#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/67/7106713.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_7106713
loop_
_publ_author_name
'Liping Cao'
'Jun-Gang Wang'
'Jiao-Yang Ding'
'Anxin Wu'
'Lyle Isaacs'
_publ_section_title
;
 Reassembly self-sorting triggered by heterodimerization
;
_journal_name_full               Chem.Commun.
_journal_page_first              8548
_journal_paper_doi               10.1039/c1cc13288a
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C37 H33 F5 N6 O10, 3(C H Cl3)'
_chemical_formula_sum            'C40 H36 Cl9 F5 N6 O10'
_chemical_formula_weight         1174.80
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                116.7660(10)
_cell_angle_beta                 97.158(2)
_cell_angle_gamma                90.808(2)
_cell_formula_units_Z            2
_cell_length_a                   10.5648(10)
_cell_length_b                   15.5841(14)
_cell_length_c                   16.8119(15)
_cell_measurement_reflns_used    7642
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.5
_cell_volume                     2444.4(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0845
_diffrn_reflns_av_sigmaI/netI    0.0754
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28452
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  0.9428
_exptl_absorpt_correction_T_min  0.8901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, (Sheldrick,1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     662
_refine_ls_number_reflns         10910
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0847P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1534
_reflns_number_gt                7029
_reflns_number_total             10910
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc13288a.txt
_cod_data_source_block           081225cm
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7106713
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2946(3) 1.2395(2) 0.35267(19) 0.0413(7) Uani 1 1 d . . .
H1A H -0.3770 1.2671 0.3507 0.062 Uiso 1 1 calc R . .
H1B H -0.2776 1.1993 0.2911 0.062 Uiso 1 1 calc R . .
H1C H -0.2265 1.2916 0.3846 0.062 Uiso 1 1 calc R . .
C2 C -0.2987(2) 1.17872(18) 0.40129(17) 0.0299(5) Uani 1 1 d . . .
C3 C -0.2210(2) 1.02895(17) 0.40045(15) 0.0254(5) Uani 1 1 d . . .
C4 C -0.1822(2) 1.06321(18) 0.49231(15) 0.0283(5) Uani 1 1 d . . .
H4 H -0.1752 1.1306 0.5310 0.034 Uiso 1 1 calc R . .
C5 C -0.1536(2) 1.00015(18) 0.52784(15) 0.0294(5) Uani 1 1 d . . .
H5 H -0.1315 1.0240 0.5911 0.035 Uiso 1 1 calc R . .
C6 C -0.1572(2) 0.90146(17) 0.47096(15) 0.0261(5) Uani 1 1 d . . .
C7 C -0.1955(2) 0.86634(16) 0.37842(15) 0.0233(5) Uani 1 1 d . . .
C8 C -0.2321(2) 0.92974(16) 0.34296(15) 0.0233(5) Uani 1 1 d . . .
C9 C -0.0939(3) 0.8668(2) 0.59379(16) 0.0377(6) Uani 1 1 d . . .
H9A H -0.0233 0.9174 0.6192 0.057 Uiso 1 1 calc R . .
H9B H -0.0691 0.8126 0.6052 0.057 Uiso 1 1 calc R . .
H9C H -0.1697 0.8927 0.6220 0.057 Uiso 1 1 calc R . .
C10 C -0.2820(2) 0.88940(16) 0.24371(14) 0.0228(5) Uani 1 1 d . . .
H10A H -0.3537 0.8404 0.2283 0.027 Uiso 1 1 calc R . .
H10B H -0.3164 0.9421 0.2320 0.027 Uiso 1 1 calc R . .
C11 C -0.1935(2) 0.75954(16) 0.31646(14) 0.0240(5) Uani 1 1 d . . .
H11A H -0.1648 0.7260 0.3526 0.029 Uiso 1 1 calc R . .
H11B H -0.2811 0.7324 0.2851 0.029 Uiso 1 1 calc R . .
C12 C -0.0841(2) 0.90333(17) 0.18481(14) 0.0235(5) Uani 1 1 d . . .
C13 C 0.0180(2) 0.72838(15) 0.26332(14) 0.0213(5) Uani 1 1 d . . .
C14 C -0.1461(2) 0.75099(16) 0.16831(14) 0.0203(5) Uani 1 1 d . . .
C15 C -0.2518(2) 0.67134(17) 0.10563(15) 0.0241(5) Uani 1 1 d . A .
