#------------------------------------------------------------------------------
#$Date: 2022-05-09 11:13:54 +0200 (lun 09 de may de 2022) $
#$Revision: 275278 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/51/8105191.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_8105191
loop_
_publ_author_name
'Xu, Xin-Yue'
'Huang, Xiao-Bo'
'Wu, Deng-Ze'
_publ_section_title
;
 The crystal structure of
 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile),
 C46H60N6O2Se2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              239
_journal_page_last               242
_journal_paper_doi               10.1515/ncrs-2021-0456
_journal_volume                  237
_journal_year                    2022
_chemical_formula_sum            'C46 H60 N6 O2 Se2'
_chemical_formula_weight         886.92
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                92.079(2)
_cell_angle_beta                 97.937(2)
_cell_angle_gamma                95.848(2)
_cell_formula_units_Z            2
_cell_length_a                   10.4701(7)
_cell_length_b                   10.6331(7)
_cell_length_c                   20.4665(14)
_cell_measurement_reflns_used    5717
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.912
_cell_measurement_theta_min      5.215
_cell_volume                     2242.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22203
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         2.607
_exptl_absorpt_coefficient_mu    1.692
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     566
_refine_ls_number_reflns         8296
_refine_ls_number_restraints     105
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0393P)²+1.7425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1183
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5396
_reflns_number_total             8296
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0456_suppl.cif
_cod_data_source_block           mo_dd19113_0m
_cod_database_code               8105191
_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   0.773
_shelx_estimated_absorpt_t_max   0.849
_shelxl_version_number           2013-4
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
Se1 Se 0.05978(4) 0.62847(4) 0.22989(2) 0.05821(15) Uani 1 1 d . . . . .
Se2 Se 0.14856(4) 0.70435(4) 0.33767(2) 0.05218(15) Uani 1 1 d . . . . .
O1 O 0.5998(3) 0.7304(3) 0.09844(13) 0.0533(7) Uani 1 1 d . . . . .
O2 O 0.0805(3) 0.1629(3) 0.48349(15) 0.0573(8) Uani 1 1 d D . . . .
N1 N 0.3575(3) 0.4411(3) 0.17419(16) 0.0492(8) Uani 1 1 d . . . . .
N2 N 0.5986(5) 1.0485(4) 0.0715(2) 0.0953(15) Uani 1 1 d . . . . .
N3 N 0.5664(3) 0.4950(3) 0.15481(16) 0.0480(8) Uani 1 1 d . . . . .
N4 N 0.3563(3) 0.4107(3) 0.40291(17) 0.0506(9) Uani 1 1 d . . . . .
N5 N -0.2423(4) 0.1623(4) 0.5104(2) 0.0720(12) Uani 1 1 d . . . . .
N6 N 0.3027(3) 0.1998(3) 0.41680(17) 0.0489(9) Uani 1 1 d . . . . .
C1 C 0.2430(4) 0.4697(4) 0.1904(2) 0.0504(10) Uani 1 1 d . . . . .
C2 C 0.2146(4) 0.5927(4) 0.19630(19) 0.0462(10) Uani 1 1 d . . . . .
C3 C 0.3005(4) 0.6916(4) 0.17560(18) 0.0439(10) Uani 1 1 d . . . . .
C4 C 0.2682(4) 0.8173(4) 0.1709(2) 0.0523(11) Uani 1 1 d . . . . .
H4 H 0.1929 0.8377 0.1862 0.063 Uiso 1 1 calc R U . . .
C5 C 0.3428(4) 0.9096(4) 0.1449(2) 0.0551(11) Uani 1 1 d . . . . .
C6 C 0.4563(4) 0.8772(4) 0.1215(2) 0.0510(11) Uani 1 1 d . . . . .
C7 C 0.4913(4) 0.7559(4) 0.12499(19) 0.0455(10) Uani 1 1 d . . . . .
C8 C 0.4181(4) 0.6606(4) 0.15508(18) 0.0410(9) Uani 1 1 d . . . . .
C9 C 0.4469(4) 0.5304(4) 0.16242(18) 0.0446(10) Uani 1 1 d . . . . .
C10 C 0.1545(5) 0.3564(4) 0.2048(3) 0.0794(16) Uani 1 1 d . . . . .
H10A H 0.1802 0.2813 0.1852 0.119 Uiso 1 1 calc R U . . .
H10B H 0.0668 0.3665 0.1865 0.119 Uiso 1 1 calc R U . . .
H10C H 0.1601 0.3494 0.2517 0.119 Uiso 1 1 calc R U . . .
C11 C 0.3042(5) 1.0423(4) 0.1383(3) 0.0821(16) Uani 1 1 d . . . . .
H11A H 0.3672 1.1007 0.1656 0.123 Uiso 1 1 calc R U . . .
H11B H 0.2207 1.0460 0.1522 0.123 Uiso 1 1 calc R U . . .
H11C H 0.3002 1.0644 0.0931 0.123 Uiso 1 1 calc R U . . .
