#------------------------------------------------------------------------------
#$Date: 2024-03-04 02:10:47 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290037 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/27/7132785.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_7132785
loop_
_publ_author_name
'Wang, Xuan'
'Li, Jianlong'
'Du, Haifang'
'Liang, Weihong'
'Luo, Cheng'
'Wu, Yunshan'
'Liu, Bo'
_publ_section_title
;
 Synthesis of 1,4-epoxy-2-aryltetrahydro-1-benzazepines via
 rhodium(III)-catalyzed C-H allylation/intramolecular 1,3-dipolar
 cycloaddition.
;
_journal_issue                   17
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2401
_journal_page_last               2404
_journal_paper_doi               10.1039/d3cc05082c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C16 H13 F2 N O'
_chemical_formula_sum            'C16 H13 F2 N O'
_chemical_formula_weight         273.27
_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             2023-09-26
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-10-12 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                77.710(3)
_cell_angle_beta                 89.322(3)
_cell_angle_gamma                71.433(3)
_cell_formula_units_Z            4
_cell_length_a                   9.7065(3)
_cell_length_b                   11.7198(4)
_cell_length_c                   12.0290(4)
_cell_measurement_reflns_used    6079
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      73.4040
_cell_measurement_theta_min      3.7390
_cell_volume                     1265.13(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  33.00   1.00    1.00    --  -40.73  38.00 -90.00   93
  2  ω      5.00  34.00   1.00    1.00    --   40.73 -99.00-180.00   29
  3  ω     60.00  90.00   1.00    1.00    --   40.73-125.00 -90.00   30
  4  ω     90.00 116.00   1.00    1.00    --  106.95-125.00 -30.00   26
  5  ω     94.00 133.00   1.00    1.00    --  106.95 -45.00  90.00   39
  6  ω     89.00 172.00   1.00    1.00    --  106.95  30.00  90.00   83
  7  ω    127.00 173.00   1.00    1.00    --  106.95  61.00  30.00   46
  8  ω     95.00 122.00   1.00    1.00    --  106.95 125.00 -30.00   27
  9  ω     78.00 123.00   1.00    1.00    --  106.95  61.00  30.00   45
 10  ω     75.00 132.00   1.00    1.00    --  106.95  77.00 -60.00   57
 11  ω     81.00 171.00   1.00    1.00    --  106.95  45.00 150.00   90
 12  ω     41.00  67.00   1.00    1.00    --  106.95-125.00 -30.00   26
 13  ω     33.00 138.00   1.00    1.00    --  106.95 -77.00 -30.00  105
 14  ω     36.00 105.00   1.00    1.00    --  106.95 -77.00-120.00   69
 15  ω     27.00 102.00   1.00    1.00    --  106.95 -94.00-180.00   75
 16  ω     34.00 121.00   1.00    1.00    --  106.95-125.00 150.00   87
 17  ω    -69.00  25.00   1.00    1.00    --  -40.73  57.00 120.00   94
 18  ω   -113.00 -22.00   1.00    1.00    --  -40.73 -57.00 -30.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1232963000
_diffrn_orient_matrix_UB_12      0.0068301000
_diffrn_orient_matrix_UB_13      -0.0831916000
_diffrn_orient_matrix_UB_21      -0.1130510000
_diffrn_orient_matrix_UB_22      0.0740049000
_diffrn_orient_matrix_UB_23      0.0710191000
_diffrn_orient_matrix_UB_31      0.0123592000
_diffrn_orient_matrix_UB_32      0.1211974000
_diffrn_orient_matrix_UB_33      -0.0726565000
_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  0.0289
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8430
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.544
_diffrn_reflns_theta_min         3.768
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0517
_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)+(0.0880P)²+0.2445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4444
_reflns_number_total             4941
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc05082c2.cif
_cod_data_source_block           ljl-39-2
_cod_database_code               7132785
_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.
