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#$Date: 2022-02-04 02:34:30 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272513 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/62/1566281.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_1566281
loop_
_publ_author_name
'Guillou, Amaury'
'Nisli, Eda'
'Klingler, Simon'
'Linden, Anthony'
'Holland, Jason P.'
_publ_section_title
;
 Photoactivatable Fluorescent Tags for Dual-Modality Positron Emission
 Tomography Optical Imaging.
;
_journal_issue                   1
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              811
_journal_page_last               823
_journal_paper_doi               10.1021/acs.jmedchem.1c01899
_journal_volume                  65
_journal_year                    2022
_chemical_formula_moiety         'C37 H47 F6 N4 O4 P, 1.5(C4 H10 O)'
_chemical_formula_sum            'C43 H62 F6 N4 O5.5 P'
_chemical_formula_weight         867.93
_chemical_name_systematic
;
N-(9-(2-(4-(tert-butoxycarbonyl)piperazine-1-carbonyl)phenyl)-6-
(diethylamino)-3H-xanthen-3-ylidene)-N-ethylethanaminium 
hexafluorophosphate 1.5 diethyl ether solvate
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                103.6966(18)
_cell_angle_beta                 99.4485(18)
_cell_angle_gamma                117.548(2)
_cell_formula_units_Z            2
_cell_length_a                   13.1015(3)
_cell_length_b                   13.9905(3)
_cell_length_c                   14.3129(3)
_cell_measurement_reflns_used    28928
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      79.0120
_cell_measurement_theta_min      3.8010
_cell_volume                     2142.83(10)
_computing_cell_refinement
'CrysAlisPro, Version 1.171.40.84a (Rigaku Oxford Diffraction, 2020)'
_computing_data_collection
'CrysAlisPro, Version 1.171.40.84a (Rigaku Oxford Diffraction, 2020)'
_computing_data_reduction
'CrysAlisPro, Version 1.171.40.84a (Rigaku Oxford Diffraction, 2020)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2018 and PLATON (Spek, 2015)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT-2018 (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(2)
_diffrn_detector                 'hybrid pixel area detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type
'Pilatus 200K hybrid pixel area detector on \k goniostat'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'four-circle κ-geometry diffractometer'
_diffrn_measurement_device_type
'Rigaku Oxford Diffraction XtaLAB Synergy, dual radiation diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            46395
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.445
_diffrn_reflns_theta_min         3.352
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray source'
_exptl_absorpt_coefficient_mu    1.226
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model 
plus an empirical absorption correction using spherical harmonics, 
implemented in the SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       needle
_exptl_crystal_F_000             922
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_platon_squeeze_details          'see _refine_special_details'
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00116(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018 (Sheldrick, 2015b)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         9146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0448
_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)+(0.0624P)²+0.7245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1302
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8239
_reflns_number_total             9146
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jm1c01899_si_001.cif
_cod_data_source_block           7
_cod_original_cell_volume        2142.82(9)
_cod_original_formula_sum        'C43 H62 F6 N4 O5.50 P'
_cod_database_code               1566281
_shelx_shelxl_version_number     2018/3
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.828
_oxdiff_exptl_absorpt_empirical_full_max 1.247
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_platon_squeeze_void_probe_radius 1.20
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
O1 O 0.38760(9) 0.40862(8) 0.54033(7) 0.0290(2) Uani 1 1 d . . . . .
O2 O 0.66385(10) 0.77761(10) 0.74222(9) 0.0414(2) Uani 1 1 d . . . . .
O3 O 0.73489(11) 1.17690(10) 0.50003(10) 0.0452(3) Uani 1 1 d . . . . .
O4 O 0.88881(10) 1.14208(10) 0.50859(9) 0.0433(3) Uani 1 1 d . . . . .
N1 N 0.19897(12) 0.44379(11) 0.24881(9) 0.0346(3) Uani 1 1 d . . . . .
N2 N 0.54415(14) 0.33005(12) 0.81591(10) 0.0426(3) Uani 1 1 d . . . . .
N3 N 0.63117(11) 0.87139(10) 0.64345(10) 0.0335(3) Uani 1 1 d . . . . .
