# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_eisrs02
_database_code_depnum_ccdc_archive 'CCDC 1446523'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;

_vrf_PLAT301_eisrs02             
; 
PROBLEM: _G Main Residue Disorder ............ Percentage = 23 
RESPONSE: The pendant phenyl ring is modeled as disordered over two 
positions (0.57:0.43). 
;

_vrf_PLAT860_eisrs02             
; 
PROBLEM: _G Number of Least-Squares Restraints ............. 13 
RESPONSE: Analogous bond lengths and angles between the two positions 
of the disordered phenyl ring were restrained to be similar. 
Anisotropic displacement parameters for pairs of proximal atoms were 
constrained to be equivalent. 
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            eisrs02
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 N2 O, F6 P'
_chemical_formula_sum            'C23 H23 F6 N2 O P'
_chemical_formula_weight         488.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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

_cell_length_a                   8.1397(9)
_cell_length_b                   15.2283(16)
_cell_length_c                   18.0213(19)
_cell_angle_alpha                90
_cell_angle_beta                 102.251(2)
_cell_angle_gamma                90
_cell_volume                     2182.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(5)
_cell_measurement_reflns_used    3726
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      37.72

_exptl_crystal_description       block
_exptl_crystal_colour            red-blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.196
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD platform'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57048
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.768
_diffrn_reflns_theta_max         38.566
_diffrn_reflns_theta_full        37.785
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             11919
_reflns_number_gt                8314
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SIR2011 (Burla et al., 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          
; 
The pendant phenyl ring is modeled as disordered over two positions 
(0.57:0.43). Analogous bond lengths and angles between the two positions 
of the disordered phenyl ring were restrained to be similar. Anisotropic 
displacement parameters for pairs of proximal atoms were constrained to 
be equivalent. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0809P)²+0.6399P] 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         11919
_refine_ls_number_parameters     321
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1622
_refine_ls_wR_factor_gt          0.1429
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_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_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 0.34027(4) 0.19872(2) 0.61994(2) 0.02714(8) Uani 1 1 d . . . . .
F1 F 0.33221(18) 0.18033(8) 0.70650(5) 0.0571(3) Uani 1 1 d . . . . .
F2 F 0.15331(13) 0.23715(9) 0.60655(6) 0.0532(3) Uani 1 1 d . . . . .
F3 F 0.34609(15) 0.21885(8) 0.53398(5) 0.0482(3) Uani 1 1 d . . . . .
F4 F 0.41229(17) 0.29447(7) 0.64498(7) 0.0539(3) Uani 1 1 d . . . . .
F5 F 0.52502(18) 0.16171(13) 0.63493(8) 0.0865(6) Uani 1 1 d . . . . .
F6 F 0.2607(2) 0.10478(7) 0.59585(7) 0.0691(4) Uani 1 1 d . . . . .
O1 O 0.07839(9) 0.12290(5) 0.98203(4) 0.01594(12) Uani 1 1 d . . . . .
N1 N 0.47369(11) -0.08627(6) 1.10004(5) 0.01805(15) Uani 1 1 d . . . . .
N2 N -0.28838(12) 0.35557(6) 0.88803(5) 0.02193(16) Uani 1 1 d . . . . .
C1 C 0.21621(12) -0.08192(6) 0.90607(5) 0.01646(15) Uani 1 1 d . . . . .
H1 H 0.1973 -0.1168 0.8614 0.020 Uiso 1 1 calc R U . . .
