#------------------------------------------------------------------------------
#$Date: 2023-09-18 10:31:01 +0300 (Mon, 18 Sep 2023) $
#$Revision: 286375 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/75/8107502.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_8107502
loop_
_publ_author_name
'Li, Na'
'Wang, Xiao-Jie'
'Qin, Yu-Cai'
'Wang, Jing-Yun'
_publ_section_title
;
 The crystal structure of tetra(1-ethylimidazole-κ 1 N)-[μ
 4-imidazole-4,5-dicarboxylato-κ 4 O, N, O′,
 N′]-trioxido-divanadium, C25H33N10O7V2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              585
_journal_page_last               587
_journal_paper_doi               10.1515/ncrs-2023-0110
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C25 H33 N10 O7 V2'
_chemical_formula_sum            'C25 H33 N10 O7 V2'
_chemical_formula_weight         687.49
_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
_cell_angle_alpha                65.3730(10)
_cell_angle_beta                 70.3510(10)
_cell_angle_gamma                88.052(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3933(4)
_cell_length_b                   12.5655(5)
_cell_length_c                   14.1841(5)
_cell_measurement_reflns_used    4598
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.93
_cell_volume                     1573.62(11)
_computing_cell_refinement       'Bruker SMART [1]'
_computing_data_collection       'Bruker SMART [1]'
_computing_data_reduction        'Bruker SAINT [1]'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009) [2]'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009) [2]'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015) [3]'
_computing_structure_solution    'Bruker SHELXTL [4]'
_diffrn_ambient_temperature      173.00
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13171
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.361
_diffrn_reflns_theta_min         2.926
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6678
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       block
_exptl_crystal_F_000             710
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_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     441
_refine_ls_number_reflns         5733
_refine_ls_number_restraints     94
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0291P)²+0.9293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0885
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4326
_reflns_number_total             5733
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0110_suppl_001.cif
_cod_data_source_block           1
_cod_original_cell_volume        1573.62(10)
_cod_database_code               8107502
_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   0.926
_shelx_estimated_absorpt_t_min   0.849
_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. Restrained distances
 C9-C10 = C19-C20 = C9'-C10' = C19'-C20'
 1.53 with sigma of 0.02
 N4-C9 \\sim N4-C9' \\sim N8-C19 \\sim N8-C19'
 with sigma of 0.02
 N4-C10 \\sim N4-C10' \\sim N8-C20 \\sim N8-C20'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C9 \\sim C10 \\sim C9' \\sim C10' \\sim C19 \\sim C20 \\sim C19' \\sim C20':
within 2A with sigma of 0.02 and sigma for terminal atoms of 0.03 within 2A
Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C9')=Sof(H9'A)=Sof(H9'B)=Sof(C10')=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(1)
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1)
 Sof(C19')=Sof(H19C)=Sof(H19D)=Sof(C20')=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(2)
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C24(H24A,H24B), C9(H9A,H9B), C9'(H9'A,H9'B), C19(H19A,H19B),
 C19'(H19C,H19D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C16(H16),
 C17(H17), C18(H18), C21(H21), C22(H22), C23(H23)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C25(H25A,H25B,H25C), C10(H10A,H10B,H10C), C10'(H10D,H10E,
 H10F), C20(H20A,H20B,H20C), C20'(H20D,H20E,H20F)
;
_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 0.2837(3) 0.8382(2) 0.56417(19) 0.0217(6) Uani 1 1 d . . . . .
H1 H 0.304385 0.921621 0.526685 0.026 Uiso 1 1 calc R U . . .
C2 C 0.2237(3) 0.6562(2) 0.60165(19) 0.0182(5) Uani 1 1 d . . . . .
C3 C 0.2558(3) 0.6569(2) 0.68855(19) 0.0191(5) Uani 1 1 d . . . . .
C4 C 0.1891(2) 0.5672(2) 0.56758(19) 0.0179(5) Uani 1 1 d . . . . .
C5 C 0.2755(3) 0.5708(2) 0.79107(19) 0.0200(6) Uani 1 1 d . . . . .