C17 C -0.3797(9) 0.4768(7) 0.0934(6) 0.048(3) Uani 0.480(18) 1 d PD A 1
H17A H -0.3241 0.4641 0.1375 0.073 Uiso 0.480(18) 1 calc PR A 1
H17B H -0.4395 0.4202 0.0556 0.073 Uiso 0.480(18) 1 calc PR A 1
H17C H -0.4278 0.5326 0.1250 0.073 Uiso 0.480(18) 1 calc PR A 1
C16 C -0.2989(9) 0.4976(5) 0.0351(6) 0.029(2) Uani 0.480(18) 1 d PD A 1
H16A H -0.2450 0.4439 0.0059 0.035 Uiso 0.480(18) 1 calc PR A 1
H16B H -0.3536 0.5070 -0.0121 0.035 Uiso 0.480(18) 1 calc PR A 1
C16' C -0.3314(10) 0.5147(7) 0.0566(10) 0.054(3) Uani 0.520(18) 1 d PD A 2
H16C H -0.4114 0.5480 0.0656 0.065 Uiso 0.520(18) 1 calc PR A 2
H16D H -0.3307 0.4764 -0.0089 0.065 Uiso 0.520(18) 1 calc PR A 2
C17' C -0.3261(11) 0.4506(6) 0.0998(6) 0.059(3) Uani 0.520(18) 1 d PD A 2
H17D H -0.2416 0.4252 0.0986 0.089 Uiso 0.520(18) 1 calc PR A 2
H17E H -0.3920 0.3969 0.0671 0.089 Uiso 0.520(18) 1 calc PR A 2
H17F H -0.3411 0.4869 0.1624 0.089 Uiso 0.520(18) 1 calc PR A 2
C18 C -0.0150(2) 0.74694(16) 0.13232(14) 0.0227(5) Uani 1 1 d . . .
C19 C -0.0111(2) 0.68064(18) 0.03206(16) 0.0315(6) Uani 1 1 d . . .
C20 C -0.1218(3) 0.6192(2) -0.11566(16) 0.0401(7) Uani 1 1 d . . .
H20A H -0.0430 0.6338 -0.1351 0.048 Uiso 1 1 calc R . .
H20B H -0.1958 0.6342 -0.1482 0.048 Uiso 1 1 calc R . .
C21 C -0.1337(3) 0.5148(2) -0.13904(18) 0.0513(8) Uani 1 1 d . . .
H21A H -0.0552 0.4980 -0.1135 0.077 Uiso 1 1 calc R . .
H21B H -0.1472 0.4762 -0.2047 0.077 Uiso 1 1 calc R . .
H21C H -0.2067 0.5017 -0.1143 0.077 Uiso 1 1 calc R . .
C22 C 0.1363(2) 0.88098(18) 0.14198(15) 0.0267(5) Uani 1 1 d . . .
H22A H 0.1264 0.9410 0.1361 0.032 Uiso 1 1 calc R . .
H22B H 0.1645 0.8324 0.0860 0.032 Uiso 1 1 calc R . .
C23 C 0.2099(2) 0.72846(16) 0.19622(16) 0.0252(5) Uani 1 1 d . . .
H23A H 0.2333 0.7007 0.1348 0.030 Uiso 1 1 calc R . .
H23B H 0.2469 0.6898 0.2253 0.030 Uiso 1 1 calc R . .
C24 C 0.2400(2) 0.90089(17) 0.22097(15) 0.0248(5) Uani 1 1 d . . .
C25 C 0.2713(2) 0.83090(16) 0.24886(15) 0.0239(5) Uani 1 1 d . . .
C26 C 0.3677(2) 0.85388(18) 0.32235(16) 0.0273(5) Uani 1 1 d . . .
C27 C 0.4344(2) 0.94334(19) 0.36416(16) 0.0323(6) Uani 1 1 d . . .
H27 H 0.4991 0.9584 0.4141 0.039 Uiso 1 1 calc R . .
C28 C 0.4081(2) 1.01171(18) 0.33418(16) 0.0324(6) Uani 1 1 d . . .
H28 H 0.4564 1.0724 0.3622 0.039 Uiso 1 1 calc R . .
C29 C 0.3115(2) 0.99119(17) 0.26346(16) 0.0283(5) Uani 1 1 d . . .
C30 C 0.3689(3) 1.1322(2) 0.2506(2) 0.0509(8) Uani 1 1 d . . .
H30A H 0.3780 1.1756 0.3154 0.076 Uiso 1 1 calc R . .
H30B H 0.3386 1.1673 0.2169 0.076 Uiso 1 1 calc R . .
H30C H 0.4520 1.1081 0.2346 0.076 Uiso 1 1 calc R . .
