#------------------------------------------------------------------------------
#$Date: 2021-09-06 12:02:51 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268507 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/84/7128484.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_7128484
loop_
_publ_author_name
'Dai, Zhen-Yao'
'Wang, Pu-Sheng'
'Gong, Liu-Zhu'
_publ_section_title
;
 Access to chiral γ-butenolides via palladium-catalyzed asymmetric
 allylic C-H alkylation of 1,4-dienes.
;
_journal_issue                   55
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6748
_journal_page_last               6751
_journal_paper_doi               10.1039/d1cc02295d
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C49 H34 F12 N3 O6 P'
_chemical_formula_sum            'C49 H34 F12 N3 O6 P'
_chemical_formula_weight         1019.76
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-17 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.284(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.5180(7)
_cell_length_b                   8.3701(4)
_cell_length_c                   19.8041(11)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      53.95
_cell_measurement_theta_min      2.90
_cell_volume                     2197.5(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      169.98
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23560
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.906
_diffrn_reflns_theta_min         2.900
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.972
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1399 before and 0.0643 after correction. The Ratio of minimum to maximum transmission is 0.7826. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.364
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     640
_refine_ls_number_reflns         7351
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0638
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1775
_reflns_Friedel_coverage         0.652
_reflns_Friedel_fraction_full    0.765
_reflns_Friedel_fraction_max     0.748
_reflns_number_gt                5579
_reflns_number_total             7351
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02295d2.cif
_cod_data_source_block           20190115dzy
_cod_depositor_comments
'Adding full bibliography for 7128483--7128484.cif.'
_cod_database_code               7128484
_shelx_shelxl_version_number     2016/6
_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   0.981
_shelx_estimated_absorpt_t_min   0.868
_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:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C13(H13A,H13B), C14(H14A,
 H14B), C15(H15A,H15B), C16(H16A,H16B), C41(H41A,H41B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), C29(H29),
 C30(H30), C31(H31), C34(H34), C36(H36), C38(H38), C43(H43), C45(H45), C47(H47)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
P1 P 0.27186(11) 0.2685(2) 0.73340(7) 0.0303(4) Uani 1 1 d . . . . .
F1 F 0.1650(4) -0.1206(6) 0.8969(3) 0.0773(16) Uani 1 1 d . . . . .
F2 F 0.0152(3) -0.0312(6) 0.8711(2) 0.0632(12) Uani 1 1 d . . . . .
F3 F 0.0866(3) -0.0551(5) 0.9762(2) 0.0608(12) Uani 1 1 d . . . . .
F4 F 0.0926(3) 0.6109(5) 1.0100(2) 0.0537(11) Uani 1 1 d . . . . .
F5 F 0.1806(4) 0.4531(6) 1.08201(18) 0.0673(14) Uani 1 1 d . . . . .
F6 F 0.2517(3) 0.6318(7) 1.0296(2) 0.0809(17) Uani 1 1 d . . . . .
F7 F 0.3897(3) 1.0806(6) 0.9259(3) 0.0744(15) Uani 1 1 d . . . . .
F8 F 0.5397(3) 1.0419(6) 0.9790(2) 0.0768(16) Uani 1 1 d . . . . .
F9 F 0.5098(5) 1.1208(7) 0.8744(3) 0.099(2) Uani 1 1 d . . . . .
F10 F 0.6771(6) 0.4644(12) 0.9574(3) 0.163(4) Uani 1 1 d . . . . .
F11 F 0.7283(4) 0.5896(8) 0.8848(6) 0.164(4) Uani 1 1 d . . . . .
F12 F 0.6475(3) 0.3813(6) 0.8564(2) 0.0670(13) Uani 1 1 d . . . . .
O1 O 0.1724(3) 0.2947(5) 0.67357(18) 0.0300(10) Uani 1 1 d . . . . .
O2 O 0.3567(3) 0.3665(6) 0.70225(18) 0.0331(10) Uani 1 1 d . . . . .
O3 O 0.0016(4) 0.0676(7) 0.7034(3) 0.0516(13) Uani 1 1 d . . . . .
O4 O -0.0366(3) 0.2342(7) 0.6175(2) 0.0477(13) Uani 1 1 d . . . . .