C6 C 0.6149(3) 0.8189(3) 0.8402(2) 0.0347(7) Uani 1 1 d . . . . .
H6 H 0.646550 0.895157 0.780268 0.042 Uiso 1 1 calc R U . . .
C7 C 0.5999(3) 0.6589(3) 0.9882(2) 0.0344(7) Uani 1 1 d . . . . .
H7 H 0.617384 0.601812 1.050696 0.041 Uiso 1 1 calc R U . . .
C8 C 0.4974(3) 0.6493(2) 0.9532(2) 0.0278(6) Uani 1 1 d . . . . .
H8 H 0.429060 0.583195 0.987680 0.033 Uiso 1 1 calc R U . . .
C11 C 0.5331(3) 0.8559(2) 0.3084(2) 0.0233(6) Uani 1 1 d . . . . .
H11 H 0.522576 0.921362 0.326391 0.028 Uiso 1 1 calc R U . . .
C12 C 0.6280(3) 0.7207(2) 0.2579(2) 0.0312(7) Uani 1 1 d . . . . .
H12 H 0.693193 0.673448 0.235017 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4910(3) 0.7083(3) 0.2788(2) 0.0304(7) Uani 1 1 d . . . . .
H13 H 0.443460 0.650278 0.271836 0.036 Uiso 1 1 calc R U . . .
C14 C 0.7885(3) 0.8590(3) 0.2671(2) 0.0357(7) Uani 1 1 d . . . . .
H14A H 0.826470 0.793323 0.314290 0.043 Uiso 1 1 calc R U . . .
H14B H 0.776768 0.920251 0.295134 0.043 Uiso 1 1 calc R U . . .
C15 C 0.8896(3) 0.9106(3) 0.1490(3) 0.0454(8) Uani 1 1 d . . . . .
H15A H 0.900830 0.850571 0.120654 0.068 Uiso 1 1 calc R U . . .
H15B H 0.978668 0.936338 0.147234 0.068 Uiso 1 1 calc R U . . .
H15C H 0.854659 0.978313 0.102740 0.068 Uiso 1 1 calc R U . . .
C16 C 0.1187(3) 0.7002(3) 0.2434(2) 0.0286(6) Uani 1 1 d . . . . .
H16 H 0.051046 0.642482 0.307502 0.034 Uiso 1 1 calc R U . . .
C17 C 0.2464(3) 0.8057(3) 0.0699(2) 0.0304(7) Uani 1 1 d . . . . .
H17 H 0.285718 0.835845 -0.008517 0.036 Uiso 1 1 calc R U . . .
C18 C 0.2815(3) 0.8445(3) 0.1346(2) 0.0296(7) Uani 1 1 d . . . . .
H18 H 0.350260 0.908074 0.108818 0.035 Uiso 1 1 calc R U . . .
C21 C -0.0872(3) 0.6773(2) 0.5116(2) 0.0243(6) Uani 1 1 d . . . . .
H21 H -0.064010 0.603493 0.511737 0.029 Uiso 1 1 calc R U . . .
C22 C -0.2066(3) 0.8131(3) 0.5446(3) 0.0386(8) Uani 1 1 d . . . . .
H22 H -0.280223 0.851901 0.571493 0.046 Uiso 1 1 calc R U . . .
C23 C -0.0753(3) 0.8617(3) 0.4795(2) 0.0312(7) Uani 1 1 d . . . . .
H23 H -0.040789 0.941996 0.452220 0.037 Uiso 1 1 calc R U . . .
C24 C -0.3350(3) 0.6078(3) 0.6257(2) 0.0380(8) Uani 1 1 d . . . . .
H24A H -0.391693 0.618163 0.692279 0.046 Uiso 1 1 calc R U . . .
H24B H -0.305735 0.527927 0.650840 0.046 Uiso 1 1 calc R U . . .
C25 C -0.4202(3) 0.6173(3) 0.5567(3) 0.0462(9) Uani 1 1 d . . . . .
H25A H -0.453423 0.694739 0.534922 0.069 Uiso 1 1 calc R U . . .
H25B H -0.498874 0.555272 0.599840 0.069 Uiso 1 1 calc R U . . .