C31 C 0.4689(2) 0.71162(19) 0.30982(16) 0.0317(6) Uani 1 1 d . . .
C32 C 0.5079(2) 0.65063(19) 0.35609(17) 0.0320(6) Uani 1 1 d . . .
C33 C 0.5772(2) 0.6876(2) 0.44116(17) 0.0345(6) Uani 1 1 d . . .
C34 C 0.6183(3) 0.6294(2) 0.47990(18) 0.0453(7) Uani 1 1 d . . .
C35 C 0.5892(3) 0.5321(2) 0.4331(2) 0.0533(8) Uani 1 1 d . . .
C36 C 0.5209(3) 0.4927(2) 0.3488(2) 0.0542(8) Uani 1 1 d . . .
C37 C 0.4823(3) 0.5513(2) 0.31088(18) 0.0418(7) Uani 1 1 d . . .
C38 C 0.5688(3) 0.8409(2) 0.01470(18) 0.0417(7) Uani 1 1 d . . .
H38 H 0.6294 0.8048 0.0366 0.050 Uiso 1 1 calc R . .
C39 C 0.9810(3) 0.1479(2) 0.1483(2) 0.0502(8) Uani 1 1 d . . .
H39 H 0.9695 0.0906 0.1594 0.060 Uiso 1 1 calc R . .
C40 C 1.0140(3) 0.5746(3) 0.3900(2) 0.0591(9) Uani 1 1 d . . .
H40 H 1.0347 0.6338 0.3836 0.071 Uiso 1 1 calc R . .
Cl1 Cl 0.64878(8) 0.95009(6) 0.03769(6) 0.0632(2) Uani 1 1 d . . .
Cl2 Cl 0.43750(8) 0.86025(8) 0.07191(6) 0.0718(3) Uani 1 1 d . . .
Cl3 Cl 0.52262(11) 0.77031(7) -0.10128(5) 0.0787(3) Uani 1 1 d . . .
Cl4 Cl 1.04402(10) 0.24719(7) 0.25060(5) 0.0676(3) Uani 1 1 d . . .
Cl5 Cl 0.83132(9) 0.17074(8) 0.10651(7) 0.0742(3) Uani 1 1 d . . .
Cl6 Cl 1.08695(9) 0.12239(6) 0.06943(6) 0.0624(2) Uani 1 1 d . . .
Cl7 Cl 0.89046(11) 0.50548(10) 0.30485(9) 0.1040(4) Uani 1 1 d . . .
Cl8 Cl 1.15150(9) 0.51073(9) 0.37948(7) 0.0810(3) Uani 1 1 d . . .
Cl9 Cl 0.96613(12) 0.61027(8) 0.49499(7) 0.0905(4) Uani 1 1 d . . .
F1 F 0.60811(14) 0.78304(11) 0.48850(10) 0.0416(4) Uani 1 1 d . . .
F2 F 0.68536(18) 0.66842(14) 0.56327(11) 0.0621(5) Uani 1 1 d . . .
F3 F 0.6284(2) 0.47560(14) 0.47062(14) 0.0787(7) Uani 1 1 d . . .
F4 F 0.4910(2) 0.39662(14) 0.30391(15) 0.0839(7) Uani 1 1 d . . .
F5 F 0.41315(17) 0.50996(13) 0.22778(11) 0.0590(5) Uani 1 1 d . . .
N1 N -0.24250(19) 1.09479(14) 0.36326(13) 0.0282(4) Uani 1 1 d D . .
H1 H -0.213(2) 1.0820(18) 0.3142(11) 0.034 Uiso 1 1 d D . .
N2 N -0.18555(17) 0.84494(13) 0.18382(12) 0.0213(4) Uani 1 1 d . . .
N3 N -0.10817(17) 0.74275(13) 0.25013(12) 0.0221(4) Uani 1 1 d . . .
N4 N 0.01194(17) 0.84619(13) 0.15042(12) 0.0229(4) Uani 1 1 d . . .
N5 N 0.07125(17) 0.71816(13) 0.18858(12) 0.0224(4) Uani 1 1 d . . .
N6 N 0.40047(19) 0.78536(15) 0.35513(13) 0.0294(5) Uani 1 1 d D . .
H6 H 0.386(2) 0.8008(18) 0.4078(9) 0.035 Uiso 1 1 d D . .
O1 O -0.35084(17) 1.20320(12) 0.46825(12) 0.0368(4) Uani 1 1 d . . .
O2 O -0.12232(16) 0.83462(12) 0.49911(10) 0.0320(4) Uani 1 1 d . . .
