#------------------------------------------------------------------------------
#$Date: 2023-10-06 02:46:59 +0200 (Fri 06 de Oct de 2023) $
#$Revision: 286795 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/95/7159545.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_7159545
loop_
_publ_author_name
'Komogortsev, Andrey N.'
'Lichitskii, Boris V.'
'Melekhina, Valeriya G.'
_publ_section_title
;
 1,1'-Carbonyldiimidazole-mediated transformation of allomaltol containing
 hydrazides into substituted 3-acetyltetronic acids.
;
_journal_issue                   35
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7224
_journal_page_last               7230
_journal_paper_doi               10.1039/d3ob01136d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C23 H24 N4 O6, C7 H8'
_chemical_formula_sum            'C30 H32 N4 O6'
_chemical_formula_weight         544.59
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-11-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-06-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.0334(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.3210(2)
_cell_length_b                   7.16745(8)
_cell_length_c                   20.9490(3)
_cell_measurement_reflns_used    15608
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      77.3470
_cell_measurement_theta_min      3.8160
_cell_volume                     2725.53(6)
_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 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00  23.00   0.50    5.50    --  -48.67  41.00-132.00  138
  2  ω   -120.00 -38.00   0.50    5.50    --  -48.67 -41.00  74.00  164
  3  ω     11.00  36.00   0.50    5.50    --   48.67 -41.00  74.00   50
  4  ω     52.00  80.00   0.50    5.50    --   48.67  41.00-132.00   56
  5  ω    -46.00 -21.00   0.50   22.00    --  -86.25  41.00-132.00   50
  6  ω   -126.00 -90.00   0.50   22.00    --  -86.25 -41.00  74.00   72
  7  ω     99.00 142.00   0.50   22.00    --  107.75  41.00-132.00   86
  8  ω    -14.00  26.00   0.50    5.50    --  -48.67  19.00   0.00   80
  9  ω   -105.00 -74.00   0.50    5.50    --  -48.67-125.00-150.00   62
 10  ω    -21.00  25.00   0.50    5.50    --   48.67 -19.00 -30.00   92
 11  ω    -44.00 -19.00   0.50   22.00    --  -86.25  45.00  60.00   50
 12  ω    120.00 163.00   0.50   22.00    --  107.75  15.00 -30.00   86
 13  ω     38.00  63.00   0.50   22.00    --  107.75 -77.00-120.00   50
 14  ω     39.00  64.00   0.50   22.00    --  107.75 -61.00 -30.00   50
 15  ω    126.00 156.00   0.50   22.00    --  107.75  30.00-180.00   60
 16  ω     40.00  71.00   0.50   22.00    --  107.75 -61.00-180.00   62
 17  ω     47.00  73.00   0.50   22.00    --  107.75-125.00   0.00   52
 18  ω    110.00 137.00   0.50   22.00    --  107.75  45.00-120.00   54
 19  ω    144.00 175.00   0.50   22.00    --  107.75  45.00-120.00   62
 20  ω     39.00  98.00   0.50   22.00    --  107.75 -98.00  35.98  118
 21  ω     40.00 105.00   0.50   22.00    --  107.75 -77.00 120.00  130
 22  ω    117.00 143.00   0.50   22.00    --  107.75 107.00-170.22   52
 23  ω     97.00 125.00   0.50   22.00    --  107.75  30.00   0.00   56
 24  ω     91.00 127.00   0.50   22.00    --  107.75  77.00  30.00   72
 25  ω    133.00 159.00   0.50   22.00    --  107.75  30.00   0.00   52
 26  ω     41.00 102.00   0.50   22.00    --  107.75 -95.00 120.00  122
 27  ω     57.00 105.00   0.50   22.00    --  107.75-103.00  84.50   96
 28  ω    101.00 127.00   0.50   22.00    --  107.75  61.00-150.00   52
 29  ω    139.00 165.00   0.50   22.00    --  107.75  61.00-150.00   52
 30  ω     54.00  80.00   0.50   22.00    --  107.75-125.00 120.00   52
 31  ω     68.00 104.00   0.50   22.00    --  107.75-125.00 -90.00   72
 32  ω    146.00 171.00   0.50   22.00    --  107.75  61.00-180.00   50
