#------------------------------------------------------------------------------
#$Date: 2024-09-06 03:52:08 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294570 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/66/7716674.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_7716674
loop_
_publ_author_name
'George, Tanner'
'Grant, Tamika'
'Munhoz, Isadora Schumann'
'Do, Thai'
'Masuda, Jason D.'
_publ_section_title
;
 Group 11 complexes of a bulky triazene ligand.
;
_journal_issue                   31
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13107
_journal_page_last               13118
_journal_paper_doi               10.1039/d4dt01561d
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C51 H63 N5'
_chemical_formula_sum            'C51 H63 N5'
_chemical_formula_weight         746.06
_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_creation_date             2024-03-13
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-17 deposited with the CCDC.	2024-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                88.4840(10)
_cell_angle_beta                 81.3940(10)
_cell_angle_gamma                65.5370(10)
_cell_formula_units_Z            2
_cell_length_a                   11.2025(4)
_cell_length_b                   11.2154(4)
_cell_length_c                   19.5845(8)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    125
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.29
_cell_volume                     2212.77(14)
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_collection       'APEX4 (Bruker AXS Inc., 2021)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      125
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_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            121195
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_min         1.996
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1394 before and 0.0555 after correction.
The Ratio of minimum to maximum transmission is 0.9257.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.989
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         10166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0772
_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)+(0.0965P)²+2.2541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1982
_refine_ls_wR_factor_ref         0.2113
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8418
_reflns_number_total             10166
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt01561d2.cif
_cod_data_source_block           mo_2021_07_16_jdm_tg01_0m_a
_cod_depositor_comments
'Adding full bibliography for 7716674--7716682.cif.'
_cod_database_code               7716674
_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   0.993
_shelx_estimated_absorpt_t_min   0.993
_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.a Ternary CH refined with riding coordinates:
 C13(H13), C22(H22), C25(H25), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C30(H30), C31(H31), C32(H32), C36(H36), C38(H38), C45(H45), C47(H47), C6(H6),
 C7(H7), C8(H8), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C49(H49A,H49B,
 H49C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C), C14(H14A,H14B,H14C), C15(H15A,
 H15B,H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C),
 C27(H27A,H27B,H27C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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
N1 N 0.80519(17) 0.30553(17) 0.75387(9) 0.0303(4) Uani 1 1 d . . . . .
N2 N 0.62984(17) 0.46878(16) 0.81010(10) 0.0323(4) Uani 1 1 d . . . . .
N3 N 0.80014(16) 0.50935(16) 0.73039(9) 0.0299(4) Uani 1 1 d . . . . .
N4 N 0.70852(16) 0.63395(16) 0.72351(9) 0.0303(4) Uani 1 1 d . . . . .
N5 N 0.76626(17) 0.70214(17) 0.69541(9) 0.0304(4) Uani 1 1 d . . . . .
C28 C 0.67510(18) 0.82794(19) 0.67848(10) 0.0265(4) Uani 1 1 d . . . . .
C29 C 0.62707(19) 0.8422(2) 0.61502(10) 0.0294(4) Uani 1 1 d . . . . .
C30 C 0.5389(2) 0.9673(2) 0.59979(10) 0.0342(4) Uani 1 1 d . . . . .
H30 H 0.502612 0.978453 0.557997 0.041 Uiso 1 1 calc R U . . .
C31 C 0.5027(2) 1.0753(2) 0.64351(11) 0.0348(4) Uani 1 1 d . . . . .
H31 H 0.440568 1.158840 0.632467 0.042 Uiso 1 1 calc R U . . .
C32 C 0.55798(19) 1.0605(2) 0.70365(11) 0.0315(4) Uani 1 1 d . . . . .
H32 H 0.536186 1.135147 0.732897 0.038 Uiso 1 1 calc R U . . .
C33 C 0.64522(19) 0.9375(2) 0.72180(10) 0.0278(4) Uani 1 1 d . . . . .
C34 C 0.7074(2) 0.92794(19) 0.78548(10) 0.0280(4) Uani 1 1 d . . . . .
