# 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 2023

####################################################################### 
# 
# 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_jd16_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1897575'
loop_
_audit_author_name
_audit_author_address
'Dr. Dinda'
;Utkal University, Bhubaneswar, India
India
;
_audit_update_record             
;
2023-09-16 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_audit_creation_date             2023-09-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 Au N6, 0.5(F12 P2)'
_chemical_formula_sum            'C24 H18 Au F6 N6 P'
_chemical_formula_weight         732.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6993(5)
_cell_length_b                   14.4139(8)
_cell_length_c                   10.5286(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.7960(10)
_cell_angle_gamma                90
_cell_volume                     1263.87(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9582
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.331
_cell_measurement_theta_min      2.466
_shelx_estimated_absorpt_T_max   0.469
_shelx_estimated_absorpt_T_min   0.124
_exptl_absorpt_coefficient_mu    5.954
_exptl_absorpt_correction_T_max  0.469
_exptl_absorpt_correction_T_min  0.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS. Ver. 2014/5. (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.924
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            65736
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.360
_diffrn_reflns_theta_min         2.685
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker AXS D8 Quest diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2465
_reflns_number_total             3151
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.962
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0250
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²+4.1969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0803
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: F1(0.5) F2(0.5) F3(0.5) F4(0.5) F5(0.5) F6(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.000000 0.500000 0.500000 0.03272(8) Uani 1 2 d S . P . .
N1 N 0.1505(4) 0.3203(2) 0.4409(3) 0.0283(6) Uani 1 1 d . . . . .
N2 N 0.3335(4) 0.4099(2) 0.5556(3) 0.0281(6) Uani 1 1 d . . . . .
N3 N -0.2715(5) 0.3002(3) 0.2398(4) 0.0481(10) Uani 1 1 d . . . . .
C1 C 0.1717(4) 0.4049(3) 0.4998(4) 0.0282(7) Uani 1 1 d . . . . .
C2 C 0.2924(5) 0.2735(3) 0.4580(4) 0.0347(8) Uani 1 1 d . . . . .
H2 H 0.305223 0.214824 0.425760 0.042 Uiso 1 1 calc R U . . .
C3 C 0.4106(5) 0.3295(3) 0.5313(4) 0.0319(8) Uani 1 1 d . . . . .
C4 C 0.5806(5) 0.3233(3) 0.5831(5) 0.0423(10) Uani 1 1 d . . . . .
H4 H 0.635008 0.271135 0.566799 0.051 Uiso 1 1 calc R U . . .
C5 C 0.6611(5) 0.3937(4) 0.6558(5) 0.0466(11) Uani 1 1 d . . . . .
H5 H 0.772344 0.390513 0.689126 0.056 Uiso 1 1 calc R U . . .
C6 C 0.5797(6) 0.4725(4) 0.6823(5) 0.0449(11) Uani 1 1 d . . . . .
H6 H 0.638067 0.519631 0.734999 0.054 Uiso 1 1 calc R U . . .
C7 C 0.4195(5) 0.4811(3) 0.6333(4) 0.0366(9) Uani 1 1 d . . . . .
H7 H 0.367360 0.533725 0.651061 0.044 Uiso 1 1 calc R U . . .
C8 C -0.0048(4) 0.2810(3) 0.3812(4) 0.0295(7) Uani 1 1 d . . . . .
C9 C -0.0397(5) 0.1936(3) 0.4179(5) 0.0423(10) Uani 1 1 d . . . . .
H9 H 0.038124 0.157948 0.476864 0.051 Uiso 1 1 calc R U . . .
C10 C -0.1932(6) 0.1607(4) 0.3647(5) 0.0515(12) Uani 1 1 d . . . . .
H10 H -0.221634 0.101840 0.386140 0.062 Uiso 1 1 calc R U . . .
C11 C -0.3046(6) 0.2173(4) 0.2784(5) 0.0545(13) Uani 1 1 d . . . . .
