#------------------------------------------------------------------------------
#$Date: 2024-12-17 04:09:21 +0200 (Tue, 17 Dec 2024) $
#$Revision: 296887 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249698.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_7249698
loop_
_publ_author_name
'Sato, Kazuyuki'
'Kuroki, Tomohiro'
'Minami, Haruka'
'Sato, Azusa'
'Karuo, Yukiko'
'Tarui, Atsushi'
'Kawai, Kentaro'
'Omote, Masaaki'
_publ_section_title
;
 Electrophilic aromatic substitution using fluorinated isoxazolines at the
 C5 position via C--F bond cleavage
;
_journal_issue                   53
_journal_name_full               'RSC Advances'
_journal_page_first              39543
_journal_page_last               39549
_journal_paper_doi               10.1039/D4RA07102F
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C20 H16 F2 N2 O'
_chemical_formula_sum            'C20 H16 F2 N2 O'
_chemical_formula_weight         338.35
_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             2024-04-10
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-04-19 deposited with the CCDC.	2024-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                96.3100(10)
_cell_angle_beta                 97.1640(10)
_cell_angle_gamma                93.9910(10)
_cell_formula_units_Z            4
_cell_length_a                   8.14050(10)
_cell_length_b                   12.07940(10)
_cell_length_c                   17.1421(3)
_cell_measurement_reflns_used    31356
_cell_measurement_temperature    120.0(5)
_cell_measurement_theta_max      77.1460
_cell_measurement_theta_min      2.6630
_cell_volume                     1656.39(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  31.00   0.50    0.17    --  -43.07  82.00  79.00  210
  2  ω    -30.00  74.00   0.50    0.17    --   43.07 -82.00 -42.00  208
  3  ω   -136.00 -30.00   0.50    0.67    -- -104.50  82.00  79.00  212
  4  ω   -174.00 -79.00   0.50    0.67    -- -104.50 -82.00 -42.00  190
  5  ω     39.00 144.00   0.50    0.67    --  113.00 -82.00 -42.00  210
  6  ω     86.00 178.00   0.50    0.67    --  113.00  82.00  79.00  184
  7  ω    -25.00  38.00   0.50    0.17    --  -43.07  19.00-120.00  126
  8  ω    -25.00  38.00   0.50    0.17    --  -43.07  19.00 120.00  126
  9  ω    -25.00  38.00   0.50    0.17    --  -43.07  19.00   0.00  126
 10  ω     12.00 124.00   0.50    0.17    --   43.07  19.00   0.00  224
 11  ω    -30.00  65.00   0.50    0.17    --   43.07 -57.00-180.00  190
 12  ω     19.00  95.00   0.50    0.17    --   43.07-125.00 120.00  152
 13  ω   -123.00 -30.00   0.50    0.67    -- -104.50 140.00 -56.36  186
 14  ω     40.00 107.00   0.50    0.67    --  113.00-109.00 145.85  134
 15  ω     41.00 112.00   0.50    0.67    --  113.00-125.00 -90.00  142
 16  ω     39.00 106.00   0.50    0.67    --  113.00 -77.00 -30.00  134
 17  ω     40.00 108.00   0.50    0.67    --  113.00-108.00 -62.39  136
 18  ω     84.00 178.00   0.50    0.67    --  113.00  77.00-180.00  188
 19  ω     38.00 106.00   0.50    0.67    --  113.00 -95.00  90.00  136
 20  ω     90.00 178.00   0.50    0.67    --  113.00  61.00-150.00  176
 21  ω     91.00 178.00   0.50    0.67    --  113.00  45.00 -60.00  174
 22  ω     89.00 178.00   0.50    0.67    --  113.00  30.00-120.00  178
 23  ω     39.00  76.00   0.50    0.67    --  113.00 -61.00   0.00   74
 24  ω     39.00  76.00   0.50    0.67    --  113.00 -61.00 -30.00   74
 25  ω     90.00 178.00   0.50    0.67    --  113.00  61.00-120.00  176
 26  ω     39.00 106.00   0.50    0.67    --  113.00 -77.00  90.00  134
 27  ω     39.00  76.00   0.50    0.67    --  113.00 -61.00 120.00   74
 28  ω     41.00 112.00   0.50    0.67    --  113.00-125.00 -60.00  142
 29  ω     38.00 106.00   0.50    0.67    --  113.00 -95.00  60.00  136
 30  ω     89.00 178.00   0.50    0.67    --  113.00  30.00  60.00  178
 31  ω     39.00 106.00   0.50    0.67    --  113.00 -77.00 -90.00  134
 32  ω     41.00 110.00   0.50    0.67    --  113.00-123.00-101.27  138
