# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_elias
_audit_block_doi                 10.5517/ccdc.csd.cc1m5fx4
_database_code_depnum_ccdc_archive 'CCDC 1494786'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7DT04531J 2018
_audit_update_record             
;
2016-07-19 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 I4 P2 Se2'
_chemical_formula_weight         1063.91

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 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   10.1210(2)
_cell_length_b                   17.1331(4)
_cell_length_c                   17.6880(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.514(2)
_cell_angle_gamma                90.00
_cell_volume                     3067.03(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    21787
_cell_measurement_theta_min      2.5790
_cell_measurement_theta_max      30.7350

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1960
_exptl_absorpt_coefficient_mu    6.557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.44249
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
'Mon Oct 19 16:40:45 2015'
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            80670
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         31.10
_reflns_number_total             9266
_reflns_number_gt                8092
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
'Mon Oct 19 16:40:45 2015'
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
'Mon Oct 19 16:40:45 2015'
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
'Mon Oct 19 16:40:45 2015'
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0129P)²+3.4719P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9266
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0481
_refine_ls_wR_factor_gt          0.0459
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.016294(16) 0.737055(10) 0.399662(9) 0.01550(4) Uani 1 1 d . . .
I2 I 0.005157(19) 0.901310(10) 0.404660(10) 0.02106(4) Uani 1 1 d . . .
I3 I 0.664504(16) 0.602613(10) 0.269965(9) 0.01583(4) Uani 1 1 d . . .
I4 I 0.656858(18) 0.608125(11) 0.110239(10) 0.02105(4) Uani 1 1 d . . .
Se1 Se 0.01059(3) 0.567421(15) 0.407015(14) 0.01551(6) Uani 1 1 d . . .
Se2 Se 0.66674(3) 0.593842(15) 0.433036(14) 0.01502(5) Uani 1 1 d . . .
P1 P 0.16849(6) 0.52609(4) 0.33671(3) 0.01037(12) Uani 1 1 d . . .
P2 P 0.48881(6) 0.65993(4) 0.45027(3) 0.01049(12) Uani 1 1 d . . .
C1 C 0.3297(2) 0.54350(14) 0.38018(13) 0.0114(5) Uani 1 1 d . . .
H1A H 0.3319 0.5204 0.4315 0.014 Uiso 1 1 calc R . .
H1B H 0.3990 0.5179 0.3498 0.014 Uiso 1 1 calc R . .
C2 C 0.3579(2) 0.63135(14) 0.38532(13) 0.0114(5) Uani 1 1 d . . .
H2A H 0.2756 0.6581 0.4005 0.014 Uiso 1 1 calc R . .
H2B H 0.3807 0.6504 0.3342 0.014 Uiso 1 1 calc R . .
C11 C 0.1502(2) 0.42188(14) 0.32589(14) 0.0124(5) Uani 1 1 d . . .
C12 C 0.1774(3) 0.38573(15) 0.25686(15) 0.0181(5) Uani 1 1 d . . .
H12 H 0.2064 0.4158 0.2151 0.022 Uiso 1 1 calc R . .
C13 C 0.1618(3) 0.30600(15) 0.24983(16) 0.0224(6) Uani 1 1 d . . .
H13 H 0.1814 0.2812 0.2032 0.027 Uiso 1 1 calc R . .
C14 C 0.1177(3) 0.26191(16) 0.31023(16) 0.0218(6) Uani 1 1 d . . .
H14 H 0.1043 0.2073 0.3044 0.026 Uiso 1 1 calc R . .
C15 C 0.0931(3) 0.29726(16) 0.37896(16) 0.0219(6) Uani 1 1 d . . .
H15 H 0.0650 0.2667 0.4207 0.026 Uiso 1 1 calc R . .
C16 C 0.1093(3) 0.37695(15) 0.38719(15) 0.0175(5) Uani 1 1 d . . .
H16 H 0.0926 0.4011 0.4345 0.021 Uiso 1 1 calc R . .
C21 C 0.1687(2) 0.56913(14) 0.24359(13) 0.0122(5) Uani 1 1 d . . .
C22 C 0.0566(3) 0.60872(14) 0.21772(15) 0.0153(5) Uani 1 1 d . . .
H22 H -0.0166 0.6161 0.2502 0.018 Uiso 1 1 calc R . .
