#------------------------------------------------------------------------------
#$Date: 2021-11-10 01:16:51 +0200 (Wed, 10 Nov 2021) $
#$Revision: 270546 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/51/1565153.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_1565153
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 H26 N4 O3'
_chemical_formula_sum            'C26 H26 N4 O3'
_chemical_formula_weight         442.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-28 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                106.178(4)
_cell_angle_beta                 93.800(3)
_cell_angle_gamma                114.614(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5216(3)
_cell_length_b                   10.7823(4)
_cell_length_c                   12.6332(5)
_cell_measurement_reflns_used    2433
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.7780
_cell_measurement_theta_min      4.7750
_cell_volume                     1107.48(8)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   0.50    1.50    --  -33.50  57.00 -60.00  174
  2  ω   -108.00 -32.00   0.50    1.50    --  -33.50 178.00 120.00  152
  3  ω   -102.00 -15.00   0.50    1.50    --  -33.50 -57.00 150.00  174
  4  ω    -34.00  59.00   0.50    1.50    --   36.47 -37.00-120.00  186
  5  ω     57.00 110.00   0.50    1.50    --   36.47 178.00-180.00  106
  6  ω     57.00 110.00   0.50    1.50    --   36.47 178.00 150.00  106
  7  ω     14.00 107.00   0.50    1.50    --   36.47  37.00  60.00  186
  8  ω     -4.00  53.00   0.50    1.50    --   36.47 -99.00  30.00  114
  9  ω     11.00  40.00   0.50    1.50    --   36.47  77.00  60.00   58
 10  ω    -32.00  19.00   0.50    1.50    --   36.47 -77.00 120.00  102
 11  ω     40.00  65.00   0.50    1.50    --   36.47 -77.00 120.00   50
 12  ω     31.00 105.00   0.50    1.50    --   36.47  57.00 -30.00  148
 13  ω     19.00  72.00   0.50    1.50    --   36.47 -99.00 120.00  106
 14  ω      5.00  75.00   0.50    1.50    --   36.47 -99.00 -90.00  140
 15  ω     61.00 105.00   0.50    1.50    --   36.47  77.00  60.00   88
 16  ω    152.00 178.00   0.50    6.50    --  108.00 111.00 150.00   52
 17  ω     44.00  99.00   0.50    6.50    --  108.00-111.00 150.00  110
 18  ω     38.00 127.00   0.50    6.50    --  108.00 -45.00   0.00  178
 19  ω     80.00 132.00   0.50    6.50    --  108.00 -77.00  90.00  104
 20  ω     76.00 108.00   0.50    6.50    --  108.00 -94.00 -60.00   64
 21  ω     45.00 123.00   0.50    6.50    --  108.00 -45.00-180.00  156
 22  ω     97.00 149.00   0.50    6.50    --  108.00  30.00  30.00  104
 23  ω     37.00 122.00   0.50    6.50    --  108.00 -30.00  90.00  170
 24  ω     76.00 109.00   0.50    6.50    --  108.00 -94.00-180.00   66
 25  ω     68.00 109.00   0.50    6.50    --  108.00-111.00  90.00   82
 26  ω     40.00 127.00   0.50    6.50    --  108.00 -45.00 -90.00  174
 27  ω     60.00 101.00   0.50    6.50    --  108.00 -94.00 -90.00   82
 28  ω     38.00 178.00   0.50    6.50    --  108.00   0.00 150.00  280
;
_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      -0.0063998000
_diffrn_orient_matrix_UB_12      0.0251273000
_diffrn_orient_matrix_UB_13      0.1253772000
_diffrn_orient_matrix_UB_21      -0.1810276000
_diffrn_orient_matrix_UB_22      -0.0903974000
_diffrn_orient_matrix_UB_23      -0.0325428000
_diffrn_orient_matrix_UB_31      0.0174674000
_diffrn_orient_matrix_UB_32      -0.1381035000
_diffrn_orient_matrix_UB_33      -0.0088731000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.068
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         3.725
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86956
