#------------------------------------------------------------------------------
#$Date: 2024-10-04 12:47:15 +0300 (Fri, 04 Oct 2024) $
#$Revision: 295042 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/27/1572775.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_1572775
loop_
_publ_author_name
'Pim, Sebastian'
'Bourgès, Anaïs C'
'Wu, Dan'
'Durán-Sampedro, Gonzalo'
'Garre, Massimiliano'
'O'Shea, Donal F'
_publ_section_title
;
 Observing bioorthogonal macrocyclizations in the nuclear envelope of live
 cells using on/on fluorescence lifetime microscopy.
;
_journal_issue                   36
_journal_name_full               'Chemical science'
_journal_page_first              14913
_journal_page_last               14923
_journal_paper_doi               10.1039/d4sc03489a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C H Cl3, C44 H36 B F2 N9 O2'
_chemical_formula_sum            'C45 H37 B Cl3 F2 N9 O2'
_chemical_formula_weight         890.99
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2024-03-06 deposited with the CCDC.	2024-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                106.314(5)
_cell_angle_beta                 104.337(4)
_cell_angle_gamma                105.219(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0839(13)
_cell_length_b                   13.719(2)
_cell_length_c                   15.383(3)
_cell_measurement_reflns_used    9097
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.28
_cell_measurement_theta_min      2.75
_cell_volume                     2031.6(6)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2017) '
_computing_data_reduction        'SAINT v8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 5.12
_diffrn_detector_type            'Bruker PHOTON 50'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_detector       'Bruker PHOTON 50'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16496
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.547
_diffrn_reflns_theta_min         2.892
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens, KFF Mo 2K -90 C'
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.745373
_exptl_absorpt_correction_T_min  0.708248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 108235 reflections, Rint = 0.0667
 (64601 with I > 3sig(I), Rint = 0.0570)
;
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             920
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         16496
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0437P)²+0.9773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1150
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13715
_reflns_number_total             16496
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc03489a8.cif
_cod_data_source_block           tcd1068_5
_cod_database_code               1572775
_shelx_shelxl_version_number     2016/6
_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_max   0.953
_shelx_estimated_absorpt_t_min   0.906
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.510(2)
 0.3536(15) 0.1361(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 Cl1-C1S \\sim Cl1A-C1S \\sim Cl3A-C1S \\sim Cl3-C1S \\sim Cl2-C1S \\sim
Cl2A-C1S
 with sigma of 0.005
4. Uiso/Uaniso restraints and constraints
Cl1A \\sim Cl1 \\sim Cl2 \\sim Cl3 \\sim Cl2A \\sim Cl3A: within 2A with sigma
of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Sof(Cl1A)=Sof(H1SA)=Sof(Cl2A)=Sof(Cl3A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(H1S)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C1S(H1S), C1S(H1SA)
6.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C53(H53A,H53B), C54(H54A,
 H54B), C55(H55A,H55B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C13(H13), C14(H14), C16(H16), C17(H17), C21(H21), C22(H22),
 C24(H24), C25(H25), C37(H37), C38(H38), C39(H39), C40(H40), C43(H43), C44(H44),
  C45(H45), C46(H46)
6.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C27(H27A,H27B,H27C)
;
_olex2_exptl_crystal_mounting_method 'mounted in oil on a MiTeGen microloop'
_olex2_submission_original_sample_id GDS423B
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl 0.8093(7) 0.0860(7) 0.2142(5) 0.0457(11) Uani 0.49(3) 1 d D U P A 2
Cl1 Cl 0.8263(11) 0.1084(13) 0.2323(11) 0.0631(18) Uani 0.51(3) 1 d D U P A 1
Cl2 Cl 0.8666(5) 0.0813(3) 0.4064(3) 0.0348(15) Uani 0.51(3) 1 d D U P A 1
Cl3 Cl 0.6700(3) -0.09896(17) 0.2420(5) 0.0397(13) Uani 0.51(3) 1 d D U P A 1
C1S C 0.7432(2) 0.04256(17) 0.29445(14) 0.0298(5) Uani 1 1 d D . . . .
H1S H 0.672905 0.072949 0.304813 0.036 Uiso 0.51(3) 1 calc R . P A 1
H1SA H 0.670335 0.071672 0.299540 0.036 Uiso 0.49(3) 1 calc R . P A 2
Cl2A Cl 0.8497(12) 0.0749(6) 0.4119(4) 0.077(2) Uani 0.49(3) 1 d D U P A 2
Cl3A Cl 0.6695(6) -0.0994(3) 0.2345(6) 0.072(2) Uani 0.49(3) 1 d D U P A 2
F1 F 0.28892(12) 0.72407(9) 0.60303(8) 0.0185(3) Uani 1 1 d . . . . .
