#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:36:43 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296683 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160133.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_7160133
loop_
_publ_author_name
'Shen, Li-Wen'
'Luo, Nian'
'Jia, Yun-Qing'
'Wang, Guang-Wei'
'Yuan, Shu-Pei'
'Xiang, Min'
_publ_section_title
;
 Lewis base promoted [4 + 2] annulation of o-acylamino-aryl MBH
 carbonates with isatin.
;
_journal_issue                   39
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7961
_journal_page_last               7964
_journal_paper_doi               10.1039/d4ob01240b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C26 H28 N2 O6'
_chemical_formula_sum            'C26 H28 N2 O6'
_chemical_formula_weight         464.50
_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             2024-05-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-06-05 deposited with the CCDC.	2024-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.953(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2639(3)
_cell_length_b                   23.4915(6)
_cell_length_c                   13.1699(4)
_cell_measurement_reflns_used    3957
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9840
_cell_measurement_theta_min      3.7540
_cell_volume                     2458.23(14)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  33.00   1.00    1.10    --  -33.50  57.00   0.00   31
  2  ω    -73.00 -35.00   1.00    1.10    --  -33.50 178.00-120.00   38
  3  ω    -41.00 -11.00   1.00    1.10    --  -33.50 -37.00-150.00   30
  4  ω    -99.00 -73.00   1.00    1.10    --  -33.50 -37.00-150.00   26
  5  ω     61.00  87.00   1.00    1.10    --   36.47 178.00 -90.00   26
  6  ω    -10.00  46.00   1.00    1.10    --   36.47 -77.00 -90.00   56
  7  ω     64.00  90.00   1.00    1.10    --   36.47  57.00  30.00   26
  8  ω     63.00 103.00   1.00    1.10    --   36.47  57.00 150.00   40
  9  ω     27.00  53.00   1.00    1.10    --   36.47  57.00 150.00   26
 10  ω    -35.00  57.00   1.00    1.10    --   36.47 -19.00  30.00   92
 11  ω     19.00  52.00   1.00    1.10    --   36.47  57.00  30.00   33
 12  ω     44.00 125.00   1.00    5.50    --  108.00 -61.00  60.00   81
 13  ω     83.00 170.00   1.00    5.50    --  108.00  30.00 -60.00   87
 14  ω    103.00 158.00   1.00    5.50    --  108.00  77.00 150.00   55
 15  ω     86.00 128.00   1.00    5.50    --  108.00 -45.00 -60.00   42
 16  ω     40.00  65.00   1.00    5.50    --  108.00 -45.00 -60.00   25
 17  ω     40.00  98.00   1.00    5.50    --  108.00-111.00 -30.00   58
 18  ω    121.00 152.00   1.00    5.50    --  108.00 111.00 150.00   31
 19  ω     44.00 101.00   1.00    5.50    --  108.00 -77.00  30.00   57
 20  ω     62.00 136.00   1.00    5.50    --  108.00 178.00 -30.00   74
;
_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      -0.1831588000
_diffrn_orient_matrix_UB_12      0.0093898000
_diffrn_orient_matrix_UB_13      0.0030278000
_diffrn_orient_matrix_UB_21      0.0327779000
_diffrn_orient_matrix_UB_22      -0.0366823000
_diffrn_orient_matrix_UB_23      0.1006263000
_diffrn_orient_matrix_UB_31      0.0545529000
_diffrn_orient_matrix_UB_32      0.0535017000
_diffrn_orient_matrix_UB_33      0.0683796000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9520
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         3.763
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
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    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4370
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0585
_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)+(0.0933P)²+0.4004P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1695
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3455
_reflns_number_total             4370
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01240b2.cif
_cod_data_source_block           202405181
_cod_depositor_comments          'Adding full bibliography for 7160133.cif.'
_cod_original_cell_volume        2458.23(13)
_cod_database_code               7160133
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N3O1
_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   0.937
_shelx_estimated_absorpt_t_min   0.904
_reflns_odcompleteness_completeness 99.54
_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
 C11-C12
 1.54 with sigma of 0.02
 O2-C11
 1.43 with sigma of 0.02
 O2-C11A
 1.43 with sigma of 0.02
 C11A-C12A
 1.54 with sigma of 0.02
3. Rigid bond restraints
 O2, C9
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C11) = Uanis(C11A)
Uanis(C12) = Uanis(C12A)
5. Others
 Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C7(H7)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C11A(H11C,H11D)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C22(H22), C23(H23), C24(H24), C25(H25)
6.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
6.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C12A(H12D,H12E,H12F), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), 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 1.186
_oxdiff_exptl_absorpt_empirical_full_min 0.924
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 0.3192(3) 0.17477(10) 0.9575(2) 0.0966(8) Uani 1 1 d . . . . .