O5 O 0.5715(4) 0.4633(8) 0.6937(3) 0.0632(15) Uani 1 1 d . . . . .
O6 O 0.7226(4) 0.3761(10) 0.6963(4) 0.100(3) Uani 1 1 d . . . . .
N1 N 0.2627(4) 0.4023(6) 0.7961(2) 0.0302(12) Uani 1 1 d . . . . .
N2 N -0.0168(4) 0.2039(8) 0.6794(3) 0.0414(15) Uani 1 1 d . . . . .
N3 N 0.6331(5) 0.3570(9) 0.6990(3) 0.0558(18) Uani 1 1 d . . . . .
C1 C 0.1500(4) 0.4449(8) 0.6432(3) 0.0279(13) Uani 1 1 d . . . . .
C2 C 0.0703(5) 0.5323(8) 0.6599(3) 0.0325(15) Uani 1 1 d . . . . .
C3 C 0.0521(5) 0.6838(9) 0.6279(3) 0.0393(16) Uani 1 1 d . . . . .
H3 H -0.003627 0.744973 0.635952 0.047 Uiso 1 1 calc R . . . .
C4 C 0.1130(5) 0.7464(8) 0.5852(3) 0.0350(15) Uani 1 1 d . . . . .
C5 C 0.0874(6) 0.9073(9) 0.5538(4) 0.0498(19) Uani 1 1 d . . . . .
H5A H 0.058113 0.973629 0.586341 0.060 Uiso 1 1 calc R . . . .
H5B H 0.035395 0.894581 0.511388 0.060 Uiso 1 1 calc R . . . .
C6 C 0.1774(6) 0.9940(11) 0.5361(4) 0.060(2) Uani 1 1 d . . . . .
H6A H 0.153877 1.088949 0.507562 0.072 Uiso 1 1 calc R . . . .
H6B H 0.222027 1.031153 0.578886 0.072 Uiso 1 1 calc R . . . .
C7 C 0.2358(6) 0.8851(10) 0.4971(4) 0.054(2) Uani 1 1 d . . . . .
H7A H 0.191374 0.849474 0.453928 0.064 Uiso 1 1 calc R . . . .
H7B H 0.293002 0.944698 0.484792 0.064 Uiso 1 1 calc R . . . .
C8 C 0.2752(5) 0.7413(9) 0.5400(3) 0.0402(16) Uani 1 1 d . . . . .
H8A H 0.332482 0.774834 0.576418 0.048 Uiso 1 1 calc R . . . .
H8B H 0.301046 0.662653 0.510334 0.048 Uiso 1 1 calc R . . . .
C9 C 0.1951(5) 0.6602(8) 0.5738(3) 0.0330(15) Uani 1 1 d . . . . .
C10 C 0.2109(5) 0.5035(8) 0.5995(3) 0.0329(15) Uani 1 1 d . . . . .
C11 C 0.2917(4) 0.3979(8) 0.5817(3) 0.0274(14) Uani 1 1 d . . . . .
C12 C 0.2935(4) 0.3587(8) 0.5123(3) 0.0326(15) Uani 1 1 d . . . . .
C13 C 0.2072(5) 0.4057(9) 0.4543(3) 0.0381(16) Uani 1 1 d . . . . .
H13A H 0.148709 0.335569 0.455801 0.046 Uiso 1 1 calc R . . . .
H13B H 0.186809 0.516819 0.461919 0.046 Uiso 1 1 calc R . . . .
C14 C 0.2336(6) 0.3942(10) 0.3839(3) 0.0452(18) Uani 1 1 d . . . . .
H14A H 0.171659 0.407326 0.348214 0.054 Uiso 1 1 calc R . . . .
H14B H 0.280740 0.481322 0.378133 0.054 Uiso 1 1 calc R . . . .
C15 C 0.2816(6) 0.2353(10) 0.3743(3) 0.0482(19) Uani 1 1 d . . . . .
H15A H 0.292591 0.225990 0.326457 0.058 Uiso 1 1 calc R . . . .
H15B H 0.236383 0.147475 0.382575 0.058 Uiso 1 1 calc R . . . .
C16 C 0.3822(5) 0.2228(9) 0.4248(3) 0.0430(18) Uani 1 1 d . . . . .