 33  ω     89.00 178.00   0.50    0.67    --  113.00  30.00-180.00  178
 34  ω     90.00 178.00   0.50    0.67    --  113.00  61.00 120.00  176
 35  ω     90.00 178.00   0.50    0.67    --  113.00  57.00 -40.19  176
 36  ω     90.00 178.00   0.50    0.67    --  113.00  61.00 -90.00  176
 37  ω     39.00  76.00   0.50    0.67    --  113.00 -61.00  30.00   74
 38  ω     41.00 112.00   0.50    0.67    --  113.00-125.00 150.00  142
 39  ω     80.00 178.00   0.50    0.67    --  113.00 125.00 -60.00  196
 40  ω     40.00 106.00   0.50    0.67    --  113.00 -93.00 137.99  132
 41  ω     41.00 117.00   0.50    0.67    --  113.00-133.00  76.88  152
 42  ω     39.00 106.00   0.50    0.67    --  113.00 -77.00-120.00  134
 43  ω     91.00 178.00   0.50    0.67    --  113.00  45.00  60.00  174
 44  ω     80.00 178.00   0.50    0.67    --  113.00 125.00  60.00  196
 45  ω     39.00 106.00   0.50    0.67    --  113.00 -77.00-180.00  134
 46  ω     38.00 106.00   0.50    0.67    --  113.00 -95.00 -60.00  136
 47  ω     38.00 106.00   0.50    0.67    --  113.00 -95.00 120.00  136
 48  ω     91.00 178.00   0.50    0.67    --  113.00  45.00  30.00  174
 49  ω     89.00 178.00   0.50    0.67    --  113.00  30.00   0.00  178
 50  ω     41.00 112.00   0.50    0.67    --  113.00-125.00  90.00  142
 51  ω     39.00  76.00   0.50    0.67    --  113.00 -61.00-180.00   74
 52  ω     39.00  76.00   0.50    0.67    --  113.00 -61.00  60.00   74
 53  ω     39.00  76.00   0.50    0.67    --  113.00 -61.00 150.00   74
 54  ω     39.00 121.00   0.50    0.67    --  113.00-138.00-130.24  164
 55  ω     89.00 178.00   0.50    0.67    --  113.00  30.00 120.00  178
 56  ω     39.00 106.00   0.50    0.67    --  113.00 -77.00 150.00  134
 57  ω     38.00 106.00   0.50    0.67    --  113.00 -95.00 -30.00  136
 58  ω     38.00 106.00   0.50    0.67    --  113.00 -95.00   0.00  136
 59  ω     41.00 112.00   0.50    0.67    --  113.00-125.00 -30.00  142
 60  ω     41.00 112.00   0.50    0.67    --  113.00-125.00  60.00  142
 61  ω     41.00 112.00   0.50    0.67    --  113.00-125.00 120.00  142
 62  ω     39.00 113.00   0.50    0.67    --  113.00 -79.00 171.54  148
 63  ω     39.00 130.00   0.50    0.67    --  113.00-151.00  40.72  182
 64  ω     84.00 178.00   0.50    0.67    --  113.00  77.00  60.00  188
 65  ω     90.00 178.00   0.50    0.67    --  113.00  61.00 150.00  176
 66  ω     14.00 117.00   0.50    0.17    --   43.07  77.00-180.00  206
 67  ω     14.00 117.00   0.50    0.17    --   43.07  77.00   0.00  206
 68  ω     14.00 117.00   0.50    0.17    --   43.07  77.00 -60.00  206
 69  ω     21.00 117.00   0.50    0.17    --   43.07  57.00 150.00  192
 70  ω     21.00 117.00   0.50    0.17    --   43.07  57.00  60.00  192
 71  ω      9.00  42.00   0.50    0.17    --   43.07  89.00  67.39   66
 72  ω     21.00 120.00   0.50    0.17    --   43.07  38.00 150.00  198
 73  ω     14.00 117.00   0.50    0.17    --   43.07  77.00-120.00  206
 74  ω     21.00 120.00   0.50    0.17    --   43.07  38.00  30.00  198
 75  ω     14.00 117.00   0.50    0.17    --   43.07  77.00  60.00  206
 76  ω     21.00 117.00   0.50    0.17    --   43.07  57.00-150.00  192
 77  ω     21.00 117.00   0.50    0.17    --   43.07  57.00 -90.00  192
 78  ω   -174.00 -75.00   0.50    0.67    -- -104.50 -77.00  41.84  198
 79  ω   -174.00 -76.00   0.50    0.67    -- -104.50 -75.00-177.09  196
 80  ω   -174.00 -75.00   0.50    0.67    -- -104.50 -77.00   0.00  198
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0842134000
_diffrn_orient_matrix_UB_12      0.0036962000
_diffrn_orient_matrix_UB_13      -0.0754287000
_diffrn_orient_matrix_UB_21      -0.1073035000
_diffrn_orient_matrix_UB_22      0.0938097000
_diffrn_orient_matrix_UB_23      -0.0244314000
_diffrn_orient_matrix_UB_31      0.1342961000
_diffrn_orient_matrix_UB_32      0.0881407000
_diffrn_orient_matrix_UB_33      0.0451366000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13056
