#------------------------------------------------------------------------------
#$Date: 2025-10-24 11:02:00 +0300 (Fri, 24 Oct 2025) $
#$Revision: 302984 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/60/1576054.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_1576054
loop_
_publ_author_name
'Abd El-Gaber, Mohammed K.'
'Herrick, Ryan'
'Sudhakar, Pranaya'
'Rana, Ashutosh'
'Roach, Brent A.'
'Dick, Jeffrey E.'
'Altman, Ryan A.'
_publ_section_title
;
 Diselenide-Enabled Photocatalytic Hydroazolation of gem-Difluoroalkenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC04074D
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H40 F2 N2 O5, 0.25(C6 H14)'
_chemical_formula_sum            'C43.5 H43.5 F2 N2 O5'
_chemical_formula_weight         712.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-01-03 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.925(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   43.884(9)
_cell_length_b                   5.5853(12)
_cell_length_c                   15.050(2)
_cell_measurement_reflns_used    7389
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      79.1913
_cell_measurement_theta_min      2.9401
_cell_volume                     3684.0(12)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'Apex5 v2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_refinement
;  
SHELXL-2019/2 (Sheldrick, 2015a, 2019), 
SHELXLE Rev1613 (Hübschle et al., 2011)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_detector_type
'PhotonIII_C14 charge-integrating and photon counting pixel array'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device       'four circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'HELIOS multilayer Montel optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       55
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18691
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.214
_diffrn_reflns_theta_min         2.016
_diffrn_source                   'I-mu-S 3.0 microsource X-ray tube'
_diffrn_source_current           '1.1 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.5559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       needle
_exptl_crystal_F_000             1506
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1376 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.23(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         7038
_refine_ls_number_restraints     292
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0530
_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)+(0.0549P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1338
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    0.907
_reflns_Friedel_fraction_max     0.778
_reflns_number_gt                4584
_reflns_number_total             7038
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc04074d2.cif
_cod_data_source_block           RMH3_258_0m
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C43.50 H43.50 F2 N2 O5'
_cod_database_code               1576054
_shelx_shelxl_version_number     2019/3
_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.
;
_shelx_estimated_absorpt_t_min   0.732
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
F1 F 0.29406(6) 0.0934(5) 0.26760(15) 0.0664(7) Uani 1 1 d . . . . .
F2 F 0.29453(5) 0.4128(4) 0.34886(14) 0.0540(6) Uani 1 1 d . . . . .
O1 O 0.32655(7) 0.4225(5) 0.15908(16) 0.0549(7) Uani 1 1 d . . . . .
O2 O 0.40854(8) 0.1461(6) 0.5018(2) 0.0711(9) Uani 1 1 d . . . . .
O3 O 0.42805(7) 0.5454(6) 0.2845(2) 0.0613(8) Uani 1 1 d . . . . .
O4 O 0.35979(6) 0.3198(5) 0.38243(15) 0.0460(7) Uani 1 1 d . . . . .
O6 O 0.38000(7) 0.7220(5) 0.16674(17) 0.0593(8) Uani 1 1 d . . . . .
N1 N 0.31017(8) 0.0706(6) 0.4130(2) 0.0456(8) Uani 1 1 d . . . . .
N2 N 0.32795(8) -0.1308(6) 0.4146(2) 0.0524(8) Uani 1 1 d . . . . .
C1 C 0.40801(11) 0.3696(9) 0.4565(3) 0.0630(12) Uani 1 1 d . . . . .
H1A H 0.429107 0.425461 0.448536 0.076 Uiso 1 1 calc R U . . .
H1B H 0.397441 0.491047 0.491613 0.076 Uiso 1 1 calc R U . . .
C2 C 0.39167(10) 0.3377(8) 0.3683(3) 0.0521(11) Uani 1 1 d . . . . .
H2 H 0.398773 0.186757 0.340162 0.062 Uiso 1 1 calc R U . . .
C3 C 0.39655(10) 0.5482(8) 0.3059(3) 0.0510(10) Uani 1 1 d . . . . .
H3 H 0.391624 0.702109 0.335917 0.061 Uiso 1 1 calc R U . . .
C4 C 0.37670(10) 0.5191(8) 0.2214(3) 0.0516(10) Uani 1 1 d . . . . .
H4 H 0.384169 0.376329 0.188875 0.062 Uiso 1 1 calc R U . . .