_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    1.327
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3949
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0570
_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)+(0.1040P)²+0.0918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1847
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2883
_reflns_number_total             3949
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc05741c2.cif
_cod_data_source_block           zzy119
_cod_original_cell_volume        1107.47(8)
_cod_database_code               1565153
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C14H15N2O4
_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   0.859
_reflns_odcompleteness_completeness 99.92
_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
2. Restrained distances
 C21A-N4
 1.45 with sigma of 0.02
 C25A-C24A
 1.52 with sigma of 0.02
 C24A-C23A
 1.52 with sigma of 0.02
 C26A-C25A
 1.52 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N4) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C25)
\\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C23) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C20) = Uanis(C20A)
Uanis(C21) = Uanis(C21A)
Uanis(N4) = Uanis(N4A)
Uanis(C22) = Uanis(C22A)
Uanis(C23) = Uanis(C23A)
Uanis(C24) = Uanis(C24A)
Uanis(C25) = Uanis(C25A)
Uanis(C26) = Uanis(C26A)
4. Others
 Sof(N4A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22C)=
 Sof(H22D)=Sof(C23A)=Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24C)=Sof(H24D)=
 Sof(C25A)=Sof(H25C)=Sof(H25D)=Sof(C26A)=Sof(H26C)=Sof(H26D)=1-FVAR(1)
 Sof(N4)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22A)=Sof(H22B)=
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=
 Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C22(H22A,H22B), C22A(H22C,H22D), C23(H23A,H23B), C23A(H23C,
 H23D), C24(H24A,H24B), C24A(H24C,H24D), C25(H25A,H25B), C25A(H25C,H25D),
 C26(H26A,H26B), C26A(H26C,H26D)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C20(H20), C20A(H20A), C21(H21), C21A(H21A)
;
_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 1.244
_oxdiff_exptl_absorpt_empirical_full_min 0.883
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.89738(19) 0.31207(18) 0.50692(17) 0.0676(5) Uani 1 1 d . . . . .
O2 O 0.5901(4) -0.3333(3) 0.1411(2) 0.1162(10) Uani 1 1 d . . . . .
O3 O 0.8335(4) -0.1799(3) 0.2243(2) 0.1010(9) Uani 1 1 d . . . . .
N1 N 0.8373(2) 0.4069(2) 0.37849(19) 0.0578(5) Uani 1 1 d . . . . .
H1 H 0.9039 0.4964 0.4120 0.069 Uiso 1 1 calc R . . . .
N2 N 0.4428(2) -0.05588(19) 0.31626(17) 0.0556(5) Uani 1 1 d . . . . .
N3 N 0.6913(4) -0.2119(3) 0.2005(2) 0.0836(8) Uani 1 1 d . . . . .
N4 N 1.1080(7) 0.2046(7) 0.1508(5) 0.0908(17) Uani 0.763(5) 1 d D U P A 1
N4A N 1.057(3) 0.169(3) 0.108(2) 0.0908(17) Uani 0.237(5) 1 d . . P A 2
C1 C 0.8214(2) 0.2996(2) 0.4190(2) 0.0521(5) Uani 1 1 d . . . . .
C2 C 0.6917(3) 0.1563(2) 0.33495(19) 0.0478(5) Uani 1 1 d . . . . .
C3 C 0.6406(3) 0.2055(2) 0.24592(19) 0.0511(5) Uani 1 1 d . . . . .
C4 C 0.7327(3) 0.3553(2) 0.2755(2) 0.0516(5) Uani 1 1 d . . . . .
C5 C 0.7174(3) 0.4325(3) 0.2093(2) 0.0612(6) Uani 1 1 d . . . . .
H5 H 0.7798 0.5322 0.2310 0.073 Uiso 1 1 calc R . . . .
C6 C 0.6066(4) 0.3574(3) 0.1098(2) 0.0733(8) Uani 1 1 d . . . . .
H6 H 0.5936 0.4068 0.0633 0.088 Uiso 1 1 calc R . . . .
C7 C 0.5146(4) 0.2093(3) 0.0782(2) 0.0796(9) Uani 1 1 d . . . . .
H7 H 0.4410 0.1605 0.0103 0.096 Uiso 1 1 calc R . . . .
C8 C 0.5299(4) 0.1315(3) 0.1462(2) 0.0686(7) Uani 1 1 d . . . . .
H8 H 0.4668 0.0320 0.1246 0.082 Uiso 1 1 calc R . . . .
C9 C 0.5605(2) 0.0844(2) 0.39509(18) 0.0448(5) Uani 1 1 d . . . . .
H9 H 0.6084 0.0673 0.4572 0.054 Uiso 1 1 calc R . . . .