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.956
_diffrn_reflns_theta_min         2.617
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethylacetate'
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         13056
_refine_ls_number_restraints     169
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0486
_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)+(0.0732P)²+0.6159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1394
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11518
_reflns_number_total             13056
_reflns_threshold_expression     'I > 2σ(I)'
_twin_special_details
;
Component 2 rotated by -179.9757° 
around [0.00 0.00 1.00] (reciprocal) or [0.27 0.16 0.95] (direct)
;
_cod_data_source_file            d4ra07102f2.cif
_cod_data_source_block           5aj_twin1_hklf4
_cod_database_code               7249698
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H16 F2 N O'
_chemical_oxdiff_usercomment     5aJ
_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   0.967
_shelx_estimated_absorpt_t_min   0.896
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6885(9)
 0.3115(9)
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
 C3A-C15A \\sim C3A-C15B
 with sigma of 0.02
 C16A-C18A \\sim C16B-C18B
 with sigma of 0.04
 C15A-C16A \\sim C15B-C16B
 with sigma of 0.02
 C15A-C20A \\sim C15B-C20B
 with sigma of 0.02
 C16A-C17A \\sim C16B-C17B
 with sigma of 0.02
 C17A-C18A \\sim C17B-C18B
 with sigma of 0.02
 C18A-C19A \\sim C18B-C19B
 with sigma of 0.02
 C16A-C20A \\sim C16B-C20B
 with sigma of 0.04
 C19A-C20A \\sim C19B-C20B
 with sigma of 0.02
 C17A-C19A \\sim C17B-C19B
 with sigma of 0.04
 C18A-C20A \\sim C18B-C20B
 with sigma of 0.04
 C3A-C16A \\sim C3A-C16B
 with sigma of 0.04
 C3A-C20A \\sim C3A-C20B
 with sigma of 0.04
 C15A-C17A \\sim C15B-C17B
 with sigma of 0.04
 C15A-C19A \\sim C15B-C19B
 with sigma of 0.04
 C15-C19 \\sim C15-C1C
 with sigma of 0.04
 C15-C20 \\sim C15-C1D
 with sigma of 0.02
 C16-C17 \\sim C21-C1B
 with sigma of 0.02
 C18-C20 \\sim C18-C1D
 with sigma of 0.04
 C17-C18 \\sim C1B-C18
 with sigma of 0.02
 C15-C17 \\sim C15-C1B
 with sigma of 0.04
 C16-C18 \\sim C21-C18
 with sigma of 0.04
 C19-C20 \\sim C1C-C1D
 with sigma of 0.02
 C18-C19 \\sim C18-C1C
 with sigma of 0.02
 C15-C16 \\sim C15-C21
 with sigma of 0.02
4. Rigid body (RIGU) restrains
 C15A, C15B, C16A, C16B, C17A, C17B, C18A, C18B, C19A, C19B, C20A, C20B
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C1B, C1C, C1D, C15, C16, C17, C18, C19, C20, C21
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
5. Others
 Sof(C15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=Sof(C18B)=Sof(H18B)=
 Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(H20B)=1-FVAR(1)
 Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=
 Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=FVAR(1)
 Sof(C1B)=Sof(H1B)=Sof(C1C)=Sof(H1C)=Sof(C1D)=Sof(H1D)=Sof(H18C)=Sof(C21)=
 Sof(H21)=1-FVAR(2)
 Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=
 Sof(H20)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C1B(H1B), C1C(H1C), C1D(H1D), C5(H5), C5A(H5A), C6(H6), C6A(H6A), C7(H7),
 C7A(H7A), C8(H8), C8A(H8A), C9(H9), C9A(H9A), C11(H11), C11A(H11A), C12(H12),
 C12A(H12A), C13(H13), C13A(H13A), C16(H16), C16A(H16A), C16B(H16B), C17(H17),
 C17A(H17A), C17B(H17B), C18(H18), C18(H18C), C18A(H18A), C18B(H18B), C19(H19),
 C19A(H19A), C19B(H19B), C20(H20), C20A(H20A), C20B(H20B), C21(H21)
6.b Idealised Me refined as rotating group:
 C14(H14D,H14E,H14F), C14A(H14A,H14B,H14C)
;
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MiTeGEN Dual Thickness MicroLoops in  perfluoropolyether oil'
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.462
_oxdiff_exptl_absorpt_empirical_full_min 0.745
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
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
C1 C 0.7754(2) 0.15671(14) 0.20655(11) 0.0208(4) Uani 1 1 d . . . . .
