#------------------------------------------------------------------------------
#$Date: 2022-11-18 04:26:24 +0200 (Fri, 18 Nov 2022) $
#$Revision: 279379 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/58/7245865.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_7245865
loop_
_publ_author_name
'Polo-Cuadrado, Efraín'
'Rojas-Peña, Cristian'
'Acosta-Quiroga, Karen'
'Camargo-Ayala, Lorena'
'Brito, Iván'
'Cisterna, Jonathan'
'Moncada, Félix'
'Trilleras, Jorge'
'Rodríguez-Núñez, Yeray A.'
'Gutierrez, Margarita'
_publ_section_title
;
 Design, synthesis, theoretical study, antioxidant, and anticholinesterase
 activities of new pyrazolo-fused phenanthrolines
;
_journal_issue                   51
_journal_name_full               'RSC Advances'
_journal_page_first              33032
_journal_page_last               33048
_journal_paper_doi               10.1039/D2RA05532E
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C31 H28 N6 O'
_chemical_formula_sum            'C31 H28 N6 O'
_chemical_formula_weight         500.59
_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   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2cyk96
_audit_creation_date             2022-08-11
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-23 deposited with the CCDC.	2022-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                101.682(5)
_cell_angle_beta                 92.413(5)
_cell_angle_gamma                114.101(5)
_cell_formula_units_Z            2
_cell_length_a                   8.156(2)
_cell_length_b                   9.356(2)
_cell_length_c                   19.728(5)
_cell_measurement_reflns_used    4363
_cell_measurement_temperature    294.94
_cell_measurement_theta_max      26.140
_cell_measurement_theta_min      2.808
_cell_volume                     1332.5(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      294.94
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25207
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.532
_diffrn_reflns_theta_min         2.808
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0713 before and 0.0598 after correction.
The Ratio of minimum to maximum transmission is 0.8501.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         5509
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1508
_refine_ls_R_factor_gt           0.0797
_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)+(0.1051P)²+1.2114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2034
_refine_ls_wR_factor_ref         0.2631
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2842
_reflns_number_total             5509
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra05532e2.cif
_cod_data_source_block           mg_al382_296k
_cod_original_cell_volume        1332.6(6)
_cod_database_code               7245865
_shelx_shelxl_version_number     2019/2
_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.
;
_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. Rigid body (RIGU) restrains
 O25, C26, C27, O1, C5, C21
 with sigma for 1-2 distances of 0.00002 and sigma for 1-3 distances of 0.00002
3. Same fragment restrains
{O1, C5, C21} sigma for 1-2: 0.02, 1-3: 0.02
as in
{O25, C26, C27}
4. Others
 Sof(O1)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=1-
 FVAR(1)
 Sof(O25)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C26(H26A,H26B), C5(H5A,H5B)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C31(H31),
 C32(H32), C34(H34), C35(H35)
5.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C27(H27A,H27B,
 H27C), C21(H21A,H21B,H21C)
;
_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
N4 N -0.3276(5) -0.0348(5) 0.44629(17) 0.0734(9) Uani 1 1 d . . . . .
N5 N -0.1723(5) 0.1100(4) 0.45855(16) 0.0698(9) Uani 1 1 d . . . . .
N8 N 0.0669(4) 0.2732(4) 0.55570(15) 0.0630(8) Uani 1 1 d . . . . .
N21 N -0.0118(4) 0.0855(4) 0.76677(16) 0.0668(9) Uani 1 1 d . . . . .
N29 N 0.3523(5) 0.1460(5) 0.9745(2) 0.0939(13) Uani 1 1 d . . . . .
N36 N 1.1051(5) 0.6299(4) 0.9279(2) 0.0848(11) Uani 1 1 d . . . . .
C1 C -0.0903(5) 0.1452(5) 0.52579(18) 0.0601(9) Uani 1 1 d . . . . .
C2 C -0.1939(5) 0.0229(5) 0.55657(19) 0.0602(9) Uani 1 1 d . . . . .