C12 C 0.5374(5) 0.9705(5) 0.0926(2) 0.0641(13) Uani 1 1 d . . . . .
C13 C 0.6837(4) 0.5644(4) 0.1927(2) 0.0578(12) Uani 1 1 d . . . . .
H13A H 0.6683 0.6515 0.2014 0.069 Uiso 1 1 calc R U . . .
H13B H 0.7548 0.5649 0.1669 0.069 Uiso 1 1 calc R U . . .
C14 C 0.7201(4) 0.5046(4) 0.2567(2) 0.0640(13) Uani 1 1 d . . . . .
H14A H 0.6524 0.5118 0.2841 0.077 Uiso 1 1 calc R U . . .
H14B H 0.7996 0.5499 0.2797 0.077 Uiso 1 1 calc R U . . .
C15 C 0.7394(5) 0.3659(5) 0.2466(2) 0.0744(14) Uani 1 1 d . . . . .
H15A H 0.8124 0.3584 0.2228 0.089 Uiso 1 1 calc R U . . .
H15B H 0.7579 0.3291 0.2890 0.089 Uiso 1 1 calc R U . . .
C16 C 0.6175(5) 0.2959(4) 0.2076(2) 0.0678(13) Uani 1 1 d . . . . .
H16A H 0.6323 0.2092 0.1976 0.081 Uiso 1 1 calc R U . . .
H16B H 0.5473 0.2942 0.2341 0.081 Uiso 1 1 calc R U . . .
C17 C 0.5796(4) 0.3597(4) 0.1442(2) 0.0571(12) Uani 1 1 d . . . . .
H17A H 0.6447 0.3506 0.1154 0.069 Uiso 1 1 calc R U . . .
H17B H 0.4979 0.3174 0.1219 0.069 Uiso 1 1 calc R U . . .
C18 C 0.5761(5) 0.6874(6) 0.0303(2) 0.0862(15) Uani 1 1 d . U . . .
H18A H 0.5501 0.7556 0.0030 0.103 Uiso 1 1 calc R U . . .
H18B H 0.5070 0.6182 0.0233 0.103 Uiso 1 1 calc R U . . .
C19 C 0.6973(6) 0.6443(7) 0.0122(3) 0.1076(15) Uani 1 1 d . U . . .
H19A H 0.7167 0.5717 0.0376 0.129 Uiso 1 1 calc R U . . .
H19B H 0.6813 0.6155 -0.0340 0.129 Uiso 1 1 calc R U . . .
C20 C 0.8094(6) 0.7342(8) 0.0217(3) 0.1279(17) Uani 1 1 d D U . . .
H20A H 0.8271 0.7632 0.0679 0.153 Uiso 1 1 calc R U . . .
H20B H 0.7919 0.8068 -0.0041 0.153 Uiso 1 1 calc R U . . .
C21 C 0.9324(7) 0.6796(8) 0.0015(4) 0.1472(19) Uani 1 1 d D U . . .
H21A H 0.9561 0.6139 0.0311 0.177 Uiso 1 1 calc R U . . .
H21B H 0.9110 0.6407 -0.0428 0.177 Uiso 1 1 calc R U . . .
C22 C 1.0402(7) 0.7711(9) 0.0031(4) 0.164(2) Uani 1 1 d D U . . .
H22A H 1.0627 0.8087 0.0476 0.197 Uiso 1 1 calc R U . . .
H22B H 1.0159 0.8377 -0.0258 0.197 Uiso 1 1 calc R U . . .
C23 C 1.1583(7) 0.7192(9) -0.0177(4) 0.174(3) Uani 1 1 d D U . . .
H23A H 1.1808 0.6506 0.0093 0.261 Uiso 1 1 calc R U . . .
H23B H 1.2295 0.7849 -0.0125 0.261 Uiso 1 1 calc R U . . .
H23C H 1.1395 0.6891 -0.0632 0.261 Uiso 1 1 calc R U . . .
C24 C 0.3215(4) 0.5257(4) 0.3856(2) 0.0480(10) Uani 1 1 d . . . . .
C25 C 0.1938(4) 0.5506(3) 0.37558(19) 0.0426(9) Uani 1 1 d . . . . .
C26 C 0.0974(4) 0.4621(3) 0.39697(18) 0.0387(9) Uani 1 1 d . . . . .
C27 C -0.0306(3) 0.4893(4) 0.39952(18) 0.0405(9) Uani 1 1 d . . . . .
H27 H -0.0567 0.5633 0.3817 0.049 Uiso 1 1 calc R U . . .
C28 C -0.1181(4) 0.4118(4) 0.42706(18) 0.0409(9) Uani 1 1 d . . . . .
C29 C -0.0766(4) 0.3005(4) 0.45485(19) 0.0429(9) Uani 1 1 d . . . . .
C30 C 0.0484(4) 0.2695(4) 0.45285(19) 0.0439(10) Uani 1 1 d . . . . .
C31 C 0.1357(4) 0.3449(3) 0.42020(19) 0.0406(9) Uani 1 1 d . . . . .