H25C H -0.364034 0.608123 0.490169 0.069 Uiso 1 1 calc R U . . .
N1 N 0.2938(2) 0.77216(18) 0.66340(16) 0.0205(5) Uani 1 1 d . . . . .
N2 N 0.2412(2) 0.77246(18) 0.52482(16) 0.0199(5) Uani 1 1 d . . . . .
N3 N 0.5071(2) 0.75076(18) 0.85937(17) 0.0232(5) Uani 1 1 d . . . . .
N4 N 0.6742(3) 0.7673(2) 0.9157(2) 0.0371(6) Uani 1 1 d D . . . .
N5 N 0.4308(2) 0.79277(19) 0.31190(17) 0.0225(5) Uani 1 1 d . . . . .
N6 N 0.6537(2) 0.8153(2) 0.27624(18) 0.0256(5) Uani 1 1 d . . . . .
N7 N 0.2010(2) 0.77671(19) 0.24488(16) 0.0231(5) Uani 1 1 d . . . . .
N8 N 0.1429(2) 0.7144(2) 0.13961(18) 0.0304(6) Uani 1 1 d D . . . .
N9 N 0.0011(2) 0.77588(18) 0.45882(16) 0.0214(5) Uani 1 1 d . . . . .
N10 N -0.2126(2) 0.6962(2) 0.56419(19) 0.0307(6) Uani 1 1 d . . . . .
O1 O 0.19169(17) 0.61322(15) 0.46655(13) 0.0194(4) Uani 1 1 d . . . . .
O2 O 0.16089(19) 0.46137(15) 0.63101(14) 0.0258(4) Uani 1 1 d . . . . .
O3 O 0.2392(2) 0.46473(16) 0.83405(15) 0.0293(5) Uani 1 1 d . . . . .
O4 O 0.33995(19) 0.62254(15) 0.82895(14) 0.0253(4) Uani 1 1 d . . . . .
O5 O 0.27083(19) 0.86327(17) 0.82264(14) 0.0274(4) Uani 1 1 d . . . . .
O6 O 0.50398(19) 0.89838(15) 0.65755(13) 0.0243(4) Uani 1 1 d . . . . .
O7 O 0.22472(19) 0.94104(16) 0.33137(14) 0.0260(4) Uani 1 1 d . . . . .
V1 V 0.38325(4) 0.79850(4) 0.76216(3) 0.01819(12) Uani 1 1 d . . . . .
V2 V 0.21698(4) 0.80033(4) 0.37792(3) 0.01870(12) Uani 1 1 d . . . . .
C9 C 0.7945(14) 0.828(2) 0.915(2) 0.054(5) Uani 0.44(3) 1 d D U P A 1
H9A H 0.782259 0.814432 0.992014 0.064 Uiso 0.44(3) 1 calc R U P A 1
H9B H 0.803103 0.913690 0.869643 0.064 Uiso 0.44(3) 1 calc R U P A 1
C10 C 0.9231(11) 0.7787(17) 0.869(2) 0.067(4) Uani 0.44(3) 1 d D U P A 1
H10A H 0.913741 0.693559 0.914111 0.100 Uiso 0.44(3) 1 calc R U P A 1
H10B H 1.003205 0.817352 0.868860 0.100 Uiso 0.44(3) 1 calc R U P A 1
H10C H 0.935582 0.793521 0.792310 0.100 Uiso 0.44(3) 1 calc R U P A 1
C9' C 0.8064(12) 0.8059(19) 0.9178(17) 0.057(4) Uani 0.56(3) 1 d D U P A 2
H9'A H 0.821092 0.748200 0.985421 0.068 Uiso 0.56(3) 1 calc R U P A 2
H9'B H 0.801139 0.883130 0.921248 0.068 Uiso 0.56(3) 1 calc R U P A 2
C10' C 0.9264(8) 0.8169(13) 0.8177(14) 0.070(3) Uani 0.56(3) 1 d D U P A 2
H10D H 0.936384 0.739270 0.817106 0.106 Uiso 0.56(3) 1 calc R U P A 2
H10E H 1.010527 0.846865 0.819975 0.106 Uiso 0.56(3) 1 calc R U P A 2