C3 C -0.3420(5) -0.0880(5) 0.5035(2) 0.0672(10) Uani 1 1 d . . . . .
C6 C -0.4884(6) -0.2438(5) 0.5072(2) 0.0853(13) Uani 1 1 d . . . . .
H6A H -0.578352 -0.283377 0.466741 0.128 Uiso 1 1 calc R U . . .
H6B H -0.543161 -0.228996 0.548590 0.128 Uiso 1 1 calc R U . . .
H6C H -0.438644 -0.320313 0.508597 0.128 Uiso 1 1 calc R U . . .
C7 C -0.1229(6) 0.1905(6) 0.4036(2) 0.0733(11) Uani 1 1 d . . . . .
C9 C 0.1214(5) 0.2769(4) 0.62090(19) 0.0592(9) Uani 1 1 d . . . . .
C10 C 0.0256(5) 0.1587(4) 0.65692(17) 0.0541(8) Uani 1 1 d . . . . .
C11 C -0.1358(5) 0.0311(4) 0.62449(18) 0.0572(9) Uani 1 1 d . . . . .
H11 H -0.202871 -0.046566 0.647578 0.069 Uiso 1 1 calc R U . . .
C12 C -0.2367(8) 0.1241(7) 0.3401(2) 0.0972(16) Uani 1 1 d . . . . .
H12 H -0.344927 0.032106 0.334620 0.117 Uiso 1 1 calc R U . . .
C13 C -0.1867(10) 0.1966(8) 0.2857(3) 0.1095(19) Uani 1 1 d . . . . .
H13 H -0.261901 0.152091 0.242982 0.131 Uiso 1 1 calc R U . . .
C14 C -0.0307(10) 0.3310(9) 0.2926(3) 0.117(2) Uani 1 1 d . . . . .
H14 H 0.001928 0.377755 0.255013 0.140 Uiso 1 1 calc R U . . .
C15 C 0.0790(9) 0.3977(9) 0.3561(3) 0.121(2) Uani 1 1 d . . . . .
H15 H 0.185804 0.490963 0.361706 0.145 Uiso 1 1 calc R U . . .
C16 C 0.0319(7) 0.3274(7) 0.4113(3) 0.1018(17) Uani 1 1 d . . . . .
H16 H 0.106388 0.373753 0.454196 0.122 Uiso 1 1 calc R U . . .
C17 C 0.2964(5) 0.4137(5) 0.6579(2) 0.0679(10) Uani 1 1 d . . . . .
H17A H 0.270844 0.496250 0.687559 0.082 Uiso 1 1 calc R U . . .
H17B H 0.368717 0.461142 0.623699 0.082 Uiso 1 1 calc R U . . .
C18 C 0.4031(5) 0.3566(5) 0.70213(18) 0.0628(10) Uani 1 1 d . . . . .
H18A H 0.446525 0.288375 0.671720 0.075 Uiso 1 1 calc R U . . .
H18B H 0.507808 0.449247 0.729634 0.075 Uiso 1 1 calc R U . . .
C19 C 0.2893(5) 0.2640(4) 0.75027(17) 0.0549(9) Uani 1 1 d . . . . .
C20 C 0.1035(5) 0.1712(4) 0.72721(17) 0.0563(9) Uani 1 1 d . . . . .
C22 C 0.3598(5) 0.2611(4) 0.81536(17) 0.0535(8) Uani 1 1 d . . . . .
C23 C 0.2407(5) 0.1699(5) 0.85530(18) 0.0622(10) Uani 1 1 d . . . . .
C24 C 0.0555(5) 0.0848(5) 0.8284(2) 0.0715(11) Uani 1 1 d . . . . .
C28 C 0.3031(5) 0.1571(5) 0.9220(2) 0.0722(11) Uani 1 1 d . . . . .
C30 C 0.5556(5) 0.3548(4) 0.84437(18) 0.0551(9) Uani 1 1 d . . . . .
C31 C 0.6908(5) 0.3316(5) 0.81052(19) 0.0626(9) Uani 1 1 d . . . . .
H31 H 0.659595 0.254646 0.768359 0.075 Uiso 1 1 calc R U . . .
