# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_Compound_7
_database_code_depnum_ccdc_archive 'CCDC 1530885'
_audit_update_record             
;
2017-02-03 deposited with the CCDC.
2017-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 Cl4 F2 N8 P4'
_chemical_formula_sum            'C20 H26 Cl4 F2 N8 P4'
_chemical_formula_weight         682.17

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5886(2)
_cell_length_b                   9.2505(3)
_cell_length_c                   9.5924(3)
_cell_angle_alpha                75.382(3)
_cell_angle_beta                 71.148(3)
_cell_angle_gamma                87.868(3)
_cell_volume                     697.06(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5449
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_T_max  0.880
_exptl_absorpt_process_details   'SADABS; Bruker, 2005'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10863
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2850
_reflns_number_gt                2523
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'WinGX publication routines (Farrugia, 2012) and PLATON (Spek, 2009)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0621P)²+0.1989P] 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         2850
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.15724(6) 0.32594(5) 0.43112(6) 0.01630(17) Uani 1 1 d . . .
P2 P 0.13593(6) 0.54732(5) 0.61628(6) 0.01682(17) Uani 1 1 d . . .
Cl1 Cl 0.17160(8) 0.48780(6) 0.82120(7) 0.0348(2) Uani 1 1 d . . .
Cl2 Cl 0.35021(7) 0.66603(7) 0.48825(8) 0.0395(2) Uani 1 1 d . . .
F1 F 0.29143(18) -0.08374(18) 1.13869(17) 0.0419(4) Uani 1 1 d . . .
N1 N 0.1253(2) 0.40188(18) 0.5684(2) 0.0191(4) Uani 1 1 d . . .
N2 N -0.0049(2) 0.6595(2) 0.6329(2) 0.0257(4) Uani 1 1 d . . .
N3 N 0.2028(2) 0.15079(18) 0.4761(2) 0.0197(4) Uani 1 1 d . . .
N4 N 0.3352(2) 0.38127(19) 0.2953(2) 0.0218(4) Uani 1 1 d . . .
C1 C 0.2521(3) -0.0543(3) 1.0068(3) 0.0273(5) Uani 1 1 d . . .
C2 C 0.1465(3) -0.1547(2) 0.9932(3) 0.0279(5) Uani 1 1 d . . .
H2 H 0.1044 -0.2407 1.0705 0.033 Uiso 1 1 calc R . .
C3 C 0.1053(3) -0.1237(2) 0.8614(3) 0.0244(5) Uani 1 1 d . . .
H3 H 0.0354 -0.1906 0.8495 0.029 Uiso 1 1 calc R . .
C4 C 0.1664(2) 0.0064(2) 0.7456(3) 0.0198(5) Uani 1 1 d . . .
C5 C 0.2734(3) 0.1036(2) 0.7647(3) 0.0228(5) Uani 1 1 d . . .
H5 H 0.3159 0.1903 0.6885 0.027 Uiso 1 1 calc R . .
C6 C 0.3177(3) 0.0728(3) 0.8959(3) 0.0271(5) Uani 1 1 d . . .
H6 H 0.3903 0.1372 0.9078 0.033 Uiso 1 1 calc R . .
C7 C 0.1059(3) 0.0394(2) 0.6098(3) 0.0230(5) Uani 1 1 d . . .
H7A H 0.1014 -0.0532 0.5809 0.028 Uiso 1 1 calc R . .
H7B H -0.0058 0.0723 0.6412 0.028 Uiso 1 1 calc R . .
C8 C 0.3677(3) 0.1212(2) 0.3841(3) 0.0247(5) Uani 1 1 d . . .
H8A H 0.3661 0.0278 0.3559 0.030 Uiso 1 1 calc R . .
H8B H 0.4449 0.1155 0.4398 0.030 Uiso 1 1 calc R . .
C9 C 0.4155(3) 0.2519(3) 0.2437(3) 0.0283(5) Uani 1 1 d . . .
H9A H 0.5341 0.2697 0.2032 0.034 Uiso 1 1 calc R . .
H9B H 0.3770 0.2326 0.1652 0.034 Uiso 1 1 calc R . .
C10 C 0.3455(3) 0.5191(3) 0.1784(3) 0.0348(6) Uani 1 1 d . . .
H10A H 0.2747 0.5900 0.2224 0.052 Uiso 1 1 calc R . .
H10B H 0.3116 0.4987 0.0989 0.052 Uiso 1 1 calc R . .
H10C H 0.4570 0.5597 0.1367 0.052 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N1 1.5884(17) . ?
P1 N2 1.6037(18) 2_566 ?
P1 N3 1.6351(16) . ?
P1 N4 1.6527(18) . ?
P2 Cl1 2.0226(8) . ?
P2 Cl2 2.0273(8) . ?
P2 N1 1.5418(16) . ?
P2 N2 1.5592(17) . ?
F1 C1 1.372(3) . ?
N2 P1 1.6037(18) 2_566 ?
N3 C7 1.451(3) . ?
N3 C8 1.465(3) . ?
N4 C9 1.472(3) . ?
N4 C10 1.454(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.365(3) . ?
