#------------------------------------------------------------------------------
#$Date: 2021-08-07 07:31:17 +0300 (Sat, 07 Aug 2021) $
#$Revision: 267990 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243887.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243887
loop_
_publ_author_name
'James, Zoe'
'Cai, Yunhe'
'Vaqueiro, Paz'
_publ_section_title
;
 Crystal structure of (C₉H₁₇N₂)₃[Bi₂I₉]
;
_journal_coeditor_code           JQ2007
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989021007799
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          '(C9 H17 N2)3 [Bi2 I9]'
_chemical_formula_moiety         '3(C9 H17 N2 +), Bi2 I9 3-'
_chemical_formula_sum            'C27 H51 Bi2 I9 N6'
_chemical_formula_weight         2019.79
_chemical_name_systematic
;
Tris(2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium)
tri-μ₂-iodido-bis[triiodidobismuth(III)]
;
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 115.861(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.2590(9)
_cell_length_b                   12.5734(3)
_cell_length_c                   21.6767(9)
_cell_measurement_reflns_used    25746
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33
_cell_measurement_theta_min      2
_cell_volume                     4723.4(4)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_molecular_graphics
;
ATOMS (Dowty, 2020) and ORIGIN (Edwards, 2002)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            38319
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         2.350
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    13.349
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.23
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2019)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.840
_exptl_crystal_description       plate
_exptl_crystal_F_000             3592
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.070
_refine_diff_density_max         2.221
_refine_diff_density_min         -2.568
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         13780
_refine_ls_number_restraints     543
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0359
_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)+(0.0423P)²+1.9329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0858
_reflns_number_gt                11096
_reflns_number_total             13780
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jq2007sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243887
_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   0.104
_shelx_estimated_absorpt_t_max   0.455
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi Bi1 0.18727(2) 0.75290(2) 0.16730(2) 0.01478(5) Uani d 1 . .
Bi Bi3 0.31503(2) 0.48511(2) 0.25029(2) 0.01518(5) Uani d 1 . .
I I2 0.18622(2) 0.60345(3) 0.28735(2) 0.01778(8) Uani d 1 . .
I I4 0.19072(2) 0.52615(3) 0.09942(2) 0.01934(8) Uani d 1 . .
I I5 0.37010(2) 0.72314(3) 0.24092(2) 0.02467(9) Uani d 1 . .
I I6 0.24567(3) 0.27208(3) 0.24502(2) 0.02245(9) Uani d 1 . .
I I7 0.42044(3) 0.48954(3) 0.40035(2) 0.02341(9) Uani d 1 . .
I I8 0.42451(3) 0.39855(3) 0.20120(2) 0.02961(10) Uani d 1 . .
I I9 0.01394(2) 0.74983(3) 0.10767(2) 0.01875(8) Uani d 1 . .
I I10 0.17891(3) 0.84909(3) 0.03995(2) 0.02861(10) Uani d 1 . .
I I11 0.21740(3) 0.95712(3) 0.24184(2) 0.02482(9) Uani d 1 . .
N N12 -0.0295(3) 0.7605(4) 0.3236(2) 0.0195(10) Uani d 1 . .
N N19 -0.0307(4) 0.7271(4) 0.4272(3) 0.0258(12) Uani d 1 . .
H H19 -0.027161 0.752892 0.466231 0.031 Uiso calc 1 . .
N N23 0.4254(4) 0.8196(5) 0.5457(3) 0.0360(15) Uani d 1 . .
N N30 0.3585(4) 0.8010(5) 0.4269(3) 0.0396(15) Uani d 1 . .
H H30 0.359982 0.793472 0.387180 0.048 Uiso calc 1 . .
C C13 -0.0306(4) 0.8352(5) 0.2708(3) 0.0229(13) Uani d 1 . .
H H13A -0.066990 0.893757 0.265999 0.028 Uiso calc 1 . .
H H13B -0.049722 0.797679 0.226308 0.028 Uiso calc 1 . .
C C14 0.0479(4) 0.8816(5) 0.2876(3) 0.0270(15) Uani d 1 . .
H H14A 0.048509 0.907961 0.244777 0.032 Uiso calc 1 . .
H H14B 0.087103 0.824650 0.306148 0.032 Uiso calc 1 . .
C C15 0.0701(5) 0.9724(5) 0.3392(3) 0.0278(15) Uani d 1 . .
H H15A 0.033195 1.031594 0.319000 0.033 Uiso calc 1 . .
H H15B 0.121944 0.998640 0.347472 0.033 Uiso calc 1 . .
C C16 0.0714(4) 0.9420(5) 0.4083(3) 0.0221(13) Uani d 1 . .
H H16A 0.108721 0.883316 0.428703 0.027 Uiso calc 1 . .