C10 C 0.2793(3) -0.0823(3) 0.3183(3) 0.0709(7) Uani 1 1 d . . . . .
H10A H 0.2240 -0.1626 0.3446 0.085 Uiso 1 1 calc R . . . .
H10B H 0.2219 -0.1017 0.2444 0.085 Uiso 1 1 calc R . . . .
C11 C 0.3015(3) 0.0579(3) 0.4000(2) 0.0597(6) Uani 1 1 d . . . . .
C12 C 0.4598(3) 0.1551(2) 0.43977(18) 0.0486(5) Uani 1 1 d . . . . .
C13 C 0.5047(3) 0.2914(3) 0.5165(2) 0.0631(6) Uani 1 1 d . . . . .
H13 H 0.6111 0.3575 0.5423 0.076 Uiso 1 1 calc R . . . .
C14 C 0.3899(4) 0.3285(4) 0.5544(3) 0.0821(9) Uani 1 1 d . . . . .
H14 H 0.4191 0.4203 0.6055 0.099 Uiso 1 1 calc R . . . .
C15 C 0.2325(4) 0.2302(4) 0.5169(3) 0.0896(10) Uani 1 1 d . . . . .
H15 H 0.1564 0.2556 0.5442 0.108 Uiso 1 1 calc R . . . .
C16 C 0.1864(3) 0.0947(4) 0.4394(3) 0.0819(9) Uani 1 1 d . . . . .
H16 H 0.0800 0.0290 0.4139 0.098 Uiso 1 1 calc R . . . .
C17 C 0.4915(3) -0.1446(2) 0.2528(2) 0.0622(7) Uani 1 1 d . . . . .
H17 H 0.4181 -0.2389 0.2102 0.075 Uiso 1 1 calc R . . . .
C18 C 0.6453(4) -0.1006(3) 0.2489(2) 0.0630(7) Uani 1 1 d . . . . .
C19 C 0.7694(3) 0.0521(3) 0.2952(3) 0.0633(7) Uani 1 1 d . . . . .
H19 H 0.834(4) 0.069(3) 0.363(3) 0.076 Uiso 1 1 d R . . . .
C20 C 0.8552(4) 0.0878(3) 0.1997(3) 0.0577(8) Uani 0.763(5) 1 d . . P A 1
H20 H 0.7981 0.0558 0.1267 0.069 Uiso 0.763(5) 1 calc R . P A 1
C20A C 0.9309(15) 0.1395(12) 0.2706(10) 0.0577(8) Uani 0.237(5) 1 d . . P A 2
H20A H 1.0168 0.2069 0.3288 0.069 Uiso 0.237(5) 1 calc R . P A 2
C21 C 1.0081(6) 0.1630(5) 0.2229(4) 0.0766(13) Uani 0.763(5) 1 d . . P A 1
H21 H 1.0570 0.1929 0.2979 0.092 Uiso 0.763(5) 1 calc R . P A 1
C21A C 0.9429(18) 0.1164(18) 0.1678(15) 0.0766(13) Uani 0.237(5) 1 d D . P A 2
H21A H 0.8485 0.0441 0.1197 0.092 Uiso 0.237(5) 1 calc R . P A 2
C22 C 1.0428(9) 0.1886(9) 0.0365(6) 0.097(2) Uani 0.763(5) 1 d . U P A 1
H22A H 0.9524 0.0939 0.0032 0.117 Uiso 0.763(5) 1 calc R . P A 1
H22B H 1.1218 0.1929 -0.0090 0.117 Uiso 0.763(5) 1 calc R . P A 1
C22A C 0.986(4) 0.170(3) 0.000(2) 0.097(2) Uani 0.237(5) 1 d . . P A 2
H22C H 1.0328 0.1392 -0.0615 0.117 Uiso 0.237(5) 1 calc R . P A 2
H22D H 0.8725 0.1129 -0.0195 0.117 Uiso 0.237(5) 1 calc R . P A 2
C23 C 0.9899(11) 0.3085(14) 0.0327(16) 0.106(2) Uani 0.763(5) 1 d . U P A 1
H23A H 0.9606 0.3011 -0.0447 0.127 Uiso 0.763(5) 1 calc R . P A 1
H23B H 0.8999 0.2971 0.0680 0.127 Uiso 0.763(5) 1 calc R . P A 1
C23A C 1.032(4) 0.315(5) 0.034(6) 0.106(2) Uani 0.237(5) 1 d D . P A 2
H23C H 0.9709 0.3284 0.0911 0.127 Uiso 0.237(5) 1 calc R . P A 2
