#------------------------------------------------------------------------------
#$Date: 2021-11-10 01:16:51 +0200 (Wed, 10 Nov 2021) $
#$Revision: 270546 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/51/1565149.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_1565149
loop_
_publ_author_name
'Wang, Lele'
'Han, Hua-Bin'
'Gu, Lijie'
'Zhang, Wenjing'
'Zhao, Junwei'
'Wang, Qi-Lin'
_publ_section_title
;
 Skeletal remodeling of chalcone-based pyridinium salts to access
 isoindoline polycycles and their bridged derivatives
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC05741C
_journal_year                    2021
_chemical_formula_moiety         'C26 H23 N3 O5'
_chemical_formula_sum            'C26 H23 N3 O5'
_chemical_formula_weight         457.47
_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     direct
_audit_creation_date             2019-12-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-18 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.324(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6642(4)
_cell_length_b                   18.5733(7)
_cell_length_c                   13.4479(6)
_cell_measurement_reflns_used    1769
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      58.1690
_cell_measurement_theta_min      4.2220
_cell_volume                     2263.57(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  31.00   0.50    8.50    --  -33.50  57.00   0.00  156
  2  ω    -32.00  64.00   0.50    8.50    --   36.47 -77.00 150.00  192
  3  ω    -14.00  18.00   0.50    8.50    --   36.47 -57.00   0.00   64
  4  ω     58.00  97.00   0.50    8.50    --   36.47 178.00 -90.00   78
  5  ω     14.00  72.00   0.50    8.50    --   36.47  37.00 -30.00  116
  6  ω     57.00 110.00   0.50    8.50    --   36.47 178.00   0.00  106
  7  ω     37.00  78.00   0.50    8.50    --   36.47  57.00-180.00   82
  8  ω    -32.00  27.00   0.50    8.50    --   36.47 -77.00-150.00  118
  9  ω     38.00  63.00   0.50    8.50    --   36.47 -77.00-150.00   50
 10  ω     40.00  78.00   0.50   35.00    --  108.00 -94.00 -90.00   76
 11  ω     82.00 176.00   0.50   35.00    --  108.00  30.00-150.00  188
 12  ω     50.00 112.00   0.50   35.00    --  108.00-111.00-150.00  124
 13  ω     48.00 129.00   0.50   35.00    --  108.00 -77.00 -90.00  162
 14  ω    101.00 130.00   0.50   35.00    --  108.00 111.00-120.00   58
 15  ω     63.00 131.00   0.50   35.00    --  108.00 -30.00 150.00  136
 16  ω    106.00 171.00   0.50   35.00    --  108.00  61.00 -60.00  130
 17  ω     79.00 144.00   0.50   35.00    --  108.00 178.00-150.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0416056000
_diffrn_orient_matrix_UB_12      0.0756337000
_diffrn_orient_matrix_UB_13      0.0273016000
_diffrn_orient_matrix_UB_21      0.1399874000
_diffrn_orient_matrix_UB_22      0.0311090000
_diffrn_orient_matrix_UB_23      -0.0138731000
_diffrn_orient_matrix_UB_31      -0.0870440000
_diffrn_orient_matrix_UB_32      0.0138644000
_diffrn_orient_matrix_UB_33      -0.1182468000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9067
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.238
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4038
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0685
_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)+(0.1138P)²+0.3704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1907
_refine_ls_wR_factor_ref         0.2181
