#------------------------------------------------------------------------------
#$Date: 2019-05-10 01:25:27 +0300 (Fri, 10 May 2019) $
#$Revision: 215020 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/09/1550995.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_1550995
loop_
_publ_author_name
'Liu, Yizhu'
'Varava, Paul'
'Fabrizio, Alberto'
'Eymann, Léonard Y. M.'
'Tskhovrebov, Alexander G.'
'Planes, Ophélie Marie'
'Solari, Euro'
'Fadaei-Tirani, Farzaneh'
'Scopelliti, Rosario'
'Sienkiewicz, Andrzej'
'Corminboeuf, Clémence'
'Severin, Kay'
_publ_section_title
;
 Synthesis of aminyl biradicals by base-induced Csp3--Csp3 coupling of
 cationic azo dyes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC01502G
_journal_year                    2019
_chemical_formula_moiety         'C60 H66 N8'
_chemical_formula_sum            'C60 H66 N8'
_chemical_formula_weight         899.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-03-18 deposited with the CCDC.    2019-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                95.280(4)
_cell_angle_beta                 100.912(4)
_cell_angle_gamma                98.331(4)
_cell_formula_units_Z            2
_cell_length_a                   12.5606(6)
_cell_length_b                   14.7631(6)
_cell_length_c                   16.2731(8)
_cell_measurement_reflns_used    4667
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.6940
_cell_measurement_theta_min      4.0820
_cell_volume                     2909.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Mercury 4.0.0 (CCDC, 2018)'
_computing_publication_material  'CIFTab (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -22.00   1.00   10.00    --  -43.01 -57.00-120.00   90
  2  ω    -71.00  24.00   1.00   10.00    --  -43.01  57.00  30.00   95
  3  ω    -86.00 -19.00   1.00   10.00    --  -43.01 125.00  90.00   67
  4  ω   -117.00 -80.00   1.00   10.00    --  -43.01 -99.00   0.00   37
  5  ω   -124.00 -99.00   1.00   10.00    --  -43.01 -99.00 -90.00   25
  6  ω    102.00 146.00   1.00   40.00    --  105.68  77.00 150.00   44
  7  ω     33.00  67.00   1.00   40.00    --  105.68 -45.00 -60.00   34
  8  ω     36.00  96.00   1.00   40.00    --  105.68 -77.00   0.00   60
  9  ω     72.00 100.00   1.00   40.00    --  105.68 -61.00  90.00   28
 10  ω     56.00 103.00   1.00   40.00    --  105.68 -94.00 -60.00   47
 11  ω     36.00 132.00   1.00   40.00    --  105.68 -45.00  90.00   96
 12  ω     82.00 122.00   1.00   40.00    --  105.68 -45.00 -60.00   40
 13  ω     37.00 118.00   1.00   40.00    --  105.68-125.00 150.00   81
 14  ω     51.00 113.00   1.00   40.00    --  105.68 -45.00-180.00   62
 15  ω     29.00  66.00   1.00   40.00    --  105.68 -94.00  90.00   37
 16  ω     53.00 108.00   1.00   40.00    --  105.68 -94.00-150.00   55
 17  ω     23.00  50.00   1.00   40.00    --  105.68 -94.00 -30.00   27
 18  ω     82.00 107.00   1.00   40.00    --  105.68 -94.00 -30.00   25
 19  ω     18.00 166.00   1.00   40.00    --  105.68   0.00 -30.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20784
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.513
_diffrn_reflns_theta_min         3.870
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.469
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense red'
_exptl_crystal_density_diffrn    1.026
_exptl_crystal_description       irregular
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.087
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.00096(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     630
_refine_ls_number_reflns         11360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0481
_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)+(0.0747P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1417
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7953
_reflns_number_total             11360
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9sc01502g2.cif
_cod_data_source_block           yzl830
_cod_database_code               1550995
_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_min   0.912
_shelx_estimated_absorpt_t_max   0.960
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
N1 N 0.39627(12) 0.72524(11) 0.34026(10) 0.0403(3) Uani 1 1 d . .
N2 N 0.39632(12) 0.71045(12) 0.20548(10) 0.0435(4) Uani 1 1 d . .
N3 N 0.54788(12) 0.66515(11) 0.28853(9) 0.0387(3) Uani 1 1 d . .
N4 N 0.60448(11) 0.67390(10) 0.36939(9) 0.0347(3) Uani 1 1 d . .
N5 N 0.00565(12) 0.85672(11) 0.34659(9) 0.0379(3) Uani 1 1 d . .
N6 N -0.07352(12) 0.81446(10) 0.21389(10) 0.0373(3) Uani 1 1 d . .
N7 N 0.11620(11) 0.90136(10) 0.25109(9) 0.0342(3) Uani 1 1 d . .
N8 N 0.12217(11) 0.88435(10) 0.16877(9) 0.0350(3) Uani 1 1 d . .
C1 C 0.45483(14) 0.69830(13) 0.28229(11) 0.0379(4) Uani 1 1 d . .
