#------------------------------------------------------------------------------
#$Date: 2026-05-04 15:11:28 +0200 (Mon, 04 May 2026) $
#$Revision: 305706 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/72/09/7720980.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_7720980
loop_
_publ_author_name
'Balayan, Kajal'
'Biswas, Arindam'
'Sharma, Himanshu'
'Tiwari, Prabhakar'
'Vanka, Kumar'
'Gonnade, Rajesh G.'
'Rath, Arup K.'
'Sen, Sakya S.'
_publ_section_title
;
 Unveiling the reactivity of N-heterocyclic methylene hydrazines.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5432
_journal_page_last               5436
_journal_paper_doi               10.1039/d6dt00611f
_journal_volume                  55
_journal_year                    2026
_chemical_formula_moiety         '2(C12 H23 N4 Cl), 0.75 (H2 O)'
_chemical_formula_sum            'C24 H47.5 Cl2 N8 O0.75'
_chemical_formula_weight         531.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'difference Fourier'
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2026-02-08 deposited with the CCDC.	2026-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.906(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5515(12)
_cell_length_b                   11.5612(13)
_cell_length_c                   21.090(2)
_cell_measurement_reflns_used    9826
_cell_measurement_temperature    201(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.56
_cell_volume                     3058.7(5)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      201(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            87615
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.861
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.1504
_exptl_absorpt_correction_T_min  0.1118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       block
_exptl_crystal_F_000             1150
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0701
_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)+(0.0831P)²+3.1623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1901
_refine_ls_wR_factor_ref         0.1991
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4793
_reflns_number_total             5672
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6dt00611f2.cif
_cod_data_source_block           mo_KB_ItbuNNCH2salt_2_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'direct method' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_cell_volume        3058.7(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C24 H47.50 Cl2 N8 O0.75'
_cod_database_code               7720980
_shelx_shelxl_version_number     2019/3
_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   0.956
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Cl1 Cl 0.57289(6) -0.02293(9) 0.62229(4) 0.0614(3) Uani 1 1 d . . . . .
N1 N 0.90340(18) 0.2566(2) 0.63290(11) 0.0421(5) Uani 1 1 d . . . . .
N2 N 0.85453(17) 0.1904(2) 0.72469(11) 0.0405(5) Uani 1 1 d . . . . .
N3 N 0.8127(2) 0.0724(2) 0.63220(13) 0.0499(6) Uani 1 1 d . . . . .
H3 H 0.748(3) 0.058(4) 0.6294(19) 0.075 Uiso 1 1 d . U . . .
N4 N 0.8863(2) -0.0130(3) 0.62053(16) 0.0659(8) Uani 1 1 d . . . . .
C1 C 0.8531(2) 0.1693(3) 0.66162(13) 0.0401(6) Uani 1 1 d . . . . .
C2 C 0.9068(2) 0.2937(3) 0.73539(13) 0.0433(6) Uani 1 1 d . . . . .
H2 H 0.918871 0.330102 0.775363 0.052 Uiso 1 1 calc R U . . .
C3 C 0.9377(2) 0.3335(3) 0.67904(13) 0.0452(7) Uani 1 1 d . . . . .
H3A H 0.976492 0.402747 0.672227 0.054 Uiso 1 1 calc R U . . .
C4 C 0.9176(2) 0.2832(3) 0.56295(13) 0.0501(7) Uani 1 1 d . . . . .
C5 C 0.8620(4) 0.3979(4) 0.54999(18) 0.0779(12) Uani 1 1 d . . . . .
H5A H 0.866188 0.417060 0.504879 0.117 Uiso 1 1 calc R U . . .
H5B H 0.896931 0.458688 0.575507 0.117 Uiso 1 1 calc R U . . .
H5C H 0.787080 0.391867 0.561219 0.117 Uiso 1 1 calc R U . . .
C6 C 0.8719(4) 0.1905(4) 0.51875(17) 0.0929(16) Uani 1 1 d . . . . .
