# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Taka-1
_database_code_depnum_ccdc_archive 'CCDC 1951120'
loop_
_audit_author_name
_audit_author_address
'Masaya Naito'
;University of Fukui
Japan
;
_audit_update_record             
;
2019-09-03 deposited with the CCDC.	2019-12-23 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C34 H44 Cl12 N4 O8'
_chemical_formula_moiety         'C34 H44 Cl12 N4 O8'
_chemical_formula_weight         1062.18
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   10.0502(3)
_cell_length_b                   10.8877(4)
_cell_length_c                   11.4091(4)
_cell_angle_alpha                84.205(6)
_cell_angle_beta                 74.087(5)
_cell_angle_gamma                78.083(6)
_cell_volume                     1173.39(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    20029
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.47
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544.00
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_T_max  0.913

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            23419
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_min         3.131
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5354
_reflns_number_gt                4494
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0836
_refine_ls_wR_factor_ref         0.2322
_refine_ls_wR_factor_gt          0.2227
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5354
_refine_ls_number_parameters     316
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1170P)²+3.2604P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         2.80
_refine_diff_density_min         -1.60
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
CL1 Cl 0.57217(14) 0.33307(12) 0.92024(13) 0.0590(4) Uani 1 1 d . . . . .
CL2 Cl 0.63603(16) 0.08382(15) 1.02637(16) 0.0767(5) Uani 1 1 d . . . . .
CL3 Cl 0.61995(18) 0.11795(16) 0.77512(13) 0.0756(5) Uani 1 1 d . . . . .
CL4 Cl 0.29981(17) 0.05792(12) 0.69535(14) 0.0651(4) Uani 1 1 d . . . . .
CL5 Cl 0.0055(2) 0.03680(19) 0.74656(19) 0.0956(6) Uani 1 1 d . . . . .
CL6 Cl 0.1889(2) -0.0232(2) 0.51163(16) 0.0993(7) Uani 1 1 d . . . . .
O1 O 0.2170(2) 0.5031(2) 0.7920(2) 0.0259(5) Uani 1 1 d . . . . .
O2 O 0.2387(3) 0.2389(2) 0.9582(2) 0.0311(5) Uani 1 1 d . . . . .
O3 O 0.2158(3) 0.5130(2) 0.5556(2) 0.0279(5) Uani 1 1 d . . . . .
O4 O 0.0911(3) 0.3430(2) 0.5175(2) 0.0311(5) Uani 1 1 d . . . . .
N1 N 0.0406(3) 0.3072(3) 0.8954(2) 0.0249(6) Uani 1 1 d . . . . .
N2 N 0.1526(3) 0.3661(3) 0.3114(2) 0.0262(6) Uani 1 1 d . . . . .
C1 C 0.3004(3) 0.5752(3) 0.7074(3) 0.0250(6) Uani 1 1 d . . . . .
C2 C 0.3010(3) 0.5821(3) 0.5836(3) 0.0250(6) Uani 1 1 d . . . . .
C3 C 0.3835(4) 0.6574(3) 0.5017(3) 0.0320(7) Uani 1 1 d . . . . .
C4 C 0.4624(4) 0.7260(3) 0.5435(4) 0.0352(8) Uani 1 1 d . . . . .
H2 H 0.519289 0.776729 0.487171 0.042 Uiso 1 1 calc R U . . .
C5 C 0.4593(4) 0.7215(3) 0.6649(4) 0.0353(8) Uani 1 1 d . . . . .
C6 C 0.3781(4) 0.6448(3) 0.7478(4) 0.0311(7) Uani 1 1 d . . . . .
C7 C 0.2618(4) 0.3701(3) 0.7756(3) 0.0268(7) Uani 1 1 d . . . . .
C8 C 0.1779(3) 0.3013(3) 0.8841(3) 0.0240(6) Uani 1 1 d . . . . .
C9 C -0.0397(4) 0.3848(3) 0.8157(3) 0.0248(6) Uani 1 1 d . . . . .
C10 C -0.1318(4) 0.5020(3) 0.8781(3) 0.0252(6) Uani 1 1 d . . . . .
C11 C -0.0377(4) 0.2386(4) 0.9983(3) 0.0325(7) Uani 1 1 d . . . . .
C12 C 0.2265(4) 0.5024(3) 0.4302(3) 0.0250(6) Uani 1 1 d . . . . .
C13 C 0.1508(3) 0.3972(3) 0.4235(3) 0.0232(6) Uani 1 1 d . . . . .
C14 C 0.2283(4) 0.4212(3) 0.1962(3) 0.0266(7) Uani 1 1 d . . . . .
C15 C 0.0813(5) 0.2648(4) 0.3017(4) 0.0382(8) Uani 1 1 d . . . . .
H18 H 0.091329 0.252828 0.215461 0.046 Uiso 1 1 calc R U . . .
H19 H 0.123578 0.186833 0.339103 0.046 Uiso 1 1 calc R U . . .
H20 H -0.018863 0.286721 0.343922 0.046 Uiso 1 1 calc R U . . .
C16 C 0.5536(4) 0.1752(4) 0.9218(4) 0.0377(8) Uani 1 1 d . . . . .
C17 C 0.1536(6) 0.0737(4) 0.6333(4) 0.0501(11) Uani 1 1 d . . . . .
H1 H 0.380(5) 0.663(4) 0.416(4) 0.038 Uiso 1 1 d . U . . .
H3 H 0.519(5) 0.772(4) 0.694(4) 0.039 Uiso 1 1 d . U . . .
H4 H 0.367(5) 0.640(5) 0.828(5) 0.041 Uiso 1 1 d . U . . .
H5 H 0.362(5) 0.344(4) 0.775(4) 0.039 Uiso 1 1 d . U . . .
H6 H 0.254(5) 0.350(4) 0.697(4) 0.036 Uiso 1 1 d . U . . .
H7 H 0.013(5) 0.407(4) 0.748(4) 0.032 Uiso 1 1 d . U . . .
