C21B N2B C19B C1 -167.3(14) . . . . ?
C22A C20A C21A N2A 179.8(6) . . . . ?
C22A C20A C21A C23A -3.9(11) . . . . ?
C22B C20B C21B N2B -179.2(9) . . . . ?
C22B C20B C21B C23B 2.0(17) . . . . ?