C1A C 0.5536(2) 0.65626(14) 0.23258(11) 0.0209(4) Uani 1 1 d . . . . .
C1B C 0.9176(18) 0.3735(6) 0.5357(4) 0.049(2) Uani 0.50(2) 1 d D . P A 2
H1B H 0.933440 0.451318 0.553220 0.059 Uiso 0.50(2) 1 calc R U P A 2
C1C C 0.883(2) 0.1867(6) 0.5664(3) 0.052(2) Uani 0.50(2) 1 d D . P A 2
H1C H 0.873848 0.135456 0.604308 0.062 Uiso 0.50(2) 1 calc R U P A 2
C1D C 0.8649(19) 0.1472(5) 0.4865(3) 0.0433(19) Uani 0.50(2) 1 d D . P A 2
H1D H 0.845227 0.069175 0.470162 0.052 Uiso 0.50(2) 1 calc R U P A 2
C2 C 0.8273(2) 0.24867(16) 0.27684(11) 0.0247(4) Uani 1 1 d . . . . .
C2A C 0.5483(2) 0.61735(15) 0.31445(11) 0.0246(4) Uani 1 1 d . . . . .
C3 C 0.8592(2) 0.17996(16) 0.34494(12) 0.0251(4) Uani 1 1 d . . . . .
C3A C 0.5530(2) 0.72728(16) 0.36666(11) 0.0242(4) Uani 1 1 d D . . . .
C4 C 0.5869(2) 0.12752(15) 0.19771(10) 0.0199(4) Uani 1 1 d . . . . .
C4A C 0.7344(2) 0.67768(15) 0.21765(10) 0.0206(4) Uani 1 1 d . . . . .
C5 C 0.5201(2) 0.03653(15) 0.23010(12) 0.0240(4) Uani 1 1 d . . . . .
H5 H 0.591393 -0.007588 0.259399 0.029 Uiso 1 1 calc R U . . .
C5A C 0.8163(2) 0.58881(17) 0.18623(12) 0.0278(4) Uani 1 1 d . . . . .
H5A H 0.761144 0.515759 0.175712 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3492(2) 0.01011(16) 0.21967(13) 0.0273(4) Uani 1 1 d . . . . .
H6 H 0.304305 -0.052851 0.241072 0.033 Uiso 1 1 calc R U . . .
C6A C 0.9791(3) 0.60730(19) 0.17030(13) 0.0333(5) Uani 1 1 d . . . . .
H6A H 1.034670 0.546652 0.149059 0.040 Uiso 1 1 calc R U . . .
C7 C 0.2441(2) 0.07505(17) 0.17827(12) 0.0278(4) Uani 1 1 d . . . . .
H7 H 0.127352 0.056881 0.171421 0.033 Uiso 1 1 calc R U . . .
C7A C 1.0604(2) 0.71373(19) 0.18528(13) 0.0310(4) Uani 1 1 d . . . . .
H7A H 1.171093 0.726138 0.174043 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3096(2) 0.16661(17) 0.14686(12) 0.0275(4) Uani 1 1 d . . . . .
H8 H 0.237397 0.211742 0.119004 0.033 Uiso 1 1 calc R U . . .
