#------------------------------------------------------------------------------
#$Date: 2023-04-04 13:04:27 +0300 (Tue, 04 Apr 2023) $
#$Revision: 282304 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/83/1568323.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_1568323
loop_
_publ_author_name
'Wang, Shiyu'
'Zhu, Chenhao'
'Ning, Lichao'
'Li, Dawei'
'Feng, Xiaoming'
'Dong, Shunxi'
_publ_section_title
;
 Regioselective C-H alkylation of anisoles with olefins by cationic
 imidazolin-2-iminato scandium(iii) alkyl complexes.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              3132
_journal_page_last               3139
_journal_paper_doi               10.1039/d2sc06725k
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C47 H64 N5 Sc'
_chemical_formula_sum            'C47 H64 N5 Sc'
_chemical_formula_weight         743.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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
;
2022-11-12 deposited with the CCDC.	2023-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.715(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.891(2)
_cell_length_b                   11.6240(12)
_cell_length_c                   20.148(2)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.51
_cell_measurement_theta_min      2.71
_cell_volume                     4297.2(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            69494
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.612
_diffrn_reflns_theta_min         2.136
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8937
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_description       block
_exptl_crystal_F_000             1608
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Toluene, Hexane'
_exptl_crystal_size_max          0.659
_exptl_crystal_size_mid          0.611
_exptl_crystal_size_min          0.340
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.419
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         7765
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.419
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.1083
_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)+19.1522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2108
_refine_ls_wR_factor_ref         0.2142
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6979
_reflns_number_total             7765
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc06725k3.cif
_cod_data_source_block           dop010
_cod_depositor_comments
'Adding full bibliography for 1568319--1568323.cif.'
_cod_original_cell_volume        4297.3(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1568323
_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   0.875
_shelx_estimated_absorpt_t_max   0.933
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Sc1 Sc 0.24325(5) 0.39017(7) 0.23124(5) 0.0158(2) Uani 1 1 d . . . . .
N1 N 0.2492(2) 0.2335(3) 0.2685(2) 0.0184(8) Uani 1 1 d . . . . .
N2 N 0.3119(2) 0.0664(3) 0.3337(2) 0.0161(8) Uani 1 1 d . . . . .
N3 N 0.1935(2) 0.0564(3) 0.2822(2) 0.0170(8) Uani 1 1 d . . . . .
N4 N 0.3495(2) 0.5002(4) 0.2977(2) 0.0250(10) Uani 1 1 d . . . . .
N5 N 0.1329(2) 0.4119(4) 0.1271(2) 0.0287(10) Uani 1 1 d . . . . .
C1 C 0.2514(2) 0.1313(4) 0.2916(2) 0.0146(9) Uani 1 1 d . . . . .
C2 C 0.2910(3) -0.0430(4) 0.3488(3) 0.0177(10) Uani 1 1 d . . . . .
C3 C 0.2182(3) -0.0488(4) 0.3177(3) 0.0184(10) Uani 1 1 d . . . . .
C4 C 0.3449(3) -0.1297(4) 0.3934(3) 0.0261(11) Uani 1 1 d . . . . .
H4A H 0.319800 -0.202242 0.393406 0.039 Uiso 1 1 calc R U . . .
H4B H 0.368327 -0.101191 0.442842 0.039 Uiso 1 1 calc R U . . .
H4C H 0.381911 -0.142471 0.373263 0.039 Uiso 1 1 calc R U . . .
C5 C 0.1668(3) -0.1418(4) 0.3178(3) 0.0267(12) Uani 1 1 d . . . . .
H5A H 0.194443 -0.208022 0.344856 0.040 Uiso 1 1 calc R U . . .
H5B H 0.137790 -0.165076 0.268184 0.040 Uiso 1 1 calc R U . . .
H5C H 0.134382 -0.113484 0.340460 0.040 Uiso 1 1 calc R U . . .
C11 C 0.3853(2) 0.1052(4) 0.3539(3) 0.0182(10) Uani 1 1 d . . . . .
C12 C 0.4227(2) 0.1463(4) 0.4243(2) 0.0175(10) Uani 1 1 d . . . . .
C13 C 0.4939(3) 0.1850(4) 0.4419(3) 0.0238(11) Uani 1 1 d . . . . .
H13A H 0.520464 0.214033 0.488862 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5267(3) 0.1820(5) 0.3928(3) 0.0275(12) Uani 1 1 d . . . . .
H14A H 0.575194 0.208966 0.406034 0.033 Uiso 1 1 calc R U . . .
C15 C 0.4888(3) 0.1398(5) 0.3243(3) 0.0275(12) Uani 1 1 d . . . . .
H15A H 0.511834 0.137851 0.290860 0.033 Uiso 1 1 calc R U . . .
C16 C 0.4175(3) 0.1002(4) 0.3033(3) 0.0226(11) Uani 1 1 d . . . . .
C17 C 0.3864(3) 0.1510(4) 0.4785(3) 0.0225(11) Uani 1 1 d . . . . .