N4 N 0.74300(11) 1.05079(10) 0.57138(9) 0.0329(2) Uani 1 1 d . . . . .
C1 C 0.25130(12) 0.48377(12) 0.34956(10) 0.0298(3) Uani 1 1 d . . . . .
C2 C 0.30063(12) 0.42864(11) 0.39661(10) 0.0289(3) Uani 1 1 d . . . . .
H2 H 0.301413 0.364436 0.356527 0.035 Uiso 1 1 calc R U . . .
C3 C 0.34682(12) 0.46904(11) 0.49998(10) 0.0269(3) Uani 1 1 d . . . . .
C4 C 0.35242(12) 0.56679(11) 0.56530(10) 0.0272(3) Uani 1 1 d . . . . .
C5 C 0.30776(12) 0.62380(11) 0.51614(10) 0.0297(3) Uani 1 1 d . . . . .
H5 H 0.312070 0.691058 0.556236 0.036 Uiso 1 1 calc R U . . .
C6 C 0.25946(13) 0.58493(12) 0.41410(10) 0.0318(3) Uani 1 1 d . . . . .
H6 H 0.230323 0.625185 0.384392 0.038 Uiso 1 1 calc R U . . .
C7 C 0.39683(12) 0.59935(11) 0.67018(10) 0.0280(3) Uani 1 1 d . . . . .
C8 C 0.50773(14) 0.39423(13) 0.78077(11) 0.0358(3) Uani 1 1 d . . . . .
C9 C 0.46559(13) 0.37110(12) 0.67594(10) 0.0320(3) Uani 1 1 d . . . . .
H9 H 0.463025 0.309315 0.628104 0.038 Uiso 1 1 calc R U . . .
C10 C 0.42829(12) 0.43784(11) 0.64304(10) 0.0284(3) Uani 1 1 d . . . . .
C11 C 0.43243(13) 0.53288(11) 0.71020(10) 0.0303(3) Uani 1 1 d . . . . .
C12 C 0.47766(15) 0.55654(13) 0.81516(11) 0.0373(3) Uani 1 1 d . . . . .
H12 H 0.483642 0.620604 0.862805 0.045 Uiso 1 1 calc R U . . .
C13 C 0.51272(16) 0.49052(14) 0.84977(11) 0.0399(3) Uani 1 1 d . . . . .
H13 H 0.540985 0.508315 0.920746 0.048 Uiso 1 1 calc R U . . .
C14 C 0.13444(16) 0.49284(15) 0.20210(12) 0.0418(3) Uani 1 1 d . . . . .
H141 H 0.119106 0.465456 0.127938 0.050 Uiso 1 1 calc R U . . .
H142 H 0.187763 0.577981 0.228653 0.050 Uiso 1 1 calc R U . . .
C15 C 0.01499(17) 0.46122(17) 0.22177(14) 0.0511(4) Uani 1 1 d . . . . .
H151 H -0.021712 0.497609 0.190074 0.077 Uiso 1 1 calc R U . . .
H152 H 0.029210 0.488380 0.295033 0.077 Uiso 1 1 calc R U . . .
H153 H -0.039916 0.377193 0.192944 0.077 Uiso 1 1 calc R U . . .
C16 C 0.19275(16) 0.34201(14) 0.18172(11) 0.0417(3) Uani 1 1 d . . . . .
H161 H 0.270702 0.346453 0.205550 0.050 Uiso 1 1 calc R U . . .
H162 H 0.182650 0.344336 0.112363 0.050 Uiso 1 1 calc R U . . .
C17 C 0.09086(18) 0.22848(15) 0.17726(14) 0.0528(4) Uani 1 1 d . . . . .
H171 H 0.091724 0.164926 0.131140 0.079 Uiso 1 1 calc R U . . .
H172 H 0.013065 0.222555 0.152529 0.079 Uiso 1 1 calc R U . . .
H173 H 0.101531 0.224151 0.245219 0.079 Uiso 1 1 calc R U . . .
C18 C 0.57011(19) 0.34235(17) 0.92431(13) 0.0518(4) Uani 1 1 d . . . . .
H181 H 0.553655 0.267557 0.929484 0.062 Uiso 1 1 calc R U . . .