F2 F 0.45291(11) 0.67356(9) 0.67895(8) 0.0183(3) Uani 1 1 d . . . . .
O18 O -0.07164(15) 0.52895(12) 0.82265(11) 0.0220(3) Uani 1 1 d . . . . .
O26 O 0.69449(16) 1.20997(12) 0.82278(11) 0.0246(3) Uani 1 1 d . . . . .
N1 N 0.45119(16) 0.69574(14) 0.52795(12) 0.0153(3) Uani 1 1 d . . . . .
N6 N 0.38996(17) 0.51257(14) 0.41565(12) 0.0168(4) Uani 1 1 d . . . . .
N8 N 0.27954(16) 0.53856(14) 0.53234(12) 0.0150(3) Uani 1 1 d . . . . .
N31 N 0.39102(17) 0.45708(13) 0.05910(12) 0.0156(3) Uani 1 1 d . . . . .
N32 N 0.33219(17) 0.52079(14) 0.02685(12) 0.0182(4) Uani 1 1 d . . . . .
N33 N 0.23328(17) 0.45778(14) -0.05438(12) 0.0171(4) Uani 1 1 d . . . . .
N50 N 0.08203(16) 0.14250(13) 0.06655(12) 0.0142(3) Uani 1 1 d . . . . .
N51 N -0.04988(17) 0.11870(14) 0.02676(12) 0.0166(3) Uani 1 1 d . . . . .
N52 N -0.07243(17) 0.12235(14) -0.06028(12) 0.0170(4) Uani 1 1 d . . . . .
C2 C 0.5329(2) 0.79495(17) 0.53701(14) 0.0168(4) Uani 1 1 d . . . . .
C3 C 0.5910(2) 0.77964(17) 0.46376(14) 0.0180(4) Uani 1 1 d . . . . .
H3 H 0.649866 0.835673 0.453213 0.022 Uiso 1 1 calc R . . . .
C4 C 0.54763(19) 0.67047(17) 0.41098(14) 0.0180(4) Uani 1 1 d . . . . .
C5 C 0.4589(2) 0.61835(17) 0.45014(14) 0.0166(4) Uani 1 1 d . . . . .
C7 C 0.3029(2) 0.47517(17) 0.45396(14) 0.0160(4) Uani 1 1 d . . . . .
C9 C 0.1751(2) 0.47174(16) 0.54445(14) 0.0159(4) Uani 1 1 d . . . . .
C10 C 0.1321(2) 0.36580(17) 0.47359(14) 0.0176(4) Uani 1 1 d . . . . .
H10 H 0.059467 0.304802 0.465555 0.021 Uiso 1 1 calc R . . . .
C11 C 0.2122(2) 0.36591(16) 0.41884(14) 0.0169(4) Uani 1 1 d . . . . .
C12 C 0.1170(2) 0.49788(16) 0.61914(14) 0.0156(4) Uani 1 1 d . . . . .
C13 C 0.1857(2) 0.57716(17) 0.71185(15) 0.0183(4) Uani 1 1 d . . . . .
H13 H 0.274827 0.623250 0.727416 0.022 Uiso 1 1 calc R . . . .
C14 C 0.1260(2) 0.58974(17) 0.78160(15) 0.0186(4) Uani 1 1 d . . . . .
H14 H 0.174510 0.643442 0.844528 0.022 Uiso 1 1 calc R . . . .
C15 C -0.0050(2) 0.52356(17) 0.75919(15) 0.0172(4) Uani 1 1 d . . . . .
C16 C -0.0765(2) 0.44608(17) 0.66640(15) 0.0182(4) Uani 1 1 d . . . . .
H16 H -0.167004 0.402651 0.650296 0.022 Uiso 1 1 calc R . . . .
C17 C -0.0160(2) 0.43248(17) 0.59810(15) 0.0170(4) Uani 1 1 d . . . . .
H17 H -0.064823 0.378025 0.535560 0.020 Uiso 1 1 calc R . . . .
C19 C 0.0022(2) 0.59924(19) 0.92125(16) 0.0243(5) Uani 1 1 d . . . . .
H19A H 0.034770 0.674619 0.925284 0.036 Uiso 1 1 calc GR . . . .
H19B H 0.078027 0.578612 0.946179 0.036 Uiso 1 1 calc GR . . . .
H19C H -0.055773 0.592623 0.959795 0.036 Uiso 1 1 calc GR . . . .
C20 C 0.5648(2) 0.90067(16) 0.61099(14) 0.0166(4) Uani 1 1 d . . . . .
