#------------------------------------------------------------------------------
#$Date: 2019-11-23 00:10:27 +0200 (Sat, 23 Nov 2019) $
#$Revision: 231627 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/61/4346135.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_4346135
loop_
_publ_author_name
'Maligaspe, Eranda'
'Pundsack, Tom J.'
'Albert, Lauren M.'
'Zatsikha, Yuriy V.'
'Solntsev, Pavlo V.'
'Blank, David A.'
'Nemykin, Victor N.'
_publ_section_title
;
 Synthesis and charge-transfer dynamics in a ferrocene-containing
 organoboryl aza-BODIPY donor-acceptor triad with boron as the hub.
;
_journal_issue                   8
_journal_name_full               'Inorganic chemistry'
_journal_page_first              4167
_journal_page_last               4174
_journal_paper_doi               10.1021/acs.inorgchem.5b00494
_journal_volume                  54
_journal_year                    2015
_chemical_formula_moiety         'C28 H19 N3'
_chemical_formula_sum            'C28 H19 N3'
_chemical_formula_weight         397.46
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   33.0628(7)
_cell_length_b                   33.0628(7)
_cell_length_c                   4.8770(3)
_cell_measurement_reflns_used    17013
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      72.4
_cell_measurement_theta_min      2.7
_cell_volume                     4617.0(3)
_computing_cell_refinement
;
CrystalClear 2.0 r12 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear 2.0 r12 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear 2.0 r12 (Rigaku, 2011)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2008 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 RX
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
scan:
	Number of images: 175
	           Slice: -85.0000 - 265.0000
	     Image width: 2.0000
	        Exp time: 540.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 151
	           Slice: -85.0000 - 217.0000
	     Image width: 2.0000
	        Exp time: 540.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 45.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 152
	           Slice: -85.0000 - 220.0000
	     Image width: 2.0000
	        Exp time: 540.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 45.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: 0.0000

;
_diffrn_measurement_device
;
Crystal Goniometer
;
_diffrn_measurement_device_type
;
Rigaku RAXIS conversion
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      0.000000
_diffrn_orient_matrix_UB_12      0.000000
_diffrn_orient_matrix_UB_13      0.000000
_diffrn_orient_matrix_UB_21      0.000000
_diffrn_orient_matrix_UB_22      0.000000
_diffrn_orient_matrix_UB_23      0.000000
_diffrn_orient_matrix_UB_31      0.000000
_diffrn_orient_matrix_UB_32      0.000000
_diffrn_orient_matrix_UB_33      0.000000
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            19130
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         72.486
_diffrn_reflns_theta_min         2.673
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.594
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.733
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       needle
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.053
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0396P)²+3.8171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1793
_reflns_number_total             1998
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic5b00494_si_002.cif
_cod_data_source_block           a0063_sq
_cod_database_code               4346135
_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   0.784
_shelx_estimated_absorpt_t_max   0.943
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
N1 N 0.53510(10) 0.48696(11) 0.5873(6) 0.0434(7) Uani 0.5 1 d . . P
N2 N 0.48686(9) 0.43487(8) 0.2232(5) 0.0417(6) Uani 0.5 1 d . . P
N3 N 0.46671(10) 0.49402(10) 0.3265(6) 0.0437(7) Uani 0.5 1 d . . P
H3 H 0.4876 0.5096 0.4544 0.052 Uiso 0.5 1 calc R U P
