#------------------------------------------------------------------------------
#$Date: 2020-06-05 11:41:08 +0200 (vie 05 de jun de 2020) $
#$Revision: 252679 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/63/7126340.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_7126340
loop_
_publ_author_name
'An, Yang'
'Zhang, Bo-Sheng'
'Zhang, Zhe'
'Liu, Ce'
'Gou, Xue-Ya'
'Ding, Ya-Nan'
'Liang, Yong-Min'
_publ_section_title
;
 A carboxylate-assisted amination/unactivated C(sp²)-H
 arylation reaction via a palladium/norbornene cooperative catalysis.
;
_journal_issue                   44
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5933
_journal_page_last               5936
_journal_paper_doi               10.1039/c9cc09265j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C17 H16 F N O2'
_chemical_formula_sum            'C17 H16 F N O2'
_chemical_formula_weight         285.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-09 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.406(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.1703(5)
_cell_length_b                   9.1104(2)
_cell_length_c                   19.1959(6)
_cell_measurement_reflns_used    2921
_cell_measurement_temperature    292.59(10)
_cell_measurement_theta_max      69.8640
_cell_measurement_theta_min      7.5500
_cell_volume                     2712.38(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      292.59(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -9.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   27.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -83.00  -34.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   30.0000 49

#__ type_ start__ end____ width___ exp.time_
  4 omega   33.00  112.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 79

#__ type_ start__ end____ width___ exp.time_
  5 omega   69.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
  6 omega   87.00  119.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
  7 omega    2.00   53.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  150.0000 51

#__ type_ start__ end____ width___ exp.time_
  8 omega   68.00  125.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 57

#__ type_ start__ end____ width___ exp.time_
  9 omega   41.00  131.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00   66.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega   43.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   37.00   68.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
 14 omega  144.00  174.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
 15 omega   64.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00  132.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
 17 omega   91.00  174.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -180.0000 83

#__ type_ start__ end____ width___ exp.time_
 18 omega   85.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   44.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 69

#__ type_ start__ end____ width___ exp.time_
 20 omega   43.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
 21 omega   69.00  104.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  150.0000 35
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0164139000
_diffrn_orient_matrix_UB_12      0.0134090000
_diffrn_orient_matrix_UB_13      0.0725922000
_diffrn_orient_matrix_UB_21      0.0798651000
_diffrn_orient_matrix_UB_22      -0.0957929000
_diffrn_orient_matrix_UB_23      0.0451189000
_diffrn_orient_matrix_UB_31      0.0567133000
_diffrn_orient_matrix_UB_32      0.1387517000
_diffrn_orient_matrix_UB_33      0.0241632000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10281
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         4.568
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0433
_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)+(0.0480P)²+0.3809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1189
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3489
_reflns_number_total             4680
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc09265j2.cif
_cod_data_source_block           anyang_2
_cod_depositor_comments
'Adding full bibliography for 7126337--7126341.cif.'
_cod_original_cell_volume        2712.40(16)
_cod_database_code               7126340
_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 97.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C17(H17A,H17B), C23(H23A,H23B), C26(H26A,H26B), C28(H28A,H28B),
 C29(H29A,H29B), C33(H33A,H33B), C36(H36A,H36B), C37(H37A,H37B), C41(H41A,H41B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C22(H22), C24(H24), C30(H30), C31(H31), C32(H32), C34(H34),
 C35(H35), C38(H38), C39(H39), C40(H40), C0AA(H0AA)
;
_olex2_date_sample_data_collection 2019-10-08
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.10160(7) 0.92757(15) 0.22093(7) 0.0613(3) Uani 1 1 d . . . . .
F2 F -0.09586(7) 0.66102(16) 0.28756(7) 0.0647(4) Uani 1 1 d . . . . .
N3 N -0.31421(8) 0.89219(16) 0.10492(8) 0.0350(3) Uani 1 1 d . . . . .