;
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.859
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C24(H24), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C23(H23A,H23B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C20(H20),
 C21(H21), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.132
_oxdiff_exptl_absorpt_empirical_full_min 0.392
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
F1 F 1.11903(11) 0.49854(9) 0.86069(10) 0.0442(3) Uani 1 1 d . . . . .
F2 F 1.32563(11) 0.49671(9) 1.00750(10) 0.0431(3) Uani 1 1 d . . . . .
O1 O 0.70018(11) 0.84982(10) 0.88645(10) 0.0295(3) Uani 1 1 d . . . . .
N1 N 0.81343(12) 0.89294(11) 0.92046(10) 0.0223(3) Uani 1 1 d . . . . .
C1 C 0.69218(14) 1.10811(13) 0.81621(12) 0.0209(3) Uani 1 1 d . . . . .
C2 C 0.67188(16) 1.20473(13) 0.72097(13) 0.0245(3) Uani 1 1 d . . . . .
H2 H 0.734773 1.194197 0.660183 0.029 Uiso 1 1 calc R U . . .
C3 C 0.56135(16) 1.31582(14) 0.71372(13) 0.0280(3) Uani 1 1 d . . . . .
H3 H 0.548678 1.380536 0.648031 0.034 Uiso 1 1 calc R U . . .
C4 C 0.46917(16) 1.33293(14) 0.80191(14) 0.0293(3) Uani 1 1 d . . . . .
H4 H 0.393636 1.409243 0.797194 0.035 Uiso 1 1 calc R U . . .
C5 C 0.48820(16) 1.23767(15) 0.89702(14) 0.0293(3) Uani 1 1 d . . . . .
H5 H 0.425191 1.248787 0.957674 0.035 Uiso 1 1 calc R U . . .
C6 C 0.59890(16) 1.12586(14) 0.90439(13) 0.0253(3) Uani 1 1 d . . . . .
H6 H 0.610937 1.061182 0.970016 0.030 Uiso 1 1 calc R U . . .
C7 C 0.81438(14) 0.98836(13) 0.81857(12) 0.0214(3) Uani 1 1 d . . . . .
H7 H 0.910149 1.003560 0.817145 0.026 Uiso 1 1 calc R U . . .
C8 C 0.79916(18) 0.92744(14) 0.71952(13) 0.0305(3) Uani 1 1 d . . . . .
H8A H 0.730345 0.987062 0.657744 0.037 Uiso 1 1 calc R U . . .
H8B H 0.894544 0.893924 0.687865 0.037 Uiso 1 1 calc R U . . .
C9 C 0.74011(17) 0.82377(15) 0.77584(15) 0.0319(4) Uani 1 1 d . . . . .
H9 H 0.653226 0.826053 0.730482 0.038 Uiso 1 1 calc R U . . .
C10 C 0.85439(17) 0.69637(14) 0.79728(15) 0.0325(4) Uani 1 1 d . . . . .
H10A H 0.809057 0.632148 0.826894 0.039 Uiso 1 1 calc R U . . .
H10B H 0.899582 0.680652 0.725454 0.039 Uiso 1 1 calc R U . . .
C11 C 0.96783(16) 0.69313(13) 0.88345(13) 0.0246(3) Uani 1 1 d . . . . .
C12 C 0.94832(15) 0.79091(13) 0.93809(12) 0.0228(3) Uani 1 1 d . . . . .
C13 C 1.05650(17) 0.79200(14) 1.01156(13) 0.0291(3) Uani 1 1 d . . . . .
H13 H 1.042420 0.860423 1.045917 0.035 Uiso 1 1 calc R U . . .
C14 C 1.18529(18) 0.69362(15) 1.03517(14) 0.0323(4) Uani 1 1 d . . . . .
H14 H 1.260095 0.694222 1.085040 0.039 Uiso 1 1 calc R U . . .
C15 C 1.20278(16) 0.59507(14) 0.98504(14) 0.0296(3) Uani 1 1 d . . . . .