C35 C 0.8445(2) 0.89547(19) 0.77987(11) 0.0300(4) Uani 1 1 d . . . . .
C36 C 0.8975(2) 0.8954(2) 0.83980(12) 0.0351(5) Uani 1 1 d . . . . .
H36 H 0.989480 0.874817 0.836108 0.042 Uiso 1 1 calc R U . . .
C37 C 0.8212(2) 0.9240(2) 0.90442(12) 0.0386(5) Uani 1 1 d . . . . .
C38 C 0.6865(2) 0.9559(2) 0.90892(11) 0.0363(5) Uani 1 1 d . . . . .
H38 H 0.632977 0.975601 0.953113 0.044 Uiso 1 1 calc R U . . .
C39 C 0.6274(2) 0.9598(2) 0.85075(11) 0.0321(4) Uani 1 1 d . . . . .
C40 C 0.9339(2) 0.8658(2) 0.71128(12) 0.0371(5) Uani 1 1 d . . . . .
H40A H 0.967166 0.772311 0.698837 0.056 Uiso 1 1 calc R U . . .
H40B H 1.008831 0.887998 0.714512 0.056 Uiso 1 1 calc R U . . .
H40C H 0.883924 0.917760 0.675811 0.056 Uiso 1 1 calc R U . . .
C41 C 0.8838(3) 0.9197(3) 0.96802(15) 0.0621(8) Uani 1 1 d . . . . .
H41A H 0.910892 0.992262 0.968220 0.093 Uiso 1 1 calc R U . . .
H41B H 0.961679 0.836223 0.967756 0.093 Uiso 1 1 calc R U . . .
H41C H 0.819358 0.927778 1.009413 0.093 Uiso 1 1 calc R U . . .
C42 C 0.4798(2) 0.9979(3) 0.85870(12) 0.0435(5) Uani 1 1 d . . . . .
H42A H 0.444930 0.997225 0.907601 0.065 Uiso 1 1 calc R U . . .
H42B H 0.463034 0.935272 0.832051 0.065 Uiso 1 1 calc R U . . .
H42C H 0.435826 1.086071 0.841604 0.065 Uiso 1 1 calc R U . . .
C43 C 0.6723(2) 0.7353(2) 0.55980(10) 0.0303(4) Uani 1 1 d . . . . .
C44 C 0.8007(2) 0.6916(2) 0.52217(11) 0.0331(4) Uani 1 1 d . . . . .
C45 C 0.8346(2) 0.6094(2) 0.46366(11) 0.0382(5) Uani 1 1 d . . . . .
H45 H 0.921469 0.580615 0.438243 0.046 Uiso 1 1 calc R U . . .
C46 C 0.7456(2) 0.5686(2) 0.44151(11) 0.0397(5) Uani 1 1 d . . . . .
C47 C 0.6205(2) 0.6091(2) 0.48041(11) 0.0386(5) Uani 1 1 d . . . . .
H47 H 0.558865 0.580365 0.466303 0.046 Uiso 1 1 calc R U . . .
C48 C 0.5822(2) 0.6905(2) 0.53954(11) 0.0353(5) Uani 1 1 d . . . . .
C49 C 0.9025(2) 0.7323(2) 0.54357(13) 0.0401(5) Uani 1 1 d . . . . .
H49A H 0.867290 0.828225 0.546147 0.060 Uiso 1 1 calc R U . . .
H49B H 0.983529 0.697193 0.509525 0.060 Uiso 1 1 calc R U . . .
H49C H 0.922907 0.698054 0.588967 0.060 Uiso 1 1 calc R U . . .
C50 C 0.7841(3) 0.4783(3) 0.37827(13) 0.0548(7) Uani 1 1 d . . . . .
H50A H 0.865673 0.476862 0.351130 0.082 Uiso 1 1 calc R U . . .
H50B H 0.712622 0.510025 0.350022 0.082 Uiso 1 1 calc R U . . .
H50C H 0.799035 0.389528 0.392703 0.082 Uiso 1 1 calc R U . . .