H17A H 0.353099 0.083103 0.468918 0.027 Uiso 1 1 calc R U . . .
C18 C 0.4404(3) 0.1420(5) 0.5561(3) 0.0365(14) Uani 1 1 d . . . . .
H18A H 0.471685 0.074633 0.561410 0.055 Uiso 1 1 calc R U . . .
H18B H 0.413809 0.133947 0.587925 0.055 Uiso 1 1 calc R U . . .
H18C H 0.470523 0.211572 0.569102 0.055 Uiso 1 1 calc R U . . .
C19 C 0.3391(3) 0.2588(5) 0.4674(3) 0.0344(13) Uani 1 1 d . . . . .
H19A H 0.305708 0.263914 0.416786 0.052 Uiso 1 1 calc R U . . .
H19B H 0.370433 0.327119 0.480253 0.052 Uiso 1 1 calc R U . . .
H19C H 0.311005 0.254495 0.497901 0.052 Uiso 1 1 calc R U . . .
C20 C 0.3765(3) 0.0520(5) 0.2281(3) 0.0340(13) Uani 1 1 d . . . . .
H20A H 0.323146 0.058138 0.217534 0.041 Uiso 1 1 calc R U . . .
C21 C 0.3942(5) -0.0746(6) 0.2251(4) 0.072(3) Uani 1 1 d . . . . .
H21A H 0.379563 -0.117943 0.259006 0.108 Uiso 1 1 calc R U . . .
H21B H 0.446716 -0.083585 0.237958 0.108 Uiso 1 1 calc R U . . .
H21C H 0.367736 -0.103781 0.176228 0.108 Uiso 1 1 calc R U . . .
C22 C 0.3913(4) 0.1184(6) 0.1700(3) 0.0462(16) Uani 1 1 d . . . . .
H22A H 0.384024 0.200752 0.175145 0.069 Uiso 1 1 calc R U . . .
H22B H 0.357841 0.092219 0.122506 0.069 Uiso 1 1 calc R U . . .
H22C H 0.441699 0.104820 0.175065 0.069 Uiso 1 1 calc R U . . .
C31 C 0.1194(2) 0.0843(4) 0.2397(3) 0.0179(10) Uani 1 1 d . . . . .
C32 C 0.0825(3) 0.1586(4) 0.2690(3) 0.0251(11) Uani 1 1 d . . . . .
C33 C 0.0103(3) 0.1836(5) 0.2280(4) 0.0392(15) Uani 1 1 d . . . . .
H33A H -0.015710 0.234472 0.246411 0.047 Uiso 1 1 calc R U . . .
C34 C -0.0238(3) 0.1364(6) 0.1620(4) 0.0461(18) Uani 1 1 d . . . . .
H34A H -0.073493 0.154572 0.134967 0.055 Uiso 1 1 calc R U . . .
C35 C 0.0118(3) 0.0632(6) 0.1333(3) 0.0456(18) Uani 1 1 d . . . . .
H35A H -0.013473 0.031273 0.086801 0.055 Uiso 1 1 calc R U . . .
C36 C 0.0855(3) 0.0347(5) 0.1721(3) 0.0310(12) Uani 1 1 d . . . . .
C37 C 0.1200(3) 0.2072(5) 0.3445(3) 0.0381(14) Uani 1 1 d D . . . .
H37X H 0.170204 0.224094 0.346949 0.046 Uiso 0.26(4) 1 calc R U P A 1
H37Y H 0.173738 0.197304 0.358933 0.046 Uiso 0.74(4) 1 calc R U P A 2
C38X C 0.135(4) 0.137(3) 0.4112(14) 0.062(3) Uani 0.26(4) 1 d D . P A 1
H38A H 0.157178 0.185978 0.453680 0.094 Uiso 0.26(4) 1 calc R U P A 1
H38B H 0.167698 0.073679 0.412751 0.094 Uiso 0.26(4) 1 calc R U P A 1
H38C H 0.088689 0.105934 0.410657 0.094 Uiso 0.26(4) 1 calc R U P A 1
C39X C 0.085(3) 0.327(2) 0.334(2) 0.062(3) Uani 0.26(4) 1 d D . P A 1
H39A H 0.092011 0.366214 0.294323 0.094 Uiso 0.26(4) 1 calc R U P A 1
H39B H 0.108616 0.372021 0.378557 0.094 Uiso 0.26(4) 1 calc R U P A 1
H39C H 0.033116 0.319635 0.323929 0.094 Uiso 0.26(4) 1 calc R U P A 1
C38Y C 0.0968(14) 0.1337(10) 0.3955(9) 0.062(3) Uani 0.74(4) 1 d D . P A 2
H38D H 0.110007 0.053194 0.392558 0.094 Uiso 0.74(4) 1 calc R U P A 2
H38E H 0.043937 0.139692 0.381448 0.094 Uiso 0.74(4) 1 calc R U P A 2
H38F H 0.121620 0.161414 0.444931 0.094 Uiso 0.74(4) 1 calc R U P A 2
C39Y C 0.1063(13) 0.3304(8) 0.3578(9) 0.062(3) Uani 0.74(4) 1 d D . P A 2
H39D H 0.118512 0.380302 0.324882 0.094 Uiso 0.74(4) 1 calc R U P A 2
H39E H 0.136587 0.351002 0.407616 0.094 Uiso 0.74(4) 1 calc R U P A 2
H39F H 0.054751 0.340401 0.349638 0.094 Uiso 0.74(4) 1 calc R U P A 2
C40 C 0.1268(4) -0.0458(5) 0.1417(3) 0.0475(17) Uani 1 1 d D . . . .