C23 C 0.0527(3) 0.63730(15) 0.14397(15) 0.0185(5) Uani 1 1 d . . .
H23 H -0.0228 0.6651 0.1263 0.022 Uiso 1 1 calc R . .
C24 C 0.1589(3) 0.62518(16) 0.09636(14) 0.0184(5) Uani 1 1 d . . .
H24 H 0.1555 0.6443 0.0459 0.022 Uiso 1 1 calc R . .
C25 C 0.2699(3) 0.58540(15) 0.12187(15) 0.0172(5) Uani 1 1 d . . .
H25 H 0.3420 0.5769 0.0888 0.021 Uiso 1 1 calc R . .
C26 C 0.2760(3) 0.55795(14) 0.19554(14) 0.0142(5) Uani 1 1 d . . .
H26 H 0.3528 0.5316 0.2133 0.017 Uiso 1 1 calc R . .
C31 C 0.5059(2) 0.76405(14) 0.43417(13) 0.0115(5) Uani 1 1 d . . .
C32 C 0.4038(3) 0.81302(15) 0.45792(14) 0.0149(5) Uani 1 1 d . . .
H32 H 0.3295 0.7919 0.4832 0.018 Uiso 1 1 calc R . .
C33 C 0.4116(3) 0.89282(15) 0.44429(15) 0.0173(5) Uani 1 1 d . . .
H33 H 0.3426 0.9264 0.4604 0.021 Uiso 1 1 calc R . .
C34 C 0.5199(3) 0.92335(16) 0.40723(15) 0.0199(6) Uani 1 1 d . . .
H34 H 0.5251 0.9779 0.3981 0.024 Uiso 1 1 calc R . .
C35 C 0.6210(3) 0.87460(16) 0.38330(15) 0.0203(6) Uani 1 1 d . . .
H35 H 0.6947 0.8959 0.3576 0.024 Uiso 1 1 calc R . .
C36 C 0.6146(3) 0.79471(15) 0.39698(14) 0.0157(5) Uani 1 1 d . . .
H36 H 0.6840 0.7614 0.3810 0.019 Uiso 1 1 calc R . .
C41 C 0.4310(3) 0.64822(14) 0.54557(13) 0.0124(5) Uani 1 1 d . . .
C42 C 0.3003(3) 0.63085(17) 0.56218(15) 0.0210(6) Uani 1 1 d . . .
H42 H 0.2381 0.6230 0.5224 0.025 Uiso 1 1 calc R . .
C43 C 0.2605(3) 0.62490(19) 0.63689(16) 0.0270(7) Uani 1 1 d . . .
H43 H 0.1715 0.6122 0.6483 0.032 Uiso 1 1 calc R . .
C44 C 0.3510(3) 0.63752(19) 0.69456(16) 0.0276(7) Uani 1 1 d . . .
H44 H 0.3235 0.6340 0.7456 0.033 Uiso 1 1 calc R . .
C45 C 0.4806(3) 0.65513(18) 0.67887(15) 0.0240(6) Uani 1 1 d . . .
H45 H 0.5419 0.6637 0.7190 0.029 Uiso 1 1 calc R . .
C46 C 0.5214(3) 0.66038(15) 0.60449(14) 0.0165(5) Uani 1 1 d . . .
H46 H 0.6109 0.6723 0.5936 0.020 Uiso 1 1 calc R . .


_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
I1 I2 2.8179(2) . ?
I1 Se1 2.9098(3) . ?
I3 I4 2.8272(2) . ?
I3 Se2 2.8882(3) . ?
Se1 P1 2.1534(7) . ?
Se2 P2 2.1512(7) . ?
P1 C21 1.805(2) . ?
P1 C11 1.805(2) . ?
P1 C1 1.822(2) . ?
P2 C41 1.800(2) . ?
P2 C2 1.813(2) . ?
P2 C31 1.815(2) . ?
C1 C2 1.534(3) . ?
C11 C16 1.396(4) . ?
C11 C12 1.399(3) . ?
C12 C13 1.381(4) . ?
C13 C14 1.386(4) . ?
C14 C15 1.383(4) . ?
C15 C16 1.383(4) . ?
C21 C22 1.395(3) . ?
C21 C26 1.398(3) . ?