H16A H 0.431440 0.295918 0.409992 0.052 Uiso 1 1 calc R . . . .
H16B H 0.408410 0.112508 0.423816 0.052 Uiso 1 1 calc R . . . .
C17 C 0.3726(4) 0.2645(8) 0.4986(3) 0.0306(14) Uani 1 1 d . . . . .
C18 C 0.4432(5) 0.2022(8) 0.5522(3) 0.0337(15) Uani 1 1 d . . . . .
H18 H 0.496138 0.137536 0.542017 0.040 Uiso 1 1 calc R . . . .
C19 C 0.4388(4) 0.2320(8) 0.6209(3) 0.0307(15) Uani 1 1 d . . . . .
C20 C 0.3622(4) 0.3296(8) 0.6330(3) 0.0313(15) Uani 1 1 d . . . . .
C21 C 0.5083(5) 0.1419(9) 0.6766(3) 0.0374(16) Uani 1 1 d . . . . .
C22 C 0.4811(5) -0.0179(10) 0.6909(3) 0.0430(17) Uani 1 1 d . . . . .
H22 H 0.417019 -0.059116 0.669756 0.052 Uiso 1 1 calc R . . . .
C23 C 0.5477(6) -0.1119(11) 0.7355(4) 0.054(2) Uani 1 1 d . . . . .
H23 H 0.530070 -0.219097 0.743512 0.065 Uiso 1 1 calc R . . . .
C24 C 0.6399(5) -0.0523(11) 0.7686(3) 0.0479(19) Uani 1 1 d . . . . .
H24 H 0.683783 -0.118565 0.800058 0.058 Uiso 1 1 calc R . . . .
C25 C 0.6693(5) 0.0994(10) 0.7572(3) 0.0448(18) Uani 1 1 d . . . . .
H25 H 0.733050 0.139545 0.779553 0.054 Uiso 1 1 calc R . . . .
C26 C 0.6017(5) 0.1944(9) 0.7110(4) 0.0450(18) Uani 1 1 d . . . . .
C27 C 0.0157(5) 0.4875(9) 0.7145(3) 0.0357(16) Uani 1 1 d . . . . .
C28 C 0.0022(5) 0.6057(10) 0.7630(3) 0.0426(17) Uani 1 1 d . . . . .
H28 H 0.023247 0.712143 0.756893 0.051 Uiso 1 1 calc R . . . .
C29 C -0.0406(5) 0.5704(11) 0.8192(4) 0.053(2) Uani 1 1 d . . . . .
H29 H -0.049813 0.653580 0.850013 0.063 Uiso 1 1 calc R . . . .
C30 C -0.0703(5) 0.4181(11) 0.8313(4) 0.052(2) Uani 1 1 d . . . . .
H30 H -0.098192 0.394947 0.870690 0.062 Uiso 1 1 calc R . . . .
C31 C -0.0586(4) 0.2987(10) 0.7850(3) 0.0446(18) Uani 1 1 d . . . . .
H31 H -0.078033 0.192277 0.792747 0.054 Uiso 1 1 calc R . . . .
C32 C -0.0189(4) 0.3338(9) 0.7278(3) 0.0371(16) Uani 1 1 d . . . . .
C33 C 0.2215(4) 0.3544(8) 0.8541(3) 0.0304(14) Uani 1 1 d . . . . .
C34 C 0.1802(5) 0.2023(9) 0.8567(3) 0.0359(16) Uani 1 1 d . . . . .
H34 H 0.178009 0.131481 0.818946 0.043 Uiso 1 1 calc R . . . .
C35 C 0.1423(4) 0.1528(8) 0.9134(3) 0.0360(15) Uani 1 1 d . . . . .
C36 C 0.1407(4) 0.2577(9) 0.9681(3) 0.0362(15) Uani 1 1 d . . . . .
H36 H 0.112259 0.226135 1.006246 0.043 Uiso 1 1 calc R . . . .
C37 C 0.1817(4) 0.4091(8) 0.9653(3) 0.0340(15) Uani 1 1 d . . . . .
C38 C 0.2222(4) 0.4575(9) 0.9086(3) 0.0343(15) Uani 1 1 d . . . . .
