#------------------------------------------------------------------------------
#$Date: 2021-06-05 21:30:18 +0200 (Sat 05 de Jun de 2021) $
#$Revision: 266180 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/80/7158052.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_7158052
loop_
_publ_author_name
'Zhang, Chao'
'Wu, You-Cai'
'Cui, Bao-Dong'
'Li, Lian'
'Han, Wen-Yong'
'Wan, Nan-Wei'
'Chen, Yong-Zheng'
_publ_section_title
;
 Palladium-catalyzed asymmetric allylic alkylation of 3-aminooxindoles to
 access chiral homoallylic aminooxindoles.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4720
_journal_page_last               4725
_journal_paper_doi               10.1039/d1ob00550b
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H29 F N2 O3'
_chemical_formula_sum            'C29 H29 F N2 O3'
_chemical_formula_weight         472.54
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-06
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-10-15 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.6850(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.4371(5)
_cell_length_b                   6.95612(16)
_cell_length_c                   15.3764(2)
_cell_measurement_reflns_used    6502
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.5800
_cell_measurement_theta_min      2.9060
_cell_volume                     2681.98(9)
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -35.00   1.00    1.00    --  -40.98 -57.00   0.00   27
  2  ω     23.00  71.00   1.00    1.00    --   40.98  57.00   0.00   48
  3  ω      9.00 117.00   1.00    1.00    --   40.98  77.00 -90.00  108
  4  ω     50.00  77.00   1.00    1.00    --   40.98  37.00   0.00   27
  5  ω    -35.00  37.00   1.00    1.00    --   40.98 -77.00  60.00   72
  6  ω     81.00 114.00   1.00    1.00    --   40.98  37.00   0.00   33
  7  ω     40.00  67.00   1.00    1.00    --   40.98  77.00-150.00   27
  8  ω     30.00  87.00   1.00    1.00    --   40.98  37.00-120.00   57
  9  ω      1.00  79.00   1.00    1.00    --   40.98 -99.00 150.00   78
 10  ω     75.00 100.00   1.00    2.00    --  106.95  77.00 -30.00   25
 11  ω    109.00 178.00   1.00    2.00    --  106.95  77.00-120.00   69
 12  ω     75.00 100.00   1.00    1.50    --  106.95  77.00-120.00   25
 13  ω     74.00 101.00   1.00    1.50    --  106.95  77.00   0.00   27
 14  ω     74.00 100.00   1.00    1.50    --  106.95  77.00 -60.00   26
 15  ω     34.00  87.00   1.00    1.50    --  106.95-124.00-180.00   53
 16  ω     74.00 101.00   1.00    1.50    --  106.95  77.00-150.00   27
 17  ω     24.00 106.00   1.00    1.50    --  106.95 -94.00-180.00   82
 18  ω     78.00 104.00   1.00    1.50    --  106.95  61.00 -90.00   26
 19  ω     78.00 104.00   1.00    1.50    --  106.95  61.00   0.00   26
 20  ω     79.00 140.00   1.00    1.50    --  106.95  61.00 -60.00   61
 21  ω     79.00 104.00   1.00    1.50    --  106.95  61.00 -30.00   25
 22  ω     82.00 109.00   1.00    1.50    --  106.95  61.00-150.00   27
 23  ω     82.00 145.00   1.00    1.50    --  106.95  45.00 -30.00   63
 24  ω     79.00 104.00   1.00    1.50    --  106.95  61.00-120.00   25
 25  ω     82.00 149.00   1.00    1.50    --  106.95  45.00-120.00   67
 26  ω     81.00 108.00   1.00    1.50    --  106.95  45.00 -60.00   27
 27  ω     81.00 178.00   1.00    1.50    --  106.95  45.00   0.00   97
 28  ω     24.00  69.00   1.00    1.50    --  106.95 -94.00 -90.00   45
;
_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      0.0078301000
_diffrn_orient_matrix_UB_12      0.0120649000
_diffrn_orient_matrix_UB_13      -0.0970437000
_diffrn_orient_matrix_UB_21      -0.0605189000
_diffrn_orient_matrix_UB_22      -0.0245871000
_diffrn_orient_matrix_UB_23      -0.0301519000
_diffrn_orient_matrix_UB_31      -0.0072132000
_diffrn_orient_matrix_UB_32      0.2197350000
_diffrn_orient_matrix_UB_33      0.0019726000
_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  0.0168
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10381
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.708
_diffrn_reflns_theta_min         2.915
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79080
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details
;
 Flack x determined using 1690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_coef       0.00110(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0325
_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)+(0.0499P)²+0.3009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    0.821
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                4489
_reflns_number_total             4740
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00550b2.cif
_cod_data_source_block           zc-2-2
_cod_depositor_comments
'Adding full bibliography for 7158051--7158052.cif.'