C2 C 0.32977(12) -0.11006(6) 0.96876(5) 0.01677(15) Uani 1 1 d . . . . .
H2 H 0.3890 -0.1634 0.9665 0.020 Uiso 1 1 calc R U . . .
C3 C 0.36080(11) -0.05989(6) 1.03803(5) 0.01549(15) Uani 1 1 d . . . . .
C4 C 0.27011(12) 0.01888(6) 1.03944(5) 0.01538(15) Uani 1 1 d . . . . .
H4 H 0.2866 0.0531 1.0845 0.018 Uiso 1 1 calc R U . . .
C5 C -0.10007(12) 0.23726(6) 0.93551(5) 0.01681(15) Uani 1 1 d . . . . .
H5 H -0.0759 0.2618 0.9851 0.020 Uiso 1 1 calc R U . . .
C6 C -0.21190(12) 0.28017(6) 0.87578(6) 0.01756(16) Uani 1 1 d . . . . .
C7 C -0.24439(13) 0.24011(7) 0.80200(6) 0.01907(17) Uani 1 1 d . . . . .
H7 H -0.3173 0.2685 0.7609 0.023 Uiso 1 1 calc R U . . .
C8 C -0.17231(12) 0.16188(7) 0.78987(5) 0.01785(16) Uani 1 1 d . . . . .
H8 H -0.1988 0.1364 0.7407 0.021 Uiso 1 1 calc R U . . .
C9 C 0.01475(11) 0.03438(6) 0.84196(5) 0.01504(15) Uani 1 1 d D . . . .
C10 C 0.12512(11) -0.00169(6) 0.90570(5) 0.01446(14) Uani 1 1 d . . . . .
C11 C 0.15767(11) 0.04585(6) 0.97524(5) 0.01446(14) Uani 1 1 d . . . . .
C12 C -0.02660(11) 0.15955(6) 0.92112(5) 0.01497(15) Uani 1 1 d . . . . .
C13 C -0.05816(11) 0.11735(6) 0.84911(5) 0.01525(15) Uani 1 1 d . . . . .
C14 C 0.50050(13) -0.03464(7) 1.17000(6) 0.02024(17) Uani 1 1 d . . . . .
H14A H 0.5298 0.0258 1.1593 0.030 Uiso 1 1 calc R U . . .
H14B H 0.5923 -0.0606 1.2077 0.030 Uiso 1 1 calc R U . . .
H14C H 0.3974 -0.0345 1.1899 0.030 Uiso 1 1 calc R U . . .
C15 C 0.56911(14) -0.16762(7) 1.10164(6) 0.02278(19) Uani 1 1 d . . . . .
H15A H 0.6243 -0.1689 1.0583 0.034 Uiso 1 1 calc R U . . .
H15B H 0.4928 -0.2179 1.0987 0.034 Uiso 1 1 calc R U . . .
H15C H 0.6543 -0.1707 1.1490 0.034 Uiso 1 1 calc R U . . .
C16 C -0.26318(19) 0.39319(8) 0.96424(7) 0.0298(2) Uani 1 1 d . . . . .
H16A H -0.1426 0.4009 0.9849 0.045 Uiso 1 1 calc R U . . .
H16B H -0.3104 0.3536 0.9972 0.045 Uiso 1 1 calc R U . . .
H16C H -0.3196 0.4503 0.9617 0.045 Uiso 1 1 calc R U . . .
C17 C -0.39111(16) 0.40471(8) 0.82510(8) 0.0292(2) Uani 1 1 d . . . . .
H17A H -0.4871 0.3687 0.8005 0.044 Uiso 1 1 calc R U . . .
H17B H -0.3231 0.4196 0.7881 0.044 Uiso 1 1 calc R U . . .
H17C H -0.4319 0.4588 0.8446 0.044 Uiso 1 1 calc R U . . .
C18 C -0.036(2) -0.0167(9) 0.7708(4) 0.0165(10) Uani 0.572(12) 1 d D . P A 1
C19 C -0.1097(16) -0.1000(7) 0.7726(5) 0.0214(8) Uani 0.572(12) 1 d D . P A 1
H19 H -0.1233 -0.1240 0.8196 0.026 Uiso 0.572(12) 1 calc R U P A 1
C20 C -0.1627(10) -0.1476(5) 0.7056(4) 0.0283(9) Uani 0.572(12) 1 d D . P A 1
H20 H -0.2117 -0.2040 0.7069 0.034 Uiso 0.572(12) 1 calc R U P A 1
C21 C -0.1434(10) -0.1120(6) 0.6364(4) 0.0339(11) Uani 0.572(12) 1 d D . P A 1
H21 H -0.1840 -0.1429 0.5904 0.041 Uiso 0.572(12) 1 calc R U P A 1
C22 C -0.0647(12) -0.0314(6) 0.6353(4) 0.0316(11) Uani 0.572(12) 1 d D . P A 1
H22 H -0.0488 -0.0082 0.5884 0.038 Uiso 0.572(12) 1 calc R U P A 1
C23 C -0.009(2) 0.0162(8) 0.7020(5) 0.0234(9) Uani 0.572(12) 1 d D . P A 1
H23 H 0.0478 0.0706 0.7008 0.028 Uiso 0.572(12) 1 calc R U P A 1
C18' C -0.019(3) -0.0120(12) 0.7678(6) 0.0165(10) Uani 0.428(12) 1 d D . P A 5
C19' C -0.098(2) -0.0942(10) 0.7629(7) 0.0214(8) Uani 0.428(12) 1 d D . P A 5
H19' H -0.1173 -0.1223 0.8072 0.026 Uiso 0.428(12) 1 calc R U P A 5
C20' C -0.1468(14) -0.1342(7) 0.6920(5) 0.0283(9) Uani 0.428(12) 1 d D . P A 5
H20' H -0.2026 -0.1893 0.6882 0.034 Uiso 0.428(12) 1 calc R U P A 5
C21' C -0.1156(14) -0.0951(8) 0.6277(6) 0.0339(11) Uani 0.428(12) 1 d D . P A 5
H21' H -0.1494 -0.1234 0.5799 0.041 Uiso 0.428(12) 1 calc R U P A 5
C22' C -0.0356(16) -0.0152(8) 0.6323(6) 0.0316(11) Uani 0.428(12) 1 d D . P A 5
H22' H -0.0112 0.0107 0.5879 0.038 Uiso 0.428(12) 1 calc R U P A 5
C23' C 0.010(3) 0.0283(11) 0.7020(8) 0.0234(9) Uani 0.428(12) 1 d D . P A 5
H23' H 0.0610 0.0847 0.7046 0.028 Uiso 0.428(12) 1 calc R U P A 5


