# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1898554'
loop_
_audit_author_name
_audit_author_address
'Jacques Pecaut '
;CEA Grenoble
France
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_audit_creation_date             2017-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            1a
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H23 Cl N3 O2, F6 P'
_chemical_formula_sum            'C16 H23 Cl F6 N3 O2 P'
_chemical_formula_weight         469.79
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N4 P F6'
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'
Cl Cl 0.1484 0.1585 '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'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   10.7226(3)
_cell_length_b                   12.3939(3)
_cell_length_c                   15.6108(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.991(3)
_cell_angle_gamma                90
_cell_volume                     2071.75(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1918
_cell_measurement_temperature    123(40)
_cell_measurement_theta_max      31.3980
_cell_measurement_theta_min      2.5090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 0 0.0960
1 1 0 0.0880
-1 1 0 0.0532
1 -1 0 0.0872
0 0 1 0.2008
0 0 -1 0.2008
-1 1 1 0.1201
1 -1 -1 0.1581
0 2 -1 0.1403
-2 0 0 0.0872
2 0 0 0.0892
-2 0 2 0.1391
-1 1 -1 0.1141

_exptl_crystal_size_max          0.405
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.14
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9840 -0.9831 -0.0004 0.0731 0.0254 0.0378
0.9840 0.9831 0.0004 -0.0731 -0.0254 -0.0378
-0.9397 0.9761 -0.0057 -0.0331 0.0598 0.0483
0.9397 -0.9761 0.0057 0.0331 -0.0598 -0.0483
-0.0185 0.0029 0.9881 0.0061 0.0292 -0.0336
0.0185 -0.0029 -0.9881 -0.0061 -0.0292 0.0336
-0.9582 0.9790 0.9824 -0.0270 0.0890 0.0147
0.9582 -0.9790 -0.9824 0.0270 -0.0890 -0.0147
0.0628 1.9563 -0.9934 -0.1123 0.0052 0.0440
-1.9237 -0.0070 -0.0060 0.0400 0.0851 0.0860
1.9237 0.0070 0.0060 -0.0400 -0.0851 -0.0860
-1.9606 -0.0012 1.9701 0.0521 0.1436 0.0189
-0.9212 0.9732 -0.9937 -0.0392 0.0305 0.0818

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6369
_diffrn_reflns_point_group_measured_fraction_full 0.690
_diffrn_reflns_point_group_measured_fraction_max 0.646
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         2.514
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123(40)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9653
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 101.00   1.00   10.00    --   25.56 178.00  30.00   66
  2  ω    -22.00  67.00   1.00   10.00    --   25.56 -99.00  30.00   89
  3  ω    -30.00  71.00   1.00   10.00    --   25.56   0.00-150.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0206072000
_diffrn_orient_matrix_UB_12      -0.0537240000
_diffrn_orient_matrix_UB_13      0.0059167000
_diffrn_orient_matrix_UB_21      -0.0444154000
_diffrn_orient_matrix_UB_22      0.0186442000
_diffrn_orient_matrix_UB_23      0.0286972000
_diffrn_orient_matrix_UB_31      -0.0446429000
_diffrn_orient_matrix_UB_32      0.0062604000
_diffrn_orient_matrix_UB_33      -0.0348105000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.294
_reflns_Friedel_fraction_full    0.379
_reflns_Friedel_fraction_max     0.294
_reflns_number_gt                3656
_reflns_number_total             4090
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 783 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4090
_refine_ls_number_restraints     140
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+1.6642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1107
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
F6B \\sim F3B \\sim F2B \\sim F1B \\sim F2 \\sim F4 \\sim F5B \\sim F6 \\sim F3
\\sim F5 \\sim F1 \\sim F4B: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(F6B) \\sim Ueq, Uanis(F3B) \\sim Ueq, Uanis(F2B) \\sim Ueq, Uanis(F1B)
\\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F5B) \\sim Ueq,
Uanis(F6) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F1) \\sim
Ueq, Uanis(F4B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of
0.01
3. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
4.a :
 F1B(F2B,F3B,F4B,F5B,F6B)
4.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
4.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,
 H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.58892(10) 0.32709(8) 0.31559(6) 0.0467(3) Uani 1 1 d . . . . .
O1 O 0.6247(2) 0.49635(17) 0.43676(16) 0.0268(5) Uani 1 1 d . . . . .
O2 O 0.8279(2) 0.5420(2) 0.4426(2) 0.0411(6) Uani 1 1 d . . . . .
N1 N 0.8179(2) 0.3212(2) 0.56777(18) 0.0248(5) Uani 1 1 d . . . . .
N2 N 0.7042(2) 0.4682(2) 0.61190(18) 0.0238(5) Uani 1 1 d . . . . .
N3 N 0.6065(3) 0.2068(2) 0.45267(17) 0.0267(5) Uani 1 1 d . . . . .
C1 C 0.6578(3) 0.3955(3) 0.4718(2) 0.0228(5) Uani 1 1 d . . . . .
C2 C 0.7278(3) 0.3942(2) 0.5531(2) 0.0210(5) Uani 1 1 d . . . . .
C3 C 0.6212(3) 0.3071(3) 0.4242(2) 0.0252(6) Uani 1 1 d . . . . .
C4 C 0.8036(3) 0.5157(3) 0.6685(2) 0.0326(7) Uani 1 1 d . . . . .
H4A H 0.795578 0.490231 0.726062 0.049 Uiso 1 1 calc GR . . . .
H4B H 0.796483 0.592889 0.667431 0.049 Uiso 1 1 calc GR . . . .
H4C H 0.883577 0.494894 0.649045 0.049 Uiso 1 1 calc GR . . . .
C5 C 0.5828(3) 0.5186(3) 0.6168(3) 0.0333(7) Uani 1 1 d . . . . .
H5A H 0.588462 0.593337 0.601287 0.050 Uiso 1 1 calc GR . . . .
H5B H 0.555678 0.512833 0.674233 0.050 Uiso 1 1 calc GR . . . .
H5C H 0.523765 0.482990 0.577988 0.050 Uiso 1 1 calc GR . . . .
C6 C 0.8536(3) 0.2840(3) 0.6551(2) 0.0324(7) Uani 1 1 d . . . . .
H6A H 0.933557 0.313668 0.672901 0.049 Uiso 1 1 calc GR . . . .
H6B H 0.858402 0.206655 0.655760 0.049 Uiso 1 1 calc GR . . . .
H6C H 0.792284 0.307430 0.693719 0.049 Uiso 1 1 calc GR . . . .
C7 C 0.8856(3) 0.2707(3) 0.5001(3) 0.0338(7) Uani 1 1 d . . . . .
H7A H 0.855155 0.198568 0.490763 0.051 Uiso 1 1 calc GR . . . .
H7B H 0.972985 0.268445 0.516769 0.051 Uiso 1 1 calc GR . . . .
H7C H 0.873201 0.311694 0.448225 0.051 Uiso 1 1 calc GR . . . .
C8 C 0.5781(3) 0.1850(3) 0.5411(2) 0.0274(6) Uani 1 1 d . . . . .
H8A H 0.652350 0.161007 0.572513 0.041 Uiso 1 1 calc GR . . . .
H8B H 0.515296 0.129890 0.542374 0.041 Uiso 1 1 calc GR . . . .
H8C H 0.547961 0.249657 0.566806 0.041 Uiso 1 1 calc GR . . . .
C9 C 0.6143(4) 0.1113(3) 0.3972(3) 0.0408(9) Uani 1 1 d . . . . .
H9A H 0.665734 0.057562 0.425820 0.061 Uiso 1 1 calc GR . . . .
H9B H 0.650298 0.131492 0.344474 0.061 Uiso 1 1 calc GR . . . .
H9C H 0.532144 0.082646 0.385097 0.061 Uiso 1 1 calc GR . . . .
C10 C 0.7215(3) 0.5636(3) 0.4212(2) 0.0282(6) Uani 1 1 d . . . . .
C11 C 0.6790(3) 0.6627(3) 0.3758(2) 0.0274(6) Uani 1 1 d . . . . .
C12 C 0.5641(4) 0.6690(3) 0.3315(2) 0.0358(8) Uani 1 1 d . . . . .
H12 H 0.509220 0.610921 0.331260 0.043 Uiso 1 1 calc R . . . .
C13 C 0.5316(4) 0.7628(3) 0.2877(3) 0.0449(9) Uani 1 1 d . . . . .
H13 H 0.455108 0.767266 0.256941 0.054 Uiso 1 1 calc R . . . .
C14 C 0.6115(5) 0.8492(3) 0.2892(3) 0.0482(11) Uani 1 1 d . . . . .
H14 H 0.588306 0.912112 0.260170 0.058 Uiso 1 1 calc R . . . .
C15 C 0.7247(4) 0.8436(3) 0.3331(3) 0.0421(9) Uani 1 1 d . . . . .
H15 H 0.778317 0.902569 0.333542 0.050 Uiso 1 1 calc R . . . .
C16 C 0.7602(4) 0.7504(3) 0.3769(2) 0.0351(7) Uani 1 1 d . . . . .
H16 H 0.837385 0.746527 0.406740 0.042 Uiso 1 1 calc R . . . .
P1 P 0.23484(8) 0.39279(7) 0.62342(6) 0.02849(18) Uani 1 1 d . . . . .
F1 F 0.1114(3) 0.4424(3) 0.6609(3) 0.0622(11) Uani 0.816(4) 1 d . U P A 1
F2 F 0.3557(3) 0.3418(3) 0.5897(3) 0.0705(13) Uani 0.816(4) 1 d . U P A 1
F3 F 0.2886(4) 0.5105(4) 0.6121(4) 0.0753(17) Uani 0.816(4) 1 d . U P A 1
F4 F 0.1630(5) 0.3991(4) 0.5336(3) 0.0819(14) Uani 0.816(4) 1 d . U P A 1
F5 F 0.1774(4) 0.2754(3) 0.6358(3) 0.0670(12) Uani 0.816(4) 1 d . U P A 1
F6 F 0.2983(4) 0.3884(5) 0.7164(3) 0.0969(16) Uani 0.816(4) 1 d . U P A 1
F1B F 0.1205(11) 0.4379(10) 0.5693(10) 0.067(4) Uani 0.184(4) 1 d . U P A 2
F2B F 0.3557(12) 0.3461(12) 0.6666(10) 0.078(4) Uani 0.184(4) 1 d G U P A 2
F3B F 0.2769(13) 0.5067(10) 0.6448(10) 0.054(4) Uani 0.184(4) 1 d G U P A 2
F4B F 0.3125(12) 0.4040(12) 0.5351(8) 0.073(3) Uani 0.184(4) 1 d G U P A 2
F5B F 0.2018(11) 0.2762(9) 0.5896(9) 0.058(4) Uani 0.184(4) 1 d G U P A 2
F6B F 0.1645(13) 0.3795(13) 0.6999(8) 0.084(3) Uani 0.184(4) 1 d G U P A 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
Cl1 C3 1.730(3) . ?
O1 C1 1.402(4) . ?
O1 C10 1.363(4) . ?
O2 C10 1.202(4) . ?
N1 C2 1.335(4) . ?
N1 C6 1.471(4) . ?
N1 C7 1.453(4) . ?
N2 C2 1.332(4) . ?
N2 C4 1.471(4) . ?
N2 C5 1.450(4) . ?
N3 C3 1.333(4) . ?
N3 C8 1.454(4) . ?
N3 C9 1.471(4) . ?
C1 C2 1.440(4) . ?
C1 C3 1.370(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.478(4) . ?
C11 C12 1.383(5) . ?
C11 C16 1.393(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.370(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.364(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(5) . ?
C16 H16 0.9300 . ?
P1 F1 1.598(3) . ?
P1 F2 1.558(3) . ?
P1 F3 1.582(5) . ?
P1 F4 1.566(4) . ?
P1 F5 1.596(4) . ?
P1 F6 1.571(4) . ?
P1 F1B 1.556(12) . ?
P1 F2B 1.541(12) . ?
P1 F3B 1.514(12) . ?
P1 F4B 1.653(12) . ?
P1 F5B 1.572(11) . ?
P1 F6B 1.455(11) . ?

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
C10 O1 C1 115.8(2) . . ?
C2 N1 C6 121.5(3) . . ?
C2 N1 C7 123.4(3) . . ?
C7 N1 C6 115.0(3) . . ?
C2 N2 C4 122.1(3) . . ?
C2 N2 C5 122.4(3) . . ?
C5 N2 C4 114.9(3) . . ?
C3 N3 C8 121.6(3) . . ?
C3 N3 C9 122.8(3) . . ?
C8 N3 C9 115.5(3) . . ?
O1 C1 C2 117.6(3) . . ?
C3 C1 O1 116.2(3) . . ?
C3 C1 C2 126.2(3) . . ?
N1 C2 C1 119.9(3) . . ?
N2 C2 N1 120.7(3) . . ?
N2 C2 C1 119.4(3) . . ?
N3 C3 Cl1 116.1(2) . . ?
N3 C3 C1 126.9(3) . . ?
C1 C3 Cl1 117.0(2) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C11 112.0(3) . . ?
O2 C10 O1 122.3(3) . . ?
O2 C10 C11 125.7(3) . . ?
C12 C11 C10 122.1(3) . . ?
C12 C11 C16 120.1(3) . . ?
C16 C11 C10 117.8(3) . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.3(4) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(4) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(4) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(4) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 120.3 . . ?
C15 C16 C11 119.3(4) . . ?
C15 C16 H16 120.3 . . ?
F2 P1 F1 178.0(3) . . ?
F2 P1 F3 91.3(2) . . ?
F2 P1 F4 95.5(3) . . ?
F2 P1 F5 90.2(2) . . ?
F2 P1 F6 88.3(3) . . ?
F3 P1 F1 90.0(2) . . ?
F3 P1 F5 178.5(2) . . ?
F4 P1 F1 86.0(2) . . ?
F4 P1 F3 91.1(3) . . ?
F4 P1 F5 88.8(3) . . ?
F4 P1 F6 176.1(3) . . ?
F5 P1 F1 88.5(2) . . ?
F6 P1 F1 90.1(3) . . ?
F6 P1 F3 89.6(3) . . ?
F6 P1 F5 90.4(3) . . ?
F1B P1 F4B 86.2(5) . . ?
F1B P1 F5B 89.5(5) . . ?
F2B P1 F1B 173.0(7) . . ?
F2B P1 F4B 87.0(4) . . ?
F2B P1 F5B 88.4(5) . . ?
F3B P1 F1B 90.1(5) . . ?
F3B P1 F2B 91.1(5) . . ?
F3B P1 F4B 87.1(4) . . ?
F3B P1 F5B 172.0(7) . . ?
F5B P1 F4B 84.9(4) . . ?
F6B P1 F1B 93.4(5) . . ?
F6B P1 F2B 93.4(6) . . ?
F6B P1 F3B 94.9(5) . . ?
F6B P1 F4B 178.0(6) . . ?
F6B P1 F5B 93.1(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
O1 C1 C2 N1 -142.1(3) . . . . ?
O1 C1 C2 N2 35.9(4) . . . . ?
O1 C1 C3 Cl1 21.5(4) . . . . ?
O1 C1 C3 N3 -157.9(3) . . . . ?
O1 C10 C11 C12 -19.1(5) . . . . ?
O1 C10 C11 C16 162.4(3) . . . . ?
O2 C10 C11 C12 160.7(4) . . . . ?
O2 C10 C11 C16 -17.8(5) . . . . ?
C1 O1 C10 O2 -6.0(5) . . . . ?
C1 O1 C10 C11 173.7(3) . . . . ?
C2 C1 C3 Cl1 -157.6(3) . . . . ?
C2 C1 C3 N3 23.0(5) . . . . ?
C3 C1 C2 N1 37.0(5) . . . . ?
C3 C1 C2 N2 -145.0(3) . . . . ?
C4 N2 C2 N1 34.7(5) . . . . ?
C4 N2 C2 C1 -143.3(3) . . . . ?
C5 N2 C2 N1 -154.2(3) . . . . ?
C5 N2 C2 C1 27.9(4) . . . . ?
C6 N1 C2 N2 29.1(4) . . . . ?
C6 N1 C2 C1 -153.0(3) . . . . ?
C7 N1 C2 N2 -152.5(3) . . . . ?
C7 N1 C2 C1 25.5(4) . . . . ?
C8 N3 C3 Cl1 -153.6(2) . . . . ?
C8 N3 C3 C1 25.7(5) . . . . ?
C9 N3 C3 Cl1 24.8(4) . . . . ?
C9 N3 C3 C1 -155.9(4) . . . . ?
C10 O1 C1 C2 59.6(4) . . . . ?
C10 O1 C1 C3 -119.6(3) . . . . ?
C10 C11 C12 C13 -177.6(4) . . . . ?
C10 C11 C16 C15 178.3(3) . . . . ?
C11 C12 C13 C14 -1.1(6) . . . . ?
C12 C11 C16 C15 -0.2(5) . . . . ?
C12 C13 C14 C15 0.8(7) . . . . ?
C13 C14 C15 C16 -0.2(6) . . . . ?
C14 C15 C16 C11 -0.1(6) . . . . ?
C16 C11 C12 C13 0.8(6) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_date_sample_data_collection 2017-12-01
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.044
_oxdiff_exptl_absorpt_empirical_full_min 0.970


####################################################################### 
# 
# 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_3d
_database_code_depnum_ccdc_archive 'CCDC 1898555'
loop_
_audit_author_name
_audit_author_address
'Jacques Pecaut '
;CEA Grenoble
France
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_audit_creation_date             2017-12-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H23 Cl2 N2 O2, F6 P'
_chemical_formula_sum            'C17 H23 Cl2 F6 N2 O2 P'
_chemical_formula_weight         503.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'O2 Cl2 N2 C17 H30'
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'
Cl Cl 0.1484 0.1585 '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'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.8795(5)
_cell_length_b                   14.5176(5)
_cell_length_c                   12.6593(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.138(4)
_cell_angle_gamma                90
_cell_volume                     2134.45(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3333
_cell_measurement_temperature    149(2)
_cell_measurement_theta_max      32.2920
_cell_measurement_theta_min      3.2500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent intense orange'
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1032
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 -1 0.3560
0 -2 1 0.3560
-2 -1 0 0.3181
2 1 0 0.2141
1 -1 -1 0.2119
-1 1 1 0.2159
-3 0 -1 0.2680
-1 -4 -7 0.2247
-8 1 2 0.2447

_exptl_crystal_size_max          0.712
_exptl_crystal_size_mid          0.532
_exptl_crystal_size_min          0.428
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.1623 1.5390 -1.0986 0.0000 0.0000 0.1000
0.1623 -1.5390 1.0986 -0.0000 -0.0000 -0.1000
-1.5533 -0.6257 -0.0302 0.0000 0.1000 0.0000
1.5533 0.6257 0.0302 -0.0000 -0.1000 -0.0000
0.6077 -1.1964 -1.4042 0.1000 0.0000 0.0000
-0.6077 1.1964 1.4042 -0.1000 -0.0000 -0.0000
-3.2689 0.2875 -1.1590 0.0000 0.2000 0.1000
-0.8380 -4.4981 -6.7757 0.4000 0.2000 0.1000
-7.5911 1.4289 1.5890 -0.2000 0.4000 0.1000

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13114
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         2.162
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9653
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  96.00   1.00    1.00    --   25.87  77.00 -90.00  100
  2  ω    -71.00  46.00   1.00    1.00    --  -27.28  19.00  90.00  117
  3  ω   -103.00 -63.00   1.00    1.00    --  -27.28-178.00 120.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0122701000
_diffrn_orient_matrix_UB_12      -0.0284486000
_diffrn_orient_matrix_UB_13      -0.0416661000
_diffrn_orient_matrix_UB_21      -0.0581052000
_diffrn_orient_matrix_UB_22      -0.0149717000
_diffrn_orient_matrix_UB_23      -0.0123920000
_diffrn_orient_matrix_UB_31      -0.0140860000
_diffrn_orient_matrix_UB_32      0.0367733000
_diffrn_orient_matrix_UB_33      -0.0374288000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5109
_reflns_number_total             6476
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         6476
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.8596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0979
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim
Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F3B) \\sim Ueq, Uanis(F4B)
\\sim Ueq, Uanis(F5B) \\sim Ueq, Uanis(F6B) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.01
2. Others
 Sof(F3B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=1-FVAR(1)
 Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.51956(3) 0.63607(3) 0.48129(3) 0.02460(9) Uani 1 1 d . . . . .
Cl2 Cl 0.20365(4) 0.42723(3) 0.23125(4) 0.03301(11) Uani 1 1 d . . . . .
O1 O 0.43567(9) 0.50966(7) 0.30670(8) 0.0191(2) Uani 1 1 d . . . . .
O2 O 0.39467(11) 0.62630(8) 0.18797(10) 0.0307(3) Uani 1 1 d . . . . .
N1 N 0.32122(11) 0.59790(8) 0.52919(10) 0.0198(2) Uani 1 1 d . . . . .
N2 N 0.14861(12) 0.58506(9) 0.30055(11) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.38235(13) 0.58949(9) 0.45303(12) 0.0179(3) Uani 1 1 d . . . . .
C2 C 0.34887(13) 0.54396(9) 0.35585(12) 0.0185(3) Uani 1 1 d . . . . .
C3 C 0.23372(14) 0.52756(10) 0.30264(12) 0.0204(3) Uani 1 1 d . . . . .
C4 C 0.34415(18) 0.66832(13) 0.61366(14) 0.0285(4) Uani 1 1 d . . . . .
H4A H 0.380(2) 0.6423(15) 0.6785(19) 0.043(6) Uiso 1 1 d . . . . .
H4B H 0.387(2) 0.7171(16) 0.5940(18) 0.046(7) Uiso 1 1 d . . . . .
H4C H 0.273(2) 0.6921(17) 0.624(2) 0.056(7) Uiso 1 1 d . . . . .
C5 C 0.22950(16) 0.53275(11) 0.53821(14) 0.0257(3) Uani 1 1 d . . . . .
H5A H 0.2412(16) 0.4774(13) 0.5023(15) 0.025(5) Uiso 1 1 d . . . . .
H5B H 0.1569(18) 0.5548(13) 0.5069(15) 0.025(5) Uiso 1 1 d . . . . .
H5C H 0.2356(16) 0.5230(13) 0.6148(16) 0.028(5) Uiso 1 1 d . . . . .
C6 C 0.16865(16) 0.68260(11) 0.32906(15) 0.0261(3) Uani 1 1 d . . . . .
H6A H 0.1645(18) 0.6932(14) 0.4037(17) 0.034(5) Uiso 1 1 d . . . . .
H6B H 0.112(2) 0.7178(14) 0.2802(17) 0.038(6) Uiso 1 1 d . . . . .
H6C H 0.2402(18) 0.6979(13) 0.3166(15) 0.026(5) Uiso 1 1 d . . . . .
C7 C 0.02753(16) 0.55920(15) 0.25927(18) 0.0340(4) Uani 1 1 d . . . . .
H7A H 0.0116(19) 0.5655(15) 0.1816(19) 0.040(6) Uiso 1 1 d . . . . .
H7B H 0.013(2) 0.4984(16) 0.2798(18) 0.046(6) Uiso 1 1 d . . . . .
H7C H -0.025(2) 0.6006(16) 0.2878(18) 0.046(6) Uiso 1 1 d . . . . .
C8 C 0.45283(13) 0.56047(9) 0.21905(12) 0.0183(3) Uani 1 1 d . . . . .
C9 C 0.55033(13) 0.52403(9) 0.17490(11) 0.0177(3) Uani 1 1 d . . . . .
C10 C 0.64663(13) 0.58067(10) 0.17844(12) 0.0201(3) Uani 1 1 d . . . . .
C11 C 0.73697(15) 0.54689(11) 0.13558(13) 0.0244(3) Uani 1 1 d . . . . .
H11 H 0.7971(17) 0.5851(13) 0.1370(15) 0.027(5) Uiso 1 1 d . . . . .
C12 C 0.73389(15) 0.45993(11) 0.08872(13) 0.0259(3) Uani 1 1 d . . . . .
C13 C 0.63621(15) 0.40649(11) 0.08484(13) 0.0243(3) Uani 1 1 d . . . . .
H13 H 0.6304(17) 0.3490(14) 0.0507(16) 0.032(5) Uiso 1 1 d . . . . .
C14 C 0.54355(14) 0.43636(10) 0.12720(12) 0.0207(3) Uani 1 1 d . . . . .
C15 C 0.65497(17) 0.67638(12) 0.22560(17) 0.0293(4) Uani 1 1 d . . . . .
H15A H 0.729(3) 0.7015(18) 0.231(2) 0.066(8) Uiso 1 1 d . . . . .
H15B H 0.604(3) 0.716(2) 0.189(2) 0.080(10) Uiso 1 1 d . . . . .
H15C H 0.642(2) 0.6793(19) 0.295(2) 0.068(8) Uiso 1 1 d . . . . .
C16 C 0.83203(19) 0.42603(15) 0.04128(19) 0.0380(4) Uani 1 1 d . . . . .
H16A H 0.806(2) 0.3846(17) -0.016(2) 0.053(7) Uiso 1 1 d . . . . .
H16B H 0.888(2) 0.3969(18) 0.094(2) 0.058(7) Uiso 1 1 d . . . . .
H16C H 0.873(2) 0.4728(18) 0.014(2) 0.055(7) Uiso 1 1 d . . . . .
C17 C 0.43820(17) 0.37715(11) 0.11653(16) 0.0292(4) Uani 1 1 d . . . . .
H17A H 0.440(2) 0.3300(18) 0.067(2) 0.061(8) Uiso 1 1 d . . . . .
H17B H 0.4291(19) 0.3528(16) 0.186(2) 0.047(6) Uiso 1 1 d . . . . .
H17C H 0.367(2) 0.4106(17) 0.0872(19) 0.055(7) Uiso 1 1 d . . . . .
P1 P 0.07433(4) 0.27853(3) 0.46569(4) 0.02903(11) Uani 1 1 d . . . . .
F1 F -0.06214(10) 0.26259(9) 0.44296(11) 0.0473(3) Uani 1 1 d . U . . .
F2 F 0.20938(11) 0.29658(10) 0.48710(11) 0.0553(4) Uani 1 1 d . U . . .
F3 F 0.09506(17) 0.17146(11) 0.48948(17) 0.0637(5) Uani 0.943(3) 1 d . U P A 1
F4 F 0.07415(14) 0.29502(16) 0.58887(12) 0.0778(7) Uani 0.943(3) 1 d . U P A 1
F5 F 0.05219(13) 0.38435(9) 0.43900(19) 0.0680(6) Uani 0.943(3) 1 d . U P A 1
F6 F 0.07520(13) 0.25806(12) 0.34251(10) 0.0485(4) Uani 0.943(3) 1 d . U P A 1
F3B F 0.103(2) 0.2024(15) 0.5437(19) 0.037(5) Uani 0.057(3) 1 d . U P A 2
F4B F 0.054(2) 0.373(2) 0.526(3) 0.063(8) Uani 0.057(3) 1 d . U P A 2
F5B F 0.0390(19) 0.3151(17) 0.3450(17) 0.039(6) Uani 0.057(3) 1 d . U P A 2
F6B F 0.060(2) 0.2006(19) 0.399(2) 0.063(8) Uani 0.057(3) 1 d . U P A 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
Cl1 C1 1.7311(15) . ?
Cl2 C3 1.7118(15) . ?
O1 C2 1.4029(17) . ?
O1 C8 1.3827(17) . ?
O2 C8 1.1964(18) . ?
N1 C1 1.3291(19) . ?
N1 C4 1.463(2) . ?
N1 C5 1.465(2) . ?
N2 C3 1.307(2) . ?
N2 C6 1.468(2) . ?
N2 C7 1.472(2) . ?
C1 C2 1.379(2) . ?
C2 C3 1.412(2) . ?
C4 H4A 0.92(2) . ?
C4 H4B 0.93(2) . ?
C4 H4C 0.95(3) . ?
C5 H5A 0.948(19) . ?
C5 H5B 0.93(2) . ?
C5 H5C 0.968(19) . ?
C6 H6A 0.97(2) . ?
C6 H6B 0.96(2) . ?
C6 H6C 0.92(2) . ?
C7 H7A 0.97(2) . ?
C7 H7B 0.94(2) . ?
C7 H7C 0.99(2) . ?
C8 C9 1.485(2) . ?
C9 C10 1.402(2) . ?
C9 C14 1.4038(19) . ?
C10 C11 1.390(2) . ?
C10 C15 1.507(2) . ?
C11 H11 0.90(2) . ?
C11 C12 1.392(2) . ?
C12 C13 1.388(2) . ?
C12 C16 1.502(2) . ?
C13 H13 0.94(2) . ?
C13 C14 1.391(2) . ?
C14 C17 1.501(2) . ?
C15 H15A 0.94(3) . ?
C15 H15B 0.90(3) . ?
C15 H15C 0.93(3) . ?
C16 H16A 0.95(3) . ?
C16 H16B 0.93(3) . ?
C16 H16C 0.94(3) . ?
C17 H17A 0.93(3) . ?
C17 H17B 0.97(2) . ?
C17 H17C 0.98(3) . ?
P1 F1 1.6026(13) . ?
P1 F2 1.5916(13) . ?
P1 F3 1.5926(16) . ?
P1 F4 1.5782(14) . ?
P1 F5 1.5831(14) . ?
P1 F6 1.5896(13) . ?
P1 F3B 1.473(19) . ?
P1 F4B 1.61(2) . ?
P1 F5B 1.59(2) . ?
P1 F6B 1.40(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
C8 O1 C2 114.37(11) . . ?
C1 N1 C4 123.24(14) . . ?
C1 N1 C5 121.73(13) . . ?
C4 N1 C5 114.92(13) . . ?
C3 N2 C6 121.75(14) . . ?
C3 N2 C7 122.56(14) . . ?
C6 N2 C7 115.41(14) . . ?
N1 C1 Cl1 116.65(11) . . ?
N1 C1 C2 126.29(14) . . ?
C2 C1 Cl1 116.99(11) . . ?
O1 C2 C3 117.21(13) . . ?
C1 C2 O1 117.69(13) . . ?
C1 C2 C3 125.10(14) . . ?
N2 C3 Cl2 117.26(12) . . ?
N2 C3 C2 124.72(14) . . ?
C2 C3 Cl2 117.97(11) . . ?
N1 C4 H4A 110.1(14) . . ?
N1 C4 H4B 111.3(14) . . ?
N1 C4 H4C 108.8(16) . . ?
H4A C4 H4B 112(2) . . ?
H4A C4 H4C 107(2) . . ?
H4B C4 H4C 108(2) . . ?
N1 C5 H5A 108.9(12) . . ?
N1 C5 H5B 112.6(12) . . ?
N1 C5 H5C 105.8(12) . . ?
H5A C5 H5B 107.8(16) . . ?
H5A C5 H5C 111.6(16) . . ?
H5B C5 H5C 110.2(16) . . ?
N2 C6 H6A 110.7(12) . . ?
N2 C6 H6B 107.4(12) . . ?
N2 C6 H6C 107.3(12) . . ?
H6A C6 H6B 111.8(17) . . ?
H6A C6 H6C 111.5(17) . . ?
H6B C6 H6C 107.9(17) . . ?
N2 C7 H7A 107.7(13) . . ?
N2 C7 H7B 111.0(15) . . ?
N2 C7 H7C 111.0(14) . . ?
H7A C7 H7B 111.1(19) . . ?
H7A C7 H7C 108.2(19) . . ?
H7B C7 H7C 107.8(19) . . ?
O1 C8 C9 111.73(12) . . ?
O2 C8 O1 121.18(14) . . ?
O2 C8 C9 127.08(14) . . ?
C10 C9 C8 118.34(12) . . ?
C10 C9 C14 121.21(14) . . ?
C14 C9 C8 120.40(14) . . ?
C9 C10 C15 122.59(14) . . ?
C11 C10 C9 118.19(14) . . ?
C11 C10 C15 119.21(15) . . ?
C10 C11 H11 116.7(12) . . ?
C10 C11 C12 122.21(16) . . ?
C12 C11 H11 121.1(12) . . ?
C11 C12 C16 120.95(17) . . ?
C13 C12 C11 117.96(15) . . ?
C13 C12 C16 121.07(16) . . ?
C12 C13 H13 119.6(13) . . ?
C12 C13 C14 122.37(14) . . ?
C14 C13 H13 118.0(13) . . ?
C9 C14 C17 121.97(14) . . ?
C13 C14 C9 118.03(15) . . ?
C13 C14 C17 119.94(14) . . ?
C10 C15 H15A 111.6(16) . . ?
C10 C15 H15B 113.9(19) . . ?
C10 C15 H15C 114.1(17) . . ?
H15A C15 H15B 108(2) . . ?
H15A C15 H15C 105(2) . . ?
H15B C15 H15C 104(2) . . ?
C12 C16 H16A 110.9(15) . . ?
C12 C16 H16B 110.9(16) . . ?
C12 C16 H16C 114.6(15) . . ?
H16A C16 H16B 109(2) . . ?
H16A C16 H16C 107(2) . . ?
H16B C16 H16C 104(2) . . ?
C14 C17 H17A 110.3(16) . . ?
C14 C17 H17B 112.1(14) . . ?
C14 C17 H17C 112.9(14) . . ?
H17A C17 H17B 111(2) . . ?
H17A C17 H17C 104(2) . . ?
H17B C17 H17C 105.8(19) . . ?
F1 P1 F4B 87.5(10) . . ?
F2 P1 F1 178.72(8) . . ?
F2 P1 F3 91.05(9) . . ?
F2 P1 F4B 91.7(10) . . ?
F3 P1 F1 90.20(9) . . ?
F4 P1 F1 89.30(8) . . ?
F4 P1 F2 91.00(8) . . ?
F4 P1 F3 89.63(12) . . ?
F4 P1 F5 91.66(12) . . ?
F4 P1 F6 177.93(11) . . ?
F5 P1 F1 89.16(8) . . ?
F5 P1 F2 89.58(8) . . ?
F5 P1 F3 178.56(13) . . ?
F5 P1 F6 90.41(11) . . ?
F6 P1 F1 90.68(7) . . ?
F6 P1 F2 89.06(7) . . ?
F6 P1 F3 88.30(10) . . ?
F3B P1 F1 95.2(9) . . ?
F3B P1 F2 86.0(9) . . ?
F3B P1 F4B 110.8(18) . . ?
F3B P1 F5B 150.7(14) . . ?
F5B P1 F1 79.8(8) . . ?
F5B P1 F2 99.3(8) . . ?
F5B P1 F4B 97.8(16) . . ?
F6B P1 F1 77.8(12) . . ?
F6B P1 F2 102.8(12) . . ?
F6B P1 F3B 77.4(16) . . ?
F6B P1 F4B 164.0(16) . . ?
F6B P1 F5B 73.3(16) . . ?

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
Cl1 C1 C2 O1 22.59(17) . . . . ?
Cl1 C1 C2 C3 -158.64(12) . . . . ?
O1 C2 C3 Cl2 32.93(17) . . . . ?
O1 C2 C3 N2 -144.46(14) . . . . ?
O1 C8 C9 C10 -116.79(14) . . . . ?
O1 C8 C9 C14 65.63(17) . . . . ?
O2 C8 C9 C10 61.7(2) . . . . ?
O2 C8 C9 C14 -115.93(18) . . . . ?
N1 C1 C2 O1 -154.47(13) . . . . ?
N1 C1 C2 C3 24.3(2) . . . . ?
C1 C2 C3 Cl2 -145.84(12) . . . . ?
C1 C2 C3 N2 36.8(2) . . . . ?
C2 O1 C8 O2 -2.0(2) . . . . ?
C2 O1 C8 C9 176.52(12) . . . . ?
C4 N1 C1 Cl1 22.11(19) . . . . ?
C4 N1 C1 C2 -160.82(15) . . . . ?
C5 N1 C1 Cl1 -154.03(12) . . . . ?
C5 N1 C1 C2 23.0(2) . . . . ?
C6 N2 C3 Cl2 -160.93(12) . . . . ?
C6 N2 C3 C2 16.5(2) . . . . ?
C7 N2 C3 Cl2 12.7(2) . . . . ?
C7 N2 C3 C2 -169.90(16) . . . . ?
C8 O1 C2 C1 -104.71(15) . . . . ?
C8 O1 C2 C3 76.43(16) . . . . ?
C8 C9 C10 C11 -179.04(14) . . . . ?
C8 C9 C10 C15 0.3(2) . . . . ?
C8 C9 C14 C13 178.50(14) . . . . ?
C8 C9 C14 C17 1.4(2) . . . . ?
C9 C10 C11 C12 0.8(2) . . . . ?
C10 C9 C14 C13 1.0(2) . . . . ?
C10 C9 C14 C17 -176.15(15) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C10 C11 C12 C16 178.89(17) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
C12 C13 C14 C9 0.3(2) . . . . ?
C12 C13 C14 C17 177.46(16) . . . . ?
C14 C9 C10 C11 -1.5(2) . . . . ?
C14 C9 C10 C15 177.86(15) . . . . ?
C15 C10 C11 C12 -178.60(16) . . . . ?
C16 C12 C13 C14 -179.42(17) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_date_sample_data_collection 2017-12-15
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.054
_oxdiff_exptl_absorpt_empirical_full_min 0.950



####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1898559'
loop_
_audit_author_name
_audit_author_address
'Jacques Pecaut '
;CEA Grenoble
France
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_audit_creation_date             2017-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 P, C28 H41 N4 O2'
_chemical_formula_sum            'C28 H41 F6 N4 O2 P'
_chemical_formula_weight         610.62
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   36.485(7)
_cell_length_b                   10.158(2)
_cell_length_c                   16.856(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.44(3)
_cell_angle_gamma                90
_cell_volume                     6242(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    39100
_cell_measurement_temperature    200
_cell_measurement_theta_max      30.000
_cell_measurement_theta_min      1.117
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.829179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.1572 before and 0.0431 after correction.
The Ratio of minimum to maximum transmission is 0.8292.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2576
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            39100
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         1.117
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  Incoatec-Bruker-AXS-enraf-noniusKappaAPEXII
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6317
_reflns_number_total             9050
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         9050
_refine_ls_number_restraints     165
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+6.5955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1496
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 P1, F9, F1, F3, F10, F5, F4, F2, F7, F6, F8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C22B, C22A, C1E, C1FB, C1FA
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
P1 \\sim F9 \\sim F1 \\sim F3 \\sim F10 \\sim F5 \\sim F4 \\sim F2 \\sim F7
\\sim F6 \\sim F8: within 1.7A with sigma of 0.04 and sigma for terminal atoms
of 0.08
C22B \\sim C22A \\sim C1E \\sim C1FB \\sim C1FA: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
4. Others
 Sof(F6)=Sof(F8)=Sof(F9)=Sof(F10)=1-FVAR(1)
 Sof(F3)=Sof(F1)=Sof(F5)=Sof(F7)=FVAR(1)
 Sof(H1EA)=Sof(C1FB)=Sof(H1FA)=Sof(H1FB)=Sof(H1FC)=Sof(C22B)=Sof(H22A)=
 Sof(H22B)=Sof(H22C)=1-FVAR(2)
 Sof(H1E)=Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=Sof(C1FA)=Sof(H1FD)=
 Sof(H1FE)=Sof(H1FF)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C17(H17), C1E(H1EA), C1E(H1E)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C14(H14), C15(H15), C16(H16), C1A(H1A), C1B(H1B), C1C(H1C), C1D(H1D)
5.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C1FB(H1FA,H1FB,H1FC),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22B(H22A,H22B,H22C), C22A(H22D,H22E,
 H22F), C1FA(H1FD,H1FE,H1FF)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.42248(2) 0.89660(5) 0.56972(3) 0.04520(14) Uani 1 1 d . U . . .
O1 O 0.40655(3) 0.61190(11) 0.27474(6) 0.0291(2) Uani 1 1 d . . . . .
O2 O 0.49108(3) 0.61049(12) 0.36533(8) 0.0392(3) Uani 1 1 d . . . . .
F3 F 0.4313(2) 0.7825(7) 0.5120(5) 0.0828(15) Uani 0.64(2) 1 d . U P A 1
F1 F 0.38946(19) 0.9374(8) 0.5154(4) 0.0910(17) Uani 0.64(2) 1 d . U P A 1
F2 F 0.39996(4) 0.7944(2) 0.62030(10) 0.0875(6) Uani 1 1 d . U . . .
F4 F 0.44630(6) 0.99158(17) 0.51825(10) 0.0918(6) Uani 1 1 d . U . . .
N4 N 0.35941(4) 0.50991(14) 0.33208(8) 0.0333(3) Uani 1 1 d . . . . .
F5 F 0.4138(3) 1.0050(7) 0.6342(4) 0.109(2) Uani 0.64(2) 1 d . U P A 1
N6 N 0.44412(4) 0.37135(13) 0.30173(9) 0.0337(3) Uani 1 1 d . . . . .
F7 F 0.45926(16) 0.8598(6) 0.6238(3) 0.0594(11) Uani 0.64(2) 1 d . U P A 1
N8 N 0.46011(4) 0.79964(13) 0.34106(9) 0.0351(3) Uani 1 1 d . . . . .
N9 N 0.43854(5) 0.40408(14) 0.43632(9) 0.0377(3) Uani 1 1 d . . . . .
C1 C 0.46225(4) 0.66990(15) 0.35098(9) 0.0290(3) Uani 1 1 d . . . . .
C2 C 0.42630(4) 0.59054(14) 0.34821(9) 0.0263(3) Uani 1 1 d . . . . .
H2 H 0.4112 0.6203 0.3915 0.032 Uiso 1 1 calc R . . . .
C3 C 0.43639(4) 0.44714(15) 0.36217(9) 0.0292(3) Uani 1 1 d . . . . .
C4 C 0.37060(4) 0.57141(15) 0.27282(9) 0.0294(3) Uani 1 1 d . . . . .
C5 C 0.32201(5) 0.47649(18) 0.34182(10) 0.0351(4) Uani 1 1 d . . . . .
C6 C 0.35184(4) 0.61163(17) 0.19694(10) 0.0319(3) Uani 1 1 d . . . . .
C7 C 0.36328(5) 0.72335(18) 0.15785(11) 0.0383(4) Uani 1 1 d . . . . .
H7 H 0.3827 0.7731 0.1794 0.046 Uiso 1 1 calc R . . . .
C8 C 0.31070(5) 0.34582(19) 0.32825(11) 0.0392(4) Uani 1 1 d . . . . .
C9 C 0.44214(7) 0.22756(17) 0.30556(14) 0.0486(5) Uani 1 1 d . . . . .
H9A H 0.4665 0.1918 0.3100 0.073 Uiso 1 1 calc GR . . . .
H9B H 0.4298 0.1946 0.2582 0.073 Uiso 1 1 calc GR . . . .
H9C H 0.4288 0.2019 0.3510 0.073 Uiso 1 1 calc GR . . . .
C10 C 0.29851(5) 0.57188(19) 0.37114(12) 0.0412(4) Uani 1 1 d . . . . .
C11 C 0.42647(6) 0.87647(17) 0.33228(12) 0.0443(4) Uani 1 1 d . . . . .
H11A H 0.4246 0.9140 0.2800 0.066 Uiso 1 1 calc GR . . . .
H11B H 0.4269 0.9457 0.3711 0.066 Uiso 1 1 calc GR . . . .
H11C H 0.4057 0.8204 0.3400 0.066 Uiso 1 1 calc GR . . . .
C12 C 0.45305(6) 0.42118(19) 0.22289(11) 0.0410(4) Uani 1 1 d . . . . .
H12A H 0.4316 0.4178 0.1881 0.062 Uiso 1 1 calc GR . . . .
H12B H 0.4720 0.3677 0.2016 0.062 Uiso 1 1 calc GR . . . .
H12C H 0.4615 0.5105 0.2276 0.062 Uiso 1 1 calc GR . . . .
C13 C 0.49387(6) 0.8757(2) 0.35265(14) 0.0520(5) Uani 1 1 d . . . . .
H13A H 0.4966 0.9032 0.4071 0.078 Uiso 1 1 calc GR . . . .
H13B H 0.4928 0.9517 0.3188 0.078 Uiso 1 1 calc GR . . . .
H13C H 0.5145 0.8221 0.3397 0.078 Uiso 1 1 calc GR . . . .
C14 C 0.31767(6) 0.6868(2) 0.05373(11) 0.0473(5) Uani 1 1 d . . . . .
H14 H 0.3065 0.7114 0.0054 0.057 Uiso 1 1 calc R . . . .
C15 C 0.27464(6) 0.3145(2) 0.34388(13) 0.0493(5) Uani 1 1 d . . . . .
H15 H 0.2664 0.2289 0.3350 0.059 Uiso 1 1 calc R . . . .
C16 C 0.32295(6) 0.5383(2) 0.16352(12) 0.0473(5) Uani 1 1 d . . . . .
H16 H 0.3149 0.4632 0.1891 0.057 Uiso 1 1 calc R . . . .
C17 C 0.33683(6) 0.2421(2) 0.29929(13) 0.0458(4) Uani 1 1 d . . . . .
H17 H 0.3582 0.2879 0.2793 0.055 Uiso 1 1 calc R . . . .
C18 C 0.41907(8) 0.4671(2) 0.50034(12) 0.0548(6) Uani 1 1 d . . . . .
H18A H 0.4338 0.5372 0.5228 0.082 Uiso 1 1 calc GR . . . .
H18B H 0.4145 0.4034 0.5408 0.082 Uiso 1 1 calc GR . . . .
H18C H 0.3962 0.5021 0.4795 0.082 Uiso 1 1 calc GR . . . .
C19 C 0.46649(7) 0.3074(2) 0.46351(14) 0.0582(6) Uani 1 1 d . . . . .
H19A H 0.4549 0.2245 0.4734 0.087 Uiso 1 1 calc GR . . . .
H19B H 0.4787 0.3383 0.5115 0.087 Uiso 1 1 calc GR . . . .
H19C H 0.4841 0.2963 0.4233 0.087 Uiso 1 1 calc GR . . . .
C1A C 0.34596(6) 0.7613(2) 0.08666(12) 0.0475(5) Uani 1 1 d . . . . .
H1A H 0.3535 0.8372 0.0611 0.057 Uiso 1 1 calc R . . . .
C1B C 0.30610(6) 0.5770(2) 0.09205(12) 0.0513(5) Uani 1 1 d . . . . .
H1B H 0.2867 0.5278 0.0700 0.062 Uiso 1 1 calc R . . . .
C1C C 0.25088(6) 0.4066(2) 0.37210(15) 0.0544(5) Uani 1 1 d . . . . .
H1C H 0.2268 0.3833 0.3820 0.065 Uiso 1 1 calc R . . . .
C1D C 0.26276(6) 0.5337(2) 0.38573(14) 0.0511(5) Uani 1 1 d . . . . .
H1D H 0.2465 0.5953 0.4051 0.061 Uiso 1 1 calc R . . . .
C1E C 0.31051(6) 0.7126(2) 0.38796(15) 0.0522(5) Uani 1 1 d . U . . .
H1EA H 0.3364 0.7172 0.3747 0.063 Uiso 0.60(3) 1 calc R . P B 2
H1E H 0.3316 0.7322 0.3557 0.063 Uiso 0.40(3) 1 calc R . P B 1
C1FB C 0.3094(4) 0.7485(18) 0.4775(8) 0.083(3) Uani 0.60(3) 1 d . U P B 2
H1FA H 0.2846 0.7428 0.4940 0.124 Uiso 0.60(3) 1 calc GR . P B 2
H1FB H 0.3183 0.8365 0.4855 0.124 Uiso 0.60(3) 1 calc GR . P B 2
H1FC H 0.3245 0.6882 0.5081 0.124 Uiso 0.60(3) 1 calc GR . P B 2
C20 C 0.35026(7) 0.1547(3) 0.36808(16) 0.0620(6) Uani 1 1 d . . . . .
H20A H 0.3631 0.2074 0.4075 0.093 Uiso 1 1 calc GR . . . .
H20B H 0.3665 0.0886 0.3489 0.093 Uiso 1 1 calc GR . . . .
H20C H 0.3296 0.1131 0.3912 0.093 Uiso 1 1 calc GR . . . .
C21 C 0.32012(8) 0.1581(3) 0.23110(16) 0.0694(7) Uani 1 1 d . . . . .
H21A H 0.2989 0.1129 0.2488 0.104 Uiso 1 1 calc GR . . . .
H21B H 0.3379 0.0950 0.2148 0.104 Uiso 1 1 calc GR . . . .
H21C H 0.3132 0.2140 0.1871 0.104 Uiso 1 1 calc GR . . . .
C22B C 0.2911(5) 0.8060(7) 0.3348(8) 0.085(3) Uani 0.60(3) 1 d . U P B 2
H22A H 0.2949 0.7825 0.2806 0.128 Uiso 0.60(3) 1 calc GR . P B 2
H22B H 0.3003 0.8933 0.3449 0.128 Uiso 0.60(3) 1 calc GR . P B 2
H22C H 0.2653 0.8035 0.3442 0.128 Uiso 0.60(3) 1 calc GR . P B 2
F6 F 0.4206(7) 0.7902(13) 0.4989(8) 0.121(5) Uani 0.36(2) 1 d . U P A 2
F8 F 0.3821(4) 0.9465(10) 0.5378(14) 0.114(4) Uani 0.36(2) 1 d . U P A 2
F9 F 0.4569(4) 0.8403(17) 0.6053(14) 0.112(4) Uani 0.36(2) 1 d . U P A 2
F10 F 0.4243(3) 1.0111(13) 0.6295(8) 0.107(3) Uani 0.36(2) 1 d . U P A 2
C22A C 0.2785(3) 0.8183(12) 0.3662(12) 0.069(3) Uani 0.40(3) 1 d . U P B 1
H22D H 0.2690 0.8030 0.3130 0.104 Uiso 0.40(3) 1 calc GR . P B 1
H22E H 0.2884 0.9057 0.3701 0.104 Uiso 0.40(3) 1 calc GR . P B 1
H22F H 0.2591 0.8089 0.4026 0.104 Uiso 0.40(3) 1 calc GR . P B 1
C1FA C 0.3214(7) 0.729(2) 0.4683(14) 0.089(6) Uani 0.40(3) 1 d . U P B 1
H1FD H 0.3011 0.7092 0.5008 0.133 Uiso 0.40(3) 1 calc GR . P B 1
H1FE H 0.3291 0.8181 0.4773 0.133 Uiso 0.40(3) 1 calc GR . P B 1
H1FF H 0.3414 0.6702 0.4816 0.133 Uiso 0.40(3) 1 calc GR . P B 1


_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 1.557(7) . ?
P1 F1 1.538(6) . ?
P1 F2 1.5937(18) . ?
P1 F4 1.5823(18) . ?
P1 F5 1.588(6) . ?
P1 F7 1.634(5) . ?
P1 F6 1.609(12) . ?
P1 F8 1.627(12) . ?
P1 F9 1.482(13) . ?
P1 F10 1.538(9) . ?
O1 C2 1.4225(18) . ?
O1 C4 1.3736(19) . ?
O2 C1 1.228(2) . ?
N4 C4 1.261(2) . ?
N4 C5 1.422(2) . ?
N6 C3 1.317(2) . ?
N6 C9 1.464(2) . ?
N6 C12 1.472(2) . ?
N8 C1 1.330(2) . ?
N8 C11 1.457(3) . ?
N8 C13 1.460(2) . ?
N9 C3 1.323(2) . ?
N9 C18 1.464(3) . ?
N9 C19 1.475(3) . ?
C1 C2 1.539(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.518(2) . ?
C4 C6 1.482(2) . ?
C5 C8 1.406(3) . ?
C5 C10 1.398(3) . ?
C6 C7 1.386(2) . ?
C6 C16 1.390(2) . ?
C7 H7 0.9300 . ?
C7 C1A 1.387(3) . ?
C8 C15 1.390(3) . ?
C8 C17 1.515(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C1D 1.393(3) . ?
C10 C1E 1.518(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C1A 1.377(3) . ?
C14 C1B 1.365(3) . ?
C15 H15 0.9300 . ?
C15 C1C 1.374(3) . ?
C16 H16 0.9300 . ?
C16 C1B 1.386(3) . ?
C17 H17 0.9800 . ?
C17 C20 1.525(3) . ?
C17 C21 1.537(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C1A H1A 0.9300 . ?
C1B H1B 0.9300 . ?
C1C H1C 0.9300 . ?
C1C C1D 1.378(3) . ?
C1D H1D 0.9300 . ?
C1E H1EA 0.9800 . ?
C1E H1E 0.9800 . ?
C1E C1FB 1.554(13) . ?
C1E C22B 1.467(8) . ?
C1E C22A 1.618(11) . ?
C1E C1FA 1.40(2) . ?
C1FB H1FA 0.9600 . ?
C1FB H1FB 0.9600 . ?
C1FB H1FC 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22B H22A 0.9600 . ?
C22B H22B 0.9600 . ?
C22B H22C 0.9600 . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9600 . ?
C1FA H1FD 0.9600 . ?
C1FA H1FE 0.9600 . ?
C1FA H1FF 0.9600 . ?

