# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1051148'
_audit_update_record             
;
2015-02-25 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H36 N4, 4(F6 P)'
_chemical_formula_sum            'C30 H36 F24 N4 P4'
_chemical_formula_weight         1032.51

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'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           72
_space_group_name_H-M_alt        'I b a m'
_space_group_name_Hall           '-I 2 2c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   23.9500(13)
_cell_length_b                   7.9241(4)
_cell_length_c                   21.1235(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4008.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2186
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.71

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_F_000             2080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.331
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6690
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  triumph
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14117
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.928
_diffrn_reflns_theta_max         28.039
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2504
_reflns_number_gt                1712
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1006P)²+11.2996P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2504
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1906
_refine_ls_wR_factor_gt          0.1694
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.12616(13) 0.9548(4) 0.34422(15) 0.0244(7) Uani 1 1 d . . . . .
H1 H 0.1539 0.8791 0.3291 0.029 Uiso 1 1 calc R U . . .
C2 C 0.07062(13) 0.9115(4) 0.33938(15) 0.0244(7) Uani 1 1 d . . . . .
H2 H 0.0601 0.8064 0.3214 0.029 Uiso 1 1 calc R U . . .
C3 C 0.03000(12) 1.0235(4) 0.36112(14) 0.0210(6) Uani 1 1 d . . . . .
C4 C 0.04684(13) 1.1784(4) 0.38584(16) 0.0256(7) Uani 1 1 d . . . . .
H4 H 0.0199 1.2583 0.3997 0.031 Uiso 1 1 calc R U . . .
C5 C 0.10301(13) 1.2145(4) 0.39000(16) 0.0248(7) Uani 1 1 d . . . . .
H5 H 0.1147 1.3195 0.4072 0.030 Uiso 1 1 calc R U . . .
C6 C 0.20189(12) 1.1386(4) 0.37926(15) 0.0250(7) Uani 1 1 d . . . . .
H6A H 0.2075 1.2622 0.3813 0.030 Uiso 1 1 calc R U . . .
H6B H 0.2232 1.0950 0.3426 0.030 Uiso 1 1 calc R U . . .
C7 C 0.22426(13) 1.0581(4) 0.43983(15) 0.0234(6) Uani 1 1 d . . . . .
H7A H 0.2651 1.0768 0.4420 0.028 Uiso 1 1 calc R U . . .
H7B H 0.2178 0.9348 0.4379 0.028 Uiso 1 1 calc R U . . .
C8 C 0.19736(18) 1.1274(5) 0.5000 0.0214(9) Uani 1 2 d S T P . .
H8A H 0.2005 1.2520 0.5000 0.026 Uiso 1 2 calc R U P . .
H8B H 0.1572 1.0984 0.5000 0.026 Uiso 1 2 calc R U P . .
F1 F 0.13288(13) 0.4844(4) 0.5000 0.0406(8) Uani 1 2 d S T P . .
F2 F 0.06541(16) 0.8322(4) 0.5000 0.0568(10) Uani 1 2 d S T P . .
F3 F 0.05872(10) 0.5885(4) 0.44598(13) 0.0562(7) Uani 1 1 d . . . . .
F4 F 0.14021(10) 0.7281(3) 0.44722(12) 0.0516(7) Uani 1 1 d . . . . .
F5 F 0.16395(12) 0.5259(3) 0.32474(11) 0.0563(8) Uani 1 1 d . . . . .
F6 F 0.1612(3) 0.3088(4) 0.25707(16) 0.178(3) Uani 1 1 d . . . . .
F7 F 0.2250(2) 0.4438(9) 0.2617(3) 0.068(2) Uani 0.5 1 d . . P . .
F8 F 0.1022(2) 0.5673(9) 0.2427(4) 0.085(2) Uani 0.5 1 d . . P . .
P1 P 0.09856(5) 0.65851(15) 0.5000 0.0238(3) Uani 1 2 d S T P . .
P2 P 0.16278(6) 0.5000 0.2500 0.0305(3) Uani 1 2 d S T P . .
N1 N 0.14152(10) 1.1023(3) 0.36995(12) 0.0210(6) 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
C1 N1 1.341(4) . ?
C1 C2 1.377(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.395(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(4) . ?
C3 C3 1.485(6) 4_575 ?
C4 C5 1.378(4) . ?
C4 H4 0.9500 . ?
C5 N1 1.350(4) . ?
C5 H5 0.9500 . ?
C6 N1 1.487(4) . ?
C6 C7 1.527(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.527(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C7 1.527(4) 12_556 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
F1 P1 1.606(3) . ?
F2 P1 1.589(3) . ?
F3 P1 1.588(2) . ?
F4 P1 1.595(2) . ?
F5 P2 1.592(2) . ?
F6 P2 1.523(3) . ?
F7 P2 1.575(5) . ?
F8 P2 1.554(5) . ?
P1 F3 1.587(2) 12_556 ?
P1 F4 1.595(2) 12_556 ?
P2 F6 1.523(3) 2_565 ?
P2 F8 1.554(5) 2_565 ?
P2 F7 1.575(5) 2_565 ?
P2 F5 1.592(2) 2_565 ?

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
N1 C1 C2 120.8(3) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 C3 120.1(3) . 4_575 ?
C2 C3 C3 121.0(3) . 4_575 ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 120.7(3) . . ?
N1 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
N1 C6 C7 111.8(3) . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C8 113.5(3) . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C7 112.6(4) 12_556 . ?
C7 C8 H8A 109.1 12_556 . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 12_556 . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
F3 P1 F3 91.9(2) 12_556 . ?
F3 P1 F2 90.15(15) 12_556 . ?
F3 P1 F2 90.15(15) . . ?
F3 P1 F4 178.18(16) 12_556 . ?
F3 P1 F4 89.68(15) . . ?
F2 P1 F4 90.74(15) . . ?
F3 P1 F4 89.68(15) 12_556 12_556 ?
F3 P1 F4 178.19(16) . 12_556 ?
F2 P1 F4 90.74(15) . 12_556 ?
F4 P1 F4 88.7(2) . 12_556 ?
F3 P1 F1 90.41(14) 12_556 . ?
F3 P1 F1 90.42(14) . . ?
F2 P1 F1 179.2(2) . . ?
F4 P1 F1 88.68(14) . . ?
F4 P1 F1 88.68(14) 12_556 . ?
F6 P2 F6 177.2(6) . 2_565 ?
F6 P2 F8 68.1(3) . 2_565 ?
F6 P2 F8 109.2(5) 2_565 2_565 ?
F6 P2 F8 109.2(5) . . ?
F6 P2 F8 68.1(3) 2_565 . ?
F6 P2 F7 108.6(4) . 2_565 ?
F6 P2 F7 74.1(4) 2_565 2_565 ?
F8 P2 F7 175.2(4) 2_565 2_565 ?
F8 P2 F7 140.5(4) . 2_565 ?
F6 P2 F7 74.1(4) . . ?
F6 P2 F7 108.6(4) 2_565 . ?
F8 P2 F7 140.5(4) 2_565 . ?
F8 P2 F7 175.2(4) . . ?
F6 P2 F5 88.24(16) . 2_565 ?
F6 P2 F5 91.81(16) 2_565 2_565 ?
F8 P2 F5 94.1(3) 2_565 2_565 ?
F8 P2 F5 87.8(3) . 2_565 ?
F7 P2 F5 82.2(3) 2_565 2_565 ?
F7 P2 F5 95.9(3) . 2_565 ?
F6 P2 F5 91.81(16) . . ?
F6 P2 F5 88.24(16) 2_565 . ?
F8 P2 F5 87.8(3) 2_565 . ?
F8 P2 F5 94.1(3) . . ?
F7 P2 F5 95.9(3) 2_565 . ?
F7 P2 F5 82.2(3) . . ?
F5 P2 F5 178.0(2) 2_565 . ?
C1 N1 C5 121.0(3) . . ?
C1 N1 C6 119.3(3) . . ?
C5 N1 C6 119.7(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
N1 C1 C2 C3 0.5(5) . . . . ?
C1 C2 C3 C4 1.5(5) . . . . ?
C1 C2 C3 C3 -175.4(2) . . . 4_575 ?
C2 C3 C4 C5 -2.1(5) . . . . ?
C3 C3 C4 C5 175.0(3) 4_575 . . . ?
C3 C4 C5 N1 0.6(5) . . . . ?
N1 C6 C7 C8 -63.6(4) . . . . ?
C6 C7 C8 C7 -174.4(2) . . . 12_556 ?
C2 C1 N1 C5 -2.1(5) . . . . ?
C2 C1 N1 C6 175.0(3) . . . . ?
C4 C5 N1 C1 1.5(5) . . . . ?
C4 C5 N1 C6 -175.5(3) . . . . ?
C7 C6 N1 C1 -82.2(3) . . . . ?
C7 C6 N1 C5 94.8(3) . . . . ?

_refine_diff_density_max         1.166
_refine_diff_density_min         -1.160
_refine_diff_density_rms         0.086

_shelxl_version_number           2013-4


_chemical_properties_physical    Air-sensitive
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1051149'
_audit_update_record             
;
2015-02-25 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H44 N4, 3(F6 P), 3(C H3 N O2)'
_chemical_formula_sum            'C37 H53 F18 N7 O6 P3'
_chemical_formula_weight         1126.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   24.2281(11)
_cell_length_b                   16.2943(7)
_cell_length_c                   25.5184(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10074.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4167
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      26.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             4632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6790
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36571
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.596
_diffrn_reflns_theta_max         27.904
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6161
_reflns_number_gt                3417
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6161
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1604
_refine_ls_R_factor_gt           0.1078
_refine_ls_wR_factor_ref         0.3587
_refine_ls_wR_factor_gt          0.3235
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_restrained_S_all      1.190
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.17434(19) 0.0913(3) 0.13301(18) 0.0466(11) Uani 1 1 d . . . . .
H1 H 0.1845 0.0499 0.1087 0.056 Uiso 1 1 calc R U . . .
C2 C 0.17875(17) 0.0758(3) 0.18526(17) 0.0430(10) Uani 1 1 d . . . . .
H2 H 0.1914 0.0239 0.1972 0.052 Uiso 1 1 calc R U . . .
C3 C 0.16445(15) 0.1369(2) 0.22127(15) 0.0311(9) Uani 1 1 d . . . . .
C4 C 0.14666(17) 0.2118(2) 0.20181(16) 0.0379(9) Uani 1 1 d . . . . .
H4 H 0.1377 0.2552 0.2252 0.045 Uiso 1 1 calc R U . . .
C5 C 0.14212(19) 0.2233(3) 0.14890(17) 0.0425(10) Uani 1 1 d . . . . .
H5 H 0.1290 0.2742 0.1358 0.051 Uiso 1 1 calc R U . . .
C6 C 0.1493(2) 0.1756(3) 0.05770(17) 0.0557(13) Uani 1 1 d . . . . .
H6A H 0.1446 0.2348 0.0503 0.067 Uiso 1 1 calc R U . . .
H6B H 0.1831 0.1568 0.0395 0.067 Uiso 1 1 calc R U . . .
C7 C 0.1023(4) 0.1310(5) 0.0377(2) 0.113(3) Uani 1 1 d . . . . .
H7A H 0.1002 0.1431 -0.0002 0.135 Uiso 1 1 calc R U . . .
H7B H 0.1114 0.0719 0.0409 0.135 Uiso 1 1 calc R U . . .
C8 C 0.0501(3) 0.1405(8) 0.0572(3) 0.166(6) Uani 1 1 d . . . . .
H8A H 0.0447 0.2006 0.0604 0.200 Uiso 1 1 calc R U . . .
H8B H 0.0516 0.1192 0.0935 0.200 Uiso 1 1 calc R U . . .
C9 C 0.0000 0.1096(9) 0.0358(4) 0.134(6) Uani 1 2 d S T P . .
H9A H 0.0000 0.0492 0.0400 0.161 Uiso 1 2 calc R U P . .
H9B H 0.0000 0.1212 -0.0023 0.161 Uiso 1 2 calc R U P . .
C10 C 0.14417(16) 0.0342(2) 0.35145(16) 0.0353(9) Uani 1 1 d . . . . .
H10 H 0.1306 -0.0164 0.3647 0.042 Uiso 1 1 calc R U . . .
C11 C 0.14620(16) 0.0463(2) 0.29830(16) 0.0349(9) Uani 1 1 d . . . . .
H11 H 0.1346 0.0042 0.2751 0.042 Uiso 1 1 calc R U . . .
C12 C 0.16529(15) 0.1202(2) 0.27862(14) 0.0297(8) Uani 1 1 d . . . . .
C13 C 0.18284(17) 0.1791(3) 0.31391(16) 0.0391(10) Uani 1 1 d . . . . .
H13 H 0.1966 0.2302 0.3016 0.047 Uiso 1 1 calc R U . . .
C14 C 0.18039(18) 0.1638(3) 0.36632(17) 0.0429(10) Uani 1 1 d . . . . .
H14 H 0.1927 0.2045 0.3903 0.052 Uiso 1 1 calc R U . . .
C15 C 0.15621(17) 0.0800(3) 0.44244(15) 0.0414(10) Uani 1 1 d . . . . .
H15A H 0.1894 0.1027 0.4599 0.050 Uiso 1 1 calc R U . . .
H15B H 0.1546 0.0205 0.4502 0.050 Uiso 1 1 calc R U . . .
C16 C 0.10499(18) 0.1217(3) 0.46421(15) 0.0372(9) Uani 1 1 d . . . . .
H16A H 0.1046 0.1151 0.5028 0.045 Uiso 1 1 calc R U . . .
H16B H 0.1071 0.1812 0.4565 0.045 Uiso 1 1 calc R U . . .
C17 C 0.05154(16) 0.0880(3) 0.44203(15) 0.0379(9) Uani 1 1 d . . . . .
H17A H 0.0507 0.0989 0.4039 0.045 Uiso 1 1 calc R U . . .
H17B H 0.0511 0.0278 0.4470 0.045 Uiso 1 1 calc R U . . .
C18 C 0.0000 0.1239(4) 0.4666(2) 0.0373(13) Uani 1 2 d S T P . .
H18A H 0.0000 0.1123 0.5047 0.045 Uiso 1 2 calc R U P . .
H18B H 0.0000 0.1842 0.4618 0.045 Uiso 1 2 calc R U P . .
C19 C 0.4165(6) 0.8895(5) 0.3316(4) 0.156(5) Uani 1 1 d . . . . .
H19A H 0.3763 0.8941 0.3288 0.234 Uiso 1 1 calc R U . . .
H19B H 0.4324 0.8809 0.2968 0.234 Uiso 1 1 calc R U . . .
H19C H 0.4315 0.9401 0.3468 0.234 Uiso 1 1 calc R U . . .
C20 C 0.5000 0.1476(5) 0.2356(4) 0.069(2) Uani 1 2 d S T P . .
H20A H 0.5194 0.1215 0.2063 0.103 Uiso 0.5 1 calc R U P . .
H20B H 0.5187 0.1989 0.2449 0.103 Uiso 0.5 1 calc R U P . .
H20C H 0.4619 0.1594 0.2252 0.103 Uiso 0.5 1 calc R U P . .
N1 N 0.15603(15) 0.1633(2) 0.11518(13) 0.0408(8) Uani 1 1 d . . . . .
N2 N 0.16093(13) 0.0921(2) 0.38494(13) 0.0332(7) Uani 1 1 d . . . . .
N3 N 0.4301(2) 0.8219(5) 0.3644(3) 0.0877(17) Uani 1 1 d . . . . .
N4 N 0.5000 0.0926(3) 0.2806(2) 0.0498(14) Uani 1 2 d S T P . .
F1 F 0.2358(2) 0.2991(3) 0.45504(19) 0.1246(18) Uani 1 1 d . . . . .
F2 F 0.18222(16) 0.3745(3) 0.4079(3) 0.125(2) Uani 1 1 d . . . . .
F3 F 0.25644(18) 0.3139(3) 0.37475(17) 0.1094(16) Uani 1 1 d . . . . .
F4 F 0.25447(16) 0.4509(3) 0.3830(2) 0.1140(17) Uani 1 1 d . . . . .
F5 F 0.31132(14) 0.37731(18) 0.43041(16) 0.0723(10) Uani 1 1 d . . . . .
F6 F 0.2352(2) 0.4392(3) 0.4637(2) 0.147(2) Uani 1 1 d . . . . .
F7 F 0.0000 0.0276(3) 0.6678(2) 0.1015(19) Uani 1 2 d S T P . .
F8 F -0.0475(4) 0.1285(3) 0.7052(3) 0.189(4) Uani 1 1 d . . . . .
F9 F 0.0000 0.2204(3) 0.6601(2) 0.0944(17) Uani 1 2 d S T P . .
F10 F 0.0458(2) 0.1200(2) 0.6204(2) 0.1197(19) Uani 1 1 d . . . . .
P1 P 0.24561(5) 0.37557(7) 0.42016(5) 0.0418(4) Uani 1 1 d . . . . .
P2 P 0.0000 0.12372(10) 0.66507(7) 0.0473(5) Uani 1 2 d S T P . .
O1 O 0.4368(3) 0.8332(8) 0.4070(3) 0.213(5) Uani 1 1 d . . . . .
O2 O 0.4298(3) 0.7560(4) 0.3439(4) 0.155(3) Uani 1 1 d . . . . .
O3 O 0.45614(16) 0.0714(3) 0.29771(19) 0.0848(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
C1 N1 1.334(6) . ?
C1 C2 1.361(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.398(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(5) . ?
C3 C12 1.489(5) . ?
C4 C5 1.367(6) . ?
C4 H4 0.9500 . ?
C5 N1 1.345(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.444(8) . ?
C6 N1 1.489(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.368(11) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.425(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C8 1.425(11) 10 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.337(5) . ?
C10 C11 1.371(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(5) . ?
C13 C14 1.362(6) . ?
C13 H13 0.9500 . ?
C14 N2 1.346(6) . ?
C14 H14 0.9500 . ?
C15 N2 1.485(5) . ?
C15 C16 1.520(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.516(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.515(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C17 1.515(5) 10 ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N3 1.422(10) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N4 1.456(10) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N3 O1 1.115(8) . ?
N3 O2 1.194(8) . ?
N4 O3 1.200(4) . ?
N4 O3 1.200(4) 10_655 ?
F1 P1 1.549(4) . ?
F2 P1 1.568(4) . ?
F3 P1 1.556(4) . ?
F4 P1 1.565(4) . ?
F5 P1 1.614(3) . ?
F6 P1 1.540(4) . ?
F7 P2 1.567(5) . ?
F8 P2 1.542(5) . ?
F9 P2 1.580(5) . ?
F10 P2 1.592(5) . ?
P2 F8 1.542(5) 10 ?
P2 F10 1.592(5) 10 ?