C21 C 0.6116(2) 0.99347(18) 0.58968(15) 0.0204(4) Uani 1 1 d . . . . .
H21 H 0.614136 0.984482 0.526718 0.024 Uiso 1 1 calc R . . . .
C22 C 0.6541(2) 1.09767(18) 0.65733(16) 0.0220(4) Uani 1 1 d . . . . .
H22 H 0.683812 1.158904 0.640381 0.026 Uiso 1 1 calc R . . . .
C23 C 0.6531(2) 1.11208(17) 0.75011(15) 0.0197(4) Uani 1 1 d . . . . .
C24 C 0.6060(2) 1.02120(17) 0.77255(15) 0.0188(4) Uani 1 1 d . . . . .
H24 H 0.603651 1.030870 0.835643 0.023 Uiso 1 1 calc R . . . .
C25 C 0.5628(2) 0.91747(17) 0.70511(15) 0.0181(4) Uani 1 1 d . . . . .
H25 H 0.531379 0.856717 0.722273 0.022 Uiso 1 1 calc R . . . .
C27 C 0.7767(2) 1.30195(18) 0.81181(18) 0.0258(5) Uani 1 1 d . . . . .
H27A H 0.803761 1.366709 0.869962 0.039 Uiso 1 1 calc GR . . . .
H27B H 0.726642 1.313238 0.755691 0.039 Uiso 1 1 calc GR . . . .
H27C H 0.856162 1.288945 0.802252 0.039 Uiso 1 1 calc GR . . . .
C28 C 0.5811(2) 0.61174(18) 0.32818(15) 0.0197(4) Uani 1 1 d . . . . .
H28A H 0.599162 0.547966 0.338056 0.024 Uiso 1 1 calc R . . . .
H28B H 0.663320 0.660481 0.326463 0.024 Uiso 1 1 calc R . . . .
C29 C 0.4692(2) 0.57351(18) 0.23150(14) 0.0196(4) Uani 1 1 d . . . . .
H29A H 0.384788 0.529975 0.234624 0.024 Uiso 1 1 calc R . . . .
H29B H 0.456929 0.637351 0.217972 0.024 Uiso 1 1 calc R . . . .
C30 C 0.5024(2) 0.50525(17) 0.15099(14) 0.0184(4) Uani 1 1 d . . . . .
H30A H 0.581383 0.551369 0.143478 0.022 Uiso 1 1 calc R . . . .
H30B H 0.525225 0.446593 0.168576 0.022 Uiso 1 1 calc R . . . .
C34 C 0.2280(2) 0.35309(16) -0.07394(14) 0.0152(4) Uani 1 1 d . . . . .
C35 C 0.32938(19) 0.35146(16) -0.00171(14) 0.0145(4) Uani 1 1 d . . . . .
C36 C 0.37504(19) 0.26447(16) 0.01463(13) 0.0145(4) Uani 1 1 d . . . . .
C37 C 0.5056(2) 0.27082(17) 0.02442(15) 0.0184(4) Uani 1 1 d . . . . .
H37 H 0.563822 0.329029 0.015832 0.022 Uiso 1 1 calc R . . . .
C38 C 0.5510(2) 0.19278(17) 0.04660(15) 0.0199(4) Uani 1 1 d . . . . .
H38 H 0.639989 0.197361 0.052954 0.024 Uiso 1 1 calc R . . . .
C39 C 0.4661(2) 0.10772(17) 0.05953(15) 0.0187(4) Uani 1 1 d . . . . .
H39 H 0.498396 0.056240 0.077973 0.022 Uiso 1 1 calc R . . . .
C40 C 0.3348(2) 0.09798(16) 0.04560(14) 0.0162(4) Uani 1 1 d . . . . .
H40 H 0.276190 0.037724 0.051455 0.019 Uiso 1 1 calc R . . . .
C41 C 0.28736(19) 0.17599(16) 0.02297(13) 0.0138(4) Uani 1 1 d . . . . .
C42 C 0.13275(19) 0.26490(16) -0.16418(14) 0.0156(4) Uani 1 1 d . . . . .
C43 C 0.1210(2) 0.28230(18) -0.25046(15) 0.0188(4) Uani 1 1 d . . . . .
H43 H 0.172260 0.350531 -0.249061 0.023 Uiso 1 1 calc R . . . .
C44 C 0.0361(2) 0.20177(18) -0.33800(15) 0.0224(5) Uani 1 1 d . . . . .
H44 H 0.030925 0.213868 -0.396448 0.027 Uiso 1 1 calc R . . . .