H8 H -0.097(4) 0.335(4) 0.790(4) 0.031 Uiso 1 1 d . U . . .
H9 H -0.072(5) 0.556(4) 0.895(4) 0.032 Uiso 1 1 d . U . . .
H10 H -0.186(5) 0.486(4) 0.954(5) 0.039 Uiso 1 1 d . U . . .
H11 H 0.023(6) 0.164(5) 1.009(5) 0.047 Uiso 1 1 d . U . . .
H12 H -0.111(6) 0.218(5) 0.969(5) 0.058 Uiso 1 1 d . U . . .
H13 H -0.062(7) 0.284(7) 1.060(7) 0.077 Uiso 1 1 d . U . . .
H14 H 0.186(4) 0.581(4) 0.396(4) 0.026 Uiso 1 1 d . U . . .
H15 H 0.329(5) 0.484(4) 0.381(4) 0.033 Uiso 1 1 d . U . . .
H16 H 0.278(4) 0.472(4) 0.212(4) 0.022 Uiso 1 1 d . U . . .
H17 H 0.294(5) 0.351(4) 0.146(4) 0.039 Uiso 1 1 d . U . . .
H21 H 0.455(5) 0.176(4) 0.945(4) 0.039 Uiso 1 1 d . U . . .
H22 H 0.136(6) 0.154(6) 0.610(6) 0.068 Uiso 1 1 d . U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
CL1 C16 1.764(5) . ?
CL2 C16 1.750(4) . ?
CL3 C16 1.750(5) . ?
CL4 C17 1.769(5) . ?
CL5 C17 1.771(6) . ?
CL6 C17 1.743(5) . ?
O1 C1 1.388(4) . ?
O1 C7 1.440(4) . ?
O2 C8 1.243(4) . ?
O3 C2 1.366(4) . ?
O3 C12 1.419(4) . ?
O4 C13 1.234(4) . ?
N1 C8 1.339(4) . ?
N1 C11 1.454(4) . ?
N1 C9 1.468(4) . ?
N2 C13 1.350(4) . ?
N2 C15 1.462(5) . ?
N2 C14 1.465(4) . ?
C1 C6 1.381(5) . ?
C1 C2 1.405(4) . ?
C2 C3 1.391(5) . ?
C3 C4 1.392(5) . ?
C3 H1 0.98(5) . ?
C4 C5 1.373(6) . ?
C4 H2 0.9500 . ?
C5 C6 1.399(5) . ?
C5 H3 1.03(5) . ?
C6 H4 0.89(5) . ?
C7 C8 1.519(4) . ?
C7 H5 0.98(5) . ?
C7 H6 0.97(5) . ?
C9 C10 1.525(5) . ?
C9 H7 0.86(5) . ?
C9 H8 0.98(4) . ?
C10 C14 1.527(4) 2_566 ?
C10 H9 0.99(5) . ?
C10 H10 0.91(5) . ?
C11 H11 0.93(5) . ?
C11 H12 0.96(6) . ?
C11 H13 0.85(7) . ?
C12 C13 1.518(5) . ?
C12 H14 0.96(4) . ?
C12 H15 1.02(5) . ?
C14 C10 1.527(4) 2_566 ?
C14 H16 0.88(4) . ?
C14 H17 1.01(5) . ?
C15 H18 0.9800 . ?
C15 H19 0.9800 . ?
C15 H20 0.9800 . ?
C16 H21 0.95(5) . ?
C17 H22 0.89(7) . ?

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
C1 O1 C7 113.4(2) . . ?
C2 O3 C12 117.5(3) . . ?
C8 N1 C11 118.1(3) . . ?
C8 N1 C9 124.7(3) . . ?
C11 N1 C9 117.1(3) . . ?
C13 N2 C15 118.6(3) . . ?
C13 N2 C14 125.0(3) . . ?
C15 N2 C14 116.3(3) . . ?
C6 C1 O1 118.9(3) . . ?
C6 C1 C2 120.4(3) . . ?
O1 C1 C2 120.7(3) . . ?
O3 C2 C3 125.7(3) . . ?
O3 C2 C1 115.0(3) . . ?
C3 C2 C1 119.2(3) . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H1 118(3) . . ?
C4 C3 H1 122(3) . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H2 119.5 . . ?
C3 C4 H2 119.5 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H3 120(3) . . ?
C6 C5 H3 120(3) . . ?
C1 C6 C5 120.0(3) . . ?
C1 C6 H4 115(3) . . ?
C5 C6 H4 125(3) . . ?
O1 C7 C8 108.3(3) . . ?
O1 C7 H5 110(3) . . ?
C8 C7 H5 107(3) . . ?
O1 C7 H6 110(3) . . ?
C8 C7 H6 115(3) . . ?
H5 C7 H6 107(4) . . ?
O2 C8 N1 121.9(3) . . ?
O2 C8 C7 119.4(3) . . ?
N1 C8 C7 118.7(3) . . ?
N1 C9 C10 111.5(3) . . ?
N1 C9 H7 113(3) . . ?
C10 C9 H7 109(3) . . ?
N1 C9 H8 110(3) . . ?
C10 C9 H8 111(2) . . ?
H7 C9 H8 103(4) . . ?
C9 C10 C14 113.3(3) . 2_566 ?
C9 C10 H9 110(3) . . ?
C14 C10 H9 109(3) 2_566 . ?
C9 C10 H10 114(3) . . ?
C14 C10 H10 108(3) 2_566 . ?
H9 C10 H10 102(4) . . ?
N1 C11 H11 106(3) . . ?
N1 C11 H12 104(3) . . ?
H11 C11 H12 108(5) . . ?
N1 C11 H13 108(5) . . ?
H11 C11 H13 112(6) . . ?
H12 C11 H13 118(6) . . ?
O3 C12 C13 106.6(3) . . ?
O3 C12 H14 110(2) . . ?
C13 C12 H14 112(2) . . ?
O3 C12 H15 111(3) . . ?
C13 C12 H15 111(2) . . ?