C16 C 1.09614(17) 0.59534(14) 0.91020(14) 0.0282(3) Uani 1 1 d . . . . .
F3 F 1.25982(12) 0.49260(9) 0.57100(10) 0.0470(3) Uani 1 1 d . . . . .
F4 F 1.09828(11) 0.50465(8) 0.38770(10) 0.0418(3) Uani 1 1 d . . . . .
O4 O 0.87419(11) 0.93781(9) 0.22506(8) 0.0246(2) Uani 1 1 d . . . . .
N2 N 0.88137(12) 0.94461(11) 0.34365(10) 0.0210(3) Uani 1 1 d . . . . .
C17 C 0.98197(15) 0.71865(13) 0.36643(13) 0.0240(3) Uani 1 1 d . . . . .
C18 C 1.08212(17) 0.60926(13) 0.42428(14) 0.0295(3) Uani 1 1 d . . . . .
C19 C 1.16481(16) 0.60325(14) 0.51864(15) 0.0310(3) Uani 1 1 d . . . . .
C20 C 1.15204(16) 0.70700(15) 0.55950(14) 0.0292(3) Uani 1 1 d . . . . .
H20 H 1.207454 0.701991 0.625987 0.035 Uiso 1 1 calc R U . . .
C21 C 1.05631(15) 0.81919(13) 0.50133(13) 0.0246(3) Uani 1 1 d . . . . .
H21 H 1.047425 0.892326 0.527011 0.029 Uiso 1 1 calc R U . . .
C22 C 0.97349(14) 0.82485(13) 0.40572(12) 0.0215(3) Uani 1 1 d . . . . .
C23 C 0.88929(17) 0.72414(14) 0.26534(13) 0.0281(3) Uani 1 1 d . . . . .
H23A H 0.830406 0.668605 0.287271 0.034 Uiso 1 1 calc R U . . .
H23B H 0.951944 0.696506 0.204246 0.034 Uiso 1 1 calc R U . . .
C24 C 0.78971(16) 0.85583(14) 0.22235(13) 0.0262(3) Uani 1 1 d . . . . .
H24 H 0.749208 0.867460 0.143161 0.031 Uiso 1 1 calc R U . . .
C25 C 0.66672(16) 0.89768(14) 0.30077(14) 0.0287(3) Uani 1 1 d . . . . .
H25A H 0.646915 0.825938 0.349708 0.034 Uiso 1 1 calc R U . . .
H25B H 0.576130 0.952329 0.255903 0.034 Uiso 1 1 calc R U . . .
C26 C 0.72608(14) 0.96842(13) 0.37322(12) 0.0216(3) Uani 1 1 d . . . . .
H26 H 0.722854 0.931952 0.455914 0.026 Uiso 1 1 calc R U . . .
C27 C 0.64274(14) 1.10538(13) 0.34901(12) 0.0227(3) Uani 1 1 d . . . . .
C28 C 0.64202(17) 1.18296(15) 0.24351(14) 0.0306(3) Uani 1 1 d . . . . .
H28 H 0.700153 1.151078 0.186031 0.037 Uiso 1 1 calc R U . . .
C29 C 0.55695(18) 1.30654(15) 0.22171(15) 0.0354(4) Uani 1 1 d . . . . .
H29 H 0.557715 1.358740 0.149661 0.043 Uiso 1 1 calc R U . . .
C30 C 0.47085(17) 1.35411(14) 0.30471(16) 0.0348(4) Uani 1 1 d . . . . .
H30 H 0.411689 1.438354 0.289227 0.042 Uiso 1 1 calc R U . . .
C31 C 0.47160(17) 1.27842(15) 0.40984(15) 0.0330(4) Uani 1 1 d . . . . .
H31 H 0.413757 1.310790 0.467229 0.040 Uiso 1 1 calc R U . . .
C32 C 0.55711(16) 1.15461(14) 0.43181(13) 0.0271(3) Uani 1 1 d . . . . .