H H16B 0.089943 1.003738 0.439604 0.027 Uiso calc 1 . .
C C17 -0.0061(4) 0.9077(5) 0.4035(3) 0.0238(13) Uani d 1 . .
H H17A -0.006610 0.918916 0.448522 0.029 Uiso calc 1 . .
H H17B -0.046909 0.952911 0.369487 0.029 Uiso calc 1 . .
C C18 -0.0238(4) 0.7931(5) 0.3832(3) 0.0183(11) Uani d 1 . .
C C20 -0.0438(5) 0.6139(5) 0.4146(3) 0.0389(19) Uani d 1 . .
H H20A -0.099868 0.598977 0.392050 0.047 Uiso calc 1 . .
H H20B -0.020771 0.574505 0.458548 0.047 Uiso calc 1 . .
C C21 -0.0072(5) 0.5788(5) 0.3692(4) 0.0374(18) Uani d 1 . .
H H21A 0.049581 0.584182 0.394607 0.045 Uiso calc 1 . .
H H21B -0.020549 0.503466 0.355954 0.045 Uiso calc 1 . .
C C22 -0.0347(5) 0.6463(5) 0.3062(3) 0.0283(15) Uani d 1 . .
H H22A -0.003083 0.631452 0.281397 0.034 Uiso calc 1 . .
H H22B -0.088950 0.627970 0.275421 0.034 Uiso calc 1 . .
C C24 0.4962(5) 0.8075(6) 0.6123(3) 0.0354(18) Uani d 1 . .
H H24A 0.518750 0.736198 0.613821 0.043 Uiso calc 1 . .
H H24B 0.481188 0.811679 0.650508 0.043 Uiso calc 1 . .
C C25 0.5580(5) 0.8926(6) 0.6230(4) 0.0354(17) Uani d 1 . .
H H25A 0.532320 0.962602 0.608853 0.043 Uiso calc 1 . .
H H25B 0.593503 0.896773 0.672436 0.043 Uiso calc 1 . .
C C26 0.6046(5) 0.8709(6) 0.5832(4) 0.0383(18) Uani d 1 . .
H H26A 0.633464 0.803665 0.600267 0.046 Uiso calc 1 . .
H H26B 0.643041 0.928566 0.593145 0.046 Uiso calc 1 . .
C C27 0.5574(5) 0.8623(5) 0.5048(4) 0.0324(16) Uani d 1 . .
H H27A 0.529891 0.930270 0.487396 0.039 Uiso calc 1 . .
H H27B 0.593515 0.852186 0.483876 0.039 Uiso calc 1 . .
C C28 0.4989(5) 0.7723(5) 0.4815(4) 0.0325(17) Uani d 1 . .
H H28A 0.486300 0.754439 0.433334 0.039 Uiso calc 1 . .
H H28B 0.522400 0.708599 0.509803 0.039 Uiso calc 1 . .
C C29 0.4259(4) 0.7989(5) 0.4868(3) 0.0244(14) Uani d 1 . .
C C31 0.2843(5) 0.8157(7) 0.4294(4) 0.0391(18) Uani d 1 . .
H H31A 0.265602 0.746710 0.438399 0.047 Uiso calc 1 . .
H H31B 0.245533 0.843192 0.384877 0.047 Uiso calc 1 . .
C C32 0.2947(5) 0.8938(6) 0.4860(4) 0.0427(19) Uani d 1 . .
H H32A 0.306527 0.965247 0.473852 0.051 Uiso calc 1 . .
H H32B 0.246359 0.898744 0.491447 0.051 Uiso calc 1 . .
C C33 0.3583(5) 0.8581(6) 0.5509(4) 0.0339(16) Uani d 1 . .
H H33A 0.373768 0.918258 0.583628 0.041 Uiso calc 1 . .
H H33B 0.338628 0.800906 0.570454 0.041 Uiso calc 1 . .