N4 N 0.31941(8) 0.68786(17) 0.39510(8) 0.0361(3) Uani 1 1 d . . . . .
O5 O -0.08354(8) 1.23841(15) 0.14541(8) 0.0496(3) Uani 1 1 d . . . . .
O6 O -0.39237(8) 0.65993(16) 0.15144(8) 0.0538(4) Uani 1 1 d . . . . .
C7 C 0.13771(10) 0.6423(2) 0.37487(9) 0.0357(4) Uani 1 1 d . . . . .
O8 O 0.08789(9) 0.34819(16) 0.36256(9) 0.0544(4) Uani 1 1 d . . . . .
C9 C 0.28129(10) 0.7386(2) 0.31458(10) 0.0383(4) Uani 1 1 d . . . . .
H9A H 0.219120 0.727640 0.292604 0.046 Uiso 1 1 calc R . . . .
H9B H 0.302712 0.678997 0.284672 0.046 Uiso 1 1 calc R . . . .
O10 O 0.39481(9) 0.91788(17) 0.34357(9) 0.0596(4) Uani 1 1 d . . . . .
C11 C 0.17356(12) 0.3800(2) 0.38424(11) 0.0453(4) Uani 1 1 d . . . . .
C12 C -0.19695(10) 1.05972(19) 0.11793(9) 0.0344(4) Uani 1 1 d . . . . .
C13 C -0.04559(10) 0.9850(2) 0.17099(9) 0.0380(4) Uani 1 1 d . . . . .
C14 C -0.01211(11) 0.7031(2) 0.32726(10) 0.0448(4) Uani 1 1 d . . . . .
C15 C 0.01809(11) 0.8843(2) 0.18068(10) 0.0430(4) Uani 1 1 d . . . . .
C16 C -0.13196(10) 0.9433(2) 0.13065(9) 0.0346(4) Uani 1 1 d . . . . .
C17 C -0.28072(10) 0.8435(2) 0.18545(9) 0.0373(4) Uani 1 1 d . . . . .
H17A H -0.306089 0.902191 0.212564 0.045 Uiso 1 1 calc R . . . .
H17B H -0.218733 0.857297 0.210596 0.045 Uiso 1 1 calc R . . . .
C18 C 0.20191(10) 0.5248(2) 0.38607(9) 0.0360(4) Uani 1 1 d . . . . .
C19 C -0.34219(11) 1.1546(2) 0.07483(11) 0.0460(4) Uani 1 1 d . . . . .
H19 H -0.400879 1.138639 0.058727 0.055 Uiso 1 1 calc R . . . .
C20 C 0.29061(10) 0.5466(2) 0.40378(9) 0.0364(4) Uani 1 1 d . . . . .
C21 C -0.28593(10) 1.03626(19) 0.09803(9) 0.0349(4) Uani 1 1 d . . . . .
C22 C -0.15025(11) 0.8019(2) 0.10034(10) 0.0414(4) Uani 1 1 d . . . . .
H22 H -0.207208 0.773234 0.071848 0.050 Uiso 1 1 calc R . . . .
C23 C 0.41292(10) 0.7094(2) 0.42855(10) 0.0444(4) Uani 1 1 d . . . . .
H23A H 0.437756 0.648413 0.401853 0.053 Uiso 1 1 calc R . . . .
H23B H 0.438360 0.681242 0.482490 0.053 Uiso 1 1 calc R . . . .
C24 C 0.00183(12) 0.7442(2) 0.15294(11) 0.0484(5) Uani 1 1 d . . . . .
H24 H 0.046387 0.678660 0.160867 0.058 Uiso 1 1 calc R . . . .
C25 C -0.16949(11) 1.2055(2) 0.12206(10) 0.0414(4) Uani 1 1 d . . . . .
C26 C -0.30168(11) 0.6842(2) 0.18913(11) 0.0454(4) Uani 1 1 d . . . . .
H26A H -0.273408 0.625122 0.164684 0.055 Uiso 1 1 calc R . . . .