C32 C 0.2663(4) 0.3192(4) 0.41250(19) 0.0434(9) Uani 1 1 d . . . . .
C33 C 0.4337(4) 0.6208(4) 0.3765(3) 0.0770(16) Uani 1 1 d . . . . .
H33A H 0.5131 0.5926 0.3970 0.116 Uiso 1 1 calc R U . . .
H33B H 0.4224 0.7012 0.3966 0.116 Uiso 1 1 calc R U . . .
H33C H 0.4370 0.6292 0.3302 0.116 Uiso 1 1 calc R U . . .
C34 C -0.2535(4) 0.4443(4) 0.4304(2) 0.0537(11) Uani 1 1 d . . . . .
H34A H -0.3147 0.3819 0.4048 0.081 Uiso 1 1 calc R U . . .
H34B H -0.2631 0.5260 0.4131 0.081 Uiso 1 1 calc R U . . .
H34C H -0.2692 0.4457 0.4756 0.081 Uiso 1 1 calc R U . . .
C35 C -0.1655(4) 0.2218(4) 0.4868(2) 0.0519(11) Uani 1 1 d . . . . .
C36 C 0.2207(4) 0.0904(4) 0.3827(2) 0.0565(12) Uani 1 1 d . . . . .
H36A H 0.1322 0.1110 0.3727 0.068 Uiso 1 1 calc R U . . .
H36B H 0.2208 0.0196 0.4113 0.068 Uiso 1 1 calc R U . . .
C37 C 0.2696(5) 0.0533(4) 0.3193(2) 0.0663(13) Uani 1 1 d . . . . .
H37A H 0.2597 0.1204 0.2888 0.080 Uiso 1 1 calc R U . . .
H37B H 0.2177 -0.0226 0.2991 0.080 Uiso 1 1 calc R U . . .
C38 C 0.4113(5) 0.0290(5) 0.3316(3) 0.0789(15) Uani 1 1 d . . . . .
H38A H 0.4205 -0.0439 0.3583 0.095 Uiso 1 1 calc R U . . .
H38B H 0.4413 0.0109 0.2898 0.095 Uiso 1 1 calc R U . . .
C39 C 0.4925(4) 0.1444(4) 0.3669(2) 0.0682(13) Uani 1 1 d . . . . .
H39A H 0.5816 0.1261 0.3778 0.082 Uiso 1 1 calc R U . . .
H39B H 0.4914 0.2146 0.3380 0.082 Uiso 1 1 calc R U . . .
C40 C 0.4403(4) 0.1807(4) 0.4294(2) 0.0569(11) Uani 1 1 d . . . . .
H40A H 0.4519 0.1147 0.4605 0.068 Uiso 1 1 calc R U . . .
H40B H 0.4895 0.2581 0.4494 0.068 Uiso 1 1 calc R U . . .
C41 C 0.1771(9) 0.1764(8) 0.5413(4) 0.0840(19) Uani 0.7 1 d D U P A 1
H41A H 0.1965 0.2656 0.5546 0.101 Uiso 0.7 1 calc R U P A 1
H41B H 0.2561 0.1463 0.5300 0.101 Uiso 0.7 1 calc R U P A 1
C42 C 0.1385(9) 0.1087(8) 0.5963(4) 0.0886(18) Uani 0.7 1 d D U P A 1
H42A H 0.1131 0.0204 0.5824 0.106 Uiso 0.7 1 calc R U P A 1
H42B H 0.0638 0.1432 0.6102 0.106 Uiso 0.7 1 calc R U P A 1
C43 C 0.2499(9) 0.1175(13) 0.6558(5) 0.100(2) Uani 0.7 1 d D U P A 1
H43A H 0.3297 0.0987 0.6402 0.120 Uiso 0.7 1 calc R U P A 1
H43B H 0.2636 0.2029 0.6755 0.120 Uiso 0.7 1 calc R U P A 1
C44 C 0.2169(12) 0.0248(12) 0.7074(6) 0.117(2) Uani 0.6 1 d D U P A 1
H44A H 0.1820 -0.0553 0.6844 0.141 Uiso 0.6 1 calc R U P A 1
H44B H 0.2975 0.0107 0.7344 0.141 Uiso 0.6 1 calc R U P A 1
C45 C 0.1298(13) 0.0560(14) 0.7504(7) 0.125(3) Uani 0.6 1 d D U P A 1
H45A H 0.0472 0.0601 0.7229 0.150 Uiso 0.6 1 calc R U P A 1
H45B H 0.1593 0.1417 0.7678 0.150 Uiso 0.6 1 calc R U P A 1
C46 C 0.0999(15) -0.0211(14) 0.8100(6) 0.127(4) Uani 0.6 1 d D U P A 1
H46A H 0.1382 -0.0993 0.8086 0.190 Uiso 0.6 1 calc R U P A 1
H46B H 0.0077 -0.0389 0.8083 0.190 Uiso 0.6 1 calc R U P A 1
H46C H 0.1352 0.0268 0.8503 0.190 Uiso 0.6 1 calc R U P A 1
C41' C 0.0908(17) 0.157(3) 0.5515(7) 0.097(4) Uani 0.3 1 d D U P A 2