C32 C 0.8728(5) 0.4211(5) 0.8382(2) 0.0646(10) Uani 1 1 d . . . . .
H32 H 0.960880 0.401629 0.814747 0.078 Uiso 1 1 calc R U . . .
C33 C 0.9252(5) 0.5392(4) 0.9005(2) 0.0615(9) Uani 1 1 d . . . . .
C34 C 0.7896(5) 0.5626(4) 0.9341(2) 0.0662(10) Uani 1 1 d . . . . .
H34 H 0.820717 0.641633 0.975574 0.079 Uiso 1 1 calc R U . . .
C35 C 0.6087(5) 0.4709(4) 0.90722(18) 0.0627(10) Uani 1 1 d . . . . .
H35 H 0.520481 0.487359 0.931762 0.075 Uiso 1 1 calc R U . . .
C37 C 1.2444(6) 0.6113(8) 0.8912(3) 0.120(2) Uani 1 1 d . . . . .
H37A H 1.216347 0.498728 0.876015 0.180 Uiso 1 1 calc R U . . .
H37B H 1.358053 0.665970 0.921552 0.180 Uiso 1 1 calc R U . . .
H37C H 1.252693 0.656744 0.851296 0.180 Uiso 1 1 calc R U . . .
C38 C 1.1542(6) 0.7557(5) 0.9910(3) 0.0965(15) Uani 1 1 d . . . . .
H38A H 1.106002 0.830778 0.984508 0.145 Uiso 1 1 calc R U . . .
H38B H 1.283970 0.811023 1.001575 0.145 Uiso 1 1 calc R U . . .
H38C H 1.105463 0.709262 1.028868 0.145 Uiso 1 1 calc R U . . .
O25 O -0.0551(11) 0.0137(18) 0.8730(7) 0.082(3) Uani 0.696(13) 1 d D . P A 1
C26 C -0.2500(10) -0.0589(9) 0.8506(4) 0.077(3) Uani 0.696(13) 1 d D . P A 1
H26A H -0.280640 0.013670 0.829541 0.092 Uiso 0.696(13) 1 calc R U P A 1
H26B H -0.312539 -0.072993 0.891196 0.092 Uiso 0.696(13) 1 calc R U P A 1
C27 C -0.3131(12) -0.2149(9) 0.8004(4) 0.087(3) Uani 0.696(13) 1 d D . P A 1
H27A H -0.255809 -0.200940 0.759202 0.130 Uiso 0.696(13) 1 calc R U P A 1
H27B H -0.442234 -0.259194 0.788154 0.130 Uiso 0.696(13) 1 calc R U P A 1
H27C H -0.282602 -0.287172 0.820924 0.130 Uiso 0.696(13) 1 calc R U P A 1
O1 O -0.040(2) -0.034(4) 0.8584(16) 0.097(10) Uani 0.304(13) 1 d D . P A 2
C5 C -0.224(2) -0.154(2) 0.8296(13) 0.101(8) Uani 0.304(13) 1 d D . P A 2
H5A H -0.257950 -0.239768 0.853832 0.121 Uiso 0.304(13) 1 calc R U P A 2
H5B H -0.226718 -0.199911 0.780662 0.121 Uiso 0.304(13) 1 calc R U P A 2
C21 C -0.355(2) -0.084(3) 0.8359(14) 0.132(11) Uani 0.304(13) 1 d D . P A 2
H21A H -0.330419 -0.007882 0.807356 0.198 Uiso 0.304(13) 1 calc R U P A 2
H21B H -0.345851 -0.030572 0.883777 0.198 Uiso 0.304(13) 1 calc R U P A 2
H21C H -0.475279 -0.168488 0.820617 0.198 Uiso 0.304(13) 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 0.0033 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
C3 N4 N5 108.2(3) . . ?
N4 N5 C7 119.3(3) . . ?
C1 N5 N4 108.8(3) . . ?
C1 N5 C7 131.8(4) . . ?
C9 N8 C1 114.2(3) . . ?