O2 O 0.2891(3) 0.25922(9) 1.02625(16) 0.0718(5) Uani 1 1 d D U . . .
O3 O -0.0520(2) 0.48824(7) 0.72396(14) 0.0560(4) Uani 1 1 d . . . . .
O4 O -0.1725(2) 0.47870(6) 0.85839(12) 0.0505(4) Uani 1 1 d . . . . .
O5 O 0.0315(2) 0.31888(6) 0.73373(12) 0.0461(4) Uani 1 1 d . . . . .
O6 O 0.2811(2) 0.41590(8) 0.79888(14) 0.0596(5) Uani 1 1 d . . . . .
N1 N -0.0898(2) 0.40129(7) 0.78654(13) 0.0402(4) Uani 1 1 d . . . . .
N2 N 0.1716(2) 0.41881(8) 0.61800(15) 0.0478(4) Uani 1 1 d . . . . .
C1 C -0.1418(3) 0.27476(10) 0.9385(2) 0.0552(6) Uani 1 1 d . . . . .
H1 H -0.0835 0.2414 0.9628 0.066 Uiso 1 1 calc R . . . .
C2 C -0.2929(4) 0.28516(12) 0.9594(3) 0.0694(8) Uani 1 1 d . . . . .
H2 H -0.3348 0.2594 0.9995 0.083 Uiso 1 1 calc R . . . .
C3 C -0.3825(3) 0.33363(12) 0.9210(3) 0.0667(7) Uani 1 1 d . . . . .
H3 H -0.4856 0.3402 0.9345 0.080 Uiso 1 1 calc R . . . .
C4 C -0.3205(3) 0.37279(10) 0.86238(19) 0.0492(5) Uani 1 1 d . . . . .
H4 H -0.3826 0.4050 0.8350 0.059 Uiso 1 1 calc R . . . .
C5 C -0.1646(3) 0.36317(9) 0.84517(15) 0.0392(4) Uani 1 1 d . . . . .
C6 C -0.0756(3) 0.31352(9) 0.88188(16) 0.0404(4) Uani 1 1 d . . . . .
C7 C 0.0800(3) 0.30470(9) 0.84524(17) 0.0437(5) Uani 1 1 d . . . . .
H7 H 0.1710 0.3297 0.8841 0.052 Uiso 1 1 calc R . . . .
C8 C 0.1392(3) 0.24340(10) 0.8521(2) 0.0550(6) Uani 1 1 d . . . . .
C9 C 0.2576(3) 0.22145(11) 0.9486(2) 0.0614(6) Uani 1 1 d . U . . .
C10 C 0.0828(5) 0.20673(12) 0.7745(3) 0.0871(10) Uani 1 1 d . . . . .
H10A H 0.1183 0.1690 0.7826 0.104 Uiso 1 1 calc R . . . .
H10B H 0.0076 0.2186 0.7118 0.104 Uiso 1 1 calc R . . . .
C11 C 0.369(2) 0.2625(11) 1.1457(12) 0.0743(12) Uani 0.174(8) 1 d D . P A 1
H11A H 0.3491 0.2267 1.1769 0.089 Uiso 0.174(8) 1 calc R . P A 1
H11B H 0.3116 0.2920 1.1742 0.089 Uiso 0.174(8) 1 calc R . P A 1
C11A C 0.3965(6) 0.2372(2) 1.1261(3) 0.0743(12) Uani 0.826(8) 1 d D . P A 2
H11C H 0.4807 0.2116 1.1133 0.089 Uiso 0.826(8) 1 calc R . P A 2
H11D H 0.3298 0.2168 1.1644 0.089 Uiso 0.826(8) 1 calc R . P A 2
C12 C 0.560(3) 0.2750(14) 1.180(2) 0.0946(16) Uani 0.174(8) 1 d D . P A 1
H12A H 0.6169 0.2492 1.1454 0.142 Uiso 0.174(8) 1 calc GR . P A 1
H12B H 0.6022 0.2702 1.2554 0.142 Uiso 0.174(8) 1 calc GR . P A 1
H12C H 0.5796 0.3134 1.1618 0.142 Uiso 0.174(8) 1 calc GR . P A 1
C12A C 0.4775(9) 0.2873(2) 1.1870(4) 0.0946(16) Uani 0.826(8) 1 d D . P A 2
H12D H 0.5368 0.3085 1.1462 0.142 Uiso 0.826(8) 1 calc GR . P A 2
H12E H 0.5552 0.2749 1.2516 0.142 Uiso 0.826(8) 1 calc GR . P A 2
H12F H 0.3930 0.3111 1.2028 0.142 Uiso 0.826(8) 1 calc GR . P A 2
C13 C -0.1031(3) 0.45988(9) 0.78516(15) 0.0417(5) Uani 1 1 d . . . . .
