#------------------------------------------------------------------------------
#$Date: 2021-11-10 01:16:51 +0200 (Wed, 10 Nov 2021) $
#$Revision: 270546 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/51/1565147.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_1565147
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 O4'
_chemical_formula_sum            'C26 H23 N3 O4'
_chemical_formula_weight         441.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-18
_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                 115.198(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0994(5)
_cell_length_b                   10.9354(3)
_cell_length_c                   16.3508(6)
_cell_measurement_reflns_used    2870
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3790
_cell_measurement_theta_min      5.0380
_cell_volume                     2281.11(15)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  35.00   1.00    2.10    --  -33.50  57.00   0.00   87
  2  ω     -4.00  77.00   1.00    2.10    --   36.47 -99.00 150.00   81
  3  ω     58.00  92.00   1.00    2.10    --   36.47 178.00 -60.00   34
  4  ω     66.00  96.00   1.00    2.10    --   36.47 178.00-150.00   30
  5  ω     76.00 110.00   1.00    2.10    --   36.47 178.00  90.00   34
  6  ω     -1.00  77.00   1.00    2.10    --   36.47 -99.00 -60.00   78
  7  ω      9.00  38.00   1.00    2.10    --   36.47  77.00  90.00   29
  8  ω     63.00 104.00   1.00    2.10    --   36.47  77.00  90.00   41
  9  ω     47.00  73.00   1.00   14.50    --  108.00 -30.00-150.00   26
 10  ω     78.00 118.00   1.00   14.50    --  108.00 -45.00 150.00   40
 11  ω     46.00 103.00   1.00   14.50    --  108.00 -94.00-180.00   57
 12  ω     98.00 127.00   1.00   14.50    --  108.00 -30.00-150.00   29
 13  ω    113.00 172.00   1.00   14.50    --  108.00 111.00 150.00   59
 14  ω     96.00 173.00   1.00   14.50    --  108.00  61.00 -60.00   77
 15  ω     45.00 109.00   1.00   14.50    --  108.00 -45.00   0.00   64
 16  ω     63.00 178.00   1.00   14.50    --  108.00  15.00-120.00  115
;
_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      0.0864300000
_diffrn_orient_matrix_UB_12      -0.0927519000
_diffrn_orient_matrix_UB_13      0.0536231000
_diffrn_orient_matrix_UB_21      -0.0744726000
_diffrn_orient_matrix_UB_22      -0.0620072000
_diffrn_orient_matrix_UB_23      0.0341683000
_diffrn_orient_matrix_UB_31      -0.0395202000
_diffrn_orient_matrix_UB_32      -0.0860887000
_diffrn_orient_matrix_UB_33      -0.0824242000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8092
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         5.029
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94327
_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    1.285
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4065
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0445
_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)+(0.0652P)²+0.2535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1275
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3204
_reflns_number_total             4065
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc05741c2.cif
_cod_data_source_block           wll148
_cod_original_cell_volume        2281.11(14)
_cod_database_code               1565147
_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   0.938
_shelx_estimated_absorpt_t_min   0.894
_reflns_odcompleteness_completeness 99.72
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C24-N3A
 1.45 with sigma of 0.02
 O4A-N3A
 1.4 with sigma of 0.02
 N2A-C11
 1.45 with sigma of 0.02
 N2A-O2A
 1.2 with sigma of 0.02
3. Rigid bond restraints
 N3, O4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N2, O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(N2) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(O4) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O4) = Uanis(O4A)
Uanis(N3) = Uanis(N3A)
Uanis(O2) = Uanis(O2A)
Uanis(O1) = Uanis(O1A)
Uanis(N2) = Uanis(N2A)
5. Others
 Sof(O4A)=Sof(N3A)=1-FVAR(1)
 Sof(O4)=Sof(N3)=FVAR(1)
 Sof(O2A)=Sof(O1A)=Sof(N2A)=1-FVAR(2)
 Sof(O1)=Sof(O2)=Sof(N2)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10)
6.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
6.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_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 1.317
_oxdiff_exptl_absorpt_empirical_full_min 0.919
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.03814(17) 0.5433(7) 0.65287(18) 0.0699(10) Uani 0.92(2) 1 d . . P A 1
O2 O 0.0891(2) 0.6671(4) 0.5752(3) 0.0639(7) Uani 0.92(2) 1 d . U P A 1
O3 O 0.37199(10) 0.34646(13) 0.47997(10) 0.0656(4) Uani 1 1 d . . . . .