H40X H 0.174032 -0.058073 0.183502 0.057 Uiso 0.39(3) 1 calc R U P B 1
H40Y H 0.167384 -0.084182 0.181849 0.057 Uiso 0.61(3) 1 calc R U P B 2
C41X C 0.151(3) 0.003(3) 0.084(2) 0.060(2) Uani 0.39(3) 1 d D . P B 1
H41A H 0.177672 -0.055222 0.069799 0.091 Uiso 0.39(3) 1 calc R U P B 1
H41B H 0.182194 0.070348 0.103829 0.091 Uiso 0.39(3) 1 calc R U P B 1
H41C H 0.107712 0.026984 0.042540 0.091 Uiso 0.39(3) 1 calc R U P B 1
C42X C 0.0977(19) -0.171(2) 0.1203(18) 0.060(2) Uani 0.39(3) 1 d . . P B 1
H42A H 0.077247 -0.199677 0.154228 0.091 Uiso 0.39(3) 1 calc R U P B 1
H42B H 0.137874 -0.220978 0.121577 0.091 Uiso 0.39(3) 1 calc R U P B 1
H42C H 0.059782 -0.170691 0.071568 0.091 Uiso 0.39(3) 1 calc R U P B 1
C41Y C 0.158(2) 0.023(2) 0.0952(13) 0.060(2) Uani 0.61(3) 1 d D . P B 2
H41D H 0.189096 0.084686 0.124068 0.091 Uiso 0.61(3) 1 calc R U P B 2
H41E H 0.117383 0.056997 0.054437 0.091 Uiso 0.61(3) 1 calc R U P B 2
H41F H 0.185984 -0.027819 0.077188 0.091 Uiso 0.61(3) 1 calc R U P B 2
C42Y C 0.0716(11) -0.1376(16) 0.0952(11) 0.060(2) Uani 0.61(3) 1 d D . P B 2
H42D H 0.035164 -0.100361 0.052968 0.091 Uiso 0.61(3) 1 calc R U P B 2
H42E H 0.047336 -0.173831 0.123860 0.091 Uiso 0.61(3) 1 calc R U P B 2
H42F H 0.097671 -0.196263 0.079488 0.091 Uiso 0.61(3) 1 calc R U P B 2
C51 C 0.3571(3) 0.6036(5) 0.2582(3) 0.0357(14) Uani 1 1 d . . . . .
H51A H 0.402823 0.643046 0.286417 0.054 Uiso 1 1 calc R U . . .
H51B H 0.316022 0.655597 0.250523 0.054 Uiso 1 1 calc R U . . .
H51C H 0.357617 0.580532 0.211622 0.054 Uiso 1 1 calc R U . . .
C52 C 0.4126(3) 0.4231(5) 0.3110(3) 0.0325(13) Uani 1 1 d . . . . .
H52A H 0.457855 0.465718 0.336010 0.049 Uiso 1 1 calc R U . . .
H52B H 0.411875 0.394305 0.265020 0.049 Uiso 1 1 calc R U . . .
H52C H 0.409769 0.358091 0.340825 0.049 Uiso 1 1 calc R U . . .
C53 C 0.3399(3) 0.5337(4) 0.3637(3) 0.0228(11) Uani 1 1 d . . . . .
C54 C 0.3979(3) 0.5455(4) 0.4295(3) 0.0298(12) Uani 1 1 d . . . . .
H54A H 0.446491 0.536384 0.432523 0.036 Uiso 1 1 calc R U . . .
C55 C 0.3850(3) 0.5704(5) 0.4906(3) 0.0363(14) Uani 1 1 d . . . . .
H55A H 0.424543 0.579498 0.535653 0.044 Uiso 1 1 calc R U . . .
C56 C 0.3148(3) 0.5820(5) 0.4859(3) 0.0352(14) Uani 1 1 d . . . . .
H56A H 0.305762 0.596337 0.528113 0.042 Uiso 1 1 calc R U . . .
C57 C 0.2570(3) 0.5730(4) 0.4204(3) 0.0274(12) Uani 1 1 d . . . . .
H57A H 0.208859 0.581799 0.418539 0.033 Uiso 1 1 calc R U . . .
C58 C 0.2674(3) 0.5511(4) 0.3563(3) 0.0209(10) Uani 1 1 d . . . . .
C59 C 0.2076(3) 0.5399(4) 0.2854(3) 0.0225(11) Uani 1 1 d . . . . .