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2516
_reflns_number_total             4038
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc05741c2.cif
_cod_data_source_block           zzy1062
_cod_database_code               1565149
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O2N4
_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   0.970
_shelx_estimated_absorpt_t_min   0.892
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N2A-C11A
 1.44 with sigma of 0.02
 C13A-N2A
 1.44 with sigma of 0.02
 C11A-C10
 1.39 with sigma of 0.02
 C14A-N2A
 2.5 with sigma of 0.02
 C13A-C15A
 2.5 with sigma of 0.02
 C13-C14
 1.53 with sigma of 0.02
 C14A-C13A
 1.53 with sigma of 0.02
 N2A-C12
 1.43 with sigma of 0.02
 N2-C11
 1.43 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C21) = Uanis(C21A)
Uanis(C20) = Uanis(C20A)
Uanis(C15) = Uanis(C15A)
Uanis(C16) = Uanis(C16A)
Uanis(C17) = Uanis(C17A)
Uanis(C18) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
Uanis(C14) = Uanis(C14A)
Uanis(C13) = Uanis(C13A)
Uanis(C11) = Uanis(C11A)
Uanis(N2) = Uanis(N2A)
4. Others
 Sof(H9B)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=1-FVAR(1)
 Sof(H9A)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=FVAR(1)
 Sof(H12A)=Sof(N2A)=Sof(C11A)=Sof(H11A)=Sof(C13A)=Sof(H13C)=Sof(H13D)=
 Sof(C19A)=Sof(H19A)=Sof(C18A)=Sof(H18A)=Sof(C17A)=Sof(H17A)=Sof(C16A)=
 Sof(H16A)=Sof(C15A)=Sof(C14A)=1-FVAR(2)
 Sof(H12)=Sof(N2)=Sof(C11)=Sof(H11)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=
 Sof(C19)=Sof(H19)=Sof(C18)=Sof(H18)=Sof(C17)=Sof(H17)=Sof(C16)=Sof(H16)=
 Sof(C15)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C9(H9A), C9(H9B), C12(H12), C12(H12A)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C13A(H13C,H13D)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4A), C11(H11), C19(H19), C18(H18),
 C17(H17), C16(H16), C20(H20), C21(H21), C11A(H11A), C19A(H19A), C18A(H18A),
 C17A(H17A), C16A(H16A), C20A(H20A), C21A(H21A)
5.d Fitted hexagon refined as free rotating group:
 C14(C19,C18,C17,C16,C15), C19A(C18A,C17A,C16A,C15A,C14A)
5.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
5.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.840
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 0.4372(3) 0.63915(16) 0.5248(2) 0.0866(8) Uani 1 1 d . . . . .
O2 O 0.5347(4) 0.81561(17) 0.1173(3) 0.1064(10) Uani 1 1 d . . . . .
O3 O 0.3951(3) 0.72123(18) 0.1022(2) 0.0898(8) Uani 1 1 d . . . . .
O4 O 0.8361(4) 0.46250(17) 0.4370(3) 0.1042(10) Uani 1 1 d . . . . .
H4 H 0.8335 0.4486 0.3784 0.156 Uiso 1 1 calc GR . . . .
O5 O 0.8021(3) 0.47147(15) 0.2454(3) 0.0998(9) Uani 1 1 d . . . . .
N1 N 0.2260(3) 0.7069(2) 0.4821(2) 0.0842(10) Uani 1 1 d . . . . .
H1 H 0.1809 0.6824 0.5157 0.101 Uiso 1 1 calc R . . . .
N3 N 0.4747(3) 0.76935(18) 0.1566(2) 0.0736(8) Uani 1 1 d . . . . .
C1 C 0.2325(4) 0.8563(2) 0.3172(3) 0.0719(9) Uani 1 1 d . . . . .
H1A H 0.2977 0.8752 0.2868 0.086 Uiso 1 1 calc R . . . .
C2 C 0.0949(5) 0.8880(3) 0.2986(4) 0.0954(13) Uani 1 1 d . . . . .
H2 H 0.0676 0.9281 0.2547 0.115 Uiso 1 1 calc R . . . .
C3 C 0.0003(5) 0.8609(4) 0.3441(4) 0.1104(18) Uani 1 1 d . . . . .
H3 H -0.0902 0.8833 0.3317 0.133 Uiso 1 1 calc R . . . .
C4 C 0.0358(4) 0.8012(3) 0.4080(3) 0.1044(16) Uani 1 1 d . . . . .
H4A H -0.0294 0.7828 0.4386 0.125 Uiso 1 1 calc R . . . .
C5 C 0.1692(4) 0.7695(2) 0.4253(3) 0.0747(10) Uani 1 1 d . . . . .
C6 C 0.2698(3) 0.79633(19) 0.3816(2) 0.0602(8) Uani 1 1 d . . . . .