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 F2 88.6(3) . . ?
F3 P1 F4 88.7(3) . . ?
F3 P1 F5 175.5(4) . . ?
F3 P1 F7 89.5(3) . . ?
F1 P1 F3 90.4(3) . . ?
F1 P1 F2 94.9(3) . . ?
F1 P1 F4 86.8(3) . . ?
F1 P1 F5 92.6(3) . . ?
F1 P1 F7 176.1(3) . . ?
F2 P1 F7 89.0(2) . . ?
F2 P1 F6 87.2(4) . . ?
F2 P1 F8 84.3(7) . . ?
F4 P1 F2 176.80(12) . . ?
F4 P1 F5 94.8(4) . . ?
F4 P1 F7 89.3(2) . . ?
F4 P1 F6 90.6(4) . . ?
F4 P1 F8 98.0(7) . . ?
F5 P1 F2 87.9(4) . . ?
F5 P1 F7 87.8(3) . . ?
F6 P1 F8 87.4(7) . . ?
F9 P1 F2 88.8(5) . . ?
F9 P1 F4 89.0(5) . . ?
F9 P1 F6 92.9(7) . . ?
F9 P1 F8 173.0(9) . . ?
F9 P1 F10 90.8(9) . . ?
F10 P1 F2 98.7(6) . . ?
F10 P1 F4 83.6(6) . . ?
F10 P1 F6 173.1(8) . . ?
F10 P1 F8 89.7(7) . . ?
C4 O1 C2 114.99(12) . . ?
C4 N4 C5 123.67(14) . . ?
C3 N6 C9 122.45(16) . . ?
C3 N6 C12 124.09(14) . . ?
C9 N6 C12 113.34(15) . . ?
C1 N8 C11 126.03(15) . . ?
C1 N8 C13 117.57(16) . . ?
C11 N8 C13 115.62(15) . . ?
C3 N9 C18 122.72(16) . . ?
C3 N9 C19 121.73(18) . . ?
C18 N9 C19 114.38(17) . . ?
O2 C1 N8 123.84(15) . . ?
O2 C1 C2 118.07(14) . . ?
N8 C1 C2 118.02(14) . . ?
O1 C2 C1 110.25(12) . . ?
O1 C2 H2 108.7 . . ?
O1 C2 C3 113.06(12) . . ?
C1 C2 H2 108.7 . . ?
C3 C2 C1 107.29(12) . . ?
C3 C2 H2 108.7 . . ?
N6 C3 N9 122.10(15) . . ?
N6 C3 C2 119.96(14) . . ?
N9 C3 C2 117.88(14) . . ?
O1 C4 C6 110.08(13) . . ?
N4 C4 O1 118.09(14) . . ?
N4 C4 C6 131.83(15) . . ?
C8 C5 N4 118.89(17) . . ?
C10 C5 N4 118.77(16) . . ?
C10 C5 C8 122.11(16) . . ?
C7 C6 C4 119.91(15) . . ?
C7 C6 C16 119.00(16) . . ?
C16 C6 C4 121.08(16) . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C1A 120.24(17) . . ?
C1A C7 H7 119.9 . . ?
C5 C8 C17 121.61(16) . . ?
C15 C8 C5 117.34(19) . . ?
C15 C8 C17 121.03(18) . . ?
N6 C9 H9A 109.5 . . ?
N6 C9 H9B 109.5 . . ?
N6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 C1E 122.83(17) . . ?
C1D C10 C5 117.56(18) . . ?
C1D C10 C1E 119.60(19) . . ?
N8 C11 H11A 109.5 . . ?
N8 C11 H11B 109.5 . . ?
N8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N6 C12 H12A 109.5 . . ?
N6 C12 H12B 109.5 . . ?
N6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N8 C13 H13A 109.5 . . ?
N8 C13 H13B 109.5 . . ?
N8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1A C14 H14 120.0 . . ?
C1B C14 H14 120.0 . . ?
C1B C14 C1A 119.99(18) . . ?
C8 C15 H15 119.1 . . ?
C1C C15 C8 121.72(19) . . ?
C1C C15 H15 119.1 . . ?
C6 C16 H16 120.0 . . ?
C1B C16 C6 120.04(19) . . ?
C1B C16 H16 120.0 . . ?
C8 C17 H17 107.6 . . ?
C8 C17 C20 110.24(19) . . ?
C8 C17 C21 113.07(19) . . ?
C20 C17 H17 107.6 . . ?
C20 C17 C21 110.5(2) . . ?
C21 C17 H17 107.6 . . ?
N9 C18 H18A 109.5 . . ?
N9 C18 H18B 109.5 . . ?
N9 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N9 C19 H19A 109.5 . . ?
N9 C19 H19B 109.5 . . ?
N9 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 C1A H1A 119.9 . . ?
C14 C1A C7 120.14(19) . . ?
C14 C1A H1A 119.9 . . ?
C14 C1B C16 120.57(19) . . ?
C14 C1B H1B 119.7 . . ?
C16 C1B H1B 119.7 . . ?
C15 C1C H1C 120.1 . . ?
C15 C1C C1D 119.81(19) . . ?
C1D C1C H1C 120.1 . . ?
C10 C1D H1D 119.3 . . ?
C1C C1D C10 121.4(2) . . ?
C1C C1D H1D 119.3 . . ?
C10 C1E H1EA 106.0 . . ?
C10 C1E H1E 108.3 . . ?
C10 C1E C1FB 112.5(7) . . ?
C10 C1E C22A 112.5(5) . . ?
C1FB C1E H1EA 106.0 . . ?
C22B C1E C10 111.5(4) . . ?
C22B C1E H1EA 106.0 . . ?
C22B C1E C1FB 114.1(7) . . ?
C22A C1E H1E 108.3 . . ?
C1FA C1E C10 111.0(11) . . ?
C1FA C1E H1E 108.3 . . ?
C1FA C1E C22A 108.2(9) . . ?
C1E C1FB H1FA 109.5 . . ?
C1E C1FB H1FB 109.5 . . ?
C1E C1FB H1FC 109.5 . . ?
H1FA C1FB H1FB 109.5 . . ?
H1FA C1FB H1FC 109.5 . . ?
H1FB C1FB H1FC 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1E C22B H22A 109.5 . . ?
C1E C22B H22B 109.5 . . ?
C1E C22B H22C 109.5 . . ?
H22A C22B H22B 109.5 . . ?
H22A C22B H22C 109.5 . . ?
H22B C22B H22C 109.5 . . ?
C1E C22A H22D 109.5 . . ?
C1E C22A H22E 109.5 . . ?
C1E C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C1E C1FA H1FD 109.5 . . ?
C1E C1FA H1FE 109.5 . . ?
C1E C1FA H1FF 109.5 . . ?
H1FD C1FA H1FE 109.5 . . ?
H1FD C1FA H1FF 109.5 . . ?
H1FE C1FA H1FF 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'


####################################################################### 
# 
# 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_8ameso
_database_code_depnum_ccdc_archive 'CCDC 1898560'
loop_
_audit_author_name
_audit_author_address
'Jacques Pecaut '
;CEA Grenoble
France
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_audit_creation_date             2019-02-11
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(F6 P), C32 H46 N6 O4, C2 H3 N'
_chemical_formula_sum            'C34 H49 F12 N7 O4 P2'
_chemical_formula_weight         909.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N4 C30 H30 P F6'
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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   24.915(2)
_cell_length_b                   8.8562(7)
_cell_length_c                   19.8464(18)
_cell_angle_alpha                90
_cell_angle_beta                 105.666(9)
_cell_angle_gamma                90
_cell_volume                     4216.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1186
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      21.3690
_cell_measurement_theta_min      2.4430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0787
1 0 0 0.0787
-1 0 1 0.1504
1 0 -1 0.1174
-1 -1 -1 0.0929
0 -1 1 0.0904
0 1 -1 0.1214
-1 2 2 0.0979
1 -2 -2 0.1049
-1 0 -2 0.1298
-2 1 1 0.0959

_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.157
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9984 -0.0009 -0.0040 0.0245 0.0165 0.0002
0.9984 0.0009 0.0040 -0.0245 -0.0165 -0.0002
-0.9991 0.0009 0.9930 0.0311 -0.0117 0.0232
0.9991 -0.0009 -0.9930 -0.0311 0.0117 -0.0232
-0.9952 -1.0023 -1.0028 -0.0113 0.0879 0.0378
0.0017 -0.9978 0.9953 -0.0227 0.0150 0.0837
-0.0017 0.9978 -0.9953 0.0227 -0.0150 -0.0837
-1.0047 2.0020 1.9935 0.0963 -0.1264 -0.0751
1.0047 -2.0020 -1.9935 -0.0963 0.1264 0.0751
-0.9969 -0.0045 -1.9980 0.0114 0.0729 -0.0459
-1.9999 0.9997 0.9907 0.0850 -0.0385 -0.0373

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9639
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.132
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9653
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00  17.00   1.00    8.00    --  -26.81 -19.00-120.00  117
  2  ω    -97.00   3.00   1.00    8.00    --  -26.81 -77.00  60.00  100
  3  ω    -47.00  -1.00   1.00    8.00    --   25.41 -37.00 -60.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0246387000
_diffrn_orient_matrix_UB_12      0.0292233000
_diffrn_orient_matrix_UB_13      0.0065443000
_diffrn_orient_matrix_UB_21      -0.0163549000
_diffrn_orient_matrix_UB_22      -0.0432340000
_diffrn_orient_matrix_UB_23      -0.0282263000
_diffrn_orient_matrix_UB_31      -0.0002018000
_diffrn_orient_matrix_UB_32      -0.0607219000
_diffrn_orient_matrix_UB_33      0.0231945000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2597
_reflns_number_total             4280
_reflns_odcompleteness_completeness 66.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         4280
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.1380
_refine_ls_R_factor_gt           0.0803
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0657P)²+9.7135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1669
_refine_ls_wR_factor_ref         0.1960
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C11 \\sim C11' \\sim C16 \\sim C16' \\sim C15 \\sim C15' \\sim C14
\\sim C14' \\sim C13 \\sim C13' \\sim C12 \\sim C12': within 1.7A with sigma of
0.01 and sigma for terminal atoms of 0.02
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F1B \\sim F2B \\sim F3B
\\sim F4B \\sim F5B \\sim F6B: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.02
P1 \\sim P1B: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(C22) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(N21) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(P1B)=Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=1-FVAR(1)
 Sof(P1)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Sof(C1')=Sof(C11')=Sof(C16')=Sof(H16')=Sof(C15')=Sof(H15')=Sof(C14')=
 Sof(H14')=Sof(C13')=Sof(H13')=Sof(C12')=Sof(H12')=1-FVAR(2)
 Sof(C1)=Sof(C11)=Sof(C16)=Sof(H16)=Sof(C15)=Sof(H15)=Sof(C14)=Sof(H14)=
 Sof(C13)=Sof(H13)=Sof(C12)=Sof(H12)=FVAR(2)
 Fixed Sof: N21(0.5) C21(0.5) C22(0.5) H22A(0.5) H22B(0.5) H22C(0.5)
4.a :
 P1(F1,F2,F3,F4,F5,F6), P1B(F1B,F2B,F3B,F4B,F5B,F6B)
4.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C16'(H16'), C15(H15), C15'(H15'), C14(H14), C14'(H14'), C13(H13),
 C13'(H13'), C12(H12), C12'(H12')
4.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C5(H5A,H5B,H5C), C4(H4A,H4B,H4C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.35347(8) 0.5071(2) 0.18803(10) 0.0414(11) Uani 0.730(5) 1 d . U P A 1
F1 F 0.39691(13) 0.6024(5) 0.24480(19) 0.103(2) Uani 0.730(5) 1 d G U P A 1
F2 F 0.30998(14) 0.4132(5) 0.13132(19) 0.107(2) Uani 0.730(5) 1 d G U P A 1
F3 F 0.40025(14) 0.4591(5) 0.15357(17) 0.0751(15) Uani 0.730(5) 1 d G U P A 1
F4 F 0.3417(2) 0.6501(4) 0.1393(2) 0.140(3) Uani 0.730(5) 1 d G U P A 1
F5 F 0.30614(13) 0.5564(5) 0.2214(2) 0.0862(19) Uani 0.730(5) 1 d G U P A 1
F6 F 0.3654(2) 0.3665(4) 0.2376(2) 0.124(2) Uani 0.730(5) 1 d G U P A 1
P1B P 0.3495(2) 0.5014(6) 0.1838(3) 0.049(3) Uani 0.270(5) 1 d . U P A 2
F1B F 0.4014(4) 0.5273(14) 0.2450(5) 0.122(6) Uani 0.270(5) 1 d G U P A 2
F2B F 0.2975(4) 0.4744(11) 0.1225(4) 0.046(3) Uani 0.270(5) 1 d G U P A 2
F3B F 0.3792(5) 0.5744(16) 0.1344(5) 0.092(4) Uani 0.270(5) 1 d G U P A 2
F4B F 0.3261(5) 0.6536(12) 0.1980(6) 0.129(5) Uani 0.270(5) 1 d G U P A 2
F5B F 0.3206(5) 0.4265(16) 0.2335(5) 0.120(5) Uani 0.270(5) 1 d G U P A 2
F6B F 0.3722(5) 0.3477(12) 0.1692(7) 0.129(5) Uani 0.270(5) 1 d G U P A 2
O2 O 0.47899(10) 0.0441(3) 0.40768(12) 0.0378(7) Uani 1 1 d . . . . .
O1 O 0.43311(11) 0.0921(3) 0.49069(12) 0.0409(7) Uani 1 1 d . . . . .
N2 N 0.43029(13) 0.0670(4) 0.25968(15) 0.0375(8) Uani 1 1 d . . . . .
N3 N 0.34912(14) -0.0280(4) 0.28117(16) 0.0394(8) Uani 1 1 d . . . . .
N1 N 0.34624(12) 0.1590(4) 0.42539(16) 0.0348(8) Uani 1 1 d . . . . .
C6 C 0.39982(16) 0.0357(4) 0.30377(19) 0.0339(9) Uani 1 1 d . . . . .
C3 C 0.42124(14) 0.0683(4) 0.37562(18) 0.0301(8) Uani 1 1 d . . . . .
C2 C 0.39642(15) 0.1049(4) 0.42616(18) 0.0295(8) Uani 1 1 d . . . . .
C1 C 0.4895(3) 0.0774(14) 0.4804(4) 0.029(3) Uani 0.58(2) 1 d . U P B 1
C1' C 0.4748(6) -0.019(2) 0.4748(6) 0.041(5) Uani 0.42(2) 1 d . . P B 2
C7 C 0.47388(18) 0.1819(5) 0.2755(2) 0.0502(12) Uani 1 1 d . . . . .
H7A H 0.509687 0.133900 0.290494 0.075 Uiso 1 1 calc GR . . . .
H7B H 0.468681 0.246354 0.312152 0.075 Uiso 1 1 calc GR . . . .
H7C H 0.471945 0.240987 0.234403 0.075 Uiso 1 1 calc GR . . . .
C8 C 0.4245(2) -0.0145(6) 0.1937(2) 0.0572(13) Uani 1 1 d . . . . .
H8A H 0.402694 0.044802 0.155550 0.086 Uiso 1 1 calc GR . . . .
H8B H 0.406283 -0.109367 0.195337 0.086 Uiso 1 1 calc GR . . . .
H8C H 0.460741 -0.032078 0.187026 0.086 Uiso 1 1 calc GR . . . .
C9 C 0.3109(2) 0.0053(6) 0.2125(2) 0.0617(14) Uani 1 1 d . . . . .
H9A H 0.310147 -0.078605 0.181644 0.093 Uiso 1 1 calc GR . . . .
H9B H 0.323505 0.093918 0.193373 0.093 Uiso 1 1 calc GR . . . .
H9C H 0.274176 0.022565 0.217519 0.093 Uiso 1 1 calc GR . . . .
C10 C 0.32807(19) -0.1342(5) 0.3244(2) 0.0497(11) Uani 1 1 d . . . . .
H10A H 0.301206 -0.084376 0.343443 0.075 Uiso 1 1 calc GR . . . .
H10B H 0.358439 -0.169780 0.361940 0.075 Uiso 1 1 calc GR . . . .
H10C H 0.310738 -0.218265 0.296306 0.075 Uiso 1 1 calc GR . . . .
C5 C 0.31111(17) 0.2303(5) 0.3630(2) 0.0433(10) Uani 1 1 d . . . . .
H5A H 0.282761 0.160624 0.339259 0.065 Uiso 1 1 calc GR . . . .
H5B H 0.333424 0.258685 0.332468 0.065 Uiso 1 1 calc GR . . . .
H5C H 0.293935 0.318557 0.376065 0.065 Uiso 1 1 calc GR . . . .
C4 C 0.32732(17) 0.1625(5) 0.4885(2) 0.0467(11) Uani 1 1 d . . . . .
H4A H 0.329203 0.264087 0.505890 0.070 Uiso 1 1 calc GR . . . .
H4B H 0.350728 0.098520 0.523380 0.070 Uiso 1 1 calc GR . . . .
H4C H 0.289537 0.127169 0.478036 0.070 Uiso 1 1 calc GR . . . .
C11 C 0.5258(5) 0.2115(14) 0.5058(6) 0.036(2) Uani 0.58(2) 1 d . U P B 1
C11' C 0.4574(7) -0.1838(18) 0.4752(10) 0.034(3) Uani 0.42(2) 1 d . U P B 2
C16 C 0.5656(9) 0.256(2) 0.4754(13) 0.043(3) Uani 0.58(2) 1 d . U P B 1
H16 H 0.566915 0.202166 0.435578 0.052 Uiso 0.58(2) 1 calc R . P B 1
C16' C 0.4261(12) -0.224(3) 0.5233(19) 0.040(4) Uani 0.42(2) 1 d . U P B 2
H16' H 0.417103 -0.161658 0.556199 0.048 Uiso 0.42(2) 1 calc R . P B 2
C15 C 0.6021(7) 0.362(2) 0.4937(11) 0.054(4) Uani 0.58(2) 1 d . U P B 1
H15 H 0.629811 0.377470 0.471161 0.065 Uiso 0.58(2) 1 calc R . P B 1
C15' C 0.4099(9) -0.394(2) 0.5098(15) 0.044(4) Uani 0.42(2) 1 d . U P B 2
H15' H 0.389765 -0.437758 0.538024 0.053 Uiso 0.42(2) 1 calc R . P B 2
C14 C 0.5971(6) 0.4514(17) 0.5502(7) 0.064(3) Uani 0.58(2) 1 d . U P B 1
H14 H 0.619942 0.535201 0.563705 0.077 Uiso 0.58(2) 1 calc R . P B 1
C14' C 0.4218(8) -0.482(2) 0.4625(11) 0.052(4) Uani 0.42(2) 1 d . U P B 2
H14' H 0.407482 -0.579551 0.456621 0.063 Uiso 0.42(2) 1 calc R . P B 2
C13 C 0.5591(7) 0.416(2) 0.5847(12) 0.056(4) Uani 0.58(2) 1 d . U P B 1
H13 H 0.558639 0.471020 0.624365 0.067 Uiso 0.58(2) 1 calc R . P B 1
C13' C 0.4553(9) -0.433(3) 0.4210(17) 0.048(4) Uani 0.42(2) 1 d . U P B 2
H13' H 0.468386 -0.497482 0.391912 0.057 Uiso 0.42(2) 1 calc R . P B 2
C12 C 0.5192(7) 0.296(2) 0.5630(10) 0.046(3) Uani 0.58(2) 1 d . U P B 1
H12 H 0.491372 0.276164 0.585011 0.055 Uiso 0.58(2) 1 calc R . P B 1
C12' C 0.4676(9) -0.280(3) 0.4266(15) 0.041(4) Uani 0.42(2) 1 d . U P B 2
H12' H 0.484427 -0.238841 0.394200 0.049 Uiso 0.42(2) 1 calc R . P B 2
N21 N 0.2456(5) -0.5027(10) 0.4749(5) 0.078(3) Uani 0.5 1 d . U P C -1
C21 C 0.2494(14) -0.3815(12) 0.4874(10) 0.065(5) Uani 0.5 1 d . U P C -1
C22 C 0.2625(7) -0.2246(11) 0.4891(11) 0.082(5) Uani 0.5 1 d . U P C -1
H22A H 0.230599 -0.169418 0.462540 0.123 Uiso 0.5 1 calc GR . P C -1
H22B H 0.293160 -0.208892 0.469238 0.123 Uiso 0.5 1 calc GR . P C -1
H22C H 0.272491 -0.189786 0.536680 0.123 Uiso 0.5 1 calc GR . P C -1


_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 F1 1.579(2) . ?
P1 F2 1.573(2) . ?
P1 F3 1.561(2) . ?
P1 F4 1.571(2) . ?
P1 F5 1.563(2) . ?
P1 F6 1.565(2) . ?
P1B F1B 1.533(6) . ?
P1B F2B 1.539(6) . ?
P1B F3B 1.522(6) . ?
P1B F4B 1.525(6) . ?
P1B F5B 1.522(6) . ?
P1B F6B 1.531(6) . ?
O2 C3 1.423(4) . ?
O2 C1 1.426(8) . ?
O2 C1' 1.473(12) . ?
O1 C2 1.363(4) . ?
O1 C1 1.479(7) . ?
O1 C1' 1.522(12) . ?
N2 C6 1.333(5) . ?
N2 C7 1.459(5) . ?
N2 C8 1.468(5) . ?
N3 C6 1.345(5) . ?
N3 C9 1.466(5) . ?
N3 C10 1.463(5) . ?
N1 C2 1.335(4) . ?
N1 C5 1.453(5) . ?
N1 C4 1.454(5) . ?
C6 C3 1.411(5) . ?
C3 C2 1.353(5) . ?
C1 C1 1.59(2) 5_656 ?
C1 C11 1.495(17) . ?
C1' C1' 1.41(3) 5_656 ?
C1' C11' 1.53(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C11 C16 1.35(2) . ?
C11 C12 1.41(2) . ?
C11' C16' 1.43(4) . ?
C11' C12' 1.36(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.29(3) . ?
C16' H16' 0.9300 . ?
C16' C15' 1.56(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.41(2) . ?
C15' H15' 0.9300 . ?
C15' C14' 1.31(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.35(2) . ?
C14' H14' 0.9300 . ?
C14' C13' 1.39(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.44(4) . ?
C13' H13' 0.9300 . ?
C13' C12' 1.39(5) . ?
C12 H12 0.9300 . ?
C12' H12' 0.9300 . ?
N21 C21 1.100(12) . ?
C21 C22 1.425(15) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
F2 P1 F1 179.6 . . ?
F3 P1 F1 90.5 . . ?
F3 P1 F2 89.7 . . ?
F3 P1 F4 89.3 . . ?
F3 P1 F5 179.1 . . ?
F3 P1 F6 91.2 . . ?
F4 P1 F1 89.2 . . ?
F4 P1 F2 90.4 . . ?
F5 P1 F1 89.9 . . ?
F5 P1 F2 89.9 . . ?
F5 P1 F4 89.9 . . ?
F5 P1 F6 89.6 . . ?
F6 P1 F1 90.0 . . ?
F6 P1 F2 90.3 . . ?
F6 P1 F4 179.1 . . ?
F1B P1B F2B 179.66(9) . . ?
F3B P1B F1B 89.6 . . ?
F3B P1B F2B 90.5 . . ?
F3B P1B F4B 91.1 . . ?
F3B P1B F5B 179.1 . . ?
F3B P1B F6B 89.3 . . ?
F4B P1B F1B 90.3 . . ?
F4B P1B F2B 90.0 . . ?
F4B P1B F6B 179.1 . . ?
F5B P1B F1B 89.9 . . ?
F5B P1B F2B 89.9 . . ?
F5B P1B F4B 89.6 . . ?
F5B P1B F6B 89.9 . . ?
F6B P1B F1B 90.4 . . ?
F6B P1B F2B 89.3 . . ?
C3 O2 C1 108.0(3) . . ?
C3 O2 C1' 98.7(5) . . ?
C2 O1 C1 107.4(3) . . ?
C2 O1 C1' 100.5(5) . . ?
C6 N2 C7 121.7(3) . . ?
C6 N2 C8 123.2(4) . . ?
C7 N2 C8 115.0(3) . . ?
C6 N3 C9 122.7(4) . . ?
C6 N3 C10 121.8(3) . . ?
C10 N3 C9 115.4(3) . . ?
C2 N1 C5 120.8(3) . . ?
C2 N1 C4 121.2(3) . . ?
C5 N1 C4 117.7(3) . . ?
N2 C6 N3 121.2(3) . . ?
N2 C6 C3 119.6(3) . . ?
N3 C6 C3 119.2(3) . . ?
C6 C3 O2 118.8(3) . . ?
C2 C3 O2 108.3(3) . . ?
C2 C3 C6 132.4(3) . . ?
N1 C2 O1 115.4(3) . . ?
N1 C2 C3 133.8(3) . . ?
C3 C2 O1 110.6(3) . . ?
O2 C1 O1 103.7(5) . . ?
O2 C1 C1 105.3(9) . 5_656 ?
O2 C1 C11 115.8(7) . . ?
O1 C1 C1 101.9(9) . 5_656 ?
O1 C1 C11 113.1(7) . . ?
C11 C1 C1 115.5(10) . 5_656 ?
O2 C1' O1 99.4(8) . . ?
O2 C1' C11' 117.1(11) . . ?
O1 C1' C11' 113.9(10) . . ?
C1' C1' O2 106.6(17) 5_656 . ?
C1' C1' O1 103.2(16) 5_656 . ?
C1' C1' C11' 114.7(19) 5_656 . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C16 C11 C1 122.0(12) . . ?
C16 C11 C12 117.8(13) . . ?
C12 C11 C1 120.3(11) . . ?
C16' C11' C1' 116.8(14) . . ?
C12' C11' C1' 119.1(15) . . ?
C12' C11' C16' 123.8(17) . . ?
C11 C16 H16 115.4 . . ?
C15 C16 C11 129(2) . . ?
C15 C16 H16 115.4 . . ?
C11' C16' H16' 126.6 . . ?
C11' C16' C15' 107(3) . . ?
C15' C16' H16' 126.6 . . ?
C16 C15 H15 122.3 . . ?
C16 C15 C14 115(2) . . ?
C14 C15 H15 122.3 . . ?
C16' C15' H15' 116.8 . . ?
C14' C15' C16' 126(3) . . ?
C14' C15' H15' 116.8 . . ?
C15 C14 H14 120.1 . . ?
C13 C14 C15 119.8(14) . . ?
C13 C14 H14 120.1 . . ?
C15' C14' H14' 119.1 . . ?
C15' C14' C13' 121.8(17) . . ?
C13' C14' H14' 119.1 . . ?
C14 C13 H13 118.5 . . ?
C14 C13 C12 123(2) . . ?
C12 C13 H13 118.5 . . ?
C14' C13' H13' 122.9 . . ?
C12' C13' C14' 114(3) . . ?
C12' C13' H13' 122.9 . . ?
C11 C12 C13 114(2) . . ?
C11 C12 H12 122.8 . . ?
C13 C12 H12 122.8 . . ?
C11' C12' C13' 126(3) . . ?
C11' C12' H12' 117.0 . . ?
C13' C12' H12' 117.0 . . ?
N21 C21 C22 164(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O2 C3 C2 O1 -6.0(4) . . . . ?
O2 C3 C2 N1 168.7(4) . . . . ?
O2 C1 C11 C16 -29.4(13) . . . . ?
O2 C1 C11 C12 150.7(9) . . . . ?
O2 C1' C11' C16' -148.3(15) . . . . ?
O2 C1' C11' C12' 25.8(16) . . . . ?
O1 C1 C11 C16 -148.9(11) . . . . ?
O1 C1 C11 C12 31.3(11) . . . . ?
O1 C1' C11' C16' -33.1(18) . . . . ?
O1 C1' C11' C12' 141.1(12) . . . . ?
N2 C6 C3 O2 -38.1(5) . . . . ?
N2 C6 C3 C2 150.6(4) . . . . ?
N3 C6 C3 O2 141.2(4) . . . . ?
N3 C6 C3 C2 -30.1(7) . . . . ?
C6 C3 C2 O1 166.0(4) . . . . ?
C6 C3 C2 N1 -19.4(8) . . . . ?
C3 O2 C1 O1 10.9(8) . . . . ?
C3 O2 C1 C1 117.6(7) . . . 5_656 ?
C3 O2 C1 C11 -113.6(7) . . . . ?
C3 O2 C1' O1 -44.7(11) . . . . ?
C3 O2 C1' C1' -151.6(14) . . . 5_656 ?
C3 O2 C1' C11' 78.3(10) . . . . ?
C2 O1 C1 O2 -14.5(8) . . . . ?
C2 O1 C1 C1 -123.7(7) . . . 5_656 ?
C2 O1 C1 C11 111.7(6) . . . . ?
C2 O1 C1' O2 42.2(11) . . . . ?
C2 O1 C1' C1' 151.9(13) . . . 5_656 ?
C2 O1 C1' C11' -83.0(9) . . . . ?
C1 O2 C3 C6 -177.0(6) . . . . ?
C1 O2 C3 C2 -3.8(7) . . . . ?
C1 O1 C2 N1 -162.8(6) . . . . ?
C1 O1 C2 C3 13.0(6) . . . . ?
C1 C1 C11 C16 94.2(13) 5_656 . . . ?
C1 C1 C11 C12 -85.6(11) 5_656 . . . ?
C1 C11 C16 C15 -175(2) . . . . ?
C1 C11 C12 C13 176.2(15) . . . . ?
C1' O2 C3 C6 -140.1(9) . . . . ?
C1' O2 C3 C2 33.1(9) . . . . ?
C1' O1 C2 N1 161.1(8) . . . . ?
C1' O1 C2 C3 -23.1(9) . . . . ?
C1' C1' C11' C16' 85.6(19) 5_656 . . . ?
C1' C1' C11' C12' -100.3(15) 5_656 . . . ?
C1' C11' C16' C15' 176.0(19) . . . . ?
C1' C11' C12' C13' 179(2) . . . . ?
C7 N2 C6 N3 156.9(4) . . . . ?
C7 N2 C6 C3 -23.8(6) . . . . ?
C8 N2 C6 N3 -25.8(6) . . . . ?
C8 N2 C6 C3 153.5(4) . . . . ?
C9 N3 C6 N2 -34.8(6) . . . . ?
C9 N3 C6 C3 145.9(4) . . . . ?
C10 N3 C6 N2 146.1(4) . . . . ?
C10 N3 C6 C3 -33.2(5) . . . . ?
C5 N1 C2 O1 157.0(3) . . . . ?
C5 N1 C2 C3 -17.5(7) . . . . ?
C4 N1 C2 O1 -16.7(5) . . . . ?
C4 N1 C2 C3 168.8(4) . . . . ?
C11 C16 C15 C14 -5(3) . . . . ?
C11' C16' C15' C14' -1(3) . . . . ?
C16 C11 C12 C13 -3.7(19) . . . . ?
C16 C15 C14 C13 6(2) . . . . ?
C16' C11' C12' C13' -8(3) . . . . ?
C16' C15' C14' C13' 5(3) . . . . ?
C15 C14 C13 C12 -6(2) . . . . ?
C15' C14' C13' C12' -9(3) . . . . ?
C14 C13 C12 C11 5(2) . . . . ?
C14' C13' C12' C11' 11(3) . . . . ?
C12 C11 C16 C15 5(3) . . . . ?
C12' C11' C16' C15' 2(3) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.052
_oxdiff_exptl_absorpt_empirical_full_min 0.957



####################################################################### 
# 
# 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_6c
_database_code_depnum_ccdc_archive 'CCDC 1898557'
loop_
_audit_author_name
_audit_author_address
'Jacques Pecaut '
;CEA Grenoble
France
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_audit_creation_date             2018-07-26
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            6c
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C22 H35 N3 O2, 1(F6 P1), 1(C F3 O3 S), 1.5(C2 H3 N)'
_chemical_formula_sum            'C26 H39.50 F9 N4.50 O5 P S'
_chemical_formula_weight         729.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H50 N3 O2 P F6'
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'
F F 0.0171 0.0103 '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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.7516(4)
_cell_length_b                   12.0558(6)
_cell_length_c                   14.8348(6)
_cell_angle_alpha                107.620(4)
_cell_angle_beta                 93.413(3)
_cell_angle_gamma                109.731(4)
_cell_volume                     1696.78(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4273
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      29.2870
_cell_measurement_theta_min      2.9270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             758
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.0490
0 0 -1 0.1521
0 -1 1 0.0470
1 0 0 0.2124
-1 0 0 0.2354
-2 1 2 0.2033
2 -1 -2 0.2743
0 -1 2 0.0726
0 -1 0 0.1259
0 0 1 0.1411

_exptl_crystal_size_max          0.542
_exptl_crystal_size_mid          0.348
_exptl_crystal_size_min          0.096
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0008 0.9997 -1.0004 0.0369 -0.0578 -0.0005
0.0000 0.0003 -1.0010 -0.0157 -0.0347 -0.0340
0.0008 -0.9997 1.0004 -0.0369 0.0578 0.0005
1.0003 0.0005 0.0014 -0.0191 -0.0320 0.0608
-1.0003 -0.0005 -0.0014 0.0191 0.0320 -0.0608
-2.0015 0.9980 1.9999 0.1223 0.1101 -0.0200
2.0015 -0.9980 -1.9999 -0.1223 -0.1101 0.0200
0.0007 -1.0000 2.0014 -0.0211 0.0924 0.0345
0.0008 -0.9994 -0.0007 -0.0526 0.0231 -0.0335
-0.0000 -0.0003 1.0010 0.0157 0.0347 0.0340

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19002
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.046
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9653
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  22.00   1.00   10.00    --   -0.62 -64.00 177.00   90
  2  ω    -13.00  77.00   1.00   60.00    --   55.51 -57.00-120.00   90
  3  ω    -13.00  77.00   1.00   60.00    --   55.51 -57.00  90.00   90
  4  ω     25.00 126.00   1.00   60.00    --   55.51  77.00   0.00  101
  5  ω    -16.00  97.00   1.00   60.00    --   55.51 -99.00  60.00  113
  6  ω     -3.00 113.00   1.00   60.00    --   55.51-125.00-120.00  116
  7  ω    -17.00 128.00   1.00   60.00    --   55.51   0.00   0.00  145
  8  ω    -77.00 -47.00   1.00   10.00    --   -0.62 178.00 -60.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0191430000
_diffrn_orient_matrix_UB_12      0.0525933000
_diffrn_orient_matrix_UB_13      0.0157348000
_diffrn_orient_matrix_UB_21      -0.0320110000
_diffrn_orient_matrix_UB_22      -0.0231831000
_diffrn_orient_matrix_UB_23      0.0346078000
_diffrn_orient_matrix_UB_31      0.0607126000
_diffrn_orient_matrix_UB_32      0.0335579000
_diffrn_orient_matrix_UB_33      0.0339997000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5151
_reflns_number_total             6815
_reflns_odcompleteness_completeness 98.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     693
_refine_ls_number_reflns         6815
_refine_ls_number_restraints     632
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0612
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0837P)²+1.4357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.1736
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
N31 \\sim C31 \\sim N32 \\sim C32 \\sim C33 \\sim N33 \\sim C35 \\sim C36:
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.01
P1 \\sim F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim S3 \\sim F1S3
\\sim F2S3 \\sim F3S3 \\sim O1S3 \\sim O2S3 \\sim O3S3 \\sim C3S: within 1.7A
with sigma of 0.01 and sigma for terminal atoms of 0.01
S2 \\sim O1S2 \\sim O2S2 \\sim O3S2 \\sim C2S \\sim F1S2 \\sim F2S2 \\sim F3S2
\\sim S1 \\sim O1S1 \\sim O2S1 \\sim O3S1 \\sim C1S \\sim F1S1 \\sim F2S1 \\sim
F3S1 \\sim P2 \\sim F11 \\sim F12 \\sim F13 \\sim F14 \\sim F15 \\sim F16:
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.01
3. Others
 1*[Sof(S1)+Sof(F1S1)+Sof(F2S1)+Sof(F3S1)+Sof(O1S1)+Sof(O2S1)+Sof(O3S1)+
 Sof(C1S)]+1*[Sof(S2)+Sof(F1S2)+Sof(F2S2)+Sof(F3S2)+Sof(O1S2)+Sof(O2S2)+
 Sof(O3S2)+Sof(C2S)]+1*[Sof(P2)+Sof(F11)+Sof(F12)+Sof(F13)+Sof(F14)+Sof(F15)+
 Sof(F16)]=1 with esd of 0.000001
 1*[Sof(P1)+Sof(F1)+Sof(F2)+Sof(F3)+Sof(F4)+Sof(F5)+Sof(F6)+Sof(S3)+Sof(F1S3)+
 Sof(F2S3)+Sof(F3S3)+Sof(O1S3)+Sof(O2S3)+Sof(O3S3)+Sof(C3S)]+1*[Sof(P2)+
 Sof(F11)+Sof(F12)+Sof(F13)+Sof(F14)+Sof(F15)+Sof(F16)]=1 with esd of 0.000001
 Sof(S1)=Sof(F1S1)=Sof(F2S1)=Sof(F3S1)=Sof(O1S1)=Sof(O2S1)=Sof(O3S1)=Sof(C1S)=
 FVAR(1)
 Sof(S3)=Sof(F1S3)=Sof(F2S3)=Sof(F3S3)=Sof(O1S3)=Sof(O2S3)=Sof(O3S3)=Sof(C3S)=
 1-FVAR(2)
 Sof(P1)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(2)
 Sof(N31)=Sof(C31)=Sof(H33D)=Sof(H33E)=Sof(H33F)=1-FVAR(3)
 Sof(N32)=Sof(C32)=Sof(H33A)=Sof(H33B)=Sof(H33C)=FVAR(3)
 Sof(S2)=Sof(F1S2)=Sof(F2S2)=Sof(F3S2)=Sof(O1S2)=Sof(O2S2)=Sof(O3S2)=Sof(C2S)=
 FVAR(4)
 Sof(P2)=Sof(F11)=Sof(F12)=Sof(F13)=Sof(F14)=Sof(F15)=Sof(F16)=FVAR(5)
 Fixed Sof: N33(0.5) C35(0.5) C36(0.5) H36A(0.5) H36B(0.5) H36C(0.5)
4.a :
 P1(F1,F2,F3,F4,F5,F6), S3(F1S3,F2S3,F3S3,O1S3,O2S3,O3S3,C3S), S1(F1S1,F2S1,
 F3S1,O1S1,O2S1,O3S1,C1S), S2(F1S2,F2S2,F3S2,O1S2,O2S2,O3S2,C2S), P2(F11,F12,
 F13,F14,F15,F16)
4.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C33(H33D,H33E,H33F), C33(H33A,H33B,H33C), C36(H36A,H36B,
 H36C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.30850(16) 0.80358(16) 0.24633(11) 0.0277(4) Uani 1 1 d . . . . .
O2 O 0.44835(15) 0.73402(15) 0.17130(11) 0.0271(4) Uani 1 1 d . . . . .
N1 N 0.0723(2) 0.8233(2) 0.15822(15) 0.0340(5) Uani 1 1 d . . . . .
N2 N 0.2223(2) 0.9249(2) 0.07442(15) 0.0317(5) Uani 1 1 d . . . . .
N3 N 0.3870(2) 0.7161(2) 0.01361(15) 0.0320(5) Uani 1 1 d . . . . .
C1 C 0.4084(2) 0.7671(2) 0.25447(17) 0.0274(5) Uani 1 1 d . . . . .
C2 C 0.2828(2) 0.7988(2) 0.15073(16) 0.0274(5) Uani 1 1 d . . . . .
C3 C 0.3687(2) 0.7512(2) 0.10347(17) 0.0267(5) Uani 1 1 d . . . . .
C4 C 0.1882(2) 0.8510(2) 0.12642(16) 0.0275(5) Uani 1 1 d . . . . .
C5 C 0.0126(3) 0.7088(4) 0.1800(2) 0.0462(7) Uani 1 1 d . . . . .
H5A H 0.017(4) 0.734(4) 0.248(3) 0.061(11) Uiso 1 1 d . . . . .
H5B H 0.059(4) 0.658(3) 0.160(2) 0.045(9) Uiso 1 1 d . . . . .
H5C H -0.079(4) 0.671(4) 0.144(3) 0.055(10) Uiso 1 1 d . . . . .
C6 C -0.0067(3) 0.9039(4) 0.1733(2) 0.0499(8) Uani 1 1 d . . . . .
H6A H 0.044(4) 0.986(4) 0.173(2) 0.049(10) Uiso 1 1 d . . . . .
H6B H -0.084(4) 0.873(3) 0.121(3) 0.054(9) Uiso 1 1 d . . . . .
H6C H -0.025(4) 0.913(4) 0.235(3) 0.055(10) Uiso 1 1 d . . . . .
C7 C 0.1241(3) 0.9385(3) 0.0092(3) 0.0425(7) Uani 1 1 d . . . . .
H7A H 0.039(4) 0.872(3) 0.001(2) 0.043(8) Uiso 1 1 d . . . . .
H7B H 0.128(4) 1.020(4) 0.033(2) 0.049(9) Uiso 1 1 d . . . . .
H7C H 0.152(4) 0.928(3) -0.050(3) 0.047(9) Uiso 1 1 d . . . . .
C8 C 0.3620(3) 0.9971(3) 0.0734(3) 0.0448(7) Uani 1 1 d . . . . .
H8A H 0.417(4) 0.999(3) 0.125(3) 0.048(9) Uiso 1 1 d . . . . .
H8B H 0.369(3) 1.081(4) 0.076(2) 0.048(9) Uiso 1 1 d . . . . .
H8C H 0.388(4) 0.963(4) 0.012(3) 0.072(12) Uiso 1 1 d . . . . .
C9 C 0.2759(4) 0.6786(4) -0.0650(2) 0.0460(7) Uani 1 1 d . . . . .
H9A H 0.204(4) 0.678(3) -0.046(3) 0.047(9) Uiso 1 1 d . . . . .
H9B H 0.303(6) 0.728(6) -0.100(4) 0.100(17) Uiso 1 1 d . . . . .
H9C H 0.269(5) 0.592(5) -0.108(3) 0.086(14) Uiso 1 1 d . . . . .
C10 C 0.4997(3) 0.6773(3) -0.0103(2) 0.0394(6) Uani 1 1 d . . . . .
H10A H 0.574(4) 0.727(3) 0.037(3) 0.045(9) Uiso 1 1 d . . . . .
H10B H 0.474(3) 0.594(4) -0.018(2) 0.045(9) Uiso 1 1 d . . . . .
H10C H 0.521(4) 0.694(3) -0.069(3) 0.053(9) Uiso 1 1 d . . . . .
C11 C 0.4662(2) 0.7606(2) 0.34109(17) 0.0288(5) Uani 1 1 d . . . . .
C12 C 0.5673(3) 0.7096(2) 0.34050(19) 0.0349(6) Uani 1 1 d . . . . .
C13 C 0.6161(3) 0.7013(3) 0.4263(2) 0.0416(7) Uani 1 1 d . . . . .
H13 H 0.681(4) 0.667(4) 0.423(3) 0.055(10) Uiso 1 1 d . . . . .
C14 C 0.5706(3) 0.7403(3) 0.5113(2) 0.0407(6) Uani 1 1 d . . . . .
C15 C 0.4739(3) 0.7935(3) 0.5103(2) 0.0403(6) Uani 1 1 d . . . . .
H15 H 0.442(3) 0.829(3) 0.570(2) 0.043(8) Uiso 1 1 d . . . . .
C16 C 0.4207(3) 0.8056(3) 0.42814(18) 0.0345(6) Uani 1 1 d . . . . .
C17 C 0.6258(4) 0.6645(4) 0.2535(2) 0.0508(8) Uani 1 1 d . . . . .
H17A H 0.667(4) 0.728(4) 0.224(3) 0.058(11) Uiso 1 1 d . . . . .
H17B H 0.565(4) 0.601(4) 0.203(3) 0.051(9) Uiso 1 1 d . . . . .
H17C H 0.685(4) 0.632(4) 0.267(3) 0.060(10) Uiso 1 1 d . . . . .
C18 C 0.6244(4) 0.7300(3) 0.6057(2) 0.0501(8) Uani 1 1 d . . . . .
P1 P 0.19491(8) 0.39765(8) 0.11237(6) 0.0306(3) Uani 0.7700(15) 1 d . U P A 1
F1 F 0.0553(2) 0.3745(2) 0.0496(2) 0.0698(12) Uani 0.7700(15) 1 d G U P A 1
F2 F 0.3343(2) 0.4206(2) 0.1742(2) 0.0704(10) Uani 0.7700(15) 1 d G U P A 1
F3 F 0.1977(3) 0.52789(18) 0.18207(16) 0.0583(9) Uani 0.7700(15) 1 d G U P A 1
F4 F 0.2738(3) 0.4681(2) 0.04531(18) 0.0754(12) Uani 0.7700(15) 1 d G U P A 1
F5 F 0.1942(3) 0.26844(18) 0.04213(15) 0.0629(9) Uani 0.7700(15) 1 d G U P A 1
F6 F 0.1142(3) 0.3262(2) 0.17778(18) 0.0768(12) Uani 0.7700(15) 1 d G U P A 1
C22 C 0.3208(4) 0.8693(4) 0.4371(2) 0.0500(8) Uani 1 1 d . . . . .
H22A H 0.346(3) 0.941(3) 0.411(2) 0.046(9) Uiso 1 1 d . . . . .
H22B H 0.309(4) 0.894(4) 0.502(3) 0.058(10) Uiso 1 1 d . . . . .
H22C H 0.232(4) 0.805(4) 0.401(3) 0.064(11) Uiso 1 1 d . . . . .
C21 C 0.5044(5) 0.6646(5) 0.6488(3) 0.0823(13) Uani 1 1 d . . . . .
H21A H 0.443360 0.707978 0.654854 0.123 Uiso 1 1 calc GR . . . .
H21B H 0.537087 0.666355 0.711074 0.123 Uiso 1 1 calc GR . . . .
H21C H 0.458519 0.579173 0.607205 0.123 Uiso 1 1 calc GR . . . .
S3 S 0.1739(3) 0.4359(3) 0.0882(3) 0.0421(8) Uani 0.2300(15) 1 d . U P A 2
F1S3 F 0.1388(12) 0.3011(12) 0.1969(7) 0.089(4) Uani 0.2300(15) 1 d G U P A 2
F2S3 F 0.2078(12) 0.2317(9) 0.0708(7) 0.080(3) Uani 0.2300(15) 1 d G U P A 2
F3S3 F 0.3414(10) 0.3883(10) 0.1868(9) 0.090(4) Uani 0.2300(15) 1 d G U P A 2
O1S3 O 0.2687(9) 0.4591(9) 0.0278(7) 0.063(3) Uani 0.2300(15) 1 d G U P A 2
O2S3 O 0.1880(11) 0.5396(7) 0.1712(5) 0.042(2) Uani 0.2300(15) 1 d G U P A 2
O3S3 O 0.0413(7) 0.3625(7) 0.0403(8) 0.061(4) Uani 0.2300(15) 1 d G U P A 2
C3S C 0.2182(7) 0.3345(7) 0.1373(4) 0.059(2) Uani 0.2300(15) 1 d G U P A 2
N31 N -0.0909(10) 0.6119(10) 0.3858(6) 0.105(3) Uani 0.637(11) 1 d . U P B 2
C31 C -0.0172(13) 0.5617(13) 0.3845(9) 0.088(2) Uani 0.637(11) 1 d . U P B 2
N32 N -0.1625(19) 0.5208(17) 0.3288(12) 0.107(3) Uani 0.363(11) 1 d . U P B 1
C32 C -0.071(3) 0.520(2) 0.3520(17) 0.093(4) Uani 0.363(11) 1 d . U P B 1
C33 C 0.0843(7) 0.5194(7) 0.3895(5) 0.1085(18) Uani 1 1 d . U . . .
H33D H 0.048781 0.429331 0.363730 0.163 Uiso 0.637(11) 1 calc GR . P B 2
H33E H 0.126899 0.547049 0.455325 0.163 Uiso 0.637(11) 1 calc GR . P B 2
H33F H 0.149011 0.551781 0.352840 0.163 Uiso 0.637(11) 1 calc GR . P B 2
H33A H 0.134725 0.517603 0.338109 0.163 Uiso 0.363(11) 1 calc GR . P B 1
H33B H 0.072166 0.446566 0.407115 0.163 Uiso 0.363(11) 1 calc GR . P B 1
H33C H 0.132231 0.593636 0.443977 0.163 Uiso 0.363(11) 1 calc GR . P B 1
N33 N -0.0085(13) 1.1308(13) 0.5894(8) 0.128(4) Uani 0.5 1 d . U P C -1
C35 C 0.028(2) 1.058(3) 0.546(2) 0.115(5) Uani 0.5 1 d . U P C -1
C36 C 0.0212(18) 0.952(3) 0.4722(16) 0.098(4) Uani 0.5 1 d . U P C -1
H36A H 0.033810 0.892465 0.498431 0.147 Uiso 0.5 1 calc GR . P C -1
H36B H 0.090330 0.975639 0.435806 0.147 Uiso 0.5 1 calc GR . P C -1
H36C H -0.065065 0.915974 0.431063 0.147 Uiso 0.5 1 calc GR . P C -1
S1 S 0.6833(2) 1.0441(3) 0.22530(17) 0.0329(6) Uani 0.459(2) 1 d . U P D 1
F1S1 F 0.9429(3) 1.1687(4) 0.2815(3) 0.0673(15) Uani 0.459(2) 1 d G U P D 1
F2S1 F 0.8233(5) 1.2263(4) 0.3819(3) 0.071(2) Uani 0.459(2) 1 d G U P D 1
F3S1 F 0.8528(4) 1.0527(4) 0.3635(3) 0.0707(13) Uani 0.459(2) 1 d G U P D 1
O1S1 O 0.5786(3) 1.0087(5) 0.2787(3) 0.041(2) Uani 0.459(2) 1 d G U P D 1
O2S1 O 0.7134(4) 0.9422(4) 0.1622(2) 0.0507(16) Uani 0.459(2) 1 d G U P D 1
O3S1 O 0.6802(4) 1.1376(4) 0.1858(3) 0.0596(18) Uani 0.459(2) 1 d G U P D 1
C1S C 0.8316(3) 1.1267(3) 0.31785(19) 0.0539(14) Uani 0.459(2) 1 d G U P D 1
C20 C 0.6948(5) 0.8618(4) 0.6786(2) 0.0682(11) Uani 1 1 d . . . . .
H20A H 0.768705 0.907899 0.654582 0.102 Uiso 1 1 calc GR . . . .
H20B H 0.727765 0.856850 0.738248 0.102 Uiso 1 1 calc GR . . . .
H20C H 0.632519 0.903676 0.688778 0.102 Uiso 1 1 calc GR . . . .
S2 S 0.6897(4) 1.0163(3) 0.2478(3) 0.0380(9) Uani 0.311(2) 1 d . U P E 2
F1S2 F 0.8310(8) 1.2246(6) 0.3875(4) 0.075(3) Uani 0.311(2) 1 d G U P E 2
F2S2 F 0.9200(5) 1.1893(6) 0.2631(6) 0.091(3) Uani 0.311(2) 1 d G U P E 2
F3S2 F 0.7536(7) 1.2500(5) 0.2620(5) 0.100(2) Uani 0.311(2) 1 d G U P E 2
O1S2 O 0.6753(6) 0.9850(5) 0.1456(3) 0.051(2) Uani 0.311(2) 1 d G U P E 2
O2S2 O 0.5723(6) 1.0227(6) 0.2880(5) 0.044(2) Uani 0.311(2) 1 d G U P E 2
O3S2 O 0.7608(7) 0.9565(5) 0.2873(4) 0.058(2) Uani 0.311(2) 1 d G U P E 2
C2S C 0.8040(5) 1.1773(4) 0.2913(3) 0.062(2) Uani 0.311(2) 1 d G U P E 2
C19 C 0.7149(7) 0.6580(6) 0.5925(3) 0.103(2) Uani 1 1 d . . . . .
H19A H 0.666490 0.574229 0.548643 0.154 Uiso 1 1 calc GR . . . .
H19B H 0.746120 0.655006 0.653367 0.154 Uiso 1 1 calc GR . . . .
H19C H 0.790363 0.698594 0.566948 0.154 Uiso 1 1 calc GR . . . .
P2 P 0.7236(4) 1.0608(4) 0.2527(3) 0.0392(10) Uani 0.2300(15) 1 d . U P F 3
F11 F 0.8756(6) 1.1144(6) 0.2329(5) 0.0616(19) Uani 0.2300(15) 1 d G U P F 3
F12 F 0.5725(6) 1.0078(8) 0.2732(6) 0.036(3) Uani 0.2300(15) 1 d G U P F 3
F13 F 0.6781(8) 1.1373(8) 0.1944(5) 0.063(3) Uani 0.2300(15) 1 d G U P F 3
F14 F 0.7634(6) 1.1811(6) 0.3498(5) 0.067(2) Uani 0.2300(15) 1 d G U P F 3
F15 F 0.7684(9) 0.9854(6) 0.3125(6) 0.062(2) Uani 0.2300(15) 1 d G U P F 3
F16 F 0.6863(7) 0.9410(7) 0.1562(5) 0.046(2) Uani 0.2300(15) 1 d G U P F 3