H182 H 0.514281 0.360998 0.951771 0.062 Uiso 1 1 calc R U . . .
C19 C 0.6994(2) 0.4347(2) 0.98835(15) 0.0642(5) Uani 1 1 d . . . . .
H191 H 0.755312 0.416625 0.961998 0.096 Uiso 1 1 calc R U . . .
H192 H 0.711205 0.437733 1.058634 0.096 Uiso 1 1 calc R U . . .
H193 H 0.715434 0.509657 0.985947 0.096 Uiso 1 1 calc R U . . .
C20 C 0.54569(17) 0.23471(15) 0.74718(12) 0.0454(4) Uani 1 1 d . . . . .
H201 H 0.608667 0.224120 0.783367 0.055 Uiso 1 1 calc R U . . .
H202 H 0.567863 0.255121 0.688802 0.055 Uiso 1 1 calc R U . . .
C21 C 0.4248(2) 0.12267(16) 0.70850(15) 0.0576(5) Uani 1 1 d . . . . .
H211 H 0.431131 0.061324 0.664988 0.086 Uiso 1 1 calc R U . . .
H212 H 0.362967 0.131381 0.669367 0.086 Uiso 1 1 calc R U . . .
H213 H 0.401916 0.102511 0.766027 0.086 Uiso 1 1 calc R U . . .
C22 C 0.40846(13) 0.70507(11) 0.73889(10) 0.0291(3) Uani 1 1 d . . . . .
C23 C 0.50639(13) 0.81347(11) 0.75401(10) 0.0303(3) Uani 1 1 d . . . . .
C24 C 0.51613(15) 0.91252(13) 0.81610(11) 0.0383(3) Uani 1 1 d . . . . .
H24 H 0.582401 0.986535 0.826317 0.046 Uiso 1 1 calc R U . . .
C25 C 0.42920(16) 0.90296(14) 0.86285(12) 0.0427(4) Uani 1 1 d . . . . .
H25 H 0.436192 0.970728 0.905071 0.051 Uiso 1 1 calc R U . . .
C26 C 0.33235(16) 0.79596(15) 0.84881(12) 0.0431(4) Uani 1 1 d . . . . .
H26 H 0.273526 0.790234 0.881735 0.052 Uiso 1 1 calc R U . . .
C27 C 0.32124(14) 0.69642(13) 0.78616(11) 0.0374(3) Uani 1 1 d . . . . .
H27 H 0.254245 0.622718 0.775679 0.045 Uiso 1 1 calc R U . . .
C28 C 0.60684(13) 0.81980(11) 0.71216(11) 0.0315(3) Uani 1 1 d . . . . .
C29 C 0.73266(14) 0.88475(13) 0.60654(12) 0.0372(3) Uani 1 1 d . . . . .
H291 H 0.701311 0.834805 0.534251 0.045 Uiso 1 1 calc R U . . .
H292 H 0.779683 0.860212 0.645389 0.045 Uiso 1 1 calc R U . . .
C30 C 0.81463(13) 1.00918(13) 0.61792(12) 0.0346(3) Uani 1 1 d . . . . .
H301 H 0.856602 1.057478 0.690745 0.041 Uiso 1 1 calc R U . . .
H302 H 0.877010 1.015391 0.584853 0.041 Uiso 1 1 calc R U . . .
C31 C 0.64176(12) 1.03724(12) 0.60844(11) 0.0320(3) Uani 1 1 d . . . . .
H311 H 0.594940 1.062553 0.570438 0.038 Uiso 1 1 calc R U . . .
H312 H 0.672873 1.085925 0.681099 0.038 Uiso 1 1 calc R U . . .
C32 C 0.56009(12) 0.91178(12) 0.59483(11) 0.0320(3) Uani 1 1 d . . . . .
H321 H 0.495234 0.903512 0.625294 0.038 Uiso 1 1 calc R U . . .
H322 H 0.521288 0.864345 0.521644 0.038 Uiso 1 1 calc R U . . .
C33 C 0.78578(13) 1.12861(12) 0.52490(12) 0.0351(3) Uani 1 1 d . . . . .