O4 O 0.5909(4) 0.8099(6) 0.6757(3) 0.0577(12) Uani 0.644(16) 1 d . U P B 1
N1 N 0.16516(12) 0.25297(14) 0.58593(10) 0.0534(4) Uani 1 1 d . . . . .
N2 N 0.0863(3) 0.5620(3) 0.6046(3) 0.0518(7) Uani 0.92(2) 1 d . U P A 1
N3 N 0.6083(5) 0.7399(7) 0.7532(6) 0.0555(14) Uani 0.644(16) 1 d . U P B 1
C1 C 0.1393(2) -0.0586(2) 0.4986(2) 0.0860(8) Uani 1 1 d . . . . .
H1 H 0.1131 -0.1124 0.5280 0.103 Uiso 1 1 calc R . . . .
C2 C 0.1548(2) -0.0963(2) 0.4252(2) 0.0944(9) Uani 1 1 d . . . . .
H2 H 0.1377 -0.1760 0.4042 0.113 Uiso 1 1 calc R . . . .
C3 C 0.1953(2) -0.0176(2) 0.38189(19) 0.0884(8) Uani 1 1 d . . . . .
H3 H 0.2043 -0.0447 0.3317 0.106 Uiso 1 1 calc R . . . .
C4 C 0.22275(18) 0.1019(2) 0.41272(15) 0.0689(5) Uani 1 1 d . . . . .
H4 H 0.2515 0.1545 0.3846 0.083 Uiso 1 1 calc R . . . .
C5 C 0.20604(14) 0.14003(16) 0.48610(13) 0.0550(4) Uani 1 1 d . . . . .
C6 C 0.16332(15) 0.06104(19) 0.52813(15) 0.0655(5) Uani 1 1 d . . . . .
C7 C 0.15004(17) 0.12451(19) 0.60367(15) 0.0681(6) Uani 1 1 d . . . . .
H7A H 0.0807 0.1109 0.6008 0.082 Uiso 1 1 calc R . . . .
H7B H 0.2024 0.0981 0.6621 0.082 Uiso 1 1 calc R . . . .
C8 C 0.22872(12) 0.26225(15) 0.53434(11) 0.0459(4) Uani 1 1 d . . . . .
H8 H 0.3029 0.2644 0.5771 0.055 Uiso 1 1 calc R . . . .
C9 C 0.20345(12) 0.37802(14) 0.47686(11) 0.0418(3) Uani 1 1 d . . . . .
H9 H 0.1359 0.3681 0.4243 0.050 Uiso 1 1 calc R . . . .
C10 C 0.19945(12) 0.49340(14) 0.53176(11) 0.0425(3) Uani 1 1 d . . . . .
H10 H 0.1648 0.5594 0.4888 0.051 Uiso 1 1 calc R . . . .
C11 C 0.13456(12) 0.46463(16) 0.58166(11) 0.0471(4) Uani 1 1 d D . . . .
C12 C 0.12248(13) 0.34853(18) 0.60606(12) 0.0526(4) Uani 1 1 d . . . . .
H12 H 0.0825 0.3364 0.6382 0.063 Uiso 1 1 calc R . . . .
C13 C 0.28917(13) 0.40021(15) 0.44476(12) 0.0471(4) Uani 1 1 d . . . . .
C14 C 0.27313(14) 0.49498(15) 0.37467(12) 0.0494(4) Uani 1 1 d . . . . .
C15 C 0.17528(16) 0.54052(19) 0.31781(13) 0.0597(5) Uani 1 1 d . . . . .
H15 H 0.1155 0.5108 0.3215 0.072 Uiso 1 1 calc R . . . .
C16 C 0.1669(2) 0.6307(2) 0.25521(15) 0.0748(6) Uani 1 1 d . . . . .
H16 H 0.1013 0.6610 0.2168 0.090 Uiso 1 1 calc R . . . .
C17 C 0.2555(2) 0.6755(2) 0.24989(18) 0.0827(7) Uani 1 1 d . . . . .
H17 H 0.2496 0.7364 0.2082 0.099 Uiso 1 1 calc R . . . .
C18 C 0.3526(2) 0.6303(2) 0.3061(2) 0.0833(7) Uani 1 1 d . . . . .
H18 H 0.4123 0.6604 0.3022 0.100 Uiso 1 1 calc R . . . .