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
N1 C1 C2 121.5(4) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C1 C2 C3 119.5(4) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 117.9(4) . . ?
C4 C3 C12 121.1(4) . . ?
C2 C3 C12 120.8(4) . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 120.8(4) . . ?
N1 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 N1 111.5(4) . . ?
C7 C6 H6A 109.3 . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
N1 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 122.9(7) . . ?
C8 C7 H7A 106.6 . . ?
C6 C7 H7A 106.6 . . ?
C8 C7 H7B 106.6 . . ?
C6 C7 H7B 106.6 . . ?
H7A C7 H7B 106.6 . . ?
C7 C8 C9 127.4(8) . . ?
C7 C8 H8A 105.4 . . ?
C9 C8 H8A 105.4 . . ?
C7 C8 H8B 105.4 . . ?
C9 C8 H8B 105.4 . . ?
H8A C8 H8B 106.0 . . ?
C8 C9 C8 117.0(12) . 10 ?
C8 C9 H9A 108.1 . . ?
C8 C9 H9A 108.1 10 . ?
C8 C9 H9B 108.1 . . ?
C8 C9 H9B 108.1 10 . ?
H9A C9 H9B 107.3 . . ?
N2 C10 C11 121.3(4) . . ?
N2 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 119.8(4) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 118.0(3) . . ?
C13 C12 C3 121.2(3) . . ?
C11 C12 C3 120.7(3) . . ?
C14 C13 C12 119.9(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N2 C14 C13 121.4(4) . . ?
N2 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
N2 C15 C16 111.4(3) . . ?
N2 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
N2 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C15 113.5(3) . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 114.2(4) . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C16 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 C17 111.1(5) 10 . ?
C17 C18 H18A 109.4 10 . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 10 . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C5 120.3(4) . . ?
C1 N1 C6 119.3(4) . . ?
C5 N1 C6 120.4(4) . . ?
C10 N2 C14 119.6(3) . . ?
C10 N2 C15 121.0(4) . . ?
C14 N2 C15 119.4(4) . . ?
O1 N3 O2 125.2(11) . . ?
O1 N3 C19 118.7(10) . . ?
O2 N3 C19 116.0(9) . . ?
O3 N4 O3 124.6(7) . 10_655 ?
O3 N4 C20 117.7(3) . . ?
O3 N4 C20 117.7(3) 10_655 . ?
F6 P1 F1 95.9(4) . . ?
F6 P1 F3 177.9(3) . . ?
F1 P1 F3 86.2(3) . . ?
F6 P1 F4 86.0(3) . . ?
F1 P1 F4 177.7(3) . . ?
F3 P1 F4 91.9(3) . . ?
F6 P1 F2 89.5(3) . . ?
F1 P1 F2 87.5(3) . . ?
F3 P1 F2 90.5(3) . . ?
F4 P1 F2 91.2(3) . . ?
F6 P1 F5 91.9(2) . . ?
F1 P1 F5 94.1(3) . . ?
F3 P1 F5 88.0(2) . . ?
F4 P1 F5 87.1(2) . . ?
F2 P1 F5 177.7(3) . . ?
F8 P2 F8 96.5(8) . 10 ?
F8 P2 F7 91.2(3) . . ?
F8 P2 F7 91.2(3) 10 . ?
F8 P2 F9 90.2(3) . . ?
F8 P2 F9 90.2(3) 10 . ?
F7 P2 F9 178.0(4) . . ?
F8 P2 F10 87.6(5) . 10 ?
F8 P2 F10 175.8(4) 10 10 ?
F7 P2 F10 89.7(2) . 10 ?
F9 P2 F10 88.9(2) . 10 ?
F8 P2 F10 175.8(4) . . ?
F8 P2 F10 87.6(5) 10 . ?
F7 P2 F10 89.7(2) . . ?
F9 P2 F10 88.9(2) . . ?
F10 P2 F10 88.3(5) 10 . ?

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
N1 C1 C2 C3 -0.8(7) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C1 C2 C3 C12 176.0(4) . . . . ?
C2 C3 C4 C5 1.8(6) . . . . ?
C12 C3 C4 C5 -174.8(4) . . . . ?
C3 C4 C5 N1 -1.7(6) . . . . ?
N1 C6 C7 C8 55.6(10) . . . . ?
C6 C7 C8 C9 169.8(11) . . . . ?
C7 C8 C9 C8 -168.2(7) . . . 10 ?
N2 C10 C11 C12 -0.8(6) . . . . ?
C10 C11 C12 C13 1.3(5) . . . . ?
C10 C11 C12 C3 -176.0(3) . . . . ?
C4 C3 C12 C13 -41.3(5) . . . . ?
C2 C3 C12 C13 142.2(4) . . . . ?
C4 C3 C12 C11 135.8(4) . . . . ?
C2 C3 C12 C11 -40.7(5) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C3 C12 C13 C14 176.5(4) . . . . ?
C12 C13 C14 N2 -0.3(7) . . . . ?
N2 C15 C16 C17 62.0(5) . . . . ?
C15 C16 C17 C18 175.2(4) . . . . ?
C16 C17 C18 C17 179.4(3) . . . 10 ?
C2 C1 N1 C5 1.0(7) . . . . ?
C2 C1 N1 C6 -177.0(4) . . . . ?
C4 C5 N1 C1 0.3(6) . . . . ?
C4 C5 N1 C6 178.2(4) . . . . ?
C7 C6 N1 C1 72.8(7) . . . . ?
C7 C6 N1 C5 -105.1(6) . . . . ?
C11 C10 N2 C14 -0.2(6) . . . . ?
C11 C10 N2 C15 177.2(3) . . . . ?
C13 C14 N2 C10 0.8(6) . . . . ?
C13 C14 N2 C15 -176.7(4) . . . . ?
C16 C15 N2 C10 -98.2(4) . . . . ?
C16 C15 N2 C14 79.2(5) . . . . ?

_refine_diff_density_max         1.109
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.101

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.250 0.118 0.750 50.8 31.4
2 0.750 0.118 0.750 50.7 31.3
3 0.250 0.382 0.250 50.8 31.4
4 0.750 0.382 0.250 50.7 31.4
5 0.250 0.618 0.750 50.7 31.3
6 0.750 0.618 0.750 50.8 31.4
7 0.250 0.882 0.250 50.7 31.4
8 0.750 0.882 0.250 50.8 31.4
_platon_squeeze_details          
;
 The residual electron density was assigned to half a molecule of the
 nitromethane solvent [251/16 = 16 e per asymmetric unit; half a molecule
 of CH3NO2 would give 16e].
;

_shelxl_version_number           2013-4


_chemical_properties_physical    Air-sensitive
####################################################################### 
# 
# 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_jwmb140703
_database_code_depnum_ccdc_archive 'CCDC 1051150'
_audit_update_record             
;
2015-02-25 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H44 N4, 2(F6 P), 2(C2 H3 N)'
_chemical_formula_sum            'C38 H50 F12 N6 P2'
_chemical_formula_weight         880.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.5413(8)
_cell_length_b                   14.3275(9)
_cell_length_c                   22.1621(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4299.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5742
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      29.03

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             1832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.188
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5892
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26866
_diffrn_reflns_av_unetI/netI     0.1018
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.692
_diffrn_reflns_theta_max         29.066
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             11473
_reflns_number_gt                5917
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1478P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         11473
_refine_ls_number_parameters     526
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1623
_refine_ls_R_factor_gt           0.0931
_refine_ls_wR_factor_ref         0.2662
_refine_ls_wR_factor_gt          0.2329
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4714(5) 0.4671(6) 0.1973(3) 0.0410(19) Uani 1 1 d . . . . .
H1 H 0.5224 0.4222 0.1927 0.049 Uiso 1 1 calc R U . . .
C2 C 0.3756(6) 0.4397(6) 0.1956(3) 0.0403(18) Uani 1 1 d . . . . .
H2 H 0.3615 0.3754 0.1900 0.048 Uiso 1 1 calc R U . . .
C3 C 0.2966(5) 0.5020(5) 0.2018(3) 0.0315(15) Uani 1 1 d . . . . .
C4 C 0.3269(5) 0.5969(5) 0.2104(3) 0.0381(16) Uani 1 1 d . . . . .
H4 H 0.2779 0.6439 0.2152 0.046 Uiso 1 1 calc R U . . .
C5 C 0.4223(5) 0.6212(5) 0.2119(3) 0.0396(17) Uani 1 1 d . . . . .
H5 H 0.4391 0.6850 0.2176 0.048 Uiso 1 1 calc R U . . .
C6 C 0.6010(5) 0.5850(7) 0.2063(3) 0.053(2) Uani 1 1 d . . . . .
H6A H 0.6062 0.6536 0.2017 0.064 Uiso 1 1 calc R U . . .
H6B H 0.6342 0.5560 0.1712 0.064 Uiso 1 1 calc R U . . .
C7 C 0.6553(5) 0.5564(6) 0.2633(3) 0.0492(19) Uani 1 1 d . . . . .
H7A H 0.6514 0.4877 0.2677 0.059 Uiso 1 1 calc R U . . .
H7B H 0.7258 0.5734 0.2592 0.059 Uiso 1 1 calc R U . . .
C8 C 0.6153(6) 0.6006(7) 0.3185(3) 0.050(2) Uani 1 1 d . . . . .
H8A H 0.5445 0.5844 0.3225 0.060 Uiso 1 1 calc R U . . .
H8B H 0.6203 0.6692 0.3146 0.060 Uiso 1 1 calc R U . . .
C9 C 0.6699(5) 0.5695(6) 0.3755(3) 0.0560(19) Uani 1 1 d . . . . .
H9A H 0.6737 0.5005 0.3759 0.067 Uiso 1 1 calc R U . . .
H9B H 0.7383 0.5939 0.3740 0.067 Uiso 1 1 calc R U . . .
C10 C 0.6219(6) 0.6021(6) 0.4339(3) 0.047(2) Uani 1 1 d . . . . .
H10A H 0.6278 0.6708 0.4367 0.057 Uiso 1 1 calc R U . . .
H10B H 0.5507 0.5865 0.4327 0.057 Uiso 1 1 calc R U . . .
C11 C 0.6668(5) 0.5590(6) 0.4894(3) 0.0482(19) Uani 1 1 d . . . . .
H11A H 0.7373 0.5770 0.4915 0.058 Uiso 1 1 calc R U . . .
H11B H 0.6638 0.4902 0.4856 0.058 Uiso 1 1 calc R U . . .
C12 C 0.6163(5) 0.5876(6) 0.5478(3) 0.0437(19) Uani 1 1 d . . . . .
H12A H 0.6508 0.5579 0.5822 0.052 Uiso 1 1 calc R U . . .
H12B H 0.6219 0.6561 0.5527 0.052 Uiso 1 1 calc R U . . .
C13 C 0.4855(6) 0.4688(6) 0.5574(3) 0.0441(19) Uani 1 1 d . . . . .
H13 H 0.5363 0.4238 0.5626 0.053 Uiso 1 1 calc R U . . .
C14 C 0.3907(5) 0.4414(5) 0.5581(3) 0.0347(16) Uani 1 1 d . . . . .
H14 H 0.3763 0.3769 0.5627 0.042 Uiso 1 1 calc R U . . .
C15 C 0.3103(5) 0.5061(5) 0.5522(3) 0.0285(14) Uani 1 1 d . . . . .
C16 C 0.3401(5) 0.6006(5) 0.5448(3) 0.0337(15) Uani 1 1 d . . . . .
H16 H 0.2908 0.6473 0.5410 0.040 Uiso 1 1 calc R U . . .
C17 C 0.4380(6) 0.6267(5) 0.5430(3) 0.0411(18) Uani 1 1 d . . . . .
H17 H 0.4552 0.6904 0.5372 0.049 Uiso 1 1 calc R U . . .
C18 C 0.0846(5) 0.3575(5) 0.5581(3) 0.0388(17) Uani 1 1 d . . . . .
H18 H 0.0685 0.2932 0.5623 0.047 Uiso 1 1 calc R U . . .
C19 C 0.1797(6) 0.3830(5) 0.5588(3) 0.0389(17) Uani 1 1 d . . . . .
H19 H 0.2292 0.3365 0.5634 0.047 Uiso 1 1 calc R U . . .
C20 C 0.2088(4) 0.4782(4) 0.5528(3) 0.0245(13) Uani 1 1 d . . . . .
C21 C 0.1290(5) 0.5431(5) 0.5463(3) 0.0333(16) Uani 1 1 d . . . . .
H21 H 0.1426 0.6079 0.5425 0.040 Uiso 1 1 calc R U . . .
C22 C 0.0346(5) 0.5129(6) 0.5457(3) 0.0387(17) Uani 1 1 d . . . . .
H22 H -0.0166 0.5577 0.5410 0.046 Uiso 1 1 calc R U . . .
C23 C -0.0934(5) 0.3908(6) 0.5490(3) 0.048(2) Uani 1 1 d . . . . .
H23A H -0.1370 0.4458 0.5538 0.058 Uiso 1 1 calc R U . . .
H23B H -0.1063 0.3481 0.5832 0.058 Uiso 1 1 calc R U . . .
C24 C -0.1199(5) 0.3413(5) 0.4906(3) 0.0398(17) Uani 1 1 d . . . . .
H24A H -0.0817 0.2825 0.4883 0.048 Uiso 1 1 calc R U . . .
H24B H -0.1908 0.3246 0.4918 0.048 Uiso 1 1 calc R U . . .
C25 C -0.1006(5) 0.3973(5) 0.4342(3) 0.0357(16) Uani 1 1 d . . . . .
H25A H -0.0289 0.4099 0.4308 0.043 Uiso 1 1 calc R U . . .
H25B H -0.1351 0.4580 0.4371 0.043 Uiso 1 1 calc R U . . .
C26 C -0.1356(4) 0.3461(4) 0.3778(3) 0.0331(12) Uani 1 1 d . . . . .
H26A H -0.1057 0.2830 0.3771 0.040 Uiso 1 1 calc R U . . .
H26B H -0.2082 0.3385 0.3798 0.040 Uiso 1 1 calc R U . . .
C27 C -0.1090(4) 0.3967(5) 0.3196(3) 0.0313(16) Uani 1 1 d . . . . .
H27A H -0.1465 0.4559 0.3175 0.038 Uiso 1 1 calc R U . . .
H27B H -0.0378 0.4122 0.3201 0.038 Uiso 1 1 calc R U . . .
C28 C -0.1313(5) 0.3393(5) 0.2639(3) 0.0373(16) Uani 1 1 d . . . . .
H28A H -0.2022 0.3224 0.2642 0.045 Uiso 1 1 calc R U . . .
H28B H -0.0929 0.2805 0.2660 0.045 Uiso 1 1 calc R U . . .
C29 C -0.1080(5) 0.3875(6) 0.2045(3) 0.0416(19) Uani 1 1 d . . . . .
H29A H -0.1222 0.3442 0.1708 0.050 Uiso 1 1 calc R U . . .
H29B H -0.1515 0.4426 0.1999 0.050 Uiso 1 1 calc R U . . .
C30 C 0.0700(5) 0.3555(5) 0.1930(3) 0.0382(17) Uani 1 1 d . . . . .
H30 H 0.0533 0.2919 0.1867 0.046 Uiso 1 1 calc R U . . .
C31 C 0.1661(6) 0.3797(5) 0.1937(3) 0.0379(16) Uani 1 1 d . . . . .
H31 H 0.2152 0.3327 0.1897 0.045 Uiso 1 1 calc R U . . .
C32 C 0.1949(5) 0.4743(5) 0.2004(3) 0.0301(15) Uani 1 1 d . . . . .
C33 C 0.1159(6) 0.5383(5) 0.2064(3) 0.0393(18) Uani 1 1 d . . . . .
H33 H 0.1301 0.6030 0.2102 0.047 Uiso 1 1 calc R U . . .
C34 C 0.0204(5) 0.5096(5) 0.2070(3) 0.0369(17) Uani 1 1 d . . . . .
H34 H -0.0307 0.5544 0.2119 0.044 Uiso 1 1 calc R U . . .
C35 C 0.9408(8) 0.1129(6) 0.1162(5) 0.078(3) Uani 1 1 d . . . . .
C36 C 0.8543(6) 0.0567(5) 0.1200(5) 0.071(2) Uani 1 1 d . . . . .
H36A H 0.8098 0.0825 0.1506 0.107 Uiso 1 1 calc R U . . .
H36B H 0.8728 -0.0071 0.1312 0.107 Uiso 1 1 calc R U . . .
H36C H 0.8210 0.0560 0.0807 0.107 Uiso 1 1 calc R U . . .
C37 C 0.5376(9) 0.8833(7) 0.1332(7) 0.097(4) Uani 1 1 d . . . . .
C38 C 0.6258(7) 0.9387(6) 0.1268(6) 0.089(3) Uani 1 1 d . . . . .
H38A H 0.6815 0.9061 0.1456 0.133 Uiso 1 1 calc R U . . .
H38B H 0.6162 0.9991 0.1467 0.133 Uiso 1 1 calc R U . . .
H38C H 0.6397 0.9485 0.0839 0.133 Uiso 1 1 calc R U . . .
N1 N 0.4948(4) 0.5584(5) 0.2055(2) 0.0410(16) Uani 1 1 d . . . . .
N2 N 0.5103(4) 0.5609(4) 0.5494(2) 0.0329(14) Uani 1 1 d . . . . .
N3 N 0.0093(4) 0.4215(5) 0.5516(2) 0.0367(14) Uani 1 1 d . . . . .
N4 N -0.0036(4) 0.4179(5) 0.2008(2) 0.0383(14) Uani 1 1 d . . . . .
N5 N 1.0086(8) 0.1581(7) 0.1128(7) 0.134(4) Uani 1 1 d . . . . .
N6 N 0.4704(9) 0.8391(8) 0.1381(8) 0.160(6) Uani 1 1 d . . . . .
F1 F 0.9161(7) 0.7255(5) 0.0873(4) 0.162(4) Uani 1 1 d . . . . .
F2 F 0.7531(7) 0.7568(5) 0.0960(4) 0.163(4) Uani 1 1 d . . . . .
F3 F 0.8146(3) 0.6238(3) 0.1308(3) 0.0753(15) Uani 1 1 d . . . . .
F4 F 0.9206(7) 0.7082(5) 0.1836(4) 0.168(4) Uani 1 1 d . . . . .
F5 F 0.7632(6) 0.7412(5) 0.1903(4) 0.149(4) Uani 1 1 d . . . . .
F6 F 0.8639(3) 0.8389(3) 0.1487(3) 0.0757(16) Uani 1 1 d . . . . .
F7 F 0.3772(3) 0.6594(3) 0.3904(2) 0.0667(15) Uani 1 1 d . . . . .
F8 F 0.2682(7) 0.7469(5) 0.3444(5) 0.194(5) Uani 1 1 d . . . . .
F9 F 0.3332(3) 0.8780(3) 0.3803(3) 0.0602(11) Uani 1 1 d . . . . .
F10 F 0.2850(8) 0.7592(5) 0.4380(4) 0.186(6) Uani 1 1 d . . . . .
F11 F 0.4216(9) 0.7732(5) 0.3294(4) 0.206(6) Uani 1 1 d . . . . .
F12 F 0.4453(6) 0.7887(5) 0.4225(5) 0.204(6) Uani 1 1 d . . . . .
P1 P 0.83916(13) 0.73170(13) 0.13914(10) 0.0468(6) Uani 1 1 d . . . . .
P2 P 0.35528(12) 0.76807(13) 0.38525(9) 0.0415(5) 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
C1 C2 1.355(10) . ?
C1 N1 1.358(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.399(10) . ?
C2 H2 0.9500 . ?
C3 C32 1.434(10) . ?
C3 C4 1.434(10) . ?
C4 C5 1.339(10) . ?
C4 H4 0.9500 . ?
C5 N1 1.340(10) . ?
C5 H5 0.9500 . ?
C6 N1 1.489(9) . ?
C6 C7 1.518(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.480(10) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.529(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.522(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.504(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.521(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N2 1.487(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.343(10) . ?
C13 N2 1.372(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.436(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.422(10) . ?
C15 C20 1.432(9) . ?
C16 C17 1.379(10) . ?
C16 H16 0.9500 . ?
C17 N2 1.367(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.339(10) . ?
C18 N3 1.380(9) . ?
C18 H18 0.9500 . ?
C19 C20 1.426(9) . ?
C19 H19 0.9500 . ?
C20 C21 1.433(9) . ?
C21 C22 1.349(10) . ?
C21 H21 0.9500 . ?
C22 N3 1.360(10) . ?
C22 H22 0.9500 . ?
C23 N3 1.461(9) . ?
C23 C24 1.518(9) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.509(9) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.525(9) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.522(8) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.513(9) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.520(9) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 N4 1.482(9) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.346(10) . ?
C30 N4 1.350(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.418(9) . ?
C31 H31 0.9500 . ?
C32 C33 1.416(10) . ?
C33 C34 1.358(10) . ?
C33 H33 0.9500 . ?
C34 N4 1.360(10) . ?
C34 H34 0.9500 . ?
C35 N5 1.125(12) . ?
C35 C36 1.424(13) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 N6 1.114(13) . ?
C37 C38 1.441(14) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
F1 P1 1.554(7) . ?
F2 P1 1.550(6) . ?
F3 P1 1.592(4) . ?
F4 P1 1.518(7) . ?
F5 P1 1.538(6) . ?
F6 P1 1.586(5) . ?
F7 P2 1.589(4) . ?
F8 P2 1.517(6) . ?
F9 P2 1.607(4) . ?
F10 P2 1.512(6) . ?
F11 P2 1.531(7) . ?
F12 P2 1.502(6) . ?

