#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/69/2226990.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_2226990
loop_
_publ_author_name
'Giffin, Nick A.'
'Hendsbee, Arthur D.'
'Masuda, Jason D.'
_publ_section_title
;
 1,3-Bis(2,6-diisopropylphenyl)imidazolidinium tetraphenylborate
 dichloromethane disolvate
;
_journal_coeditor_code           LH5077
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2090
_journal_page_last               o2091
_journal_paper_doi               10.1107/S1600536810028424
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C27 H39 N2 +, C24 H20 B -, 2C H2 Cl2'
_chemical_formula_moiety         'C27 H39 N2 +, C24 H20 B -, 2(C H2 Cl2)'
_chemical_formula_sum            'C53 H63 B Cl4 N2'
_chemical_formula_weight         880.66
_chemical_melting_point_gt       472
_chemical_melting_point_lt       475
_chemical_name_systematic
;
1,3-Bis(2,6-diisopropylphenyl)imidazolidinium tetraphenylborate
dichloromethane disolvate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.7600(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.4648(14)
_cell_length_b                   10.3964(7)
_cell_length_c                   22.7524(15)
_cell_measurement_reflns_used    7600
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.76
_cell_measurement_theta_min      2.18
_cell_volume                     5066.4(6)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0128
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17851
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2010)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          .4874
_exptl_crystal_size_mid          .3442
_exptl_crystal_size_min          .2911
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.440
_refine_ls_abs_structure_details 'Flack (1983), 3456 Friedels'
_refine_ls_abs_structure_Flack   -0.11(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.352
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         8396
_refine_ls_number_restraints     892
_refine_ls_restrained_S_all      1.532
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0624
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0829P)²+1.5238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1786
_refine_ls_wR_factor_ref         0.1864
_reflns_number_gt                7118
_reflns_number_total             8396
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5077.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'C -2yc '
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2226990
_cod_database_fobs_code          2226990
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.32237(14) 0.8042(3) 0.34114(15) 0.0434(7) Uani d . 1 . .
H H1 0.2942 0.8353 0.3118 0.052 Uiso calc R 1 . .
C C2 0.39497(16) 0.8011(3) 0.41785(18) 0.0519(9) Uani d . 1 . .
H H2A 0.3814 0.8215 0.4566 0.062 Uiso calc R 1 . .
H H2B 0.4396 0.8151 0.4177 0.062 Uiso calc R 1 . .
C C3 0.37791(15) 0.6632(3) 0.40044(16) 0.0461(8) Uani d . 1 . .
H H3A 0.4129 0.6188 0.3846 0.055 Uiso calc R 1 . .
H H3B 0.3640 0.6149 0.4336 0.055 Uiso calc R 1 . .
C C4 0.36517(16) 1.0162(3) 0.3702(2) 0.0583(6) Uani d U 1 . .
C C5 0.4123(2) 1.0698(4) 0.3383(2) 0.0696(7) Uani d U 1 . .
C C6 0.4195(2) 1.2020(4) 0.3413(3) 0.0763(7) Uani d U 1 . .
H H6 0.4503 1.2417 0.3207 0.092 Uiso calc R 1 . .
C C7 0.3818(2) 1.2746(5) 0.3742(3) 0.0799(8) Uani d U 1 . .
H H7 0.3876 1.3632 0.3757 0.096 Uiso calc R 1 . .
C C8 0.3361(2) 1.2214(4) 0.4047(3) 0.0740(7) Uani d U 1 . .
H H8 0.3109 1.2739 0.4262 0.089 Uiso calc R 1 . .
C C9 0.32666(18) 1.0890(4) 0.4041(2) 0.0657(7) Uani d U 1 . .
C C10 0.4535(2) 0.9890(5) 0.3013(3) 0.0765(7) Uani d U 1 . .
H H10 0.4493 0.8989 0.3130 0.092 Uiso calc R 1 . .
C C11 0.4323(3) 1.0003(8) 0.2363(3) 0.1121(14) Uani d U 1 . .