O3 O -0.08362(15) 0.99030(11) 0.21077(10) 0.0261(4) Uani 1 1 d . . .
O4 O 0.07552(15) 0.72350(11) 0.32852(11) 0.0280(4) Uani 1 1 d . . .
O5 O -0.35024(16) 0.68614(12) 0.07252(11) 0.0325(4) Uani 1 1 d . . .
O6 O -0.21880(17) 0.58682(12) 0.09720(14) 0.0466(5) Uani 1 1 d D . .
O7 O 0.0799(2) 0.6408(2) 0.00448(14) 0.0772(8) Uani 1 1 d . . .
O8 O -0.11675(17) 0.67999(12) -0.01779(11) 0.0355(4) Uani 1 1 d . . .
O9 O 0.27912(17) 1.05324(12) 0.22879(12) 0.0363(4) Uani 1 1 d . . .
O10 O 0.49949(16) 0.69207(14) 0.23633(12) 0.0389(4) Uani 1 1 d . . .
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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 123.5(2) . . ?
O1 C2 C1 122.1(2) . . ?
N1 C2 C1 114.4(2) . . ?
C4 C3 C8 120.1(2) . . ?
C4 C3 N1 120.3(2) . . ?
C8 C3 N1 119.5(2) . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
O2 C6 C5 124.2(2) . . ?
O2 C6 C7 116.1(2) . . ?
C5 C6 C7 119.7(2) . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 C11 119.45(19) . . ?
C8 C7 C11 120.31(19) . . ?
C3 C8 C7 119.1(2) . . ?
C3 C8 C10 121.7(2) . . ?
C7 C8 C10 119.3(2) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C8 114.44(17) . . ?
N2 C10 H10A 108.7 . . ?
C8 C10 H10A 108.7 . . ?
N2 C10 H10B 108.7 . . ?
C8 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N3 C11 C7 111.22(18) . . ?
N3 C11 H11A 109.4 . . ?
C7 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
C7 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
O3 C12 N4 126.8(2) . . ?
O3 C12 N2 125.2(2) . . ?
N4 C12 N2 108.01(19) . . ?
O4 C13 N3 126.7(2) . . ?
O4 C13 N5 125.0(2) . . ?
N3 C13 N5 108.33(18) . . ?
N2 C14 N3 113.68(17) . . ?
N2 C14 C15 110.70(17) . . ?
N3 C14 C15 110.43(17) . . ?
N2 C14 C18 103.43(16) . . ?
N3 C14 C18 101.94(16) . . ?
C15 C14 C18 116.36(17) . . ?
O5 C15 O6 125.7(2) . . ?
O5 C15 C14 124.0(2) . . ?
O6 C15 C14 110.22(19) . . ?
O6 C16 C17 105.2(5) . . ?
O6 C16 H16A 110.7 . . ?
C17 C16 H16A 110.7 . . ?
O6 C16 H16B 110.7 . . ?
C17 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C17' C16' O6 109.1(6) . . ?
C17' C16' H16C 109.9 . . ?
O6 C16' H16C 109.9 . . ?
C17' C16' H16D 109.9 . . ?
O6 C16' H16D 109.9 . . ?
H16C C16' H16D 108.3 . . ?
C16' C17' H17D 109.5 . . ?
C16' C17' H17E 109.5 . . ?
H17D C17' H17E 109.5 . . ?
C16' C17' H17F 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
N5 C18 N4 113.20(18) . . ?
N5 C18 C19 110.84(18) . . ?
N4 C18 C19 108.88(18) . . ?
N5 C18 C14 103.65(17) . . ?
N4 C18 C14 102.21(16) . . ?
C19 C18 C14 117.88(18) . . ?
O7 C19 O8 125.2(2) . . ?
O7 C19 C18 123.3(2) . . ?
O8 C19 C18 111.4(2) . . ?
O8 C20 C21 111.1(2) . . ?
O8 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
O8 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C22 C24 113.92(18) . . ?
N4 C22 H22A 108.8 . . ?
C24 C22 H22A 108.8 . . ?
N4 C22 H22B 108.8 . . ?
C24 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
N5 C23 C25 115.67(18) . . ?
N5 C23 H23A 108.4 . . ?
C25 C23 H23A 108.4 . . ?
N5 C23 H23B 108.4 . . ?
C25 C23 H23B 108.4 . . ?
H23A C23 H23B 107.4 . . ?
C25 C24 C29 119.3(2) . . ?
C25 C24 C22 122.1(2) . . ?
C29 C24 C22 118.5(2) . . ?