_cod_database_code               7158052
_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.
;
_reflns_odcompleteness_completeness 98.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C)
;
_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 1.347
_oxdiff_exptl_absorpt_empirical_full_min 0.656
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 0.66568(6) 0.4129(3) 1.07656(8) 0.0817(5) Uani 1 1 d . . . . .
O1 O 0.59884(8) 0.0505(2) 0.77954(11) 0.0768(5) Uani 1 1 d . . . . .
O2 O 0.72450(7) 0.1617(3) 0.79533(10) 0.0747(5) Uani 1 1 d . . . . .
O3 O 0.73351(6) 0.2139(3) 0.65237(10) 0.0720(5) Uani 1 1 d . . . . .
N1 N 0.62562(7) 0.2348(3) 0.90312(10) 0.0559(4) Uani 1 1 d . . . . .
N2 N 0.66480(7) 0.3365(3) 0.70241(11) 0.0568(4) Uani 1 1 d . . . . .
H2 H 0.6579(10) 0.392(4) 0.6490(17) 0.070(7) Uiso 1 1 d . . . . .
C1 C 0.65643(7) 0.5053(3) 0.84227(12) 0.0477(4) Uani 1 1 d . . . . .
C2 C 0.68257(8) 0.6774(3) 0.84290(14) 0.0587(5) Uani 1 1 d . . . . .
H2A H 0.686533 0.737202 0.790298 0.070 Uiso 1 1 calc R U . . .
C3 C 0.70311(9) 0.7611(4) 0.92353(16) 0.0733(7) Uani 1 1 d . . . . .
H3 H 0.720939 0.878076 0.924914 0.088 Uiso 1 1 calc R U . . .
C4 C 0.69726(9) 0.6723(4) 1.00147(16) 0.0719(7) Uani 1 1 d . . . . .
H4 H 0.711152 0.728938 1.055223 0.086 Uiso 1 1 calc R U . . .
C5 C 0.67095(8) 0.5005(4) 0.99941(13) 0.0597(6) Uani 1 1 d . . . . .
C6 C 0.65044(7) 0.4137(3) 0.92058(12) 0.0488(4) Uani 1 1 d . . . . .
C7 C 0.61738(9) 0.1970(3) 0.81488(13) 0.0551(5) Uani 1 1 d . . . . .
C8 C 0.63128(7) 0.3794(3) 0.76674(11) 0.0470(4) Uani 1 1 d . . . . .
C9 C 0.57686(7) 0.4568(3) 0.71487(12) 0.0491(4) Uani 1 1 d . . . . .
H9 H 0.562350 0.355069 0.673621 0.059 Uiso 1 1 calc R U . . .
C10 C 0.58488(7) 0.6289(3) 0.66000(12) 0.0498(4) Uani 1 1 d . . . . .
H10 H 0.597665 0.741259 0.688872 0.060 Uiso 1 1 calc R U . . .
C11 C 0.57476(7) 0.6299(3) 0.57262(12) 0.0533(5) Uani 1 1 d . . . . .
H11 H 0.562602 0.515210 0.545300 0.064 Uiso 1 1 calc R U . . .
C12 C 0.58070(8) 0.7930(4) 0.51426(12) 0.0549(5) Uani 1 1 d . . . . .
C13 C 0.55904(9) 0.7796(5) 0.42513(14) 0.0705(7) Uani 1 1 d . . . . .
H13 H 0.541334 0.668022 0.403531 0.085 Uiso 1 1 calc R U . . .