C1 C 0.5680(7) 0.4911(5) 0.748(4) 0.056(5) Uani 0.5 1 d D . P
C2 C 0.5759(3) 0.4550(4) 0.678(3) 0.068(5) Uani 0.5 1 d D . P
C3 C 0.5469(4) 0.4334(4) 0.457(2) 0.070(3) Uani 0.5 1 d D . P
C4 C 0.52038(10) 0.44914(10) 0.4108(6) 0.0399(7) Uani 0.5 1 d D . P
C5 C 0.6007(4) 0.4389(3) 0.797(3) 0.096(4) Uani 0.5 1 d D . P
H5 H 0.6187 0.4534 0.9562 0.116 Uiso 0.5 1 calc R U P
C6 C 0.5997(5) 0.4004(4) 0.682(3) 0.102(4) Uani 0.5 1 d D . P
H6 H 0.6182 0.3886 0.7567 0.122 Uiso 0.5 1 calc R U P
C7 C 0.5718(7) 0.3791(6) 0.459(4) 0.086(5) Uani 0.5 1 d D . P
H7 H 0.5742 0.3546 0.3722 0.104 Uiso 0.5 1 calc R U P
C8 C 0.5410(7) 0.3909(5) 0.354(3) 0.086(5) Uani 0.5 1 d D . P
H8 H 0.5177 0.3723 0.2234 0.103 Uiso 0.5 1 calc R U P
C9 C 0.5908(5) 0.5278(4) 0.960(3) 0.043(4) Uani 0.5 1 d D . P
C10 C 0.6297(4) 0.5393(5) 1.112(3) 0.072(4) Uani 0.5 1 d D . P
H10 H 0.6452 0.5223 1.0720 0.087 Uiso 0.5 1 calc R U P
C11 C 0.6502(3) 0.5736(2) 1.3222(17) 0.0361(15) Uani 0.5 1 d D . P
H11 H 0.6763 0.5778 1.4268 0.043 Uiso 0.5 1 calc R U P
C12 C 0.6292(2) 0.6005(3) 1.3625(15) 0.036(3) Uani 0.5 1 d D . P
H12 H 0.6416 0.6244 1.4976 0.043 Uiso 0.5 1 calc R U P
C13 C 0.5910(4) 0.5934(4) 1.212(2) 0.068(4) Uani 0.5 1 d D . P
H13 H 0.5769 0.6121 1.2403 0.081 Uiso 0.5 1 calc R U P
C14 C 0.5740(4) 0.5584(3) 1.020(3) 0.060(4) Uani 0.5 1 d D . P
H14 H 0.5480 0.5544 0.9162 0.072 Uiso 0.5 1 calc R U P
C15 C 0.46215(10) 0.45562(10) 0.1834(6) 0.0402(7) Uani 0.5 1 d . . P
C16 C 0.4291(4) 0.4422(2) -0.005(2) 0.040(3) Uani 0.5 1 d D . P
C17 C 0.4072(5) 0.4690(4) 0.028(3) 0.050(4) Uani 0.5 1 d D . P
C18 C 0.4322(6) 0.5038(5) 0.232(4) 0.036(3) Uani 0.5 1 d D . P
C19 C 0.4097(3) 0.4061(3) -0.1997(17) 0.041(3) Uani 0.5 1 d D . P
H19 H 0.4233 0.3870 -0.2264 0.049 Uiso 0.5 1 calc R U P
C20 C 0.3721(4) 0.3980(4) -0.349(2) 0.076(5) Uani 0.5 1 d D . P
H20 H 0.3595 0.3742 -0.4850 0.091 Uiso 0.5 1 calc R U P
C21 C 0.3527(5) 0.4257(4) -0.298(3) 0.090(4) Uani 0.5 1 d D . P
H21 H 0.3250 0.4180 -0.3971 0.108 Uiso 0.5 1 calc R U P
C22 C 0.3680(3) 0.4625(3) -0.125(2) 0.042(3) Uani 0.5 1 d D . P
H22 H 0.3541 0.4816 -0.1081 0.050 Uiso 0.5 1 calc R U P
C23 C 0.4274(4) 0.5442(3) 0.330(2) 0.056(4) Uani 0.5 1 d D . P
C24 C 0.3910(3) 0.5545(3) 0.246(2) 0.071(3) Uani 0.5 1 d D . P
H24 H 0.3675 0.5341 0.1213 0.085 Uiso 0.5 1 calc R U P
C25 C 0.3902(3) 0.5928(4) 0.343(3) 0.071(3) Uani 0.5 1 d D . P
H25 H 0.3670 0.5992 0.2747 0.085 Uiso 0.5 1 calc R U P
C26 C 0.4219(5) 0.6233(5) 0.539(3) 0.0521(19) Uani 0.5 1 d D . P
H26 H 0.4224 0.6510 0.5963 0.063 Uiso 0.5 1 calc R U P
C27 C 0.4522(5) 0.6103(4) 0.6431(18) 0.050(2) Uani 0.5 1 d D . P
H27 H 0.4701 0.6263 0.7999 0.060 Uiso 0.5 1 calc R U P
C28 C 0.4580(3) 0.5751(4) 0.5311(19) 0.057(3) Uani 0.5 1 d D . P
H28 H 0.4833 0.5715 0.5918 0.068 Uiso 0.5 1 calc R U P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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_
_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
N3 N1 C1 89.3(7) 10_666 .
N3 N1 C18 80.6(7) 10_666 10_666
C1 N1 C18 8.7(10) . 10_666
N3 N1 C4 157.2(5) 10_666 .
C1 N1 C4 111.6(6) . .
C18 N1 C4 120.3(6) 10_666 .
C15 N2 C4 122.7(3) . .
C15 N3 C18 108.3(6) . .
C15 N3 H3 125.8 . .
C18 N3 H3 125.8 . .
C18 C1 N1 90(10) 10_666 .
C18 C1 C23 167(10) 10_666 10_666
N1 C1 C23 101.3(11) . 10_666
C18 C1 C2 163(10) 10_666 .
N1 C1 C2 105.6(8) . .
C23 C1 C2 4.4(7) 10_666 .
C18 C1 C9 35(10) 10_666 .
N1 C1 C9 124.4(11) . .
C23 C1 C9 134.3(16) 10_666 .
C2 C1 C9 130.0(14) . .
C18 C1 N3 59(10) 10_666 10_666
N1 C1 N3 31.4(5) . 10_666
C23 C1 N3 132.1(14) 10_666 10_666
C2 C1 N3 136.5(11) . 10_666
C9 C1 N3 93.3(8) . 10_666
C18 C1 C17 35(10) 10_666 10_666
N1 C1 C17 124.2(12) . 10_666
C23 C1 C17 134.5(16) 10_666 10_666
C2 C1 C17 130.2(14) . 10_666
C9 C1 C17 0.8(12) . 10_666
N3 C1 C17 93.2(9) 10_666 10_666
C23 C2 C5 165(10) 10_666 .
C23 C2 C24 178(10) 10_666 10_666
C5 C2 C24 14.1(8) . 10_666
C23 C2 C3 56(9) 10_666 .
C5 C2 C3 123.2(12) . .
C24 C2 C3 122.4(12) 10_666 .
C23 C2 C1 50(9) 10_666 .