N N34 0.7076(14) 0.569(2) 0.4694(6) 0.018(2) Uani d 0.571(13) A 1
C C35 0.7601(11) 0.5636(16) 0.5432(7) 0.018(3) Uani d 0.571(13) A 1
H H35A 0.813909 0.558906 0.549092 0.022 Uiso calc 0.571(13) A 1
H H35B 0.748948 0.498240 0.562769 0.022 Uiso calc 0.571(13) A 1
C C36 0.7528(11) 0.6591(18) 0.5828(10) 0.025(3) Uani d 0.571(13) A 1
H H36A 0.774972 0.639947 0.631953 0.030 Uiso calc 0.571(13) A 1
H H36B 0.697209 0.673716 0.567634 0.030 Uiso calc 0.571(13) A 1
C C37 0.7915(15) 0.7619(14) 0.5756(10) 0.024(3) Uani d 0.571(13) A 1
H H37A 0.777857 0.819481 0.599494 0.029 Uiso calc 0.571(13) A 1
H H37B 0.848090 0.751928 0.599731 0.029 Uiso calc 0.571(13) A 1
C C38 0.7712(11) 0.7984(14) 0.5031(10) 0.027(3) Uani d 0.571(13) A 1
H H38A 0.802108 0.862452 0.505442 0.032 Uiso calc 0.571(13) A 1
H H38B 0.716141 0.819577 0.481252 0.032 Uiso calc 0.571(13) A 1
C C39 0.7844(9) 0.7154(13) 0.4570(8) 0.024(3) Uani d 0.571(13) A 1
H H39A 0.788929 0.752081 0.418453 0.028 Uiso calc 0.571(13) A 1
H H39B 0.833494 0.677330 0.483789 0.028 Uiso calc 0.571(13) A 1
C C40 0.7199(12) 0.6369(17) 0.4291(7) 0.024(4) Uani d 0.571(13) A 1
N N41 0.6722(8) 0.6439(10) 0.3640(6) 0.031(3) Uani d 0.571(13) A 1
H H41 0.682573 0.690516 0.338939 0.037 Uiso calc 0.571(13) A 1
C C42 0.6022(8) 0.5786(10) 0.3302(6) 0.031(3) Uani d 0.571(13) A 1
H H42A 0.590982 0.566712 0.281668 0.037 Uiso calc 0.571(13) A 1
H H42B 0.557524 0.615825 0.331593 0.037 Uiso calc 0.571(13) A 1
C C43 0.6149(8) 0.4726(8) 0.3674(5) 0.027(2) Uani d 0.571(13) A 1
H H43A 0.565860 0.432290 0.349771 0.033 Uiso calc 0.571(13) A 1
H H43B 0.653090 0.429953 0.358891 0.033 Uiso calc 0.571(13) A 1
C C44 0.6436(8) 0.4913(12) 0.4427(6) 0.020(3) Uani d 0.571(13) A 1
H H44A 0.600588 0.517838 0.451858 0.024 Uiso calc 0.571(13) A 1
H H44B 0.661310 0.422934 0.467339 0.024 Uiso calc 0.571(13) A 1
N N34A 0.7037(19) 0.565(3) 0.4637(9) 0.020(3) Uani d 0.429(13) A 2
C C35A 0.7431(15) 0.557(2) 0.5392(9) 0.018(4) Uani d 0.429(13) A 2
H H35C 0.798368 0.541270 0.553819 0.021 Uiso calc 0.429(13) A 2
H H35D 0.720485 0.498255 0.554487 0.021 Uiso calc 0.429(13) A 2
C C36A 0.7363(15) 0.660(2) 0.5737(12) 0.020(3) Uani d 0.429(13) A 2
H H36C 0.741545 0.643507 0.620154 0.024 Uiso calc 0.429(13) A 2
H H36D 0.684452 0.691150 0.546985 0.024 Uiso calc 0.429(13) A 2
C C37A 0.7984(19) 0.7428(19) 0.5793(12) 0.022(4) Uani d 0.429(13) A 2
H H37C 0.795358 0.804298 0.606510 0.026 Uiso calc 0.429(13) A 2
H H37D 0.850144 0.710386 0.603988 0.026 Uiso calc 0.429(13) A 2
C C38A 0.7887(14) 0.7819(16) 0.5091(12) 0.022(4) Uani d 0.429(13) A 2
H H38C 0.826561 0.839271 0.515949 0.026 Uiso calc 0.429(13) A 2
H H38D 0.736426 0.812666 0.484167 0.026 Uiso calc 0.429(13) A 2
C C39A 0.7998(11) 0.6933(16) 0.4645(11) 0.019(3) Uani d 0.429(13) A 2
H H39C 0.813384 0.726348 0.429756 0.022 Uiso calc 0.429(13) A 2
H H39D 0.843318 0.647143 0.493943 0.022 Uiso calc 0.429(13) A 2
C C40A 0.7293(14) 0.626(2) 0.4290(8) 0.017(3) Uani d 0.429(13) A 2
N N41A 0.6957(8) 0.6272(12) 0.3614(8) 0.018(3) Uani d 0.429(13) A 2
H H41A 0.717128 0.664894 0.340134 0.022 Uiso calc 0.429(13) A 2
C C42A 0.6248(11) 0.5690(16) 0.3198(8) 0.029(3) Uani d 0.429(13) A 2
H H42C 0.637673 0.498814 0.306758 0.035 Uiso calc 0.429(13) A 2
H H42D 0.593866 0.609199 0.277302 0.035 Uiso calc 0.429(13) A 2
C C43A 0.5791(9) 0.5543(12) 0.3608(7) 0.027(3) Uani d 0.429(13) A 2
H H43C 0.558783 0.623766 0.366852 0.032 Uiso calc 0.429(13) A 2
H H43D 0.534828 0.506463 0.335744 0.032 Uiso calc 0.429(13) A 2
C C44A 0.6295(13) 0.5075(19) 0.4294(8) 0.026(4) Uani d 0.429(13) A 2
H H44C 0.602112 0.510448 0.458819 0.031 Uiso calc 0.429(13) A 2
H H44D 0.639682 0.431902 0.423618 0.031 Uiso calc 0.429(13) 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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
I10 Bi1 I11 . . 94.180(13) ?