C5 C 0.34352(10) 0.4765(7) 0.2403(2) 0.0480(10) Uani 1 1 d . . . . .
H5 H 0.334904 0.622688 0.268082 0.058 Uiso 1 1 calc R U . . .
C6 C 0.34207(10) 0.2646(8) 0.3047(2) 0.0475(9) Uani 1 1 d . . . . .
H6 H 0.350634 0.119078 0.276356 0.057 Uiso 1 1 calc R U . . .
C7 C 0.31034(10) 0.2094(7) 0.3339(3) 0.0492(10) Uani 1 1 d . . . . .
C8 C 0.32499(10) -0.2281(8) 0.4930(3) 0.0510(10) Uani 1 1 d . . . . .
H8 H 0.334727 -0.372277 0.512176 0.061 Uiso 1 1 calc R U . . .
C9 C 0.30548(9) -0.0916(7) 0.5455(2) 0.0437(9) Uani 1 1 d . . . . .
C10 C 0.29465(9) -0.1159(8) 0.6312(2) 0.0469(9) Uani 1 1 d . . . . .
H10 H 0.300691 -0.247789 0.667874 0.056 Uiso 1 1 calc R U . . .
C11 C 0.27512(9) 0.0554(8) 0.6609(2) 0.0483(10) Uani 1 1 d . . . . .
H11 H 0.267536 0.042173 0.718657 0.058 Uiso 1 1 calc R U . . .
C12 C 0.26632(9) 0.2495(8) 0.6065(2) 0.0490(10) Uani 1 1 d . . . . .
H12 H 0.252915 0.365968 0.628789 0.059 Uiso 1 1 calc R U . . .
C13 C 0.27632(9) 0.2781(7) 0.5221(2) 0.0441(9) Uani 1 1 d . . . . .
H13 H 0.270112 0.410167 0.485715 0.053 Uiso 1 1 calc R U . . .
C14 C 0.29605(8) 0.1031(7) 0.4926(2) 0.0412(9) Uani 1 1 d . . . . .
C15 C 0.42047(12) 0.1638(11) 0.5916(3) 0.0774(15) Uani 1 1 d . . . . .
H15A H 0.441143 0.234975 0.592322 0.093 Uiso 1 1 calc R U . . .
H15B H 0.422294 0.001373 0.617662 0.093 Uiso 1 1 calc R U . . .
C16 C 0.40035(12) 0.3153(9) 0.6475(3) 0.0642(13) Uani 1 1 d . . . . .
C17 C 0.36946(12) 0.2621(10) 0.6511(3) 0.0672(13) Uani 1 1 d . . . . .
H17 H 0.361224 0.127409 0.619721 0.081 Uiso 1 1 calc R U . . .
C18 C 0.35095(12) 0.4018(11) 0.6993(3) 0.0705(13) Uani 1 1 d . . . . .
H18 H 0.329903 0.363322 0.701170 0.085 Uiso 1 1 calc R U . . .
C19 C 0.36234(13) 0.5978(10) 0.7453(3) 0.0736(14) Uani 1 1 d . . . . .
H19 H 0.349308 0.694842 0.778678 0.088 Uiso 1 1 calc R U . . .
C20 C 0.39291(14) 0.6515(10) 0.7423(4) 0.0783(15) Uani 1 1 d . . . . .
H20 H 0.401071 0.785498 0.774258 0.094 Uiso 1 1 calc R U . . .
C21 C 0.41167(13) 0.5121(11) 0.6933(4) 0.0759(15) Uani 1 1 d . . . . .
H21 H 0.432663 0.552020 0.691029 0.091 Uiso 1 1 calc R U . . .
C22 C 0.44232(12) 0.7728(9) 0.2875(3) 0.0663(13) Uani 1 1 d . . . . .