H59A H 0.201587 0.611727 0.257216 0.027 Uiso 1 1 calc R U . . .
H59B H 0.161151 0.521881 0.290308 0.027 Uiso 1 1 calc R U . . .
C61 C 0.1089(4) 0.3009(5) 0.0888(3) 0.0403(15) Uani 1 1 d . . . . .
H61A H 0.064474 0.313041 0.045796 0.060 Uiso 1 1 calc R U . . .
H61B H 0.099081 0.245693 0.120681 0.060 Uiso 1 1 calc R U . . .
H61C H 0.147401 0.270672 0.074566 0.060 Uiso 1 1 calc R U . . .
C62 C 0.0723(3) 0.4560(6) 0.1454(3) 0.0399(15) Uani 1 1 d . . . . .
H62A H 0.027463 0.458308 0.101847 0.060 Uiso 1 1 calc R U . . .
H62B H 0.084046 0.533718 0.165380 0.060 Uiso 1 1 calc R U . . .
H62C H 0.065217 0.405206 0.180957 0.060 Uiso 1 1 calc R U . . .
C63 C 0.1556(3) 0.4913(5) 0.0831(3) 0.0305(13) Uani 1 1 d . . . . .
C64 C 0.1090(4) 0.5749(5) 0.0398(3) 0.0435(16) Uani 1 1 d . . . . .
H64A H 0.059984 0.579839 0.036206 0.052 Uiso 1 1 calc R U . . .
C65 C 0.1350(5) 0.6510(6) 0.0019(3) 0.059(2) Uani 1 1 d . . . . .
H65A H 0.103551 0.707932 -0.028160 0.071 Uiso 1 1 calc R U . . .
C66 C 0.2059(6) 0.6441(6) 0.0077(4) 0.066(2) Uani 1 1 d . . . . .
H66A H 0.223731 0.697441 -0.017262 0.079 Uiso 1 1 calc R U . . .
C67 C 0.2513(4) 0.5601(6) 0.0498(3) 0.0519(19) Uani 1 1 d . . . . .
H67A H 0.300230 0.556678 0.053124 0.062 Uiso 1 1 calc R U . . .
C68 C 0.2276(4) 0.4793(5) 0.0877(3) 0.0349(14) Uani 1 1 d . . . . .
C69 C 0.2755(3) 0.3907(6) 0.1341(3) 0.0373(14) Uani 1 1 d . . . . .
H69A H 0.327505 0.411382 0.148264 0.045 Uiso 1 1 calc R U . . .
H69B H 0.266528 0.314855 0.109933 0.045 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 0.0033 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'
Sc Sc 0.2519 0.3716 '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
N1 Sc1 C69 109.7(2) . . ?
N1 Sc1 C59 120.35(17) . . ?
C69 Sc1 C59 130.0(2) . . ?
N1 Sc1 N4 111.99(16) . . ?
C69 Sc1 N4 89.88(19) . . ?
C59 Sc1 N4 72.40(16) . . ?
N1 Sc1 N5 109.48(16) . . ?
C69 Sc1 N5 73.42(19) . . ?
C59 Sc1 N5 89.42(16) . . ?
N4 Sc1 N5 138.42(15) . . ?
C1 N1 Sc1 178.6(4) . . ?
C1 N2 C2 111.2(4) . . ?
C1 N2 C11 123.3(4) . . ?
C2 N2 C11 125.3(4) . . ?
C1 N3 C3 111.4(4) . . ?
C1 N3 C31 123.1(4) . . ?
C3 N3 C31 125.4(4) . . ?
C53 N4 C52 113.2(4) . . ?
C53 N4 C51 110.3(4) . . ?
C52 N4 C51 109.5(4) . . ?
C53 N4 Sc1 104.7(3) . . ?
C52 N4 Sc1 106.4(3) . . ?
C51 N4 Sc1 112.7(3) . . ?
C63 N5 C62 113.7(4) . . ?
C63 N5 C61 110.2(4) . . ?
C62 N5 C61 107.5(5) . . ?
C63 N5 Sc1 101.7(3) . . ?
C62 N5 Sc1 112.2(3) . . ?
C61 N5 Sc1 111.5(3) . . ?
N1 C1 N2 128.9(4) . . ?
N1 C1 N3 128.5(4) . . ?
N2 C1 N3 102.6(4) . . ?
C3 C2 N2 107.5(4) . . ?
C3 C2 C4 130.1(4) . . ?
N2 C2 C4 122.4(4) . . ?
C2 C3 N3 107.3(4) . . ?
C2 C3 C5 130.9(4) . . ?
N3 C3 C5 121.8(4) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C16 C11 C12 122.4(4) . . ?
C16 C11 N2 118.9(4) . . ?
C12 C11 N2 118.7(4) . . ?
C13 C12 C11 117.1(4) . . ?
C13 C12 C17 121.4(4) . . ?
C11 C12 C17 121.4(4) . . ?
C14 C13 C12 121.6(5) . . ?
C14 C13 H13A 119.2 . . ?
C12 C13 H13A 119.2 . . ?