C22 C23 1.394(4) . ?
C23 C24 1.387(4) . ?
C24 C25 1.386(4) . ?
C25 C26 1.386(3) . ?
C31 C36 1.390(3) . ?
C31 C32 1.399(3) . ?
C32 C33 1.391(4) . ?
C33 C34 1.385(4) . ?
C34 C35 1.390(4) . ?
C35 C36 1.392(4) . ?
C41 C42 1.390(4) . ?
C41 C46 1.396(3) . ?
C42 C43 1.389(4) . ?
C43 C44 1.382(4) . ?
C44 C45 1.376(4) . ?
C45 C46 1.386(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
I2 I1 Se1 174.428(9) . . ?
I4 I3 Se2 178.454(9) . . ?
P1 Se1 I1 106.707(19) . . ?
P2 Se2 I3 96.606(19) . . ?
C21 P1 C11 107.96(11) . . ?
C21 P1 C1 108.05(11) . . ?
C11 P1 C1 107.29(11) . . ?
C21 P1 Se1 113.56(9) . . ?
C11 P1 Se1 108.09(9) . . ?
C1 P1 Se1 111.65(8) . . ?
C41 P2 C2 108.73(12) . . ?
C41 P2 C31 106.78(11) . . ?
C2 P2 C31 103.66(11) . . ?
C41 P2 Se2 110.71(8) . . ?
C2 P2 Se2 112.09(8) . . ?
C31 P2 Se2 114.46(8) . . ?
C2 C1 P1 110.54(16) . . ?
C1 C2 P2 115.90(17) . . ?
C16 C11 C12 119.7(2) . . ?
C16 C11 P1 119.61(19) . . ?
C12 C11 P1 120.66(19) . . ?
C13 C12 C11 119.6(2) . . ?
C12 C13 C14 120.5(3) . . ?
C15 C14 C13 120.1(3) . . ?
C16 C15 C14 120.2(3) . . ?
C15 C16 C11 119.9(2) . . ?
C22 C21 C26 120.1(2) . . ?
C22 C21 P1 119.35(19) . . ?
C26 C21 P1 120.40(19) . . ?
C23 C22 C21 119.6(2) . . ?
C24 C23 C22 120.0(2) . . ?
C25 C24 C23 120.4(2) . . ?
C26 C25 C24 120.1(2) . . ?
C25 C26 C21 119.8(2) . . ?
C36 C31 C32 120.4(2) . . ?
C36 C31 P2 121.51(19) . . ?
C32 C31 P2 118.08(19) . . ?
C33 C32 C31 119.6(2) . . ?
C34 C33 C32 120.0(2) . . ?
C33 C34 C35 120.3(3) . . ?
C34 C35 C36 120.2(3) . . ?
C31 C36 C35 119.5(2) . . ?
C42 C41 C46 119.5(2) . . ?
C42 C41 P2 122.7(2) . . ?
C46 C41 P2 117.75(19) . . ?
C43 C42 C41 120.1(3) . . ?
C44 C43 C42 119.7(3) . . ?
C45 C44 C43 120.8(3) . . ?
C44 C45 C46 119.9(3) . . ?
C45 C46 C41 120.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.939
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.041
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.125


# end of cif file
####################################################################### 
# 
# 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_o4_36mo
_audit_block_doi                 10.5517/cc8xlqg
_database_code_depnum_ccdc_archive 'CCDC 265816'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/anie.200462254 2005
_audit_update_record             
;
2005-03-09 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H55 F13 N4 O6 P2'
_chemical_formula_weight         1092.90

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 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   16.396(4)
_cell_length_b                   13.046(3)
_cell_length_c                   11.979(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.386(4)
_cell_angle_gamma                90.00
_cell_volume                     2445.1(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3398
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.06

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          1.30
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1132
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7883
_exptl_absorpt_correction_T_max  0.9717
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        <2.0
_diffrn_reflns_number            5780
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3827
_reflns_number_gt                3279
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    ORTEP3
_computing_publication_material  WinGX

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1012P)²+8.4757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_number_reflns         3827
_refine_ls_number_parameters     383
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0813
_refine_ls_wR_factor_ref         0.2134
_refine_ls_wR_factor_gt          0.2008
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.0000 0.3244(3) 0.0000 0.0388(10) Uani 1 2 d S . .