H H11A 0.4347 1.0885 0.2242 0.168 Uiso calc R 1 . .
H H11B 0.3899 0.9708 0.2303 0.168 Uiso calc R 1 . .
H H11C 0.4588 0.9486 0.2134 0.168 Uiso calc R 1 . .
C C12 0.5217(2) 1.0247(6) 0.3085(3) 0.0886(12) Uani d U 1 . .
H H12A 0.5279 1.1069 0.2906 0.133 Uiso calc R 1 . .
H H12B 0.5460 0.9609 0.2899 0.133 Uiso calc R 1 . .
H H12C 0.5345 1.0291 0.3497 0.133 Uiso calc R 1 . .
C C13 0.27496(19) 1.0312(4) 0.4373(2) 0.0700(7) Uani d U 1 . .
H H13 0.2771 0.9376 0.4325 0.084 Uiso calc R 1 . .
C C14 0.2814(3) 1.0592(6) 0.5022(3) 0.0930(11) Uani d U 1 . .
H H14A 0.3187 1.0193 0.5192 0.139 Uiso calc R 1 . .
H H14B 0.2459 1.0257 0.5206 0.139 Uiso calc R 1 . .
H H14C 0.2839 1.1505 0.5083 0.139 Uiso calc R 1 . .
C C15 0.2115(2) 1.0757(5) 0.4093(3) 0.0831(11) Uani d U 1 . .
H H15A 0.2056 1.1651 0.4178 0.125 Uiso calc R 1 . .
H H15B 0.1788 1.0262 0.4251 0.125 Uiso calc R 1 . .
H H15C 0.2106 1.0635 0.3674 0.125 Uiso calc R 1 . .
C C16 0.29202(19) 0.5791(4) 0.3253(2) 0.0599(6) Uani d U 1 . .
C C17 0.3132(2) 0.5293(4) 0.2739(2) 0.0692(7) Uani d U 1 . .
C C18 0.2803(2) 0.4256(4) 0.2483(2) 0.0752(8) Uani d U 1 . .
H H18 0.2931 0.3896 0.2136 0.090 Uiso calc R 1 . .
C C19 0.2297(2) 0.3767(4) 0.2736(2) 0.0766(8) Uani d U 1 . .
H H19 0.2086 0.3074 0.2558 0.092 Uiso calc R 1 . .
C C20 0.2087(2) 0.4267(4) 0.3249(2) 0.0715(7) Uani d U 1 . .
H H20 0.1740 0.3912 0.3411 0.086 Uiso calc R 1 . .
C C21 0.23988(19) 0.5310(4) 0.3526(2) 0.0623(6) Uani d U 1 . .
C C22 0.2165(2) 0.5901(4) 0.4072(2) 0.0673(7) Uani d U 1 . .
H H22 0.2524 0.6303 0.4287 0.081 Uiso calc R 1 . .
C C23 0.1891(2) 0.4947(5) 0.4486(3) 0.0830(10) Uani d U 1 . .
H H23A 0.1542 0.4517 0.4286 0.125 Uiso calc R 1 . .
H H23B 0.1753 0.5393 0.4823 0.125 Uiso calc R 1 . .
H H23C 0.2203 0.4325 0.4610 0.125 Uiso calc R 1 . .
C C24 0.1694(2) 0.6984(5) 0.3905(3) 0.0860(11) Uani d U 1 . .
H H24A 0.1898 0.7650 0.3698 0.129 Uiso calc R 1 . .
H H24B 0.1536 0.7334 0.4256 0.129 Uiso calc R 1 . .
H H24C 0.1354 0.6642 0.3657 0.129 Uiso calc R 1 . .
C C25 0.3687(3) 0.5847(5) 0.2449(2) 0.0779(8) Uani d U 1 . .
H H25 0.3918 0.6392 0.2740 0.094 Uiso calc R 1 . .
C C26 0.4138(3) 0.4820(6) 0.2250(3) 0.0993(13) Uani d U 1 . .
H H26A 0.4349 0.4427 0.2588 0.149 Uiso calc R 1 . .