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
C2 C1 N1 120.4(7) . . ?
C2 C1 H1 119.8 . . ?
N1 C1 H1 119.8 . . ?
C1 C2 C3 123.0(8) . . ?
C1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
C2 C3 C32 123.8(7) . . ?
C2 C3 C4 113.6(6) . . ?
C32 C3 C4 122.7(7) . . ?
C5 C4 C3 121.7(7) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 N1 122.0(7) . . ?
C4 C5 H5 119.0 . . ?
N1 C5 H5 119.0 . . ?
N1 C6 C7 114.1(6) . . ?
N1 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
N1 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C6 113.3(7) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C9 112.4(6) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 114.0(5) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 113.4(6) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 113.8(6) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
N2 C12 C11 112.7(6) . . ?
N2 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
N2 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 N2 121.1(7) . . ?
C14 C13 H13 119.5 . . ?
N2 C13 H13 119.5 . . ?
C13 C14 C15 122.4(7) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C16 C15 C20 122.7(6) . . ?
C16 C15 C14 114.2(6) . . ?
C20 C15 C14 123.2(7) . . ?
C17 C16 C15 122.4(7) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
N2 C17 C16 119.8(7) . . ?
N2 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 N3 122.0(7) . . ?
C19 C18 H18 119.0 . . ?
N3 C18 H18 119.0 . . ?
C18 C19 C20 121.7(7) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C19 C20 C15 122.2(6) . . ?
C19 C20 C21 115.0(6) . . ?
C15 C20 C21 122.8(6) . . ?
C22 C21 C20 120.5(7) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 N3 123.1(7) . . ?
C21 C22 H22 118.5 . . ?
N3 C22 H22 118.5 . . ?
N3 C23 C24 113.5(5) . . ?
N3 C23 H23A 108.9 . . ?
C24 C23 H23A 108.9 . . ?
N3 C23 H23B 108.9 . . ?
C24 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C25 C24 C23 114.6(6) . . ?
C25 C24 H24A 108.6 . . ?
C23 C24 H24A 108.6 . . ?
C25 C24 H24B 108.6 . . ?
C23 C24 H24B 108.6 . . ?
H24A C24 H24B 107.6 . . ?
C24 C25 C26 111.7(6) . . ?
C24 C25 H25A 109.3 . . ?
C26 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
C26 C25 H25B 109.3 . . ?
H25A C25 H25B 107.9 . . ?
C27 C26 C25 113.1(5) . . ?
C27 C26 H26A 109.0 . . ?
C25 C26 H26A 109.0 . . ?
C27 C26 H26B 109.0 . . ?
C25 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
C28 C27 C26 112.7(6) . . ?
C28 C27 H27A 109.1 . . ?
C26 C27 H27A 109.1 . . ?
C28 C27 H27B 109.1 . . ?
C26 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?
C27 C28 C29 114.7(6) . . ?
C27 C28 H28A 108.6 . . ?
C29 C28 H28A 108.6 . . ?
C27 C28 H28B 108.6 . . ?
C29 C28 H28B 108.6 . . ?
H28A C28 H28B 107.6 . . ?
N4 C29 C28 112.3(5) . . ?
N4 C29 H29A 109.1 . . ?
C28 C29 H29A 109.1 . . ?
N4 C29 H29B 109.1 . . ?
C28 C29 H29B 109.1 . . ?
H29A C29 H29B 107.9 . . ?
C31 C30 N4 122.8(7) . . ?
C31 C30 H30 118.6 . . ?
N4 C30 H30 118.6 . . ?
C30 C31 C32 120.8(7) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C33 C32 C31 114.9(6) . . ?
C33 C32 C3 123.0(7) . . ?
C31 C32 C3 122.1(7) . . ?
C34 C33 C32 121.6(7) . . ?
C34 C33 H33 119.2 . . ?
C32 C33 H33 119.2 . . ?
C33 C34 N4 121.3(7) . . ?
C33 C34 H34 119.4 . . ?
N4 C34 H34 119.4 . . ?
N5 C35 C36 179.2(15) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N6 C37 C38 178.9(12) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C5 N1 C1 119.3(6) . . ?
C5 N1 C6 122.3(7) . . ?
C1 N1 C6 118.3(7) . . ?
C17 N2 C13 120.2(6) . . ?
C17 N2 C12 120.7(7) . . ?
C13 N2 C12 119.1(6) . . ?
C22 N3 C18 117.7(6) . . ?
C22 N3 C23 121.7(7) . . ?
C18 N3 C23 120.5(7) . . ?
C30 N4 C34 118.4(6) . . ?
C30 N4 C29 121.1(7) . . ?
C34 N4 C29 120.4(7) . . ?
F4 P1 F5 91.5(6) . . ?
F4 P1 F2 177.6(6) . . ?
F5 P1 F2 86.1(5) . . ?
F4 P1 F1 88.9(6) . . ?
F5 P1 F1 178.2(4) . . ?
F2 P1 F1 93.5(5) . . ?
F4 P1 F6 88.5(3) . . ?
F5 P1 F6 87.5(3) . . ?
F2 P1 F6 90.9(3) . . ?
F1 P1 F6 90.7(3) . . ?
F4 P1 F3 90.7(4) . . ?
F5 P1 F3 91.8(3) . . ?
F2 P1 F3 89.8(3) . . ?
F1 P1 F3 90.0(3) . . ?
F6 P1 F3 178.9(4) . . ?
F12 P2 F10 95.9(7) . . ?
F12 P2 F8 176.7(7) . . ?
F10 P2 F8 87.5(7) . . ?
F12 P2 F11 87.7(7) . . ?
F10 P2 F11 176.2(7) . . ?
F8 P2 F11 89.0(7) . . ?
F12 P2 F7 90.1(3) . . ?
F10 P2 F7 88.9(3) . . ?
F8 P2 F7 89.6(3) . . ?
F11 P2 F7 89.7(4) . . ?
F12 P2 F9 89.8(3) . . ?
F10 P2 F9 91.0(3) . . ?
F8 P2 F9 90.6(3) . . ?
F11 P2 F9 90.4(4) . . ?
F7 P2 F9 179.8(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
N1 C1 C2 C3 0.2(11) . . . . ?
C1 C2 C3 C32 -179.7(6) . . . . ?
C1 C2 C3 C4 -0.3(10) . . . . ?
C2 C3 C4 C5 0.2(10) . . . . ?
C32 C3 C4 C5 179.7(6) . . . . ?
C3 C4 C5 N1 -0.1(11) . . . . ?
N1 C6 C7 C8 -61.8(11) . . . . ?
C6 C7 C8 C9 179.1(7) . . . . ?
C7 C8 C9 C10 -171.6(8) . . . . ?
C8 C9 C10 C11 171.0(8) . . . . ?
C9 C10 C11 C12 -177.4(7) . . . . ?
C10 C11 C12 N2 60.1(10) . . . . ?
N2 C13 C14 C15 -1.6(11) . . . . ?
C13 C14 C15 C16 0.7(10) . . . . ?
C13 C14 C15 C20 180.0(6) . . . . ?
C20 C15 C16 C17 -178.6(6) . . . . ?
C14 C15 C16 C17 0.7(10) . . . . ?
C15 C16 C17 N2 -1.1(10) . . . . ?
N3 C18 C19 C20 0.0(11) . . . . ?
C18 C19 C20 C15 -178.7(6) . . . . ?
C18 C19 C20 C21 0.3(10) . . . . ?
C16 C15 C20 C19 178.5(7) . . . . ?
C14 C15 C20 C19 -0.6(9) . . . . ?
C16 C15 C20 C21 -0.4(9) . . . . ?
C14 C15 C20 C21 -179.5(6) . . . . ?
C19 C20 C21 C22 -0.6(9) . . . . ?
C15 C20 C21 C22 178.4(6) . . . . ?
C20 C21 C22 N3 0.6(11) . . . . ?
N3 C23 C24 C25 -56.6(9) . . . . ?
C23 C24 C25 C26 -175.9(6) . . . . ?
C24 C25 C26 C27 -174.9(6) . . . . ?
C25 C26 C27 C28 172.0(6) . . . . ?
C26 C27 C28 C29 178.8(5) . . . . ?
C27 C28 C29 N4 56.6(9) . . . . ?
N4 C30 C31 C32 -2.7(11) . . . . ?
C30 C31 C32 C33 0.5(10) . . . . ?
C30 C31 C32 C3 179.5(6) . . . . ?
C2 C3 C32 C33 -179.7(7) . . . . ?
C4 C3 C32 C33 1.0(10) . . . . ?
C2 C3 C32 C31 1.4(10) . . . . ?
C4 C3 C32 C31 -178.0(7) . . . . ?
C31 C32 C33 C34 1.4(10) . . . . ?
C3 C32 C33 C34 -177.7(6) . . . . ?
C32 C33 C34 N4 -1.1(11) . . . . ?
C4 C5 N1 C1 0.0(10) . . . . ?
C4 C5 N1 C6 179.2(6) . . . . ?
C2 C1 N1 C5 -0.1(10) . . . . ?
C2 C1 N1 C6 -179.3(6) . . . . ?
C7 C6 N1 C5 107.4(9) . . . . ?
C7 C6 N1 C1 -73.4(9) . . . . ?
C16 C17 N2 C13 0.2(10) . . . . ?
C16 C17 N2 C12 -179.8(6) . . . . ?
C14 C13 N2 C17 1.1(10) . . . . ?
C14 C13 N2 C12 -178.8(6) . . . . ?
C11 C12 N2 C17 -106.3(8) . . . . ?
C11 C12 N2 C13 73.7(9) . . . . ?
C21 C22 N3 C18 -0.3(10) . . . . ?
C21 C22 N3 C23 -178.2(6) . . . . ?
C19 C18 N3 C22 0.0(10) . . . . ?
C19 C18 N3 C23 177.9(6) . . . . ?
C24 C23 N3 C22 106.2(8) . . . . ?
C24 C23 N3 C18 -71.6(9) . . . . ?
C31 C30 N4 C34 2.9(10) . . . . ?
C31 C30 N4 C29 -175.1(6) . . . . ?
C33 C34 N4 C30 -1.0(10) . . . . ?
C33 C34 N4 C29 177.0(6) . . . . ?
C28 C29 N4 C30 72.8(8) . . . . ?
C28 C29 N4 C34 -105.1(8) . . . . ?

_refine_diff_density_max         1.060
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.080

_shelxl_version_number           2013-4


_chemical_properties_physical    Air-sensitive
####################################################################### 
# 
# 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_jwmb140916
_database_code_depnum_ccdc_archive 'CCDC 1051151'
_audit_update_record             
;
2015-02-25 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H44 N4, 2(C12 H14 N2), 5(F6 P)'
_chemical_formula_sum            'C58 H72 F30 N8 P5'
_chemical_formula_weight         1606.08

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'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           72
_space_group_name_H-M_alt        'I b a m'
_space_group_name_Hall           '-I 2 2c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.8988(4)
_cell_length_b                   21.8945(7)
_cell_length_c                   25.6947(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6693.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9013
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      29.97

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             3284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.267
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  triumph
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28616
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.860
_diffrn_reflns_theta_max         30.009
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4987
_reflns_number_gt                3873
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0678P)²+16.9999P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4987
_refine_ls_number_parameters     258
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1685
_refine_ls_wR_factor_gt          0.1522
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.65734(17) 0.11124(9) 0.12818(7) 0.0235(4) Uani 1 1 d . . . . .
H1 H 0.6578 0.1546 0.1272 0.028 Uiso 1 1 calc R U . . .
C2 C 0.55693(15) 0.08098(8) 0.12527(7) 0.0202(3) Uani 1 1 d . . . . .
H2 H 0.4891 0.1037 0.1226 0.024 Uiso 1 1 calc R U . . .
C3 C 0.55260(14) 0.01633(7) 0.12611(6) 0.0177(3) Uani 1 1 d . . . . .
C4 C 0.65808(15) -0.01397(8) 0.12894(7) 0.0217(3) Uani 1 1 d . . . . .
H4 H 0.6606 -0.0573 0.1282 0.026 Uiso 1 1 calc R U . . .
C5 C 0.75596(16) 0.01850(9) 0.13274(8) 0.0247(4) Uani 1 1 d . . . . .
H5 H 0.8252 -0.0028 0.1357 0.030 Uiso 1 1 calc R U . . .
C6 C 0.86315(18) 0.11574(11) 0.13561(9) 0.0330(5) Uani 1 1 d . . . . .
H6A H 0.9212 0.0910 0.1534 0.040 Uiso 1 1 calc R U . A 1
H6B H 0.8516 0.1538 0.1557 0.040 Uiso 1 1 calc R U . A 1
C7 C 0.9031(3) 0.13177(18) 0.07787(17) 0.0274(5) Uani 0.5 1 d . . P B 1
H7A H 0.8376 0.1444 0.0567 0.033 Uiso 0.5 1 calc R U P B 1
H7B H 0.9572 0.1661 0.0788 0.033 Uiso 0.5 1 calc R U P B 1
C8 C 0.9584(4) 0.0763(2) 0.05328(18) 0.0304(6) Uani 0.5 1 d . . P B 1
H8A H 1.0210 0.0627 0.0759 0.036 Uiso 0.5 1 calc R U P B 1
H8B H 0.9029 0.0427 0.0517 0.036 Uiso 0.5 1 calc R U P B 1
C7B C 0.9525(3) 0.09335(18) 0.09714(17) 0.0274(5) Uani 0.5 1 d . . P B 2
H7C H 1.0223 0.1173 0.1018 0.033 Uiso 0.5 1 calc R U P B 2
H7D H 0.9700 0.0499 0.1042 0.033 Uiso 0.5 1 calc R U P B 2
C8B C 0.9108(4) 0.1001(2) 0.04156(17) 0.0304(6) Uani 0.5 1 d . . P B 2
H8C H 0.8817 0.1421 0.0367 0.036 Uiso 0.5 1 calc R U P B 2
H8D H 0.8476 0.0715 0.0359 0.036 Uiso 0.5 1 calc R U P B 2
C9 C 1.0029(2) 0.08765(14) 0.0000 0.0299(6) Uani 1 2 d S T P . .
H9A H 1.0767 0.0668 0.0000 0.036 Uiso 1 2 calc R U P B 1
H9B H 1.0204 0.1319 0.0000 0.036 Uiso 1 2 calc R U P B 1
C10 C 0.5101(4) 0.77124(16) 0.0000 0.0441(8) Uani 1 2 d DS T P . .
C11 C 0.6039(3) 0.87141(14) 0.0000 0.0315(6) Uani 1 2 d S T P . .
H11 H 0.6737 0.8503 0.0000 0.038 Uiso 1 2 calc R U P . .
C12 C 0.6043(2) 0.93347(14) 0.0000 0.0288(6) Uani 1 2 d S T P . .
H12 H 0.6739 0.9547 0.0000 0.035 Uiso 1 2 calc R U P . .
C13 C 0.5016(2) 0.96726(13) 0.0000 0.0232(5) Uani 1 2 d S T P . .
C14 C 0.4025(2) 0.93119(14) 0.0000 0.0268(5) Uani 1 2 d S T P . .
H14 H 0.3313 0.9508 0.0000 0.032 Uiso 1 2 calc R U P . .
C15 C 0.4074(3) 0.86886(14) 0.0000 0.0291(6) Uani 1 2 d S T P . .
H15 H 0.3394 0.8461 0.0000 0.035 Uiso 1 2 calc R U P . .
C16 C 0.5000 0.22866(16) 0.2500 0.0445(8) Uani 1 2 d S T P . .
H16A H 0.4551 0.2436 0.2207 0.067 Uiso 0.5 1 calc R U P . .
H16B H 0.5773 0.2436 0.2466 0.067 Uiso 0.5 1 calc R U P . .
H16C H 0.4676 0.2436 0.2827 0.067 Uiso 0.5 1 calc R U P . .
C17 C 0.40203(19) 0.13030(11) 0.24610(8) 0.0324(4) Uani 1 1 d . . . . .
H17 H 0.3335 0.1523 0.2432 0.039 Uiso 1 1 calc R U . . .
C18 C 0.39945(17) 0.06746(10) 0.24627(8) 0.0281(4) Uani 1 1 d . . . . .
H18 H 0.3294 0.0468 0.2438 0.034 Uiso 1 1 calc R U . . .
C19 C 0.5000 0.03328(14) 0.2500 0.0247(5) Uani 1 2 d S T P . .
F1 F 0.30445(16) 0.65788(8) 0.07936(8) 0.0638(5) Uani 1 1 d . . . . .
F2 F 0.24774(15) 0.74813(8) 0.17380(6) 0.0510(4) Uani 1 1 d . . . . .
F3 F 0.24135(17) 0.75486(8) 0.08607(7) 0.0552(4) Uani 1 1 d . . . . .
F4 F 0.14956(15) 0.67876(9) 0.12688(9) 0.0705(6) Uani 1 1 d . . . . .
F5 F 0.30911(19) 0.65103(9) 0.16710(9) 0.0700(6) Uani 1 1 d . . . . .
F6 F 0.40121(14) 0.72792(9) 0.12635(7) 0.0581(5) Uani 1 1 d . . . . .
F7 F 0.0000 0.0000 0.18740(8) 0.0464(5) Uani 1 2 d S T P . .
F8 F 0.1306(2) 0.0000 0.2500 0.136(2) Uani 1 2 d S T P . .
F9 F 0.0000 0.07021(15) 0.2500 0.141(2) Uani 1 2 d S T P . .
P1 P 0.27623(5) 0.70250(3) 0.12664(3) 0.03440(16) Uani 1 1 d . . . . .
P2 P 0.0000 0.0000 0.2500 0.0353(3) Uani 1 4 d S T P . .
N1 N 0.75629(14) 0.08085(8) 0.13243(6) 0.0237(3) Uani 1 1 d . . . . .
N2 N 0.5073(2) 0.83856(11) 0.0000 0.0297(5) Uani 1 2 d S T P . .
N3 N 0.5000 0.16140(13) 0.2500 0.0327(6) Uani 1 2 d S T P . .
H10A H 0.437(2) 0.753(3) 0.0000 0.11(2) Uiso 1 2 d DS . P . .
H10B H 0.545(4) 0.758(2) -0.0311(2) 0.130(19) Uiso 1 1 d 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
C1 N1 1.357(3) . ?
C1 C2 1.368(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.417(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.422(2) . ?
C3 C3 1.442(3) 4_655 ?
C4 C5 1.368(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.365(3) . ?
C5 H5 0.9500 . ?
C6 N1 1.486(2) . ?
C6 C7B 1.532(5) . ?
C6 C7 1.597(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.519(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.488(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C7B C8B 1.519(6) . ?
C7B H7C 0.9900 . ?
C7B H7D 0.9900 . ?
C8B C9 1.554(5) . ?
C8B H8C 0.9900 . ?
C8B H8D 0.9900 . ?
C9 C8 1.489(5) 12 ?
C9 C8B 1.554(5) 12 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.474(4) . ?
C10 H10A 0.958(10) . ?
C10 H10B 0.94(3) . ?
C11 N2 1.357(4) . ?
C11 C12 1.359(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.429(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.419(4) . ?
C13 C13 1.434(6) 9_675 ?
C14 C15 1.366(4) . ?
C14 H14 0.9500 . ?
C15 N2 1.361(4) . ?
C15 H15 0.9500 . ?
C16 N3 1.473(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N3 1.354(3) . ?
C17 C18 1.376(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.414(3) . ?
C18 H18 0.9500 . ?
C19 C18 1.414(3) 3_655 ?
C19 C19 1.457(6) 2 ?
F1 P1 1.5946(17) . ?
F2 P1 1.6068(17) . ?
F3 P1 1.6041(18) . ?
F4 P1 1.5944(17) . ?
F5 P1 1.5825(19) . ?
F6 P1 1.5879(16) . ?
F7 P2 1.609(2) . ?
F8 P2 1.554(3) . ?
F9 P2 1.537(3) . ?
P2 F9 1.537(3) 2 ?
P2 F8 1.554(3) 3 ?
P2 F7 1.609(2) 2 ?
N3 C17 1.354(3) 3_655 ?