C24 C25 C26 119.3(2) . . ?
C24 C25 C23 120.8(2) . . ?
C26 C25 C23 119.7(2) . . ?
C27 C26 C25 120.3(2) . . ?
C27 C26 N6 118.4(2) . . ?
C25 C26 N6 121.3(2) . . ?
C26 C27 C28 120.8(2) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C29 C28 C27 119.7(2) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
O9 C29 C28 124.1(2) . . ?
O9 C29 C24 115.4(2) . . ?
C28 C29 C24 120.5(2) . . ?
O9 C30 H30A 109.5 . . ?
O9 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O9 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O10 C31 N6 124.7(2) . . ?
O10 C31 C32 120.1(2) . . ?
N6 C31 C32 115.1(2) . . ?
C33 C32 C37 116.3(2) . . ?
C33 C32 C31 123.2(2) . . ?
C37 C32 C31 120.3(2) . . ?
F1 C33 C32 119.9(2) . . ?
F1 C33 C34 118.1(2) . . ?
C32 C33 C34 122.1(3) . . ?
F2 C34 C35 120.4(3) . . ?
F2 C34 C33 120.2(3) . . ?
C35 C34 C33 119.4(3) . . ?
F3 C35 C36 120.1(3) . . ?
F3 C35 C34 119.5(3) . . ?
C36 C35 C34 120.4(3) . . ?
F4 C36 C35 119.8(3) . . ?
F4 C36 C37 120.7(3) . . ?
C35 C36 C37 119.5(3) . . ?
F5 C37 C36 118.0(3) . . ?
F5 C37 C32 119.7(2) . . ?
C36 C37 C32 122.3(3) . . ?
Cl2 C38 Cl1 110.86(16) . . ?
Cl2 C38 Cl3 110.91(16) . . ?
Cl1 C38 Cl3 111.06(14) . . ?
Cl2 C38 H38 108.0 . . ?
Cl1 C38 H38 108.0 . . ?
Cl3 C38 H38 108.0 . . ?
Cl6 C39 Cl4 110.33(17) . . ?
Cl6 C39 Cl5 110.32(16) . . ?
Cl4 C39 Cl5 110.27(18) . . ?
Cl6 C39 H39 108.6 . . ?
Cl4 C39 H39 108.6 . . ?
Cl5 C39 H39 108.6 . . ?
Cl7 C40 Cl9 110.37(19) . . ?
Cl7 C40 Cl8 110.4(2) . . ?
Cl9 C40 Cl8 111.39(17) . . ?
Cl7 C40 H40 108.2 . . ?
Cl9 C40 H40 108.2 . . ?
Cl8 C40 H40 108.2 . . ?
C2 N1 C3 125.9(2) . . ?
C2 N1 H1 116.7(17) . . ?
C3 N1 H1 117.4(17) . . ?
C12 N2 C14 111.07(17) . . ?
C12 N2 C10 118.92(18) . . ?
C14 N2 C10 120.03(17) . . ?
C13 N3 C14 113.43(17) . . ?
C13 N3 C11 123.51(18) . . ?
C14 N3 C11 122.70(17) . . ?
C12 N4 C18 113.03(18) . . ?
C12 N4 C22 124.78(19) . . ?
C18 N4 C22 121.81(18) . . ?
C13 N5 C18 110.65(17) . . ?
C13 N5 C23 118.42(18) . . ?
C18 N5 C23 123.41(18) . . ?
C31 N6 C26 120.5(2) . . ?
C31 N6 H6 123.4(18) . . ?
C26 N6 H6 115.2(18) . . ?
C6 O2 C9 117.34(19) . . ?
C15 O6 C16 120.9(4) . . ?
C15 O6 C16' 110.3(4) . . ?
C16 O6 C16' 20.0(6) . . ?
C19 O8 C20 115.57(19) . . ?
C29 O9 C30 117.4(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.508(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.220(3) . ?
C2 N1 1.355(3) . ?
C3 C4 1.390(3) . ?
C3 C8 1.400(3) . ?
C3 N1 1.430(3) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(3) . ?
C5 H5 0.9500 . ?
C6 O2 1.362(3) . ?
C6 C7 1.398(3) . ?
C7 C8 1.402(3) . ?
C7 C11 1.517(3) . ?
C8 C10 1.511(3) . ?
C9 O2 1.426(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N2 1.476(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N3 1.455(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O3 1.222(3) . ?
C12 N4 1.366(3) . ?
C12 N2 1.390(3) . ?
C13 O4 1.219(3) . ?
C13 N3 1.363(3) . ?