C5 C2 C1 131.4(12) . .
C24 C2 C1 131.4(11) 10_666 .
C3 C2 C1 105.0(9) . .
C23 C2 C28 60(9) 10_666 10_666
C5 C2 C28 116.8(11) . 10_666
C24 C2 C28 118.1(11) 10_666 10_666
C3 C2 C28 9.4(10) . 10_666
C1 C2 C28 110.3(10) . 10_666
C23 C2 C18 52(10) 10_666 10_666
C5 C2 C18 129.4(11) . 10_666
C24 C2 C18 129.6(10) 10_666 10_666
C3 C2 C18 107.0(12) . 10_666
C1 C2 C18 2.1(14) . 10_666
C28 C2 C18 112.2(13) 10_666 10_666
C28 C3 C4 109(5) 10_666 .
C28 C3 C23 109(4) 10_666 10_666
C4 C3 C23 107.5(9) . 10_666
C28 C3 C2 107(4) 10_666 .
C4 C3 C2 112.2(8) . .
C23 C3 C2 4.7(9) 10_666 .
C28 C3 C8 44(4) 10_666 .
C4 C3 C8 125.2(11) . .
C23 C3 C8 124.9(13) 10_666 .
C2 C3 C8 120.6(13) . .
C28 C3 C27 48(4) 10_666 10_666
C4 C3 C27 133.2(9) . 10_666
C23 C3 C27 117.9(11) 10_666 10_666
C2 C3 C27 113.5(11) . 10_666
C8 C3 C27 8.3(13) . 10_666
C3 C4 N2 127.8(5) . .
C3 C4 C28 10.2(10) . 10_666
N2 C4 C28 122.1(4) . 10_666
C3 C4 N1 105.2(5) . .
N2 C4 N1 126.9(3) . .
C28 C4 N1 110.8(4) 10_666 .
C2 C5 C6 117.5(12) . .
C2 C5 H5 121.3 . .
C6 C5 H5 121.3 . .
C7 C6 C5 119.9(14) . .
C7 C6 H6 120.0 . .
C5 C6 H6 120.0 . .
C8 C7 C6 123.9(16) . .
C8 C7 H7 118.0 . .
C6 C7 H7 118.0 . .
C7 C8 C3 113.6(15) . .
C7 C8 H8 123.2 . .
C3 C8 H8 123.2 . .
C17 C9 C18 168(10) 10_666 10_666
C17 C9 C10 52(10) 10_666 .
C18 C9 C10 133.8(12) 10_666 .
C17 C9 C14 59(10) 10_666 .
C18 C9 C14 116.1(13) 10_666 .
C10 C9 C14 110.0(11) . .
C17 C9 C16 63(10) 10_666 10_666
C18 C9 C16 111.6(12) 10_666 10_666
C10 C9 C16 114.4(11) . 10_666
C14 C9 C16 4.5(9) . 10_666
C17 C9 C22 55(10) 10_666 10_666
C18 C9 C22 131.3(11) 10_666 10_666
C10 C9 C22 3.1(10) . 10_666
C14 C9 C22 112.6(10) . 10_666
C16 C9 C22 117.0(10) 10_666 10_666
C17 C9 C1 169(10) 10_666 .
C18 C9 C1 4.9(14) 10_666 .
C10 C9 C1 128.9(11) . .
C14 C9 C1 121.0(10) . .
C16 C9 C1 116.6(11) 10_666 .
C22 C9 C1 126.4(11) 10_666 .
C9 C10 C11 128.3(12) . .
C9 C10 H10 115.8 . .
C11 C10 H10 115.8 . .
C12 C11 C10 114.8(9) . .
C12 C11 H11 122.6 . .
C10 C11 H11 122.6 . .
C13 C12 C11 121.9(7) . .
C13 C12 H12 119.1 . .
C11 C12 H12 119.1 . .
C14 C13 C12 117.3(9) . .
C14 C13 H13 121.3 . .
C12 C13 H13 121.3 . .
C13 C14 C9 127.5(11) . .
C13 C14 H14 116.3 . .
C9 C14 H14 116.3 . .
N2 C15 C16 123.4(4) . .
N2 C15 N3 126.1(3) . .
C16 C15 N3 110.4(3) . .
N2 C15 C14 124.4(5) . 10_666
C16 C15 C14 0.9(6) . 10_666
N3 C15 C14 109.5(5) . 10_666
C14 C16 C15 169(8) 10_666 .
C14 C16 C17 61(8) 10_666 .
C15 C16 C17 108.1(7) . .
C14 C16 C19 57(7) 10_666 .
C15 C16 C19 134.8(7) . .
C17 C16 C19 116.8(10) . .
C14 C16 C13 55(7) 10_666 10_666
C15 C16 C13 136.8(7) . 10_666
C17 C16 C13 115.0(9) . 10_666
C19 C16 C13 2.4(8) . 10_666
C14 C16 C9 65(8) 10_666 10_666
C15 C16 C9 104.2(7) . 10_666
C17 C16 C9 4.0(10) . 10_666
C19 C16 C9 120.7(10) . 10_666
C13 C16 C9 118.9(10) 10_666 10_666
C9 C17 C10 124(10) 10_666 10_666
C9 C17 C14 117(10) 10_666 10_666
C10 C17 C14 117.8(12) 10_666 10_666
C9 C17 C16 113(10) 10_666 .