H26B H -0.279986 0.653908 0.242621 0.055 Uiso 1 1 calc R . . . .
C27 C 0.05075(10) 0.6015(2) 0.33587(9) 0.0390(4) Uani 1 1 d . . . . .
C28 C -0.40698(10) 0.8652(2) 0.06607(10) 0.0434(4) Uani 1 1 d . . . . .
H28A H -0.428702 0.891631 0.012038 0.052 Uiso 1 1 calc R . . . .
H28B H -0.436353 0.925061 0.089205 0.052 Uiso 1 1 calc R . . . .
C29 C 0.03166(12) 0.4481(2) 0.30585(11) 0.0484(5) Uani 1 1 d . . . . .
H29A H -0.027834 0.424198 0.293679 0.058 Uiso 1 1 calc R . . . .
H29B H 0.039664 0.439680 0.258967 0.058 Uiso 1 1 calc R . . . .
C30 C 0.15727(11) 0.7847(2) 0.40439(10) 0.0415(4) Uani 1 1 d . . . . .
H30 H 0.214486 0.813615 0.431061 0.050 Uiso 1 1 calc R . . . .
C31 C 0.00550(12) 0.8431(2) 0.35516(11) 0.0506(5) Uani 1 1 d . . . . .
H31 H -0.038507 0.909028 0.348397 0.061 Uiso 1 1 calc R . . . .
C32 C -0.22620(13) 1.3228(2) 0.10029(13) 0.0537(5) Uani 1 1 d . . . . .
H32 H -0.206102 1.418293 0.102593 0.064 Uiso 1 1 calc R . . . .
C33 C -0.02758(11) 1.1376(2) 0.20210(11) 0.0462(4) Uani 1 1 d . . . . .
H33A H -0.036723 1.144237 0.248484 0.055 Uiso 1 1 calc R . . . .
H33B H 0.032042 1.162599 0.215377 0.055 Uiso 1 1 calc R . . . .
C34 C -0.08389(12) 0.7034(2) 0.11241(11) 0.0480(5) Uani 1 1 d . . . . .
H34 H -0.097128 0.608510 0.093006 0.058 Uiso 1 1 calc R . . . .
C35 C 0.34601(12) 0.4271(2) 0.42765(12) 0.0509(5) Uani 1 1 d . . . . .
H35 H 0.404613 0.441503 0.442495 0.061 Uiso 1 1 calc R . . . .
C36 C -0.42438(12) 0.7049(3) 0.07339(12) 0.0556(5) Uani 1 1 d . . . . .
H36A H -0.486030 0.687373 0.047972 0.067 Uiso 1 1 calc R . . . .
H36B H -0.397563 0.646228 0.047485 0.067 Uiso 1 1 calc R . . . .
C37 C 0.30378(12) 0.8969(2) 0.31053(12) 0.0501(5) Uani 1 1 d . . . . .
H37A H 0.278932 0.928390 0.257094 0.060 Uiso 1 1 calc R . . . .
H37B H 0.279235 0.956930 0.337844 0.060 Uiso 1 1 calc R . . . .
C38 C 0.09148(13) 0.8831(2) 0.39396(11) 0.0492(5) Uani 1 1 d . . . . .
H38 H 0.105315 0.977890 0.413383 0.059 Uiso 1 1 calc R . . . .
C39 C 0.22984(15) 0.2620(2) 0.40668(14) 0.0610(6) Uani 1 1 d . . . . .
H39 H 0.209474 0.167152 0.406038 0.073 Uiso 1 1 calc R . . . .
C40 C 0.31610(15) 0.2873(2) 0.42985(15) 0.0643(6) Uani 1 1 d . . . . .
H40 H 0.354844 0.209615 0.447226 0.077 Uiso 1 1 calc R . . . .
C41 C 0.43192(13) 0.8686(3) 0.42111(13) 0.0598(6) Uani 1 1 d . . . . .