H41C H 0.0276 0.0912 0.5624 0.117 Uiso 0.3 1 calc R U P A 2
H41D H 0.0713 0.2372 0.5702 0.117 Uiso 0.3 1 calc R U P A 2
C42' C 0.2265(17) 0.131(3) 0.5819(9) 0.104(4) Uani 0.3 1 d D U P A 2
H42C H 0.2919 0.1973 0.5733 0.124 Uiso 0.3 1 calc R U P A 2
H42D H 0.2477 0.0501 0.5656 0.124 Uiso 0.3 1 calc R U P A 2
C43' C 0.213(2) 0.130(3) 0.6564(11) 0.111(4) Uani 0.3 1 d D U P A 2
H43C H 0.3013 0.1300 0.6781 0.133 Uiso 0.3 1 calc R U P A 2
H43D H 0.1888 0.2134 0.6665 0.133 Uiso 0.3 1 calc R U P A 2
C44' C 0.1350(16) 0.0450(19) 0.6963(8) 0.116(4) Uani 0.4 1 d D U P A 2
H44C H 0.1215 -0.0395 0.6753 0.140 Uiso 0.4 1 calc R U P A 2
H44D H 0.0506 0.0750 0.6964 0.140 Uiso 0.4 1 calc R U P A 2
C45' C 0.2002(16) 0.0379(19) 0.7688(8) 0.122(4) Uani 0.4 1 d D U P A 2
H45C H 0.2839 0.0052 0.7727 0.146 Uiso 0.4 1 calc R U P A 2
H45D H 0.2052 0.1166 0.7949 0.146 Uiso 0.4 1 calc R U P A 2
C46' C 0.088(2) -0.061(2) 0.7811(10) 0.131(5) Uani 0.4 1 d D U P A 2
H46D H 0.0153 -0.0184 0.7904 0.196 Uiso 0.4 1 calc R U P A 2
H46E H 0.1164 -0.1094 0.8180 0.196 Uiso 0.4 1 calc R U P A 2
H46F H 0.0622 -0.1168 0.7425 0.196 Uiso 0.4 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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
C2 Se1 Se2 99.84(12) . .
C25 Se2 Se1 100.43(12) . .
C7 O1 C18 114.8(3) . .
C30 O2 C41' 121.0(10) . .
C30 O2 C41 118.4(4) . .
C9 N1 C1 121.1(3) . .
C9 N3 C17 118.7(3) . .
C9 N3 C13 119.7(3) . .
C17 N3 C13 112.3(3) . .
C32 N4 C24 119.8(3) . .
C32 N6 C40 120.2(3) . .
C32 N6 C36 121.4(3) . .
C40 N6 C36 113.4(3) . .
N1 C1 C2 121.9(4) . .
N1 C1 C10 114.0(4) . .
C2 C1 C10 124.0(4) . .
C1 C2 C3 119.0(4) . .
C1 C2 Se1 119.9(3) . .
C3 C2 Se1 121.1(3) . .
C4 C3 C8 119.2(4) . .
C4 C3 C2 122.0(4) . .
C8 C3 C2 118.6(3) . .
C5 C4 C3 122.7(4) . .
C5 C4 H4 118.7 . .
C3 C4 H4 118.7 . .
C4 C5 C6 118.1(4) . .
C4 C5 C11 121.8(4) . .
C6 C5 C11 120.1(4) . .
C7 C6 C5 121.2(4) . .
C7 C6 C12 118.5(4) . .
C5 C6 C12 120.3(4) . .
O1 C7 C6 117.7(4) . .
O1 C7 C8 121.0(3) . .
C6 C7 C8 121.3(4) . .
C7 C8 C3 117.3(3) . .
C7 C8 C9 126.1(3) . .
C3 C8 C9 116.5(3) . .
N1 C9 N3 117.4(4) . .
N1 C9 C8 121.2(4) . .
N3 C9 C8 121.3(4) . .
C1 C10 H10A 109.5 . .
C1 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C1 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C5 C11 H11A 109.5 . .
C5 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C5 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N2 C12 C6 176.5(5) . .
N3 C13 C14 110.9(4) . .
N3 C13 H13A 109.5 . .
C14 C13 H13A 109.5 . .
N3 C13 H13B 109.5 . .
C14 C13 H13B 109.5 . .
H13A C13 H13B 108.0 . .
C13 C14 C15 112.1(4) . .
C13 C14 H14A 109.2 . .
C15 C14 H14A 109.2 . .
C13 C14 H14B 109.2 . .
C15 C14 H14B 109.2 . .
H14A C14 H14B 107.9 . .
C16 C15 C14 109.4(4) . .
C16 C15 H15A 109.8 . .
C14 C15 H15A 109.8 . .
C16 C15 H15B 109.8 . .
C14 C15 H15B 109.8 . .