C10 C17 C16 122.2(11) 10_666 .
C14 C17 C16 4.5(9) 10_666 .
C9 C17 C22 121(10) 10_666 .
C10 C17 C22 3.0(10) 10_666 .
C14 C17 C22 120.1(12) 10_666 .
C16 C17 C22 124.6(11) . .
C9 C17 C18 11(10) 10_666 .
C10 C17 C18 129.6(13) 10_666 .
C14 C17 C18 112.6(12) 10_666 .
C16 C17 C18 108.1(11) . .
C22 C17 C18 127.3(11) . .
C9 C17 C1 10(10) 10_666 10_666
C10 C17 C1 125.1(12) 10_666 10_666
C14 C17 C1 117.1(12) 10_666 10_666
C16 C17 C1 112.7(12) . 10_666
C22 C17 C1 122.7(11) . 10_666
C18 C17 C1 4.6(13) . 10_666
C1 C18 N1 81(10) 10_666 10_666
C1 C18 C9 140(10) 10_666 10_666
N1 C18 C9 137.9(12) 10_666 10_666
C1 C18 N3 114(10) 10_666 .
N1 C18 N3 33.2(5) 10_666 .
C9 C18 N3 105.1(10) 10_666 .
C1 C18 C17 141(10) 10_666 .
N1 C18 C17 137.3(12) 10_666 .
C9 C18 C17 0.9(9) 10_666 .
N3 C18 C17 104.6(9) . .
C1 C18 C23 11(10) 10_666 .
N1 C18 C23 91.2(9) 10_666 .
C9 C18 C23 130.9(15) 10_666 .
N3 C18 C23 123.9(12) . .
C17 C18 C23 131.4(14) . .
C1 C18 C2 14(10) 10_666 10_666
N1 C18 C2 95.0(10) 10_666 10_666
C9 C18 C2 127.1(15) 10_666 10_666
N3 C18 C2 127.8(13) . 10_666
C17 C18 C2 127.6(14) . 10_666
C23 C18 C2 3.9(7) . 10_666
C20 C19 C16 121.3(9) . .
C20 C19 H19 119.3 . .
C16 C19 H19 119.3 . .
C19 C20 C21 117.3(11) . .
C19 C20 H20 121.4 . .
C21 C20 H20 121.3 . .
C22 C21 C20 128.4(13) . .
C22 C21 H21 115.8 . .
C20 C21 H21 115.8 . .
C21 C22 C17 111.5(11) . .
C21 C22 H22 124.3 . .
C17 C22 H22 124.3 . .
C2 C23 C1 125(10) 10_666 10_666
C2 C23 C3 119(10) 10_666 10_666
C1 C23 C3 113.8(13) 10_666 10_666
C2 C23 C28 115(10) 10_666 .
C1 C23 C28 119.2(12) 10_666 .
C3 C23 C28 9.7(11) 10_666 .
C2 C23 C5 14(10) 10_666 10_666
C1 C23 C5 127.3(12) 10_666 10_666
C3 C23 C5 118.9(10) 10_666 10_666
C28 C23 C5 112.7(9) . 10_666
C2 C23 C24 2(9) 10_666 .
C1 C23 C24 126.9(12) 10_666 .
C3 C23 C24 117.9(9) 10_666 .
C28 C23 C24 113.7(8) . .
C5 C23 C24 12.8(7) 10_666 .
C2 C23 C18 124(10) 10_666 .
C1 C23 C18 1.7(16) 10_666 .
C3 C23 C18 115.3(10) 10_666 .
C28 C23 C18 120.6(9) . .
C5 C23 C18 125.7(11) 10_666 .
C24 C23 C18 125.6(11) . .
C25 C24 C23 121.1(8) . .
C25 C24 H24 119.4 . .
C23 C24 H24 119.4 . .
C24 C25 C26 123.1(11) . .
C24 C25 H25 118.4 . .
C26 C25 H25 118.4 . .
C27 C26 C25 115.4(13) . .
C27 C26 H26 122.3 . .
C25 C26 H26 122.3 . .
C26 C27 C28 123.3(10) . .
C26 C27 H27 118.3 . .
C28 C27 H27 118.3 . .
C27 C28 C23 122.2(9) . .
C27 C28 H28 118.9 . .
C23 C28 H28 118.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 N3 0.783(3) 10_666
N1 C1 1.29(2) .
N1 C18 1.308(18) 10_666
N1 C4 1.390(4) .
N2 C15 1.318(4) .
N2 C4 1.329(4) .
N3 C15 1.389(4) .
N3 C18 1.410(19) .
N3 H3 0.8800 .
C1 C18 0.20(2) 10_666
C1 C23 1.306(19) 10_666
C1 C2 1.384(16) .
C1 C9 1.481(15) .
C1 N3 1.504(18) 10_666
C1 C17 1.59(2) 10_666
C2 C23 0.129(19) 10_666
C2 C5 1.316(12) .
C2 C24 1.334(16) 10_666
C2 C3 1.379(13) .
C2 C28 1.471(12) 10_666
C2 C18 1.576(19) 10_666
C3 C28 0.25(2) 10_666
C3 C4 1.243(12) .
C3 C23 1.312(15) 10_666
C3 C8 1.411(14) .
C3 C27 1.541(17) 10_666
C4 C28 1.344(11) 10_666
C5 C6 1.377(13) .