C7 C 0.4017(3) 0.74648(17) 0.4121(2) 0.0566(7) Uani 1 1 d . . . . .
C8 C 0.3594(4) 0.6891(2) 0.4783(2) 0.0667(8) Uani 1 1 d . . . . .
C9 C 0.4280(3) 0.71405(17) 0.3124(2) 0.0580(7) Uani 1 1 d . . . . .
H9A H 0.3298 0.7055 0.2598 0.070 Uiso 0.808(6) 1 calc R . P A 1
H9B H 0.3399 0.6923 0.2608 0.070 Uiso 0.192(6) 1 calc R . P A 2
C10 C 0.4975(3) 0.77216(18) 0.2662(3) 0.0598(8) Uani 1 1 d D . . . .
C12 C 0.5490(3) 0.78086(18) 0.4842(3) 0.0649(8) Uani 1 1 d D . . . .
H12 H 0.6252 0.7435 0.5078 0.078 Uiso 0.695(17) 1 calc R . P B 1
H12A H 0.6190 0.7413 0.5118 0.078 Uiso 0.305(17) 1 calc R . P B 2
C22 C 0.7078(5) 0.5594(2) 0.3313(4) 0.0863(11) Uani 1 1 d . . . . .
C23 C 0.7624(5) 0.5228(2) 0.4266(4) 0.0944(13) Uani 1 1 d . . . . .
C24 C 0.7467(7) 0.5481(4) 0.5276(4) 0.139(2) Uani 1 1 d . . . . .
H24A H 0.7060 0.5101 0.5573 0.208 Uiso 1 1 calc GR . . . .
H24B H 0.6822 0.5891 0.5135 0.208 Uiso 1 1 calc GR . . . .
H24C H 0.8418 0.5614 0.5769 0.208 Uiso 1 1 calc GR . . . .
C25 C 0.7283(5) 0.5280(2) 0.2406(4) 0.0878(12) Uani 1 1 d . . . . .
C26 C 0.6601(6) 0.5626(3) 0.1319(4) 0.1078(15) Uani 1 1 d . . . . .
H26A H 0.7337 0.5672 0.0994 0.162 Uiso 1 1 calc GR . . . .
H26B H 0.6227 0.6094 0.1395 0.162 Uiso 1 1 calc GR . . . .
H26C H 0.5807 0.5330 0.0882 0.162 Uiso 1 1 calc GR . . . .
N2 N 0.5992(19) 0.8383(5) 0.4291(9) 0.0661(17) Uani 0.695(17) 1 d D . P B 1
C11 C 0.5766(16) 0.8232(5) 0.3281(8) 0.0610(19) Uani 0.695(17) 1 d D . P B 1
H11 H 0.6245 0.8537 0.2958 0.073 Uiso 0.695(17) 1 calc R . P B 1
C13 C 0.6581(13) 0.8999(5) 0.4957(8) 0.077(2) Uani 0.695(17) 1 d D . P B 1
H13A H 0.6205 0.9446 0.4587 0.092 Uiso 0.695(17) 1 calc R . P B 1
H13B H 0.7651 0.9005 0.5201 0.092 Uiso 0.695(17) 1 calc R . P B 1
C14 C 0.6042(11) 0.8885(4) 0.5840(6) 0.0799(17) Uani 0.695(17) 1 d D U P B 1
C19 C 0.6173(9) 0.9346(4) 0.6682(7) 0.092(2) Uani 0.695(17) 1 d G U P B 1
H19 H 0.6604 0.9797 0.6710 0.110 Uiso 0.695(17) 1 calc R . P B 1
C18 C 0.5658(9) 0.9134(5) 0.7482(6) 0.099(3) Uani 0.695(17) 1 d G U P B 1
H18 H 0.5746 0.9442 0.8046 0.119 Uiso 0.695(17) 1 calc R . P B 1
C17 C 0.5013(9) 0.8460(5) 0.7441(5) 0.089(2) Uani 0.695(17) 1 d G U P B 1
H17 H 0.4669 0.8318 0.7976 0.106 Uiso 0.695(17) 1 calc R . P B 1
C16 C 0.4882(10) 0.7999(4) 0.6599(5) 0.0735(16) Uani 0.695(17) 1 d G U P B 1
H16 H 0.4450 0.7549 0.6571 0.088 Uiso 0.695(17) 1 calc R . P B 1