C45 C -0.0417(2) 0.10318(18) -0.33999(15) 0.0222(4) Uani 1 1 d . . . . .
H45 H -0.098600 0.046848 -0.400011 0.027 Uiso 1 1 calc R . . . .
C46 C -0.0363(2) 0.08687(17) -0.25439(15) 0.0183(4) Uani 1 1 d . . . . .
H46 H -0.092917 0.020374 -0.256233 0.022 Uiso 1 1 calc R . . . .
C47 C 0.0505(2) 0.16626(16) -0.16582(14) 0.0153(4) Uani 1 1 d . . . . .
C48 C 0.04619(19) 0.15063(16) -0.07519(14) 0.0150(4) Uani 1 1 d . . . . .
C49 C 0.14608(19) 0.16233(15) 0.00525(14) 0.0146(4) Uani 1 1 d . . . . .
C53 C 0.1360(2) 0.15528(16) 0.16771(14) 0.0165(4) Uani 1 1 d . . . . .
H53A H 0.225076 0.148794 0.180685 0.020 Uiso 1 1 calc R . . . .
H53B H 0.077258 0.095851 0.179235 0.020 Uiso 1 1 calc R . . . .
C54 C 0.1484(2) 0.26413(16) 0.23751(14) 0.0169(4) Uani 1 1 d . . . . .
H54A H 0.059219 0.269748 0.228286 0.020 Uiso 1 1 calc R . . . .
H54B H 0.204468 0.324412 0.225325 0.020 Uiso 1 1 calc R . . . .
C55 C 0.2121(2) 0.27174(16) 0.34088(14) 0.0177(4) Uani 1 1 d . . . . .
H55A H 0.164231 0.203798 0.347429 0.021 Uiso 1 1 calc R . . . .
H55B H 0.305476 0.276168 0.351073 0.021 Uiso 1 1 calc R . . . .
B1 B 0.3675(2) 0.66174(19) 0.59003(16) 0.0160(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'
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'
F F 0.0171 0.0103 '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'
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
Cl1A C1S H1SA 107.9 . . ?
Cl1A C1S Cl2A 119.1(7) . . ?
Cl1A C1S Cl3A 103.6(5) . . ?
Cl1 C1S H1S 108.6 . . ?
Cl2 C1S Cl1 103.7(6) . . ?
Cl2 C1S H1S 108.6 . . ?
Cl3 C1S Cl1 117.1(7) . . ?
Cl3 C1S Cl2 109.9(3) . . ?
Cl3 C1S H1S 108.6 . . ?
Cl2A C1S H1SA 107.9 . . ?
Cl2A C1S Cl3A 110.1(4) . . ?
Cl3A C1S H1SA 107.9 . . ?
C15 O18 C19 117.62(17) . . ?
C23 O26 C27 117.13(17) . . ?
C2 N1 C5 106.64(17) . . ?
C2 N1 B1 131.77(17) . . ?
C5 N1 B1 121.48(17) . . ?
C7 N6 C5 119.05(17) . . ?
C7 N8 B1 121.78(17) . . ?
C9 N8 C7 106.77(17) . . ?
C9 N8 B1 131.43(16) . . ?
N32 N31 C30 119.57(16) . . ?
N32 N31 C35 110.98(16) . . ?
C35 N31 C30 129.40(17) . . ?
N33 N32 N31 107.49(16) . . ?
N32 N33 C34 108.80(17) . . ?
N51 N50 C49 111.11(16) . . ?
N51 N50 C53 118.47(16) . . ?
C49 N50 C53 130.01(17) . . ?
N52 N51 N50 107.36(15) . . ?
N51 N52 C48 108.71(16) . . ?
N1 C2 C3 108.84(18) . . ?
N1 C2 C20 127.74(18) . . ?
C3 C2 C20 123.34(19) . . ?
C2 C3 H3 125.7 . . ?
C4 C3 C2 108.54(18) . . ?
C4 C3 H3 125.7 . . ?
C3 C4 C5 106.19(18) . . ?
C3 C4 C28 129.87(19) . . ?
C5 C4 C28 123.94(19) . . ?
N1 C5 C4 109.76(18) . . ?
N6 C5 N1 125.26(18) . . ?
N6 C5 C4 124.93(18) . . ?
N6 C7 N8 124.91(19) . . ?
N6 C7 C11 125.61(18) . . ?
N8 C7 C11 109.37(18) . . ?
N8 C9 C10 108.98(17) . . ?
N8 C9 C12 127.93(18) . . ?
C10 C9 C12 123.02(18) . . ?
C9 C10 H10 125.6 . . ?
C11 C10 C9 108.88(18) . . ?
C11 C10 H10 125.6 . . ?