C5 H5 0.9500 .
C6 C7 1.370(14) .
C6 H6 0.9500 .
C7 C8 1.362(15) .
C7 H7 0.9500 .
C8 H8 0.9500 .
C9 C17 0.11(2) 10_666
C9 C18 1.32(2) 10_666
C9 C10 1.365(13) .
C9 C14 1.406(13) .
C9 C16 1.454(12) 10_666
C9 C22 1.475(16) 10_666
C10 C11 1.425(12) .
C10 H10 0.9500 .
C11 C12 1.388(10) .
C11 H11 0.9500 .
C12 C13 1.377(12) .
C12 H12 0.9500 .
C13 C14 1.372(11) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 C16 1.322(11) .
C15 C14 1.441(13) 10_666
C16 C14 0.12(2) 10_666
C16 C17 1.407(13) .
C16 C19 1.405(9) .
C16 C13 1.439(16) 10_666
C16 C9 1.454(12) 10_666
C17 C9 0.11(2) 10_666
C17 C10 1.30(2) 10_666
C17 C14 1.351(16) 10_666
C17 C22 1.415(13) .
C17 C18 1.432(17) .
C17 C1 1.59(2) 10_666
C18 C1 0.20(2) 10_666
C18 N1 1.308(18) 10_666
C18 C9 1.32(2) 10_666
C18 C23 1.500(14) .
C18 C2 1.576(19) 10_666
C19 C20 1.348(13) .
C19 H19 0.9500 .
C20 C21 1.380(13) .
C20 H20 0.9500 .
C21 C22 1.354(13) .
C21 H21 0.9500 .
C22 H22 0.9500 .
C23 C2 0.129(19) 10_666
C23 C1 1.306(19) 10_666
C23 C3 1.312(15) 10_666
C23 C28 1.412(12) .
C23 C5 1.441(16) 10_666
C23 C24 1.463(11) .
C24 C25 1.368(11) .
C24 H24 0.9500 .
C25 C26 1.406(11) .
C25 H25 0.9500 .
C26 C27 1.366(14) .
C26 H26 0.9500 .
C27 C28 1.384(12) .
C27 H27 0.9500 .
C28 H28 0.9500 .
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_4
N3 N1 C1 C18 -3(11) 10_666 10_666
C4 N1 C1 C18 -174(11) . 10_666
N3 N1 C1 C23 170.0(13) 10_666 10_666
C18 N1 C1 C23 173(12) 10_666 10_666
C4 N1 C1 C23 -0.6(16) . 10_666
N3 N1 C1 C2 170.8(13) 10_666 .
C18 N1 C1 C2 174(12) 10_666 .
C4 N1 C1 C2 0.2(16) . .
N3 N1 C1 C9 -9.1(18) 10_666 .
C18 N1 C1 C9 -6(10) 10_666 .
C4 N1 C1 C9 -179.7(14) . .
C18 N1 C1 N3 3(11) 10_666 10_666
C4 N1 C1 N3 -170.6(6) . 10_666
N3 N1 C1 C17 -10.0(17) 10_666 10_666
C18 N1 C1 C17 -7(10) 10_666 10_666
C4 N1 C1 C17 179.4(14) . 10_666
C18 C1 C2 C23 149(47) 10_666 10_666
N1 C1 C2 C23 -10(13) . 10_666
C9 C1 C2 C23 170(13) . 10_666
N3 C1 C2 C23 -3(13) 10_666 10_666
C17 C1 C2 C23 171(13) 10_666 10_666
C18 C1 C2 C5 -10(45) 10_666 .
N1 C1 C2 C5 -169.8(13) . .
C23 C1 C2 C5 -160(14) 10_666 .
C9 C1 C2 C5 10(3) . .
N3 C1 C2 C5 -162.8(16) 10_666 .
C17 C1 C2 C5 11(3) 10_666 .
C18 C1 C2 C24 -29(45) 10_666 10_666
N1 C1 C2 C24 171.4(13) . 10_666
C23 C1 C2 C24 -179(100) 10_666 10_666
C9 C1 C2 C24 -9(3) . 10_666
N3 C1 C2 C24 178.4(16) 10_666 10_666
C17 C1 C2 C24 -8(3) 10_666 10_666
C18 C1 C2 C3 163(44) 10_666 .
N1 C1 C2 C3 3.7(17) . .
C23 C1 C2 C3 14(13) 10_666 .
C9 C1 C2 C3 -176.4(18) . .
N3 C1 C2 C3 11(3) 10_666 .
C17 C1 C2 C3 -175.4(18) 10_666 .
C18 C1 C2 C28 155(44) 10_666 10_666
N1 C1 C2 C28 -4.4(18) . 10_666
C23 C1 C2 C28 5(12) 10_666 10_666
C9 C1 C2 C28 175.5(18) . 10_666
N3 C1 C2 C28 3(3) 10_666 10_666
C17 C1 C2 C28 176.4(17) 10_666 10_666
N1 C1 C2 C18 -159(45) . 10_666
C23 C1 C2 C18 -149(47) 10_666 10_666
C9 C1 C2 C18 21(42) . 10_666
N3 C1 C2 C18 -152(46) 10_666 10_666
C17 C1 C2 C18 22(42) 10_666 10_666
C23 C2 C3 C28 -113(13) 10_666 10_666
C5 C2 C3 C28 48(5) . 10_666
C24 C2 C3 C28 65(5) 10_666 10_666
C1 C2 C3 C28 -126(5) . 10_666
C18 C2 C3 C28 -125(5) 10_666 10_666
C23 C2 C3 C4 6(12) 10_666 .