C15 C 0.5397(11) 0.8212(4) 0.5798(5) 0.0654(15) Uani 0.695(17) 1 d G U P B 1
C20 C 0.5065(5) 0.6428(2) 0.3289(3) 0.0573(10) Uani 0.808(6) 1 d . . P A 1
H20 H 0.4588 0.6035 0.3454 0.069 Uiso 0.808(6) 1 calc R . P A 1
C21 C 0.6360(5) 0.6315(2) 0.3219(4) 0.0680(11) Uani 0.808(6) 1 d . . P A 1
H21 H 0.6873 0.6711 0.3103 0.082 Uiso 0.808(6) 1 calc R . P A 1
N2A N 0.607(5) 0.8248(12) 0.415(2) 0.0661(17) Uani 0.305(17) 1 d D . P B 2
C11A C 0.568(4) 0.8351(12) 0.308(2) 0.0610(19) Uani 0.305(17) 1 d D . P B 2
H11A H 0.5856 0.8750 0.2718 0.073 Uiso 0.305(17) 1 calc R . P B 2
C13A C 0.663(4) 0.8986(13) 0.4600(17) 0.077(2) Uani 0.305(17) 1 d D . P B 2
H13C H 0.6109 0.9369 0.4126 0.092 Uiso 0.305(17) 1 calc R . P B 2
H13D H 0.7678 0.9034 0.4750 0.092 Uiso 0.305(17) 1 calc R . P B 2
C19A C 0.636(2) 0.9517(8) 0.6371(15) 0.092(2) Uani 0.305(17) 1 d . . P B 2
H19A H 0.6752 0.9964 0.6298 0.110 Uiso 0.305(17) 1 calc R . P B 2
C18A C 0.589(2) 0.9390(9) 0.7222(13) 0.099(3) Uani 0.305(17) 1 d G . P B 2
H18A H 0.5967 0.9751 0.7717 0.119 Uiso 0.305(17) 1 calc R . P B 2
C17A C 0.531(2) 0.8722(10) 0.7332(12) 0.089(2) Uani 0.305(17) 1 d G . P B 2
H17A H 0.4997 0.8637 0.7901 0.106 Uiso 0.305(17) 1 calc R . P B 2
C16A C 0.520(2) 0.8183(9) 0.6592(15) 0.0735(16) Uani 0.305(17) 1 d G . P B 2
H16A H 0.4812 0.7736 0.6666 0.088 Uiso 0.305(17) 1 calc R . P B 2
C15A C 0.567(3) 0.8311(9) 0.5742(15) 0.0654(15) Uani 0.305(17) 1 d DG . P B 2
C14A C 0.625(3) 0.8978(10) 0.5631(14) 0.0799(17) Uani 0.305(17) 1 d DG . P B 2
C20A C 0.578(2) 0.6567(11) 0.3555(17) 0.0573(10) Uani 0.192(6) 1 d . . P A 2
H20A H 0.6662 0.6687 0.4089 0.069 Uiso 0.192(6) 1 calc R . P A 2
C21A C 0.556(2) 0.5954(10) 0.3064(16) 0.0680(11) Uani 0.192(6) 1 d . . P A 2
H21A H 0.4659 0.5766 0.2639 0.082 Uiso 0.192(6) 1 calc R . 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_
_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
C23 O4 H4 109.5 . . ?
C5 N1 H1 123.7 . . ?
C8 N1 H1 123.7 . . ?
C8 N1 C5 112.6(3) . . ?
O2 N3 C10 119.2(3) . . ?
O3 N3 O2 122.0(3) . . ?
O3 N3 C10 118.9(3) . . ?
C2 C1 H1A 120.7 . . ?
C6 C1 H1A 120.7 . . ?
C6 C1 C2 118.6(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(4) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4A 120.9 . . ?
C5 C4 C3 118.2(4) . . ?
C5 C4 H4A 120.9 . . ?
C4 C5 N1 128.5(4) . . ?