C19 C 0.36178(18) 0.54068(19) 0.36825(16) 0.0647(5) Uani 1 1 d . . . . .
H19 H 0.4276 0.5105 0.4061 0.078 Uiso 1 1 calc R . . . .
C20 C 0.30715(12) 0.53676(15) 0.59563(11) 0.0454(4) Uani 1 1 d . . . . .
H20 H 0.3482 0.4859 0.6432 0.054 Uiso 1 1 calc R . . . .
C21 C 0.34598(13) 0.64322(15) 0.58740(12) 0.0465(4) Uani 1 1 d . . . . .
H21 H 0.3022 0.6927 0.5402 0.056 Uiso 1 1 calc R . . . .
C22 C 0.52020(14) 0.66567(17) 0.73192(12) 0.0534(4) Uani 1 1 d . . . . .
C23 C 0.44943(13) 0.69252(15) 0.64357(12) 0.0462(4) Uani 1 1 d . . . . .
C24 C 0.50008(14) 0.78096(16) 0.61666(13) 0.0519(4) Uani 1 1 d D . . . .
C25 C 0.51349(19) 0.5802(2) 0.79967(15) 0.0762(6) Uani 1 1 d . . . . .
H25A H 0.5251 0.4981 0.7852 0.114 Uiso 1 1 calc GR . . . .
H25B H 0.4452 0.5860 0.7990 0.114 Uiso 1 1 calc GR . . . .
H25C H 0.5658 0.6013 0.8587 0.114 Uiso 1 1 calc GR . . . .
C26 C 0.46731(17) 0.8468(2) 0.52998(16) 0.0682(5) Uani 1 1 d . . . . .
H26A H 0.4119 0.9028 0.5228 0.102 Uiso 1 1 calc GR . . . .
H26B H 0.4429 0.7892 0.4811 0.102 Uiso 1 1 calc GR . . . .
H26C H 0.5259 0.8914 0.5297 0.102 Uiso 1 1 calc GR . . . .
O4A O 0.6033(10) 0.7187(10) 0.7624(11) 0.0577(12) Uani 0.356(16) 1 d D . P B 2
N3A N 0.5982(8) 0.7984(16) 0.6957(10) 0.0555(14) Uani 0.356(16) 1 d D . P B 2
O2A O 0.098(3) 0.641(4) 0.597(4) 0.0639(7) Uani 0.08(2) 1 d D . P A 2
O1A O 0.034(2) 0.491(6) 0.660(2) 0.0699(10) Uani 0.08(2) 1 d . . P A 2
N2A N 0.071(3) 0.541(4) 0.612(3) 0.0518(7) Uani 0.08(2) 1 d D . 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
C24 O4 N3 106.3(5) . . ?
C7 N1 C8 110.74(16) . . ?
C12 N1 C7 126.16(16) . . ?
C12 N1 C8 122.91(15) . . ?
O1 N2 C11 119.9(2) . . ?
O2 N2 O1 120.3(4) . . ?
O2 N2 C11 119.7(4) . . ?
C22 N3 O4 107.2(6) . . ?
C2 C1 H1 120.6 . . ?
C2 C1 C6 118.8(3) . . ?
C6 C1 H1 120.6 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 C6 120.77(19) . . ?
C4 C5 C8 129.93(18) . . ?
C6 C5 C8 109.30(18) . . ?
C1 C6 C5 120.5(2) . . ?
C1 C6 C7 128.9(2) . . ?
C5 C6 C7 110.64(18) . . ?
N1 C7 C6 101.59(16) . . ?
N1 C7 H7A 111.5 . . ?
N1 C7 H7B 111.5 . . ?
C6 C7 H7A 111.5 . . ?
C6 C7 H7B 111.5 . . ?
H7A C7 H7B 109.3 . . ?
N1 C8 C5 101.09(14) . . ?
N1 C8 H8 108.5 . . ?
N1 C8 C9 111.75(14) . . ?
C5 C8 H8 108.5 . . ?
C5 C8 C9 117.97(14) . . ?
C9 C8 H8 108.5 . . ?
C8 C9 H9 109.4 . . ?
C8 C9 C10 111.83(13) . . ?
C8 C9 C13 109.38(13) . . ?
C10 C9 H9 109.4 . . ?
C13 C9 H9 109.4 . . ?
C13 C9 C10 107.23(13) . . ?
C9 C10 H10 108.2 . . ?
