#------------------------------------------------------------------------------
#$Date: 2025-04-09 03:57:33 +0300 (Wed, 09 Apr 2025) $
#$Revision: 299229 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/04/7160492.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_7160492
loop_
_publ_author_name
'Sadhukhan, Juheli'
'Mandal, Pabitra'
'Pramanik, Smritimoy'
'Guria, Subhajit'
'Kabir, Alomgir Shah'
'Das, Debojyoti'
'Adhikari, Susanta Sekhar'
_publ_section_title
;
 Recognition of GC base pairs of B-DNA by coumarin-based
 benzimidazopyrimidines.
;
_journal_name_full               'Organic & biomolecular chemistry'
_journal_paper_doi               10.1039/d4ob02055c
_journal_year                    2025
_chemical_formula_moiety         'C33 H30 N4 O4'
_chemical_formula_sum            'C33 H30 N4 O4'
_chemical_formula_weight         546.61
_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   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2kw05n
_audit_creation_date             2024-07-29
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-08-23 deposited with the CCDC.	2025-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                95.812(7)
_cell_angle_beta                 91.348(6)
_cell_angle_gamma                93.311(6)
_cell_formula_units_Z            2
_cell_length_a                   7.2081(14)
_cell_length_b                   10.733(2)
_cell_length_c                   18.339(4)
_cell_measurement_reflns_used    9372
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      64.90
_cell_measurement_theta_min      2.42
_cell_volume                     1408.5(5)
_computing_cell_refinement       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            47723
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        65.100
_diffrn_reflns_theta_max         65.100
_diffrn_reflns_theta_min         2.423
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  0.5835
_exptl_absorpt_correction_T_min  0.4954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1186 before and 0.0626 after correction.
The Ratio of minimum to maximum transmission is 0.8490.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0052(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         4801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0491
_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)+(0.0806P)²+0.2762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4387
_reflns_number_total             4801
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob02055c2.cif
_cod_data_source_block           nd_3_68_0m_a
_cod_database_code               7160492
_shelx_shelxl_version_number     2016/6
_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   0.903
_shelx_estimated_absorpt_t_min   0.862
_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. Uiso/Uaniso restraints and constraints
Uanis(C32) = Uanis(C32A)
Uanis(C33) = Uanis(C33A)
3. Others
 Sof(C32)=Sof(H32C)=Sof(H32D)=Sof(C33)=Sof(H33D)=Sof(H33E)=Sof(H33F)=1-FVAR(1)
 Sof(C32A)=Sof(H32A)=Sof(H32B)=Sof(C33A)=Sof(H33A)=Sof(H33B)=Sof(H33C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C30(H30A,H30B), C32A(H32A,H32B), C32(H32C,H32D)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C18(H18), C19(H19), C20(H20), C21(H21),
 C24(H24), C25(H25), C27(H27), C28(H28)
4.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C33A(H33A,H33B,
 H33C), C33(H33D,H33E,H33F)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.63972(15) 0.11141(11) 0.17359(7) 0.0619(3) Uani 1 1 d . . . . .
O2 O 0.81148(16) 0.25338(13) 0.24354(7) 0.0663(3) Uani 1 1 d . . . . .
O3 O 0.6908(2) 0.47325(14) 0.17158(7) 0.0759(4) Uani 1 1 d . . . . .
O4 O 0.91757(17) 0.53393(14) 0.25574(7) 0.0706(4) Uani 1 1 d . . . . .
N1 N 0.36154(17) 0.38078(12) 0.35122(7) 0.0518(3) Uani 1 1 d . . . . .
N2 N 0.48157(16) 0.58616(12) 0.40193(7) 0.0471(3) Uani 1 1 d . . . . .
N3 N 0.23839(17) 0.49121(12) 0.45597(7) 0.0526(3) Uani 1 1 d . . . . .
N4 N 0.3131(3) -0.2186(2) 0.02179(13) 0.1000(7) Uani 1 1 d . . . . .
C1 C 0.3114(3) -0.11505(19) 0.07171(12) 0.0745(6) Uani 1 1 d . . . . .
C2 C 0.1419(3) -0.0690(2) 0.09848(13) 0.0793(6) Uani 1 1 d . . . . .
