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#$Date: 2024-07-05 20:36:13 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293190 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/32/7063215.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_7063215
loop_
_publ_author_name
'Krishnan, Ashokkumar'
'Kamaraj, Sriraghavan'
_publ_section_title
;
 High-yielding regioselective synthesis of p-quinone fused
 5-substituted-1,4-benzodiazepine scaffolds via Pictet--Spengler type
 cycloannulation
;
_journal_issue                   22
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10045
_journal_page_last               10052
_journal_paper_doi               10.1039/D4NJ00993B
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C35 H26 F3 N3 O2'
_chemical_formula_sum            'C35 H26 F3 N3 O2'
_chemical_formula_weight         577.59
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-07-12 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                106.897(2)
_cell_angle_beta                 95.882(2)
_cell_angle_gamma                109.7260(10)
_cell_formula_units_Z            2
_cell_length_a                   10.8114(5)
_cell_length_b                   11.3929(5)
_cell_length_c                   12.8702(6)
_cell_measurement_reflns_used    9271
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      25.06
_cell_measurement_theta_min      2.26
_cell_volume                     1391.96(11)
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            39038
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.337
_diffrn_reflns_theta_min         2.025
_diffrn_source                   'i-mu-s microfocus source'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         6939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0729
_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)+(0.1168P)²+0.7156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1951
_refine_ls_wR_factor_ref         0.2429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4004
_reflns_number_total             6939
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj00993b2.cif
_cod_data_source_block           KSA_5_230623_0m_a
_cod_depositor_comments
'Adding full bibliography for 7063215--7063217.cif.'
_cod_database_code               7063215
_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   0.973
_shelx_estimated_absorpt_t_max   0.994
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
F1 F 0.9170(4) 0.0862(4) 0.1053(5) 0.226(3) Uani 1 1 d . . . . .
F2 F 0.7251(4) -0.0333(3) 0.0433(5) 0.222(3) Uani 1 1 d . . . . .
F3 F 0.8279(7) 0.0756(6) -0.0361(4) 0.245(3) Uani 1 1 d . . . . .
O1 O 0.28448(18) 0.1424(2) 0.38781(17) 0.0561(5) Uani 1 1 d . . . . .
O2 O 0.78994(19) 0.50283(19) 0.56949(16) 0.0576(5) Uani 1 1 d . . . . .
N1 N 0.6742(2) 0.2780(2) 0.65010(17) 0.0450(5) Uani 1 1 d . . . . .
N2 N 0.3802(2) 0.3143(2) 0.2915(2) 0.0539(6) Uani 1 1 d . . . . .
H1 H 0.298(4) 0.249(4) 0.279(3) 0.081 Uiso 1 1 d . U . . .
N3 N 0.6513(2) 0.5282(2) 0.39878(18) 0.0464(5) Uani 1 1 d . . . . .
H1B H 0.744(3) 0.575(3) 0.436(3) 0.070 Uiso 1 1 d . U . . .
C1 C 0.4584(3) 0.1261(2) 0.5830(2) 0.0423(6) Uani 1 1 d . . . . .
C2 C 0.5794(3) 0.1663(3) 0.6610(2) 0.0444(6) Uani 1 1 d . . . . .
C3 C 0.5916(3) 0.1000(3) 0.7340(2) 0.0560(7) Uani 1 1 d . . . . .
H3 H 0.672038 0.127141 0.784892 0.067 Uiso 1 1 calc R U . . .
C4 C 0.4802(3) -0.0071(3) 0.7279(3) 0.0603(8) Uani 1 1 d . . . . .
H4 H 0.485426 -0.053210 0.776060 0.072 Uiso 1 1 calc R U . . .
C5 C 0.3592(3) -0.0491(3) 0.6514(2) 0.0573(7) Uani 1 1 d . . . . .
H5 H 0.285599 -0.122000 0.649842 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3471(3) 0.0156(3) 0.5785(2) 0.0484(6) Uani 1 1 d . . . . .
H6 H 0.266558 -0.013340 0.527216 0.058 Uiso 1 1 calc R U . . .
C7 C 0.4837(2) 0.2161(2) 0.5238(2) 0.0412(6) Uani 1 1 d . . . . .
C8 C 0.6146(2) 0.3068(2) 0.5670(2) 0.0419(6) Uani 1 1 d . . . . .
C9 C 0.4018(3) 0.2199(3) 0.4297(2) 0.0429(6) Uani 1 1 d . . . . .