C2 C 0.30133(16) 0.75409(15) 0.29796(14) 0.0493(5) Uani 1 1 d . .
H2 H 0.246494 0.776404 0.323371 0.059 Uiso 1 1 calc R U
C3 C 0.30174(16) 0.74466(15) 0.21626(14) 0.0507(5) Uani 1 1 d . .
H3 H 0.247034 0.758794 0.172703 0.061 Uiso 1 1 calc R U
C4 C 0.41003(14) 0.70686(12) 0.42643(12) 0.0369(4) Uani 1 1 d . .
C5 C 0.38327(15) 0.61628(13) 0.44333(12) 0.0417(4) Uani 1 1 d . .
C6 C 0.39478(17) 0.60116(13) 0.52743(13) 0.0451(4) Uani 1 1 d . .
H6 H 0.378296 0.539920 0.540419 0.054 Uiso 1 1 calc R U
C7 C 0.42945(16) 0.67244(14) 0.59277(13) 0.0449(4) Uani 1 1 d . .
C8 C 0.45330(16) 0.76129(13) 0.57312(13) 0.0445(4) Uani 1 1 d . .
H8 H 0.476461 0.810775 0.617543 0.053 Uiso 1 1 calc R U
C9 C 0.44435(15) 0.78028(12) 0.49009(13) 0.0415(4) Uani 1 1 d . .
C10 C 0.3457(2) 0.53838(15) 0.37332(15) 0.0580(6) Uani 1 1 d . .
H10A H 0.283479 0.552303 0.332987 0.087 Uiso 1 1 calc R U
H10B H 0.322746 0.481506 0.396558 0.087 Uiso 1 1 calc R U
H10C H 0.406151 0.530327 0.344586 0.087 Uiso 1 1 calc R U
C11 C 0.4436(2) 0.65416(18) 0.68330(14) 0.0627(6) Uani 1 1 d . .
H11A H 0.485153 0.709275 0.719999 0.094 Uiso 1 1 calc R U
H11B H 0.483744 0.602380 0.691386 0.094 Uiso 1 1 calc R U
H11C H 0.371255 0.638902 0.697497 0.094 Uiso 1 1 calc R U
C12 C 0.4746(2) 0.87767(14) 0.47147(16) 0.0586(6) Uani 1 1 d . .
H12A H 0.524679 0.878753 0.432027 0.088 Uiso 1 1 calc R U
H12B H 0.510791 0.917105 0.523969 0.088 Uiso 1 1 calc R U
H12C H 0.407882 0.900507 0.446297 0.088 Uiso 1 1 calc R U
C13 C 0.43218(15) 0.69331(15) 0.12777(12) 0.0443(4) Uani 1 1 d . .
C14 C 0.51880(15) 0.75443(15) 0.11195(12) 0.0459(4) Uani 1 1 d . .
C15 C 0.55523(17) 0.73423(19) 0.03743(14) 0.0601(6) Uani 1 1 d . .
H15 H 0.614767 0.774504 0.025129 0.072 Uiso 1 1 calc R U
C16 C 0.5066(2) 0.6572(2) -0.01849(14) 0.0746(8) Uani 1 1 d . .
C17 C 0.4193(2) 0.5993(2) -0.00082(16) 0.0787(9) Uani 1 1 d . .
H17 H 0.385491 0.546275 -0.039611 0.094 Uiso 1 1 calc R U
C18 C 0.37984(19) 0.61660(18) 0.07222(14) 0.0603(6) Uani 1 1 d . .
C19 C 0.57234(18) 0.83836(16) 0.17235(16) 0.0568(5) Uani 1 1 d . .
H19A H 0.515875 0.872830 0.186558 0.085 Uiso 1 1 calc R U
H19B H 0.623023 0.877535 0.146277 0.085 Uiso 1 1 calc R U
H19C H 0.613200 0.819713 0.223779 0.085 Uiso 1 1 calc R U
C20 C 0.5490(3) 0.6363(4) -0.09840(18) 0.1191(17) Uani 1 1 d . .
H20A H 0.504828 0.660220 -0.145263 0.179 Uiso 1 1 calc R U
H20B H 0.543490 0.569399 -0.111375 0.179 Uiso 1 1 calc R U
H20C H 0.625984 0.665690 -0.090150 0.179 Uiso 1 1 calc R U
C21 C 0.2839(3) 0.5526(2) 0.0905(2) 0.0869(9) Uani 1 1 d . .
H21A H 0.304303 0.533687 0.146711 0.130 Uiso 1 1 calc R U
H21B H 0.264545 0.498011 0.048218 0.130 Uiso 1 1 calc R U
H21C H 0.220585 0.584811 0.088354 0.130 Uiso 1 1 calc R U
C22 C 0.69226(12) 0.63135(11) 0.38279(10) 0.0306(3) Uani 1 1 d . .
C23 C 0.75158(13) 0.64645(11) 0.46988(10) 0.0315(3) Uani 1 1 d . .