C7 C11 C55 125.70(19) . . ?
C10 C11 C7 105.93(18) . . ?
C10 C11 C55 128.32(19) . . ?
C13 C12 C9 125.00(19) . . ?
C13 C12 C17 117.80(18) . . ?
C17 C12 C9 117.03(18) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.14(19) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.88(19) . . ?
C15 C14 H14 120.1 . . ?
O18 C15 C14 124.26(19) . . ?
O18 C15 C16 115.84(18) . . ?
C14 C15 C16 119.90(19) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.97(19) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.26(19) . . ?
C16 C17 H17 119.4 . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C2 117.67(18) . . ?
C21 C20 C25 117.14(19) . . ?
C25 C20 C2 124.97(19) . . ?
C20 C21 H21 118.9 . . ?
C22 C21 C20 122.2(2) . . ?
C22 C21 H21 118.9 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.6(2) . . ?
C23 C22 H22 120.2 . . ?
O26 C23 C22 124.8(2) . . ?
O26 C23 C24 115.98(19) . . ?
C22 C23 C24 119.18(19) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.31(19) . . ?
C25 C24 H24 119.3 . . ?
C20 C25 H25 119.7 . . ?
C24 C25 C20 120.59(19) . . ?
C24 C25 H25 119.7 . . ?
O26 C27 H27A 109.5 . . ?
O26 C27 H27B 109.5 . . ?
O26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C4 C28 H28A 109.1 . . ?
C4 C28 H28B 109.1 . . ?
C4 C28 C29 112.38(17) . . ?
H28A C28 H28B 107.9 . . ?
C29 C28 H28A 109.1 . . ?
C29 C28 H28B 109.1 . . ?
C28 C29 H29A 109.6 . . ?
C28 C29 H29B 109.6 . . ?
H29A C29 H29B 108.1 . . ?
C30 C29 C28 110.33(17) . . ?
C30 C29 H29A 109.6 . . ?
C30 C29 H29B 109.6 . . ?
N31 C30 C29 111.80(17) . . ?
N31 C30 H30A 109.3 . . ?
N31 C30 H30B 109.3 . . ?
C29 C30 H30A 109.3 . . ?
C29 C30 H30B 109.3 . . ?
H30A C30 H30B 107.9 . . ?
N33 C34 C35 108.63(18) . . ?
N33 C34 C42 121.17(18) . . ?
C35 C34 C42 129.98(18) . . ?
N31 C35 C34 104.10(17) . . ?
N31 C35 C36 122.55(17) . . ?
C34 C35 C36 133.33(18) . . ?
C37 C36 C35 120.58(18) . . ?
C37 C36 C41 119.80(18) . . ?
C41 C36 C35 119.60(18) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 C36 120.42(19) . . ?
C38 C37 H37 119.8 . . ?
C37 C38 H38 120.1 . . ?
C37 C38 C39 119.9(2) . . ?
C39 C38 H38 120.1 . . ?
C38 C39 H39 120.0 . . ?
C40 C39 C38 120.09(19) . . ?
C40 C39 H39 120.0 . . ?
C39 C40 H40 119.7 . . ?
C39 C40 C41 120.65(19) . . ?
C41 C40 H40 119.7 . . ?
C36 C41 C49 121.09(17) . . ?
C40 C41 C36 119.03(18) . . ?
C40 C41 C49 119.85(18) . . ?
C43 C42 C34 118.08(18) . . ?
C43 C42 C47 119.37(19) . . ?
C47 C42 C34 122.50(18) . . ?
C42 C43 H43 119.5 . . ?
C44 C43 C42 121.0(2) . . ?
C44 C43 H43 119.5 . . ?
C43 C44 H44 120.2 . . ?
C43 C44 C45 119.6(2) . . ?
C45 C44 H44 120.2 . . ?
C44 C45 H45 120.0 . . ?
C46 C45 C44 120.0(2) . . ?
C46 C45 H45 120.0 . . ?
C45 C46 H46 119.5 . . ?
C45 C46 C47 121.09(19) . . ?
C47 C46 H46 119.5 . . ?
C42 C47 C48 121.00(18) . . ?
C46 C47 C42 118.79(18) . . ?
C46 C47 C48 119.94(18) . . ?
N52 C48 C47 120.00(17) . . ?
N52 C48 C49 108.65(17) . . ?
C49 C48 C47 131.33(18) . . ?
N50 C49 C41 123.60(18) . . ?
N50 C49 C48 104.15(17) . . ?
C48 C49 C41 131.66(18) . . ?
N50 C53 H53A 109.1 . . ?
N50 C53 H53B 109.1 . . ?
