#------------------------------------------------------------------------------
#$Date: 2024-08-05 21:59:28 +0200 (Mon 05 de Aug de 2024) $
#$Revision: 293937 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/99/7159987.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_7159987
loop_
_publ_author_name
'Mamale, Ajay G.'
'Paul, Sayantan'
'Gonnade, Rajesh G.'
'Bhattacharya, Asish K.'
_publ_section_title
;
 1,6-Conjugate addition of in situ generated aryldiazenes to
 p-quinone methides.
;
_journal_issue                   27
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5636
_journal_page_last               5645
_journal_paper_doi               10.1039/d4ob00618f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C28 H33 N3 O4'
_chemical_formula_sum            'C28 H33 N3 O4'
_chemical_formula_weight         475.57
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'difference Fourier'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-08-17 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.653(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2116(9)
_cell_length_b                   19.3030(17)
_cell_length_c                   10.9565(9)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      2.21
_cell_volume                     2474.3(4)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1164
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            134255
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.364
_diffrn_reflns_theta_min         2.736
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.2092
_exptl_absorpt_correction_T_min  0.1748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         6174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0450
_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)+(0.0397P)²+1.3550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1151
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4263
_reflns_number_total             6174
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00618f2.cif
_cod_data_source_block           mo_aR_5L_0ma_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'direct method' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159985--7159987.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159987
_shelx_shelxl_version_number     2018/3
_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_min   0.989
_shelx_estimated_absorpt_t_max   0.991
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 0.72189(11) 0.36129(8) 1.09816(13) 0.0449(4) Uani 1 1 d . . . . .
H1 H -0.0919(19) 0.6722(13) 0.382(2) 0.052(7) Uiso 1 1 d . . . . .
O2 O 0.76156(10) 0.43091(7) 0.96300(13) 0.0340(3) Uani 1 1 d . . . . .
O3 O -0.06446(9) 0.63451(6) 0.35694(11) 0.0206(2) Uani 1 1 d . . . . .
O4 O 0.72274(9) 0.71627(6) 0.32081(11) 0.0254(3) Uani 1 1 d . . . . .
N1 N 0.45605(11) 0.55477(7) 0.64889(13) 0.0210(3) Uani 1 1 d . . . . .
N2 N 0.38281(11) 0.52443(7) 0.70629(13) 0.0230(3) Uani 1 1 d . . . . .
H2N H 0.3051(17) 0.5303(10) 0.6731(18) 0.032(5) Uiso 1 1 d . . . . .
N3 N 0.69304(12) 0.40105(8) 1.00721(14) 0.0273(3) Uani 1 1 d . . . . .
C1 C 0.41139(13) 0.59383(8) 0.55111(14) 0.0185(3) Uani 1 1 d . . . . .
C2 C 0.42231(13) 0.47547(8) 0.80089(15) 0.0207(3) Uani 1 1 d . . . . .
C3 C 0.53862(13) 0.46202(8) 0.85307(15) 0.0214(3) Uani 1 1 d . . . . .
H3 H 0.594316 0.485395 0.823074 0.026 Uiso 1 1 calc R U . . .
C4 C 0.57022(13) 0.41372(8) 0.94956(15) 0.0226(3) Uani 1 1 d . . . . .
C5 C 0.49343(15) 0.37719(9) 0.99629(16) 0.0267(4) Uani 1 1 d . . . . .
H5 H 0.518548 0.344059 1.062551 0.032 Uiso 1 1 calc R U . . .
C6 C 0.37851(15) 0.39096(9) 0.94241(17) 0.0282(4) Uani 1 1 d . . . . .
H6 H 0.323278 0.366760 0.971901 0.034 Uiso 1 1 calc R U . . .
C7 C 0.34291(14) 0.43936(9) 0.84642(16) 0.0252(4) Uani 1 1 d . . . . .
H7 H 0.263593 0.448211 0.810951 0.030 Uiso 1 1 calc R U . . .
C8 C 0.28566(13) 0.60626(8) 0.50076(14) 0.0181(3) Uani 1 1 d . . . . .
C9 C 0.23379(13) 0.66001(8) 0.54704(14) 0.0187(3) Uani 1 1 d . . . . .
H9 H 0.279455 0.689000 0.611938 0.022 Uiso 1 1 calc R U . . .
C10 C 0.11653(13) 0.67301(8) 0.50147(14) 0.0170(3) Uani 1 1 d . . . . .