H41A H 0.409987 0.927909 0.450726 0.072 Uiso 1 1 calc R . . . .
H41B H 0.493883 0.882403 0.442828 0.072 Uiso 1 1 calc R . . . .
C0AA C -0.31271(13) 1.2955(2) 0.07521(13) 0.0557(5) Uani 1 1 d . . . . .
H0AA H -0.351786 1.372834 0.058314 0.067 Uiso 1 1 calc R . . . .
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
C21 N3 C17 112.40(13) . . ?
C21 N3 C28 116.60(14) . . ?
C28 N3 C17 109.60(13) . . ?
C20 N4 C9 112.91(13) . . ?
C20 N4 C23 116.33(14) . . ?
C23 N4 C9 109.18(13) . . ?
C25 O5 C33 112.52(14) . . ?
C36 O6 C26 109.61(14) . . ?
C27 C7 C18 116.12(16) . . ?
C30 C7 C18 125.18(15) . . ?
C30 C7 C27 118.55(16) . . ?
C11 O8 C29 112.40(14) . . ?
N4 C9 H9A 109.6 . . ?
N4 C9 H9B 109.6 . . ?
N4 C9 C37 110.32(15) . . ?
H9A C9 H9B 108.1 . . ?
C37 C9 H9A 109.6 . . ?
C37 C9 H9B 109.6 . . ?
C41 O10 C37 109.75(14) . . ?
O8 C11 C18 121.34(17) . . ?
O8 C11 C39 116.31(18) . . ?
C39 C11 C18 122.31(18) . . ?
C21 C12 C16 125.64(16) . . ?
C25 C12 C16 117.26(15) . . ?
C25 C12 C21 117.02(16) . . ?
C15 C13 C16 119.04(18) . . ?
C15 C13 C33 123.40(16) . . ?
C16 C13 C33 117.56(16) . . ?
F2 C14 C27 117.59(19) . . ?
F2 C14 C31 119.01(17) . . ?
C31 C14 C27 123.39(18) . . ?
F1 C15 C13 117.69(18) . . ?
F1 C15 C24 118.77(17) . . ?
C24 C15 C13 123.54(17) . . ?
C13 C16 C12 116.20(16) . . ?
C22 C16 C12 125.05(15) . . ?
C22 C16 C13 118.52(16) . . ?
N3 C17 H17A 109.6 . . ?
N3 C17 H17B 109.6 . . ?
N3 C17 C26 110.34(14) . . ?
H17A C17 H17B 108.1 . . ?
C26 C17 H17A 109.6 . . ?
C26 C17 H17B 109.6 . . ?
C11 C18 C7 116.53(15) . . ?
C11 C18 C20 117.45(16) . . ?
C20 C18 C7 125.86(16) . . ?
C21 C19 H19 119.4 . . ?
C0AA C19 H19 119.4 . . ?
C0AA C19 C21 121.22(17) . . ?
N4 C20 C18 119.36(15) . . ?
C35 C20 N4 121.87(15) . . ?
C35 C20 C18 118.75(17) . . ?
C12 C21 N3 118.87(14) . . ?
C19 C21 N3 121.83(15) . . ?
C19 C21 C12 119.27(16) . . ?
C16 C22 H22 119.8 . . ?
C34 C22 C16 120.40(17) . . ?
C34 C22 H22 119.8 . . ?
N4 C23 H23A 109.8 . . ?
N4 C23 H23B 109.8 . . ?
N4 C23 C41 109.21(16) . . ?
H23A C23 H23B 108.3 . . ?
C41 C23 H23A 109.8 . . ?
C41 C23 H23B 109.8 . . ?
C15 C24 H24 121.3 . . ?
C15 C24 C34 117.34(17) . . ?
C34 C24 H24 121.3 . . ?
O5 C25 C12 120.80(16) . . ?
O5 C25 C32 116.52(17) . . ?
C32 C25 C12 122.62(17) . . ?