H22A H 0.446033 0.823268 0.350214 0.080 Uiso 1 1 calc R U . A 1
H22B H 0.428793 0.892576 0.257239 0.080 Uiso 1 1 calc R U . A 1
C23 C 0.47197(11) 0.7609(9) 0.2427(3) 0.0621(11) Uani 0.533(19) 1 d D U P B 1
C24 C 0.4957(3) 0.927(2) 0.2661(10) 0.073(3) Uani 0.533(19) 1 d D U P B 1
H24 H 0.493244 1.036658 0.313371 0.088 Uiso 0.533(19) 1 calc R U P B 1
C25 C 0.5223(3) 0.929(3) 0.2201(10) 0.080(3) Uani 0.533(19) 1 d D U P B 1
H25 H 0.538738 1.030207 0.238968 0.096 Uiso 0.533(19) 1 calc R U P B 1
C26 C 0.5248(5) 0.782(4) 0.1470(16) 0.082(3) Uani 0.533(19) 1 d D U P B 1
H26 H 0.541271 0.802437 0.108954 0.099 Uiso 0.533(19) 1 calc R U P B 1
C27 C 0.5033(4) 0.607(3) 0.1297(10) 0.082(3) Uani 0.533(19) 1 d D U P B 1
H27 H 0.506249 0.490638 0.084821 0.098 Uiso 0.533(19) 1 calc R U P B 1
C28 C 0.4771(4) 0.601(3) 0.1787(9) 0.069(3) Uani 0.533(19) 1 d D U P B 1
H28 H 0.462374 0.479630 0.166203 0.083 Uiso 0.533(19) 1 calc R U P B 1
C23B C 0.47197(11) 0.7609(9) 0.2427(3) 0.0621(11) Uani 0.467(19) 1 d D U P B 2
C24B C 0.4878(3) 0.972(2) 0.2312(11) 0.071(3) Uani 0.467(19) 1 d D U P B 2
H24B H 0.479853 1.118929 0.252096 0.086 Uiso 0.467(19) 1 calc R U P B 2
C25B C 0.5151(4) 0.970(3) 0.1893(12) 0.080(3) Uani 0.467(19) 1 d D U P B 2
H25B H 0.526035 1.114810 0.182311 0.096 Uiso 0.467(19) 1 calc R U P B 2
C26B C 0.5266(6) 0.760(4) 0.1577(19) 0.082(3) Uani 0.467(19) 1 d D U P B 2
H26B H 0.546581 0.754341 0.136448 0.098 Uiso 0.467(19) 1 calc R U P B 2
C27B C 0.5087(4) 0.558(3) 0.1572(12) 0.079(3) Uani 0.467(19) 1 d D U P B 2
H27B H 0.515069 0.417693 0.127585 0.094 Uiso 0.467(19) 1 calc R U P B 2
C28B C 0.4810(4) 0.558(3) 0.2003(11) 0.069(3) Uani 0.467(19) 1 d D U P B 2
H28B H 0.468683 0.418045 0.199950 0.082 Uiso 0.467(19) 1 calc R U P B 2
C29 C 0.38703(17) 0.6600(11) 0.0785(3) 0.0903(19) Uani 1 1 d . . . . .
H29A H 0.369044 0.584103 0.047677 0.108 Uiso 1 1 calc R U . . .
H29B H 0.404018 0.543122 0.080163 0.108 Uiso 1 1 calc R U . . .
C30 C 0.39597(12) 0.8799(9) 0.0281(3) 0.0627(12) Uani 1 1 d . . . . .
C31 C 0.37792(14) 0.9748(11) -0.0382(3) 0.0774(15) Uani 1 1 d . . . . .
H31 H 0.358028 0.911946 -0.050387 0.093 Uiso 1 1 calc R U . . .
C32 C 0.3881(2) 1.1609(12) -0.0878(4) 0.099(2) Uani 1 1 d . . . . .
H32 H 0.375387 1.222684 -0.135448 0.119 Uiso 1 1 calc R U . . .
C33 C 0.4161(2) 1.2583(12) -0.0699(4) 0.093(2) Uani 1 1 d . . . . .
H33 H 0.422594 1.390250 -0.103894 0.112 Uiso 1 1 calc R U . . .
C34 C 0.43438(15) 1.1695(11) -0.0047(4) 0.0860(17) Uani 1 1 d . . . . .
H34 H 0.453942 1.237917 0.007867 0.103 Uiso 1 1 calc R U . . .
C35 C 0.42480(14) 0.9776(11) 0.0444(3) 0.0823(17) Uani 1 1 d . . . . .
H35 H 0.438085 0.911561 0.089801 0.099 Uiso 1 1 calc R U . . .
C36 C 0.30770(11) 0.6140(8) 0.1266(3) 0.0586(11) Uani 1 1 d . . . . .
H36A H 0.319147 0.766528 0.131580 0.070 Uiso 1 1 calc R U . . .
H36B H 0.289578 0.627399 0.162897 0.070 Uiso 1 1 calc R U . . .