C34 C 0.95133(16) 1.21896(15) 0.45618(16) 0.0494(4) Uani 1 1 d . . . . .
C35 C 1.05686(18) 1.20150(19) 0.45373(18) 0.0581(5) Uani 1 1 d . . . . .
H351 H 1.105883 1.223229 0.523211 0.087 Uiso 1 1 calc R U . . .
H352 H 1.107161 1.249796 0.420491 0.087 Uiso 1 1 calc R U . . .
H353 H 1.025788 1.120198 0.415906 0.087 Uiso 1 1 calc R U . . .
C36 C 0.8697(2) 1.1800(3) 0.35072(19) 0.0743(7) Uani 1 1 d . . . . .
H361 H 0.839266 1.098338 0.315057 0.111 Uiso 1 1 calc R U . . .
H362 H 0.915445 1.226111 0.313902 0.111 Uiso 1 1 calc R U . . .
H363 H 0.801090 1.190129 0.354449 0.111 Uiso 1 1 calc R U . . .
C37 C 0.9965(2) 1.34303(18) 0.5184(2) 0.0799(8) Uani 1 1 d . . . . .
H371 H 0.927323 1.353422 0.516636 0.120 Uiso 1 1 calc R U . . .
H372 H 1.051498 1.394875 0.490131 0.120 Uiso 1 1 calc R U . . .
H373 H 1.040028 1.360942 0.588744 0.120 Uiso 1 1 calc R U . . .
P1 P 0.87787(4) 0.23726(4) 0.91329(3) 0.04960(13) Uani 1 1 d . . . . .
F1 F 0.91272(14) 0.36594(11) 0.96303(12) 0.0903(5) Uani 1 1 d . . . . .
F2 F 0.83945(15) 0.10594(11) 0.86281(9) 0.0746(4) Uani 1 1 d . . . . .
F3 F 0.87000(14) 0.21761(14) 1.01813(9) 0.0798(4) Uani 1 1 d . . . . .
F4 F 0.88290(16) 0.25295(12) 0.80806(10) 0.0928(5) Uani 1 1 d . . . . .
F5 F 0.73674(12) 0.19421(12) 0.88340(12) 0.0857(4) Uani 1 1 d . . . . .
F6 F 1.01589(13) 0.27653(16) 0.94605(12) 0.0971(5) 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -2 1 0.1331
0 2 -1 0.1321
1 0 0 0.0281
-1 0 0 0.0281
0 0 1 0.0405
0 0 -1 0.0334
1 -5 2 0.1378
-1 5 -2 0.1454
-5 2 5 0.0800
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
C10 O1 C3 120.60(10) . . ?
C33 O4 C34 121.53(12) . . ?
C1 N1 C16 121.14(11) . . ?
C1 N1 C14 121.12(12) . . ?
C16 N1 C14 117.45(11) . . ?
C8 N2 C20 121.69(12) . . ?
C8 N2 C18 121.72(13) . . ?
C20 N2 C18 116.17(12) . . ?
C28 N3 C29 119.98(11) . . ?
C28 N3 C32 126.12(12) . . ?
C29 N3 C32 113.80(11) . . ?
C33 N4 C31 118.58(11) . . ?
C33 N4 C30 123.39(12) . . ?
C31 N4 C30 114.63(11) . . ?
N1 C1 C2 121.73(12) . . ?
N1 C1 C6 120.64(12) . . ?
C2 C1 C6 117.63(12) . . ?
C3 C2 C1 119.36(12) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 O1 116.23(11) . . ?
C2 C3 C4 123.82(11) . . ?
O1 C3 C4 119.94(11) . . ?
C7 C4 C3 119.94(11) . . ?
C7 C4 C5 124.30(12) . . ?
C3 C4 C5 115.74(12) . . ?
C6 C5 C4 121.97(12) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 121.37(12) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C4 C7 C11 119.29(11) . . ?
C4 C7 C22 120.12(11) . . ?
C11 C7 C22 120.58(12) . . ?
N2 C8 C9 121.79(13) . . ?
N2 C8 C13 120.58(13) . . ?
C9 C8 C13 117.63(12) . . ?
C10 C9 C8 120.08(12) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
O1 C10 C9 116.20(11) . . ?