C4 C5 C6 122.2(4) . . ?
C6 C5 N1 109.3(3) . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 C7 132.5(3) . . ?
C5 C6 C7 108.3(3) . . ?
C6 C7 C8 102.3(3) . . ?
C6 C7 C9 112.0(2) . . ?
C6 C7 C12 114.9(3) . . ?
C8 C7 C9 112.6(3) . . ?
C8 C7 C12 107.1(3) . . ?
C12 C7 C9 107.8(2) . . ?
O1 C8 N1 126.5(3) . . ?
O1 C8 C7 125.8(3) . . ?
N1 C8 C7 107.6(3) . . ?
C7 C9 H9A 106.0 . . ?
C7 C9 H9B 113.8 . . ?
C7 C9 C20A 108.4(7) . . ?
C10 C9 C7 107.7(3) . . ?
C10 C9 H9A 106.0 . . ?
C10 C9 H9B 113.8 . . ?
C10 C9 C20A 97.9(7) . . ?
C20 C9 C7 115.8(3) . . ?
C20 C9 H9A 106.0 . . ?
C20 C9 C10 114.5(3) . . ?
C20A C9 H9B 113.8 . . ?
N3 C10 C9 118.1(3) . . ?
C11 C10 N3 122.1(6) . . ?
C11 C10 C9 119.8(6) . . ?
C11A C10 N3 109.2(12) . . ?
C11A C10 C9 132.2(13) . . ?
C7 C12 H12 109.5 . . ?
C7 C12 H12A 106.9 . . ?
N2 C12 C7 111.9(6) . . ?
N2 C12 H12 109.5 . . ?
N2 C12 C15 101.3(4) . . ?
C15 C12 C7 114.8(4) . . ?
C15 C12 H12 109.5 . . ?
N2A C12 C7 107.1(14) . . ?
N2A C12 H12A 106.9 . . ?
N2A C12 C15A 101.7(11) . . ?
C15A C12 C7 126.0(9) . . ?
C15A C12 H12A 106.9 . . ?
C23 C22 C25 118.1(4) . . ?
C23 C22 C21 122.3(4) . . ?
C23 C22 C21A 116.3(8) . . ?
C25 C22 C21 119.5(4) . . ?
C25 C22 C21A 113.3(8) . . ?
O4 C23 C22 122.4(5) . . ?
O4 C23 C24 113.3(4) . . ?
C22 C23 C24 124.2(4) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C25 C22 122.8(4) . . ?
O5 C25 C26 116.7(4) . . ?
C22 C25 C26 120.4(4) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C11 N2 C12 113.3(9) . . ?
C11 N2 C13 133.8(9) . . ?
C13 N2 C12 113.0(6) . . ?
C10 C11 N2 130.7(11) . . ?
C10 C11 H11 114.7 . . ?
N2 C11 H11 114.7 . . ?
N2 C13 H13A 111.3 . . ?
N2 C13 H13B 111.3 . . ?
N2 C13 C14 102.3(6) . . ?
H13A C13 H13B 109.2 . . ?
C14 C13 H13A 111.3 . . ?
C14 C13 H13B 111.3 . . ?
C19 C14 C13 127.8(4) . . ?
C19 C14 C15 120.0 . . ?
C15 C14 C13 112.2(4) . . ?
C14 C19 H19 120.0 . . ?
C14 C19 C18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C14 C15 C12 108.7(4) . . ?
C16 C15 C12 131.2(4) . . ?
C16 C15 C14 120.0 . . ?
C9 C20 H20 117.3 . . ?
C21 C20 C9 125.4(4) . . ?
C21 C20 H20 117.3 . . ?
C22 C21 H21 117.7 . . ?
C20 C21 C22 124.6(4) . . ?
C20 C21 H21 117.7 . . ?
C12 N2A C13A 113.7(13) . . ?
C11A N2A C12 136(3) . . ?
C11A N2A C13A 103.0(18) . . ?
C10 C11A H11A 128.6 . . ?
N2A C11A C10 102.9(19) . . ?
N2A C11A H11A 128.6 . . ?
N2A C13A H13C 111.6 . . ?