H6A H 0.880574 0.214355 0.474617 0.139 Uiso 1 1 calc R U . . .
H6B H 0.796034 0.179989 0.526557 0.139 Uiso 1 1 calc R U . . .
H6C H 0.909815 0.117526 0.526556 0.139 Uiso 1 1 calc R U . . .
C7 C 1.0361(3) 0.2961(4) 0.55356(18) 0.0765(11) Uani 1 1 d . . . . .
H7A H 1.047927 0.322638 0.510225 0.115 Uiso 1 1 calc R U . . .
H7B H 1.071272 0.221330 0.560496 0.115 Uiso 1 1 calc R U . . .
H7C H 1.065647 0.352809 0.583879 0.115 Uiso 1 1 calc R U . . .
C8 C 0.7982(2) 0.1221(3) 0.77521(14) 0.0465(7) Uani 1 1 d . . . . .
C9 C 0.6791(2) 0.1399(4) 0.76450(17) 0.0628(9) Uani 1 1 d . . . . .
H9A H 0.640952 0.102117 0.798615 0.094 Uiso 1 1 calc R U . . .
H9B H 0.656379 0.106087 0.723627 0.094 Uiso 1 1 calc R U . . .
H9C H 0.663118 0.222829 0.764336 0.094 Uiso 1 1 calc R U . . .
C10 C 0.8335(3) 0.1683(4) 0.83977(16) 0.0681(10) Uani 1 1 d . . . . .
H10A H 0.799939 0.123036 0.872939 0.102 Uiso 1 1 calc R U . . .
H10B H 0.812202 0.249555 0.843273 0.102 Uiso 1 1 calc R U . . .
H10C H 0.911199 0.162251 0.844873 0.102 Uiso 1 1 calc R U . . .
C11 C 0.8284(3) -0.0049(3) 0.77078(19) 0.0712(11) Uani 1 1 d . . . . .
H11A H 0.800584 -0.046755 0.807091 0.107 Uiso 1 1 calc R U . . .
H11B H 0.906188 -0.012207 0.771055 0.107 Uiso 1 1 calc R U . . .
H11C H 0.797840 -0.037554 0.731341 0.107 Uiso 1 1 calc R U . . .
C12 C 0.8510(4) -0.1036(4) 0.5946(2) 0.0850(13) Uani 1 1 d . . . . .
H12A H 0.777090 -0.110566 0.584113 0.102 Uiso 1 1 calc R U . . .
H12B H 0.898199 -0.165196 0.585502 0.102 Uiso 1 1 calc R U . . .
Cl2 Cl 0.07313(6) 0.59987(7) 0.62820(3) 0.0520(2) Uani 1 1 d . . . . .
N5 N 0.39530(19) 0.3354(2) 0.64154(12) 0.0475(6) Uani 1 1 d . . . . .
N6 N 0.35473(18) 0.3992(2) 0.73536(12) 0.0449(6) Uani 1 1 d . . . . .
N7 N 0.3145(2) 0.5241(3) 0.64555(15) 0.0586(8) Uani 1 1 d . . . . .
H7 H 0.249(4) 0.541(4) 0.635(2) 0.088 Uiso 1 1 d . U . . .
N8 N 0.3921(2) 0.6043(3) 0.63331(15) 0.0654(8) Uani 1 1 d . . . . .
C13 C 0.3509(2) 0.4241(3) 0.67296(14) 0.0446(7) Uani 1 1 d . . . . .
C14 C 0.4295(2) 0.2552(3) 0.68600(16) 0.0523(8) Uani 1 1 d . . . . .
H14 H 0.465582 0.184983 0.677393 0.063 Uiso 1 1 calc R U . . .
C15 C 0.4133(3) 0.3190(3) 0.57177(16) 0.0618(9) Uani 1 1 d . . . . .
C16 C 0.4034(2) 0.2930(3) 0.74326(15) 0.0495(7) Uani 1 1 d . . . . .
H16 H 0.416082 0.253753 0.782372 0.059 Uiso 1 1 calc R U . . .