O1 C10 C11 120.90(11) . . ?
C9 C10 C11 122.89(12) . . ?
C7 C11 C10 119.20(12) . . ?
C7 C11 C12 124.47(12) . . ?
C10 C11 C12 116.28(12) . . ?
C13 C12 C11 122.06(13) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C8 121.03(13) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
N1 C14 C15 113.83(14) . . ?
N1 C14 H141 108.8 . . ?
C15 C14 H141 108.8 . . ?
N1 C14 H142 108.8 . . ?
C15 C14 H142 108.8 . . ?
H141 C14 H142 107.7 . . ?
C14 C15 H151 109.5 . . ?
C14 C15 H152 109.5 . . ?
H151 C15 H152 109.5 . . ?
C14 C15 H153 109.5 . . ?
H151 C15 H153 109.5 . . ?
H152 C15 H153 109.5 . . ?
N1 C16 C17 113.84(14) . . ?
N1 C16 H161 108.8 . . ?
C17 C16 H161 108.8 . . ?
N1 C16 H162 108.8 . . ?
C17 C16 H162 108.8 . . ?
H161 C16 H162 107.7 . . ?
C16 C17 H171 109.5 . . ?
C16 C17 H172 109.5 . . ?
H171 C17 H172 109.5 . . ?
C16 C17 H173 109.5 . . ?
H171 C17 H173 109.5 . . ?
H172 C17 H173 109.5 . . ?
N2 C18 C19 113.35(16) . . ?
N2 C18 H181 108.9 . . ?
C19 C18 H181 108.9 . . ?
N2 C18 H182 108.9 . . ?
C19 C18 H182 108.9 . . ?
H181 C18 H182 107.7 . . ?
C18 C19 H191 109.5 . . ?
C18 C19 H192 109.5 . . ?
H191 C19 H192 109.5 . . ?
C18 C19 H193 109.5 . . ?
H191 C19 H193 109.5 . . ?
H192 C19 H193 109.5 . . ?
N2 C20 C21 112.49(15) . . ?
N2 C20 H201 109.1 . . ?
C21 C20 H201 109.1 . . ?
N2 C20 H202 109.1 . . ?
C21 C20 H202 109.1 . . ?
H201 C20 H202 107.8 . . ?
C20 C21 H211 109.5 . . ?
C20 C21 H212 109.5 . . ?
H211 C21 H212 109.5 . . ?
C20 C21 H213 109.5 . . ?
H211 C21 H213 109.5 . . ?
H212 C21 H213 109.5 . . ?
C27 C22 C23 119.87(12) . . ?
C27 C22 C7 120.64(12) . . ?
C23 C22 C7 119.48(12) . . ?
C24 C23 C22 119.72(13) . . ?
C24 C23 C28 121.30(13) . . ?
C22 C23 C28 118.60(11) . . ?
C25 C24 C23 119.95(14) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C24 120.72(13) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 119.77(14) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C22 119.97(14) . . ?
C26 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?
O2 C28 N3 122.32(13) . . ?
O2 C28 C23 118.64(12) . . ?
N3 C28 C23 119.04(11) . . ?
N3 C29 C30 110.47(11) . . ?
N3 C29 H291 109.6 . . ?
C30 C29 H291 109.6 . . ?
N3 C29 H292 109.6 . . ?
C30 C29 H292 109.6 . . ?
H291 C29 H292 108.1 . . ?
N4 C30 C29 110.00(12) . . ?
N4 C30 H301 109.7 . . ?
C29 C30 H301 109.7 . . ?
N4 C30 H302 109.7 . . ?
C29 C30 H302 109.7 . . ?
H301 C30 H302 108.2 . . ?
N4 C31 C32 109.60(11) . . ?
N4 C31 H311 109.8 . . ?
C32 C31 H311 109.8 . . ?
N4 C31 H312 109.8 . . ?
C32 C31 H312 109.8 . . ?
H311 C31 H312 108.2 . . ?
N3 C32 C31 109.86(11) . . ?
N3 C32 H321 109.7 . . ?
C31 C32 H321 109.7 . . ?
N3 C32 H322 109.7 . . ?