H23D H 0.9849 0.3271 -0.0300 0.127 Uiso 0.237(5) 1 calc R . P A 2
C24 C 1.1295(9) 0.4523(9) 0.0960(7) 0.116(2) Uani 0.763(5) 1 d . U P A 1
H24A H 1.0977 0.5285 0.1038 0.139 Uiso 0.763(5) 1 calc R . P A 1
H24B H 1.2115 0.4686 0.0523 0.139 Uiso 0.763(5) 1 calc R . P A 1
C24A C 1.188(3) 0.451(3) 0.080(3) 0.116(2) Uani 0.237(5) 1 d D . P A 2
H24C H 1.2625 0.4472 0.0316 0.139 Uiso 0.237(5) 1 calc R . P A 2
H24D H 1.1741 0.5364 0.0867 0.139 Uiso 0.237(5) 1 calc R . P A 2
C25 C 1.1976(11) 0.4627(10) 0.2129(8) 0.120(2) Uani 0.763(5) 1 d . U P A 1
H25A H 1.2900 0.5558 0.2475 0.144 Uiso 0.763(5) 1 calc R . P A 1
H25B H 1.1199 0.4580 0.2596 0.144 Uiso 0.763(5) 1 calc R . P A 1
C25A C 1.242(4) 0.448(3) 0.193(3) 0.120(2) Uani 0.237(5) 1 d D . P A 2
H25C H 1.1724 0.4582 0.2439 0.144 Uiso 0.237(5) 1 calc R . P A 2
H25D H 1.3495 0.5213 0.2277 0.144 Uiso 0.237(5) 1 calc R . P A 2
C26 C 1.2431(9) 0.3436(8) 0.2091(6) 0.113(2) Uani 0.763(5) 1 d . U P A 1
H26A H 1.3296 0.3541 0.1700 0.135 Uiso 0.763(5) 1 calc R . P A 1
H26B H 1.2779 0.3496 0.2851 0.135 Uiso 0.763(5) 1 calc R . P A 1
C26A C 1.228(3) 0.297(3) 0.156(2) 0.113(2) Uani 0.237(5) 1 d D . P A 2
H26C H 1.2762 0.2836 0.2194 0.135 Uiso 0.237(5) 1 calc R . P A 2
H26D H 1.2898 0.2893 0.0980 0.135 Uiso 0.237(5) 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
C1 N1 H1 124.0 . . ?
C1 N1 C4 111.99(19) . . ?
C4 N1 H1 124.0 . . ?
C9 N2 C10 113.92(19) . . ?
C17 N2 C9 118.9(2) . . ?
C17 N2 C10 127.2(2) . . ?
O2 N3 O3 123.3(3) . . ?
O2 N3 C18 119.6(3) . . ?
O3 N3 C18 117.1(3) . . ?
C21 N4 C22 120.1(5) . . ?
C21 N4 C26 110.8(5) . . ?
C26 N4 C22 113.5(6) . . ?
C21A N4A C22A 111(2) . . ?
C21A N4A C26A 128(2) . . ?
C22A N4A C26A 111(2) . . ?
O1 C1 N1 126.6(2) . . ?
O1 C1 C2 125.20(19) . . ?
N1 C1 C2 108.2(2) . . ?
C1 C2 C9 109.78(18) . . ?
C1 C2 C19 107.18(19) . . ?
C3 C2 C1 102.06(17) . . ?
C3 C2 C9 114.53(18) . . ?
C3 C2 C19 115.52(19) . . ?
C9 C2 C19 107.37(17) . . ?
C4 C3 C2 108.6(2) . . ?
C8 C3 C2 132.4(2) . . ?
C8 C3 C4 118.9(2) . . ?
C3 C4 N1 109.1(2) . . ?
C5 C4 N1 128.1(2) . . ?
C5 C4 C3 122.8(2) . . ?
C4 C5 H5 121.1 . . ?
C4 C5 C6 117.7(2) . . ?
C6 C5 H5 121.1 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.7(2) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.3(3) . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C7 118.5(2) . . ?
C3 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
N2 C9 C2 109.31(17) . . ?
N2 C9 H9 108.1 . . ?
N2 C9 C12 102.10(17) . . ?