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
N1 C1 C2 121.65(17) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C1 C2 C3 120.99(17) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 115.78(15) . . ?
C2 C3 C3 121.8(2) . 4_655 ?
C4 C3 C3 122.35(19) . 4_655 ?
C5 C4 C3 120.85(16) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C5 C4 121.45(17) . . ?
N1 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
N1 C6 C7B 113.2(2) . . ?
N1 C6 C7 108.5(2) . . ?
N1 C6 H6A 110.0 . . ?
C7 C6 H6A 110.0 . . ?
N1 C6 H6B 110.0 . . ?
C7 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
C8 C7 C6 109.9(3) . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 113.8(3) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C8B C7B C6 110.4(3) . . ?
C8B C7B H7C 109.6 . . ?
C6 C7B H7C 109.6 . . ?
C8B C7B H7D 109.6 . . ?
C6 C7B H7D 109.6 . . ?
H7C C7B H7D 108.1 . . ?
C7B C8B C9 113.5(3) . . ?
C7B C8B H8C 108.9 . . ?
C9 C8B H8C 108.9 . . ?
C7B C8B H8D 108.9 . . ?
C9 C8B H8D 108.9 . . ?
H8C C8B H8D 107.7 . . ?
C8 C9 C8 133.8(4) . 12 ?
C8B C9 C8B 86.8(4) . 12 ?
C8 C9 H9A 103.8 . . ?
C8 C9 H9A 103.8 12 . ?
C8 C9 H9B 103.8 . . ?
C8 C9 H9B 103.8 12 . ?
H9A C9 H9B 105.4 . . ?
N2 C10 H10A 113(4) . . ?
N2 C10 H10B 108(3) . . ?
H10A C10 H10B 106(3) . . ?
N2 C11 C12 122.2(3) . . ?
N2 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 115.0(3) . . ?
C14 C13 C13 122.3(3) . 9_675 ?
C12 C13 C13 122.7(3) . 9_675 ?
C15 C14 C13 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
N2 C15 C14 121.6(3) . . ?
N2 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 C18 121.5(2) . . ?
N3 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C19 120.7(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C18 116.1(3) 3_655 . ?
C18 C19 C19 121.94(14) 3_655 2 ?
C18 C19 C19 121.94(14) . 2 ?
F5 P1 F6 91.21(12) . . ?
F5 P1 F4 89.94(12) . . ?
F6 P1 F4 178.51(11) . . ?
F5 P1 F1 90.70(12) . . ?
F6 P1 F1 90.80(10) . . ?
F4 P1 F1 90.14(11) . . ?
F5 P1 F3 179.21(12) . . ?
F6 P1 F3 89.36(11) . . ?
F4 P1 F3 89.49(11) . . ?
F1 P1 F3 89.84(11) . . ?
F5 P1 F2 89.97(11) . . ?
F6 P1 F2 89.03(10) . . ?
F4 P1 F2 90.02(11) . . ?
F1 P1 F2 179.32(11) . . ?
F3 P1 F2 89.50(10) . . ?
F9 P2 F9 180.0 2 . ?
F9 P2 F8 90.0 2 3 ?
F9 P2 F8 90.0 . 3 ?
F9 P2 F8 90.0 2 . ?
F9 P2 F8 90.0 . . ?
F8 P2 F8 180.0 3 . ?
F9 P2 F7 90.0 2 . ?
F9 P2 F7 90.0 . . ?
F8 P2 F7 90.0 3 . ?
F8 P2 F7 90.0 . . ?
F9 P2 F7 90.0 2 2 ?
F9 P2 F7 90.0 . 2 ?
F8 P2 F7 90.0 3 2 ?
F8 P2 F7 90.0 . 2 ?
F7 P2 F7 180.0 . 2 ?
C1 N1 C5 119.23(16) . . ?
C1 N1 C6 119.67(17) . . ?
C5 N1 C6 121.08(17) . . ?
C11 N2 C15 118.8(3) . . ?
C11 N2 C10 120.7(3) . . ?
C15 N2 C10 120.5(3) . . ?
C17 N3 C17 119.6(3) 3_655 . ?
C17 N3 C16 120.20(14) 3_655 . ?
C17 N3 C16 120.20(14) . . ?

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
N1 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C1 C2 C3 C3 176.35(13) . . . 4_655 ?
C2 C3 C4 C5 2.6(3) . . . . ?
C3 C3 C4 C5 -175.11(13) 4_655 . . . ?
C3 C4 C5 N1 -2.0(3) . . . . ?
N1 C6 C7 C8 -79.0(3) . . . . ?
C7B C6 C7 C8 25.5(3) . . . . ?
C6 C7 C8 C9 -177.6(3) . . . . ?
N1 C6 C7B C8B 61.0(4) . . . . ?
C7 C6 C7B C8B -31.5(3) . . . . ?
C6 C7B C8B C9 171.3(3) . . . . ?
C7 C8 C9 C8 -97.2(5) . . . 12 ?
C7 C8 C9 C8B -35.7(4) . . . . ?
C7 C8 C9 C8B -67.0(4) . . . 12 ?
C7B C8B C9 C8 27.4(4) . . . . ?
C7B C8B C9 C8 163.2(3) . . . 12 ?
C7B C8B C9 C8B 179.0(2) . . . 12 ?
N2 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C11 C12 C13 C13 180.0 . . . 9_675 ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C13 C14 C15 180.0 9_675 . . . ?
C13 C14 C15 N2 0.0 . . . . ?
N3 C17 C18 C19 -0.7(3) . . . . ?
C17 C18 C19 C18 0.32(14) . . . 3_655 ?
C17 C18 C19 C19 -179.67(14) . . . 2 ?
C2 C1 N1 C5 1.4(3) . . . . ?
C2 C1 N1 C6 -179.84(18) . . . . ?
C4 C5 N1 C1 -0.1(3) . . . . ?
C4 C5 N1 C6 -178.87(18) . . . . ?
C7B C6 N1 C1 -129.9(2) . . . . ?
C7 C6 N1 C1 -84.4(3) . . . . ?
C7B C6 N1 C5 48.9(3) . . . . ?
C7 C6 N1 C5 94.4(3) . . . . ?
C12 C11 N2 C15 0.0 . . . . ?
C12 C11 N2 C10 180.0 . . . . ?
C14 C15 N2 C11 0.0 . . . . ?
C14 C15 N2 C10 180.0 . . . . ?
C18 C17 N3 C17 0.34(14) . . . 3_655 ?
C18 C17 N3 C16 -179.66(14) . . . . ?

_refine_diff_density_max         1.245
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-4


_chemical_properties_physical    Air-sensitive
####################################################################### 
# 
# 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_jwmb150219
_database_code_depnum_ccdc_archive 'CCDC 1051152'
_audit_update_record             
;
2015-02-25 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H44 N4, C6 H4 S4, 4(F6 P), 2(C2 H3 N)'
_chemical_formula_sum            'C44 H54 F24 N6 P4 S4'
_chemical_formula_weight         1375.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.0815(7)
_cell_length_b                   13.6749(10)
_cell_length_c                   23.3545(14)
_cell_angle_alpha                90
_cell_angle_beta                 115.451(3)
_cell_angle_gamma                90
_cell_volume                     2907.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8726
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.67

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_F_000             1400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.389
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6432
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  triumph
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28352
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.775
_diffrn_reflns_theta_max         28.010
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7028
_reflns_number_gt                5188
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1785P)²+6.4071P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7028
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0861
_refine_ls_wR_factor_ref         0.2952
_refine_ls_wR_factor_gt          0.2660
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3831(4) 0.7445(3) 0.85856(18) 0.0318(8) Uani 1 1 d . . . . .
H1 H 0.4659 0.7036 0.8675 0.038 Uiso 1 1 calc R U . . .
C2 C 0.3900(4) 0.8418(3) 0.84522(18) 0.0297(7) Uani 1 1 d . . . . .
H2 H 0.4773 0.8679 0.8452 0.036 Uiso 1 1 calc R U . . .
C3 C 0.2694(4) 0.9018(3) 0.83180(17) 0.0264(7) Uani 1 1 d . . . . .
C4 C 0.1449(4) 0.8611(3) 0.8339(2) 0.0334(8) Uani 1 1 d . . . . .
H4 H 0.0612 0.9007 0.8256 0.040 Uiso 1 1 calc R U . . .
C5 C 0.1429(4) 0.7643(3) 0.84776(19) 0.0350(8) Uani 1 1 d . . . . .
H5 H 0.0581 0.7371 0.8495 0.042 Uiso 1 1 calc R U . . .
C6 C 0.2544(5) 0.6018(3) 0.87438(19) 0.0367(9) Uani 1 1 d . . . . .
H6A H 0.3356 0.5660 0.8706 0.044 Uiso 1 1 calc R U . . .
H6B H 0.1605 0.5733 0.8436 0.044 Uiso 1 1 calc R U . . .
C7 C 0.2662(5) 0.5898(3) 0.94053(19) 0.0351(8) Uani 1 1 d . . . . .
H7A H 0.2555 0.5196 0.9481 0.042 Uiso 1 1 calc R U . . .
H7B H 0.1841 0.6254 0.9437 0.042 Uiso 1 1 calc R U . . .
C8 C 0.4106(4) 0.6270(3) 0.99200(17) 0.0302(7) Uani 1 1 d . . . . .
H8A H 0.4234 0.6965 0.9837 0.036 Uiso 1 1 calc R U . . .
H8B H 0.4928 0.5896 0.9901 0.036 Uiso 1 1 calc R U . . .
C9 C 0.4179(4) 0.6176(3) 1.05833(18) 0.0324(8) Uani 1 1 d . . . . .
H9A H 0.3338 0.6531 1.0598 0.039 Uiso 1 1 calc R U . . .
H9B H 0.4086 0.5478 1.0672 0.039 Uiso 1 1 calc R U . . .
C10 C 0.5599(4) 0.6579(3) 1.10943(18) 0.0330(8) Uani 1 1 d . . . . .
H10A H 0.5700 0.7273 1.0998 0.040 Uiso 1 1 calc R U . . .
H10B H 0.6437 0.6215 1.1083 0.040 Uiso 1 1 calc R U . . .
C11 C 0.4317(4) 1.3488(3) 0.82412(18) 0.0324(8) Uani 1 1 d . . . . .
H11A H 0.5162 1.3133 0.8231 0.039 Uiso 1 1 calc R U . . .
H11B H 0.4400 1.4183 0.8142 0.039 Uiso 1 1 calc R U . . .
C12 C 0.2903(4) 1.3070(3) 0.77329(18) 0.0327(8) Uani 1 1 d . . . . .
H12A H 0.2049 1.3426 0.7734 0.039 Uiso 1 1 calc R U . . .
H12B H 0.2897 1.3152 0.7311 0.039 Uiso 1 1 calc R U . . .
C13 C 0.3612(4) 1.1363(3) 0.77197(19) 0.0322(8) Uani 1 1 d . . . . .
H13 H 0.4205 1.1578 0.7519 0.039 Uiso 1 1 calc R U . . .
C14 C 0.3604(4) 1.0387(3) 0.78671(19) 0.0326(8) Uani 1 1 d . . . . .
H14 H 0.4199 0.9935 0.7773 0.039 Uiso 1 1 calc R U . . .
C15 C 0.2725(4) 1.0063(3) 0.81535(17) 0.0268(7) Uani 1 1 d . . . . .
C16 C 0.1877(4) 1.0755(3) 0.82881(19) 0.0318(8) Uani 1 1 d . . . . .
H16 H 0.1280 1.0559 0.8491 0.038 Uiso 1 1 calc R U . . .
C17 C 0.1908(4) 1.1717(3) 0.8126(2) 0.0331(8) Uani 1 1 d . . . . .
H17 H 0.1304 1.2181 0.8205 0.040 Uiso 1 1 calc R U . . .
C18 C 0.5618(7) 0.5033(4) 0.4969(3) 0.0601(13) Uani 1 1 d . . . . .
C19 C 0.7941(9) 0.4742(7) 0.4801(4) 0.085(2) Uani 1 1 d . . . . .
H19 H 0.8728 0.4446 0.4744 0.102 Uiso 1 1 calc R U . . .
C20 C 0.7892(8) 0.5649(6) 0.4864(4) 0.0801(19) Uani 1 1 d . . . . .
H20 H 0.8613 0.6056 0.4826 0.096 Uiso 1 1 calc R U . . .
C21 C 0.9734(5) 0.3864(3) 0.8532(2) 0.0431(10) Uani 1 1 d . . . . .
C22 C 0.8947(9) 0.3672(5) 0.8919(3) 0.079(2) Uani 1 1 d . . . . .
H22A H 0.7917 0.3524 0.8642 0.119 Uiso 1 1 calc R U . . .
H22B H 0.9001 0.4249 0.9176 0.119 Uiso 1 1 calc R U . . .
H22C H 0.9396 0.3112 0.9198 0.119 Uiso 1 1 calc R U . . .
N1 N 0.2609(3) 0.7068(2) 0.85905(14) 0.0289(6) Uani 1 1 d . . . . .
N2 N 0.2788(3) 1.2012(2) 0.78570(14) 0.0279(6) Uani 1 1 d . . . . .
N3 N 1.0292(6) 0.4004(4) 0.8226(3) 0.0622(13) Uani 1 1 d . . . . .
F1 F 0.2481(5) 0.1880(4) 0.53746(19) 0.0906(13) Uani 1 1 d . . . . .
F2 F 0.2896(4) 0.2541(3) 0.63205(18) 0.0694(10) Uani 1 1 d . . . . .
F3 F 0.1279(3) 0.1487(3) 0.64140(15) 0.0598(8) Uani 1 1 d . . . . .
F4 F 0.0877(4) 0.0811(3) 0.54788(17) 0.0788(11) Uani 1 1 d . . . . .
F5 F 0.0558(4) 0.2416(3) 0.5539(2) 0.0825(11) Uani 1 1 d . . . . .
F6 F 0.3189(4) 0.0941(3) 0.62532(19) 0.0714(10) Uani 1 1 d . . . . .
F7 F 0.9176(3) 0.0769(4) 0.87131(14) 0.0758(12) Uani 1 1 d . . . . .
F8 F 0.6999(4) -0.0063(2) 0.82311(17) 0.0648(9) Uani 1 1 d . . . . .
F9 F 0.6314(3) 0.0940(2) 0.74070(12) 0.0497(7) Uani 1 1 d . . . . .
F10 F 0.8477(4) 0.1757(2) 0.78759(18) 0.0647(9) Uani 1 1 d . . . . .
F11 F 0.7036(3) 0.1549(3) 0.84017(17) 0.0664(10) Uani 1 1 d . . . . .
F12 F 0.8450(3) 0.0142(2) 0.77287(16) 0.0586(8) Uani 1 1 d . . . . .
P1 P 0.18676(13) 0.16775(10) 0.58868(6) 0.0465(3) Uani 1 1 d . . . . .
P2 P 0.77508(11) 0.08675(8) 0.80674(5) 0.0332(3) Uani 1 1 d . . . . .
S1 S 0.6508(2) 0.40330(14) 0.48222(11) 0.0818(6) Uani 1 1 d . . . . .
S2 S 0.6515(2) 0.61616(12) 0.50201(8) 0.0700(5) 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
C1 N1 1.341(5) . ?
C1 C2 1.374(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(5) . ?
C3 C15 1.484(5) . ?
C4 C5 1.364(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.354(5) . ?
C5 H5 0.9500 . ?
C6 N1 1.488(5) . ?
C6 C7 1.506(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.523(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.524(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.520(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.520(5) 3_677 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C10 1.520(5) 3_677 ?
C11 C12 1.521(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N2 1.489(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N2 1.346(5) . ?
C13 C14 1.379(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(5) . ?
C16 C17 1.373(5) . ?
C16 H16 0.9500 . ?
C17 N2 1.350(5) . ?
C17 H17 0.9500 . ?
C18 C18 1.319(12) 3_666 ?
C18 S1 1.749(6) . ?
C18 S2 1.766(6) . ?
C19 C20 1.253(11) . ?
C19 S1 1.757(8) . ?
C19 H19 0.9500 . ?
C20 S2 1.728(8) . ?
C20 H20 0.9500 . ?
C21 N3 1.100(6) . ?
C21 C22 1.460(7) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
F1 P1 1.589(4) . ?
F2 P1 1.610(3) . ?
F3 P1 1.601(3) . ?
F4 P1 1.579(3) . ?
F5 P1 1.582(4) . ?
F6 P1 1.594(4) . ?
F7 P2 1.579(3) . ?
F8 P2 1.609(3) . ?
F9 P2 1.602(3) . ?
F10 P2 1.581(3) . ?
F11 P2 1.575(3) . ?
F12 P2 1.608(3) . ?