C14 C 0.56358(11) 0.9304(6) 0.36846(16) 0.0870(9) Uani 1 1 d . . . . .
H14 H 0.548127 0.920701 0.309352 0.104 Uiso 1 1 calc R U . . .
C15 C 0.59059(13) 1.0937(5) 0.39842(18) 0.0905(9) Uani 1 1 d . . . . .
H15 H 0.593772 1.194586 0.359938 0.109 Uiso 1 1 calc R U . . .
C16 C 0.61305(15) 1.1074(5) 0.48619(18) 0.0929(9) Uani 1 1 d . . . . .
H16 H 0.631900 1.217263 0.506973 0.112 Uiso 1 1 calc R U . . .
C17 C 0.60770(12) 0.9593(4) 0.54310(14) 0.0753(7) Uani 1 1 d . . . . .
H17 H 0.622603 0.971405 0.602369 0.090 Uiso 1 1 calc R U . . .
C18 C 0.53594(7) 0.4912(3) 0.77491(12) 0.0533(5) Uani 1 1 d . . . . .
C19 C 0.53415(9) 0.6599(4) 0.82098(15) 0.0633(5) Uani 1 1 d . . . . .
H19 H 0.558711 0.756554 0.815931 0.076 Uiso 1 1 calc R U . . .
C20 C 0.49618(11) 0.6878(5) 0.87493(18) 0.0841(8) Uani 1 1 d . . . . .
H20 H 0.495671 0.802228 0.906080 0.101 Uiso 1 1 calc R U . . .
C21 C 0.45936(12) 0.5468(7) 0.8824(2) 0.0988(11) Uani 1 1 d . . . . .
H21 H 0.433806 0.565419 0.918281 0.119 Uiso 1 1 calc R U . . .
C22 C 0.46062(12) 0.3799(7) 0.8369(2) 0.1044(12) Uani 1 1 d . . . . .
H22 H 0.435766 0.284171 0.841794 0.125 Uiso 1 1 calc R U . . .
C23 C 0.49839(10) 0.3508(5) 0.78331(18) 0.0808(8) Uani 1 1 d . . . . .
H23 H 0.498645 0.235809 0.752548 0.097 Uiso 1 1 calc R U . . .
C24 C 0.60841(14) 0.1062(4) 0.96705(17) 0.0872(9) Uani 1 1 d . . . . .
H24A H 0.637627 0.082272 1.014045 0.131 Uiso 1 1 calc R U . . .
H24B H 0.596640 -0.013026 0.938853 0.131 Uiso 1 1 calc R U . . .
H24C H 0.579557 0.164205 0.990578 0.131 Uiso 1 1 calc R U . . .
C25 C 0.70980(9) 0.2302(4) 0.72334(13) 0.0574(5) Uani 1 1 d . . . . .
C26 C 0.78321(10) 0.1029(5) 0.65622(18) 0.0848(9) Uani 1 1 d . . . . .
C27 C 0.79370(14) 0.1221(7) 0.5624(2) 0.1138(13) Uani 1 1 d . . . . .
H27A H 0.763138 0.077827 0.522033 0.171 Uiso 1 1 calc R U . . .
H27B H 0.824224 0.046186 0.555362 0.171 Uiso 1 1 calc R U . . .
H27C H 0.800375 0.254482 0.550296 0.171 Uiso 1 1 calc R U . . .
C28 C 0.77357(18) -0.1045(6) 0.6786(3) 0.1268(15) Uani 1 1 d . . . . .
H28B H 0.803569 -0.181068 0.669486 0.190 Uiso 1 1 calc R U . . .
H28A H 0.742007 -0.150461 0.641204 0.190 Uiso 1 1 calc R U . . .
H28C H 0.769011 -0.113487 0.739138 0.190 Uiso 1 1 calc R U . . .
C29 C 0.82699(13) 0.1975(8) 0.7211(2) 0.1267(16) Uani 1 1 d . . . . .
H29A H 0.828697 0.331732 0.707383 0.190 Uiso 1 1 calc R U . . .
H29B H 0.860530 0.137776 0.717116 0.190 Uiso 1 1 calc R U . . .
H29C H 0.819491 0.182818 0.779860 0.190 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
C25 O3 C26 120.87(17) . . ?