O1 O 0.2016(3) 0.1749(4) 0.1821(5) 0.0772(17) Uani 1 1 d . A .
H1 H 0.1972 0.1389 0.1224 0.116 Uiso 1 1 calc R . .
N1 N 0.1751(2) 0.3917(4) 0.2372(3) 0.0362(10) Uani 1 1 d . . .
C1 C 0.0000 0.4297(6) 0.0000 0.0327(16) Uani 1 2 d S . .
C2 C 0.0757(3) 0.4791(4) 0.0553(4) 0.0288(10) Uani 1 1 d . . .
C3 C 0.0755(3) 0.5854(4) 0.0527(4) 0.0323(11) Uani 1 1 d . . .
H3 H 0.1268 0.6224 0.0868 0.039 Uiso 1 1 calc R . .
C4 C 0.0000 0.6373(5) 0.0000 0.0365(17) Uani 1 2 d S . .
H4 H 0.0000 0.7102 0.0000 0.044 Uiso 1 2 calc SR . .
C5 C 0.1554(3) 0.4153(4) 0.1076(4) 0.0365(12) Uani 1 1 d . . .
H5A H 0.2049 0.4519 0.0953 0.044 Uiso 1 1 calc R . .
H5B H 0.1492 0.3497 0.0644 0.044 Uiso 1 1 calc R . .
C6 C 0.2599(3) 0.3297(5) 0.2805(5) 0.0441(13) Uani 1 1 d . A .
H6 H 0.3080 0.3791 0.2883 0.053 Uiso 1 1 calc R . .
C7 C 0.2658(4) 0.2917(5) 0.4048(5) 0.0495(15) Uani 1 1 d . . .
H7A H 0.2483 0.2188 0.4012 0.059 Uiso 1 1 calc R . .
H7B H 0.3257 0.2966 0.4553 0.059 Uiso 1 1 calc R . .
C8 C 0.2084(4) 0.3553(6) 0.4577(5) 0.0609(19) Uani 1 1 d . . .
H8 H 0.2218 0.3398 0.5431 0.073 Uiso 1 1 calc R . .
C9 C 0.2218(4) 0.4692(5) 0.4402(5) 0.0501(15) Uani 1 1 d . . .
H9 H 0.1837 0.5078 0.4768 0.060 Uiso 1 1 calc R . .
C10 C 0.1894(3) 0.4901(5) 0.3068(4) 0.0394(12) Uani 1 1 d . . .
H10A H 0.1351 0.5290 0.2882 0.047 Uiso 1 1 calc R . .
H10B H 0.2317 0.5328 0.2840 0.047 Uiso 1 1 calc R . .
C11 C 0.1017(3) 0.3369(5) 0.2625(5) 0.0436(13) Uani 1 1 d . . .
H11A H 0.0955 0.2677 0.2270 0.052 Uiso 1 1 calc R . .
H11B H 0.0481 0.3752 0.2265 0.052 Uiso 1 1 calc R . .
C12 C 0.1157(4) 0.3271(6) 0.3945(5) 0.0554(16) Uani 1 1 d . . .
H12A H 0.0765 0.3736 0.4190 0.066 Uiso 1 1 calc R . .
H12B H 0.1040 0.2559 0.4141 0.066 Uiso 1 1 calc R . .
C13 C 0.3124(6) 0.5031(7) 0.5007(6) 0.075(2) Uani 1 1 d . . .
H13 H 0.3310 0.4889 0.5822 0.090 Uiso 1 1 calc R . .
C14 C 0.3664(5) 0.5453(9) 0.4648(8) 0.097(3) Uani 1 1 d . . .
H14A H 0.3537 0.5625 0.3843 0.117 Uiso 1 1 calc R . .
H14B H 0.4210 0.5608 0.5173 0.117 Uiso 1 1 calc R . .
C15 C 0.2694(4) 0.2444(6) 0.1972(5) 0.0577(19) Uani 1 1 d . . .
H15 H 0.272(4) 0.279(6) 0.128(6) 0.059(19) Uiso 1 1 d . . .