C13 C14 C15 119.9(5) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C14 C15 C16 121.3(5) . . ?
C14 C15 H15A 119.3 . . ?
C16 C15 H15A 119.3 . . ?
C15 C16 C11 117.6(5) . . ?
C15 C16 C20 121.1(4) . . ?
C11 C16 C20 121.3(4) . . ?
C18 C17 C12 113.1(4) . . ?
C18 C17 C19 110.9(4) . . ?
C12 C17 C19 111.0(4) . . ?
C18 C17 H17A 107.2 . . ?
C12 C17 H17A 107.2 . . ?
C19 C17 H17A 107.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C16 110.7(5) . . ?
C21 C20 C22 110.0(5) . . ?
C16 C20 C22 112.9(5) . . ?
C21 C20 H20A 107.7 . . ?
C16 C20 H20A 107.7 . . ?
C22 C20 H20A 107.7 . . ?
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 . . ?
C36 C31 C32 122.3(5) . . ?
C36 C31 N3 119.4(4) . . ?
C32 C31 N3 118.3(4) . . ?
C33 C32 C31 117.9(5) . . ?
C33 C32 C37 121.0(5) . . ?
C31 C32 C37 121.1(4) . . ?
C34 C33 C32 120.8(6) . . ?
C34 C33 H33A 119.6 . . ?
C32 C33 H33A 119.6 . . ?
C33 C34 C35 121.5(5) . . ?
C33 C34 H34A 119.2 . . ?
C35 C34 H34A 119.2 . . ?
C34 C35 C36 120.5(6) . . ?
C34 C35 H35A 119.8 . . ?
C36 C35 H35A 119.8 . . ?
C31 C36 C35 117.0(5) . . ?
C31 C36 C40 121.1(5) . . ?
C35 C36 C40 121.9(5) . . ?
C38X C37 C32 123.0(16) . . ?
C39Y C37 C32 118.7(9) . . ?
C38X C37 C39X 122(3) . . ?
C32 C37 C39X 100.6(16) . . ?
C39Y C37 C38Y 106.7(8) . . ?
C32 C37 C38Y 107.7(8) . . ?
C38X C37 H37X 102.6 . . ?
C32 C37 H37X 102.6 . . ?
C39X C37 H37X 102.6 . . ?
C39Y C37 H37Y 107.8 . . ?
C32 C37 H37Y 107.8 . . ?
C38Y C37 H37Y 107.8 . . ?
C37 C38X H38A 109.5 . . ?
C37 C38X H38B 109.5 . . ?
H38A C38X H38B 109.5 . . ?
C37 C38X H38C 109.5 . . ?
H38A C38X H38C 109.5 . . ?
H38B C38X H38C 109.5 . . ?
C37 C39X H39A 109.5 . . ?
C37 C39X H39B 109.5 . . ?
H39A C39X H39B 109.5 . . ?
C37 C39X H39C 109.5 . . ?
H39A C39X H39C 109.5 . . ?
H39B C39X H39C 109.5 . . ?
C37 C38Y H38D 109.5 . . ?
C37 C38Y H38E 109.5 . . ?
H38D C38Y H38E 109.5 . . ?
C37 C38Y H38F 109.5 . . ?
H38D C38Y H38F 109.5 . . ?
H38E C38Y H38F 109.5 . . ?
C37 C39Y H39D 109.5 . . ?
C37 C39Y H39E 109.5 . . ?
H39D C39Y H39E 109.5 . . ?
C37 C39Y H39F 109.5 . . ?
H39D C39Y H39F 109.5 . . ?
H39E C39Y H39F 109.5 . . ?
C41X C40 C36 117(2) . . ?
C36 C40 C41Y 109.3(12) . . ?
C36 C40 C42Y 107.4(8) . . ?
C41Y C40 C42Y 110.2(10) . . ?
C41X C40 C42X 109.3(14) . . ?
C36 C40 C42X 118.9(11) . . ?
C41X C40 H40X 103.1 . . ?
C36 C40 H40X 103.1 . . ?
C42X C40 H40X 103.1 . . ?
C36 C40 H40Y 110.0 . . ?
C41Y C40 H40Y 110.0 . . ?
C42Y C40 H40Y 110.0 . . ?
C40 C41X H41A 109.5 . . ?
C40 C41X H41B 109.5 . . ?
H41A C41X H41B 109.5 . . ?
C40 C41X H41C 109.5 . . ?
H41A C41X H41C 109.5 . . ?
H41B C41X H41C 109.5 . . ?
C40 C42X H42A 109.5 . . ?
C40 C42X H42B 109.5 . . ?
H42A C42X H42B 109.5 . . ?
C40 C42X H42C 109.5 . . ?
H42A C42X H42C 109.5 . . ?
H42B C42X H42C 109.5 . . ?
C40 C41Y H41D 109.5 . . ?
C40 C41Y H41E 109.5 . . ?
H41D C41Y H41E 109.5 . . ?
C40 C41Y H41F 109.5 . . ?