N50 C53 C54 112.59(16) . . ?
H53A C53 H53B 107.8 . . ?
C54 C53 H53A 109.1 . . ?
C54 C53 H53B 109.1 . . ?
C53 C54 H54A 110.0 . . ?
C53 C54 H54B 110.0 . . ?
C53 C54 C55 108.45(16) . . ?
H54A C54 H54B 108.4 . . ?
C55 C54 H54A 110.0 . . ?
C55 C54 H54B 110.0 . . ?
C11 C55 C54 115.32(16) . . ?
C11 C55 H55A 108.4 . . ?
C11 C55 H55B 108.4 . . ?
C54 C55 H55A 108.4 . . ?
C54 C55 H55B 108.4 . . ?
H55A C55 H55B 107.5 . . ?
F1 B1 F2 110.54(16) . . ?
F1 B1 N1 110.28(17) . . ?
F1 B1 N8 110.95(17) . . ?
F2 B1 N1 109.66(16) . . ?
F2 B1 N8 109.26(17) . . ?
N1 B1 N8 106.04(15) . . ?
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
Cl1A C1S 1.747(4) . ?
Cl1 C1S 1.751(4) . ?
Cl2 C1S 1.748(3) . ?
Cl3 C1S 1.746(3) . ?
C1S H1S 1.0000 . ?
C1S H1SA 1.0000 . ?
C1S Cl2A 1.754(4) . ?
C1S Cl3A 1.758(4) . ?
F1 B1 1.383(2) . ?
F2 B1 1.395(3) . ?
O18 C15 1.360(2) . ?
O18 C19 1.432(3) . ?
O26 C23 1.358(3) . ?
O26 C27 1.430(3) . ?
N1 C2 1.370(3) . ?
N1 C5 1.397(3) . ?
N1 B1 1.566(3) . ?
N6 C5 1.325(3) . ?
N6 C7 1.317(3) . ?
N8 C7 1.400(3) . ?
N8 C9 1.364(3) . ?
N8 B1 1.568(3) . ?
N31 N32 1.348(2) . ?
N31 C30 1.463(3) . ?
N31 C35 1.358(2) . ?
N32 N33 1.314(2) . ?
N33 C34 1.364(3) . ?
N50 N51 1.346(2) . ?
N50 C49 1.357(2) . ?
N50 C53 1.463(2) . ?
N51 N52 1.318(2) . ?
N52 C48 1.365(3) . ?
C2 C3 1.423(3) . ?
C2 C20 1.459(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.371(3) . ?
C4 C5 1.417(3) . ?
C4 C28 1.491(3) . ?
C7 C11 1.426(3) . ?
C9 C10 1.420(3) . ?
C9 C12 1.456(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.367(3) . ?
C11 C55 1.495(3) . ?
C12 C13 1.397(3) . ?
C12 C17 1.411(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(3) . ?
C15 C16 1.393(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.376(3) . ?
C17 H17 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.403(3) . ?
C20 C25 1.408(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.388(3) . ?
C23 C24 1.391(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.378(3) . ?
C25 H25 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.527(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.517(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C34 C35 1.381(3) . ?
C34 C42 1.472(3) . ?
C35 C36 1.472(3) . ?
C36 C37 1.394(3) . ?
C36 C41 1.401(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.385(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.391(3) . ?
C39 H39 0.9500 . ?
C39 C40 1.381(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.399(3) . ?
C41 C49 1.472(3) . ?
C42 C43 1.394(3) . ?
C42 C47 1.409(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.382(3) . ?
C44 H44 0.9500 . ?
C44 C45 1.387(3) . ?
C45 H45 0.9500 . ?
C45 C46 1.386(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.391(3) . ?
C47 C48 1.479(3) . ?
C48 C49 1.378(3) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C53 C54 1.523(3) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C54 C55 1.533(3) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
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
C13 H13 F2 0.95 2.29 3.136(2) 148.5 .
C25 H25 F2 0.95 2.27 3.115(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
O18 C15 C16 C17 -178.06(18) . . . . ?
O26 C23 C24 C25 -179.20(19) . . . . ?
N1 C2 C3 C4 -1.5(2) . . . . ?
N1 C2 C20 C21 -158.6(2) . . . . ?
N1 C2 C20 C25 26.8(3) . . . . ?
N6 C7 C11 C10 -173.93(19) . . . . ?
N6 C7 C11 C55 8.7(3) . . . . ?
N8 C7 C11 C10 2.5(2) . . . . ?
N8 C7 C11 C55 -174.94(18) . . . . ?
N8 C9 C10 C11 1.6(2) . . . . ?