H14 C12 H15 105(3) . . ?
O4 C13 N2 122.2(3) . . ?
O4 C13 C12 120.6(3) . . ?
N2 C13 C12 117.2(3) . . ?
N2 C14 C10 113.7(3) . 2_566 ?
N2 C14 H16 109(3) . . ?
C10 C14 H16 107(3) 2_566 . ?
N2 C14 H17 108(3) . . ?
C10 C14 H17 109(3) 2_566 . ?
H16 C14 H17 109(4) . . ?
N2 C15 H18 109.5 . . ?
N2 C15 H19 109.5 . . ?
H18 C15 H19 109.5 . . ?
N2 C15 H20 109.5 . . ?
H18 C15 H20 109.5 . . ?
H19 C15 H20 109.5 . . ?
CL3 C16 CL2 111.8(2) . . ?
CL3 C16 CL1 110.5(2) . . ?
CL2 C16 CL1 110.0(2) . . ?
CL3 C16 H21 108(3) . . ?
CL2 C16 H21 111(3) . . ?
CL1 C16 H21 106(3) . . ?
CL6 C17 CL4 112.0(3) . . ?
CL6 C17 CL5 108.8(3) . . ?
CL4 C17 CL5 110.4(3) . . ?
CL6 C17 H22 112(4) . . ?
CL4 C17 H22 105(4) . . ?
CL5 C17 H22 109(4) . . ?

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
C7 O1 C1 C6 -115.2(3) . . . . ?
C7 O1 C1 C2 67.8(4) . . . . ?
C12 O3 C2 C3 9.4(5) . . . . ?
C12 O3 C2 C1 -171.6(3) . . . . ?
C6 C1 C2 O3 -177.5(3) . . . . ?
O1 C1 C2 O3 -0.5(4) . . . . ?
C6 C1 C2 C3 1.6(5) . . . . ?
O1 C1 C2 C3 178.6(3) . . . . ?
O3 C2 C3 C4 178.0(3) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C3 C4 C5 C6 1.3(6) . . . . ?
O1 C1 C6 C5 -177.9(3) . . . . ?
C2 C1 C6 C5 -0.8(5) . . . . ?
C4 C5 C6 C1 -0.6(5) . . . . ?
C1 O1 C7 C8 171.2(3) . . . . ?
C11 N1 C8 O2 0.5(5) . . . . ?
C9 N1 C8 O2 176.2(3) . . . . ?
C11 N1 C8 C7 178.7(3) . . . . ?
C9 N1 C8 C7 -5.6(5) . . . . ?
O1 C7 C8 O2 -111.5(3) . . . . ?
O1 C7 C8 N1 70.3(4) . . . . ?
C8 N1 C9 C10 -103.6(4) . . . . ?
C11 N1 C9 C10 72.2(4) . . . . ?
N1 C9 C10 C14 -174.2(3) . . . 2_566 ?
C2 O3 C12 C13 166.1(3) . . . . ?
C15 N2 C13 O4 0.0(5) . . . . ?
C14 N2 C13 O4 -176.2(3) . . . . ?
C15 N2 C13 C12 179.7(3) . . . . ?
C14 N2 C13 C12 3.6(4) . . . . ?
O3 C12 C13 O4 2.6(4) . . . . ?
O3 C12 C13 N2 -177.1(3) . . . . ?
C13 N2 C14 C10 -114.3(4) . . . 2_566 ?
C15 N2 C14 C10 69.4(4) . . . 2_566 ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_common            Taka-1
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Nakamura-2
_database_code_depnum_ccdc_archive 'CCDC 1951121'
loop_
_audit_author_name
_audit_author_address
'Masaya Naito'
;University of Fukui
Japan
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2019-12-23 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C78 H108 F12 N8 O10 P2'
_chemical_formula_moiety         'C78 H108 F12 N8 O10 P2'
_chemical_formula_weight         1607.69
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.6936
_cell_length_b                   11.5504
_cell_length_c                   22.9713
_cell_angle_alpha                79.0140
_cell_angle_beta                 79.4470
_cell_angle_gamma                65.7020
_cell_volume                     2049.6102
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7537
_cell_measurement_theta_min      1.03
_cell_measurement_theta_max      28.57
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.010
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             850.00
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.81078
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.333
_diffrn_reflns_number            21047
_diffrn_reflns_av_unetI/netI     0.1278
_diffrn_reflns_av_R_equivalents  0.1011
_diffrn_reflns_theta_max         29.237
_diffrn_reflns_theta_min         1.037
_diffrn_reflns_theta_full        29.109
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             7436
_reflns_number_gt                4631
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1962
_refine_ls_R_factor_gt           0.1434
_refine_ls_wR_factor_ref         0.4088
_refine_ls_wR_factor_gt          0.3772
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         7436
_refine_ls_number_parameters     535
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1532P)²+8.9415P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.4266(3) 0.0322(2) 0.29040(12) 0.0559(7) Uani 1 1 d . . . . .
F1 F 1.5971(6) 0.0343(5) 0.3062(2) 0.0686(15) Uani 1 1 d . . . . .
F2 F 1.2549(7) 0.0299(5) 0.2746(3) 0.0861(19) Uani 1 1 d . . . . .
F3 F 1.4368(7) 0.1218(5) 0.2295(2) 0.0734(16) Uani 1 1 d . . . . .
F4 F 1.4143(6) -0.0563(5) 0.3527(2) 0.0683(15) Uani 1 1 d . . . . .
F5 F 1.5353(7) -0.0945(5) 0.2594(2) 0.0725(15) Uani 1 1 d . . . . .
F6 F 1.3140(8) 0.1582(5) 0.3227(3) 0.0818(18) Uani 1 1 d . . . . .
O1 O 0.8117(6) 0.2350(5) 0.5802(2) 0.0471(13) Uani 1 1 d . . . . .
O2 O 0.8489(6) 0.2293(5) 0.4637(2) 0.0473(13) Uani 1 1 d . . . . .