C14 C -0.2185(3) 0.53961(10) 0.86149(19) 0.0546(6) Uani 1 1 d . . . . .
C15 C -0.3022(6) 0.53995(16) 0.9503(3) 0.1024(13) Uani 1 1 d . . . . .
H15A H -0.4033 0.5176 0.9304 0.154 Uiso 1 1 calc GR . . . .
H15B H -0.3296 0.5784 0.9642 0.154 Uiso 1 1 calc GR . . . .
H15C H -0.2268 0.5241 1.0128 0.154 Uiso 1 1 calc GR . . . .
C16 C -0.0610(5) 0.57550(12) 0.8899(2) 0.0772(9) Uani 1 1 d . . . . .
H16A H 0.0185 0.5595 0.9504 0.116 Uiso 1 1 calc GR . . . .
H16B H -0.0886 0.6136 0.9057 0.116 Uiso 1 1 calc GR . . . .
H16C H -0.0126 0.5763 0.8314 0.116 Uiso 1 1 calc GR . . . .
C17 C -0.3365(4) 0.55674(13) 0.7569(2) 0.0754(8) Uani 1 1 d . . . . .
H17A H -0.2782 0.5551 0.7031 0.113 Uiso 1 1 calc GR . . . .
H17B H -0.3756 0.5949 0.7617 0.113 Uiso 1 1 calc GR . . . .
H17C H -0.4308 0.5312 0.7391 0.113 Uiso 1 1 calc GR . . . .
C18 C 0.1685(3) 0.40787(9) 0.71921(17) 0.0444(5) Uani 1 1 d . . . . .
C19 C -0.0022(3) 0.37732(9) 0.71258(16) 0.0398(4) Uani 1 1 d . . . . .
C20 C -0.0938(3) 0.38293(9) 0.59737(16) 0.0407(4) Uani 1 1 d . . . . .
C21 C 0.0157(3) 0.40676(9) 0.54581(17) 0.0443(5) Uani 1 1 d . . . . .
C22 C -0.0342(4) 0.41668(11) 0.43857(19) 0.0578(6) Uani 1 1 d . . . . .
H22 H 0.0386 0.4329 0.4040 0.069 Uiso 1 1 calc R . . . .
C23 C -0.1980(4) 0.40154(12) 0.3839(2) 0.0654(7) Uani 1 1 d . . . . .
H23 H -0.2343 0.4071 0.3112 0.078 Uiso 1 1 calc R . . . .
C24 C -0.3077(3) 0.37846(12) 0.4351(2) 0.0619(7) Uani 1 1 d . . . . .
H24 H -0.4168 0.3691 0.3970 0.074 Uiso 1 1 calc R . . . .
C25 C -0.2555(3) 0.36926(10) 0.54347(18) 0.0492(5) Uani 1 1 d . . . . .
H25 H -0.3290 0.3541 0.5786 0.059 Uiso 1 1 calc R . . . .
C26 C 0.3118(4) 0.44507(12) 0.5899(2) 0.0645(7) Uani 1 1 d . . . . .
H26A H 0.3440 0.4218 0.5387 0.097 Uiso 1 1 calc GR . . . .
H26B H 0.4051 0.4487 0.6518 0.097 Uiso 1 1 calc GR . . . .
H26C H 0.2792 0.4821 0.5605 0.097 Uiso 1 1 calc GR . . . .
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
C9 O2 C11 139.9(10) . . ?
C9 O2 C11A 113.5(3) . . ?
C13 O4 C14 120.45(17) . . ?
C19 O5 C7 114.04(15) . . ?
C5 N1 C19 118.74(16) . . ?
C13 N1 C5 125.94(17) . . ?
C13 N1 C19 115.08(16) . . ?
C18 N2 C21 111.32(18) . . ?
C18 N2 C26 124.1(2) . . ?
C21 N2 C26 124.2(2) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.5(2) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 N1 123.06(19) . . ?
C4 C5 C6 120.4(2) . . ?
C6 C5 N1 116.54(18) . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 C7 125.6(2) . . ?
C5 C6 C7 114.81(18) . . ?
O5 C7 C6 105.66(16) . . ?
O5 C7 H7 110.5 . . ?
O5 C7 C8 105.89(18) . . ?