I10 Bi1 I9 . . 90.328(14) ?
I11 Bi1 I9 . . 99.358(13) ?
I10 Bi1 I5 . . 96.536(14) ?
I11 Bi1 I5 . . 85.283(13) ?
I9 Bi1 I5 . . 171.439(12) ?
I10 Bi1 I2 . . 168.049(13) ?
I11 Bi1 I2 . . 97.725(12) ?
I9 Bi1 I2 . . 86.722(12) ?
I5 Bi1 I2 . . 85.519(12) ?
I10 Bi1 I4 . . 86.507(12) ?
I11 Bi1 I4 . . 168.754(14) ?
I9 Bi1 I4 . . 91.859(12) ?
I5 Bi1 I4 . . 83.488(12) ?
I2 Bi1 I4 . . 82.022(10) ?
I8 Bi3 I6 . . 91.922(13) ?
I8 Bi3 I7 . . 98.404(15) ?
I6 Bi3 I7 . . 97.988(12) ?
I8 Bi3 I4 . . 91.439(13) ?
I6 Bi3 I4 . . 88.991(12) ?
I7 Bi3 I4 . . 167.695(12) ?
I8 Bi3 I5 . . 90.760(13) ?
I6 Bi3 I5 . . 173.004(14) ?
I7 Bi3 I5 . . 88.005(12) ?
I4 Bi3 I5 . . 84.482(12) ?
I8 Bi3 I2 . . 172.288(13) ?
I6 Bi3 I2 . . 92.465(12) ?
I7 Bi3 I2 . . 87.263(12) ?
I4 Bi3 I2 . . 82.301(11) ?
I5 Bi3 I2 . . 84.183(11) ?
Bi1 I2 Bi3 . . 78.144(9) ?
Bi3 I4 Bi1 . . 80.095(10) ?
Bi1 I5 Bi3 . . 79.516(11) ?
C18 N12 C13 . . 122.1(5) ?
C18 N12 C22 . . 121.5(5) ?
C13 N12 C22 . . 116.4(4) ?
C18 N19 C20 . . 123.2(5) ?
C18 N19 H19 . . 118.4 ?
C20 N19 H19 . . 118.4 ?
C29 N23 C33 . . 122.4(7) ?
C29 N23 C24 . . 121.9(6) ?
C33 N23 C24 . . 115.6(5) ?
C29 N30 C31 . . 120.1(6) ?
C29 N30 H30 . . 119.9 ?
C31 N30 H30 . . 119.9 ?
N12 C13 C14 . . 112.7(5) ?
N12 C13 H13A . . 109.0 ?
C14 C13 H13A . . 109.0 ?
N12 C13 H13B . . 109.0 ?
C14 C13 H13B . . 109.0 ?
H13A C13 H13B . . 107.8 ?
C13 C14 C15 . . 113.4(5) ?
C13 C14 H14A . . 108.9 ?
C15 C14 H14A . . 108.9 ?
C13 C14 H14B . . 108.9 ?
C15 C14 H14B . . 108.9 ?
H14A C14 H14B . . 107.7 ?
C14 C15 C16 . . 114.2(5) ?
C14 C15 H15A . . 108.7 ?
C16 C15 H15A . . 108.7 ?
C14 C15 H15B . . 108.7 ?
C16 C15 H15B . . 108.7 ?
H15A C15 H15B . . 107.6 ?
C17 C16 C15 . . 114.2(5) ?
C17 C16 H16A . . 108.7 ?
C15 C16 H16A . . 108.7 ?
C17 C16 H16B . . 108.7 ?
C15 C16 H16B . . 108.7 ?
H16A C16 H16B . . 107.6 ?
C18 C17 C16 . . 112.6(5) ?
C18 C17 H17A . . 109.1 ?
C16 C17 H17A . . 109.1 ?
C18 C17 H17B . . 109.1 ?
C16 C17 H17B . . 109.1 ?
H17A C17 H17B . . 107.8 ?