O3 O 0.5708(7) 0.3148(5) 0.4079(3) 0.0503(14) Uani 1 1 d . . . . .
O4 O 0.4868(7) 0.6149(5) 0.3716(2) 0.0479(13) Uani 1 1 d . . . . .
O5 O -0.1781(9) 0.5295(8) 0.8358(4) 0.088(2) Uani 1 1 d . . . . .
N1 N 0.7212(8) 0.2976(6) 0.3155(3) 0.0508(17) Uani 1 1 d . . . . .
N2 N 0.4084(8) 0.6572(6) 0.2784(3) 0.0495(17) Uani 1 1 d . . . . .
N3 N -0.0739(12) 0.4644(9) 0.7918(4) 0.080(3) Uani 1 1 d . . . . .
N4 N 0.4576(8) 0.3507(6) 0.5211(3) 0.0453(16) Uani 1 1 d . . . . .
H4A H 0.507262 0.323406 0.555526 0.054 Uiso 1 1 calc R U . . .
H4B H 0.533548 0.307731 0.491916 0.054 Uiso 1 1 calc R U . . .
C1 C 0.9701(9) 0.1608(7) 0.5546(4) 0.048(2) Uani 1 1 d . . . . .
C2 C 0.9905(10) 0.1609(7) 0.4929(4) 0.047(2) Uani 1 1 d . . . . .
C3 C 1.1494(10) 0.0918(7) 0.4644(4) 0.048(2) Uani 1 1 d . . . . .
H3 H 1.165940 0.092807 0.422270 0.057 Uiso 1 1 calc R U . . .
C4 C 1.2841(10) 0.0211(8) 0.4980(4) 0.049(2) Uani 1 1 d . . . . .
H4 H 1.392066 -0.026405 0.478233 0.058 Uiso 1 1 calc R U . . .
C5 C 1.2659(10) 0.0180(7) 0.5574(4) 0.052(2) Uani 1 1 d . . . . .
H5 H 1.359143 -0.032064 0.579500 0.062 Uiso 1 1 calc R U . . .
C6 C 1.1071(10) 0.0898(7) 0.5866(4) 0.048(2) Uani 1 1 d . . . . .
H6 H 1.093623 0.089607 0.628635 0.058 Uiso 1 1 calc R U . . .
C7 C 0.7973(10) 0.2358(7) 0.6424(4) 0.0446(18) Uani 1 1 d . . . . .
H7A H 0.884013 0.262394 0.651561 0.053 Uiso 1 1 calc R U . . .
H7B H 0.816851 0.148727 0.663471 0.053 Uiso 1 1 calc R U . . .
C8 C 0.8780(10) 0.2225(7) 0.4007(4) 0.047(2) Uani 1 1 d . . . . .
H8A H 0.937665 0.131976 0.393269 0.057 Uiso 1 1 calc R U . . .
H8B H 0.950608 0.269315 0.380880 0.057 Uiso 1 1 calc R U . . .
C9 C 0.7084(10) 0.2814(7) 0.3749(4) 0.047(2) Uani 1 1 d . . . . .
C10 C 0.8811(11) 0.2452(11) 0.2775(4) 0.071(3) Uani 1 1 d . . . . .
H10A H 0.861373 0.215826 0.243307 0.085 Uiso 1 1 calc R U . . .
H10B H 0.962767 0.172966 0.300433 0.085 Uiso 1 1 calc R U . . .
H10C H 0.926604 0.311721 0.263174 0.085 Uiso 1 1 calc R U . . .
C11 C 0.5634(11) 0.3567(8) 0.2845(4) 0.055(2) Uani 1 1 d . . . . .
H11A H 0.464130 0.396430 0.313525 0.066 Uiso 1 1 calc R U . . .
H11B H 0.545733 0.288879 0.269427 0.066 Uiso 1 1 calc R U . . .
C12 C 0.5750(11) 0.4567(8) 0.2332(4) 0.057(2) Uani 1 1 d . . . . .
H12A H 0.476754 0.483298 0.210583 0.068 Uiso 1 1 calc R U . . .
H12B H 0.679505 0.418012 0.206019 0.068 Uiso 1 1 calc R U . . .
C13 C 0.5778(10) 0.5755(9) 0.2523(4) 0.055(2) Uani 1 1 d . . . . .
H13A H 0.659390 0.548709 0.281963 0.066 Uiso 1 1 calc R U . . .
H13B H 0.616778 0.625254 0.217165 0.066 Uiso 1 1 calc R U . . .
C14 C 0.2873(11) 0.7364(9) 0.2363(4) 0.056(2) Uani 1 1 d . . . . .
H14A H 0.327496 0.704916 0.197360 0.068 Uiso 1 1 calc R U . . .
H14B H 0.276626 0.825296 0.232271 0.068 Uiso 1 1 calc R U . . .
H14C H 0.176292 0.732179 0.251036 0.068 Uiso 1 1 calc R U . . .
C15 C 0.3828(10) 0.6695(8) 0.3364(4) 0.048(2) Uani 1 1 d . . . . .
C16 C -0.1740(14) 0.3357(11) 0.9027(4) 0.070(3) Uani 1 1 d . . . . .
C17 C -0.0590(13) 0.2108(12) 0.8888(4) 0.071(3) Uani 1 1 d . . . . .
H17 H 0.055185 0.197586 0.873148 0.085 Uiso 1 1 calc R U . . .
C18 C -0.1103(12) 0.1065(11) 0.8977(4) 0.068(3) Uani 1 1 d . . . . .
C19 C -0.2775(12) 0.1312(10) 0.9225(4) 0.063(2) Uani 1 1 d . . . . .
H19 H -0.314832 0.062519 0.930973 0.075 Uiso 1 1 calc R U . . .
C20 C -0.3928(12) 0.2523(10) 0.9353(4) 0.063(2) Uani 1 1 d . . . . .
C21 C -0.3358(13) 0.3507(11) 0.9257(5) 0.069(3) Uani 1 1 d . . . . .
H21 H -0.413330 0.432630 0.935663 0.083 Uiso 1 1 calc R U . . .