H15A C15 H15B 108.2 . .
C17 C16 C15 110.6(4) . .
C17 C16 H16A 109.5 . .
C15 C16 H16A 109.5 . .
C17 C16 H16B 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 108.1 . .
N3 C17 C16 112.9(3) . .
N3 C17 H17A 109.0 . .
C16 C17 H17A 109.0 . .
N3 C17 H17B 109.0 . .
C16 C17 H17B 109.0 . .
H17A C17 H17B 107.8 . .
O1 C18 C19 108.2(4) . .
O1 C18 H18A 110.1 . .
C19 C18 H18A 110.1 . .
O1 C18 H18B 110.1 . .
C19 C18 H18B 110.1 . .
H18A C18 H18B 108.4 . .
C20 C19 C18 116.9(6) . .
C20 C19 H19A 108.1 . .
C18 C19 H19A 108.1 . .
C20 C19 H19B 108.1 . .
C18 C19 H19B 108.1 . .
H19A C19 H19B 107.3 . .
C19 C20 C21 113.0(6) . .
C19 C20 H20A 109.0 . .
C21 C20 H20A 109.0 . .
C19 C20 H20B 109.0 . .
C21 C20 H20B 109.0 . .
H20A C20 H20B 107.8 . .
C22 C21 C20 113.7(7) . .
C22 C21 H21A 108.8 . .
C20 C21 H21A 108.8 . .
C22 C21 H21B 108.8 . .
C20 C21 H21B 108.8 . .
H21A C21 H21B 107.7 . .
C21 C22 C23 113.9(8) . .
C21 C22 H22A 108.8 . .
C23 C22 H22A 108.8 . .
C21 C22 H22B 108.8 . .
C23 C22 H22B 108.8 . .
H22A C22 H22B 107.7 . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
N4 C24 C25 122.2(4) . .
N4 C24 C33 114.1(4) . .
C25 C24 C33 123.6(4) . .
C24 C25 C26 118.7(3) . .
C24 C25 Se2 120.2(3) . .
C26 C25 Se2 121.0(3) . .
C27 C26 C31 119.0(3) . .
C27 C26 C25 122.7(3) . .
C31 C26 C25 118.2(3) . .
C28 C27 C26 122.8(3) . .
C28 C27 H27 118.6 . .
C26 C27 H27 118.6 . .
C27 C28 C29 117.9(3) . .
C27 C28 C34 121.8(4) . .
C29 C28 C34 120.2(3) . .
C30 C29 C28 121.1(4) . .
C30 C29 C35 120.5(4) . .
C28 C29 C35 118.4(3) . .
O2 C30 C29 116.5(3) . .
O2 C30 C31 122.6(4) . .
C29 C30 C31 120.8(4) . .
C30 C31 C26 117.7(3) . .
C30 C31 C32 125.8(3) . .
C26 C31 C32 116.3(3) . .
N4 C32 N6 117.1(3) . .
N4 C32 C31 121.6(3) . .
N6 C32 C31 121.2(3) . .
C24 C33 H33A 109.5 . .
C24 C33 H33B 109.5 . .
H33A C33 H33B 109.5 . .
C24 C33 H33C 109.5 . .
H33A C33 H33C 109.5 . .
H33B C33 H33C 109.5 . .
C28 C34 H34A 109.5 . .
C28 C34 H34B 109.5 . .
H34A C34 H34B 109.5 . .
C28 C34 H34C 109.5 . .
H34A C34 H34C 109.5 . .
H34B C34 H34C 109.5 . .
N5 C35 C29 176.0(5) . .
N6 C36 C37 110.7(4) . .
N6 C36 H36A 109.5 . .
C37 C36 H36A 109.5 . .
N6 C36 H36B 109.5 . .
C37 C36 H36B 109.5 . .
H36A C36 H36B 108.1 . .
C36 C37 C38 111.7(4) . .
C36 C37 H37A 109.3 . .
C38 C37 H37A 109.3 . .
C36 C37 H37B 109.3 . .
C38 C37 H37B 109.3 . .
H37A C37 H37B 107.9 . .
C39 C38 C37 109.8(4) . .
C39 C38 H38A 109.7 . .
C37 C38 H38A 109.7 . .
C39 C38 H38B 109.7 . .
C37 C38 H38B 109.7 . .
H38A C38 H38B 108.2 . .
C40 C39 C38 110.6(4) . .
C40 C39 H39A 109.5 . .
C38 C39 H39A 109.5 . .
C40 C39 H39B 109.5 . .
C38 C39 H39B 109.5 . .
H39A C39 H39B 108.1 . .
N6 C40 C39 112.1(4) . .
N6 C40 H40A 109.2 . .
C39 C40 H40A 109.2 . .
N6 C40 H40B 109.2 . .
C39 C40 H40B 109.2 . .
H40A C40 H40B 107.9 . .
O2 C41 C42 113.7(7) . .
O2 C41 H41A 108.8 . .
C42 C41 H41A 108.8 . .