C24 C 0.84056(13) 0.60381(12) 0.49362(11) 0.0346(3) Uani 1 1 d . .
H24 H 0.878656 0.615048 0.550811 0.042 Uiso 1 1 calc R U
C25 C 0.87827(14) 0.54355(12) 0.43645(12) 0.0375(4) Uani 1 1 d . .
C26 C 0.82027(14) 0.53148(12) 0.35127(11) 0.0375(4) Uani 1 1 d . .
H26 H 0.844913 0.492714 0.311439 0.045 Uiso 1 1 calc R U
C27 C 0.73135(13) 0.57199(11) 0.32287(11) 0.0341(3) Uani 1 1 d . .
C28 C 0.71140(15) 0.70579(13) 0.53323(11) 0.0404(4) Uani 1 1 d . .
H28A H 0.707819 0.766752 0.514620 0.061 Uiso 1 1 calc R U
H28B H 0.762084 0.712404 0.588004 0.061 Uiso 1 1 calc R U
H28C H 0.638024 0.677044 0.538513 0.061 Uiso 1 1 calc R U
C29 C 0.96835(15) 0.49703(13) 0.45911(13) 0.0407(4) Uani 1 1 d . .
H29 H 0.987396 0.458926 0.415707 0.049 Uiso 1 1 calc R U
C30 C 0.67719(15) 0.54973(13) 0.23070(11) 0.0409(4) Uani 1 1 d . .
H30A H 0.600050 0.521990 0.225315 0.061 Uiso 1 1 calc R U
H30B H 0.715339 0.506232 0.203154 0.061 Uiso 1 1 calc R U
H30C H 0.681013 0.606502 0.203794 0.061 Uiso 1 1 calc R U
C31 C 0.02162(13) 0.86026(12) 0.26565(11) 0.0336(3) Uani 1 1 d . .
C32 C -0.14686(15) 0.78224(13) 0.26358(13) 0.0430(4) Uani 1 1 d . .
H32 H -0.218926 0.748458 0.243383 0.052 Uiso 1 1 calc R U
C33 C -0.09799(15) 0.80722(13) 0.34426(12) 0.0424(4) Uani 1 1 d . .
H33 H -0.128563 0.793615 0.391710 0.051 Uiso 1 1 calc R U
C34 C 0.08738(14) 0.89206(13) 0.42150(11) 0.0383(4) Uani 1 1 d . .
C35 C 0.13480(15) 0.82908(14) 0.46974(12) 0.0435(4) Uani 1 1 d . .
C36 C 0.21127(16) 0.86464(16) 0.54347(13) 0.0492(5) Uani 1 1 d . .
H36 H 0.243901 0.823118 0.577652 0.059 Uiso 1 1 calc R U
C37 C 0.24124(16) 0.95839(17) 0.56853(13) 0.0525(5) Uani 1 1 d . .
C38 C 0.19346(16) 1.01851(16) 0.51818(13) 0.0503(5) Uani 1 1 d . .
H38 H 0.215276 1.083051 0.534177 0.060 Uiso 1 1 calc R U
C39 C 0.11405(15) 0.98702(14) 0.44446(12) 0.0427(4) Uani 1 1 d . .
C40 C 0.10600(18) 0.72696(15) 0.44545(16) 0.0551(5) Uani 1 1 d . .
H40A H 0.041978 0.702959 0.468028 0.083 Uiso 1 1 calc R U
H40B H 0.168465 0.697683 0.468559 0.083 Uiso 1 1 calc R U
H40C H 0.088674 0.713339 0.383843 0.083 Uiso 1 1 calc R U
C41 C 0.3228(2) 0.9953(2) 0.64934(16) 0.0763(8) Uani 1 1 d . .
H41A H 0.344965 1.061954 0.650903 0.115 Uiso 1 1 calc R U
H41B H 0.387566 0.964945 0.652148 0.115 Uiso 1 1 calc R U
H41C H 0.288787 0.982935 0.697513 0.115 Uiso 1 1 calc R U
C42 C 0.05936(17) 1.05359(14) 0.39334(14) 0.0497(5) Uani 1 1 d . .
H42A H 0.077845 1.049243 0.337397 0.075 Uiso 1 1 calc R U
H42B H 0.085117 1.116520 0.421913 0.075 Uiso 1 1 calc R U
H42C H -0.020517 1.038407 0.387390 0.075 Uiso 1 1 calc R U
C43 C 0.21238(13) 0.92423(12) 0.14488(11) 0.0332(3) Uani 1 1 d . .
C44 C 0.30349(14) 0.99163(13) 0.19283(11) 0.0376(4) Uani 1 1 d . .
C45 C 0.38953(14) 1.01947(13) 0.15519(12) 0.0404(4) Uani 1 1 d . .
H45 H 0.447907 1.065045 0.186514 0.048 Uiso 1 1 calc R U
C46 C 0.39726(13) 0.98490(13) 0.07282(11) 0.0373(4) Uani 1 1 d . .
