#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:58:05 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296721 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/23/1572394.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_1572394
loop_
_publ_author_name
'Li, Chengchuang'
'Zhu, Teng'
'Tang, Jie'
'Lei, Caijin'
'Yu, Guoyang'
'Yang, Yanqiang'
'Yang, Hongwei'
'Xiao, Chuan'
'Cheng, Guangbin'
_publ_section_title
;
 An advanced furoxan-bridged heat-resistant explosive.
;
_journal_issue                   22
_journal_name_full               'Materials horizons'
_journal_page_first              5701
_journal_page_last               5708
_journal_paper_doi               10.1039/d4mh00999a
_journal_volume                  11
_journal_year                    2024
_chemical_formula_moiety         'C12 H4 N16 O10, 4(C H4 O)'
_chemical_formula_sum            'C16 H20 N16 O14'
_chemical_formula_weight         660.48
_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_creation_date             2024-08-20
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-20 deposited with the CCDC.	2024-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                105.307(4)
_cell_angle_beta                 91.114(4)
_cell_angle_gamma                99.187(4)
_cell_formula_units_Z            2
_cell_length_a                   9.2092(11)
_cell_length_b                   10.8368(13)
_cell_length_c                   14.1420(16)
_cell_measurement_reflns_used    2209
_cell_measurement_temperature    198.00
_cell_measurement_theta_max      20.945
_cell_measurement_theta_min      2.245
_cell_volume                     1341.0(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      198.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_av_unetI/netI     0.0803
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18604
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         1.977
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0841 before and 0.0681 after correction.
The Ratio of minimum to maximum transmission is 0.8712.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         4856
_refine_ls_number_restraints     112
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0626
_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)+(0.0659P)²+0.9288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1751
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2967
_reflns_number_total             4856
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4mh00999a3.cif
_cod_data_source_block           mo_20230228_ys_nlg_lcc_a321_0m
_cod_depositor_comments
'Adding full bibliography for 1572391--1572394.cif.'
_cod_database_code               1572394
_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_max   0.986
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C8-C9 \\sim C8-C9A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10
 with sigma of 0.02
 C9-N14 \\sim C9A-N14A
 with sigma of 0.02
 N14-O7 \\sim N14A-O7A
 with sigma of 0.02
 N14-O8 \\sim N14A-O8A
 with sigma of 0.02
 C8-N14 \\sim C8-N14A
 with sigma of 0.04
 C9-O7 \\sim C9A-O7A
 with sigma of 0.04
 C9-O8 \\sim C9A-O8A
 with sigma of 0.04
 C10-N14 \\sim C10-N14A
 with sigma of 0.04
 O7-O8 \\sim O7A-O8A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O8: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
O8A \\sim N14 \\sim O8 \\sim N14A \\sim O7A \\sim O7 \\sim C9 \\sim C9A: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(O6A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(N14A)=Sof(O8A)=Sof(O7A)=Sof(C9A)=1-FVAR(1)
 Sof(C9)=Sof(N14)=Sof(O7)=Sof(O8)=FVAR(1)
 Sof(O6A)=1-FVAR(2)
 Sof(O6)=FVAR(2)
5.a X=CH2 refined with riding coordinates:
 N11(H11A,H11B), N16(H16A,H16B)
5.b Idealised Me refined as rotating group:
 C16(H16C,H16D,H16E), C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
5.c Idealised tetrahedral OH refined as rotating group:
 O14(H14), O12(H12), O11(H11), O13(H13)
;
_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
C1 C 0.1102(4) 0.2105(4) 0.5128(3) 0.0351(9) Uani 1 1 d . . . . .
C2 C 0.0988(4) 0.1776(4) 0.4103(3) 0.0332(9) Uani 1 1 d . . . . .
C3 C 0.3523(4) 0.2867(3) 0.4344(3) 0.0311(9) Uani 1 1 d . . . . .
C4 C 0.4560(4) 0.3093(3) 0.3691(3) 0.0319(9) Uani 1 1 d . . . . .
C5 C 0.3915(4) 0.2499(3) 0.2748(3) 0.0304(9) Uani 1 1 d . . . . .
C6 C 0.4450(4) 0.2376(3) 0.1765(3) 0.0356(9) Uani 1 1 d . . . . .
C7 C 0.5123(4) 0.3326(4) 0.1330(3) 0.0337(9) Uani 1 1 d . . . . .
C8 C 0.5565(4) 0.4732(4) 0.1726(3) 0.0328(9) Uani 1 1 d D . . . .