H41D C41Y H41F 109.5 . . ?
H41E C41Y H41F 109.5 . . ?
C40 C42Y H42D 109.5 . . ?
C40 C42Y H42E 109.5 . . ?
H42D C42Y H42E 109.5 . . ?
C40 C42Y H42F 109.5 . . ?
H42D C42Y H42F 109.5 . . ?
H42E C42Y H42F 109.5 . . ?
N4 C51 H51A 109.5 . . ?
N4 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
N4 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N4 C52 H52A 109.5 . . ?
N4 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
N4 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C54 C53 C58 121.9(5) . . ?
C54 C53 N4 122.7(5) . . ?
C58 C53 N4 115.4(4) . . ?
C55 C54 C53 119.9(5) . . ?
C55 C54 H54A 120.0 . . ?
C53 C54 H54A 120.0 . . ?
C56 C55 C54 119.6(5) . . ?
C56 C55 H55A 120.2 . . ?
C54 C55 H55A 120.2 . . ?
C55 C56 C57 120.7(5) . . ?
C55 C56 H56A 119.7 . . ?
C57 C56 H56A 119.7 . . ?
C56 C57 C58 121.9(5) . . ?
C56 C57 H57A 119.0 . . ?
C58 C57 H57A 119.0 . . ?
C53 C58 C57 115.8(5) . . ?
C53 C58 C59 120.1(4) . . ?
C57 C58 C59 124.0(5) . . ?
C58 C59 Sc1 104.2(3) . . ?
C58 C59 H59A 110.9 . . ?
Sc1 C59 H59A 110.9 . . ?
C58 C59 H59B 110.9 . . ?
Sc1 C59 H59B 110.9 . . ?
H59A C59 H59B 108.9 . . ?
N5 C61 H61A 109.5 . . ?
N5 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
N5 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
N5 C62 H62A 109.5 . . ?
N5 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
N5 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C64 C63 C68 121.8(5) . . ?
C64 C63 N5 122.0(6) . . ?
C68 C63 N5 116.2(5) . . ?
C63 C64 C65 119.2(7) . . ?
C63 C64 H64A 120.4 . . ?
C65 C64 H64A 120.4 . . ?
C66 C65 C64 120.2(7) . . ?
C66 C65 H65A 119.9 . . ?
C64 C65 H65A 119.9 . . ?
C65 C66 C67 120.2(6) . . ?
C65 C66 H66A 119.9 . . ?
C67 C66 H66A 119.9 . . ?
C66 C67 C68 122.1(7) . . ?
C66 C67 H67A 119.0 . . ?
C68 C67 H67A 119.0 . . ?
C67 C68 C63 116.5(6) . . ?
C67 C68 C69 123.0(6) . . ?
C63 C68 C69 120.4(5) . . ?
C68 C69 Sc1 102.7(4) . . ?
C68 C69 H69A 111.2 . . ?
Sc1 C69 H69A 111.2 . . ?
C68 C69 H69B 111.2 . . ?
Sc1 C69 H69B 111.2 . . ?
H69A C69 H69B 109.1 . . ?
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
Sc1 N1 1.956(4) . ?
Sc1 C69 2.283(5) . ?
Sc1 C59 2.306(5) . ?
Sc1 N4 2.389(4) . ?
Sc1 N5 2.393(4) . ?
N1 C1 1.270(6) . ?
N2 C1 1.396(6) . ?
N2 C2 1.408(6) . ?
N2 C11 1.429(6) . ?
N3 C1 1.397(6) . ?
N3 C3 1.406(6) . ?
N3 C31 1.428(6) . ?
N4 C53 1.468(6) . ?
N4 C52 1.480(6) . ?
N4 C51 1.480(6) . ?
N5 C63 1.467(7) . ?
N5 C62 1.482(7) . ?
N5 C61 1.484(7) . ?
C2 C3 1.338(7) . ?
C2 C4 1.493(7) . ?
C3 C5 1.488(6) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C11 C16 1.401(7) . ?
C11 C12 1.406(7) . ?
C12 C13 1.394(7) . ?
C12 C17 1.525(6) . ?
C13 C14 1.380(7) . ?
C13 H13A 0.9500 . ?
C14 C15 1.382(7) . ?
C14 H14A 0.9500 . ?
C15 C16 1.391(7) . ?
C15 H15A 0.9500 . ?
C16 C20 1.522(7) . ?
C17 C18 1.522(7) . ?
C17 C19 1.530(7) . ?
C17 H17A 1.0000 . ?
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(9) . ?
C20 C22 1.524(8) . ?
C20 H20A 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C31 C36 1.390(7) . ?
C31 C32 1.402(7) . ?
C32 C33 1.384(7) . ?
C32 C37 1.520(8) . ?
C33 C34 1.354(9) . ?
C33 H33A 0.9500 . ?
C34 C35 1.370(10) . ?
C34 H34A 0.9500 . ?
C35 C36 1.410(8) . ?
C35 H35A 0.9500 . ?
C36 C40 1.522(9) . ?
C37 C38X 1.500(15) . ?