 33  ω     36.00  61.00   0.50   22.00    --  107.75 -61.00 120.00   50
 34  ω     42.00  72.00   0.50   22.00    --  107.75-125.00  30.00   60
 35  ω     82.00 107.00   0.50   22.00    --  107.75-125.00  30.00   50
 36  ω    103.00 132.00   0.50   22.00    --  107.75  30.00  60.00   58
 37  ω    142.00 168.00   0.50   22.00    --  107.75  30.00  60.00   52
 38  ω     93.00 119.00   0.50   22.00    --  107.75  61.00-180.00   52
 39  ω     67.00 114.00   0.50   22.00    --  107.75-143.00 -28.98   94
 40  ω     69.00  98.00   0.50   22.00    --  107.75 -77.00-120.00   58
 41  ω    138.00 164.00   0.50   22.00    --  107.75  77.00  30.00   52
 42  ω     95.00 134.00   0.50   22.00    --  107.75  61.00 150.00   78
 43  ω     98.00 136.00   0.50   22.00    --  107.75  15.00   0.00   76
 44  ω    145.00 178.00   0.50   22.00    --  107.75  15.00   0.00   66
 45  ω     39.00  94.00   0.50   22.00    --  107.75 -77.00 -60.00  110
 46  ω     37.00  62.00   0.50   22.00    --  107.75 -77.00  90.00   50
 47  ω     37.00  62.00   0.50   22.00    --  107.75 -77.00   0.00   50
 48  ω     78.00 104.00   0.50   22.00    --  107.75 -77.00   0.00   52
 49  ω     49.00  74.00   0.50   22.00    --  107.75 -95.00-180.00   50
 50  ω     40.00  80.00   0.50   22.00    --  107.75 -95.00 150.00   80
 51  ω    115.00 141.00   0.50   22.00    --  107.75 122.00-133.21   52
 52  ω    117.00 143.00   0.50   22.00    --  107.75  45.00-150.00   52
 53  ω    135.00 178.00   0.50   22.00    --  107.75  30.00 -90.00   86
 54  ω    139.00 175.00   0.50   22.00    --  107.75 125.00   0.00   72
 55  ω     95.00 121.00   0.50   22.00    --  107.75 -88.00 -74.45   52
 56  ω     37.00  68.00   0.50   22.00    --  107.75 -61.00 -60.00   62
;
_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  0.0450
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            33634
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.833
_diffrn_reflns_theta_min         2.687
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66569
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0413
_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)+(0.0513P)²+1.3167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4980
_reflns_number_total             5757
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01136d2.cif
_cod_data_source_block           kjoket5m
_cod_depositor_comments
'Adding full bibliography for 7159539--7159545.cif.'
_cod_database_code               7159545
_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   0.887
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C10(H10), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C30(H30A,H30B,H30C)
;
_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 0.48301(5) 0.21431(13) 0.19493(4) 0.0185(2) Uani 1 1 d . . . . .
O2 O 0.59311(5) 0.09422(14) 0.39339(5) 0.0249(2) Uani 1 1 d . . . . .
O3 O 0.46233(5) 0.27018(13) 0.36063(4) 0.0183(2) Uani 1 1 d . . . . .
O4 O 0.43486(6) 0.00512(14) 0.40669(5) 0.0263(2) Uani 1 1 d . . . . .
O5 O 0.44495(6) 0.78263(14) 0.23266(5) 0.0263(2) Uani 1 1 d . . . . .
O6 O 0.21984(5) 0.16896(15) 0.16779(5) 0.0255(2) Uani 1 1 d . . . . .
N1 N 0.48057(6) 0.47961(15) 0.26166(5) 0.0169(2) Uani 1 1 d . . . . .
N2 N 0.55144(6) 0.51196(16) 0.30753(6) 0.0181(2) Uani 1 1 d . . . . .
H2 H 0.5530(10) 0.558(3) 0.3466(10) 0.032(5) Uiso 1 1 d . . . . .
N3 N 0.42519(6) 0.29466(17) 0.45013(5) 0.0200(2) Uani 1 1 d . . . . .
N4 N 0.40950(7) 0.3851(2) 0.54518(6) 0.0281(3) Uani 1 1 d . . . . .
C1 C 0.45425(7) 0.29198(18) 0.24485(6) 0.0164(3) Uani 1 1 d . . . . .
C2 C 0.47771(7) 0.16721(18) 0.30819(6) 0.0170(3) Uani 1 1 d . . . . .
H2A H 0.447520 0.050516 0.298290 0.020 Uiso 1 1 calc R U . . .
C3 C 0.55964(7) 0.11557(19) 0.33256(7) 0.0200(3) Uani 1 1 d . . . . .