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
N1 C1 C2 120.7(3) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 118.1(3) . . ?
C2 C3 C15 121.0(3) . . ?
C4 C3 C15 120.9(3) . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 120.6(3) . . ?
N1 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
N1 C6 C7 111.1(3) . . ?
N1 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 113.6(3) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C9 112.7(3) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 112.6(3) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 113.6(3) . 3_677 ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 3_677 . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 3_677 . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 113.3(3) 3_677 . ?
C10 C11 H11A 108.9 3_677 . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 3_677 . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
N2 C12 C11 109.8(3) . . ?
N2 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
N2 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
N2 C13 C14 120.6(3) . . ?
N2 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 118.0(3) . . ?
C14 C15 C3 121.3(3) . . ?
C16 C15 C3 120.7(3) . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
N2 C17 C16 120.8(3) . . ?
N2 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C18 C18 S1 123.8(6) 3_666 . ?
C18 C18 S2 122.2(7) 3_666 . ?
S1 C18 S2 113.9(3) . . ?
C20 C19 S1 118.0(7) . . ?
C20 C19 H19 121.0 . . ?
S1 C19 H19 121.0 . . ?
C19 C20 S2 120.1(6) . . ?
C19 C20 H20 119.9 . . ?
S2 C20 H20 119.9 . . ?
N3 C21 C22 178.0(6) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 N1 C5 120.5(3) . . ?
C1 N1 C6 120.6(3) . . ?
C5 N1 C6 118.8(3) . . ?
C13 N2 C17 120.7(3) . . ?
C13 N2 C12 119.1(3) . . ?
C17 N2 C12 120.2(3) . . ?
F4 P1 F5 89.9(2) . . ?
F4 P1 F1 91.5(2) . . ?
F5 P1 F1 90.7(3) . . ?
F4 P1 F6 90.9(2) . . ?
F5 P1 F6 178.6(2) . . ?
F1 P1 F6 90.5(2) . . ?
F4 P1 F3 89.7(2) . . ?
F5 P1 F3 89.8(2) . . ?
F1 P1 F3 178.8(2) . . ?
F6 P1 F3 89.11(19) . . ?
F4 P1 F2 178.3(2) . . ?
F5 P1 F2 91.4(2) . . ?
F1 P1 F2 89.6(2) . . ?
F6 P1 F2 87.8(2) . . ?
F3 P1 F2 89.26(19) . . ?
F11 P2 F7 90.00(19) . . ?
F11 P2 F10 92.9(2) . . ?
F7 P2 F10 89.7(2) . . ?
F11 P2 F9 91.33(17) . . ?
F7 P2 F9 178.5(2) . . ?
F10 P2 F9 90.97(18) . . ?
F11 P2 F12 178.1(2) . . ?
F7 P2 F12 90.32(18) . . ?
F10 P2 F12 88.92(19) . . ?
F9 P2 F12 88.34(16) . . ?
F11 P2 F8 89.3(2) . . ?
F7 P2 F8 91.9(2) . . ?
F10 P2 F8 177.3(2) . . ?
F9 P2 F8 87.39(18) . . ?
F12 P2 F8 88.83(19) . . ?
C18 S1 C19 94.1(3) . . ?
C20 S2 C18 93.8(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.3(6) . . . . ?
C1 C2 C3 C4 1.5(6) . . . . ?
C1 C2 C3 C15 -178.1(3) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C15 C3 C4 C5 178.6(4) . . . . ?
C3 C4 C5 N1 -0.6(6) . . . . ?
N1 C6 C7 C8 -61.9(5) . . . . ?
C6 C7 C8 C9 177.8(3) . . . . ?
C7 C8 C9 C10 -178.1(3) . . . . ?
C8 C9 C10 C11 178.9(3) . . . 3_677 ?
C10 C11 C12 N2 -61.1(4) 3_677 . . . ?
N2 C13 C14 C15 0.8(6) . . . . ?
C13 C14 C15 C16 -0.5(6) . . . . ?
C13 C14 C15 C3 -180.0(4) . . . . ?
C2 C3 C15 C14 27.9(5) . . . . ?
C4 C3 C15 C14 -151.8(4) . . . . ?
C2 C3 C15 C16 -151.6(4) . . . . ?
C4 C3 C15 C16 28.8(5) . . . . ?
C14 C15 C16 C17 1.2(6) . . . . ?
C3 C15 C16 C17 -179.3(4) . . . . ?
C15 C16 C17 N2 -2.2(6) . . . . ?
S1 C19 C20 S2 4.3(10) . . . . ?
C2 C1 N1 C5 -1.5(6) . . . . ?
C2 C1 N1 C6 -179.1(3) . . . . ?
C4 C5 N1 C1 1.9(6) . . . . ?
C4 C5 N1 C6 179.7(4) . . . . ?
C7 C6 N1 C1 104.4(4) . . . . ?
C7 C6 N1 C5 -73.3(5) . . . . ?
C14 C13 N2 C17 -1.8(6) . . . . ?
C14 C13 N2 C12 175.7(4) . . . . ?
C16 C17 N2 C13 2.5(6) . . . . ?
C16 C17 N2 C12 -175.0(4) . . . . ?
C11 C12 N2 C13 -76.1(4) . . . . ?
C11 C12 N2 C17 101.4(4) . . . . ?
C18 C18 S1 C19 179.4(8) 3_666 . . . ?
S2 C18 S1 C19 -0.1(5) . . . . ?
C20 C19 S1 C18 -2.5(8) . . . . ?
C19 C20 S2 C18 -3.6(8) . . . . ?
C18 C18 S2 C20 -177.8(8) 3_666 . . . ?
S1 C18 S2 C20 1.7(4) . . . . ?

_refine_diff_density_max         0.988
_refine_diff_density_min         -1.495
_refine_diff_density_rms         0.140

_shelxl_version_number           2013-4


_chemical_properties_physical    Air-sensitive
####################################################################### 
# 
# 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_jwmb150108
_database_code_depnum_ccdc_archive 'CCDC 1051241'
_audit_update_record             
;
2015-02-25 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C30 H36 N4), 4(F6 P), C4 H10 O, 2(C2 H3 N)'
_chemical_formula_sum            'C68 H88 F24 N10 O P4'
_chemical_formula_weight         1641.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.7788(5)
_cell_length_b                   17.1208(7)
_cell_length_c                   28.0061(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7565.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9861
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      28.97