N2A C13A H13D 111.6 . . ?
N2A C13A C14A 100.9(11) . . ?
H13C C13A H13D 109.4 . . ?
C14A C13A H13C 111.6 . . ?
C14A C13A H13D 111.6 . . ?
C18A C19A H19A 120.0 . . ?
C18A C19A C14A 120.0 . . ?
C14A C19A H19A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C17A C18A C19A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C18A C17A C16A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C15A C16A C17A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C16A C15A C12 125.6(10) . . ?
C16A C15A C14A 120.0 . . ?
C14A C15A C12 114.2(10) . . ?
C19A C14A C13A 130.5(10) . . ?
C15A C14A C13A 109.4(10) . . ?
C15A C14A C19A 120.0 . . ?
C9 C20A H20A 123.1 . . ?
C21A C20A C9 113.7(18) . . ?
C21A C20A H20A 123.1 . . ?
C22 C21A H21A 126.3 . . ?
C20A C21A C22 107.3(18) . . ?
C20A C21A H21A 126.3 . . ?
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 C8 1.221(4) . ?
O2 N3 1.252(4) . ?
O3 N3 1.239(4) . ?
O4 H4 0.8200 . ?
O4 C23 1.309(5) . ?
O5 C25 1.258(5) . ?
N1 H1 0.8600 . ?
N1 C5 1.394(5) . ?
N1 C8 1.349(5) . ?
N3 C10 1.414(4) . ?
C1 H1A 0.9300 . ?
C1 C2 1.395(5) . ?
C1 C6 1.380(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.362(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(8) . ?
C4 H4A 0.9300 . ?
C4 C5 1.361(5) . ?
C5 C6 1.391(5) . ?
C6 C7 1.513(4) . ?
C7 C8 1.533(5) . ?
C7 C9 1.568(4) . ?
C7 C12 1.554(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 C10 1.513(4) . ?
C9 C20 1.503(5) . ?
C9 C20A 1.73(2) . ?
C10 C11 1.317(9) . ?
C10 C11A 1.371(19) . ?
C12 H12 0.9800 . ?
C12 H12A 0.9800 . ?
C12 N2 1.474(9) . ?
C12 C15 1.518(6) . ?
C12 N2A 1.487(18) . ?
C12 C15A 1.489(12) . ?
C22 C23 1.384(6) . ?
C22 C25 1.425(6) . ?
C22 C21 1.493(6) . ?
C22 C21A 1.536(19) . ?
C23 C24 1.493(7) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.522(6) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N2 C11 1.328(9) . ?
N2 C13 1.443(9) . ?
C11 H11 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.469(8) . ?
C14 C19 1.3900 . ?
C14 C15 1.3900 . ?
C19 H19 0.9300 . ?
C19 C18 1.3900 . ?
C18 H18 0.9300 . ?
C18 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C16 1.3900 . ?
C16 H16 0.9300 . ?
C16 C15 1.3900 . ?
C20 H20 0.9300 . ?
C20 C21 1.304(7) . ?
C21 H21 0.9300 . ?
N2A C11A 1.370(18) . ?
N2A C13A 1.520(18) . ?
C11A H11A 0.9300 . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C13A C14A 1.550(14) . ?
C19A H19A 0.9300 . ?
C19A C18A 1.3900 . ?
C19A C14A 1.3900 . ?
C18A H18A 0.9300 . ?
C18A C17A 1.3900 . ?
C17A H17A 0.9300 . ?
C17A C16A 1.3900 . ?
C16A H16A 0.9300 . ?
C16A C15A 1.3900 . ?
C15A C14A 1.3900 . ?
C20A H20A 0.9300 . ?
C20A C21A 1.30(3) . ?
C21A H21A 0.9300 . ?
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
O4 H4 O5 0.82 1.76 2.486(5) 146.8 .
N1 H1 O2 0.86 2.28 3.039(4) 147.1 4_576
N1 H1 O4 0.86 2.78 3.450(5) 135.5 3_666
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
O2 N3 C10 C9 -177.9(3) . . . . ?
O2 N3 C10 C11 2.0(9) . . . . ?