C11 C 0.05206(12) 0.62751(8) 0.40790(14) 0.0165(3) Uani 1 1 d . . . . .
C12 C 0.10090(12) 0.57103(8) 0.36077(14) 0.0167(3) Uani 1 1 d . . . . .
C13 C 0.21873(13) 0.56291(8) 0.40794(14) 0.0180(3) Uani 1 1 d . . . . .
H13 H 0.254590 0.526452 0.375497 0.022 Uiso 1 1 calc R U . . .
C14 C 0.06404(13) 0.73493(8) 0.55363(14) 0.0181(3) Uani 1 1 d . . . . .
C15 C 0.15402(14) 0.77263(8) 0.66031(15) 0.0228(3) Uani 1 1 d . . . . .
H15A H 0.215290 0.789904 0.627023 0.034 Uiso 1 1 calc R U . . .
H15B H 0.186020 0.740378 0.730564 0.034 Uiso 1 1 calc R U . . .
H15C H 0.118062 0.811636 0.691308 0.034 Uiso 1 1 calc R U . . .
C16 C -0.03018(14) 0.71166(9) 0.61229(16) 0.0242(3) Uani 1 1 d . . . . .
H16A H -0.094013 0.691870 0.545656 0.036 Uiso 1 1 calc R U . . .
H16B H -0.057141 0.751633 0.650697 0.036 Uiso 1 1 calc R U . . .
H16C H 0.000554 0.676629 0.677922 0.036 Uiso 1 1 calc R U . . .
C17 C 0.01592(14) 0.78805(8) 0.44772(15) 0.0225(3) Uani 1 1 d . . . . .
H17A H 0.078164 0.806444 0.417271 0.034 Uiso 1 1 calc R U . . .
H17B H -0.020284 0.826039 0.481177 0.034 Uiso 1 1 calc R U . . .
H17C H -0.040869 0.765616 0.377035 0.034 Uiso 1 1 calc R U . . .
C18 C 0.02878(13) 0.51907(8) 0.26416(14) 0.0181(3) Uani 1 1 d . . . . .
C19 C -0.05568(13) 0.48233(8) 0.32316(15) 0.0213(3) Uani 1 1 d . . . . .
H19A H -0.105109 0.451497 0.259803 0.032 Uiso 1 1 calc R U . . .
H19B H -0.102627 0.516956 0.350192 0.032 Uiso 1 1 calc R U . . .
H19C H -0.013097 0.455142 0.397079 0.032 Uiso 1 1 calc R U . . .
C20 C -0.03392(14) 0.55518(8) 0.13828(15) 0.0212(3) Uani 1 1 d . . . . .
H20A H 0.022121 0.572587 0.097195 0.032 Uiso 1 1 calc R U . . .
H20B H -0.078982 0.593951 0.155802 0.032 Uiso 1 1 calc R U . . .
H20C H -0.084815 0.521985 0.081687 0.032 Uiso 1 1 calc R U . . .
C21 C 0.10295(14) 0.46206(8) 0.23003(15) 0.0223(3) Uani 1 1 d . . . . .
H21A H 0.053998 0.429658 0.169570 0.033 Uiso 1 1 calc R U . . .
H21B H 0.144115 0.437080 0.307457 0.033 Uiso 1 1 calc R U . . .
H21C H 0.158006 0.483110 0.191321 0.033 Uiso 1 1 calc R U . . .
C22 C 0.48966(13) 0.62561(8) 0.48665(15) 0.0190(3) Uani 1 1 d . . . . .
C23 C 0.45371(13) 0.67870(8) 0.39802(15) 0.0222(3) Uani 1 1 d . . . . .
H23 H 0.376499 0.693793 0.376998 0.027 Uiso 1 1 calc R U . . .
C24 C 0.52812(13) 0.71023(8) 0.33939(15) 0.0224(3) Uani 1 1 d . . . . .
H24 H 0.501944 0.746574 0.279690 0.027 Uiso 1 1 calc R U . . .
C25 C 0.64075(13) 0.68805(8) 0.36902(15) 0.0209(3) Uani 1 1 d . . . . .
C26 C 0.67668(13) 0.63278(8) 0.45356(15) 0.0221(3) Uani 1 1 d . . . . .
H26 H 0.752611 0.615817 0.470732 0.026 Uiso 1 1 calc R U . . .
C27 C 0.60293(13) 0.60295(8) 0.51178(15) 0.0208(3) Uani 1 1 d . . . . .
H27 H 0.629186 0.566138 0.570417 0.025 Uiso 1 1 calc R U . . .