_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 F5 1.5746(12) . ?
P1 F3 1.5898(10) . ?
P1 F6 1.5922(11) . ?
P1 F1 1.5998(10) . ?
P1 F2 1.6002(11) . ?
P1 F4 1.6004(10) . ?
O1 C11 1.3570(12) . ?
O1 C12 1.3597(11) . ?
N1 C3 1.3486(12) . ?
N1 C15 1.4593(14) . ?
N1 C14 1.4624(13) . ?
N2 C6 1.3464(14) . ?
N2 C16 1.4618(16) . ?
N2 C17 1.4638(15) . ?
C1 C2 1.3679(13) . ?
C1 C10 1.4285(13) . ?
C1 H1 0.9500 . ?
C2 C3 1.4396(13) . ?
C2 H2 0.9500 . ?
C3 C4 1.4115(14) . ?
C4 C11 1.3768(13) . ?
C4 H4 0.9500 . ?
C5 C12 1.3752(14) . ?
C5 C6 1.4136(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.4357(14) . ?
C7 C8 1.3659(15) . ?
C7 H7 0.9500 . ?
C8 C13 1.4290(13) . ?
C8 H8 0.9500 . ?
C9 C10 1.4108(13) . ?
C9 C13 1.4134(14) . ?
C9 C18 1.483(4) . ?
C9 C18' 1.485(6) . ?
C10 C11 1.4227(13) . ?
C12 C13 1.4217(13) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.398(7) . ?
C18 C19 1.406(7) . ?
C19 C20 1.397(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.398(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.396(7) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C18' C19' 1.398(10) . ?
C18' C23' 1.401(10) . ?
C19' C20' 1.395(10) . ?
C19' H19' 0.9500 . ?
C20' C21' 1.374(9) . ?
C20' H20' 0.9500 . ?
C21' C22' 1.375(9) . ?
C21' H21' 0.9500 . ?
C22' C23' 1.398(10) . ?
C22' H22' 0.9500 . ?
C23' H23' 0.9500 . ?

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
F5 P1 F3 90.65(8) . . ?
F5 P1 F6 92.51(10) . . ?
F3 P1 F6 90.12(7) . . ?
F5 P1 F1 90.31(8) . . ?
F3 P1 F1 178.79(7) . . ?
F6 P1 F1 90.58(7) . . ?
F5 P1 F2 178.75(7) . . ?
F3 P1 F2 90.37(6) . . ?
F6 P1 F2 88.20(8) . . ?
F1 P1 F2 88.66(7) . . ?
F5 P1 F4 89.91(9) . . ?
F3 P1 F4 90.82(6) . . ?
F6 P1 F4 177.40(8) . . ?
F1 P1 F4 88.44(6) . . ?
F2 P1 F4 89.37(7) . . ?
C11 O1 C12 120.76(8) . . ?
C3 N1 C15 122.38(9) . . ?
C3 N1 C14 120.34(9) . . ?
C15 N1 C14 117.25(8) . . ?
C6 N2 C16 120.71(9) . . ?
C6 N2 C17 121.13(10) . . ?
C16 N2 C17 118.08(10) . . ?
C2 C1 C10 122.07(9) . . ?
C2 C1 H1 119.0 . . ?
C10 C1 H1 119.0 . . ?
C1 C2 C3 120.89(9) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
N1 C3 C4 120.34(9) . . ?
N1 C3 C2 121.59(9) . . ?
C4 C3 C2 118.06(8) . . ?
C11 C4 C3 119.69(9) . . ?
C11 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C12 C5 C6 119.32(9) . . ?
C12 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
N2 C6 C5 120.99(9) . . ?
N2 C6 C7 120.90(9) . . ?
C5 C6 C7 118.10(9) . . ?
C8 C7 C6 121.19(9) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C13 121.84(9) . . ?
C7 C8 H8 119.1 . . ?
C13 C8 H8 119.1 . . ?
C10 C9 C13 118.75(8) . . ?
C10 C9 C18 120.9(8) . . ?
C13 C9 C18 120.2(8) . . ?
C10 C9 C18' 120.8(11) . . ?
C13 C9 C18' 120.4(10) . . ?
C9 C10 C11 119.11(8) . . ?
C9 C10 C1 125.24(8) . . ?
C11 C10 C1 115.57(8) . . ?
O1 C11 C4 115.22(8) . . ?
O1 C11 C10 121.08(8) . . ?
C4 C11 C10 123.70(9) . . ?
O1 C12 C5 115.14(8) . . ?
O1 C12 C13 120.82(8) . . ?
C5 C12 C13 124.02(8) . . ?
C9 C13 C12 119.29(8) . . ?
C9 C13 C8 125.11(9) . . ?
C12 C13 C8 115.49(9) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 119.6(5) . . ?
C23 C18 C9 120.7(7) . . ?
C19 C18 C9 119.7(7) . . ?
C20 C19 C18 120.1(6) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.9(5) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 119.7(6) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.9(6) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C18 119.5(6) . . ?
C22 C23 H23 120.2 . . ?
C18 C23 H23 120.2 . . ?
C19' C18' C23' 119.8(7) . . ?
C19' C18' C9 118.5(9) . . ?
C23' C18' C9 121.4(10) . . ?
C20' C19' C18' 119.2(8) . . ?
C20' C19' H19' 120.4 . . ?
C18' C19' H19' 120.4 . . ?
C21' C20' C19' 121.0(8) . . ?
C21' C20' H20' 119.5 . . ?
C19' C20' H20' 119.5 . . ?
C20' C21' C22' 120.1(9) . . ?
C20' C21' H21' 119.9 . . ?
C22' C21' H21' 119.9 . . ?
C21' C22' C23' 120.4(9) . . ?
C21' C22' H22' 119.8 . . ?
C23' C22' H22' 119.8 . . ?
C22' C23' C18' 119.4(9) . . ?
C22' C23' H23' 120.3 . . ?
C18' C23' H23' 120.3 . . ?