C37 C 0.29774(10) 0.5692(8) 0.0312(2) 0.0514(10) Uani 1 1 d D . . . .
C38 C 0.27851(12) 0.7340(8) -0.0122(3) 0.0612(12) Uani 1 1 d D . . . .
H38 H 0.271898 0.870466 0.019193 0.073 Uiso 1 1 calc R U . . .
C39 C 0.26890(12) 0.7030(9) -0.0997(3) 0.0650(13) Uani 1 1 d D . . . .
H39 H 0.255658 0.817158 -0.128192 0.078 Uiso 1 1 calc R U . . .
C40 C 0.27839(12) 0.5074(9) -0.1461(3) 0.0617(12) Uani 1 1 d D . . . .
H40 H 0.272013 0.486815 -0.206862 0.074 Uiso 1 1 calc R U . . .
C41 C 0.29721(12) 0.3415(8) -0.1039(3) 0.0654(13) Uani 1 1 d D . . . .
H41 H 0.303540 0.204721 -0.135599 0.078 Uiso 1 1 calc R U . . .
C42 C 0.30700(11) 0.3713(8) -0.0160(3) 0.0599(12) Uani 1 1 d D . . . .
H42 H 0.320127 0.255839 0.012232 0.072 Uiso 1 1 calc R U . . .
C43 C 0.5013(15) 0.540(6) 0.477(3) 0.125(11) Uani 0.25 1 d D U P C -1
H43A H 0.506483 0.675891 0.515933 0.188 Uiso 0.25 1 calc R U P C -1
H43B H 0.515442 0.535447 0.428328 0.188 Uiso 0.25 1 calc R U P C -1
H43C H 0.480388 0.559298 0.451550 0.188 Uiso 0.25 1 calc R U P C -1
C44 C 0.5039(10) 0.296(6) 0.532(2) 0.118(8) Uani 0.25 1 d D U P C -1
H44A H 0.524930 0.273783 0.558105 0.142 Uiso 0.25 1 calc R U P C -1
H44B H 0.489692 0.297760 0.581449 0.142 Uiso 0.25 1 calc R U P C -1
C45 C 0.4956(8) 0.098(6) 0.4675(16) 0.120(7) Uani 0.25 1 d D U P C -1
H45A H 0.511703 0.076935 0.424389 0.144 Uiso 0.25 1 calc R U P C -1
H45B H 0.476045 0.132791 0.434468 0.144 Uiso 0.25 1 calc R U P C -1
C46 C 0.4928(7) -0.135(5) 0.5274(18) 0.114(7) Uani 0.25 1 d D U P C -1
H46A H 0.501580 -0.105920 0.588221 0.137 Uiso 0.25 1 calc R U P C -1
H46B H 0.471066 -0.181106 0.531303 0.137 Uiso 0.25 1 calc R U P C -1
C47 C 0.5100(8) -0.330(7) 0.483(2) 0.123(8) Uani 0.25 1 d D U P C -1
H47A H 0.532310 -0.302526 0.489472 0.148 Uiso 0.25 1 calc R U P C -1
H47B H 0.503768 -0.342960 0.419129 0.148 Uiso 0.25 1 calc R U P C -1
C48 C 0.5001(11) -0.568(7) 0.538(3) 0.135(11) Uani 0.25 1 d D U P C -1
H48A H 0.510235 -0.708660 0.514235 0.202 Uiso 0.25 1 calc R U P C -1
H48B H 0.506249 -0.548293 0.600995 0.202 Uiso 0.25 1 calc R U P C -1
H48C H 0.477951 -0.588382 0.531251 0.202 Uiso 0.25 1 calc R U P C -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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'
F F 0.0727 0.0534 '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
C36 O1 C5 113.7(3) . . ?
C1 O2 C15 112.9(4) . . ?
C22 O3 C3 114.4(3) . . ?
C6 O4 C2 113.3(3) . . ?
C4 O6 C29 112.5(4) . . ?
N2 N1 C14 111.8(3) . . ?
N2 N1 C7 115.8(3) . . ?
C14 N1 C7 132.3(3) . . ?
C8 N2 N1 105.9(3) . . ?
O2 C1 C2 108.5(4) . . ?
O2 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
O2 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
O4 C2 C1 107.8(3) . . ?
O4 C2 C3 108.3(3) . . ?
C1 C2 C3 112.4(4) . . ?