C2 H2 0.9300 . ?
C3 C2 1.380(3) . ?
C3 C4 1.397(3) . ?
C3 H3 0.9300 . ?
C4 C7 1.512(3) . ?
C5 C4 1.393(3) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.517(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 N2 112.07(9) . 2_566 ?
N1 P1 N3 112.27(9) . . ?
N1 P1 N4 113.26(9) . . ?
N2 P1 N3 110.27(9) 2_566 . ?
N2 P1 N4 112.74(10) 2_566 . ?
N3 P1 N4 95.12(9) . . ?
Cl1 P2 Cl2 100.08(4) . . ?
N1 P2 Cl1 106.97(7) . . ?
N1 P2 Cl2 111.09(7) . . ?
N1 P2 N2 122.78(9) . . ?
N2 P2 Cl1 105.67(8) . . ?
N2 P2 Cl2 107.73(8) . . ?
P2 N1 P1 146.41(13) . . ?
P2 N2 P1 129.33(11) . 2_566 ?
C7 N3 P1 124.43(14) . . ?
C7 N3 C8 121.45(16) . . ?
C8 N3 P1 113.24(14) . . ?
C9 N4 P1 109.83(14) . . ?
C10 N4 P1 119.08(15) . . ?
C10 N4 C9 116.83(18) . . ?
F1 C1 C2 118.2(2) . . ?
C6 C1 F1 118.9(2) . . ?
C6 C1 C2 123.0(2) . . ?
C1 C2 C3 118.0(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C7 118.52(18) . . ?
C5 C4 C3 118.4(2) . . ?
C5 C4 C7 123.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.4(2) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
N3 C7 C4 116.24(17) . . ?
N3 C7 H7A 108.2 . . ?
N3 C7 H7B 108.2 . . ?
C4 C7 H7A 108.2 . . ?
C4 C7 H7B 108.2 . . ?
H7A C7 H7B 107.4 . . ?
N3 C8 C9 105.32(16) . . ?
N3 C8 H8A 110.7 . . ?
N3 C8 H8B 110.7 . . ?
C9 C8 H8A 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
N4 C9 C8 105.49(18) . . ?
N4 C9 H9A 110.6 . . ?
N4 C9 H9B 110.6 . . ?
C8 C9 H9A 110.6 . . ?
C8 C9 H9B 110.6 . . ?
H9A C9 H9B 108.8 . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 P1 N1 P2 -86.2(2) 2_566 . . . ?
N3 P1 N1 P2 149.0(2) . . . . ?
N4 P1 N1 P2 42.7(2) . . . . ?
N1 P1 N3 C7 51.57(18) . . . . ?
N1 P1 N3 C8 -117.81(16) . . . . ?
N2 P1 N3 C7 -74.17(18) 2_566 . . . ?
N2 P1 N3 C8 116.44(16) 2_566 . . . ?
N4 P1 N3 C7 169.29(17) . . . . ?
N4 P1 N3 C8 -0.10(16) . . . . ?
N1 P1 N4 C9 137.32(15) . . . . ?
N1 P1 N4 C10 -84.14(19) . . . . ?
N2 P1 N4 C9 -94.10(16) 2_566 . . . ?
N2 P1 N4 C10 44.4(2) 2_566 . . . ?
N3 P1 N4 C9 20.41(16) . . . . ?
N3 P1 N4 C10 158.95(18) . . . . ?
Cl1 P2 N1 P1 -150.00(19) . . . . ?
Cl2 P2 N1 P1 -41.7(2) . . . . ?
N2 P2 N1 P1 87.8(2) . . . . ?
Cl1 P2 N2 P1 -139.54(15) . . . 2_566 ?
Cl2 P2 N2 P1 114.17(15) . . . 2_566 ?
N1 P2 N2 P1 -16.8(2) . . . 2_566 ?
P1 N3 C7 C4 -98.7(2) . . . . ?
C8 N3 C7 C4 69.8(2) . . . . ?
P1 N3 C8 C9 -19.1(2) . . . . ?
C7 N3 C8 C9 171.15(18) . . . . ?
P1 N4 C9 C8 -33.6(2) . . . . ?
C10 N4 C9 C8 -173.1(2) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
F1 C1 C2 C3 179.06(18) . . . . ?
F1 C1 C6 C5 -178.23(18) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
C4 C3 C2 C1 -0.8(3) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C2 C3 C4 C7 -175.31(19) . . . . ?
C3 C4 C7 N3 -163.96(17) . . . . ?
C5 C4 C7 N3 19.6(3) . . . . ?
C6 C5 C4 C3 -0.4(3) . . . . ?
C6 C5 C4 C7 176.00(19) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
N3 C8 C9 N4 32.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.090
####################################################################### 
# 
# 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_Compound_12
_database_code_depnum_ccdc_archive 'CCDC 1530887'
_audit_update_record             
;
2017-02-03 deposited with the CCDC.
