# 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 2024

####################################################################### 
# 
# 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 2312871'
loop_
_audit_author_name
_audit_author_address
'Tuncer Hokelek'
;Hacettepe University
Turkey
;
_audit_update_record             
;
2024-02-20 deposited with the CCDC.	2024-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H46 Cl2 F2 N10 P4'
_chemical_formula_sum            'C28 H46 Cl2 F2 N10 P4'
_chemical_formula_weight         755.53

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.376(4)
_cell_length_b                   9.322(4)
_cell_length_c                   12.011(6)
_cell_angle_alpha                99.753(18)
_cell_angle_beta                 94.602(19)
_cell_angle_gamma                94.902(19)
_cell_volume                     916.6(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    7503
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      28.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.398
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            24667
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.053
_diffrn_reflns_theta_max         28.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4529
_reflns_number_gt                3718
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2; Bruker, 2012 '
_computing_cell_refinement       'SAINT; Bruker, 2012'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
'WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)'
_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)+(0.0760P)²+1.9091P] 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     'SHELXL-2018/3 (Sheldrick 2015b)'
_refine_ls_extinction_coef       0.053(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4529
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.2025
_refine_ls_wR_factor_gt          0.1957
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.152
_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
P1 P 0.36406(10) 0.28727(9) 0.42723(7) 0.0268(2) Uani 1 1 d . . . . .
P2 P 0.47552(10) 0.56810(9) 0.35806(7) 0.0270(2) Uani 1 1 d . . . . .
Cl1 Cl 0.67490(13) 0.48204(11) 0.28755(9) 0.0481(3) Uani 1 1 d . . . . .
N1 N 0.3651(4) 0.4363(3) 0.3820(2) 0.0324(6) Uani 1 1 d . . . . .
N2 N 0.5437(4) 0.7033(3) 0.4505(2) 0.0337(6) Uani 1 1 d . . . . .
N3 N 0.1769(4) 0.2139(3) 0.4198(3) 0.0378(7) Uani 1 1 d . . . . .
N4 N 0.4244(4) 0.1513(3) 0.3377(2) 0.0328(6) Uani 1 1 d . . . . .
N5 N 0.3838(4) 0.6357(3) 0.2575(3) 0.0366(7) Uani 1 1 d . . . . .
F1 F 0.8475(7) -0.1753(5) -0.0222(4) 0.1182(17) Uani 1 1 d . . . . .
C1 C 0.0487(5) 0.3030(5) 0.4553(4) 0.0498(10) Uani 1 1 d . . . . .
H1A H -0.022738 0.312382 0.387753 0.060 Uiso 1 1 calc R U . . .
H1B H 0.096488 0.402244 0.491870 0.060 Uiso 1 1 calc R U . . .
C2 C -0.0494(6) 0.2367(7) 0.5374(4) 0.0625(13) Uani 1 1 d . . . . .
H2A H -0.133263 0.299666 0.560177 0.094 Uiso 1 1 calc R U . . .
H2B H 0.020966 0.227747 0.604563 0.094 Uiso 1 1 calc R U . . .
H2C H -0.099530 0.139593 0.500617 0.094 Uiso 1 1 calc R U . . .
C3 C 0.1406(5) 0.1011(5) 0.3187(4) 0.0494(10) Uani 1 1 d . . . . .
H3A H 0.108673 0.144522 0.251537 0.059 Uiso 1 1 calc R U . . .
H3B H 0.052737 0.028075 0.329274 0.059 Uiso 1 1 calc R U . . .
C4 C 0.2963(5) 0.0319(4) 0.3051(4) 0.0459(9) Uani 1 1 d . . . . .
H4A H 0.306607 -0.042016 0.354787 0.055 Uiso 1 1 calc R U . . .
H4B H 0.300434 -0.016208 0.225452 0.055 Uiso 1 1 calc R U . . .