C6 N1 C24 126.57(19) . . ?
C7 N1 C6 110.53(16) . . ?
C7 N1 C24 122.9(2) . . ?
C8 N2 H2 119.4(17) . . ?
C25 N2 H2 118.7(16) . . ?
C25 N2 C8 121.57(17) . . ?
C2 C1 C6 121.19(18) . . ?
C2 C1 C8 131.00(18) . . ?
C6 C1 C8 107.80(17) . . ?
C1 C2 H2A 120.6 . . ?
C1 C2 C3 118.8(2) . . ?
C3 C2 H2A 120.6 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
F1 C5 C4 119.4(2) . . ?
F1 C5 C6 119.6(2) . . ?
C4 C5 C6 121.0(2) . . ?
C1 C6 N1 110.63(16) . . ?
C5 C6 N1 130.58(19) . . ?
C5 C6 C1 118.7(2) . . ?
O1 C7 N1 126.2(2) . . ?
O1 C7 C8 125.49(18) . . ?
N1 C7 C8 108.09(17) . . ?
N2 C8 C1 115.17(16) . . ?
N2 C8 C7 111.68(17) . . ?
N2 C8 C9 107.14(15) . . ?
C1 C8 C7 102.15(15) . . ?
C1 C8 C9 114.51(16) . . ?
C7 C8 C9 105.80(15) . . ?
C8 C9 H9 106.5 . . ?
C10 C9 C8 111.58(15) . . ?
C10 C9 H9 106.5 . . ?
C10 C9 C18 112.80(17) . . ?
C18 C9 C8 112.32(15) . . ?
C18 C9 H9 106.5 . . ?
C9 C10 H10 118.2 . . ?
C11 C10 C9 123.6(2) . . ?
C11 C10 H10 118.2 . . ?
C10 C11 H11 116.5 . . ?
C10 C11 C12 126.9(2) . . ?
C12 C11 H11 116.5 . . ?
C13 C12 C11 119.0(2) . . ?
C17 C12 C11 123.20(18) . . ?
C17 C12 C13 117.8(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.3(3) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.3 . . ?
C16 C17 C12 121.4(2) . . ?
C16 C17 H17 119.3 . . ?
C19 C18 C9 122.14(19) . . ?
C19 C18 C23 118.0(2) . . ?
C23 C18 C9 119.8(2) . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 120.9(2) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.7(3) . . ?
C23 C22 H22 119.6 . . ?
C18 C23 H23 119.6 . . ?
C22 C23 C18 120.8(3) . . ?
C22 C23 H23 119.6 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O2 C25 O3 127.1(2) . . ?
O2 C25 N2 123.58(19) . . ?
O3 C25 N2 109.35(17) . . ?
O3 C26 C27 101.7(2) . . ?
O3 C26 C28 109.8(3) . . ?
O3 C26 C29 109.3(3) . . ?
C28 C26 C27 111.2(3) . . ?
C28 C26 C29 113.2(3) . . ?
C29 C26 C27 111.1(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28B C28 H28A 109.5 . . ?
H28B C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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 C5 1.360(3) . ?
O1 C7 1.212(3) . ?
O2 C25 1.206(2) . ?
O3 C25 1.337(2) . ?
O3 C26 1.474(3) . ?
N1 C6 1.401(3) . ?
N1 C7 1.363(3) . ?
N1 C24 1.450(3) . ?
N2 H2 0.90(3) . ?
N2 C8 1.442(2) . ?
N2 C25 1.355(3) . ?
C1 C2 1.368(3) . ?
C1 C6 1.393(3) . ?
C1 C8 1.509(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.390(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(4) . ?
C5 C6 1.376(3) . ?
C7 C8 1.540(3) . ?
C8 C9 1.572(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.498(3) . ?
C9 C18 1.522(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.325(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.470(3) . ?
C12 C13 1.392(3) . ?
C12 C17 1.380(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.367(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(3) . ?
C18 C23 1.387(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.359(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(4) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C26 C27 1.517(4) . ?
C26 C28 1.513(6) . ?
C26 C29 1.514(5) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
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
F1 C5 C6 N1 -3.8(3) . . . . ?