O2 N3 C10 C11A 9.2(18) . . . . ?
O3 N3 C10 C9 2.5(4) . . . . ?
O3 N3 C10 C11 -177.7(8) . . . . ?
O3 N3 C10 C11A -170.5(18) . . . . ?
N1 C5 C6 C1 176.6(3) . . . . ?
N1 C5 C6 C7 0.5(4) . . . . ?
N3 C10 C11 N2 173.3(15) . . . . ?
N3 C10 C11A N2A -169(3) . . . . ?
C1 C2 C3 C4 -1.1(8) . . . . ?
C1 C6 C7 C8 -175.5(3) . . . . ?
C1 C6 C7 C9 -54.7(5) . . . . ?
C1 C6 C7 C12 68.8(5) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
C2 C1 C6 C7 175.3(4) . . . . ?
C2 C3 C4 C5 0.3(8) . . . . ?
C3 C4 C5 N1 -176.4(4) . . . . ?
C3 C4 C5 C6 0.8(7) . . . . ?
C4 C5 C6 C1 -1.0(6) . . . . ?
C4 C5 C6 C7 -177.2(4) . . . . ?
C5 N1 C8 O1 176.3(3) . . . . ?
C5 N1 C8 C7 0.7(4) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C5 C6 C7 C9 120.8(3) . . . . ?
C5 C6 C7 C12 -115.8(3) . . . . ?
C6 C1 C2 C3 0.8(6) . . . . ?
C6 C7 C8 O1 -176.0(3) . . . . ?
C6 C7 C8 N1 -0.3(3) . . . . ?
C6 C7 C9 C10 76.3(3) . . . . ?
C6 C7 C9 C20 -154.0(3) . . . . ?
C6 C7 C9 C20A -178.8(8) . . . . ?
C6 C7 C12 N2 -65.9(6) . . . . ?
C6 C7 C12 C15 48.9(5) . . . . ?
C6 C7 C12 N2A -78.9(13) . . . . ?
C6 C7 C12 C15A 40.2(11) . . . . ?
C7 C9 C10 N3 -153.1(3) . . . . ?
C7 C9 C10 C11 27.1(8) . . . . ?
C7 C9 C10 C11A 18(2) . . . . ?
C7 C9 C20 C21 -115.5(5) . . . . ?
C7 C9 C20A C21A 133.7(15) . . . . ?
C7 C12 N2 C11 -39.0(16) . . . . ?
C7 C12 N2 C13 139.1(11) . . . . ?
C7 C12 C15 C14 -130.8(4) . . . . ?
C7 C12 C15 C16 53.5(8) . . . . ?
C7 C12 N2A C11A -7(5) . . . . ?
C7 C12 N2A C13A 135(3) . . . . ?
C7 C12 C15A C16A 53.7(19) . . . . ?
C7 C12 C15A C14A -120.6(10) . . . . ?
C8 N1 C5 C4 176.7(4) . . . . ?
C8 N1 C5 C6 -0.8(4) . . . . ?
C8 C7 C9 C10 -169.0(3) . . . . ?
C8 C7 C9 C20 -39.3(4) . . . . ?
C8 C7 C9 C20A -64.1(8) . . . . ?
C8 C7 C12 N2 -178.8(6) . . . . ?
C8 C7 C12 C15 -64.0(5) . . . . ?
C8 C7 C12 N2A 168.2(13) . . . . ?
C8 C7 C12 C15A -72.6(11) . . . . ?
C9 C7 C8 O1 63.5(4) . . . . ?
C9 C7 C8 N1 -120.8(3) . . . . ?
C9 C7 C12 N2 59.7(6) . . . . ?
C9 C7 C12 C15 174.5(4) . . . . ?
C9 C7 C12 N2A 46.8(13) . . . . ?
C9 C7 C12 C15A 165.9(11) . . . . ?
C9 C10 C11 N2 -7(2) . . . . ?
C9 C10 C11A N2A 19(4) . . . . ?
C9 C20 C21 C22 -175.6(4) . . . . ?
C9 C20A C21A C22 165.4(11) . . . . ?
C10 C9 C20 C21 10.8(6) . . . . ?