O2 C41 H41B 108.8 . .
C42 C41 H41B 108.8 . .
H41A C41 H41B 107.7 . .
C41 C42 C43 111.9(8) . .
C41 C42 H42A 109.2 . .
C43 C42 H42A 109.2 . .
C41 C42 H42B 109.2 . .
C43 C42 H42B 109.2 . .
H42A C42 H42B 107.9 . .
C44 C43 C42 110.7(9) . .
C44 C43 H43A 109.5 . .
C42 C43 H43A 109.5 . .
C44 C43 H43B 109.5 . .
C42 C43 H43B 109.5 . .
H43A C43 H43B 108.1 . .
C45 C44 C43 118.8(11) . .
C45 C44 H44A 107.6 . .
C43 C44 H44A 107.6 . .
C45 C44 H44B 107.6 . .
C43 C44 H44B 107.6 . .
H44A C44 H44B 107.0 . .
C44 C45 C46 124.3(12) . .
C44 C45 H45A 106.3 . .
C46 C45 H45A 106.3 . .
C44 C45 H45B 106.3 . .
C46 C45 H45B 106.3 . .
H45A C45 H45B 106.4 . .
C45 C46 H46A 109.5 . .
C45 C46 H46B 109.5 . .
H46A C46 H46B 109.5 . .
C45 C46 H46C 109.5 . .
H46A C46 H46C 109.5 . .
H46B C46 H46C 109.5 . .
O2 C41' C42' 111.7(14) . .
O2 C41' H41C 109.3 . .
C42' C41' H41C 109.3 . .
O2 C41' H41D 109.3 . .
C42' C41' H41D 109.3 . .
H41C C41' H41D 107.9 . .
C41' C42' C43' 101.6(15) . .
C41' C42' H42C 111.5 . .
C43' C42' H42C 111.5 . .
C41' C42' H42D 111.5 . .
C43' C42' H42D 111.4 . .
H42C C42' H42D 109.3 . .
C44' C43' C42' 133(3) . .
C44' C43' H43C 103.9 . .
C42' C43' H43C 103.9 . .
C44' C43' H43D 103.9 . .
C42' C43' H43D 103.9 . .
H43C C43' H43D 105.4 . .
C43' C44' C45' 113.4(16) . .
C43' C44' H44C 108.9 . .
C45' C44' H44C 108.9 . .
C43' C44' H44D 108.9 . .
C45' C44' H44D 108.9 . .
H44C C44' H44D 107.7 . .
C46' C45' C44' 89.8(15) . .
C46' C45' H45C 113.7 . .
C44' C45' H45C 113.7 . .
C46' C45' H45D 113.7 . .
C44' C45' H45D 113.7 . .
H45C C45' H45D 110.9 . .
C45' C46' H46D 109.5 . .
C45' C46' H46E 109.5 . .
H46D C46' H46E 109.5 . .
C45' C46' H46F 109.5 . .
H46D C46' H46F 109.5 . .
H46E C46' H46F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 C2 1.913(4) .
Se1 Se2 2.3521(7) .
Se2 C25 1.909(4) .
O1 C7 1.372(4) .
O1 C18 1.433(5) .
O2 C30 1.365(4) .
O2 C41' 1.385(14) .
O2 C41 1.439(8) .
N1 C9 1.317(5) .
N1 C1 1.347(5) .
N2 C12 1.130(5) .
N3 C9 1.370(5) .
N3 C17 1.471(5) .
N3 C13 1.472(5) .
N4 C32 1.323(5) .
N4 C24 1.357(5) .
N5 C35 1.144(5) .
N6 C32 1.365(5) .
N6 C40 1.464(5) .
N6 C36 1.466(5) .
C1 C2 1.375(5) .
C1 C10 1.507(6) .
C2 C3 1.428(5) .
C3 C4 1.415(5) .
C3 C8 1.420(5) .
C4 C5 1.361(5) .
C4 H4 0.9300 .
C5 C6 1.410(6) .
C5 C11 1.512(6) .
C6 C7 1.378(5) .
C6 C12 1.437(6) .
C7 C8 1.418(5) .
C8 C9 1.455(5) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C13 C14 1.495(6) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.520(6) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.517(6) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.511(6) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C19 1.481(7) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 C20 1.422(8) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 C21 1.565(8) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 C22 1.409(8) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 C23 1.511(8) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C24 C25 1.379(5) .
C24 C33 1.506(5) .
C25 C26 1.434(5) .
C26 C27 1.407(5) .
C26 C31 1.425(5) .
C27 C28 1.363(5) .
C27 H27 0.9300 .
C28 C29 1.413(5) .
C28 C34 1.503(5) .
C29 C30 1.387(5) .
C29 C35 1.429(6) .
C30 C31 1.409(5) .
C31 C32 1.450(5) .
C33 H33A 0.9600 .
C33 H33B 0.9600 .
C33 H33C 0.9600 .
C34 H34A 0.9600 .
C34 H34B 0.9600 .
C34 H34C 0.9600 .