_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 C1 1.303(3) . ?
O1 C2 1.409(3) . ?
O2 C1 1.321(3) . ?
O2 C3 1.390(3) . ?
N1 C4 1.330(3) . ?
N1 C5 1.456(4) . ?
N1 C6 1.471(4) . ?
N2 C4 1.323(3) . ?
N2 C7 1.474(3) . ?
N2 C8 1.463(4) . ?
N3 C3 1.319(3) . ?
N3 C9 1.464(4) . ?
N3 C10 1.465(3) . ?
C1 C11 1.429(3) . ?
C2 C3 1.365(3) . ?
C2 C4 1.444(3) . ?
C5 H5A 0.95(4) . ?
C5 H5B 0.91(4) . ?
C5 H5C 0.98(4) . ?
C6 H6A 0.96(4) . ?
C6 H6B 0.98(4) . ?
C6 H6C 0.93(4) . ?
C7 H7A 0.96(4) . ?
C7 H7B 0.92(4) . ?
C7 H7C 0.94(4) . ?
C8 H8A 0.93(4) . ?
C8 H8B 0.98(4) . ?
C8 H8C 0.98(5) . ?
C9 H9A 0.84(4) . ?
C9 H9B 0.89(6) . ?
C9 H9C 1.02(5) . ?
C10 H10A 0.92(4) . ?
C10 H10B 0.92(4) . ?
C10 H10C 0.97(4) . ?
C11 C12 1.418(3) . ?
C11 C16 1.425(4) . ?
C12 C13 1.392(4) . ?
C12 C17 1.502(4) . ?
C13 H13 0.92(4) . ?
C13 C14 1.385(4) . ?
C14 C15 1.394(4) . ?
C14 C18 1.540(4) . ?
C15 H15 1.00(3) . ?
C15 C16 1.385(4) . ?
C16 C22 1.508(4) . ?
C17 H17A 0.98(4) . ?
C17 H17B 0.91(4) . ?
C17 H17C 0.89(4) . ?
C18 C21 1.553(6) . ?
C18 C20 1.522(5) . ?
C18 C19 1.493(5) . ?
P1 F1 1.6097(15) . ?
P1 F2 1.6015(15) . ?
P1 F3 1.5867(15) . ?
P1 F4 1.5985(15) . ?
P1 F5 1.5876(15) . ?
P1 F6 1.5931(15) . ?
C22 H22A 1.01(4) . ?
C22 H22B 0.95(4) . ?
C22 H22C 1.00(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
S3 O1S3 1.411(5) . ?
S3 O2S3 1.421(5) . ?
S3 O3S3 1.402(5) . ?
S3 C3S 1.772(7) . ?
F1S3 C3S 1.322(5) . ?
F2S3 C3S 1.294(5) . ?
F3S3 C3S 1.315(5) . ?
N31 C31 1.146(12) . ?
C31 C33 1.359(12) . ?
N32 C32 1.03(2) . ?
C32 C33 1.73(3) . ?
C33 H33D 0.9600 . ?
C33 H33E 0.9600 . ?
C33 H33F 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
N33 C35 1.12(3) . ?
C35 C36 1.379(16) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
S1 O1S1 1.4372(18) . ?
S1 O2S1 1.4483(18) . ?
S1 O3S1 1.4281(17) . ?
S1 C1S 1.805(2) . ?
F1S1 C1S 1.3458(16) . ?
F2S1 C1S 1.3205(16) . ?
F3S1 C1S 1.3383(16) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
S2 O1S2 1.432(3) . ?
S2 O2S2 1.443(3) . ?
S2 O3S2 1.423(3) . ?
S2 C2S 1.797(4) . ?
F1S2 C2S 1.339(3) . ?
F2S2 C2S 1.315(3) . ?
F3S2 C2S 1.332(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
P2 F11 1.623(4) . ?
P2 F12 1.617(4) . ?
P2 F13 1.605(4) . ?
P2 F14 1.614(4) . ?
P2 F15 1.606(4) . ?
P2 F16 1.608(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
C1 O1 C2 107.66(18) . . ?
C1 O2 C3 107.88(17) . . ?
C4 N1 C5 122.2(2) . . ?
C4 N1 C6 123.4(3) . . ?
C5 N1 C6 114.4(3) . . ?
C4 N2 C7 123.4(2) . . ?
C4 N2 C8 123.0(2) . . ?
C8 N2 C7 113.5(2) . . ?
C3 N3 C9 119.7(2) . . ?
C3 N3 C10 120.5(2) . . ?
C9 N3 C10 117.2(2) . . ?
O1 C1 O2 111.2(2) . . ?
O1 C1 C11 124.9(2) . . ?
O2 C1 C11 123.9(2) . . ?
O1 C2 C4 118.4(2) . . ?
C3 C2 O1 106.45(19) . . ?
C3 C2 C4 134.9(2) . . ?
N3 C3 O2 117.5(2) . . ?
N3 C3 C2 135.7(2) . . ?
C2 C3 O2 106.7(2) . . ?
N1 C4 C2 118.3(2) . . ?
N2 C4 N1 123.6(2) . . ?
N2 C4 C2 118.0(2) . . ?
N1 C5 H5A 106(2) . . ?
N1 C5 H5B 109(2) . . ?
N1 C5 H5C 104(2) . . ?
H5A C5 H5B 112(3) . . ?
H5A C5 H5C 113(3) . . ?
H5B C5 H5C 111(3) . . ?
N1 C6 H6A 112(2) . . ?
N1 C6 H6B 113(2) . . ?
N1 C6 H6C 105(2) . . ?
H6A C6 H6B 103(3) . . ?
H6A C6 H6C 107(3) . . ?
H6B C6 H6C 117(3) . . ?
N2 C7 H7A 107(2) . . ?
N2 C7 H7B 108(2) . . ?
N2 C7 H7C 108(2) . . ?
H7A C7 H7B 118(3) . . ?
H7A C7 H7C 109(3) . . ?
H7B C7 H7C 106(3) . . ?
N2 C8 H8A 109(2) . . ?
N2 C8 H8B 109(2) . . ?
N2 C8 H8C 111(3) . . ?
H8A C8 H8B 112(3) . . ?
H8A C8 H8C 112(3) . . ?
H8B C8 H8C 104(3) . . ?
N3 C9 H9A 113(2) . . ?
N3 C9 H9B 108(4) . . ?
N3 C9 H9C 104(3) . . ?
H9A C9 H9B 114(4) . . ?
H9A C9 H9C 113(4) . . ?
H9B C9 H9C 105(4) . . ?
N3 C10 H10A 110(2) . . ?
N3 C10 H10B 108(2) . . ?
N3 C10 H10C 107(2) . . ?
H10A C10 H10B 112(3) . . ?
H10A C10 H10C 107(3) . . ?
H10B C10 H10C 113(3) . . ?
C12 C11 C1 120.4(2) . . ?
C12 C11 C16 120.3(2) . . ?
C16 C11 C1 119.3(2) . . ?
C11 C12 C17 124.3(2) . . ?
C13 C12 C11 117.8(2) . . ?
C13 C12 C17 117.9(2) . . ?
C12 C13 H13 116(2) . . ?
C14 C13 C12 123.2(3) . . ?
C14 C13 H13 121(2) . . ?
C13 C14 C15 117.7(2) . . ?
C13 C14 C18 122.9(3) . . ?
C15 C14 C18 119.4(3) . . ?
C14 C15 H15 121.8(18) . . ?
C16 C15 C14 122.6(3) . . ?
C16 C15 H15 115.5(18) . . ?
C11 C16 C22 124.0(2) . . ?
C15 C16 C11 118.3(2) . . ?
C15 C16 C22 117.7(2) . . ?
C12 C17 H17A 115(2) . . ?
C12 C17 H17B 115(2) . . ?
C12 C17 H17C 111(2) . . ?
H17A C17 H17B 102(3) . . ?
H17A C17 H17C 110(3) . . ?
H17B C17 H17C 104(3) . . ?
C14 C18 C21 109.3(3) . . ?
C20 C18 C14 108.5(3) . . ?
C20 C18 C21 105.7(3) . . ?
C19 C18 C14 112.8(3) . . ?
C19 C18 C21 108.8(4) . . ?
C19 C18 C20 111.4(4) . . ?
F2 P1 F1 179.6 . . ?
F3 P1 F1 90.5 . . ?
F3 P1 F2 89.7 . . ?
F3 P1 F4 89.4 . . ?
F3 P1 F5 179.1 . . ?
F3 P1 F6 91.1 . . ?
F4 P1 F1 89.1 . . ?
F4 P1 F2 90.6 . . ?
F5 P1 F1 89.9 . . ?
F5 P1 F2 89.9 . . ?
F5 P1 F4 89.9 . . ?
F5 P1 F6 89.7 . . ?
F6 P1 F1 90.0 . . ?
F6 P1 F2 90.3 . . ?
F6 P1 F4 179.1 . . ?
C16 C22 H22A 112.7(19) . . ?
C16 C22 H22B 108(2) . . ?
C16 C22 H22C 108(2) . . ?
H22A C22 H22B 113(3) . . ?
H22A C22 H22C 109(3) . . ?
H22B C22 H22C 105(3) . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1S3 S3 O2S3 115.9 . . ?
O1S3 S3 C3S 102.6 . . ?
O2S3 S3 C3S 102.9 . . ?
O3S3 S3 O1S3 115.0 . . ?
O3S3 S3 O2S3 115.0 . . ?
O3S3 S3 C3S 102.7 . . ?
F1S3 C3S S3 111.8 . . ?
F2S3 C3S S3 111.4 . . ?
F2S3 C3S F1S3 106.4 . . ?
F2S3 C3S F3S3 108.7 . . ?
F3S3 C3S S3 111.8 . . ?
F3S3 C3S F1S3 106.5 . . ?
N31 C31 C33 171.6(14) . . ?
N32 C32 C33 179(2) . . ?
C31 C33 H33D 109.5 . . ?
C31 C33 H33E 109.5 . . ?
C31 C33 H33F 109.5 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33D C33 H33E 109.5 . . ?
H33D C33 H33F 109.5 . . ?
H33E C33 H33F 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N33 C35 C36 156.8(19) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O1S1 S1 O2S1 115.8 . . ?
O1S1 S1 C1S 102.7 . . ?
O2S1 S1 C1S 103.0 . . ?
O3S1 S1 O1S1 115.0 . . ?
O3S1 S1 O2S1 114.9 . . ?
O3S1 S1 C1S 102.7 . . ?
F1S1 C1S S1 111.8 . . ?
F2S1 C1S S1 111.5 . . ?
F2S1 C1S F1S1 106.3 . . ?
F2S1 C1S F3S1 108.7 . . ?
F3S1 C1S S1 111.7 . . ?
F3S1 C1S F1S1 106.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1S2 S2 O2S2 115.8 . . ?
O1S2 S2 C2S 102.6 . . ?
O2S2 S2 C2S 103.0 . . ?
O3S2 S2 O1S2 115.1 . . ?
O3S2 S2 O2S2 114.9 . . ?
O3S2 S2 C2S 102.6 . . ?
F1S2 C2S S2 111.8 . . ?
F2S2 C2S S2 111.6 . . ?
F2S2 C2S F1S2 106.3 . . ?
F2S2 C2S F3S2 108.7 . . ?
F3S2 C2S S2 111.6 . . ?
F3S2 C2S F1S2 106.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F12 P2 F11 179.6 . . ?
F13 P2 F11 90.5 . . ?
F13 P2 F12 89.7 . . ?
F13 P2 F14 89.3 . . ?
F13 P2 F15 179.1 . . ?
F13 P2 F16 91.2 . . ?
F14 P2 F11 89.2 . . ?
F14 P2 F12 90.4 . . ?
F15 P2 F11 89.9 . . ?
F15 P2 F12 89.9 . . ?
F15 P2 F14 89.9 . . ?
F15 P2 F16 89.6 . . ?
F16 P2 F11 90.0 . . ?
F16 P2 F12 90.3 . . ?
F16 P2 F14 179.1 . . ?

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
O1 C1 C11 C12 174.6(2) . . . . ?
O1 C1 C11 C16 -5.2(4) . . . . ?
O1 C2 C3 O2 -2.8(2) . . . . ?
O1 C2 C3 N3 173.9(3) . . . . ?
O1 C2 C4 N1 -45.5(3) . . . . ?
O1 C2 C4 N2 133.8(2) . . . . ?
O2 C1 C11 C12 -3.9(4) . . . . ?
O2 C1 C11 C16 176.3(2) . . . . ?
C1 O1 C2 C3 3.2(3) . . . . ?
C1 O1 C2 C4 -171.7(2) . . . . ?
C1 O2 C3 N3 -175.9(2) . . . . ?
C1 O2 C3 C2 1.5(2) . . . . ?
C1 C11 C12 C13 -177.6(2) . . . . ?
C1 C11 C12 C17 2.8(4) . . . . ?
C1 C11 C16 C15 177.3(2) . . . . ?
C1 C11 C16 C22 -4.5(4) . . . . ?
C2 O1 C1 O2 -2.3(3) . . . . ?
C2 O1 C1 C11 179.0(2) . . . . ?
C3 O2 C1 O1 0.5(3) . . . . ?
C3 O2 C1 C11 179.2(2) . . . . ?
C3 C2 C4 N1 141.4(3) . . . . ?
C3 C2 C4 N2 -39.3(4) . . . . ?
C4 C2 C3 O2 170.8(3) . . . . ?
C4 C2 C3 N3 -12.4(5) . . . . ?
C5 N1 C4 N2 154.7(3) . . . . ?
C5 N1 C4 C2 -26.0(3) . . . . ?
C6 N1 C4 N2 -24.5(4) . . . . ?
C6 N1 C4 C2 154.8(2) . . . . ?
C7 N2 C4 N1 -29.2(4) . . . . ?
C7 N2 C4 C2 151.5(3) . . . . ?
C8 N2 C4 N1 153.3(3) . . . . ?
C8 N2 C4 C2 -26.0(4) . . . . ?
C9 N3 C3 O2 152.9(3) . . . . ?
C9 N3 C3 C2 -23.7(5) . . . . ?
C10 N3 C3 O2 -8.4(4) . . . . ?
C10 N3 C3 C2 175.0(3) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C11 C16 C15 -2.5(4) . . . . ?
C12 C11 C16 C22 175.7(3) . . . . ?
C12 C13 C14 C15 -1.8(5) . . . . ?
C12 C13 C14 C18 179.6(3) . . . . ?
C13 C14 C15 C16 1.5(5) . . . . ?
C13 C14 C18 C21 -129.3(4) . . . . ?
C13 C14 C18 C20 115.9(4) . . . . ?
C13 C14 C18 C19 -8.0(5) . . . . ?
C14 C15 C16 C11 0.7(4) . . . . ?
C14 C15 C16 C22 -177.7(3) . . . . ?
C15 C14 C18 C21 52.1(4) . . . . ?
C15 C14 C18 C20 -62.7(4) . . . . ?
C15 C14 C18 C19 173.4(4) . . . . ?
C16 C11 C12 C13 2.2(4) . . . . ?
C16 C11 C12 C17 -177.4(3) . . . . ?
C17 C12 C13 C14 179.7(3) . . . . ?
C18 C14 C15 C16 -179.9(3) . . . . ?
O1S3 S3 C3S F1S3 -179.8 . . . . ?
O1S3 S3 C3S F2S3 -60.9 . . . . ?
O1S3 S3 C3S F3S3 60.9 . . . . ?
O2S3 S3 C3S F1S3 59.6 . . . . ?
O2S3 S3 C3S F2S3 178.5 . . . . ?
O2S3 S3 C3S F3S3 -59.7 . . . . ?
O3S3 S3 C3S F1S3 -60.1 . . . . ?
O3S3 S3 C3S F2S3 58.8 . . . . ?
O3S3 S3 C3S F3S3 -179.4 . . . . ?
O1S1 S1 C1S F1S1 -179.8 . . . . ?
O1S1 S1 C1S F2S1 -60.9 . . . . ?
O1S1 S1 C1S F3S1 60.9 . . . . ?
O2S1 S1 C1S F1S1 59.6 . . . . ?
O2S1 S1 C1S F2S1 178.5 . . . . ?
O2S1 S1 C1S F3S1 -59.7 . . . . ?
O3S1 S1 C1S F1S1 -60.1 . . . . ?
O3S1 S1 C1S F2S1 58.8 . . . . ?
O3S1 S1 C1S F3S1 -179.4 . . . . ?
O1S2 S2 C2S F1S2 -179.8 . . . . ?
O1S2 S2 C2S F2S2 -60.9 . . . . ?
O1S2 S2 C2S F3S2 60.9 . . . . ?
O2S2 S2 C2S F1S2 59.6 . . . . ?
O2S2 S2 C2S F2S2 178.5 . . . . ?
O2S2 S2 C2S F3S2 -59.7 . . . . ?
O3S2 S2 C2S F1S2 -60.1 . . . . ?
O3S2 S2 C2S F2S2 58.8 . . . . ?
O3S2 S2 C2S F3S2 -179.4 . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_date_sample_data_collection 2018-07-25
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.078
_oxdiff_exptl_absorpt_empirical_full_min 0.930



####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1898564'
loop_
_audit_author_name
_audit_author_address
'Jacques Pecaut '
;CEA Grenoble
France
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_audit_creation_date             2018-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H29 Cl N3 O2, F6 P'
_chemical_formula_sum            'C19 H29 Cl F6 N3 O2 P'
_chemical_formula_weight         511.87
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H29ClF6N3O2P
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'
Cl Cl 0.1484 0.1585 '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'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.59057(19)
_cell_length_b                   26.3895(7)
_cell_length_c                   12.4880(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.133(3)
_cell_angle_gamma                90
_cell_volume                     2390.47(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5838
_cell_measurement_temperature    149.95(10)
_cell_measurement_theta_max      31.6930
_cell_measurement_theta_min      2.8430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0361
1 -1 -2 0.3348
-1 1 2 0.3198
-1 1 -2 0.2655
1 -1 2 0.2325
1 -1 0 0.0782
-1 1 0 0.0812
0 1 0 0.0361

_exptl_crystal_size_max          0.774
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.073
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0002 -0.9994 -0.0009 -0.0049 0.0264 -0.0011
0.9997 -0.9967 -1.9986 -0.0527 0.0128 -0.1208
-0.9997 0.9967 1.9986 0.0527 -0.0128 0.1208
-0.9989 0.9976 -1.9993 0.1478 -0.0034 -0.0968
0.9989 -0.9976 1.9993 -0.1478 0.0034 0.0968
0.9993 -0.9972 0.0003 -0.1003 0.0081 -0.0120
-0.9993 0.9972 -0.0003 0.1003 -0.0081 0.0120
-0.0000 0.9999 0.0002 0.0049 -0.0264 0.0010

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28619
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.505
_diffrn_reflns_theta_min         2.301
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9653
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  74.00   1.00   30.00    --   25.72   0.00  60.00   99
  2  ω   -102.00 -61.00   1.00   30.00    --  -27.28-178.00 120.00   41
  3  ω      4.00  67.00   1.00   30.00    --   25.41 -99.00  90.00   63
  4  ω    -25.00   1.00   1.00   30.00    --   25.41 -99.00  90.00   26
  5  ω    -97.00 -72.00   1.00   30.00    --  -26.97 -77.00 150.00   25
  6  ω     -8.00  86.00   1.00   30.00    --   25.41  19.00 120.00   94
  7  ω   -104.00 -76.00   1.00   30.00    --  -26.97 178.00-120.00   28
  8  ω    -87.00 -10.00   1.00   30.00    --  -26.97 129.00 136.00   77
  9  ω    -97.00 -53.00   1.00   30.00    --  -26.97 -77.00-150.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0954253000
_diffrn_orient_matrix_UB_12      0.0049202000
_diffrn_orient_matrix_UB_13      -0.0237899000
_diffrn_orient_matrix_UB_21      -0.0182289000
_diffrn_orient_matrix_UB_22      -0.0264012000
_diffrn_orient_matrix_UB_23      -0.0023716000
_diffrn_orient_matrix_UB_31      -0.0110246000
_diffrn_orient_matrix_UB_32      0.0010100000
_diffrn_orient_matrix_UB_33      0.0544348000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5933
_reflns_number_total             7291
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         7291
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+1.1724P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1058
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(F5B) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F4B) \\sim Ueq, Uanis(F4)
\\sim Ueq, Uanis(F3B) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F6B) \\sim Ueq,
Uanis(F6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
2. Others
 Sof(F3B)=Sof(F4B)=Sof(F6B)=Sof(F5B)=1-FVAR(1)
 Sof(F5)=Sof(F3)=Sof(F4)=Sof(F6)=FVAR(1)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.83496(5) 0.47848(2) 0.60288(3) 0.03192(10) Uani 1 1 d . . . . .
O1 O 0.69220(13) 0.42912(4) 0.38800(8) 0.02084(19) Uani 1 1 d . . . . .
O2 O 0.40771(15) 0.40997(5) 0.39641(9) 0.0342(3) Uani 1 1 d . . . . .
N1 N 0.74696(17) 0.32568(5) 0.35225(10) 0.0224(2) Uani 1 1 d . . . . .
N2 N 0.67647(17) 0.31098(5) 0.51859(10) 0.0234(2) Uani 1 1 d . . . . .
N3 N 0.97700(19) 0.38865(5) 0.66386(10) 0.0297(3) Uani 1 1 d . . . . .
C1 C 0.76279(18) 0.39541(5) 0.47775(11) 0.0201(3) Uani 1 1 d . . . . .
C2 C 0.72991(18) 0.34195(5) 0.44982(11) 0.0193(2) Uani 1 1 d . . . . .
C3 C 0.85889(19) 0.41432(5) 0.57964(11) 0.0225(3) Uani 1 1 d . . . . .
C4 C 0.8729(2) 0.34960(7) 0.29832(14) 0.0299(3) Uani 1 1 d . . . . .
H4A H 0.946(3) 0.3739(7) 0.3459(16) 0.028(5) Uiso 1 1 d . . . . .
H4B H 0.804(3) 0.3650(8) 0.2301(18) 0.042(6) Uiso 1 1 d . . . . .
H4C H 0.946(3) 0.3245(8) 0.2809(18) 0.044(6) Uiso 1 1 d . . . . .
C5 C 0.6385(3) 0.28364(7) 0.28898(14) 0.0327(3) Uani 1 1 d . . . . .
H5A H 0.602(3) 0.2941(8) 0.2107(18) 0.036(5) Uiso 1 1 d . . . . .
H5B H 0.709(3) 0.2538(8) 0.2979(17) 0.040(5) Uiso 1 1 d . . . . .
H5C H 0.530(3) 0.2786(7) 0.3122(16) 0.033(5) Uiso 1 1 d . . . . .
C6 C 0.7164(2) 0.25642(6) 0.52515(15) 0.0321(3) Uani 1 1 d . . . . .
H6A H 0.610(3) 0.2376(8) 0.4876(18) 0.043(6) Uiso 1 1 d . . . . .
H6B H 0.759(3) 0.2482(8) 0.6026(19) 0.045(6) Uiso 1 1 d . . . . .
H6C H 0.815(3) 0.2489(8) 0.4938(17) 0.036(5) Uiso 1 1 d . . . . .
C7 C 0.5867(3) 0.32931(7) 0.59998(14) 0.0336(4) Uani 1 1 d . . . . .
H7A H 0.492(3) 0.3059(8) 0.6019(17) 0.044(6) Uiso 1 1 d . . . . .
H7B H 0.533(3) 0.3627(8) 0.5796(18) 0.042(6) Uiso 1 1 d . . . . .
H7C H 0.674(3) 0.3316(8) 0.6742(19) 0.045(6) Uiso 1 1 d . . . . .
C8 C 1.0743(3) 0.34389(7) 0.64354(16) 0.0372(4) Uani 1 1 d . . . . .
H8A H 1.009(3) 0.3134(9) 0.6611(18) 0.048(6) Uiso 1 1 d . . . . .
H8B H 1.195(3) 0.3447(8) 0.6940(17) 0.039(5) Uiso 1 1 d . . . . .
H8C H 1.079(3) 0.3431(8) 0.5701(19) 0.045(6) Uiso 1 1 d . . . . .
C9 C 1.0177(3) 0.40431(10) 0.78109(14) 0.0434(5) Uani 1 1 d . . . . .
H9A H 1.024(3) 0.3753(10) 0.825(2) 0.062(7) Uiso 1 1 d . . . . .
H9B H 1.136(3) 0.4186(9) 0.8060(19) 0.051(6) Uiso 1 1 d . . . . .
H9C H 0.930(4) 0.4246(10) 0.798(2) 0.063(8) Uiso 1 1 d . . . . .
C10 C 0.50329(19) 0.43137(5) 0.34976(11) 0.0210(3) Uani 1 1 d . . . . .
C11 C 0.43687(18) 0.46118(5) 0.24388(11) 0.0203(3) Uani 1 1 d . . . . .
C12 C 0.49426(19) 0.51130(5) 0.23809(12) 0.0232(3) Uani 1 1 d . . . . .
C13 C 0.4249(2) 0.53764(6) 0.13792(13) 0.0280(3) Uani 1 1 d . . . . .
H13 H 0.463(3) 0.5714(8) 0.1334(16) 0.037(5) Uiso 1 1 d . . . . .
C14 C 0.3020(2) 0.51540(6) 0.04447(12) 0.0281(3) Uani 1 1 d . . . . .
C15 C 0.2473(2) 0.46596(6) 0.05335(12) 0.0282(3) Uani 1 1 d . . . . .
H15 H 0.161(3) 0.4511(7) -0.0067(16) 0.032(5) Uiso 1 1 d . . . . .
C16 C 0.3120(2) 0.43782(6) 0.15167(12) 0.0237(3) Uani 1 1 d . . . . .
C17 C 0.6233(2) 0.53802(6) 0.33720(15) 0.0315(3) Uani 1 1 d . . . . .
H17A H 0.625(3) 0.5724(8) 0.3199(17) 0.040(5) Uiso 1 1 d . . . . .
H17B H 0.749(3) 0.5254(8) 0.3542(17) 0.038(5) Uiso 1 1 d . . . . .
H17C H 0.583(3) 0.5339(8) 0.4029(18) 0.040(5) Uiso 1 1 d . . . . .
C18 C 0.2323(3) 0.54464(8) -0.06369(15) 0.0381(4) Uani 1 1 d . . . . .
H18A H 0.189(4) 0.5767(11) -0.051(2) 0.069(8) Uiso 1 1 d . . . . .
H18B H 0.133(4) 0.5291(11) -0.116(3) 0.079(9) Uiso 1 1 d . . . . .
H18C H 0.324(4) 0.5468(11) -0.103(2) 0.085(9) Uiso 1 1 d . . . . .
C19 C 0.2498(3) 0.38366(7) 0.15289(16) 0.0369(4) Uani 1 1 d . . . . .
H19A H 0.171(4) 0.3735(11) 0.087(3) 0.080(9) Uiso 1 1 d . . . . .
H19B H 0.345(5) 0.3608(12) 0.174(3) 0.097(11) Uiso 1 1 d . . . . .
H19C H 0.175(4) 0.3789(11) 0.200(3) 0.089(10) Uiso 1 1 d . . . . .
P1 P 0.17405(6) 0.20252(2) 0.43600(3) 0.02722(9) Uani 1 1 d . . . . .
F1 F 0.28849(16) 0.23065(5) 0.36488(9) 0.0511(3) Uani 1 1 d . . . . .
F2 F 0.05878(17) 0.17438(5) 0.50642(10) 0.0492(3) Uani 1 1 d . . . . .
F3B F 0.112(2) 0.1551(4) 0.3504(9) 0.071(4) Uani 0.178(6) 1 d . U P A 2
F4B F 0.0040(17) 0.2274(6) 0.3616(13) 0.079(4) Uani 0.178(6) 1 d . U P A 2
F5 F 0.1110(4) 0.25563(8) 0.4747(3) 0.0720(8) Uani 0.822(6) 1 d . U P A 1
F6B F 0.3390(14) 0.1706(6) 0.5050(11) 0.077(4) Uani 0.178(6) 1 d . U P A 2
F3 F 0.2363(5) 0.15167(7) 0.3957(3) 0.0763(10) Uani 0.822(6) 1 d . U P A 1
F4 F -0.0021(3) 0.20360(15) 0.32998(17) 0.0746(10) Uani 0.822(6) 1 d . U P A 1
F5B F 0.215(2) 0.2466(5) 0.5108(10) 0.082(4) Uani 0.178(6) 1 d . U P A 2
F6 F 0.3488(3) 0.20378(14) 0.54352(14) 0.0695(9) Uani 0.822(6) 1 d . U P A 1


_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 C3 1.7363(15) . ?
O1 C1 1.4075(16) . ?
O1 C10 1.3727(16) . ?
O2 C10 1.1974(18) . ?
N1 C2 1.3336(17) . ?
N1 C4 1.465(2) . ?
N1 C5 1.4661(19) . ?
N2 C2 1.3324(18) . ?
N2 C6 1.469(2) . ?
N2 C7 1.463(2) . ?
N3 C3 1.3465(19) . ?
N3 C8 1.454(2) . ?
N3 C9 1.464(2) . ?
C1 C2 1.4570(19) . ?
C1 C3 1.3614(18) . ?
C4 H4A 0.94(2) . ?
C4 H4B 0.95(2) . ?
C4 H4C 0.93(2) . ?
C5 H5A 0.97(2) . ?
C5 H5B 0.94(2) . ?
C5 H5C 0.96(2) . ?
C6 H6A 0.94(2) . ?
C6 H6B 0.95(2) . ?
C6 H6C 0.97(2) . ?
C7 H7A 0.96(2) . ?
C7 H7B 0.97(2) . ?
C7 H7C 0.97(2) . ?
C8 H8A 1.00(2) . ?
C8 H8B 0.94(2) . ?
C8 H8C 0.93(2) . ?
C9 H9A 0.93(3) . ?
C9 H9B 0.94(2) . ?
C9 H9C 0.92(3) . ?
C10 C11 1.4928(18) . ?
C11 C12 1.401(2) . ?
C11 C16 1.4004(19) . ?
C12 C13 1.392(2) . ?
C12 C17 1.508(2) . ?
C13 H13 0.94(2) . ?
C13 C14 1.391(2) . ?
C14 C15 1.383(2) . ?
C14 C18 1.510(2) . ?
C15 H15 0.927(19) . ?
C15 C16 1.395(2) . ?
C16 C19 1.507(2) . ?
C17 H17A 0.93(2) . ?
C17 H17B 0.97(2) . ?
C17 H17C 0.96(2) . ?
C18 H18A 0.94(3) . ?
C18 H18B 0.94(3) . ?
C18 H18C 0.96(3) . ?
C19 H19A 0.90(3) . ?
C19 H19B 0.92(4) . ?
C19 H19C 0.94(3) . ?
P1 F1 1.5966(11) . ?
P1 F2 1.5948(11) . ?
P1 F3B 1.623(8) . ?
P1 F4B 1.501(9) . ?
P1 F5 1.601(2) . ?
P1 F6B 1.543(8) . ?
P1 F3 1.5546(18) . ?
P1 F4 1.580(2) . ?
P1 F5B 1.467(9) . ?
P1 F6 1.5859(17) . ?

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
C10 O1 C1 114.71(10) . . ?
C2 N1 C4 122.24(12) . . ?
C2 N1 C5 123.07(13) . . ?
C4 N1 C5 114.67(13) . . ?
C2 N2 C6 122.71(13) . . ?
C2 N2 C7 122.53(13) . . ?
C7 N2 C6 114.58(13) . . ?
C3 N3 C8 121.85(13) . . ?
C3 N3 C9 122.34(15) . . ?
C8 N3 C9 115.80(15) . . ?
O1 C1 C2 115.03(11) . . ?
C3 C1 O1 119.08(12) . . ?
C3 C1 C2 125.84(12) . . ?
N1 C2 C1 118.34(12) . . ?
N2 C2 N1 121.42(13) . . ?
N2 C2 C1 120.18(12) . . ?
N3 C3 Cl1 116.00(11) . . ?
N3 C3 C1 126.56(14) . . ?
C1 C3 Cl1 117.39(11) . . ?
N1 C4 H4A 110.5(11) . . ?
N1 C4 H4B 109.8(13) . . ?
N1 C4 H4C 108.4(13) . . ?
H4A C4 H4B 110.0(17) . . ?
H4A C4 H4C 110.5(18) . . ?
H4B C4 H4C 107.6(17) . . ?
N1 C5 H5A 105.9(12) . . ?
N1 C5 H5B 111.0(13) . . ?
N1 C5 H5C 109.8(12) . . ?
H5A C5 H5B 109.8(17) . . ?
H5A C5 H5C 109.1(17) . . ?
H5B C5 H5C 111.0(18) . . ?
N2 C6 H6A 110.8(13) . . ?
N2 C6 H6B 106.4(13) . . ?
N2 C6 H6C 110.6(12) . . ?
H6A C6 H6B 111.6(18) . . ?
H6A C6 H6C 110.0(18) . . ?
H6B C6 H6C 107.2(18) . . ?
N2 C7 H7A 108.2(13) . . ?
N2 C7 H7B 111.4(12) . . ?
N2 C7 H7C 111.1(13) . . ?
H7A C7 H7B 109.3(18) . . ?
H7A C7 H7C 108.8(17) . . ?
H7B C7 H7C 108.0(18) . . ?
N3 C8 H8A 107.9(13) . . ?
N3 C8 H8B 107.8(13) . . ?
N3 C8 H8C 111.1(14) . . ?
H8A C8 H8B 108.3(18) . . ?
H8A C8 H8C 111.3(19) . . ?
H8B C8 H8C 110.3(19) . . ?
N3 C9 H9A 108.1(16) . . ?
N3 C9 H9B 110.1(14) . . ?
N3 C9 H9C 115.8(16) . . ?
H9A C9 H9B 105(2) . . ?
H9A C9 H9C 105(2) . . ?
H9B C9 H9C 112(2) . . ?
O1 C10 C11 112.12(11) . . ?
O2 C10 O1 122.06(12) . . ?
O2 C10 C11 125.77(13) . . ?
C12 C11 C10 120.94(12) . . ?
C16 C11 C10 117.80(13) . . ?
C16 C11 C12 121.23(13) . . ?
C11 C12 C17 122.40(13) . . ?
C13 C12 C11 118.47(14) . . ?
C13 C12 C17 119.10(14) . . ?
C12 C13 H13 119.0(12) . . ?
C14 C13 C12 121.73(15) . . ?
C14 C13 H13 119.3(12) . . ?
C13 C14 C18 120.44(16) . . ?
C15 C14 C13 118.26(13) . . ?
C15 C14 C18 121.29(16) . . ?
C14 C15 H15 119.6(12) . . ?
C14 C15 C16 122.45(14) . . ?
C16 C15 H15 117.9(12) . . ?
C11 C16 C19 123.20(13) . . ?
C15 C16 C11 117.83(14) . . ?
C15 C16 C19 118.94(14) . . ?
C12 C17 H17A 108.4(13) . . ?
C12 C17 H17B 112.1(12) . . ?
C12 C17 H17C 110.8(13) . . ?
H17A C17 H17B 107.6(18) . . ?
H17A C17 H17C 109.7(18) . . ?
H17B C17 H17C 108.2(17) . . ?
C14 C18 H18A 111.3(16) . . ?
C14 C18 H18B 113.7(18) . . ?
C14 C18 H18C 111.6(18) . . ?
H18A C18 H18B 105(2) . . ?
H18A C18 H18C 112(2) . . ?
H18B C18 H18C 103(2) . . ?
C16 C19 H19A 113.5(19) . . ?
C16 C19 H19B 114(2) . . ?
C16 C19 H19C 112.6(19) . . ?
H19A C19 H19B 109(3) . . ?
H19A C19 H19C 100(3) . . ?
H19B C19 H19C 108(3) . . ?
F1 P1 F3B 95.4(3) . . ?
F1 P1 F5 91.18(10) . . ?
F2 P1 F1 179.68(7) . . ?
F2 P1 F3B 84.4(3) . . ?
F2 P1 F5 88.85(10) . . ?
F4B P1 F1 87.8(5) . . ?
F4B P1 F2 91.9(5) . . ?
F4B P1 F3B 84.2(7) . . ?
F4B P1 F6B 172.7(8) . . ?
F6B P1 F1 94.5(4) . . ?
F6B P1 F2 85.7(4) . . ?
F6B P1 F3B 88.8(7) . . ?
F3 P1 F1 87.38(10) . . ?
F3 P1 F2 92.58(9) . . ?
F3 P1 F5 178.45(13) . . ?
F3 P1 F4 90.41(15) . . ?
F3 P1 F6 91.96(15) . . ?
F4 P1 F1 89.44(10) . . ?
F4 P1 F2 90.25(11) . . ?
F4 P1 F5 89.00(15) . . ?
F4 P1 F6 177.60(16) . . ?
F5B P1 F1 86.5(5) . . ?
F5B P1 F2 93.7(5) . . ?
F5B P1 F3B 175.3(8) . . ?
F5B P1 F4B 91.6(8) . . ?
F5B P1 F6B 95.4(8) . . ?
F6 P1 F1 90.26(8) . . ?
F6 P1 F2 90.06(8) . . ?
F6 P1 F5 88.62(14) . . ?