C13 N5 1.385(3) . ?
C14 N2 1.444(3) . ?
C14 N3 1.446(3) . ?
C14 C15 1.545(3) . ?
C14 C18 1.570(3) . ?
C15 O5 1.193(3) . ?
C15 O6 1.316(3) . ?
C17 C16 1.509(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C16 O6 1.476(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16' C17' 1.474(8) . ?
C16' O6 1.488(8) . ?
C16' H16C 0.9900 . ?
C16' H16D 0.9900 . ?
C17' H17D 0.9800 . ?
C17' H17E 0.9800 . ?
C17' H17F 0.9800 . ?
C18 N5 1.451(3) . ?
C18 N4 1.452(3) . ?
C18 C19 1.536(3) . ?
C19 O7 1.180(3) . ?
C19 O8 1.307(3) . ?
C20 O8 1.477(3) . ?
C20 C21 1.490(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 N4 1.462(3) . ?
C22 C24 1.522(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 N5 1.455(3) . ?
C23 C25 1.519(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.397(3) . ?
C24 C29 1.411(3) . ?
C25 C26 1.404(3) . ?
C26 C27 1.378(3) . ?
C26 N6 1.434(3) . ?
C27 C28 1.387(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.379(3) . ?
C28 H28 0.9500 . ?
C29 O9 1.363(3) . ?
C30 O9 1.422(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 O10 1.219(3) . ?
C31 N6 1.340(3) . ?
C31 C32 1.508(3) . ?
C32 C33 1.378(3) . ?
C32 C37 1.388(4) . ?
C33 F1 1.344(3) . ?
C33 C34 1.382(4) . ?
C34 F2 1.345(3) . ?
C34 C35 1.366(4) . ?
C35 F3 1.339(3) . ?
C35 C36 1.361(4) . ?
C36 F4 1.349(4) . ?
C36 C37 1.371(4) . ?
C37 F5 1.350(3) . ?
C38 Cl2 1.739(3) . ?
C38 Cl1 1.745(3) . ?
C38 Cl3 1.751(3) . ?
C38 H38 1.0000 . ?
C39 Cl6 1.754(3) . ?
C39 Cl4 1.756(3) . ?
C39 Cl5 1.757(3) . ?
C39 H39 1.0000 . ?
C40 Cl7 1.737(4) . ?
C40 Cl9 1.740(3) . ?
C40 Cl8 1.755(3) . ?
C40 H40 1.0000 . ?
N1 H1 0.855(10) . ?
N6 H6 0.843(10) . ?
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
C23 H23A O7 0.99 2.35 3.004(3) 122.7 .
C40 H40 O4 1.00 2.06 3.027(4) 161.7 1_655
C38 H38 O5 1.00 2.19 3.075(3) 146.1 1_655
C30 H30A F2 0.98 2.54 3.393(4) 145.9 2_676
C17' H17D O7 0.98 2.48 3.295(12) 140.2 2_565
C11 H11B O10 0.99 2.34 3.314(3) 168.8 1_455
C4 H4 O4 0.95 2.52 3.380(3) 151.1 2_576
N6 H6 O1 0.843(10) 2.188(12) 3.006(3) 164(2) 2_576
N1 H1 O3 0.855(10) 2.315(16) 3.071(2) 148(2) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C3 C4 C5 0.3(3) . . . . ?
N1 C3 C4 C5 -176.0(2) . . . . ?
C3 C4 C5 C6 3.3(3) . . . . ?
C4 C5 C6 O2 175.4(2) . . . . ?
C4 C5 C6 C7 -3.0(3) . . . . ?
O2 C6 C7 C8 -179.48(19) . . . . ?
C5 C6 C7 C8 -1.0(3) . . . . ?
O2 C6 C7 C11 -1.2(3) . . . . ?
C5 C6 C7 C11 177.3(2) . . . . ?
C4 C3 C8 C7 -4.2(3) . . . . ?
N1 C3 C8 C7 172.11(19) . . . . ?
C4 C3 C8 C10 176.1(2) . . . . ?
N1 C3 C8 C10 -7.6(3) . . . . ?
C6 C7 C8 C3 4.5(3) . . . . ?
C11 C7 C8 C3 -173.7(2) . . . . ?
C6 C7 C8 C10 -175.7(2) . . . . ?
C11 C7 C8 C10 6.0(3) . . . . ?
C3 C8 C10 N2 112.1(2) . . . . ?
C7 C8 C10 N2 -67.6(3) . . . . ?
C6 C7 C11 N3 -119.6(2) . . . . ?