C24 N21 C20 118.3(3) . . ?
C33 N36 C37 120.7(4) . . ?
C33 N36 C38 119.8(4) . . ?
C37 N36 C38 119.2(4) . . ?
N5 C1 C2 107.9(3) . . ?
N8 C1 N5 125.9(4) . . ?
N8 C1 C2 126.2(3) . . ?
C1 C2 C3 105.4(3) . . ?
C11 C2 C1 118.4(3) . . ?
C11 C2 C3 136.2(4) . . ?
N4 C3 C2 109.6(4) . . ?
N4 C3 C6 122.1(4) . . ?
C2 C3 C6 128.2(4) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 N5 118.3(5) . . ?
C16 C7 N5 122.0(4) . . ?
C16 C7 C12 119.8(4) . . ?
N8 C9 C10 124.0(3) . . ?
N8 C9 C17 117.9(3) . . ?
C10 C9 C17 118.1(3) . . ?
C9 C10 C20 119.0(3) . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 C20 121.2(3) . . ?
C2 C11 C10 117.5(3) . . ?
C2 C11 H11 121.2 . . ?
C10 C11 H11 121.2 . . ?
C7 C12 H12 120.6 . . ?
C13 C12 C7 118.9(6) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.6(5) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.0(5) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.5(6) . . ?
C16 C15 H15 119.8 . . ?
C7 C16 C15 120.3(5) . . ?
C7 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C9 C17 H17A 109.4 . . ?
C9 C17 H17B 109.4 . . ?
C9 C17 C18 111.2(3) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C17 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 C17 111.7(3) . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C20 C19 C18 118.0(3) . . ?
C22 C19 C18 123.5(3) . . ?
C22 C19 C20 118.4(3) . . ?
N21 C20 C10 116.5(3) . . ?
N21 C20 C19 122.9(3) . . ?
C19 C20 C10 120.6(3) . . ?
C19 C22 C23 118.3(3) . . ?
C19 C22 C30 122.5(3) . . ?
C23 C22 C30 119.1(3) . . ?
C22 C23 C24 118.9(3) . . ?
C22 C23 C28 121.8(3) . . ?
C24 C23 C28 119.2(3) . . ?
N21 C24 C23 123.1(3) . . ?
N21 C24 O25 120.9(6) . . ?
N21 C24 O1 118.8(10) . . ?
O25 C24 C23 115.7(5) . . ?
O1 C24 C23 115.2(9) . . ?
N29 C28 C23 179.6(5) . . ?
C31 C30 C22 122.2(3) . . ?
C31 C30 C35 117.3(3) . . ?
C35 C30 C22 120.5(3) . . ?
C30 C31 H31 119.4 . . ?
C30 C31 C32 121.3(3) . . ?
C32 C31 H31 119.4 . . ?
C31 C32 H32 119.5 . . ?
C33 C32 C31 121.1(4) . . ?
C33 C32 H32 119.5 . . ?
N36 C33 C32 121.5(4) . . ?
N36 C33 C34 121.0(4) . . ?
C34 C33 C32 117.5(3) . . ?
C33 C34 H34 119.3 . . ?
C33 C34 C35 121.3(4) . . ?
C35 C34 H34 119.3 . . ?
C30 C35 H35 119.3 . . ?
C34 C35 C30 121.5(4) . . ?
C34 C35 H35 119.3 . . ?
N36 C37 H37A 109.5 . . ?
N36 C37 H37B 109.5 . . ?
N36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N36 C38 H38A 109.5 . . ?
N36 C38 H38B 109.5 . . ?
N36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C24 O25 C26 117.7(11) . . ?
O25 C26 H26A 109.1 . . ?
O25 C26 H26B 109.1 . . ?
O25 C26 C27 112.5(9) . . ?
H26A C26 H26B 107.8 . . ?
C27 C26 H26A 109.1 . . ?
C27 C26 H26B 109.1 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 O1 C5 123(2) . . ?
O1 C5 H5A 109.1 . . ?
O1 C5 H5B 109.1 . . ?