C5 C 0.5849(5) 0.1083(5) 0.3592(3) 0.0411(9) Uani 1 1 d . . . . .
H5A H 0.582917 0.043613 0.416605 0.049 Uiso 1 1 calc R U . . .
H5B H 0.659035 0.196704 0.391328 0.049 Uiso 1 1 calc R U . . .
C6 C 0.6491(5) 0.0298(4) 0.2543(3) 0.0390(8) Uani 1 1 d . . . . .
C7 C 0.7140(5) -0.1002(4) 0.2562(4) 0.0415(8) Uani 1 1 d . . . . .
H7 H 0.713151 -0.142899 0.322638 0.050 Uiso 1 1 calc R U . . .
C8 C 0.7806(6) -0.1697(5) 0.1628(5) 0.0580(12) Uani 1 1 d . . . . .
H8 H 0.824975 -0.259867 0.164354 0.070 Uiso 1 1 calc R U . . .
C9 C 0.7818(8) -0.1081(6) 0.0700(5) 0.0709(16) Uani 1 1 d . . . . .
C10 C 0.7180(12) 0.0189(7) 0.0634(5) 0.106(3) Uani 1 1 d . . . . .
H10 H 0.719209 0.059423 -0.004030 0.127 Uiso 1 1 calc R U . . .
C11 C 0.6509(10) 0.0889(6) 0.1570(4) 0.088(2) Uani 1 1 d . . . . .
H11 H 0.605731 0.178358 0.153808 0.106 Uiso 1 1 calc R U . . .
C12 C 0.2976(5) 0.5453(5) 0.1543(3) 0.0444(9) Uani 1 1 d . . . . .
H12 H 0.341173 0.447895 0.142417 0.053 Uiso 1 1 calc R U . . .
C13 C 0.3302(11) 0.6184(9) 0.0546(5) 0.104(3) Uani 1 1 d . . . . .
H13A H 0.445965 0.626052 0.046548 0.156 Uiso 1 1 calc R U . . .
H13B H 0.293764 0.716520 0.067099 0.156 Uiso 1 1 calc R U . . .
H13C H 0.272059 0.560228 -0.014639 0.156 Uiso 1 1 calc R U . . .
C14 C 0.1218(7) 0.5221(9) 0.1674(6) 0.088(2) Uani 1 1 d . . . . .
H14A H 0.106618 0.481051 0.236132 0.132 Uiso 1 1 calc R U . . .
H14B H 0.067921 0.454171 0.101133 0.132 Uiso 1 1 calc R U . . .
H14C H 0.075523 0.615882 0.173382 0.132 Uiso 1 1 calc R U . . .
H5 H 0.427(5) 0.704(5) 0.252(4) 0.032(11) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N1 1.574(3) . ?
P1 N2 1.589(3) 2_666 ?
P1 N3 1.645(3) . ?
P1 N4 1.659(3) . ?
P2 N1 1.554(3) . ?
P2 N2 1.564(3) . ?
P2 N5 1.624(3) . ?
P2 Cl1 2.0917(15) . ?
N3 C3 1.459(5) . ?
N3 C1 1.459(5) . ?
N4 C5 1.451(5) . ?
N4 C4 1.458(5) . ?
N5 C12 1.471(5) . ?
N5 H5 0.72(4) . ?
F1 C9 1.358(5) . ?
C1 C2 1.509(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.512(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.508(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.374(5) . ?
C6 C11 1.375(6) . ?
C7 C8 1.380(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.337(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.352(8) . ?
C10 C11 1.386(7) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C14 1.495(8) . ?
C12 C13 1.507(7) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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 115.19(16) . 2_666 ?
N1 P1 N3 108.88(16) . . ?
N2 P1 N3 112.13(17) 2_666 . ?
N1 P1 N4 114.21(16) . . ?
N2 P1 N4 109.56(16) 2_666 . ?
N3 P1 N4 95.17(16) . . ?
N1 P2 N2 123.95(17) . . ?