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
C5 H5B F4B 0.94(2) 2.25(2) 3.040(10) 140.7(18) 1_655
C5 H5B F4 0.94(2) 2.49(2) 3.368(4) 155.4(18) 1_655
C5 H5C F1 0.96(2) 2.47(2) 3.376(2) 157.2(16) .
C6 H6A F1 0.94(2) 2.48(2) 3.345(2) 152.5(18) .
C6 H6A F6 0.94(2) 2.46(2) 3.184(3) 133.7(17) .
C6 H6C F4B 0.97(2) 2.55(3) 3.487(14) 164.2(17) 1_655
C6 H6C F5 0.97(2) 2.33(2) 3.238(3) 156.0(17) 1_655
C7 H7A F5B 0.96(2) 2.60(3) 3.483(13) 153.8(17) .
C7 H7B O2 0.97(2) 2.53(2) 3.287(2) 134.4(16) .
C7 H7C F3B 0.97(2) 2.41(2) 3.105(9) 128.5(17) 4_666

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
O1 C1 C2 N1 40.30(17) . . . . ?
O1 C1 C2 N2 -136.86(13) . . . . ?
O1 C1 C3 Cl1 17.30(18) . . . . ?
O1 C1 C3 N3 -160.12(14) . . . . ?
O1 C10 C11 C12 -56.07(17) . . . . ?
O1 C10 C11 C16 125.49(13) . . . . ?
O2 C10 C11 C12 126.30(17) . . . . ?
O2 C10 C11 C16 -52.1(2) . . . . ?
C1 O1 C10 O2 6.81(19) . . . . ?
C1 O1 C10 C11 -170.92(11) . . . . ?
C2 C1 C3 Cl1 -165.18(11) . . . . ?
C2 C1 C3 N3 17.4(2) . . . . ?
C3 C1 C2 N1 -137.32(15) . . . . ?
C3 C1 C2 N2 45.5(2) . . . . ?
C4 N1 C2 N2 -153.60(14) . . . . ?
C4 N1 C2 C1 29.3(2) . . . . ?
C5 N1 C2 N2 28.2(2) . . . . ?
C5 N1 C2 C1 -148.96(14) . . . . ?
C6 N2 C2 N1 30.2(2) . . . . ?
C6 N2 C2 C1 -152.69(13) . . . . ?
C7 N2 C2 N1 -154.89(14) . . . . ?
C7 N2 C2 C1 22.2(2) . . . . ?
C8 N3 C3 Cl1 -151.87(13) . . . . ?
C8 N3 C3 C1 25.6(2) . . . . ?
C9 N3 C3 Cl1 27.2(2) . . . . ?
C9 N3 C3 C1 -155.33(16) . . . . ?
C10 O1 C1 C2 68.19(15) . . . . ?
C10 O1 C1 C3 -114.03(14) . . . . ?
C10 C11 C12 C13 -178.65(13) . . . . ?
C10 C11 C12 C17 -0.6(2) . . . . ?
C10 C11 C16 C15 178.85(13) . . . . ?
C10 C11 C16 C19 -3.1(2) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C11 C16 C15 0.4(2) . . . . ?
C12 C11 C16 C19 178.47(15) . . . . ?
C12 C13 C14 C15 0.8(2) . . . . ?
C12 C13 C14 C18 -178.74(14) . . . . ?
C13 C14 C15 C16 -0.6(2) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
C14 C15 C16 C19 -178.11(16) . . . . ?
C16 C11 C12 C13 -0.3(2) . . . . ?
C16 C11 C12 C17 177.83(14) . . . . ?
C17 C12 C13 C14 -178.50(15) . . . . ?
C18 C14 C15 C16 178.90(15) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_date_sample_data_collection 2018-01-17
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.103
_oxdiff_exptl_absorpt_empirical_full_min 0.884


####################################################################### 
# 
# 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_9b
_database_code_depnum_ccdc_archive 'CCDC 1898558'
loop_
_audit_author_name
_audit_author_address
'Jacques Pecaut '
;CEA Grenoble
France
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_audit_creation_date             2018-01-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            9b
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H29 N3 O2, F6 P, C2 H3 N'
_chemical_formula_sum            'C21 H32 F6 N4 O2 P'
_chemical_formula_weight         517.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cl O2 N3 P F6 C20 H40'
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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.3903(10)
_cell_length_b                   16.1931(10)
_cell_length_c                   13.6174(11)
_cell_angle_alpha                90
_cell_angle_beta                 113.783(10)
_cell_angle_gamma                90
_cell_volume                     2500.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3156
_cell_measurement_temperature    149.95(10)
_cell_measurement_theta_max      28.2540
_cell_measurement_theta_min      2.9970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1084
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -2 0 0.2312
-1 -1 0 0.2442
0 1 0 0.0305
0 -1 0 0.0505
0 0 -1 0.0800
0 0 1 0.0640
0 -1 1 0.0601
0 1 -1 0.0611
0 2 1 0.0450
0 -2 -1 0.0610
2 0 -1 0.3812
-1 -1 1 0.2115
1 -1 -2 0.2066

_exptl_crystal_size_max          0.722
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.081
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9887 -2.0163 0.0061 0.0311 0.0081 -0.1030
-1.0068 -1.0158 0.0055 0.0249 -0.0729 0.0015
0.0060 1.0107 -0.0039 -0.0187 0.0216 0.0338
-0.0060 -1.0107 0.0039 0.0187 -0.0216 -0.0338
-0.0067 -0.0065 -0.9961 -0.0445 -0.0353 -0.0023
0.0067 0.0065 0.9961 0.0445 0.0353 0.0023
0.0007 -1.0042 0.9999 0.0632 0.0137 -0.0316
-0.0007 1.0042 -0.9999 -0.0632 -0.0137 0.0316
0.0188 2.0279 0.9883 0.0072 0.0785 0.0700
-0.0188 -2.0279 -0.9883 -0.0072 -0.0785 -0.0700
1.9948 0.0037 -0.9994 -0.0570 0.0672 -0.0730
-1.0001 -1.0093 1.0016 0.0694 -0.0376 0.0038
0.9813 -1.0186 -1.9899 -0.0766 -0.0409 -0.0737

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23721
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.062
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9653
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  41.00   1.00   10.00    --   -0.62 -99.00  60.00   66
  2  ω     34.00 125.00   1.00   60.00    --   55.51  52.00  23.00   91
  3  ω     25.00 126.00   1.00   60.00    --   55.51  77.00 120.00  101
  4  ω    -13.00  77.00   1.00   60.00    --   55.51 -57.00  60.00   90
  5  ω     73.00 127.00   1.00   60.00    --   55.51 125.00 -60.00   54
  6  ω     73.00 127.00   1.00   60.00    --   55.51 125.00  60.00   54
  7  ω     25.00 126.00   1.00   60.00    --   55.51  77.00  60.00  101
  8  ω    -15.00  86.00   1.00   60.00    --   55.51 -77.00-120.00  101
  9  ω   -129.00-117.00   1.00   60.00    --  -56.76 -99.00   0.00   12
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0060584000
_diffrn_orient_matrix_UB_12      -0.0182482000
_diffrn_orient_matrix_UB_13      0.0448381000
_diffrn_orient_matrix_UB_21      0.0511865000
_diffrn_orient_matrix_UB_22      0.0211952000
_diffrn_orient_matrix_UB_23      0.0349698000
_diffrn_orient_matrix_UB_31      -0.0354947000
_diffrn_orient_matrix_UB_32      0.0337049000
_diffrn_orient_matrix_UB_33      0.0022994000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3569
_reflns_number_total             5052
_reflns_odcompleteness_completeness 98.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         5052
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+1.8405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1473
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
F1 \\sim F4 \\sim F5 \\sim F3 \\sim F2 \\sim F6 \\sim F6B \\sim F2B \\sim F5B
\\sim F3B \\sim F4B: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.01
Uanis(P1) \\sim Ueq, Uanis(P1B) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
2. Others
 Sof(P1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=1-FVAR(1)
 Sof(P1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.49409(14) 0.50331(11) 0.61699(14) 0.0355(4) Uani 1 1 d . . . . .
O2 O 0.34239(16) 0.42318(12) 0.51958(17) 0.0442(5) Uani 1 1 d . . . . .
N1 N 0.71355(18) 0.56114(15) 0.76355(17) 0.0385(5) Uani 1 1 d . . . . .
N2 N 0.64979(18) 0.69130(14) 0.69570(17) 0.0386(5) Uani 1 1 d . . . . .
N3 N 0.38362(19) 0.68089(13) 0.71007(17) 0.0358(5) Uani 1 1 d . . . . .
C1 C 0.6270(2) 0.61323(17) 0.71030(19) 0.0340(5) Uani 1 1 d . . . . .
C2 C 0.5073(2) 0.58299(15) 0.66544(19) 0.0319(5) Uani 1 1 d . . . . .
C3 C 0.4029(2) 0.61347(15) 0.65934(18) 0.0292(5) Uani 1 1 d . . . . .
C4 C 0.3049(2) 0.55242(14) 0.59651(18) 0.0274(5) Uani 1 1 d . . . . .
C5 C 0.3773(2) 0.48450(15) 0.5711(2) 0.0324(5) Uani 1 1 d . . . . .
C6 C 0.2141(2) 0.58590(14) 0.49110(18) 0.0282(5) Uani 1 1 d . . . . .
C7 C 0.0992(2) 0.57641(14) 0.4639(2) 0.0288(5) Uani 1 1 d . . . . .
H7 H 0.047(3) 0.5983(19) 0.396(3) 0.044(8) Uiso 1 1 d . . . . .
C8 C 0.0411(2) 0.53775(14) 0.5310(2) 0.0287(5) Uani 1 1 d . . . . .
C9 C 0.1337(2) 0.50893(14) 0.6358(2) 0.0299(5) Uani 1 1 d . . . . .
H9 H 0.103(2) 0.4876(16) 0.684(2) 0.029(6) Uiso 1 1 d . . . . .
C10 C 0.2496(2) 0.51486(14) 0.66817(19) 0.0299(5) Uani 1 1 d . . . . .
C11 C 0.6955(3) 0.4892(2) 0.8198(3) 0.0456(7) Uani 1 1 d . . . . .
H11A H 0.768(3) 0.486(2) 0.892(3) 0.064(10) Uiso 1 1 d . . . . .
H11B H 0.622(3) 0.4958(18) 0.828(3) 0.043(8) Uiso 1 1 d . . . . .
H11C H 0.686(4) 0.439(3) 0.775(4) 0.084(13) Uiso 1 1 d . . . . .
C12 C 0.8326(2) 0.5690(3) 0.7648(3) 0.0509(8) Uani 1 1 d . . . . .
H12A H 0.888(3) 0.583(2) 0.838(3) 0.063(10) Uiso 1 1 d . . . . .
H12B H 0.828(3) 0.609(2) 0.707(3) 0.062(10) Uiso 1 1 d . . . . .
H12C H 0.857(3) 0.513(2) 0.746(3) 0.058(9) Uiso 1 1 d . . . . .
C13 C 0.7494(3) 0.7375(2) 0.7750(3) 0.0508(8) Uani 1 1 d . . . . .
H13A H 0.778(3) 0.707(2) 0.846(3) 0.051(8) Uiso 1 1 d . . . . .
H13B H 0.813(4) 0.745(2) 0.747(3) 0.070(11) Uiso 1 1 d . . . . .
H13C H 0.716(3) 0.795(3) 0.785(3) 0.065(10) Uiso 1 1 d . . . . .
C14 C 0.5759(3) 0.7377(2) 0.6006(3) 0.0497(8) Uani 1 1 d . . . . .
H14A H 0.626(4) 0.768(3) 0.583(4) 0.071(11) Uiso 1 1 d . . . . .
H14B H 0.525(3) 0.701(2) 0.544(3) 0.052(9) Uiso 1 1 d . . . . .
H14C H 0.528(4) 0.775(3) 0.623(4) 0.088(14) Uiso 1 1 d . . . . .
C15 C 0.4784(3) 0.7165(2) 0.8032(3) 0.0486(7) Uani 1 1 d . . . . .
H15A H 0.544(3) 0.6758(19) 0.834(3) 0.042(8) Uiso 1 1 d . . . . .
H15B H 0.519(3) 0.765(2) 0.786(3) 0.054(9) Uiso 1 1 d . . . . .
H15C H 0.444(3) 0.738(2) 0.848(3) 0.060(10) Uiso 1 1 d . . . . .
C16 C 0.2694(3) 0.71848(19) 0.6810(3) 0.0423(6) Uani 1 1 d . . . . .
H16A H 0.277(3) 0.780(2) 0.670(3) 0.052(9) Uiso 1 1 d . . . . .
H16B H 0.211(3) 0.696(2) 0.624(3) 0.056(9) Uiso 1 1 d . . . . .
H16C H 0.245(5) 0.708(3) 0.741(5) 0.110(17) Uiso 1 1 d . . . . .
C17 C 0.2640(2) 0.62981(19) 0.4216(2) 0.0381(6) Uani 1 1 d . . . . .
H17A H 0.301(3) 0.6831(19) 0.454(2) 0.040(7) Uiso 1 1 d . . . . .
H17B H 0.322(3) 0.596(2) 0.409(3) 0.063(10) Uiso 1 1 d . . . . .
H17C H 0.198(3) 0.6449(18) 0.353(3) 0.045(8) Uiso 1 1 d . . . . .
C18 C -0.0358(3) 0.60365(17) 0.5533(3) 0.0386(6) Uani 1 1 d . . . . .
H18A H -0.095(3) 0.623(2) 0.488(3) 0.052(9) Uiso 1 1 d . . . . .
H18B H 0.013(2) 0.6493(18) 0.591(2) 0.034(7) Uiso 1 1 d . . . . .
H18C H -0.077(3) 0.581(2) 0.594(3) 0.048(8) Uiso 1 1 d . . . . .
C19 C 0.3345(3) 0.4833(2) 0.7752(2) 0.0404(6) Uani 1 1 d . . . . .
H19A H 0.390(3) 0.4446(18) 0.764(2) 0.036(7) Uiso 1 1 d . . . . .
H19B H 0.380(3) 0.528(2) 0.819(3) 0.050(9) Uiso 1 1 d . . . . .
H19C H 0.290(3) 0.455(2) 0.811(3) 0.061(10) Uiso 1 1 d . . . . .
F1 F 0.9650(2) 0.80119(13) 0.51206(18) 0.0772(6) Uani 1 1 d . U . . .
P1 P 0.9483(4) 0.8557(4) 0.6003(5) 0.0322(8) Uani 0.549(5) 1 d . U P A 1
F2 F 0.9431(7) 0.9157(4) 0.6906(5) 0.0794(17) Uani 0.549(5) 1 d . U P A 1
F3 F 0.9501(8) 0.7771(4) 0.6681(6) 0.0915(18) Uani 0.549(5) 1 d . U P A 1
F4 F 1.0838(4) 0.8594(4) 0.6511(4) 0.0937(18) Uani 0.549(5) 1 d . U P A 1
F5 F 0.9443(6) 0.9346(2) 0.5333(4) 0.0757(13) Uani 0.549(5) 1 d . U P A 1
F6 F 0.8070(4) 0.8544(5) 0.5441(6) 0.1137(19) Uani 0.549(5) 1 d . U P A 1
P1B P 0.9302(6) 0.8448(5) 0.6031(6) 0.0395(13) Uani 0.451(5) 1 d . U P A 2
F2B F 0.8897(8) 0.8835(5) 0.6858(7) 0.086(2) Uani 0.451(5) 1 d . U P A 2
F3B F 1.0141(6) 0.7851(5) 0.6942(5) 0.068(2) Uani 0.451(5) 1 d . U P A 2
F4B F 1.0400(8) 0.9077(5) 0.6424(7) 0.115(2) Uani 0.451(5) 1 d . U P A 2
F5B F 0.8574(10) 0.9049(5) 0.5128(5) 0.104(2) Uani 0.451(5) 1 d . U P A 2
F6B F 0.8375(5) 0.7777(4) 0.5719(5) 0.0826(16) Uani 0.451(5) 1 d . U P A 2
N21 N 0.3532(3) 0.8640(2) 0.4873(4) 0.0903(11) Uani 1 1 d . . . . .
C21 C 0.2548(3) 0.8699(2) 0.4449(3) 0.0562(8) Uani 1 1 d . . . . .
C22 C 0.1291(3) 0.8793(3) 0.3899(4) 0.0646(10) Uani 1 1 d . . . . .
H22A H 0.094(6) 0.856(4) 0.423(6) 0.13(2) Uiso 1 1 d . . . . .
H22B H 0.109(6) 0.937(4) 0.373(6) 0.13(2) Uiso 1 1 d . . . . .
H22C H 0.086(6) 0.839(4) 0.329(6) 0.13(2) Uiso 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 C2 1.428(3) . ?
O1 C5 1.360(3) . ?
O2 C5 1.192(3) . ?
N1 C1 1.326(3) . ?
N1 C11 1.460(4) . ?
N1 C12 1.473(4) . ?
N2 C1 1.328(4) . ?
N2 C13 1.475(4) . ?
N2 C14 1.458(4) . ?
N3 C3 1.364(3) . ?
N3 C15 1.455(4) . ?
N3 C16 1.441(4) . ?
C1 C2 1.443(3) . ?
C2 C3 1.356(4) . ?
C3 C4 1.531(3) . ?
C4 C5 1.544(3) . ?
C4 C6 1.522(3) . ?
C4 C10 1.527(3) . ?
C6 C7 1.328(3) . ?
C6 C17 1.502(3) . ?
C7 H7 0.96(3) . ?
C7 C8 1.509(3) . ?
C8 C8 1.597(5) 3_566 ?
C8 C9 1.500(4) . ?
C8 C18 1.540(3) . ?
C9 H9 0.95(3) . ?
C9 C10 1.324(4) . ?
C10 C19 1.502(4) . ?
C11 H11A 1.03(4) . ?
C11 H11B 0.97(3) . ?
C11 H11C 1.00(5) . ?
C12 H12A 0.98(4) . ?
C12 H12B 1.00(4) . ?
C12 H12C 1.03(4) . ?
C13 H13A 1.01(4) . ?
C13 H13B 1.02(4) . ?
C13 H13C 1.05(4) . ?
C14 H14A 0.89(4) . ?
C14 H14B 0.97(4) . ?
C14 H14C 0.99(5) . ?
C15 H15A 0.99(3) . ?
C15 H15B 1.01(4) . ?
C15 H15C 0.95(4) . ?
C16 H16A 1.01(4) . ?
C16 H16B 0.90(4) . ?
C16 H16C 0.99(6) . ?
C17 H17A 0.99(3) . ?
C17 H17B 0.97(4) . ?
C17 H17C 1.00(3) . ?
C18 H18A 0.95(4) . ?
C18 H18B 0.96(3) . ?
C18 H18C 0.96(4) . ?
C19 H19A 0.99(3) . ?
C19 H19B 0.96(4) . ?
C19 H19C 0.98(4) . ?
F1 P1 1.571(6) . ?
F1 P1B 1.629(9) . ?
P1 F2 1.588(8) . ?
P1 F3 1.567(8) . ?
P1 F4 1.538(7) . ?
P1 F5 1.559(7) . ?
P1 F6 1.603(7) . ?
P1B F2B 1.538(11) . ?
P1B F3B 1.587(10) . ?
P1B F4B 1.609(9) . ?
P1B F5B 1.542(9) . ?
P1B F6B 1.512(8) . ?
N21 C21 1.124(5) . ?
C21 C22 1.438(5) . ?
C22 H22A 0.83(7) . ?
C22 H22B 0.98(7) . ?
C22 H22C 1.02(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
C5 O1 C2 108.51(18) . . ?
C1 N1 C11 122.2(2) . . ?
C1 N1 C12 122.4(2) . . ?
C11 N1 C12 115.3(2) . . ?
C1 N2 C13 122.6(2) . . ?
C1 N2 C14 122.0(2) . . ?
C14 N2 C13 115.4(2) . . ?
C3 N3 C15 120.9(2) . . ?
C3 N3 C16 123.5(2) . . ?
C16 N3 C15 115.4(2) . . ?
N1 C1 N2 120.9(2) . . ?
N1 C1 C2 118.8(2) . . ?
N2 C1 C2 120.3(2) . . ?
O1 C2 C1 114.2(2) . . ?
C3 C2 O1 111.8(2) . . ?
C3 C2 C1 134.0(2) . . ?
N3 C3 C4 122.6(2) . . ?
C2 C3 N3 128.2(2) . . ?
C2 C3 C4 108.7(2) . . ?
C3 C4 C5 100.62(18) . . ?
C6 C4 C3 114.51(19) . . ?
C6 C4 C5 108.51(19) . . ?
C6 C4 C10 113.11(19) . . ?
C10 C4 C3 111.05(19) . . ?
C10 C4 C5 108.10(19) . . ?
O1 C5 C4 110.11(19) . . ?
O2 C5 O1 121.6(2) . . ?
O2 C5 C4 128.3(2) . . ?
C7 C6 C4 121.6(2) . . ?
C7 C6 C17 123.1(2) . . ?
C17 C6 C4 115.3(2) . . ?
C6 C7 H7 116.9(18) . . ?
C6 C7 C8 126.8(2) . . ?
C8 C7 H7 116.2(18) . . ?
C7 C8 C8 110.8(2) . 3_566 ?
C7 C8 C18 108.4(2) . . ?
C9 C8 C7 109.64(19) . . ?
C9 C8 C8 110.2(2) . 3_566 ?
C9 C8 C18 109.0(2) . . ?
C18 C8 C8 108.8(2) . 3_566 ?
C8 C9 H9 114.2(16) . . ?
C10 C9 C8 127.2(2) . . ?
C10 C9 H9 118.4(16) . . ?
C9 C10 C4 121.5(2) . . ?
C9 C10 C19 122.6(2) . . ?
C19 C10 C4 115.9(2) . . ?
N1 C11 H11A 106(2) . . ?
N1 C11 H11B 109.0(18) . . ?
N1 C11 H11C 110(3) . . ?
H11A C11 H11B 113(3) . . ?
H11A C11 H11C 112(3) . . ?
H11B C11 H11C 106(3) . . ?
N1 C12 H12A 109(2) . . ?
N1 C12 H12B 108(2) . . ?
N1 C12 H12C 108(2) . . ?
H12A C12 H12B 116(3) . . ?
H12A C12 H12C 108(3) . . ?
H12B C12 H12C 108(3) . . ?
N2 C13 H13A 108.4(19) . . ?
N2 C13 H13B 110(2) . . ?
N2 C13 H13C 107(2) . . ?
H13A C13 H13B 113(3) . . ?
H13A C13 H13C 108(3) . . ?
H13B C13 H13C 111(3) . . ?
N2 C14 H14A 105(3) . . ?
N2 C14 H14B 111(2) . . ?
N2 C14 H14C 106(3) . . ?
H14A C14 H14B 115(3) . . ?
H14A C14 H14C 109(4) . . ?
H14B C14 H14C 110(4) . . ?
N3 C15 H15A 109.7(18) . . ?
N3 C15 H15B 114(2) . . ?
N3 C15 H15C 107(2) . . ?
H15A C15 H15B 102(3) . . ?
H15A C15 H15C 118(3) . . ?
H15B C15 H15C 106(3) . . ?
N3 C16 H16A 108.4(19) . . ?
N3 C16 H16B 115(2) . . ?
N3 C16 H16C 107(3) . . ?
H16A C16 H16B 112(3) . . ?
H16A C16 H16C 111(4) . . ?
H16B C16 H16C 104(4) . . ?
C6 C17 H17A 111.8(18) . . ?
C6 C17 H17B 111(2) . . ?
C6 C17 H17C 108.5(18) . . ?
H17A C17 H17B 109(3) . . ?
H17A C17 H17C 105(2) . . ?
H17B C17 H17C 111(3) . . ?
C8 C18 H18A 110(2) . . ?
C8 C18 H18B 109.4(17) . . ?
C8 C18 H18C 111.0(19) . . ?
H18A C18 H18B 109(3) . . ?
H18A C18 H18C 107(3) . . ?
H18B C18 H18C 111(3) . . ?
C10 C19 H19A 109.1(17) . . ?
C10 C19 H19B 111(2) . . ?
C10 C19 H19C 109(2) . . ?
H19A C19 H19B 108(3) . . ?
H19A C19 H19C 110(3) . . ?
H19B C19 H19C 111(3) . . ?
F1 P1 F2 174.2(5) . . ?
F1 P1 F6 94.7(4) . . ?
F2 P1 F6 90.0(5) . . ?
F3 P1 F1 91.1(4) . . ?
F3 P1 F2 92.1(5) . . ?
F3 P1 F6 91.4(5) . . ?
F4 P1 F1 84.8(4) . . ?
F4 P1 F2 90.3(4) . . ?
F4 P1 F3 90.7(5) . . ?
F4 P1 F5 90.1(4) . . ?
F4 P1 F6 177.8(6) . . ?
F5 P1 F1 89.8(4) . . ?
F5 P1 F2 87.1(4) . . ?
F5 P1 F3 178.8(5) . . ?
F5 P1 F6 87.7(5) . . ?
F2B P1B F1 176.4(6) . . ?
F2B P1B F3B 88.9(6) . . ?
F2B P1B F4B 88.9(6) . . ?
F2B P1B F5B 93.9(6) . . ?
F3B P1B F1 92.3(5) . . ?
F3B P1B F4B 85.8(5) . . ?
F4B P1B F1 94.6(5) . . ?
F5B P1B F1 85.2(5) . . ?
F5B P1B F3B 175.4(7) . . ?
F5B P1B F4B 90.6(7) . . ?
F6B P1B F1 83.0(4) . . ?
F6B P1B F2B 93.6(5) . . ?
F6B P1B F3B 88.0(5) . . ?
F6B P1B F4B 173.3(7) . . ?
F6B P1B F5B 95.5(6) . . ?
N21 C21 C22 178.8(4) . . ?
C21 C22 H22A 111(5) . . ?
C21 C22 H22B 110(4) . . ?
C21 C22 H22C 117(4) . . ?
H22A C22 H22B 116(6) . . ?
H22A C22 H22C 86(6) . . ?
H22B C22 H22C 115(6) . . ?

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
C11 H11A F5B 1.03(4) 2.37(4) 3.102(6) 128(3) 4_576
C12 H12A F5 0.98(4) 2.48(4) 3.348(6) 147(3) 4_576
C12 H12C F4B 1.03(4) 2.29(4) 3.049(7) 129(3) 2_746
C13 H13A F1 1.01(4) 2.50(4) 3.315(4) 137(2) 4_576
C13 H13B F3 1.02(4) 2.40(4) 3.412(8) 173(3) .
C13 H13B F6B 1.02(4) 2.57(4) 3.421(7) 140(3) .
C22 H22B F2 0.98(7) 2.52(7) 3.497(8) 174(6) 3_676
C22 H22C F3B 1.02(7) 2.62(7) 3.626(8) 168(5) 4_475

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
O1 C2 C3 N3 169.2(2) . . . . ?
O1 C2 C3 C4 -2.9(3) . . . . ?
N1 C1 C2 O1 -41.1(3) . . . . ?
N1 C1 C2 C3 138.4(3) . . . . ?
N2 C1 C2 O1 137.0(2) . . . . ?
N2 C1 C2 C3 -43.4(4) . . . . ?
N3 C3 C4 C5 -172.5(2) . . . . ?
N3 C3 C4 C6 71.4(3) . . . . ?
N3 C3 C4 C10 -58.2(3) . . . . ?
C1 C2 C3 N3 -10.4(5) . . . . ?
C1 C2 C3 C4 177.6(3) . . . . ?
C2 O1 C5 O2 175.3(2) . . . . ?
C2 O1 C5 C4 -4.6(3) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 C6 -116.1(2) . . . . ?
C2 C3 C4 C10 114.3(2) . . . . ?
C3 C4 C5 O1 2.8(2) . . . . ?
C3 C4 C5 O2 -177.1(3) . . . . ?
C3 C4 C6 C7 -133.4(2) . . . . ?
C3 C4 C6 C17 46.6(3) . . . . ?
C3 C4 C10 C9 134.1(2) . . . . ?
C3 C4 C10 C19 -47.6(3) . . . . ?
C4 C6 C7 C8 3.7(4) . . . . ?
C5 O1 C2 C1 -175.6(2) . . . . ?
C5 O1 C2 C3 4.8(3) . . . . ?
C5 C4 C6 C7 115.1(2) . . . . ?
C5 C4 C6 C17 -64.9(3) . . . . ?
C5 C4 C10 C9 -116.4(2) . . . . ?
C5 C4 C10 C19 61.9(3) . . . . ?
C6 C4 C5 O1 123.4(2) . . . . ?
C6 C4 C5 O2 -56.6(3) . . . . ?
C6 C4 C10 C9 3.7(3) . . . . ?
C6 C4 C10 C19 -178.0(2) . . . . ?
C6 C7 C8 C8 -122.9(3) . . . 3_566 ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C6 C7 C8 C18 117.8(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C8 C9 C10 122.1(3) 3_566 . . . ?
C8 C9 C10 C4 -1.5(4) . . . . ?
C8 C9 C10 C19 -179.7(2) . . . . ?
C10 C4 C5 O1 -113.6(2) . . . . ?
C10 C4 C5 O2 66.4(3) . . . . ?
C10 C4 C6 C7 -4.8(3) . . . . ?
C10 C4 C6 C17 175.1(2) . . . . ?
C11 N1 C1 N2 153.8(3) . . . . ?
C11 N1 C1 C2 -28.1(4) . . . . ?
C12 N1 C1 N2 -29.9(4) . . . . ?
C12 N1 C1 C2 148.2(3) . . . . ?
C13 N2 C1 N1 -32.8(4) . . . . ?
C13 N2 C1 C2 149.1(3) . . . . ?
C14 N2 C1 N1 148.6(3) . . . . ?
C14 N2 C1 C2 -29.5(4) . . . . ?
C15 N3 C3 C2 -17.9(4) . . . . ?
C15 N3 C3 C4 153.2(3) . . . . ?
C16 N3 C3 C2 166.1(3) . . . . ?
C16 N3 C3 C4 -22.8(4) . . . . ?
C17 C6 C7 C8 -176.2(2) . . . . ?
C18 C8 C9 C10 -118.6(3) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_date_sample_data_collection 2018-01-18
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.253
_oxdiff_exptl_absorpt_empirical_full_min 0.855




####################################################################### 
# 
# 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_6a
_database_code_depnum_ccdc_archive 'CCDC 1898562'
loop_
_audit_author_name
_audit_author_address
'Jacques Pecaut '
;CEA Grenoble
France
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_audit_creation_date             2017-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            6a
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(F6 P), C16 H23 N3 O2'
_chemical_formula_sum            'C16 H23 F12 N3 O2 P2'
_chemical_formula_weight         579.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'P2 F12 O5 N3 C15 H20'
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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.5891(2)
_cell_length_b                   16.2883(4)
_cell_length_c                   13.9030(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.985(2)
_cell_angle_gamma                90
_cell_volume                     2336.64(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9242
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      28.0140
_cell_measurement_theta_min      2.3170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent intense yellow'
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1176
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.0762
0 -1 1 0.1032
0 2 1 0.0734
0 -2 -1 0.0594
-1 -1 1 0.0734
2 -1 0 0.1362
1 -1 -1 0.1248
-1 2 2 0.0545
0 -1 0 0.0754
0 1 0 0.0754
1 0 -1 0.1178

_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.133
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0027 0.9954 -0.9988 -0.0379 0.0126 -0.0549
-0.0027 -0.9954 0.9988 0.0379 -0.0126 0.0549
0.0002 1.9862 0.9955 0.0687 0.0498 -0.0547
-0.0002 -1.9862 -0.9955 -0.0687 -0.0498 0.0547
-0.9999 -0.9929 0.9972 0.0037 0.0426 0.0767
1.9933 -0.9988 0.0042 0.0583 -0.1313 -0.0071
0.9980 -0.9948 -0.9950 -0.0242 -0.0842 -0.0036
-0.9988 1.9872 1.9916 0.0826 0.1132 -0.0146
-0.0010 -0.9939 0.0011 -0.0103 -0.0208 0.0365
0.0010 0.9939 -0.0011 0.0103 0.0208 -0.0365
0.9989 -0.0010 -0.9961 -0.0139 -0.0634 -0.0401

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            55687
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         1.955
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9653
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  47.00   1.00   60.00    --   25.56 -57.00 -90.00   90
  2  ω    -25.00  67.00   1.00   60.00    --   25.56 -99.00-150.00   92
  3  ω    -25.00  67.00   1.00   60.00    --   25.56 -99.00  30.00   92
  4  ω    -47.00  51.00   1.00   60.00    --   25.56 -37.00  60.00   98
  5  ω    -97.00   3.00   1.00   60.00    --  -26.97 -77.00 150.00  100
  6  ω    -96.00  -6.00   1.00   60.00    --  -26.97 -57.00-150.00   90
  7  ω    -96.00  -6.00   1.00   60.00    --  -26.97 -57.00 -60.00   90
  8  ω    -97.00   3.00   1.00   60.00    --  -26.97 -77.00  60.00  100
  9  ω     -4.00  96.00   1.00   60.00    --   25.56  77.00 -30.00  100
 10  ω    -25.00  53.00   1.00   60.00    --   25.56 -99.00 -90.00   78
 11  ω   -104.00 -32.00   1.00   60.00    --  -26.97 178.00   0.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0343171000
_diffrn_orient_matrix_UB_12      0.0103509000
_diffrn_orient_matrix_UB_13      -0.0483756000
_diffrn_orient_matrix_UB_21      0.0553733000
_diffrn_orient_matrix_UB_22      0.0209931000
_diffrn_orient_matrix_UB_23      -0.0081229000
_diffrn_orient_matrix_UB_31      0.0219876000
_diffrn_orient_matrix_UB_32      -0.0367179000
_diffrn_orient_matrix_UB_33      -0.0182809000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5022
_reflns_number_total             7121
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         7121
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+1.4518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1245
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(F5A) \\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F3)
\\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F4A) \\sim Ueq, Uanis(F2) \\sim Ueq,
Uanis(F6) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F4) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
2. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.17697(5) 0.36672(3) -0.01814(4) 0.02875(13) Uani 1 1 d . . . . .
F1 F 0.1864(6) 0.3862(4) 0.0942(4) 0.0583(12) Uani 0.767(16) 1 d . U P A 1
F1A F 0.234(2) 0.4053(14) 0.0892(15) 0.075(6) Uani 0.233(16) 1 d . U P A 2
F2 F 0.1667(6) 0.3457(4) -0.1314(3) 0.0647(14) Uani 0.767(16) 1 d . U P A 1
F2A F 0.136(2) 0.3287(11) -0.1205(14) 0.067(5) Uani 0.233(16) 1 d . U P A 2
F3 F 0.3223(6) 0.3941(4) -0.0076(6) 0.0676(18) Uani 0.767(16) 1 d . U P A 1
F3A F 0.328(2) 0.3632(16) -0.0170(17) 0.069(5) Uani 0.233(16) 1 d . U P A 2
F4 F 0.2267(5) 0.2748(3) 0.0098(3) 0.0508(11) Uani 0.767(16) 1 d . U P A 1
F4A F 0.193(2) 0.2827(13) 0.040(2) 0.088(6) Uani 0.233(16) 1 d . U P A 2
F5 F 0.0297(5) 0.3375(4) -0.0309(5) 0.0692(14) Uani 0.767(16) 1 d . U P A 1
F5A F 0.0388(15) 0.3741(18) -0.0062(12) 0.075(5) Uani 0.233(16) 1 d . U P A 2
F6 F 0.1256(6) 0.4572(3) -0.0494(4) 0.0588(13) Uani 0.767(16) 1 d . U P A 1
F6A F 0.1715(18) 0.4533(11) -0.0648(17) 0.072(5) Uani 0.233(16) 1 d . U P A 2
P2 P 0.75412(6) 0.11142(3) 0.09980(5) 0.03326(14) Uani 1 1 d . . . . .
F11 F 0.85018(12) 0.04422(8) 0.07084(11) 0.0401(3) Uani 1 1 d . . . . .
F12 F 0.65936(19) 0.17791(9) 0.12869(16) 0.0748(6) Uani 1 1 d . . . . .
F13 F 0.82795(16) 0.18133(9) 0.05320(12) 0.0533(4) Uani 1 1 d . . . . .
F14 F 0.65725(16) 0.09677(12) -0.00303(13) 0.0673(5) Uani 1 1 d . . . . .
F15 F 0.68480(13) 0.04088(8) 0.14880(12) 0.0465(4) Uani 1 1 d . . . . .
F16 F 0.85493(18) 0.12525(10) 0.20203(12) 0.0623(5) Uani 1 1 d . . . . .
O1 O 0.57799(12) 0.37367(8) 0.45056(9) 0.0235(3) Uani 1 1 d . . . . .
O2 O 0.77426(12) 0.38230(8) 0.42988(10) 0.0232(3) Uani 1 1 d . . . . .
N1 N 0.45881(15) 0.33148(11) 0.29826(12) 0.0267(3) Uani 1 1 d . . . . .
N2 N 0.86667(16) 0.33427(11) 0.25805(13) 0.0294(4) Uani 1 1 d . . . . .
N3 N 0.67818(17) 0.39627(11) 0.16732(12) 0.0297(4) Uani 1 1 d . . . . .
C1 C 0.70052(17) 0.38851(11) 0.49150(14) 0.0232(4) Uani 1 1 d . . . . .
C2 C 0.57146(18) 0.35504(11) 0.35144(13) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.69366(17) 0.36389(12) 0.33623(14) 0.0234(4) Uani 1 1 d . . . . .
C4 C 0.3392(2) 0.3431(2) 0.3319(2) 0.0457(6) Uani 1 1 d . . . . .
H4A H 0.350(3) 0.3903(19) 0.375(2) 0.061(9) Uiso 1 1 d . . . . .
H4B H 0.275(3) 0.352(2) 0.279(2) 0.067(10) Uiso 1 1 d . . . . .
H4C H 0.311(3) 0.293(2) 0.357(2) 0.068(10) Uiso 1 1 d . . . . .
C5 C 0.4546(2) 0.27930(15) 0.21194(17) 0.0319(4) Uani 1 1 d . . . . .
H5A H 0.531(3) 0.2495(16) 0.2192(18) 0.040(7) Uiso 1 1 d . . . . .
H5B H 0.393(3) 0.2413(19) 0.209(2) 0.058(9) Uiso 1 1 d . . . . .
H5C H 0.438(2) 0.3102(16) 0.156(2) 0.044(7) Uiso 1 1 d . . . . .
C6 C 0.74892(18) 0.36482(12) 0.25069(15) 0.0252(4) Uani 1 1 d . . . . .
C7 C 0.5853(2) 0.46287(14) 0.16616(18) 0.0349(5) Uani 1 1 d . . . . .
H7A H 0.591(2) 0.4837(16) 0.228(2) 0.040(7) Uiso 1 1 d . . . . .
H7B H 0.604(2) 0.5042(17) 0.1292(19) 0.043(7) Uiso 1 1 d . . . . .
H7C H 0.498(3) 0.4426(16) 0.1356(19) 0.046(7) Uiso 1 1 d . . . . .
C8 C 0.6873(3) 0.36847(16) 0.06860(17) 0.0393(5) Uani 1 1 d . . . . .
H8A H 0.740(3) 0.3203(18) 0.0748(19) 0.047(8) Uiso 1 1 d . . . . .
H8B H 0.596(3) 0.3600(16) 0.032(2) 0.049(8) Uiso 1 1 d . . . . .
H8C H 0.731(3) 0.4101(18) 0.037(2) 0.055(8) Uiso 1 1 d . . . . .
C9 C 0.9261(2) 0.27680(15) 0.33626(18) 0.0346(5) Uani 1 1 d . . . . .
H9A H 0.970(2) 0.2349(16) 0.3070(18) 0.040(7) Uiso 1 1 d . . . . .
H9B H 0.862(2) 0.2492(16) 0.3606(18) 0.039(7) Uiso 1 1 d . . . . .
H9C H 0.986(2) 0.3058(15) 0.3880(18) 0.036(6) Uiso 1 1 d . . . . .
C10 C 0.9519(3) 0.35987(18) 0.1931(2) 0.0448(6) Uani 1 1 d . . . . .
H10A H 0.921(2) 0.4124(17) 0.1601(19) 0.043(7) Uiso 1 1 d . . . . .
H10B H 1.035(3) 0.3718(17) 0.241(2) 0.052(8) Uiso 1 1 d . . . . .
H10C H 0.958(3) 0.3174(19) 0.148(2) 0.059(9) Uiso 1 1 d . . . . .
C11 C 0.74514(18) 0.40718(11) 0.59397(14) 0.0250(4) Uani 1 1 d . . . . .
C12 C 0.6584(2) 0.40335(15) 0.65579(16) 0.0347(5) Uani 1 1 d . . . . .
H12 H 0.573(2) 0.3909(15) 0.6305(18) 0.038(7) Uiso 1 1 d . . . . .
C13 C 0.7035(2) 0.42052(17) 0.75487(18) 0.0429(6) Uani 1 1 d . . . . .
H13 H 0.650(2) 0.4180(16) 0.7966(19) 0.044(7) Uiso 1 1 d . . . . .
C14 C 0.8333(2) 0.43946(15) 0.79151(17) 0.0402(5) Uani 1 1 d . . . . .
H14 H 0.862(3) 0.4468(17) 0.862(2) 0.051(8) Uiso 1 1 d . . . . .
C15 C 0.9183(2) 0.44187(14) 0.72965(17) 0.0359(5) Uani 1 1 d . . . . .
H15 H 1.003(3) 0.4537(17) 0.754(2) 0.051(8) Uiso 1 1 d . . . . .
C16 C 0.8753(2) 0.42642(13) 0.63016(16) 0.0296(4) Uani 1 1 d . . . . .
H16 H 0.933(2) 0.4265(14) 0.5836(18) 0.034(6) Uiso 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
P1 F1 1.574(5) . ?
P1 F1A 1.607(16) . ?
P1 F2 1.591(5) . ?
P1 F2A 1.523(15) . ?
P1 F3 1.578(6) . ?
P1 F3A 1.60(2) . ?
P1 F4 1.605(4) . ?
P1 F4A 1.577(18) . ?
P1 F5 1.602(4) . ?
P1 F5A 1.514(14) . ?
P1 F6 1.597(5) . ?
P1 F6A 1.548(16) . ?
P2 F11 1.6059(13) . ?
P2 F12 1.5881(15) . ?
P2 F13 1.5986(15) . ?
P2 F14 1.5792(18) . ?
P2 F15 1.5963(14) . ?
P2 F16 1.5902(17) . ?
O1 C1 1.317(2) . ?
O1 C2 1.397(2) . ?
O2 C1 1.286(2) . ?
O2 C3 1.419(2) . ?
N1 C2 1.312(2) . ?
N1 C4 1.457(3) . ?
N1 C5 1.463(3) . ?
N2 C6 1.325(2) . ?
N2 C9 1.465(3) . ?
N2 C10 1.473(3) . ?
N3 C6 1.333(3) . ?
N3 C7 1.462(3) . ?
N3 C8 1.469(3) . ?
C1 C11 1.429(3) . ?
C2 C3 1.365(3) . ?
C3 C6 1.439(3) . ?
C4 H4A 0.97(3) . ?
C4 H4B 0.89(3) . ?
C4 H4C 0.97(3) . ?
C5 H5A 0.93(3) . ?
C5 H5B 0.90(3) . ?
C5 H5C 0.91(3) . ?
C7 H7A 0.91(3) . ?
C7 H7B 0.89(3) . ?
C7 H7C 0.99(3) . ?
C8 H8A 0.95(3) . ?
C8 H8B 0.99(3) . ?
C8 H8C 0.98(3) . ?
C9 H9A 0.97(3) . ?
C9 H9B 0.94(3) . ?
C9 H9C 0.97(3) . ?
C10 H10A 0.99(3) . ?
C10 H10B 0.99(3) . ?
C10 H10C 0.95(3) . ?
C11 C12 1.393(3) . ?
C11 C16 1.393(3) . ?
C12 H12 0.91(2) . ?
C12 C13 1.381(3) . ?
C13 H13 0.90(3) . ?
C13 C14 1.388(4) . ?
C14 H14 0.96(3) . ?
C14 C15 1.378(3) . ?
C15 H15 0.90(3) . ?
C15 C16 1.379(3) . ?
C16 H16 0.98(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
F1 P1 F2 179.2(3) . . ?
F1 P1 F3 90.4(3) . . ?
F1 P1 F4 90.2(2) . . ?
F1 P1 F5 90.8(2) . . ?
F1 P1 F6 91.4(3) . . ?
F2 P1 F4 89.1(3) . . ?
F2 P1 F5 88.7(3) . . ?
F2 P1 F6 89.2(3) . . ?
F2A P1 F1A 174.7(9) . . ?
F2A P1 F3A 94.0(11) . . ?
F2A P1 F4A 95.7(10) . . ?
F2A P1 F6A 90.1(10) . . ?
F3 P1 F2 90.0(3) . . ?
F3 P1 F4 88.9(3) . . ?
F3 P1 F5 178.7(3) . . ?
F3 P1 F6 91.7(2) . . ?
F3A P1 F1A 80.8(10) . . ?
F4A P1 F1A 83.7(9) . . ?
F4A P1 F3A 88.3(9) . . ?
F5 P1 F4 90.5(2) . . ?
F5A P1 F1A 92.1(7) . . ?
F5A P1 F2A 93.2(9) . . ?
F5A P1 F3A 172.8(11) . . ?
F5A P1 F4A 90.5(9) . . ?
F5A P1 F6A 91.6(7) . . ?
F6 P1 F4 178.2(2) . . ?
F6 P1 F5 88.9(2) . . ?
F6A P1 F1A 90.2(10) . . ?
F6A P1 F3A 88.8(8) . . ?
F6A P1 F4A 173.7(10) . . ?
F12 P2 F11 179.86(13) . . ?
F12 P2 F13 90.63(8) . . ?
F12 P2 F15 90.32(8) . . ?
F12 P2 F16 90.73(11) . . ?
F13 P2 F11 89.37(7) . . ?
F14 P2 F11 89.38(9) . . ?
F14 P2 F12 90.76(11) . . ?
F14 P2 F13 91.03(10) . . ?
F14 P2 F15 90.58(10) . . ?
F14 P2 F16 178.37(10) . . ?
F15 P2 F11 89.67(7) . . ?
F15 P2 F13 178.11(10) . . ?
F16 P2 F11 89.13(9) . . ?
F16 P2 F13 88.29(9) . . ?
F16 P2 F15 90.07(9) . . ?
C1 O1 C2 106.96(14) . . ?
C1 O2 C3 107.32(14) . . ?
C2 N1 C4 121.81(18) . . ?
C2 N1 C5 119.25(17) . . ?
C4 N1 C5 118.02(18) . . ?
C6 N2 C9 122.49(18) . . ?
C6 N2 C10 122.8(2) . . ?
C9 N2 C10 114.55(19) . . ?
C6 N3 C7 122.68(18) . . ?
C6 N3 C8 123.48(19) . . ?
C7 N3 C8 113.83(19) . . ?
O1 C1 C11 122.88(17) . . ?
O2 C1 O1 112.60(16) . . ?
O2 C1 C11 124.50(17) . . ?
N1 C2 O1 117.16(16) . . ?
N1 C2 C3 135.84(18) . . ?
C3 C2 O1 106.93(15) . . ?
O2 C3 C6 118.93(15) . . ?
C2 C3 O2 106.01(16) . . ?
C2 C3 C6 134.83(17) . . ?
N1 C4 H4A 108.4(18) . . ?
N1 C4 H4B 109(2) . . ?
N1 C4 H4C 111.6(19) . . ?
H4A C4 H4B 110(3) . . ?
H4A C4 H4C 117(3) . . ?
H4B C4 H4C 101(3) . . ?
N1 C5 H5A 110.4(15) . . ?
N1 C5 H5B 108.8(19) . . ?
N1 C5 H5C 110.0(17) . . ?
H5A C5 H5B 105(2) . . ?
H5A C5 H5C 112(2) . . ?
H5B C5 H5C 110(2) . . ?
N2 C6 N3 123.14(18) . . ?
N2 C6 C3 118.86(18) . . ?
N3 C6 C3 118.00(17) . . ?
N3 C7 H7A 111.5(16) . . ?
N3 C7 H7B 109.5(17) . . ?
N3 C7 H7C 108.8(15) . . ?
H7A C7 H7B 106(2) . . ?
H7A C7 H7C 113(2) . . ?
H7B C7 H7C 108(2) . . ?
N3 C8 H8A 109.1(16) . . ?
N3 C8 H8B 104.9(16) . . ?
N3 C8 H8C 110.2(17) . . ?
H8A C8 H8B 114(2) . . ?
H8A C8 H8C 107(2) . . ?
H8B C8 H8C 111(2) . . ?
N2 C9 H9A 107.8(15) . . ?
N2 C9 H9B 110.3(15) . . ?
N2 C9 H9C 109.9(15) . . ?
H9A C9 H9B 106(2) . . ?
H9A C9 H9C 111(2) . . ?
H9B C9 H9C 112(2) . . ?
N2 C10 H10A 110.3(15) . . ?
N2 C10 H10B 102.7(17) . . ?
N2 C10 H10C 110.3(18) . . ?
H10A C10 H10B 107(2) . . ?
H10A C10 H10C 113(2) . . ?
H10B C10 H10C 114(2) . . ?
C12 C11 C1 119.29(18) . . ?
C16 C11 C1 119.13(18) . . ?
C16 C11 C12 121.56(19) . . ?
C11 C12 H12 120.2(16) . . ?
C13 C12 C11 118.5(2) . . ?
C13 C12 H12 121.3(16) . . ?
C12 C13 H13 120.3(17) . . ?
C12 C13 C14 120.2(2) . . ?
C14 C13 H13 119.5(17) . . ?
C13 C14 H14 117.6(16) . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 121.7(16) . . ?
C14 C15 H15 120.2(18) . . ?
C14 C15 C16 120.4(2) . . ?
C16 C15 H15 119.4(18) . . ?
C11 C16 H16 118.2(14) . . ?
C15 C16 C11 118.7(2) . . ?
C15 C16 H16 123.1(14) . . ?