C17 C 0.3491(5) 0.4020(5) 0.5304(2) 0.1085(19) Uani 1 1 d . . . . .
H17A H 0.347399 0.374251 0.486462 0.163 Uiso 1 1 calc R U . . .
H17B H 0.382165 0.478751 0.532413 0.163 Uiso 1 1 calc R U . . .
H17C H 0.276260 0.406703 0.545477 0.163 Uiso 1 1 calc R U . . .
C18 C 0.5318(4) 0.3301(6) 0.5635(2) 0.115(2) Uani 1 1 d . . . . .
H18A H 0.547893 0.317196 0.518900 0.172 Uiso 1 1 calc R U . . .
H18B H 0.569315 0.272417 0.589985 0.172 Uiso 1 1 calc R U . . .
H18C H 0.555209 0.407785 0.576255 0.172 Uiso 1 1 calc R U . . .
C19 C 0.3760(4) 0.1980(4) 0.5553(2) 0.0880(13) Uani 1 1 d . . . . .
H19A H 0.383827 0.184369 0.509846 0.132 Uiso 1 1 calc R U . . .
H19B H 0.300940 0.189533 0.565818 0.132 Uiso 1 1 calc R U . . .
H19C H 0.419102 0.141729 0.579619 0.132 Uiso 1 1 calc R U . . .
C20 C 0.3033(2) 0.4681(3) 0.78732(15) 0.0501(7) Uani 1 1 d . . . . .
C21 C 0.1835(3) 0.4521(4) 0.77875(17) 0.0626(9) Uani 1 1 d . . . . .
H21A H 0.147805 0.486686 0.814766 0.094 Uiso 1 1 calc R U . . .
H21B H 0.166842 0.369296 0.776560 0.094 Uiso 1 1 calc R U . . .
H21C H 0.158514 0.489798 0.739383 0.094 Uiso 1 1 calc R U . . .
C22 C 0.3355(3) 0.5951(3) 0.7836(2) 0.0754(11) Uani 1 1 d . . . . .
H22A H 0.309681 0.636493 0.820605 0.113 Uiso 1 1 calc R U . . .
H22B H 0.304149 0.629453 0.744783 0.113 Uiso 1 1 calc R U . . .
H22C H 0.413340 0.600970 0.782944 0.113 Uiso 1 1 calc R U . . .
C23 C 0.3419(3) 0.4185(4) 0.85108(17) 0.0690(10) Uani 1 1 d . . . . .
H23A H 0.305617 0.457953 0.885373 0.103 Uiso 1 1 calc R U . . .
H23B H 0.419017 0.430025 0.856411 0.103 Uiso 1 1 calc R U . . .
H23C H 0.325821 0.335582 0.852403 0.103 Uiso 1 1 calc R U . . .
C24 C 0.3614(4) 0.6970(3) 0.60714(18) 0.0744(11) Uani 1 1 d . . . . .
H24A H 0.287872 0.708634 0.596936 0.089 Uiso 1 1 calc R U . . .
H24B H 0.411745 0.755328 0.597634 0.089 Uiso 1 1 calc R U . . .
O1 O 0.3738(4) 0.9233(4) 0.5206(2) 0.0892(12) Uani 0.75 1 d G . P . .
H1A H 0.385043 0.948144 0.482440 0.134 Uiso 0.75 1 d G U P . .
H1B H 0.430579 0.934268 0.544544 0.134 Uiso 0.75 1 d G U P . .
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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C3 107.9(2) . . ?
C1 N1 C4 131.2(2) . . ?
C3 N1 C4 120.7(2) . . ?
C1 N2 C2 108.0(2) . . ?
C1 N2 C8 127.2(2) . . ?
C2 N2 C8 124.5(2) . . ?
C1 N3 N4 115.2(2) . . ?
C1 N3 H3 123(3) . . ?
N4 N3 H3 120(3) . . ?
C12 N4 N3 116.5(3) . . ?