C10 C 0.4666(3) 0.3252(3) 0.3825(2) 0.0432(6) Uani 1 1 d . . . . .
C11 C 0.5921(2) 0.4205(2) 0.4316(2) 0.0407(6) Uani 1 1 d . . . . .
C12 C 0.6751(3) 0.4167(2) 0.5271(2) 0.0425(6) Uani 1 1 d . . . . .
C13 C 0.3842(3) 0.3938(3) 0.2257(2) 0.0465(6) Uani 1 1 d . . . . .
C14 C 0.5034(3) 0.4916(3) 0.2223(2) 0.0446(6) Uani 1 1 d . . . . .
C15 C 0.6391(3) 0.5055(3) 0.2787(2) 0.0457(6) Uani 1 1 d . . . . .
H15 H 0.704783 0.586005 0.273074 0.055 Uiso 1 1 calc R U . . .
C16 C 0.2617(3) 0.3670(3) 0.1589(2) 0.0528(7) Uani 1 1 d . . . . .
H16 H 0.184687 0.298971 0.159611 0.063 Uiso 1 1 calc R U . . .
C17 C 0.2523(3) 0.4398(3) 0.0914(2) 0.0551(7) Uani 1 1 d . . . . .
C18 C 0.3675(3) 0.5428(3) 0.0947(2) 0.0542(7) Uani 1 1 d . . . . .
H18 H 0.361451 0.595911 0.053114 0.065 Uiso 1 1 calc R U . . .
C19 C 0.4920(3) 0.5698(3) 0.1582(2) 0.0482(6) Uani 1 1 d . . . . .
C20 C 0.8148(3) 0.3415(3) 0.7114(2) 0.0498(7) Uani 1 1 d . . . . .
H20A H 0.818643 0.339308 0.786400 0.060 Uiso 1 1 calc R U . . .
H20B H 0.849465 0.434022 0.716921 0.060 Uiso 1 1 calc R U . . .
C21 C 0.9040(3) 0.2766(3) 0.6583(2) 0.0497(7) Uani 1 1 d . . . . .
C22 C 0.9421(3) 0.2925(3) 0.5616(2) 0.0567(7) Uani 1 1 d . . . . .
H22 H 0.910693 0.342632 0.528470 0.068 Uiso 1 1 calc R U . . .
C23 C 1.0259(3) 0.2349(3) 0.5141(3) 0.0693(9) Uani 1 1 d . . . . .
H23 H 1.049193 0.244955 0.448760 0.083 Uiso 1 1 calc R U . . .
C24 C 1.0744(3) 0.1634(3) 0.5630(4) 0.0784(11) Uani 1 1 d . . . . .
H24 H 1.132528 0.126601 0.531599 0.094 Uiso 1 1 calc R U . . .
C25 C 1.0384(3) 0.1450(4) 0.6578(4) 0.0791(11) Uani 1 1 d . . . . .
H25 H 1.070779 0.094791 0.689962 0.095 Uiso 1 1 calc R U . . .
C26 C 0.9529(3) 0.2021(3) 0.7060(3) 0.0629(8) Uani 1 1 d . . . . .
H26 H 0.928752 0.189980 0.770571 0.075 Uiso 1 1 calc R U . . .
C27 C 0.6796(3) 0.3906(3) 0.2194(2) 0.0446(6) Uani 1 1 d . . . . .
C28 C 0.6024(3) 0.2895(3) 0.1209(2) 0.0532(7) Uani 1 1 d . . . . .
H28 H 0.520868 0.288702 0.088970 0.064 Uiso 1 1 calc R U . . .
C29 C 0.6444(3) 0.1894(3) 0.0689(3) 0.0596(8) Uani 1 1 d . . . . .
H29 H 0.590978 0.122523 0.002677 0.071 Uiso 1 1 calc R U . . .
C30 C 0.7642(3) 0.1885(3) 0.1147(3) 0.0604(8) Uani 1 1 d . . . . .
C31 C 0.8428(3) 0.2882(4) 0.2129(3) 0.0692(9) Uani 1 1 d . . . . .
H31 H 0.924420 0.288557 0.244132 0.083 Uiso 1 1 calc R U . . .
C32 C 0.8006(3) 0.3877(3) 0.2649(3) 0.0636(8) Uani 1 1 d . . . . .
H32 H 0.853990 0.453886 0.331510 0.076 Uiso 1 1 calc R U . . .
C33 C 0.1201(3) 0.4078(4) 0.0170(3) 0.0760(10) Uani 1 1 d . . . . .