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
C4 H4B F1 0.89(3) 2.59(3) 3.410(6) 152(3) .
C5 H5A F12 0.93(3) 2.36(3) 3.146(3) 142(2) .
C5 H5C F3A 0.91(3) 2.58(4) 3.45(2) 161(2) .
C7 H7A F16 0.91(3) 2.52(3) 3.199(3) 132(2) 2_655
C7 H7C F3 0.99(3) 2.52(3) 3.438(7) 154(2) .
C8 H8A F13 0.95(3) 2.49(3) 3.420(3) 164(2) .
C8 H8C F6 0.98(3) 2.63(3) 3.506(7) 150(2) 3_665
C8 H8C F6A 0.98(3) 2.45(3) 3.271(16) 141(2) 3_665
C9 H9B F2 0.94(3) 2.60(3) 3.505(6) 161(2) 4_666
C9 H9B F3A 0.94(3) 2.58(3) 3.38(2) 143(2) 4_666
C9 H9C F14 0.97(3) 2.62(3) 3.573(3) 168(2) 4_666
C10 H10A F6 0.99(3) 2.60(3) 3.578(6) 168(2) 3_665
C10 H10A F6A 0.99(3) 2.63(3) 3.619(17) 176(2) 3_665

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
O1 C1 C11 C12 5.3(3) . . . . ?
O1 C1 C11 C16 -176.57(17) . . . . ?
O1 C2 C3 O2 4.11(19) . . . . ?
O1 C2 C3 C6 -170.1(2) . . . . ?
O2 C1 C11 C12 -172.93(19) . . . . ?
O2 C1 C11 C16 5.2(3) . . . . ?
O2 C3 C6 N2 40.1(3) . . . . ?
O2 C3 C6 N3 -140.23(18) . . . . ?
N1 C2 C3 O2 -172.7(2) . . . . ?
N1 C2 C3 C6 13.1(4) . . . . ?
C1 O1 C2 N1 174.52(17) . . . . ?
C1 O1 C2 C3 -3.0(2) . . . . ?
C1 O2 C3 C2 -3.8(2) . . . . ?
C1 O2 C3 C6 171.46(17) . . . . ?
C1 C11 C12 C13 179.2(2) . . . . ?
C1 C11 C16 C15 -178.03(19) . . . . ?
C2 O1 C1 O2 0.6(2) . . . . ?
C2 O1 C1 C11 -177.86(17) . . . . ?
C2 C3 C6 N2 -146.3(2) . . . . ?
C2 C3 C6 N3 33.4(3) . . . . ?
C3 O2 C1 O1 2.0(2) . . . . ?
C3 O2 C1 C11 -179.57(17) . . . . ?
C4 N1 C2 O1 14.8(3) . . . . ?
C4 N1 C2 C3 -168.5(3) . . . . ?
C5 N1 C2 O1 -153.97(18) . . . . ?
C5 N1 C2 C3 22.7(3) . . . . ?
C7 N3 C6 N2 -148.9(2) . . . . ?
C7 N3 C6 C3 31.4(3) . . . . ?
C8 N3 C6 N2 30.2(3) . . . . ?
C8 N3 C6 C3 -149.5(2) . . . . ?
C9 N2 C6 N3 -159.34(19) . . . . ?
C9 N2 C6 C3 20.3(3) . . . . ?
C10 N2 C6 N3 25.3(3) . . . . ?
C10 N2 C6 C3 -155.0(2) . . . . ?
C11 C12 C13 C14 -1.3(4) . . . . ?
C12 C11 C16 C15 0.1(3) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
C14 C15 C16 C11 -1.0(3) . . . . ?
C16 C11 C12 C13 1.1(3) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_date_sample_data_collection 2017-11-10
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.105
_oxdiff_exptl_absorpt_empirical_full_min 0.936



####################################################################### 
# 
# 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_3d_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1898565'
loop_
_audit_author_name
_audit_author_address
'Jacques Pecaut '
;CEA Grenoble
France
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_audit_creation_date             2018-02-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H41 Cl2 N2 O2, F6 P'
_chemical_formula_sum            'C26 H41 Cl2 F6 N2 O2 P'
_chemical_formula_weight         629.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cl2 O2 N2 C40 H60'
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'
Cl Cl 0.1484 0.1585 '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'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   18.6093(7)
_cell_length_b                   10.7780(3)
_cell_length_c                   15.4265(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.706(4)
_cell_angle_gamma                90
_cell_volume                     3029.76(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2339
_cell_measurement_temperature    149(3)
_cell_measurement_theta_max      29.1650
_cell_measurement_theta_min      2.2430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent intense yellow'
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1320
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0148
0 0 -1 0.2639
-1 2 2 0.1574
-1 0 2 0.1744
1 -2 -1 0.1319
0 1 -1 0.1393
0 -1 1 0.1393
-1 0 0 0.0148

_exptl_crystal_size_max          0.437
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0003 -0.0009 -0.0007 0.0383 0.0060 -0.0041
-0.0011 -0.0003 -1.0002 -0.0174 0.0239 -0.0365
-0.9943 2.0005 1.9992 -0.0123 0.0541 0.1519
-0.9982 0.0015 2.0011 -0.0035 -0.0538 0.0771
0.9953 -2.0002 -0.9989 0.0297 -0.0780 -0.1155
0.0009 0.9992 -1.0012 -0.0217 0.0779 0.0009
-0.0009 -0.9992 1.0012 0.0217 -0.0779 -0.0009
-1.0003 0.0009 0.0007 -0.0383 -0.0060 0.0041

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16439
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         2.195
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9653
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 101.00   1.00   30.00    --   25.56 178.00-150.00   66
  2  ω      0.00  98.00   1.00   30.00    --   25.56  37.00   0.00   98
  3  ω    -19.00  77.00   1.00   30.00    --   25.56  19.00 -60.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0382535000
_diffrn_orient_matrix_UB_12      -0.0044532000
_diffrn_orient_matrix_UB_13      0.0173113000
_diffrn_orient_matrix_UB_21      0.0059906000
_diffrn_orient_matrix_UB_22      0.0539216000
_diffrn_orient_matrix_UB_23      -0.0239393000
_diffrn_orient_matrix_UB_31      -0.0040786000
_diffrn_orient_matrix_UB_32      0.0374834000
_diffrn_orient_matrix_UB_33      0.0364689000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4943
_reflns_number_total             7522
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         7522
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+0.6768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1170
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C15B \\sim C15: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02
3. Others
 Sof(C15B)=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(1)
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
4.a Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C15B(H15D,H15E,H15F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.34186(4) 0.05785(6) 0.56468(4) 0.03404(17) Uani 1 1 d . . . . .
Cl2 Cl 0.35046(3) 0.36555(5) 0.83691(4) 0.02511(14) Uani 1 1 d . . . . .
O1 O 0.29397(8) 0.27957(13) 0.64300(10) 0.0179(3) Uani 1 1 d . . . . .
O2 O 0.19792(9) 0.28625(15) 0.71193(10) 0.0249(4) Uani 1 1 d . . . . .
N1 N 0.42374(11) 0.03531(17) 0.72095(13) 0.0241(4) Uani 1 1 d . . . . .
N2 N 0.32738(10) 0.12974(17) 0.85499(12) 0.0201(4) Uani 1 1 d . . . . .
C1 C 0.22393(12) 0.3145(2) 0.64966(15) 0.0190(5) Uani 1 1 d . . . . .
C2 C 0.18656(12) 0.3885(2) 0.57029(14) 0.0194(5) Uani 1 1 d . . . . .
C3 C 0.14155(12) 0.3241(2) 0.49917(15) 0.0231(5) Uani 1 1 d . . . . .
C4 C 0.10706(14) 0.3945(3) 0.42679(16) 0.0294(6) Uani 1 1 d . . . . .
H4 H 0.0776(12) 0.350(2) 0.3780(15) 0.017(6) Uiso 1 1 d . . . . .
C5 C 0.11170(13) 0.5221(3) 0.42244(16) 0.0289(6) Uani 1 1 d . . . . .
C6 C 0.15523(13) 0.5817(2) 0.49380(17) 0.0272(6) Uani 1 1 d . . . . .
H6 H 0.1587(12) 0.669(2) 0.4916(14) 0.014(6) Uiso 1 1 d . . . . .
C7 C 0.19379(12) 0.5201(2) 0.56835(15) 0.0217(5) Uani 1 1 d . . . . .
C8 C 0.12566(14) 0.1823(2) 0.48947(16) 0.0299(6) Uani 1 1 d . . . . .
C9 C 0.04197(19) 0.1629(4) 0.4605(3) 0.0526(9) Uani 1 1 d . . . . .
H9A H 0.0190(19) 0.190(3) 0.505(2) 0.064(11) Uiso 1 1 d . . . . .
H9B H 0.018(2) 0.206(3) 0.410(2) 0.070(12) Uiso 1 1 d . . . . .
H9C H 0.0335(19) 0.073(3) 0.456(2) 0.070(11) Uiso 1 1 d . . . . .
C10 C 0.14838(19) 0.1019(3) 0.5716(2) 0.0377(7) Uani 1 1 d . . . . .
H10A H 0.2000(15) 0.101(2) 0.5943(17) 0.029(7) Uiso 1 1 d . . . . .
H10B H 0.1324(15) 0.017(3) 0.5552(18) 0.042(8) Uiso 1 1 d . . . . .
H10C H 0.1228(15) 0.130(2) 0.6181(19) 0.043(8) Uiso 1 1 d . . . . .
C11 C 0.1625(2) 0.1329(3) 0.4162(2) 0.0419(7) Uani 1 1 d . . . . .
H11A H 0.1521(17) 0.047(3) 0.409(2) 0.058(10) Uiso 1 1 d . . . . .
H11B H 0.2151(16) 0.137(2) 0.4325(18) 0.036(8) Uiso 1 1 d . . . . .
H11C H 0.1470(14) 0.177(2) 0.3608(18) 0.030(7) Uiso 1 1 d . . . . .
C12 C 0.06723(14) 0.5913(3) 0.34213(18) 0.0388(7) Uani 1 1 d . . . . .
C13 C -0.01456(18) 0.5694(4) 0.3396(3) 0.0554(10) Uani 1 1 d . . . . .
H13A H -0.0411(19) 0.618(3) 0.298(2) 0.066(11) Uiso 1 1 d . . . . .
H13B H -0.027(2) 0.479(3) 0.330(2) 0.082(13) Uiso 1 1 d . . . . .
H13C H -0.0274(19) 0.601(3) 0.396(2) 0.068(11) Uiso 1 1 d . . . . .
C14 C 0.0815(2) 0.7304(4) 0.3468(3) 0.0633(11) Uani 1 1 d . . . . .
H14A H 0.054(2) 0.768(3) 0.298(2) 0.074(12) Uiso 1 1 d . . . . .
H14B H 0.0696(17) 0.777(3) 0.404(2) 0.055(10) Uiso 1 1 d . . . . .
H14C H 0.134(2) 0.754(3) 0.352(2) 0.075(12) Uiso 1 1 d . . . . .
C15 C 0.0827(10) 0.5269(18) 0.2545(10) 0.044(3) Uani 0.61(5) 1 d . U P A 1
H15A H 0.133703 0.535532 0.252527 0.065 Uiso 0.61(5) 1 calc GR . P A 1
H15B H 0.053367 0.566042 0.203408 0.065 Uiso 0.61(5) 1 calc GR . P A 1
H15C H 0.070348 0.440456 0.254743 0.065 Uiso 0.61(5) 1 calc GR . P A 1
C16 C 0.24083(13) 0.5994(2) 0.64273(16) 0.0240(5) Uani 1 1 d . . . . .
C17 C 0.32277(14) 0.5724(2) 0.65020(19) 0.0262(5) Uani 1 1 d . . . . .
H17A H 0.3489(13) 0.620(2) 0.6964(17) 0.024(7) Uiso 1 1 d . . . . .
H17B H 0.3396(14) 0.597(2) 0.6008(19) 0.034(7) Uiso 1 1 d . . . . .
H17C H 0.3370(13) 0.489(2) 0.6594(16) 0.024(6) Uiso 1 1 d . . . . .
C18 C 0.21653(16) 0.5801(3) 0.73102(19) 0.0320(6) Uani 1 1 d . . . . .
H18A H 0.2446(14) 0.631(2) 0.7731(17) 0.029(7) Uiso 1 1 d . . . . .
H18B H 0.2212(14) 0.496(3) 0.7507(17) 0.035(8) Uiso 1 1 d . . . . .
H18C H 0.1691(16) 0.606(2) 0.7261(17) 0.034(7) Uiso 1 1 d . . . . .
C19 C 0.23256(19) 0.7399(3) 0.6231(2) 0.0400(7) Uani 1 1 d . . . . .
H19A H 0.2474(15) 0.764(2) 0.5662(19) 0.036(8) Uiso 1 1 d . . . . .
H19B H 0.1837(18) 0.768(3) 0.6169(19) 0.047(9) Uiso 1 1 d . . . . .
H19C H 0.2653(16) 0.786(2) 0.6753(19) 0.045(8) Uiso 1 1 d . . . . .
C20 C 0.32999(12) 0.19409(19) 0.70631(15) 0.0188(5) Uani 1 1 d . . . . .
C21 C 0.36751(13) 0.0981(2) 0.67488(15) 0.0213(5) Uani 1 1 d . . . . .
C22 C 0.45016(19) -0.0812(3) 0.6883(2) 0.0369(7) Uani 1 1 d . . . . .
H22A H 0.4829(18) -0.064(3) 0.651(2) 0.059(10) Uiso 1 1 d . . . . .
H22B H 0.4101(18) -0.126(3) 0.654(2) 0.053(10) Uiso 1 1 d . . . . .
H22C H 0.4752(18) -0.122(3) 0.738(2) 0.062(11) Uiso 1 1 d . . . . .
C23 C 0.47165(15) 0.0866(3) 0.7997(2) 0.0315(6) Uani 1 1 d . . . . .
H23A H 0.4605(14) 0.055(2) 0.8558(18) 0.031(7) Uiso 1 1 d . . . . .
H23B H 0.4641(15) 0.176(3) 0.8034(18) 0.040(8) Uiso 1 1 d . . . . .
H23C H 0.5220(17) 0.068(2) 0.7953(19) 0.045(8) Uiso 1 1 d . . . . .
C24 C 0.33407(12) 0.21673(19) 0.79769(15) 0.0184(5) Uani 1 1 d . . . . .
C25 C 0.29578(16) 0.0088(2) 0.82535(19) 0.0269(6) Uani 1 1 d . . . . .
H25A H 0.2683(15) -0.020(2) 0.8663(18) 0.035(7) Uiso 1 1 d . . . . .
H25B H 0.2638(13) 0.018(2) 0.7690(16) 0.020(6) Uiso 1 1 d . . . . .
H25C H 0.3325(15) -0.048(2) 0.8191(17) 0.035(8) Uiso 1 1 d . . . . .
C26 C 0.34743(17) 0.1452(3) 0.95198(16) 0.0285(6) Uani 1 1 d . . . . .
H26A H 0.3825(15) 0.211(2) 0.9659(17) 0.030(7) Uiso 1 1 d . . . . .
H26B H 0.3695(14) 0.071(2) 0.9752(18) 0.035(8) Uiso 1 1 d . . . . .
H26C H 0.3019(18) 0.152(3) 0.971(2) 0.056(10) Uiso 1 1 d . . . . .
P1 P 0.56167(4) 0.23356(6) 0.56887(5) 0.03027(17) Uani 1 1 d . . . . .
F1 F 0.49040(11) 0.2460(2) 0.61081(12) 0.0667(6) Uani 1 1 d . . . . .
F2 F 0.63268(11) 0.2242(2) 0.52756(14) 0.0741(6) Uani 1 1 d . . . . .
F3 F 0.51051(10) 0.21302(16) 0.47435(11) 0.0558(5) Uani 1 1 d . . . . .
F4 F 0.55924(11) 0.37861(14) 0.55186(12) 0.0574(5) Uani 1 1 d . . . . .
F5 F 0.61210(10) 0.25649(16) 0.66470(11) 0.0541(5) Uani 1 1 d . . . . .
F6 F 0.56461(13) 0.09030(15) 0.58588(16) 0.0856(7) Uani 1 1 d . . . . .
C15B C 0.0954(19) 0.571(4) 0.2632(18) 0.063(6) Uani 0.39(5) 1 d . U P A 2
H15D H 0.143136 0.608314 0.269952 0.094 Uiso 0.39(5) 1 calc GR . P A 2
H15E H 0.062924 0.608080 0.213582 0.094 Uiso 0.39(5) 1 calc GR . P A 2
H15F H 0.099072 0.483679 0.253243 0.094 Uiso 0.39(5) 1 calc GR . P A 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
Cl1 C21 1.725(2) . ?
Cl2 C24 1.720(2) . ?
O1 C1 1.380(3) . ?
O1 C20 1.409(3) . ?
O2 C1 1.199(3) . ?
N1 C21 1.325(3) . ?
N1 C22 1.473(3) . ?
N1 C23 1.462(3) . ?
N2 C24 1.312(3) . ?
N2 C25 1.464(3) . ?
N2 C26 1.476(3) . ?
C1 C2 1.508(3) . ?
C2 C3 1.419(3) . ?
C2 C7 1.426(3) . ?
C3 C4 1.394(3) . ?
C3 C8 1.558(3) . ?
C4 H4 0.96(2) . ?
C4 C5 1.380(4) . ?
C5 C6 1.385(4) . ?
C5 C12 1.537(3) . ?
C6 H6 0.95(2) . ?
C6 C7 1.394(3) . ?
C7 C16 1.551(3) . ?
C8 C9 1.545(4) . ?
C8 C10 1.522(4) . ?
C8 C11 1.533(4) . ?
C9 H9A 0.93(4) . ?
C9 H9B 0.94(4) . ?
C9 H9C 0.99(3) . ?
C10 H10A 0.95(3) . ?
C10 H10B 0.98(3) . ?
C10 H10C 0.99(3) . ?
C11 H11A 0.94(3) . ?
C11 H11B 0.96(3) . ?
C11 H11C 0.97(3) . ?
C12 C13 1.533(4) . ?
C12 C14 1.521(5) . ?
C12 C15 1.598(17) . ?
C12 C15B 1.44(3) . ?
C13 H13A 0.90(3) . ?
C13 H13B 1.00(4) . ?
C13 H13C 1.00(4) . ?
C14 H14A 0.92(4) . ?
C14 H14B 1.07(3) . ?
C14 H14C 1.00(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.533(3) . ?
C16 C18 1.534(4) . ?
C16 C19 1.547(4) . ?
C17 H17A 0.93(3) . ?
C17 H17B 0.92(3) . ?
C17 H17C 0.94(2) . ?
C18 H18A 0.93(3) . ?
C18 H18B 0.95(3) . ?
C18 H18C 0.92(3) . ?
C19 H19A 1.01(3) . ?
C19 H19B 0.94(3) . ?
C19 H19C 1.03(3) . ?
C20 C21 1.390(3) . ?
C20 C24 1.417(3) . ?
C22 H22A 0.93(3) . ?
C22 H22B 0.95(3) . ?
C22 H22C 0.92(3) . ?
C23 H23A 0.99(3) . ?
C23 H23B 0.97(3) . ?
C23 H23C 0.97(3) . ?
C25 H25A 0.94(3) . ?
C25 H25B 0.95(2) . ?
C25 H25C 0.94(3) . ?
C26 H26A 0.96(3) . ?
C26 H26B 0.93(3) . ?
C26 H26C 0.95(3) . ?
P1 F1 1.595(2) . ?
P1 F2 1.583(2) . ?
P1 F3 1.5869(17) . ?
P1 F4 1.5843(16) . ?
P1 F5 1.6013(18) . ?
P1 F6 1.5653(18) . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?

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 C20 116.75(16) . . ?
C21 N1 C22 122.3(2) . . ?
C21 N1 C23 122.3(2) . . ?
C23 N1 C22 114.6(2) . . ?
C24 N2 C25 120.8(2) . . ?
C24 N2 C26 124.3(2) . . ?
C25 N2 C26 114.8(2) . . ?
O1 C1 C2 111.76(18) . . ?
O2 C1 O1 122.1(2) . . ?
O2 C1 C2 126.2(2) . . ?
C3 C2 C1 118.1(2) . . ?
C3 C2 C7 120.9(2) . . ?
C7 C2 C1 120.90(19) . . ?
C2 C3 C8 128.7(2) . . ?
C4 C3 C2 117.2(2) . . ?
C4 C3 C8 114.2(2) . . ?
C3 C4 H4 117.1(13) . . ?
C5 C4 C3 123.9(2) . . ?
C5 C4 H4 119.0(13) . . ?
C4 C5 C6 117.1(2) . . ?
C4 C5 C12 119.6(2) . . ?
C6 C5 C12 123.2(3) . . ?
C5 C6 H6 117.9(13) . . ?
C5 C6 C7 123.7(2) . . ?
C7 C6 H6 118.4(14) . . ?
C2 C7 C16 125.0(2) . . ?
C6 C7 C2 117.1(2) . . ?
C6 C7 C16 117.9(2) . . ?
C9 C8 C3 108.7(2) . . ?
C10 C8 C3 117.6(2) . . ?
C10 C8 C9 104.9(3) . . ?
C10 C8 C11 109.0(2) . . ?
C11 C8 C3 107.9(2) . . ?
C11 C8 C9 108.4(3) . . ?
C8 C9 H9A 109(2) . . ?
C8 C9 H9B 117(2) . . ?
C8 C9 H9C 107(2) . . ?
H9A C9 H9B 104(3) . . ?
H9A C9 H9C 105(3) . . ?
H9B C9 H9C 113(3) . . ?
C8 C10 H10A 113.7(16) . . ?
C8 C10 H10B 107.5(16) . . ?
C8 C10 H10C 109.8(16) . . ?
H10A C10 H10B 108(2) . . ?
H10A C10 H10C 110(2) . . ?
H10B C10 H10C 108(2) . . ?
C8 C11 H11A 108.4(19) . . ?
C8 C11 H11B 111.9(17) . . ?
C8 C11 H11C 112.3(15) . . ?
H11A C11 H11B 105(2) . . ?
H11A C11 H11C 111(2) . . ?
H11B C11 H11C 108(2) . . ?
C5 C12 C15 108.1(6) . . ?
C13 C12 C5 108.3(2) . . ?
C13 C12 C15 105.1(7) . . ?
C14 C12 C5 112.3(3) . . ?
C14 C12 C13 108.4(3) . . ?
C14 C12 C15 114.1(7) . . ?
C15B C12 C5 112.4(11) . . ?
C15B C12 C13 119.1(16) . . ?
C15B C12 C14 95.6(19) . . ?
C12 C13 H13A 109(2) . . ?
C12 C13 H13B 111(2) . . ?
C12 C13 H13C 110(2) . . ?
H13A C13 H13B 113(3) . . ?
H13A C13 H13C 103(3) . . ?
H13B C13 H13C 111(3) . . ?
C12 C14 H14A 110(2) . . ?
C12 C14 H14B 115.7(17) . . ?
C12 C14 H14C 115(2) . . ?
H14A C14 H14B 107(3) . . ?
H14A C14 H14C 109(3) . . ?
H14B C14 H14C 100(3) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C7 110.78(19) . . ?
C17 C16 C18 112.1(2) . . ?
C17 C16 C19 105.0(2) . . ?
C18 C16 C7 111.0(2) . . ?
C18 C16 C19 105.7(2) . . ?
C19 C16 C7 112.1(2) . . ?
C16 C17 H17A 108.2(15) . . ?
C16 C17 H17B 112.5(17) . . ?
C16 C17 H17C 115.9(15) . . ?
H17A C17 H17B 105(2) . . ?
H17A C17 H17C 109(2) . . ?
H17B C17 H17C 106(2) . . ?
C16 C18 H18A 108.4(16) . . ?
C16 C18 H18B 112.8(16) . . ?
C16 C18 H18C 109.7(17) . . ?
H18A C18 H18B 110(2) . . ?
H18A C18 H18C 106(2) . . ?
H18B C18 H18C 110(2) . . ?
C16 C19 H19A 113.2(15) . . ?
C16 C19 H19B 112.6(18) . . ?
C16 C19 H19C 107.4(15) . . ?
H19A C19 H19B 105(2) . . ?
H19A C19 H19C 109(2) . . ?
H19B C19 H19C 109(2) . . ?
O1 C20 C24 119.91(18) . . ?
C21 C20 O1 116.55(19) . . ?
C21 C20 C24 123.1(2) . . ?
N1 C21 Cl1 115.51(17) . . ?
N1 C21 C20 126.2(2) . . ?
C20 C21 Cl1 118.22(18) . . ?
N1 C22 H22A 110.1(19) . . ?
N1 C22 H22B 110.1(19) . . ?
N1 C22 H22C 106(2) . . ?
H22A C22 H22B 107(3) . . ?
H22A C22 H22C 109(3) . . ?
H22B C22 H22C 115(3) . . ?
N1 C23 H23A 113.3(15) . . ?
N1 C23 H23B 110.5(16) . . ?
N1 C23 H23C 107.2(17) . . ?
H23A C23 H23B 103(2) . . ?
H23A C23 H23C 112(2) . . ?
H23B C23 H23C 111(2) . . ?
N2 C24 Cl2 117.64(17) . . ?
N2 C24 C20 123.6(2) . . ?
C20 C24 Cl2 118.71(16) . . ?
N2 C25 H25A 109.1(16) . . ?
N2 C25 H25B 108.9(14) . . ?
N2 C25 H25C 111.2(16) . . ?
H25A C25 H25B 109(2) . . ?
H25A C25 H25C 111(2) . . ?
H25B C25 H25C 108(2) . . ?
N2 C26 H26A 109.3(16) . . ?
N2 C26 H26B 107.1(17) . . ?
N2 C26 H26C 105.1(19) . . ?
H26A C26 H26B 108(2) . . ?
H26A C26 H26C 119(2) . . ?
H26B C26 H26C 107(2) . . ?
F1 P1 F5 89.56(10) . . ?
F2 P1 F1 178.81(12) . . ?
F2 P1 F3 90.88(11) . . ?
F2 P1 F4 89.68(11) . . ?
F2 P1 F5 90.05(11) . . ?
F3 P1 F1 89.50(10) . . ?
F3 P1 F5 178.78(11) . . ?
F4 P1 F1 89.19(11) . . ?
F4 P1 F3 89.65(10) . . ?
F4 P1 F5 89.56(9) . . ?
F6 P1 F1 91.08(13) . . ?
F6 P1 F2 90.05(13) . . ?
F6 P1 F3 90.60(11) . . ?
F6 P1 F4 179.63(13) . . ?
F6 P1 F5 90.20(11) . . ?
C12 C15B H15D 109.5 . . ?
C12 C15B H15E 109.5 . . ?
C12 C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?

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
C10 H10A Cl1 0.95(3) 2.81(3) 3.654(4) 148(2) .
C22 H22A F6 0.93(3) 2.59(3) 3.437(4) 151(2) .
C26 H26A F3 0.96(3) 2.50(3) 3.353(4) 149(2) 4_566

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
O1 C1 C2 C3 93.7(2) . . . . ?
O1 C1 C2 C7 -88.9(2) . . . . ?
O1 C20 C21 Cl1 -22.6(3) . . . . ?
O1 C20 C21 N1 155.0(2) . . . . ?
O1 C20 C24 Cl2 -40.3(3) . . . . ?
O1 C20 C24 N2 141.0(2) . . . . ?
O2 C1 C2 C3 -85.7(3) . . . . ?
O2 C1 C2 C7 91.8(3) . . . . ?
C1 O1 C20 C21 136.2(2) . . . . ?
C1 O1 C20 C24 -51.2(3) . . . . ?
C1 C2 C3 C4 179.5(2) . . . . ?
C1 C2 C3 C8 -1.5(3) . . . . ?
C1 C2 C7 C6 -177.7(2) . . . . ?
C1 C2 C7 C16 2.1(3) . . . . ?
C2 C3 C4 C5 -3.0(4) . . . . ?
C2 C3 C8 C9 131.6(3) . . . . ?
C2 C3 C8 C10 12.7(4) . . . . ?
C2 C3 C8 C11 -111.0(3) . . . . ?
C2 C7 C16 C17 67.2(3) . . . . ?
C2 C7 C16 C18 -58.0(3) . . . . ?
C2 C7 C16 C19 -176.0(2) . . . . ?
C3 C2 C7 C6 -0.3(3) . . . . ?
C3 C2 C7 C16 179.4(2) . . . . ?
C3 C4 C5 C6 2.0(4) . . . . ?
C3 C4 C5 C12 -175.8(2) . . . . ?
C4 C3 C8 C9 -49.4(3) . . . . ?
C4 C3 C8 C10 -168.3(2) . . . . ?
C4 C3 C8 C11 68.0(3) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C4 C5 C12 C13 62.6(3) . . . . ?
C4 C5 C12 C14 -177.6(3) . . . . ?
C4 C5 C12 C15 -50.8(8) . . . . ?
C4 C5 C12 C15B -71(2) . . . . ?
C5 C6 C7 C2 -0.7(3) . . . . ?
C5 C6 C7 C16 179.5(2) . . . . ?
C6 C5 C12 C13 -115.1(3) . . . . ?
C6 C5 C12 C14 4.7(4) . . . . ?
C6 C5 C12 C15 131.5(8) . . . . ?
C6 C5 C12 C15B 111(2) . . . . ?
C6 C7 C16 C17 -113.1(2) . . . . ?
C6 C7 C16 C18 121.7(2) . . . . ?
C6 C7 C16 C19 3.8(3) . . . . ?
C7 C2 C3 C4 2.1(3) . . . . ?
C7 C2 C3 C8 -179.0(2) . . . . ?
C8 C3 C4 C5 177.9(2) . . . . ?
C12 C5 C6 C7 177.7(2) . . . . ?
C20 O1 C1 O2 8.9(3) . . . . ?
C20 O1 C1 C2 -170.44(17) . . . . ?
C21 C20 C24 Cl2 131.8(2) . . . . ?
C21 C20 C24 N2 -46.9(3) . . . . ?
C22 N1 C21 Cl1 -15.4(3) . . . . ?
C22 N1 C21 C20 166.9(2) . . . . ?
C23 N1 C21 Cl1 153.72(19) . . . . ?
C23 N1 C21 C20 -24.0(4) . . . . ?
C24 C20 C21 Cl1 165.08(18) . . . . ?
C24 C20 C21 N1 -17.3(4) . . . . ?
C25 N2 C24 Cl2 164.67(18) . . . . ?
C25 N2 C24 C20 -16.6(3) . . . . ?
C26 N2 C24 Cl2 -12.9(3) . . . . ?
C26 N2 C24 C20 165.8(2) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_date_sample_data_collection 2018-02-23
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.025
_oxdiff_exptl_absorpt_empirical_full_min 0.975



####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 1898563'
loop_
_audit_author_name
_audit_author_address
'Jacques Pecaut '
;CEA Grenoble
France
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_audit_creation_date             2019-02-21
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C28 H47 Cl N3 O2, 0.44(C4 H10 O), F6 P, 0.5(C1.12 H2.24 Cl2.24)'
_chemical_formula_sum            'C30.33 H52.53 Cl2.12 F6 N3 O2.44 P'
_chemical_formula_weight         718.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'P1 F6 O5 N3 C40 H80'
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'
Cl Cl 0.1484 0.1585 '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'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5322(4)
_cell_length_b                   18.6061(7)
_cell_length_c                   21.1198(11)
_cell_angle_alpha                83.275(4)
_cell_angle_beta                 88.086(4)
_cell_angle_gamma                80.993(3)
_cell_volume                     3673.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6650
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      24.7400
_cell_measurement_theta_min      2.3270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'long plate'
_exptl_crystal_F_000             1520
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0295
-1 0 0 0.2682
1 0 0 0.2382
0 2 1 0.0650
-1 -1 -2 0.2184
0 1 0 0.0672
0 0 1 0.0205
0 -1 0 0.0872
0 -2 -1 0.0850

_exptl_crystal_size_max          0.536
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0008 0.0012 -1.0023 0.0032 0.0308 0.0139
-1.0016 0.0065 -0.0075 -0.0330 0.0298 -0.0610
1.0016 -0.0065 0.0075 0.0330 -0.0298 0.0610
0.0020 2.0037 0.9974 -0.0760 -0.0254 0.0132
-1.0013 -0.9936 -2.0096 0.0099 0.0887 -0.0468
0.0014 1.0024 -0.0024 -0.0364 0.0027 0.0135
-0.0008 -0.0012 1.0023 -0.0032 -0.0308 -0.0139
-0.0014 -1.0024 0.0024 0.0364 -0.0027 -0.0135
-0.0020 -2.0037 -0.9974 0.0760 0.0254 -0.0132