2017-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H30 Cl4 F2 N8 P4'
_chemical_formula_sum            'C22 H30 Cl4 F2 N8 P4'
_chemical_formula_weight         710.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1020 0.0940 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'

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

_cell_length_a                   37.3694(12)
_cell_length_b                   10.3766(3)
_cell_length_c                   15.8615(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6150.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8340
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      24.20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2912
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6479
_exptl_absorpt_correction_T_max  0.7175
_exptl_absorpt_process_details   'SADABS; Bruker, 2005'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            85778
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.09
_diffrn_reflns_theta_max         27.48
_reflns_number_total             7035
_reflns_number_gt                4848
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'WinGX publication routines (Farrugia, 2012) and PLATON (Spek, 2009)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0295P)²+6.4117P] 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         7035
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group

P1 P 0.405751(18) 0.25268(6) 0.04106(4) 0.01836(16) Uani 1 1 d . . .
P2 P 0.416328(18) 0.45753(6) 0.16344(5) 0.01937(16) Uani 1 1 d . . .
P3 P 0.414454(19) 0.27003(6) 0.29975(5) 0.02023(16) Uani 1 1 d . . .
P4 P 0.431007(19) 0.07992(7) 0.17340(5) 0.02247(17) Uani 1 1 d . . .
Cl1 Cl 0.377355(19) 0.59004(6) 0.14076(5) 0.02899(17) Uani 1 1 d . . .
Cl2 Cl 0.458813(19) 0.57745(7) 0.17622(5) 0.03151(18) Uani 1 1 d . . .
Cl3 Cl 0.40469(3) -0.08266(7) 0.20896(5) 0.0449(2) Uani 1 1 d . . .
Cl4 Cl 0.47870(2) 0.00392(9) 0.14144(6) 0.0504(2) Uani 1 1 d . . .
F1 F 0.20405(5) 0.0543(2) 0.02902(14) 0.0631(6) Uani 1 1 d . . .
F2 F 0.21314(5) 0.03255(19) 0.26796(14) 0.0570(6) Uani 1 1 d . . .
N1 N 0.42407(6) 0.3774(2) 0.08336(14) 0.0232(5) Uani 1 1 d . . .
N2 N 0.40595(6) 0.39979(19) 0.25056(14) 0.0205(5) Uani 1 1 d . . .
N3 N 0.43849(6) 0.1661(2) 0.25132(14) 0.0238(5) Uani 1 1 d . . .
N4 N 0.41124(6) 0.1230(2) 0.09213(14) 0.0248(5) Uani 1 1 d . . .
N5 N 0.42190(6) 0.2350(2) -0.05495(14) 0.0219(5) Uani 1 1 d . . .
N6 N 0.36249(6) 0.2689(2) 0.02397(13) 0.0225(5) Uani 1 1 d . . .
N7 N 0.43479(6) 0.3094(2) 0.38875(14) 0.0270(5) Uani 1 1 d . . .
N8 N 0.37612(6) 0.2020(2) 0.32762(14) 0.0228(5) Uani 1 1 d . . .
C1 C 0.46051(8) 0.2155(3) -0.0603(2) 0.0416(8) Uani 1 1 d . . .
H1A H 0.4677 0.1517 -0.0199 0.062 Uiso 1 1 calc R . .
H1B H 0.4726 0.2952 -0.0486 0.062 Uiso 1 1 calc R . .
H1C H 0.4667 0.1868 -0.1160 0.062 Uiso 1 1 calc R . .
C2 C 0.40917(7) 0.3295(3) -0.11843(18) 0.0269(7) Uani 1 1 d . . .
H2A H 0.4196 0.3093 -0.1729 0.032 Uiso 1 1 calc R . .
H2B H 0.4170 0.4153 -0.1025 0.032 Uiso 1 1 calc R . .
C3 C 0.36893(7) 0.3272(3) -0.12524(17) 0.0276(7) Uani 1 1 d . . .
H3A H 0.3612 0.2421 -0.1428 0.033 Uiso 1 1 calc R . .
H3B H 0.3614 0.3883 -0.1680 0.033 Uiso 1 1 calc R . .
C4 C 0.35133(7) 0.3607(3) -0.04237(17) 0.0255(6) Uani 1 1 d . . .
H4A H 0.3580 0.4475 -0.0260 0.031 Uiso 1 1 calc R . .
H4B H 0.3255 0.3579 -0.0488 0.031 Uiso 1 1 calc R . .
C5 C 0.33884(7) 0.2685(3) 0.09816(17) 0.0250(6) Uani 1 1 d . . .
H5A H 0.3358 0.3562 0.1182 0.030 Uiso 1 1 calc R . .
H5B H 0.3500 0.2190 0.1429 0.030 Uiso 1 1 calc R . .
C6 C 0.30263(7) 0.2116(3) 0.07822(17) 0.0221(6) Uani 1 1 d . . .
C7 C 0.29982(8) 0.0988(3) 0.03147(18) 0.0312(7) Uani 1 1 d . . .
H7 H 0.3204 0.0589 0.0113 0.037 Uiso 1 1 calc R . .
C8 C 0.26662(9) 0.0452(3) 0.0146(2) 0.0403(8) Uani 1 1 d . . .
H8 H 0.2645 -0.0295 -0.0174 0.048 Uiso 1 1 calc R . .