H10F H 0.910566 0.871599 0.750421 0.106 Uiso 0.56(3) 1 calc R U P A 2
C19 C 0.049(2) 0.6577(19) 0.110(2) 0.030(4) Uani 0.35(3) 1 d D U P B 3
H19A H 0.045447 0.712126 0.036463 0.036 Uiso 0.35(3) 1 calc R U P B 3
H19B H -0.044885 0.638786 0.165483 0.036 Uiso 0.35(3) 1 calc R U P B 3
C20 C 0.1041(19) 0.5449(18) 0.105(2) 0.048(4) Uani 0.35(3) 1 d D U P B 3
H20A H 0.199977 0.563442 0.054481 0.071 Uiso 0.35(3) 1 calc R U P B 3
H20B H 0.048262 0.510366 0.079031 0.071 Uiso 0.35(3) 1 calc R U P B 3
H20C H 0.099066 0.488426 0.179660 0.071 Uiso 0.35(3) 1 calc R U P B 3
C19' C 0.0823(16) 0.6386(13) 0.1056(14) 0.046(3) Uani 0.65(3) 1 d D U P B 4
H19C H 0.117168 0.672550 0.023611 0.055 Uiso 0.65(3) 1 calc R U P B 4
H19D H -0.018800 0.638803 0.131127 0.055 Uiso 0.65(3) 1 calc R U P B 4
C20' C 0.1133(14) 0.5134(9) 0.1501(12) 0.058(3) Uani 0.65(3) 1 d D U P B 4
H20D H 0.213124 0.512054 0.123949 0.087 Uiso 0.65(3) 1 calc R U P B 4
H20E H 0.070160 0.468308 0.124163 0.087 Uiso 0.65(3) 1 calc R U P B 4
H20F H 0.076723 0.478170 0.231400 0.087 Uiso 0.65(3) 1 calc R U P B 4
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'
V V 0.3005 0.5294 '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
N1 C1 H1 124.2 . .
N2 C1 H1 124.2 . .
N2 C1 N1 111.7(2) . .
C3 C2 C4 137.5(2) . .
N2 C2 C3 106.8(2) . .
N2 C2 C4 115.4(2) . .
C2 C3 C5 138.4(2) . .
N1 C3 C2 107.9(2) . .
N1 C3 C5 113.2(2) . .
O1 C4 C2 112.9(2) . .
O2 C4 C2 122.1(2) . .
O2 C4 O1 125.0(2) . .
O3 C5 C3 124.7(2) . .
O3 C5 O4 123.9(2) . .
O4 C5 C3 111.4(2) . .
N3 C6 H6 124.3 . .
N3 C6 N4 111.3(2) . .
N4 C6 H6 124.3 . .
C8 C7 H7 126.8 . .
C8 C7 N4 106.3(2) . .
N4 C7 H7 126.8 . .
C7 C8 H8 125.3 . .
C7 C8 N3 109.4(2) . .
N3 C8 H8 125.3 . .
N5 C11 H11 124.4 . .
N5 C11 N6 111.1(2) . .
N6 C11 H11 124.4 . .
C13 C12 H12 126.9 . .
C13 C12 N6 106.2(2) . .
N6 C12 H12 126.9 . .
C12 C13 H13 125.2 . .
C12 C13 N5 109.7(3) . .
N5 C13 H13 125.2 . .
H14A C14 H14B 107.9 . .
C15 C14 H14A 109.1 . .
C15 C14 H14B 109.1 . .
N6 C14 H14A 109.1 . .
N6 C14 H14B 109.1 . .
N6 C14 C15 112.3(3) . .
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 . .
N7 C16 H16 124.4 . .
N7 C16 N8 111.2(2) . .
N8 C16 H16 124.4 . .
C18 C17 H17 126.7 . .
C18 C17 N8 106.5(2) . .
N8 C17 H17 126.7 . .
C17 C18 H18 125.4 . .
C17 C18 N7 109.2(3) . .
N7 C18 H18 125.4 . .
N9 C21 H21 124.5 . .