C4 C 0.58888(7) 0.08289(19) 0.27907(7) 0.0216(3) Uani 1 1 d . . . . .
H4 H 0.636448 0.029336 0.289462 0.026 Uiso 1 1 calc R U . . .
C5 C 0.54959(7) 0.12733(19) 0.21452(7) 0.0197(3) Uani 1 1 d . . . . .
C6 C 0.57151(8) 0.0864(2) 0.15445(7) 0.0259(3) Uani 1 1 d . . . . .
H6A H 0.536285 -0.001232 0.124398 0.039 Uiso 1 1 calc R U . . .
H6B H 0.620876 0.031014 0.169606 0.039 Uiso 1 1 calc R U . . .
H6C H 0.571824 0.202387 0.129790 0.039 Uiso 1 1 calc R U . . .
C7 C 0.44113(7) 0.1713(2) 0.40478(6) 0.0198(3) Uani 1 1 d . . . . .
C8 C 0.42038(8) 0.2415(2) 0.51167(7) 0.0252(3) Uani 1 1 d . . . . .
H8 H 0.424456 0.116475 0.527592 0.030 Uiso 1 1 calc R U . . .
C9 C 0.40648(7) 0.5397(2) 0.50406(7) 0.0250(3) Uani 1 1 d . . . . .
H9 H 0.398248 0.664167 0.515275 0.030 Uiso 1 1 calc R U . . .
C10 C 0.41689(7) 0.4879(2) 0.44599(7) 0.0217(3) Uani 1 1 d . . . . .
H10 H 0.418260 0.566611 0.409953 0.026 Uiso 1 1 calc R U . . .
C11 C 0.43324(7) 0.61614(19) 0.22583(7) 0.0193(3) Uani 1 1 d . . . . .
C12 C 0.36707(7) 0.51689(19) 0.17732(7) 0.0203(3) Uani 1 1 d . . . . .
H12A H 0.369991 0.512831 0.131078 0.024 Uiso 1 1 calc R U . . .
H12B H 0.320937 0.580949 0.175207 0.024 Uiso 1 1 calc R U . . .
C13 C 0.36966(7) 0.31845(18) 0.20628(6) 0.0173(3) Uani 1 1 d . . . . .
C14 C 0.32469(7) 0.3119(2) 0.25441(7) 0.0203(3) Uani 1 1 d . . . . .
H14A H 0.336382 0.195707 0.281543 0.024 Uiso 1 1 calc R U . . .
H14B H 0.338630 0.418849 0.286196 0.024 Uiso 1 1 calc R U . . .
C15 C 0.24216(7) 0.3193(2) 0.21473(7) 0.0240(3) Uani 1 1 d . . . . .
H15A H 0.214692 0.313522 0.246835 0.029 Uiso 1 1 calc R U . . .
H15B H 0.230021 0.439099 0.189838 0.029 Uiso 1 1 calc R U . . .
C16 C 0.25573(7) 0.1829(2) 0.11887(7) 0.0246(3) Uani 1 1 d . . . . .
H16A H 0.242972 0.303863 0.094886 0.029 Uiso 1 1 calc R U . . .
H16B H 0.237641 0.082287 0.084819 0.029 Uiso 1 1 calc R U . . .
C17 C 0.33903(7) 0.16810(19) 0.15120(7) 0.0206(3) Uani 1 1 d . . . . .
H17A H 0.361764 0.182837 0.115719 0.025 Uiso 1 1 calc R U . . .
H17B H 0.352213 0.042933 0.171762 0.025 Uiso 1 1 calc R U . . .
C18 C 0.60578(7) 0.57722(18) 0.28291(6) 0.0182(3) Uani 1 1 d . . . . .
C19 C 0.59856(8) 0.5731(2) 0.21435(7) 0.0213(3) Uani 1 1 d . . . . .
H19 H 0.554307 0.528809 0.181491 0.026 Uiso 1 1 calc R U . . .
C20 C 0.65624(8) 0.6339(2) 0.19422(7) 0.0249(3) Uani 1 1 d . . . . .
H20 H 0.651249 0.629221 0.147529 0.030 Uiso 1 1 calc R U . . .
C21 C 0.72111(8) 0.7015(2) 0.24135(8) 0.0258(3) Uani 1 1 d . . . . .
H21 H 0.759952 0.745128 0.227136 0.031 Uiso 1 1 calc R U . . .