C9 C 0.23707(8) 0.1054(3) 0.0465(2) 0.0398(8) Uani 1 1 d . . .
C10 C 0.23851(8) 0.2156(3) 0.0921(2) 0.0372(8) Uani 1 1 d . . .
H10 H 0.2178 0.2543 0.1123 0.045 Uiso 1 1 calc R . .
C11 C 0.27196(7) 0.2691(3) 0.10790(18) 0.0281(7) Uani 1 1 d . . .
H11 H 0.2736 0.3448 0.1390 0.034 Uiso 1 1 calc R . .
C12 C 0.46996(8) 0.3705(3) 0.3795(2) 0.0407(8) Uani 1 1 d . . .
H12A H 0.4689 0.4347 0.3360 0.061 Uiso 1 1 calc R . .
H12B H 0.4874 0.3064 0.3646 0.061 Uiso 1 1 calc R . .
H12C H 0.4767 0.4103 0.4318 0.061 Uiso 1 1 calc R . .
C13 C 0.43442(9) 0.2116(3) 0.4566(2) 0.0408(8) Uani 1 1 d . . .
H13A H 0.4437 0.2498 0.5079 0.049 Uiso 1 1 calc R . .
H13B H 0.4501 0.1411 0.4410 0.049 Uiso 1 1 calc R . .
C14 C 0.39736(9) 0.1587(3) 0.47354(19) 0.0399(8) Uani 1 1 d . . .
H14A H 0.3821 0.2273 0.4945 0.048 Uiso 1 1 calc R . .
H14B H 0.3988 0.0926 0.5166 0.048 Uiso 1 1 calc R . .
C15 C 0.38101(9) 0.1022(3) 0.39439(18) 0.0321(7) Uani 1 1 d . . .
H15A H 0.3964 0.0343 0.3732 0.039 Uiso 1 1 calc R . .
H15B H 0.3580 0.0643 0.4080 0.039 Uiso 1 1 calc R . .
C16 C 0.34395(7) 0.2805(3) 0.33898(18) 0.0266(7) Uani 1 1 d . . .
H16A H 0.3451 0.3538 0.3011 0.032 Uiso 1 1 calc R . .
H16B H 0.3435 0.3133 0.3962 0.032 Uiso 1 1 calc R . .
C17 C 0.30955(7) 0.2066(3) 0.32238(18) 0.0250(6) Uani 1 1 d . . .
C18 C 0.30842(8) 0.0907(3) 0.27904(18) 0.0299(7) Uani 1 1 d . . .
H18 H 0.3297 0.0525 0.2615 0.036 Uiso 1 1 calc R . .
C19 C 0.27605(8) 0.0308(3) 0.2614(2) 0.0349(7) Uani 1 1 d . . .
H19 H 0.2754 -0.0468 0.2321 0.042 Uiso 1 1 calc R . .
C20 C 0.24505(8) 0.0889(3) 0.2881(2) 0.0382(8) Uani 1 1 d . . .
C21 C 0.24490(8) 0.2022(3) 0.3321(2) 0.0388(8) Uani 1 1 d . . .
H21 H 0.2235 0.2396 0.3495 0.047 Uiso 1 1 calc R . .
C22 C 0.27753(8) 0.2598(3) 0.35002(19) 0.0327(7) Uani 1 1 d . . .
H22 H 0.2780 0.3357 0.3812 0.039 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N1 1.611(2) . ?
P1 N4 1.584(2) . ?
P1 N5 1.648(2) . ?
P1 N6 1.648(2) . ?
P2 N1 1.545(2) . ?
P2 N2 1.555(2) . ?
P3 N2 1.588(2) . ?
P3 N3 1.600(2) . ?
P3 N7 1.655(2) . ?
P3 N8 1.657(2) . ?
P4 Cl3 2.0326(10) . ?
P4 Cl4 2.0137(10) . ?
P4 N3 1.551(2) . ?
P4 N4 1.552(2) . ?
Cl1 P2 2.0350(9) . ?
Cl2 P2 2.0274(9) . ?
F1 C9 1.371(3) . ?
F2 C20 1.366(3) . ?
N5 C1 1.460(3) . ?
N5 C2 1.484(3) . ?
N6 C4 1.479(3) . ?
N6 C5 1.471(3) . ?
N7 C13 1.479(4) . ?
N8 C15 1.492(3) . ?
N8 C16 1.464(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.508(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C3 1.510(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C5 1.510(4) . ?
C6 C7 1.389(4) . ?
C7 H7 0.9300 . ?
C8 C7 1.386(4) . ?
C8 H8 0.9300 . ?
C9 C8 1.366(4) . ?
C9 C10 1.354(5) . ?
C10 H10 0.9300 . ?
C11 C6 1.375(4) . ?
C11 C10 1.390(4) . ?
C11 H11 0.9300 . ?
C12 N7 1.466(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.514(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C14 1.514(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C16 1.520(4) . ?
C17 C18 1.385(4) . ?
C17 C22 1.389(4) . ?
C18 H18 0.9300 . ?
C19 C18 1.389(4) . ?
C19 H19 0.9300 . ?
C20 C19 1.372(4) . ?