C31 C32 H322 109.7 . . ?
H321 C32 H322 108.2 . . ?
O3 C33 O4 125.44(13) . . ?
O3 C33 N4 123.73(13) . . ?
O4 C33 N4 110.81(12) . . ?
O4 C34 C36 110.31(16) . . ?
O4 C34 C35 101.43(13) . . ?
C36 C34 C35 111.11(17) . . ?
O4 C34 C37 110.10(16) . . ?
C36 C34 C37 112.64(19) . . ?
C35 C34 C37 110.69(17) . . ?
C34 C35 H351 109.5 . . ?
C34 C35 H352 109.5 . . ?
H351 C35 H352 109.5 . . ?
C34 C35 H353 109.5 . . ?
H351 C35 H353 109.5 . . ?
H352 C35 H353 109.5 . . ?
C34 C36 H361 109.5 . . ?
C34 C36 H362 109.5 . . ?
H361 C36 H362 109.5 . . ?
C34 C36 H363 109.5 . . ?
H361 C36 H363 109.5 . . ?
H362 C36 H363 109.5 . . ?
C34 C37 H371 109.5 . . ?
C34 C37 H372 109.5 . . ?
H371 C37 H372 109.5 . . ?
C34 C37 H373 109.5 . . ?
H371 C37 H373 109.5 . . ?
H372 C37 H373 109.5 . . ?
F6 P1 F1 90.28(9) . . ?
F6 P1 F4 91.22(10) . . ?
F1 P1 F4 90.87(9) . . ?
F6 P1 F2 90.97(9) . . ?
F1 P1 F2 178.70(9) . . ?
F4 P1 F2 89.44(7) . . ?
F6 P1 F5 177.42(10) . . ?
F1 P1 F5 90.78(8) . . ?
F4 P1 F5 91.11(10) . . ?
F2 P1 F5 87.95(8) . . ?
F6 P1 F3 89.54(9) . . ?
F1 P1 F3 90.54(9) . . ?
F4 P1 F3 178.39(8) . . ?
F2 P1 F3 89.13(8) . . ?
F5 P1 F3 88.10(8) . . ?
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
O1 C10 1.3672(15) . ?
O1 C3 1.3714(15) . ?
O2 C28 1.2303(17) . ?
O3 C33 1.2167(17) . ?
O4 C33 1.3419(17) . ?
O4 C34 1.4695(19) . ?
N1 C1 1.3420(18) . ?
N1 C16 1.4751(18) . ?
N1 C14 1.4835(18) . ?
N2 C8 1.3484(18) . ?
N2 C20 1.4688(19) . ?
N2 C18 1.483(2) . ?
N3 C28 1.3477(18) . ?
N3 C29 1.4594(18) . ?
N3 C32 1.4597(16) . ?
N4 C33 1.3576(18) . ?
N4 C31 1.4570(17) . ?
N4 C30 1.4653(17) . ?
C1 C2 1.4249(18) . ?
C1 C6 1.4410(18) . ?
C2 C3 1.3669(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.4245(17) . ?
C4 C7 1.3942(18) . ?
C4 C5 1.4268(17) . ?
C5 C6 1.3533(19) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C11 1.4058(18) . ?
C7 C22 1.4938(17) . ?
C8 C9 1.4120(19) . ?
C8 C13 1.436(2) . ?
C9 C10 1.3737(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.4162(18) . ?
C11 C12 1.4172(19) . ?
C12 C13 1.358(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.512(2) . ?
C14 H141 0.9900 . ?
C14 H142 0.9900 . ?
C15 H151 0.9800 . ?
C15 H152 0.9800 . ?
C15 H153 0.9800 . ?
C16 C17 1.507(3) . ?
C16 H161 0.9900 . ?
C16 H162 0.9900 . ?
C17 H171 0.9800 . ?
C17 H172 0.9800 . ?
C17 H173 0.9800 . ?
C18 C19 1.511(3) . ?
C18 H181 0.9900 . ?
C18 H182 0.9900 . ?
C19 H191 0.9800 . ?
C19 H192 0.9800 . ?
C19 H193 0.9800 . ?
C20 C21 1.509(3) . ?