C36 C37 1.511(6) .
C36 H36A 0.9700 .
C36 H36B 0.9700 .
C37 C38 1.519(6) .
C37 H37A 0.9700 .
C37 H37B 0.9700 .
C38 C39 1.518(6) .
C38 H38A 0.9700 .
C38 H38B 0.9700 .
C39 C40 1.511(6) .
C39 H39A 0.9700 .
C39 H39B 0.9700 .
C40 H40A 0.9700 .
C40 H40B 0.9700 .
C41 C42 1.441(9) .
C41 H41A 0.9700 .
C41 H41B 0.9700 .
C42 C43 1.558(11) .
C42 H42A 0.9700 .
C42 H42B 0.9700 .
C43 C44 1.522(12) .
C43 H43A 0.9700 .
C43 H43B 0.9700 .
C44 C45 1.406(12) .
C44 H44A 0.9700 .
C44 H44B 0.9700 .
C45 C46 1.545(13) .
C45 H45A 0.9700 .
C45 H45B 0.9700 .
C46 H46A 0.9600 .
C46 H46B 0.9600 .
C46 H46C 0.9600 .
C41' C42' 1.528(15) .
C41' H41C 0.9700 .
C41' H41D 0.9700 .
C42' C43' 1.551(18) .
C42' H42C 0.9700 .
C42' H42D 0.9700 .
C43' C44' 1.494(18) .
C43' H43C 0.9700 .
C43' H43D 0.9700 .
C44' C45' 1.553(16) .
C44' H44C 0.9700 .
C44' H44D 0.9700 .
C45' C46' 1.551(17) .
C45' H45C 0.9700 .
C45' H45D 0.9700 .
C46' H46D 0.9600 .
C46' H46E 0.9600 .
C46' H46F 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C42 H42B Se2 0.97 3.16 4.118(9) 170.8 2_566
C41 H41B N6 0.97 2.50 3.030(9) 113.9 .
C37 H37B Se2 0.97 3.08 3.845(5) 137.1 1_545
C36 H36B N5 0.97 2.56 3.531(6) 175.0 2_556
C14 H14B Se1 0.97 3.09 3.784(5) 130.1 1_655
C14 H14B Se1 0.97 3.09 3.784(5) 130.1 1_655
C36 H36B N5 0.97 2.56 3.531(6) 175.0 2_556
C37 H37B Se2 0.97 3.08 3.845(5) 137.1 1_545
C41 H41B N6 0.97 2.50 3.030(9) 113.9 .
C42 H42B Se2 0.97 3.16 4.118(9) 170.8 2_566
C14 H14B Se1 0.97 3.09 3.784(5) 130.1 1_655
C36 H36B N5 0.97 2.56 3.531(6) 175.0 2_556
C37 H37B Se2 0.97 3.08 3.845(5) 137.1 1_545
C41 H41B N6 0.97 2.50 3.030(9) 113.9 .
C42 H42B Se2 0.97 3.16 4.118(9) 170.8 2_566
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
C9 N1 C1 C2 -0.9(6) . . . .
C9 N1 C1 C10 -177.7(4) . . . .
N1 C1 C2 C3 9.2(6) . . . .
C10 C1 C2 C3 -174.4(4) . . . .
N1 C1 C2 Se1 -172.3(3) . . . .
C10 C1 C2 Se1 4.1(6) . . . .
C1 C2 C3 C4 170.3(4) . . . .
Se1 C2 C3 C4 -8.2(5) . . . .
C1 C2 C3 C8 -5.5(6) . . . .
Se1 C2 C3 C8 176.0(3) . . . .
C8 C3 C4 C5 2.7(6) . . . .
C2 C3 C4 C5 -173.1(4) . . . .
C3 C4 C5 C6 0.4(6) . . . .
C3 C4 C5 C11 178.0(4) . . . .
C4 C5 C6 C7 -0.3(6) . . . .
C11 C5 C6 C7 -178.0(4) . . . .
C4 C5 C6 C12 179.0(4) . . . .
C11 C5 C6 C12 1.3(7) . . . .
C18 O1 C7 C6 -90.2(5) . . . .
C18 O1 C7 C8 89.9(5) . . . .
C5 C6 C7 O1 177.0(4) . . . .
C12 C6 C7 O1 -2.2(6) . . . .
C5 C6 C7 C8 -3.0(6) . . . .
C12 C6 C7 C8 177.7(4) . . . .
O1 C7 C8 C3 -174.1(3) . . . .
C6 C7 C8 C3 6.0(6) . . . .
O1 C7 C8 C9 0.9(6) . . . .
C6 C7 C8 C9 -179.1(4) . . . .
C4 C3 C8 C7 -5.8(5) . . . .
C2 C3 C8 C7 170.2(3) . . . .
C4 C3 C8 C9 178.8(3) . . . .
C2 C3 C8 C9 -5.2(5) . . . .
C1 N1 C9 N3 171.7(4) . . . .
C1 N1 C9 C8 -10.8(6) . . . .