C16 C 0.3642(4) 0.2029(7) 0.2491(10) 0.051(4) Uani 0.622(18) 1 d PG A 1
C17 C 0.3657(4) 0.1058(7) 0.2976(9) 0.045(3) Uani 0.622(18) 1 d PG A 1
H17 H 0.3139 0.0739 0.2987 0.054 Uiso 0.622(18) 1 calc PR A 1
C18 C 0.4431(4) 0.0555(5) 0.3445(8) 0.037(3) Uani 0.622(18) 1 d PG A 1
H18 H 0.4442 -0.0109 0.3777 0.044 Uiso 0.622(18) 1 calc PR A 1
N2 N 0.5190(4) 0.1021(5) 0.3430(7) 0.049(4) Uani 0.622(18) 1 d PG A 1
C19 C 0.5174(4) 0.1992(5) 0.2945(5) 0.067(5) Uani 0.622(18) 1 d PG A 1
C20 C 0.4400(4) 0.2496(6) 0.2476(6) 0.045(3) Uani 0.622(18) 1 d PG A 1
C21 C 0.4385(6) 0.3466(7) 0.1991(8) 0.053(4) Uani 0.622(18) 1 d PG A 1
H21 H 0.3856 0.3810 0.1670 0.064 Uiso 0.622(18) 1 calc PR A 1
C22 C 0.5144(7) 0.3933(6) 0.1976(7) 0.136(13) Uani 0.622(18) 1 d PGD A 1
C23 C 0.5918(6) 0.3429(6) 0.2445(8) 0.069(4) Uani 0.622(18) 1 d PG A 1
H23 H 0.6436 0.3748 0.2434 0.083 Uiso 0.622(18) 1 calc PR A 1
C24 C 0.5933(4) 0.2459(6) 0.2930(8) 0.096(9) Uani 0.622(18) 1 d PG A 1
H24 H 0.6462 0.2114 0.3251 0.116 Uiso 0.622(18) 1 calc PR A 1
O2 O 0.5404(6) 0.4829(10) 0.1614(11) 0.112(5) Uani 0.622(18) 1 d PD A 1
C25 C 0.4712(11) 0.5573(16) 0.136(3) 0.162(13) Uani 0.622(18) 1 d PD A 1
H25A H 0.4251 0.5350 0.0677 0.243 Uiso 0.622(18) 1 calc PR A 1
H25B H 0.4925 0.6243 0.1209 0.243 Uiso 0.622(18) 1 calc PR A 1
H25C H 0.4493 0.5625 0.2039 0.243 Uiso 0.622(18) 1 calc PR A 1
C116 C 0.3514(8) 0.1824(10) 0.2486(16) 0.026(5) Uani 0.378(18) 1 d PG A 2
C117 C 0.3581(11) 0.0880(10) 0.3044(17) 0.051(7) Uiso 0.378(18) 1 d PG A 2
H117 H 0.3079 0.0522 0.3058 0.061 Uiso 0.378(18) 1 calc PR A 2
C118 C 0.4381(12) 0.0460(8) 0.3582(14) 0.15(2) Uani 0.378(18) 1 d PG A 2
H118 H 0.4426 -0.0185 0.3964 0.178 Uiso 0.378(18) 1 calc PR A 2
N12 N 0.5115(10) 0.0983(8) 0.3562(13) 0.082(12) Uani 0.378(18) 1 d PG A 2
C119 C 0.5048(8) 0.1927(7) 0.3003(10) 0.029(4) Uiso 0.378(18) 1 d PG A 2
C120 C 0.4248(7) 0.2347(7) 0.2465(10) 0.032(5) Uiso 0.378(18) 1 d PG A 2
C121 C 0.4181(6) 0.3291(7) 0.1906(9) 0.081(10) Uani 0.378(18) 1 d PG A 2
H121 H 0.3635 0.3579 0.1538 0.097 Uiso 0.378(18) 1 calc PR A 2
C122 C 0.4915(6) 0.3815(6) 0.1886(6) 0.072(10) Uani 0.378(18) 1 d PGD A 2
C123 C 0.5715(6) 0.3394(9) 0.2424(12) 0.32(7) Uani 0.378(18) 1 d PG A 2
H123 H 0.6217 0.3752 0.2409 0.383 Uiso 0.378(18) 1 calc PR A 2
C124 C 0.5782(7) 0.2451(9) 0.2982(14) 0.056(6) Uiso 0.378(18) 1 d PG A 2
H124 H 0.6329 0.2163 0.3350 0.068 Uiso 0.378(18) 1 calc PR A 2
O22 O 0.4764(7) 0.4852(7) 0.1242(8) 0.049(5) Uani 0.378(18) 1 d PGD A 2
C125 C 0.5456(8) 0.5553(8) 0.1474(11) 0.116(14) Uani 0.378(18) 1 d PGD A 2
H12C H 0.5785 0.5516 0.2304 0.174 Uiso 0.378(18) 1 calc PR A 2
H12D H 0.5234 0.6250 0.1286 0.174 Uiso 0.378(18) 1 calc PR A 2
H12E H 0.5826 0.5378 0.0994 0.174 Uiso 0.378(18) 1 calc PR A 2
P1 P 0.17163(19) 0.2789(3) 0.8093(2) 0.1233(14) Uani 1 1 d . . .