H33A H 0.132863 0.465828 -0.025567 0.114 Uiso 1 1 calc R U . . .
H33B H 0.056502 0.419987 0.061753 0.114 Uiso 1 1 calc R U . . .
H33C H 0.086334 0.317155 -0.032517 0.114 Uiso 1 1 calc R U . . .
C34 C 0.6131(3) 0.6845(3) 0.1564(3) 0.0599(8) Uani 1 1 d . . . . .
H34A H 0.585251 0.726700 0.109151 0.090 Uiso 1 1 calc R U . . .
H34B H 0.678424 0.651686 0.128209 0.090 Uiso 1 1 calc R U . . .
H34C H 0.652355 0.747713 0.230544 0.090 Uiso 1 1 calc R U . . .
C35 C 0.8056(4) 0.0793(4) 0.0604(4) 0.0848(11) Uani 1 1 d . . . . .
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'
F F 0.0171 0.0103 '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
C8 N1 C2 107.8(2) . . ?
C8 N1 C20 127.9(2) . . ?
C2 N1 C20 124.1(2) . . ?
C10 N2 C13 133.8(2) . . ?
C10 N2 H1 111(2) . . ?
C13 N2 H1 114(2) . . ?
C11 N3 C15 118.6(2) . . ?
C11 N3 H1B 111(2) . . ?
C15 N3 H1B 109.2(19) . . ?
C6 C1 C2 119.1(2) . . ?
C6 C1 C7 134.7(3) . . ?
C2 C1 C7 106.2(2) . . ?
C3 C2 N1 129.4(3) . . ?
C3 C2 C1 122.1(3) . . ?
N1 C2 C1 108.5(2) . . ?
C4 C3 C2 117.2(3) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C3 C4 C5 121.9(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
C8 C7 C1 107.7(2) . . ?
C8 C7 C9 120.5(2) . . ?
C1 C7 C9 131.6(2) . . ?
N1 C8 C7 109.8(2) . . ?
N1 C8 C12 127.3(2) . . ?
C7 C8 C12 122.9(2) . . ?
O1 C9 C7 123.7(2) . . ?
O1 C9 C10 119.5(2) . . ?
C7 C9 C10 116.8(2) . . ?
C11 C10 N2 127.2(2) . . ?
C11 C10 C9 121.8(2) . . ?
N2 C10 C9 110.8(2) . . ?
C10 C11 N3 124.3(2) . . ?
C10 C11 C12 121.0(2) . . ?
N3 C11 C12 114.6(2) . . ?
O2 C12 C8 123.3(2) . . ?
O2 C12 C11 120.2(2) . . ?
C8 C12 C11 116.5(2) . . ?
C16 C13 N2 115.7(2) . . ?
C16 C13 C14 120.7(2) . . ?
N2 C13 C14 123.6(2) . . ?
C19 C14 C13 117.7(2) . . ?
C19 C14 C15 121.1(2) . . ?
C13 C14 C15 121.1(2) . . ?
N3 C15 C14 112.7(2) . . ?
N3 C15 C27 112.1(2) . . ?
C14 C15 C27 112.9(2) . . ?
N3 C15 H15 106.2 . . ?
C14 C15 H15 106.2 . . ?
C27 C15 H15 106.2 . . ?
C17 C16 C13 121.1(3) . . ?
C17 C16 H16 119.4 . . ?
C13 C16 H16 119.4 . . ?
C18 C17 C16 118.1(3) . . ?
C18 C17 C33 121.1(3) . . ?
C16 C17 C33 120.8(3) . . ?
C17 C18 C19 122.1(3) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C18 C19 C14 120.0(3) . . ?
C18 C19 C34 118.5(3) . . ?
C14 C19 C34 121.6(3) . . ?
N1 C20 C21 113.5(2) . . ?
N1 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
N1 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C26 C21 C22 118.2(3) . . ?
C26 C21 C20 120.8(3) . . ?
C22 C21 C20 121.0(3) . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.1(4) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.6(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C26 119.7(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C21 C26 C25 120.5(3) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C28 C27 C32 117.6(3) . . ?
C28 C27 C15 123.2(2) . . ?
C32 C27 C15 119.2(2) . . ?
C27 C28 C29 121.3(3) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 H28 119.3 . . ?
C30 C29 C28 120.3(3) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 119.4(3) . . ?
C29 C30 C35 119.8(3) . . ?
C31 C30 C35 120.8(3) . . ?
C30 C31 C32 120.2(3) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C31 C32 C27 121.2(3) . . ?