C20 C21 1.368(5) . ?
C21 C22 1.387(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

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 P1 N5 108.58(12) . . ?
N1 P1 N6 113.78(12) . . ?
N4 P1 N1 114.51(12) . . ?
N4 P1 N5 109.30(12) . . ?
N4 P1 N6 107.34(12) . . ?
N6 P1 N5 102.63(11) . . ?
Cl2 P2 Cl1 99.40(4) . . ?
N1 P2 Cl1 110.61(9) . . ?
N1 P2 Cl2 105.42(9) . . ?
N1 P2 N2 124.73(12) . . ?
N2 P2 Cl1 103.82(9) . . ?
N2 P2 Cl2 110.05(9) . . ?
N2 P3 N3 116.61(12) . . ?
N2 P3 N7 107.56(11) . . ?
N2 P3 N8 108.62(11) . . ?
N3 P3 N7 108.55(12) . . ?
N3 P3 N8 109.03(12) . . ?
N7 P3 N8 105.95(12) . . ?
Cl4 P4 Cl3 99.97(5) . . ?
N3 P4 Cl3 110.17(9) . . ?
N3 P4 Cl4 105.48(9) . . ?
N3 P4 N4 125.58(12) . . ?
N4 P4 Cl3 103.84(9) . . ?
N4 P4 Cl4 108.96(10) . . ?
P2 N1 P1 134.04(15) . . ?
P2 N2 P3 135.49(14) . . ?
P4 N3 P3 132.06(15) . . ?
P4 N4 P1 136.99(15) . . ?
C1 N5 P1 115.55(19) . . ?
C1 N5 C2 111.6(2) . . ?
C2 N5 P1 115.85(17) . . ?
C4 N6 P1 117.34(17) . . ?
C5 N6 P1 117.21(17) . . ?
C5 N6 C4 113.7(2) . . ?
C12 N7 P3 115.7(2) . . ?
C12 N7 C13 112.2(2) . . ?
C13 N7 P3 116.53(19) . . ?
C15 N8 P3 112.27(18) . . ?
C16 N8 P3 120.36(17) . . ?
C16 N8 C15 113.6(2) . . ?
N5 C1 H1A 109.5 . . ?
N5 C1 H1B 109.5 . . ?
N5 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N5 C2 C3 111.0(2) . . ?
N5 C2 H2A 109.4 . . ?
N5 C2 H2B 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 111.6(2) . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
N6 C4 C3 110.4(2) . . ?
N6 C4 H4A 109.6 . . ?
N6 C4 H4B 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N6 C5 C6 111.8(2) . . ?
N6 C5 H5A 109.3 . . ?
N6 C5 H5B 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 120.6(2) . . ?
C11 C6 C5 120.3(2) . . ?
C11 C6 C7 119.0(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 121.0 . . ?
C9 C8 C7 117.9(3) . . ?
C9 C8 H8 121.0 . . ?
C8 C9 F1 118.4(3) . . ?
C10 C9 F1 118.0(3) . . ?
C10 C9 C8 123.5(3) . . ?
C9 C10 C11 118.0(3) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
C6 C11 C10 121.0(3) . . ?
C6 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
N7 C12 H12A 109.5 . . ?
N7 C12 H12B 109.5 . . ?
N7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N7 C13 C14 112.7(2) . . ?
N7 C13 H13A 109.0 . . ?
N7 C13 H13B 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 111.2(3) . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N8 C15 C14 111.7(2) . . ?
N8 C15 H15A 109.3 . . ?
N8 C15 H15B 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
N8 C16 C17 113.1(2) . . ?
N8 C16 H16A 109.0 . . ?
N8 C16 H16B 109.0 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 123.4(2) . . ?
C18 C17 C22 118.4(3) . . ?
C22 C17 C16 118.2(3) . . ?
C17 C18 C19 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 120.8 . . ?
C20 C19 C18 118.5(3) . . ?
C20 C19 H19 120.8 . . ?
F2 C20 C19 118.5(3) . . ?
F2 C20 C21 118.9(3) . . ?
C21 C20 C19 122.6(3) . . ?
C20 C21 C22 118.1(3) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
C17 C22 H22 119.3 . . ?
C21 C22 C17 121.4(3) . . ?
C21 C22 H22 119.3 . . ?

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
N5 P1 N1 P2 167.91(19) . . . . ?
N6 P1 N1 P2 54.3(2) . . . . ?
N4 P1 N1 P2 -69.7(2) . . . . ?
N1 P1 N4 P4 -2.3(3) . . . . ?
N5 P1 N4 P4 119.8(2) . . . . ?
N6 P1 N4 P4 -129.6(2) . . . . ?
N1 P1 N5 C1 60.4(2) . . . . ?
N1 P1 N5 C2 -72.9(2) . . . . ?
N4 P1 N5 C1 -65.1(2) . . . . ?
N4 P1 N5 C2 161.58(19) . . . . ?
N6 P1 N5 C1 -178.8(2) . . . . ?
N6 P1 N5 C2 47.9(2) . . . . ?
N1 P1 N6 C4 69.4(2) . . . . ?