O4 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
O3 C3 C4 109.3(3) . . ?
O3 C3 C2 107.3(3) . . ?
C4 C3 C2 110.0(4) . . ?
O3 C3 H3 110.1 . . ?
C4 C3 H3 110.1 . . ?
C2 C3 H3 110.1 . . ?
O6 C4 C3 109.4(4) . . ?
O6 C4 C5 111.3(4) . . ?
C3 C4 C5 112.1(3) . . ?
O6 C4 H4 108.0 . . ?
C3 C4 H4 108.0 . . ?
C5 C4 H4 108.0 . . ?
O1 C5 C4 109.6(3) . . ?
O1 C5 C6 109.9(3) . . ?
C4 C5 C6 108.1(3) . . ?
O1 C5 H5 109.7 . . ?
C4 C5 H5 109.7 . . ?
C6 C5 H5 109.7 . . ?
O4 C6 C7 106.3(3) . . ?
O4 C6 C5 108.5(3) . . ?
C7 C6 C5 114.2(3) . . ?
O4 C6 H6 109.2 . . ?
C7 C6 H6 109.2 . . ?
C5 C6 H6 109.2 . . ?
F2 C7 F1 105.5(3) . . ?
F2 C7 N1 107.1(3) . . ?
F1 C7 N1 109.2(3) . . ?
F2 C7 C6 111.3(3) . . ?
F1 C7 C6 109.9(3) . . ?
N1 C7 C6 113.5(3) . . ?
N2 C8 C9 111.7(4) . . ?
N2 C8 H8 124.2 . . ?
C9 C8 H8 124.2 . . ?
C14 C9 C10 119.6(4) . . ?
C14 C9 C8 105.7(3) . . ?
C10 C9 C8 134.7(4) . . ?
C11 C10 C9 118.5(4) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C10 C11 C12 120.5(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 122.6(4) . . ?
C13 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C12 C13 C14 116.4(4) . . ?
C12 C13 H13 121.8 . . ?
C14 C13 H13 121.8 . . ?
N1 C14 C13 132.7(4) . . ?
N1 C14 C9 104.9(3) . . ?
C13 C14 C9 122.4(3) . . ?
O2 C15 C16 111.7(4) . . ?
O2 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
O2 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C21 C16 C17 118.5(5) . . ?
C21 C16 C15 121.3(5) . . ?
C17 C16 C15 120.1(5) . . ?
C18 C17 C16 120.5(5) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.8(5) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C20 119.1(6) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C21 C20 C19 120.4(6) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C16 120.7(5) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
O3 C22 C23B 109.8(4) . . ?
O3 C22 C23 109.8(4) . . ?
O3 C22 H22A 109.7 . . ?
C23 C22 H22A 109.7 . . ?
O3 C22 H22B 109.7 . . ?
C23 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C28 C23 C24 117.6(9) . . ?
C28 C23 C22 122.3(8) . . ?
C24 C23 C22 120.0(6) . . ?
C25 C24 C23 120.3(10) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 119.8(13) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C27 C26 C25 119.3(14) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C27 C28 119.4(13) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C23 C28 C27 122.5(12) . . ?
C23 C28 H28 118.7 . . ?
C27 C28 H28 118.7 . . ?
C28B C23B C24B 119.2(9) . . ?
C28B C23B C22 121.7(9) . . ?
C24B C23B C22 118.1(7) . . ?
C23B C24B C25B 120.0(11) . . ?
C23B C24B H24B 120.0 . . ?
C25B C24B H24B 120.0 . . ?
C26B C25B C24B 120.6(14) . . ?
C26B C25B H25B 119.7 . . ?
C24B C25B H25B 119.7 . . ?
C25B C26B C27B 119.0(16) . . ?
C25B C26B H26B 120.5 . . ?
C27B C26B H26B 120.5 . . ?
C26B C27B C28B 120.3(14) . . ?
C26B C27B H27B 119.9 . . ?
C28B C27B H27B 119.9 . . ?
C23B C28B C27B 119.5(13) . . ?
C23B C28B H28B 120.2 . . ?
C27B C28B H28B 120.2 . . ?
O6 C29 C30 110.2(4) . . ?
O6 C29 H29A 109.6 . . ?
C30 C29 H29A 109.6 . . ?
O6 C29 H29B 109.6 . . ?
C30 C29 H29B 109.6 . . ?
H29A C29 H29B 108.1 . . ?