C2 C9 H9 108.1 . . ?
C12 C9 C2 120.44(17) . . ?
C12 C9 H9 108.1 . . ?
N2 C10 H10A 111.4 . . ?
N2 C10 H10B 111.4 . . ?
N2 C10 C11 101.83(19) . . ?
H10A C10 H10B 109.3 . . ?
C11 C10 H10A 111.4 . . ?
C11 C10 H10B 111.4 . . ?
C12 C11 C10 111.6(2) . . ?
C12 C11 C16 120.3(3) . . ?
C16 C11 C10 128.1(3) . . ?
C11 C12 C9 110.2(2) . . ?
C13 C12 C9 129.3(2) . . ?
C13 C12 C11 120.3(2) . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.3(3) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 H16 120.5 . . ?
C15 C16 C11 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
N2 C17 H17 119.4 . . ?
N2 C17 C18 121.3(2) . . ?
C18 C17 H17 119.4 . . ?
N3 C18 C19 118.5(3) . . ?
C17 C18 N3 116.7(3) . . ?
C17 C18 C19 124.7(2) . . ?
C2 C19 H19 102.6(19) . . ?
C18 C19 C2 110.0(2) . . ?
C18 C19 H19 111.0(19) . . ?
C18 C19 C20 107.6(2) . . ?
C18 C19 C20A 135.3(5) . . ?
C20 C19 C2 109.2(2) . . ?
C20 C19 H19 116.4(19) . . ?
C20A C19 C2 108.3(4) . . ?
C20A C19 H19 81.8(19) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 C19 119.1(4) . . ?
C21 C20 H20 120.4 . . ?
C19 C20A H20A 121.1 . . ?
C21A C20A C19 117.7(12) . . ?
C21A C20A H20A 121.1 . . ?
N4 C21 H21 115.7 . . ?
C20 C21 N4 128.7(5) . . ?
C20 C21 H21 115.7 . . ?
N4A C21A H21A 111.1 . . ?
C20A C21A N4A 137.7(18) . . ?
C20A C21A H21A 111.1 . . ?
N4 C22 H22A 108.9 . . ?
N4 C22 H22B 108.9 . . ?
N4 C22 C23 113.5(9) . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
N4A C22A H22C 112.4 . . ?
N4A C22A H22D 112.4 . . ?
H22C C22A H22D 110.0 . . ?
C23A C22A N4A 97(4) . . ?
C23A C22A H22C 112.4 . . ?
C23A C22A H22D 112.4 . . ?
C22 C23 H23A 110.5 . . ?
C22 C23 H23B 110.5 . . ?
H23A C23 H23B 108.7 . . ?
C24 C23 C22 106.3(9) . . ?
C24 C23 H23A 110.5 . . ?
C24 C23 H23B 110.5 . . ?
C22A C23A H23C 103.3 . . ?
C22A C23A H23D 103.3 . . ?
C22A C23A C24A 135(4) . . ?
H23C C23A H23D 105.2 . . ?
C24A C23A H23C 103.3 . . ?
C24A C23A H23D 103.3 . . ?
C23 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
C23 C24 C25 113.3(10) . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C23A C24A H24C 111.2 . . ?
C23A C24A H24D 111.2 . . ?
H24C C24A H24D 109.1 . . ?
C25A C24A C23A 103(4) . . ?
C25A C24A H24C 111.2 . . ?
C25A C24A H24D 111.2 . . ?
C24 C25 H25A 109.1 . . ?
C24 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 C24 112.5(7) . . ?
C26 C25 H25A 109.1 . . ?
C26 C25 H25B 109.1 . . ?
C24A C25A H25C 112.1 . . ?
C24A C25A H25D 112.1 . . ?
C24A C25A C26A 98(2) . . ?
H25C C25A H25D 109.7 . . ?
C26A C25A H25C 112.1 . . ?
C26A C25A H25D 112.1 . . ?
N4 C26 C25 109.2(7) . . ?
N4 C26 H26A 109.8 . . ?
N4 C26 H26B 109.8 . . ?
C25 C26 H26A 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.3 . . ?
N4A C26A H26C 108.2 . . ?
N4A C26A H26D 108.2 . . ?
C25A C26A N4A 116(3) . . ?
C25A C26A H26C 108.2 . . ?
C25A C26A H26D 108.2 . . ?