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             3400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_exptl_absorpt_coefficient_mu    0.208
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6575
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45215
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.454
_diffrn_reflns_theta_max         29.031
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             19627
_reflns_number_gt                12614
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0959P)²+16.1486P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.63(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         19627
_refine_ls_number_parameters     969
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.0884
_refine_ls_wR_factor_ref         0.2402
_refine_ls_wR_factor_gt          0.2103
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0558(4) 0.7047(4) 0.1433(2) 0.0274(13) Uani 1 1 d . . . . .
H1 H 0.0310 0.6638 0.1252 0.033 Uiso 1 1 calc R U . . .
C2 C 0.0534(4) 0.7011(4) 0.1920(2) 0.0265(13) Uani 1 1 d . . . . .
H2 H 0.0260 0.6584 0.2072 0.032 Uiso 1 1 calc R U . . .
C3 C 0.0911(4) 0.7602(4) 0.2202(2) 0.0206(12) Uani 1 1 d . . . . .
C4 C 0.1288(4) 0.8225(4) 0.1953(2) 0.0259(13) Uani 1 1 d . . . . .
H4 H 0.1540 0.8642 0.2126 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1297(4) 0.8239(4) 0.1465(2) 0.0275(13) Uani 1 1 d . . . . .
H5 H 0.1564 0.8662 0.1304 0.033 Uiso 1 1 calc R U . . .
C6 C 0.0980(4) 0.7662(4) 0.0675(2) 0.0299(14) Uani 1 1 d . . . . .
H6A H 0.1063 0.8205 0.0563 0.036 Uiso 1 1 calc R U . . .
H6B H 0.0439 0.7469 0.0542 0.036 Uiso 1 1 calc R U . . .
C7 C 0.1708(5) 0.7153(4) 0.0491(2) 0.0341(15) Uani 1 1 d . . . . .
H7A H 0.1595 0.6604 0.0582 0.041 Uiso 1 1 calc R U . . .
H7B H 0.1713 0.7179 0.0138 0.041 Uiso 1 1 calc R U . . .
C8 C 0.2582(4) 0.7379(4) 0.0674(2) 0.0328(15) Uani 1 1 d . . . . .
H8A H 0.2576 0.7367 0.1028 0.039 Uiso 1 1 calc R U . . .
H8B H 0.2999 0.6987 0.0563 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2864(4) 0.8182(4) 0.0510(2) 0.0317(15) Uani 1 1 d . . . . .
H9A H 0.2447 0.8574 0.0622 0.038 Uiso 1 1 calc R U . . .
H9B H 0.2867 0.8195 0.0157 0.038 Uiso 1 1 calc R U . . .
C10 C 0.3751(4) 0.8413(5) 0.0694(2) 0.0330(15) Uani 1 1 d . . . . .
H10A H 0.4176 0.8045 0.0564 0.040 Uiso 1 1 calc R U . . .
H10B H 0.3893 0.8943 0.0577 0.040 Uiso 1 1 calc R U . . .
C11 C 0.4086(4) 0.7768(4) 0.1462(2) 0.0300(14) Uani 1 1 d . . . . .
H11 H 0.4289 0.7331 0.1287 0.036 Uiso 1 1 calc R U . . .
C12 C 0.4090(4) 0.7743(4) 0.1945(2) 0.0282(13) Uani 1 1 d . . . . .
H12 H 0.4298 0.7288 0.2100 0.034 Uiso 1 1 calc R U . . .
C13 C 0.3793(4) 0.8371(4) 0.2228(2) 0.0229(12) Uani 1 1 d . . . . .
C14 C 0.3499(4) 0.9022(4) 0.1965(2) 0.0272(13) Uani 1 1 d . . . . .
H14 H 0.3295 0.9467 0.2132 0.033 Uiso 1 1 calc R U . . .
C15 C 0.3501(4) 0.9027(4) 0.1477(2) 0.0280(13) Uani 1 1 d . . . . .
H15 H 0.3292 0.9472 0.1312 0.034 Uiso 1 1 calc R U . . .
C16 C 0.4005(4) 0.7682(4) 0.3494(2) 0.0328(15) Uani 1 1 d . . . . .
H16 H 0.4185 0.7227 0.3661 0.039 Uiso 1 1 calc R U . . .
C17 C 0.4032(4) 0.7685(4) 0.3004(2) 0.0286(13) Uani 1 1 d . . . . .
H17 H 0.4222 0.7233 0.2840 0.034 Uiso 1 1 calc R U . . .
C18 C 0.3780(4) 0.8354(4) 0.2739(2) 0.0216(12) Uani 1 1 d . . . . .
C19 C 0.3516(4) 0.9001(4) 0.3017(2) 0.0253(12) Uani 1 1 d . . . . .
H19 H 0.3352 0.9470 0.2861 0.030 Uiso 1 1 calc R U . . .
C20 C 0.3490(4) 0.8970(4) 0.3506(2) 0.0297(14) Uani 1 1 d . . . . .
H20 H 0.3303 0.9414 0.3681 0.036 Uiso 1 1 calc R U . . .
C21 C 0.3665(4) 0.8276(5) 0.4275(2) 0.0347(15) Uani 1 1 d . . . . .
H21A H 0.3802 0.8796 0.4408 0.042 Uiso 1 1 calc R U . . .
H21B H 0.4086 0.7899 0.4400 0.042 Uiso 1 1 calc R U . . .
C22 C 0.2786(4) 0.8036(5) 0.4440(2) 0.0357(16) Uani 1 1 d . . . . .
H22A H 0.2373 0.8429 0.4327 0.043 Uiso 1 1 calc R U . . .
H22B H 0.2774 0.8040 0.4794 0.043 Uiso 1 1 calc R U . . .
C23 C 0.2505(4) 0.7232(4) 0.4266(2) 0.0322(15) Uani 1 1 d . . . . .
H23A H 0.2925 0.6841 0.4375 0.039 Uiso 1 1 calc R U . . .
H23B H 0.2512 0.7232 0.3913 0.039 Uiso 1 1 calc R U . . .
C24 C 0.1628(5) 0.6975(4) 0.4434(2) 0.0361(16) Uani 1 1 d . . . . .
H24A H 0.1616 0.6987 0.4788 0.043 Uiso 1 1 calc R U . . .
H24B H 0.1534 0.6428 0.4333 0.043 Uiso 1 1 calc R U . . .
C25 C 0.0901(4) 0.7478(4) 0.4245(2) 0.0272(13) Uani 1 1 d . . . . .
H25A H 0.0357 0.7261 0.4362 0.033 Uiso 1 1 calc R U . . .
H25B H 0.0959 0.8013 0.4374 0.033 Uiso 1 1 calc R U . . .
C26 C 0.0502(4) 0.6934(4) 0.3460(2) 0.0269(13) Uani 1 1 d . . . . .
H26 H 0.0242 0.6509 0.3621 0.032 Uiso 1 1 calc R U . . .
C27 C 0.0500(4) 0.6952(4) 0.2972(2) 0.0266(13) Uani 1 1 d . . . . .
H27 H 0.0230 0.6543 0.2800 0.032 Uiso 1 1 calc R U . . .
C28 C 0.0894(4) 0.7571(4) 0.2714(2) 0.0213(12) Uani 1 1 d . . . . .
C29 C 0.1270(4) 0.8163(4) 0.3000(2) 0.0266(13) Uani 1 1 d . . . . .
H29 H 0.1543 0.8591 0.2848 0.032 Uiso 1 1 calc R U . . .
C30 C 0.1247(4) 0.8130(4) 0.3486(2) 0.0260(13) Uani 1 1 d . . . . .
H30 H 0.1497 0.8540 0.3666 0.031 Uiso 1 1 calc R U . . .
C31 C 0.6046(4) 0.8328(4) 0.1455(2) 0.0301(14) Uani 1 1 d . . . . .
H31 H 0.6224 0.7876 0.1285 0.036 Uiso 1 1 calc R U . . .
C32 C 0.6019(4) 0.8307(4) 0.1941(2) 0.0271(13) Uani 1 1 d . . . . .
H32 H 0.6183 0.7844 0.2104 0.033 Uiso 1 1 calc R U . . .
C33 C 0.5749(4) 0.8968(4) 0.2211(2) 0.0221(12) Uani 1 1 d . . . . .
C34 C 0.5508(4) 0.9631(4) 0.1940(2) 0.0258(13) Uani 1 1 d . . . . .
H34 H 0.5312 1.0086 0.2100 0.031 Uiso 1 1 calc R U . . .
C35 C 0.5553(4) 0.9627(4) 0.1451(2) 0.0278(13) Uani 1 1 d . . . . .
H35 H 0.5393 1.0083 0.1280 0.033 Uiso 1 1 calc R U . . .
C36 C 0.5905(4) 0.9022(4) 0.0683(2) 0.0318(15) Uani 1 1 d . . . . .
H36A H 0.5438 0.9340 0.0550 0.038 Uiso 1 1 calc R U . . .
H36B H 0.5858 0.8489 0.0548 0.038 Uiso 1 1 calc R U . . .
C37 C 0.6757(4) 0.9379(5) 0.0535(2) 0.0320(14) Uani 1 1 d . . . . .
H37A H 0.6774 0.9420 0.0182 0.038 Uiso 1 1 calc R U . . .
H37B H 0.6795 0.9915 0.0666 0.038 Uiso 1 1 calc R U . . .
C38 C 0.7527(4) 0.8914(4) 0.0703(2) 0.0332(15) Uani 1 1 d . . . . .
H38A H 0.7517 0.8885 0.1056 0.040 Uiso 1 1 calc R U . . .
H38B H 0.7481 0.8374 0.0578 0.040 Uiso 1 1 calc R U . . .
C39 C 0.8365(5) 0.9252(5) 0.0548(3) 0.0403(17) Uani 1 1 d . . . . .
H39A H 0.8419 0.9786 0.0680 0.048 Uiso 1 1 calc R U . . .
H39B H 0.8369 0.9295 0.0195 0.048 Uiso 1 1 calc R U . . .
C40 C 0.9135(4) 0.8772(5) 0.0704(2) 0.0386(16) Uani 1 1 d . . . . .
H40A H 0.9100 0.8244 0.0561 0.046 Uiso 1 1 calc R U . . .
H40B H 0.9658 0.9025 0.0585 0.046 Uiso 1 1 calc R U . . .
C41 C 0.8811(4) 0.8080(4) 0.1455(2) 0.0325(15) Uani 1 1 d . . . . .
H41 H 0.8565 0.7675 0.1270 0.039 Uiso 1 1 calc R U . . .
C42 C 0.8786(4) 0.8031(4) 0.1942(2) 0.0288(14) Uani 1 1 d . . . . .
H42 H 0.8513 0.7599 0.2088 0.035 Uiso 1 1 calc R U . . .
C43 C 0.9160(4) 0.8613(4) 0.2230(2) 0.0264(13) Uani 1 1 d . . . . .
C44 C 0.9549(4) 0.9233(4) 0.1982(3) 0.0342(15) Uani 1 1 d . . . . .
H44 H 0.9810 0.9642 0.2158 0.041 Uiso 1 1 calc R U . . .
C45 C 0.9562(4) 0.9260(4) 0.1497(3) 0.0358(16) Uani 1 1 d . . . . .
H45 H 0.9842 0.9681 0.1342 0.043 Uiso 1 1 calc R U . . .
C46 C 0.8708(4) 0.7928(4) 0.3480(2) 0.0329(15) Uani 1 1 d . . . . .
H46 H 0.8446 0.7498 0.3635 0.040 Uiso 1 1 calc R U . . .
C47 C 0.8737(4) 0.7947(4) 0.2992(2) 0.0320(14) Uani 1 1 d . . . . .
H47 H 0.8491 0.7530 0.2816 0.038 Uiso 1 1 calc R U . . .
C48 C 0.9124(4) 0.8570(4) 0.2742(2) 0.0265(13) Uani 1 1 d . . . . .
C49 C 0.9494(5) 0.9154(4) 0.3040(3) 0.0391(17) Uani 1 1 d . . . . .
H49 H 0.9782 0.9581 0.2897 0.047 Uiso 1 1 calc R U . . .
C50 C 0.9444(4) 0.9114(5) 0.3522(3) 0.0384(17) Uani 1 1 d . . . . .
H50 H 0.9694 0.9518 0.3707 0.046 Uiso 1 1 calc R U . . .
C51 C 0.8967(5) 0.8525(5) 0.4270(2) 0.0423(19) Uani 1 1 d . . . . .
H51A H 0.9499 0.8721 0.4414 0.051 Uiso 1 1 calc R U . . .
H51B H 0.8875 0.7985 0.4386 0.051 Uiso 1 1 calc R U . . .
C52 C 0.8221(5) 0.9046(5) 0.4432(3) 0.0445(19) Uani 1 1 d . . . . .
H52A H 0.8211 0.9062 0.4785 0.053 Uiso 1 1 calc R U . . .
H52B H 0.8321 0.9584 0.4316 0.053 Uiso 1 1 calc R U . . .
C53 C 0.7367(5) 0.8773(5) 0.4255(2) 0.0357(16) Uani 1 1 d . . . . .
H53A H 0.7267 0.8235 0.4371 0.043 Uiso 1 1 calc R U . . .
H53B H 0.7376 0.8757 0.3902 0.043 Uiso 1 1 calc R U . . .
C54 C 0.6636(4) 0.9287(4) 0.4415(2) 0.0329(15) Uani 1 1 d . . . . .
H54A H 0.6721 0.9820 0.4286 0.039 Uiso 1 1 calc R U . . .
H54B H 0.6641 0.9324 0.4768 0.039 Uiso 1 1 calc R U . . .
C55 C 0.5774(5) 0.8986(4) 0.4254(2) 0.0335(15) Uani 1 1 d . . . . .
H55A H 0.5685 0.8454 0.4383 0.040 Uiso 1 1 calc R U . . .
H55B H 0.5325 0.9328 0.4384 0.040 Uiso 1 1 calc R U . . .
C56 C 0.5940(4) 0.8309(4) 0.3487(2) 0.0296(14) Uani 1 1 d . . . . .
H56 H 0.6088 0.7852 0.3660 0.035 Uiso 1 1 calc R U . . .
C57 C 0.5966(4) 0.8299(4) 0.2998(2) 0.0271(13) Uani 1 1 d . . . . .
H57 H 0.6148 0.7838 0.2839 0.033 Uiso 1 1 calc R U . . .
C58 C 0.5729(4) 0.8960(3) 0.2722(2) 0.0215(12) Uani 1 1 d . . . . .
C59 C 0.5464(4) 0.9628(4) 0.2994(2) 0.0270(13) Uani 1 1 d . . . . .
H59 H 0.5283 1.0087 0.2833 0.032 Uiso 1 1 calc R U . . .
C60 C 0.5469(4) 0.9614(4) 0.3479(2) 0.0292(14) Uani 1 1 d . . . . .
H60 H 0.5304 1.0068 0.3650 0.035 Uiso 1 1 calc R U . . .
C61 C 0.3846(6) 0.1236(4) 0.2059(3) 0.048(2) Uani 1 1 d . . . . .
C62 C 0.3092(6) 0.1224(5) 0.1758(3) 0.054(2) Uani 1 1 d . . . . .
H62A H 0.2671 0.0869 0.1897 0.080 Uiso 1 1 calc R U . . .
H62B H 0.3245 0.1042 0.1438 0.080 Uiso 1 1 calc R U . . .
H62C H 0.2854 0.1751 0.1737 0.080 Uiso 1 1 calc R U . . .
C63 C 0.3943(9) -0.0753(8) -0.0496(4) 0.093(4) Uani 1 1 d . . . . .
C64 C 0.3172(7) -0.0333(6) -0.0508(4) 0.065(3) Uani 1 1 d . . . . .
H64A H 0.2699 -0.0699 -0.0543 0.098 Uiso 1 1 calc R U . . .
H64B H 0.3177 0.0029 -0.0778 0.098 Uiso 1 1 calc R U . . .
H64C H 0.3106 -0.0039 -0.0210 0.098 Uiso 1 1 calc R U . . .
C65 C 0.2672(11) 0.6019(8) 0.1994(10) 0.167(10) Uani 1 1 d . . . . .
H65A H 0.2431 0.6551 0.1972 0.200 Uiso 1 1 calc R U . . .
H65B H 0.3297 0.6056 0.1974 0.200 Uiso 1 1 calc R U . . .
C66 C 0.2369(10) 0.5564(9) 0.1641(7) 0.128(6) Uani 1 1 d . . . . .
H66A H 0.2580 0.5030 0.1682 0.192 Uiso 1 1 calc R U . . .
H66B H 0.2559 0.5769 0.1333 0.192 Uiso 1 1 calc R U . . .
H66C H 0.1749 0.5563 0.1652 0.192 Uiso 1 1 calc R U . . .
C67 C 0.2656(11) 0.5972(9) 0.2881(7) 0.120(6) Uani 1 1 d . . . . .
H67A H 0.2425 0.6508 0.2900 0.144 Uiso 1 1 calc R U . . .
H67B H 0.3282 0.6010 0.2891 0.144 Uiso 1 1 calc R U . . .
C68 C 0.2379(9) 0.5546(9) 0.3278(5) 0.102(4) Uani 1 1 d . . . . .
H68A H 0.1777 0.5655 0.3335 0.153 Uiso 1 1 calc R U . . .
H68B H 0.2709 0.5699 0.3560 0.153 Uiso 1 1 calc R U . . .
H68C H 0.2456 0.4987 0.3218 0.153 Uiso 1 1 calc R U . . .
N1 N 0.0931(4) 0.7657(3) 0.12031(17) 0.0270(12) Uani 1 1 d . . . . .
N2 N 0.3798(3) 0.8406(3) 0.12224(19) 0.0293(12) Uani 1 1 d . . . . .
N3 N 0.3731(3) 0.8305(4) 0.37474(19) 0.0306(12) Uani 1 1 d . . . . .
N4 N 0.0873(3) 0.7519(3) 0.37199(17) 0.0258(11) Uani 1 1 d . . . . .
N5 N 0.5822(3) 0.8984(3) 0.12039(18) 0.0274(12) Uani 1 1 d . . . . .
N6 N 0.9184(4) 0.8699(4) 0.1230(2) 0.0331(13) Uani 1 1 d . . . . .
N7 N 0.9050(4) 0.8518(4) 0.3751(2) 0.0362(14) Uani 1 1 d . . . . .
N8 N 0.5706(3) 0.8963(3) 0.37275(18) 0.0289(12) Uani 1 1 d . . . . .
N9 N 0.4419(6) 0.1249(5) 0.2302(3) 0.068(2) Uani 1 1 d . . . . .
N10 N 0.4538(12) -0.1101(12) -0.0480(4) 0.197(10) Uani 1 1 d . . . . .
O1 O 0.2416(7) 0.5644(5) 0.2449(4) 0.110(3) Uani 1 1 d . . . . .
F1 F 0.7375(4) 0.5667(4) 0.1883(5) 0.154(5) Uani 1 1 d . . . . .
F2 F 0.8506(5) 0.6257(3) 0.16143(18) 0.087(2) Uani 1 1 d . . . . .
F3 F 0.8416(6) 0.4936(3) 0.1666(2) 0.109(3) Uani 1 1 d . . . . .
F4 F 0.9260(4) 0.5607(5) 0.2156(5) 0.164(5) Uani 1 1 d . . . . .
F5 F 0.8102(5) 0.5023(3) 0.2423(2) 0.092(2) Uani 1 1 d . . . . .
F6 F 0.8230(7) 0.6328(3) 0.2377(2) 0.130(4) Uani 1 1 d . . . . .
F7 F 0.4955(4) 0.2016(3) 0.02324(19) 0.0676(17) Uani 1 1 d . . . . .
F8 F 0.4626(9) 0.1607(7) 0.0963(3) 0.192(7) Uani 1 1 d . . . . .
F9 F 0.5396(5) 0.0900(6) 0.0475(6) 0.253(10) Uani 1 1 d . . . . .
F10 F 0.4157(3) 0.0487(3) 0.07106(17) 0.0502(12) Uani 1 1 d . . . . .
F11 F 0.4288(10) 0.1013(6) -0.0020(3) 0.185(7) Uani 1 1 d . . . . .
F12 F 0.3643(5) 0.1612(7) 0.0477(6) 0.194(7) Uani 1 1 d . . . . .
F13 F 0.5310(4) 0.7110(3) 0.0485(2) 0.082(2) Uani 1 1 d . . . . .
F14 F 0.6102(6) 0.6172(4) 0.0160(2) 0.116(3) Uani 1 1 d . . . . .
F15 F 0.6485(7) 0.6675(5) 0.0817(4) 0.139(4) Uani 1 1 d . . . . .
F16 F 0.5985(4) 0.5440(3) 0.08099(18) 0.0605(14) Uani 1 1 d . . . . .
F17 F 0.5263(8) 0.6383(5) 0.1140(3) 0.166(6) Uani 1 1 d . . . . .
F18 F 0.4828(7) 0.5876(6) 0.0480(6) 0.199(7) Uani 1 1 d . . . . .
F19 F 0.1494(10) 0.1502(4) 0.0721(3) 0.202(7) Uani 1 1 d . . . . .
F20 F 0.2207(5) 0.0391(7) 0.0849(3) 0.146(4) Uani 1 1 d . . . . .
F21 F 0.1495(5) 0.0564(4) 0.01837(18) 0.095(2) Uani 1 1 d . . . . .
F22 F 0.1062(5) -0.0267(3) 0.0740(2) 0.090(2) Uani 1 1 d . . . . .
F23 F 0.0328(6) 0.0785(7) 0.0635(3) 0.150(4) Uani 1 1 d . . . . .
F24 F 0.1074(5) 0.0710(5) 0.12785(18) 0.087(2) Uani 1 1 d . . . . .
P1 P 0.83196(13) 0.56364(11) 0.20159(7) 0.0370(4) Uani 1 1 d . . . . .
P2 P 0.45477(13) 0.12517(11) 0.04730(6) 0.0358(4) Uani 1 1 d . . . . .
P3 P 0.56443(16) 0.62665(12) 0.06392(7) 0.0470(6) Uani 1 1 d . . . . .
P4 P 0.12898(14) 0.06336(13) 0.07263(7) 0.0429(5) 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
C1 N1 1.361(8) . ?
C1 C2 1.365(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.416(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.406(9) . ?
C3 C28 1.435(7) . ?
C4 C5 1.369(8) . ?
C4 H4 0.9500 . ?
C5 N1 1.365(8) . ?
C5 H5 0.9500 . ?
C6 N1 1.481(7) . ?
C6 C7 1.531(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.521(10) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.516(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.543(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.480(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.353(9) . ?
C11 N2 1.361(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.416(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.414(9) . ?
C13 C18 1.430(8) . ?
C14 C15 1.367(9) . ?
C14 H14 0.9500 . ?
C15 N2 1.363(8) . ?
C15 H15 0.9500 . ?
C16 N3 1.352(9) . ?
C16 C17 1.372(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.422(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.418(8) . ?
C19 C20 1.370(9) . ?
C19 H19 0.9500 . ?
C20 N3 1.378(9) . ?
C20 H20 0.9500 . ?
C21 N3 1.482(8) . ?
C21 C22 1.519(10) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.525(10) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.527(10) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.529(10) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N4 1.472(7) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.368(9) . ?
C26 N4 1.369(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.425(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.419(9) . ?
C29 C30 1.364(8) . ?
C29 H29 0.9500 . ?
C30 N4 1.369(8) . ?
C30 H30 0.9500 . ?
C31 C32 1.364(9) . ?
C31 N5 1.371(9) . ?
C31 H31 0.9500 . ?
C32 C33 1.425(9) . ?
C32 H32 0.9500 . ?
C33 C34 1.417(9) . ?
C33 C58 1.432(8) . ?
C34 C35 1.370(9) . ?
C34 H34 0.9500 . ?
C35 N5 1.369(9) . ?
C35 H35 0.9500 . ?
C36 N5 1.466(8) . ?