C47 C 0.30758(13) 0.91873(13) 0.02692(11) 0.0361(4) Uani 1 1 d . .
H47 H 0.310175 0.893234 -0.028298 0.043 Uiso 1 1 calc R U
C48 C 0.21778(13) 0.89054(12) 0.05943(11) 0.0352(3) Uani 1 1 d . .
C49 C 0.30718(17) 1.03302(16) 0.28138(12) 0.0522(5) Uani 1 1 d . .
H49A H 0.242669 1.062949 0.282589 0.078 Uiso 1 1 calc R U
H49B H 0.374182 1.078809 0.300888 0.078 Uiso 1 1 calc R U
H49C H 0.307109 0.984317 0.318432 0.078 Uiso 1 1 calc R U
C50 C 0.49144(15) 1.01661(14) 0.03993(12) 0.0424(4) Uani 1 1 d . .
H50 H 0.546330 1.063161 0.073967 0.051 Uiso 1 1 calc R U
C51 C 0.12302(16) 0.82293(14) 0.00722(12) 0.0452(4) Uani 1 1 d . .
H51A H 0.115842 0.765507 0.032987 0.068 Uiso 1 1 calc R U
H51B H 0.136168 0.810105 -0.049856 0.068 Uiso 1 1 calc R U
H51C H 0.055180 0.849034 0.004411 0.068 Uiso 1 1 calc R U
C52 C -0.10487(14) 0.80731(12) 0.12344(12) 0.0373(4) Uani 1 1 d . .
C53 C -0.10891(14) 0.72285(13) 0.07622(13) 0.0411(4) Uani 1 1 d . .
C54 C -0.14357(15) 0.71668(14) -0.01103(13) 0.0451(4) Uani 1 1 d . .
H54 H -0.147809 0.659477 -0.044399 0.054 Uiso 1 1 calc R U
C55 C -0.17199(15) 0.79155(14) -0.05046(13) 0.0460(4) Uani 1 1 d . .
C56 C -0.16698(16) 0.87451(14) -0.00059(13) 0.0458(4) Uani 1 1 d . .
H56 H -0.186760 0.926153 -0.027012 0.055 Uiso 1 1 calc R U
C57 C -0.13394(14) 0.88407(13) 0.08657(12) 0.0409(4) Uani 1 1 d . .
C58 C -0.0710(2) 0.64270(14) 0.11761(15) 0.0546(5) Uani 1 1 d . .
H58A H 0.003631 0.662069 0.151358 0.082 Uiso 1 1 calc R U
H58B H -0.071130 0.592072 0.074159 0.082 Uiso 1 1 calc R U
H58C H -0.120788 0.621820 0.154221 0.082 Uiso 1 1 calc R U
C59 C -0.2035(2) 0.78476(18) -0.14548(14) 0.0622(6) Uani 1 1 d . .
H59A H -0.273366 0.807055 -0.161607 0.093 Uiso 1 1 calc R U
H59B H -0.211350 0.720327 -0.169846 0.093 Uiso 1 1 calc R U
H59C H -0.146087 0.822515 -0.166576 0.093 Uiso 1 1 calc R U
C60 C -0.12568(18) 0.97497(14) 0.13905(14) 0.0503(5) Uani 1 1 d . .
H60A H -0.160172 0.965280 0.187450 0.075 Uiso 1 1 calc R U
H60B H -0.163372 1.016618 0.104798 0.075 Uiso 1 1 calc R U
H60C H -0.048108 1.002319 0.159152 0.075 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 9 3 0.0873
6 3 -8 0.0588
6 0 -9 0.0596
-6 -2 8 0.1034
3 6 4 0.0946
-6 4 -5 0.0216
5 -8 2 0.0673
0 -9 -2 0.1033
6 -3 6 0.0607
5 2 6 0.0810
8 -1 -1 0.0574
5 7 1 0.0820
-3 -3 10 0.0886
-3 0 10 0.1014
-2 -7 7 0.1085
1 0 10 0.0783
1 -5 9 0.0656
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
C1 N1 C2 108.77(16) .
C1 N1 C4 127.17(15) .
C2 N1 C4 122.34(16) .
C1 N2 C3 109.29(17) .
C1 N2 C13 123.75(16) .
C3 N2 C13 126.92(16) .
C1 N3 N4 112.39(15) .
C22 N4 N3 116.24(15) .
C31 N5 C33 109.27(15) .
C31 N5 C34 124.84(14) .
C33 N5 C34 125.70(15) .
C31 N6 C32 108.84(15) .
C31 N6 C52 128.58(14) .
C32 N6 C52 122.17(14) .
C31 N7 N8 111.65(14) .
C43 N8 N7 117.80(14) .
N3 C1 N2 120.76(17) .
N3 C1 N1 133.11(16) .
N2 C1 N1 106.12(15) .
C3 C2 N1 107.83(18) .