H32 H 0.556980 1.103060 0.504351 0.032 Uiso 1 1 calc R U . . .
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'
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
N1 O1 C9 103.89(10) . . ?
O1 N1 C7 101.28(10) . . ?
O1 N1 C12 107.91(10) . . ?
C12 N1 C7 111.42(11) . . ?
C2 C1 C7 118.42(12) . . ?
C6 C1 C2 118.48(13) . . ?
C6 C1 C7 123.10(12) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.95(14) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.25(14) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.37(14) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.50(14) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.45(14) . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C1 111.48(11) . . ?
N1 C7 H7 109.7 . . ?
N1 C7 C8 102.95(11) . . ?
C1 C7 H7 109.7 . . ?
C1 C7 C8 113.24(12) . . ?
C8 C7 H7 109.7 . . ?
C7 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C9 C8 C7 103.30(12) . . ?
C9 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
O1 C9 C8 103.94(12) . . ?
O1 C9 H9 110.8 . . ?
O1 C9 C10 106.89(13) . . ?
C8 C9 H9 110.8 . . ?
C10 C9 C8 113.29(13) . . ?
C10 C9 H9 110.8 . . ?
C9 C10 H10A 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C11 C10 C9 107.61(12) . . ?
C11 C10 H10A 110.2 . . ?
C11 C10 H10B 110.2 . . ?
C12 C11 C10 121.00(13) . . ?
C16 C11 C10 121.71(14) . . ?
C16 C11 C12 117.27(14) . . ?
C11 C12 N1 120.74(13) . . ?
C13 C12 N1 118.13(13) . . ?
C13 C12 C11 121.12(13) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.28(14) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.81(14) . . ?
C15 C14 H14 120.6 . . ?
F2 C15 C14 120.50(14) . . ?
F2 C15 C16 118.73(14) . . ?
C14 C15 C16 120.77(14) . . ?
F1 C16 C11 119.38(14) . . ?
F1 C16 C15 118.94(14) . . ?
C15 C16 C11 121.67(14) . . ?
N2 O4 C24 104.54(10) . . ?
O4 N2 C26 102.20(10) . . ?
C22 N2 O4 106.87(10) . . ?
C22 N2 C26 111.44(10) . . ?
C18 C17 C22 116.59(14) . . ?
C18 C17 C23 121.88(14) . . ?
C22 C17 C23 121.52(13) . . ?
F4 C18 C17 119.08(15) . . ?
F4 C18 C19 118.83(14) . . ?
C19 C18 C17 122.08(14) . . ?
F3 C19 C18 118.56(15) . . ?
F3 C19 C20 120.37(15) . . ?
C18 C19 C20 121.07(14) . . ?
C19 C20 H20 120.8 . . ?
C19 C20 C21 118.47(15) . . ?
C21 C20 H20 120.8 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.21(14) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 N2 120.04(13) . . ?
C21 C22 N2 118.43(12) . . ?
C21 C22 C17 121.49(13) . . ?
C17 C23 H23A 109.8 . . ?
C17 C23 H23B 109.8 . . ?
C17 C23 C24 109.20(12) . . ?
H23A C23 H23B 108.3 . . ?
C24 C23 H23A 109.8 . . ?
C24 C23 H23B 109.8 . . ?
O4 C24 C23 107.95(12) . . ?
O4 C24 H24 110.6 . . ?
O4 C24 C25 103.20(11) . . ?
C23 C24 H24 110.6 . . ?
C23 C24 C25 113.75(13) . . ?
C25 C24 H24 110.6 . . ?
C24 C25 H25A 111.0 . . ?
C24 C25 H25B 111.0 . . ?
C24 C25 C26 103.81(11) . . ?
H25A C25 H25B 109.0 . . ?
C26 C25 H25A 111.0 . . ?
C26 C25 H25B 111.0 . . ?
N2 C26 C25 104.30(11) . . ?
N2 C26 H26 109.2 . . ?