N12 C18 N19 . . 121.7(5) ?
N12 C18 C17 . . 120.0(5) ?
N19 C18 C17 . . 118.3(5) ?
N19 C20 C21 . . 108.6(6) ?
N19 C20 H20A . . 110.0 ?
C21 C20 H20A . . 110.0 ?
N19 C20 H20B . . 110.0 ?
C21 C20 H20B . . 110.0 ?
H20A C20 H20B . . 108.4 ?
C22 C21 C20 . . 110.6(6) ?
C22 C21 H21A . . 109.5 ?
C20 C21 H21A . . 109.5 ?
C22 C21 H21B . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 108.1 ?
N12 C22 C21 . . 111.1(5) ?
N12 C22 H22A . . 109.4 ?
C21 C22 H22A . . 109.4 ?
N12 C22 H22B . . 109.4 ?
C21 C22 H22B . . 109.4 ?
H22A C22 H22B . . 108.0 ?
N23 C24 C25 . . 113.1(5) ?
N23 C24 H24A . . 109.0 ?
C25 C24 H24A . . 109.0 ?
N23 C24 H24B . . 109.0 ?
C25 C24 H24B . . 109.0 ?
H24A C24 H24B . . 107.8 ?
C26 C25 C24 . . 113.6(6) ?
C26 C25 H25A . . 108.9 ?
C24 C25 H25A . . 108.9 ?
C26 C25 H25B . . 108.9 ?
C24 C25 H25B . . 108.9 ?
H25A C25 H25B . . 107.7 ?
C25 C26 C27 . . 115.3(7) ?
C25 C26 H26A . . 108.4 ?
C27 C26 H26A . . 108.4 ?
C25 C26 H26B . . 108.4 ?
C27 C26 H26B . . 108.4 ?
H26A C26 H26B . . 107.5 ?
C28 C27 C26 . . 114.4(6) ?
C28 C27 H27A . . 108.7 ?
C26 C27 H27A . . 108.7 ?
C28 C27 H27B . . 108.7 ?
C26 C27 H27B . . 108.7 ?
H27A C27 H27B . . 107.6 ?
C29 C28 C27 . . 113.2(5) ?
C29 C28 H28A . . 108.9 ?
C27 C28 H28A . . 108.9 ?
C29 C28 H28B . . 108.9 ?
C27 C28 H28B . . 108.9 ?
H28A C28 H28B . . 107.7 ?
N23 C29 N30 . . 120.6(6) ?
N23 C29 C28 . . 121.7(6) ?
N30 C29 C28 . . 117.6(5) ?
N30 C31 C32 . . 108.9(6) ?
N30 C31 H31A . . 109.9 ?
C32 C31 H31A . . 109.9 ?
N30 C31 H31B . . 109.9 ?
C32 C31 H31B . . 109.9 ?
H31A C31 H31B . . 108.3 ?
C33 C32 C31 . . 109.6(7) ?
C33 C32 H32A . . 109.7 ?
C31 C32 H32A . . 109.7 ?
C33 C32 H32B . . 109.7 ?
C31 C32 H32B . . 109.7 ?
H32A C32 H32B . . 108.2 ?
N23 C33 C32 . . 115.5(6) ?
N23 C33 H33A . . 108.4 ?
C32 C33 H33A . . 108.4 ?
N23 C33 H33B . . 108.4 ?
C32 C33 H33B . . 108.4 ?
H33A C33 H33B . . 107.5 ?
C40 N34 C35 . . 120.7(11) ?
C40 N34 C44 . . 122.0(10) ?
C35 N34 C44 . . 117.2(10) ?
N34 C35 C36 . . 113.0(13) ?
N34 C35 H35A . . 109.0 ?
C36 C35 H35A . . 109.0 ?
N34 C35 H35B . . 109.0 ?
C36 C35 H35B . . 109.0 ?
H35A C35 H35B . . 107.8 ?
C35 C36 C37 . . 116.2(12) ?
C35 C36 H36A . . 108.2 ?
C37 C36 H36A . . 108.2 ?
C35 C36 H36B . . 108.2 ?
C37 C36 H36B . . 108.2 ?
H36A C36 H36B . . 107.4 ?
C38 C37 C36 . . 116.3(13) ?
C38 C37 H37A . . 108.2 ?
C36 C37 H37A . . 108.2 ?
C38 C37 H37B . . 108.2 ?
C36 C37 H37B . . 108.2 ?
H37A C37 H37B . . 107.4 ?
C37 C38 C39 . . 115.2(12) ?
C37 C38 H38A . . 108.5 ?
C39 C38 H38A . . 108.5 ?
C37 C38 H38B . . 108.5 ?