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
C10 C1 C2 C3 0.82(15) . . . . ?
C15 N1 C3 C4 179.30(9) . . . . ?
C14 N1 C3 C4 1.46(14) . . . . ?
C15 N1 C3 C2 -1.15(15) . . . . ?
C14 N1 C3 C2 -179.00(9) . . . . ?
C1 C2 C3 N1 -179.26(9) . . . . ?
C1 C2 C3 C4 0.29(14) . . . . ?
N1 C3 C4 C11 178.74(9) . . . . ?
C2 C3 C4 C11 -0.82(13) . . . . ?
C16 N2 C6 C5 -2.58(16) . . . . ?
C17 N2 C6 C5 173.92(10) . . . . ?
C16 N2 C6 C7 176.09(10) . . . . ?
C17 N2 C6 C7 -7.40(16) . . . . ?
C12 C5 C6 N2 178.86(9) . . . . ?
C12 C5 C6 C7 0.15(14) . . . . ?
N2 C6 C7 C8 -177.42(10) . . . . ?
C5 C6 C7 C8 1.30(15) . . . . ?
C6 C7 C8 C13 -1.68(15) . . . . ?
C13 C9 C10 C11 0.86(13) . . . . ?
C18 C9 C10 C11 -173.8(6) . . . . ?
C18' C9 C10 C11 178.4(8) . . . . ?
C13 C9 C10 C1 -175.91(9) . . . . ?
C18 C9 C10 C1 9.5(6) . . . . ?
C18' C9 C10 C1 1.6(8) . . . . ?
C2 C1 C10 C9 175.55(9) . . . . ?
C2 C1 C10 C11 -1.32(13) . . . . ?
C12 O1 C11 C4 175.35(8) . . . . ?
C12 O1 C11 C10 -4.14(13) . . . . ?
C3 C4 C11 O1 -179.19(8) . . . . ?
C3 C4 C11 C10 0.28(14) . . . . ?
C9 C10 C11 O1 3.14(13) . . . . ?
C1 C10 C11 O1 -179.79(8) . . . . ?
C9 C10 C11 C4 -176.29(9) . . . . ?
C1 C10 C11 C4 0.78(13) . . . . ?
C11 O1 C12 C5 179.55(8) . . . . ?
C11 O1 C12 C13 1.07(13) . . . . ?
C6 C5 C12 O1 -179.71(8) . . . . ?
C6 C5 C12 C13 -1.28(15) . . . . ?
C10 C9 C13 C12 -3.79(13) . . . . ?
C18 C9 C13 C12 170.9(5) . . . . ?
C18' C9 C13 C12 178.7(8) . . . . ?
C10 C9 C13 C8 -179.73(9) . . . . ?
C18 C9 C13 C8 -5.1(5) . . . . ?
C18' C9 C13 C8 2.7(8) . . . . ?
O1 C12 C13 C9 2.94(13) . . . . ?
C5 C12 C13 C9 -175.41(9) . . . . ?
O1 C12 C13 C8 179.26(8) . . . . ?
C5 C12 C13 C8 0.92(14) . . . . ?
C7 C8 C13 C9 176.67(9) . . . . ?
C7 C8 C13 C12 0.59(14) . . . . ?
C10 C9 C18 C23 -123.3(15) . . . . ?
C13 C9 C18 C23 62.2(19) . . . . ?
C10 C9 C18 C19 55.3(18) . . . . ?
C13 C9 C18 C19 -119.2(14) . . . . ?
C23 C18 C19 C20 -3(3) . . . . ?
C9 C18 C19 C20 178.1(12) . . . . ?
C18 C19 C20 C21 -0.4(19) . . . . ?
C19 C20 C21 C22 3.0(14) . . . . ?
C20 C21 C22 C23 -1.9(16) . . . . ?
C21 C22 C23 C18 -2(2) . . . . ?
C19 C18 C23 C22 4(3) . . . . ?
C9 C18 C23 C22 -177.1(14) . . . . ?
C10 C9 C18' C19' 63(2) . . . . ?
C13 C9 C18' C19' -119.1(19) . . . . ?
C10 C9 C18' C23' -123(2) . . . . ?
C13 C9 C18' C23' 54(3) . . . . ?
C23' C18' C19' C20' -1(4) . . . . ?
C9 C18' C19' C20' 173.1(17) . . . . ?
C18' C19' C20' C21' 2(3) . . . . ?
C19' C20' C21' C22' 0(2) . . . . ?
C20' C21' C22' C23' -2(2) . . . . ?
C21' C22' C23' C18' 3(3) . . . . ?
C19' C18' C23' C22' -2(4) . . . . ?
C9 C18' C23' C22' -175.1(19) . . . . ?