H H26B 0.4438 0.5211 0.2011 0.149 Uiso calc R 1 . .
H H26C 0.3908 0.4176 0.2024 0.149 Uiso calc R 1 . .
C C27 0.3473(4) 0.6694(6) 0.1931(3) 0.1047(13) Uani d U 1 . .
H H27A 0.3293 0.6168 0.1618 0.157 Uiso calc R 1 . .
H H27B 0.3825 0.7154 0.1797 0.157 Uiso calc R 1 . .
H H27C 0.3167 0.7295 0.2052 0.157 Uiso calc R 1 . .
C C28 0.56734(17) 0.4344(3) 0.57017(18) 0.0519(7) Uani d U 1 . .
C C29 0.5472(3) 0.3788(4) 0.6212(2) 0.0755(10) Uani d U 1 . .
H H29 0.5109 0.4098 0.6364 0.091 Uiso calc R 1 . .
C C30 0.5791(3) 0.2785(5) 0.6505(3) 0.0988(14) Uani d U 1 . .
H H30 0.5649 0.2456 0.6852 0.119 Uiso calc R 1 . .
C C31 0.6317(3) 0.2287(5) 0.6279(3) 0.1040(15) Uani d U 1 . .
H H31 0.6526 0.1605 0.6467 0.125 Uiso calc R 1 . .
C C32 0.6528(3) 0.2785(5) 0.5786(3) 0.0925(13) Uani d U 1 . .
H H32 0.6886 0.2449 0.5634 0.111 Uiso calc R 1 . .
C C33 0.62107(19) 0.3813(4) 0.5497(2) 0.0685(9) Uani d U 1 . .
H H33 0.6367 0.4149 0.5158 0.082 Uiso calc R 1 . .
C C34 0.54183(14) 0.5733(3) 0.46984(17) 0.0475(6) Uani d U 1 . .
C C35 0.53663(18) 0.4641(4) 0.4336(2) 0.0611(8) Uani d U 1 . .
H H35 0.5308 0.3845 0.4511 0.073 Uiso calc R 1 . .
C C36 0.5398(2) 0.4689(5) 0.3730(2) 0.0739(9) Uani d U 1 . .
H H36 0.5363 0.3936 0.3510 0.089 Uiso calc R 1 . .
C C37 0.5479(2) 0.5841(6) 0.3457(2) 0.0784(10) Uani d U 1 . .
H H37 0.5505 0.5879 0.3051 0.094 Uiso calc R 1 . .
C C38 0.55225(18) 0.6931(5) 0.3788(2) 0.0702(9) Uani d U 1 . .
H H38 0.5575 0.7720 0.3605 0.084 Uiso calc R 1 . .
C C39 0.54900(15) 0.6885(4) 0.43912(19) 0.0570(7) Uani d U 1 . .
H H39 0.5517 0.7650 0.4603 0.068 Uiso calc R 1 . .
C C40 0.45929(16) 0.5707(3) 0.54864(17) 0.0503(7) Uani d U 1 . .
C C41 0.42234(18) 0.4617(4) 0.5400(2) 0.0597(8) Uani d U 1 . .
H H41 0.4411 0.3839 0.5313 0.072 Uiso calc R 1 . .
C C42 0.35757(19) 0.4663(5) 0.5439(2) 0.0717(10) Uani d U 1 . .
H H42 0.3345 0.3909 0.5388 0.086 Uiso calc R 1 . .
C C43 0.3276(2) 0.5772(5) 0.5550(2) 0.0760(10) Uani d U 1 . .
H H43 0.2844 0.5794 0.5566 0.091 Uiso calc R 1 . .
C C44 0.3623(2) 0.6847(5) 0.5637(2) 0.0743(10) Uani d U 1 . .
H H44 0.3428 0.7615 0.5725 0.089 Uiso calc R 1 . .
C C45 0.42724(18) 0.6826(4) 0.5598(2) 0.0631(9) Uani d U 1 . .
H H45 0.4495 0.7590 0.5648 0.076 Uiso calc R 1 . .