C39 C38 H38B . . 108.5 ?
H38A C38 H38B . . 107.5 ?
C40 C39 C38 . . 111.4(12) ?
C40 C39 H39A . . 109.3 ?
C38 C39 H39A . . 109.3 ?
C40 C39 H39B . . 109.3 ?
C38 C39 H39B . . 109.3 ?
H39A C39 H39B . . 108.0 ?
N41 C40 N34 . . 120.9(11) ?
N41 C40 C39 . . 117.4(11) ?
N34 C40 C39 . . 121.4(11) ?
C40 N41 C42 . . 124.0(11) ?
C40 N41 H41 . . 118.0 ?
C42 N41 H41 . . 118.0 ?
N41 C42 C43 . . 108.9(10) ?
N41 C42 H42A . . 109.9 ?
C43 C42 H42A . . 109.9 ?
N41 C42 H42B . . 109.9 ?
C43 C42 H42B . . 109.9 ?
H42A C42 H42B . . 108.3 ?
C44 C43 C42 . . 109.7(10) ?
C44 C43 H43A . . 109.7 ?
C42 C43 H43A . . 109.7 ?
C44 C43 H43B . . 109.7 ?
C42 C43 H43B . . 109.7 ?
H43A C43 H43B . . 108.2 ?
N34 C44 C43 . . 112.3(10) ?
N34 C44 H44A . . 109.2 ?
C43 C44 H44A . . 109.2 ?
N34 C44 H44B . . 109.2 ?
C43 C44 H44B . . 109.2 ?
H44A C44 H44B . . 107.9 ?
C40A N34A C35A . . 121.9(14) ?
C40A N34A C44A . . 121.3(13) ?
C35A N34A C44A . . 116.4(14) ?
N34A C35A C36A . . 112.3(17) ?
N34A C35A H35C . . 109.1 ?
C36A C35A H35C . . 109.1 ?
N34A C35A H35D . . 109.1 ?
C36A C35A H35D . . 109.1 ?
H35C C35A H35D . . 107.9 ?
C35A C36A C37A . . 112.2(16) ?
C35A C36A H36C . . 109.2 ?
C37A C36A H36C . . 109.2 ?
C35A C36A H36D . . 109.2 ?
C37A C36A H36D . . 109.2 ?
H36C C36A H36D . . 107.9 ?
C38A C37A C36A . . 112.5(17) ?
C38A C37A H37C . . 109.1 ?
C36A C37A H37C . . 109.1 ?
C38A C37A H37D . . 109.1 ?
C36A C37A H37D . . 109.1 ?
H37C C37A H37D . . 107.8 ?
C37A C38A C39A . . 113.5(14) ?
C37A C38A H38C . . 108.9 ?
C39A C38A H38C . . 108.9 ?
C37A C38A H38D . . 108.9 ?
C39A C38A H38D . . 108.9 ?
H38C C38A H38D . . 107.7 ?
C40A C39A C38A . . 112.6(15) ?
C40A C39A H39C . . 109.1 ?
C38A C39A H39C . . 109.1 ?
C40A C39A H39D . . 109.1 ?
C38A C39A H39D . . 109.1 ?
H39C C39A H39D . . 107.8 ?
N41A C40A N34A . . 120.9(13) ?
N41A C40A C39A . . 117.7(14) ?
N34A C40A C39A . . 121.3(13) ?
C40A N41A C42A . . 123.8(13) ?
C40A N41A H41A . . 118.1 ?
C42A N41A H41A . . 118.1 ?
N41A C42A C43A . . 108.9(12) ?
N41A C42A H42C . . 109.9 ?
C43A C42A H42C . . 109.9 ?
N41A C42A H42D . . 109.9 ?
C43A C42A H42D . . 109.9 ?
H42C C42A H42D . . 108.3 ?
C44A C43A C42A . . 110.0(15) ?
C44A C43A H43C . . 109.7 ?
C42A C43A H43C . . 109.7 ?
C44A C43A H43D . . 109.7 ?
C42A C43A H43D . . 109.7 ?
H43C C43A H43D . . 108.2 ?
N34A C44A C43A . . 112.0(14) ?
N34A C44A H44C . . 109.2 ?
C43A C44A H44C . . 109.2 ?
N34A C44A H44D . . 109.2 ?
C43A C44A H44D . . 109.2 ?
H44C C44A H44D . . 107.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Bi1 I10 . 2.9532(4) ?
Bi1 I11 . 2.9534(4) ?
Bi1 I9 . 3.0085(5) ?
Bi1 I5 . 3.1911(5) ?
Bi1 I2 . 3.2169(4) ?
Bi1 I4 . 3.2224(4) ?
Bi3 I8 . 2.9530(5) ?