C8A C 0.9796(2) 0.80157(18) 0.21661(13) 0.0287(4) Uani 1 1 d . . . . .
H8A H 1.035036 0.874552 0.226774 0.034 Uiso 1 1 calc R U . . .
C9 C 0.4809(2) 0.19289(16) 0.15588(11) 0.0237(4) Uani 1 1 d . . . . .
H9 H 0.525319 0.255166 0.133604 0.028 Uiso 1 1 calc R U . . .
C9A C 0.8170(2) 0.78391(16) 0.23347(12) 0.0244(4) Uani 1 1 d . . . . .
H9A H 0.762880 0.844573 0.255760 0.029 Uiso 1 1 calc R U . . .
C10 C 0.8330(2) 0.17817(16) 0.12959(11) 0.0222(4) Uani 1 1 d . . . . .
C10A C 0.4506(2) 0.58505(15) 0.16431(11) 0.0224(4) Uani 1 1 d . . . . .
C11 C 0.9002(2) 0.27408(17) 0.10451(12) 0.0255(4) Uani 1 1 d . . . . .
H11 H 0.927253 0.344517 0.135683 0.031 Uiso 1 1 calc R U . . .
C11A C 0.3744(2) 0.47810(16) 0.15762(13) 0.0270(4) Uani 1 1 d . . . . .
H11A H 0.370309 0.432093 0.198979 0.032 Uiso 1 1 calc R U . . .
C12 C 0.9215(2) 0.24862(18) 0.02416(12) 0.0292(4) Uani 1 1 d . . . . .
H12 H 0.964883 0.298619 -0.008748 0.035 Uiso 1 1 calc R U . . .
C12A C 0.3037(2) 0.44990(17) 0.07791(13) 0.0295(4) Uani 1 1 d . . . . .
H12A H 0.243741 0.381060 0.055683 0.035 Uiso 1 1 calc R U . . .
C13 C 0.8679(2) 0.13843(19) 0.00274(12) 0.0297(4) Uani 1 1 d . . . . .
H13 H 0.869088 0.098284 -0.048029 0.036 Uiso 1 1 calc R U . . .
C13A C 0.3370(2) 0.53908(17) 0.03852(12) 0.0287(4) Uani 1 1 d . . . . .
H13A H 0.302866 0.543210 -0.016069 0.034 Uiso 1 1 calc R U . . .
C14 C 0.7409(3) -0.01947(17) 0.06344(13) 0.0325(4) Uani 1 1 d . . . . .
H14D H 0.795510 -0.053671 0.107930 0.049 Uiso 1 1 calc R U . . .
H14E H 0.757429 -0.062343 0.013488 0.049 Uiso 1 1 calc R U . . .
H14F H 0.621694 -0.019473 0.067072 0.049 Uiso 1 1 calc R U . . .
C14A C 0.4935(3) 0.72726(17) 0.06758(12) 0.0292(4) Uani 1 1 d . . . . .
H14A H 0.474175 0.789036 0.106523 0.044 Uiso 1 1 calc R U . . .
H14B H 0.437591 0.738066 0.015274 0.044 Uiso 1 1 calc R U . . .
H14C H 0.613111 0.725458 0.065615 0.044 Uiso 1 1 calc R U . . .
C15 C 0.8757(3) 0.22125(19) 0.42972(12) 0.0320(4) Uani 1 1 d D . . . .