_refine_diff_density_max         0.673
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_eisrs03
_database_code_depnum_ccdc_archive 'CCDC 1446524'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;

_vrf_PLAT301_eisrs03             
; 
PROBLEM: _G Main Residue Disorder ............ Percentage = 20 
RESPONSE: The thiophenyl group is modeled as disordered over two 
positions (0.81:0.19). 
;

_vrf_PLAT605_eisrs03             
; 
PROBLEM: _G Structure Contains Solvent Accessible VOIDS of 132 A**3. 
RESPONSE: Two pocket volumes per unit cell, located at crystallographic 
inversion centers, contain highly disordered solvent (likely methanol). 
Reflection contributions from these solvent volumes were fixed and then 
added to the calculated structure factors using the SQUEEZE function of 
program PLATON (Spek, 2009), which determined there to be 81 electrons 
in 263 \%A^3^ accounted for. Because the exact identity and amount of 
solvent are unknown, no solvent was included in the atom list or the 
molecular formula. Thus all calculated quantities that derive from the 
molecular formula (e.g., F(000), molecular weight, density, etc.) are 
known to be incorrect. 
;

_vrf_PLAT860_eisrs03             
; 
PROBLEM: _G Number of Least-Squares Restraints ............. 13 
RESPONSE: Analogous bond lengths and angles between the two 
orientations of the thiophenyl group disorder were restrained to 
be similar. Anisotropic displacement parameters for pairs of 
proximal atoms were constrained to be equivalent. 
;

_vrf_PLAT869_eisrs03             
;
PROBLEM: _G ALERTS Related to the use of SQUEEZE Suppressed! 
RESPONSE: See above response to alert PLAT605.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            eisrs03
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N2 O S, F6 P'
_chemical_formula_sum            'C21 H21 F6 N2 O P S'
_chemical_formula_weight         494.43

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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

_cell_length_a                   15.031(2)
_cell_length_b                   21.396(3)
_cell_length_c                   7.4045(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.883(3)
_cell_angle_gamma                90
_cell_volume                     2321.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(5)
_cell_measurement_reflns_used    4078
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      24.48

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow-violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.272
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5916
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD platform'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23326
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_av_R_equivalents  0.0988
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.904
_diffrn_reflns_theta_max         25.066
_diffrn_reflns_theta_full        25.028
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4105
_reflns_number_gt                2636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SIR2011 (Burla et al., 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          
; 
Two pocket volumes per unit cell, located at crystallographic inversion 
centers, contain highly disordered solvent (likely methanol). Reflection 
contributions from these solvent volumes were fixed and then added to 
the calculated structure factors using the SQUEEZE function of program 
PLATON (Spek, 2009), which determined there to be 81 electrons in 263 
Å³ accounted for. Because the exact identity and amount of solvent 
are unknown, no solvent was included in the atom list or the molecular 
formula. Thus all calculated quantities that derive from the molecular 
formula (e.g., F(000), molecular weight, density, etc.) are known to be 
incorrect. 
  