C31 C30 C35 118.1(5) . . ?
C31 C30 C29 122.3(5) . . ?
C35 C30 C29 119.4(5) . . ?
C30 C31 C32 120.4(6) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C33 C32 C31 120.8(6) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C34 C33 C32 120.2(6) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 119.7(6) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C34 C35 C30 120.7(5) . . ?
C34 C35 H35 119.6 . . ?
C30 C35 H35 119.6 . . ?
O1 C36 C37 109.8(3) . . ?
O1 C36 H36A 109.7 . . ?
C37 C36 H36A 109.7 . . ?
O1 C36 H36B 109.7 . . ?
C37 C36 H36B 109.7 . . ?
H36A C36 H36B 108.2 . . ?
C42 C37 C38 118.3(4) . . ?
C42 C37 C36 123.0(4) . . ?
C38 C37 C36 118.7(4) . . ?
C39 C38 C37 121.1(4) . . ?
C39 C38 H38 119.4 . . ?
C37 C38 H38 119.4 . . ?
C40 C39 C38 120.1(4) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C39 C40 C41 119.5(4) . . ?
C39 C40 H40 120.3 . . ?
C41 C40 H40 120.3 . . ?
C40 C41 C42 120.8(4) . . ?
C40 C41 H41 119.6 . . ?
C42 C41 H41 119.6 . . ?
C41 C42 C37 120.1(4) . . ?
C41 C42 H42 119.9 . . ?
C37 C42 H42 119.9 . . ?
C44 C43 H43A 109.5 . . ?
C44 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C44 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C45 C44 C43 106.1(18) . . ?
C45 C44 H44A 110.5 . . ?
C43 C44 H44A 110.5 . . ?
C45 C44 H44B 110.5 . . ?
C43 C44 H44B 110.5 . . ?
H44A C44 H44B 108.7 . . ?
C44 C45 C46 104.9(16) . . ?
C44 C45 H45A 110.8 . . ?
C46 C45 H45A 110.8 . . ?
C44 C45 H45B 110.8 . . ?
C46 C45 H45B 110.8 . . ?
H45A C45 H45B 108.8 . . ?
C47 C46 C45 106.6(17) . . ?
C47 C46 H46A 110.4 . . ?
C45 C46 H46A 110.4 . . ?
C47 C46 H46B 110.4 . . ?
C45 C46 H46B 110.4 . . ?
H46A C46 H46B 108.6 . . ?
C46 C47 C48 102.2(19) . . ?
C46 C47 H47A 111.3 . . ?
C48 C47 H47A 111.3 . . ?
C46 C47 H47B 111.3 . . ?
C48 C47 H47B 111.3 . . ?
H47A C47 H47B 109.2 . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
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
F1 C7 1.361(5) . ?
F2 C7 1.356(5) . ?
O1 C36 1.423(5) . ?
O1 C5 1.431(5) . ?
O2 C1 1.422(6) . ?
O2 C15 1.428(6) . ?
O3 C22 1.416(6) . ?
O3 C3 1.435(5) . ?
O4 C6 1.405(5) . ?
O4 C2 1.430(5) . ?
O6 C4 1.412(5) . ?
O6 C29 1.422(5) . ?
N1 N2 1.369(5) . ?
N1 C14 1.390(5) . ?
N1 C7 1.421(5) . ?
N2 C8 1.311(5) . ?
C1 C2 1.486(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.527(6) . ?
C2 H2 1.0000 . ?
C3 C4 1.512(6) . ?
C3 H3 1.0000 . ?
C4 C5 1.516(6) . ?
C4 H4 1.0000 . ?
C5 C6 1.533(5) . ?
C5 H5 1.0000 . ?
C6 C7 1.513(6) . ?
C6 H6 1.0000 . ?
C8 C9 1.417(6) . ?
C8 H8 0.9500 . ?
C9 C14 1.398(5) . ?
C9 C10 1.404(5) . ?
C10 C11 1.374(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.401(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(6) . ?
C13 H13 0.9500 . ?
C15 C16 1.510(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.377(7) . ?
C16 C17 1.391(7) . ?
C17 C18 1.362(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.378(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(8) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23B 1.497(7) . ?
C22 C23 1.497(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C28 1.340(12) . ?
C23 C24 1.423(11) . ?
C24 C25 1.388(12) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(17) . ?
C25 H25 0.9500 . ?
C26 C27 1.376(15) . ?