O6 C26 C17 110.92(15) . . ?
O6 C26 H26A 109.5 . . ?
O6 C26 H26B 109.5 . . ?
C17 C26 H26A 109.5 . . ?
C17 C26 H26B 109.5 . . ?
H26A C26 H26B 108.0 . . ?
C7 C27 C29 117.46(16) . . ?
C14 C27 C7 119.05(18) . . ?
C14 C27 C29 123.48(17) . . ?
N3 C28 H28A 109.8 . . ?
N3 C28 H28B 109.8 . . ?
N3 C28 C36 109.34(15) . . ?
H28A C28 H28B 108.3 . . ?
C36 C28 H28A 109.8 . . ?
C36 C28 H28B 109.8 . . ?
O8 C29 C27 109.71(15) . . ?
O8 C29 H29A 109.7 . . ?
O8 C29 H29B 109.7 . . ?
C27 C29 H29A 109.7 . . ?
C27 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
C7 C30 H30 119.9 . . ?
C38 C30 C7 120.13(17) . . ?
C38 C30 H30 119.9 . . ?
C14 C31 H31 121.2 . . ?
C14 C31 C38 117.51(18) . . ?
C38 C31 H31 121.2 . . ?
C25 C32 H32 120.6 . . ?
C0AA C32 C25 118.75(18) . . ?
C0AA C32 H32 120.6 . . ?
O5 C33 C13 109.68(15) . . ?
O5 C33 H33A 109.7 . . ?
O5 C33 H33B 109.7 . . ?
C13 C33 H33A 109.7 . . ?
C13 C33 H33B 109.7 . . ?
H33A C33 H33B 108.2 . . ?
C22 C34 H34 119.4 . . ?
C24 C34 C22 121.13(19) . . ?
C24 C34 H34 119.4 . . ?
C20 C35 H35 119.3 . . ?
C40 C35 C20 121.48(18) . . ?
C40 C35 H35 119.3 . . ?
O6 C36 C28 112.05(17) . . ?
O6 C36 H36A 109.2 . . ?
O6 C36 H36B 109.2 . . ?
C28 C36 H36A 109.2 . . ?
C28 C36 H36B 109.2 . . ?
H36A C36 H36B 107.9 . . ?
C9 C37 H37A 109.4 . . ?
C9 C37 H37B 109.4 . . ?
O10 C37 C9 111.25(16) . . ?
O10 C37 H37A 109.4 . . ?
O10 C37 H37B 109.4 . . ?
H37A C37 H37B 108.0 . . ?
C30 C38 H38 119.3 . . ?
C31 C38 C30 121.4(2) . . ?
C31 C38 H38 119.3 . . ?
C11 C39 H39 120.6 . . ?
C40 C39 C11 118.85(19) . . ?
C40 C39 H39 120.6 . . ?
C35 C40 H40 119.7 . . ?
C39 C40 C35 120.66(19) . . ?
C39 C40 H40 119.7 . . ?
O10 C41 C23 112.73(17) . . ?
O10 C41 H41A 109.0 . . ?
O10 C41 H41B 109.0 . . ?
C23 C41 H41A 109.0 . . ?
C23 C41 H41B 109.0 . . ?
H41A C41 H41B 107.8 . . ?
C19 C0AA H0AA 119.7 . . ?
C32 C0AA C19 120.65(18) . . ?
C32 C0AA H0AA 119.7 . . ?
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 C15 1.363(2) . ?
F2 C14 1.362(2) . ?
N3 C17 1.468(2) . ?
N3 C21 1.425(2) . ?
N3 C28 1.4611(19) . ?
N4 C9 1.471(2) . ?
N4 C20 1.414(2) . ?
N4 C23 1.4643(19) . ?
O5 C25 1.379(2) . ?
O5 C33 1.433(2) . ?
O6 C26 1.425(2) . ?
O6 C36 1.417(2) . ?
C7 C18 1.484(2) . ?
C7 C27 1.403(2) . ?