C5 C2 C3 C4 167.2(11) . .
C24 C2 C3 C4 -176.0(10) 10_666 .
C1 C2 C3 C4 -6.9(15) . .
C28 C2 C3 C4 119(5) 10_666 .
C18 C2 C3 C4 -6.3(15) 10_666 .
C5 C2 C3 C23 162(13) . 10_666
C24 C2 C3 C23 178(100) 10_666 10_666
C1 C2 C3 C23 -13(11) . 10_666
C28 C2 C3 C23 113(13) 10_666 10_666
C18 C2 C3 C23 -12(11) 10_666 10_666
C23 C2 C3 C8 -159(12) 10_666 .
C5 C2 C3 C8 2.8(19) . .
C24 C2 C3 C8 19.6(19) 10_666 .
C1 C2 C3 C8 -171.3(14) . .
C28 C2 C3 C8 -46(4) 10_666 .
C18 C2 C3 C8 -170.7(13) 10_666 .
C23 C2 C3 C27 -164(12) 10_666 10_666
C5 C2 C3 C27 -2.1(17) . 10_666
C24 C2 C3 C27 14.7(16) 10_666 10_666
C1 C2 C3 C27 -176.2(12) . 10_666
C28 C2 C3 C27 -50(4) 10_666 10_666
C18 C2 C3 C27 -175.6(11) 10_666 10_666
C28 C3 C4 N2 -59(5) 10_666 .
C23 C3 C4 N2 -176.1(6) 10_666 .
C2 C3 C4 N2 -176.6(7) . .
C8 C3 C4 N2 -13.1(17) . .
C27 C3 C4 N2 -10.2(18) 10_666 .
C23 C3 C4 C28 -117(5) 10_666 10_666
C2 C3 C4 C28 -118(5) . 10_666
C8 C3 C4 C28 46(4) . 10_666
C27 C3 C4 C28 49(4) 10_666 10_666
C28 C3 C4 N1 125(4) 10_666 .
C23 C3 C4 N1 7.4(11) 10_666 .
C2 C3 C4 N1 6.9(11) . .
C8 C3 C4 N1 170.4(11) . .
C27 C3 C4 N1 173.3(12) 10_666 .
C15 N2 C4 C3 -176.7(8) . .
C15 N2 C4 C28 173.0(7) . 10_666
C15 N2 C4 N1 -0.9(5) . .
N3 N1 C4 C3 -159.4(13) 10_666 .
C1 N1 C4 C3 -4.4(12) . .
C18 N1 C4 C3 -5.5(12) 10_666 .
N3 N1 C4 N2 24.0(13) 10_666 .
C1 N1 C4 N2 179.0(10) . .
C18 N1 C4 N2 178.0(10) 10_666 .
N3 N1 C4 C28 -150.5(12) 10_666 10_666
C1 N1 C4 C28 4.5(12) . 10_666
C18 N1 C4 C28 3.5(11) 10_666 10_666
C23 C2 C5 C6 87(40) 10_666 .
C24 C2 C5 C6 -87(4) 10_666 .
C3 C2 C5 C6 4.3(18) . .
C1 C2 C5 C6 176.7(15) . .
C28 C2 C5 C6 12.2(17) 10_666 .
C18 C2 C5 C6 176.3(14) 10_666 .
C2 C5 C6 C7 -3(2) . .
C5 C6 C7 C8 -6(3) . .
C6 C7 C8 C3 13(3) . .
C28 C3 C8 C7 -93(6) 10_666 .
C4 C3 C8 C7 -173.1(14) . .
C23 C3 C8 C7 -13(2) 10_666 .
C2 C3 C8 C7 -11(2) . .
C27 C3 C8 C7 22(6) 10_666 .
C18 C1 C9 C17 -87(63) 10_666 10_666
N1 C1 C9 C17 -78(61) . 10_666
C23 C1 C9 C17 104(60) 10_666 10_666
C2 C1 C9 C17 103(60) . 10_666
N3 C1 C9 C17 -82(61) 10_666 10_666
N1 C1 C9 C18 10(17) . 10_666
C23 C1 C9 C18 -169(21) 10_666 10_666
C2 C1 C9 C18 -170(21) . 10_666
N3 C1 C9 C18 5(18) 10_666 10_666
C17 C1 C9 C18 87(64) 10_666 10_666
C18 C1 C9 C10 -180(100) 10_666 .
N1 C1 C9 C10 -169.7(15) . .
C23 C1 C9 C10 12(3) 10_666 .
C2 C1 C9 C10 10(3) . .
N3 C1 C9 C10 -174.4(13) 10_666 .
C17 C1 C9 C10 -92(61) 10_666 .
C18 C1 C9 C14 -3(19) 10_666 .
N1 C1 C9 C14 7(3) . .
C23 C1 C9 C14 -171.7(19) 10_666 .
C2 C1 C9 C14 -172.8(16) . .
N3 C1 C9 C14 2.3(17) 10_666 .
C17 C1 C9 C14 85(60) 10_666 .
