#------------------------------------------------------------------------------
#$Date: 2021-06-05 21:30:18 +0200 (Sat 05 de Jun de 2021) $
#$Revision: 266180 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/80/7158051.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_7158051
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           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-27
_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                 106.0020(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.32490(16)
_cell_length_b                   10.11966(12)
_cell_length_c                   11.47015(15)
_cell_measurement_reflns_used    6888
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3460
_cell_measurement_theta_min      3.9860
_cell_volume                     1263.59(3)
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00  -5.00   1.00    1.00    --  -40.98 124.00 -30.00   80
  2  ω   -112.00  -6.00   1.00    1.00    --  -40.98 -19.00-120.00  106
  3  ω     44.00  88.00   1.00    1.00    --   40.98-124.00-120.00   44
  4  ω     35.00 134.00   1.00    1.50    --  106.95 -61.00-180.00   99
  5  ω     64.00 121.00   1.00    1.50    --  106.95-124.00-150.00   57
  6  ω     54.00 130.00   1.00    1.50    --  106.95 -45.00 -90.00   76
  7  ω     82.00 174.00   1.00    1.50    --  106.95  45.00   0.00   92
  8  ω    153.00 178.00   1.00    1.50    --  106.95 124.00  30.00   25
  9  ω     94.00 177.00   1.00    1.50    --  106.95  61.00-120.00   83
 10  ω    145.00 172.00   1.00    1.50    --  106.95 124.00-180.00   27
 11  ω    100.00 130.00   1.00    1.50    --  106.95 124.00-180.00   30
 12  ω     90.00 176.00   1.00    1.50    --  106.95  45.00 -60.00   86
 13  ω     56.00 127.00   1.00    1.50    --  106.95 -45.00  60.00   71
 14  ω     29.00  91.00   1.00    1.50    --  106.95 -94.00  90.00   62
 15  ω     28.00 109.00   1.00    1.50    --  106.95 -94.00 -30.00   81
 16  ω     23.00  53.00   1.00    1.00    --   40.98-124.00 150.00   30
 17  ω   -114.00 -34.00   1.00    1.00    --  -40.98 -37.00-180.00   80
;
_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      0.0539667000
_diffrn_orient_matrix_UB_12      -0.0436533000
_diffrn_orient_matrix_UB_13      0.1326146000
_diffrn_orient_matrix_UB_21      -0.1232179000
_diffrn_orient_matrix_UB_22      0.0312684000
_diffrn_orient_matrix_UB_23      0.0263444000
_diffrn_orient_matrix_UB_31      -0.0439243000
_diffrn_orient_matrix_UB_32      -0.1425201000
_diffrn_orient_matrix_UB_33      -0.0350617000
_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  0.0245
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8662
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.716
_diffrn_reflns_theta_min         4.009
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61642
_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    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1644 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_coef       0.0050(5)
_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   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4383
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0268
_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)+(0.0405P)²+0.0948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0709
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_full    0.750
_reflns_Friedel_fraction_max     0.715
_reflns_number_gt                4295
_reflns_number_total             4383
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00550b2.cif
_cod_data_source_block           zc-3
_cod_depositor_comments
'Adding full bibliography for 7158051--7158052.cif.'
_cod_database_code               7158051
_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 100.00
_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), C11(H11), C12(H12), 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:
 C26(H26A,H26B,H26C), 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 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.669
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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 -0.05856(10) 0.44148(14) 0.35673(11) 0.0410(3) Uani 1 1 d . . . . .
O1 O 0.34943(11) 0.43591(13) 0.26286(10) 0.0247(3) Uani 1 1 d . . . . .
O2 O 0.53363(11) 0.53102(13) 0.26820(10) 0.0263(3) Uani 1 1 d . . . . .
O3 O 0.40308(11) 0.28845(12) 0.52156(11) 0.0257(3) Uani 1 1 d . . . . .
N1 N 0.20661(13) 0.37107(15) 0.45281(12) 0.0230(3) Uani 1 1 d . . . . .
N2 N 0.46242(13) 0.54429(15) 0.42944(13) 0.0224(3) Uani 1 1 d . . . . .
H2 H 0.520(2) 0.599(2) 0.456(2) 0.025(5) Uiso 1 1 d . . . . .
C1 C 0.24543(15) 0.59092(18) 0.42893(14) 0.0217(3) Uani 1 1 d . . . . .
C2 C 0.21748(18) 0.72064(19) 0.39631(16) 0.0276(4) Uani 1 1 d . . . . .
H2A H 0.279285 0.783584 0.406160 0.033 Uiso 1 1 calc R U . . .
C3 C 0.09389(19) 0.7557(2) 0.34796(17) 0.0340(4) Uani 1 1 d . . . . .
H3 H 0.073067 0.842463 0.324272 0.041 Uiso 1 1 calc R U . . .