C17 N3 C9 N1 14.5(5) . . . .
C13 N3 C9 N1 -129.6(4) . . . .
C17 N3 C9 C8 -163.0(3) . . . .
C13 N3 C9 C8 52.9(5) . . . .
C7 C8 C9 N1 -161.3(4) . . . .
C3 C8 C9 N1 13.7(5) . . . .
C7 C8 C9 N3 16.1(6) . . . .
C3 C8 C9 N3 -168.9(3) . . . .
C9 N3 C13 C14 91.4(5) . . . .
C17 N3 C13 C14 -54.8(5) . . . .
N3 C13 C14 C15 56.5(5) . . . .
C13 C14 C15 C16 -56.2(5) . . . .
C14 C15 C16 C17 54.0(5) . . . .
C9 N3 C17 C16 -92.1(5) . . . .
C13 N3 C17 C16 54.5(5) . . . .
C15 C16 C17 N3 -54.2(5) . . . .
C7 O1 C18 C19 -170.9(4) . . . .
O1 C18 C19 C20 -57.7(8) . . . .
C18 C19 C20 C21 179.8(6) . . . .
C19 C20 C21 C22 172.8(7) . . . .
C20 C21 C22 C23 -178.8(7) . . . .
C32 N4 C24 C25 -1.8(6) . . . .
C32 N4 C24 C33 179.8(4) . . . .
N4 C24 C25 C26 13.0(6) . . . .
C33 C24 C25 C26 -168.8(4) . . . .
N4 C24 C25 Se2 -169.9(3) . . . .
C33 C24 C25 Se2 8.3(6) . . . .
C24 C25 C26 C27 168.6(4) . . . .
Se2 C25 C26 C27 -8.5(5) . . . .
C24 C25 C26 C31 -7.5(5) . . . .
Se2 C25 C26 C31 175.3(3) . . . .
C31 C26 C27 C28 4.2(5) . . . .
C25 C26 C27 C28 -172.0(3) . . . .
C26 C27 C28 C29 0.9(5) . . . .
C26 C27 C28 C34 178.7(4) . . . .
C27 C28 C29 C30 -1.5(5) . . . .
C34 C28 C29 C30 -179.3(4) . . . .
C27 C28 C29 C35 176.9(3) . . . .
C34 C28 C29 C35 -0.9(5) . . . .
C41' O2 C30 C29 -67.6(11) . . . .
C41 O2 C30 C29 -113.5(6) . . . .
C41' O2 C30 C31 112.9(11) . . . .
C41 O2 C30 C31 67.0(6) . . . .
C28 C29 C30 O2 177.4(3) . . . .
C35 C29 C30 O2 -1.0(5) . . . .
C28 C29 C30 C31 -3.1(6) . . . .
C35 C29 C30 C31 178.5(4) . . . .
O2 C30 C31 C26 -172.5(3) . . . .
C29 C30 C31 C26 8.0(5) . . . .
O2 C30 C31 C32 2.2(6) . . . .
C29 C30 C31 C32 -177.3(4) . . . .
C27 C26 C31 C30 -8.4(5) . . . .
C25 C26 C31 C30 167.9(3) . . . .
C27 C26 C31 C32 176.4(3) . . . .
C25 C26 C31 C32 -7.3(5) . . . .
C24 N4 C32 N6 167.3(4) . . . .
C24 N4 C32 C31 -14.6(6) . . . .
C40 N6 C32 N4 17.1(6) . . . .
C36 N6 C32 N4 -136.1(4) . . . .
C40 N6 C32 C31 -161.1(4) . . . .
C36 N6 C32 C31 45.8(6) . . . .
C30 C31 C32 N4 -155.9(4) . . . .
C26 C31 C32 N4 18.9(6) . . . .
C30 C31 C32 N6 22.2(6) . . . .
C26 C31 C32 N6 -163.0(4) . . . .
C32 N6 C36 C37 100.0(4) . . . .
C40 N6 C36 C37 -54.8(5) . . . .
N6 C36 C37 C38 55.1(5) . . . .
C36 C37 C38 C39 -55.6(6) . . . .
C37 C38 C39 C40 54.6(6) . . . .
C32 N6 C40 C39 -99.9(4) . . . .
C36 N6 C40 C39 55.2(5) . . . .
C38 C39 C40 N6 -54.7(5) . . . .
C30 O2 C41 C42 130.8(7) . . . .
C41' O2 C41 C42 25.4(16) . . . .
O2 C41 C42 C43 175.6(7) . . . .
C41 C42 C43 C44 -168.7(9) . . . .
C42 C43 C44 C45 -78.0(17) . . . .
C43 C44 C45 C46 -172.6(12) . . . .
C30 O2 C41' C42' -120.5(18) . . . .
C41 O2 C41' C42' -22.3(13) . . . .
O2 C41' C42' C43' 180(2) . . . .
C41' C42' C43' C44' 66(3) . . . .
C42' C43' C44' C45' 151(2) . . . .
C43' C44' C45' C46' -176.9(18) . . . .