C22 C 0.0105(15) -0.0246(12) 0.8839(5) 0.078(3) Uani 1 1 d . . . . .
C23A C 0.109(3) -0.0049(18) 0.8169(11) 0.070(7) Uani 0.58(3) 1 d . . P A 1
H23A H 0.145863 0.065644 0.813976 0.105 Uiso 0.58(3) 1 calc R U P A 1
H23B H 0.031155 0.015134 0.787017 0.105 Uiso 0.58(3) 1 calc R U P A 1
H23C H 0.208005 -0.083847 0.809658 0.105 Uiso 0.58(3) 1 calc R U P A 1
C24A C 0.161(4) -0.066(3) 0.9239(13) 0.117(14) Uani 0.58(3) 1 d . . P A 1
H24A H 0.228635 -0.014791 0.908645 0.176 Uiso 0.58(3) 1 calc R U P A 1
H24B H 0.232757 -0.157112 0.922269 0.176 Uiso 0.58(3) 1 calc R U P A 1
H24C H 0.112821 -0.052585 0.965254 0.176 Uiso 0.58(3) 1 calc R U P A 1
C25A C -0.052(4) -0.111(2) 0.8852(15) 0.075(8) Uani 0.58(3) 1 d . . P A 1
H25A H 0.033777 -0.196888 0.895904 0.112 Uiso 0.58(3) 1 calc R U P A 1
H25B H -0.084103 -0.106369 0.845774 0.112 Uiso 0.58(3) 1 calc R U P A 1
H25C H -0.152649 -0.095615 0.914920 0.112 Uiso 0.58(3) 1 calc R U P A 1
C26 C -0.5798(13) 0.2769(11) 0.9640(5) 0.074(3) Uani 1 1 d . . . . .
C27 C -0.6996(14) 0.4150(11) 0.9517(5) 0.081(3) Uani 1 1 d . . . . .
H27A H -0.657337 0.470059 0.965876 0.097 Uiso 1 1 calc R U . . .
H27B H -0.812672 0.426157 0.972702 0.097 Uiso 1 1 calc R U . . .
H27C H -0.706646 0.438309 0.908721 0.097 Uiso 1 1 calc R U . . .
C28 C -0.6452(15) 0.1939(12) 0.9391(7) 0.108(5) Uani 1 1 d . . . . .
H28A H -0.571203 0.103452 0.947846 0.129 Uiso 1 1 calc R U . . .
H28B H -0.645066 0.217400 0.895776 0.129 Uiso 1 1 calc R U . . .
H28C H -0.761177 0.207842 0.957710 0.129 Uiso 1 1 calc R U . . .
C29 C -0.5804(16) 0.2409(12) 1.0316(5) 0.089(3) Uani 1 1 d . . . . .
H29A H -0.503972 0.151101 1.040515 0.106 Uiso 1 1 calc R U . . .
H29B H -0.695883 0.252652 1.050074 0.106 Uiso 1 1 calc R U . . .
H29C H -0.541643 0.295813 1.047591 0.106 Uiso 1 1 calc R U . . .
C30 C -0.1189(17) 0.4450(12) 0.8919(5) 0.084(3) Uani 1 1 d . . . . .
H30A H 0.006592 0.411775 0.888745 0.100 Uiso 1 1 calc R U . . .
H30B H -0.166075 0.495270 0.926003 0.100 Uiso 1 1 calc R U . . .
C31 C -0.1277(13) 0.5338(10) 0.7383(5) 0.063(2) Uani 1 1 d . . . . .
H31 H -0.222657 0.613425 0.735688 0.076 Uiso 1 1 calc R U . . .
C32 C -0.0251(10) 0.4736(8) 0.6859(4) 0.050(2) Uani 1 1 d . . . . .
C33 C 0.1120(10) 0.3513(8) 0.6909(4) 0.049(2) Uani 1 1 d . . . . .
H33 H 0.134545 0.302591 0.728933 0.059 Uiso 1 1 calc R U . . .
C34 C 0.2105(10) 0.3048(8) 0.6402(4) 0.050(2) Uani 1 1 d . . . . .
H34 H 0.301562 0.223180 0.643674 0.059 Uiso 1 1 calc R U . . .
C35 C 0.1819(9) 0.3730(7) 0.5840(4) 0.047(2) Uani 1 1 d . . . . .
C36 C 0.0458(9) 0.4917(7) 0.5799(4) 0.0465(19) Uani 1 1 d . . . . .
H36 H 0.023588 0.540426 0.541826 0.056 Uiso 1 1 calc R U . . .
C37 C -0.0566(11) 0.5392(8) 0.6302(4) 0.054(2) Uani 1 1 d . . . . .
H37 H -0.150825 0.618964 0.626248 0.065 Uiso 1 1 calc R U . . .
C38 C 0.3031(10) 0.3197(7) 0.5296(4) 0.050(2) Uani 1 1 d . . . . .
H38A H 0.338430 0.225536 0.534600 0.060 Uiso 1 1 calc R U . . .
H38B H 0.243167 0.356033 0.493549 0.060 Uiso 1 1 calc R U . . .
C39 C 0.4163(9) 0.4905(7) 0.5047(4) 0.0418(18) Uani 1 1 d . . . . .
H39A H 0.338128 0.538358 0.536977 0.050 Uiso 1 1 calc R U . . .
H39B H 0.360624 0.522051 0.467610 0.050 Uiso 1 1 calc R U . . .