H26C C26A H26D 107.4 . . ?
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 1.227(3) . ?
O2 N3 1.229(4) . ?
O3 N3 1.242(4) . ?
N1 H1 0.8600 . ?
N1 C1 1.348(3) . ?
N1 C4 1.399(3) . ?
N2 C9 1.461(3) . ?
N2 C10 1.464(3) . ?
N2 C17 1.328(3) . ?
N3 C18 1.439(3) . ?
N4 C21 1.386(8) . ?
N4 C22 1.468(8) . ?
N4 C26 1.448(9) . ?
N4A C21A 1.38(3) . ?
N4A C22A 1.49(3) . ?
N4A C26A 1.57(4) . ?
C1 C2 1.537(3) . ?
C2 C3 1.502(3) . ?
C2 C9 1.545(3) . ?
C2 C19 1.578(3) . ?
C3 C4 1.400(3) . ?
C3 C8 1.378(4) . ?
C4 C5 1.373(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.382(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.396(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9800 . ?
C9 C12 1.504(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.493(4) . ?
C11 C12 1.383(3) . ?
C11 C16 1.390(4) . ?
C12 C13 1.382(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.347(4) . ?
C18 C19 1.483(4) . ?
C19 H19 0.94(3) . ?
C19 C20 1.550(4) . ?
C19 C20A 1.540(12) . ?
C20 H20 0.9300 . ?
C20 C21 1.300(6) . ?
C20A H20A 0.9300 . ?
C20A C21A 1.27(2) . ?
C21 H21 0.9300 . ?
C21A H21A 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.581(18) . ?
C22A H22C 0.9700 . ?
C22A H22D 0.9700 . ?
C22A C23A 1.36(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.505(10) . ?
C23A H23C 0.9700 . ?
C23A H23D 0.9700 . ?
C23A C24A 1.51(2) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.528(9) . ?
C24A H24C 0.9700 . ?
C24A H24D 0.9700 . ?
C24A C25A 1.50(2) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.508(10) . ?
C25A H25C 0.9700 . ?
C25A H25D 0.9700 . ?
C25A C26A 1.513(19) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26A H26C 0.9700 . ?
C26A H26D 0.9700 . ?
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
N1 H1 O1 0.86 2.05 2.890(2) 165.2 2_766
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 C3 179.7(2) . . . . ?
O1 C1 C2 C9 57.8(3) . . . . ?
O1 C1 C2 C19 -58.5(3) . . . . ?
O2 N3 C18 C17 18.0(4) . . . . ?
O2 N3 C18 C19 -164.8(3) . . . . ?
O3 N3 C18 C17 -160.2(2) . . . . ?
O3 N3 C18 C19 17.1(4) . . . . ?
N1 C1 C2 C3 -1.0(2) . . . . ?
N1 C1 C2 C9 -122.9(2) . . . . ?
N1 C1 C2 C19 120.8(2) . . . . ?
N1 C4 C5 C6 179.1(2) . . . . ?
N2 C9 C12 C11 6.4(2) . . . . ?
N2 C9 C12 C13 -178.7(2) . . . . ?
N2 C10 C11 C12 0.7(3) . . . . ?
N2 C10 C11 C16 -177.2(3) . . . . ?
N2 C17 C18 N3 165.4(2) . . . . ?
N2 C17 C18 C19 -11.6(4) . . . . ?
N3 C18 C19 C2 175.6(2) . . . . ?
N3 C18 C19 C20 56.7(3) . . . . ?
N3 C18 C19 C20A 28.1(8) . . . . ?
N4 C22 C23 C24 52.7(12) . . . . ?
N4A C22A C23A C24A 58(8) . . . . ?
C1 N1 C4 C3 0.6(3) . . . . ?
C1 N1 C4 C5 -178.9(2) . . . . ?
C1 C2 C3 C4 1.3(2) . . . . ?
C1 C2 C3 C8 179.1(3) . . . . ?
C1 C2 C9 N2 -176.54(16) . . . . ?
C1 C2 C9 C12 65.8(2) . . . . ?
C1 C2 C19 C18 159.5(2) . . . . ?
C1 C2 C19 C20 -82.6(3) . . . . ?
C1 C2 C19 C20A -44.0(6) . . . . ?
C2 C3 C4 N1 -1.3(2) . . . . ?
C2 C3 C4 C5 178.3(2) . . . . ?