C51 C 0.4493(2) 0.7218(3) 0.58228(13) 0.0466(6) Uani 1 1 d . . . . .
H51A H 0.397956 0.689190 0.557775 0.070 Uiso 1 1 calc R U . . .
H51B H 0.401435 0.816952 0.590249 0.070 Uiso 1 1 calc R U . . .
H51C H 0.461553 0.679706 0.626746 0.070 Uiso 1 1 calc R U . . .
C13 C 0.7732(2) 0.2308(2) 0.62085(11) 0.0344(4) Uani 1 1 d . . . . .
H13 H 0.710841 0.228892 0.662672 0.041 Uiso 1 1 calc R U . . .
C14 C 0.7685(3) 0.1408(2) 0.56459(13) 0.0479(6) Uani 1 1 d . . . . .
H14A H 0.821798 0.147451 0.521403 0.072 Uiso 1 1 calc R U . . .
H14B H 0.676384 0.167442 0.557289 0.072 Uiso 1 1 calc R U . . .
H14C H 0.804187 0.049949 0.579170 0.072 Uiso 1 1 calc R U . . .
C15 C 0.7217(2) 0.3712(2) 0.59627(13) 0.0412(5) Uani 1 1 d . . . . .
H15A H 0.722300 0.429896 0.632288 0.062 Uiso 1 1 calc R U . . .
H15B H 0.630840 0.398420 0.586711 0.062 Uiso 1 1 calc R U . . .
H15C H 0.778809 0.375445 0.554041 0.062 Uiso 1 1 calc R U . . .
C1 C 0.7444(2) 0.4367(2) 0.76366(10) 0.0299(4) Uani 1 1 d . . . . .
C22 C 0.3629(2) 0.6465(2) 0.79390(12) 0.0382(5) Uani 1 1 d . . . . .
H22 H 0.433089 0.582718 0.758849 0.046 Uiso 1 1 calc R U . . .
C23 C 0.2587(3) 0.5931(3) 0.81620(15) 0.0494(6) Uani 1 1 d . . . . .
H23A H 0.300260 0.507240 0.836189 0.074 Uiso 1 1 calc R U . . .
H23B H 0.220141 0.583959 0.775955 0.074 Uiso 1 1 calc R U . . .
H23C H 0.188596 0.653715 0.850780 0.074 Uiso 1 1 calc R U . . .
C24 C 0.3021(2) 0.7780(3) 0.75935(13) 0.0467(6) Uani 1 1 d . . . . .
H24A H 0.230410 0.841584 0.792112 0.070 Uiso 1 1 calc R U . . .
H24B H 0.266406 0.766052 0.718595 0.070 Uiso 1 1 calc R U . . .
H24C H 0.370564 0.810517 0.745263 0.070 Uiso 1 1 calc R U . . .
C25 C 0.7715(3) 0.5122(2) 0.91525(14) 0.0451(6) Uani 1 1 d . . . . .
H25 H 0.803892 0.438966 0.879677 0.054 Uiso 1 1 calc R U . . .
C26 C 0.7905(4) 0.4516(4) 0.9853(2) 0.0906(13) Uani 1 1 d . . . . .
H26A H 0.885120 0.397966 0.985941 0.136 Uiso 1 1 calc R U . . .
H26B H 0.741528 0.396401 0.993694 0.136 Uiso 1 1 calc R U . . .
H26C H 0.757222 0.521271 1.021474 0.136 Uiso 1 1 calc R U . . .
C27 C 0.8534(3) 0.5901(3) 0.8982(2) 0.0749(10) Uani 1 1 d . . . . .
H27A H 0.823371 0.663286 0.932094 0.112 Uiso 1 1 calc R U . . .
H27B H 0.843012 0.624370 0.851864 0.112 Uiso 1 1 calc R U . . .
H27C H 0.947018 0.533389 0.899540 0.112 Uiso 1 1 calc R U . . .
C4 C 0.9229(2) 0.2317(2) 0.70530(11) 0.0330(4) Uani 1 1 d . . . . .