C24B C 0.032(6) -0.131(4) 0.9503(13) 0.121(19) Uani 0.42(3) 1 d . . P A 2
H24D H -0.077459 -0.137127 0.965855 0.182 Uiso 0.42(3) 1 calc R U P A 2
H24E H 0.068384 -0.099259 0.979835 0.182 Uiso 0.42(3) 1 calc R U P A 2
H24F H 0.117032 -0.215580 0.942440 0.182 Uiso 0.42(3) 1 calc R U P A 2
C25B C -0.095(6) -0.092(5) 0.8583(15) 0.078(11) Uani 0.42(3) 1 d . . P A 2
H25D H -0.202981 -0.078908 0.883692 0.117 Uiso 0.42(3) 1 calc R U P A 2
H25E H -0.026928 -0.183997 0.858670 0.117 Uiso 0.42(3) 1 calc R U P A 2
H25F H -0.117552 -0.052852 0.817320 0.117 Uiso 0.42(3) 1 calc R U P A 2
C23B C 0.166(5) -0.066(6) 0.8515(17) 0.136(19) Uani 0.42(3) 1 d . . P A 2
H23D H 0.228152 -0.157166 0.864558 0.204 Uiso 0.42(3) 1 calc R U P A 2
H23E H 0.229197 -0.016902 0.857274 0.204 Uiso 0.42(3) 1 calc R U P A 2
H23F H 0.151776 -0.054311 0.809062 0.204 Uiso 0.42(3) 1 calc R U P A 2


#==============================================================================
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 F3 1.585(6) . ?
P1 F5 1.598(6) . ?
P1 F1 1.600(5) . ?
P1 F4 1.606(6) . ?
P1 F2 1.610(6) . ?
P1 F6 1.612(6) . ?
O1 C1 1.379(9) . ?
O1 C7 1.411(9) . ?
O2 C2 1.374(9) . ?
O2 C8 1.435(10) . ?
O3 C9 1.246(10) . ?
O4 C15 1.214(9) . ?
O5 N3 1.342(10) . ?
O5 C30 1.492(13) . ?
N1 C9 1.332(11) . ?
N1 C10 1.458(11) . ?
N1 C11 1.502(10) . ?
N2 C15 1.334(11) . ?
N2 C14 1.458(10) . ?
N2 C13 1.472(10) . ?
N3 C31 1.377(13) . ?
N4 C39 1.489(9) . ?
N4 C38 1.498(10) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
C1 C6 1.386(11) . ?
C1 C2 1.396(12) . ?
C2 C3 1.391(11) . ?
C3 C4 1.392(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.341(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(11) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C15 1.549(11) 2_666 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.526(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.505(13) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.528(12) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C7 1.549(11) 2_666 ?
C16 C21 1.360(14) . ?
C16 C17 1.433(15) . ?
C16 C30 1.489(15) . ?
C17 C18 1.417(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(13) . ?
C18 C22 1.500(15) . ?
C19 C20 1.394(13) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(14) . ?
C20 C26 1.567(14) . ?
C21 H21 0.9500 . ?
C22 C25A 1.32(3) . ?
C22 C23B 1.36(4) . ?
C22 C24A 1.59(2) . ?
C22 C23A 1.64(2) . ?
C22 C25B 1.66(4) . ?
C22 C24B 1.75(4) . ?
C23Aa H23A 0.9800 . ?
C23Aa H23B 0.9800 . ?
C23Aa H23C 0.9800 . ?
C24Aa H24A 0.9800 . ?
C24Aa H24B 0.9800 . ?
C24Aa H24C 0.9800 . ?
C25Aa H25A 0.9800 . ?
C25Aa H25B 0.9800 . ?
C25Aa H25C 0.9800 . ?
C26 C27 1.509(15) . ?
C26 C29 1.529(15) . ?
C26 C28 1.532(16) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.465(13) . ?
C31 H31 0.9500 . ?
C32 C37 1.368(12) . ?
C32 C33 1.426(11) . ?
C33 C34 1.368(12) . ?
C33 H33 0.9500 . ?
C34 C35 1.385(12) . ?
C34 H34 0.9500 . ?
C35 C36 1.395(11) . ?
C35 C38 1.525(12) . ?
C36 C37 1.376(12) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C39 1.531(15) 2_666 ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C24Bb H24D 0.9800 . ?
C24Bb H24E 0.9800 . ?
C24Bb H24F 0.9800 . ?
C25Bb H25D 0.9800 . ?
C25Bb H25E 0.9800 . ?
C25Bb H25F 0.9800 . ?
C23Bb H23D 0.9800 . ?
C23Bb H23E 0.9800 . ?
C23Bb H23F 0.9800 . ?

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
F3 P1 F5 92.0(3) . . ?
F3 P1 F1 90.6(3) . . ?
F5 P1 F1 90.3(3) . . ?
F3 P1 F4 178.9(3) . . ?
F5 P1 F4 89.0(3) . . ?
F1 P1 F4 89.4(3) . . ?
F3 P1 F2 89.5(3) . . ?
F5 P1 F2 89.7(3) . . ?
F1 P1 F2 179.9(4) . . ?
F4 P1 F2 90.5(3) . . ?
F3 P1 F6 89.1(3) . . ?
F5 P1 F6 178.5(4) . . ?
F1 P1 F6 90.6(3) . . ?
F4 P1 F6 89.8(3) . . ?
F2 P1 F6 89.4(3) . . ?
C1 O1 C7 115.3(6) . . ?
C2 O2 C8 114.1(6) . . ?
N3 O5 C30 104.6(9) . . ?
C9 N1 C10 123.6(7) . . ?
C9 N1 C11 119.9(7) . . ?
C10 N1 C11 116.0(7) . . ?
C15 N2 C14 123.7(7) . . ?
C15 N2 C13 119.3(7) . . ?
C14 N2 C13 116.1(7) . . ?
O5 N3 C31 107.7(9) . . ?
C39 N4 C38 112.2(6) . . ?
C39 N4 H4A 109.2 . . ?
C38 N4 H4A 109.2 . . ?
C39 N4 H4B 109.2 . . ?
C38 N4 H4B 109.2 . . ?
H4A N4 H4B 107.9 . . ?
O1 C1 C6 123.5(8) . . ?
O1 C1 C2 116.9(7) . . ?
C6 C1 C2 119.6(7) . . ?
O2 C2 C3 123.6(8) . . ?
O2 C2 C1 117.1(7) . . ?
C3 C2 C1 119.3(7) . . ?