O1 C5 C21 112.3(18) . . ?
H5A C5 H5B 107.9 . . ?
C21 C5 H5A 109.1 . . ?
C21 C5 H5B 109.1 . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
N4 N5 1.392(5) . ?
N4 C3 1.315(5) . ?
N5 C1 1.372(4) . ?
N5 C7 1.422(5) . ?
N8 C1 1.350(5) . ?
N8 C9 1.332(4) . ?
N21 C20 1.355(4) . ?
N21 C24 1.315(5) . ?
N29 C28 1.136(5) . ?
N36 C33 1.377(5) . ?
N36 C37 1.423(6) . ?
N36 C38 1.440(6) . ?
C1 C2 1.388(5) . ?
C2 C3 1.435(5) . ?
C2 C11 1.379(5) . ?
C3 C6 1.478(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C12 1.390(6) . ?
C7 C16 1.357(7) . ?
C9 C10 1.413(5) . ?
C9 C17 1.500(5) . ?
C10 C11 1.380(5) . ?
C10 C20 1.463(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.374(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.352(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.373(7) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.520(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.505(5) . ?
C19 C20 1.401(5) . ?
C19 C22 1.395(4) . ?
C22 C23 1.397(5) . ?
C22 C30 1.491(5) . ?
C23 C24 1.406(5) . ?
C23 C28 1.435(5) . ?
C24 O25 1.358(15) . ?
C24 O1 1.34(3) . ?
C30 C31 1.382(5) . ?
C30 C35 1.389(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.391(5) . ?
C32 H32 0.9300 . ?
C32 C33 1.391(5) . ?
C33 C34 1.382(5) . ?
C34 H34 0.9300 . ?
C34 C35 1.382(5) . ?
C35 H35 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
O25 C26 1.456(10) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.461(9) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
O1 C5 1.456(17) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C21 1.459(17) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C16 H16 N8 0.93 2.36 3.014(6) 127.1 . 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
N4 N5 C1 N8 177.6(3) . . . . ?
N4 N5 C1 C2 -0.2(4) . . . . ?
N4 N5 C7 C12 2.5(5) . . . . ?
N4 N5 C7 C16 -176.4(4) . . . . ?
N5 N4 C3 C2 0.3(4) . . . . ?
N5 N4 C3 C6 -177.1(3) . . . . ?
N5 C1 C2 C3 0.4(4) . . . . ?
N5 C1 C2 C11 178.9(3) . . . . ?
N5 C7 C12 C13 -177.1(4) . . . . ?
N5 C7 C16 C15 177.0(5) . . . . ?
N8 C1 C2 C3 -177.4(3) . . . . ?
N8 C1 C2 C11 1.2(5) . . . . ?
N8 C9 C10 C11 -0.8(5) . . . . ?
N8 C9 C10 C20 176.9(3) . . . . ?
N8 C9 C17 C18 -141.4(3) . . . . ?
N21 C24 O25 C26 -1.0(15) . . . . ?
N21 C24 O1 C5 -7(3) . . . . ?
N36 C33 C34 C35 -179.4(4) . . . . ?
C1 N5 C7 C12 -179.7(4) . . . . ?
C1 N5 C7 C16 1.4(7) . . . . ?
C1 N8 C9 C10 0.0(5) . . . . ?
C1 N8 C9 C17 179.1(3) . . . . ?
C1 C2 C3 N4 -0.4(4) . . . . ?
C1 C2 C3 C6 176.8(4) . . . . ?
C1 C2 C11 C10 -1.9(5) . . . . ?
C3 N4 N5 C1 -0.1(4) . . . . ?
C3 N4 N5 C7 178.3(3) . . . . ?
C3 C2 C11 C10 176.1(4) . . . . ?
C7 N5 C1 N8 -0.5(6) . . . . ?
C7 N5 C1 C2 -178.2(4) . . . . ?
C7 C12 C13 C14 -0.5(8) . . . . ?
C9 N8 C1 N5 -177.5(3) . . . . ?
C9 N8 C1 C2 -0.2(5) . . . . ?