C C46 0.57412(16) 0.6805(3) 0.57753(18) 0.0528(7) Uani d U 1 . .
C C47 0.5579(2) 0.7240(5) 0.6326(2) 0.0745(10) Uani d U 1 . .
H H47 0.5218 0.6929 0.6481 0.089 Uiso calc R 1 . .
C C48 0.5949(3) 0.8135(6) 0.6650(3) 0.0917(13) Uani d U 1 . .
H H48 0.5823 0.8418 0.7011 0.110 Uiso calc R 1 . .
C C49 0.6482(3) 0.8594(5) 0.6452(3) 0.0913(13) Uani d U 1 . .
H H49 0.6722 0.9183 0.6674 0.110 Uiso calc R 1 . .
C C50 0.6665(2) 0.8187(4) 0.5921(3) 0.0786(11) Uani d U 1 . .
H H50 0.7034 0.8493 0.5780 0.094 Uiso calc R 1 . .
C C51 0.62988(18) 0.7313(4) 0.5591(2) 0.0615(8) Uani d U 1 . .
H H51 0.6431 0.7052 0.5229 0.074 Uiso calc R 1 . .
C C52 0.1967(3) 0.9707(6) 0.1819(3) 0.109(2) Uani d . 1 . .
H H52B 0.1940 0.8877 0.1624 0.130 Uiso calc R 1 . .
H H52A 0.1664 1.0279 0.1622 0.130 Uiso calc R 1 . .
C C53 0.5164(3) 0.0513(8) 0.5452(3) 0.115(2) Uani d . 1 . .
H H53B 0.5442 0.1185 0.5607 0.138 Uiso calc R 1 . .
H H53A 0.5363 -0.0309 0.5541 0.138 Uiso calc R 1 . .
B B1 0.53552(17) 0.5659(4) 0.54107(19) 0.0459(8) Uani d . 1 . .
Cl Cl1 0.18097(19) 0.9538(4) 0.25374(12) 0.2196(19) Uani d . 1 . .
Cl Cl2 0.26822(14) 1.0308(4) 0.1782(2) 0.230(2) Uani d . 1 . .
Cl Cl3 0.44650(12) 0.0595(2) 0.57959(13) 0.1433(8) Uani d . 1 . .
Cl Cl4 0.50522(12) 0.0685(2) 0.47076(10) 0.1297(7) Uani d . 1 . .
N N1 0.32668(13) 0.6829(2) 0.35495(13) 0.0462(6) Uani d . 1 . .
N N2 0.36081(11) 0.8780(2) 0.37186(13) 0.0442(6) Uani d . 1 . .
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
N2 C1 N1 . . 114.2(3) ?
N2 C1 H1 . . 122.9 ?
N1 C1 H1 . . 122.9 ?
N2 C2 C3 . . 103.1(3) ?
N2 C2 H2A . . 111.2 ?
C3 C2 H2A . . 111.2 ?
N2 C2 H2B . . 111.2 ?
C3 C2 H2B . . 111.2 ?
H2A C2 H2B . . 109.1 ?
N1 C3 C2 . . 101.9(2) ?
N1 C3 H3A . . 111.4 ?
C2 C3 H3A . . 111.4 ?
N1 C3 H3B . . 111.4 ?
C2 C3 H3B . . 111.4 ?
H3A C3 H3B . . 109.2 ?
C9 C4 C5 . . 123.2(4) ?
C9 C4 N2 . . 119.0(3) ?
C5 C4 N2 . . 117.5(4) ?
C6 C5 C4 . . 116.9(4) ?
C6 C5 C10 . . 120.6(4) ?
C4 C5 C10 . . 122.4(4) ?
C7 C6 C5 . . 120.4(4) ?
C7 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C8 C7 C6 . . 122.0(4) ?
C8 C7 H7 . . 119.0 ?
C6 C7 H7 . . 119.0 ?
C7 C8 C9 . . 120.5(4) ?
C7 C8 H8 . . 119.7 ?
C9 C8 H8 . . 119.7 ?