C4 C 0.00284(18) 0.6613(2) 0.33545(17) 0.0349(4) Uani 1 1 d . . . . .
H4 H -0.079127 0.685135 0.304152 0.042 Uiso 1 1 calc R U . . .
C5 C 0.03296(16) 0.5320(2) 0.36917(16) 0.0296(4) Uani 1 1 d . . . . .
C6 C 0.15450(16) 0.49439(18) 0.41447(15) 0.0230(3) Uani 1 1 d . . . . .
C7 C 0.33158(15) 0.38053(17) 0.49026(14) 0.0204(3) Uani 1 1 d . . . . .
C8 C 0.36721(15) 0.52765(17) 0.49055(14) 0.0194(3) Uani 1 1 d . . . . .
C9 C 0.41492(15) 0.58236(17) 0.62270(14) 0.0200(3) Uani 1 1 d . . . . .
H9 H 0.428313 0.677395 0.615936 0.024 Uiso 1 1 calc R U . . .
C10 C 0.31757(15) 0.56686(17) 0.69168(14) 0.0208(3) Uani 1 1 d . . . . .
C11 C 0.29929(16) 0.44628(19) 0.74323(15) 0.0251(3) Uani 1 1 d . . . . .
H11 H 0.346624 0.373415 0.735559 0.030 Uiso 1 1 calc R U . . .
C12 C 0.21083(17) 0.4343(2) 0.80598(16) 0.0300(4) Uani 1 1 d . . . . .
H12 H 0.199618 0.353632 0.840218 0.036 Uiso 1 1 calc R U . . .
C13 C 0.13954(17) 0.5415(2) 0.81777(16) 0.0317(4) Uani 1 1 d . . . . .
H13 H 0.079775 0.532883 0.858938 0.038 Uiso 1 1 calc R U . . .
C14 C 0.15757(17) 0.6615(2) 0.76806(16) 0.0320(4) Uani 1 1 d . . . . .
H14 H 0.110321 0.734116 0.776676 0.038 Uiso 1 1 calc R U . . .
C15 C 0.24588(16) 0.67473(19) 0.70517(15) 0.0258(4) Uani 1 1 d . . . . .
H15 H 0.257153 0.756002 0.671926 0.031 Uiso 1 1 calc R U . . .
C16 C 0.53535(15) 0.52422(18) 0.69529(14) 0.0204(3) Uani 1 1 d . . . . .
H16 H 0.543309 0.432853 0.701765 0.024 Uiso 1 1 calc R U . . .
C17 C 0.63089(15) 0.59996(17) 0.75052(14) 0.0217(3) Uani 1 1 d . . . . .
H17 H 0.627010 0.688738 0.728826 0.026 Uiso 1 1 calc R U . . .
C18 C 0.74172(15) 0.55557(18) 0.84262(14) 0.0228(4) Uani 1 1 d . . . . .
C19 C 0.76662(17) 0.4228(2) 0.87242(16) 0.0282(4) Uani 1 1 d . . . . .
H19 H 0.717528 0.357899 0.825564 0.034 Uiso 1 1 calc R U . . .
C20 C 0.86292(18) 0.3859(2) 0.97032(17) 0.0359(5) Uani 1 1 d . . . . .
H20 H 0.877171 0.296971 0.989455 0.043 Uiso 1 1 calc R U . . .
C21 C 0.93849(17) 0.4818(3) 1.04018(17) 0.0392(5) Uani 1 1 d . . . . .
H21 H 1.003262 0.457281 1.106057 0.047 Uiso 1 1 calc R U . . .
C22 C 0.91643(17) 0.6139(3) 1.01082(17) 0.0364(5) Uani 1 1 d . . . . .
H22 H 0.966525 0.678345 1.057319 0.044 Uiso 1 1 calc R U . . .
C23 C 0.81982(16) 0.6508(2) 0.91221(16) 0.0290(4) Uani 1 1 d . . . . .
H23 H 0.806965 0.739693 0.892274 0.035 Uiso 1 1 calc R U . . .
C24 C 0.44039(16) 0.49910(17) 0.31407(15) 0.0215(3) Uani 1 1 d . . . . .
C25 C 0.51641(16) 0.52400(18) 0.13572(14) 0.0238(3) Uani 1 1 d . . . . .
C26 C 0.4115(2) 0.6143(2) 0.07301(18) 0.0336(4) Uani 1 1 d . . . . .
H26A H 0.336407 0.581936 0.085794 0.050 Uiso 1 1 calc R U . . .
H26B H 0.404293 0.616478 -0.012347 0.050 Uiso 1 1 calc R U . . .
H26C H 0.427401 0.701886 0.105839 0.050 Uiso 1 1 calc R U . . .