C3 C2 H2 126.1 .
N1 C2 H2 126.1 .
C2 C3 N2 107.99(17) .
C2 C3 H3 126.0 .
N2 C3 H3 126.0 .
C9 C4 C5 122.13(17) .
C9 C4 N1 118.84(16) .
C5 C4 N1 118.95(17) .
C6 C5 C4 117.51(17) .
C6 C5 C10 121.47(18) .
C4 C5 C10 121.01(18) .
C7 C6 C5 122.11(18) .
C7 C6 H6 118.9 .
C5 C6 H6 118.9 .
C8 C7 C6 118.44(18) .
C8 C7 C11 120.40(19) .
C6 C7 C11 121.15(19) .
C7 C8 C9 121.87(18) .
C7 C8 H8 119.1 .
C9 C8 H8 119.1 .
C4 C9 C8 117.91(17) .
C4 C9 C12 121.85(18) .
C8 C9 C12 120.21(18) .
C5 C10 H10A 109.5 .
C5 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
C5 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
C7 C11 H11A 109.5 .
C7 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
C7 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
C9 C12 H12A 109.5 .
C9 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C9 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C18 C13 C14 122.8(2) .
C18 C13 N2 118.71(19) .
C14 C13 N2 118.49(18) .
C13 C14 C15 117.4(2) .
C13 C14 C19 121.7(2) .
C15 C14 C19 120.9(2) .
C16 C15 C14 121.3(2) .
C16 C15 H15 119.3 .
C14 C15 H15 119.3 .
C15 C16 C17 119.2(2) .
C15 C16 C20 120.2(3) .
C17 C16 C20 120.6(3) .
C16 C17 C18 121.6(2) .
C16 C17 H17 119.2 .
C18 C17 H17 119.2 .
C13 C18 C17 117.6(2) .
C13 C18 C21 121.4(2) .
C17 C18 C21 121.0(2) .
C14 C19 H19A 109.5 .
C14 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
C14 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
C16 C20 H20A 109.5 .
C16 C20 H20B 109.5 .
H20A C20 H20B 109.5 .
C16 C20 H20C 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
C18 C21 H21A 109.5 .
C18 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
C18 C21 H21C 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
N4 C22 C23 113.46(15) .
N4 C22 C27 128.43(15) .
C23 C22 C27 118.09(14) .
C24 C23 C22 119.89(16) .
C24 C23 C28 121.00(15) .
C22 C23 C28 119.07(14) .
C23 C24 C25 122.87(16) .
C23 C24 H24 118.6 .
C25 C24 H24 118.6 .
C29 C25 C24 124.36(17) .
C29 C25 C26 119.51(17) .
C24 C25 C26 116.12(16) .
C27 C26 C25 124.29(17) .
C27 C26 H26 117.9 .
C25 C26 H26 117.9 .
C26 C27 C22 118.70(15) .
C26 C27 C30 117.55(16) .
C22 C27 C30 123.73(15) .
C23 C28 H28A 109.5 .
C23 C28 H28B 109.5 .
H28A C28 H28B 109.5 .
C23 C28 H28C 109.5 .
H28A C28 H28C 109.5 .
H28B C28 H28C 109.5 .
C29 C29 C25 124.9(2) 2_766
C29 C29 H29 117.6 2_766
C25 C29 H29 117.6 .
C27 C30 H30A 109.5 .
C27 C30 H30B 109.5 .
H30A C30 H30B 109.5 .
C27 C30 H30C 109.5 .
H30A C30 H30C 109.5 .
H30B C30 H30C 109.5 .
N7 C31 N6 133.09(16) .
N7 C31 N5 120.88(15) .
N6 C31 N5 106.02(14) .
C33 C32 N6 108.05(15) .
C33 C32 H32 126.0 .
N6 C32 H32 126.0 .
C32 C33 N5 107.81(16) .
C32 C33 H33 126.1 .
N5 C33 H33 126.1 .
C39 C34 C35 122.59(18) .
C39 C34 N5 119.07(17) .
C35 C34 N5 118.32(17) .
C36 C35 C34 117.42(19) .
C36 C35 C40 119.83(19) .
C34 C35 C40 122.74(19) .
C37 C36 C35 122.1(2) .
C37 C36 H36 118.9 .
C35 C36 H36 118.9 .
C36 C37 C38 118.57(19) .
C36 C37 C41 121.2(2) .
C38 C37 C41 120.2(2) .
C37 C38 C39 122.0(2) .
C37 C38 H38 119.0 .
C39 C38 H38 119.0 .
C34 C39 C38 117.23(19) .
C34 C39 C42 121.84(18) .
C38 C39 C42 120.93(19) .
C35 C40 H40A 109.5 .
C35 C40 H40B 109.5 .
H40A C40 H40B 109.5 .
C35 C40 H40C 109.5 .
H40A C40 H40C 109.5 .
H40B C40 H40C 109.5 .
C37 C41 H41A 109.5 .
C37 C41 H41B 109.5 .