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1134
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            65540
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.472
_diffrn_reflns_theta_min         2.127
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9653
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  37.00   1.00   10.00    --   -0.62  90.00 -38.00   75
  2  ω    -69.00  21.00   1.00   10.00    --   -0.62 -57.00-150.00   90
  3  ω    -20.00  22.00   1.00   10.00    --   24.00 104.00  46.13   42
  4  ω    -14.00  12.00   1.00  100.00    --   36.00 114.00-108.77   26
  5  ω     -3.00  23.00   1.00  100.00    --   40.00 101.00 179.27   26
  6  ω      5.00  32.00   1.00  100.00    --   44.00  93.00  67.07   27
  7  ω     12.00  39.00   1.00  100.00    --   48.00  87.00 -16.98   27
  8  ω     11.00  37.00   1.00  100.00    --   48.00  90.00-170.39   26
  9  ω     18.00  46.00   1.00  100.00    --   52.00  84.00  91.99   28
 10  ω    -13.00  77.00   1.00  100.00    --   55.51 -57.00  30.00   90
 11  ω     -3.00 113.00   1.00  100.00    --   55.51-125.00-120.00  116
 12  ω     25.00 126.00   1.00  100.00    --   55.51  78.00 163.71  101
 13  ω     24.00 125.00   1.00  100.00    --   55.51  79.00 -56.84  101
 14  ω    -13.00  74.00   1.00  100.00    --   55.51 -57.00  90.00   87
 15  ω      5.00  97.00   1.00  100.00    --   55.51 -99.00   0.00   92
 16  ω     24.00 125.00   1.00  100.00    --   55.51  79.00-110.52  101
 17  ω     25.00 125.00   1.00  100.00    --   55.51  77.00  60.00  100
 18  ω     73.00 126.00   1.00  100.00    --   55.51 125.00  60.00   53
 19  ω     25.00  53.00   1.00  100.00    --   55.51  77.00 120.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0327008000
_diffrn_orient_matrix_UB_12      -0.0363737000
_diffrn_orient_matrix_UB_13      -0.0032173000
_diffrn_orient_matrix_UB_21      -0.0295329000
_diffrn_orient_matrix_UB_22      0.0026600000
_diffrn_orient_matrix_UB_23      -0.0307254000
_diffrn_orient_matrix_UB_31      0.0611218000
_diffrn_orient_matrix_UB_32      0.0133811000
_diffrn_orient_matrix_UB_33      -0.0137652000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9764
_reflns_number_total             15036
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     22.44
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     976
_refine_ls_number_reflns         15036
_refine_ls_number_restraints     179
_refine_ls_R_factor_all          0.1554
_refine_ls_R_factor_gt           0.1108
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1051P)²+14.3851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2715
_refine_ls_wR_factor_ref         0.2951
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C51B-C52B = C51B-C54B = C51B-C53B
 1.5 with sigma of 0.02
 Cl6-C66 = Cl5-C66
 1.75 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C22 \\sim C23 \\sim C24 \\sim C22B \\sim C23B \\sim C24B: within 1.7A with
sigma of 0.01 and sigma for terminal atoms of 0.02
F13 \\sim F14 \\sim F15 \\sim F16 \\sim F13B \\sim F14B \\sim F15B \\sim F16B:
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
C51 \\sim C52 \\sim C53 \\sim C54 \\sim C51B \\sim C52B \\sim C53B \\sim C54B:
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(Cl6) \\sim Ueq, Uanis(C66) \\sim Ueq, Uanis(Cl5) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C22B)=Sof(H22D)=Sof(H22E)=Sof(H22F)=Sof(C23B)=Sof(H23D)=Sof(H23E)=
 Sof(H23F)=Sof(C24B)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=
 Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(1)
 Sof(F13B)=Sof(F14B)=Sof(F15B)=Sof(F16B)=1-FVAR(2)
 Sof(F13)=Sof(F14)=Sof(F15)=Sof(F16)=FVAR(2)
 Sof(Cl5)=Sof(Cl6)=Sof(C66)=Sof(H66A)=Sof(H66B)=1-FVAR(3)
 Sof(O61)=Sof(C61)=Sof(H61A)=Sof(H61B)=Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(H62C)=
 Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(H64C)=FVAR(3)
 Sof(C51B)=Sof(C52B)=Sof(H52D)=Sof(H52E)=Sof(H52F)=Sof(C53B)=Sof(H53D)=
 Sof(H53E)=Sof(H53F)=Sof(C54B)=Sof(H54D)=Sof(H54E)=Sof(H54F)=1-FVAR(4)
 Sof(C51)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=Sof(C53)=Sof(H53A)=Sof(H53B)=
 Sof(H53C)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(H54C)=FVAR(4)
5.a Secondary CH2 refined with riding coordinates:
 C61(H61A,H61B), C63(H63A,H63B), C65(H65A,H65B), C66(H66A,H66B)
5.b Me refined with riding coordinates:
 C52B(H52D,H52E,H52F), C53B(H53D,H53E,H53F), C54B(H54D,H54E,H54F)
5.c Aromatic/amide H refined with riding coordinates:
 C43(H43), C45(H45), C13(H13), C15(H15)
5.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,
 H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C48(H48A,H48B,H48C), C49(H49A,
 H49B,H49C), C50(H50A,H50B,H50C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C),
 C58(H58A,H58B,H58C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C54(H54A,H54B,
 H54C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C),
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C),
 C22B(H22D,H22E,H22F), C23B(H23D,H23E,H23F), C24B(H24D,H24E,H24F), C62(H62A,
 H62B,H62C), C64(H64A,H64B,H64C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
# end Validation Reply Form
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
Cl2 Cl 0.25585(17) 0.48374(8) 0.75194(7) 0.0395(4) Uani 1 1 d . . . . .
O31 O 0.1302(3) 0.62526(19) 0.78416(15) 0.0232(7) Uani 1 1 d . . . . .
O32 O 0.2398(4) 0.7227(2) 0.79284(17) 0.0284(8) Uani 1 1 d . . . . .
N31 N 0.1115(5) 0.6464(2) 0.9232(2) 0.0276(9) Uani 1 1 d . . . . .
N32 N 0.3564(5) 0.6139(3) 0.9151(2) 0.0293(10) Uani 1 1 d . . . . .
N33 N 0.3097(5) 0.4602(2) 0.8742(2) 0.0304(10) Uani 1 1 d . . . . .
C31 C 0.2266(5) 0.6156(3) 0.8932(2) 0.0241(10) Uani 1 1 d . . . . .
C32 C 0.2111(5) 0.5830(3) 0.8345(2) 0.0238(10) Uani 1 1 d . . . . .
C33 C 0.2605(5) 0.5123(3) 0.8270(2) 0.0258(11) Uani 1 1 d . . . . .
C34 C -0.0269(6) 0.6208(3) 0.9210(3) 0.0342(12) Uani 1 1 d . . . . .
H34A H -0.047736 0.595777 0.961823 0.051 Uiso 1 1 calc GR . . . .
H34B H -0.023196 0.587844 0.889041 0.051 Uiso 1 1 calc GR . . . .
H34C H -0.099702 0.661991 0.910810 0.051 Uiso 1 1 calc GR . . . .
C35 C 0.1123(7) 0.7038(3) 0.9649(3) 0.0411(14) Uani 1 1 d . . . . .
H35A H 0.112898 0.682577 1.008639 0.062 Uiso 1 1 calc GR . . . .
H35B H 0.029048 0.739828 0.957599 0.062 Uiso 1 1 calc GR . . . .
H35C H 0.195577 0.726527 0.955964 0.062 Uiso 1 1 calc GR . . . .
C36 C 0.3860(7) 0.6122(3) 0.9831(3) 0.0363(13) Uani 1 1 d . . . . .
H36A H 0.413166 0.657965 0.990757 0.054 Uiso 1 1 calc GR . . . .
H36B H 0.461856 0.573078 0.995160 0.054 Uiso 1 1 calc GR . . . .
H36C H 0.302322 0.604469 1.007910 0.054 Uiso 1 1 calc GR . . . .
C37 C 0.4837(6) 0.6055(4) 0.8749(3) 0.0409(14) Uani 1 1 d . . . . .
H37A H 0.519670 0.554405 0.874629 0.061 Uiso 1 1 calc GR . . . .
H37B H 0.554462 0.629498 0.891454 0.061 Uiso 1 1 calc GR . . . .
H37C H 0.460982 0.627141 0.832273 0.061 Uiso 1 1 calc GR . . . .
C38 C 0.2397(6) 0.4557(3) 0.9370(3) 0.0369(13) Uani 1 1 d . . . . .
H38A H 0.148181 0.485934 0.934537 0.055 Uiso 1 1 calc GR . . . .
H38B H 0.296739 0.472464 0.967199 0.055 Uiso 1 1 calc GR . . . .
H38C H 0.228143 0.405878 0.950526 0.055 Uiso 1 1 calc GR . . . .
C39 C 0.4049(7) 0.3935(4) 0.8613(3) 0.0451(15) Uani 1 1 d . . . . .
H39A H 0.462080 0.404044 0.824047 0.068 Uiso 1 1 calc GR . . . .
H39B H 0.349668 0.356394 0.854114 0.068 Uiso 1 1 calc GR . . . .
H39C H 0.465356 0.376546 0.897117 0.068 Uiso 1 1 calc GR . . . .
C40 C 0.1650(5) 0.6929(3) 0.7636(2) 0.0249(10) Uani 1 1 d . . . . .
C41 C 0.0946(5) 0.7235(3) 0.7012(2) 0.0238(10) Uani 1 1 d . . . . .
C42 C 0.1762(6) 0.7173(3) 0.6440(2) 0.0284(11) Uani 1 1 d . . . . .
C43 C 0.1095(6) 0.7488(4) 0.5868(3) 0.0379(13) Uani 1 1 d . . . . .
H43 H 0.161090 0.745074 0.548860 0.045 Uiso 1 1 calc R . . . .
C44 C -0.0277(6) 0.7845(3) 0.5840(3) 0.0350(13) Uani 1 1 d . . . . .
C45 C -0.1039(6) 0.7894(3) 0.6408(3) 0.0317(12) Uani 1 1 d . . . . .
H45 H -0.197115 0.813502 0.639368 0.038 Uiso 1 1 calc R . . . .
C46 C -0.0474(5) 0.7599(3) 0.6998(2) 0.0256(10) Uani 1 1 d . . . . .
C47 C 0.3292(6) 0.6749(3) 0.6349(3) 0.0350(13) Uani 1 1 d . . . . .
C48 C 0.4194(7) 0.7217(4) 0.5908(4) 0.0550(19) Uani 1 1 d . . . . .
H48A H 0.510780 0.693589 0.583698 0.082 Uiso 1 1 calc GR . . . .
H48B H 0.431204 0.764405 0.610249 0.082 Uiso 1 1 calc GR . . . .
H48C H 0.372499 0.736327 0.550746 0.082 Uiso 1 1 calc GR . . . .
C49 C 0.3113(8) 0.6075(4) 0.6030(3) 0.0533(18) Uani 1 1 d . . . . .
H49A H 0.249691 0.579414 0.628784 0.080 Uiso 1 1 calc GR . . . .
H49B H 0.402290 0.577954 0.598406 0.080 Uiso 1 1 calc GR . . . .
H49C H 0.270500 0.622670 0.561718 0.080 Uiso 1 1 calc GR . . . .
C50 C 0.4164(6) 0.6496(4) 0.6954(3) 0.0407(14) Uani 1 1 d . . . . .
H50A H 0.427028 0.691345 0.716572 0.061 Uiso 1 1 calc GR . . . .
H50B H 0.508471 0.625000 0.684155 0.061 Uiso 1 1 calc GR . . . .
H50C H 0.368410 0.616606 0.723483 0.061 Uiso 1 1 calc GR . . . .
C55 C -0.1485(5) 0.7668(3) 0.7586(2) 0.0281(11) Uani 1 1 d . . . . .
C56 C -0.2067(6) 0.6937(4) 0.7762(3) 0.0391(14) Uani 1 1 d . . . . .
H56A H -0.128778 0.654504 0.784057 0.059 Uiso 1 1 calc GR . . . .
H56B H -0.261699 0.684480 0.741611 0.059 Uiso 1 1 calc GR . . . .
H56C H -0.265565 0.696920 0.813830 0.059 Uiso 1 1 calc GR . . . .
C57 C -0.2787(7) 0.8266(4) 0.7442(3) 0.0451(15) Uani 1 1 d . . . . .
H57A H -0.331304 0.814401 0.710040 0.068 Uiso 1 1 calc GR . . . .
H57B H -0.247403 0.872914 0.732076 0.068 Uiso 1 1 calc GR . . . .
H57C H -0.338466 0.829632 0.781617 0.068 Uiso 1 1 calc GR . . . .
C58 C -0.0783(6) 0.7887(3) 0.8156(3) 0.0340(12) Uani 1 1 d . . . . .
H58A H -0.036364 0.831891 0.802775 0.051 Uiso 1 1 calc GR . . . .
H58B H -0.005857 0.749531 0.831617 0.051 Uiso 1 1 calc GR . . . .
H58C H -0.148347 0.798464 0.848511 0.051 Uiso 1 1 calc GR . . . .
C51 C -0.1016(14) 0.8145(7) 0.5211(7) 0.052(2) Uani 0.764(10) 1 d . U P A 1
C52 C -0.2066(12) 0.7655(6) 0.5076(5) 0.064(3) Uani 0.764(10) 1 d . U P A 1
H52A H -0.253289 0.784277 0.468138 0.096 Uiso 0.764(10) 1 calc GR . P A 1
H52B H -0.275994 0.764279 0.541562 0.096 Uiso 0.764(10) 1 calc GR . P A 1
H52C H -0.157431 0.716924 0.504482 0.096 Uiso 0.764(10) 1 calc GR . P A 1
C53 C -0.1824(14) 0.8917(7) 0.5266(5) 0.066(2) Uani 0.764(10) 1 d . U P A 1
H53A H -0.118763 0.921755 0.540383 0.098 Uiso 0.764(10) 1 calc GR . P A 1
H53B H -0.258858 0.888815 0.557089 0.098 Uiso 0.764(10) 1 calc GR . P A 1
H53C H -0.219988 0.912702 0.485827 0.098 Uiso 0.764(10) 1 calc GR . P A 1
C54 C 0.0014(12) 0.8195(8) 0.4657(5) 0.068(3) Uani 0.764(10) 1 d . U P A 1
H54A H 0.044476 0.771125 0.457804 0.102 Uiso 0.764(10) 1 calc GR . P A 1
H54B H 0.073707 0.846886 0.475498 0.102 Uiso 0.764(10) 1 calc GR . P A 1
H54C H -0.048326 0.843705 0.428425 0.102 Uiso 0.764(10) 1 calc GR . P A 1
C51B C -0.092(4) 0.828(2) 0.519(2) 0.060(3) Uani 0.236(10) 1 d D U P A 2
C52B C -0.027(4) 0.899(2) 0.5042(17) 0.070(4) Uani 0.236(10) 1 d D U P A 2
H52D H 0.074448 0.886566 0.499499 0.104 Uiso 0.236(10) 1 calc R . P A 2
H52E H -0.065496 0.925263 0.465434 0.104 Uiso 0.236(10) 1 calc R . P A 2
H52F H -0.048467 0.928257 0.538609 0.104 Uiso 0.236(10) 1 calc R . P A 2
C53B C -0.246(4) 0.859(2) 0.5242(16) 0.060(4) Uani 0.236(10) 1 d D U P A 2
H53D H -0.259590 0.889471 0.558409 0.090 Uiso 0.236(10) 1 calc R . P A 2
H53E H -0.275857 0.888078 0.484963 0.090 Uiso 0.236(10) 1 calc R . P A 2
H53F H -0.300624 0.819954 0.532708 0.090 Uiso 0.236(10) 1 calc R . P A 2
C54B C -0.044(4) 0.779(2) 0.4682(15) 0.063(4) Uani 0.236(10) 1 d D U P A 2
H54D H 0.056774 0.763169 0.470649 0.095 Uiso 0.236(10) 1 calc R . P A 2
H54E H -0.091634 0.736461 0.474662 0.095 Uiso 0.236(10) 1 calc R . P A 2
H54F H -0.066868 0.804585 0.426917 0.095 Uiso 0.236(10) 1 calc R . P A 2
Cl1 Cl -0.1003(2) -0.04500(14) 0.94402(10) 0.0789(8) Uani 1 1 d . . . . .
O1 O 0.0839(4) 0.0824(2) 0.81382(17) 0.0318(9) Uani 1 1 d . . . . .
O2 O -0.0485(4) 0.0762(2) 0.72912(19) 0.0355(9) Uani 1 1 d . . . . .
N1 N -0.1862(6) 0.1657(3) 0.8588(2) 0.0465(14) Uani 1 1 d . . . . .
N2 N -0.2750(5) 0.0605(3) 0.8435(3) 0.0389(12) Uani 1 1 d . . . . .
N3 N 0.1608(7) -0.0331(4) 0.9092(4) 0.084(3) Uani 1 1 d . . . . .
C1 C -0.1660(7) 0.0945(3) 0.8517(3) 0.0366(13) Uani 1 1 d . . . . .
C2 C -0.0215(6) 0.0537(3) 0.8542(3) 0.0356(13) Uani 1 1 d . . . . .
C3 C 0.0256(8) -0.0040(4) 0.8970(3) 0.057(2) Uani 1 1 d . . . . .
C4 C -0.0865(11) 0.1973(5) 0.8957(4) 0.072(3) Uani 1 1 d . . . . .
H4A H -0.001872 0.162406 0.903793 0.109 Uiso 1 1 calc GR . . . .
H4B H -0.130565 0.209170 0.935495 0.109 Uiso 1 1 calc GR . . . .
H4C H -0.062408 0.240984 0.871801 0.109 Uiso 1 1 calc GR . . . .
C5 C -0.3052(9) 0.2174(4) 0.8323(5) 0.067(2) Uani 1 1 d . . . . .
H5A H -0.377115 0.225512 0.864692 0.101 Uiso 1 1 calc GR . . . .
H5B H -0.343682 0.198022 0.797631 0.101 Uiso 1 1 calc GR . . . .
H5C H -0.273642 0.262935 0.816974 0.101 Uiso 1 1 calc GR . . . .
C6 C -0.4149(8) 0.0816(5) 0.8737(5) 0.075(3) Uani 1 1 d . . . . .
H6A H -0.409529 0.120181 0.899595 0.112 Uiso 1 1 calc GR . . . .
H6B H -0.441613 0.040033 0.899921 0.112 Uiso 1 1 calc GR . . . .
H6C H -0.484441 0.098352 0.841294 0.112 Uiso 1 1 calc GR . . . .
C7 C -0.2651(6) -0.0059(3) 0.8134(3) 0.0392(14) Uani 1 1 d . . . . .
H7A H -0.283018 -0.045440 0.844538 0.059 Uiso 1 1 calc GR . . . .
H7B H -0.171658 -0.017179 0.795301 0.059 Uiso 1 1 calc GR . . . .
H7C H -0.334170 0.000794 0.780305 0.059 Uiso 1 1 calc GR . . . .
C8 C 0.2037(11) -0.1111(7) 0.9302(7) 0.137(7) Uani 1 1 d . . . . .
H8A H 0.190922 -0.119886 0.975531 0.205 Uiso 1 1 calc GR . . . .
H8B H 0.301812 -0.125287 0.919117 0.205 Uiso 1 1 calc GR . . . .
H8C H 0.146358 -0.139288 0.909556 0.205 Uiso 1 1 calc GR . . . .
C9 C 0.2746(10) 0.0129(7) 0.9037(5) 0.103(5) Uani 1 1 d . . . . .
H9A H 0.323090 0.009092 0.863364 0.155 Uiso 1 1 calc GR . . . .
H9B H 0.340797 -0.003495 0.937551 0.155 Uiso 1 1 calc GR . . . .
H9C H 0.233875 0.062999 0.906576 0.155 Uiso 1 1 calc GR . . . .
C10 C 0.0631(6) 0.0849(3) 0.7493(3) 0.0292(11) Uani 1 1 d . . . . .
C11 C 0.1946(6) 0.0959(3) 0.7115(3) 0.0308(12) Uani 1 1 d . . . . .
C12 C 0.2728(6) 0.0339(3) 0.6854(3) 0.0396(14) Uani 1 1 d . . . . .
C13 C 0.3965(6) 0.0448(3) 0.6512(3) 0.0444(16) Uani 1 1 d . . . . .
H13 H 0.448743 0.005284 0.633591 0.053 Uiso 1 1 calc R . . . .
C14 C 0.4455(6) 0.1109(3) 0.6422(3) 0.0400(14) Uani 1 1 d . . . . .
C15 C 0.3654(6) 0.1695(3) 0.6665(3) 0.0347(13) Uani 1 1 d . . . . .
H15 H 0.397196 0.214582 0.659752 0.042 Uiso 1 1 calc R . . . .
C16 C 0.2392(6) 0.1651(3) 0.7006(3) 0.0297(11) Uani 1 1 d . . . . .
C17 C 0.2306(7) -0.0436(3) 0.6919(4) 0.056(2) Uani 1 1 d . . . . .
C18 C 0.1090(10) -0.0426(5) 0.6454(5) 0.075(3) Uani 1 1 d . . . . .
H18A H 0.026877 -0.010279 0.658021 0.113 Uiso 1 1 calc GR . . . .
H18B H 0.086143 -0.091139 0.646188 0.113 Uiso 1 1 calc GR . . . .
H18C H 0.138206 -0.025719 0.603036 0.113 Uiso 1 1 calc GR . . . .
C19 C 0.1905(9) -0.0715(4) 0.7591(5) 0.077(3) Uani 1 1 d . . . . .
H19A H 0.201261 -0.124049 0.763434 0.115 Uiso 1 1 calc GR . . . .
H19B H 0.093564 -0.051884 0.767933 0.115 Uiso 1 1 calc GR . . . .
H19C H 0.251372 -0.056436 0.788689 0.115 Uiso 1 1 calc GR . . . .
C20 C 0.3526(11) -0.1013(5) 0.6733(7) 0.101(4) Uani 1 1 d . . . . .
H20A H 0.321176 -0.148218 0.676712 0.152 Uiso 1 1 calc GR . . . .
H20B H 0.430846 -0.103669 0.701287 0.152 Uiso 1 1 calc GR . . . .
H20C H 0.382393 -0.088349 0.630135 0.152 Uiso 1 1 calc GR . . . .
C21 C 0.5876(7) 0.1177(4) 0.6046(4) 0.057(2) Uani 1 1 d . . . . .
C25 C 0.1603(7) 0.2359(3) 0.7247(3) 0.0391(14) Uani 1 1 d . . . . .
C26 C 0.1888(9) 0.3048(4) 0.6800(4) 0.062(2) Uani 1 1 d . . . . .
H26A H 0.280715 0.316087 0.688722 0.093 Uiso 1 1 calc GR . . . .
H26B H 0.117382 0.345569 0.687466 0.093 Uiso 1 1 calc GR . . . .
H26C H 0.186009 0.295454 0.636407 0.093 Uiso 1 1 calc GR . . . .
C27 C -0.0024(6) 0.2404(3) 0.7260(3) 0.0409(14) Uani 1 1 d . . . . .
H27A H -0.029652 0.205222 0.759235 0.061 Uiso 1 1 calc GR . . . .
H27B H -0.033154 0.230027 0.685688 0.061 Uiso 1 1 calc GR . . . .
H27C H -0.045707 0.288702 0.733970 0.061 Uiso 1 1 calc GR . . . .
C28 C 0.2159(9) 0.2409(5) 0.7915(4) 0.062(2) Uani 1 1 d . . . . .
H28A H 0.315903 0.243162 0.788725 0.093 Uiso 1 1 calc GR . . . .
H28B H 0.199611 0.198523 0.819628 0.093 Uiso 1 1 calc GR . . . .
H28C H 0.166873 0.284207 0.807794 0.093 Uiso 1 1 calc GR . . . .
C22 C 0.7080(14) 0.0595(11) 0.6341(9) 0.074(5) Uani 0.646(12) 1 d . U P B 1
H22A H 0.672259 0.014302 0.646217 0.112 Uiso 0.646(12) 1 calc GR . P B 1
H22B H 0.743117 0.076056 0.670995 0.112 Uiso 0.646(12) 1 calc GR . P B 1
H22C H 0.783753 0.051794 0.603294 0.112 Uiso 0.646(12) 1 calc GR . P B 1
C23 C 0.5743(11) 0.0946(7) 0.5330(5) 0.051(3) Uani 0.646(12) 1 d . U P B 1
H23A H 0.492692 0.123857 0.512638 0.076 Uiso 0.646(12) 1 calc GR . P B 1
H23B H 0.564303 0.043789 0.535780 0.076 Uiso 0.646(12) 1 calc GR . P B 1
H23C H 0.658240 0.102636 0.508485 0.076 Uiso 0.646(12) 1 calc GR . P B 1
C24 C 0.6200(16) 0.1924(8) 0.5943(8) 0.073(4) Uani 0.646(12) 1 d . U P B 1
H24A H 0.622693 0.211086 0.634649 0.109 Uiso 0.646(12) 1 calc GR . P B 1
H24B H 0.547901 0.222776 0.568442 0.109 Uiso 0.646(12) 1 calc GR . P B 1
H24C H 0.710586 0.192310 0.573066 0.109 Uiso 0.646(12) 1 calc GR . P B 1
C22B C 0.672(3) 0.0506(19) 0.6007(18) 0.081(8) Uani 0.354(12) 1 d . U P B 2
H22D H 0.636897 0.026758 0.567855 0.121 Uiso 0.354(12) 1 calc GR . P B 2
H22E H 0.668421 0.020607 0.640830 0.121 Uiso 0.354(12) 1 calc GR . P B 2
H22F H 0.767774 0.057804 0.590846 0.121 Uiso 0.354(12) 1 calc GR . P B 2
C23B C 0.6817(17) 0.1590(12) 0.6593(9) 0.050(5) Uani 0.354(12) 1 d . U P B 2
H23D H 0.709517 0.124075 0.695482 0.075 Uiso 0.354(12) 1 calc GR . P B 2
H23E H 0.621111 0.200695 0.673168 0.075 Uiso 0.354(12) 1 calc GR . P B 2
H23F H 0.764677 0.174500 0.638393 0.075 Uiso 0.354(12) 1 calc GR . P B 2
C24B C 0.559(2) 0.1756(16) 0.5540(11) 0.066(5) Uani 0.354(12) 1 d . U P B 2
H24D H 0.496064 0.215736 0.569348 0.100 Uiso 0.354(12) 1 calc GR . P B 2
H24E H 0.514143 0.158320 0.519809 0.100 Uiso 0.354(12) 1 calc GR . P B 2
H24F H 0.645786 0.191659 0.538879 0.100 Uiso 0.354(12) 1 calc GR . P B 2
O61 O -0.2270(7) 0.5704(3) 0.5589(3) 0.0593(16) Uani 0.882(7) 1 d . . P C 1
C61 C -0.2175(14) 0.5602(7) 0.4914(5) 0.083(3) Uani 0.882(7) 1 d . . P C 1
H61A H -0.156141 0.592284 0.469375 0.100 Uiso 0.882(7) 1 calc R . P C 1
H61B H -0.176634 0.510049 0.486478 0.100 Uiso 0.882(7) 1 calc R . P C 1
C62 C -0.3585(14) 0.5767(7) 0.4638(5) 0.087(4) Uani 0.882(7) 1 d . . P C 1
H62A H -0.415697 0.541402 0.482444 0.131 Uiso 0.882(7) 1 calc GR . P C 1
H62B H -0.350574 0.574759 0.418596 0.131 Uiso 0.882(7) 1 calc GR . P C 1
H62C H -0.401998 0.624852 0.472199 0.131 Uiso 0.882(7) 1 calc GR . P C 1
C63 C -0.0950(12) 0.5594(8) 0.5882(6) 0.087(4) Uani 0.882(7) 1 d . . P C 1
H63A H -0.034951 0.591153 0.564766 0.105 Uiso 0.882(7) 1 calc R . P C 1
H63B H -0.050522 0.509179 0.585738 0.105 Uiso 0.882(7) 1 calc R . P C 1
C64 C -0.1024(13) 0.5732(7) 0.6538(5) 0.080(3) Uani 0.882(7) 1 d . . P C 1
H64A H -0.163855 0.543053 0.677242 0.119 Uiso 0.882(7) 1 calc GR . P C 1
H64B H -0.139174 0.623867 0.656518 0.119 Uiso 0.882(7) 1 calc GR . P C 1
H64C H -0.009055 0.562023 0.671597 0.119 Uiso 0.882(7) 1 calc GR . P C 1
P2 P 0.38177(16) 0.19811(8) 1.01092(7) 0.0345(4) Uani 1 1 d . . . . .
F11 F 0.2228(5) 0.1879(3) 1.0277(3) 0.0773(15) Uani 1 1 d . . . . .
F12 F 0.5425(4) 0.2087(3) 0.9933(3) 0.0735(13) Uani 1 1 d . . . . .
F13 F 0.3520(6) 0.2045(5) 0.9381(3) 0.084(2) Uani 0.881(7) 1 d . U P D 1
F14 F 0.4310(6) 0.1125(3) 1.0099(3) 0.0765(18) Uani 0.881(7) 1 d . U P D 1
F15 F 0.4171(7) 0.1907(5) 1.0839(2) 0.090(2) Uani 0.881(7) 1 d . U P D 1
F16 F 0.3373(6) 0.2844(3) 1.0108(4) 0.0686(18) Uani 0.881(7) 1 d . U P D 1
F13B F 0.345(5) 0.148(3) 0.963(2) 0.080(7) Uani 0.119(7) 1 d . U P D 2
F14B F 0.394(5) 0.141(3) 1.069(2) 0.080(7) Uani 0.119(7) 1 d . U P D 2
F15B F 0.355(5) 0.268(3) 1.046(3) 0.067(7) Uani 0.119(7) 1 d . U P D 2
F16B F 0.328(5) 0.259(3) 0.960(3) 0.081(7) Uani 0.119(7) 1 d . U P D 2
P1 P -0.15036(17) 0.43741(9) 0.84793(8) 0.0392(4) Uani 1 1 d . . . . .
F1 F -0.1214(6) 0.3994(3) 0.7848(2) 0.0750(14) Uani 1 1 d . . . . .
F2 F -0.1842(8) 0.4755(3) 0.9108(3) 0.109(3) Uani 1 1 d . . . . .
F3 F -0.0566(5) 0.4972(3) 0.8223(2) 0.0684(13) Uani 1 1 d . . . . .
F4 F -0.2859(5) 0.4850(3) 0.8149(3) 0.0991(19) Uani 1 1 d . . . . .
F5 F -0.2440(6) 0.3762(3) 0.8760(2) 0.0767(14) Uani 1 1 d . . . . .
F6 F -0.0164(6) 0.3873(4) 0.8800(3) 0.104(2) Uani 1 1 d . . . . .
Cl3 Cl 0.7810(3) 0.36587(15) 0.58688(12) 0.0903(8) Uani 1 1 d . . . . .
Cl4 Cl 0.5738(3) 0.36652(19) 0.69073(14) 0.0975(9) Uani 1 1 d . . . . .
C65 C 0.7002(11) 0.4132(5) 0.6502(4) 0.073(2) Uani 1 1 d . . . . .
H65A H 0.772590 0.418707 0.679708 0.088 Uiso 1 1 calc R . . . .
H65B H 0.655373 0.461712 0.633196 0.088 Uiso 1 1 calc R . . . .
Cl5 Cl -0.212(3) 0.5817(18) 0.6165(16) 0.120(11) Uani 0.118(7) 1 d D U P C 2
Cl6 Cl 0.046(3) 0.4831(16) 0.6152(14) 0.108(10) Uani 0.118(7) 1 d D U P C 2
C66 C -0.139(4) 0.491(3) 0.608(8) 0.15(5) Uani 0.118(7) 1 d D U P C 2
H66A H -0.162507 0.477863 0.567156 0.181 Uiso 0.118(7) 1 calc R . P C 2
H66B H -0.176648 0.457781 0.641378 0.181 Uiso 0.118(7) 1 calc R . P C 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
Cl2 C33 1.733(5) . ?
O31 C32 1.418(6) . ?
O31 C40 1.370(6) . ?
O32 C40 1.196(6) . ?
N31 C31 1.334(7) . ?
N31 C34 1.475(7) . ?
N31 C35 1.463(7) . ?
N32 C31 1.330(7) . ?
N32 C36 1.470(7) . ?
N32 C37 1.455(7) . ?
N33 C33 1.348(7) . ?
N33 C38 1.464(7) . ?
N33 C39 1.465(7) . ?
C31 C32 1.463(7) . ?
C32 C33 1.353(7) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 C41 1.507(7) . ?
C41 C42 1.421(7) . ?
C41 C46 1.415(7) . ?
C42 C43 1.406(8) . ?
C42 C47 1.564(8) . ?
C43 H43 0.9300 . ?
C43 C44 1.372(9) . ?
C44 C45 1.385(8) . ?
C44 C51 1.529(16) . ?
C44 C51B 1.60(5) . ?
C45 H45 0.9300 . ?
C45 C46 1.392(7) . ?
C46 C55 1.551(7) . ?
C47 C48 1.536(9) . ?
C47 C49 1.526(10) . ?
C47 C50 1.534(8) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C55 C56 1.548(8) . ?
C55 C57 1.545(8) . ?
C55 C58 1.524(8) . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C51 C52 1.510(16) . ?
C51 C53 1.534(17) . ?
C51 C54 1.506(16) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 0.9600 . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C51B C52B 1.53(2) . ?
C51B C53B 1.50(2) . ?
C51B C54B 1.51(2) . ?
C52B H52D 0.9600 . ?
C52B H52E 0.9600 . ?
C52B H52F 0.9600 . ?
C53B H53D 0.9600 . ?
C53B H53E 0.9600 . ?
C53B H53F 0.9600 . ?
C54B H54D 0.9600 . ?
C54B H54E 0.9600 . ?
C54B H54F 0.9600 . ?
Cl1 C3 1.743(6) . ?
O1 C2 1.424(6) . ?
O1 C10 1.379(7) . ?
O2 C10 1.200(7) . ?
N1 C1 1.334(8) . ?
N1 C4 1.479(10) . ?
N1 C5 1.449(11) . ?
N2 C1 1.325(8) . ?
N2 C6 1.475(8) . ?
N2 C7 1.443(8) . ?
N3 C3 1.338(10) . ?
N3 C8 1.466(13) . ?
N3 C9 1.476(9) . ?
C1 C2 1.465(9) . ?
C2 C3 1.348(9) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.492(7) . ?
C11 C12 1.429(8) . ?
C11 C16 1.409(7) . ?
C12 C13 1.392(8) . ?
C12 C17 1.546(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(9) . ?
C14 C15 1.370(9) . ?
C14 C21 1.561(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.391(8) . ?
C16 C25 1.543(8) . ?
C17 C18 1.540(13) . ?
C17 C19 1.512(13) . ?
C17 C20 1.529(11) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.542(16) . ?
C21 C23 1.634(14) . ?
C21 C24 1.461(15) . ?
C21 C22B 1.38(3) . ?
C21 C23B 1.80(2) . ?
C21 C24B 1.43(3) . ?
C25 C26 1.554(9) . ?
C25 C27 1.539(9) . ?
C25 C28 1.543(10) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C22B H22D 0.9600 . ?
C22B H22E 0.9600 . ?
C22B H22F 0.9600 . ?
C23B H23D 0.9600 . ?
C23B H23E 0.9600 . ?
C23B H23F 0.9600 . ?
C24B H24D 0.9600 . ?
C24B H24E 0.9600 . ?
C24B H24F 0.9600 . ?
O61 C61 1.457(12) . ?
O61 C63 1.396(13) . ?
C61 H61A 0.9700 . ?
C61 H61B 0.9700 . ?
C61 C62 1.456(17) . ?
C62 H62A 0.9600 . ?
C62 H62B 0.9600 . ?
C62 H62C 0.9600 . ?
C63 H63A 0.9700 . ?
C63 H63B 0.9700 . ?
C63 C64 1.437(16) . ?
C64 H64A 0.9600 . ?
C64 H64B 0.9600 . ?
C64 H64C 0.9600 . ?
P2 F11 1.580(5) . ?
P2 F12 1.601(4) . ?
P2 F13 1.561(6) . ?
P2 F14 1.591(5) . ?
P2 F15 1.575(6) . ?
P2 F16 1.594(5) . ?
P2 F13B 1.54(5) . ?
P2 F14B 1.53(4) . ?
P2 F15B 1.55(5) . ?
P2 F16B 1.51(4) . ?
P1 F1 1.579(4) . ?
P1 F2 1.578(5) . ?
P1 F3 1.571(4) . ?
P1 F4 1.580(6) . ?
P1 F5 1.603(4) . ?
P1 F6 1.579(5) . ?
Cl3 C65 1.775(10) . ?
Cl4 C65 1.739(10) . ?
C65 H65A 0.9700 . ?
C65 H65B 0.9700 . ?
Cl5 C66 1.75(2) . ?
Cl6 C66 1.76(2) . ?
C66 H66A 0.9700 . ?
C66 H66B 0.9700 . ?

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
C40 O31 C32 117.1(4) . . ?
C31 N31 C34 122.0(5) . . ?
C31 N31 C35 123.8(5) . . ?
C35 N31 C34 113.9(5) . . ?
C31 N32 C36 123.0(5) . . ?
C31 N32 C37 123.1(5) . . ?
C37 N32 C36 113.6(4) . . ?
C33 N33 C38 121.3(4) . . ?
C33 N33 C39 121.7(5) . . ?
C38 N33 C39 114.6(5) . . ?
N31 C31 C32 119.7(4) . . ?
N32 C31 N31 121.5(5) . . ?
N32 C31 C32 118.7(5) . . ?
O31 C32 C31 119.1(4) . . ?
C33 C32 O31 117.1(4) . . ?
C33 C32 C31 123.5(4) . . ?
N33 C33 Cl2 116.1(4) . . ?
N33 C33 C32 125.1(5) . . ?
C32 C33 Cl2 118.8(4) . . ?
N31 C34 H34A 109.5 . . ?
N31 C34 H34B 109.5 . . ?
N31 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N31 C35 H35A 109.5 . . ?
N31 C35 H35B 109.5 . . ?
N31 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N32 C36 H36A 109.5 . . ?
N32 C36 H36B 109.5 . . ?
N32 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N32 C37 H37A 109.5 . . ?
N32 C37 H37B 109.5 . . ?
N32 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N33 C38 H38A 109.5 . . ?
N33 C38 H38B 109.5 . . ?
N33 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N33 C39 H39A 109.5 . . ?
N33 C39 H39B 109.5 . . ?
N33 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O31 C40 C41 110.8(4) . . ?
O32 C40 O31 123.0(4) . . ?
O32 C40 C41 126.1(5) . . ?
C42 C41 C40 118.3(4) . . ?
C46 C41 C40 120.9(4) . . ?
C46 C41 C42 120.7(4) . . ?
C41 C42 C47 128.6(5) . . ?
C43 C42 C41 117.1(5) . . ?
C43 C42 C47 114.2(5) . . ?
C42 C43 H43 118.3 . . ?
C44 C43 C42 123.4(5) . . ?
C44 C43 H43 118.3 . . ?
C43 C44 C45 117.8(5) . . ?
C43 C44 C51 122.7(7) . . ?
C43 C44 C51B 121.2(13) . . ?
C45 C44 C51 119.3(7) . . ?
C45 C44 C51B 120.5(13) . . ?
C44 C45 H45 118.5 . . ?
C44 C45 C46 123.0(5) . . ?
C46 C45 H45 118.5 . . ?
C41 C46 C55 125.2(4) . . ?
C45 C46 C41 117.9(5) . . ?
C45 C46 C55 116.8(5) . . ?
C48 C47 C42 110.8(5) . . ?
C49 C47 C42 106.2(5) . . ?
C49 C47 C48 108.6(5) . . ?
C49 C47 C50 108.5(5) . . ?
C50 C47 C42 116.7(4) . . ?
C50 C47 C48 105.9(5) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C47 C49 H49A 109.5 . . ?
C47 C49 H49B 109.5 . . ?
C47 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C47 C50 H50A 109.5 . . ?
C47 C50 H50B 109.5 . . ?
C47 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C56 C55 C46 109.2(5) . . ?
C57 C55 C46 111.7(4) . . ?
C57 C55 C56 106.6(5) . . ?
C58 C55 C46 113.0(4) . . ?
C58 C55 C56 110.9(4) . . ?
C58 C55 C57 105.3(5) . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56B 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C55 C57 H57A 109.5 . . ?
C55 C57 H57B 109.5 . . ?
C55 C57 H57C 109.5 . . ?
H57A C57 H57B 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C55 C58 H58A 109.5 . . ?
C55 C58 H58B 109.5 . . ?
C55 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C44 C51 C53 109.4(10) . . ?
C52 C51 C44 109.3(9) . . ?
C52 C51 C53 108.7(11) . . ?
C54 C51 C44 112.6(10) . . ?
C54 C51 C52 108.9(12) . . ?
C54 C51 C53 107.9(11) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C51 C54 H54A 109.5 . . ?
C51 C54 H54B 109.5 . . ?
C51 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C52B C51B C44 109(3) . . ?
C53B C51B C44 113(3) . . ?
C53B C51B C52B 100(3) . . ?
C53B C51B C54B 119(4) . . ?
C54B C51B C44 105(3) . . ?
C54B C51B C52B 109(4) . . ?
C51B C52B H52D 109.5 . . ?
C51B C52B H52E 109.5 . . ?
C51B C52B H52F 109.5 . . ?
H52D C52B H52E 109.5 . . ?
H52D C52B H52F 109.5 . . ?
H52E C52B H52F 109.5 . . ?
C51B C53B H53D 109.5 . . ?
C51B C53B H53E 109.5 . . ?
C51B C53B H53F 109.5 . . ?
H53D C53B H53E 109.5 . . ?
H53D C53B H53F 109.5 . . ?
H53E C53B H53F 109.5 . . ?
C51B C54B H54D 109.5 . . ?
C51B C54B H54E 109.5 . . ?
C51B C54B H54F 109.5 . . ?
H54D C54B H54E 109.5 . . ?
H54D C54B H54F 109.5 . . ?
H54E C54B H54F 109.5 . . ?
C10 O1 C2 115.6(4) . . ?
C1 N1 C4 121.3(7) . . ?
C1 N1 C5 123.7(6) . . ?
C5 N1 C4 115.1(7) . . ?
C1 N2 C6 121.6(6) . . ?
C1 N2 C7 124.4(5) . . ?
C7 N2 C6 113.4(5) . . ?
C3 N3 C8 122.3(7) . . ?
C3 N3 C9 121.2(7) . . ?
C8 N3 C9 116.4(7) . . ?
N1 C1 C2 119.2(5) . . ?
N2 C1 N1 120.8(6) . . ?
N2 C1 C2 120.0(5) . . ?
O1 C2 C1 117.7(5) . . ?
C3 C2 O1 116.0(6) . . ?
C3 C2 C1 125.7(6) . . ?
N3 C3 Cl1 114.9(5) . . ?
N3 C3 C2 127.2(6) . . ?
C2 C3 Cl1 117.8(5) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C11 111.8(4) . . ?
O2 C10 O1 121.2(5) . . ?
O2 C10 C11 127.0(5) . . ?
C12 C11 C10 117.5(5) . . ?
C16 C11 C10 121.5(5) . . ?
C16 C11 C12 120.9(5) . . ?
C11 C12 C17 125.4(5) . . ?
C13 C12 C11 116.8(5) . . ?
C13 C12 C17 117.9(6) . . ?
C12 C13 H13 118.3 . . ?
C14 C13 C12 123.5(6) . . ?
C14 C13 H13 118.3 . . ?
C13 C14 C21 120.0(6) . . ?
C15 C14 C13 117.9(5) . . ?
C15 C14 C21 122.1(6) . . ?
C14 C15 H15 118.3 . . ?
C14 C15 C16 123.5(5) . . ?
C16 C15 H15 118.3 . . ?
C11 C16 C25 125.1(5) . . ?
C15 C16 C11 117.3(5) . . ?
C15 C16 C25 117.5(5) . . ?
C18 C17 C12 108.1(6) . . ?
C19 C17 C12 113.9(7) . . ?
C19 C17 C18 111.3(7) . . ?
C19 C17 C20 104.2(7) . . ?
C20 C17 C12 112.2(6) . . ?
C20 C17 C18 106.9(8) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C21 C23 109.1(6) . . ?
C14 C21 C23B 101.4(8) . . ?
C22 C21 C14 110.1(8) . . ?
C22 C21 C23 103.2(10) . . ?
C24 C21 C14 113.7(8) . . ?
C24 C21 C22 115.3(11) . . ?
C24 C21 C23 104.6(9) . . ?
C22B C21 C14 112.7(12) . . ?
C22B C21 C23B 103.1(19) . . ?
C22B C21 C24B 126.4(19) . . ?
C24B C21 C14 107.6(10) . . ?
C24B C21 C23B 101.9(14) . . ?
C16 C25 C26 111.3(5) . . ?
C27 C25 C16 113.4(5) . . ?
C27 C25 C26 104.7(6) . . ?
C27 C25 C28 110.9(6) . . ?
C28 C25 C16 108.0(5) . . ?
C28 C25 C26 108.4(6) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C22B H22D 109.5 . . ?
C21 C22B H22E 109.5 . . ?
C21 C22B H22F 109.5 . . ?
H22D C22B H22E 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C21 C23B H23D 109.5 . . ?
C21 C23B H23E 109.5 . . ?
C21 C23B H23F 109.5 . . ?
H23D C23B H23E 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C21 C24B H24D 109.5 . . ?
C21 C24B H24E 109.5 . . ?
C21 C24B H24F 109.5 . . ?
H24D C24B H24E 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
C63 O61 C61 113.4(9) . . ?
O61 C61 H61A 109.7 . . ?
O61 C61 H61B 109.7 . . ?
H61A C61 H61B 108.2 . . ?
C62 C61 O61 109.8(10) . . ?
C62 C61 H61A 109.7 . . ?
C62 C61 H61B 109.7 . . ?
C61 C62 H62A 109.5 . . ?
C61 C62 H62B 109.5 . . ?
C61 C62 H62C 109.5 . . ?
H62A C62 H62B 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
O61 C63 H63A 108.8 . . ?
O61 C63 H63B 108.8 . . ?
O61 C63 C64 113.9(10) . . ?
H63A C63 H63B 107.7 . . ?
C64 C63 H63A 108.8 . . ?
C64 C63 H63B 108.8 . . ?
C63 C64 H64A 109.5 . . ?
C63 C64 H64B 109.5 . . ?
C63 C64 H64C 109.5 . . ?
H64A C64 H64B 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
F11 P2 F12 179.5(3) . . ?
F11 P2 F14 92.5(3) . . ?
F11 P2 F16 89.3(3) . . ?
F13 P2 F11 91.0(3) . . ?
F13 P2 F12 88.5(3) . . ?
F13 P2 F14 88.8(4) . . ?
F13 P2 F15 178.1(4) . . ?
F13 P2 F16 90.7(4) . . ?
F14 P2 F12 87.5(3) . . ?
F14 P2 F16 178.1(3) . . ?
F15 P2 F11 90.7(4) . . ?
F15 P2 F12 89.8(4) . . ?
F15 P2 F14 90.3(4) . . ?
F15 P2 F16 90.1(4) . . ?
F16 P2 F12 90.6(3) . . ?
F13B P2 F11 75.4(18) . . ?
F13B P2 F12 104.3(18) . . ?
F13B P2 F15B 153(3) . . ?
F14B P2 F11 76.3(19) . . ?
F14B P2 F12 104.2(19) . . ?
F14B P2 F13B 97(3) . . ?
F14B P2 F15B 99(3) . . ?
F15B P2 F11 87.6(18) . . ?
F15B P2 F12 92.6(18) . . ?
F16B P2 F11 88.7(18) . . ?
F16B P2 F12 90.8(18) . . ?
F16B P2 F13B 84(3) . . ?
F16B P2 F14B 164(3) . . ?
F16B P2 F15B 76(3) . . ?
F1 P1 F4 87.7(3) . . ?
F1 P1 F5 90.2(3) . . ?
F1 P1 F6 90.8(4) . . ?
F2 P1 F1 178.3(4) . . ?
F2 P1 F4 90.9(4) . . ?
F2 P1 F5 88.8(3) . . ?
F2 P1 F6 90.5(4) . . ?
F3 P1 F1 91.0(3) . . ?
F3 P1 F2 90.1(2) . . ?
F3 P1 F4 90.9(3) . . ?
F3 P1 F5 178.4(3) . . ?
F3 P1 F6 90.6(3) . . ?
F4 P1 F5 90.3(3) . . ?
F6 P1 F4 177.9(4) . . ?
F6 P1 F5 88.3(3) . . ?
Cl3 C65 H65A 109.4 . . ?
Cl3 C65 H65B 109.4 . . ?
Cl4 C65 Cl3 111.4(5) . . ?
Cl4 C65 H65A 109.4 . . ?
Cl4 C65 H65B 109.4 . . ?
H65A C65 H65B 108.0 . . ?
Cl5 C66 Cl6 107(2) . . ?
Cl5 C66 H66A 110.2 . . ?
Cl5 C66 H66B 110.2 . . ?
Cl6 C66 H66A 110.2 . . ?
Cl6 C66 H66B 110.2 . . ?
H66A C66 H66B 108.5 . . ?

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
O31 C32 C33 Cl2 13.7(6) . . . . ?
O31 C32 C33 N33 -163.9(5) . . . . ?
O31 C40 C41 C42 -99.4(5) . . . . ?
O31 C40 C41 C46 83.1(6) . . . . ?
O32 C40 C41 C42 81.7(7) . . . . ?
O32 C40 C41 C46 -95.8(6) . . . . ?
N31 C31 C32 O31 52.0(6) . . . . ?
N31 C31 C32 C33 -122.5(6) . . . . ?
N32 C31 C32 O31 -127.6(5) . . . . ?
N32 C31 C32 C33 57.9(7) . . . . ?
C31 C32 C33 Cl2 -171.7(4) . . . . ?
C31 C32 C33 N33 10.7(8) . . . . ?
C32 O31 C40 O32 -14.1(7) . . . . ?
C32 O31 C40 C41 166.9(4) . . . . ?
C34 N31 C31 N32 -150.1(5) . . . . ?
C34 N31 C31 C32 30.3(7) . . . . ?
C35 N31 C31 N32 24.9(8) . . . . ?
C35 N31 C31 C32 -154.8(5) . . . . ?
C36 N32 C31 N31 29.4(8) . . . . ?
C36 N32 C31 C32 -151.0(5) . . . . ?
C37 N32 C31 N31 -157.6(5) . . . . ?
C37 N32 C31 C32 22.0(7) . . . . ?
C38 N33 C33 Cl2 -137.1(5) . . . . ?
C38 N33 C33 C32 40.6(8) . . . . ?
C39 N33 C33 Cl2 24.1(7) . . . . ?
C39 N33 C33 C32 -158.3(6) . . . . ?
C40 O31 C32 C31 52.9(6) . . . . ?
C40 O31 C32 C33 -132.3(5) . . . . ?
C40 C41 C42 C43 -177.6(5) . . . . ?
C40 C41 C42 C47 7.4(8) . . . . ?
C40 C41 C46 C45 177.4(5) . . . . ?
C40 C41 C46 C55 -5.6(8) . . . . ?
C41 C42 C43 C44 0.3(9) . . . . ?
C41 C42 C47 C48 -135.3(6) . . . . ?
C41 C42 C47 C49 106.9(6) . . . . ?
C41 C42 C47 C50 -14.1(9) . . . . ?
C41 C46 C55 C56 -78.0(6) . . . . ?
C41 C46 C55 C57 164.4(5) . . . . ?
C41 C46 C55 C58 46.0(7) . . . . ?
C42 C41 C46 C45 0.0(8) . . . . ?
C42 C41 C46 C55 177.0(5) . . . . ?
C42 C43 C44 C45 -0.3(9) . . . . ?
C42 C43 C44 C51 -176.3(8) . . . . ?
C42 C43 C44 C51B 172.0(16) . . . . ?
C43 C42 C47 C48 49.5(7) . . . . ?
C43 C42 C47 C49 -68.2(6) . . . . ?
C43 C42 C47 C50 170.8(5) . . . . ?
C43 C44 C45 C46 0.1(9) . . . . ?
C43 C44 C51 C52 105.2(10) . . . . ?
C43 C44 C51 C53 -136.0(9) . . . . ?
C43 C44 C51 C54 -16.0(14) . . . . ?
C43 C44 C51B C52B -73(3) . . . . ?
C43 C44 C51B C53B 176(2) . . . . ?
C43 C44 C51B C54B 44(3) . . . . ?
C44 C45 C46 C41 0.0(8) . . . . ?
C44 C45 C46 C55 -177.2(5) . . . . ?
C45 C44 C51 C52 -70.8(11) . . . . ?
C45 C44 C51 C53 48.1(12) . . . . ?
C45 C44 C51 C54 168.0(10) . . . . ?
C45 C44 C51B C52B 99(3) . . . . ?
C45 C44 C51B C53B -12(3) . . . . ?
C45 C44 C51B C54B -144(2) . . . . ?
C45 C46 C55 C56 99.0(6) . . . . ?
C45 C46 C55 C57 -18.6(7) . . . . ?
C45 C46 C55 C58 -137.0(5) . . . . ?
C46 C41 C42 C43 -0.1(8) . . . . ?
C46 C41 C42 C47 -175.2(5) . . . . ?
C47 C42 C43 C44 176.0(6) . . . . ?
C51 C44 C45 C46 176.3(7) . . . . ?
C51B C44 C45 C46 -172.2(16) . . . . ?
O1 C2 C3 Cl1 -175.8(5) . . . . ?
O1 C2 C3 N3 6.1(13) . . . . ?
O1 C10 C11 C12 104.4(6) . . . . ?
O1 C10 C11 C16 -76.9(6) . . . . ?
O2 C10 C11 C12 -72.9(8) . . . . ?
O2 C10 C11 C16 105.8(7) . . . . ?
N1 C1 C2 O1 -52.3(7) . . . . ?
N1 C1 C2 C3 118.9(7) . . . . ?
N2 C1 C2 O1 128.8(6) . . . . ?
N2 C1 C2 C3 -60.0(9) . . . . ?
C1 C2 C3 Cl1 12.9(10) . . . . ?
C1 C2 C3 N3 -165.3(8) . . . . ?
C2 O1 C10 O2 13.0(7) . . . . ?
C2 O1 C10 C11 -164.5(5) . . . . ?
C4 N1 C1 N2 151.7(6) . . . . ?
C4 N1 C1 C2 -27.3(8) . . . . ?
C5 N1 C1 N2 -27.7(9) . . . . ?
C5 N1 C1 C2 153.4(6) . . . . ?
C6 N2 C1 N1 -33.1(9) . . . . ?
C6 N2 C1 C2 145.8(7) . . . . ?
C7 N2 C1 N1 156.6(6) . . . . ?
C7 N2 C1 C2 -24.5(9) . . . . ?
C8 N3 C3 Cl1 32.7(14) . . . . ?
C8 N3 C3 C2 -149.1(11) . . . . ?
C9 N3 C3 Cl1 -145.6(8) . . . . ?
C9 N3 C3 C2 32.5(15) . . . . ?
C10 O1 C2 C1 -64.4(7) . . . . ?
C10 O1 C2 C3 123.6(6) . . . . ?
C10 C11 C12 C13 -178.9(6) . . . . ?
C10 C11 C12 C17 1.3(9) . . . . ?
C10 C11 C16 C15 178.1(5) . . . . ?
C10 C11 C16 C25 -0.8(9) . . . . ?
C11 C12 C13 C14 0.4(10) . . . . ?
C11 C12 C17 C18 76.5(9) . . . . ?
C11 C12 C17 C19 -47.8(10) . . . . ?
C11 C12 C17 C20 -165.9(8) . . . . ?
C11 C16 C25 C26 -151.9(6) . . . . ?
C11 C16 C25 C27 -34.2(8) . . . . ?
C11 C16 C25 C28 89.1(7) . . . . ?
C12 C11 C16 C15 -3.2(8) . . . . ?
C12 C11 C16 C25 177.9(6) . . . . ?
C12 C13 C14 C15 -2.1(10) . . . . ?
C12 C13 C14 C21 178.4(7) . . . . ?
C13 C12 C17 C18 -103.3(7) . . . . ?
C13 C12 C17 C19 132.4(7) . . . . ?
C13 C12 C17 C20 14.3(11) . . . . ?
C13 C14 C15 C16 1.2(10) . . . . ?
C13 C14 C21 C22 -53.7(12) . . . . ?
C13 C14 C21 C23 58.9(9) . . . . ?
C13 C14 C21 C24 175.2(10) . . . . ?
C13 C14 C21 C22B -19(2) . . . . ?
C13 C14 C21 C23B -128.1(9) . . . . ?
C13 C14 C21 C24B 125.4(14) . . . . ?
C14 C15 C16 C11 1.4(9) . . . . ?
C14 C15 C16 C25 -179.6(6) . . . . ?
C15 C14 C21 C22 126.8(11) . . . . ?
C15 C14 C21 C23 -120.6(8) . . . . ?
C15 C14 C21 C24 -4.2(12) . . . . ?
C15 C14 C21 C22B 162(2) . . . . ?
C15 C14 C21 C23B 52.4(10) . . . . ?
C15 C14 C21 C24B -54.1(15) . . . . ?
C15 C16 C25 C26 29.2(8) . . . . ?
C15 C16 C25 C27 146.9(5) . . . . ?
C15 C16 C25 C28 -89.8(6) . . . . ?
C16 C11 C12 C13 2.4(9) . . . . ?
C16 C11 C12 C17 -177.4(6) . . . . ?
C17 C12 C13 C14 -179.9(7) . . . . ?
C21 C14 C15 C16 -179.3(6) . . . . ?
C61 O61 C63 C64 176.7(10) . . . . ?
C63 O61 C61 C62 -176.8(10) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.087
_oxdiff_exptl_absorpt_empirical_full_min 0.906
# start Validation Reply Form
_vrf_PLAT411_1d                  
;
PROBLEM: Short Inter H...H Contact H65A ..H66B . 1.17 Ang.
RESPONSE: H65a and H66b belong to a disordered terbutyl group
;

####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 1898556'
loop_
_audit_author_name
_audit_author_address
'Jacques Pecaut '
;CEA Grenoble
France
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_audit_creation_date             2019-02-20
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H35 Cl N3 O2, F6 P'
_chemical_formula_sum            'C22 H35 Cl F6 N3 O2 P'
_chemical_formula_weight         553.95
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H50 N3 O2 P F6 Cl'
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'
Cl Cl 0.1484 0.1585 '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'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.7678(13)
_cell_length_b                   11.6389(10)
_cell_length_c                   36.278(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.051(7)
_cell_angle_gamma                90
_cell_volume                     5377.6(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    602
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      19.4960
_cell_measurement_theta_min      2.3620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.996
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2320
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0132
-1 0 0 0.0726
1 0 0 0.0666
0 -1 0 0.0393
0 1 0 0.0473
0 0 1 0.0042

_exptl_crystal_size_max          0.141
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.017
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0001 -0.0001 -1.0004 -0.0052 0.0106 -0.0156
-1.0003 -0.0008 0.0004 0.0472 0.0296 -0.0006
1.0003 0.0008 -0.0004 -0.0472 -0.0296 0.0006
-0.0000 -1.0010 -0.0014 -0.0254 0.0415 0.0367
0.0000 1.0010 0.0014 0.0254 -0.0415 -0.0367
-0.0001 0.0001 1.0004 0.0052 -0.0106 0.0156