C26 H26 0.9500 . ?
C27 C28 1.399(13) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C23B C28B 1.371(14) . ?
C23B C24B 1.384(12) . ?
C24B C25B 1.384(14) . ?
C24B H24B 0.9500 . ?
C25B C26B 1.369(18) . ?
C25B H25B 0.9500 . ?
C26B C27B 1.375(16) . ?
C26B H26B 0.9500 . ?
C27B C28B 1.406(14) . ?
C27B H27B 0.9500 . ?
C28B H28B 0.9500 . ?
C29 C30 1.506(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.350(7) . ?
C30 C35 1.388(8) . ?
C31 C32 1.368(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.358(10) . ?
C32 H32 0.9500 . ?
C33 C34 1.331(9) . ?
C33 H33 0.9500 . ?
C34 C35 1.380(8) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C37 1.500(6) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C42 1.386(6) . ?
C37 C38 1.389(6) . ?
C38 C39 1.373(6) . ?
C38 H38 0.9500 . ?
C39 C40 1.373(6) . ?
C39 H39 0.9500 . ?
C40 C41 1.375(6) . ?
C40 H40 0.9500 . ?
C41 C42 1.380(6) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C44 1.60(2) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 C45 1.51(2) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.59(2) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 C47 1.50(2) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.63(2) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
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
C14 N1 N2 C8 1.0(4) . . . . ?
C7 N1 N2 C8 178.8(3) . . . . ?
C15 O2 C1 C2 -172.8(4) . . . . ?
C6 O4 C2 C1 -173.9(3) . . . . ?
C6 O4 C2 C3 64.3(4) . . . . ?
O2 C1 C2 O4 74.7(4) . . . . ?
O2 C1 C2 C3 -166.0(4) . . . . ?
C22 O3 C3 C4 105.0(4) . . . . ?
C22 O3 C3 C2 -135.9(4) . . . . ?
O4 C2 C3 O3 -173.4(3) . . . . ?
C1 C2 C3 O3 67.6(4) . . . . ?
O4 C2 C3 C4 -54.7(4) . . . . ?
C1 C2 C3 C4 -173.7(4) . . . . ?
C29 O6 C4 C3 128.4(4) . . . . ?
C29 O6 C4 C5 -107.2(5) . . . . ?
O3 C3 C4 O6 -66.1(4) . . . . ?
C2 C3 C4 O6 176.4(3) . . . . ?
O3 C3 C4 C5 169.9(3) . . . . ?
C2 C3 C4 C5 52.4(4) . . . . ?
C36 O1 C5 C4 -105.4(4) . . . . ?
C36 O1 C5 C6 135.9(4) . . . . ?
O6 C4 C5 O1 63.9(4) . . . . ?
C3 C4 C5 O1 -173.2(3) . . . . ?
O6 C4 C5 C6 -176.3(3) . . . . ?
C3 C4 C5 C6 -53.4(4) . . . . ?
C2 O4 C6 C7 170.2(3) . . . . ?
C2 O4 C6 C5 -66.6(4) . . . . ?
O1 C5 C6 O4 178.0(3) . . . . ?
C4 C5 C6 O4 58.4(4) . . . . ?
O1 C5 C6 C7 -63.6(4) . . . . ?
C4 C5 C6 C7 176.8(3) . . . . ?
N2 N1 C7 F2 -173.0(3) . . . . ?
C14 N1 C7 F2 4.3(6) . . . . ?
N2 N1 C7 F1 73.3(4) . . . . ?
C14 N1 C7 F1 -109.5(4) . . . . ?
N2 N1 C7 C6 -49.7(5) . . . . ?
C14 N1 C7 C6 127.5(4) . . . . ?
O4 C6 C7 F2 79.8(4) . . . . ?
C5 C6 C7 F2 -39.8(4) . . . . ?
O4 C6 C7 F1 -163.7(3) . . . . ?
C5 C6 C7 F1 76.7(4) . . . . ?
O4 C6 C7 N1 -41.1(4) . . . . ?
C5 C6 C7 N1 -160.7(3) . . . . ?
N1 N2 C8 C9 -0.8(5) . . . . ?
N2 C8 C9 C14 0.3(5) . . . . ?
N2 C8 C9 C10 179.1(4) . . . . ?
C14 C9 C10 C11 -0.5(6) . . . . ?
C8 C9 C10 C11 -179.2(4) . . . . ?