C8 C9 C4 . . 116.8(4) ?
C8 C9 C13 . . 120.1(4) ?
C4 C9 C13 . . 123.0(3) ?
C12 C10 C5 . . 113.6(4) ?
C12 C10 C11 . . 108.3(5) ?
C5 C10 C11 . . 110.5(5) ?
C12 C10 H10 . . 108.1 ?
C5 C10 H10 . . 108.1 ?
C11 C10 H10 . . 108.1 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C10 C12 H12A . . 109.5 ?
C10 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C10 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 C9 . . 113.0(4) ?
C14 C13 C15 . . 111.9(4) ?
C9 C13 C15 . . 109.5(4) ?
C14 C13 H13 . . 107.4 ?
C9 C13 H13 . . 107.4 ?
C15 C13 H13 . . 107.4 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C13 C15 H15A . . 109.5 ?
C13 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C13 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C17 C16 C21 . . 123.7(4) ?
C17 C16 N1 . . 119.0(4) ?
C21 C16 N1 . . 117.2(4) ?
C16 C17 C18 . . 117.3(5) ?
C16 C17 C25 . . 122.6(4) ?
C18 C17 C25 . . 120.1(5) ?
C19 C18 C17 . . 120.4(5) ?
C19 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C18 C19 C20 . . 122.2(4) ?
C18 C19 H19 . . 118.9 ?
C20 C19 H19 . . 118.9 ?
C19 C20 C21 . . 119.9(5) ?
C19 C20 H20 . . 120.1 ?
C21 C20 H20 . . 120.1 ?
C20 C21 C16 . . 116.5(4) ?
C20 C21 C22 . . 120.8(4) ?
C16 C21 C22 . . 122.6(3) ?
C21 C22 C23 . . 114.3(4) ?
C21 C22 C24 . . 110.2(4) ?
C23 C22 C24 . . 110.9(4) ?
C21 C22 H22 . . 107.1 ?
C23 C22 H22 . . 107.1 ?
C24 C22 H22 . . 107.1 ?
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 ?
C22 C24 H24A . . 109.5 ?
C22 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C22 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C17 C25 C27 . . 110.6(5) ?
C17 C25 C26 . . 113.3(4) ?
C27 C25 C26 . . 109.8(5) ?
C17 C25 H25 . . 107.6 ?
C27 C25 H25 . . 107.6 ?
C26 C25 H25 . . 107.6 ?
C25 C26 H26A . . 109.5 ?
C25 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C25 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C25 C27 H27A . . 109.5 ?
C25 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C25 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C29 C28 C33 . . 115.2(4) ?
C29 C28 B1 . . 122.5(4) ?
C33 C28 B1 . . 121.8(4) ?
C28 C29 C30 . . 122.7(5) ?
C28 C29 H29 . . 118.7 ?
C30 C29 H29 . . 118.7 ?
C31 C30 C29 . . 119.6(6) ?
C31 C30 H30 . . 120.2 ?
C29 C30 H30 . . 120.2 ?
C32 C31 C30 . . 120.0(5) ?
C32 C31 H31 . . 120.0 ?
C30 C31 H31 . . 120.0 ?
C31 C32 C33 . . 120.3(6) ?
C31 C32 H32 . . 119.9 ?
C33 C32 H32 . . 119.9 ?
C28 C33 C32 . . 122.3(5) ?
C28 C33 H33 . . 118.9 ?
C32 C33 H33 . . 118.9 ?
C39 C34 C35 . . 113.9(4) ?
C39 C34 B1 . . 123.6(3) ?
C35 C34 B1 . . 122.4(3) ?
C36 C35 C34 . . 123.3(4) ?
C36 C35 H35 . . 118.4 ?
C34 C35 H35 . . 118.4 ?
C37 C36 C35 . . 120.1(5) ?
C37 C36 H36 . . 120.0 ?
C35 C36 H36 . . 120.0 ?
C36 C37 C38 . . 118.9(5) ?
C36 C37 H37 . . 120.6 ?