C2 C3 C4 119.5(8) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 121.9(8) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 119.2(8) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 120.4(8) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C7 C15 109.2(6) . 2_666 ?
O1 C7 H7A 109.8 . . ?
C15 C7 H7A 109.8 2_666 . ?
O1 C7 H7B 109.8 . . ?
C15 C7 H7B 109.8 2_666 . ?
H7A C7 H7B 108.3 . . ?
O2 C8 C9 109.6(6) . . ?
O2 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
O2 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
O3 C9 N1 124.0(7) . . ?
O3 C9 C8 121.4(8) . . ?
N1 C9 C8 114.6(7) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 111.8(7) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 113.9(8) . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
N2 C13 C12 111.4(7) . . ?
N2 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 N2 125.7(7) . . ?
O4 C15 C7 120.0(8) . 2_666 ?
N2 C15 C7 114.3(7) . 2_666 ?
C21 C16 C17 117.4(10) . . ?
C21 C16 C30 121.3(11) . . ?
C17 C16 C30 121.3(10) . . ?
C18 C17 C16 122.0(9) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C19 C18 C17 116.2(10) . . ?
C19 C18 C22 121.7(11) . . ?
C17 C18 C22 122.0(10) . . ?
C18 C19 C20 122.9(10) . . ?
C18 C19 H19 118.5 . . ?
C20 C19 H19 118.5 . . ?
C21 C20 C19 118.4(9) . . ?
C21 C20 C26 119.7(9) . . ?
C19 C20 C26 121.8(9) . . ?
C16 C21 C20 123.1(10) . . ?
C16 C21 H21 118.5 . . ?
C20 C21 H21 118.5 . . ?
C25Aa C22 C18 118.2(15) . . ?
C23Bb C22 C18 132(3) . . ?
C25Aa C22 C24A 115.3(19) . . ?
C18 C22 C24A 105.9(11) . . ?
C25Aa C22 C23A 108.5(16) . . ?
C18 C22 C23A 106.3(11) . . ?
C24Aa C22 C23A 101.0(17) . . ?
C23Bb C22 C25B 104(2) . . ?
C18 C22 C25B 108.6(19) . . ?
C23Bb C22 C24B 105(2) . . ?
C18 C22 C24B 108.7(13) . . ?
C25Bb C22 C24B 92(2) . . ?
C22 C23Aa H23A 109.5 . . ?
C22 C23Aa H23B 109.5 . . ?
H23Aa C23Aa H23B 109.5 . . ?
C22 C23Aa H23C 109.5 . . ?
H23Aa C23Aa H23C 109.5 . . ?
H23Ba C23Aa H23C 109.5 . . ?
C22 C24Aa H24A 109.5 . . ?
C22 C24Aa H24B 109.5 . . ?
H24Aa C24Aa H24B 109.5 . . ?
C22 C24Aa H24C 109.5 . . ?
H24Aa C24Aa H24C 109.5 . . ?
H24Ba C24Aa H24C 109.5 . . ?
C22 C25Aa H25A 109.5 . . ?
C22 C25Aa H25B 109.5 . . ?
H25Aa C25Aa H25B 109.5 . . ?
C22 C25Aa H25C 109.5 . . ?
H25Aa C25Aa H25C 109.5 . . ?
H25Ba C25Aa H25C 109.5 . . ?
C27 C26 C29 108.2(9) . . ?
C27 C26 C28 108.2(9) . . ?
C29 C26 C28 109.6(11) . . ?
C27 C26 C20 112.8(9) . . ?
C29 C26 C20 108.5(9) . . ?
C28 C26 C20 109.5(9) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C16 C30 O5 110.7(8) . . ?
C16 C30 H30A 109.5 . . ?
O5 C30 H30A 109.5 . . ?
C16 C30 H30B 109.5 . . ?
O5 C30 H30B 109.5 . . ?
H30A C30 H30B 108.1 . . ?
N3 C31 C32 113.8(9) . . ?
N3 C31 H31 123.1 . . ?
C32 C31 H31 123.1 . . ?
C37 C32 C33 118.7(8) . . ?
C37 C32 C31 119.0(8) . . ?
C33 C32 C31 122.2(9) . . ?
C34 C33 C32 119.1(8) . . ?
C34 C33 H33 120.4 . . ?
C32 C33 H33 120.4 . . ?
C33 C34 C35 122.2(8) . . ?
C33 C34 H34 118.9 . . ?
C35 C34 H34 118.9 . . ?
C34 C35 C36 117.9(8) . . ?
C34 C35 C38 119.6(7) . . ?
C36 C35 C38 122.4(8) . . ?
C37 C36 C35 120.8(8) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C32 C37 C36 121.2(8) . . ?
C32 C37 H37 119.4 . . ?
C36 C37 H37 119.4 . . ?
N4 C38 C35 111.7(6) . . ?
N4 C38 H38A 109.3 . . ?
C35 C38 H38A 109.3 . . ?
N4 C38 H38B 109.3 . . ?
C35 C38 H38B 109.3 . . ?
H38A C38 H38B 107.9 . . ?
N4 C39 C39 107.4(7) . 2_666 ?
N4 C39 H39A 110.2 . . ?
C39 C39 H39A 110.2 2_666 . ?
N4 C39 H39B 110.2 . . ?
C39 C39 H39B 110.2 2_666 . ?
H39A C39 H39B 108.5 . . ?
C22 C24Bb H24D 109.5 . . ?
C22 C24Bb H24E 109.5 . . ?
H24Db C24Bb H24E 109.5 . . ?
C22 C24Bb H24F 109.5 . . ?
H24Db C24Bb H24F 109.5 . . ?
H24Eb C24Bb H24F 109.5 . . ?
C22 C25Bb H25D 109.5 . . ?
C22 C25Bb H25E 109.5 . . ?
H25Db C25Bb H25E 109.5 . . ?
C22 C25Bb H25F 109.5 . . ?
H25Db C25Bb H25F 109.5 . . ?
H25Eb C25Bb H25F 109.5 . . ?