C9 C 0.6897(9) 0.5531(5) 0.1678(9) 0.031(2) Uani 0.791(11) 1 d D U P A 1
C10 C 0.6717(4) 0.6794(4) 0.2131(3) 0.0325(9) Uani 1 1 d D . . . .
C11 C 0.4772(4) 0.7666(3) 0.3072(3) 0.0302(9) Uani 1 1 d . . . . .
C12 C 0.5768(4) 0.8833(3) 0.3179(3) 0.0324(9) Uani 1 1 d . . . . .
N1 N 0.2300(3) 0.2741(3) 0.5702(2) 0.0373(8) Uani 1 1 d . . . . .
N2 N 0.3533(3) 0.3145(3) 0.5341(2) 0.0364(8) Uani 1 1 d . . . . .
N3 N 0.2305(3) 0.2182(3) 0.3755(2) 0.0305(7) Uani 1 1 d . . . . .
N4 N 0.2518(3) 0.1945(3) 0.2789(2) 0.0347(8) Uani 1 1 d . . . . .
N5 N 0.4195(4) 0.1230(3) 0.1123(3) 0.0490(10) Uani 1 1 d . . . . .
N6 N 0.5212(4) 0.2759(3) 0.0389(3) 0.0420(9) Uani 1 1 d . . . . .
N7 N 0.4620(3) 0.5401(3) 0.2249(2) 0.0316(7) Uani 1 1 d . . . . .
N8 N 0.5343(3) 0.6644(3) 0.2486(2) 0.0289(7) Uani 1 1 d . . . . .
N9 N 0.7584(3) 0.7974(3) 0.2255(3) 0.0394(9) Uani 1 1 d . . . . .
N10 N 0.7062(3) 0.8974(3) 0.2791(3) 0.0360(8) Uani 1 1 d . . . . .
N11 N -0.0126(3) 0.1219(3) 0.3468(3) 0.0472(10) Uani 1 1 d . . . . .
H11A H -0.001782 0.111504 0.283594 0.057 Uiso 1 1 calc R U . . .
H11B H -0.098536 0.094847 0.367099 0.057 Uiso 1 1 calc R U . . .
N12 N -0.0147(4) 0.1749(3) 0.5659(3) 0.0424(9) Uani 1 1 d . . . . .
N13 N 0.6078(3) 0.3708(3) 0.3928(3) 0.0383(8) Uani 1 1 d . . . . .
N14 N 0.8242(5) 0.5131(5) 0.1346(5) 0.0335(13) Uani 0.791(11) 1 d D U P A 1
N15 N 0.5406(3) 1.0062(3) 0.3749(3) 0.0387(8) Uani 1 1 d . . . . .
N16 N 0.3492(3) 0.7423(3) 0.3418(2) 0.0362(8) Uani 1 1 d . . . . .
H16A H 0.300784 0.662166 0.327642 0.043 Uiso 1 1 calc R U . . .
H16B H 0.310847 0.806062 0.379248 0.043 Uiso 1 1 calc R U . . .
O1 O -0.1231(3) 0.0996(3) 0.5178(2) 0.0606(9) Uani 1 1 d . . . . .
O2 O -0.0107(3) 0.2185(4) 0.6544(2) 0.0601(9) Uani 1 1 d . . . . .
O3 O 0.6503(3) 0.4119(3) 0.4800(2) 0.0489(8) Uani 1 1 d . . . . .
O4 O 0.6851(3) 0.3760(3) 0.3240(2) 0.0497(8) Uani 1 1 d . . . . .
O5 O 0.4665(3) 0.1397(3) 0.0245(2) 0.0516(8) Uani 1 1 d . . . . .
O6 O 0.5594(4) 0.3117(3) -0.0340(3) 0.0531(12) Uani 0.924(8) 1 d . . P B 1
O7 O 0.8235(12) 0.3971(6) 0.1036(6) 0.050(2) Uani 0.791(11) 1 d D U P A 1
O8 O 0.9338(4) 0.5967(3) 0.1407(4) 0.0428(15) Uani 0.791(11) 1 d D U P A 1
O9 O 0.4159(3) 1.0049(3) 0.4060(2) 0.0494(8) Uani 1 1 d . . . . .
O10 O 0.6324(3) 1.1047(2) 0.3886(3) 0.0512(8) Uani 1 1 d . . . . .
C16 C 0.1706(5) 0.8364(5) 0.1448(4) 0.0617(14) Uani 1 1 d . . . . .