C2 C3 C8 C7 -177.3(3) . . . . ?
C2 C9 C12 C11 127.6(2) . . . . ?
C2 C9 C12 C13 -57.5(3) . . . . ?
C2 C19 C20 C21 102.3(4) . . . . ?
C2 C19 C20A C21A -106.4(11) . . . . ?
C3 C2 C9 N2 69.4(2) . . . . ?
C3 C2 C9 C12 -48.3(3) . . . . ?
C3 C2 C19 C18 -87.6(2) . . . . ?
C3 C2 C19 C20 30.3(3) . . . . ?
C3 C2 C19 C20A 68.9(6) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 N1 C1 O1 179.6(2) . . . . ?
C4 N1 C1 C2 0.3(3) . . . . ?
C4 C3 C8 C7 0.3(4) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C5 C6 C7 C8 0.5(5) . . . . ?
C6 C7 C8 C3 -0.6(5) . . . . ?
C8 C3 C4 N1 -179.4(2) . . . . ?
C8 C3 C4 C5 0.1(4) . . . . ?
C9 N2 C10 C11 3.7(3) . . . . ?
C9 N2 C17 C18 -8.8(3) . . . . ?
C9 C2 C3 C4 119.9(2) . . . . ?
C9 C2 C3 C8 -62.4(3) . . . . ?
C9 C2 C19 C18 41.6(3) . . . . ?
C9 C2 C19 C20 159.5(2) . . . . ?
C9 C2 C19 C20A -161.9(5) . . . . ?
C9 C12 C13 C14 -173.3(2) . . . . ?
C10 N2 C9 C2 -134.8(2) . . . . ?
C10 N2 C9 C12 -6.2(2) . . . . ?
C10 N2 C17 C18 171.8(2) . . . . ?
C10 C11 C12 C9 -4.6(3) . . . . ?
C10 C11 C12 C13 180.0(2) . . . . ?
C10 C11 C16 C15 178.8(3) . . . . ?
C11 C12 C13 C14 1.1(4) . . . . ?
C12 C11 C16 C15 1.2(4) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C13 C14 C15 C16 -1.4(5) . . . . ?
C14 C15 C16 C11 0.5(5) . . . . ?
C16 C11 C12 C9 173.4(2) . . . . ?
C16 C11 C12 C13 -2.0(4) . . . . ?
C17 N2 C9 C2 45.7(3) . . . . ?
C17 N2 C9 C12 174.38(19) . . . . ?
C17 N2 C10 C11 -176.9(2) . . . . ?
C17 C18 C19 C2 -7.4(4) . . . . ?
C17 C18 C19 C20 -126.3(3) . . . . ?
C17 C18 C19 C20A -154.9(7) . . . . ?
C18 C19 C20 C21 -138.3(3) . . . . ?
C18 C19 C20A C21A 41.4(14) . . . . ?
C19 C2 C3 C4 -114.6(2) . . . . ?
C19 C2 C3 C8 63.2(3) . . . . ?
C19 C2 C9 N2 -60.3(2) . . . . ?
C19 C2 C9 C12 -178.0(2) . . . . ?
C19 C20 C21 N4 178.7(5) . . . . ?
C19 C20A C21A N4A 178(2) . . . . ?
C21 N4 C22 C23 76.5(9) . . . . ?
C21 N4 C26 C25 -81.8(6) . . . . ?
C21A N4A C22A C23A 103(3) . . . . ?
C21A N4A C26A C25A -75(3) . . . . ?
C22 N4 C21 C20 12.0(9) . . . . ?
C22 N4 C26 C25 56.8(8) . . . . ?
C22 C23 C24 C25 -51.5(12) . . . . ?
C22A N4A C21A C20A -145(2) . . . . ?
C22A N4A C26A C25A 67(3) . . . . ?
C22A C23A C24A C25A -68(8) . . . . ?
C23 C24 C25 C26 55.9(10) . . . . ?
C23A C24A C25A C26A 53(3) . . . . ?
C24 C25 C26 N4 -55.1(7) . . . . ?
C24A C25A C26A N4A -67(3) . . . . ?
C26 N4 C21 C20 147.5(5) . . . . ?
C26 N4 C22 C23 -57.9(8) . . . . ?
C26A N4A C21A C20A -4(4) . . . . ?
C26A N4A C22A C23A -45(3) . . . . ?