C37 C39Y 1.502(10) . ?
C37 C39X 1.534(16) . ?
C37 C38Y 1.538(10) . ?
C37 H37X 1.0000 . ?
C37 H37Y 1.0000 . ?
C38X H38A 0.9800 . ?
C38X H38B 0.9800 . ?
C38X H38C 0.9800 . ?
C39X H39A 0.9800 . ?
C39X H39B 0.9800 . ?
C39X H39C 0.9800 . ?
C38Y H38D 0.9800 . ?
C38Y H38E 0.9800 . ?
C38Y H38F 0.9800 . ?
C39Y H39D 0.9800 . ?
C39Y H39E 0.9800 . ?
C39Y H39F 0.9800 . ?
C40 C41X 1.520(15) . ?
C40 C41Y 1.529(12) . ?
C40 C42Y 1.559(13) . ?
C40 C42X 1.56(3) . ?
C40 H40X 1.0000 . ?
C40 H40Y 1.0000 . ?
C41X H41A 0.9800 . ?
C41X H41B 0.9800 . ?
C41X H41C 0.9800 . ?
C42X H42A 0.9800 . ?
C42X H42B 0.9800 . ?
C42X H42C 0.9800 . ?
C41Y H41D 0.9800 . ?
C41Y H41E 0.9800 . ?
C41Y H41F 0.9800 . ?
C42Y H42D 0.9800 . ?
C42Y H42E 0.9800 . ?
C42Y H42F 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 C54 1.387(7) . ?
C53 C58 1.407(7) . ?
C54 C55 1.383(8) . ?
C54 H54A 0.9500 . ?
C55 C56 1.369(8) . ?
C55 H55A 0.9500 . ?
C56 C57 1.378(8) . ?
C56 H56A 0.9500 . ?
C57 C58 1.408(7) . ?
C57 H57A 0.9500 . ?
C58 C59 1.469(7) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?
C63 C64 1.393(8) . ?
C63 C68 1.405(8) . ?
C64 C65 1.394(10) . ?
C64 H64A 0.9500 . ?
C65 C66 1.371(11) . ?
C65 H65A 0.9500 . ?
C66 C67 1.377(11) . ?
C66 H66A 0.9500 . ?
C67 C68 1.402(8) . ?
C67 H67A 0.9500 . ?
C68 C69 1.468(8) . ?
C69 H69A 0.9900 . ?
C69 H69B 0.9900 . ?
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
C2 N2 C1 N1 178.9(4) . . . . ?
C11 N2 C1 N1 -5.0(7) . . . . ?
C2 N2 C1 N3 0.2(5) . . . . ?
C11 N2 C1 N3 176.2(4) . . . . ?
C3 N3 C1 N1 -178.5(5) . . . . ?
C31 N3 C1 N1 3.5(7) . . . . ?
C3 N3 C1 N2 0.3(5) . . . . ?
C31 N3 C1 N2 -177.7(4) . . . . ?
C1 N2 C2 C3 -0.6(5) . . . . ?
C11 N2 C2 C3 -176.5(4) . . . . ?
C1 N2 C2 C4 -179.5(4) . . . . ?
C11 N2 C2 C4 4.5(7) . . . . ?
N2 C2 C3 N3 0.7(5) . . . . ?
C4 C2 C3 N3 179.6(5) . . . . ?
N2 C2 C3 C5 -177.8(5) . . . . ?
C4 C2 C3 C5 1.0(9) . . . . ?
C1 N3 C3 C2 -0.7(5) . . . . ?
C31 N3 C3 C2 177.3(4) . . . . ?
C1 N3 C3 C5 178.0(4) . . . . ?
C31 N3 C3 C5 -4.0(7) . . . . ?
C1 N2 C11 C16 -77.6(6) . . . . ?
C2 N2 C11 C16 97.8(5) . . . . ?
C1 N2 C11 C12 102.8(5) . . . . ?
C2 N2 C11 C12 -81.7(6) . . . . ?
C16 C11 C12 C13 1.3(7) . . . . ?
N2 C11 C12 C13 -179.1(4) . . . . ?
C16 C11 C12 C17 179.9(4) . . . . ?
N2 C11 C12 C17 -0.5(7) . . . . ?
C11 C12 C13 C14 -0.7(7) . . . . ?
C17 C12 C13 C14 -179.3(5) . . . . ?
C12 C13 C14 C15 -0.1(8) . . . . ?
C13 C14 C15 C16 0.2(8) . . . . ?
C14 C15 C16 C11 0.4(8) . . . . ?
C14 C15 C16 C20 -179.0(5) . . . . ?
C12 C11 C16 C15 -1.2(7) . . . . ?
N2 C11 C16 C15 179.3(4) . . . . ?
C12 C11 C16 C20 178.2(5) . . . . ?
N2 C11 C16 C20 -1.3(7) . . . . ?
C13 C12 C17 C18 -28.8(7) . . . . ?
C11 C12 C17 C18 152.7(5) . . . . ?