C5 C 1.0475(2) 0.1983(2) 0.72477(13) 0.0388(5) Uani 1 1 d . . . . .
C6 C 1.1589(2) 0.1196(3) 0.67788(15) 0.0489(6) Uani 1 1 d . . . . .
H6 H 1.245044 0.096615 0.689315 0.059 Uiso 1 1 calc R U . . .
C7 C 1.1466(3) 0.0753(3) 0.61632(14) 0.0514(6) Uani 1 1 d . . . . .
H7 H 1.223592 0.020485 0.585921 0.062 Uiso 1 1 calc R U . . .
C2 C 0.7452(2) 0.2399(2) 0.80392(11) 0.0330(4) Uani 1 1 d . . . . .
H2A H 0.796911 0.207702 0.842501 0.040 Uiso 1 1 calc R U . . .
H2B H 0.737236 0.165641 0.781904 0.040 Uiso 1 1 calc R U . . .
C8 C 1.0230(2) 0.1099(2) 0.59812(13) 0.0447(6) Uani 1 1 d . . . . .
H8 H 1.015481 0.079123 0.554935 0.054 Uiso 1 1 calc R U . . .
C9 C 0.9083(2) 0.1896(2) 0.64206(11) 0.0347(4) Uani 1 1 d . . . . .
C10 C 1.0629(2) 0.2471(3) 0.79277(14) 0.0452(6) Uani 1 1 d . . . . .
H10 H 0.972750 0.309762 0.815063 0.054 Uiso 1 1 calc R U . . .
C11 C 1.1147(4) 0.1352(3) 0.84172(17) 0.0658(8) Uani 1 1 d . . . . .
H11A H 1.204259 0.073257 0.821862 0.099 Uiso 1 1 calc R U . . .
H11B H 1.055759 0.089887 0.848333 0.099 Uiso 1 1 calc R U . . .
H11C H 1.117444 0.170625 0.886391 0.099 Uiso 1 1 calc R U . . .
C12 C 1.1507(4) 0.3211(4) 0.7829(2) 0.0753(10) Uani 1 1 d . . . . .
H12A H 1.162534 0.346153 0.828088 0.113 Uiso 1 1 calc R U . . .
H12B H 1.108920 0.400086 0.757151 0.113 Uiso 1 1 calc R U . . .
H12C H 1.237345 0.264870 0.756918 0.113 Uiso 1 1 calc R U . . .
C3 C 0.6095(2) 0.3495(2) 0.82849(13) 0.0378(5) Uani 1 1 d . . . . .
H3A H 0.540647 0.343002 0.804369 0.045 Uiso 1 1 calc R U . . .
H3B H 0.583445 0.347734 0.878971 0.045 Uiso 1 1 calc R U . . .
C16 C 0.5634(2) 0.58007(19) 0.85714(11) 0.0327(4) Uani 1 1 d . . . . .
C17 C 0.4287(2) 0.6597(2) 0.85362(11) 0.0350(4) Uani 1 1 d . . . . .
C18 C 0.3561(3) 0.7520(2) 0.90699(13) 0.0431(5) Uani 1 1 d . . . . .
H18 H 0.264825 0.805800 0.906263 0.052 Uiso 1 1 calc R U . . .
C19 C 0.4169(3) 0.7658(3) 0.96170(13) 0.0487(6) Uani 1 1 d . . . . .
H19 H 0.365944 0.826916 0.998815 0.058 Uiso 1 1 calc R U . . .
C20 C 0.5498(3) 0.6916(2) 0.96225(13) 0.0451(6) Uani 1 1 d . . . . .
H20 H 0.590431 0.706016 0.998514 0.054 Uiso 1 1 calc R U . . .
C21 C 0.6260(2) 0.5959(2) 0.91104(12) 0.0379(5) Uani 1 1 d . . . . .
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'
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 C4 126.88(17) . . ?
C1 N1 C2 111.63(16) . . ?
C4 N1 C2 121.26(16) . . ?
C1 N2 C3 109.83(16) . . ?
C1 N2 C16 128.65(17) . . ?
C16 N2 C3 117.25(17) . . ?