N1 C1 N2 108.4(2) . . ?
N1 C1 N3 125.6(3) . . ?
N2 C1 N3 125.9(3) . . ?
C3 C2 N2 107.6(2) . . ?
C3 C2 H2 126.2 . . ?
N2 C2 H2 126.2 . . ?
C2 C3 N1 108.1(3) . . ?
C2 C3 H3A 125.9 . . ?
N1 C3 H3A 125.9 . . ?
C7 C4 C5 109.7(3) . . ?
C7 C4 C6 109.9(3) . . ?
C5 C4 C6 110.1(3) . . ?
C7 C4 N1 107.1(3) . . ?
C5 C4 N1 106.4(3) . . ?
C6 C4 N1 113.5(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 C8 C9 110.1(3) . . ?
C10 C8 N2 108.5(3) . . ?
C9 C8 N2 107.7(2) . . ?
C10 C8 C11 109.3(3) . . ?
C9 C8 C11 111.6(3) . . ?
N2 C8 C11 109.7(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 H12A 120.0 . . ?
N4 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C13 N5 C14 107.5(3) . . ?
C13 N5 C15 130.6(3) . . ?
C14 N5 C15 121.8(3) . . ?
C13 N6 C16 108.1(3) . . ?
C13 N6 C20 126.2(2) . . ?
C16 N6 C20 125.3(2) . . ?
C13 N7 N8 114.9(3) . . ?
C13 N7 H7 127(3) . . ?
N8 N7 H7 118(3) . . ?
C24 N8 N7 116.6(3) . . ?
N6 C13 N5 108.4(2) . . ?
N6 C13 N7 126.6(3) . . ?
N5 C13 N7 125.0(3) . . ?
C16 C14 N5 108.4(3) . . ?
C16 C14 H14 125.8 . . ?
N5 C14 H14 125.8 . . ?
N5 C15 C18 106.4(3) . . ?
N5 C15 C17 112.9(3) . . ?
C18 C15 C17 112.8(4) . . ?
N5 C15 C19 106.5(3) . . ?
C18 C15 C19 110.5(4) . . ?
C17 C15 C19 107.4(4) . . ?
C14 C16 N6 107.6(3) . . ?
C14 C16 H16 126.2 . . ?
N6 C16 H16 126.2 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N6 C20 C21 107.0(3) . . ?
N6 C20 C22 110.4(3) . . ?
C21 C20 C22 112.0(3) . . ?
N6 C20 C23 108.0(3) . . ?
C21 C20 C23 110.0(3) . . ?
C22 C20 C23 109.3(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N8 C24 H24A 120.0 . . ?
N8 C24 H24B 120.0 . . ?
H24A C24 H24B 120.0 . . ?
H1A O1 H1B 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
N1 C1 1.345(4) . ?
N1 C3 1.377(4) . ?
N1 C4 1.523(4) . ?
N2 C1 1.352(4) . ?
N2 C2 1.377(4) . ?
N2 C8 1.519(4) . ?
N3 C1 1.370(4) . ?
N3 N4 1.380(4) . ?
N3 H3 0.83(4) . ?
N4 C12 1.255(5) . ?
C2 C3 1.344(4) . ?
C2 H2 0.9500 . ?
C3 H3A 0.9500 . ?
C4 C7 1.514(5) . ?
C4 C5 1.519(5) . ?
C4 C6 1.519(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C10 1.515(5) . ?
C8 C9 1.519(4) . ?
C8 C11 1.520(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9500 . ?
C12 H12B 0.9500 . ?
N5 C13 1.351(4) . ?
N5 C14 1.377(4) . ?
N5 C15 1.508(4) . ?
N6 C13 1.347(4) . ?
N6 C16 1.379(4) . ?
N6 C20 1.517(4) . ?
N7 C13 1.365(4) . ?
N7 N8 1.375(4) . ?
N7 H7 0.87(5) . ?
N8 C24 1.260(4) . ?
C14 C16 1.335(5) . ?