N8 C9 C12 C13 -28.0(3) . . . . ?
N8 C9 C12 C17 156.81(19) . . . . ?
N31 N32 N33 C34 0.5(2) . . . . ?
N31 C35 C36 C37 -56.3(3) . . . . ?
N31 C35 C36 C41 122.0(2) . . . . ?
N32 N31 C30 C29 50.8(2) . . . . ?
N32 N31 C35 C34 -0.1(2) . . . . ?
N32 N31 C35 C36 178.44(17) . . . . ?
N32 N33 C34 C35 -0.6(2) . . . . ?
N32 N33 C34 C42 -175.71(17) . . . . ?
N33 C34 C35 N31 0.4(2) . . . . ?
N33 C34 C35 C36 -177.9(2) . . . . ?
N33 C34 C42 C43 46.5(3) . . . . ?
N33 C34 C42 C47 -131.1(2) . . . . ?
N50 N51 N52 C48 -1.1(2) . . . . ?
N50 C53 C54 C55 -177.18(16) . . . . ?
N51 N50 C49 C41 -171.45(17) . . . . ?
N51 N50 C49 C48 0.6(2) . . . . ?
N51 N50 C53 C54 -76.8(2) . . . . ?
N51 N52 C48 C47 -176.84(17) . . . . ?
N51 N52 C48 C49 1.5(2) . . . . ?
N52 C48 C49 N50 -1.3(2) . . . . ?
N52 C48 C49 C41 169.9(2) . . . . ?
C2 N1 C5 N6 -177.14(19) . . . . ?
C2 N1 C5 C4 0.5(2) . . . . ?
C2 N1 B1 F1 51.6(3) . . . . ?
C2 N1 B1 F2 -70.4(3) . . . . ?
C2 N1 B1 N8 171.77(19) . . . . ?
C2 C3 C4 C5 1.8(2) . . . . ?
C2 C3 C4 C28 -178.5(2) . . . . ?
C2 C20 C21 C22 -175.05(19) . . . . ?
C2 C20 C25 C24 174.19(19) . . . . ?
C3 C2 C20 C21 25.0(3) . . . . ?
C3 C2 C20 C25 -149.5(2) . . . . ?
C3 C4 C5 N1 -1.4(2) . . . . ?
C3 C4 C5 N6 176.22(19) . . . . ?
C3 C4 C28 C29 -103.7(3) . . . . ?
C4 C28 C29 C30 -174.64(18) . . . . ?
C5 N1 C2 C3 0.6(2) . . . . ?
C5 N1 C2 C20 -176.18(19) . . . . ?
C5 N1 B1 F1 -132.78(18) . . . . ?
C5 N1 B1 F2 105.3(2) . . . . ?
C5 N1 B1 N8 -12.6(2) . . . . ?
C5 N6 C7 N8 -2.5(3) . . . . ?
C5 N6 C7 C11 173.36(19) . . . . ?
C5 C4 C28 C29 75.9(3) . . . . ?
C7 N6 C5 N1 2.6(3) . . . . ?
C7 N6 C5 C4 -174.74(19) . . . . ?
C7 N8 C9 C10 0.0(2) . . . . ?
C7 N8 C9 C12 176.92(19) . . . . ?
C7 N8 B1 F1 132.43(18) . . . . ?
C7 N8 B1 F2 -105.4(2) . . . . ?
C7 N8 B1 N1 12.7(2) . . . . ?
C7 C11 C55 C54 -79.2(3) . . . . ?
C9 N8 C7 N6 174.94(19) . . . . ?
C9 N8 C7 C11 -1.5(2) . . . . ?
C9 N8 B1 F1 -49.2(3) . . . . ?
C9 N8 B1 F2 72.9(3) . . . . ?
C9 N8 B1 N1 -168.97(18) . . . . ?
C9 C10 C11 C7 -2.5(2) . . . . ?
C9 C10 C11 C55 174.86(19) . . . . ?
C9 C12 C13 C14 -173.80(19) . . . . ?
C9 C12 C17 C16 175.50(18) . . . . ?
C10 C9 C12 C13 148.5(2) . . . . ?
C10 C9 C12 C17 -26.6(3) . . . . ?
C10 C11 C55 C54 104.0(2) . . . . ?
C12 C9 C10 C11 -175.52(18) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C12 C17 C16 0.0(3) . . . . ?
C13 C14 C15 O18 179.37(19) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C14 C15 C16 C17 2.3(3) . . . . ?
C15 C16 C17 C12 -1.8(3) . . . . ?
C17 C12 C13 C14 1.3(3) . . . . ?
C19 O18 C15 C14 -6.8(3) . . . . ?