C1 N3 N4 111.45(16) . . ?
N5 N4 N3 109.57(16) . . ?
N4 N5 C28 112.29(16) . . ?
C29 C28 N5 119.11(17) . . ?
C33 C28 N5 119.59(17) . . ?
C33 C28 C29 120.99(18) . . ?
C28 C29 C43 124.82(18) . . ?
C30 C29 C28 117.56(18) . . ?
C30 C29 C43 117.42(17) . . ?
C29 C30 H30 118.9 . . ?
C31 C30 C29 122.16(19) . . ?
C31 C30 H30 118.9 . . ?
C30 C31 H31 120.4 . . ?
C30 C31 C32 119.3(2) . . ?
C32 C31 H31 120.4 . . ?
C31 C32 H32 119.6 . . ?
C31 C32 C33 120.89(19) . . ?
C33 C32 H32 119.6 . . ?
C28 C33 C34 122.38(18) . . ?
C32 C33 C28 118.86(18) . . ?
C32 C33 C34 118.71(18) . . ?
C35 C34 C33 120.17(17) . . ?
C39 C34 C33 119.82(17) . . ?
C39 C34 C35 119.88(18) . . ?
C34 C35 C40 122.24(18) . . ?
C36 C35 C34 118.62(19) . . ?
C36 C35 C40 119.11(19) . . ?
C35 C36 H36 118.8 . . ?
C37 C36 C35 122.4(2) . . ?
C37 C36 H36 118.8 . . ?
C36 C37 C38 118.17(19) . . ?
C36 C37 C41 120.4(2) . . ?
C38 C37 C41 121.4(2) . . ?
C37 C38 H38 119.0 . . ?
C37 C38 C39 122.1(2) . . ?
C39 C38 H38 119.0 . . ?
C34 C39 C42 121.45(18) . . ?
C38 C39 C34 118.8(2) . . ?
C38 C39 C42 119.7(2) . . ?
C35 C40 H40A 109.5 . . ?
C35 C40 H40B 109.5 . . ?
C35 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C37 C41 H41A 109.5 . . ?
C37 C41 H41B 109.5 . . ?
C37 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C44 C43 C29 119.65(18) . . ?
C44 C43 C48 119.31(19) . . ?
C48 C43 C29 120.55(18) . . ?
C43 C44 C49 121.30(19) . . ?
C45 C44 C43 119.4(2) . . ?
C45 C44 C49 119.3(2) . . ?
C44 C45 H45 119.0 . . ?
C46 C45 C44 122.0(2) . . ?
C46 C45 H45 119.0 . . ?
C45 C46 C47 118.0(2) . . ?
C45 C46 C50 121.4(2) . . ?
C47 C46 C50 120.6(2) . . ?
C46 C47 H47 118.9 . . ?
C46 C47 C48 122.2(2) . . ?
C48 C47 H47 118.9 . . ?
C43 C48 C51 121.56(19) . . ?
C47 C48 C43 119.1(2) . . ?
C47 C48 C51 119.3(2) . . ?
C44 C49 H49A 109.5 . . ?
C44 C49 H49B 109.5 . . ?
C44 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C46 C50 H50A 109.5 . . ?
C46 C50 H50B 109.5 . . ?
C46 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C48 C51 H51A 109.5 . . ?
C48 C51 H51B 109.5 . . ?
C48 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C14 C13 H13 107.6 . . ?
C15 C13 H13 107.6 . . ?
C15 C13 C14 108.80(19) . . ?
C9 C13 H13 107.6 . . ?
C9 C13 C14 114.07(19) . . ?
C9 C13 C15 111.02(18) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C1 N2 108.98(17) . . ?
N3 C1 N1 118.97(18) . . ?
N3 C1 N2 132.04(19) . . ?
C23 C22 H22 107.8 . . ?
C23 C22 C24 110.7(2) . . ?
C24 C22 H22 107.8 . . ?
C17 C22 H22 107.8 . . ?
C17 C22 C23 112.1(2) . . ?
C17 C22 C24 110.60(19) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 H25 107.6 . . ?