C8 C7 C11 N3 58.6(3) . . . . ?
N2 C14 C15 O5 2.4(3) . . . . ?
N3 C14 C15 O5 129.2(2) . . . . ?
C18 C14 C15 O5 -115.3(2) . . . . ?
N2 C14 C15 O6 -175.44(19) . . . . ?
N3 C14 C15 O6 -48.6(2) . . . . ?
C18 C14 C15 O6 66.9(2) . . . . ?
N2 C14 C18 N5 129.06(17) . . . . ?
N3 C14 C18 N5 10.9(2) . . . . ?
C15 C14 C18 N5 -109.3(2) . . . . ?
N2 C14 C18 N4 11.2(2) . . . . ?
N3 C14 C18 N4 -106.99(18) . . . . ?
C15 C14 C18 N4 132.80(18) . . . . ?
N2 C14 C18 C19 -108.1(2) . . . . ?
N3 C14 C18 C19 133.7(2) . . . . ?
C15 C14 C18 C19 13.5(3) . . . . ?
N5 C18 C19 O7 -28.6(4) . . . . ?
N4 C18 C19 O7 96.5(3) . . . . ?
C14 C18 C19 O7 -147.8(3) . . . . ?
N5 C18 C19 O8 155.8(2) . . . . ?
N4 C18 C19 O8 -79.1(2) . . . . ?
C14 C18 C19 O8 36.6(3) . . . . ?
N4 C22 C24 C25 55.3(3) . . . . ?
N4 C22 C24 C29 -128.7(2) . . . . ?
C29 C24 C25 C26 4.1(3) . . . . ?
C22 C24 C25 C26 -179.9(2) . . . . ?
C29 C24 C25 C23 -171.03(19) . . . . ?
C22 C24 C25 C23 5.0(3) . . . . ?
N5 C23 C25 C24 -60.3(3) . . . . ?
N5 C23 C25 C26 124.6(2) . . . . ?
C24 C25 C26 C27 -2.6(3) . . . . ?
C23 C25 C26 C27 172.5(2) . . . . ?
C24 C25 C26 N6 178.07(19) . . . . ?
C23 C25 C26 N6 -6.8(3) . . . . ?
C25 C26 C27 C28 -0.4(3) . . . . ?
N6 C26 C27 C28 178.9(2) . . . . ?
C26 C27 C28 C29 2.0(4) . . . . ?
C27 C28 C29 O9 -179.5(2) . . . . ?
C27 C28 C29 C24 -0.5(3) . . . . ?
C25 C24 C29 O9 176.52(19) . . . . ?
C22 C24 C29 O9 0.3(3) . . . . ?
C25 C24 C29 C28 -2.5(3) . . . . ?
C22 C24 C29 C28 -178.7(2) . . . . ?
O10 C31 C32 C33 123.5(3) . . . . ?
N6 C31 C32 C33 -56.7(3) . . . . ?
O10 C31 C32 C37 -51.8(3) . . . . ?
N6 C31 C32 C37 128.0(3) . . . . ?
C37 C32 C33 F1 178.6(2) . . . . ?
C31 C32 C33 F1 3.1(4) . . . . ?
C37 C32 C33 C34 -0.5(4) . . . . ?
C31 C32 C33 C34 -176.0(2) . . . . ?
F1 C33 C34 F2 1.2(4) . . . . ?
C32 C33 C34 F2 -179.8(2) . . . . ?
F1 C33 C34 C35 -179.5(2) . . . . ?
C32 C33 C34 C35 -0.4(4) . . . . ?
F2 C34 C35 F3 -0.3(5) . . . . ?
C33 C34 C35 F3 -179.7(3) . . . . ?
F2 C34 C35 C36 179.7(3) . . . . ?
C33 C34 C35 C36 0.4(5) . . . . ?
F3 C35 C36 F4 1.1(5) . . . . ?
C34 C35 C36 F4 -178.9(3) . . . . ?
F3 C35 C36 C37 -179.4(3) . . . . ?
C34 C35 C36 C37 0.5(5) . . . . ?
F4 C36 C37 F5 0.4(5) . . . . ?
C35 C36 C37 F5 -179.1(3) . . . . ?
F4 C36 C37 C32 178.0(3) . . . . ?
C35 C36 C37 C32 -1.5(5) . . . . ?
C33 C32 C37 F5 179.0(2) . . . . ?
C31 C32 C37 F5 -5.4(4) . . . . ?
C33 C32 C37 C36 1.4(4) . . . . ?
C31 C32 C37 C36 177.0(3) . . . . ?