Bi3 I6 . 2.9730(4) ?
Bi3 I7 . 2.9908(5) ?
Bi3 I4 . 3.1405(5) ?
Bi3 I5 . 3.2111(4) ?
Bi3 I2 . 3.2788(4) ?
N12 C18 . 1.313(7) ?
N12 C13 . 1.473(7) ?
N12 C22 . 1.477(7) ?
N19 C18 . 1.314(7) ?
N19 C20 . 1.451(8) ?
N19 H19 . 0.8800 ?
N23 C29 . 1.308(7) ?
N23 C33 . 1.430(10) ?
N23 C24 . 1.500(10) ?
N30 C29 . 1.379(9) ?
N30 C31 . 1.465(10) ?
N30 H30 . 0.8800 ?
C13 C14 . 1.510(9) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.523(8) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.536(8) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 C17 . 1.512(9) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C18 . 1.502(8) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C20 C21 . 1.505(11) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C21 C22 . 1.495(9) ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C24 C25 . 1.541(11) ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C25 C26 . 1.517(10) ?
C25 H25A . 0.9900 ?
C25 H25B . 0.9900 ?
C26 C27 . 1.542(11) ?
C26 H26A . 0.9900 ?
C26 H26B . 0.9900 ?
C27 C28 . 1.519(11) ?
C27 H27A . 0.9900 ?
C27 H27B . 0.9900 ?
C28 C29 . 1.497(10) ?
C28 H28A . 0.9900 ?
C28 H28B . 0.9900 ?
C31 C32 . 1.515(10) ?
C31 H31A . 0.9900 ?
C31 H31B . 0.9900 ?
C32 C33 . 1.476(11) ?
C32 H32A . 0.9900 ?
C32 H32B . 0.9900 ?
C33 H33A . 0.9900 ?
C33 H33B . 0.9900 ?
N34 C40 . 1.318(11) ?
N34 C35 . 1.475(12) ?
N34 C44 . 1.475(13) ?
C35 C36 . 1.516(12) ?
C35 H35A . 0.9900 ?
C35 H35B . 0.9900 ?
C36 C37 . 1.533(13) ?
C36 H36A . 0.9900 ?
C36 H36B . 0.9900 ?
C37 C38 . 1.516(13) ?
C37 H37A . 0.9900 ?
C37 H37B . 0.9900 ?
C38 C39 . 1.543(13) ?
C38 H38A . 0.9900 ?
C38 H38B . 0.9900 ?
C39 C40 . 1.493(13) ?
C39 H39A . 0.9900 ?
C39 H39B . 0.9900 ?
C40 N41 . 1.308(12) ?
N41 C42 . 1.472(14) ?
N41 H41 . 0.8800 ?
C42 C43 . 1.521(14) ?
C42 H42A . 0.9900 ?
C42 H42B . 0.9900 ?
C43 C44 . 1.497(16) ?
C43 H43A . 0.9900 ?
C43 H43B . 0.9900 ?
C44 H44A . 0.9900 ?
C44 H44B . 0.9900 ?
N34A C40A . 1.319(13) ?
N34A C35A . 1.476(13) ?
N34A C44A . 1.477(15) ?
C35A C36A . 1.525(14) ?
C35A H35C . 0.9900 ?
C35A H35D . 0.9900 ?
C36A C37A . 1.549(16) ?
C36A H36C . 0.9900 ?
C36A H36D . 0.9900 ?
C37A C38A . 1.530(14) ?
C37A H37C . 0.9900 ?
C37A H37D . 0.9900 ?
C38A C39A . 1.551(15) ?
C38A H38C . 0.9900 ?
C38A H38D . 0.9900 ?
C39A C40A . 1.492(14) ?
C39A H39C . 0.9900 ?
C39A H39D . 0.9900 ?
C40A N41A . 1.317(13) ?
N41A C42A . 1.462(15) ?
N41A H41A . 0.8800 ?
C42A C43A . 1.510(16) ?
C42A H42C . 0.9900 ?
C42A H42D . 0.9900 ?
C43A C44A . 1.497(18) ?
C43A H43C . 0.9900 ?
C43A H43D . 0.9900 ?
C44A H44C . 0.9900 ?
C44A H44D . 0.9900 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N19 H19 I9 4_576 0.88 2.81 3.632(5) 155.5 yes
N41 H41 I6 2_655 0.88 2.91 3.735(13) 156.9 yes
N41 H41 I8 2_655 0.88 3.21 3.663(14) 114.7 yes
N41A H41A I6 2_655 0.88 2.62 3.492(15) 168.5 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C18 N12 C13 C14 . . . . 74.6(7) ?
C22 N12 C13 C14 . . . . -105.1(6) ?