C9 C10 C11 C2 1.8(5) . . . . ?
C9 C10 C20 N21 162.0(3) . . . . ?
C9 C10 C20 C19 -19.9(5) . . . . ?
C9 C17 C18 C19 -52.2(4) . . . . ?
C10 C9 C17 C18 37.8(5) . . . . ?
C11 C2 C3 N4 -178.6(4) . . . . ?
C11 C2 C3 C6 -1.4(7) . . . . ?
C11 C10 C20 N21 -20.3(5) . . . . ?
C11 C10 C20 C19 157.8(3) . . . . ?
C12 C7 C16 C15 -1.9(8) . . . . ?
C12 C13 C14 C15 -0.9(9) . . . . ?
C13 C14 C15 C16 0.9(9) . . . . ?
C14 C15 C16 C7 0.5(9) . . . . ?
C16 C7 C12 C13 1.9(7) . . . . ?
C17 C9 C10 C11 -180.0(3) . . . . ?
C17 C9 C10 C20 -2.2(5) . . . . ?
C17 C18 C19 C20 32.9(5) . . . . ?
C17 C18 C19 C22 -149.5(3) . . . . ?
C18 C19 C20 N21 -178.8(3) . . . . ?
C18 C19 C20 C10 3.2(5) . . . . ?
C18 C19 C22 C23 -179.6(3) . . . . ?
C18 C19 C22 C30 2.0(5) . . . . ?
C19 C22 C23 C24 0.2(6) . . . . ?
C19 C22 C23 C28 178.3(4) . . . . ?
C19 C22 C30 C31 -59.6(5) . . . . ?
C19 C22 C30 C35 120.0(4) . . . . ?
C20 N21 C24 C23 0.6(6) . . . . ?
C20 N21 C24 O25 173.8(8) . . . . ?
C20 N21 C24 O1 -159.4(16) . . . . ?
C20 C10 C11 C2 -176.0(3) . . . . ?
C20 C19 C22 C23 -2.0(5) . . . . ?
C20 C19 C22 C30 179.6(3) . . . . ?
C22 C19 C20 N21 3.4(5) . . . . ?
C22 C19 C20 C10 -174.6(3) . . . . ?
C22 C23 C24 N21 0.6(7) . . . . ?
C22 C23 C24 O25 -172.9(8) . . . . ?
C22 C23 C24 O1 161.2(16) . . . . ?
C22 C30 C31 C32 179.5(3) . . . . ?
C22 C30 C35 C34 -178.0(3) . . . . ?
C23 C22 C30 C31 122.1(4) . . . . ?
C23 C22 C30 C35 -58.3(5) . . . . ?
C23 C24 O25 C26 172.7(8) . . . . ?
C23 C24 O1 C5 -168.6(19) . . . . ?
C24 N21 C20 C10 175.4(4) . . . . ?
C24 N21 C20 C19 -2.7(6) . . . . ?
C24 O25 C26 C27 77.3(14) . . . . ?
C24 O1 C5 C21 -70(3) . . . . ?
C28 C23 C24 N21 -177.6(4) . . . . ?
C28 C23 C24 O25 8.9(9) . . . . ?
C28 C23 C24 O1 -16.9(17) . . . . ?
C30 C22 C23 C24 178.5(4) . . . . ?
C30 C22 C23 C28 -3.3(6) . . . . ?
C30 C31 C32 C33 -1.1(6) . . . . ?
C31 C30 C35 C34 1.6(5) . . . . ?
C31 C32 C33 N36 -179.1(4) . . . . ?
C31 C32 C33 C34 0.8(6) . . . . ?
C32 C33 C34 C35 0.7(6) . . . . ?
C33 C34 C35 C30 -2.0(6) . . . . ?
C35 C30 C31 C32 -0.1(5) . . . . ?
C37 N36 C33 C32 3.3(6) . . . . ?
C37 N36 C33 C34 -176.5(4) . . . . ?
C38 N36 C33 C32 177.3(4) . . . . ?
C38 N36 C33 C34 -2.5(6) . . . . ?