C6 C7 H7 110.5 . . ?
C6 C7 C8 113.66(19) . . ?
C8 C7 H7 110.5 . . ?
C9 C8 C7 120.9(2) . . ?
C10 C8 C7 122.3(3) . . ?
C10 C8 C9 116.8(2) . . ?
O1 C9 O2 123.3(3) . . ?
O1 C9 C8 124.7(3) . . ?
O2 C9 C8 112.1(2) . . ?
C8 C10 H10A 120.0 . . ?
C8 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
O2 C11 H11A 108.4 . . ?
O2 C11 H11B 108.4 . . ?
O2 C11 C12 115.3(16) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
O2 C11A H11C 110.5 . . ?
O2 C11A H11D 110.5 . . ?
O2 C11A C12A 106.2(4) . . ?
H11C C11A H11D 108.7 . . ?
C12A C11A H11C 110.5 . . ?
C12A C11A H11D 110.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11A C12A H12D 109.5 . . ?
C11A C12A H12E 109.5 . . ?
C11A C12A H12F 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
O3 C13 O4 127.00(19) . . ?
O3 C13 N1 121.16(19) . . ?
O4 C13 N1 111.83(17) . . ?
O4 C14 C15 101.6(2) . . ?
O4 C14 C16 109.6(2) . . ?
O4 C14 C17 109.8(2) . . ?
C16 C14 C15 110.6(3) . . ?
C17 C14 C15 112.8(3) . . ?
C17 C14 C16 112.0(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O6 C18 N2 126.9(2) . . ?
O6 C18 C19 125.9(2) . . ?
N2 C18 C19 106.90(18) . . ?
O5 C19 N1 110.29(16) . . ?
O5 C19 C18 107.98(16) . . ?
O5 C19 C20 107.55(16) . . ?
N1 C19 C18 112.73(17) . . ?
N1 C19 C20 115.50(17) . . ?
C20 C19 C18 102.25(16) . . ?
C21 C20 C19 108.28(18) . . ?
C25 C20 C19 130.7(2) . . ?
C25 C20 C21 121.0(2) . . ?
C20 C21 N2 110.48(19) . . ?
C22 C21 N2 128.4(2) . . ?
C22 C21 C20 121.1(2) . . ?
C21 C22 H22 121.3 . . ?
C21 C22 C23 117.5(2) . . ?
C23 C22 H22 121.3 . . ?
C22 C23 H23 119.2 . . ?
C24 C23 C22 121.5(2) . . ?
C24 C23 H23 119.2 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.2(2) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 118.7(2) . . ?
C20 C25 H25 120.7 . . ?
C24 C25 H25 120.7 . . ?
N2 C26 H26A 109.5 . . ?
N2 C26 H26B 109.5 . . ?
N2 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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 C9 1.201(3) . ?
O2 C9 1.324(4) . ?
O2 C11 1.532(15) . ?
O2 C11A 1.464(4) . ?
O3 C13 1.208(3) . ?
O4 C13 1.326(3) . ?
O4 C14 1.484(2) . ?
O5 C7 1.451(3) . ?
O5 C19 1.413(2) . ?
O6 C18 1.211(3) . ?
N1 C5 1.429(3) . ?
N1 C13 1.380(3) . ?
N1 C19 1.475(3) . ?
N2 C18 1.365(3) . ?
N2 C21 1.404(3) . ?
N2 C26 1.448(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.372(4) . ?
C1 C6 1.382(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(3) . ?
C5 C6 1.393(3) . ?
C6 C7 1.507(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.516(3) . ?
C8 C9 1.468(4) . ?
C8 C10 1.320(4) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.548(19) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C11A C12A 1.476(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12A H12D 0.9600 . ?
C12A H12E 0.9600 . ?
C12A H12F 0.9600 . ?
C14 C15 1.514(4) . ?
C14 C16 1.509(4) . ?
C14 C17 1.507(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.564(3) . ?
C19 C20 1.504(3) . ?
C20 C21 1.390(3) . ?
C20 C25 1.368(3) . ?
C21 C22 1.378(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.393(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.381(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.390(3) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
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
O5 C7 C8 C9 155.2(2) . . . . ?
O5 C7 C8 C10 -27.6(3) . . . . ?
O5 C19 C20 C21 -107.57(19) . . . . ?
O5 C19 C20 C25 73.1(3) . . . . ?
O6 C18 C19 O5 -70.0(3) . . . . ?
O6 C18 C19 N1 52.1(3) . . . . ?
O6 C18 C19 C20 176.8(2) . . . . ?
N1 C5 C6 C1 -179.6(2) . . . . ?