N1 P2 N5 108.38(18) . . ?
N2 P2 N5 105.31(16) . . ?
N1 P2 Cl1 106.60(13) . . ?
N2 P2 Cl1 106.28(14) . . ?
N5 P2 Cl1 104.88(14) . . ?
P2 N1 P1 144.1(2) . . ?
P2 N2 P1 130.96(19) . 2_666 ?
C3 N3 C1 117.6(3) . . ?
C3 N3 P1 110.3(3) . . ?
C1 N3 P1 120.9(3) . . ?
C5 N4 C4 115.8(3) . . ?
C5 N4 P1 118.8(2) . . ?
C4 N4 P1 110.8(3) . . ?
C12 N5 P2 123.5(3) . . ?
C12 N5 H5 118(3) . . ?
P2 N5 H5 110(3) . . ?
N3 C1 C2 111.6(4) . . ?
N3 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N3 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 C3 C4 104.2(3) . . ?
N3 C3 H3A 110.9 . . ?
C4 C3 H3A 110.9 . . ?
N3 C3 H3B 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
N4 C4 C3 105.8(3) . . ?
N4 C4 H4A 110.6 . . ?
C3 C4 H4A 110.6 . . ?
N4 C4 H4B 110.6 . . ?
C3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
N4 C5 C6 113.2(3) . . ?
N4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
N4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C11 118.5(4) . . ?
C7 C6 C5 120.1(4) . . ?
C11 C6 C5 121.3(4) . . ?
C6 C7 C8 120.8(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 119.0(4) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 122.5(4) . . ?
C8 C9 F1 119.5(5) . . ?
C10 C9 F1 118.0(5) . . ?
C9 C10 C11 118.6(5) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C6 C11 C10 120.5(5) . . ?
C6 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
N5 C12 C14 110.6(4) . . ?
N5 C12 C13 108.5(4) . . ?
C14 C12 C13 112.3(5) . . ?
N5 C12 H12 108.5 . . ?
C14 C12 H12 108.5 . . ?
C13 C12 H12 108.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 P2 N1 P1 -82.7(4) . . . . ?
N5 P2 N1 P1 153.3(3) . . . . ?
Cl1 P2 N1 P1 40.9(4) . . . . ?
N2 P1 N1 P2 54.0(4) 2_666 . . . ?
N3 P1 N1 P2 -179.1(3) . . . . ?
N4 P1 N1 P2 -74.1(4) . . . . ?
N1 P2 N2 P1 50.5(4) . . . 2_666 ?
N5 P2 N2 P1 175.8(3) . . . 2_666 ?
Cl1 P2 N2 P1 -73.2(3) . . . 2_666 ?
N1 P1 N3 C3 99.4(3) . . . . ?
N2 P1 N3 C3 -131.9(3) 2_666 . . . ?
N4 P1 N3 C3 -18.4(3) . . . . ?
N1 P1 N3 C1 -43.6(4) . . . . ?
N2 P1 N3 C1 85.0(3) 2_666 . . . ?
N4 P1 N3 C1 -161.4(3) . . . . ?
N1 P1 N4 C5 103.7(3) . . . . ?
N2 P1 N4 C5 -27.2(3) 2_666 . . . ?
N3 P1 N4 C5 -142.9(3) . . . . ?
N1 P1 N4 C4 -118.7(3) . . . . ?
N2 P1 N4 C4 110.4(3) 2_666 . . . ?
N3 P1 N4 C4 -5.3(3) . . . . ?
N1 P2 N5 C12 -43.7(4) . . . . ?
N2 P2 N5 C12 -178.2(3) . . . . ?
Cl1 P2 N5 C12 69.9(4) . . . . ?
C3 N3 C1 C2 90.6(5) . . . . ?
P1 N3 C1 C2 -129.0(4) . . . . ?
C1 N3 C3 C4 179.4(3) . . . . ?
P1 N3 C3 C4 35.0(4) . . . . ?