C10 C9 C20A C21A -114.6(16) . . . . ?
C12 C7 C8 O1 -54.8(4) . . . . ?
C12 C7 C8 N1 120.8(3) . . . . ?
C12 C7 C9 C10 -51.1(3) . . . . ?
C12 C7 C9 C20 78.6(4) . . . . ?
C12 C7 C9 C20A 53.9(8) . . . . ?
C12 N2 C11 C10 12(3) . . . . ?
C12 N2 C13 C14 -15.9(16) . . . . ?
C12 N2A C11A C10 -26(6) . . . . ?
C12 N2A C13A C14A -3(4) . . . . ?
C12 C15A C14A C13A -3.0(19) . . . . ?
C12 C15A C14A C19A 174.7(18) . . . . ?
C23 C22 C25 O5 -5.0(7) . . . . ?
C23 C22 C25 C26 175.1(4) . . . . ?
C23 C22 C21 C20 -71.2(7) . . . . ?
C23 C22 C21A C20A 82.2(16) . . . . ?
C25 C22 C23 O4 2.6(7) . . . . ?
C25 C22 C23 C24 -178.7(5) . . . . ?
C25 C22 C21 C20 112.1(6) . . . . ?
C25 C22 C21A C20A -136.0(13) . . . . ?
N2 C12 C15 C14 -9.9(8) . . . . ?
N2 C12 C15 C16 174.3(9) . . . . ?
N2 C13 C14 C19 -174.2(9) . . . . ?
N2 C13 C14 C15 8.8(12) . . . . ?
C11 N2 C13 C14 161.7(19) . . . . ?
C13 N2 C11 C10 -165.3(14) . . . . ?
C13 C14 C19 C18 -176.7(11) . . . . ?
C13 C14 C15 C12 0.9(7) . . . . ?
C13 C14 C15 C16 177.2(9) . . . . ?
C14 C19 C18 C17 0.0 . . . . ?
C19 C14 C15 C12 -176.3(7) . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
C19 C18 C17 C16 0.0 . . . . ?
C18 C17 C16 C15 0.0 . . . . ?
C17 C16 C15 C12 175.4(9) . . . . ?
C17 C16 C15 C14 0.0 . . . . ?
C15 C12 N2 C11 -161.8(13) . . . . ?
C15 C12 N2 C13 16.3(14) . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
C20 C9 C10 N3 76.5(4) . . . . ?
C20 C9 C10 C11 -103.3(8) . . . . ?
C21 C22 C23 O4 -174.2(4) . . . . ?
C21 C22 C23 C24 4.5(8) . . . . ?
C21 C22 C25 O5 171.9(4) . . . . ?
C21 C22 C25 C26 -8.0(6) . . . . ?
N2A C12 C15A C16A 175(2) . . . . ?
N2A C12 C15A C14A 1(2) . . . . ?
N2A C13A C14A C19A -174(2) . . . . ?
N2A C13A C14A C15A 4(3) . . . . ?
C11A N2A C13A C14A 151(3) . . . . ?
C13A N2A C11A C10 -171(3) . . . . ?
C19A C18A C17A C16A 0.0 . . . . ?
C18A C19A C14A C13A 177(3) . . . . ?
C18A C19A C14A C15A 0.0 . . . . ?
C18A C17A C16A C15A 0.0 . . . . ?
C17A C16A C15A C12 -174(2) . . . . ?
C17A C16A C15A C14A 0.0 . . . . ?
C16A C15A C14A C13A -178(2) . . . . ?
C16A C15A C14A C19A 0.0 . . . . ?
C15A C12 N2A C11A -141(4) . . . . ?
C15A C12 N2A C13A 2(4) . . . . ?
C14A C19A C18A C17A 0.0 . . . . ?
C20A C9 C10 N3 94.6(8) . . . . ?
C20A C9 C10 C11A -94(2) . . . . ?
C21A C22 C23 O4 142.5(9) . . . . ?
C21A C22 C23 C24 -38.8(11) . . . . ?
C21A C22 C25 O5 -146.0(9) . . . . ?
C21A C22 C25 C26 34.1(10) . . . . ?