C7 C30 1.398(3) . ?
O8 C11 1.377(2) . ?
O8 C29 1.430(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C37 1.504(3) . ?
O10 C37 1.425(2) . ?
O10 C41 1.417(3) . ?
C11 C18 1.402(3) . ?
C11 C39 1.385(3) . ?
C12 C16 1.482(2) . ?
C12 C21 1.423(2) . ?
C12 C25 1.400(3) . ?
C13 C15 1.378(3) . ?
C13 C16 1.399(2) . ?
C13 C33 1.493(3) . ?
C14 C27 1.377(3) . ?
C14 C31 1.366(3) . ?
C15 C24 1.365(3) . ?
C16 C22 1.393(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C26 1.504(3) . ?
C18 C20 1.425(2) . ?
C19 H19 0.9300 . ?
C19 C21 1.388(2) . ?
C19 C0AA 1.378(3) . ?
C20 C35 1.388(3) . ?
C22 H22 0.9300 . ?
C22 C34 1.390(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C41 1.506(3) . ?
C24 H24 0.9300 . ?
C24 C34 1.388(3) . ?
C25 C32 1.384(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C29 1.493(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C36 1.510(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30 0.9300 . ?
C30 C38 1.388(3) . ?
C31 H31 0.9300 . ?
C31 C38 1.387(3) . ?
C32 H32 0.9300 . ?
C32 C0AA 1.374(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C35 C40 1.380(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C39 C40 1.371(3) . ?
C40 H40 0.9300 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C0AA H0AA 0.9300 . ?
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 C15 C24 C34 179.80(15) . . . . ?
F2 C14 C27 C7 178.49(14) . . . . ?
F2 C14 C27 C29 -1.6(3) . . . . ?
F2 C14 C31 C38 -178.72(16) . . . . ?
N3 C17 C26 O6 -58.25(19) . . . . ?
N3 C28 C36 O6 58.4(2) . . . . ?
N4 C9 C37 O10 58.2(2) . . . . ?
N4 C20 C35 C40 -174.56(19) . . . . ?
N4 C23 C41 O10 -58.2(2) . . . . ?
O5 C25 C32 C0AA 178.82(18) . . . . ?
C7 C18 C20 N4 -14.1(2) . . . . ?
C7 C18 C20 C35 167.19(16) . . . . ?
C7 C27 C29 O8 43.2(2) . . . . ?
C7 C30 C38 C31 0.7(3) . . . . ?
O8 C11 C18 C7 8.8(3) . . . . ?
O8 C11 C18 C20 -175.55(15) . . . . ?
O8 C11 C39 C40 -179.15(19) . . . . ?
C9 N4 C20 C18 -64.44(19) . . . . ?
C9 N4 C20 C35 114.22(18) . . . . ?
C9 N4 C23 C41 56.42(19) . . . . ?
C11 O8 C29 C27 -57.2(2) . . . . ?
C11 C18 C20 N4 170.65(15) . . . . ?
C11 C18 C20 C35 -8.0(2) . . . . ?
C11 C39 C40 C35 -2.8(4) . . . . ?
C12 C16 C22 C34 176.49(16) . . . . ?
C12 C25 C32 C0AA 1.5(3) . . . . ?
C13 C15 C24 C34 0.5(3) . . . . ?
C13 C16 C22 C34 2.2(3) . . . . ?
C14 C27 C29 O8 -136.75(17) . . . . ?
C14 C31 C38 C30 -0.2(3) . . . . ?
C15 C13 C16 C12 -176.13(15) . . . . ?
C15 C13 C16 C22 -1.3(2) . . . . ?
C15 C13 C33 O5 137.41(16) . . . . ?
C15 C24 C34 C22 0.4(3) . . . . ?
C16 C12 C21 N3 13.1(2) . . . . ?
C16 C12 C21 C19 -168.87(16) . . . . ?
C16 C12 C25 O5 -7.0(2) . . . . ?