C18 C1 C9 C16 -3(19) 10_666 10_666
N1 C1 C9 C16 7(2) . 10_666
C23 C1 C9 C16 -172.2(19) 10_666 10_666
C2 C1 C9 C16 -173.3(16) . 10_666
N3 C1 C9 C16 1.8(16) 10_666 10_666
C17 C1 C9 C16 84(60) 10_666 10_666
C18 C1 C9 C22 178(18) 10_666 10_666
N1 C1 C9 C22 -172.1(14) . 10_666
C23 C1 C9 C22 9(3) 10_666 10_666
C2 C1 C9 C22 8(3) . 10_666
N3 C1 C9 C22 -176.8(12) 10_666 10_666
C17 C1 C9 C22 -95(61) 10_666 10_666
C17 C9 C10 C11 16(19) 10_666 .
C18 C9 C10 C11 -177.4(16) 10_666 .
C14 C9 C10 C11 5.6(19) . .
C16 C9 C10 C11 6(2) 10_666 .
C22 C9 C10 C11 -139(19) 10_666 .
C1 C9 C10 C11 -177.4(15) . .
C9 C10 C11 C12 -4.6(18) . .
C10 C11 C12 C13 1.1(13) . .
C11 C12 C13 C14 0.4(14) . .
C12 C13 C14 C9 1.0(18) . .
C17 C9 C14 C13 -14(17) 10_666 .
C18 C9 C14 C13 178.7(14) 10_666 .
C10 C9 C14 C13 -3.7(18) . .
C16 C9 C14 C13 -175(12) 10_666 .
C22 C9 C14 C13 -1.7(18) 10_666 .
C1 C9 C14 C13 179.0(14) . .
C4 N2 C15 C16 179.2(5) . .
C4 N2 C15 N3 -0.4(4) . .
C4 N2 C15 C14 179.1(6) . 10_666
C18 N3 C15 N2 -176.9(8) . .
C18 N3 C15 C16 3.4(9) . .
C18 N3 C15 C14 3.5(10) . 10_666
N2 C15 C16 C14 -178(100) . 10_666
N3 C15 C16 C14 2(62) . 10_666
N2 C15 C16 C17 174.5(7) . .
N3 C15 C16 C17 -5.9(9) . .
C14 C15 C16 C17 -7(61) 10_666 .
N2 C15 C16 C19 1.4(13) . .
N3 C15 C16 C19 -178.9(10) . .
C14 C15 C16 C19 180(100) 10_666 .
N2 C15 C16 C13 -0.7(15) . 10_666
N3 C15 C16 C13 179.0(11) . 10_666
C14 C15 C16 C13 177(100) 10_666 10_666
N2 C15 C16 C9 175.7(6) . 10_666
N3 C15 C16 C9 -4.7(9) . 10_666
C14 C15 C16 C9 -6(61) 10_666 10_666
C14 C16 C17 C9 -162(20) 10_666 10_666
C15 C16 C17 C9 17(16) . 10_666
C19 C16 C17 C9 -169(15) . 10_666
C13 C16 C17 C9 -167(16) 10_666 10_666
C14 C16 C17 C10 8(11) 10_666 10_666
C15 C16 C17 C10 -173.4(13) . 10_666
C19 C16 C17 C10 1.1(19) . 10_666
C13 C16 C17 C10 3.0(18) 10_666 10_666
C9 C16 C17 C10 170(17) 10_666 10_666
C15 C16 C17 C14 178(100) . 10_666
C19 C16 C17 C14 -7(10) . 10_666
C13 C16 C17 C14 -5(10) 10_666 10_666
C9 C16 C17 C14 162(20) 10_666 10_666
C14 C16 C17 C22 6(11) 10_666 .
C15 C16 C17 C22 -175.6(11) . .
C19 C16 C17 C22 -1.1(17) . .
C13 C16 C17 C22 0.7(17) 10_666 .
C9 C16 C17 C22 168(17) 10_666 .
C14 C16 C17 C18 -172(11) 10_666 .
C15 C16 C17 C18 6.1(14) . .
C19 C16 C17 C18 -179.4(11) . .
C13 C16 C17 C18 -177.6(12) 10_666 .
C9 C16 C17 C18 -11(15) 10_666 .
C14 C16 C17 C1 -173(11) 10_666 10_666
C15 C16 C17 C1 5.8(15) . 10_666
C19 C16 C17 C1 -179.7(12) . 10_666
C13 C16 C17 C1 -177.9(12) 10_666 10_666
C9 C16 C17 C1 -11(15) 10_666 10_666
C15 N3 C18 C1 176(12) . 10_666
C15 N3 C18 N1 171.7(5) . 10_666
C15 N3 C18 C9 -0.4(14) . 10_666
C15 N3 C18 C17 0.4(13) . .
C15 N3 C18 C23 -177.3(12) . .
C15 N3 C18 C2 -177.6(13) . 10_666
C9 C17 C18 C1 65(63) 10_666 10_666
C10 C17 C18 C1 3(20) 10_666 10_666
C14 C17 C18 C1 -178(19) 10_666 10_666
C16 C17 C18 C1 -177(19) . 10_666
C22 C17 C18 C1 5(19) . 10_666
C9 C17 C18 N1 -129(60) 10_666 10_666
C10 C17 C18 N1 168.6(18) 10_666 10_666
C14 C17 C18 N1 -11(3) 10_666 10_666
C16 C17 C18 N1 -11(3) . 10_666
C22 C17 C18 N1 170.9(16) . 10_666
C1 C17 C18 N1 166(21) 10_666 10_666
C10 C17 C18 C9 -62(60) 10_666 10_666
C14 C17 C18 C9 118(61) 10_666 10_666
C16 C17 C18 C9 118(61) . 10_666
C22 C17 C18 C9 -60(60) . 10_666
C1 C17 C18 C9 -65(63) 10_666 10_666
C9 C17 C18 N3 -122(61) 10_666 .