C11 C10 C9 108.87(13) . . ?
C11 C10 H10 108.2 . . ?
C11 C10 C20 110.98(13) . . ?
C20 C10 C9 112.32(13) . . ?
C20 C10 H10 108.2 . . ?
N2 C11 C10 117.9(3) . . ?
C12 C11 N2 119.6(3) . . ?
C12 C11 C10 122.50(16) . . ?
C12 C11 N2A 105(2) . . ?
N2A C11 C10 132(2) . . ?
N1 C12 C11 122.61(16) . . ?
N1 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
O3 C13 C9 120.19(15) . . ?
O3 C13 C14 120.21(16) . . ?
C14 C13 C9 119.44(14) . . ?
C15 C14 C13 123.20(16) . . ?
C15 C14 C19 119.32(18) . . ?
C19 C14 C13 117.46(17) . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.4(2) . . ?
C18 C19 H19 119.8 . . ?
C10 C20 H20 118.4 . . ?
C21 C20 C10 123.18(15) . . ?
C21 C20 H20 118.4 . . ?
C20 C21 H21 116.2 . . ?
C20 C21 C23 127.65(16) . . ?
C23 C21 H21 116.2 . . ?
N3 C22 C25 120.8(4) . . ?
C23 C22 N3 107.7(4) . . ?
C23 C22 C25 131.46(17) . . ?
O4A C22 C23 117.9(8) . . ?
O4A C22 C25 110.7(8) . . ?
C22 C23 C21 131.20(16) . . ?
C24 C23 C21 124.99(17) . . ?
C24 C23 C22 103.81(16) . . ?
O4 C24 C23 115.0(4) . . ?
O4 C24 C26 114.1(3) . . ?
C23 C24 C26 130.85(18) . . ?
C23 C24 N3A 103.6(8) . . ?
N3A C24 C26 125.6(9) . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 O4A N3A 105.2(13) . . ?
O4A N3A C24 109.4(13) . . ?
O2A N2A C11 99(3) . . ?
O2A N2A O1A 141(4) . . ?
O1A N2A C11 117(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 N2 1.257(3) . ?
O2 N2 1.253(3) . ?
O3 C13 1.212(2) . ?
O4 N3 1.410(5) . ?
O4 C24 1.272(6) . ?
N1 C7 1.468(2) . ?
N1 C8 1.473(2) . ?
N1 C12 1.316(3) . ?
N2 C11 1.399(3) . ?
N3 C22 1.398(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.372(4) . ?
C1 C6 1.386(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(3) . ?
C5 C6 1.391(3) . ?
C5 C8 1.515(2) . ?
C6 C7 1.497(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9800 . ?
C8 C9 1.526(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.563(2) . ?
C9 C13 1.528(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.496(2) . ?
C10 C20 1.507(2) . ?
C11 C12 1.363(3) . ?
C11 N2A 1.46(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.489(2) . ?
C14 C15 1.387(3) . ?
C14 C19 1.391(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.318(2) . ?
C21 H21 0.9300 . ?
C21 C23 1.456(2) . ?
C22 C23 1.393(3) . ?
C22 C25 1.483(3) . ?
C22 O4A 1.209(11) . ?
C23 C24 1.381(2) . ?
C24 C26 1.478(3) . ?
C24 N3A 1.448(9) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
O4A N3A 1.374(10) . ?
O2A N2A 1.21(2) . ?
O1A N2A 1.23(5) . ?
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 N2 C11 C10 -174.2(2) . . . . ?
O1 N2 C11 C12 4.9(4) . . . . ?
O2 N2 C11 C10 7.5(5) . . . . ?
O2 N2 C11 C12 -173.4(3) . . . . ?
O3 C13 C14 C15 165.34(19) . . . . ?
O3 C13 C14 C19 -16.0(3) . . . . ?
O4 N3 C22 C23 -1.4(4) . . . . ?
O4 N3 C22 C25 -179.9(3) . . . . ?
N1 C8 C9 C10 46.75(18) . . . . ?
N1 C8 C9 C13 165.40(13) . . . . ?
N2 C11 C12 N1 179.5(2) . . . . ?
N3 O4 C24 C23 -1.5(4) . . . . ?
N3 O4 C24 C26 179.4(3) . . . . ?
N3 C22 C23 C21 -180.0(4) . . . . ?
N3 C22 C23 C24 0.6(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C1 C6 C7 N1 -166.9(2) . . . . ?