N1 P1 N6 C5 -71.4(2) . . . . ?
N4 P1 N6 C4 -162.88(19) . . . . ?
N4 P1 N6 C5 56.4(2) . . . . ?
N5 P1 N6 C4 -47.7(2) . . . . ?
N5 P1 N6 C5 171.53(19) . . . . ?
Cl1 P2 N1 P1 -83.2(2) . . . . ?
Cl2 P2 N1 P1 170.24(17) . . . . ?
N2 P2 N1 P1 41.6(3) . . . . ?
Cl1 P2 N2 P3 158.30(18) . . . . ?
Cl2 P2 N2 P3 -96.10(19) . . . . ?
N1 P2 N2 P3 30.6(3) . . . . ?
N3 P3 N2 P2 -2.2(3) . . . . ?
N7 P3 N2 P2 119.9(2) . . . . ?
N8 P3 N2 P2 -125.8(2) . . . . ?
N2 P3 N3 P4 -68.9(2) . . . . ?
N7 P3 N3 P4 169.48(18) . . . . ?
N8 P3 N3 P4 54.5(2) . . . . ?
N2 P3 N7 C12 -64.7(2) . . . . ?
N2 P3 N7 C13 160.2(2) . . . . ?
N3 P3 N7 C12 62.2(2) . . . . ?
N3 P3 N7 C13 -72.8(2) . . . . ?
N8 P3 N7 C12 179.2(2) . . . . ?
N8 P3 N7 C13 44.1(2) . . . . ?
N2 P3 N8 C15 -163.36(18) . . . . ?
N2 P3 N8 C16 -25.6(2) . . . . ?
N3 P3 N8 C15 68.6(2) . . . . ?
N3 P3 N8 C16 -153.6(2) . . . . ?
N7 P3 N8 C15 -48.1(2) . . . . ?
N7 P3 N8 C16 89.7(2) . . . . ?
Cl3 P4 N3 P3 -83.7(2) . . . . ?
Cl4 P4 N3 P3 169.26(17) . . . . ?
N4 P4 N3 P3 41.5(3) . . . . ?
Cl3 P4 N4 P1 156.9(2) . . . . ?
Cl4 P4 N4 P1 -97.2(2) . . . . ?
N3 P4 N4 P1 29.1(3) . . . . ?
P1 N5 C2 C3 -57.4(3) . . . . ?
C1 N5 C2 C3 167.6(2) . . . . ?
P1 N6 C4 C3 55.8(3) . . . . ?
C5 N6 C4 C3 -162.1(2) . . . . ?
P1 N6 C5 C6 -148.44(19) . . . . ?
C4 N6 C5 C6 69.4(3) . . . . ?
P3 N7 C13 C14 -50.0(3) . . . . ?
C12 N7 C13 C14 173.4(3) . . . . ?
P3 N8 C15 C14 59.8(3) . . . . ?
C16 N8 C15 C14 -81.0(3) . . . . ?
P3 N8 C16 C17 152.1(2) . . . . ?
C15 N8 C16 C17 -70.6(3) . . . . ?
N5 C2 C3 C4 60.3(3) . . . . ?
N6 C4 C3 C2 -58.9(3) . . . . ?
C7 C6 C5 N6 44.7(4) . . . . ?
C11 C6 C5 N6 -136.9(3) . . . . ?
C5 C6 C7 C8 178.7(3) . . . . ?
C11 C6 C7 C8 0.3(4) . . . . ?
C9 C8 C7 C6 -1.1(5) . . . . ?
F1 C9 C8 C7 179.0(3) . . . . ?
C10 C9 C8 C7 1.3(5) . . . . ?
F1 C9 C10 C11 -178.4(3) . . . . ?
C8 C9 C10 C11 -0.7(5) . . . . ?
C10 C11 C6 C5 -178.1(3) . . . . ?
C10 C11 C6 C7 0.4(4) . . . . ?
C6 C11 C10 C9 -0.2(5) . . . . ?
N7 C13 C14 C15 56.6(3) . . . . ?
N8 C15 C14 C13 -62.6(3) . . . . ?
C18 C17 C16 N8 -17.0(4) . . . . ?
C22 C17 C16 N8 164.9(2) . . . . ?
C16 C17 C18 C19 -176.2(3) . . . . ?
C22 C17 C18 C19 1.9(4) . . . . ?
C16 C17 C22 C21 175.5(3) . . . . ?
C18 C17 C22 C21 -2.6(4) . . . . ?
C20 C19 C18 C17 -0.2(4) . . . . ?
F2 C20 C19 C18 177.6(3) . . . . ?
C21 C20 C19 C18 -0.8(5) . . . . ?
F2 C20 C21 C22 -178.3(3) . . . . ?
C19 C20 C21 C22 0.0(5) . . . . ?
C20 C21 C22 C17 1.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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_Compound_9
_database_code_depnum_ccdc_archive 'CCDC 1530886'
_audit_update_record             
;
2017-02-03 deposited with the CCDC.