C9 C10 C11 C12 0.0(6) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
N2 N1 C14 C13 179.9(4) . . . . ?
C7 N1 C14 C13 2.6(7) . . . . ?
N2 N1 C14 C9 -0.8(4) . . . . ?
C7 N1 C14 C9 -178.1(4) . . . . ?
C12 C13 C14 N1 179.0(4) . . . . ?
C12 C13 C14 C9 -0.3(6) . . . . ?
C10 C9 C14 N1 -178.8(3) . . . . ?
C8 C9 C14 N1 0.3(4) . . . . ?
C10 C9 C14 C13 0.7(6) . . . . ?
C8 C9 C14 C13 179.7(3) . . . . ?
C1 O2 C15 C16 64.8(5) . . . . ?
O2 C15 C16 C21 -123.9(5) . . . . ?
O2 C15 C16 C17 53.9(6) . . . . ?
C21 C16 C17 C18 -0.2(6) . . . . ?
C15 C16 C17 C18 -178.1(4) . . . . ?
C16 C17 C18 C19 0.0(7) . . . . ?
C17 C18 C19 C20 -0.2(7) . . . . ?
C18 C19 C20 C21 0.6(7) . . . . ?
C19 C20 C21 C16 -0.9(7) . . . . ?
C17 C16 C21 C20 0.7(7) . . . . ?
C15 C16 C21 C20 178.5(4) . . . . ?
C3 O3 C22 C23B -165.8(4) . . . . ?
C3 O3 C22 C23 -165.8(4) . . . . ?
O3 C22 C23 C28 26.5(10) . . . . ?
O3 C22 C23 C24 -155.1(9) . . . . ?
C28 C23 C24 C25 3.4(15) . . . . ?
C22 C23 C24 C25 -175.1(9) . . . . ?
C23 C24 C25 C26 5(2) . . . . ?
C24 C25 C26 C27 -11(3) . . . . ?
C25 C26 C27 C28 9(3) . . . . ?
C24 C23 C28 C27 -5.9(16) . . . . ?
C22 C23 C28 C27 172.5(9) . . . . ?
C26 C27 C28 C23 0(2) . . . . ?
O3 C22 C23B C28B 4.9(11) . . . . ?
O3 C22 C23B C24B 173.6(10) . . . . ?
C28B C23B C24B C25B -10.3(18) . . . . ?
C22 C23B C24B C25B -179.3(10) . . . . ?
C23B C24B C25B C26B 1(3) . . . . ?
C24B C25B C26B C27B 9(4) . . . . ?
C25B C26B C27B C28B -9(3) . . . . ?
C24B C23B C28B C27B 9.7(18) . . . . ?
C22 C23B C28B C27B 178.3(10) . . . . ?
C26B C27B C28B C23B 0(2) . . . . ?
C4 O6 C29 C30 -169.6(5) . . . . ?
O6 C29 C30 C31 -109.4(6) . . . . ?
O6 C29 C30 C35 76.5(7) . . . . ?
C35 C30 C31 C32 0.4(8) . . . . ?
C29 C30 C31 C32 -173.8(5) . . . . ?
C30 C31 C32 C33 -2.0(10) . . . . ?
C31 C32 C33 C34 1.7(10) . . . . ?
C32 C33 C34 C35 0.1(10) . . . . ?
C33 C34 C35 C30 -1.7(9) . . . . ?
C31 C30 C35 C34 1.4(8) . . . . ?
C29 C30 C35 C34 175.7(5) . . . . ?
C5 O1 C36 C37 164.5(3) . . . . ?
O1 C36 C37 C42 -1.8(6) . . . . ?
O1 C36 C37 C38 178.6(4) . . . . ?
C42 C37 C38 C39 -0.2(7) . . . . ?
C36 C37 C38 C39 179.4(5) . . . . ?
C37 C38 C39 C40 -0.4(8) . . . . ?
C38 C39 C40 C41 0.9(8) . . . . ?
C39 C40 C41 C42 -1.0(8) . . . . ?
C40 C41 C42 C37 0.5(7) . . . . ?
C38 C37 C42 C41 0.1(7) . . . . ?
C36 C37 C42 C41 -179.5(5) . . . . ?
C43 C44 C45 C46 -170(4) . . . . ?
C44 C45 C46 C47 -133(3) . . . . ?
C45 C46 C47 C48 -169(3) . . . . ?