C26 C25 C21 111.8(3) . . ?
C27 C25 H25 107.6 . . ?
C27 C25 C26 111.0(3) . . ?
C27 C25 C21 111.0(2) . . ?
C21 C25 H25 107.6 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C5 C4 N1 119.1(2) . . ?
C9 C4 N1 118.74(18) . . ?
C9 C4 C5 122.0(2) . . ?
C4 C5 C6 117.3(2) . . ?
C4 C5 C10 121.8(2) . . ?
C6 C5 C10 120.9(2) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.6(2) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.1(2) . . ?
C8 C7 H7 119.9 . . ?
N1 C2 H2A 111.4 . . ?
N1 C2 H2B 111.4 . . ?
N1 C2 C3 102.00(16) . . ?
H2A C2 H2B 109.2 . . ?
C3 C2 H2A 111.4 . . ?
C3 C2 H2B 111.4 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.1(2) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C13 121.26(18) . . ?
C4 C9 C8 117.9(2) . . ?
C8 C9 C13 120.9(2) . . ?
C5 C10 H10 107.5 . . ?
C5 C10 C11 111.3(2) . . ?
C5 C10 C12 112.1(2) . . ?
C11 C10 H10 107.5 . . ?
C12 C10 H10 107.5 . . ?
C12 C10 C11 110.6(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C3 C2 102.89(16) . . ?
N2 C3 H3A 111.2 . . ?
N2 C3 H3B 111.2 . . ?
C2 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C17 C16 N2 117.71(18) . . ?
C21 C16 N2 119.77(19) . . ?
C21 C16 C17 121.83(19) . . ?
C16 C17 C22 121.78(18) . . ?
C18 C17 C22 120.0(2) . . ?
C18 C17 C16 118.2(2) . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.5(2) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.2 . . ?
C19 C20 C21 121.5(2) . . ?
C21 C20 H20 119.2 . . ?
C16 C21 C25 122.6(2) . . ?
C20 C21 C25 119.8(2) . . ?
C20 C21 C16 117.6(2) . . ?
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 1.346(3) . ?
N1 C4 1.446(3) . ?
N1 C2 1.459(3) . ?
N2 C1 1.375(3) . ?
N2 C3 1.475(3) . ?
N2 C16 1.431(3) . ?
N3 N4 1.367(2) . ?
N3 C1 1.323(3) . ?
N4 N5 1.260(2) . ?
N5 C28 1.424(3) . ?
C28 C29 1.406(3) . ?
C28 C33 1.404(3) . ?
C29 C30 1.397(3) . ?
C29 C43 1.505(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.382(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.386(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.395(3) . ?
C33 C34 1.498(3) . ?
C34 C35 1.412(3) . ?
C34 C39 1.408(3) . ?
C35 C36 1.392(3) . ?
C35 C40 1.504(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.381(3) . ?
C37 C38 1.388(3) . ?
C37 C41 1.509(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.392(3) . ?
C39 C42 1.510(3) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C44 1.404(3) . ?
C43 C48 1.407(3) . ?
C44 C45 1.394(3) . ?
C44 C49 1.506(3) . ?
C45 H45 0.9500 . ?
C45 C46 1.382(3) . ?
C46 C47 1.386(3) . ?
C46 C50 1.513(3) . ?
C47 H47 0.9500 . ?
C47 C48 1.394(3) . ?
C48 C51 1.500(3) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C14 1.535(3) . ?
C13 C15 1.528(3) . ?
C13 C9 1.508(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C22 H22 1.0000 . ?
C22 C23 1.525(4) . ?
C22 C24 1.533(4) . ?
C22 C17 1.514(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25 1.0000 . ?
C25 C26 1.519(4) . ?
C25 C27 1.508(4) . ?
C25 C21 1.521(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C4 C5 1.397(3) . ?
C4 C9 1.393(3) . ?
C5 C6 1.403(3) . ?
C5 C10 1.513(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.363(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.376(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.523(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.396(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.527(4) . ?
C10 C12 1.518(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C16 C17 1.411(3) . ?