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2429
_diffrn_reflns_av_unetI/netI     0.2667
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            36736
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.242
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9653
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.3681
_diffrn_measured_fraction_theta_max 0.9948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  68.00   1.00   60.00    --   -0.62  57.00-150.00   90
  2  ω    -15.00  86.00   1.00  270.00    --   55.51 -77.00-150.00  101
  3  ω     34.00 124.00   1.00  270.00    --   55.51  57.00   0.00   90
  4  ω     25.00 126.00   1.00  270.00    --   55.51  77.00  90.00  101
  5  ω    -77.00 -32.00   1.00   60.00    --   -0.62 178.00 -60.00   45
  6  ω     30.00  67.00   1.00  270.00    --   55.51  37.00 -90.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0472204000
_diffrn_orient_matrix_UB_12      0.0253998000
_diffrn_orient_matrix_UB_13      0.0052283000
_diffrn_orient_matrix_UB_21      -0.0295448000
_diffrn_orient_matrix_UB_22      -0.0414882000
_diffrn_orient_matrix_UB_23      -0.0106230000
_diffrn_orient_matrix_UB_31      0.0006424000
_diffrn_orient_matrix_UB_32      -0.0367017000
_diffrn_orient_matrix_UB_33      0.0156168000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3964
_reflns_number_total             10955
_reflns_odcompleteness_completeness 36.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     45.18
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     692
_refine_ls_number_reflns         10955
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.2373
_refine_ls_R_factor_gt           0.0847
_refine_ls_restrained_S_all      0.934
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.2095
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C20 \\sim C21 \\sim C20B \\sim C21B: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.01
F16B \\sim F15 \\sim F15B \\sim F16: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.01
3. Others
 Sof(C20B)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C21B)=Sof(H21D)=Sof(H21E)=
 Sof(H21F)=1-FVAR(1)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=
 FVAR(1)
 Fixed Sof: F15(0.5) F16(0.5) F15B(0.5) F16B(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C43(H43), C45(H45)
4.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,
 H8B,H8C), C9(H9A,H9B,H9C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C22(H22A,
 H22B,H22C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C20B(H20D,H20E,H20F),
 C21B(H21D,H21E,H21F), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C47(H47A,
 H47B,H47C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C),
 C52(H52A,H52B,H52C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
# end Validation Reply Form
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 0.53371(14) 0.18447(16) 0.30602(5) 0.0415(5) Uani 1 1 d . . . . .
O1 O 0.7962(4) 0.3611(7) 0.32190(13) 0.082(3) Uani 1 1 d . . . . .
O2 O 0.6369(3) 0.3730(4) 0.34273(10) 0.0282(10) Uani 1 1 d . . . . .
N1 N 0.6346(4) 0.5999(5) 0.31572(13) 0.0273(12) Uani 1 1 d . . . . .
N2 N 0.6623(4) 0.5200(5) 0.25827(13) 0.0269(12) Uani 1 1 d . . . . .
N3 N 0.4667(4) 0.3391(5) 0.25840(13) 0.0318(13) Uani 1 1 d . . . . .
C1 C 0.6305(5) 0.5096(6) 0.29295(16) 0.0261(15) Uani 1 1 d . . . . .
C2 C 0.5972(5) 0.4004(5) 0.30639(15) 0.0228(14) Uani 1 1 d . . . . .
C3 C 0.5343(5) 0.3232(6) 0.28817(15) 0.0255(14) Uani 1 1 d . . . . .
C4 C 0.5629(5) 0.6084(6) 0.34604(16) 0.0301(15) Uani 1 1 d . . . . .
H4A H 0.517172 0.542820 0.345327 0.045 Uiso 1 1 calc GR . . . .
H4B H 0.521779 0.677212 0.343057 0.045 Uiso 1 1 calc GR . . . .
H4C H 0.603389 0.610550 0.369357 0.045 Uiso 1 1 calc GR . . . .
C5 C 0.7050(6) 0.6983(7) 0.31358(18) 0.0403(18) Uani 1 1 d . . . . .
H5A H 0.667436 0.761383 0.301857 0.060 Uiso 1 1 calc GR . . . .
H5B H 0.762937 0.677730 0.299435 0.060 Uiso 1 1 calc GR . . . .
H5C H 0.730844 0.720343 0.338052 0.060 Uiso 1 1 calc GR . . . .
C6 C 0.6563(6) 0.6249(6) 0.23652(17) 0.0366(17) Uani 1 1 d . . . . .
H6A H 0.725081 0.658106 0.236155 0.055 Uiso 1 1 calc GR . . . .
H6B H 0.610123 0.678346 0.247312 0.055 Uiso 1 1 calc GR . . . .
H6C H 0.629907 0.607460 0.211721 0.055 Uiso 1 1 calc GR . . . .
C7 C 0.7030(5) 0.4207(6) 0.23891(17) 0.0326(16) Uani 1 1 d . . . . .
H7A H 0.649346 0.391405 0.221542 0.049 Uiso 1 1 calc GR . . . .
H7B H 0.723630 0.361877 0.256518 0.049 Uiso 1 1 calc GR . . . .
H7C H 0.762684 0.443693 0.226019 0.049 Uiso 1 1 calc GR . . . .
C8 C 0.4318(5) 0.4542(6) 0.24667(18) 0.0355(17) Uani 1 1 d . . . . .
H8A H 0.469903 0.478530 0.226165 0.053 Uiso 1 1 calc GR . . . .
H8B H 0.444463 0.507105 0.266806 0.053 Uiso 1 1 calc GR . . . .
H8C H 0.358035 0.452507 0.239361 0.053 Uiso 1 1 calc GR . . . .
C9 C 0.4199(6) 0.2445(7) 0.23686(18) 0.045(2) Uani 1 1 d . . . . .
H9A H 0.359521 0.216631 0.248435 0.068 Uiso 1 1 calc GR . . . .
H9B H 0.470248 0.183692 0.235548 0.068 Uiso 1 1 calc GR . . . .
H9C H 0.398942 0.270860 0.212359 0.068 Uiso 1 1 calc GR . . . .
C10 C 0.7421(5) 0.3573(7) 0.34712(18) 0.0367(18) Uani 1 1 d . . . . .
C11 C 0.7793(5) 0.3305(7) 0.38649(16) 0.0334(17) Uani 1 1 d . . . . .
C12 C 0.7790(5) 0.2175(7) 0.39851(18) 0.0407(19) Uani 1 1 d . . . . .
C13 C 0.8177(5) 0.1960(8) 0.43481(18) 0.0435(19) Uani 1 1 d . . . . .
H13 H 0.819039 0.120373 0.443130 0.052 Uiso 1 1 calc R . . . .
C14 C 0.8544(6) 0.2815(8) 0.45920(19) 0.045(2) Uani 1 1 d . . . . .
C15 C 0.8562(5) 0.3919(8) 0.44534(18) 0.047(2) Uani 1 1 d . . . . .
H15 H 0.883457 0.450294 0.460644 0.057 Uiso 1 1 calc R . . . .
C16 C 0.8183(5) 0.4199(7) 0.40895(18) 0.0415(19) Uani 1 1 d . . . . .
C17 C 0.7415(6) 0.1210(8) 0.3743(2) 0.049(2) Uani 1 1 d . . . . .
H17A H 0.769163 0.129159 0.350524 0.073 Uiso 1 1 calc GR . . . .
H17B H 0.666140 0.121998 0.371499 0.073 Uiso 1 1 calc GR . . . .
H17C H 0.764810 0.049571 0.385245 0.073 Uiso 1 1 calc GR . . . .
C18 C 0.8923(6) 0.2540(8) 0.4991(2) 0.056(2) Uani 1 1 d . . . . .
C19 C 0.8127(9) 0.1802(11) 0.5164(2) 0.087(4) Uani 1 1 d . . . . .
H19A H 0.746210 0.219103 0.515256 0.131 Uiso 1 1 calc GR . . . .
H19B H 0.835465 0.165704 0.541806 0.131 Uiso 1 1 calc GR . . . .
H19C H 0.805442 0.108623 0.503365 0.131 Uiso 1 1 calc GR . . . .
C22 C 0.8244(6) 0.5425(7) 0.39623(19) 0.048(2) Uani 1 1 d . . . . .
H22A H 0.760962 0.582023 0.401282 0.072 Uiso 1 1 calc GR . . . .
H22B H 0.832834 0.544203 0.370152 0.072 Uiso 1 1 calc GR . . . .
H22C H 0.883265 0.579684 0.409147 0.072 Uiso 1 1 calc GR . . . .
C20 C 0.9996(16) 0.210(2) 0.5003(5) 0.084(5) Uani 0.618(18) 1 d . U P A 1
H20A H 1.001750 0.142765 0.485011 0.126 Uiso 0.618(18) 1 calc GR . P A 1
H20B H 1.022439 0.190255 0.525306 0.126 Uiso 0.618(18) 1 calc GR . P A 1
H20C H 1.045227 0.267674 0.491428 0.126 Uiso 0.618(18) 1 calc GR . P A 1
C21 C 0.8887(16) 0.3696(16) 0.5246(4) 0.066(5) Uani 0.618(18) 1 d . U P A 1
H21A H 0.933183 0.427376 0.515099 0.099 Uiso 0.618(18) 1 calc GR . P A 1
H21B H 0.912795 0.351453 0.549561 0.099 Uiso 0.618(18) 1 calc GR . P A 1
H21C H 0.817905 0.397712 0.524021 0.099 Uiso 0.618(18) 1 calc GR . P A 1
C20B C 0.978(3) 0.136(3) 0.4957(8) 0.078(6) Uani 0.382(18) 1 d . U P A 2
H20D H 0.938868 0.069183 0.487622 0.116 Uiso 0.382(18) 1 calc GR . P A 2
H20E H 1.013817 0.120946 0.519473 0.116 Uiso 0.382(18) 1 calc GR . P A 2
H20F H 1.029185 0.153225 0.478249 0.116 Uiso 0.382(18) 1 calc GR . P A 2
C21B C 0.956(3) 0.334(3) 0.5154(7) 0.077(5) Uani 0.382(18) 1 d . U P A 2
H21D H 1.010363 0.353233 0.499377 0.116 Uiso 0.382(18) 1 calc GR . P A 2
H21E H 0.987551 0.304606 0.538305 0.116 Uiso 0.382(18) 1 calc GR . P A 2
H21F H 0.916314 0.401850 0.520146 0.116 Uiso 0.382(18) 1 calc GR . P A 2
Cl2 Cl 0.46862(12) 0.19172(16) 0.40393(4) 0.0381(4) Uani 1 1 d . . . . .
O31 O 0.3021(4) 0.4183(5) 0.44069(12) 0.0471(14) Uani 1 1 d . . . . .
O32 O 0.3810(3) 0.4135(4) 0.38702(10) 0.0278(10) Uani 1 1 d . . . . .
N31 N 0.1911(4) 0.4498(5) 0.34349(14) 0.0324(13) Uani 1 1 d . . . . .
N32 N 0.1252(4) 0.2905(5) 0.37351(14) 0.0328(14) Uani 1 1 d . . . . .
N33 N 0.3117(4) 0.1189(5) 0.36090(14) 0.0318(13) Uani 1 1 d . . . . .
C31 C 0.2064(5) 0.3538(6) 0.36386(15) 0.0246(14) Uani 1 1 d . . . . .
C32 C 0.3128(4) 0.3220(6) 0.37591(15) 0.0238(14) Uani 1 1 d . . . . .
C33 C 0.3512(5) 0.2144(6) 0.37779(15) 0.0284(15) Uani 1 1 d . . . . .
C34 C 0.2682(6) 0.4915(7) 0.31925(18) 0.0427(19) Uani 1 1 d . . . . .
H34A H 0.322058 0.434719 0.317339 0.064 Uiso 1 1 calc GR . . . .
H34B H 0.298945 0.561243 0.329165 0.064 Uiso 1 1 calc GR . . . .
H34C H 0.234701 0.506327 0.295191 0.064 Uiso 1 1 calc GR . . . .
C35 C 0.0946(6) 0.5197(7) 0.3445(2) 0.051(2) Uani 1 1 d . . . . .
H35A H 0.061789 0.504348 0.367037 0.076 Uiso 1 1 calc GR . . . .
H35B H 0.046996 0.500471 0.323788 0.076 Uiso 1 1 calc GR . . . .
H35C H 0.112353 0.599742 0.343484 0.076 Uiso 1 1 calc GR . . . .
C36 C 0.0263(5) 0.2816(8) 0.3503(2) 0.050(2) Uani 1 1 d . . . . .
H36A H 0.036627 0.310113 0.325984 0.075 Uiso 1 1 calc GR . . . .
H36B H -0.027001 0.326160 0.361034 0.075 Uiso 1 1 calc GR . . . .
H36C H 0.004715 0.202616 0.348694 0.075 Uiso 1 1 calc GR . . . .
C37 C 0.1294(6) 0.2193(7) 0.40683(18) 0.0443(19) Uani 1 1 d . . . . .
H37A H 0.189489 0.240536 0.422783 0.066 Uiso 1 1 calc GR . . . .
H37B H 0.134895 0.139865 0.400051 0.066 Uiso 1 1 calc GR . . . .
H37C H 0.066733 0.230636 0.419491 0.066 Uiso 1 1 calc GR . . . .
C38 C 0.2442(5) 0.1273(7) 0.32630(17) 0.0384(18) Uani 1 1 d . . . . .
H38A H 0.250054 0.202892 0.316067 0.058 Uiso 1 1 calc GR . . . .
H38B H 0.172567 0.113044 0.331358 0.058 Uiso 1 1 calc GR . . . .
H38C H 0.266062 0.071413 0.308952 0.058 Uiso 1 1 calc GR . . . .
C39 C 0.3363(7) 0.0031(7) 0.3730(2) 0.052(2) Uani 1 1 d . . . . .
H39A H 0.346701 0.001487 0.399437 0.078 Uiso 1 1 calc GR . . . .
H39B H 0.399142 -0.022108 0.362386 0.078 Uiso 1 1 calc GR . . . .
H39C H 0.279280 -0.047026 0.365129 0.078 Uiso 1 1 calc GR . . . .
C40 C 0.3658(5) 0.4559(6) 0.42153(17) 0.0321(16) Uani 1 1 d . . . . .
C41 C 0.4392(5) 0.5534(6) 0.43046(16) 0.0259(14) Uani 1 1 d . . . . .
C42 C 0.5360(5) 0.5332(6) 0.45089(16) 0.0294(15) Uani 1 1 d . . . . .
C43 C 0.5988(5) 0.6279(6) 0.46071(16) 0.0320(16) Uani 1 1 d . . . . .
H43 H 0.663140 0.615205 0.473751 0.038 Uiso 1 1 calc R . . . .
C44 C 0.5699(5) 0.7405(6) 0.45193(17) 0.0322(16) Uani 1 1 d . . . . .
C45 C 0.4735(5) 0.7561(7) 0.43192(18) 0.0356(17) Uani 1 1 d . . . . .
H45 H 0.452327 0.830329 0.425533 0.043 Uiso 1 1 calc R . . . .
C46 C 0.4081(5) 0.6648(6) 0.42116(16) 0.0306(16) Uani 1 1 d . . . . .
C47 C 0.5732(5) 0.4153(6) 0.46174(18) 0.0362(17) Uani 1 1 d . . . . .
H47A H 0.607297 0.381063 0.441692 0.054 Uiso 1 1 calc GR . . . .
H47B H 0.514311 0.368880 0.467423 0.054 Uiso 1 1 calc GR . . . .
H47C H 0.621947 0.420177 0.483086 0.054 Uiso 1 1 calc GR . . . .
C48 C 0.6413(5) 0.8411(6) 0.46440(17) 0.0330(16) Uani 1 1 d . . . . .
C49 C 0.6567(9) 0.8408(8) 0.5070(2) 0.079(3) Uani 1 1 d . . . . .
H49A H 0.694404 0.772957 0.515094 0.118 Uiso 1 1 calc GR . . . .
H49B H 0.589356 0.841582 0.517234 0.118 Uiso 1 1 calc GR . . . .
H49C H 0.695780 0.907640 0.515159 0.118 Uiso 1 1 calc GR . . . .
C50 C 0.7448(7) 0.8285(9) 0.4471(3) 0.072(3) Uani 1 1 d . . . . .
H50A H 0.732373 0.821747 0.420818 0.108 Uiso 1 1 calc GR . . . .
H50B H 0.780164 0.760866 0.456710 0.108 Uiso 1 1 calc GR . . . .
H50C H 0.787584 0.894737 0.452904 0.108 Uiso 1 1 calc GR . . . .
C51 C 0.5928(6) 0.9581(7) 0.4530(2) 0.055(2) Uani 1 1 d . . . . .
H51A H 0.528316 0.968431 0.464715 0.082 Uiso 1 1 calc GR . . . .
H51B H 0.579021 0.960444 0.426682 0.082 Uiso 1 1 calc GR . . . .
H51C H 0.640895 1.018462 0.460610 0.082 Uiso 1 1 calc GR . . . .
C52 C 0.3057(5) 0.6897(7) 0.39900(19) 0.0415(18) Uani 1 1 d . . . . .
H52A H 0.260459 0.623937 0.399653 0.062 Uiso 1 1 calc GR . . . .
H52B H 0.319525 0.706082 0.373867 0.062 Uiso 1 1 calc GR . . . .
H52C H 0.272264 0.754720 0.409414 0.062 Uiso 1 1 calc GR . . . .
P2 P -0.00546(18) 0.8695(2) 0.36766(5) 0.0477(5) Uani 1 1 d . . . . .
F11 F 0.0172(6) 0.7600(5) 0.39239(15) 0.112(3) Uani 1 1 d . . . . .
F12 F -0.0214(5) 0.9788(6) 0.34187(15) 0.096(2) Uani 1 1 d . . . . .
F13 F 0.1074(5) 0.8573(7) 0.3510(2) 0.120(3) Uani 1 1 d . . . . .
F14 F -0.0450(5) 0.7870(6) 0.33455(14) 0.098(2) Uani 1 1 d . . . . .
F15 F -0.1032(12) 0.8768(13) 0.3877(3) 0.086(3) Uani 0.5 1 d . U P B 1
F16 F 0.0716(12) 0.9381(10) 0.3975(3) 0.079(3) Uani 0.5 1 d . U P B 1
F15B F -0.1376(10) 0.8708(12) 0.3651(4) 0.088(4) Uani 0.5 1 d . U P B 2
F16B F -0.0126(13) 0.9597(12) 0.3994(3) 0.090(3) Uani 0.5 1 d . U P B 2
P1 P 0.41040(15) 0.84794(18) 0.27116(5) 0.0388(5) Uani 1 1 d . . . . .
F1 F 0.3739(4) 0.9776(4) 0.26508(13) 0.0640(14) Uani 1 1 d . . . . .
F2 F 0.4451(4) 0.7179(4) 0.27732(13) 0.0665(14) Uani 1 1 d . . . . .
F3 F 0.4888(4) 0.8860(5) 0.30468(12) 0.0641(14) Uani 1 1 d . . . . .
F4 F 0.5009(4) 0.8660(5) 0.24388(13) 0.0738(15) Uani 1 1 d . . . . .
F5 F 0.3320(4) 0.8105(4) 0.23724(11) 0.0636(14) Uani 1 1 d . . . . .
F6 F 0.3195(3) 0.8312(5) 0.29820(12) 0.0640(14) 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
Cl1 C3 1.740(7) . ?
O1 C10 1.186(8) . ?
O2 C2 1.415(6) . ?
O2 C10 1.353(7) . ?
N1 C1 1.335(8) . ?
N1 C4 1.483(8) . ?
N1 C5 1.461(9) . ?
N2 C1 1.355(8) . ?
N2 C6 1.452(8) . ?
N2 C7 1.467(8) . ?
N3 C3 1.346(7) . ?
N3 C8 1.467(9) . ?
N3 C9 1.454(9) . ?
C1 C2 1.436(9) . ?
C2 C3 1.347(9) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.506(9) . ?
C11 C12 1.386(11) . ?
C11 C16 1.392(11) . ?
C12 C13 1.396(9) . ?
C12 C17 1.484(11) . ?
C13 H13 0.9300 . ?
C13 C14 1.391(11) . ?
C14 C15 1.380(12) . ?
C14 C18 1.528(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.412(9) . ?
C16 C22 1.503(11) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.503(12) . ?
C18 C20 1.46(2) . ?
C18 C21 1.63(2) . ?
C18 C20B 1.77(4) . ?
C18 C21B 1.35(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
Cl2 C33 1.736(6) . ?
O31 C40 1.190(8) . ?
O32 C32 1.416(7) . ?
O32 C40 1.372(7) . ?
N31 C31 1.346(8) . ?
N31 C34 1.450(9) . ?
N31 C35 1.479(9) . ?
N32 C31 1.338(8) . ?
N32 C36 1.471(8) . ?
N32 C37 1.464(9) . ?
N33 C33 1.350(9) . ?
N33 C38 1.475(8) . ?
N33 C39 1.444(10) . ?
C31 C32 1.445(8) . ?
C32 C33 1.345(9) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 C41 1.492(10) . ?
C41 C42 1.415(9) . ?
C41 C46 1.391(9) . ?
C42 C43 1.394(10) . ?
C42 C47 1.496(10) . ?
C43 H43 0.9300 . ?
C43 C44 1.393(10) . ?
C44 C45 1.395(9) . ?
C44 C48 1.533(10) . ?
C45 H45 0.9300 . ?
C45 C46 1.391(10) . ?
C46 C52 1.513(9) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 C49 1.544(10) . ?
C48 C50 1.508(11) . ?
C48 C51 1.541(11) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
P2 F11 1.573(6) . ?
P2 F12 1.584(6) . ?
P2 F13 1.608(7) . ?
P2 F14 1.592(6) . ?
P2 F15 1.491(13) . ?
P2 F16 1.620(11) . ?
P2 F15B 1.683(13) . ?
P2 F16B 1.564(12) . ?
P1 F1 1.590(5) . ?
P1 F2 1.588(5) . ?
P1 F3 1.583(4) . ?
P1 F4 1.587(5) . ?
P1 F5 1.591(4) . ?
P1 F6 1.584(5) . ?

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
C10 O2 C2 115.3(5) . . ?
C1 N1 C4 120.8(5) . . ?
C1 N1 C5 125.6(6) . . ?
C5 N1 C4 113.7(5) . . ?
C1 N2 C6 124.9(6) . . ?
C1 N2 C7 120.9(5) . . ?
C6 N2 C7 114.1(5) . . ?
C3 N3 C8 121.5(5) . . ?
C3 N3 C9 122.9(6) . . ?
C9 N3 C8 115.5(5) . . ?
N1 C1 N2 120.2(6) . . ?
N1 C1 C2 119.1(5) . . ?
N2 C1 C2 120.7(6) . . ?
O2 C2 C1 114.9(5) . . ?
C3 C2 O2 118.0(5) . . ?
C3 C2 C1 127.2(5) . . ?
N3 C3 Cl1 114.0(5) . . ?
N3 C3 C2 128.9(6) . . ?
C2 C3 Cl1 117.0(4) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 O2 122.1(5) . . ?
O1 C10 C11 125.3(6) . . ?
O2 C10 C11 112.6(5) . . ?
C12 C11 C10 119.2(7) . . ?
C12 C11 C16 122.3(6) . . ?
C16 C11 C10 118.5(7) . . ?
C11 C12 C13 117.3(7) . . ?
C11 C12 C17 122.7(6) . . ?
C13 C12 C17 120.0(8) . . ?
C12 C13 H13 118.2 . . ?
C14 C13 C12 123.5(8) . . ?
C14 C13 H13 118.2 . . ?
C13 C14 C18 121.5(8) . . ?
C15 C14 C13 116.6(6) . . ?
C15 C14 C18 121.8(8) . . ?
C14 C15 H15 118.6 . . ?
C14 C15 C16 122.9(8) . . ?
C16 C15 H15 118.6 . . ?
C11 C16 C15 117.3(7) . . ?
C11 C16 C22 123.7(6) . . ?
C15 C16 C22 119.0(7) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 C21 110.1(8) . . ?
C14 C18 C20B 104.7(11) . . ?
C19 C18 C14 109.8(6) . . ?
C19 C18 C21 100.8(9) . . ?
C19 C18 C20B 91.5(15) . . ?
C20 C18 C14 109.6(9) . . ?
C20 C18 C19 116.6(13) . . ?
C20 C18 C21 109.6(11) . . ?
C21B C18 C14 114.4(13) . . ?
C21B C18 C19 128.2(15) . . ?
C21B C18 C20B 102.0(17) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C20B H20D 109.5 . . ?
C18 C20B H20E 109.5 . . ?
C18 C20B H20F 109.5 . . ?
H20D C20B H20E 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C18 C21B H21D 109.5 . . ?
C18 C21B H21E 109.5 . . ?
C18 C21B H21F 109.5 . . ?
H21D C21B H21E 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C40 O32 C32 114.0(5) . . ?
C31 N31 C34 122.2(6) . . ?
C31 N31 C35 122.1(6) . . ?
C34 N31 C35 115.7(6) . . ?
C31 N32 C36 122.6(6) . . ?
C31 N32 C37 122.9(5) . . ?
C37 N32 C36 114.4(6) . . ?
C33 N33 C38 120.6(6) . . ?
C33 N33 C39 124.4(5) . . ?
C39 N33 C38 114.9(6) . . ?
N31 C31 C32 118.4(6) . . ?
N32 C31 N31 121.0(5) . . ?
N32 C31 C32 120.6(6) . . ?
O32 C32 C31 116.1(5) . . ?
C33 C32 O32 118.1(5) . . ?
C33 C32 C31 125.9(6) . . ?
N33 C33 Cl2 113.8(5) . . ?
C32 C33 Cl2 117.9(5) . . ?
C32 C33 N33 128.3(5) . . ?
N31 C34 H34A 109.5 . . ?
N31 C34 H34B 109.5 . . ?
N31 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N31 C35 H35A 109.5 . . ?
N31 C35 H35B 109.5 . . ?
N31 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N32 C36 H36A 109.5 . . ?
N32 C36 H36B 109.5 . . ?
N32 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N32 C37 H37A 109.5 . . ?
N32 C37 H37B 109.5 . . ?
N32 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N33 C38 H38A 109.5 . . ?
N33 C38 H38B 109.5 . . ?
N33 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N33 C39 H39A 109.5 . . ?
N33 C39 H39B 109.5 . . ?
N33 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O31 C40 O32 123.2(6) . . ?
O31 C40 C41 126.7(6) . . ?
O32 C40 C41 110.1(6) . . ?
C42 C41 C40 120.0(6) . . ?
C46 C41 C40 119.4(5) . . ?
C46 C41 C42 120.4(6) . . ?
C41 C42 C47 122.7(6) . . ?
C43 C42 C41 117.9(6) . . ?
C43 C42 C47 119.4(5) . . ?
C42 C43 H43 118.4 . . ?
C44 C43 C42 123.1(6) . . ?
C44 C43 H43 118.4 . . ?
C43 C44 C45 116.8(7) . . ?
C43 C44 C48 120.6(6) . . ?
C45 C44 C48 122.6(6) . . ?
C44 C45 H45 118.8 . . ?
C46 C45 C44 122.5(7) . . ?
C46 C45 H45 118.8 . . ?
C41 C46 C52 121.9(6) . . ?
C45 C46 C41 119.2(6) . . ?
C45 C46 C52 118.9(6) . . ?
C42 C47 H47A 109.5 . . ?
C42 C47 H47B 109.5 . . ?
C42 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C44 C48 C49 108.9(6) . . ?
C44 C48 C51 112.1(5) . . ?
C50 C48 C44 108.9(6) . . ?
C50 C48 C49 111.3(7) . . ?
C50 C48 C51 108.8(7) . . ?
C51 C48 C49 106.9(7) . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C48 C50 H50A 109.5 . . ?
C48 C50 H50B 109.5 . . ?
C48 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C48 C51 H51A 109.5 . . ?
C48 C51 H51B 109.5 . . ?
C48 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C46 C52 H52A 109.5 . . ?
C46 C52 H52B 109.5 . . ?
C46 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
F11 P2 F12 176.5(4) . . ?
F11 P2 F13 90.5(4) . . ?
F11 P2 F14 88.7(3) . . ?
F11 P2 F16 86.6(4) . . ?
F11 P2 F15B 100.5(6) . . ?
F12 P2 F13 86.0(4) . . ?
F12 P2 F14 91.0(3) . . ?
F12 P2 F16 92.6(5) . . ?
F12 P2 F15B 82.7(6) . . ?
F13 P2 F16 77.1(6) . . ?
F13 P2 F15B 154.4(6) . . ?
F14 P2 F13 84.7(4) . . ?
F14 P2 F16 161.1(6) . . ?
F14 P2 F15B 72.6(5) . . ?
F15 P2 F11 83.9(6) . . ?
F15 P2 F12 99.5(6) . . ?
F15 P2 F13 172.7(6) . . ?
F15 P2 F14 99.9(6) . . ?
F15 P2 F16 97.8(8) . . ?
F16B P2 F11 98.2(6) . . ?
F16B P2 F12 83.3(6) . . ?
F16B P2 F13 115.9(7) . . ?
F16B P2 F14 158.0(7) . . ?
F16B P2 F15B 85.6(7) . . ?
F1 P1 F5 89.5(3) . . ?
F2 P1 F1 179.1(3) . . ?
F2 P1 F5 90.1(3) . . ?
F3 P1 F1 90.2(3) . . ?
F3 P1 F2 90.2(3) . . ?
F3 P1 F4 89.6(3) . . ?
F3 P1 F5 179.5(3) . . ?
F3 P1 F6 90.6(3) . . ?
F4 P1 F1 90.4(3) . . ?
F4 P1 F2 90.3(3) . . ?
F4 P1 F5 90.0(3) . . ?
F6 P1 F1 89.0(3) . . ?
F6 P1 F2 90.3(3) . . ?
F6 P1 F4 179.4(3) . . ?
F6 P1 F5 89.8(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
O1 C10 C11 C12 -90.9(10) . . . . ?
O1 C10 C11 C16 85.5(11) . . . . ?
O2 C2 C3 Cl1 -15.5(8) . . . . ?
O2 C2 C3 N3 161.2(6) . . . . ?
O2 C10 C11 C12 86.8(8) . . . . ?
O2 C10 C11 C16 -96.8(8) . . . . ?
N1 C1 C2 O2 -40.9(8) . . . . ?
N1 C1 C2 C3 139.7(7) . . . . ?
N2 C1 C2 O2 135.8(5) . . . . ?
N2 C1 C2 C3 -43.6(9) . . . . ?
C1 C2 C3 Cl1 164.0(5) . . . . ?
C1 C2 C3 N3 -19.4(11) . . . . ?
C2 O2 C10 O1 -3.2(11) . . . . ?
C2 O2 C10 C11 179.0(6) . . . . ?
C4 N1 C1 N2 153.9(5) . . . . ?
C4 N1 C1 C2 -29.4(8) . . . . ?
C5 N1 C1 N2 -24.9(9) . . . . ?
C5 N1 C1 C2 151.8(6) . . . . ?
C6 N2 C1 N1 -29.9(9) . . . . ?
C6 N2 C1 C2 153.4(6) . . . . ?
C7 N2 C1 N1 152.6(6) . . . . ?
C7 N2 C1 C2 -24.1(8) . . . . ?
C8 N3 C3 Cl1 160.6(5) . . . . ?
C8 N3 C3 C2 -16.2(10) . . . . ?
C9 N3 C3 Cl1 -16.5(8) . . . . ?
C9 N3 C3 C2 166.8(7) . . . . ?
C10 O2 C2 C1 -66.0(7) . . . . ?
C10 O2 C2 C3 113.5(7) . . . . ?
C10 C11 C12 C13 177.7(6) . . . . ?
C10 C11 C12 C17 -1.2(10) . . . . ?
C10 C11 C16 C15 -177.8(6) . . . . ?
C10 C11 C16 C22 0.7(10) . . . . ?
C11 C12 C13 C14 1.0(10) . . . . ?
C12 C11 C16 C15 -1.5(10) . . . . ?
C12 C11 C16 C22 177.1(7) . . . . ?
C12 C13 C14 C15 -3.2(11) . . . . ?
C12 C13 C14 C18 177.7(7) . . . . ?
C13 C14 C15 C16 3.1(11) . . . . ?
C13 C14 C18 C19 -48.9(11) . . . . ?
C13 C14 C18 C20 80.3(14) . . . . ?
C13 C14 C18 C21 -159.0(10) . . . . ?
C13 C14 C18 C20B 48.2(16) . . . . ?
C13 C14 C18 C21B 159(2) . . . . ?
C14 C15 C16 C11 -0.9(11) . . . . ?
C14 C15 C16 C22 -179.5(7) . . . . ?
C15 C14 C18 C19 132.0(9) . . . . ?
C15 C14 C18 C20 -98.7(15) . . . . ?
C15 C14 C18 C21 22.0(13) . . . . ?
C15 C14 C18 C20B -130.9(16) . . . . ?
C15 C14 C18 C21B -20(2) . . . . ?
C16 C11 C12 C13 1.4(10) . . . . ?
C16 C11 C12 C17 -177.5(6) . . . . ?
C17 C12 C13 C14 179.9(7) . . . . ?
C18 C14 C15 C16 -177.8(7) . . . . ?
O31 C40 C41 C42 85.2(9) . . . . ?
O31 C40 C41 C46 -89.6(9) . . . . ?
O32 C32 C33 Cl2 15.7(8) . . . . ?
O32 C32 C33 N33 -162.3(6) . . . . ?
O32 C40 C41 C42 -95.0(7) . . . . ?
O32 C40 C41 C46 90.1(7) . . . . ?
N31 C31 C32 O32 39.0(7) . . . . ?
N31 C31 C32 C33 -141.8(7) . . . . ?
N32 C31 C32 O32 -139.5(6) . . . . ?
N32 C31 C32 C33 39.7(9) . . . . ?
C31 C32 C33 Cl2 -163.5(5) . . . . ?
C31 C32 C33 N33 18.5(11) . . . . ?
C32 O32 C40 O31 1.0(9) . . . . ?
C32 O32 C40 C41 -178.7(5) . . . . ?
C34 N31 C31 N32 -152.1(6) . . . . ?
C34 N31 C31 C32 29.5(8) . . . . ?
C35 N31 C31 N32 28.2(9) . . . . ?
C35 N31 C31 C32 -150.2(6) . . . . ?
C36 N32 C31 N31 31.1(9) . . . . ?
C36 N32 C31 C32 -150.5(6) . . . . ?
C37 N32 C31 N31 -152.7(6) . . . . ?
C37 N32 C31 C32 25.8(9) . . . . ?
C38 N33 C33 Cl2 -152.7(5) . . . . ?
C38 N33 C33 C32 25.4(10) . . . . ?
C39 N33 C33 Cl2 23.0(9) . . . . ?
C39 N33 C33 C32 -159.0(7) . . . . ?
C40 O32 C32 C31 76.9(6) . . . . ?
C40 O32 C32 C33 -102.3(6) . . . . ?
C40 C41 C42 C43 -175.7(6) . . . . ?
C40 C41 C42 C47 5.0(9) . . . . ?
C40 C41 C46 C45 175.3(6) . . . . ?
C40 C41 C46 C52 -5.9(9) . . . . ?
C41 C42 C43 C44 1.1(9) . . . . ?
C42 C41 C46 C45 0.5(9) . . . . ?
C42 C41 C46 C52 179.3(6) . . . . ?
C42 C43 C44 C45 -0.8(10) . . . . ?
C42 C43 C44 C48 178.4(6) . . . . ?
C43 C44 C45 C46 0.4(10) . . . . ?
C43 C44 C48 C49 -59.9(9) . . . . ?
C43 C44 C48 C50 61.6(8) . . . . ?
C43 C44 C48 C51 -177.9(6) . . . . ?
C44 C45 C46 C41 -0.2(10) . . . . ?
C44 C45 C46 C52 -179.1(6) . . . . ?
C45 C44 C48 C49 119.4(8) . . . . ?
C45 C44 C48 C50 -119.1(8) . . . . ?
C45 C44 C48 C51 1.3(9) . . . . ?
C46 C41 C42 C43 -1.0(9) . . . . ?
C46 C41 C42 C47 179.8(6) . . . . ?
C47 C42 C43 C44 -179.6(6) . . . . ?
C48 C44 C45 C46 -178.9(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.054
_oxdiff_exptl_absorpt_empirical_full_min 0.967
# start Validation Reply Form
_vrf_PLAT413_1c                  
;
PROBLEM: Short Inter XH3 .. XHn H19C ..H20D . 1.89 Ang.
RESPONSE: H19c and H20d belong to a disordered terbutyl group
;

####################################################################### 
# 
# 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_8adl
_database_code_depnum_ccdc_archive 'CCDC 1898561'
loop_
_audit_author_name
_audit_author_address
'Jacques Pecaut '
;CEA Grenoble
France
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_audit_creation_date             2019-02-11
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C32 H46 N6 O4, 2(F6 P), 0.5(C2 H3 N), 0.08(H2 O)'
_chemical_formula_sum            'C33 H47.66 F12 N6.50 O4.08 P2'
_chemical_formula_weight         890.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.1931(3)
_cell_length_b                   15.3991(4)
_cell_length_c                   22.7102(5)
_cell_angle_alpha                95.650(2)
_cell_angle_beta                 102.392(2)
_cell_angle_gamma                94.7722(19)
_cell_volume                     4120.62(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17228
_cell_measurement_temperature    149.95(10)
_cell_measurement_theta_max      29.6870
_cell_measurement_theta_min      2.4030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.996
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent pale yellow'
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1847
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.1092
0 -1 -1 0.1092
1 2 -2 0.0879
-1 -2 2 0.1659
1 1 0 0.1094
0 0 1 0.0882
0 0 -1 0.0882
1 -1 0 0.0925
-1 1 0 0.1411
0 1 -1 0.0747
-1 0 -1 0.1081
-1 0 1 0.1570

_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.176
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 1.0000 1.0000 -0.0367 -0.0405 -0.0240
0.0000 -1.0000 -1.0000 0.0367 0.0405 0.0240
1.0000 2.0000 -2.0000 -0.0591 -0.0677 0.0798
-1.0000 -2.0000 2.0000 0.0591 0.0677 -0.0798
1.0000 1.0000 0.0000 -0.0139 -0.0757 0.0207
0.0000 0.0000 1.0000 0.0028 -0.0162 -0.0277
-0.0000 -0.0000 -1.0000 -0.0028 0.0162 0.0277
1.0000 -1.0000 -0.0000 0.0652 -0.0271 0.0133
-1.0000 1.0000 0.0000 -0.0652 0.0271 -0.0133
-0.0000 1.0000 -1.0000 -0.0424 -0.0081 0.0314
-1.0000 -0.0000 -1.0000 -0.0285 0.0676 0.0107
-1.0000 0.0000 1.0000 -0.0228 0.0352 -0.0447

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            88692
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.149
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9653
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  -1.00   1.00    5.00    --   18.00 131.00 -58.44   42
  2  ω      9.00  39.00   1.00   15.00    --   45.45  88.00-147.44   30
  3  ω    -23.00  67.00   1.00   15.00    --   45.45 -57.00 150.00   90
  4  ω     -3.00 103.00   1.00   15.00    --   45.45-125.00 150.00  106
  5  ω      9.00  38.00   1.00   15.00    --   45.45  89.00  -8.21   29
  6  ω    -25.00  76.00   1.00   15.00    --   45.45 -77.00-120.00  101
  7  ω     20.00 118.00   1.00   15.00    --   45.45  37.00 -30.00   98
  8  ω      7.00  33.00   1.00   15.00    --   45.45  92.00 131.66   26
  9  ω      9.00  39.00   1.00   15.00    --   45.45  88.00  66.42   30
 10  ω     25.00 114.00   1.00   15.00    --   45.45  57.00-120.00   89
 11  ω     20.00 118.00   1.00   15.00    --   45.45  37.00  60.00   98
 12  ω      9.00  38.00   1.00   15.00    --   45.45  89.00 -89.01   29
 13  ω     25.00 114.00   1.00   15.00    --   45.45  57.00-180.00   89
 14  ω     20.00 118.00   1.00   15.00    --   45.45  37.00 150.00   98
 15  ω    -77.00  23.00   1.00   15.00    --  -46.70  77.00  30.00  100
 16  ω   -118.00 -73.00   1.00   15.00    --  -46.70-125.00 150.00   45
 17  ω   -118.00 -73.00   1.00   15.00    --  -46.70-125.00-150.00   45
 18  ω    -32.00   7.00   1.00    5.00    --   22.00 120.00 158.06   39
 19  ω      9.00  38.00   1.00   15.00    --   45.45  89.00 -29.75   29
 20  ω   -118.00 -73.00   1.00   15.00    --  -46.70-125.00  60.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0256379000
_diffrn_orient_matrix_UB_12      -0.0395276000
_diffrn_orient_matrix_UB_13      0.0028334000
_diffrn_orient_matrix_UB_21      -0.0514061000
_diffrn_orient_matrix_UB_22      -0.0243168000
_diffrn_orient_matrix_UB_23      -0.0161792000
_diffrn_orient_matrix_UB_31      0.0169955000
_diffrn_orient_matrix_UB_32      0.0036904000
_diffrn_orient_matrix_UB_33      -0.0277054000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                12757
_reflns_number_total             16766
_reflns_odcompleteness_completeness 48.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     40.15
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1122
_refine_ls_number_reflns         16766
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²+4.7619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1370
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
F13B \\sim F14B \\sim F15B \\sim F16B \\sim F13 \\sim F14 \\sim F15 \\sim F16:
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.01
C42B \\sim N41 \\sim C41 \\sim C42: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.01
3. Others
 Sof(F13)=Sof(F14)=Sof(F15)=Sof(F16)=1-FVAR(1)
 Sof(F13B)=Sof(F14B)=Sof(F15B)=Sof(F16B)=FVAR(1)
 Sof(C42B)=Sof(H42A)=Sof(H42B)=Sof(H42C)=1-FVAR(2)
 Sof(C42)=Sof(H42D)=Sof(H42E)=Sof(H42F)=FVAR(2)
 Sof(O1W)=Sof(H1WA)=Sof(H1WB)=FVAR(3)
4.a Free rotating group:
 O1W(H1WA,H1WB)
4.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C14(H14), C13(H13), C12(H12), C16'(H16'), C15'(H15'),
 C14'(H14'), C13'(H13'), C12'(H12'), C32(H32), C33(H33), C34(H34), C35(H35),
 C36(H36), C36'(H36'), C35'(H35'), C34'(H34'), C33'(H33'), C32'(H32')
4.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C8(H8A,H8B,H8C), C7(H7A,H7B,H7C), C4'(H4'A,H4'B,H4'C), C5'(H5'A,H5'B,H5'C),
 C10'(H10D,H10E,H10F), C9'(H9'A,H9'B,H9'C), C8'(H8'A,H8'B,H8'C), C7'(H7'A,H7'B,
 H7'C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C30(H30A,H30B,H30C), C29(H29A,
 H29B,H29C), C28(H28A,H28B,H28C), C27(H27A,H27B,H27C), C24'(H24D,H24E,H24F),
 C25'(H25D,H25E,H25F), C30'(H30D,H30E,H30F), C29'(H29D,H29E,H29F), C28'(H28D,
 H28E,H28F), C27'(H27D,H27E,H27F), C42B(H42A,H42B,H42C), C42(H42D,H42E,H42F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O2 O 0.88088(14) 0.48551(11) 0.74667(8) 0.0295(4) Uani 1 1 d . . . . .
O1 O 0.70700(14) 0.47579(11) 0.68148(8) 0.0293(4) Uani 1 1 d . . . . .
O2' O 0.84271(14) 0.34422(12) 0.65884(7) 0.0285(4) Uani 1 1 d . . . . .
O1' O 0.84835(14) 0.30124(11) 0.75328(7) 0.0263(4) Uani 1 1 d . . . . .
N1 N 0.72205(18) 0.59343(15) 0.62949(10) 0.0322(5) Uani 1 1 d . . . . .
N3 N 0.99589(18) 0.62642(14) 0.65342(10) 0.0295(5) Uani 1 1 d . . . . .
N2 N 1.05670(18) 0.62829(13) 0.75793(10) 0.0275(5) Uani 1 1 d . . . . .
N1' N 1.01251(19) 0.23690(14) 0.77162(10) 0.0323(5) Uani 1 1 d . . . . .
N3' N 1.13984(17) 0.34906(14) 0.67610(9) 0.0274(5) Uani 1 1 d . . . . .
N2' N 1.00210(18) 0.30776(14) 0.58764(9) 0.0283(5) Uani 1 1 d . . . . .
C1 C 0.7722(2) 0.43742(16) 0.73135(11) 0.0261(5) Uani 1 1 d . . . . .
C2 C 0.7725(2) 0.54539(16) 0.67044(11) 0.0241(5) Uani 1 1 d . . . . .
C3 C 0.8785(2) 0.55094(15) 0.70684(10) 0.0230(5) Uani 1 1 d . . . . .
C11 C 0.7171(2) 0.44507(16) 0.78495(12) 0.0311(6) Uani 1 1 d . . . . .
C16 C 0.6012(3) 0.44581(17) 0.77655(15) 0.0384(7) Uani 1 1 d . . . . .
H16 H 0.555799 0.438638 0.737508 0.046 Uiso 1 1 calc R . . . .
C15 C 0.5531(3) 0.45732(18) 0.82662(18) 0.0544(10) Uani 1 1 d . . . . .
H15 H 0.475440 0.458768 0.821030 0.065 Uiso 1 1 calc R . . . .
C14 C 0.6202(4) 0.46659(19) 0.88463(18) 0.0599(11) Uani 1 1 d . . . . .
H14 H 0.587879 0.474328 0.918056 0.072 Uiso 1 1 calc R . . . .
C13 C 0.7346(4) 0.4644(2) 0.89291(15) 0.0571(10) Uani 1 1 d . . . . .
H13 H 0.779521 0.470081 0.932037 0.068 Uiso 1 1 calc R . . . .
C12 C 0.7840(3) 0.45372(18) 0.84330(13) 0.0416(7) Uani 1 1 d . . . . .
H12 H 0.861688 0.452383 0.849208 0.050 Uiso 1 1 calc R . . . .
C4 C 0.6171(3) 0.5588(3) 0.58628(16) 0.0576(9) Uani 1 1 d . . . . .
H4A H 0.607862 0.496003 0.584102 0.086 Uiso 1 1 calc GR . . . .
H4B H 0.619802 0.575459 0.546927 0.086 Uiso 1 1 calc GR . . . .
H4C H 0.554624 0.582309 0.599385 0.086 Uiso 1 1 calc GR . . . .
C5 C 0.7606(3) 0.68629(19) 0.63062(15) 0.0455(8) Uani 1 1 d . . . . .
H5A H 0.817276 0.705386 0.667043 0.068 Uiso 1 1 calc GR . . . .
H5B H 0.697849 0.720320 0.629662 0.068 Uiso 1 1 calc GR . . . .
H5C H 0.791829 0.694074 0.595897 0.068 Uiso 1 1 calc GR . . . .
C6 C 0.9788(2) 0.60321(15) 0.70656(11) 0.0231(5) Uani 1 1 d . . . . .
C9 C 0.9556(2) 0.56825(19) 0.59648(12) 0.0356(6) Uani 1 1 d . . . . .
H9A H 1.015490 0.564616 0.575265 0.053 Uiso 1 1 calc GR . . . .
H9B H 0.893082 0.591172 0.571695 0.053 Uiso 1 1 calc GR . . . .
H9C H 0.931678 0.510810 0.605118 0.053 Uiso 1 1 calc GR . . . .
C10 C 1.0505(3) 0.71332(19) 0.64878(15) 0.0424(7) Uani 1 1 d . . . . .
H10A H 1.054465 0.751394 0.685453 0.064 Uiso 1 1 calc GR . . . .
H10B H 1.007308 0.737490 0.614941 0.064 Uiso 1 1 calc GR . . . .
H10C H 1.125385 0.707895 0.642908 0.064 Uiso 1 1 calc GR . . . .
C8 C 1.1765(2) 0.64922(19) 0.75921(14) 0.0366(6) Uani 1 1 d . . . . .
H8A H 1.191212 0.628176 0.720736 0.055 Uiso 1 1 calc GR . . . .
H8B H 1.221236 0.621571 0.790704 0.055 Uiso 1 1 calc GR . . . .
H8C H 1.195689 0.711651 0.767014 0.055 Uiso 1 1 calc GR . . . .
C7 C 1.0275(2) 0.63594(18) 0.81698(12) 0.0333(6) Uani 1 1 d . . . . .
H7A H 0.946836 0.628441 0.811492 0.050 Uiso 1 1 calc GR . . . .
H7B H 1.056586 0.692878 0.838413 0.050 Uiso 1 1 calc GR . . . .
H7C H 1.059781 0.591555 0.839967 0.050 Uiso 1 1 calc GR . . . .
C1' C 0.7816(2) 0.34200(16) 0.70525(11) 0.0241(5) Uani 1 1 d . . . . .
C2' C 0.9455(2) 0.28383(16) 0.73630(11) 0.0242(5) Uani 1 1 d . . . . .
C3' C 0.9481(2) 0.31432(16) 0.68212(11) 0.0242(5) Uani 1 1 d . . . . .
C11' C 0.6677(2) 0.28979(15) 0.68131(11) 0.0240(5) Uani 1 1 d . . . . .
C16' C 0.6093(2) 0.29379(17) 0.62206(12) 0.0284(5) Uani 1 1 d . . . . .
H16' H 0.642268 0.325487 0.596362 0.034 Uiso 1 1 calc R . . . .
C15' C 0.5015(2) 0.25027(18) 0.60154(13) 0.0337(6) Uani 1 1 d . . . . .
H15' H 0.462159 0.252784 0.561955 0.040 Uiso 1 1 calc R . . . .
C14' C 0.4523(2) 0.20295(17) 0.63986(14) 0.0344(6) Uani 1 1 d . . . . .
H14' H 0.379988 0.173762 0.625928 0.041 Uiso 1 1 calc R . . . .
C13' C 0.5104(2) 0.19919(17) 0.69864(13) 0.0321(6) Uani 1 1 d . . . . .
H13' H 0.477247 0.167613 0.724326 0.039 Uiso 1 1 calc R . . . .
C12' C 0.6183(2) 0.24239(16) 0.71946(12) 0.0270(5) Uani 1 1 d . . . . .
H12' H 0.657482 0.239593 0.759037 0.032 Uiso 1 1 calc R . . . .
C4' C 0.9982(3) 0.2227(2) 0.83217(12) 0.0422(7) Uani 1 1 d . . . . .
H4'A H 0.942699 0.258255 0.842805 0.063 Uiso 1 1 calc GR . . . .
H4'B H 1.068871 0.238646 0.860977 0.063 Uiso 1 1 calc GR . . . .
H4'C H 0.973676 0.161975 0.832605 0.063 Uiso 1 1 calc GR . . . .
C5' C 1.0960(3) 0.1900(2) 0.74784(15) 0.0459(8) Uani 1 1 d . . . . .
H5'A H 1.071538 0.177375 0.704516 0.069 Uiso 1 1 calc GR . . . .
H5'B H 1.104065 0.136126 0.765489 0.069 Uiso 1 1 calc GR . . . .
H5'C H 1.167318 0.225773 0.757872 0.069 Uiso 1 1 calc GR . . . .
C6' C 1.0323(2) 0.32319(15) 0.64802(11) 0.0230(5) Uani 1 1 d . . . . .
C10' C 1.1716(2) 0.40725(19) 0.73301(12) 0.0366(6) Uani 1 1 d . . . . .
H10D H 1.105319 0.429087 0.742711 0.055 Uiso 1 1 calc GR . . . .
H10E H 1.223381 0.455564 0.728920 0.055 Uiso 1 1 calc GR . . . .
H10F H 1.206992 0.375436 0.764896 0.055 Uiso 1 1 calc GR . . . .
C9' C 1.2355(2) 0.3217(2) 0.65158(14) 0.0423(7) Uani 1 1 d . . . . .
H9'A H 1.209422 0.273371 0.620238 0.063 Uiso 1 1 calc GR . . . .
H9'B H 1.291348 0.304078 0.683507 0.063 Uiso 1 1 calc GR . . . .
H9'C H 1.268091 0.369945 0.634980 0.063 Uiso 1 1 calc GR . . . .
C8' C 1.0582(3) 0.3550(2) 0.54761(13) 0.0393(7) Uani 1 1 d . . . . .
H8'A H 1.109950 0.402545 0.571236 0.059 Uiso 1 1 calc GR . . . .
H8'B H 1.002682 0.377949 0.518172 0.059 Uiso 1 1 calc GR . . . .
H8'C H 1.098808 0.315684 0.527153 0.059 Uiso 1 1 calc GR . . . .
C7' C 0.9029(3) 0.2479(2) 0.55679(14) 0.0462(8) Uani 1 1 d . . . . .
H7'A H 0.879405 0.212404 0.585232 0.069 Uiso 1 1 calc GR . . . .
H7'B H 0.921263 0.210808 0.524549 0.069 Uiso 1 1 calc GR . . . .
H7'C H 0.842824 0.281131 0.540268 0.069 Uiso 1 1 calc GR . . . .
O21 O 0.66838(13) 0.97631(11) 0.89242(8) 0.0256(4) Uani 1 1 d . . . . .
O22 O 0.48064(13) 0.92968(10) 0.87941(7) 0.0231(4) Uani 1 1 d . . . . .
O21' O 0.63962(13) 0.99514(11) 0.76914(7) 0.0238(4) Uani 1 1 d . . . . .
O22' O 0.45199(13) 0.95583(11) 0.75304(7) 0.0258(4) Uani 1 1 d . . . . .
N21 N 0.75103(17) 0.90316(14) 0.96977(9) 0.0294(5) Uani 1 1 d . . . . .
N23 N 0.53686(19) 0.73496(13) 0.94895(10) 0.0307(5) Uani 1 1 d . . . . .
N22 N 0.38371(17) 0.81563(13) 0.94796(9) 0.0251(4) Uani 1 1 d . . . . .
N21' N 0.66551(16) 1.01680(13) 0.67489(9) 0.0221(4) Uani 1 1 d . . . . .
N23' N 0.43053(18) 0.88547(13) 0.59533(9) 0.0253(4) Uani 1 1 d . . . . .
N22' N 0.29239(16) 0.94612(13) 0.63819(9) 0.0247(4) Uani 1 1 d . . . . .
C21 C 0.5572(2) 0.98212(17) 0.85619(11) 0.0270(5) Uani 1 1 d . . . . .
C22 C 0.6571(2) 0.91439(15) 0.93046(10) 0.0206(5) Uani 1 1 d . . . . .
C23 C 0.54630(19) 0.88131(14) 0.92129(10) 0.0197(5) Uani 1 1 d . . . . .
C31 C 0.5288(2) 1.07668(16) 0.85783(12) 0.0283(5) Uani 1 1 d . . . . .
C32 C 0.6132(2) 1.14606(16) 0.86691(11) 0.0284(5) Uani 1 1 d . . . . .
H32 H 0.688218 1.135232 0.871307 0.034 Uiso 1 1 calc R . . . .
C33 C 0.5854(3) 1.23096(17) 0.86938(13) 0.0369(6) Uani 1 1 d . . . . .
H33 H 0.641958 1.277694 0.876961 0.044 Uiso 1 1 calc R . . . .
C34 C 0.4732(3) 1.24674(18) 0.86055(14) 0.0433(7) Uani 1 1 d . . . . .
H34 H 0.454551 1.304093 0.860774 0.052 Uiso 1 1 calc R . . . .
C35 C 0.3894(2) 1.17851(19) 0.85149(12) 0.0359(6) Uani 1 1 d . . . . .
H35 H 0.314498 1.189827 0.846951 0.043 Uiso 1 1 calc R . . . .
C36 C 0.4161(2) 1.09282(18) 0.84910(12) 0.0311(6) Uani 1 1 d . . . . .
H36 H 0.359182 1.046368 0.841706 0.037 Uiso 1 1 calc R . . . .
C24 C 0.8610(2) 0.9439(2) 0.96526(14) 0.0402(7) Uani 1 1 d . . . . .
H24A H 0.860691 0.949206 0.923467 0.060 Uiso 1 1 calc GR . . . .
H24B H 0.918579 0.908141 0.981202 0.060 Uiso 1 1 calc GR . . . .
H24C H 0.875959 1.001077 0.988153 0.060 Uiso 1 1 calc GR . . . .
C25 C 0.7454(3) 0.8680(2) 1.02661(12) 0.0413(7) Uani 1 1 d . . . . .
H25A H 0.668700 0.863446 1.031143 0.062 Uiso 1 1 calc GR . . . .
H25B H 0.792067 0.906497 1.060043 0.062 Uiso 1 1 calc GR . . . .
H25C H 0.771684 0.810929 1.026011 0.062 Uiso 1 1 calc GR . . . .
C26 C 0.4886(2) 0.80919(15) 0.94024(10) 0.0225(5) Uani 1 1 d . . . . .
C30 C 0.6219(3) 0.70650(19) 0.91696(14) 0.0407(7) Uani 1 1 d . . . . .
H30A H 0.629292 0.744639 0.886737 0.061 Uiso 1 1 calc GR . . . .
H30B H 0.599159 0.647475 0.897735 0.061 Uiso 1 1 calc GR . . . .
H30C H 0.693057 0.708668 0.945382 0.061 Uiso 1 1 calc GR . . . .
C29 C 0.5071(3) 0.6756(2) 0.99137(16) 0.0514(8) Uani 1 1 d . . . . .
H29A H 0.463172 0.704343 1.016236 0.077 Uiso 1 1 calc GR . . . .
H29B H 0.574860 0.660542 1.016708 0.077 Uiso 1 1 calc GR . . . .
H29C H 0.463898 0.623270 0.968863 0.077 Uiso 1 1 calc GR . . . .
C28 C 0.2949(3) 0.7418(2) 0.93308(16) 0.0468(8) Uani 1 1 d . . . . .
H28A H 0.319739 0.693752 0.910937 0.070 Uiso 1 1 calc GR . . . .
H28B H 0.227846 0.759505 0.908676 0.070 Uiso 1 1 calc GR . . . .
H28C H 0.278704 0.723679 0.969859 0.070 Uiso 1 1 calc GR . . . .
C27 C 0.3450(2) 0.89995(17) 0.96424(12) 0.0311(6) Uani 1 1 d . . . . .
H27A H 0.409057 0.942381 0.981143 0.047 Uiso 1 1 calc GR . . . .
H27B H 0.299780 0.893654 0.993667 0.047 Uiso 1 1 calc GR . . . .
H27C H 0.300632 0.919296 0.928641 0.047 Uiso 1 1 calc GR . . . .
C21' C 0.5560(2) 0.94141(17) 0.79124(12) 0.0274(5) Uani 1 1 d . . . . .
C22' C 0.5952(2) 0.99021(14) 0.70829(10) 0.0203(5) Uani 1 1 d . . . . .
C23' C 0.4824(2) 0.96009(15) 0.69606(10) 0.0215(5) Uani 1 1 d . . . . .
C31' C 0.5790(2) 0.84576(16) 0.78564(11) 0.0274(5) Uani 1 1 d . . . . .
C36' C 0.4886(3) 0.78049(17) 0.77023(12) 0.0351(6) Uani 1 1 d . . . . .
H36' H 0.415444 0.794744 0.768597 0.042 Uiso 1 1 calc R . . . .
C35' C 0.5078(3) 0.6946(2) 0.75738(14) 0.0518(9) Uani 1 1 d . . . . .
H35' H 0.447425 0.650749 0.745920 0.062 Uiso 1 1 calc R . . . .
C34' C 0.6168(4) 0.6737(2) 0.76156(17) 0.0629(11) Uani 1 1 d . . . . .
H34' H 0.629744 0.615473 0.753534 0.076 Uiso 1 1 calc R . . . .
C33' C 0.7064(3) 0.7382(2) 0.77750(16) 0.0525(9) Uani 1 1 d . . . . .
H33' H 0.779625 0.723592 0.779919 0.063 Uiso 1 1 calc R . . . .
C32' C 0.6879(2) 0.82453(17) 0.78989(12) 0.0316(6) Uani 1 1 d . . . . .
H32' H 0.748467 0.868178 0.801053 0.038 Uiso 1 1 calc R . . . .
C24' C 0.7870(2) 1.03482(19) 0.69994(13) 0.0335(6) Uani 1 1 d . . . . .
H24D H 0.806589 1.096918 0.710607 0.050 Uiso 1 1 calc GR . . . .
H24E H 0.826918 1.013891 0.670198 0.050 Uiso 1 1 calc GR . . . .
H24F H 0.807318 1.005509 0.735497 0.050 Uiso 1 1 calc GR . . . .
C25' C 0.6241(2) 1.04206(16) 0.61453(11) 0.0260(5) Uani 1 1 d . . . . .
H25D H 0.641865 1.000289 0.584633 0.039 Uiso 1 1 calc GR . . . .
H25E H 0.659507 1.099249 0.612062 0.039 Uiso 1 1 calc GR . . . .
H25F H 0.543777 1.043279 0.607145 0.039 Uiso 1 1 calc GR . . . .
C26' C 0.4001(2) 0.93058(14) 0.64214(10) 0.0210(5) Uani 1 1 d . . . . .
C30' C 0.5202(2) 0.82730(16) 0.60530(12) 0.0305(6) Uani 1 1 d . . . . .
H30D H 0.587055 0.854761 0.596019 0.046 Uiso 1 1 calc GR . . . .
H30E H 0.496037 0.772880 0.579445 0.046 Uiso 1 1 calc GR . . . .
H30F H 0.536287 0.816132 0.646970 0.046 Uiso 1 1 calc GR . . . .
C29' C 0.3801(3) 0.8914(2) 0.53174(12) 0.0375(6) Uani 1 1 d . . . . .
H29D H 0.337202 0.836530 0.513648 0.056 Uiso 1 1 calc GR . . . .
H29E H 0.438757 0.904123 0.510623 0.056 Uiso 1 1 calc GR . . . .
H29F H 0.331312 0.937287 0.529076 0.056 Uiso 1 1 calc GR . . . .
C28' C 0.1959(2) 0.89098(18) 0.59847(13) 0.0368(6) Uani 1 1 d . . . . .
H28D H 0.166280 0.920575 0.564170 0.055 Uiso 1 1 calc GR . . . .
H28E H 0.138350 0.879940 0.620568 0.055 Uiso 1 1 calc GR . . . .
H28F H 0.219908 0.836298 0.584644 0.055 Uiso 1 1 calc GR . . . .
C27' C 0.2614(2) 1.01589(17) 0.67795(13) 0.0313(6) Uani 1 1 d . . . . .
H27D H 0.230811 0.990722 0.708810 0.047 Uiso 1 1 calc GR . . . .
H27E H 0.205748 1.046976 0.654502 0.047 Uiso 1 1 calc GR . . . .
H27F H 0.327116 1.055811 0.696651 0.047 Uiso 1 1 calc GR . . . .
P2 P 0.29132(6) 0.58531(6) 0.56983(4) 0.04146(19) Uani 1 1 d . . . . .
F11 F 0.36035(17) 0.61615(14) 0.52222(10) 0.0646(6) Uani 1 1 d . . . . .
F12 F 0.22211(16) 0.55418(13) 0.61851(9) 0.0568(5) Uani 1 1 d . . . . .
F13B F 0.2369(3) 0.67779(17) 0.56968(15) 0.0711(9) Uani 0.818(4) 1 d . U P A 1
F14B F 0.3924(3) 0.6296(2) 0.62176(12) 0.0766(10) Uani 0.818(4) 1 d . U P A 1
F15B F 0.3421(3) 0.4964(2) 0.56632(17) 0.0650(9) Uani 0.818(4) 1 d . U P A 1
F16B F 0.1860(3) 0.5467(2) 0.51620(13) 0.0611(8) Uani 0.818(4) 1 d . U P A 1
F13 F 0.3004(13) 0.6714(9) 0.6088(7) 0.070(3) Uani 0.182(4) 1 d . U P A 2
F14 F 0.3992(10) 0.5556(11) 0.6250(5) 0.066(3) Uani 0.182(4) 1 d . U P A 2
F15 F 0.2824(15) 0.4768(11) 0.5450(8) 0.075(4) Uani 0.182(4) 1 d . U P A 2
F16 F 0.1861(13) 0.5924(12) 0.5327(8) 0.070(3) Uani 0.182(4) 1 d . U P A 2
P1 P 0.80709(6) 0.88050(5) 0.51573(3) 0.03083(16) Uani 1 1 d . . . . .
F1 F 0.8508(2) 0.98202(13) 0.53217(10) 0.0710(6) Uani 1 1 d . . . . .
F2 F 0.75927(15) 0.77979(11) 0.49923(8) 0.0480(4) Uani 1 1 d . . . . .
F3 F 0.67988(16) 0.90524(13) 0.49569(9) 0.0604(5) Uani 1 1 d . . . . .
F4 F 0.79055(17) 0.87777(13) 0.58310(8) 0.0537(5) Uani 1 1 d . . . . .
F5 F 0.93085(15) 0.85389(15) 0.53575(9) 0.0620(5) Uani 1 1 d . . . . .
F6 F 0.82002(19) 0.88315(16) 0.44798(8) 0.0699(6) Uani 1 1 d . . . . .
P3 P 0.23040(7) 0.45228(5) 0.91364(3) 0.03428(17) Uani 1 1 d . . . . .
F21 F 0.1983(3) 0.53737(14) 0.94824(10) 0.0850(8) Uani 1 1 d . . . . .
F22 F 0.2653(2) 0.36933(13) 0.87824(9) 0.0688(6) Uani 1 1 d . . . . .
F23 F 0.10590(17) 0.43045(14) 0.87440(12) 0.0761(7) Uani 1 1 d . . . . .
F24 F 0.2064(2) 0.39332(16) 0.96318(11) 0.0826(7) Uani 1 1 d . . . . .
F25 F 0.3562(2) 0.47481(14) 0.95135(12) 0.0880(8) Uani 1 1 d . . . . .
F26 F 0.2577(2) 0.51132(14) 0.86360(9) 0.0677(6) Uani 1 1 d . . . . .
P4 P 0.05524(6) 0.91833(5) 0.81409(4) 0.04024(19) Uani 1 1 d . . . . .
F31 F 0.14148(19) 1.00160(16) 0.84135(13) 0.0911(8) Uani 1 1 d . . . . .
F32 F -0.0302(2) 0.83514(16) 0.78179(15) 0.0987(9) Uani 1 1 d . . . . .
F33 F -0.04783(16) 0.96880(14) 0.82545(10) 0.0631(5) Uani 1 1 d . . . . .
F34 F 0.0690(3) 0.8838(2) 0.87735(13) 0.1175(12) Uani 1 1 d . . . . .
F35 F 0.1570(2) 0.86647(17) 0.80291(15) 0.0975(9) Uani 1 1 d . . . . .
F36 F 0.0415(2) 0.95327(19) 0.74966(11) 0.0859(8) Uani 1 1 d . . . . .
C42B C 1.0101(17) 0.6430(15) 0.9876(11) 0.096(4) Uani 0.39(2) 1 d . U P B 2
H42A H 1.061336 0.618587 0.965392 0.144 Uiso 0.39(2) 1 calc GR . P B 2
H42B H 0.936047 0.638199 0.961581 0.144 Uiso 0.39(2) 1 calc GR . P B 2
H42C H 1.007555 0.611442 1.021771 0.144 Uiso 0.39(2) 1 calc GR . P B 2
N41 N 1.0990(4) 0.8015(4) 1.0398(2) 0.1091(15) Uani 1 1 d . U . . .
C41 C 1.0516(4) 0.7417(4) 1.0104(2) 0.0834(13) Uani 1 1 d . U . . .
C42 C 0.9831(10) 0.6765(11) 0.9639(7) 0.094(3) Uani 0.61(2) 1 d . U P B 1
H42D H 0.936195 0.638835 0.981888 0.141 Uiso 0.61(2) 1 calc GR . P B 1
H42E H 1.031246 0.642094 0.945105 0.141 Uiso 0.61(2) 1 calc GR . P B 1
H42F H 0.936329 0.705173 0.933777 0.141 Uiso 0.61(2) 1 calc GR . P B 1
O1W O 0.9877(15) 0.9085(12) 0.3904(7) 0.068(7) Uani 0.159(9) 1 d . . P . .
H1WA H 1.043418 0.935947 0.416610 0.102 Uiso 0.159(9) 1 d G . P . .
H1WB H 0.937659 0.889379 0.408255 0.102 Uiso 0.159(9) 1 d G . P . .