C20 H201 0.9900 . ?
C20 H202 0.9900 . ?
C21 H211 0.9800 . ?
C21 H212 0.9800 . ?
C21 H213 0.9800 . ?
C22 C27 1.394(2) . ?
C22 C23 1.3953(19) . ?
C23 C24 1.3936(18) . ?
C23 C28 1.5083(19) . ?
C24 C25 1.384(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.381(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.394(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C29 C30 1.513(2) . ?
C29 H291 0.9900 . ?
C29 H292 0.9900 . ?
C30 H301 0.9900 . ?
C30 H302 0.9900 . ?
C31 C32 1.5153(19) . ?
C31 H311 0.9900 . ?
C31 H312 0.9900 . ?
C32 H321 0.9900 . ?
C32 H322 0.9900 . ?
C34 C36 1.504(3) . ?
C34 C35 1.516(2) . ?
C34 C37 1.517(3) . ?
C35 H351 0.9800 . ?
C35 H352 0.9800 . ?
C35 H353 0.9800 . ?
C36 H361 0.9800 . ?
C36 H362 0.9800 . ?
C36 H363 0.9800 . ?
C37 H371 0.9800 . ?
C37 H372 0.9800 . ?
C37 H373 0.9800 . ?
P1 F6 1.5724(14) . ?
P1 F1 1.5755(14) . ?
P1 F4 1.5802(14) . ?
P1 F2 1.5960(12) . ?
P1 F5 1.5977(14) . ?
P1 F3 1.5993(14) . ?
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
C16 N1 C1 C2 -1.5(2) . . . . ?
C14 N1 C1 C2 172.26(13) . . . . ?
C16 N1 C1 C6 178.48(13) . . . . ?
C14 N1 C1 C6 -7.8(2) . . . . ?
N1 C1 C2 C3 -176.37(13) . . . . ?
C6 C1 C2 C3 3.69(19) . . . . ?
C1 C2 C3 O1 177.05(11) . . . . ?
C1 C2 C3 C4 -2.0(2) . . . . ?
C10 O1 C3 C2 -175.86(12) . . . . ?
C10 O1 C3 C4 3.19(18) . . . . ?
C2 C3 C4 C7 177.55(13) . . . . ?
O1 C3 C4 C7 -1.43(19) . . . . ?
C2 C3 C4 C5 -0.97(19) . . . . ?
O1 C3 C4 C5 -179.95(11) . . . . ?
C7 C4 C5 C6 -176.31(13) . . . . ?
C3 C4 C5 C6 2.14(19) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
N1 C1 C6 C5 177.45(13) . . . . ?
C2 C1 C6 C5 -2.6(2) . . . . ?
C3 C4 C7 C11 -1.79(19) . . . . ?
C5 C4 C7 C11 176.60(13) . . . . ?
C3 C4 C7 C22 177.05(12) . . . . ?
C5 C4 C7 C22 -4.6(2) . . . . ?
C20 N2 C8 C9 2.0(3) . . . . ?
C18 N2 C8 C9 -170.33(16) . . . . ?
C20 N2 C8 C13 -176.92(16) . . . . ?
C18 N2 C8 C13 10.8(3) . . . . ?
N2 C8 C9 C10 179.45(14) . . . . ?
C13 C8 C9 C10 -1.6(2) . . . . ?
C3 O1 C10 C9 179.10(12) . . . . ?
C3 O1 C10 C11 -1.71(19) . . . . ?
C8 C9 C10 O1 -179.29(13) . . . . ?
C8 C9 C10 C11 1.5(2) . . . . ?
C4 C7 C11 C10 3.2(2) . . . . ?
C22 C7 C11 C10 -175.60(12) . . . . ?
C4 C7 C11 C12 -179.33(14) . . . . ?
C22 C7 C11 C12 1.8(2) . . . . ?
O1 C10 C11 C7 -1.5(2) . . . . ?
C9 C10 C11 C7 177.59(13) . . . . ?
O1 C10 C11 C12 -179.18(13) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C7 C11 C12 C13 -178.87(15) . . . . ?
C10 C11 C12 C13 -1.4(2) . . . . ?
C11 C12 C13 C8 1.3(3) . . . . ?