H2 H 0.029582 -0.110899 0.082340 0.095 Uiso 1 1 calc R U . . .
C3 C 0.1416(3) 0.03567(19) 0.14749(11) 0.0690(5) Uani 1 1 d . . . . .
H3 H 0.028484 0.063723 0.163648 0.083 Uiso 1 1 calc R U . . .
C4 C 0.3056(2) 0.10175(16) 0.17403(9) 0.0567(4) Uani 1 1 d . . . . .
C5 C 0.4715(2) 0.05398(16) 0.14872(10) 0.0571(4) Uani 1 1 d . . . . .
C6 C 0.4777(3) -0.04969(18) 0.09874(11) 0.0680(5) Uani 1 1 d . . . . .
H6 H 0.591495 -0.076713 0.082755 0.082 Uiso 1 1 calc R U . . .
C7 C 0.3177(2) 0.21224(15) 0.22381(9) 0.0544(4) Uani 1 1 d . . . . .
H7 H 0.208621 0.245158 0.241121 0.065 Uiso 1 1 calc R U . . .
C8 C 0.4827(2) 0.27136(15) 0.24694(9) 0.0521(4) Uani 1 1 d . . . . .
C9 C 0.6551(2) 0.21760(16) 0.22350(9) 0.0549(4) Uani 1 1 d . . . . .
C10 C 0.4882(2) 0.38468(15) 0.30085(9) 0.0502(4) Uani 1 1 d . . . . .
C11 C 0.6186(2) 0.48978(15) 0.29769(9) 0.0505(4) Uani 1 1 d . . . . .
C12 C 0.6147(2) 0.59118(15) 0.34989(8) 0.0483(4) Uani 1 1 d . . . . .
C13 C 0.7446(2) 0.49653(16) 0.23457(10) 0.0586(4) Uani 1 1 d . . . . .
C14 C 1.0495(4) 0.5536(3) 0.19951(15) 0.1131(10) Uani 1 1 d . . . . .
H14A H 1.103114 0.475002 0.183376 0.136 Uiso 1 1 calc R U . . .
H14B H 0.986649 0.582726 0.157647 0.136 Uiso 1 1 calc R U . . .
C15 C 1.1939(3) 0.6445(3) 0.22727(16) 0.1053(9) Uani 1 1 d . . . . .
H15A H 1.289858 0.648270 0.191995 0.158 Uiso 1 1 calc R U . . .
H15B H 1.245189 0.620756 0.272274 0.158 Uiso 1 1 calc R U . . .
H15C H 1.143462 0.725272 0.236149 0.158 Uiso 1 1 calc R U . . .
C16 C 0.3555(2) 0.47996(14) 0.40234(9) 0.0479(3) Uani 1 1 d . . . . .
C17 C 0.2843(2) 0.60808(15) 0.49265(8) 0.0496(4) Uani 1 1 d . . . . .
C18 C 0.2011(2) 0.66623(17) 0.55427(9) 0.0565(4) Uani 1 1 d . . . . .
H18 H 0.103257 0.625908 0.576516 0.068 Uiso 1 1 calc R U . . .
C19 C 0.2685(2) 0.78451(18) 0.58071(10) 0.0613(4) Uani 1 1 d . . . . .
H19 H 0.215654 0.824591 0.621801 0.074 Uiso 1 1 calc R U . . .
C20 C 0.4150(2) 0.84674(18) 0.54753(10) 0.0634(4) Uani 1 1 d . . . . .
H20 H 0.455294 0.927622 0.566601 0.076 Uiso 1 1 calc R U . . .
C21 C 0.5006(2) 0.79139(16) 0.48757(10) 0.0580(4) Uani 1 1 d . . . . .
H21 H 0.598649 0.832522 0.465900 0.070 Uiso 1 1 calc R U . . .
C22 C 0.4338(2) 0.67086(15) 0.46078(8) 0.0481(4) Uani 1 1 d . . . . .
C23 C 0.7406(2) 0.70588(15) 0.35288(9) 0.0502(4) Uani 1 1 d . . . . .
C24 C 0.7165(2) 0.79568(17) 0.30516(10) 0.0583(4) Uani 1 1 d . . . . .