_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
O2 C1 1.419(3) . ?
O2 C3 1.417(3) . ?
O1 C1 1.445(3) . ?
O1 C2 1.358(3) . ?
O2' C1' 1.417(3) . ?
O2' C3' 1.413(3) . ?
O1' C1' 1.444(3) . ?
O1' C2' 1.361(3) . ?
N1 C2 1.325(3) . ?
N1 C4 1.459(4) . ?
N1 C5 1.463(4) . ?
N3 C6 1.344(3) . ?
N3 C9 1.464(4) . ?
N3 C10 1.468(3) . ?
N2 C6 1.337(3) . ?
N2 C8 1.463(3) . ?
N2 C7 1.456(3) . ?
N1' C2' 1.328(3) . ?
N1' C4' 1.458(3) . ?
N1' C5' 1.460(4) . ?
N3' C6' 1.338(3) . ?
N3' C10' 1.457(3) . ?
N3' C9' 1.470(3) . ?
N2' C6' 1.333(3) . ?
N2' C8' 1.462(3) . ?
N2' C7' 1.458(4) . ?
C1 C11 1.511(3) . ?
C1 C1' 1.552(4) . ?
C2 C3 1.368(3) . ?
C3 C6 1.409(3) . ?
C11 C16 1.386(4) . ?
C11 C12 1.386(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.391(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.381(6) . ?
C14 H14 0.9300 . ?
C14 C13 1.370(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.389(4) . ?
C12 H12 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C1' C11' 1.508(3) . ?
C2' C3' 1.365(3) . ?
C3' C6' 1.418(3) . ?
C11' C16' 1.391(3) . ?
C11' C12' 1.387(3) . ?
C16' H16' 0.9300 . ?
C16' C15' 1.386(4) . ?
C15' H15' 0.9300 . ?
C15' C14' 1.388(4) . ?
C14' H14' 0.9300 . ?
C14' C13' 1.380(4) . ?
C13' H13' 0.9300 . ?
C13' C12' 1.386(4) . ?
C12' H12' 0.9300 . ?
C4' H4'A 0.9600 . ?
C4' H4'B 0.9600 . ?
C4' H4'C 0.9600 . ?
C5' H5'A 0.9600 . ?
C5' H5'B 0.9600 . ?
C5' H5'C 0.9600 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
C9' H9'A 0.9600 . ?
C9' H9'B 0.9600 . ?
C9' H9'C 0.9600 . ?
C8' H8'A 0.9600 . ?
C8' H8'B 0.9600 . ?
C8' H8'C 0.9600 . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
O21 C21 1.442(3) . ?
O21 C22 1.366(3) . ?
O22 C21 1.404(3) . ?
O22 C23 1.419(3) . ?
O21' C21' 1.462(3) . ?
O21' C22' 1.364(3) . ?
O22' C21' 1.422(3) . ?
O22' C23' 1.427(3) . ?
N21 C22 1.328(3) . ?
N21 C24 1.460(3) . ?
N21 C25 1.461(3) . ?
N23 C26 1.341(3) . ?
N23 C30 1.459(4) . ?
N23 C29 1.471(3) . ?
N22 C26 1.337(3) . ?
N22 C28 1.464(3) . ?
N22 C27 1.459(3) . ?
N21' C22' 1.327(3) . ?
N21' C24' 1.461(3) . ?
N21' C25' 1.458(3) . ?
N23' C26' 1.348(3) . ?
N23' C30' 1.465(3) . ?
N23' C29' 1.458(3) . ?
N22' C26' 1.341(3) . ?
N22' C28' 1.465(3) . ?
N22' C27' 1.462(3) . ?
C21 C31 1.523(3) . ?
C21 C21' 1.541(4) . ?
C22 C23 1.368(3) . ?
C23 C26 1.417(3) . ?
C31 C32 1.388(4) . ?
C31 C36 1.392(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.376(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.385(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.371(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.384(4) . ?
C36 H36 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C21' C31' 1.520(3) . ?
C22' C23' 1.373(3) . ?
C23' C26' 1.414(3) . ?
C31' C36' 1.389(4) . ?
C31' C32' 1.380(4) . ?
C36' H36' 0.9300 . ?
C36' C35' 1.377(4) . ?
C35' H35' 0.9300 . ?
C35' C34' 1.379(5) . ?
C34' H34' 0.9300 . ?
C34' C33' 1.376(5) . ?
C33' H33' 0.9300 . ?
C33' C32' 1.379(4) . ?
C32' H32' 0.9300 . ?
C24' H24D 0.9600 . ?
C24' H24E 0.9600 . ?
C24' H24F 0.9600 . ?
C25' H25D 0.9600 . ?
C25' H25E 0.9600 . ?
C25' H25F 0.9600 . ?
C30' H30D 0.9600 . ?
C30' H30E 0.9600 . ?
C30' H30F 0.9600 . ?
C29' H29D 0.9600 . ?
C29' H29E 0.9600 . ?
C29' H29F 0.9600 . ?
C28' H28D 0.9600 . ?
C28' H28E 0.9600 . ?
C28' H28F 0.9600 . ?
C27' H27D 0.9600 . ?
C27' H27E 0.9600 . ?
C27' H27F 0.9600 . ?
P2 F11 1.590(2) . ?
P2 F12 1.613(2) . ?
P2 F13B 1.620(3) . ?
P2 F14B 1.566(3) . ?
P2 F15B 1.551(3) . ?
P2 F16B 1.595(3) . ?
P2 F13 1.502(13) . ?
P2 F14 1.736(12) . ?
P2 F15 1.697(17) . ?
P2 F16 1.395(16) . ?
P1 F1 1.590(2) . ?
P1 F2 1.5896(18) . ?
P1 F3 1.6086(19) . ?
P1 F4 1.5899(18) . ?
P1 F5 1.5801(19) . ?
P1 F6 1.5840(19) . ?
P3 F21 1.582(2) . ?
P3 F22 1.5793(19) . ?
P3 F23 1.577(2) . ?
P3 F24 1.573(2) . ?
P3 F25 1.579(2) . ?
P3 F26 1.595(2) . ?
P4 F31 1.573(2) . ?
P4 F32 1.590(2) . ?
P4 F33 1.585(2) . ?
P4 F34 1.561(2) . ?
P4 F35 1.582(2) . ?
P4 F36 1.588(2) . ?
C42B H42A 0.9600 . ?
C42B H42B 0.9600 . ?
C42B H42C 0.9600 . ?
C42B C41 1.56(2) . ?
N41 C41 1.119(6) . ?
C41 C42 1.448(11) . ?
C42 H42D 0.9600 . ?
C42 H42E 0.9600 . ?
C42 H42F 0.9600 . ?
O1W H1WA 0.8507 . ?
O1W H1WB 0.8507 . ?

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
C3 O2 C1 106.59(18) . . ?
C2 O1 C1 107.78(18) . . ?
C3' O2' C1' 106.43(17) . . ?
C2' O1' C1' 107.39(17) . . ?
C2 N1 C4 121.0(2) . . ?
C2 N1 C5 121.6(2) . . ?
C4 N1 C5 117.0(2) . . ?
C6 N3 C9 121.8(2) . . ?
C6 N3 C10 121.8(2) . . ?
C9 N3 C10 116.3(2) . . ?
C6 N2 C8 122.9(2) . . ?
C6 N2 C7 121.8(2) . . ?
C7 N2 C8 115.3(2) . . ?
C2' N1' C4' 122.0(2) . . ?
C2' N1' C5' 120.0(2) . . ?
C4' N1' C5' 117.7(2) . . ?
C6' N3' C10' 122.8(2) . . ?
C6' N3' C9' 122.6(2) . . ?
C10' N3' C9' 114.6(2) . . ?
C6' N2' C8' 123.1(2) . . ?
C6' N2' C7' 121.7(2) . . ?
C7' N2' C8' 115.0(2) . . ?
O2 C1 O1 106.51(17) . . ?
O2 C1 C11 110.2(2) . . ?
O2 C1 C1' 109.5(2) . . ?
O1 C1 C11 110.0(2) . . ?
O1 C1 C1' 105.34(19) . . ?
C11 C1 C1' 114.88(19) . . ?
O1 C2 C3 110.1(2) . . ?
N1 C2 O1 115.8(2) . . ?
N1 C2 C3 134.1(2) . . ?
C2 C3 O2 108.8(2) . . ?
C2 C3 C6 131.2(2) . . ?
C6 C3 O2 119.7(2) . . ?
C16 C11 C1 120.9(3) . . ?
C16 C11 C12 119.7(3) . . ?
C12 C11 C1 119.4(3) . . ?
C11 C16 H16 120.1 . . ?
C11 C16 C15 119.9(3) . . ?
C15 C16 H16 120.1 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 119.9 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C14 C13 H13 119.8 . . ?
C14 C13 C12 120.5(4) . . ?
C12 C13 H13 119.8 . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C3 118.8(2) . . ?
N2 C6 N3 120.4(2) . . ?
N2 C6 C3 120.8(2) . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2' C1' O1' 106.66(18) . . ?
O2' C1' C1 109.12(19) . . ?
O2' C1' C11' 110.38(19) . . ?
O1' C1' C1 107.46(19) . . ?
O1' C1' C11' 110.54(19) . . ?
C11' C1' C1 112.47(19) . . ?
O1' C2' C3' 110.2(2) . . ?
N1' C2' O1' 116.2(2) . . ?
N1' C2' C3' 133.4(2) . . ?
O2' C3' C6' 117.5(2) . . ?
C2' C3' O2' 108.8(2) . . ?
C2' C3' C6' 133.7(2) . . ?
C16' C11' C1' 119.8(2) . . ?
C12' C11' C1' 120.0(2) . . ?
C12' C11' C16' 120.0(2) . . ?
C11' C16' H16' 120.2 . . ?
C15' C16' C11' 119.6(2) . . ?
C15' C16' H16' 120.2 . . ?
C16' C15' H15' 119.9 . . ?
C16' C15' C14' 120.2(3) . . ?
C14' C15' H15' 119.9 . . ?
C15' C14' H14' 120.0 . . ?
C13' C14' C15' 120.0(2) . . ?
C13' C14' H14' 120.0 . . ?
C14' C13' H13' 119.9 . . ?
C14' C13' C12' 120.1(2) . . ?
C12' C13' H13' 119.9 . . ?
C11' C12' H12' 120.0 . . ?
C13' C12' C11' 120.0(2) . . ?
C13' C12' H12' 120.0 . . ?
N1' C4' H4'A 109.5 . . ?
N1' C4' H4'B 109.5 . . ?
N1' C4' H4'C 109.5 . . ?
H4'A C4' H4'B 109.5 . . ?
H4'A C4' H4'C 109.5 . . ?
H4'B C4' H4'C 109.5 . . ?
N1' C5' H5'A 109.5 . . ?
N1' C5' H5'B 109.5 . . ?
N1' C5' H5'C 109.5 . . ?
H5'A C5' H5'B 109.5 . . ?
H5'A C5' H5'C 109.5 . . ?
H5'B C5' H5'C 109.5 . . ?
N3' C6' C3' 120.3(2) . . ?
N2' C6' N3' 120.7(2) . . ?
N2' C6' C3' 119.0(2) . . ?
N3' C10' H10D 109.5 . . ?
N3' C10' H10E 109.5 . . ?
N3' C10' H10F 109.5 . . ?
H10D C10' H10E 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
N3' C9' H9'A 109.5 . . ?
N3' C9' H9'B 109.5 . . ?
N3' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
N2' C8' H8'A 109.5 . . ?
N2' C8' H8'B 109.5 . . ?
N2' C8' H8'C 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?
N2' C7' H7'A 109.5 . . ?
N2' C7' H7'B 109.5 . . ?
N2' C7' H7'C 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
C22 O21 C21 106.93(17) . . ?
C21 O22 C23 106.50(17) . . ?
C22' O21' C21' 103.76(17) . . ?
C21' O22' C23' 101.88(17) . . ?
C22 N21 C24 121.3(2) . . ?
C22 N21 C25 120.5(2) . . ?
C24 N21 C25 116.7(2) . . ?
C26 N23 C30 122.9(2) . . ?
C26 N23 C29 122.2(2) . . ?
C30 N23 C29 114.9(2) . . ?
C26 N22 C28 123.2(2) . . ?
C26 N22 C27 121.9(2) . . ?
C27 N22 C28 114.4(2) . . ?
C22' N21' C24' 121.6(2) . . ?
C22' N21' C25' 121.5(2) . . ?
C25' N21' C24' 116.27(19) . . ?
C26' N23' C30' 121.5(2) . . ?
C26' N23' C29' 123.8(2) . . ?
C29' N23' C30' 114.8(2) . . ?
C26' N22' C28' 123.7(2) . . ?
C26' N22' C27' 121.8(2) . . ?
C27' N22' C28' 114.2(2) . . ?
O21 C21 C31 111.5(2) . . ?
O21 C21 C21' 106.68(19) . . ?
O22 C21 O21 107.06(18) . . ?
O22 C21 C31 111.1(2) . . ?
O22 C21 C21' 108.5(2) . . ?
C31 C21 C21' 111.9(2) . . ?
O21 C22 C23 110.27(19) . . ?
N21 C22 O21 115.4(2) . . ?
N21 C22 C23 134.1(2) . . ?
C22 C23 O22 108.19(18) . . ?
C22 C23 C26 134.7(2) . . ?
C26 C23 O22 116.9(2) . . ?
C32 C31 C21 120.9(2) . . ?
C32 C31 C36 120.1(2) . . ?
C36 C31 C21 119.0(2) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 C31 119.8(3) . . ?
C33 C32 H32 120.1 . . ?
C32 C33 H33 120.0 . . ?
C32 C33 C34 119.9(3) . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 119.7 . . ?
C35 C34 C33 120.5(3) . . ?
C35 C34 H34 119.7 . . ?
C34 C35 H35 119.9 . . ?
C34 C35 C36 120.1(3) . . ?
C36 C35 H35 119.9 . . ?
C31 C36 H36 120.3 . . ?
C35 C36 C31 119.5(3) . . ?
C35 C36 H36 120.3 . . ?
N21 C24 H24A 109.5 . . ?
N21 C24 H24B 109.5 . . ?
N21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N21 C25 H25A 109.5 . . ?
N21 C25 H25B 109.5 . . ?
N21 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N23 C26 C23 120.8(2) . . ?
N22 C26 N23 120.4(2) . . ?
N22 C26 C23 118.8(2) . . ?
N23 C30 H30A 109.5 . . ?
N23 C30 H30B 109.5 . . ?
N23 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N23 C29 H29A 109.5 . . ?
N23 C29 H29B 109.5 . . ?
N23 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N22 C28 H28A 109.5 . . ?
N22 C28 H28B 109.5 . . ?
N22 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N22 C27 H27A 109.5 . . ?
N22 C27 H27B 109.5 . . ?
N22 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O21' C21' C21 107.32(19) . . ?
O21' C21' C31' 110.2(2) . . ?
O22' C21' O21' 103.08(18) . . ?
O22' C21' C21 107.76(19) . . ?
O22' C21' C31' 112.8(2) . . ?
C31' C21' C21 114.9(2) . . ?
O21' C22' C23' 109.63(19) . . ?
N21' C22' O21' 116.0(2) . . ?
N21' C22' C23' 134.4(2) . . ?
C22' C23' O22' 107.11(19) . . ?
C22' C23' C26' 134.0(2) . . ?
C26' C23' O22' 118.75(19) . . ?
C36' C31' C21' 119.3(2) . . ?
C32' C31' C21' 120.1(2) . . ?
C32' C31' C36' 120.3(2) . . ?
C31' C36' H36' 120.2 . . ?
C35' C36' C31' 119.7(3) . . ?
C35' C36' H36' 120.2 . . ?
C36' C35' H35' 120.1 . . ?
C36' C35' C34' 119.8(3) . . ?
C34' C35' H35' 120.1 . . ?
C35' C34' H34' 119.7 . . ?
C33' C34' C35' 120.5(3) . . ?
C33' C34' H34' 119.7 . . ?
C34' C33' H33' 120.0 . . ?
C34' C33' C32' 120.1(3) . . ?
C32' C33' H33' 120.0 . . ?
C31' C32' H32' 120.2 . . ?
C33' C32' C31' 119.6(3) . . ?
C33' C32' H32' 120.2 . . ?
N21' C24' H24D 109.5 . . ?
N21' C24' H24E 109.5 . . ?
N21' C24' H24F 109.5 . . ?
H24D C24' H24E 109.5 . . ?
H24D C24' H24F 109.5 . . ?
H24E C24' H24F 109.5 . . ?
N21' C25' H25D 109.5 . . ?
N21' C25' H25E 109.5 . . ?
N21' C25' H25F 109.5 . . ?
H25D C25' H25E 109.5 . . ?
H25D C25' H25F 109.5 . . ?
H25E C25' H25F 109.5 . . ?
N23' C26' C23' 119.5(2) . . ?
N22' C26' N23' 120.4(2) . . ?
N22' C26' C23' 120.1(2) . . ?
N23' C30' H30D 109.5 . . ?
N23' C30' H30E 109.5 . . ?
N23' C30' H30F 109.5 . . ?
H30D C30' H30E 109.5 . . ?
H30D C30' H30F 109.5 . . ?
H30E C30' H30F 109.5 . . ?
N23' C29' H29D 109.5 . . ?
N23' C29' H29E 109.5 . . ?
N23' C29' H29F 109.5 . . ?
H29D C29' H29E 109.5 . . ?
H29D C29' H29F 109.5 . . ?
H29E C29' H29F 109.5 . . ?
N22' C28' H28D 109.5 . . ?
N22' C28' H28E 109.5 . . ?
N22' C28' H28F 109.5 . . ?
H28D C28' H28E 109.5 . . ?
H28D C28' H28F 109.5 . . ?
H28E C28' H28F 109.5 . . ?
N22' C27' H27D 109.5 . . ?
N22' C27' H27E 109.5 . . ?
N22' C27' H27F 109.5 . . ?
H27D C27' H27E 109.5 . . ?
H27D C27' H27F 109.5 . . ?
H27E C27' H27F 109.5 . . ?
F11 P2 F12 179.59(13) . . ?
F11 P2 F13B 88.97(13) . . ?
F11 P2 F16B 90.86(15) . . ?
F11 P2 F14 100.7(4) . . ?
F11 P2 F15 94.9(5) . . ?
F12 P2 F13B 91.12(13) . . ?
F12 P2 F14 78.9(4) . . ?
F12 P2 F15 85.2(5) . . ?
F14B P2 F11 88.15(14) . . ?
F14B P2 F12 91.45(13) . . ?
F14B P2 F13B 88.99(19) . . ?
F14B P2 F16B 176.1(2) . . ?
F15B P2 F11 88.95(15) . . ?
F15B P2 F12 90.97(15) . . ?
F15B P2 F13B 177.02(18) . . ?
F15B P2 F14B 93.1(2) . . ?
F15B P2 F16B 90.64(19) . . ?
F16B P2 F12 89.55(14) . . ?
F16B P2 F13B 87.26(19) . . ?
F13 P2 F11 98.8(5) . . ?
F13 P2 F12 81.0(5) . . ?
F13 P2 F14 87.7(8) . . ?
F13 P2 F15 163.6(9) . . ?
F15 P2 F14 81.0(8) . . ?
F16 P2 F11 94.3(7) . . ?
F16 P2 F12 86.1(7) . . ?
F16 P2 F13 96.6(10) . . ?
F16 P2 F14 163.6(8) . . ?
F16 P2 F15 91.3(9) . . ?
F1 P1 F3 89.66(12) . . ?
F2 P1 F1 178.12(12) . . ?
F2 P1 F3 88.53(10) . . ?
F2 P1 F4 90.25(10) . . ?
F4 P1 F1 89.25(12) . . ?
F4 P1 F3 89.29(11) . . ?
F5 P1 F1 91.64(13) . . ?
F5 P1 F2 90.17(11) . . ?
F5 P1 F3 178.57(13) . . ?
F5 P1 F4 90.12(11) . . ?
F5 P1 F6 91.35(12) . . ?
F6 P1 F1 91.14(12) . . ?
F6 P1 F2 89.31(11) . . ?
F6 P1 F3 89.23(12) . . ?
F6 P1 F4 178.46(12) . . ?
F21 P3 F26 88.05(12) . . ?
F22 P3 F21 178.09(15) . . ?
F22 P3 F26 90.28(12) . . ?
F23 P3 F21 91.59(14) . . ?
F23 P3 F22 89.29(13) . . ?
F23 P3 F25 178.44(15) . . ?
F23 P3 F26 88.60(13) . . ?
F24 P3 F21 92.76(13) . . ?
F24 P3 F22 88.88(13) . . ?
F24 P3 F23 92.51(14) . . ?
F24 P3 F25 88.93(14) . . ?
F24 P3 F26 178.61(14) . . ?
F25 P3 F21 88.92(15) . . ?
F25 P3 F22 90.15(14) . . ?
F25 P3 F26 89.95(13) . . ?
F31 P4 F32 175.81(17) . . ?
F31 P4 F33 91.62(13) . . ?
F31 P4 F35 89.21(14) . . ?
F31 P4 F36 88.11(16) . . ?
F33 P4 F32 89.86(14) . . ?
F33 P4 F36 89.28(13) . . ?
F34 P4 F31 91.92(19) . . ?
F34 P4 F32 91.98(19) . . ?
F34 P4 F33 90.89(14) . . ?
F34 P4 F35 88.59(16) . . ?
F34 P4 F36 179.83(18) . . ?
F35 P4 F32 89.35(15) . . ?
F35 P4 F33 179.04(15) . . ?
F35 P4 F36 91.24(16) . . ?
F36 P4 F32 87.99(16) . . ?
H42A C42B H42B 109.5 . . ?
H42A C42B H42C 109.5 . . ?
H42B C42B H42C 109.5 . . ?
C41 C42B H42A 109.5 . . ?
C41 C42B H42B 109.5 . . ?
C41 C42B H42C 109.5 . . ?
N41 C41 C42B 160.0(13) . . ?
N41 C41 C42 168.7(11) . . ?
C41 C42 H42D 109.5 . . ?
C41 C42 H42E 109.5 . . ?
C41 C42 H42F 109.5 . . ?
H42D C42 H42E 109.5 . . ?
H42D C42 H42F 109.5 . . ?
H42E C42 H42F 109.5 . . ?
H1WA O1W H1WB 109.4 . . ?

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
O1W H1WA F1 0.85 1.85 2.681(16) 166.9 2_776
O1W H1WB F6 0.85 1.85 2.676(17) 162.6 .

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
O2 C1 C11 C16 146.6(2) . . . . ?
O2 C1 C11 C12 -31.7(3) . . . . ?
O2 C1 C1' O2' -50.6(2) . . . . ?
O2 C1 C1' O1' 64.6(2) . . . . ?
O2 C1 C1' C11' -173.47(18) . . . . ?
O2 C3 C6 N3 143.1(2) . . . . ?
O2 C3 C6 N2 -35.9(3) . . . . ?
O1 C1 C11 C16 29.5(3) . . . . ?
O1 C1 C11 C12 -148.8(2) . . . . ?
O1 C1 C1' O2' 63.6(2) . . . . ?
O1 C1 C1' O1' 178.84(17) . . . . ?
O1 C1 C1' C11' -59.3(2) . . . . ?
O1 C2 C3 O2 -4.1(3) . . . . ?
O1 C2 C3 C6 170.2(2) . . . . ?
O2' C1' C11' C16' -36.2(3) . . . . ?
O2' C1' C11' C12' 148.0(2) . . . . ?
O2' C3' C6' N3' 138.8(2) . . . . ?
O2' C3' C6' N2' -39.3(3) . . . . ?
O1' C1' C11' C16' -153.9(2) . . . . ?
O1' C1' C11' C12' 30.2(3) . . . . ?
O1' C2' C3' O2' -6.9(3) . . . . ?
O1' C2' C3' C6' 171.1(3) . . . . ?
N1 C2 C3 O2 173.9(3) . . . . ?
N1 C2 C3 C6 -11.9(5) . . . . ?
N1' C2' C3' O2' 167.4(3) . . . . ?
N1' C2' C3' C6' -14.6(5) . . . . ?
C1 O2 C3 C2 2.1(3) . . . . ?
C1 O2 C3 C6 -172.9(2) . . . . ?
C1 O1 C2 N1 -174.0(2) . . . . ?
C1 O1 C2 C3 4.4(3) . . . . ?
C1 C11 C16 C15 -176.8(2) . . . . ?
C1 C11 C12 C13 177.4(2) . . . . ?
C1 C1' C11' C16' 86.0(3) . . . . ?
C1 C1' C11' C12' -89.9(3) . . . . ?
C2 O1 C1 O2 -2.9(3) . . . . ?
C2 O1 C1 C11 116.5(2) . . . . ?
C2 O1 C1 C1' -119.2(2) . . . . ?
C2 C3 C6 N3 -30.7(4) . . . . ?
C2 C3 C6 N2 150.3(3) . . . . ?
C3 O2 C1 O1 0.5(2) . . . . ?
C3 O2 C1 C11 -118.8(2) . . . . ?
C3 O2 C1 C1' 113.9(2) . . . . ?
C11 C1 C1' O2' -175.2(2) . . . . ?
C11 C1 C1' O1' -59.9(3) . . . . ?
C11 C1 C1' C11' 62.0(3) . . . . ?
C11 C16 C15 C14 -1.0(4) . . . . ?
C16 C11 C12 C13 -1.0(4) . . . . ?
C16 C15 C14 C13 -0.1(4) . . . . ?
C15 C14 C13 C12 0.6(5) . . . . ?
C14 C13 C12 C11 -0.1(4) . . . . ?
C12 C11 C16 C15 1.5(4) . . . . ?
C4 N1 C2 O1 -18.5(4) . . . . ?
C4 N1 C2 C3 163.6(3) . . . . ?
C5 N1 C2 O1 153.5(2) . . . . ?
C5 N1 C2 C3 -24.4(4) . . . . ?
C9 N3 C6 N2 145.0(2) . . . . ?
C9 N3 C6 C3 -34.0(3) . . . . ?
C10 N3 C6 N2 -38.4(3) . . . . ?
C10 N3 C6 C3 142.6(2) . . . . ?
C8 N2 C6 N3 -25.1(3) . . . . ?
C8 N2 C6 C3 153.9(2) . . . . ?
C7 N2 C6 N3 155.4(2) . . . . ?
C7 N2 C6 C3 -25.6(3) . . . . ?
C1' O2' C3' C2' 8.0(3) . . . . ?
C1' O2' C3' C6' -170.4(2) . . . . ?
C1' O1' C2' N1' -172.5(2) . . . . ?
C1' O1' C2' C3' 2.9(3) . . . . ?
C1' C1 C11 C16 -89.1(3) . . . . ?
C1' C1 C11 C12 92.5(3) . . . . ?
C1' C11' C16' C15' -175.8(2) . . . . ?
C1' C11' C12' C13' 175.7(2) . . . . ?
C2' O1' C1' O2' 2.2(2) . . . . ?
C2' O1' C1' C1 -114.7(2) . . . . ?
C2' O1' C1' C11' 122.2(2) . . . . ?
C2' C3' C6' N3' -39.1(4) . . . . ?
C2' C3' C6' N2' 142.8(3) . . . . ?
C3' O2' C1' O1' -6.1(2) . . . . ?
C3' O2' C1' C1 109.6(2) . . . . ?
C3' O2' C1' C11' -126.3(2) . . . . ?
C11' C16' C15' C14' 0.0(4) . . . . ?
C16' C11' C12' C13' -0.2(4) . . . . ?
C16' C15' C14' C13' 0.1(4) . . . . ?
C15' C14' C13' C12' -0.2(4) . . . . ?
C14' C13' C12' C11' 0.3(4) . . . . ?
C12' C11' C16' C15' 0.1(4) . . . . ?
C4' N1' C2' O1' -14.4(4) . . . . ?
C4' N1' C2' C3' 171.7(3) . . . . ?
C5' N1' C2' O1' 159.2(2) . . . . ?
C5' N1' C2' C3' -14.8(4) . . . . ?
C10' N3' C6' N2' 147.8(2) . . . . ?
C10' N3' C6' C3' -30.3(4) . . . . ?
C9' N3' C6' N2' -31.5(4) . . . . ?
C9' N3' C6' C3' 150.4(3) . . . . ?
C8' N2' C6' N3' -31.6(3) . . . . ?
C8' N2' C6' C3' 146.6(2) . . . . ?
C7' N2' C6' N3' 154.5(3) . . . . ?
C7' N2' C6' C3' -27.4(4) . . . . ?
O21 C21 C31 C32 28.3(3) . . . . ?
O21 C21 C31 C36 -152.7(2) . . . . ?
O21 C21 C21' O21' -62.7(2) . . . . ?
O21 C21 C21' O22' -173.10(17) . . . . ?
O21 C21 C21' C31' 60.2(3) . . . . ?
O21 C22 C23 O22 -5.7(3) . . . . ?
O21 C22 C23 C26 168.8(2) . . . . ?
O22 C21 C31 C32 147.6(2) . . . . ?
O22 C21 C31 C36 -33.4(3) . . . . ?
O22 C21 C21' O21' -177.71(17) . . . . ?
O22 C21 C21' O22' 71.9(2) . . . . ?
O22 C21 C21' C31' -54.8(3) . . . . ?
O22 C23 C26 N23 142.1(2) . . . . ?
O22 C23 C26 N22 -36.3(3) . . . . ?
O21' C21' C31' C36' -143.7(2) . . . . ?
O21' C21' C31' C32' 29.9(3) . . . . ?
O21' C22' C23' O22' 7.0(2) . . . . ?
O21' C22' C23' C26' -169.0(2) . . . . ?
O22' C21' C31' C36' -29.1(3) . . . . ?
O22' C21' C31' C32' 144.5(2) . . . . ?
O22' C23' C26' N23' -140.8(2) . . . . ?
O22' C23' C26' N22' 38.0(3) . . . . ?
N21 C22 C23 O22 169.4(2) . . . . ?
N21 C22 C23 C26 -16.1(5) . . . . ?
N21' C22' C23' O22' -170.5(2) . . . . ?
N21' C22' C23' C26' 13.4(5) . . . . ?
C21 O21 C22 N21 -176.8(2) . . . . ?
C21 O21 C22 C23 -0.7(3) . . . . ?
C21 O22 C23 C22 9.9(2) . . . . ?
C21 O22 C23 C26 -165.8(2) . . . . ?
C21 C31 C32 C33 -178.7(2) . . . . ?
C21 C31 C36 C35 178.9(2) . . . . ?
C21 C21' C31' C36' 95.0(3) . . . . ?
C21 C21' C31' C32' -91.4(3) . . . . ?
C22 O21 C21 O22 6.8(2) . . . . ?
C22 O21 C21 C31 128.5(2) . . . . ?
C22 O21 C21 C21' -109.2(2) . . . . ?
C22 C23 C26 N23 -32.1(4) . . . . ?
C22 C23 C26 N22 149.5(3) . . . . ?
C23 O22 C21 O21 -10.1(2) . . . . ?
C23 O22 C21 C31 -132.0(2) . . . . ?
C23 O22 C21 C21' 104.7(2) . . . . ?
C31 C21 C21' O21' 59.4(2) . . . . ?
C31 C21 C21' O22' -51.0(3) . . . . ?
C31 C21 C21' C31' -177.6(2) . . . . ?
C31 C32 C33 C34 -2.4(4) . . . . ?
C32 C31 C36 C35 -2.1(4) . . . . ?
C32 C33 C34 C35 2.3(4) . . . . ?
C33 C34 C35 C36 -2.1(4) . . . . ?
C34 C35 C36 C31 2.0(4) . . . . ?
C36 C31 C32 C33 2.3(4) . . . . ?
C24 N21 C22 O21 -9.7(3) . . . . ?
C24 N21 C22 C23 175.4(3) . . . . ?
C25 N21 C22 O21 155.5(2) . . . . ?
C25 N21 C22 C23 -19.4(4) . . . . ?
C30 N23 C26 N22 151.1(2) . . . . ?
C30 N23 C26 C23 -27.3(4) . . . . ?
C29 N23 C26 N22 -28.4(4) . . . . ?
C29 N23 C26 C23 153.2(3) . . . . ?
C28 N22 C26 N23 -34.7(4) . . . . ?
C28 N22 C26 C23 143.7(2) . . . . ?
C27 N22 C26 N23 153.7(2) . . . . ?
C27 N22 C26 C23 -27.8(3) . . . . ?
C21' O21' C22' N21' -165.3(2) . . . . ?
C21' O21' C22' C23' 16.6(2) . . . . ?
C21' O22' C23' C22' -28.2(2) . . . . ?
C21' O22' C23' C26' 148.6(2) . . . . ?
C21' C21 C31 C32 -91.0(3) . . . . ?
C21' C21 C31 C36 88.0(3) . . . . ?
C21' C31' C36' C35' 171.6(2) . . . . ?
C21' C31' C32' C33' -172.2(3) . . . . ?
C22' O21' C21' O22' -33.9(2) . . . . ?
C22' O21' C21' C21 -147.53(19) . . . . ?
C22' O21' C21' C31' 86.7(2) . . . . ?
C22' C23' C26' N23' 34.9(4) . . . . ?
C22' C23' C26' N22' -146.3(3) . . . . ?
C23' O22' C21' O21' 37.4(2) . . . . ?
C23' O22' C21' C21 150.65(19) . . . . ?
C23' O22' C21' C31' -81.5(2) . . . . ?
C31' C36' C35' C34' 1.8(4) . . . . ?
C36' C31' C32' C33' 1.4(4) . . . . ?
C36' C35' C34' C33' -1.1(5) . . . . ?
C35' C34' C33' C32' 0.5(5) . . . . ?
C34' C33' C32' C31' -0.6(5) . . . . ?
C32' C31' C36' C35' -2.0(4) . . . . ?
C24' N21' C22' O21' 10.8(3) . . . . ?
C24' N21' C22' C23' -171.8(3) . . . . ?
C25' N21' C22' O21' -159.9(2) . . . . ?
C25' N21' C22' C23' 17.6(4) . . . . ?
C30' N23' C26' N22' -146.2(2) . . . . ?
C30' N23' C26' C23' 32.6(3) . . . . ?
C29' N23' C26' N22' 35.1(3) . . . . ?
C29' N23' C26' C23' -146.1(2) . . . . ?
C28' N22' C26' N23' 25.4(3) . . . . ?
C28' N22' C26' C23' -153.4(2) . . . . ?
C27' N22' C26' N23' -160.4(2) . . . . ?
C27' N22' C26' C23' 20.8(3) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.073
_oxdiff_exptl_absorpt_empirical_full_min 0.981