H11 H -0.409249 0.195475 0.245519 0.065 Uiso 1 1 calc R U . . .
C12 C -0.1198(5) 0.3314(3) 0.2897(4) 0.0370(9) Uani 1 1 d . . . . .
H12 H -0.091936 0.388461 0.261458 0.044 Uiso 1 1 calc R U . . .
P1 P 1.000000 0.500000 1.000000 0.0316(3) Uani 1 2 d S . P . .
F1 F 0.9978(14) 0.4689(8) 0.8539(10) 0.054(2) Uani 0.5 1 d . . P A 1
F2 F 1.163(3) 0.5432(16) 0.9834(15) 0.049(3) Uani 0.5 1 d . . P A 2
F3 F 0.927(2) 0.5983(11) 0.941(2) 0.072(5) Uani 0.5 1 d . . P A 1
F4 F 0.9846(15) 0.4305(9) 0.8823(14) 0.081(4) Uani 0.5 1 d . . P A 2
F5 F 0.905(2) 0.5753(11) 0.905(2) 0.090(6) Uani 0.5 1 d . . P A 2
F6 F 1.181(2) 0.5333(16) 1.0223(14) 0.045(3) Uani 0.5 1 d . . P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C1 2.028(4) . ?
Au1 C1 2.028(4) 3_566 ?
N1 C1 1.356(5) . ?
N1 C2 1.372(5) . ?
N1 C8 1.432(5) . ?
N2 C1 1.361(5) . ?
N2 C3 1.400(5) . ?
N2 C7 1.388(5) . ?
N3 C11 1.320(8) . ?
N3 C12 1.349(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.359(5) . ?
C3 C4 1.424(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.340(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.409(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.345(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(6) . ?
C8 C12 1.379(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
P1 F1 1.597(11) . ?
P1 F1 1.597(11) 3_767 ?
P1 F2 1.60(2) . ?
P1 F2 1.60(2) 3_767 ?
P1 F3 1.602(18) 3_767 ?
P1 F3 1.602(18) . ?
P1 F4 1.569(11) 3_767 ?
P1 F4 1.568(11) . ?
P1 F5 1.542(19) . ?
P1 F5 1.542(19) 3_767 ?
P1 F6 1.60(2) 3_767 ?
P1 F6 1.60(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Au1 C1 180.0 . 3_566 ?
C1 N1 C2 112.5(3) . . ?
C1 N1 C8 122.9(3) . . ?
C2 N1 C8 124.2(3) . . ?
C1 N2 C3 111.5(3) . . ?
C1 N2 C7 127.5(4) . . ?
C7 N2 C3 120.9(3) . . ?
C11 N3 C12 117.3(4) . . ?
N1 C1 Au1 127.3(3) . . ?
N1 C1 N2 103.5(3) . . ?
N2 C1 Au1 129.3(3) . . ?
N1 C2 H2 126.7 . . ?
C3 C2 N1 106.7(3) . . ?
C3 C2 H2 126.7 . . ?
N2 C3 C4 118.8(4) . . ?
C2 C3 N2 105.8(3) . . ?
C2 C3 C4 135.4(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.0(4) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.9(4) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.6(4) . . ?
C7 C6 H6 119.2 . . ?
N2 C7 H7 120.7 . . ?
C6 C7 N2 118.7(4) . . ?
C6 C7 H7 120.7 . . ?
C9 C8 N1 119.7(4) . . ?
C9 C8 C12 120.3(4) . . ?
C12 C8 N1 120.0(4) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 C8 117.9(4) . . ?
C10 C9 H9 121.0 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.5(5) . . ?
C11 C10 H10 120.7 . . ?
N3 C11 C10 124.1(4) . . ?
N3 C11 H11 118.0 . . ?
C10 C11 H11 118.0 . . ?
N3 C12 C8 121.8(4) . . ?
N3 C12 H12 119.1 . . ?
C8 C12 H12 119.1 . . ?