C22 C 0.72812(7) 0.7042(2) 0.30965(7) 0.0239(3) Uani 1 1 d . . . . .
H22 H 0.772310 0.749404 0.342355 0.029 Uiso 1 1 calc R U . . .
C23 C 0.67153(7) 0.6418(2) 0.33059(7) 0.0211(3) Uani 1 1 d . . . . .
H23 H 0.677365 0.642949 0.377495 0.025 Uiso 1 1 calc R U . . .
C24 C 0.27053(9) 0.5676(3) -0.01950(8) 0.0349(4) Uani 1 1 d . . . . .
H24 H 0.218425 0.555081 -0.036218 0.042 Uiso 1 1 calc R U . . .
C25 C 0.30166(11) 0.7372(3) 0.00741(9) 0.0403(4) Uani 1 1 d . . . . .
H25 H 0.270841 0.838556 0.009501 0.048 Uiso 1 1 calc R U . . .
C26 C 0.37734(11) 0.7593(3) 0.03120(9) 0.0435(4) Uani 1 1 d . . . . .
H26 H 0.398722 0.875761 0.049110 0.052 Uiso 1 1 calc R U . . .
C27 C 0.42146(10) 0.6099(3) 0.02860(9) 0.0460(5) Uani 1 1 d . . . . .
H27 H 0.473495 0.624130 0.044855 0.055 Uiso 1 1 calc R U . . .
C28 C 0.39071(10) 0.4399(3) 0.00259(9) 0.0392(4) Uani 1 1 d . . . . .
H28 H 0.421784 0.338000 0.001640 0.047 Uiso 1 1 calc R U . . .
C29 C 0.31363(9) 0.4167(2) -0.02250(8) 0.0333(4) Uani 1 1 d . . . . .
C30 C 0.27834(11) 0.2360(3) -0.05214(9) 0.0415(4) Uani 1 1 d . . . . .
H30A H 0.248607 0.189430 -0.025883 0.062 Uiso 1 1 calc R U . . .
H30B H 0.316619 0.144565 -0.050516 0.062 Uiso 1 1 calc R U . . .
H30C H 0.246671 0.255592 -0.099436 0.062 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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
C5 O1 C1 120.93(10) . . ?
C7 O3 C2 116.73(10) . . ?
C15 O6 C16 109.72(11) . . ?
N2 N1 C1 120.31(10) . . ?
C11 N1 N2 124.75(11) . . ?
C11 N1 C1 114.77(10) . . ?
N1 N2 H2 114.7(13) . . ?
N1 N2 C18 118.97(10) . . ?
C18 N2 H2 115.3(13) . . ?
C8 N3 C7 123.97(12) . . ?
C8 N3 C10 106.85(12) . . ?
C10 N3 C7 129.02(12) . . ?
C8 N4 C9 105.99(12) . . ?
O1 C1 C2 109.07(10) . . ?
O1 C1 C13 105.30(9) . . ?
N1 C1 O1 110.13(10) . . ?
N1 C1 C2 111.00(10) . . ?
N1 C1 C13 103.41(10) . . ?
C2 C1 C13 117.61(10) . . ?
O3 C2 C1 106.54(10) . . ?
O3 C2 H2A 109.2 . . ?
O3 C2 C3 109.27(10) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 C1 113.22(11) . . ?
C3 C2 H2A 109.2 . . ?
O2 C3 C2 119.56(12) . . ?
O2 C3 C4 125.63(13) . . ?
C4 C3 C2 114.63(11) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.61(12) . . ?
C5 C4 H4 119.7 . . ?
O1 C5 C6 110.43(11) . . ?
C4 C5 O1 124.23(12) . . ?
C4 C5 C6 125.33(13) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 N3 108.92(11) . . ?
O4 C7 O3 127.45(13) . . ?
O4 C7 N3 123.62(13) . . ?
N3 C8 H8 124.4 . . ?
N4 C8 N3 111.16(13) . . ?
N4 C8 H8 124.4 . . ?
N4 C9 H9 124.7 . . ?
C10 C9 N4 110.55(13) . . ?
C10 C9 H9 124.7 . . ?
N3 C10 H10 127.3 . . ?
C9 C10 N3 105.44(13) . . ?
C9 C10 H10 127.3 . . ?
O5 C11 N1 125.00(12) . . ?
O5 C11 C12 128.51(12) . . ?
N1 C11 C12 106.48(11) . . ?
C11 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
C11 C12 C13 105.30(10) . . ?