C36 C37 1.534(9) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.527(9) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.507(10) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.530(10) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 N6 1.479(9) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.365(9) . ?
C41 N6 1.367(9) . ?
C41 H41 0.9500 . ?
C42 C43 1.411(9) . ?
C42 H42 0.9500 . ?
C43 C44 1.410(9) . ?
C43 C48 1.437(9) . ?
C44 C45 1.358(10) . ?
C44 H44 0.9500 . ?
C45 N6 1.356(10) . ?
C45 H45 0.9500 . ?
C46 C47 1.369(9) . ?
C46 N7 1.373(9) . ?
C46 H46 0.9500 . ?
C47 C48 1.415(9) . ?
C47 H47 0.9500 . ?
C48 C49 1.427(10) . ?
C49 C50 1.354(11) . ?
C49 H49 0.9500 . ?
C50 N7 1.355(10) . ?
C50 H50 0.9500 . ?
C51 N7 1.461(9) . ?
C51 C52 1.544(11) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 C53 1.510(10) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 C54 1.517(10) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 C55 1.523(10) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C55 N8 1.478(8) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C56 N8 1.358(9) . ?
C56 C57 1.371(9) . ?
C56 H56 0.9500 . ?
C57 C58 1.420(9) . ?
C57 H57 0.9500 . ?
C58 C59 1.438(8) . ?
C59 C60 1.358(9) . ?
C59 H59 0.9500 . ?
C60 N8 1.364(9) . ?
C60 H60 0.9500 . ?
C61 N9 1.132(12) . ?
C61 C62 1.458(13) . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?
C63 N10 1.112(16) . ?
C63 C64 1.414(16) . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?
C65 C66 1.35(2) . ?
C65 O1 1.48(2) . ?
C65 H65A 0.9900 . ?
C65 H65B 0.9900 . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
C66 H66C 0.9800 . ?
C67 O1 1.386(19) . ?
C67 C68 1.40(2) . ?
C67 H67A 0.9900 . ?
C67 H67B 0.9900 . ?
C68 H68A 0.9800 . ?
C68 H68B 0.9800 . ?
C68 H68C 0.9800 . ?
F1 P1 1.537(7) . ?
F2 P1 1.575(5) . ?
F3 P1 1.556(5) . ?
F4 P1 1.535(7) . ?
F5 P1 1.588(5) . ?
F6 P1 1.565(6) . ?
F7 P2 1.607(5) . ?
F8 P2 1.507(8) . ?
F9 P2 1.468(7) . ?
F10 P2 1.593(5) . ?
F11 P2 1.498(7) . ?
F12 P2 1.556(9) . ?
F13 P3 1.598(5) . ?
F14 P3 1.533(6) . ?
F15 P3 1.580(9) . ?
F16 P3 1.588(5) . ?
F17 P3 1.538(7) . ?
F18 P3 1.518(9) . ?
F19 P4 1.521(7) . ?
F20 P4 1.544(8) . ?
F21 P4 1.558(5) . ?
F22 P4 1.584(6) . ?
F23 P4 1.561(8) . ?
F24 P4 1.589(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
N1 C1 C2 121.4(6) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C1 C2 C3 120.9(6) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 116.3(5) . . ?
C4 C3 C28 122.1(6) . . ?
C2 C3 C28 121.5(6) . . ?
C5 C4 C3 120.9(6) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
N1 C5 C4 121.3(6) . . ?
N1 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
N1 C6 C7 111.9(5) . . ?
N1 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 114.9(5) . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C7 113.3(6) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 113.4(6) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
N2 C10 C9 112.1(5) . . ?
N2 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 N2 121.3(6) . . ?
C12 C11 H11 119.3 . . ?
N2 C11 H11 119.3 . . ?
C11 C12 C13 122.3(6) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C12 114.5(6) . . ?
C14 C13 C18 122.2(6) . . ?
C12 C13 C18 123.3(6) . . ?
C15 C14 C13 121.8(6) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
N2 C15 C14 121.3(6) . . ?
N2 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
N3 C16 C17 122.0(6) . . ?
N3 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C16 C17 C18 121.2(6) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 115.1(5) . . ?
C19 C18 C13 122.5(6) . . ?
C17 C18 C13 122.4(6) . . ?
C20 C19 C18 121.9(6) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 N3 120.9(6) . . ?
C19 C20 H20 119.6 . . ?
N3 C20 H20 119.6 . . ?
N3 C21 C22 112.1(5) . . ?
N3 C21 H21A 109.2 . . ?
C22 C21 H21A 109.2 . . ?
N3 C21 H21B 109.2 . . ?
C22 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 C23 114.3(6) . . ?
C21 C22 H22A 108.7 . . ?
C23 C22 H22A 108.7 . . ?
C21 C22 H22B 108.7 . . ?
C23 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 C24 115.1(6) . . ?
C22 C23 H23A 108.5 . . ?
C24 C23 H23A 108.5 . . ?
C22 C23 H23B 108.5 . . ?
C24 C23 H23B 108.5 . . ?
H23A C23 H23B 107.5 . . ?
C23 C24 C25 114.3(5) . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24B 108.7 . . ?
C25 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
N4 C25 C24 113.3(5) . . ?
N4 C25 H25A 108.9 . . ?
C24 C25 H25A 108.9 . . ?
N4 C25 H25B 108.9 . . ?
C24 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C27 C26 N4 121.1(6) . . ?
C27 C26 H26 119.5 . . ?
N4 C26 H26 119.5 . . ?
C26 C27 C28 121.4(6) . . ?
C26 C27 H27 119.3 . . ?
C28 C27 H27 119.3 . . ?
C29 C28 C27 115.4(5) . . ?
C29 C28 C3 121.8(6) . . ?
C27 C28 C3 122.8(6) . . ?
C30 C29 C28 121.5(6) . . ?
C30 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C29 C30 N4 121.3(6) . . ?
C29 C30 H30 119.3 . . ?
N4 C30 H30 119.3 . . ?
C32 C31 N5 121.7(6) . . ?
C32 C31 H31 119.2 . . ?
N5 C31 H31 119.2 . . ?
C31 C32 C33 121.2(6) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C34 C33 C32 115.7(5) . . ?
C34 C33 C58 122.5(6) . . ?
C32 C33 C58 121.8(6) . . ?
C35 C34 C33 121.1(6) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
N5 C35 C34 121.7(6) . . ?
N5 C35 H35 119.1 . . ?
C34 C35 H35 119.1 . . ?
N5 C36 C37 111.4(5) . . ?
N5 C36 H36A 109.3 . . ?
C37 C36 H36A 109.3 . . ?
N5 C36 H36B 109.3 . . ?
C37 C36 H36B 109.3 . . ?
H36A C36 H36B 108.0 . . ?
C38 C37 C36 113.9(6) . . ?
C38 C37 H37A 108.8 . . ?
C36 C37 H37A 108.8 . . ?
C38 C37 H37B 108.8 . . ?
C36 C37 H37B 108.8 . . ?
H37A C37 H37B 107.7 . . ?
C39 C38 C37 114.2(6) . . ?
C39 C38 H38A 108.7 . . ?
C37 C38 H38A 108.7 . . ?
C39 C38 H38B 108.7 . . ?
C37 C38 H38B 108.7 . . ?
H38A C38 H38B 107.6 . . ?
C38 C39 C40 114.1(6) . . ?
C38 C39 H39A 108.7 . . ?
C40 C39 H39A 108.7 . . ?
C38 C39 H39B 108.7 . . ?
C40 C39 H39B 108.7 . . ?
H39A C39 H39B 107.6 . . ?
N6 C40 C39 111.8(6) . . ?
N6 C40 H40A 109.3 . . ?
C39 C40 H40A 109.3 . . ?
N6 C40 H40B 109.3 . . ?
C39 C40 H40B 109.3 . . ?
H40A C40 H40B 107.9 . . ?
C42 C41 N6 121.4(7) . . ?
C42 C41 H41 119.3 . . ?
N6 C41 H41 119.3 . . ?
C41 C42 C43 121.0(6) . . ?
C41 C42 H42 119.5 . . ?
C43 C42 H42 119.5 . . ?
C44 C43 C42 115.6(6) . . ?
C44 C43 C48 123.1(6) . . ?
C42 C43 C48 121.2(6) . . ?
C45 C44 C43 121.6(7) . . ?
C45 C44 H44 119.2 . . ?
C43 C44 H44 119.2 . . ?
N6 C45 C44 121.5(6) . . ?
N6 C45 H45 119.3 . . ?
C44 C45 H45 119.3 . . ?
C47 C46 N7 121.4(7) . . ?
C47 C46 H46 119.3 . . ?
N7 C46 H46 119.3 . . ?
C46 C47 C48 121.8(7) . . ?
C46 C47 H47 119.1 . . ?
C48 C47 H47 119.1 . . ?
C47 C48 C49 114.5(6) . . ?
C47 C48 C43 123.3(6) . . ?
C49 C48 C43 122.2(7) . . ?
C50 C49 C48 121.6(7) . . ?
C50 C49 H49 119.2 . . ?
C48 C49 H49 119.2 . . ?
C49 C50 N7 122.4(7) . . ?
C49 C50 H50 118.8 . . ?
N7 C50 H50 118.8 . . ?
N7 C51 C52 111.3(6) . . ?
N7 C51 H51A 109.4 . . ?
C52 C51 H51A 109.4 . . ?
N7 C51 H51B 109.4 . . ?
C52 C51 H51B 109.4 . . ?
H51A C51 H51B 108.0 . . ?
C53 C52 C51 114.0(6) . . ?
C53 C52 H52A 108.8 . . ?
C51 C52 H52A 108.8 . . ?
C53 C52 H52B 108.8 . . ?
C51 C52 H52B 108.8 . . ?
H52A C52 H52B 107.6 . . ?
C52 C53 C54 113.8(6) . . ?
C52 C53 H53A 108.8 . . ?
C54 C53 H53A 108.8 . . ?
C52 C53 H53B 108.8 . . ?
C54 C53 H53B 108.8 . . ?
H53A C53 H53B 107.7 . . ?
C53 C54 C55 113.2(6) . . ?
C53 C54 H54A 108.9 . . ?
C55 C54 H54A 108.9 . . ?
C53 C54 H54B 108.9 . . ?
C55 C54 H54B 108.9 . . ?
H54A C54 H54B 107.7 . . ?
N8 C55 C54 111.7(6) . . ?
N8 C55 H55A 109.3 . . ?
C54 C55 H55A 109.3 . . ?
N8 C55 H55B 109.3 . . ?
C54 C55 H55B 109.3 . . ?
H55A C55 H55B 107.9 . . ?
N8 C56 C57 121.0(6) . . ?
N8 C56 H56 119.5 . . ?
C57 C56 H56 119.5 . . ?
C56 C57 C58 121.7(6) . . ?
C56 C57 H57 119.2 . . ?
C58 C57 H57 119.2 . . ?
C57 C58 C33 123.1(6) . . ?
C57 C58 C59 115.0(5) . . ?
C33 C58 C59 121.9(6) . . ?
C60 C59 C58 120.9(6) . . ?
C60 C59 H59 119.5 . . ?
C58 C59 H59 119.5 . . ?
C59 C60 N8 121.8(6) . . ?
C59 C60 H60 119.1 . . ?
N8 C60 H60 119.1 . . ?
N9 C61 C62 178.4(10) . . ?
C61 C62 H62A 109.5 . . ?
C61 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C61 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
N10 C63 C64 178(2) . . ?
C63 C64 H64A 109.5 . . ?
C63 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
C63 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C66 C65 O1 106.5(13) . . ?
C66 C65 H65A 110.4 . . ?
O1 C65 H65A 110.4 . . ?
C66 C65 H65B 110.4 . . ?
O1 C65 H65B 110.4 . . ?
H65A C65 H65B 108.6 . . ?
C65 C66 H66A 109.5 . . ?
C65 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
C65 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
O1 C67 C68 113.4(15) . . ?
O1 C67 H67A 108.9 . . ?
C68 C67 H67A 108.9 . . ?
O1 C67 H67B 108.9 . . ?
C68 C67 H67B 108.9 . . ?
H67A C67 H67B 107.7 . . ?
C67 C68 H68A 109.5 . . ?
C67 C68 H68B 109.5 . . ?
H68A C68 H68B 109.5 . . ?
C67 C68 H68C 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
C1 N1 C5 119.3(5) . . ?
C1 N1 C6 120.1(6) . . ?
C5 N1 C6 120.6(6) . . ?
C11 N2 C15 118.8(5) . . ?
C11 N2 C10 121.1(6) . . ?
C15 N2 C10 119.9(6) . . ?
C16 N3 C20 118.9(5) . . ?
C16 N3 C21 121.2(6) . . ?
C20 N3 C21 119.8(6) . . ?
C30 N4 C26 119.3(5) . . ?
C30 N4 C25 120.1(5) . . ?
C26 N4 C25 120.6(5) . . ?
C35 N5 C31 118.7(5) . . ?
C35 N5 C36 119.7(6) . . ?
C31 N5 C36 121.5(6) . . ?
C45 N6 C41 118.9(6) . . ?
C45 N6 C40 120.9(6) . . ?
C41 N6 C40 120.1(6) . . ?
C50 N7 C46 118.2(6) . . ?
C50 N7 C51 120.4(7) . . ?
C46 N7 C51 121.3(7) . . ?
C56 N8 C60 119.6(5) . . ?
C56 N8 C55 119.7(6) . . ?
C60 N8 C55 120.5(6) . . ?
C67 O1 C65 120.0(14) . . ?
F4 P1 F1 179.2(7) . . ?
F4 P1 F3 92.3(6) . . ?
F1 P1 F3 88.2(5) . . ?
F4 P1 F6 87.0(6) . . ?
F1 P1 F6 92.5(6) . . ?
F3 P1 F6 178.6(4) . . ?
F4 P1 F2 91.3(5) . . ?
F1 P1 F2 89.2(5) . . ?
F3 P1 F2 93.0(3) . . ?
F6 P1 F2 88.2(3) . . ?
F4 P1 F5 90.2(5) . . ?
F1 P1 F5 89.2(5) . . ?
F3 P1 F5 87.9(3) . . ?
F6 P1 F5 91.0(3) . . ?
F2 P1 F5 178.2(4) . . ?
F9 P2 F11 98.1(10) . . ?
F9 P2 F8 95.0(10) . . ?
F11 P2 F8 166.7(9) . . ?
F9 P2 F12 178.9(5) . . ?
F11 P2 F12 82.2(8) . . ?
F8 P2 F12 84.7(9) . . ?
F9 P2 F10 90.8(3) . . ?
F11 P2 F10 93.1(4) . . ?
F8 P2 F10 89.0(4) . . ?
F12 P2 F10 88.2(4) . . ?
F9 P2 F7 88.3(4) . . ?
F11 P2 F7 86.9(4) . . ?
F8 P2 F7 91.2(4) . . ?
F12 P2 F7 92.7(4) . . ?
F10 P2 F7 179.1(3) . . ?
F18 P3 F14 95.5(8) . . ?
F18 P3 F17 89.6(8) . . ?
F14 P3 F17 174.8(7) . . ?
F18 P3 F15 178.6(8) . . ?
F14 P3 F15 85.8(6) . . ?
F17 P3 F15 89.0(7) . . ?
F18 P3 F16 89.0(4) . . ?
F14 P3 F16 90.6(3) . . ?
F17 P3 F16 88.5(3) . . ?
F15 P3 F16 90.9(4) . . ?
F18 P3 F13 92.2(4) . . ?
F14 P3 F13 90.8(3) . . ?
F17 P3 F13 90.0(4) . . ?
F15 P3 F13 87.9(4) . . ?
F16 P3 F13 178.1(4) . . ?
F19 P4 F20 93.8(8) . . ?
F19 P4 F21 91.2(4) . . ?
F20 P4 F21 90.1(5) . . ?
F19 P4 F23 92.4(8) . . ?
F20 P4 F23 173.0(7) . . ?
F21 P4 F23 93.1(5) . . ?
F19 P4 F22 178.8(5) . . ?
F20 P4 F22 86.9(6) . . ?
F21 P4 F22 89.7(3) . . ?
F23 P4 F22 86.9(6) . . ?
F19 P4 F24 88.5(4) . . ?
F20 P4 F24 90.4(4) . . ?
F21 P4 F24 179.5(5) . . ?
F23 P4 F24 86.5(4) . . ?
F22 P4 F24 90.5(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -1.2(10) . . . . ?
C1 C2 C3 C4 1.4(9) . . . . ?
C1 C2 C3 C28 -179.8(6) . . . . ?
C2 C3 C4 C5 -1.3(9) . . . . ?
C28 C3 C4 C5 179.9(6) . . . . ?
C3 C4 C5 N1 1.1(10) . . . . ?
N1 C6 C7 C8 -58.1(8) . . . . ?
C6 C7 C8 C9 -64.4(8) . . . . ?
C7 C8 C9 C10 -179.9(5) . . . . ?
C8 C9 C10 N2 -58.4(8) . . . . ?
N2 C11 C12 C13 0.3(10) . . . . ?
C11 C12 C13 C14 -0.2(9) . . . . ?
C11 C12 C13 C18 179.1(6) . . . . ?
C12 C13 C14 C15 0.5(9) . . . . ?
C18 C13 C14 C15 -178.8(6) . . . . ?
C13 C14 C15 N2 -0.8(10) . . . . ?
N3 C16 C17 C18 0.8(11) . . . . ?
C16 C17 C18 C19 0.7(9) . . . . ?
C16 C17 C18 C13 -179.4(6) . . . . ?
C14 C13 C18 C19 -3.6(10) . . . . ?
C12 C13 C18 C19 177.1(6) . . . . ?
C14 C13 C18 C17 176.5(6) . . . . ?
C12 C13 C18 C17 -2.8(10) . . . . ?
C17 C18 C19 C20 -1.4(9) . . . . ?
C13 C18 C19 C20 178.6(6) . . . . ?
C18 C19 C20 N3 0.7(10) . . . . ?
N3 C21 C22 C23 59.9(8) . . . . ?
C21 C22 C23 C24 179.2(6) . . . . ?
C22 C23 C24 C25 64.7(8) . . . . ?
C23 C24 C25 N4 56.9(8) . . . . ?
N4 C26 C27 C28 1.0(10) . . . . ?
C26 C27 C28 C29 -0.9(9) . . . . ?
C26 C27 C28 C3 179.2(6) . . . . ?
C4 C3 C28 C29 -1.1(10) . . . . ?
C2 C3 C28 C29 -179.8(6) . . . . ?
C4 C3 C28 C27 178.7(6) . . . . ?
C2 C3 C28 C27 0.0(10) . . . . ?
C27 C28 C29 C30 -0.1(9) . . . . ?
C3 C28 C29 C30 179.8(6) . . . . ?
C28 C29 C30 N4 1.0(10) . . . . ?
N5 C31 C32 C33 0.5(10) . . . . ?
C31 C32 C33 C34 0.6(9) . . . . ?
C31 C32 C33 C58 -179.1(6) . . . . ?
C32 C33 C34 C35 -1.2(9) . . . . ?
C58 C33 C34 C35 178.5(6) . . . . ?
C33 C34 C35 N5 0.7(10) . . . . ?
N5 C36 C37 C38 61.5(8) . . . . ?
C36 C37 C38 C39 178.6(6) . . . . ?
C37 C38 C39 C40 -178.4(6) . . . . ?
C38 C39 C40 N6 -60.0(9) . . . . ?
N6 C41 C42 C43 -1.3(11) . . . . ?
C41 C42 C43 C44 0.1(10) . . . . ?
C41 C42 C43 C48 179.1(6) . . . . ?
C42 C43 C44 C45 -0.2(10) . . . . ?
C48 C43 C44 C45 -179.2(7) . . . . ?
C43 C44 C45 N6 1.5(11) . . . . ?
N7 C46 C47 C48 0.4(11) . . . . ?
C46 C47 C48 C49 1.7(10) . . . . ?
C46 C47 C48 C43 -179.4(6) . . . . ?
C44 C43 C48 C47 -179.7(6) . . . . ?
C42 C43 C48 C47 1.4(10) . . . . ?
C44 C43 C48 C49 -0.8(11) . . . . ?
C42 C43 C48 C49 -179.7(6) . . . . ?
C47 C48 C49 C50 -2.2(10) . . . . ?
C43 C48 C49 C50 178.9(7) . . . . ?
C48 C49 C50 N7 0.6(12) . . . . ?
N7 C51 C52 C53 62.2(9) . . . . ?
C51 C52 C53 C54 -180.0(6) . . . . ?
C52 C53 C54 C55 -177.4(6) . . . . ?
C53 C54 C55 N8 -62.2(8) . . . . ?
N8 C56 C57 C58 -1.8(10) . . . . ?
C56 C57 C58 C33 180.0(6) . . . . ?
C56 C57 C58 C59 0.1(9) . . . . ?
C34 C33 C58 C57 179.9(5) . . . . ?
C32 C33 C58 C57 -0.5(10) . . . . ?
C34 C33 C58 C59 -0.2(9) . . . . ?
C32 C33 C58 C59 179.4(5) . . . . ?
C57 C58 C59 C60 1.5(9) . . . . ?
C33 C58 C59 C60 -178.4(6) . . . . ?
C58 C59 C60 N8 -1.4(10) . . . . ?
C2 C1 N1 C5 0.9(10) . . . . ?
C2 C1 N1 C6 177.3(6) . . . . ?
C4 C5 N1 C1 -0.8(10) . . . . ?
C4 C5 N1 C6 -177.2(6) . . . . ?
C7 C6 N1 C1 -80.0(7) . . . . ?
C7 C6 N1 C5 96.4(7) . . . . ?
C12 C11 N2 C15 -0.6(10) . . . . ?
C12 C11 N2 C10 -176.6(6) . . . . ?
C14 C15 N2 C11 0.8(9) . . . . ?
C14 C15 N2 C10 176.9(6) . . . . ?
C9 C10 N2 C11 94.9(7) . . . . ?
C9 C10 N2 C15 -81.1(8) . . . . ?
C17 C16 N3 C20 -1.6(10) . . . . ?
C17 C16 N3 C21 176.9(6) . . . . ?
C19 C20 N3 C16 0.8(10) . . . . ?
C19 C20 N3 C21 -177.6(6) . . . . ?
C22 C21 N3 C16 -93.2(8) . . . . ?
C22 C21 N3 C20 85.3(8) . . . . ?
C29 C30 N4 C26 -1.0(10) . . . . ?
C29 C30 N4 C25 176.6(6) . . . . ?
C27 C26 N4 C30 0.0(9) . . . . ?
C27 C26 N4 C25 -177.6(6) . . . . ?
C24 C25 N4 C30 -95.3(7) . . . . ?
C24 C25 N4 C26 82.2(7) . . . . ?
C34 C35 N5 C31 0.4(9) . . . . ?
C34 C35 N5 C36 -176.6(6) . . . . ?
C32 C31 N5 C35 -1.1(9) . . . . ?
C32 C31 N5 C36 175.9(6) . . . . ?
C37 C36 N5 C35 83.4(7) . . . . ?
C37 C36 N5 C31 -93.6(7) . . . . ?
C44 C45 N6 C41 -2.6(10) . . . . ?
C44 C45 N6 C40 174.4(6) . . . . ?
C42 C41 N6 C45 2.5(10) . . . . ?
C42 C41 N6 C40 -174.5(6) . . . . ?
C39 C40 N6 C45 -85.4(8) . . . . ?
C39 C40 N6 C41 91.5(8) . . . . ?
C49 C50 N7 C46 1.6(11) . . . . ?
C49 C50 N7 C51 -176.3(7) . . . . ?
C47 C46 N7 C50 -2.1(10) . . . . ?
C47 C46 N7 C51 175.7(6) . . . . ?
C52 C51 N7 C50 80.7(8) . . . . ?
C52 C51 N7 C46 -97.1(9) . . . . ?
C57 C56 N8 C60 1.9(10) . . . . ?
C57 C56 N8 C55 -173.3(6) . . . . ?
C59 C60 N8 C56 -0.3(10) . . . . ?
C59 C60 N8 C55 174.8(6) . . . . ?
C54 C55 N8 C56 90.0(8) . . . . ?
C54 C55 N8 C60 -85.1(8) . . . . ?
C68 C67 O1 C65 -179.1(13) . . . . ?
C66 C65 O1 C67 178.5(13) . . . . ?