F2 F 0.1239(4) 0.3718(5) 0.8456(4) 0.114(2) Uani 1 1 d . . .
F3 F 0.2543(4) 0.3045(8) 0.9131(4) 0.162(4) Uani 1 1 d . . .
F4 F 0.2030(4) 0.3608(8) 0.7289(5) 0.167(4) Uani 1 1 d . . .
F5 F 0.0890(5) 0.2509(9) 0.7123(9) 0.215(6) Uani 1 1 d . . .
F6 F 0.1484(6) 0.2187(6) 0.9132(8) 0.162(3) Uani 1 1 d . . .
F7 F 0.2248(7) 0.1995(10) 0.7712(10) 0.261(7) Uani 1 1 d . . .
O1W O 0.2117(9) 0.0411(16) 0.0125(18) 0.103(8) Uani 0.48(3) 1 d P B 1
O2W O 0.1899(11) -0.0227(18) 0.0649(14) 0.112(7) Uani 0.52(3) 1 d P B 2


_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
F1 C1 1.374(8) . ?
O1 C15 1.404(10) . ?
N1 C11 1.508(7) . ?
N1 C10 1.511(7) . ?
N1 C5 1.519(6) . ?
N1 C6 1.556(6) . ?
C1 C2 1.380(5) 2 ?
C1 C2 1.380(5) . ?
C2 C3 1.387(7) . ?
C2 C5 1.517(6) . ?
C3 C4 1.387(6) . ?
C4 C3 1.387(6) 2 ?
C6 C15 1.534(8) . ?
C6 C7 1.545(8) . ?
C7 C8 1.527(8) . ?
C8 C9 1.526(10) . ?
C8 C12 1.527(9) . ?
C9 C13 1.511(10) . ?
C9 C10 1.550(7) . ?
C11 C12 1.533(7) . ?
C13 C14 1.225(12) . ?
C15 C116 1.532(15) . ?
C15 C16 1.587(8) . ?
C16 C17 1.3900 . ?
C16 C20 1.3900 . ?
C17 C18 1.3900 . ?
C18 N2 1.3900 . ?
N2 C19 1.3900 . ?
C19 C20 1.3900 . ?
C19 C24 1.3900 . ?
C20 C21 1.3900 . ?
C21 C22 1.3900 . ?
C22 O2 1.360(13) . ?
C22 C23 1.3900 . ?
C23 C24 1.3900 . ?
O2 C25 1.455(15) . ?
C116 C117 1.3900 . ?
C116 C120 1.3900 . ?
C117 C118 1.3900 . ?
C118 N12 1.3900 . ?
N12 C119 1.3900 . ?
C119 C120 1.3900 . ?
C119 C124 1.3900 . ?
C120 C121 1.3900 . ?
C121 C122 1.3900 . ?
C122 C123 1.3900 . ?
C122 O22 1.5403 . ?
C123 C124 1.3900 . ?
O22 C125 1.4185 . ?
P1 F7 1.509(7) . ?
P1 F5 1.542(8) . ?
P1 F2 1.573(6) . ?
P1 F3 1.577(8) . ?
P1 F6 1.610(11) . ?
P1 F4 1.622(9) . ?

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
C11 N1 C10 107.0(4) . . ?
C11 N1 C5 111.3(4) . . ?
C10 N1 C5 110.0(4) . . ?