C28 C 0.68853(15) 0.77262(9) 0.23313(17) 0.0295(4) Uani 1 1 d . . . . .
H28A H 0.754073 0.788284 0.205689 0.044 Uiso 1 1 calc R U . . .
H28B H 0.660709 0.810917 0.274889 0.044 Uiso 1 1 calc R U . . .
H28C H 0.627395 0.757217 0.158805 0.044 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C11 O3 H1 113.5(15) . . ?
C25 O4 C28 117.08(12) . . ?
C1 N1 N2 117.06(13) . . ?
N1 N2 C2 120.32(13) . . ?
N1 N2 H2N 120.2(12) . . ?
C2 N2 H2N 118.6(12) . . ?
O2 N3 O1 123.10(14) . . ?
O2 N3 C4 118.68(14) . . ?
O1 N3 C4 118.22(14) . . ?
N1 C1 C22 117.45(13) . . ?
N1 C1 C8 122.89(14) . . ?
C22 C1 C8 119.65(13) . . ?
N2 C2 C3 121.99(14) . . ?
N2 C2 C7 118.66(14) . . ?
C3 C2 C7 119.34(15) . . ?
C4 C3 C2 117.93(15) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 123.91(15) . . ?
C3 C4 N3 117.93(14) . . ?
C5 C4 N3 118.16(14) . . ?
C6 C5 C4 117.15(16) . . ?
C6 C5 H5 121.4 . . ?
C4 C5 H5 121.4 . . ?
C7 C6 C5 120.97(16) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 120.68(15) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C9 C8 C13 119.00(14) . . ?
C9 C8 C1 120.94(14) . . ?
C13 C8 C1 120.05(13) . . ?
C8 C9 C10 122.20(14) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C9 C10 C11 116.77(13) . . ?
C9 C10 C14 119.95(13) . . ?
C11 C10 C14 123.29(13) . . ?
O3 C11 C10 122.09(13) . . ?
O3 C11 C12 115.05(13) . . ?
C10 C11 C12 122.86(13) . . ?
C13 C12 C11 116.87(13) . . ?
C13 C12 C18 120.61(13) . . ?
C11 C12 C18 122.50(13) . . ?
C8 C13 C12 122.24(14) . . ?
C8 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C17 C14 C16 109.96(13) . . ?
C17 C14 C15 107.09(13) . . ?
C16 C14 C15 106.13(13) . . ?
C17 C14 C10 110.35(12) . . ?
C16 C14 C10 111.66(13) . . ?
C15 C14 C10 111.48(12) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C21 C18 C19 106.54(12) . . ?
C21 C18 C12 111.89(12) . . ?
C19 C18 C12 109.38(12) . . ?
C21 C18 C20 106.41(12) . . ?
C19 C18 C20 111.35(12) . . ?
C12 C18 C20 111.16(12) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 117.57(14) . . ?
C23 C22 C1 121.44(14) . . ?
C27 C22 C1 120.99(14) . . ?
C22 C23 C24 121.69(14) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C25 C24 C23 119.40(15) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
O4 C25 C24 124.85(15) . . ?
O4 C25 C26 115.66(13) . . ?
C24 C25 C26 119.49(15) . . ?
C27 C26 C25 120.36(14) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C22 121.39(15) . . ?
C26 C27 H27 119.3 . . ?
C22 C27 H27 119.3 . . ?
O4 C28 H28A 109.5 . . ?
O4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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 N3 1.2268(18) . ?
O2 N3 1.2245(18) . ?
O3 C11 1.3782(17) . ?
O3 H1 0.88(2) . ?
O4 C25 1.3715(19) . ?
O4 C28 1.432(2) . ?
N1 C1 1.296(2) . ?
N1 N2 1.3641(18) . ?
N2 C2 1.383(2) . ?
N2 H2N 0.92(2) . ?
N3 C4 1.472(2) . ?
C1 C22 1.475(2) . ?
C1 C8 1.495(2) . ?
C2 C3 1.395(2) . ?
C2 C7 1.397(2) . ?
C3 C4 1.379(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(2) . ?
C5 C6 1.383(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.385(2) . ?
C8 C13 1.388(2) . ?
C9 C10 1.397(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.407(2) . ?
C10 C14 1.541(2) . ?
C11 C12 1.410(2) . ?
C12 C13 1.391(2) . ?
C12 C18 1.539(2) . ?
C13 H13 0.9500 . ?