C5 N4 C4 C3 165.0(3) . . . . ?
P1 N4 C4 C3 26.0(4) . . . . ?
N3 C3 C4 N4 -37.4(4) . . . . ?
C4 N4 C5 C6 66.9(4) . . . . ?
P1 N4 C5 C6 -157.5(3) . . . . ?
N4 C5 C6 C7 -130.5(4) . . . . ?
N4 C5 C6 C11 52.5(7) . . . . ?
C11 C6 C7 C8 0.4(7) . . . . ?
C5 C6 C7 C8 -176.7(4) . . . . ?
C6 C7 C8 C9 0.3(8) . . . . ?
C7 C8 C9 C10 -1.0(10) . . . . ?
C7 C8 C9 F1 179.8(5) . . . . ?
C8 C9 C10 C11 0.9(13) . . . . ?
F1 C9 C10 C11 -179.8(7) . . . . ?
C7 C6 C11 C10 -0.5(11) . . . . ?
C5 C6 C11 C10 176.6(7) . . . . ?
C9 C10 C11 C6 -0.1(13) . . . . ?
P2 N5 C12 C14 96.3(5) . . . . ?
P2 N5 C12 C13 -140.2(5) . . . . ?

_refine_diff_density_max         0.783
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2312872'
loop_
_audit_author_name
_audit_author_address
'Tuncer Hokelek'
;Hacettepe University
Turkey
;
_audit_update_record             
;
2024-02-20 deposited with the CCDC.	2024-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.1703(3)
_cell_length_b                   9.7421(3)
_cell_length_c                   9.8703(4)
_cell_angle_alpha                74.561(4)
_cell_angle_beta                 82.140(4)
_cell_angle_gamma                63.676(3)
_cell_volume                     761.65(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7063
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.43

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.641
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            9924
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.141
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3498
_reflns_number_gt                3261
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'WinGX publication routines (Farrugia, 2012) and PLATON (Spek, 2009)'
_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)+(0.0390P)²+0.6082P] 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     'SHELXL-2018/3 (Sheldrick 2015b)'
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3498
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P -0.14928(5) 0.86929(5) 1.01401(5) 0.01734(13) Uani 1 1 d . . . . .
P2 P 0.16736(5) 0.86709(5) 0.89652(5) 0.01988(14) Uani 1 1 d . . . . .
Cl1 Cl 0.09207(9) 0.96330(8) 0.69287(6) 0.04575(18) Uani 1 1 d . . . . .
Cl2 Cl 0.36149(6) 0.66936(6) 0.87544(8) 0.04365(18) Uani 1 1 d . . . . .
F1 F -0.3995(2) 0.39620(18) 1.69843(16) 0.0546(4) Uani 1 1 d . . . . .
N1 N 0.04048(19) 0.81711(19) 0.98586(18) 0.0253(3) Uani 1 1 d . . . . .
N2 N 0.23791(19) 0.96880(19) 0.93728(19) 0.0269(4) Uani 1 1 d . . . . .
N3 N -0.17844(19) 0.72617(18) 1.12862(16) 0.0212(3) Uani 1 1 d . . . . .
N4 N -0.24743(19) 0.87158(18) 0.88553(16) 0.0220(3) Uani 1 1 d . . . . .
C1 C -0.3374(3) 0.9865(3) 0.6411(2) 0.0423(5) Uani 1 1 d . . . . .
H1A H -0.382507 1.084770 0.573005 0.063 Uiso 1 1 calc R U . . .
H1B H -0.403611 0.931178 0.648844 0.063 Uiso 1 1 calc R U . . .
H1C H -0.228910 0.923884 0.611926 0.063 Uiso 1 1 calc R U . . .
C2 C -0.3328(3) 1.0175(2) 0.7818(2) 0.0292(4) Uani 1 1 d . . . . .
H2A H -0.278541 1.085734 0.770900 0.035 Uiso 1 1 calc R U . . .