C14 H14 0.9500 . ?
C15 C18 1.509(6) . ?
C15 C17 1.511(6) . ?
C15 C19 1.512(6) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.520(4) . ?
C20 C22 1.525(5) . ?
C20 C23 1.526(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9500 . ?
C24 H24B 0.9500 . ?
O1 H1A 0.8701 . ?
O1 H1B 0.8699 . ?
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 N3 N4 C12 178.8(4) . . . . ?
C3 N1 C1 N2 0.5(3) . . . . ?
C4 N1 C1 N2 -174.3(3) . . . . ?
C3 N1 C1 N3 -176.3(3) . . . . ?
C4 N1 C1 N3 9.0(5) . . . . ?
C2 N2 C1 N1 0.1(3) . . . . ?
C8 N2 C1 N1 173.5(2) . . . . ?
C2 N2 C1 N3 176.9(3) . . . . ?
C8 N2 C1 N3 -9.8(4) . . . . ?
N4 N3 C1 N1 80.8(4) . . . . ?
N4 N3 C1 N2 -95.4(4) . . . . ?
C1 N2 C2 C3 -0.7(3) . . . . ?
C8 N2 C2 C3 -174.3(3) . . . . ?
N2 C2 C3 N1 1.0(3) . . . . ?
C1 N1 C3 C2 -0.9(3) . . . . ?
C4 N1 C3 C2 174.5(3) . . . . ?
C1 N1 C4 C7 -125.4(3) . . . . ?
C3 N1 C4 C7 60.3(4) . . . . ?
C1 N1 C4 C5 117.3(3) . . . . ?
C3 N1 C4 C5 -56.9(4) . . . . ?
C1 N1 C4 C6 -3.9(5) . . . . ?
C3 N1 C4 C6 -178.2(3) . . . . ?
C1 N2 C8 C10 173.0(3) . . . . ?
C2 N2 C8 C10 -14.6(4) . . . . ?
C1 N2 C8 C9 -67.9(4) . . . . ?
C2 N2 C8 C9 104.5(3) . . . . ?
C1 N2 C8 C11 53.7(4) . . . . ?
C2 N2 C8 C11 -133.9(3) . . . . ?
C13 N7 N8 C24 179.0(3) . . . . ?
C16 N6 C13 N5 0.5(3) . . . . ?
C20 N6 C13 N5 -172.9(3) . . . . ?
C16 N6 C13 N7 -175.9(3) . . . . ?
C20 N6 C13 N7 10.7(5) . . . . ?
C14 N5 C13 N6 -1.4(3) . . . . ?
C15 N5 C13 N6 -178.9(3) . . . . ?
C14 N5 C13 N7 175.1(3) . . . . ?
C15 N5 C13 N7 -2.3(5) . . . . ?
N8 N7 C13 N6 95.8(4) . . . . ?
N8 N7 C13 N5 -80.0(4) . . . . ?
C13 N5 C14 C16 1.9(4) . . . . ?
C15 N5 C14 C16 179.5(3) . . . . ?
C13 N5 C15 C18 108.6(4) . . . . ?
C14 N5 C15 C18 -68.4(5) . . . . ?
C13 N5 C15 C17 -15.7(5) . . . . ?
C14 N5 C15 C17 167.2(4) . . . . ?
C13 N5 C15 C19 -133.4(4) . . . . ?
C14 N5 C15 C19 49.5(4) . . . . ?
N5 C14 C16 N6 -1.5(4) . . . . ?
C13 N6 C16 C14 0.6(3) . . . . ?
C20 N6 C16 C14 174.1(3) . . . . ?
C13 N6 C20 C21 69.8(4) . . . . ?
C16 N6 C20 C21 -102.5(3) . . . . ?
C13 N6 C20 C22 -52.3(4) . . . . ?
C16 N6 C20 C22 135.4(3) . . . . ?
C13 N6 C20 C23 -171.8(3) . . . . ?
C16 N6 C20 C23 15.9(4) . . . . ?