C27 C 0.49547(19) 0.3829(2) 0.09005(16) 0.0306(4) Uani 1 1 d . . . . .
H27A H 0.557965 0.326849 0.139310 0.046 Uiso 1 1 calc R U . . .
H27B H 0.498942 0.379145 0.007430 0.046 Uiso 1 1 calc R U . . .
H27C H 0.416250 0.353458 0.094499 0.046 Uiso 1 1 calc R U . . .
C28 C 0.6383(2) 0.5754(2) 0.12400(19) 0.0388(5) Uani 1 1 d . . . . .
H28A H 0.652161 0.662839 0.157456 0.058 Uiso 1 1 calc R U . . .
H28B H 0.636767 0.577871 0.039922 0.058 Uiso 1 1 calc R U . . .
H28C H 0.703211 0.518063 0.167180 0.058 Uiso 1 1 calc R U . . .
C29 C 0.14487(19) 0.2437(2) 0.43262(19) 0.0335(4) Uani 1 1 d . . . . .
H29A H 0.124057 0.222437 0.347824 0.050 Uiso 1 1 calc R U . . .
H29B H 0.071358 0.247729 0.458702 0.050 Uiso 1 1 calc R U . . .
H29C H 0.198439 0.176949 0.478005 0.050 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
C24 O2 C25 119.71(13) . . ?
C6 N1 C29 126.73(14) . . ?
C7 N1 C6 110.34(14) . . ?
C7 N1 C29 121.60(15) . . ?
C8 N2 H2 120.4(15) . . ?
C24 N2 H2 119.2(15) . . ?
C24 N2 C8 118.13(14) . . ?
C2 C1 C6 121.86(16) . . ?
C2 C1 C8 130.07(16) . . ?
C6 C1 C8 107.94(15) . . ?
C1 C2 H2A 120.7 . . ?
C1 C2 C3 118.58(19) . . ?
C3 C2 H2A 120.7 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.04(19) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.39(17) . . ?
C5 C4 H4 119.8 . . ?
F1 C5 C4 119.10(16) . . ?
F1 C5 C6 120.30(18) . . ?
C4 C5 C6 120.60(18) . . ?
C1 C6 N1 110.71(14) . . ?
C5 C6 N1 130.77(17) . . ?
C5 C6 C1 118.51(17) . . ?
O3 C7 N1 125.80(16) . . ?
O3 C7 C8 125.72(15) . . ?
N1 C7 C8 108.45(14) . . ?
N2 C8 C1 115.49(13) . . ?
N2 C8 C7 109.89(14) . . ?
N2 C8 C9 108.88(13) . . ?
C1 C8 C7 101.76(13) . . ?
C1 C8 C9 109.33(13) . . ?
C7 C8 C9 111.36(13) . . ?
C8 C9 H9 106.9 . . ?
C10 C9 C8 111.03(13) . . ?
C10 C9 H9 106.9 . . ?
C16 C9 C8 114.55(13) . . ?
C16 C9 H9 106.9 . . ?
C16 C9 C10 110.18(13) . . ?
C11 C10 C9 121.34(15) . . ?
C15 C10 C9 120.07(16) . . ?
C15 C10 C11 118.59(16) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.49(18) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.44(19) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.57(17) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.52(18) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.40(18) . . ?
C14 C15 H15 119.8 . . ?
C9 C16 H16 119.0 . . ?
C17 C16 C9 121.97(16) . . ?
C17 C16 H16 119.0 . . ?
C16 C17 H17 117.1 . . ?
C16 C17 C18 125.82(16) . . ?
C18 C17 H17 117.1 . . ?
C19 C18 C17 123.02(16) . . ?
C19 C18 C23 118.01(17) . . ?
C23 C18 C17 118.66(17) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.29(19) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.1(2) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.46(18) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.38(19) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 H23 119.6 . . ?
C22 C23 C18 120.7(2) . . ?
C22 C23 H23 119.6 . . ?
O1 C24 O2 126.14(15) . . ?
O1 C24 N2 123.46(16) . . ?
O2 C24 N2 110.37(14) . . ?
O2 C25 C26 108.84(14) . . ?
O2 C25 C27 111.33(14) . . ?
O2 C25 C28 102.08(14) . . ?
C26 C25 C27 112.13(15) . . ?
C26 C25 C28 111.41(17) . . ?
C28 C25 C27 110.60(16) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N1 C29 H29A 109.5 . . ?
N1 C29 H29B 109.5 . . ?
N1 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 1.361(2) . ?
O1 C24 1.217(2) . ?
O2 C24 1.343(2) . ?
O2 C25 1.4794(19) . ?
O3 C7 1.222(2) . ?
N1 C6 1.399(2) . ?
N1 C7 1.364(2) . ?
N1 C29 1.454(2) . ?
N2 H2 0.85(2) . ?
N2 C8 1.449(2) . ?