H12A C12 H12B 108.8 . . ?
C13 C12 H12A 110.7 . . ?
C13 C12 H12B 110.7 . . ?
C12 C13 C1 101.67(10) . . ?
C12 C13 C14 109.64(11) . . ?
C12 C13 C17 113.48(11) . . ?
C14 C13 C1 112.41(10) . . ?
C14 C13 C17 108.11(11) . . ?
C17 C13 C1 111.51(10) . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C13 111.15(11) . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
O6 C15 C14 111.28(11) . . ?
O6 C15 H15A 109.4 . . ?
O6 C15 H15B 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O6 C16 H16A 109.2 . . ?
O6 C16 H16B 109.2 . . ?
O6 C16 C17 112.12(11) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C13 C17 H17A 109.4 . . ?
C13 C17 H17B 109.4 . . ?
C16 C17 C13 111.16(11) . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 N2 123.33(12) . . ?
C19 C18 C23 119.23(12) . . ?
C23 C18 N2 117.38(12) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.87(13) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.02(13) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.6 . . ?
C20 C21 C22 118.81(13) . . ?
C22 C21 H21 120.6 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.83(13) . . ?
C23 C22 H22 119.6 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.22(13) . . ?
C22 C23 H23 119.9 . . ?
C25 C24 H24 119.3 . . ?
C29 C24 H24 119.3 . . ?
C29 C24 C25 121.39(16) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.30(18) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.4 . . ?
C27 C26 C25 119.20(18) . . ?
C27 C26 H26 120.4 . . ?
C26 C27 H27 119.6 . . ?
C26 C27 C28 120.71(17) . . ?
C28 C27 H27 119.6 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.48(18) . . ?
C29 C28 H28 119.8 . . ?
C24 C29 C28 117.92(16) . . ?
C24 C29 C30 120.08(16) . . ?
C28 C29 C30 122.00(17) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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 C1 1.4528(15) . ?
O1 C5 1.3601(16) . ?
O2 C3 1.2252(17) . ?
O3 C2 1.4364(15) . ?
O3 C7 1.3362(16) . ?
O4 C7 1.1994(18) . ?
O5 C11 1.2139(17) . ?
O6 C15 1.4227(17) . ?
O6 C16 1.4240(18) . ?
N1 N2 1.3967(14) . ?
N1 C1 1.4382(16) . ?
N1 C11 1.3736(17) . ?
N2 H2 0.87(2) . ?
N2 C18 1.3994(17) . ?
N3 C7 1.4069(18) . ?
N3 C8 1.3777(18) . ?
N3 C10 1.3936(19) . ?
N4 C8 1.303(2) . ?
N4 C9 1.392(2) . ?
C1 C2 1.5342(17) . ?
C1 C13 1.5668(17) . ?
C2 H2A 1.0000 . ?
C2 C3 1.5328(18) . ?
C3 C4 1.436(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3429(19) . ?
C5 C6 1.4880(19) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.351(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.5109(18) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5404(18) . ?
C13 C14 1.5408(18) . ?
C13 C17 1.5412(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5260(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5210(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.3948(18) . ?
C18 C23 1.3988(18) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.387(3) . ?
C24 C29 1.379(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.383(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.381(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.383(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.409(2) . ?
C29 C30 1.496(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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 C1 C2 O3 167.55(9) . . . . ?
O1 C1 C2 C3 47.43(14) . . . . ?
O1 C1 C13 C12 -89.14(11) . . . . ?
O1 C1 C13 C14 153.70(10) . . . . ?
O1 C1 C13 C17 32.10(14) . . . . ?
O2 C3 C4 C5 -173.76(14) . . . . ?
O3 C2 C3 O2 28.68(17) . . . . ?
O3 C2 C3 C4 -155.77(11) . . . . ?
O5 C11 C12 C13 -161.88(14) . . . . ?
O6 C16 C17 C13 -57.12(15) . . . . ?
N1 N2 C18 C19 -14.79(19) . . . . ?
N1 N2 C18 C23 168.04(12) . . . . ?
N1 C1 C2 O3 46.04(13) . . . . ?
N1 C1 C2 C3 -74.09(13) . . . . ?
N1 C1 C13 C12 26.46(12) . . . . ?
N1 C1 C13 C14 -90.70(12) . . . . ?
N1 C1 C13 C17 147.70(11) . . . . ?
N1 C11 C12 C13 19.18(14) . . . . ?
N2 N1 C1 O1 -79.95(13) . . . . ?