The thiophenyl group is modeled as disordered over two positions 
(0.81:0.19). Analogous bond lengths and angles between the two 
orientations were restrained to be similar. Anisotropic displacement 
parameters for pairs of proximal atoms were constrained to be equivalent. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+1.6810P] 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         4105
_refine_ls_number_parameters     307
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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_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
O1 O 0.19123(13) 0.31440(9) 0.7450(3) 0.0235(5) Uani 1 1 d . . . . .
N1 N 0.48881(17) 0.35593(12) 0.6704(4) 0.0260(7) Uani 1 1 d . . . . .
N2 N -0.11292(18) 0.29652(13) 0.8099(4) 0.0304(7) Uani 1 1 d . . . . .
C1 C 0.3791(2) 0.20690(15) 0.7239(4) 0.0258(8) Uani 1 1 d . . . . .
H1A H 0.3945 0.1638 0.7321 0.031 Uiso 1 1 calc R U . . .
C2 C 0.4442(2) 0.24876(15) 0.7070(5) 0.0270(8) Uani 1 1 d . . . . .
H2A H 0.5035 0.2343 0.7028 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4257(2) 0.31442(15) 0.6953(4) 0.0233(7) Uani 1 1 d . . . . .
C4 C 0.3382(2) 0.33394(15) 0.7119(4) 0.0232(7) Uani 1 1 d . . . . .
H4A H 0.3241 0.3772 0.7116 0.028 Uiso 1 1 calc R U . . .
C5 C 0.0422(2) 0.30471(15) 0.7761(4) 0.0236(7) Uani 1 1 d . . . . .
H5A H 0.0392 0.3490 0.7778 0.028 Uiso 1 1 calc R U . . .
C6 C -0.0348(2) 0.26859(15) 0.7900(5) 0.0266(8) Uani 1 1 d . . . . .
C7 C -0.0276(2) 0.20244(15) 0.7777(5) 0.0275(8) Uani 1 1 d . . . . .
H7A H -0.0794 0.1772 0.7798 0.033 Uiso 1 1 calc R U . . .
C8 C 0.0517(2) 0.17472(15) 0.7628(5) 0.0265(8) Uani 1 1 d . . . . .
H8A H 0.0539 0.1304 0.7556 0.032 Uiso 1 1 calc R U . . .
C9 C 0.2168(2) 0.18419(14) 0.7439(4) 0.0229(7) Uani 1 1 d . . . . .
C10 C 0.2885(2) 0.22465(14) 0.7300(4) 0.0207(7) Uani 1 1 d . . . . .
C11 C 0.2737(2) 0.29072(14) 0.7284(4) 0.0216(7) Uani 1 1 d . . . . .
C12 C 0.1209(2) 0.27562(14) 0.7602(4) 0.0222(7) Uani 1 1 d . . . . .
C13 C 0.1316(2) 0.20972(14) 0.7577(4) 0.0225(7) Uani 1 1 d . . . . .
C14 C 0.5818(2) 0.33485(17) 0.6692(5) 0.0340(9) Uani 1 1 d . . . . .
H14A H 0.5797 0.3060 0.5656 0.051 Uiso 1 1 calc R U . . .
H14B H 0.6080 0.3135 0.7860 0.051 Uiso 1 1 calc R U . . .
H14C H 0.6196 0.3710 0.6552 0.051 Uiso 1 1 calc R U . . .
C15 C 0.4678(2) 0.42245(15) 0.6501(5) 0.0338(9) Uani 1 1 d . . . . .
H15A H 0.4148 0.4287 0.5475 0.051 Uiso 1 1 calc R U . . .
H15B H 0.5204 0.4449 0.6242 0.051 Uiso 1 1 calc R U . . .
H15C H 0.4542 0.4384 0.7650 0.051 Uiso 1 1 calc R U . . .
C16 C -0.1209(2) 0.36440(16) 0.8075(6) 0.0383(9) Uani 1 1 d . . . . .
H16A H -0.1058 0.3808 0.6944 0.057 Uiso 1 1 calc R U . . .
H16B H -0.0787 0.3819 0.9160 0.057 Uiso 1 1 calc R U . . .
H16C H -0.1836 0.3762 0.8105 0.057 Uiso 1 1 calc R U . . .
C17 C -0.1917(2) 0.26075(17) 0.8354(6) 0.0392(10) Uani 1 1 d . . . . .
H17A H -0.1710 0.2245 0.9144 0.059 Uiso 1 1 calc R U . . .
H17B H -0.2269 0.2465 0.7146 0.059 Uiso 1 1 calc R U . . .
H17C H -0.2303 0.2872 0.8943 0.059 Uiso 1 1 calc R U . . .
C18 C 0.2283(2) 0.11583(15) 0.7459(5) 0.0257(8) Uani 0.815(4) 1 d D . P A 1
C19 C 0.2060(12) 0.0756(7) 0.8696(19) 0.0285(16) Uani 0.815(4) 1 d D . P A 1
H19A H 0.1798 0.0889 0.9687 0.034 Uiso 0.815(4) 1 calc R U P A 1
C20 C 0.2251(3) 0.0113(3) 0.8387(8) 0.0322(13) Uani 0.815(4) 1 d D . P A 1
H20A H 0.2140 -0.0226 0.9137 0.039 Uiso 0.815(4) 1 calc R U P A 1
C21 C 0.2613(4) 0.0057(2) 0.6867(8) 0.0339(12) Uani 0.815(4) 1 d D . P A 1
H21A H 0.2781 -0.0332 0.6419 0.041 Uiso 0.815(4) 1 calc R U P A 1
S1 S 0.27349(10) 0.07580(6) 0.5849(2) 0.0362(4) Uani 0.815(4) 1 d D . P A 1
C18' C 0.2283(2) 0.11583(15) 0.7459(5) 0.0257(8) Uani 0.185(4) 1 d D . P A 5
C19' C 0.2719(13) 0.0873(11) 0.627(3) 0.0362(4) Uani 0.185(4) 1 d D . P A 5
H19B H 0.2907 0.1078 0.5278 0.043 Uiso 0.185(4) 1 calc R U P A 5
C20' C 0.2859(17) 0.0215(9) 0.671(4) 0.0339(12) Uani 0.185(4) 1 d D . P A 5
H20B H 0.3152 -0.0068 0.6039 0.041 Uiso 0.185(4) 1 calc R U P A 5
C21' C 0.2521(16) 0.0055(11) 0.818(4) 0.0322(13) Uani 0.185(4) 1 d D . P A 5
H21B H 0.2550 -0.0357 0.8666 0.039 Uiso 0.185(4) 1 calc R U P A 5
S1' S 0.2036(14) 0.0662(8) 0.909(2) 0.0285(16) Uani 0.185(4) 1 d D . P A 5
P1 P 0.33229(6) 0.59964(5) 0.78471(14) 0.0346(3) Uani 1 1 d . . . . .
F1 F 0.29299(17) 0.52988(10) 0.7628(3) 0.0557(7) Uani 1 1 d . . . . .
F2 F 0.36940(16) 0.66942(11) 0.8070(4) 0.0591(7) Uani 1 1 d . . . . .
F3 F 0.26552(15) 0.61837(10) 0.5927(3) 0.0476(6) Uani 1 1 d . . . . .
F4 F 0.25373(15) 0.61830(10) 0.8901(3) 0.0465(6) Uani 1 1 d . . . . .
F5 F 0.39666(16) 0.58042(12) 0.9770(3) 0.0599(7) Uani 1 1 d . . . . .
F6 F 0.40852(18) 0.58030(13) 0.6788(4) 0.0764(9) Uani 1 1 d . . . . .