N2 C8 C13 C12 179.18(16) . . . . ?
C9 C8 C13 C12 0.2(2) . . . . ?
C1 N1 C14 C15 -71.39(19) . . . . ?
C16 N1 C14 C15 102.55(16) . . . . ?
C1 N1 C16 C17 80.91(18) . . . . ?
C14 N1 C16 C17 -93.03(16) . . . . ?
C8 N2 C18 C19 -87.5(2) . . . . ?
C20 N2 C18 C19 99.75(19) . . . . ?
C8 N2 C20 C21 -86.28(19) . . . . ?
C18 N2 C20 C21 86.43(18) . . . . ?
C4 C7 C22 C27 100.32(16) . . . . ?
C11 C7 C22 C27 -80.85(17) . . . . ?
C4 C7 C22 C23 -78.34(16) . . . . ?
C11 C7 C22 C23 100.49(15) . . . . ?
C27 C22 C23 C24 -0.2(2) . . . . ?
C7 C22 C23 C24 178.47(12) . . . . ?
C27 C22 C23 C28 172.83(12) . . . . ?
C7 C22 C23 C28 -8.50(18) . . . . ?
C22 C23 C24 C25 0.4(2) . . . . ?
C28 C23 C24 C25 -172.49(14) . . . . ?
C23 C24 C25 C26 0.0(2) . . . . ?
C24 C25 C26 C27 -0.6(2) . . . . ?
C25 C26 C27 C22 0.7(2) . . . . ?
C23 C22 C27 C26 -0.3(2) . . . . ?
C7 C22 C27 C26 -179.00(13) . . . . ?
C29 N3 C28 O2 -3.6(2) . . . . ?
C32 N3 C28 O2 172.48(13) . . . . ?
C29 N3 C28 C23 176.28(12) . . . . ?
C32 N3 C28 C23 -7.6(2) . . . . ?
C24 C23 C28 O2 112.49(16) . . . . ?
C22 C23 C28 O2 -60.42(18) . . . . ?
C24 C23 C28 N3 -67.43(18) . . . . ?
C22 C23 C28 N3 119.65(14) . . . . ?
C28 N3 C29 C30 -127.60(14) . . . . ?
C32 N3 C29 C30 55.82(16) . . . . ?
C33 N4 C30 C29 -146.55(14) . . . . ?
C31 N4 C30 C29 54.65(16) . . . . ?
N3 C29 C30 N4 -52.21(16) . . . . ?
C33 N4 C31 C32 144.32(13) . . . . ?
C30 N4 C31 C32 -55.79(15) . . . . ?
C28 N3 C32 C31 126.81(14) . . . . ?
C29 N3 C32 C31 -56.87(15) . . . . ?
N4 C31 C32 N3 54.52(15) . . . . ?
C34 O4 C33 O3 -0.6(3) . . . . ?
C34 O4 C33 N4 177.97(14) . . . . ?
C31 N4 C33 O3 -10.2(2) . . . . ?
C30 N4 C33 O3 -168.23(15) . . . . ?
C31 N4 C33 O4 171.22(12) . . . . ?
C30 N4 C33 O4 13.2(2) . . . . ?
C33 O4 C34 C36 -60.4(2) . . . . ?
C33 O4 C34 C35 -178.23(15) . . . . ?
C33 O4 C34 C37 64.5(2) . . . . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.000 -0.000 -0.000 406 110 ' '
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0037 -2.0010 0.9975 0.2205 -0.1159 -0.0070
-0.0037 2.0010 -0.9975 -0.2205 0.1159 0.0070
0.9977 0.0007 0.0033 0.0022 0.1227 0.0667
-0.9977 -0.0007 -0.0033 -0.0022 -0.1227 -0.0667
-0.0027 -0.0001 1.0011 0.0046 -0.0203 0.1150
0.0027 0.0001 -1.0011 -0.0046 0.0203 -0.1150
1.0084 -5.0018 1.9965 0.5513 -0.1568 -0.0084
-1.0084 5.0018 -1.9965 -0.5513 0.1568 0.0084
-5.0084 1.9967 4.9924 -0.2040 -0.6198 0.3635