N9 C21 N10 111.0(2) . .
N10 C21 H21 124.5 . .
C23 C22 H22 126.8 . .
C23 C22 N10 106.4(3) . .
N10 C22 H22 126.8 . .
C22 C23 H23 125.3 . .
C22 C23 N9 109.3(3) . .
N9 C23 H23 125.3 . .
H24A C24 H24B 107.9 . .
C25 C24 H24A 109.2 . .
C25 C24 H24B 109.2 . .
N10 C24 H24A 109.2 . .
N10 C24 H24B 109.2 . .
N10 C24 C25 112.0(2) . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25B 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C1 N1 C3 106.4(2) . .
C1 N1 V1 135.59(18) . .
C3 N1 V1 116.63(15) . .
C1 N2 C2 107.2(2) . .
C1 N2 V2 136.19(17) . .
C2 N2 V2 116.26(17) . .
C6 N3 C8 105.6(2) . .
C6 N3 V1 123.80(17) . .
C8 N3 V1 130.63(19) . .
C6 N4 C7 107.4(2) . .
C6 N4 C9 122.1(12) . .
C6 N4 C9' 129.2(9) . .
C7 N4 C9 130.5(12) . .
C7 N4 C9' 122.9(9) . .
C11 N5 C13 105.4(2) . .
C11 N5 V2 127.60(18) . .
C13 N5 V2 126.33(19) . .
C11 N6 C12 107.6(2) . .
C11 N6 C14 127.1(3) . .
C12 N6 C14 125.3(2) . .
C16 N7 C18 105.5(2) . .
C16 N7 V2 130.38(18) . .
C18 N7 V2 124.13(19) . .
C16 N8 C17 107.6(2) . .
C16 N8 C19 123.2(11) . .
C16 N8 C19' 127.0(7) . .
C17 N8 C19 127.8(11) . .
C17 N8 C19' 125.1(7) . .
C21 N9 C23 105.4(2) . .
C21 N9 V2 129.59(18) . .
C23 N9 V2 124.55(18) . .
C21 N10 C22 107.8(2) . .
C21 N10 C24 124.9(3) . .
C22 N10 C24 127.2(2) . .
C4 O1 V2 118.91(16) . .
C5 O4 V1 122.03(15) . .
N1 V1 N3 152.33(9) . .
O4 V1 N1 76.33(8) . .
O4 V1 N3 80.95(8) . .
O5 V1 N1 102.33(9) . .
O5 V1 N3 101.40(9) . .
O5 V1 O4 114.77(9) . .
O5 V1 O6 108.68(10) . .
O6 V1 N1 93.64(9) . .
O6 V1 N3 92.06(9) . .
O6 V1 O4 136.54(9) . .
N2 V2 N5 88.08(8) . .
N2 V2 N7 163.25(9) . .
N2 V2 N9 89.36(8) . .
N2 V2 O1 76.09(7) . .
N5 V2 O1 87.78(7) . .
N7 V2 N5 86.92(8) . .
N7 V2 N9 92.84(8) . .
N7 V2 O1 87.74(8) . .
N9 V2 N5 170.09(8) . .
N9 V2 O1 82.31(7) . .
O7 V2 N2 95.69(9) . .
O7 V2 N5 97.11(9) . .
O7 V2 N7 100.78(9) . .
O7 V2 N9 92.67(9) . .
O7 V2 O1 170.35(8) . .
N4 C9 H9A 109.9 . .
N4 C9 H9B 109.9 . .
N4 C9 C10 108.8(12) . .
H9A C9 H9B 108.3 . .
C10 C9 H9A 109.9 . .
C10 C9 H9B 109.9 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10B 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N4 C9' H9'A 109.2 . .
N4 C9' H9'B 109.2 . .
N4 C9' C10' 112.0(11) . .
H9'A C9' H9'B 107.9 . .
C10' C9' H9'A 109.2 . .
C10' C9' H9'B 109.2 . .
C9' C10' H10D 109.5 . .
C9' C10' H10E 109.5 . .
C9' C10' H10F 109.5 . .
H10D C10' H10E 109.5 . .
H10D C10' H10F 109.5 . .