F1 C5 C6 C1 -179.77(17) . . . . ?
O1 C7 C8 N2 -52.0(3) . . . . ?
O1 C7 C8 C1 -175.6(2) . . . . ?
O1 C7 C8 C9 64.2(3) . . . . ?
N1 C7 C8 N2 132.65(18) . . . . ?
N1 C7 C8 C1 9.0(2) . . . . ?
N1 C7 C8 C9 -111.10(18) . . . . ?
N2 C8 C9 C10 -57.2(2) . . . . ?
N2 C8 C9 C18 175.01(17) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C1 C8 C9 C10 71.9(2) . . . . ?
C1 C8 C9 C18 -55.9(2) . . . . ?
C2 C1 C6 N1 -176.05(18) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C8 N2 50.3(3) . . . . ?
C2 C1 C8 C7 171.6(2) . . . . ?
C2 C1 C8 C9 -74.6(3) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 F1 179.5(2) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 N1 175.2(2) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C6 N1 C7 O1 176.6(2) . . . . ?
C6 N1 C7 C8 -8.1(2) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C6 C1 C8 N2 -128.07(18) . . . . ?
C6 C1 C8 C7 -6.8(2) . . . . ?
C6 C1 C8 C9 107.02(18) . . . . ?
C7 N1 C6 C1 3.6(2) . . . . ?
C7 N1 C6 C5 -172.6(2) . . . . ?
C7 C8 C9 C10 -176.47(15) . . . . ?
C7 C8 C9 C18 55.7(2) . . . . ?
C8 N2 C25 O2 1.4(4) . . . . ?
C8 N2 C25 O3 -179.3(2) . . . . ?
C8 C1 C2 C3 -178.6(2) . . . . ?
C8 C1 C6 N1 2.5(2) . . . . ?
C8 C1 C6 C5 179.26(17) . . . . ?
C8 C9 C10 C11 114.2(2) . . . . ?
C8 C9 C18 C19 85.0(2) . . . . ?
C8 C9 C18 C23 -96.0(2) . . . . ?
C9 C10 C11 C12 178.91(18) . . . . ?
C9 C18 C19 C20 179.6(2) . . . . ?
C9 C18 C23 C22 -179.4(3) . . . . ?
C10 C9 C18 C19 -42.2(3) . . . . ?
C10 C9 C18 C23 136.8(2) . . . . ?
C10 C11 C12 C13 -168.2(2) . . . . ?
C10 C11 C12 C17 13.0(3) . . . . ?
C11 C12 C13 C14 179.6(2) . . . . ?
C11 C12 C17 C16 179.0(3) . . . . ?
C12 C13 C14 C15 1.6(4) . . . . ?
C13 C12 C17 C16 0.2(4) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C14 C15 C16 C17 -0.9(5) . . . . ?
C15 C16 C17 C12 1.0(5) . . . . ?
C17 C12 C13 C14 -1.5(4) . . . . ?
C18 C9 C10 C11 -118.3(2) . . . . ?
C18 C19 C20 C21 -0.6(4) . . . . ?
C19 C18 C23 C22 -0.4(4) . . . . ?
C19 C20 C21 C22 0.3(5) . . . . ?
C20 C21 C22 C23 0.0(6) . . . . ?
C21 C22 C23 C18 0.1(5) . . . . ?
C23 C18 C19 C20 0.6(4) . . . . ?
C24 N1 C6 C1 -174.0(2) . . . . ?
C24 N1 C6 C5 9.8(4) . . . . ?
C24 N1 C7 O1 -5.6(4) . . . . ?
C24 N1 C7 C8 169.7(2) . . . . ?
C25 O3 C26 C27 178.9(3) . . . . ?
C25 O3 C26 C28 61.1(4) . . . . ?
C25 O3 C26 C29 -63.6(3) . . . . ?
C25 N2 C8 C1 65.4(3) . . . . ?
C25 N2 C8 C7 -50.5(3) . . . . ?
C25 N2 C8 C9 -165.91(19) . . . . ?
C26 O3 C25 O2 0.0(4) . . . . ?
C26 O3 C25 N2 -179.2(2) . . . . ?