_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
O1 C12 1.369(4) . ?
O1 C11 1.370(3) . ?
N1 C3 1.342(4) . ?
N1 C15 1.458(4) . ?
N1 C14 1.470(4) . ?
N2 C6 1.355(4) . ?
N2 C16 1.457(4) . ?
N2 C17 1.457(4) . ?
C1 C2 1.353(4) . ?
C1 C10 1.424(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.431(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.412(4) . ?
C4 C11 1.364(4) . ?
C4 H4A 0.9500 . ?
C5 C12 1.364(4) . ?
C5 C6 1.415(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.424(4) . ?
C7 C8 1.358(4) . ?
C7 H7A 0.9500 . ?
C8 C13 1.423(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.405(4) . ?
C9 C13 1.417(4) . ?
C9 C18' 1.472(4) . ?
C9 C18 1.472(4) . ?
C10 C11 1.431(4) . ?
C12 C13 1.420(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.352(10) . ?
C18 S1 1.726(3) . ?
C19 C20 1.435(15) . ?
C19 H19A 0.9500 . ?
C20 C21 1.361(6) . ?
C20 H20A 0.9500 . ?
C21 S1 1.708(5) . ?
C21 H21A 0.9500 . ?
C18' C19' 1.355(18) . ?
C18' S1' 1.708(9) . ?
C19' C20' 1.45(2) . ?
C19' H19B 0.9500 . ?
C20' C21' 1.346(17) . ?
C20' H20B 0.9500 . ?
C21' S1' 1.698(19) . ?
C21' H21B 0.9500 . ?
P1 F6 1.581(2) . ?
P1 F5 1.587(2) . ?
P1 F2 1.589(2) . ?
P1 F3 1.598(2) . ?
P1 F1 1.600(2) . ?
P1 F4 1.604(2) . ?

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
C12 O1 C11 121.0(2) . . ?
C3 N1 C15 121.1(3) . . ?
C3 N1 C14 120.0(3) . . ?
C15 N1 C14 118.9(3) . . ?
C6 N2 C16 120.6(3) . . ?
C6 N2 C17 122.1(3) . . ?
C16 N2 C17 117.3(3) . . ?
C2 C1 C10 122.9(3) . . ?
C2 C1 H1A 118.6 . . ?
C10 C1 H1A 118.6 . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
N1 C3 C4 121.2(3) . . ?
N1 C3 C2 121.6(3) . . ?
C4 C3 C2 117.2(3) . . ?
C11 C4 C3 120.1(3) . . ?
C11 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C12 C5 C6 119.7(3) . . ?
C12 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
N2 C6 C5 120.7(3) . . ?
N2 C6 C7 121.7(3) . . ?
C5 C6 C7 117.6(3) . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7A 119.3 . . ?
C6 C7 H7A 119.3 . . ?
C7 C8 C13 122.2(3) . . ?
C7 C8 H8A 118.9 . . ?
C13 C8 H8A 118.9 . . ?
C10 C9 C13 119.3(3) . . ?
C10 C9 C18' 121.5(3) . . ?
C13 C9 C18' 119.2(3) . . ?
C10 C9 C18 121.5(3) . . ?
C13 C9 C18 119.2(3) . . ?
C9 C10 C1 126.4(3) . . ?
C9 C10 C11 119.3(3) . . ?
C1 C10 C11 114.3(3) . . ?
C4 C11 O1 115.6(3) . . ?
C4 C11 C10 123.9(3) . . ?
O1 C11 C10 120.5(3) . . ?
C5 C12 O1 115.5(3) . . ?
C5 C12 C13 123.9(3) . . ?
O1 C12 C13 120.6(3) . . ?
C9 C13 C12 119.4(3) . . ?
C9 C13 C8 125.5(3) . . ?
C12 C13 C8 115.1(3) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C9 126.3(8) . . ?
C19 C18 S1 110.3(7) . . ?
C9 C18 S1 123.3(3) . . ?
C18 C19 C20 114.4(11) . . ?
C18 C19 H19A 122.8 . . ?
C20 C19 H19A 122.8 . . ?
C21 C20 C19 110.4(6) . . ?
C21 C20 H20A 124.8 . . ?
C19 C20 H20A 124.8 . . ?
C20 C21 S1 112.9(4) . . ?
C20 C21 H21A 123.5 . . ?
S1 C21 H21A 123.5 . . ?
C21 S1 C18 91.9(2) . . ?
C19' C18' C9 120.9(12) . . ?
C19' C18' S1' 113.1(10) . . ?
C9 C18' S1' 125.5(7) . . ?
C18' C19' C20' 111.0(17) . . ?
C18' C19' H19B 124.5 . . ?
C20' C19' H19B 124.5 . . ?
C21' C20' C19' 111.5(19) . . ?
C21' C20' H20B 124.3 . . ?
C19' C20' H20B 124.3 . . ?
C20' C21' S1' 113.5(18) . . ?
C20' C21' H21B 123.3 . . ?
S1' C21' H21B 123.3 . . ?
C21' S1' C18' 91.0(10) . . ?
F6 P1 F5 90.74(14) . . ?
F6 P1 F2 91.20(15) . . ?
F5 P1 F2 91.18(14) . . ?
F6 P1 F3 90.29(14) . . ?
F5 P1 F3 178.69(14) . . ?
F2 P1 F3 89.60(13) . . ?
F6 P1 F1 89.87(15) . . ?
F5 P1 F1 89.24(13) . . ?
F2 P1 F1 178.85(15) . . ?
F3 P1 F1 89.96(12) . . ?
F6 P1 F4 178.95(16) . . ?
F5 P1 F4 89.76(14) . . ?
F2 P1 F4 89.72(13) . . ?
F3 P1 F4 89.19(13) . . ?
F1 P1 F4 89.21(13) . . ?