N2 C24 1.357(2) . ?
C1 C2 1.378(3) . ?
C1 C6 1.396(2) . ?
C1 C8 1.508(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.402(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C5 C6 1.384(2) . ?
C7 C8 1.542(2) . ?
C8 C9 1.563(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.532(2) . ?
C9 C16 1.508(2) . ?
C10 C11 1.396(3) . ?
C10 C15 1.394(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.391(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.335(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.470(2) . ?
C18 C19 1.396(3) . ?
C18 C23 1.399(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.392(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.390(3) . ?
C23 H23 0.9300 . ?
C25 C26 1.514(3) . ?
C25 C27 1.517(3) . ?
C25 C28 1.516(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 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 0.4(3) . . . . ?
F1 C5 C6 C1 -178.26(15) . . . . ?
O3 C7 C8 N2 50.2(2) . . . . ?
O3 C7 C8 C1 173.03(15) . . . . ?
O3 C7 C8 C9 -70.6(2) . . . . ?
N1 C7 C8 N2 -131.74(13) . . . . ?
N1 C7 C8 C1 -8.86(16) . . . . ?
N1 C7 C8 C9 107.53(15) . . . . ?
N2 C8 C9 C10 -179.88(14) . . . . ?
N2 C8 C9 C16 -54.29(19) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C1 C8 C9 C10 53.11(18) . . . . ?
C1 C8 C9 C16 178.70(14) . . . . ?
C2 C1 C6 N1 179.25(15) . . . . ?
C2 C1 C6 C5 -1.8(2) . . . . ?
C2 C1 C8 N2 -57.3(2) . . . . ?
C2 C1 C8 C7 -176.26(17) . . . . ?
C2 C1 C8 C9 65.9(2) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 F1 179.49(17) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 N1 -179.29(17) . . . . ?
C4 C5 C6 C1 2.1(3) . . . . ?
C6 N1 C7 O3 -175.10(16) . . . . ?
C6 N1 C7 C8 6.79(17) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C6 C1 C8 N2 126.80(15) . . . . ?
C6 C1 C8 C7 7.82(16) . . . . ?
C6 C1 C8 C9 -110.04(15) . . . . ?
C7 N1 C6 C1 -1.59(19) . . . . ?
C7 N1 C6 C5 179.68(17) . . . . ?
C7 C8 C9 C10 -58.55(17) . . . . ?
C7 C8 C9 C16 67.04(17) . . . . ?
C8 N2 C24 O1 -6.3(3) . . . . ?
C8 N2 C24 O2 175.43(14) . . . . ?
C8 C1 C2 C3 -175.06(17) . . . . ?
C8 C1 C6 N1 -4.43(18) . . . . ?
C8 C1 C6 C5 174.48(14) . . . . ?
C8 C9 C10 C11 80.07(18) . . . . ?
C8 C9 C10 C15 -100.62(18) . . . . ?
C8 C9 C16 C17 126.77(17) . . . . ?
C9 C10 C11 C12 179.71(15) . . . . ?
C9 C10 C15 C14 -179.78(15) . . . . ?
C9 C16 C17 C18 166.58(15) . . . . ?
C10 C9 C16 C17 -107.20(18) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C10 C15 C14 -0.4(2) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C10 -0.1(3) . . . . ?
C15 C10 C11 C12 0.4(2) . . . . ?
C16 C9 C10 C11 -47.9(2) . . . . ?
C16 C9 C10 C15 131.39(16) . . . . ?
C16 C17 C18 C19 8.3(3) . . . . ?
C16 C17 C18 C23 -165.10(17) . . . . ?
C17 C18 C19 C20 -171.25(16) . . . . ?
C17 C18 C23 C22 171.38(16) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C19 C18 C23 C22 -2.4(2) . . . . ?
C19 C20 C21 C22 0.0(3) . . . . ?
C20 C21 C22 C23 -0.2(3) . . . . ?
C21 C22 C23 C18 1.4(3) . . . . ?
C23 C18 C19 C20 2.2(3) . . . . ?
C24 O2 C25 C26 58.7(2) . . . . ?
C24 O2 C25 C27 -65.4(2) . . . . ?
C24 O2 C25 C28 176.54(16) . . . . ?
C24 N2 C8 C1 -58.5(2) . . . . ?
C24 N2 C8 C7 55.84(19) . . . . ?
C24 N2 C8 C9 178.05(15) . . . . ?
C25 O2 C24 O1 17.8(3) . . . . ?
C25 O2 C24 N2 -163.90(15) . . . . ?
C29 N1 C6 C1 -168.44(16) . . . . ?
C29 N1 C6 C5 12.8(3) . . . . ?
C29 N1 C7 O3 -7.5(2) . . . . ?
C29 N1 C7 C8 174.44(15) . . . . ?