H38 H 0.250237 0.561352 0.907743 0.041 Uiso 1 1 calc R . . . .
C39 C 0.1770(5) 0.5241(10) 1.0206(3) 0.0427(18) Uani 1 1 d . . . . .
C40 C 0.1031(5) -0.0104(9) 0.9151(4) 0.0413(17) Uani 1 1 d . . . . .
C41 C 0.2820(4) 0.5754(8) 0.7879(3) 0.0311(14) Uani 1 1 d . . . . .
H41A H 0.225109 0.636812 0.799606 0.037 Uiso 1 1 calc R . . . .
H41B H 0.283532 0.596664 0.738911 0.037 Uiso 1 1 calc R . . . .
C42 C 0.3799(4) 0.6358(9) 0.8320(3) 0.0321(15) Uani 1 1 d . . . . .
C43 C 0.3838(4) 0.7907(8) 0.8563(3) 0.0326(14) Uani 1 1 d . . . . .
H43 H 0.324493 0.854484 0.847320 0.039 Uiso 1 1 calc R . . . .
C44 C 0.4729(5) 0.8556(8) 0.8936(3) 0.0328(14) Uani 1 1 d . . . . .
C45 C 0.5601(5) 0.7609(9) 0.9072(3) 0.0375(15) Uani 1 1 d . . . . .
H45 H 0.621133 0.801072 0.933780 0.045 Uiso 1 1 calc R . . . .
C46 C 0.5549(5) 0.6073(9) 0.8808(3) 0.0361(15) Uani 1 1 d . . . . .
C47 C 0.4664(5) 0.5421(8) 0.8434(3) 0.0352(15) Uani 1 1 d . . . . .
H47 H 0.465087 0.436194 0.826042 0.042 Uiso 1 1 calc R . . . .
C48 C 0.6492(5) 0.5089(11) 0.8934(4) 0.056(2) Uani 1 1 d . . . . .
C49 C 0.4785(5) 1.0208(10) 0.9185(4) 0.0454(18) 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 0.0148 0.0070 '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 0.0599 0.0411 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2596 0.3354 '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
O1 P1 O2 101.5(2) . . ?
O1 P1 N1 106.0(2) . . ?
O2 P1 N1 95.9(2) . . ?
C1 O1 P1 120.9(4) . . ?
C20 O2 P1 115.5(4) . . ?
C33 N1 P1 119.9(4) . . ?
C33 N1 C41 117.7(5) . . ?
C41 N1 P1 121.7(4) . . ?
O3 N2 C32 117.5(6) . . ?
O4 N2 O3 124.1(6) . . ?
O4 N2 C32 118.4(6) . . ?
O5 N3 O6 124.5(8) . . ?
O5 N3 C26 119.0(6) . . ?
O6 N3 C26 116.5(7) . . ?
C2 C1 O1 118.8(5) . . ?
C2 C1 C10 122.7(6) . . ?
C10 C1 O1 118.5(5) . . ?
C1 C2 C3 116.0(6) . . ?
C1 C2 C27 124.2(6) . . ?
C3 C2 C27 119.2(6) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.4(6) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 118.3(6) . . ?
C9 C4 C3 119.6(6) . . ?
C9 C4 C5 122.1(6) . . ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C4 C5 C6 113.4(6) . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 C5 110.6(7) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 C6 110.9(6) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C7 C8 C9 113.3(6) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C4 C9 C8 119.9(6) . . ?
C4 C9 C10 119.9(6) . . ?
C10 C9 C8 119.9(6) . . ?
C1 C10 C9 119.0(6) . . ?
C1 C10 C11 118.9(6) . . ?
C9 C10 C11 122.0(6) . . ?
C12 C11 C10 121.0(5) . . ?
C20 C11 C10 120.2(5) . . ?
C20 C11 C12 118.6(5) . . ?
C11 C12 C13 121.1(5) . . ?
C17 C12 C11 118.6(5) . . ?
C17 C12 C13 120.1(5) . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C12 113.4(5) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C13 111.0(6) . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C14 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
C14 C15 C16 109.2(6) . . ?
H15A C15 H15B 108.3 . . ?