H2B H -0.443164 1.071607 0.815392 0.035 Uiso 1 1 calc R U . . .
C3 C -0.3288(2) 0.7663(2) 0.9321(2) 0.0252(4) Uani 1 1 d . . . . .
H3A H -0.323188 0.714905 0.858550 0.030 Uiso 1 1 calc R U . . .
H3B H -0.442233 0.824967 0.955696 0.030 Uiso 1 1 calc R U . . .
C4 C -0.2393(2) 0.6457(2) 1.0606(2) 0.0247(4) Uani 1 1 d . . . . .
H4A H -0.312361 0.609440 1.123829 0.030 Uiso 1 1 calc R U . . .
H4B H -0.149802 0.555690 1.033421 0.030 Uiso 1 1 calc R U . . .
C5 C -0.0669(2) 0.6277(2) 1.2440(2) 0.0282(4) Uani 1 1 d . . . . .
H5A H -0.022941 0.689304 1.272836 0.034 Uiso 1 1 calc R U . . .
H5B H 0.022983 0.541127 1.212497 0.034 Uiso 1 1 calc R U . . .
C6 C -0.1534(2) 0.5636(2) 1.3673(2) 0.0254(4) Uani 1 1 d . . . . .
C7 C -0.1339(3) 0.4098(2) 1.3950(2) 0.0314(4) Uani 1 1 d . . . . .
H7 H -0.064304 0.343957 1.338069 0.038 Uiso 1 1 calc R U . . .
C8 C -0.2169(3) 0.3522(2) 1.5067(2) 0.0364(5) Uani 1 1 d . . . . .
H8 H -0.203693 0.248635 1.525178 0.044 Uiso 1 1 calc R U . . .
C9 C -0.3181(3) 0.4511(3) 1.5885(2) 0.0346(5) Uani 1 1 d . . . . .
C10 C -0.3408(3) 0.6049(3) 1.5647(2) 0.0383(5) Uani 1 1 d . . . . .
H10 H -0.410008 0.669834 1.622411 0.046 Uiso 1 1 calc R U . . .
C11 C -0.2578(3) 0.6600(2) 1.4525(2) 0.0339(5) Uani 1 1 d . . . . .
H11 H -0.272516 0.763956 1.433998 0.041 Uiso 1 1 calc R U . . .


_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 1.5881(16) . ?
P1 N2 1.5936(16) 2_577 ?
P1 N4 1.6427(15) . ?
P1 N3 1.6442(15) . ?
P2 N1 1.5368(16) . ?
P2 N2 1.5538(16) . ?
P2 Cl2 1.9985(7) . ?
P2 Cl1 2.0489(7) . ?
F1 C9 1.358(2) . ?
N3 C5 1.460(2) . ?
N3 C4 1.466(2) . ?
N4 C2 1.463(2) . ?
N4 C3 1.468(2) . ?
C1 C2 1.507(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.516(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.506(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.382(3) . ?
C6 C7 1.382(3) . ?
C7 C8 1.389(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.363(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(3) . ?
C10 C11 1.382(3) . ?
C10 H10 0.9300 . ?
C11 H11 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 N2 112.93(9) . 2_577 ?
N1 P1 N4 115.00(9) . . ?
N2 P1 N4 110.77(9) 2_577 . ?
N1 P1 N3 109.16(8) . . ?
N2 P1 N3 111.71(9) 2_577 . ?
N4 P1 N3 96.09(8) . . ?
N1 P2 N2 124.05(9) . . ?
N1 P2 Cl2 106.75(7) . . ?
N2 P2 Cl2 104.79(6) . . ?
N1 P2 Cl1 109.34(7) . . ?
N2 P2 Cl1 108.43(7) . . ?
Cl2 P2 Cl1 100.95(4) . . ?
P2 N1 P1 143.62(11) . . ?
P2 N2 P1 130.85(11) . 2_577 ?