C16 C21 1.405(3) . ?
C17 C18 1.389(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.396(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.374(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(3) . ?
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
N1 C4 C5 C6 176.0(2) . . . . ?
N1 C4 C5 C10 -5.4(3) . . . . ?
N1 C4 C9 C13 6.2(3) . . . . ?
N1 C4 C9 C8 -175.15(19) . . . . ?
N1 C2 C3 N2 -20.5(2) . . . . ?
N2 C16 C17 C22 -12.2(3) . . . . ?
N2 C16 C17 C18 167.6(2) . . . . ?
N2 C16 C21 C25 10.5(3) . . . . ?
N2 C16 C21 C20 -168.9(2) . . . . ?
N3 N4 N5 C28 172.25(15) . . . . ?
N4 N3 C1 N1 156.17(17) . . . . ?
N4 N3 C1 N2 -24.7(3) . . . . ?
N4 N5 C28 C29 -86.0(2) . . . . ?
N4 N5 C28 C33 100.4(2) . . . . ?
N5 C28 C29 C30 -179.32(17) . . . . ?
N5 C28 C29 C43 -4.7(3) . . . . ?
N5 C28 C33 C32 178.58(17) . . . . ?
N5 C28 C33 C34 0.9(3) . . . . ?
C28 C29 C30 C31 2.4(3) . . . . ?
C28 C29 C43 C44 -69.9(3) . . . . ?
C28 C29 C43 C48 118.2(2) . . . . ?
C28 C33 C34 C35 66.9(3) . . . . ?
C28 C33 C34 C39 -117.3(2) . . . . ?
C29 C28 C33 C32 5.1(3) . . . . ?
C29 C28 C33 C34 -172.60(17) . . . . ?
C29 C30 C31 C32 1.8(3) . . . . ?
C29 C43 C44 C45 -169.14(19) . . . . ?
C29 C43 C44 C49 10.6(3) . . . . ?
C29 C43 C48 C47 168.66(19) . . . . ?
C29 C43 C48 C51 -15.0(3) . . . . ?
C30 C29 C43 C44 104.7(2) . . . . ?
C30 C29 C43 C48 -67.2(3) . . . . ?
C30 C31 C32 C33 -2.6(3) . . . . ?
C31 C32 C33 C28 -0.8(3) . . . . ?
C31 C32 C33 C34 176.98(18) . . . . ?
C32 C33 C34 C35 -110.8(2) . . . . ?
C32 C33 C34 C39 65.0(2) . . . . ?
C33 C28 C29 C30 -5.8(3) . . . . ?
C33 C28 C29 C43 168.74(18) . . . . ?
C33 C34 C35 C36 176.09(18) . . . . ?
C33 C34 C35 C40 -1.7(3) . . . . ?
C33 C34 C39 C38 -177.16(18) . . . . ?
C33 C34 C39 C42 2.8(3) . . . . ?
C34 C35 C36 C37 0.9(3) . . . . ?
C35 C34 C39 C38 -1.3(3) . . . . ?
C35 C34 C39 C42 178.7(2) . . . . ?
C35 C36 C37 C38 -1.0(3) . . . . ?
C35 C36 C37 C41 178.7(2) . . . . ?
C36 C37 C38 C39 -0.1(3) . . . . ?
C37 C38 C39 C34 1.3(3) . . . . ?
C37 C38 C39 C42 -178.7(2) . . . . ?
C39 C34 C35 C36 0.3(3) . . . . ?
C39 C34 C35 C40 -177.52(19) . . . . ?
C40 C35 C36 C37 178.8(2) . . . . ?
C41 C37 C38 C39 -179.8(2) . . . . ?
C43 C29 C30 C31 -172.61(19) . . . . ?
C43 C44 C45 C46 -0.4(3) . . . . ?
C44 C43 C48 C47 -3.3(3) . . . . ?
C44 C43 C48 C51 173.1(2) . . . . ?
C44 C45 C46 C47 -1.6(3) . . . . ?
C44 C45 C46 C50 -179.4(2) . . . . ?