C38 C37 H37 . . 120.6 ?
C37 C38 C39 . . 121.1(4) ?
C37 C38 H38 . . 119.5 ?
C39 C38 H38 . . 119.5 ?
C38 C39 C34 . . 122.8(4) ?
C38 C39 H39 . . 118.6 ?
C34 C39 H39 . . 118.6 ?
C45 C40 C41 . . 115.2(3) ?
C45 C40 B1 . . 123.4(3) ?
C41 C40 B1 . . 121.2(3) ?
C42 C41 C40 . . 121.5(4) ?
C42 C41 H41 . . 119.2 ?
C40 C41 H41 . . 119.2 ?
C43 C42 C41 . . 121.8(4) ?
C43 C42 H42 . . 119.1 ?
C41 C42 H42 . . 119.1 ?
C44 C43 C42 . . 117.9(4) ?
C44 C43 H43 . . 121.0 ?
C42 C43 H43 . . 121.0 ?
C43 C44 C45 . . 121.3(4) ?
C43 C44 H44 . . 119.4 ?
C45 C44 H44 . . 119.4 ?
C40 C45 C44 . . 122.2(4) ?
C40 C45 H45 . . 118.9 ?
C44 C45 H45 . . 118.9 ?
C47 C46 C51 . . 114.5(4) ?
C47 C46 B1 . . 122.7(4) ?
C51 C46 B1 . . 122.4(4) ?
C48 C47 C46 . . 121.3(5) ?
C48 C47 H47 . . 119.3 ?
C46 C47 H47 . . 119.3 ?
C49 C48 C47 . . 121.6(5) ?
C49 C48 H48 . . 119.2 ?
C47 C48 H48 . . 119.2 ?
C50 C49 C48 . . 119.3(5) ?
C50 C49 H49 . . 120.3 ?
C48 C49 H49 . . 120.3 ?
C49 C50 C51 . . 119.6(5) ?
C49 C50 H50 . . 120.2 ?
C51 C50 H50 . . 120.2 ?
C50 C51 C46 . . 123.5(5) ?
C50 C51 H51 . . 118.3 ?
C46 C51 H51 . . 118.3 ?
Cl2 C52 Cl1 . . 109.2(4) ?
Cl2 C52 H52B . . 109.8 ?
Cl1 C52 H52B . . 109.8 ?
Cl2 C52 H52A . . 109.8 ?
Cl1 C52 H52A . . 109.8 ?
H52B C52 H52A . . 108.3 ?
Cl4 C53 Cl3 . . 111.8(3) ?
Cl4 C53 H53B . . 109.3 ?
Cl3 C53 H53B . . 109.3 ?
Cl4 C53 H53A . . 109.3 ?
Cl3 C53 H53A . . 109.3 ?
H53B C53 H53A . . 107.9 ?
C46 B1 C34 . . 113.2(3) ?
C46 B1 C28 . . 102.5(3) ?
C34 B1 C28 . . 112.2(3) ?
C46 B1 C40 . . 113.2(3) ?
C34 B1 C40 . . 104.4(3) ?
C28 B1 C40 . . 111.7(3) ?
C1 N1 C16 . . 125.6(3) ?
C1 N1 C3 . . 110.0(3) ?
C16 N1 C3 . . 123.9(3) ?
C1 N2 C4 . . 128.0(3) ?
C1 N2 C2 . . 109.3(2) ?
C4 N2 C2 . . 122.0(3) ?
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
C1 N2 . 1.297(4) ?
C1 N1 . 1.301(4) ?
C1 H1 . 0.9300 ?
C2 N2 . 1.474(4) ?
C2 C3 . 1.526(5) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N1 . 1.474(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C9 . 1.391(6) ?
C4 C5 . 1.398(6) ?
C4 N2 . 1.441(5) ?
C5 C6 . 1.385(6) ?
C5 C10 . 1.514(7) ?
C6 C7 . 1.366(7) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.357(7) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.392(6) ?
C8 H8 . 0.9300 ?
C9 C13 . 1.507(7) ?