_refine_diff_density_max         1.266
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.090

_shelxl_version_number           2013-4


_chemical_properties_physical    Air-sensitive
####################################################################### 
# 
# 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_jwmb150205
_database_code_depnum_ccdc_archive 'CCDC 1051242'
_audit_update_record             
;
2015-02-25 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H36 N4, 2(F6 P), C7 H8, C2 H3 N'
_chemical_formula_sum            'C39 H47 F12 N5 P2'
_chemical_formula_weight         875.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.767(5)
_cell_length_b                   15.632(5)
_cell_length_c                   18.005(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4156(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5374
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.27

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             1816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6915
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23293
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.725
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10033
_reflns_number_gt                6541
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0817P)²+1.4664P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2277 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.00(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         10033
_refine_ls_number_parameters     531
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1658
_refine_ls_wR_factor_gt          0.1429
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2107(3) 0.5927(3) 0.7953(2) 0.0419(11) Uani 1 1 d . . . . .
H1 H -0.2502 0.6135 0.8328 0.050 Uiso 1 1 calc R U . . .
C2 C -0.1213(3) 0.5908(3) 0.8085(2) 0.0405(11) Uani 1 1 d . . . . .
H2 H -0.0991 0.6120 0.8544 0.049 Uiso 1 1 calc R U . . .
C3 C -0.0584(3) 0.5575(3) 0.7552(2) 0.0329(9) Uani 1 1 d . . . . .
C4 C -0.0986(3) 0.5306(3) 0.6870(2) 0.0397(11) Uani 1 1 d . . . . .
H4 H -0.0612 0.5091 0.6484 0.048 Uiso 1 1 calc R U . . .
C5 C -0.1893(3) 0.5353(3) 0.6763(3) 0.0415(11) Uani 1 1 d . . . . .
H5 H -0.2136 0.5167 0.6302 0.050 Uiso 1 1 calc R U . . .
C6 C -0.3461(3) 0.5659(3) 0.7173(3) 0.0419(11) Uani 1 1 d . . . . .
H6A H -0.3592 0.5554 0.6642 0.050 Uiso 1 1 calc R U . . .
H6B H -0.3703 0.6230 0.7303 0.050 Uiso 1 1 calc R U . . .
C7 C -0.3936(3) 0.4989(3) 0.7636(3) 0.0519(13) Uani 1 1 d . . . . .
H7A H -0.3966 0.5225 0.8146 0.062 Uiso 1 1 calc R U . A 1
H7B H -0.4567 0.4970 0.7452 0.062 Uiso 1 1 calc R U . A 1
C8 C -0.3654(6) 0.4098(7) 0.7719(5) 0.0415(16) Uani 0.5 1 d . . P B 1
H8A H -0.4030 0.3816 0.8103 0.050 Uiso 0.5 1 calc R U P B 1
H8B H -0.3015 0.4076 0.7883 0.050 Uiso 0.5 1 calc R U P B 1
C9 C -0.3757(7) 0.3603(7) 0.6956(6) 0.0428(16) Uani 0.5 1 d . . P B 1
H9A H -0.3341 0.3850 0.6582 0.051 Uiso 0.5 1 calc R U P B 1
H9B H -0.4385 0.3661 0.6769 0.051 Uiso 0.5 1 calc R U P B 1
C8B C -0.3559(6) 0.4061(7) 0.7176(6) 0.0415(16) Uani 0.5 1 d . . P B 2
H8B1 H -0.3730 0.4087 0.6645 0.050 Uiso 0.5 1 calc R U P B 2
H8B2 H -0.2891 0.4022 0.7208 0.050 Uiso 0.5 1 calc R U P B 2
C9B C -0.3965(6) 0.3318(6) 0.7519(6) 0.0428(16) Uani 0.5 1 d . . P B 2
H9B1 H -0.4631 0.3314 0.7455 0.051 Uiso 0.5 1 calc R U P B 2
H9B2 H -0.3817 0.3283 0.8054 0.051 Uiso 0.5 1 calc R U P B 2
C10 C -0.3521(3) 0.2610(4) 0.7085(4) 0.0614(16) Uani 1 1 d . . . . .
H10A H -0.3920 0.2370 0.7475 0.074 Uiso 0.5 1 calc R U P B 1
H10B H -0.3626 0.2285 0.6621 0.074 Uiso 0.5 1 calc R U P B 1
H10C H -0.3844 0.2065 0.7176 0.074 Uiso 0.5 1 calc R U P B 2
H10D H -0.3554 0.2738 0.6547 0.074 Uiso 0.5 1 calc R U P B 2
C11 C -0.1882(3) 0.2759(4) 0.6837(3) 0.0474(12) Uani 1 1 d . . . . .
H11 H -0.2032 0.2920 0.6344 0.057 Uiso 1 1 calc R U . . .
C12 C -0.1000(3) 0.2767(3) 0.7052(3) 0.0421(11) Uani 1 1 d . . . . .
H12 H -0.0546 0.2923 0.6702 0.050 Uiso 1 1 calc R U . . .
C13 C -0.0741(3) 0.2547(3) 0.7789(2) 0.0376(10) Uani 1 1 d . . . . .
C14 C -0.1472(3) 0.2302(3) 0.8262(3) 0.0442(11) Uani 1 1 d . . . . .
H14 H -0.1349 0.2130 0.8758 0.053 Uiso 1 1 calc R U . . .
C15 C -0.2338(3) 0.2310(4) 0.8015(3) 0.0477(12) Uani 1 1 d . . . . .
H15 H -0.2809 0.2159 0.8350 0.057 Uiso 1 1 calc R U . . .
C16 C 0.1779(3) 0.2774(3) 0.7795(3) 0.0413(11) Uani 1 1 d . . . . .
H16 H 0.2250 0.2923 0.7459 0.050 Uiso 1 1 calc R U . . .
C17 C 0.0907(3) 0.2799(3) 0.7556(3) 0.0389(10) Uani 1 1 d . . . . .
H17 H 0.0780 0.2985 0.7065 0.047 Uiso 1 1 calc R U . . .
C18 C 0.0183(3) 0.2554(3) 0.8027(2) 0.0339(9) Uani 1 1 d . . . . .
C19 C 0.0438(3) 0.2334(3) 0.8767(2) 0.0427(11) Uani 1 1 d . . . . .
H19 H -0.0017 0.2182 0.9116 0.051 Uiso 1 1 calc R U . . .
C20 C 0.1313(3) 0.2339(3) 0.8978(2) 0.0432(11) Uani 1 1 d . . . . .
H20 H 0.1460 0.2196 0.9477 0.052 Uiso 1 1 calc R U . . .
C21 C 0.2944(3) 0.2520(3) 0.8761(3) 0.0429(11) Uani 1 1 d . . . . .
H21A H 0.3355 0.2581 0.8330 0.051 Uiso 1 1 calc R U . . .
H21B H 0.3064 0.1956 0.8992 0.051 Uiso 1 1 calc R U . . .
C22 C 0.3150(3) 0.3218(3) 0.9319(3) 0.0440(11) Uani 1 1 d . . . . .
H22A H 0.3803 0.3197 0.9442 0.053 Uiso 1 1 calc R U . . .
H22B H 0.2809 0.3099 0.9781 0.053 Uiso 1 1 calc R U . . .
C23 C 0.2919(3) 0.4116(3) 0.9060(3) 0.0425(11) Uani 1 1 d . . . . .
H23A H 0.3056 0.4522 0.9467 0.051 Uiso 1 1 calc R U . . .
H23B H 0.2260 0.4146 0.8963 0.051 Uiso 1 1 calc R U . . .
C24 C 0.3422(3) 0.4406(3) 0.8364(3) 0.0422(11) Uani 1 1 d . . . . .
H24A H 0.4081 0.4348 0.8450 0.051 Uiso 1 1 calc R U . . .
H24B H 0.3258 0.4022 0.7948 0.051 Uiso 1 1 calc R U . . .
C25 C 0.3220(3) 0.5318(3) 0.8139(3) 0.0440(12) Uani 1 1 d . . . . .
H25A H 0.3402 0.5709 0.8545 0.053 Uiso 1 1 calc R U . . .
H25B H 0.3580 0.5466 0.7693 0.053 Uiso 1 1 calc R U . . .
C26 C 0.1658(3) 0.5707(3) 0.8515(3) 0.0413(11) Uani 1 1 d . . . . .
H26 H 0.1893 0.5866 0.8986 0.050 Uiso 1 1 calc R U . . .
C27 C 0.0747(3) 0.5753(3) 0.8398(2) 0.0402(11) Uani 1 1 d . . . . .
H27 H 0.0360 0.5934 0.8789 0.048 Uiso 1 1 calc R U . . .
C28 C 0.0364(3) 0.5534(3) 0.7694(2) 0.0352(10) Uani 1 1 d . . . . .
C29 C 0.0997(3) 0.5249(3) 0.7154(2) 0.0374(10) Uani 1 1 d . . . . .
H29 H 0.0783 0.5081 0.6678 0.045 Uiso 1 1 calc R U . . .
C30 C 0.1899(3) 0.5209(3) 0.7298(3) 0.0411(11) Uani 1 1 d . . . . .
H30 H 0.2301 0.5019 0.6920 0.049 Uiso 1 1 calc R U . . .
C31 C 0.3915(4) 0.2958(5) 0.6272(4) 0.0678(18) Uani 1 1 d . . . . .
C32 C 0.4006(4) 0.3350(5) 0.5550(4) 0.081(2) Uani 1 1 d . . . . .
H32A H 0.3660 0.3021 0.5184 0.121 Uiso 1 1 calc R U . . .
H32B H 0.4647 0.3358 0.5406 0.121 Uiso 1 1 calc R U . . .
H32C H 0.3775 0.3937 0.5569 0.121 Uiso 1 1 calc R U . . .
C33 C 0.7181(4) 0.4160(4) 0.9610(3) 0.0620(15) Uani 1 1 d . . . . .
H33 H 0.7090 0.3581 0.9469 0.074 Uiso 1 1 calc R U . . .
C34 C 0.8050(5) 0.4473(6) 0.9703(4) 0.0759(19) Uani 1 1 d . . . . .
H34 H 0.8551 0.4101 0.9629 0.091 Uiso 1 1 calc R U . . .
C35 C 0.8203(5) 0.5298(6) 0.9899(3) 0.081(2) Uani 1 1 d . . . . .
H35 H 0.8802 0.5500 0.9975 0.097 Uiso 1 1 calc R U . . .
C36 C 0.7482(5) 0.5829(5) 0.9982(3) 0.077(2) Uani 1 1 d . . . . .
H36 H 0.7589 0.6412 1.0102 0.093 Uiso 1 1 calc R U . . .
C37 C 0.6603(5) 0.5554(4) 0.9901(3) 0.0639(16) Uani 1 1 d . . . . .
H37 H 0.6113 0.5940 0.9965 0.077 Uiso 1 1 calc R U . . .
C38 C 0.6444(4) 0.4692(4) 0.9722(3) 0.0556(14) Uani 1 1 d . . . . .
C39 C 0.5515(4) 0.4368(6) 0.9657(4) 0.082(2) Uani 1 1 d . . . . .
H39A H 0.5521 0.3815 0.9401 0.124 Uiso 1 1 calc R U . . .
H39B H 0.5149 0.4776 0.9372 0.124 Uiso 1 1 calc R U . . .
H39C H 0.5254 0.4297 1.0153 0.124 Uiso 1 1 calc R U . . .
N1 N -0.2467(2) 0.5654(3) 0.7288(2) 0.0409(9) Uani 1 1 d . . . . .
N2 N -0.2559(2) 0.2524(3) 0.7314(2) 0.0476(10) Uani 1 1 d . . . . .
N3 N 0.1998(2) 0.2542(3) 0.8498(2) 0.0385(9) Uani 1 1 d . . . . .
N4 N 0.2241(2) 0.5437(3) 0.7975(2) 0.0376(9) Uani 1 1 d . . . . .
N5 N 0.3834(4) 0.2655(6) 0.6828(4) 0.102(2) Uani 1 1 d . . . . .
F1 F -0.0227(3) 0.3392(3) 1.0519(4) 0.127(2) Uani 1 1 d . . . . .
F2 F 0.0472(4) 0.3595(4) 1.1603(2) 0.132(2) Uani 1 1 d . . . . .
F3 F 0.1238(3) 0.3070(3) 1.0641(2) 0.0915(13) Uani 1 1 d . . . . .
F4 F 0.1480(3) 0.4385(4) 1.1063(4) 0.140(2) Uani 1 1 d . . . . .
F5 F 0.0802(3) 0.4211(3) 0.9972(2) 0.1032(15) Uani 1 1 d . . . . .
F6 F 0.0000(3) 0.4709(3) 1.0923(2) 0.0913(13) Uani 1 1 d . . . . .
F7 F 0.1808(3) 0.3125(5) 0.5947(2) 0.127(2) Uani 1 1 d . . . . .
F8 F 0.1538(5) 0.4236(4) 0.5202(4) 0.161(3) Uani 1 1 d . . . . .
F9 F 0.2010(3) 0.3058(4) 0.4736(2) 0.1189(19) Uani 1 1 d . . . . .
F10 F 0.0573(3) 0.3456(4) 0.4553(2) 0.1032(16) Uani 1 1 d . . . . .
F11 F 0.0844(4) 0.2379(3) 0.5335(5) 0.153(3) Uani 1 1 d . . . . .
F12 F 0.0389(3) 0.3610(3) 0.5778(2) 0.1021(16) Uani 1 1 d . . . . .
P1 P 0.06287(9) 0.38948(11) 1.07737(8) 0.0540(4) Uani 1 1 d . . . . .
P2 P 0.11880(9) 0.33016(11) 0.52513(8) 0.0541(4) 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
C1 C2 1.341(6) . ?
C1 N1 1.377(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.432(6) . ?
C2 H2 0.9500 . ?
C3 C28 1.426(6) . ?
C3 C4 1.428(6) . ?
C4 C5 1.355(6) . ?
C4 H4 0.9500 . ?
C5 N1 1.354(6) . ?
C5 H5 0.9500 . ?
C6 N1 1.483(5) . ?
C6 C7 1.511(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.461(11) . ?
C7 C8B 1.760(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.583(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.609(12) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C8B C9B 1.446(14) . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9B C10 1.505(11) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C10 N2 1.485(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 H10C 0.9900 . ?
C10 H10D 0.9900 . ?
C11 C12 1.358(6) . ?
C11 N2 1.369(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.425(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.427(6) . ?
C13 C18 1.430(6) . ?
C14 C15 1.354(7) . ?
C14 H14 0.9500 . ?
C15 N2 1.346(7) . ?
C15 H15 0.9500 . ?
C16 N3 1.355(6) . ?
C16 C17 1.359(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.417(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.427(6) . ?
C19 C20 1.348(7) . ?
C19 H19 0.9500 . ?
C20 N3 1.369(6) . ?
C20 H20 0.9500 . ?
C21 N3 1.475(5) . ?
C21 C22 1.515(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.518(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.526(7) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.510(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N4 1.488(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.364(6) . ?
C26 N4 1.366(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.429(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.420(6) . ?
C29 C30 1.359(6) . ?
C29 H29 0.9500 . ?
C30 N4 1.366(6) . ?
C30 H30 0.9500 . ?
C31 N5 1.114(9) . ?
C31 C32 1.444(10) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C38 1.384(8) . ?
C33 C34 1.384(9) . ?
C33 H33 0.9500 . ?
C34 C35 1.355(11) . ?
C34 H34 0.9500 . ?
C35 C36 1.359(11) . ?
C35 H35 0.9500 . ?
C36 C37 1.374(9) . ?
C36 H36 0.9500 . ?
C37 C38 1.406(9) . ?
C37 H37 0.9500 . ?
C38 C39 1.467(8) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
F1 P1 1.557(5) . ?
F2 P1 1.582(4) . ?
F3 P1 1.590(4) . ?
F4 P1 1.561(5) . ?
F5 P1 1.547(4) . ?
F6 P1 1.597(4) . ?
F7 P2 1.576(4) . ?
F8 P2 1.552(5) . ?
F9 P2 1.574(4) . ?
F10 P2 1.569(4) . ?
F11 P2 1.536(5) . ?
F12 P2 1.588(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
C2 C1 N1 121.7(4) . . ?
C2 C1 H1 119.1 . . ?
N1 C1 H1 119.1 . . ?
C1 C2 C3 121.9(4) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C28 C3 C4 123.3(4) . . ?
C28 C3 C2 122.3(4) . . ?
C4 C3 C2 114.4(4) . . ?
C5 C4 C3 121.2(4) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
N1 C5 C4 122.6(4) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
N1 C6 C7 112.2(4) . . ?
N1 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 125.8(5) . . ?
C6 C7 C8B 99.5(5) . . ?
C8 C7 H7A 105.9 . . ?
C6 C7 H7A 105.9 . . ?
C8 C7 H7B 105.9 . . ?
C6 C7 H7B 105.9 . . ?
H7A C7 H7B 106.2 . . ?
C7 C8 C9 110.5(7) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 109.0(7) . . ?
C8 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C9B C8B C7 109.3(7) . . ?
C9B C8B H8B1 109.8 . . ?
C7 C8B H8B1 109.8 . . ?
C9B C8B H8B2 109.8 . . ?
C7 C8B H8B2 109.8 . . ?
H8B1 C8B H8B2 108.3 . . ?
C8B C9B C10 100.9(8) . . ?
C8B C9B H9B1 111.6 . . ?
C10 C9B H9B1 111.6 . . ?
C8B C9B H9B2 111.6 . . ?
C10 C9B H9B2 111.6 . . ?
H9B1 C9B H9B2 109.4 . . ?
N2 C10 C9B 109.8(5) . . ?
N2 C10 C9 109.5(5) . . ?
N2 C10 H10A 109.8 . . ?
C9 C10 H10A 109.8 . . ?
N2 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
N2 C10 H10C 109.7 . . ?
C9B C10 H10C 109.7 . . ?
N2 C10 H10D 109.7 . . ?
C9B C10 H10D 109.7 . . ?
H10C C10 H10D 108.2 . . ?
C12 C11 N2 121.7(5) . . ?
C12 C11 H11 119.2 . . ?
N2 C11 H11 119.2 . . ?
C11 C12 C13 121.3(4) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C14 114.7(4) . . ?
C12 C13 C18 122.2(4) . . ?
C14 C13 C18 123.1(4) . . ?
C15 C14 C13 121.1(5) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
N2 C15 C14 122.6(4) . . ?
N2 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
N3 C16 C17 122.0(4) . . ?
N3 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C16 C17 C18 121.2(4) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C19 115.1(4) . . ?
C17 C18 C13 122.9(4) . . ?
C19 C18 C13 121.9(4) . . ?
C20 C19 C18 121.0(4) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 N3 122.1(4) . . ?
C19 C20 H20 118.9 . . ?
N3 C20 H20 118.9 . . ?
N3 C21 C22 112.7(4) . . ?
N3 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
N3 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 C23 114.7(4) . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 C24 114.7(4) . . ?
C22 C23 H23A 108.6 . . ?
C24 C23 H23A 108.6 . . ?
C22 C23 H23B 108.6 . . ?
C24 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
C25 C24 C23 113.9(4) . . ?
C25 C24 H24A 108.8 . . ?
C23 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
N4 C25 C24 111.3(4) . . ?
N4 C25 H25A 109.4 . . ?
C24 C25 H25A 109.4 . . ?
N4 C25 H25B 109.4 . . ?
C24 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
C27 C26 N4 121.9(4) . . ?
C27 C26 H26 119.1 . . ?
N4 C26 H26 119.1 . . ?
C26 C27 C28 120.9(4) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C29 C28 C3 122.6(4) . . ?
C29 C28 C27 115.0(4) . . ?
C3 C28 C27 122.4(4) . . ?
C30 C29 C28 122.0(4) . . ?
C30 C29 H29 119.0 . . ?
C28 C29 H29 119.0 . . ?
C29 C30 N4 121.3(4) . . ?
C29 C30 H30 119.3 . . ?
N4 C30 H30 119.3 . . ?
N5 C31 C32 179.3(7) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C38 C33 C34 120.0(7) . . ?
C38 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C35 C34 C33 121.4(7) . . ?
C35 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C34 C35 C36 118.7(7) . . ?
C34 C35 H35 120.7 . . ?
C36 C35 H35 120.7 . . ?
C35 C36 C37 122.5(8) . . ?
C35 C36 H36 118.8 . . ?
C37 C36 H36 118.8 . . ?
C36 C37 C38 118.8(7) . . ?
C36 C37 H37 120.6 . . ?
C38 C37 H37 120.6 . . ?
C33 C38 C37 118.5(6) . . ?
C33 C38 C39 121.1(6) . . ?
C37 C38 C39 120.4(6) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C5 N1 C1 118.2(4) . . ?
C5 N1 C6 121.6(4) . . ?
C1 N1 C6 120.1(4) . . ?
C15 N2 C11 118.5(4) . . ?
C15 N2 C10 121.0(5) . . ?
C11 N2 C10 120.1(5) . . ?
C16 N3 C20 118.4(4) . . ?
C16 N3 C21 122.2(4) . . ?
C20 N3 C21 119.4(4) . . ?
C30 N4 C26 118.9(4) . . ?
C30 N4 C25 120.2(4) . . ?
C26 N4 C25 120.7(4) . . ?
F5 P1 F1 91.2(3) . . ?
F5 P1 F4 91.2(3) . . ?
F1 P1 F4 177.6(4) . . ?
F5 P1 F2 178.2(4) . . ?
F1 P1 F2 90.6(4) . . ?
F4 P1 F2 87.1(4) . . ?
F5 P1 F3 91.5(3) . . ?
F1 P1 F3 90.3(3) . . ?
F4 P1 F3 89.6(3) . . ?
F2 P1 F3 89.1(2) . . ?
F5 P1 F6 89.9(3) . . ?
F1 P1 F6 88.9(3) . . ?
F4 P1 F6 91.2(3) . . ?
F2 P1 F6 89.5(2) . . ?
F3 P1 F6 178.4(3) . . ?
F11 P2 F8 177.7(4) . . ?
F11 P2 F10 91.8(4) . . ?
F8 P2 F10 90.1(4) . . ?
F11 P2 F9 94.9(4) . . ?
F8 P2 F9 86.4(4) . . ?
F10 P2 F9 90.6(2) . . ?
F11 P2 F7 87.1(4) . . ?
F8 P2 F7 91.0(4) . . ?
F10 P2 F7 178.7(4) . . ?
F9 P2 F7 88.8(2) . . ?
F11 P2 F12 88.9(4) . . ?
F8 P2 F12 89.7(4) . . ?
F10 P2 F12 90.1(2) . . ?
F9 P2 F12 176.1(3) . . ?
F7 P2 F12 90.6(2) . . ?

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
N1 C1 C2 C3 -2.1(8) . . . . ?
C1 C2 C3 C28 -178.6(5) . . . . ?
C1 C2 C3 C4 2.5(7) . . . . ?
C28 C3 C4 C5 179.6(5) . . . . ?
C2 C3 C4 C5 -1.5(7) . . . . ?
C3 C4 C5 N1 0.1(8) . . . . ?
N1 C6 C7 C8 -45.9(8) . . . . ?
N1 C6 C7 C8B -69.9(5) . . . . ?
C6 C7 C8 C9 -66.8(9) . . . . ?
C8B C7 C8 C9 -21.2(7) . . . . ?
C7 C8 C9 C10 -175.3(6) . . . . ?
C8 C7 C8B C9B 37.9(8) . . . . ?
C6 C7 C8B C9B -178.0(6) . . . . ?
C7 C8B C9B C10 -176.7(6) . . . . ?
C8B C9B C10 N2 73.0(8) . . . . ?
C8B C9B C10 C9 -24.8(6) . . . . ?
C8 C9 C10 N2 -63.5(8) . . . . ?
C8 C9 C10 C9B 35.0(7) . . . . ?
N2 C11 C12 C13 -1.3(8) . . . . ?
C11 C12 C13 C14 1.6(7) . . . . ?
C11 C12 C13 C18 -179.8(5) . . . . ?
C12 C13 C14 C15 -1.9(7) . . . . ?
C18 C13 C14 C15 179.5(5) . . . . ?
C13 C14 C15 N2 1.9(8) . . . . ?
N3 C16 C17 C18 -2.2(8) . . . . ?
C16 C17 C18 C19 3.5(7) . . . . ?
C16 C17 C18 C13 -178.0(5) . . . . ?
C12 C13 C18 C17 1.6(7) . . . . ?
C14 C13 C18 C17 -179.9(5) . . . . ?
C12 C13 C18 C19 179.9(5) . . . . ?
C14 C13 C18 C19 -1.5(7) . . . . ?
C17 C18 C19 C20 -2.0(7) . . . . ?
C13 C18 C19 C20 179.5(5) . . . . ?
C18 C19 C20 N3 -0.8(8) . . . . ?
N3 C21 C22 C23 -53.8(6) . . . . ?
C21 C22 C23 C24 -60.4(5) . . . . ?
C22 C23 C24 C25 -176.9(4) . . . . ?
C23 C24 C25 N4 -60.5(5) . . . . ?
N4 C26 C27 C28 -1.1(8) . . . . ?
C4 C3 C28 C29 2.3(7) . . . . ?
C2 C3 C28 C29 -176.5(5) . . . . ?
C4 C3 C28 C27 -175.7(5) . . . . ?
C2 C3 C28 C27 5.4(7) . . . . ?
C26 C27 C28 C29 1.7(7) . . . . ?
C26 C27 C28 C3 179.9(5) . . . . ?
C3 C28 C29 C30 -179.7(5) . . . . ?
C27 C28 C29 C30 -1.5(7) . . . . ?
C28 C29 C30 N4 0.5(8) . . . . ?
C38 C33 C34 C35 -0.5(10) . . . . ?
C33 C34 C35 C36 -1.9(10) . . . . ?
C34 C35 C36 C37 2.3(10) . . . . ?
C35 C36 C37 C38 -0.2(9) . . . . ?
C34 C33 C38 C37 2.6(8) . . . . ?
C34 C33 C38 C39 -177.5(6) . . . . ?
C36 C37 C38 C33 -2.2(8) . . . . ?
C36 C37 C38 C39 177.8(6) . . . . ?
C4 C5 N1 C1 0.4(8) . . . . ?
C4 C5 N1 C6 -176.9(5) . . . . ?
C2 C1 N1 C5 0.6(7) . . . . ?
C2 C1 N1 C6 178.0(5) . . . . ?
C7 C6 N1 C5 107.4(5) . . . . ?
C7 C6 N1 C1 -69.9(6) . . . . ?
C14 C15 N2 C11 -1.4(8) . . . . ?
C14 C15 N2 C10 -173.8(5) . . . . ?
C12 C11 N2 C15 1.1(8) . . . . ?
C12 C11 N2 C10 173.6(5) . . . . ?
C9B C10 N2 C15 62.5(8) . . . . ?
C9 C10 N2 C15 108.4(7) . . . . ?
C9B C10 N2 C11 -109.9(7) . . . . ?
C9 C10 N2 C11 -63.9(7) . . . . ?
C17 C16 N3 C20 -0.8(7) . . . . ?
C17 C16 N3 C21 -179.5(5) . . . . ?
C19 C20 N3 C16 2.3(7) . . . . ?
C19 C20 N3 C21 -178.9(5) . . . . ?
C22 C21 N3 C16 110.1(5) . . . . ?
C22 C21 N3 C20 -68.6(6) . . . . ?
C29 C30 N4 C26 0.2(7) . . . . ?
C29 C30 N4 C25 174.8(5) . . . . ?
C27 C26 N4 C30 0.1(7) . . . . ?
C27 C26 N4 C25 -174.5(5) . . . . ?
C24 C25 N4 C30 -81.7(5) . . . . ?
C24 C25 N4 C26 92.8(5) . . . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4


_chemical_properties_physical    Air-sensitive