N2 C26 C27 111.41(11) . . ?
C25 C26 H26 109.2 . . ?
C27 C26 C25 113.28(12) . . ?
C27 C26 H26 109.2 . . ?
C28 C27 C26 122.00(13) . . ?
C32 C27 C26 119.35(13) . . ?
C32 C27 C28 118.53(14) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.53(15) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 119.8 . . ?
C30 C29 C28 120.31(15) . . ?
C30 C29 H29 119.8 . . ?
C29 C30 H30 120.2 . . ?
C31 C30 C29 119.68(14) . . ?
C31 C30 H30 120.2 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.02(15) . . ?
C32 C31 H31 120.0 . . ?
C27 C32 C31 120.92(15) . . ?
C27 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
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 C16 1.3473(17) . ?
F2 C15 1.3504(17) . ?
O1 N1 1.4435(15) . ?
O1 C9 1.449(2) . ?
N1 C7 1.4750(17) . ?
N1 C12 1.4459(17) . ?
C1 C2 1.395(2) . ?
C1 C6 1.393(2) . ?
C1 C7 1.5169(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(2) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.544(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.532(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.521(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.507(2) . ?
C11 C12 1.400(2) . ?
C11 C16 1.383(2) . ?
C12 C13 1.385(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(2) . ?
C15 C16 1.379(2) . ?
F3 C19 1.3540(17) . ?
F4 C18 1.3516(18) . ?
O4 N2 1.4492(15) . ?
O4 C24 1.4534(17) . ?
N2 C22 1.4482(17) . ?
N2 C26 1.4961(17) . ?
C17 C18 1.384(2) . ?
C17 C22 1.401(2) . ?
C17 C23 1.499(2) . ?
C18 C19 1.374(2) . ?
C19 C20 1.376(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.518(2) . ?
C24 H24 1.0000 . ?
C24 C25 1.534(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.550(2) . ?
C26 H26 1.0000 . ?
C26 C27 1.5151(19) . ?
C27 C28 1.394(2) . ?
C27 C32 1.391(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.389(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.388(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.380(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.392(2) . ?
C32 H32 0.9500 . ?
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
F2 C15 C16 F1 -1.0(2) . . . . ?
F2 C15 C16 C11 -179.97(14) . . . . ?
O1 N1 C7 C1 79.92(12) . . . . ?
O1 N1 C7 C8 -41.79(12) . . . . ?
O1 N1 C12 C11 24.33(16) . . . . ?
O1 N1 C12 C13 -154.82(13) . . . . ?
O1 C9 C10 C11 -48.73(16) . . . . ?
N1 O1 C9 C8 -38.13(13) . . . . ?
N1 O1 C9 C10 81.94(13) . . . . ?
N1 C7 C8 C9 18.56(14) . . . . ?
N1 C12 C13 C14 177.13(14) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C1 C7 C8 C9 -101.95(13) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C1 C7 N1 -175.42(12) . . . . ?
C2 C1 C7 C8 -59.88(17) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C6 C1 C7 N1 4.24(19) . . . . ?
C6 C1 C7 C8 119.78(15) . . . . ?
C7 N1 C12 C11 -86.01(15) . . . . ?
C7 N1 C12 C13 94.84(15) . . . . ?
C7 C1 C2 C3 179.48(13) . . . . ?
C7 C1 C6 C5 -179.64(13) . . . . ?
C7 C8 C9 O1 11.23(14) . . . . ?
C7 C8 C9 C10 -104.42(14) . . . . ?
C8 C9 C10 C11 65.15(17) . . . . ?
C9 O1 N1 C7 50.74(12) . . . . ?
C9 O1 N1 C12 -66.37(13) . . . . ?
C9 C10 C11 C12 7.1(2) . . . . ?
C9 C10 C11 C16 -171.57(15) . . . . ?
C10 C11 C12 N1 5.2(2) . . . . ?
C10 C11 C12 C13 -175.64(14) . . . . ?