F1 P1 F1 180.0 3_767 . ?
F1 P1 F2 76.6(8) 3_767 3_767 ?
F1 P1 F2 103.4(8) . 3_767 ?
F1 P1 F3 91.0(9) . 3_767 ?
F1 P1 F3 89.0(9) 3_767 3_767 ?
F1 P1 F3 89.0(9) . . ?
F1 P1 F3 91.0(9) 3_767 . ?
F1 P1 F6 92.1(8) . 3_767 ?
F1 P1 F6 87.9(8) 3_767 3_767 ?
F1 P1 F6 92.1(8) 3_767 . ?
F1 P1 F6 87.9(8) . . ?
F3 P1 F3 180.0(17) 3_767 . ?
F4 P1 F2 87.8(10) 3_767 . ?
F4 P1 F2 92.2(10) . . ?
F4 P1 F6 80.6(9) . 3_767 ?
F4 P1 F6 99.4(9) 3_767 3_767 ?
F5 P1 F2 88.8(10) . . ?
F5 P1 F2 91.2(10) 3_767 . ?
F5 P1 F4 88.3(10) 3_767 . ?
F5 P1 F4 91.7(10) . . ?
F5 P1 F6 101.8(10) 3_767 3_767 ?
F5 P1 F6 78.2(10) . 3_767 ?
F6 P1 F2 15.1(7) 3_767 3_767 ?
F6 P1 F2 164.9(7) . 3_767 ?
F6 P1 F3 93.1(9) . . ?
F6 P1 F3 86.9(9) 3_767 . ?
F6 P1 F3 86.9(9) . 3_767 ?
F6 P1 F3 93.1(9) 3_767 3_767 ?
F6 P1 F6 180.0 3_767 . ?

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 C2 C3 N2 -0.2(4) . . . . ?
N1 C2 C3 C4 179.8(4) . . . . ?
N1 C8 C9 C10 176.0(4) . . . . ?
N1 C8 C12 N3 -174.2(4) . . . . ?
N2 C3 C4 C5 1.3(6) . . . . ?
C1 N1 C2 C3 0.2(5) . . . . ?
C1 N1 C8 C9 -126.8(4) . . . . ?
C1 N1 C8 C12 51.8(5) . . . . ?
C1 N2 C3 C2 0.1(4) . . . . ?
C1 N2 C3 C4 -179.9(4) . . . . ?
C1 N2 C7 C6 178.5(4) . . . . ?
C2 N1 C1 Au1 179.1(3) . . . . ?
C2 N1 C1 N2 -0.2(4) . . . . ?
C2 N1 C8 C9 45.6(5) . . . . ?
C2 N1 C8 C12 -135.8(4) . . . . ?
C2 C3 C4 C5 -178.7(5) . . . . ?
C3 N2 C1 Au1 -179.2(3) . . . . ?
C3 N2 C1 N1 0.1(4) . . . . ?
C3 N2 C7 C6 1.6(6) . . . . ?
C3 C4 C5 C6 0.8(7) . . . . ?
C4 C5 C6 C7 -1.7(8) . . . . ?
C5 C6 C7 N2 0.5(7) . . . . ?
C7 N2 C1 Au1 3.7(6) . . . . ?
C7 N2 C1 N1 -177.1(4) . . . . ?
C7 N2 C3 C2 177.4(4) . . . . ?
C7 N2 C3 C4 -2.5(5) . . . . ?
C8 N1 C1 Au1 -7.7(5) . . . . ?
C8 N1 C1 N2 173.1(3) . . . . ?
C8 N1 C2 C3 -172.9(3) . . . . ?
C8 C9 C10 C11 -0.6(7) . . . . ?
C9 C8 C12 N3 4.4(6) . . . . ?
C9 C10 C11 N3 2.5(8) . . . . ?
C11 N3 C12 C8 -2.6(7) . . . . ?
C12 N3 C11 C10 -0.9(7) . . . . ?