2017-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H30 Cl4 F2 N8 P4'
_chemical_formula_sum            'C22 H30 Cl4 F2 N8 P4'
_chemical_formula_weight         710.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1020 0.0940 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   8.8404(3)
_cell_length_b                   19.0391(5)
_cell_length_c                   9.1699(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.828(2)
_cell_angle_gamma                90.00
_cell_volume                     1510.64(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3225
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.69

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_T_max  0.896
_exptl_absorpt_process_details   'SADABS; Bruker, 2005'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Kappa APEXII CCD area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14525
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         29.31
_reflns_number_total             3709
_reflns_number_gt                2831
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
'WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0644P)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         3709
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.17854(7) 0.14509(3) 0.18250(7) 0.02611(17) Uani 1 1 d . . .
Cl2 Cl 0.40756(6) 0.02461(3) 0.18837(7) 0.02577(17) Uani 1 1 d . . .
P1 P -0.03033(6) -0.04890(3) 0.21072(7) 0.01322(15) Uani 1 1 d . . .
P2 P 0.18573(6) 0.04186(3) 0.12420(7) 0.01338(15) Uani 1 1 d . . .
N1 N 0.1149(2) -0.00072(10) 0.2406(2) 0.0167(4) Uani 1 1 d . . .
N2 N 0.1437(2) 0.03243(10) -0.0517(2) 0.0171(4) Uani 1 1 d . . .
N3 N 0.0219(2) -0.13140(9) 0.2330(2) 0.0171(4) Uani 1 1 d . . .
N4 N -0.1188(2) -0.03600(9) 0.3519(2) 0.0145(4) Uani 1 1 d . . .
F1 F 0.56809(17) -0.29766(10) 0.59822(19) 0.0429(5) Uani 1 1 d . . .
C1 C 0.4655(3) -0.26410(15) 0.4895(3) 0.0272(6) Uani 1 1 d . . .
C2 C 0.4616(3) -0.19247(15) 0.4906(3) 0.0264(6) Uani 1 1 d . . .
H2 H 0.5282 -0.1669 0.5632 0.032 Uiso 1 1 calc R . .
C3 C 0.3554(3) -0.15872(13) 0.3801(3) 0.0213(5) Uani 1 1 d . . .
H3 H 0.3505 -0.1099 0.3787 0.026 Uiso 1 1 calc R . .
C4 C 0.2558(2) -0.19717(12) 0.2711(3) 0.0170(5) Uani 1 1 d . . .
C5 C 0.2653(3) -0.26993(12) 0.2728(3) 0.0214(5) Uani 1 1 d . . .
H5 H 0.2006 -0.2960 0.1997 0.026 Uiso 1 1 calc R . .
C6 C 0.3710(3) -0.30412(13) 0.3831(3) 0.0265(6) Uani 1 1 d . . .
H6 H 0.3777 -0.3529 0.3850 0.032 Uiso 1 1 calc R . .
C7 C 0.1371(3) -0.15887(12) 0.1563(3) 0.0180(5) Uani 1 1 d . . .
H7A H 0.1855 -0.1209 0.1122 0.022 Uiso 1 1 calc R . .
H7B H 0.0896 -0.1908 0.0777 0.022 Uiso 1 1 calc R . .
C8 C -0.0851(3) -0.18433(12) 0.2632(3) 0.0202(5) Uani 1 1 d . . .
H8A H -0.0315 -0.2287 0.2854 0.024 Uiso 1 1 calc R . .
H8B H -0.1668 -0.1908 0.1759 0.024 Uiso 1 1 calc R . .
C9 C -0.1557(3) -0.16164(12) 0.3966(3) 0.0216(5) Uani 1 1 d . . .
H9A H -0.2331 -0.1956 0.4109 0.026 Uiso 1 1 calc R . .
H9B H -0.0754 -0.1609 0.4863 0.026 Uiso 1 1 calc R . .
C10 C -0.2286(3) -0.09024(12) 0.3719(3) 0.0192(5) Uani 1 1 d . . .
H10A H -0.3115 -0.0917 0.2844 0.023 Uiso 1 1 calc R . .
H10B H -0.2735 -0.0782 0.4567 0.023 Uiso 1 1 calc R . .
C11 C -0.1775(3) 0.03573(12) 0.3579(3) 0.0187(5) Uani 1 1 d . . .
H11A H -0.0997 0.0686 0.3432 0.028 Uiso 1 1 calc R . .
H11B H -0.2030 0.0438 0.4534 0.028 Uiso 1 1 calc R . .
H11C H -0.2683 0.0418 0.2811 0.028 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 P2 2.0412(8) . ?
P1 N1 1.5558(18) . ?
P1 N2 1.6221(19) 3 ?
P1 N3 1.6381(19) . ?
P1 N4 1.663(2) . ?
P2 Cl2 1.9562(7) . ?
P2 N1 1.569(2) . ?
P2 N2 1.589(2) . ?
N2 P1 1.6221(19) 3 ?
N3 C7 1.449(3) . ?
N3 C8 1.448(3) . ?
N4 C10 1.454(3) . ?
N4 C11 1.466(3) . ?
F1 C1 1.361(3) . ?
C2 C1 1.364(4) . ?
C2 H2 0.9300 . ?