C2 C1 C6 C5 -2.4(3) . . . . ?
C2 C1 C6 C7 177.7(2) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 C8 179.35(19) . . . . ?
C4 C5 C6 C1 1.7(3) . . . . ?
C4 C5 C6 C7 -178.31(18) . . . . ?
C4 C5 C8 N1 164.00(19) . . . . ?
C4 C5 C8 C9 41.9(3) . . . . ?
C5 C6 C7 N1 13.1(2) . . . . ?
C5 C8 C9 C10 163.27(15) . . . . ?
C5 C8 C9 C13 -78.09(18) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
C6 C5 C8 N1 -16.78(18) . . . . ?
C6 C5 C8 C9 -138.90(16) . . . . ?
C7 N1 C8 C5 25.92(18) . . . . ?
C7 N1 C8 C9 152.28(15) . . . . ?
C7 N1 C12 C11 -175.27(17) . . . . ?
C8 N1 C7 C6 -24.67(19) . . . . ?
C8 N1 C12 C11 -0.8(3) . . . . ?
C8 C5 C6 C1 -177.57(18) . . . . ?
C8 C5 C6 C7 2.4(2) . . . . ?
C8 C9 C10 C11 -47.43(17) . . . . ?
C8 C9 C10 C20 75.90(17) . . . . ?
C8 C9 C13 O3 -15.1(2) . . . . ?
C8 C9 C13 C14 169.40(14) . . . . ?
C9 C10 C11 N2 -155.0(2) . . . . ?
C9 C10 C11 C12 25.9(2) . . . . ?
C9 C10 C11 N2A -152(3) . . . . ?
C9 C10 C20 C21 115.10(18) . . . . ?
C9 C13 C14 C15 -19.1(3) . . . . ?
C9 C13 C14 C19 159.51(17) . . . . ?
C10 C9 C13 O3 106.37(19) . . . . ?
C10 C9 C13 C14 -69.14(18) . . . . ?
C10 C11 C12 N1 -1.4(3) . . . . ?
C10 C11 N2A O2A -10(6) . . . . ?
C10 C11 N2A O1A -173(2) . . . . ?
C10 C20 C21 C23 -178.30(16) . . . . ?
C11 C10 C20 C21 -122.76(18) . . . . ?
C12 N1 C7 C6 150.39(18) . . . . ?
C12 N1 C8 C5 -149.33(16) . . . . ?
C12 N1 C8 C9 -23.0(2) . . . . ?
C12 C11 N2A O2A 172(4) . . . . ?
C12 C11 N2A O1A 9(4) . . . . ?
C13 C9 C10 C11 -167.34(13) . . . . ?
C13 C9 C10 C20 -44.01(17) . . . . ?
C13 C14 C15 C16 178.75(18) . . . . ?
C13 C14 C19 C18 -178.7(2) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C14 C19 C18 0.1(3) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C17 C18 C19 C14 0.1(4) . . . . ?
C19 C14 C15 C16 0.1(3) . . . . ?
C20 C10 C11 N2 80.9(2) . . . . ?
C20 C10 C11 C12 -98.21(18) . . . . ?
C20 C10 C11 N2A 84(3) . . . . ?
C20 C21 C23 C22 -22.8(3) . . . . ?
C20 C21 C23 C24 156.53(18) . . . . ?
C21 C23 C24 O4 -178.9(3) . . . . ?
C21 C23 C24 C26 0.0(3) . . . . ?
C21 C23 C24 N3A 179.7(6) . . . . ?
C22 C23 C24 O4 0.6(3) . . . . ?
C22 C23 C24 C26 179.5(2) . . . . ?
C22 C23 C24 N3A -0.9(6) . . . . ?
C22 O4A N3A C24 -3.1(10) . . . . ?
C23 C22 O4A N3A 2.7(9) . . . . ?
C23 C24 N3A O4A 2.4(9) . . . . ?
C24 O4 N3 C22 1.8(4) . . . . ?
C25 C22 C23 C21 -1.7(4) . . . . ?
C25 C22 C23 C24 178.8(2) . . . . ?
C25 C22 O4A N3A -177.3(6) . . . . ?
C26 C24 N3A O4A -177.9(5) . . . . ?
O4A C22 C23 C21 178.2(7) . . . . ?
O4A C22 C23 C24 -1.2(7) . . . . ?
N2A C11 C12 N1 177(2) . . . . ?