C12 C8 C9 C10 -2.6(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jd15_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1898678'
loop_
_audit_author_name
_audit_author_address
'Dr. Dinda'
;Utkal University, Bhubaneswar, India
India
;
_audit_update_record             
;
2023-09-16 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_audit_creation_date             2023-09-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 N3, F6 P'
_chemical_formula_sum            'C12 H10 F6 N3 P'
_chemical_formula_weight         341.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.3998(12)
_cell_length_b                   9.7138(6)
_cell_length_c                   15.2920(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.451(2)
_cell_angle_gamma                90
_cell_volume                     2724.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.510
_cell_measurement_theta_min      2.221
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.852
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS. Ver. 2014/5. (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            47331
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.406
_diffrn_reflns_theta_min         3.509
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker AXS D8 Quest diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2472
_reflns_number_total             3365
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0599P)²+3.1056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1488
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: F1(0.5) F2(0.5) F3(0.5) F4(0.5) F5(0.5) F6(0.5) F7(0.5) F8(0.5)
 F9(0.5) F10(0.5) F11(0.5) F12(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11),
 C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.39910(9) 0.29900(19) 0.36033(12) 0.0430(4) Uani 1 1 d . . . . .
N2 N 0.37036(8) 0.51199(17) 0.36980(10) 0.0383(4) Uani 1 1 d . . . . .
N3 N 0.21579(13) 0.7512(3) 0.34018(19) 0.0715(7) Uani 1 1 d . . . . .
C1 C 0.34328(11) 0.3853(2) 0.36369(14) 0.0429(5) Uani 1 1 d . . . . .
H1 H 0.294263 0.361311 0.362069 0.051 Uiso 1 1 calc R U . . .
C2 C 0.44456(11) 0.5080(2) 0.36997(15) 0.0454(5) Uani 1 1 d . . . . .
H2 H 0.475950 0.583140 0.373304 0.055 Uiso 1 1 calc R U . . .
C3 C 0.46383(11) 0.3738(2) 0.36438(14) 0.0441(5) Uani 1 1 d . . . . .
C4 C 0.53096(13) 0.3014(3) 0.36287(17) 0.0583(6) Uani 1 1 d . . . . .
H4 H 0.574969 0.348713 0.364040 0.070 Uiso 1 1 calc R U . . .
C5 C 0.52938(15) 0.1632(3) 0.35972(18) 0.0650(7) Uani 1 1 d . . . . .
H5 H 0.572864 0.114179 0.360612 0.078 Uiso 1 1 calc R U . . .
C6 C 0.46216(16) 0.0911(3) 0.35506(19) 0.0670(7) Uani 1 1 d . . . . .
H6 H 0.462659 -0.004490 0.352104 0.080 Uiso 1 1 calc R U . . .
C7 C 0.39838(15) 0.1558(2) 0.35477(18) 0.0575(6) Uani 1 1 d . . . . .
H7 H 0.354752 0.107035 0.350975 0.069 Uiso 1 1 calc R U . . .
C8 C 0.32725(11) 0.6342(2) 0.37751(13) 0.0408(5) Uani 1 1 d . . . . .
C9 C 0.35457(15) 0.7424(2) 0.42705(17) 0.0554(6) Uani 1 1 d . . . . .
H9 H 0.400968 0.739021 0.455797 0.066 Uiso 1 1 calc R U . . .
C10 C 0.31068(18) 0.8569(3) 0.43275(19) 0.0684(8) Uani 1 1 d . . . . .
H10 H 0.326733 0.933071 0.465618 0.082 Uiso 1 1 calc R U . . .
C11 C 0.24264(18) 0.8554(3) 0.3886(2) 0.0749(9) Uani 1 1 d . . . . .
H11 H 0.213426 0.932812 0.393067 0.090 Uiso 1 1 calc R U . . .
C12 C 0.25873(13) 0.6420(3) 0.33538(17) 0.0546(6) Uani 1 1 d . . . . .