C15A C 0.590(6) 0.7444(10) 0.4538(6) 0.0289(17) Uani 0.50(2) 1 d D . P B 1
C15B C 0.588(6) 0.7441(11) 0.4528(7) 0.0296(17) Uani 0.50(2) 1 d D . P B 2
C16 C 0.8380(15) 0.3278(6) 0.4560(3) 0.0378(15) Uani 0.50(2) 1 d D . P A 1
H16 H 0.798774 0.375991 0.418864 0.045 Uiso 0.50(2) 1 calc R U P A 1
C16A C 0.6370(13) 0.6560(5) 0.4956(3) 0.0330(14) Uani 0.50(2) 1 d D . P B 1
H16A H 0.648373 0.585029 0.467919 0.040 Uiso 0.50(2) 1 calc R U P B 1
C16B C 0.5769(17) 0.6577(5) 0.4983(4) 0.0415(18) Uani 0.50(2) 1 d D . P B 2
H16B H 0.545909 0.583588 0.473616 0.050 Uiso 0.50(2) 1 calc R U P B 2
C17 C 0.8576(17) 0.3646(7) 0.5370(4) 0.046(2) Uani 0.50(2) 1 d D . P A 1
H17 H 0.832437 0.438139 0.554561 0.055 Uiso 0.50(2) 1 calc R U P A 1
C17A C 0.6671(15) 0.6723(6) 0.5779(4) 0.0402(17) Uani 0.50(2) 1 d D . P B 1
H17A H 0.691147 0.611119 0.606559 0.048 Uiso 0.50(2) 1 calc R U P B 1
C17B C 0.6112(19) 0.6782(6) 0.5808(4) 0.051(2) Uani 0.50(2) 1 d D . P B 2
H17B H 0.613201 0.617091 0.611197 0.061 Uiso 0.50(2) 1 calc R U P B 2
C18 C 0.9119(4) 0.2968(2) 0.59089(15) 0.0459(5) Uani 1 1 d D . . . .
H18 H 0.922655 0.321891 0.645925 0.055 Uiso 0.50(2) 1 calc R U P A 1
H18C H 0.928797 0.322543 0.645911 0.055 Uiso 0.50(2) 1 calc R U P A 2
C18A C 0.662(2) 0.7742(7) 0.6169(6) 0.0399(17) Uani 0.50(2) 1 d D . P B 1
H18A H 0.651758 0.783191 0.671771 0.048 Uiso 0.50(2) 1 calc R U P B 1
C18B C 0.642(2) 0.7856(8) 0.6187(6) 0.045(2) Uani 0.50(2) 1 d D . P B 2
H18B H 0.693057 0.801587 0.672135 0.054 Uiso 0.50(2) 1 calc R U P B 2
C19 C 0.9528(16) 0.1874(6) 0.5642(4) 0.0474(17) Uani 0.50(2) 1 d D . P A 1
H19 H 0.993435 0.139750 0.601458 0.057 Uiso 0.50(2) 1 calc R U P A 1
C19A C 0.6727(18) 0.8687(5) 0.5744(3) 0.046(2) Uani 0.50(2) 1 d D . P B 1
H19A H 0.702194 0.941417 0.601860 0.055 Uiso 0.50(2) 1 calc R U P B 1
C19B C 0.5961(17) 0.8650(5) 0.5752(3) 0.0445(17) Uani 0.50(2) 1 d D . P B 2
H19B H 0.582551 0.936785 0.601041 0.053 Uiso 0.50(2) 1 calc R U P B 2
C20 C 0.9330(15) 0.1507(5) 0.4839(3) 0.0391(15) Uani 0.50(2) 1 d D . P A 1
H20 H 0.958625 0.077448 0.465989 0.047 Uiso 0.50(2) 1 calc R U P A 1
C20A C 0.6393(17) 0.8535(5) 0.4924(3) 0.0394(17) Uani 0.50(2) 1 d D . P B 1
H20A H 0.649422 0.915032 0.462743 0.047 Uiso 0.50(2) 1 calc R U P B 1
C20B C 0.5669(16) 0.8468(5) 0.4933(3) 0.0385(15) Uani 0.50(2) 1 d D . P B 2
H20B H 0.532038 0.905704 0.464424 0.046 Uiso 0.50(2) 1 calc R U P B 2
C21 C 0.9000(18) 0.3361(5) 0.4549(3) 0.0422(18) Uani 0.50(2) 1 d D . P A 2
H21 H 0.904580 0.388052 0.417313 0.051 Uiso 0.50(2) 1 calc R U P A 2
F1 F 0.71264(16) 0.32326(10) 0.28472(7) 0.0333(3) Uani 1 1 d . . . . .
F1A F 0.67225(17) 0.55272(10) 0.33519(7) 0.0349(3) Uani 1 1 d . . . . .
F2 F 0.97216(16) 0.31023(11) 0.27145(7) 0.0361(3) Uani 1 1 d . . . . .
F2A F 0.40378(17) 0.55561(10) 0.32071(7) 0.0359(3) Uani 1 1 d . . . . .
N1 N 0.8827(2) 0.07870(14) 0.32014(9) 0.0257(3) Uani 1 1 d . . . . .
N1A N 0.5086(2) 0.80521(13) 0.32564(9) 0.0246(3) Uani 1 1 d . . . . .