C10 C12 . 1.509(6) ?
C10 C11 . 1.523(9) ?
C10 H10 . 0.9800 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.503(8) ?
C13 C15 . 1.536(6) ?
C13 H13 . 0.9800 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 C17 . 1.381(7) ?
C16 C21 . 1.407(7) ?
C16 N1 . 1.452(4) ?
C17 C18 . 1.396(6) ?
C17 C25 . 1.514(7) ?
C18 C19 . 1.361(8) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.381(7) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.401(6) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.502(7) ?
C22 C23 . 1.513(7) ?
C22 C24 . 1.544(6) ?
C22 H22 . 0.9800 ?
C23 H23A . 0.9600 ?
C23 H23B . 0.9600 ?
C23 H23C . 0.9600 ?
C24 H24A . 0.9600 ?
C24 H24B . 0.9600 ?
C24 H24C . 0.9600 ?
C25 C27 . 1.518(8) ?
C25 C26 . 1.530(8) ?
C25 H25 . 0.9800 ?
C26 H26A . 0.9600 ?
C26 H26B . 0.9600 ?
C26 H26C . 0.9600 ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 0.9600 ?
C28 C29 . 1.390(6) ?
C28 C33 . 1.386(6) ?
C28 B1 . 1.648(5) ?
C29 C30 . 1.393(7) ?
C29 H29 . 0.9300 ?
C30 C31 . 1.372(10) ?
C30 H30 . 0.9300 ?
C31 C32 . 1.340(10) ?
C31 H31 . 0.9300 ?
C32 C33 . 1.407(7) ?
C32 H32 . 0.9300 ?
C33 H33 . 0.9300 ?
C34 C39 . 1.400(5) ?
C34 C35 . 1.403(5) ?
C34 B1 . 1.637(6) ?
C35 C36 . 1.384(7) ?
C35 H35 . 0.9300 ?
C36 C37 . 1.367(7) ?
C36 H36 . 0.9300 ?
C37 C38 . 1.362(7) ?
C37 H37 . 0.9300 ?
C38 C39 . 1.378(6) ?
C38 H38 . 0.9300 ?
C39 H39 . 0.9300 ?
C40 C45 . 1.383(5) ?
C40 C41 . 1.390(5) ?
C40 B1 . 1.657(5) ?
C41 C42 . 1.400(6) ?
C41 H41 . 0.9300 ?
C42 C43 . 1.352(7) ?
C42 H42 . 0.9300 ?
C43 C44 . 1.350(7) ?
C43 H43 . 0.9300 ?
C44 C45 . 1.403(6) ?
C44 H44 . 0.9300 ?
C45 H45 . 0.9300 ?
C46 C47 . 1.397(6) ?
C46 C51 . 1.397(6) ?
C46 B1 . 1.645(5) ?
C47 C48 . 1.401(7) ?
C47 H47 . 0.9300 ?
C48 C49 . 1.344(9) ?
C48 H48 . 0.9300 ?
C49 C50 . 1.362(8) ?
C49 H49 . 0.9300 ?
C50 C51 . 1.389(6) ?
C50 H50 . 0.9300 ?
C51 H51 . 0.9300 ?
C52 Cl2 . 1.665(8) ?
C52 Cl1 . 1.699(9) ?
C52 H52B . 0.9700 ?
C52 H52A . 0.9700 ?
C53 Cl4 . 1.705(8) ?
C53 Cl3 . 1.739(8) ?
C53 H53B . 0.9700 ?
C53 H53A . 0.9700 ?
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
C3 H3A Cg2 . 0.97 2.87 3.677(4) 141
C3 H3B Cg3 . 0.97 2.75 3.562(4) 141
C52 H52A Cg1 4_464 0.97 2.44 3.406(7) 171
C52 H52B Cg4 4_464 0.97 2.62 3.434(7) 141
C53 H53A Cg4 1_545 0.97 2.88 3.818(8) 162
C53 H53B Cg1 . 0.97 2.63 3.585(8) 169
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656164
2 PubChem 139079371