H16C H 0.162127 0.747816 0.102162 0.093 Uiso 1 1 calc R U . . .
H16D H 0.196257 0.837286 0.212569 0.093 Uiso 1 1 calc R U . . .
H16E H 0.247698 0.893875 0.122623 0.093 Uiso 1 1 calc R U . . .
O14 O 0.0386(4) 0.8789(3) 0.1406(3) 0.0766(12) Uani 1 1 d . . . . .
H14 H -0.025043 0.835683 0.166332 0.115 Uiso 1 1 calc R U . . .
C15 C 0.1685(6) 0.3626(6) 0.0516(5) 0.0806(18) Uani 1 1 d . . . . .
H15A H 0.232479 0.446900 0.060801 0.121 Uiso 1 1 calc R U . . .
H15B H 0.067993 0.368937 0.031747 0.121 Uiso 1 1 calc R U . . .
H15C H 0.205430 0.296984 0.000383 0.121 Uiso 1 1 calc R U . . .
O12 O 0.1680(4) 0.3284(3) 0.1362(2) 0.0561(9) Uani 1 1 d . . . . .
H12 H 0.109279 0.258407 0.129213 0.084 Uiso 1 1 calc R U . . .
C13 C -0.1793(5) 0.0847(5) 0.1054(4) 0.0704(16) Uani 1 1 d . . . . .
H13A H -0.190391 0.025694 0.038971 0.106 Uiso 1 1 calc R U . . .
H13B H -0.207275 0.167607 0.103372 0.106 Uiso 1 1 calc R U . . .
H13C H -0.243162 0.046040 0.148355 0.106 Uiso 1 1 calc R U . . .
O11 O -0.0318(3) 0.1061(3) 0.1419(3) 0.0542(9) Uani 1 1 d . . . . .
H11 H 0.001169 0.036073 0.125885 0.081 Uiso 1 1 calc R U . . .
C14 C 0.0367(5) 0.4785(5) 0.3491(4) 0.0599(14) Uani 1 1 d . . . . .
H14A H -0.004842 0.385867 0.325652 0.090 Uiso 1 1 calc R U . . .
H14B H -0.026798 0.528909 0.324187 0.090 Uiso 1 1 calc R U . . .
H14C H 0.042956 0.505190 0.421087 0.090 Uiso 1 1 calc R U . . .
O13 O 0.1787(3) 0.5007(3) 0.3151(2) 0.0578(9) Uani 1 1 d . . . . .
H13 H 0.183010 0.446492 0.260929 0.087 Uiso 1 1 calc R U . . .
N14A N 0.800(2) 0.5134(17) 0.0953(18) 0.040(3) Uani 0.209(11) 1 d D U P A 2
O8A O 0.8883(18) 0.5960(15) 0.0739(16) 0.052(5) Uani 0.209(11) 1 d D U P A 2
O7A O 0.811(4) 0.399(2) 0.073(2) 0.041(6) Uani 0.209(11) 1 d D U P A 2
C9A C 0.680(4) 0.5550(18) 0.153(4) 0.035(4) Uani 0.209(11) 1 d D U P A 2
O6A O 0.400(4) 0.022(4) 0.130(3) 0.054(14) Uani 0.076(8) 1 d . U P B 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
C2 C1 N12 120.1(3) . . ?
N1 C1 C2 125.9(3) . . ?
N1 C1 N12 114.0(4) . . ?
N3 C2 C1 110.2(3) . . ?
N11 C2 C1 131.6(3) . . ?
N11 C2 N3 118.1(4) . . ?
N2 C3 C4 134.2(3) . . ?
N2 C3 N3 121.7(3) . . ?
N3 C3 C4 104.0(3) . . ?
C3 C4 C5 107.3(3) . . ?
C3 C4 N13 126.8(4) . . ?
C5 C4 N13 125.6(3) . . ?
C4 C5 C6 133.3(3) . . ?
N4 C5 C4 110.4(3) . . ?
N4 C5 C6 116.3(3) . . ?
C7 C6 C5 130.5(3) . . ?
N5 C6 C5 118.6(3) . . ?
N5 C6 C7 110.7(4) . . ?
C6 C7 C8 131.2(4) . . ?
N6 C7 C6 107.7(3) . . ?
N6 C7 C8 120.9(4) . . ?
C9 C8 C7 129.9(4) . . ?
N7 C8 C7 118.4(3) . . ?
N7 C8 C9 111.7(3) . . ?
N7 C8 C9A 112.1(8) . . ?