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
C10 C1 C2 C3 0.4(5) . . . . ?
C15 N1 C3 C4 -3.2(5) . . . . ?
C14 N1 C3 C4 174.9(3) . . . . ?
C15 N1 C3 C2 177.1(3) . . . . ?
C14 N1 C3 C2 -4.8(5) . . . . ?
C1 C2 C3 N1 -177.0(3) . . . . ?
C1 C2 C3 C4 3.2(5) . . . . ?
N1 C3 C4 C11 176.9(3) . . . . ?
C2 C3 C4 C11 -3.4(5) . . . . ?
C16 N2 C6 C5 3.3(5) . . . . ?
C17 N2 C6 C5 -176.4(3) . . . . ?
C16 N2 C6 C7 -175.1(3) . . . . ?
C17 N2 C6 C7 5.2(5) . . . . ?
C12 C5 C6 N2 178.6(3) . . . . ?
C12 C5 C6 C7 -3.0(5) . . . . ?
N2 C6 C7 C8 -178.2(3) . . . . ?
C5 C6 C7 C8 3.4(5) . . . . ?
C6 C7 C8 C13 -0.3(5) . . . . ?
C13 C9 C10 C1 176.8(3) . . . . ?
C18' C9 C10 C1 -2.7(5) . . . . ?
C18 C9 C10 C1 -2.7(5) . . . . ?
C13 C9 C10 C11 -0.5(4) . . . . ?
C18' C9 C10 C11 179.9(3) . . . . ?
C18 C9 C10 C11 179.9(3) . . . . ?
C2 C1 C10 C9 178.8(3) . . . . ?
C2 C1 C10 C11 -3.8(5) . . . . ?
C3 C4 C11 O1 179.6(3) . . . . ?
C3 C4 C11 C10 -0.1(5) . . . . ?
C12 O1 C11 C4 179.2(3) . . . . ?
C12 O1 C11 C10 -1.1(4) . . . . ?
C9 C10 C11 C4 -178.7(3) . . . . ?
C1 C10 C11 C4 3.6(5) . . . . ?
C9 C10 C11 O1 1.6(4) . . . . ?
C1 C10 C11 O1 -176.1(3) . . . . ?
C6 C5 C12 O1 179.1(3) . . . . ?
C6 C5 C12 C13 -0.5(5) . . . . ?
C11 O1 C12 C5 179.9(3) . . . . ?
C11 O1 C12 C13 -0.5(4) . . . . ?
C10 C9 C13 C12 -1.0(5) . . . . ?
C18' C9 C13 C12 178.5(3) . . . . ?
C18 C9 C13 C12 178.5(3) . . . . ?
C10 C9 C13 C8 176.5(3) . . . . ?
C18' C9 C13 C8 -4.0(5) . . . . ?
C18 C9 C13 C8 -4.0(5) . . . . ?
C5 C12 C13 C9 -178.9(3) . . . . ?
O1 C12 C13 C9 1.5(5) . . . . ?
C5 C12 C13 C8 3.4(5) . . . . ?
O1 C12 C13 C8 -176.2(3) . . . . ?
C7 C8 C13 C9 179.5(3) . . . . ?
C7 C8 C13 C12 -2.9(5) . . . . ?
C10 C9 C18 C19 130.1(10) . . . . ?
C13 C9 C18 C19 -49.4(10) . . . . ?
C10 C9 C18 S1 -49.9(4) . . . . ?
C13 C9 C18 S1 130.6(3) . . . . ?
C9 C18 C19 C20 -179.8(6) . . . . ?
S1 C18 C19 C20 0.3(14) . . . . ?
C18 C19 C20 C21 -0.6(14) . . . . ?
C19 C20 C21 S1 0.7(8) . . . . ?
C20 C21 S1 C18 -0.5(4) . . . . ?
C19 C18 S1 C21 0.1(8) . . . . ?
C9 C18 S1 C21 -179.9(3) . . . . ?
C10 C9 C18' C19' -43.7(10) . . . . ?
C13 C9 C18' C19' 136.8(10) . . . . ?
C10 C9 C18' S1' 127.5(9) . . . . ?
C13 C9 C18' S1' -52.0(10) . . . . ?
C9 C18' C19' C20' 172.2(8) . . . . ?
S1' C18' C19' C20' 0.0(2) . . . . ?
C18' C19' C20' C21' 0.0(3) . . . . ?
C19' C20' C21' S1' -0.1(5) . . . . ?
C20' C21' S1' C18' 0.1(4) . . . . ?
C19' C18' S1' C21' 0.0(3) . . . . ?
C9 C18' S1' C21' -171.8(8) . . . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.059