H24 H 0.618800 0.785250 0.270653 0.070 Uiso 1 1 calc R U . . .
C25 C 0.8378(3) 0.90134(17) 0.30859(10) 0.0642(5) Uani 1 1 d . . . . .
H25 H 0.819833 0.961544 0.276453 0.077 Uiso 1 1 calc R U . . .
C26 C 0.9849(2) 0.91867(17) 0.35894(10) 0.0621(4) Uani 1 1 d . . . . .
C27 C 1.0056(2) 0.82838(18) 0.40689(11) 0.0647(5) Uani 1 1 d . . . . .
H27 H 1.103086 0.838955 0.441507 0.078 Uiso 1 1 calc R U . . .
C28 C 0.8855(2) 0.72324(17) 0.40467(10) 0.0599(4) Uani 1 1 d . . . . .
H28 H 0.901677 0.664246 0.437730 0.072 Uiso 1 1 calc R U . . .
C29 C 1.1219(3) 1.0310(2) 0.36145(15) 0.0900(7) Uani 1 1 d . . . . .
H29A H 1.238587 1.004772 0.343023 0.135 Uiso 1 1 calc R U . . .
H29B H 1.139712 1.068137 0.411160 0.135 Uiso 1 1 calc R U . . .
H29C H 1.074652 1.091388 0.331756 0.135 Uiso 1 1 calc R U . . .
C30 C 0.4885(3) -0.2667(2) -0.00461(13) 0.0877(7) Uani 1 1 d . . . . .
H30A H 0.574133 -0.197076 -0.013295 0.105 Uiso 1 1 calc R U . . .
H30B H 0.465468 -0.318809 -0.050686 0.105 Uiso 1 1 calc R U . . .
C31 C 0.5737(4) -0.3421(3) 0.05033(16) 0.1050(8) Uani 1 1 d . . . . .
H31A H 0.683102 -0.378051 0.030610 0.157 Uiso 1 1 calc R U . . .
H31B H 0.485956 -0.407908 0.061178 0.157 Uiso 1 1 calc R U . . .
H31C H 0.606809 -0.288651 0.094453 0.157 Uiso 1 1 calc R U . . .
C32A C 0.1622(12) -0.2489(7) -0.0338(4) 0.0780(8) Uani 0.313(4) 1 d . . P A 1
H32A H 0.081958 -0.179862 -0.036211 0.094 Uiso 0.313(4) 1 calc R U P A 1
H32B H 0.210108 -0.271938 -0.082011 0.094 Uiso 0.313(4) 1 calc R U P A 1
C33A C 0.0665(14) -0.3563(11) -0.0043(5) 0.0994(11) Uani 0.313(4) 1 d . . P A 1
H33A H -0.035269 -0.388558 -0.036872 0.149 Uiso 0.313(4) 1 calc R U P A 1
H33B H 0.019973 -0.330017 0.043030 0.149 Uiso 0.313(4) 1 calc R U P A 1
H33C H 0.151943 -0.420648 0.000113 0.149 Uiso 0.313(4) 1 calc R U P A 1
C32 C 0.1388(5) -0.3066(3) 0.0089(2) 0.0780(8) Uani 0.687(4) 1 d . . P A 2
H32C H 0.172470 -0.392382 -0.002943 0.094 Uiso 0.687(4) 1 calc R U P A 2
H32D H 0.065003 -0.303023 0.052546 0.094 Uiso 0.687(4) 1 calc R U P A 2
C33 C 0.0292(6) -0.2633(4) -0.0546(2) 0.0994(11) Uani 0.687(4) 1 d . . P A 2
H33D H 0.104762 -0.265348 -0.097079 0.149 Uiso 0.687(4) 1 calc R U P A 2
H33E H -0.006085 -0.179215 -0.041705 0.149 Uiso 0.687(4) 1 calc R U P A 2
H33F H -0.080330 -0.317988 -0.065196 0.149 Uiso 0.687(4) 1 calc R U 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
C5 O1 C9 122.88(12) . . ?
C13 O4 C14 117.70(17) . . ?
C10 N1 C16 118.34(13) . . ?
C12 N2 C16 121.15(13) . . ?