H12 H 0.241538 0.567287 0.301855 0.065 Uiso 1 1 calc R U . . .
P1 P 0.37195(3) 0.25228(6) 0.62241(4) 0.04502(19) Uani 1 1 d . . . . .
F1 F 0.3831(3) 0.3869(7) 0.5595(5) 0.0681(14) Uani 0.5 1 d . . P A 2
F2 F 0.3512(6) 0.1300(11) 0.5646(7) 0.142(4) Uani 0.5 1 d . . P A 2
F3 F 0.2964(4) 0.3041(10) 0.6503(5) 0.083(2) Uani 0.5 1 d . . P A 1
F4 F 0.3517(8) 0.1349(14) 0.6818(12) 0.136(5) Uani 0.5 1 d . . P A 2
F5 F 0.3954(6) 0.3699(9) 0.6882(7) 0.102(3) Uani 0.5 1 d . . P A 2
F6 F 0.4534(6) 0.2060(9) 0.6243(9) 0.142(5) Uani 0.5 1 d . . P A 2
F7 F 0.2908(5) 0.3074(10) 0.6240(8) 0.127(4) Uani 0.5 1 d . . P A 2
F8 F 0.3300(4) 0.1746(10) 0.5388(6) 0.096(2) Uani 0.5 1 d . . P A 1
F9 F 0.3805(6) 0.3505(9) 0.5498(6) 0.149(4) Uani 0.5 1 d . . P A 1
F10 F 0.4449(5) 0.1988(12) 0.5909(7) 0.103(3) Uani 0.5 1 d . . P A 1
F11 F 0.4085(6) 0.3407(11) 0.6979(7) 0.113(4) Uani 0.5 1 d . . P A 1
F12 F 0.3695(8) 0.1417(13) 0.6989(11) 0.136(5) Uani 0.5 1 d . . P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.330(3) . ?
N1 C3 1.393(3) . ?
N1 C7 1.394(3) . ?
N2 C1 1.328(3) . ?
N2 C2 1.366(2) . ?
N2 C8 1.437(3) . ?
N3 C11 1.327(4) . ?
N3 C12 1.328(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.355(3) . ?
C3 C4 1.423(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.344(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.418(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.331(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.369(3) . ?
C8 C12 1.373(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
P1 F1 1.645(7) . ?
P1 F2 1.512(10) . ?
P1 F3 1.568(6) . ?
P1 F4 1.521(11) . ?
P1 F5 1.561(7) . ?
P1 F6 1.563(10) . ?
P1 F7 1.589(10) . ?
P1 F8 1.627(8) . ?
P1 F9 1.482(8) . ?
P1 F10 1.551(8) . ?
P1 F11 1.550(9) . ?
P1 F12 1.592(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C3 109.24(18) . . ?
C1 N1 C7 128.9(2) . . ?
C3 N1 C7 121.87(19) . . ?
C1 N2 C2 110.06(18) . . ?
C1 N2 C8 124.37(16) . . ?
C2 N2 C8 125.55(17) . . ?
C11 N3 C12 116.3(3) . . ?
N1 C1 H1 126.3 . . ?
N2 C1 N1 107.47(17) . . ?
N2 C1 H1 126.3 . . ?
N2 C2 H2 126.5 . . ?
C3 C2 N2 107.09(18) . . ?
C3 C2 H2 126.5 . . ?
N1 C3 C4 118.8(2) . . ?
C2 C3 N1 106.13(18) . . ?
C2 C3 C4 135.1(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(2) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 118.9 . . ?
C7 C6 C5 122.2(3) . . ?
C7 C6 H6 118.9 . . ?
N1 C7 H7 121.1 . . ?
C6 C7 N1 117.8(2) . . ?
C6 C7 H7 121.1 . . ?
C9 C8 N2 119.9(2) . . ?
C9 C8 C12 120.1(2) . . ?