C45 C46 C47 C48 1.2(3) . . . . ?
C46 C47 C48 C43 1.3(3) . . . . ?
C46 C47 C48 C51 -175.2(2) . . . . ?
C48 C43 C44 C45 2.9(3) . . . . ?
C48 C43 C44 C49 -177.4(2) . . . . ?
C49 C44 C45 C46 179.9(2) . . . . ?
C50 C46 C47 C48 179.0(2) . . . . ?
C14 C13 C9 C4 -159.2(2) . . . . ?
C14 C13 C9 C8 22.1(3) . . . . ?
C15 C13 C9 C4 77.4(2) . . . . ?
C15 C13 C9 C8 -101.2(2) . . . . ?
C1 N1 C4 C5 86.1(3) . . . . ?
C1 N1 C4 C9 -97.7(2) . . . . ?
C1 N1 C2 C3 19.9(2) . . . . ?
C1 N2 C3 C2 16.0(2) . . . . ?
C1 N2 C16 C17 124.6(2) . . . . ?
C1 N2 C16 C21 -64.7(3) . . . . ?
C1 N3 N4 N5 176.03(17) . . . . ?
C22 C17 C18 C19 -179.1(2) . . . . ?
C23 C22 C17 C16 112.1(2) . . . . ?
C23 C22 C17 C18 -67.7(3) . . . . ?
C24 C22 C17 C16 -123.8(2) . . . . ?
C24 C22 C17 C18 56.4(3) . . . . ?
C26 C25 C21 C16 -128.2(3) . . . . ?
C26 C25 C21 C20 51.1(3) . . . . ?
C27 C25 C21 C16 107.2(3) . . . . ?
C27 C25 C21 C20 -73.5(3) . . . . ?
C4 N1 C1 N2 174.95(19) . . . . ?
C4 N1 C1 N3 -5.7(3) . . . . ?
C4 N1 C2 C3 -165.25(19) . . . . ?
C4 C5 C6 C7 -1.2(4) . . . . ?
C4 C5 C10 C11 112.0(3) . . . . ?
C4 C5 C10 C12 -123.4(3) . . . . ?
C5 C4 C9 C13 -177.7(2) . . . . ?
C5 C4 C9 C8 1.0(3) . . . . ?
C5 C6 C7 C8 1.5(4) . . . . ?
C6 C5 C10 C11 -69.5(3) . . . . ?
C6 C5 C10 C12 55.1(3) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C7 C8 C9 C13 178.0(2) . . . . ?
C7 C8 C9 C4 -0.7(3) . . . . ?
C2 N1 C1 N2 -10.6(2) . . . . ?
C2 N1 C1 N3 168.79(18) . . . . ?
C2 N1 C4 C5 -87.9(2) . . . . ?
C2 N1 C4 C9 88.3(2) . . . . ?
C9 C4 C5 C6 -0.1(3) . . . . ?
C9 C4 C5 C10 178.4(2) . . . . ?
C10 C5 C6 C7 -179.7(2) . . . . ?
C3 N2 C1 N1 -4.2(2) . . . . ?
C3 N2 C1 N3 176.6(2) . . . . ?
C3 N2 C16 C17 -81.2(3) . . . . ?
C3 N2 C16 C21 89.5(2) . . . . ?
C16 N2 C1 N1 151.6(2) . . . . ?
C16 N2 C1 N3 -27.7(4) . . . . ?
C16 N2 C3 C2 -142.83(19) . . . . ?
C16 C17 C18 C19 1.1(4) . . . . ?
C17 C16 C21 C25 -179.2(2) . . . . ?
C17 C16 C21 C20 1.4(3) . . . . ?
C17 C18 C19 C20 2.1(4) . . . . ?
C18 C19 C20 C21 -3.7(4) . . . . ?
C19 C20 C21 C25 -177.5(2) . . . . ?
C19 C20 C21 C16 1.9(4) . . . . ?
C21 C16 C17 C22 177.3(2) . . . . ?
C21 C16 C17 C18 -2.9(3) . . . . ?