C16 C12 C25 C32 170.27(17) . . . . ?
C16 C13 C15 F1 -179.32(14) . . . . ?
C16 C13 C15 C24 0.0(3) . . . . ?
C16 C13 C33 O5 -43.2(2) . . . . ?
C16 C22 C34 C24 -1.7(3) . . . . ?
C17 N3 C21 C12 67.37(19) . . . . ?
C17 N3 C21 C19 -110.58(18) . . . . ?
C17 N3 C28 C36 -55.95(19) . . . . ?
C18 C7 C27 C14 176.50(15) . . . . ?
C18 C7 C27 C29 -3.4(2) . . . . ?
C18 C7 C30 C38 -176.27(16) . . . . ?
C18 C11 C39 C40 -1.5(3) . . . . ?
C18 C20 C35 C40 4.1(3) . . . . ?
C20 N4 C9 C37 171.58(14) . . . . ?
C20 N4 C23 C41 -174.37(15) . . . . ?
C20 C35 C40 C39 1.5(4) . . . . ?
C21 N3 C17 C26 -171.96(13) . . . . ?
C21 N3 C28 C36 174.95(15) . . . . ?
C21 C12 C16 C13 -161.87(15) . . . . ?
C21 C12 C16 C22 23.7(3) . . . . ?
C21 C12 C25 O5 176.10(15) . . . . ?
C21 C12 C25 C32 -6.7(3) . . . . ?
C21 C19 C0AA C32 -1.4(3) . . . . ?
C23 N4 C9 C37 -57.36(18) . . . . ?
C23 N4 C20 C18 168.18(14) . . . . ?
C23 N4 C20 C35 -13.2(2) . . . . ?
C25 O5 C33 C13 57.23(19) . . . . ?
C25 C12 C16 C13 21.5(2) . . . . ?
C25 C12 C16 C22 -152.94(17) . . . . ?
C25 C12 C21 N3 -170.23(15) . . . . ?
C25 C12 C21 C19 7.8(2) . . . . ?
C25 C32 C0AA C19 2.7(3) . . . . ?
C26 O6 C36 C28 -59.3(2) . . . . ?
C27 C7 C18 C11 -23.2(2) . . . . ?
C27 C7 C18 C20 161.50(15) . . . . ?
C27 C7 C30 C38 -0.9(3) . . . . ?
C27 C14 C31 C38 0.1(3) . . . . ?
C28 N3 C17 C26 56.68(18) . . . . ?
C28 N3 C21 C12 -164.89(14) . . . . ?
C28 N3 C21 C19 17.2(2) . . . . ?
C29 O8 C11 C18 32.6(2) . . . . ?
C29 O8 C11 C39 -149.68(19) . . . . ?
C30 C7 C18 C11 152.23(17) . . . . ?
C30 C7 C18 C20 -23.0(3) . . . . ?
C30 C7 C27 C14 0.7(2) . . . . ?
C30 C7 C27 C29 -179.20(15) . . . . ?
C31 C14 C27 C7 -0.3(3) . . . . ?
C31 C14 C27 C29 179.61(17) . . . . ?
C33 O5 C25 C12 -33.6(2) . . . . ?
C33 O5 C25 C32 149.03(18) . . . . ?
C33 C13 C15 F1 0.1(3) . . . . ?
C33 C13 C15 C24 179.35(17) . . . . ?
C33 C13 C16 C12 4.4(2) . . . . ?
C33 C13 C16 C22 179.27(16) . . . . ?
C36 O6 C26 C17 58.8(2) . . . . ?
C37 O10 C41 C23 58.1(2) . . . . ?
C39 C11 C18 C7 -168.78(19) . . . . ?
C39 C11 C18 C20 6.9(3) . . . . ?
C41 O10 C37 C9 -57.5(2) . . . . ?
C0AA C19 C21 N3 173.95(18) . . . . ?
C0AA C19 C21 C12 -4.0(3) . . . . ?