C11 N1 C6 112.0(4) . . ?
C10 N1 C6 106.4(4) . . ?
C5 N1 C6 110.0(3) . . ?
F1 C1 C2 117.8(3) . 2 ?
F1 C1 C2 117.8(3) . . ?
C2 C1 C2 124.4(7) 2 . ?
C1 C2 C3 117.3(5) . . ?
C1 C2 C5 118.9(5) . . ?
C3 C2 C5 123.6(4) . . ?
C4 C3 C2 119.7(5) . . ?
C3 C4 C3 121.5(6) 2 . ?
C2 C5 N1 115.3(4) . . ?
C15 C6 C7 113.9(6) . . ?
C15 C6 N1 114.4(4) . . ?
C7 C6 N1 106.3(4) . . ?
C8 C7 C6 110.9(5) . . ?
C9 C8 C12 109.2(5) . . ?
C9 C8 C7 109.9(6) . . ?
C12 C8 C7 108.0(5) . . ?
C13 C9 C8 112.3(5) . . ?
C13 C9 C10 115.4(6) . . ?
C8 C9 C10 107.1(5) . . ?
N1 C10 C9 111.6(5) . . ?
N1 C11 C12 111.4(5) . . ?
C8 C12 C11 108.2(5) . . ?
C14 C13 C9 132.3(8) . . ?
O1 C15 C116 106.1(7) . . ?
O1 C15 C6 108.8(5) . . ?
C116 C15 C6 111.7(9) . . ?
O1 C15 C16 118.3(7) . . ?
C116 C15 C16 12.3(5) . . ?
C6 C15 C16 105.7(6) . . ?
C17 C16 C20 120.0 . . ?
C17 C16 C15 111.6(6) . . ?
C20 C16 C15 128.4(6) . . ?
C18 C17 C16 120.0 . . ?
C17 C18 N2 120.0 . . ?
C19 N2 C18 120.0 . . ?
C20 C19 N2 120.0 . . ?
C20 C19 C24 120.0 . . ?
N2 C19 C24 120.0 . . ?
C21 C20 C19 120.0 . . ?
C21 C20 C16 120.0 . . ?
C19 C20 C16 120.0 . . ?
C22 C21 C20 120.0 . . ?
O2 C22 C21 138.5(7) . . ?
O2 C22 C23 101.5(7) . . ?
C21 C22 C23 120.0 . . ?
C24 C23 C22 120.0 . . ?
C23 C24 C19 120.0 . . ?
C22 O2 C25 109.8(10) . . ?
C117 C116 C120 120.0 . . ?
C117 C116 C15 126.5(5) . . ?
C120 C116 C15 113.2(5) . . ?
C116 C117 C118 120.0 . . ?
C117 C118 N12 120.0 . . ?
C118 N12 C119 120.0 . . ?
C120 C119 N12 120.0 . . ?
C120 C119 C124 120.0 . . ?
N12 C119 C124 120.0 . . ?
C121 C120 C119 120.0 . . ?
C121 C120 C116 120.0 . . ?
C119 C120 C116 120.0 . . ?
C120 C121 C122 120.0 . . ?
C121 C122 C123 120.0 . . ?
C121 C122 O22 115.4 . . ?
C123 C122 O22 124.6 . . ?
C124 C123 C122 120.0 . . ?
C123 C124 C119 120.0 . . ?
C125 O22 C122 117.9 . . ?
F7 P1 F5 93.8(5) . . ?
F7 P1 F2 172.9(7) . . ?
F5 P1 F2 89.6(4) . . ?
F7 P1 F3 86.9(5) . . ?
F5 P1 F3 177.1(7) . . ?
F2 P1 F3 90.0(4) . . ?
F7 P1 F6 101.0(7) . . ?
F5 P1 F6 96.3(6) . . ?
F2 P1 F6 84.8(3) . . ?
F3 P1 F6 80.8(4) . . ?
F7 P1 F4 87.6(7) . . ?
F5 P1 F4 94.1(6) . . ?
F2 P1 F4 86.0(4) . . ?
F3 P1 F4 88.8(5) . . ?
F6 P1 F4 166.0(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1W 0.84 1.90 2.720(15) 165.8 .
O1 H1 O2W 0.84 2.21 2.91(2) 141.4 .

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.072