N2 N 0.8123(2) 0.09522(14) 0.06614(9) 0.0252(3) Uani 1 1 d . . . . .
N2A N 0.4274(2) 0.62170(14) 0.09043(10) 0.0239(3) Uani 1 1 d . . . . .
O1 O 0.85939(16) 0.06334(11) 0.23602(8) 0.0230(3) Uani 1 1 d . . . . .
O1A O 0.48229(16) 0.76410(10) 0.24393(8) 0.0220(3) 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'
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
C4 C1 C2 109.47(15) . . ?
C10 C1 C2 116.29(15) . . ?
C10 C1 C4 112.03(15) . . ?
O1 C1 C2 100.65(14) . . ?
O1 C1 C4 108.72(14) . . ?
O1 C1 C10 108.89(14) . . ?
C2A C1A C4A 110.10(15) . . ?
C10A C1A C2A 116.33(15) . . ?
C10A C1A C4A 111.90(15) . . ?
O1A C1A C2A 100.70(14) . . ?
O1A C1A C4A 108.49(14) . . ?
O1A C1A C10A 108.51(14) . . ?
C21 C1B C18 120.2(6) . . ?
C18 C1C C1D 120.6(5) . . ?
C1C C1D C15 120.6(5) . . ?
C3 C2 C1 101.52(15) . . ?
F1 C2 C1 112.97(15) . . ?
F1 C2 C3 115.38(16) . . ?
F1 C2 F2 105.74(15) . . ?
F2 C2 C1 113.46(16) . . ?
F2 C2 C3 107.91(15) . . ?
C3A C2A C1A 101.82(15) . . ?
F1A C2A C1A 113.17(15) . . ?
F1A C2A C3A 114.83(16) . . ?
F1A C2A F2A 105.66(15) . . ?
F2A C2A C1A 113.52(16) . . ?
F2A C2A C3A 107.96(15) . . ?
C15 C3 C2 126.36(18) . . ?
N1 C3 C2 111.30(17) . . ?
N1 C3 C15 122.18(18) . . ?
C15A C3A C2A 126.1(5) . . ?
C15B C3A C2A 126.2(5) . . ?
N1A C3A C2A 110.90(17) . . ?
N1A C3A C15A 122.8(6) . . ?
N1A C3A C15B 122.7(6) . . ?
C5 C4 C1 121.19(16) . . ?
C5 C4 C9 119.46(17) . . ?
C9 C4 C1 119.35(16) . . ?
C5A C4A C1A 119.20(16) . . ?
C9A C4A C1A 121.36(16) . . ?
C9A C4A C5A 119.43(17) . . ?
C6 C5 C4 120.15(17) . . ?
C6A C5A C4A 119.99(19) . . ?
C7 C6 C5 120.34(18) . . ?
C7A C6A C5A 120.38(19) . . ?
C6 C7 C8 119.81(18) . . ?
C8A C7A C6A 119.66(18) . . ?
C7 C8 C9 120.36(17) . . ?
C7A C8A C9A 120.49(19) . . ?
C8 C9 C4 119.87(18) . . ?
C4A C9A C8A 120.04(18) . . ?
C11 C10 C1 131.59(17) . . ?
C11 C10 N2 107.62(17) . . ?
N2 C10 C1 120.66(17) . . ?
C11A C10A C1A 131.61(18) . . ?
C11A C10A N2A 107.77(17) . . ?
N2A C10A C1A 120.49(16) . . ?
C10 C11 C12 107.69(18) . . ?
C10A C11A C12A 107.18(18) . . ?
C13 C12 C11 107.02(18) . . ?
C13A C12A C11A 107.70(18) . . ?
C12 C13 N2 109.08(18) . . ?
C12A C13A N2A 108.80(18) . . ?
C1D C15 C3 120.9(3) . . ?
C1D C15 C21 118.8(4) . . ?
C16 C15 C3 121.8(3) . . ?
C16 C15 C20 120.0(4) . . ?
C20 C15 C3 118.2(3) . . ?
C21 C15 C3 120.3(3) . . ?
C16A C15A C3A 120.4(10) . . ?
C16A C15A C20A 116.3(14) . . ?
C20A C15A C3A 119.2(10) . . ?
C16B C15B C3A 122.6(10) . . ?
C16B C15B C20B 113.0(15) . . ?
C20B C15B C3A 119.6(11) . . ?
C15 C16 C17 120.1(5) . . ?