C13 C12 C17 C19 96.6(5) . . . . ?
C11 C12 C17 C19 -81.9(6) . . . . ?
C15 C16 C20 C21 84.7(7) . . . . ?
C11 C16 C20 C21 -94.7(6) . . . . ?
C15 C16 C20 C22 -39.1(7) . . . . ?
C11 C16 C20 C22 141.5(5) . . . . ?
C1 N3 C31 C36 104.6(5) . . . . ?
C3 N3 C31 C36 -73.1(6) . . . . ?
C1 N3 C31 C32 -77.4(6) . . . . ?
C3 N3 C31 C32 104.9(5) . . . . ?
C36 C31 C32 C33 -0.8(7) . . . . ?
N3 C31 C32 C33 -178.8(4) . . . . ?
C36 C31 C32 C37 177.2(5) . . . . ?
N3 C31 C32 C37 -0.9(7) . . . . ?
C31 C32 C33 C34 0.7(8) . . . . ?
C37 C32 C33 C34 -177.2(5) . . . . ?
C32 C33 C34 C35 -0.3(9) . . . . ?
C33 C34 C35 C36 0.0(9) . . . . ?
C32 C31 C36 C35 0.5(7) . . . . ?
N3 C31 C36 C35 178.5(4) . . . . ?
C32 C31 C36 C40 -179.9(5) . . . . ?
N3 C31 C36 C40 -1.9(7) . . . . ?
C34 C35 C36 C31 -0.1(8) . . . . ?
C34 C35 C36 C40 -179.6(5) . . . . ?
C33 C32 C37 C38X 103(3) . . . . ?
C31 C32 C37 C38X -75(3) . . . . ?
C33 C32 C37 C39Y -42.0(11) . . . . ?
C31 C32 C37 C39Y 140.1(10) . . . . ?
C33 C32 C37 C39X -37(2) . . . . ?
C31 C32 C37 C39X 145(2) . . . . ?
C33 C32 C37 C38Y 79.3(10) . . . . ?
C31 C32 C37 C38Y -98.6(10) . . . . ?
C31 C36 C40 C41X -104(2) . . . . ?
C35 C36 C40 C41X 76(2) . . . . ?
C31 C36 C40 C41Y -94.0(15) . . . . ?
C35 C36 C40 C41Y 85.6(15) . . . . ?
C31 C36 C40 C42Y 146.5(10) . . . . ?
C35 C36 C40 C42Y -34.0(11) . . . . ?
C31 C36 C40 C42X 121.7(17) . . . . ?
C35 C36 C40 C42X -58.7(18) . . . . ?
C52 N4 C53 C54 31.3(6) . . . . ?
C51 N4 C53 C54 -91.8(6) . . . . ?
Sc1 N4 C53 C54 146.7(4) . . . . ?
C52 N4 C53 C58 -147.5(4) . . . . ?
C51 N4 C53 C58 89.4(5) . . . . ?
Sc1 N4 C53 C58 -32.1(5) . . . . ?
C58 C53 C54 C55 2.6(8) . . . . ?
N4 C53 C54 C55 -176.1(5) . . . . ?
C53 C54 C55 C56 0.8(8) . . . . ?
C54 C55 C56 C57 -2.3(9) . . . . ?
C55 C56 C57 C58 0.4(8) . . . . ?
C54 C53 C58 C57 -4.3(7) . . . . ?
N4 C53 C58 C57 174.5(4) . . . . ?
C54 C53 C58 C59 178.8(5) . . . . ?
N4 C53 C58 C59 -2.4(6) . . . . ?
C56 C57 C58 C53 2.8(7) . . . . ?
C56 C57 C58 C59 179.6(5) . . . . ?
C53 C58 C59 Sc1 36.8(5) . . . . ?
C57 C58 C59 Sc1 -139.8(4) . . . . ?
C62 N5 C63 C64 -24.0(7) . . . . ?
C61 N5 C63 C64 96.8(6) . . . . ?
Sc1 N5 C63 C64 -144.9(4) . . . . ?
C62 N5 C63 C68 155.3(5) . . . . ?
C61 N5 C63 C68 -83.9(6) . . . . ?
Sc1 N5 C63 C68 34.5(5) . . . . ?
C68 C63 C64 C65 -2.2(8) . . . . ?
N5 C63 C64 C65 177.2(5) . . . . ?
C63 C64 C65 C66 -0.5(9) . . . . ?
C64 C65 C66 C67 1.6(11) . . . . ?
C65 C66 C67 C68 0.0(10) . . . . ?
C66 C67 C68 C63 -2.5(9) . . . . ?
C66 C67 C68 C69 -178.6(6) . . . . ?
C64 C63 C68 C67 3.6(8) . . . . ?
N5 C63 C68 C67 -175.8(5) . . . . ?
C64 C63 C68 C69 179.8(5) . . . . ?
N5 C63 C68 C69 0.4(7) . . . . ?
C67 C68 C69 Sc1 138.8(5) . . . . ?
C63 C68 C69 Sc1 -37.2(6) . . . . ?