C9A C8 C7 128.9(7) . . ?
C8 C9 N14 127.1(5) . . ?
C10 C9 C8 106.6(4) . . ?
C10 C9 N14 125.8(5) . . ?
N8 C10 C9 103.5(3) . . ?
N8 C10 C9A 103.8(7) . . ?
N9 C10 C9 133.5(4) . . ?
N9 C10 N8 123.0(3) . . ?
N9 C10 C9A 132.3(7) . . ?
N8 C11 C12 109.6(3) . . ?
N16 C11 C12 131.8(3) . . ?
N16 C11 N8 118.6(3) . . ?
C11 C12 N15 120.4(3) . . ?
N10 C12 C11 127.0(3) . . ?
N10 C12 N15 112.7(3) . . ?
N2 N1 C1 122.1(3) . . ?
N1 N2 C3 116.1(3) . . ?
C2 N3 C3 123.9(3) . . ?
N4 N3 C2 122.6(3) . . ?
N4 N3 C3 113.5(3) . . ?
C5 N4 N3 104.7(3) . . ?
C6 N5 O5 107.2(3) . . ?
O6A N5 C6 127(2) . . ?
O6A N5 O5 123.2(18) . . ?
C7 N6 O5 106.6(3) . . ?
O6 N6 C7 136.1(4) . . ?
O6 N6 O5 117.3(3) . . ?
C8 N7 N8 103.6(3) . . ?
C10 N8 C11 122.8(3) . . ?
N7 N8 C10 114.4(3) . . ?
N7 N8 C11 122.8(3) . . ?
N10 N9 C10 115.8(3) . . ?
N9 N10 C12 121.6(3) . . ?
C2 N11 H11A 120.0 . . ?
C2 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
O1 N12 C1 117.6(3) . . ?
O2 N12 C1 119.7(4) . . ?
O2 N12 O1 122.7(3) . . ?
O3 N13 C4 117.7(3) . . ?
O4 N13 C4 117.2(3) . . ?
O4 N13 O3 125.1(3) . . ?
O7 N14 C9 117.3(6) . . ?
O7 N14 O8 124.1(6) . . ?
O8 N14 C9 118.5(4) . . ?
O9 N15 C12 117.5(3) . . ?
O10 N15 C12 119.2(3) . . ?
O10 N15 O9 123.3(3) . . ?
C11 N16 H16A 120.0 . . ?
C11 N16 H16B 120.0 . . ?
H16A N16 H16B 120.0 . . ?
N5 O5 N6 107.7(3) . . ?
H16C C16 H16D 109.5 . . ?
H16C C16 H16E 109.5 . . ?
H16D C16 H16E 109.5 . . ?
O14 C16 H16C 109.5 . . ?
O14 C16 H16D 109.5 . . ?
O14 C16 H16E 109.5 . . ?
C16 O14 H14 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O12 C15 H15A 109.5 . . ?
O12 C15 H15B 109.5 . . ?
O12 C15 H15C 109.5 . . ?
C15 O12 H12 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O11 C13 H13A 109.5 . . ?
O11 C13 H13B 109.5 . . ?
O11 C13 H13C 109.5 . . ?
C13 O11 H11 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O13 C14 H14A 109.5 . . ?
O13 C14 H14B 109.5 . . ?
O13 C14 H14C 109.5 . . ?
C14 O13 H13 109.5 . . ?
O8A N14A C9A 117.7(15) . . ?
O7A N14A O8A 123(2) . . ?
O7A N14A C9A 119(2) . . ?
C8 C9A N14A 125.9(13) . . ?
C10 C9A C8 104.9(11) . . ?
C10 C9A N14A 128.5(14) . . ?
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
C1 C2 1.396(6) . ?
C1 N1 1.333(5) . ?
C1 N12 1.443(5) . ?
C2 N3 1.369(4) . ?
C2 N11 1.305(5) . ?
C3 C4 1.380(5) . ?
C3 N2 1.360(5) . ?
C3 N3 1.369(5) . ?
C4 C5 1.393(5) . ?
C4 N13 1.441(4) . ?
C5 C6 1.464(5) . ?
C5 N4 1.340(4) . ?
C6 C7 1.403(5) . ?
C6 N5 1.312(5) . ?
C7 C8 1.464(5) . ?
C7 N6 1.320(5) . ?
C8 C9 1.397(6) . ?
C8 N7 1.332(4) . ?
C8 C9A 1.410(16) . ?
C9 C10 1.388(6) . ?