C22 C23Bb H23D 109.5 . . ?
C22 C23Bb H23E 109.5 . . ?
H23Db C23Bb H23E 109.5 . . ?
C22 C23Bb H23F 109.5 . . ?
H23Db C23Bb H23F 109.5 . . ?
H23Eb C23Bb H23F 109.5 . . ?

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
C30 O5 N3 C31 176.5(7) . . . . ?
C7 O1 C1 C6 0.8(11) . . . . ?
C7 O1 C1 C2 -178.0(7) . . . . ?
C8 O2 C2 C3 0.7(10) . . . . ?
C8 O2 C2 C1 -178.4(7) . . . . ?
O1 C1 C2 O2 -3.3(10) . . . . ?
C6 C1 C2 O2 177.8(7) . . . . ?
O1 C1 C2 C3 177.4(7) . . . . ?
C6 C1 C2 C3 -1.4(12) . . . . ?
O2 C2 C3 C4 -177.5(7) . . . . ?
C1 C2 C3 C4 1.7(11) . . . . ?
C2 C3 C4 C5 -0.5(12) . . . . ?
C3 C4 C5 C6 -1.0(12) . . . . ?
O1 C1 C6 C5 -178.9(7) . . . . ?
C2 C1 C6 C5 -0.1(12) . . . . ?
C4 C5 C6 C1 1.3(12) . . . . ?
C1 O1 C7 C15 175.9(6) . . . 2_666 ?
C2 O2 C8 C9 170.1(6) . . . . ?
C10 N1 C9 O3 -172.6(8) . . . . ?
C11 N1 C9 O3 -1.4(11) . . . . ?
C10 N1 C9 C8 9.8(11) . . . . ?
C11 N1 C9 C8 -179.0(7) . . . . ?
O2 C8 C9 O3 -7.3(10) . . . . ?
O2 C8 C9 N1 170.4(6) . . . . ?
C9 N1 C11 C12 134.6(8) . . . . ?
C10 N1 C11 C12 -53.5(10) . . . . ?
N1 C11 C12 C13 -67.0(9) . . . . ?
C15 N2 C13 C12 112.5(8) . . . . ?
C14 N2 C13 C12 -77.5(9) . . . . ?
C11 C12 C13 N2 -74.5(9) . . . . ?
C14 N2 C15 O4 -172.0(8) . . . . ?
C13 N2 C15 O4 -2.8(12) . . . . ?
C14 N2 C15 C7 7.4(11) . . . 2_666 ?
C13 N2 C15 C7 176.5(7) . . . 2_666 ?
C21 C16 C17 C18 0.9(13) . . . . ?
C30 C16 C17 C18 -178.8(8) . . . . ?
C16 C17 C18 C19 -2.0(13) . . . . ?
C16 C17 C18 C22 -179.2(8) . . . . ?
C17 C18 C19 C20 3.2(13) . . . . ?
C22 C18 C19 C20 -179.6(8) . . . . ?
C18 C19 C20 C21 -3.2(14) . . . . ?
C18 C19 C20 C26 -179.2(8) . . . . ?
C17 C16 C21 C20 -0.9(14) . . . . ?
C30 C16 C21 C20 178.8(9) . . . . ?
C19 C20 C21 C16 2.0(14) . . . . ?
C26 C20 C21 C16 178.1(9) . . . . ?
C19 C18 C22 C25Aa 13(2) . . . . ?
C17 C18 C22 C25Aa -170.4(19) . . . . ?
C19 C18 C22 C23Bb 167(2) . . . . ?
C17 C18 C22 C23Bb -16(3) . . . . ?
C19 C18 C22 C24Aa -118.5(19) . . . . ?
C17 C18 C22 C24Aa 59(2) . . . . ?
C19 C18 C22 C23Aa 134.7(13) . . . . ?
C17 C18 C22 C23Aa -48.2(15) . . . . ?
C19 C18 C22 C25Bb 38.1(18) . . . . ?
C17 C18 C22 C25Bb -144.9(16) . . . . ?
C19 C18 C22 C24Bb -60(2) . . . . ?
C17 C18 C22 C24Bb 117(2) . . . . ?
C21 C20 C26 C27 27.3(13) . . . . ?
C19 C20 C26 C27 -156.8(9) . . . . ?
C21 C20 C26 C29 -92.6(11) . . . . ?
C19 C20 C26 C29 83.3(11) . . . . ?
C21 C20 C26 C28 147.8(10) . . . . ?
C19 C20 C26 C28 -36.3(13) . . . . ?
C21 C16 C30 O5 -78.7(12) . . . . ?
C17 C16 C30 O5 100.9(11) . . . . ?
N3 O5 C30 C16 -75.4(11) . . . . ?
O5 N3 C31 C32 -179.9(7) . . . . ?
N3 C31 C32 C37 -174.0(7) . . . . ?
N3 C31 C32 C33 3.0(11) . . . . ?
C37 C32 C33 C34 1.8(11) . . . . ?
C31 C32 C33 C34 -175.2(7) . . . . ?
C32 C33 C34 C35 0.2(12) . . . . ?
C33 C34 C35 C36 -1.0(11) . . . . ?
C33 C34 C35 C38 176.2(7) . . . . ?
C34 C35 C36 C37 -0.1(11) . . . . ?
C38 C35 C36 C37 -177.2(7) . . . . ?
C33 C32 C37 C36 -3.0(12) . . . . ?
C31 C32 C37 C36 174.2(7) . . . . ?
C35 C36 C37 C32 2.1(12) . . . . ?
C39 N4 C38 C35 -67.2(9) . . . . ?
C34 C35 C38 N4 -82.9(9) . . . . ?
C36 C35 C38 N4 94.2(9) . . . . ?
C38 N4 C39 C39 -178.2(7) . . . 2_666 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N4 H4A O4 . . 2_666 2.726(10) 0.910 1.957 141.2 no
N4 H4B O3 . . . 2.655(9) 0.910 1.890 140.4 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