C3 C2 1.390(3) . ?
C3 H3 0.9300 . ?
C4 C3 1.396(3) . ?
C4 C5 1.388(3) . ?
C5 C6 1.390(3) . ?
C5 H5 0.9300 . ?
C6 C1 1.377(4) . ?
C6 H6 0.9300 . ?
C7 C4 1.512(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.545(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C9 1.501(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 N2 112.34(10) . 3 ?
N1 P1 N3 109.99(10) . . ?
N1 P1 N4 106.18(10) . . ?
N2 P1 N3 113.84(10) 3 . ?
N2 P1 N4 111.64(10) 3 . ?
N3 P1 N4 102.14(10) . . ?
Cl2 P2 Cl1 99.55(3) . . ?
N1 P2 Cl1 106.32(8) . . ?
N1 P2 Cl2 102.94(7) . . ?
N1 P2 N2 126.10(10) . . ?
N2 P2 Cl1 111.17(7) . . ?
N2 P2 Cl2 107.31(8) . . ?
P1 N1 P2 127.92(13) . . ?
P2 N2 P1 149.70(13) . 3 ?
C7 N3 P1 119.60(15) . . ?
C8 N3 P1 120.83(15) . . ?
C8 N3 C7 113.17(18) . . ?
C10 N4 P1 115.21(15) . . ?
C10 N4 C11 114.00(17) . . ?
C11 N4 P1 113.17(15) . . ?
F1 C1 C2 118.6(2) . . ?
F1 C1 C6 118.4(2) . . ?
C2 C1 C6 123.1(2) . . ?
C1 C2 C3 118.1(2) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C7 119.4(2) . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 C7 121.4(2) . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.4(2) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
N3 C7 C4 107.00(19) . . ?
N3 C7 H7A 110.3 . . ?
N3 C7 H7B 110.3 . . ?
C4 C7 H7A 110.3 . . ?
C4 C7 H7B 110.3 . . ?
H7A C7 H7B 108.6 . . ?
N3 C8 C9 110.04(19) . . ?
N3 C8 H8A 109.7 . . ?
N3 C8 H8B 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 C8 111.4(2) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N4 C10 C9 112.67(18) . . ?
N4 C10 H10A 109.1 . . ?
N4 C10 H10B 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
N4 C11 H11A 109.5 . . ?
N4 C11 H11B 109.5 . . ?
N4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag

N2 P1 N1 P2 -19.98(19) 3 . . . ?
N3 P1 N1 P2 107.94(16) . . . . ?
N4 P1 N1 P2 -142.28(15) . . . . ?
N1 P1 N4 C10 -161.84(15) . . . . ?
N1 P1 N4 C11 64.50(16) . . . . ?
N2 P1 N4 C10 75.42(17) 3 . . . ?
N2 P1 N4 C11 -58.24(17) 3 . . . ?
N3 P1 N4 C10 -46.59(17) . . . . ?
N3 P1 N4 C11 179.75(15) . . . . ?
N1 P1 N3 C7 -51.7(2) . . . . ?
N1 P1 N3 C8 158.33(18) . . . . ?
N2 P1 N3 C7 75.42(19) 3 . . . ?
N2 P1 N3 C8 -74.6(2) 3 . . . ?
N4 P1 N3 C7 -164.08(17) . . . . ?
N4 P1 N3 C8 45.9(2) . . . . ?
Cl1 P2 N1 P1 119.46(14) . . . . ?
Cl2 P2 N1 P1 -136.37(13) . . . . ?
N2 P2 N1 P1 -13.3(2) . . . . ?
Cl1 P2 N2 P1 -48.9(3) . . . 3 ?
Cl2 P2 N2 P1 -156.8(2) . . . 3 ?
N1 P2 N2 P1 82.0(3) . . . 3 ?
P1 N3 C7 C4 130.72(17) . . . . ?
C8 N3 C7 C4 -77.1(2) . . . . ?
P1 N3 C8 C9 -52.2(2) . . . . ?
C7 N3 C8 C9 156.01(19) . . . . ?
P1 N4 C10 C9 58.5(2) . . . . ?
C11 N4 C10 C9 -168.2(2) . . . . ?
C3 C2 C1 F1 -179.3(2) . . . . ?
C3 C2 C1 C6 1.0(4) . . . . ?
C4 C3 C2 C1 -0.1(4) . . . . ?
C5 C4 C3 C2 -0.9(4) . . . . ?
C7 C4 C3 C2 177.5(2) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C7 C4 C5 C6 -177.3(2) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C5 C6 C1 F1 179.5(2) . . . . ?
C5 C6 C1 C2 -0.9(4) . . . . ?
N3 C7 C4 C3 -70.5(3) . . . . ?
N3 C7 C4 C5 107.8(2) . . . . ?
N3 C8 C9 C10 54.6(2) . . . . ?
N4 C10 C9 C8 -60.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C8 H8B F1 0.97 2.32 3.147(3) 143 4_455 yes

_diffrn_measured_fraction_theta_max 0.895
_diffrn_reflns_theta_full        29.31
_diffrn_measured_fraction_theta_full 0.895
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.092