O1 C2 N1 C3 -8.3(4) . . . . ?
C1 C2 N1 C3 173.0(2) . . . . ?
C4 C3 N1 C2 -39.7(3) . . . . ?
C8 C3 N1 C2 144.0(2) . . . . ?
O3 C12 N2 C14 -167.36(19) . . . . ?
N4 C12 N2 C14 13.8(2) . . . . ?
O3 C12 N2 C10 -21.7(3) . . . . ?
N4 C12 N2 C10 159.41(17) . . . . ?
N3 C14 N2 C12 94.2(2) . . . . ?
C15 C14 N2 C12 -140.84(17) . . . . ?
C18 C14 N2 C12 -15.5(2) . . . . ?
N3 C14 N2 C10 -51.0(3) . . . . ?
C15 C14 N2 C10 73.9(2) . . . . ?
C18 C14 N2 C10 -160.72(17) . . . . ?
C8 C10 N2 C12 -66.9(2) . . . . ?
C8 C10 N2 C14 75.6(2) . . . . ?
O4 C13 N3 C14 176.4(2) . . . . ?
N5 C13 N3 C14 -4.8(2) . . . . ?
O4 C13 N3 C11 3.2(3) . . . . ?
N5 C13 N3 C11 -177.92(18) . . . . ?
N2 C14 N3 C13 -114.8(2) . . . . ?
C15 C14 N3 C13 120.1(2) . . . . ?
C18 C14 N3 C13 -4.2(2) . . . . ?
N2 C14 N3 C11 58.5(3) . . . . ?
C15 C14 N3 C11 -66.6(2) . . . . ?
C18 C14 N3 C11 169.08(18) . . . . ?
C7 C11 N3 C13 90.8(2) . . . . ?
C7 C11 N3 C14 -81.8(2) . . . . ?
O3 C12 N4 C18 175.5(2) . . . . ?
N2 C12 N4 C18 -5.6(2) . . . . ?
O3 C12 N4 C22 2.6(3) . . . . ?
N2 C12 N4 C22 -178.58(18) . . . . ?
N5 C18 N4 C12 -114.6(2) . . . . ?
C19 C18 N4 C12 121.62(19) . . . . ?
C14 C18 N4 C12 -3.8(2) . . . . ?
N5 C18 N4 C22 58.6(3) . . . . ?
C19 C18 N4 C22 -65.2(2) . . . . ?
C14 C18 N4 C22 169.40(18) . . . . ?
C24 C22 N4 C12 94.4(2) . . . . ?
C24 C22 N4 C18 -78.0(3) . . . . ?
O4 C13 N5 C18 -168.5(2) . . . . ?
N3 C13 N5 C18 12.6(2) . . . . ?
O4 C13 N5 C23 -17.7(3) . . . . ?
N3 C13 N5 C23 163.39(18) . . . . ?
N4 C18 N5 C13 95.3(2) . . . . ?
C19 C18 N5 C13 -141.99(19) . . . . ?
C14 C18 N5 C13 -14.6(2) . . . . ?
N4 C18 N5 C23 -53.7(3) . . . . ?
C19 C18 N5 C23 68.9(3) . . . . ?
C14 C18 N5 C23 -163.67(18) . . . . ?
C25 C23 N5 C13 -74.7(2) . . . . ?
C25 C23 N5 C18 72.2(3) . . . . ?
O10 C31 N6 C26 -6.0(4) . . . . ?
C32 C31 N6 C26 174.2(2) . . . . ?
C27 C26 N6 C31 -104.0(3) . . . . ?
C25 C26 N6 C31 75.3(3) . . . . ?
C5 C6 O2 C9 7.1(3) . . . . ?
C7 C6 O2 C9 -174.5(2) . . . . ?
O5 C15 O6 C16 7.0(5) . . . . ?
C14 C15 O6 C16 -175.2(4) . . . . ?
O5 C15 O6 C16' -11.9(7) . . . . ?
C14 C15 O6 C16' 165.9(7) . . . . ?
C17 C16 O6 C15 -97.4(9) . . . . ?
C17 C16 O6 C16' -35.0(16) . . . . ?
C17' C16' O6 C15 -142.0(10) . . . . ?
C17' C16' O6 C16 92.2(19) . . . . ?
O7 C19 O8 C20 3.8(4) . . . . ?
C18 C19 O8 C20 179.3(2) . . . . ?
C21 C20 O8 C19 71.4(3) . . . . ?
C28 C29 O9 C30 16.5(3) . . . . ?
C24 C29 O9 C30 -162.5(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139182036