N2 N1 C1 C2 40.94(15) . . . . ?
N2 N1 C1 C13 167.95(10) . . . . ?
N2 N1 C11 O5 -5.1(2) . . . . ?
N2 N1 C11 C12 173.90(11) . . . . ?
N2 C18 C19 C20 -177.50(13) . . . . ?
N2 C18 C23 C22 178.50(13) . . . . ?
N4 C9 C10 N3 1.21(15) . . . . ?
C1 O1 C5 C4 9.56(19) . . . . ?
C1 O1 C5 C6 -171.40(11) . . . . ?
C1 N1 N2 C18 107.32(14) . . . . ?
C1 N1 C11 O5 179.63(13) . . . . ?
C1 N1 C11 C12 -1.38(15) . . . . ?
C1 C2 C3 O2 147.24(12) . . . . ?
C1 C2 C3 C4 -37.21(16) . . . . ?
C1 C13 C14 C15 -174.55(11) . . . . ?
C1 C13 C17 C16 174.32(11) . . . . ?
C2 O3 C7 O4 1.73(19) . . . . ?
C2 O3 C7 N3 -177.23(10) . . . . ?
C2 C1 C13 C12 149.17(11) . . . . ?
C2 C1 C13 C14 32.01(15) . . . . ?
C2 C1 C13 C17 -89.58(13) . . . . ?
C2 C3 C4 C5 11.00(19) . . . . ?
C3 C4 C5 O1 4.0(2) . . . . ?
C3 C4 C5 C6 -174.89(13) . . . . ?
C5 O1 C1 N1 87.11(13) . . . . ?
C5 O1 C1 C2 -34.94(15) . . . . ?
C5 O1 C1 C13 -162.02(11) . . . . ?
C7 O3 C2 C1 146.02(10) . . . . ?
C7 O3 C2 C3 -91.33(12) . . . . ?
C7 N3 C8 N4 176.08(12) . . . . ?
C7 N3 C10 C9 -176.40(12) . . . . ?
C8 N3 C7 O3 -162.53(12) . . . . ?
C8 N3 C7 O4 18.5(2) . . . . ?
C8 N3 C10 C9 -0.94(14) . . . . ?
C8 N4 C9 C10 -1.03(16) . . . . ?
C9 N4 C8 N3 0.40(16) . . . . ?
C10 N3 C7 O3 12.23(18) . . . . ?
C10 N3 C7 O4 -166.77(13) . . . . ?
C10 N3 C8 N4 0.34(16) . . . . ?
C11 N1 N2 C18 -67.72(17) . . . . ?
C11 N1 C1 O1 95.57(12) . . . . ?
C11 N1 C1 C2 -143.54(11) . . . . ?
C11 N1 C1 C13 -16.54(14) . . . . ?
C11 C12 C13 C1 -27.74(13) . . . . ?
C11 C12 C13 C14 91.41(12) . . . . ?
C11 C12 C13 C17 -147.60(11) . . . . ?
C12 C13 C14 C15 73.14(14) . . . . ?
C12 C13 C17 C16 -71.58(15) . . . . ?
C13 C1 C2 O3 -72.72(13) . . . . ?
C13 C1 C2 C3 167.15(11) . . . . ?
C13 C14 C15 O6 58.42(15) . . . . ?
C14 C13 C17 C16 50.26(14) . . . . ?
C15 O6 C16 C17 62.27(15) . . . . ?
C16 O6 C15 C14 -62.61(14) . . . . ?
C17 C13 C14 C15 -51.04(14) . . . . ?
C18 C19 C20 C21 -0.8(2) . . . . ?
C19 C18 C23 C22 1.2(2) . . . . ?
C19 C20 C21 C22 1.2(2) . . . . ?
C20 C21 C22 C23 -0.4(2) . . . . ?
C21 C22 C23 C18 -0.8(2) . . . . ?
C23 C18 C19 C20 -0.4(2) . . . . ?
C24 C25 C26 C27 -0.8(3) . . . . ?
C25 C24 C29 C28 -0.1(2) . . . . ?
C25 C24 C29 C30 -179.71(15) . . . . ?
C25 C26 C27 C28 0.0(3) . . . . ?
C26 C27 C28 C29 0.8(3) . . . . ?
C27 C28 C29 C24 -0.7(2) . . . . ?
C27 C28 C29 C30 178.89(16) . . . . ?
C29 C24 C25 C26 0.9(3) . . . . ?