C9 N14 1.425(7) . ?
C10 N8 1.371(4) . ?
C10 N9 1.361(5) . ?
C10 C9A 1.408(16) . ?
C11 C12 1.410(5) . ?
C11 N8 1.382(4) . ?
C11 N16 1.300(4) . ?
C12 N10 1.326(5) . ?
C12 N15 1.455(5) . ?
N1 N2 1.313(4) . ?
N3 N4 1.346(4) . ?
N5 O5 1.369(5) . ?
N5 O6A 1.17(4) . ?
N6 O5 1.440(4) . ?
N6 O6 1.233(5) . ?
N7 N8 1.355(4) . ?
N9 N10 1.314(4) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
N12 O1 1.243(4) . ?
N12 O2 1.213(4) . ?
N13 O3 1.229(4) . ?
N13 O4 1.225(4) . ?
N14 O7 1.216(6) . ?
N14 O8 1.229(5) . ?
N15 O9 1.237(4) . ?
N15 O10 1.219(4) . ?
N16 H16A 0.8800 . ?
N16 H16B 0.8800 . ?
C16 H16C 0.9800 . ?
C16 H16D 0.9800 . ?
C16 H16E 0.9800 . ?
C16 O14 1.372(6) . ?
O14 H14 0.8400 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 O12 1.343(7) . ?
O12 H12 0.8400 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 O11 1.405(5) . ?
O11 H11 0.8400 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 O13 1.408(5) . ?
O13 H13 0.8400 . ?
N14A O8A 1.216(15) . ?
N14A O7A 1.212(16) . ?
N14A C9A 1.438(15) . ?
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 C2 N3 C3 -2.8(5) . . . . ?
C1 C2 N3 N4 177.4(3) . . . . ?
C1 N1 N2 C3 -0.6(5) . . . . ?
C2 C1 N1 N2 0.7(6) . . . . ?
C2 C1 N12 O1 9.8(6) . . . . ?
C2 C1 N12 O2 -170.2(4) . . . . ?
C2 N3 N4 C5 179.4(3) . . . . ?
C3 C4 C5 C6 -178.8(4) . . . . ?
C3 C4 C5 N4 1.5(4) . . . . ?
C3 C4 N13 O3 -2.5(6) . . . . ?
C3 C4 N13 O4 176.2(4) . . . . ?
C3 N3 N4 C5 -0.3(4) . . . . ?
C4 C3 N2 N1 -178.9(4) . . . . ?
C4 C3 N3 C2 -178.5(3) . . . . ?
C4 C3 N3 N4 1.3(4) . . . . ?
C4 C5 C6 C7 -52.8(7) . . . . ?
C4 C5 C6 N5 133.1(5) . . . . ?
C4 C5 N4 N3 -0.7(4) . . . . ?
C5 C4 N13 O3 -175.6(4) . . . . ?
C5 C4 N13 O4 3.2(6) . . . . ?
C5 C6 C7 C8 3.0(7) . . . . ?
C5 C6 C7 N6 -171.2(4) . . . . ?
C5 C6 N5 O5 174.0(3) . . . . ?
C5 C6 N5 O6A -25(3) . . . . ?
C6 C5 N4 N3 179.5(3) . . . . ?
C6 C7 C8 C9 131.6(9) . . . . ?
C6 C7 C8 N7 -45.7(6) . . . . ?
C6 C7 C8 C9A 144(4) . . . . ?
C6 C7 N6 O5 -3.7(4) . . . . ?
C6 C7 N6 O6 174.1(4) . . . . ?
C6 N5 O5 N6 -1.2(4) . . . . ?
C7 C6 N5 O5 -1.1(5) . . . . ?
C7 C6 N5 O6A 160(3) . . . . ?
C7 C8 C9 C10 177.2(5) . . . . ?
C7 C8 C9 N14 -10.0(17) . . . . ?
C7 C8 N7 N8 -179.1(4) . . . . ?
C7 C8 C9A C10 -177.9(15) . . . . ?
C7 C8 C9A N14A -7(8) . . . . ?
C7 N6 O5 N5 3.2(4) . . . . ?
C8 C7 N6 O5 -178.7(3) . . . . ?
C8 C7 N6 O6 -0.9(7) . . . . ?
C8 C9 C10 N8 4.9(10) . . . . ?
C8 C9 C10 N9 -175.5(5) . . . . ?
C8 C9 N14 O7 2.8(16) . . . . ?
C8 C9 N14 O8 -175.7(10) . . . . ?