C5 N3 C4 116.31(15) . . ?
C5 N3 P1 121.09(12) . . ?
C4 N3 P1 111.24(12) . . ?
C2 N4 C3 116.30(15) . . ?
C2 N4 P1 120.94(13) . . ?
C3 N4 P1 111.65(12) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N4 C2 C1 111.70(17) . . ?
N4 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N4 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
N4 C3 C4 106.29(14) . . ?
N4 C3 H3A 110.5 . . ?
C4 C3 H3A 110.5 . . ?
N4 C3 H3B 110.5 . . ?
C4 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
N3 C4 C3 105.91(14) . . ?
N3 C4 H4A 110.6 . . ?
C3 C4 H4A 110.6 . . ?
N3 C4 H4B 110.6 . . ?
C3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
N3 C5 C6 110.65(15) . . ?
N3 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C11 C6 C7 118.80(19) . . ?
C11 C6 C5 120.14(18) . . ?
C7 C6 C5 121.04(19) . . ?
C6 C7 C8 120.9(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 118.35(19) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
F1 C9 C8 119.01(19) . . ?
F1 C9 C10 118.4(2) . . ?
C8 C9 C10 122.6(2) . . ?
C9 C10 C11 118.1(2) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
C6 C11 C10 121.28(19) . . ?
C6 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?

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
N2 P2 N1 P1 88.1(2) . . . . ?
Cl2 P2 N1 P1 -150.21(18) . . . . ?
Cl1 P2 N1 P1 -41.8(2) . . . . ?
N2 P1 N1 P2 -59.9(2) 2_577 . . . ?
N4 P1 N1 P2 68.6(2) . . . . ?
N3 P1 N1 P2 175.22(18) . . . . ?
N1 P2 N2 P1 -49.66(19) . . . 2_577 ?
Cl2 P2 N2 P1 -172.22(13) . . . 2_577 ?
Cl1 P2 N2 P1 80.62(15) . . . 2_577 ?
N1 P1 N3 C5 35.77(17) . . . . ?
N2 P1 N3 C5 -89.85(16) 2_577 . . . ?
N4 P1 N3 C5 154.91(15) . . . . ?
N1 P1 N3 C4 -106.39(14) . . . . ?
N2 P1 N3 C4 128.00(13) 2_577 . . . ?
N4 P1 N3 C4 12.76(14) . . . . ?
N1 P1 N4 C2 -96.42(16) . . . . ?
N2 P1 N4 C2 33.12(17) 2_577 . . . ?
N3 P1 N4 C2 149.12(15) . . . . ?
N1 P1 N4 C3 121.05(13) . . . . ?
N2 P1 N4 C3 -109.40(14) 2_577 . . . ?
N3 P1 N4 C3 6.60(14) . . . . ?
C3 N4 C2 C1 -68.8(2) . . . . ?
P1 N4 C2 C1 150.29(16) . . . . ?
C2 N4 C3 C4 -167.22(16) . . . . ?
P1 N4 C3 C4 -22.82(18) . . . . ?
C5 N3 C4 C3 -171.22(16) . . . . ?
P1 N3 C4 C3 -27.10(18) . . . . ?
N4 C3 C4 N3 30.5(2) . . . . ?
C4 N3 C5 C6 -66.8(2) . . . . ?
P1 N3 C5 C6 152.80(14) . . . . ?
N3 C5 C6 C11 -75.5(2) . . . . ?
N3 C5 C6 C7 102.5(2) . . . . ?
C11 C6 C7 C8 -0.3(3) . . . . ?
C5 C6 C7 C8 -178.41(19) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 F1 -179.7(2) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
F1 C9 C10 C11 -179.9(2) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C7 C6 C11 C10 0.7(3) . . . . ?
C5 C6 C11 C10 178.8(2) . . . . ?
C9 C10 C11 C6 -0.8(4) . . . . ?

_refine_diff_density_max         0.898
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.070