H10E C10' H10F 109.5 . .
N8 C19 H19A 110.0 . .
N8 C19 H19B 110.0 . .
N8 C19 C20 108.6(12) . .
H19A C19 H19B 108.4 . .
C20 C19 H19A 110.0 . .
C20 C19 H19B 110.0 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
N8 C19' H19C 108.8 . .
N8 C19' H19D 108.8 . .
N8 C19' C20' 113.9(8) . .
H19C C19' H19D 107.7 . .
C20' C19' H19C 108.8 . .
C20' C19' H19D 108.8 . .
C19' C20' H20D 109.5 . .
C19' C20' H20E 109.5 . .
C19' C20' H20F 109.5 . .
H20D C20' H20E 109.5 . .
H20D C20' H20F 109.5 . .
H20E C20' H20F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 0.9500 .
C1 N1 1.342(3) .
C1 N2 1.327(3) .
C2 C3 1.384(3) .
C2 C4 1.487(4) .
C2 N2 1.383(3) .
C3 C5 1.484(3) .
C3 N1 1.376(3) .
C4 O1 1.293(3) .
C4 O2 1.231(3) .
C5 O3 1.222(3) .
C5 O4 1.312(3) .
C6 H6 0.9500 .
C6 N3 1.315(4) .
C6 N4 1.336(3) .
C7 H7 0.9500 .
C7 C8 1.344(4) .
C7 N4 1.372(4) .
C8 H8 0.9500 .
C8 N3 1.383(3) .
C11 H11 0.9500 .
C11 N5 1.324(3) .
C11 N6 1.344(3) .
C12 H12 0.9500 .
C12 C13 1.353(4) .
C12 N6 1.371(4) .
C13 H13 0.9500 .
C13 N5 1.383(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C14 C15 1.512(4) .
C14 N6 1.467(4) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16 0.9500 .
C16 N7 1.320(4) .
C16 N8 1.340(3) .
C17 H17 0.9500 .
C17 C18 1.350(4) .
C17 N8 1.369(4) .
C18 H18 0.9500 .
C18 N7 1.389(3) .
C21 H21 0.9500 .
C21 N9 1.334(3) .
C21 N10 1.336(3) .
C22 H22 0.9500 .
C22 C23 1.352(4) .
C22 N10 1.375(4) .
C23 H23 0.9500 .
C23 N9 1.389(3) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C24 C25 1.494(5) .
C24 N10 1.468(4) .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
N1 V1 2.054(2) .
N2 V2 2.066(2) .
N3 V1 2.090(2) .
N4 C9 1.483(12) .
N4 C9' 1.487(10) .
N5 V2 2.117(2) .
N7 V2 2.087(2) .
N8 C19 1.488(13) .
N8 C19' 1.471(9) .
N9 V2 2.113(2) .
O1 V2 2.1292(17) .
O4 V1 2.0060(18) .
O5 V1 1.6145(18) .
O6 V1 1.6292(18) .
O7 V2 1.6031(18) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C9 C10 1.515(17) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C9' H9'A 0.9900 .
C9' H9'B 0.9900 .
C9' C10' 1.500(15) .
C10' H10D 0.9800 .
C10' H10E 0.9800 .
C10' H10F 0.9800 .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C19 C20 1.527(16) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C19' H19C 0.9900 .
C19' H19D 0.9900 .
C19' C20' 1.500(11) .
C20' H20D 0.9800 .
C20' H20E 0.9800 .
C20' H20F 0.9800 .
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
C2 C3 C5 O3 -15.1(5) . . . .
C2 C3 C5 O4 163.5(3) . . . .
C2 C3 N1 C1 0.3(3) . . . .
C2 C3 N1 V1 -168.36(16) . . . .
C2 C4 O1 V2 -7.8(3) . . . .
C3 C2 C4 O1 -168.0(3) . . . .
C3 C2 C4 O2 12.2(5) . . . .
C3 C2 N2 C1 0.9(3) . . . .
C3 C2 N2 V2 174.97(16) . . . .
C3 C5 O4 V1 6.5(3) . . . .