H41A C41 H41B 109.5 .
C37 C41 H41C 109.5 .
H41A C41 H41C 109.5 .
H41B C41 H41C 109.5 .
C39 C42 H42A 109.5 .
C39 C42 H42B 109.5 .
H42A C42 H42B 109.5 .
C39 C42 H42C 109.5 .
H42A C42 H42C 109.5 .
H42B C42 H42C 109.5 .
N8 C43 C44 129.25(16) .
N8 C43 C48 113.05(15) .
C44 C43 C48 117.66(14) .
C45 C44 C43 118.37(16) .
C45 C44 C49 118.70(16) .
C43 C44 C49 122.93(15) .
C44 C45 C46 124.43(16) .
C44 C45 H45 117.8 .
C46 C45 H45 117.8 .
C45 C46 C47 116.43(15) .
C45 C46 C50 120.27(16) .
C47 C46 C50 123.30(16) .
C48 C47 C46 122.11(16) .
C48 C47 H47 118.9 .
C46 C47 H47 118.9 .
C47 C48 C43 120.92(16) .
C47 C48 C51 120.16(16) .
C43 C48 C51 118.92(15) .
C44 C49 H49A 109.5 .
C44 C49 H49B 109.5 .
H49A C49 H49B 109.5 .
C44 C49 H49C 109.5 .
H49A C49 H49C 109.5 .
H49B C49 H49C 109.5 .
C50 C50 C46 124.3(2) 2_675
C50 C50 H50 117.8 2_675
C46 C50 H50 117.8 .
C48 C51 H51A 109.5 .
C48 C51 H51B 109.5 .
H51A C51 H51B 109.5 .
C48 C51 H51C 109.5 .
H51A C51 H51C 109.5 .
H51B C51 H51C 109.5 .
C53 C52 C57 122.39(18) .
C53 C52 N6 118.71(16) .
C57 C52 N6 118.86(16) .
C52 C53 C54 117.66(18) .
C52 C53 C58 121.01(18) .
C54 C53 C58 121.24(18) .
C55 C54 C53 121.91(18) .
C55 C54 H54 119.0 .
C53 C54 H54 119.0 .
C54 C55 C56 118.36(19) .
C54 C55 C59 121.03(19) .
C56 C55 C59 120.6(2) .
C57 C56 C55 121.99(19) .
C57 C56 H56 119.0 .
C55 C56 H56 119.0 .
C56 C57 C52 117.68(17) .
C56 C57 C60 121.19(18) .
C52 C57 C60 121.09(18) .
C53 C58 H58A 109.5 .
C53 C58 H58B 109.5 .
H58A C58 H58B 109.5 .
C53 C58 H58C 109.5 .
H58A C58 H58C 109.5 .
H58B C58 H58C 109.5 .
C55 C59 H59A 109.5 .
C55 C59 H59B 109.5 .
H59A C59 H59B 109.5 .
C55 C59 H59C 109.5 .
H59A C59 H59C 109.5 .
H59B C59 H59C 109.5 .
C57 C60 H60A 109.5 .
C57 C60 H60B 109.5 .
H60A C60 H60B 109.5 .
C57 C60 H60C 109.5 .
H60A C60 H60C 109.5 .
H60B C60 H60C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.366(2) .
N1 C2 1.403(2) .
N1 C4 1.436(2) .
N2 C1 1.366(2) .
N2 C3 1.391(3) .
N2 C13 1.434(3) .
N3 C1 1.321(2) .
N3 N4 1.357(2) .
N4 C22 1.339(2) .
N5 C31 1.374(2) .
N5 C33 1.389(2) .
N5 C34 1.437(2) .
N6 C31 1.369(2) .
N6 C32 1.398(2) .
N6 C52 1.440(2) .
N7 C31 1.327(2) .
N7 N8 1.358(2) .
N8 C43 1.341(2) .
C2 C3 1.325(3) .
C2 H2 0.9500 .
C3 H3 0.9500 .
C4 C9 1.387(3) .
C4 C5 1.396(3) .
C5 C6 1.391(3) .
C5 C10 1.497(3) .
C6 C7 1.383(3) .
C6 H6 0.9500 .
C7 C8 1.383(3) .
C7 C11 1.504(3) .
C8 C9 1.392(3) .
C8 H8 0.9500 .
C9 C12 1.506(3) .
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 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C18 1.379(3) .
C13 C14 1.389(3) .
C14 C15 1.397(3) .
C14 C19 1.496(3) .
C15 C16 1.375(4) .
C15 H15 0.9500 .
C16 C17 1.382(4) .
C16 C20 1.518(4) .
C17 C18 1.389(4) .
C17 H17 0.9500 .
C18 C21 1.514(4) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 C23 1.452(2) .
C22 C27 1.452(2) .
C23 C24 1.371(2) .
C23 C28 1.498(3) .
C24 C25 1.421(3) .
C24 H24 0.9500 .
C25 C29 1.415(3) .