C16 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C15 C16 C17 112.2(5) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C12 C17 C16 121.7(5) . . ?
C18 C17 C12 120.2(5) . . ?
C18 C17 C16 118.1(6) . . ?
C17 C18 H18 119.1 . . ?
C17 C18 C19 121.7(6) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C21 119.0(5) . . ?
C20 C19 C18 117.0(5) . . ?
C20 C19 C21 123.6(5) . . ?
C11 C20 O2 117.5(5) . . ?
C11 C20 C19 123.7(5) . . ?
C19 C20 O2 118.7(5) . . ?
C22 C21 C19 117.8(6) . . ?
C26 C21 C19 125.5(7) . . ?
C26 C21 C22 116.4(6) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.0(7) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.9(8) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.5(7) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 H25 121.2 . . ?
C24 C25 C26 117.5(7) . . ?
C26 C25 H25 121.2 . . ?
C21 C26 N3 118.8(6) . . ?
C21 C26 C25 123.7(7) . . ?
C25 C26 N3 117.4(7) . . ?
C28 C27 C2 118.0(7) . . ?
C32 C27 C2 127.0(6) . . ?
C32 C27 C28 114.7(6) . . ?
C27 C28 H28 119.1 . . ?
C29 C28 C27 121.8(8) . . ?
C29 C28 H28 119.1 . . ?
C28 C29 H29 119.2 . . ?
C30 C29 C28 121.5(7) . . ?
C30 C29 H29 119.2 . . ?
C29 C30 H30 120.7 . . ?
C29 C30 C31 118.6(7) . . ?
C31 C30 H30 120.7 . . ?
C30 C31 H31 119.9 . . ?
C32 C31 C30 120.3(7) . . ?
C32 C31 H31 119.9 . . ?
C27 C32 N2 120.5(6) . . ?
C31 C32 N2 116.4(6) . . ?
C31 C32 C27 123.1(6) . . ?
C34 C33 N1 120.5(5) . . ?
C38 C33 N1 120.6(6) . . ?
C38 C33 C34 118.8(5) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 C33 121.1(6) . . ?
C35 C34 H34 119.4 . . ?
C34 C35 C36 120.3(7) . . ?
C34 C35 C40 119.3(6) . . ?
C36 C35 C40 120.4(6) . . ?
C35 C36 H36 120.8 . . ?
C37 C36 C35 118.4(6) . . ?
C37 C36 H36 120.8 . . ?
C36 C37 C38 121.1(6) . . ?
C36 C37 C39 119.5(6) . . ?
C38 C37 C39 119.3(6) . . ?
C33 C38 C37 120.2(7) . . ?
C33 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
F4 C39 F5 105.2(5) . . ?
F4 C39 F6 104.7(6) . . ?
F4 C39 C37 113.6(5) . . ?
F5 C39 C37 112.7(6) . . ?
F6 C39 F5 106.4(5) . . ?
F6 C39 C37 113.5(5) . . ?
F1 C40 C35 112.8(5) . . ?
F2 C40 F1 104.9(6) . . ?
F2 C40 C35 112.6(6) . . ?
F3 C40 F1 106.0(6) . . ?
F3 C40 F2 105.7(5) . . ?
F3 C40 C35 114.2(6) . . ?
N1 C41 H41A 108.7 . . ?
N1 C41 H41B 108.7 . . ?
N1 C41 C42 114.4(5) . . ?
H41A C41 H41B 107.6 . . ?
C42 C41 H41A 108.7 . . ?
C42 C41 H41B 108.7 . . ?
C43 C42 C41 118.8(6) . . ?
C43 C42 C47 120.0(6) . . ?
C47 C42 C41 121.0(6) . . ?
C42 C43 H43 119.3 . . ?
C42 C43 C44 121.4(6) . . ?
C44 C43 H43 119.3 . . ?
C43 C44 C45 119.2(6) . . ?
C43 C44 C49 121.9(6) . . ?
C45 C44 C49 118.9(6) . . ?
C44 C45 H45 120.8 . . ?
C46 C45 C44 118.3(6) . . ?
C46 C45 H45 120.8 . . ?
C45 C46 C47 122.7(6) . . ?
C45 C46 C48 118.1(6) . . ?