C12 N2 C22 132.98(13) . . ?
C22 N2 C16 105.87(12) . . ?
C16 N3 C17 104.86(13) . . ?
C1 N4 C30 121.17(19) . . ?
C1 N4 C32A 121.3(3) . . ?
C1 N4 C32 119.6(2) . . ?
C30 N4 C32A 111.0(3) . . ?
C30 N4 C32 117.1(2) . . ?
N4 C1 C2 121.49(19) . . ?
N4 C1 C6 121.21(18) . . ?
C6 C1 C2 117.30(17) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.06(18) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.04(17) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 116.43(16) . . ?
C3 C4 C7 125.70(15) . . ?
C5 C4 C7 117.87(16) . . ?
O1 C5 C4 120.25(15) . . ?
C6 C5 O1 116.46(15) . . ?
C6 C5 C4 123.29(17) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.86(17) . . ?
C5 C6 H6 120.1 . . ?
C4 C7 H7 118.9 . . ?
C8 C7 C4 122.20(15) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 C9 119.68(15) . . ?
C7 C8 C10 120.14(14) . . ?
C9 C8 C10 119.99(14) . . ?
O1 C9 C8 116.96(14) . . ?
O2 C9 O1 115.48(14) . . ?
O2 C9 C8 127.55(16) . . ?
N1 C10 C8 114.19(14) . . ?
N1 C10 C11 122.92(14) . . ?
C11 C10 C8 122.88(14) . . ?
C10 C11 C13 120.92(14) . . ?
C12 C11 C10 119.27(14) . . ?
C12 C11 C13 119.51(14) . . ?
N2 C12 C11 117.23(13) . . ?
N2 C12 C23 117.90(14) . . ?
C11 C12 C23 124.86(14) . . ?
O3 C13 O4 124.77(16) . . ?
O3 C13 C11 122.74(16) . . ?
O4 C13 C11 112.47(14) . . ?
O4 C14 H14A 109.6 . . ?
O4 C14 H14B 109.6 . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 O4 110.1(2) . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
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 . . ?
N1 C16 N2 121.08(13) . . ?
N3 C16 N1 126.05(14) . . ?
N3 C16 N2 112.87(13) . . ?
N3 C17 C18 128.02(15) . . ?
N3 C17 C22 112.19(13) . . ?
C18 C17 C22 119.79(15) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 C17 117.76(16) . . ?
C19 C18 H18 121.1 . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.77(16) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.69(17) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 H21 121.6 . . ?
C20 C21 C22 116.84(16) . . ?
C22 C21 H21 121.6 . . ?
N2 C22 C17 104.21(13) . . ?
C21 C22 N2 133.65(15) . . ?
C21 C22 C17 122.13(15) . . ?
C24 C23 C12 121.37(14) . . ?
C24 C23 C28 119.38(15) . . ?
C28 C23 C12 119.25(14) . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.15(16) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.10(17) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C27 117.95(16) . . ?
C25 C26 C29 121.62(19) . . ?
C27 C26 C29 120.42(18) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 C26 121.75(16) . . ?
C28 C27 H27 119.1 . . ?
C23 C28 H28 120.2 . . ?
C27 C28 C23 119.66(16) . . ?
C27 C28 H28 120.2 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N4 C30 H30A 109.5 . . ?
N4 C30 H30B 109.5 . . ?
N4 C30 C31 110.6(2) . . ?
H30A C30 H30B 108.1 . . ?
C31 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N4 C32A H32A 111.7 . . ?
N4 C32A H32B 111.7 . . ?
H32A C32A H32B 109.5 . . ?
C33A C32A N4 100.3(7) . . ?
C33A C32A H32A 111.7 . . ?
C33A C32A H32B 111.7 . . ?
C32A C33A H33A 109.5 . . ?
C32A C33A H33B 109.5 . . ?
C32A C33A H33C 109.5 . . ?
H33A C33A H33B 109.5 . . ?
H33A C33A H33C 109.5 . . ?
H33B C33A H33C 109.5 . . ?
N4 C32 H32C 110.3 . . ?
N4 C32 H32D 110.3 . . ?
H32C C32 H32D 108.6 . . ?