C17A C16A C15A 119.9(7) . . ?
C15B C16B C17B 120.3(7) . . ?
C18 C17 C16 120.8(6) . . ?
C18A C17A C16A 120.2(6) . . ?
C18B C17B C16B 121.2(7) . . ?
C1C C18 C1B 120.3(4) . . ?
C17 C18 C19 119.4(4) . . ?
C17A C18A C19A 118.6(8) . . ?
C19B C18B C17B 115.0(9) . . ?
C20 C19 C18 119.9(5) . . ?
C20A C19A C18A 119.3(6) . . ?
C18B C19B C20B 122.3(6) . . ?
C19 C20 C15 119.8(5) . . ?
C19A C20A C15A 118.7(6) . . ?
C19B C20B C15B 121.1(6) . . ?
C1B C21 C15 119.4(5) . . ?
C3 N1 O1 109.58(15) . . ?
C3A N1A O1A 109.99(15) . . ?
C10 N2 C14 127.60(17) . . ?
C13 N2 C10 108.58(17) . . ?
C13 N2 C14 123.80(17) . . ?
C10A N2A C14A 127.56(16) . . ?
C13A N2A C10A 108.54(17) . . ?
C13A N2A C14A 123.82(17) . . ?
N1 O1 C1 109.35(13) . . ?
N1A O1A C1A 109.11(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.542(3) . ?
C1 C4 1.535(2) . ?
C1 C10 1.497(3) . ?
C1 O1 1.463(2) . ?
C1A C2A 1.533(3) . ?
C1A C4A 1.534(2) . ?
C1A C10A 1.499(3) . ?
C1A O1A 1.466(2) . ?
C1B C18 1.398(7) . ?
C1B C21 1.395(7) . ?
C1C C1D 1.387(7) . ?
C1C C18 1.346(7) . ?
C1D C15 1.399(6) . ?
C2 C3 1.512(3) . ?
C2 F1 1.350(2) . ?
C2 F2 1.368(2) . ?
C2A C3A 1.513(3) . ?
C2A F1A 1.355(2) . ?
C2A F2A 1.371(2) . ?
C3 C15 1.470(3) . ?
C3 N1 1.285(3) . ?
C3A C15A 1.475(11) . ?
C3A C15B 1.457(11) . ?
C3A N1A 1.281(3) . ?
C4 C5 1.392(3) . ?
C4 C9 1.396(2) . ?
C4A C5A 1.396(3) . ?
C4A C9A 1.390(3) . ?
C5 C6 1.390(3) . ?
C5A C6A 1.394(3) . ?
C6 C7 1.384(3) . ?
C6A C7A 1.387(3) . ?
C7 C8 1.385(3) . ?
C7A C8A 1.381(3) . ?
C8 C9 1.394(3) . ?
C8A C9A 1.397(3) . ?
C10 C11 1.381(3) . ?
C10 N2 1.381(2) . ?
C10A C11A 1.380(3) . ?
C10A N2A 1.382(2) . ?
C11 C12 1.413(3) . ?
C11A C12A 1.410(3) . ?
C12 C13 1.367(3) . ?
C12A C13A 1.362(3) . ?
C13 N2 1.368(3) . ?
C13A N2A 1.367(3) . ?
C14 N2 1.458(3) . ?
C14A N2A 1.461(2) . ?
C15 C16 1.384(6) . ?
C15 C20 1.389(6) . ?
C15 C21 1.399(6) . ?
C15A C16A 1.399(14) . ?
C15A C20A 1.415(15) . ?
C15B C16B 1.375(15) . ?
C15B C20B 1.386(16) . ?
C16 C17 1.397(7) . ?
C16A C17A 1.391(7) . ?
C16B C17B 1.397(7) . ?
C17 C18 1.354(7) . ?
C17A C18A 1.340(8) . ?
C17B C18B 1.377(10) . ?
C18 C19 1.426(7) . ?
C18A C19A 1.424(10) . ?
C18B C19B 1.324(10) . ?
C19 C20 1.385(7) . ?
C19A C20A 1.387(6) . ?
C19B C20B 1.385(6) . ?
N1 O1 1.421(2) . ?
N1A O1A 1.418(2) . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6885(9) 34247 29318 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.3115(9) 33996 29318 nmt -0.9997 0.0003 0.0015 -0.0004 -0.9999 0.0010 0.5664
0.3395 0.9990