C25 C26 1.421(3) .
C26 C27 1.367(2) .
C26 H26 0.9500 .
C27 C30 1.509(2) .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C29 C29 1.403(4) 2_766
C29 H29 0.9500 .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
C32 C33 1.333(3) .
C32 H32 0.9500 .
C33 H33 0.9500 .
C34 C39 1.392(3) .
C34 C35 1.398(3) .
C35 C36 1.393(3) .
C35 C40 1.496(3) .
C36 C37 1.382(3) .
C36 H36 0.9500 .
C37 C38 1.386(3) .
C37 C41 1.507(3) .
C38 C39 1.400(3) .
C38 H38 0.9500 .
C39 C42 1.503(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 1.448(2) .
C43 C48 1.450(2) .
C44 C45 1.371(2) .
C44 C49 1.502(3) .
C45 C46 1.416(3) .
C45 H45 0.9500 .
C46 C47 1.417(2) .
C46 C50 1.425(2) .
C47 C48 1.362(2) .
C47 H47 0.9500 .
C48 C51 1.501(2) .
C49 H49A 0.9800 .
C49 H49B 0.9800 .
C49 H49C 0.9800 .
C50 C50 1.412(4) 2_675
C50 H50 0.9500 .
C51 H51A 0.9800 .
C51 H51B 0.9800 .
C51 H51C 0.9800 .
C52 C53 1.392(3) .
C52 C57 1.393(3) .
C53 C54 1.394(3) .
C53 C58 1.506(3) .
C54 C55 1.385(3) .
C54 H54 0.9500 .
C55 C56 1.392(3) .
C55 C59 1.512(3) .
C56 C57 1.388(3) .
C56 H56 0.9500 .
C57 C60 1.502(3) .
C58 H58A 0.9800 .
C58 H58B 0.9800 .
C58 H58C 0.9800 .
C59 H59A 0.9800 .
C59 H59B 0.9800 .
C59 H59C 0.9800 .
C60 H60A 0.9800 .
C60 H60B 0.9800 .
C60 H60C 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_4
C1 N3 N4 C22 171.50(15) .
C31 N7 N8 C43 178.01(15) .
N4 N3 C1 N2 168.46(16) .
N4 N3 C1 N1 -12.5(3) .
C3 N2 C1 N3 179.16(17) .
C13 N2 C1 N3 -3.2(3) .
C3 N2 C1 N1 -0.1(2) .
C13 N2 C1 N1 177.54(17) .
C2 N1 C1 N3 -179.2(2) .
C4 N1 C1 N3 -14.1(3) .
C2 N1 C1 N2 0.0(2) .
C4 N1 C1 N2 165.10(17) .
C1 N1 C2 C3 0.2(2) .
C4 N1 C2 C3 -165.79(18) .
N1 C2 C3 N2 -0.3(2) .
C1 N2 C3 C2 0.3(2) .
C13 N2 C3 C2 -177.3(2) .
C1 N1 C4 C9 115.3(2) .
C2 N1 C4 C9 -81.4(2) .
C1 N1 C4 C5 -67.8(2) .
C2 N1 C4 C5 95.5(2) .
C9 C4 C5 C6 -1.6(3) .
N1 C4 C5 C6 -178.34(17) .
C9 C4 C5 C10 179.56(19) .
N1 C4 C5 C10 2.8(3) .
C4 C5 C6 C7 1.1(3) .
C10 C5 C6 C7 180.0(2) .
C5 C6 C7 C8 -0.1(3) .
C5 C6 C7 C11 -178.7(2) .
C6 C7 C8 C9 -0.6(3) .
C11 C7 C8 C9 178.0(2) .
C5 C4 C9 C8 0.9(3) .
N1 C4 C9 C8 177.70(16) .
C5 C4 C9 C12 179.16(19) .
N1 C4 C9 C12 -4.1(3) .
C7 C8 C9 C4 0.2(3) .
C7 C8 C9 C12 -178.1(2) .
C1 N2 C13 C18 107.2(2) .
C3 N2 C13 C18 -75.5(3) .
C1 N2 C13 C14 -72.3(3) .
C3 N2 C13 C14 104.9(2) .
C18 C13 C14 C15 -2.1(3) .
N2 C13 C14 C15 177.43(18) .
C18 C13 C14 C19 178.5(2) .
N2 C13 C14 C19 -2.0(3) .
C13 C14 C15 C16 0.5(4) .
C19 C14 C15 C16 180.0(2) .
C14 C15 C16 C17 0.6(4) .
C14 C15 C16 C20 -179.1(3) .
C15 C16 C17 C18 -0.4(5) .
C20 C16 C17 C18 179.4(3) .
C14 C13 C18 C17 2.4(4) .
N2 C13 C18 C17 -177.2(2) .
C14 C13 C18 C21 -178.5(2) .
N2 C13 C18 C21 2.0(4) .
C16 C17 C18 C13 -1.1(5) .