C8 N7 N8 C10 0.2(4) . . . . ?
C8 N7 N8 C11 -177.1(3) . . . . ?
C9 C8 N7 N8 3.1(8) . . . . ?
C9 C10 N8 C11 174.0(7) . . . . ?
C9 C10 N8 N7 -3.3(8) . . . . ?
C9 C10 N9 N10 -175.8(9) . . . . ?
C10 C9 N14 O7 174.2(10) . . . . ?
C10 C9 N14 O8 -4.4(15) . . . . ?
C10 N9 N10 C12 -0.3(6) . . . . ?
C11 C12 N10 N9 -1.6(7) . . . . ?
C11 C12 N15 O9 -5.8(6) . . . . ?
C11 C12 N15 O10 175.2(4) . . . . ?
C12 C11 N8 C10 3.5(5) . . . . ?
C12 C11 N8 N7 -179.5(3) . . . . ?
N1 C1 C2 N3 0.9(6) . . . . ?
N1 C1 C2 N11 -176.2(4) . . . . ?
N1 C1 N12 O1 -169.9(4) . . . . ?
N1 C1 N12 O2 10.2(6) . . . . ?
N2 C3 C4 C5 176.3(4) . . . . ?
N2 C3 C4 N13 2.2(7) . . . . ?
N2 C3 N3 C2 3.2(6) . . . . ?
N2 C3 N3 N4 -177.0(3) . . . . ?
N3 C3 C4 C5 -1.6(4) . . . . ?
N3 C3 C4 N13 -175.7(3) . . . . ?
N3 C3 N2 N1 -1.3(5) . . . . ?
N4 C5 C6 C7 126.9(4) . . . . ?
N4 C5 C6 N5 -47.2(5) . . . . ?
N5 C6 C7 C8 177.5(4) . . . . ?
N5 C6 C7 N6 3.2(5) . . . . ?
N6 C7 C8 C9 -54.8(10) . . . . ?
N6 C7 C8 N7 127.9(4) . . . . ?
N6 C7 C8 C9A -42(4) . . . . ?
N7 C8 C9 C10 -5.3(11) . . . . ?
N7 C8 C9 N14 167.4(9) . . . . ?
N7 C8 C9A C10 11(5) . . . . ?
N7 C8 C9A N14A -178(4) . . . . ?
N8 C10 N9 N10 3.8(6) . . . . ?
N8 C10 C9A C8 -10(4) . . . . ?
N8 C10 C9A N14A 179(5) . . . . ?
N8 C11 C12 N10 0.0(6) . . . . ?
N8 C11 C12 N15 178.6(3) . . . . ?
N9 C10 N8 C11 -5.7(6) . . . . ?
N9 C10 N8 N7 177.0(4) . . . . ?
N9 C10 C9A C8 -179.3(12) . . . . ?
N9 C10 C9A N14A 10(8) . . . . ?
N10 C12 N15 O9 173.1(4) . . . . ?
N10 C12 N15 O10 -6.0(5) . . . . ?
N11 C2 N3 C3 174.7(3) . . . . ?
N11 C2 N3 N4 -5.0(6) . . . . ?
N12 C1 C2 N3 -178.7(3) . . . . ?
N12 C1 C2 N11 4.2(7) . . . . ?
N12 C1 N1 N2 -179.6(3) . . . . ?
N13 C4 C5 C6 -4.6(7) . . . . ?
N13 C4 C5 N4 175.7(3) . . . . ?
N14 C9 C10 N8 -167.9(10) . . . . ?
N14 C9 C10 N9 11.7(18) . . . . ?
N15 C12 N10 N9 179.7(3) . . . . ?
N16 C11 C12 N10 179.9(4) . . . . ?
N16 C11 C12 N15 -1.4(7) . . . . ?
N16 C11 N8 C10 -176.5(4) . . . . ?
N16 C11 N8 N7 0.6(6) . . . . ?
O6 N6 O5 N5 -175.1(3) . . . . ?
O8A N14A C9A C8 170(4) . . . . ?
O8A N14A C9A C10 -21(7) . . . . ?
O7A N14A C9A C8 -12(8) . . . . ?
O7A N14A C9A C10 157(5) . . . . ?
C9A C8 N7 N8 -7(3) . . . . ?
C9A C10 N8 C11 -176(3) . . . . ?
C9A C10 N8 N7 7(3) . . . . ?
C9A C10 N9 N10 171(4) . . . . ?
O6A N5 O5 N6 -163(3) . . . . ?