C31 C32 H32 119.4 . . ?
C27 C32 H32 119.4 . . ?
C17 C33 H33A 109.5 . . ?
C17 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C17 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C19 C34 H34A 109.5 . . ?
C19 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C19 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
F2 C35 F1 106.5(5) . . ?
F2 C35 F3 103.3(5) . . ?
F1 C35 F3 98.8(4) . . ?
F2 C35 C30 116.2(3) . . ?
F1 C35 C30 116.4(4) . . ?
F3 C35 C30 113.4(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
F1 C35 1.248(5) . ?
F2 C35 1.223(5) . ?
F3 C35 1.281(5) . ?
O1 C9 1.227(3) . ?
O2 C12 1.237(3) . ?
N1 C8 1.369(3) . ?
N1 C2 1.394(3) . ?
N1 C20 1.461(3) . ?
N2 C10 1.369(3) . ?
N2 C13 1.402(3) . ?
N2 H1 0.91(4) . ?
N3 C11 1.384(3) . ?
N3 C15 1.475(3) . ?
N3 H1B 0.95(3) . ?
C1 C6 1.399(4) . ?
C1 C2 1.410(4) . ?
C1 C7 1.419(3) . ?
C2 C3 1.387(4) . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.378(3) . ?
C7 C9 1.444(4) . ?
C8 C12 1.465(4) . ?
C9 C10 1.498(4) . ?
C10 C11 1.361(3) . ?
C11 C12 1.466(4) . ?
C13 C16 1.388(4) . ?
C13 C14 1.405(4) . ?
C14 C19 1.403(4) . ?
C14 C15 1.503(4) . ?
C15 C27 1.537(4) . ?
C15 H15 0.9800 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(4) . ?
C17 C33 1.502(4) . ?
C18 C19 1.387(4) . ?
C18 H18 0.9300 . ?
C19 C34 1.513(4) . ?
C20 C21 1.505(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C26 1.385(4) . ?
C21 C22 1.393(4) . ?
C22 C23 1.381(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.361(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.369(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.397(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.384(4) . ?
C27 C32 1.392(4) . ?
C28 C29 1.386(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.371(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.380(5) . ?
C30 C35 1.473(5) . ?
C31 C32 1.383(4) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
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
N2 H1 O1 0.91(4) 2.08(4) 2.598(3) 115(3) . yes
N3 H1B O2 0.95(3) 2.19(3) 2.673(3) 110(2) . yes
C20 H20B O2 0.97 2.36 2.995(3) 122.0 . 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
C8 N1 C2 C3 -179.6(3) . . . . ?
C20 N1 C2 C3 5.6(4) . . . . ?
C8 N1 C2 C1 -0.3(3) . . . . ?
C20 N1 C2 C1 -175.1(2) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C7 C1 C2 C3 180.0(2) . . . . ?
C6 C1 C2 N1 -179.6(2) . . . . ?
C7 C1 C2 N1 0.6(3) . . . . ?
N1 C2 C3 C4 178.9(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C7 C1 C6 C5 -179.5(3) . . . . ?
C6 C1 C7 C8 179.5(3) . . . . ?
C2 C1 C7 C8 -0.7(3) . . . . ?
C6 C1 C7 C9 -4.6(5) . . . . ?
C2 C1 C7 C9 175.2(2) . . . . ?
C2 N1 C8 C7 -0.2(3) . . . . ?
C20 N1 C8 C7 174.4(2) . . . . ?
C2 N1 C8 C12 179.2(2) . . . . ?
C20 N1 C8 C12 -6.3(4) . . . . ?
C1 C7 C8 N1 0.6(3) . . . . ?
C9 C7 C8 N1 -175.9(2) . . . . ?
C1 C7 C8 C12 -178.8(2) . . . . ?
C9 C7 C8 C12 4.7(4) . . . . ?
C8 C7 C9 O1 -179.6(2) . . . . ?
C1 C7 C9 O1 4.9(4) . . . . ?
C8 C7 C9 C10 0.4(3) . . . . ?
C1 C7 C9 C10 -175.1(2) . . . . ?
C13 N2 C10 C11 -4.6(5) . . . . ?
C13 N2 C10 C9 171.8(3) . . . . ?
O1 C9 C10 C11 174.2(2) . . . . ?
C7 C9 C10 C11 -5.8(3) . . . . ?
O1 C9 C10 N2 -2.4(3) . . . . ?
C7 C9 C10 N2 177.6(2) . . . . ?