C47 C46 C48 119.2(7) . . ?
C42 C47 C46 118.3(6) . . ?
C42 C47 H47 120.8 . . ?
C46 C47 H47 120.8 . . ?
F10 C48 C46 113.1(7) . . ?
F11 C48 F10 100.7(8) . . ?
F11 C48 C46 112.7(8) . . ?
F12 C48 F10 106.5(8) . . ?
F12 C48 F11 106.2(7) . . ?
F12 C48 C46 116.1(6) . . ?
F7 C49 F9 104.1(7) . . ?
F7 C49 C44 113.7(6) . . ?
F8 C49 F7 105.5(5) . . ?
F8 C49 F9 106.5(6) . . ?
F8 C49 C44 114.3(6) . . ?
F9 C49 C44 111.8(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
P1 O1 1.624(4) . ?
P1 O2 1.626(4) . ?
P1 N1 1.694(5) . ?
F1 C40 1.341(8) . ?
F2 C40 1.341(8) . ?
F3 C40 1.327(8) . ?
F4 C39 1.335(8) . ?
F5 C39 1.346(8) . ?
F6 C39 1.339(8) . ?
F7 C49 1.335(8) . ?
F8 C49 1.327(8) . ?
F9 C49 1.337(9) . ?
F10 C48 1.305(10) . ?
F11 C48 1.304(11) . ?
F12 C48 1.292(9) . ?
O1 C1 1.401(7) . ?
O2 C20 1.421(6) . ?
O3 N2 1.242(8) . ?
O4 N2 1.227(7) . ?
O5 N3 1.208(8) . ?
O6 N3 1.232(8) . ?
N1 C33 1.429(7) . ?
N1 C41 1.486(8) . ?
N2 C32 1.454(9) . ?
N3 C26 1.459(10) . ?
C1 C2 1.394(9) . ?
C1 C10 1.395(8) . ?
C2 C3 1.417(10) . ?
C2 C27 1.472(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(9) . ?
C4 C5 1.496(10) . ?
C4 C9 1.378(9) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.515(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.513(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.509(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.538(9) . ?
C9 C10 1.408(10) . ?
C10 C11 1.499(9) . ?
C11 C12 1.418(8) . ?
C11 C20 1.374(8) . ?
C12 C13 1.520(8) . ?
C12 C17 1.397(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.509(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.507(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.526(9) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.533(8) . ?
C17 C18 1.384(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.396(8) . ?
C19 C20 1.376(8) . ?
C19 C21 1.504(9) . ?
C21 C22 1.431(11) . ?
C21 C26 1.383(9) . ?
C22 H22 0.9500 . ?
C22 C23 1.377(10) . ?
C23 H23 0.9500 . ?
C23 C24 1.384(11) . ?
C24 H24 0.9500 . ?
C24 C25 1.362(11) . ?
C25 H25 0.9500 . ?
C25 C26 1.406(10) . ?
C27 C28 1.417(10) . ?
C27 C32 1.411(10) . ?
C28 H28 0.9500 . ?
C28 C29 1.382(10) . ?
C29 H29 0.9500 . ?
C29 C30 1.372(12) . ?
C30 H30 0.9500 . ?
C30 C31 1.387(11) . ?
C31 H31 0.9500 . ?
C31 C32 1.375(9) . ?
C33 C34 1.395(9) . ?
C33 C38 1.381(9) . ?
C34 H34 0.9500 . ?
C34 C35 1.385(9) . ?
C35 C36 1.398(9) . ?
C35 C40 1.468(10) . ?
C36 H36 0.9500 . ?
C36 C37 1.389(10) . ?
C37 C38 1.402(8) . ?
C37 C39 1.468(10) . ?
C38 H38 0.9500 . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C41 C42 1.523(8) . ?
C42 C43 1.380(10) . ?
C42 C47 1.389(9) . ?
C43 H43 0.9500 . ?
C43 C44 1.394(9) . ?
C44 C45 1.403(9) . ?
C44 C49 1.465(10) . ?
C45 H45 0.9500 . ?
C45 C46 1.383(10) . ?
C46 C47 1.390(9) . ?
C46 C48 1.498(10) . ?
C47 H47 0.9500 . ?