C16 C17 C18 C21 179.8(3) .
N3 N4 C22 C23 177.69(13) .
N3 N4 C22 C27 -4.2(2) .
N4 C22 C23 C24 177.19(15) .
C27 C22 C23 C24 -1.1(2) .
N4 C22 C23 C28 -0.4(2) .
C27 C22 C23 C28 -178.71(15) .
C22 C23 C24 C25 -0.6(2) .
C28 C23 C24 C25 176.97(16) .
C23 C24 C25 C29 -178.70(17) .
C23 C24 C25 C26 1.8(2) .
C29 C25 C26 C27 179.02(17) .
C24 C25 C26 C27 -1.5(3) .
C25 C26 C27 C22 -0.1(3) .
C25 C26 C27 C30 -178.29(17) .
N4 C22 C27 C26 -176.57(16) .
C23 C22 C27 C26 1.5(2) .
N4 C22 C27 C30 1.5(3) .
C23 C22 C27 C30 179.50(15) .
C24 C25 C29 C29 0.9(4) 2_766
C26 C25 C29 C29 -179.7(2) 2_766
N8 N7 C31 N6 -8.9(3) .
N8 N7 C31 N5 169.87(15) .
C32 N6 C31 N7 178.27(19) .
C52 N6 C31 N7 -9.1(3) .
C32 N6 C31 N5 -0.6(2) .
C52 N6 C31 N5 172.05(17) .
C33 N5 C31 N7 -177.80(16) .
C34 N5 C31 N7 -2.7(3) .
C33 N5 C31 N6 1.3(2) .
C34 N5 C31 N6 176.39(16) .
C31 N6 C32 C33 -0.3(2) .
C52 N6 C32 C33 -173.50(17) .
N6 C32 C33 N5 1.0(2) .
C31 N5 C33 C32 -1.5(2) .
C34 N5 C33 C32 -176.53(18) .
C31 N5 C34 C39 74.2(2) .
C33 N5 C34 C39 -111.4(2) .
C31 N5 C34 C35 -107.5(2) .
C33 N5 C34 C35 66.8(2) .
C39 C34 C35 C36 0.2(3) .
N5 C34 C35 C36 -178.03(15) .
C39 C34 C35 C40 179.74(17) .
N5 C34 C35 C40 1.5(3) .
C34 C35 C36 C37 -0.8(3) .
C40 C35 C36 C37 179.62(18) .
C35 C36 C37 C38 -0.2(3) .
C35 C36 C37 C41 178.96(19) .
C36 C37 C38 C39 1.8(3) .
C41 C37 C38 C39 -177.32(19) .
C35 C34 C39 C38 1.4(2) .
N5 C34 C39 C38 179.54(15) .
C35 C34 C39 C42 -177.88(17) .
N5 C34 C39 C42 0.3(2) .
C37 C38 C39 C34 -2.4(3) .
C37 C38 C39 C42 176.87(18) .
N7 N8 C43 C44 -6.4(3) .
N7 N8 C43 C48 171.15(15) .
N8 C43 C44 C45 177.24(18) .
C48 C43 C44 C45 -0.3(3) .
N8 C43 C44 C49 -3.5(3) .
C48 C43 C44 C49 179.03(19) .
C43 C44 C45 C46 -1.8(3) .
C49 C44 C45 C46 178.9(2) .
C44 C45 C46 C47 1.6(3) .
C44 C45 C46 C50 -178.47(19) .
C45 C46 C47 C48 0.9(3) .
C50 C46 C47 C48 -179.06(18) .
C46 C47 C48 C43 -2.9(3) .
C46 C47 C48 C51 177.74(18) .
N8 C43 C48 C47 -175.31(16) .
C44 C43 C48 C47 2.6(3) .
N8 C43 C48 C51 4.0(2) .
C44 C43 C48 C51 -178.08(17) .
C45 C46 C50 C50 177.2(2) 2_675
C47 C46 C50 C50 -2.8(4) 2_675
C31 N6 C52 C53 109.3(2) .
C32 N6 C52 C53 -78.9(2) .
C31 N6 C52 C57 -73.0(2) .
C32 N6 C52 C57 98.8(2) .
C57 C52 C53 C54 0.0(3) .
N6 C52 C53 C54 177.59(15) .
C57 C52 C53 C58 176.60(18) .
N6 C52 C53 C58 -5.8(3) .
C52 C53 C54 C55 0.8(3) .
C58 C53 C54 C55 -175.80(19) .
C53 C54 C55 C56 -1.0(3) .
C53 C54 C55 C59 176.67(19) .
C54 C55 C56 C57 0.4(3) .
C59 C55 C56 C57 -177.26(19) .
C55 C56 C57 C52 0.3(3) .
C55 C56 C57 C60 178.06(18) .
C53 C52 C57 C56 -0.6(3) .
N6 C52 C57 C56 -178.13(16) .
C53 C52 C57 C60 -178.28(18) .
N6 C52 C57 C60 4.2(3) .