C4 C2 C3 C5 1.7(6) . . . .
C4 C2 C3 N1 172.9(3) . . . .
C4 C2 N2 C1 -174.3(2) . . . .
C4 C2 N2 V2 -0.2(3) . . . .
C5 C3 N1 C1 173.9(2) . . . .
C5 C3 N1 V1 5.2(3) . . . .
C6 N4 C9 C10 -103(2) . . . .
C6 N4 C9' C10' -59(2) . . . .
C7 C8 N3 C6 -0.1(3) . . . .
C7 C8 N3 V1 -179.2(2) . . . .
C7 N4 C9 C10 80(2) . . . .
C7 N4 C9' C10' 111.5(15) . . . .
C8 C7 N4 C6 -0.1(4) . . . .
C8 C7 N4 C9 177.1(10) . . . .
C8 C7 N4 C9' -172.5(9) . . . .
C12 C13 N5 C11 1.0(3) . . . .
C12 C13 N5 V2 -170.28(18) . . . .
C13 C12 N6 C11 0.6(3) . . . .
C13 C12 N6 C14 177.9(3) . . . .
C15 C14 N6 C11 -116.2(3) . . . .
C15 C14 N6 C12 67.1(4) . . . .
C16 N8 C19 C20 -97(2) . . . .
C16 N8 C19' C20' -60.4(15) . . . .
C17 C18 N7 C16 -0.8(3) . . . .
C17 C18 N7 V2 179.33(19) . . . .
C17 N8 C19 C20 98.6(19) . . . .
C17 N8 C19' C20' 112.1(11) . . . .
C18 C17 N8 C16 -0.2(3) . . . .
C18 C17 N8 C19 166.3(11) . . . .
C18 C17 N8 C19' -173.9(8) . . . .
C22 C23 N9 C21 0.6(3) . . . .
C22 C23 N9 V2 -172.21(19) . . . .
C23 C22 N10 C21 0.1(3) . . . .
C23 C22 N10 C24 -176.5(3) . . . .
C25 C24 N10 C21 -96.0(3) . . . .
C25 C24 N10 C22 80.0(4) . . . .
N1 C1 N2 C2 -0.7(3) . . . .
N1 C1 N2 V2 -173.07(18) . . . .
N1 C3 C5 O3 174.1(2) . . . .
N1 C3 C5 O4 -7.3(3) . . . .
N2 C1 N1 C3 0.3(3) . . . .
N2 C1 N1 V1 165.72(19) . . . .
N2 C2 C3 C5 -171.8(3) . . . .
N2 C2 C3 N1 -0.7(3) . . . .
N2 C2 C4 O1 5.2(3) . . . .
N2 C2 C4 O2 -174.6(2) . . . .
N3 C6 N4 C7 0.0(4) . . . .
N3 C6 N4 C9 -177.5(9) . . . .
N3 C6 N4 C9' 171.8(10) . . . .
N4 C6 N3 C8 0.0(4) . . . .
N4 C6 N3 V1 179.2(2) . . . .
N4 C7 C8 N3 0.1(4) . . . .
N5 C11 N6 C12 0.0(3) . . . .
N5 C11 N6 C14 -177.2(2) . . . .
N6 C11 N5 C13 -0.6(3) . . . .
N6 C11 N5 V2 170.55(16) . . . .
N6 C12 C13 N5 -1.0(3) . . . .
N7 C16 N8 C17 -0.3(3) . . . .
N7 C16 N8 C19 -167.6(10) . . . .
N7 C16 N8 C19' 173.3(8) . . . .
N8 C16 N7 C18 0.7(3) . . . .
N8 C16 N7 V2 -179.46(18) . . . .
N8 C17 C18 N7 0.6(3) . . . .
N9 C21 N10 C22 0.3(3) . . . .
N9 C21 N10 C24 176.9(2) . . . .
N10 C21 N9 C23 -0.5(3) . . . .
N10 C21 N9 V2 171.74(17) . . . .
N10 C22 C23 N9 -0.4(3) . . . .
O2 C4 O1 V2 172.02(19) . . . .
O3 C5 O4 V1 -174.91(19) . . . .