C19 O18 C15 C16 173.56(18) . . . . ?
C20 C2 C3 C4 175.44(18) . . . . ?
C20 C21 C22 C23 1.1(3) . . . . ?
C21 C20 C25 C24 -0.4(3) . . . . ?
C21 C22 C23 O26 178.81(19) . . . . ?
C21 C22 C23 C24 -1.6(3) . . . . ?
C22 C23 C24 C25 1.2(3) . . . . ?
C23 C24 C25 C20 -0.2(3) . . . . ?
C25 C20 C21 C22 -0.1(3) . . . . ?
C27 O26 C23 C22 -17.6(3) . . . . ?
C27 O26 C23 C24 162.79(19) . . . . ?
C28 C4 C5 N1 178.83(18) . . . . ?
C28 C4 C5 N6 -3.5(3) . . . . ?
C28 C29 C30 N31 173.58(17) . . . . ?
C30 N31 N32 N33 -177.82(16) . . . . ?
C30 N31 C35 C34 177.19(18) . . . . ?
C30 N31 C35 C36 -4.2(3) . . . . ?
C34 C35 C36 C37 121.8(2) . . . . ?
C34 C35 C36 C41 -59.9(3) . . . . ?
C34 C42 C43 C44 178.25(19) . . . . ?
C34 C42 C47 C46 -179.66(18) . . . . ?
C34 C42 C47 C48 6.2(3) . . . . ?
C35 N31 N32 N33 -0.2(2) . . . . ?
C35 N31 C30 C29 -126.4(2) . . . . ?
C35 C34 C42 C43 -127.5(2) . . . . ?
C35 C34 C42 C47 54.8(3) . . . . ?
C35 C36 C37 C38 175.40(18) . . . . ?
C35 C36 C41 C40 -175.30(17) . . . . ?
C35 C36 C41 C49 6.7(3) . . . . ?
C36 C37 C38 C39 -0.2(3) . . . . ?
C36 C41 C49 N50 -130.6(2) . . . . ?
C36 C41 C49 C48 59.7(3) . . . . ?
C37 C36 C41 C40 3.0(3) . . . . ?
C37 C36 C41 C49 -175.01(18) . . . . ?
C37 C38 C39 C40 3.2(3) . . . . ?
C38 C39 C40 C41 -3.1(3) . . . . ?
C39 C40 C41 C36 0.0(3) . . . . ?
C39 C40 C41 C49 178.00(18) . . . . ?
C40 C41 C49 N50 51.4(3) . . . . ?
C40 C41 C49 C48 -118.3(2) . . . . ?
C41 C36 C37 C38 -2.9(3) . . . . ?
C42 C34 C35 N31 175.00(19) . . . . ?
C42 C34 C35 C36 -3.3(4) . . . . ?
C42 C43 C44 C45 1.9(3) . . . . ?
C42 C47 C48 N52 123.6(2) . . . . ?
C42 C47 C48 C49 -54.3(3) . . . . ?
C43 C42 C47 C46 2.7(3) . . . . ?
C43 C42 C47 C48 -171.35(18) . . . . ?
C43 C44 C45 C46 1.6(3) . . . . ?
C44 C45 C46 C47 -2.9(3) . . . . ?
C45 C46 C47 C42 0.7(3) . . . . ?
C45 C46 C47 C48 174.84(19) . . . . ?
C46 C47 C48 N52 -50.4(3) . . . . ?
C46 C47 C48 C49 131.6(2) . . . . ?
C47 C42 C43 C44 -4.0(3) . . . . ?
C47 C48 C49 N50 176.84(19) . . . . ?
C47 C48 C49 C41 -12.0(4) . . . . ?
C49 N50 N51 N52 0.3(2) . . . . ?
C49 N50 C53 C54 95.1(2) . . . . ?
C53 N50 N51 N52 173.65(16) . . . . ?
C53 N50 C49 C41 16.2(3) . . . . ?
C53 N50 C49 C48 -171.74(18) . . . . ?
C53 C54 C55 C11 -170.85(18) . . . . ?
B1 N1 C2 C3 176.73(19) . . . . ?
B1 N1 C2 C20 -0.1(3) . . . . ?
B1 N1 C5 N6 6.2(3) . . . . ?
B1 N1 C5 C4 -176.11(17) . . . . ?
B1 N8 C7 N6 -6.3(3) . . . . ?
B1 N8 C7 C11 177.22(17) . . . . ?
B1 N8 C9 C10 -178.58(19) . . . . ?
B1 N8 C9 C12 -1.6(3) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.510(2)
2 0.3536(15)
3 0.1361(14)