C12 C8 N2 120.0(2) . . ?
C8 C9 H9 121.2 . . ?
C8 C9 C10 117.5(3) . . ?
C10 C9 H9 121.2 . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.4(3) . . ?
C11 C10 H10 120.8 . . ?
N3 C11 C10 124.6(3) . . ?
N3 C11 H11 117.7 . . ?
C10 C11 H11 117.7 . . ?
N3 C12 C8 123.2(3) . . ?
N3 C12 H12 118.4 . . ?
C8 C12 H12 118.4 . . ?
F2 P1 F1 108.7(5) . . ?
F2 P1 F4 72.4(9) . . ?
F2 P1 F5 175.2(6) . . ?
F2 P1 F6 89.0(6) . . ?
F2 P1 F7 94.5(6) . . ?
F3 P1 F8 89.2(4) . . ?
F3 P1 F12 86.6(6) . . ?
F4 P1 F1 172.6(7) . . ?
F4 P1 F5 103.4(8) . . ?
F4 P1 F6 93.0(7) . . ?
F4 P1 F7 88.3(7) . . ?
F5 P1 F1 75.8(5) . . ?
F5 P1 F6 89.0(6) . . ?
F5 P1 F7 87.5(6) . . ?
F6 P1 F1 94.3(4) . . ?
F6 P1 F7 176.5(5) . . ?
F7 P1 F1 84.3(4) . . ?
F9 P1 F3 98.3(6) . . ?
F9 P1 F8 77.4(5) . . ?
F9 P1 F10 80.7(6) . . ?
F9 P1 F11 97.8(6) . . ?
F9 P1 F12 175.1(7) . . ?
F10 P1 F3 177.4(5) . . ?
F10 P1 F8 88.3(5) . . ?
F10 P1 F12 94.4(7) . . ?
F11 P1 F3 87.8(5) . . ?
F11 P1 F8 173.9(6) . . ?
F11 P1 F10 94.7(6) . . ?
F11 P1 F12 82.1(7) . . ?
F12 P1 F8 103.1(7) . . ?

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 C3 C4 C5 -1.6(3) . . . . ?
N2 C2 C3 N1 0.4(2) . . . . ?
N2 C2 C3 C4 -178.9(2) . . . . ?
N2 C8 C9 C10 -179.5(2) . . . . ?
N2 C8 C12 N3 179.5(2) . . . . ?
C1 N1 C3 C2 -0.2(2) . . . . ?
C1 N1 C3 C4 179.2(2) . . . . ?
C1 N1 C7 C6 -177.9(2) . . . . ?
C1 N2 C2 C3 -0.4(2) . . . . ?
C1 N2 C8 C9 145.4(2) . . . . ?
C1 N2 C8 C12 -34.4(3) . . . . ?
C2 N2 C1 N1 0.3(2) . . . . ?
C2 N2 C8 C9 -32.8(3) . . . . ?
C2 N2 C8 C12 147.4(2) . . . . ?
C2 C3 C4 C5 177.6(3) . . . . ?
C3 N1 C1 N2 -0.1(2) . . . . ?
C3 N1 C7 C6 1.2(4) . . . . ?
C3 C4 C5 C6 2.1(4) . . . . ?
C4 C5 C6 C7 -0.9(4) . . . . ?
C5 C6 C7 N1 -0.8(4) . . . . ?
C7 N1 C1 N2 179.2(2) . . . . ?
C7 N1 C3 C2 -179.5(2) . . . . ?
C7 N1 C3 C4 -0.1(3) . . . . ?
C8 N2 C1 N1 -178.12(17) . . . . ?
C8 N2 C2 C3 177.97(18) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C8 C12 N3 -0.4(4) . . . . ?
C9 C10 C11 N3 -0.2(4) . . . . ?
C11 N3 C12 C8 0.1(4) . . . . ?
C12 N3 C11 C10 0.2(4) . . . . ?
C12 C8 C9 C10 0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