N1 C5 C6 C7 -5.5(3) . . . . ?
N1 C19 C20 C21 128.80(19) . . . . ?
N1 C19 C20 C25 -50.6(3) . . . . ?
N2 C18 C19 O5 104.65(19) . . . . ?
N2 C18 C19 N1 -133.26(18) . . . . ?
N2 C18 C19 C20 -8.6(2) . . . . ?
N2 C21 C22 C23 -179.0(2) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
C1 C6 C7 O5 129.7(2) . . . . ?
C1 C6 C7 C8 14.1(3) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C2 C1 C6 C7 -173.9(3) . . . . ?
C2 C3 C4 C5 -1.6(4) . . . . ?
C3 C4 C5 N1 -179.5(2) . . . . ?
C3 C4 C5 C6 3.1(4) . . . . ?
C4 C5 C6 C1 -2.0(3) . . . . ?
C4 C5 C6 C7 172.0(2) . . . . ?
C5 N1 C13 O3 -171.3(2) . . . . ?
C5 N1 C13 O4 10.1(3) . . . . ?
C5 N1 C19 O5 -16.0(2) . . . . ?
C5 N1 C19 C18 -136.76(18) . . . . ?
C5 N1 C19 C20 106.2(2) . . . . ?
C5 C6 C7 O5 -43.9(2) . . . . ?
C5 C6 C7 C8 -159.6(2) . . . . ?
C6 C1 C2 C3 2.0(5) . . . . ?
C6 C7 C8 C9 -89.2(3) . . . . ?
C6 C7 C8 C10 88.0(3) . . . . ?
C7 O5 C19 N1 -38.2(2) . . . . ?
C7 O5 C19 C18 85.33(19) . . . . ?
C7 O5 C19 C20 -165.00(16) . . . . ?
C7 C8 C9 O1 -174.5(3) . . . . ?
C7 C8 C9 O2 5.8(3) . . . . ?
C9 O2 C11 C12 90(2) . . . . ?
C9 O2 C11A C12A 156.1(4) . . . . ?
C10 C8 C9 O1 8.1(4) . . . . ?
C10 C8 C9 O2 -171.6(3) . . . . ?
C11 O2 C9 O1 -13.3(13) . . . . ?
C11 O2 C9 C8 166.4(13) . . . . ?
C11A O2 C9 O1 -4.2(4) . . . . ?
C11A O2 C9 C8 175.6(3) . . . . ?
C13 O4 C14 C15 176.2(3) . . . . ?
C13 O4 C14 C16 -66.8(3) . . . . ?
C13 O4 C14 C17 56.6(3) . . . . ?
C13 N1 C5 C4 35.1(3) . . . . ?
C13 N1 C5 C6 -147.4(2) . . . . ?
C13 N1 C19 O5 169.32(17) . . . . ?
C13 N1 C19 C18 48.5(2) . . . . ?
C13 N1 C19 C20 -68.5(2) . . . . ?
C14 O4 C13 O3 9.4(4) . . . . ?
C14 O4 C13 N1 -172.11(18) . . . . ?
C18 N2 C21 C20 -4.6(3) . . . . ?
C18 N2 C21 C22 174.1(2) . . . . ?
C18 C19 C20 C21 6.0(2) . . . . ?
C18 C19 C20 C25 -173.4(2) . . . . ?
C19 O5 C7 C6 68.7(2) . . . . ?
C19 O5 C7 C8 -170.47(18) . . . . ?
C19 N1 C5 C4 -138.9(2) . . . . ?
C19 N1 C5 C6 38.6(3) . . . . ?
C19 N1 C13 O3 2.9(3) . . . . ?
C19 N1 C13 O4 -175.66(17) . . . . ?
C19 C20 C21 N2 -1.5(2) . . . . ?
C19 C20 C21 C22 179.7(2) . . . . ?
C19 C20 C25 C24 -179.3(2) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C21 N2 C18 O6 -177.1(2) . . . . ?
C21 N2 C18 C19 8.3(2) . . . . ?
C21 C20 C25 C24 1.5(3) . . . . ?
C21 C22 C23 C24 1.2(4) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C23 C24 C25 C20 -0.7(4) . . . . ?
C25 C20 C21 N2 177.9(2) . . . . ?
C25 C20 C21 C22 -0.9(3) . . . . ?
C26 N2 C18 O6 -3.2(4) . . . . ?
C26 N2 C18 C19 -177.7(2) . . . . ?
C26 N2 C21 C20 -178.5(2) . . . . ?
C26 N2 C21 C22 0.2(4) . . . . ?