C10 C11 C16 F1 -2.0(2) . . . . ?
C10 C11 C16 C15 176.93(15) . . . . ?
C11 C12 C13 C14 -2.0(2) . . . . ?
C12 N1 C7 C1 -165.56(11) . . . . ?
C12 N1 C7 C8 72.73(13) . . . . ?
C12 C11 C16 F1 179.27(13) . . . . ?
C12 C11 C16 C15 -1.8(2) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
C13 C14 C15 F2 -178.87(15) . . . . ?
C13 C14 C15 C16 1.8(3) . . . . ?
C14 C15 C16 F1 178.31(14) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C16 C11 C12 N1 -176.01(13) . . . . ?
C16 C11 C12 C13 3.1(2) . . . . ?
F3 C19 C20 C21 178.19(14) . . . . ?
F4 C18 C19 F3 0.3(2) . . . . ?
F4 C18 C19 C20 -179.77(14) . . . . ?
O4 N2 C22 C17 -28.88(15) . . . . ?
O4 N2 C22 C21 148.62(12) . . . . ?
O4 N2 C26 C25 33.38(12) . . . . ?
O4 N2 C26 C27 -89.16(12) . . . . ?
O4 C24 C25 C26 -19.67(14) . . . . ?
N2 O4 C24 C23 -78.64(13) . . . . ?
N2 O4 C24 C25 42.08(13) . . . . ?
N2 C26 C27 C28 52.09(18) . . . . ?
N2 C26 C27 C32 -131.83(13) . . . . ?
C17 C18 C19 F3 179.60(14) . . . . ?
C17 C18 C19 C20 -0.4(2) . . . . ?
C17 C23 C24 O4 41.98(15) . . . . ?
C17 C23 C24 C25 -71.89(15) . . . . ?
C18 C17 C22 N2 174.30(13) . . . . ?
C18 C17 C22 C21 -3.1(2) . . . . ?
C18 C17 C23 C24 179.13(13) . . . . ?
C18 C19 C20 C21 -1.8(2) . . . . ?
C19 C20 C21 C22 1.5(2) . . . . ?
C20 C21 C22 N2 -176.42(13) . . . . ?
C20 C21 C22 C17 1.0(2) . . . . ?
C22 N2 C26 C25 -80.44(13) . . . . ?
C22 N2 C26 C27 157.02(12) . . . . ?
C22 C17 C18 F4 -177.84(12) . . . . ?
C22 C17 C18 C19 2.8(2) . . . . ?
C22 C17 C23 C24 -2.17(19) . . . . ?
C23 C17 C18 F4 0.9(2) . . . . ?
C23 C17 C18 C19 -178.40(14) . . . . ?
C23 C17 C22 N2 -4.5(2) . . . . ?
C23 C17 C22 C21 178.12(13) . . . . ?
C23 C24 C25 C26 97.01(14) . . . . ?
C24 O4 N2 C22 69.38(12) . . . . ?
C24 O4 N2 C26 -47.78(12) . . . . ?
C24 C25 C26 N2 -8.31(14) . . . . ?
C24 C25 C26 C27 112.99(13) . . . . ?
C25 C26 C27 C28 -65.12(17) . . . . ?
C25 C26 C27 C32 110.95(15) . . . . ?
C26 N2 C22 C17 81.99(15) . . . . ?
C26 N2 C22 C21 -100.51(14) . . . . ?
C26 C27 C28 C29 175.81(14) . . . . ?
C26 C27 C32 C31 -175.76(13) . . . . ?
C27 C28 C29 C30 -0.4(2) . . . . ?
C28 C27 C32 C31 0.5(2) . . . . ?
C28 C29 C30 C31 0.9(2) . . . . ?
C29 C30 C31 C32 -0.8(2) . . . . ?
C30 C31 C32 C27 0.1(2) . . . . ?
C32 C27 C28 C29 -0.3(2) . . . . ?