C14 C17 1.534(2) . ?
C14 C16 1.537(2) . ?
C14 C15 1.539(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C21 1.538(2) . ?
C18 C19 1.538(2) . ?
C18 C20 1.539(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.393(2) . ?
C22 C27 1.401(2) . ?
C23 C24 1.394(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.398(2) . ?
C26 C27 1.371(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
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
_geom_hbond_publ_flag
O3 H1 O4 0.88(2) 2.33(2) 2.9683(15) 129.8(19) 1_455 yes
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
C1 N1 N2 C2 171.98(14) . . . . ?
N2 N1 C1 C22 -178.66(13) . . . . ?
N2 N1 C1 C8 0.0(2) . . . . ?
N1 N2 C2 C3 8.8(2) . . . . ?
N1 N2 C2 C7 -172.21(15) . . . . ?
N2 C2 C3 C4 178.16(15) . . . . ?
C7 C2 C3 C4 -0.8(2) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C2 C3 C4 N3 -178.21(14) . . . . ?
O2 N3 C4 C3 -3.8(2) . . . . ?
O1 N3 C4 C3 175.66(16) . . . . ?
O2 N3 C4 C5 176.95(15) . . . . ?
O1 N3 C4 C5 -3.6(2) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
N3 C4 C5 C6 178.73(15) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C2 0.3(3) . . . . ?
N2 C2 C7 C6 -178.79(16) . . . . ?
C3 C2 C7 C6 0.2(2) . . . . ?
N1 C1 C8 C9 88.59(19) . . . . ?
C22 C1 C8 C9 -92.81(18) . . . . ?
N1 C1 C8 C13 -90.24(19) . . . . ?
C22 C1 C8 C13 88.36(18) . . . . ?
C13 C8 C9 C10 -1.4(2) . . . . ?
C1 C8 C9 C10 179.77(14) . . . . ?
C8 C9 C10 C11 1.7(2) . . . . ?
C8 C9 C10 C14 -178.14(14) . . . . ?
C9 C10 C11 O3 179.13(13) . . . . ?
C14 C10 C11 O3 -1.1(2) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C14 C10 C11 C12 179.97(14) . . . . ?
O3 C11 C12 C13 178.77(13) . . . . ?
C10 C11 C12 C13 -2.2(2) . . . . ?
O3 C11 C12 C18 -2.7(2) . . . . ?
C10 C11 C12 C18 176.37(14) . . . . ?
C9 C8 C13 C12 -0.8(2) . . . . ?
C1 C8 C13 C12 178.03(14) . . . . ?
C11 C12 C13 C8 2.5(2) . . . . ?
C18 C12 C13 C8 -176.06(14) . . . . ?
C9 C10 C14 C17 115.36(15) . . . . ?
C11 C10 C14 C17 -64.45(18) . . . . ?
C9 C10 C14 C16 -122.02(15) . . . . ?
C11 C10 C14 C16 58.16(19) . . . . ?
C9 C10 C14 C15 -3.51(19) . . . . ?
C11 C10 C14 C15 176.68(14) . . . . ?
C13 C12 C18 C21 -0.74(19) . . . . ?
C11 C12 C18 C21 -179.24(13) . . . . ?
C13 C12 C18 C19 117.07(15) . . . . ?
C11 C12 C18 C19 -61.43(18) . . . . ?
C13 C12 C18 C20 -119.56(15) . . . . ?
C11 C12 C18 C20 61.94(18) . . . . ?
N1 C1 C22 C23 -166.98(15) . . . . ?
C8 C1 C22 C23 14.3(2) . . . . ?
N1 C1 C22 C27 13.6(2) . . . . ?
C8 C1 C22 C27 -165.12(14) . . . . ?
C27 C22 C23 C24 -2.3(2) . . . . ?
C1 C22 C23 C24 178.21(15) . . . . ?
C22 C23 C24 C25 0.5(2) . . . . ?
C28 O4 C25 C24 -0.2(2) . . . . ?
C28 O4 C25 C26 179.52(14) . . . . ?
C23 C24 C25 O4 -177.92(15) . . . . ?
C23 C24 C25 C26 2.3(2) . . . . ?
O4 C25 C26 C27 176.96(14) . . . . ?
C24 C25 C26 C27 -3.3(2) . . . . ?
C25 C26 C27 C22 1.4(2) . . . . ?
C23 C22 C27 C26 1.4(2) . . . . ?
C1 C22 C27 C26 -179.15(15) . . . . ?