N12 C13 C14 C15 . . . . -79.8(7) ?
C13 C14 C15 C16 . . . . 58.5(8) ?
C14 C15 C16 C17 . . . . -62.5(8) ?
C15 C16 C17 C18 . . . . 82.5(6) ?
C13 N12 C18 N19 . . . . 173.0(6) ?
C22 N12 C18 N19 . . . . -7.4(10) ?
C13 N12 C18 C17 . . . . -9.3(9) ?
C22 N12 C18 C17 . . . . 170.3(6) ?
C20 N19 C18 N12 . . . . 1.0(11) ?
C20 N19 C18 C17 . . . . -176.7(7) ?
C16 C17 C18 N12 . . . . -61.7(8) ?
C16 C17 C18 N19 . . . . 116.1(6) ?
C18 N19 C20 C21 . . . . 29.8(10) ?
N19 C20 C21 C22 . . . . -53.0(8) ?
C18 N12 C22 C21 . . . . -18.5(9) ?
C13 N12 C22 C21 . . . . 161.1(6) ?
C20 C21 C22 N12 . . . . 48.4(9) ?
C29 N23 C24 C25 . . . . 70.8(8) ?
C33 N23 C24 C25 . . . . -107.4(7) ?
N23 C24 C25 C26 . . . . -78.4(8) ?
C24 C25 C26 C27 . . . . 58.7(8) ?
C25 C26 C27 C28 . . . . -61.5(8) ?
C26 C27 C28 C29 . . . . 80.3(7) ?
C33 N23 C29 N30 . . . . -8.1(10) ?
C24 N23 C29 N30 . . . . 173.8(6) ?
C33 N23 C29 C28 . . . . 171.9(6) ?
C24 N23 C29 C28 . . . . -6.2(10) ?
C31 N30 C29 N23 . . . . -6.3(10) ?
C31 N30 C29 C28 . . . . 173.7(6) ?
C27 C28 C29 N23 . . . . -62.7(8) ?
C27 C28 C29 N30 . . . . 117.3(7) ?
C29 N30 C31 C32 . . . . 37.4(9) ?
N30 C31 C32 C33 . . . . -53.5(9) ?
C29 N23 C33 C32 . . . . -12.0(10) ?
C24 N23 C33 C32 . . . . 166.2(6) ?
C31 C32 C33 N23 . . . . 42.8(9) ?
C40 N34 C35 C36 . . . . 71(3) ?
C44 N34 C35 C36 . . . . -111(2) ?
N34 C35 C36 C37 . . . . -77.1(19) ?
C35 C36 C37 C38 . . . . 52(2) ?
C36 C37 C38 C39 . . . . -55(2) ?
C37 C38 C39 C40 . . . . 80.1(16) ?
C35 N34 C40 N41 . . . . -178(2) ?
C44 N34 C40 N41 . . . . 5(5) ?
C35 N34 C40 C39 . . . . -3(4) ?
C44 N34 C40 C39 . . . . 179(2) ?
C38 C39 C40 N41 . . . . 108(2) ?
C38 C39 C40 N34 . . . . -67(3) ?
N34 C40 N41 C42 . . . . 0(4) ?
C39 C40 N41 C42 . . . . -174.6(15) ?
C40 N41 C42 C43 . . . . -29(2) ?
N41 C42 C43 C44 . . . . 50.9(15) ?
C40 N34 C44 C43 . . . . 21(4) ?
C35 N34 C44 C43 . . . . -156.7(18) ?
C42 C43 C44 N34 . . . . -48(2) ?
C40A N34A C35A C36A . . . . 69(4) ?
C44A N34A C35A C36A . . . . -105(3) ?
N34A C35A C36A C37A . . . . -84(2) ?
C35A C36A C37A C38A . . . . 65(3) ?
C36A C37A C38A C39A . . . . -64(3) ?
C37A C38A C39A C40A . . . . 81(2) ?
C35A N34A C40A N41A . . . . 176(3) ?
C44A N34A C40A N41A . . . . -10(6) ?
C35A N34A C40A C39A . . . . 0(6) ?
C44A N34A C40A C39A . . . . 173(3) ?
C38A C39A C40A N41A . . . . 117(2) ?
C38A C39A C40A N34A . . . . -66(4) ?
N34A C40A N41A C42A . . . . 6(5) ?
C39A C40A N41A C42A . . . . -177.6(18) ?
C40A N41A C42A C43A . . . . 26(3) ?
N41A C42A C43A C44A . . . . -51(2) ?
C40A N34A C44A C43A . . . . -18(5) ?
C35A N34A C44A C43A . . . . 156(3) ?
C42A C43A C44A N34A . . . . 49(3) ?

_cod_database_fobs_code 2243887