C10 C17 C18 N3 175.6(15) 10_666 .
C14 C17 C18 N3 -4.5(18) 10_666 .
C16 C17 C18 N3 -3.8(16) . .
C22 C17 C18 N3 177.9(12) . .
C1 C17 C18 N3 173(20) 10_666 .
C9 C17 C18 C23 55(61) 10_666 .
C10 C17 C18 C23 -7(3) 10_666 .
C14 C17 C18 C23 173.0(15) 10_666 .
C16 C17 C18 C23 173.6(15) . .
C22 C17 C18 C23 -5(3) . .
C1 C17 C18 C23 -10(17) 10_666 .
C9 C17 C18 C2 56(61) 10_666 10_666
C10 C17 C18 C2 -6(3) 10_666 10_666
C14 C17 C18 C2 173.6(15) 10_666 10_666
C16 C17 C18 C2 174.2(14) . 10_666
C22 C17 C18 C2 -4(3) . 10_666
C1 C17 C18 C2 -9(17) 10_666 10_666
C14 C16 C19 C20 -7(12) 10_666 .
C15 C16 C19 C20 173.1(11) . .
C17 C16 C19 C20 0.5(14) . .
C13 C16 C19 C20 -43(17) 10_666 .
C9 C16 C19 C20 -0.4(15) 10_666 .
C16 C19 C20 C21 -1.8(16) . .
C19 C20 C21 C22 4(2) . .
C20 C21 C22 C17 -5(2) . .
C9 C17 C22 C21 169(17) 10_666 .
C10 C17 C22 C21 -36(19) 10_666 .
C14 C17 C22 C21 3.4(18) 10_666 .
C16 C17 C22 C21 2.8(18) . .
C18 C17 C22 C21 -179.2(15) . .
C1 C17 C22 C21 -178.7(14) 10_666 .
C1 C18 C23 C2 -141(59) 10_666 10_666
N1 C18 C23 C2 -170(13) 10_666 10_666
C9 C18 C23 C2 8(13) 10_666 10_666
N3 C18 C23 C2 -176(13) . 10_666
C17 C18 C23 C2 7(13) . 10_666
N1 C18 C23 C1 -29(56) 10_666 10_666
C9 C18 C23 C1 149(58) 10_666 10_666
N3 C18 C23 C1 -35(56) . 10_666
C17 C18 C23 C1 148(58) . 10_666
C2 C18 C23 C1 141(59) 10_666 10_666
C1 C18 C23 C3 25(57) 10_666 10_666
N1 C18 C23 C3 -4.1(14) 10_666 10_666
C9 C18 C23 C3 174.0(17) 10_666 10_666
N3 C18 C23 C3 -10(2) . 10_666
C17 C18 C23 C3 172.9(17) . 10_666
C2 C18 C23 C3 166(13) 10_666 10_666
C1 C18 C23 C28 35(57) 10_666 .
N1 C18 C23 C28 5.1(15) 10_666 .
C9 C18 C23 C28 -176.8(16) 10_666 .
N3 C18 C23 C28 -1(2) . .
C17 C18 C23 C28 -177.9(16) . .
C2 C18 C23 C28 175(13) 10_666 .
C1 C18 C23 C5 -158(56) 10_666 10_666
N1 C18 C23 C5 173.0(11) 10_666 10_666
C9 C18 C23 C5 -9(3) 10_666 10_666
N3 C18 C23 C5 167.0(12) . 10_666
C17 C18 C23 C5 -10(2) . 10_666
C2 C18 C23 C5 -17(12) 10_666 10_666
C1 C18 C23 C24 -142(56) 10_666 .
N1 C18 C23 C24 -171.2(10) 10_666 .
C9 C18 C23 C24 7(3) 10_666 .
N3 C18 C23 C24 -177.2(11) . .
C17 C18 C23 C24 6(2) . .
C2 C18 C23 C24 -1(12) 10_666 .
C2 C23 C24 C25 148(100) 10_666 .
C1 C23 C24 C25 180.0(15) 10_666 .
C3 C23 C24 C25 14.5(16) 10_666 .
C28 C23 C24 C25 4.7(15) . .
C5 C23 C24 C25 -84(3) 10_666 .
C18 C23 C24 C25 -178.7(12) . .
C23 C24 C25 C26 -3.8(18) . .
C24 C25 C26 C27 -4(2) . .
C25 C26 C27 C28 12(2) . .
C26 C27 C28 C23 -11.2(19) . .
C2 C23 C28 C27 1(12) 10_666 .
C1 C23 C28 C27 -173.3(15) 10_666 .
C3 C23 C28 C27 -115(5) 10_666 .
C5 C23 C28 C27 16.2(16) 10_666 .
C24 C23 C28 C27 2.3(15) . .
C18 C23 C28 C27 -174.4(12) . .