C33 C32 N4 107.0(3) . . ?
C33 C32 H32C 110.3 . . ?
C33 C32 H32D 110.3 . . ?
C32 C33 H33D 109.5 . . ?
C32 C33 H33E 109.5 . . ?
C32 C33 H33F 109.5 . . ?
H33D C33 H33E 109.5 . . ?
H33D C33 H33F 109.5 . . ?
H33E C33 H33F 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 C5 1.374(2) . ?
O1 C9 1.385(2) . ?
O2 C9 1.206(2) . ?
O3 C13 1.207(2) . ?
O4 C13 1.324(2) . ?
O4 C14 1.442(2) . ?
N1 C10 1.316(2) . ?
N1 C16 1.349(2) . ?
N2 C12 1.3719(19) . ?
N2 C16 1.4167(19) . ?
N2 C22 1.4017(19) . ?
N3 C16 1.312(2) . ?
N3 C17 1.381(2) . ?
N4 C1 1.367(3) . ?
N4 C30 1.467(3) . ?
N4 C32A 1.472(8) . ?
N4 C32 1.527(4) . ?
C1 C2 1.424(3) . ?
C1 C6 1.406(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(2) . ?
C4 C5 1.399(2) . ?
C4 C7 1.419(2) . ?
C5 C6 1.372(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.353(2) . ?
C8 C9 1.456(2) . ?
C8 C10 1.486(2) . ?
C10 C11 1.433(2) . ?
C11 C12 1.377(2) . ?
C11 C13 1.493(2) . ?
C12 C23 1.482(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.432(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 C18 1.400(2) . ?
C17 C22 1.408(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.401(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.391(2) . ?
C23 C24 1.381(2) . ?
C23 C28 1.387(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.387(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.381(3) . ?
C26 C27 1.385(3) . ?
C26 C29 1.510(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.378(2) . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.497(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32A H32A 0.9700 . ?
C32A H32B 0.9700 . ?
C32A C33A 1.466(14) . ?
C33A H33A 0.9600 . ?
C33A H33B 0.9600 . ?
C33A H33C 0.9600 . ?
C32 H32C 0.9700 . ?
C32 H32D 0.9700 . ?
C32 C33 1.518(6) . ?
C33 H33D 0.9600 . ?
C33 H33E 0.9600 . ?
C33 H33F 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
O1 C5 C6 C1 178.82(18) . . . . ?
N1 C10 C11 C12 1.0(2) . . . . ?
N1 C10 C11 C13 -172.65(15) . . . . ?
N2 C12 C23 C24 -102.95(18) . . . . ?
N2 C12 C23 C28 77.11(19) . . . . ?
N3 C17 C18 C19 -178.85(16) . . . . ?
N3 C17 C22 N2 -0.62(17) . . . . ?
N3 C17 C22 C21 178.34(14) . . . . ?
N4 C1 C2 C3 -179.0(2) . . . . ?
N4 C1 C6 C5 179.9(2) . . . . ?
C1 N4 C30 C31 79.5(3) . . . . ?
C1 N4 C32A C33A -106.8(6) . . . . ?
C1 N4 C32 C33 92.8(3) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C2 C3 C4 C7 178.8(2) . . . . ?
C3 C4 C5 O1 -178.27(16) . . . . ?
C3 C4 C5 C6 2.0(3) . . . . ?
C3 C4 C7 C8 -179.82(18) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C4 C7 C8 C9 -3.2(3) . . . . ?
C4 C7 C8 C10 -178.16(15) . . . . ?
C5 O1 C9 O2 175.89(15) . . . . ?
C5 O1 C9 C8 -2.8(2) . . . . ?
C5 C4 C7 C8 0.0(3) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
C7 C4 C5 O1 1.9(3) . . . . ?
C7 C4 C5 C6 -177.81(17) . . . . ?
C7 C8 C9 O1 4.6(2) . . . . ?
C7 C8 C9 O2 -173.92(17) . . . . ?
C7 C8 C10 N1 36.8(2) . . . . ?
C7 C8 C10 C11 -142.42(16) . . . . ?
C8 C10 C11 C12 -179.88(14) . . . . ?