N2 C10 C11 N3 3.1(4) . . . . ?
C9 C10 C11 N3 -172.8(2) . . . . ?
N2 C10 C11 C12 -178.0(2) . . . . ?
C9 C10 C11 C12 6.0(4) . . . . ?
C15 N3 C11 C10 -43.8(4) . . . . ?
C15 N3 C11 C12 137.3(2) . . . . ?
N1 C8 C12 O2 -3.5(4) . . . . ?
C7 C8 C12 O2 175.8(2) . . . . ?
N1 C8 C12 C11 176.1(2) . . . . ?
C7 C8 C12 C11 -4.6(3) . . . . ?
C10 C11 C12 O2 178.7(2) . . . . ?
N3 C11 C12 O2 -2.4(3) . . . . ?
C10 C11 C12 C8 -0.9(3) . . . . ?
N3 C11 C12 C8 178.1(2) . . . . ?
C10 N2 C13 C16 -163.4(3) . . . . ?
C10 N2 C13 C14 19.0(5) . . . . ?
C16 C13 C14 C19 6.4(4) . . . . ?
N2 C13 C14 C19 -176.1(2) . . . . ?
C16 C13 C14 C15 -169.4(2) . . . . ?
N2 C13 C14 C15 8.2(4) . . . . ?
C11 N3 C15 C14 78.2(3) . . . . ?
C11 N3 C15 C27 -50.4(3) . . . . ?
C19 C14 C15 N3 127.1(3) . . . . ?
C13 C14 C15 N3 -57.3(3) . . . . ?
C19 C14 C15 C27 -104.7(3) . . . . ?
C13 C14 C15 C27 70.9(3) . . . . ?
N2 C13 C16 C17 179.1(3) . . . . ?
C14 C13 C16 C17 -3.1(4) . . . . ?
C13 C16 C17 C18 -2.0(4) . . . . ?
C13 C16 C17 C33 178.4(3) . . . . ?
C16 C17 C18 C19 3.8(4) . . . . ?
C33 C17 C18 C19 -176.6(3) . . . . ?
C17 C18 C19 C14 -0.4(4) . . . . ?
C17 C18 C19 C34 179.7(3) . . . . ?
C13 C14 C19 C18 -4.6(4) . . . . ?
C15 C14 C19 C18 171.2(2) . . . . ?
C13 C14 C19 C34 175.2(2) . . . . ?
C15 C14 C19 C34 -9.0(4) . . . . ?
C8 N1 C20 C21 -90.0(3) . . . . ?
C2 N1 C20 C21 83.7(3) . . . . ?
N1 C20 C21 C26 -108.1(3) . . . . ?
N1 C20 C21 C22 73.5(3) . . . . ?
C26 C21 C22 C23 0.4(4) . . . . ?
C20 C21 C22 C23 178.8(3) . . . . ?
C21 C22 C23 C24 -1.2(5) . . . . ?
C22 C23 C24 C25 1.6(5) . . . . ?
C23 C24 C25 C26 -1.1(5) . . . . ?
C22 C21 C26 C25 0.1(4) . . . . ?
C20 C21 C26 C25 -178.4(3) . . . . ?
C24 C25 C26 C21 0.2(5) . . . . ?
N3 C15 C27 C28 132.0(3) . . . . ?
C14 C15 C27 C28 3.5(3) . . . . ?
N3 C15 C27 C32 -49.0(3) . . . . ?
C14 C15 C27 C32 -177.5(2) . . . . ?
C32 C27 C28 C29 -0.4(4) . . . . ?
C15 C27 C28 C29 178.5(2) . . . . ?
C27 C28 C29 C30 0.1(4) . . . . ?
C28 C29 C30 C31 -0.1(5) . . . . ?
C28 C29 C30 C35 178.1(3) . . . . ?
C29 C30 C31 C32 0.4(5) . . . . ?
C35 C30 C31 C32 -177.8(3) . . . . ?
C30 C31 C32 C27 -0.7(5) . . . . ?
C28 C27 C32 C31 0.7(4) . . . . ?
C15 C27 C32 C31 -178.3(3) . . . . ?
C29 C30 C35 F2 -54.7(6) . . . . ?
C31 C30 C35 F2 123.5(5) . . . . ?
C29 C30 C35 F1 178.6(5) . . . . ?
C31 C30 C35 F1 -3.2(7) . . . . ?
C29 C30 C35 F3 64.9(6) . . . . ?
C31 C30 C35 F3 -116.9(5) . . . . ?