C8 C10 C11 C13 6.5(2) . . . . ?
C9 O1 C5 C4 -0.4(3) . . . . ?
C9 O1 C5 C6 179.32(16) . . . . ?
C9 C8 C10 N1 -138.09(16) . . . . ?
C9 C8 C10 C11 42.7(2) . . . . ?
C10 N1 C16 N2 0.2(2) . . . . ?
C10 N1 C16 N3 179.85(15) . . . . ?
C10 C8 C9 O1 179.49(14) . . . . ?
C10 C8 C9 O2 1.0(3) . . . . ?
C10 C11 C12 N2 -1.1(2) . . . . ?
C10 C11 C12 C23 -179.71(14) . . . . ?
C10 C11 C13 O3 46.1(2) . . . . ?
C10 C11 C13 O4 -135.76(16) . . . . ?
C11 C12 C23 C24 75.6(2) . . . . ?
C11 C12 C23 C28 -104.33(19) . . . . ?
C12 N2 C16 N1 -0.5(2) . . . . ?
C12 N2 C16 N3 179.84(13) . . . . ?
C12 N2 C22 C17 180.00(15) . . . . ?
C12 N2 C22 C21 1.2(3) . . . . ?
C12 C11 C13 O3 -127.52(19) . . . . ?
C12 C11 C13 O4 50.7(2) . . . . ?
C12 C23 C24 C25 -179.18(16) . . . . ?
C12 C23 C28 C27 178.68(16) . . . . ?
C13 O4 C14 C15 153.1(2) . . . . ?
C13 C11 C12 N2 172.55(14) . . . . ?
C13 C11 C12 C23 -6.0(2) . . . . ?
C14 O4 C13 O3 2.9(3) . . . . ?
C14 O4 C13 C11 -175.3(2) . . . . ?
C16 N1 C10 C8 -179.71(13) . . . . ?
C16 N1 C10 C11 -0.5(2) . . . . ?
C16 N2 C12 C11 0.9(2) . . . . ?
C16 N2 C12 C23 179.62(13) . . . . ?
C16 N2 C22 C17 0.85(15) . . . . ?
C16 N2 C22 C21 -177.93(17) . . . . ?
C16 N3 C17 C18 179.78(15) . . . . ?
C16 N3 C17 C22 0.09(17) . . . . ?
C17 N3 C16 N1 -179.13(15) . . . . ?
C17 N3 C16 N2 0.50(17) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C18 C17 C22 N2 179.66(13) . . . . ?
C18 C17 C22 C21 -1.4(2) . . . . ?
C18 C19 C20 C21 -1.2(3) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C20 C21 C22 N2 179.23(16) . . . . ?
C20 C21 C22 C17 0.6(2) . . . . ?
C22 N2 C12 C11 -178.09(14) . . . . ?
C22 N2 C12 C23 0.6(2) . . . . ?
C22 N2 C16 N1 178.76(13) . . . . ?
C22 N2 C16 N3 -0.89(17) . . . . ?
C22 C17 C18 C19 0.8(2) . . . . ?
C23 C24 C25 C26 0.5(3) . . . . ?
C24 C23 C28 C27 -1.3(3) . . . . ?
C24 C25 C26 C27 -1.2(3) . . . . ?
C24 C25 C26 C29 177.77(19) . . . . ?
C25 C26 C27 C28 0.7(3) . . . . ?
C26 C27 C28 C23 0.5(3) . . . . ?
C28 C23 C24 C25 0.8(3) . . . . ?
C29 C26 C27 C28 -178.30(19) . . . . ?
C30 N4 C1 C2 -179.0(2) . . . . ?
C30 N4 C1 C6 1.0(4) . . . . ?
C30 N4 C32A C33A 101.4(6) . . . . ?
C30 N4 C32 C33 -103.6(3) . . . . ?
C32A N4 C1 C2 32.1(5) . . . . ?
C32A N4 C1 C6 -147.9(4) . . . . ?
C32A N4 C30 C31 -128.7(4) . . . . ?
C32 N4 C1 C2 -16.1(4) . . . . ?
C32 N4 C1 C6 163.9(3) . . . . ?
C32 N4 C30 C31 -83.8(3) . . . . ?
