# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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. 
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#######################################################################

data_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc27q022
_database_code_depnum_ccdc_archive 'CCDC 2076723'
loop_
_audit_author_name
_audit_author_address
'Dr. Sundar N Dhuri'
;Professor 
India
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-12-17 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         ?
_chemical_formula_sum            'C16 H22 Cl Cr F6 N5 O P'
_chemical_formula_weight         532.81

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'
Cr Cr 0.3209 0.6236 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.2977(4)
_cell_length_b                   18.0900(8)
_cell_length_c                   12.9340(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.379(2)
_cell_angle_gamma                90
_cell_volume                     2161.97(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6363
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      27.21

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_F_000             1084
_exptl_transmission_factor_min   0.6981
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.797
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32063
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.754
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5365
_reflns_number_gt                3786
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0884P)²+6.0400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5365
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1302
_refine_ls_R_factor_gt           0.0939
_refine_ls_wR_factor_ref         0.2279
_refine_ls_wR_factor_gt          0.2085
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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
Cr1 Cr 0.53968(8) 0.65715(4) 0.69725(6) 0.0323(2) Uani 1 1 d . . . . .
O1 O 0.5215(9) 0.7955(5) 0.6173(6) 0.093(2) Uani 1 1 d . . . . .
F1 F 0.0764(12) 0.8877(7) 0.7713(6) 0.232(5) Uani 1 1 d . . . . .
P1 P -0.02623(19) 0.91567(9) 0.68322(12) 0.0487(4) Uani 1 1 d . . . . .
C1 C 0.7117(6) 0.5830(3) 0.5332(4) 0.0434(12) Uani 1 1 d . . . . .
H1 H 0.625295 0.559739 0.508764 0.052 Uiso 1 1 calc R U . . .
Cl1 Cl 0.36794(17) 0.60595(10) 0.57492(13) 0.0604(4) Uani 1 1 d . . . . .
N1 N 0.7138(4) 0.6275(2) 0.6165(3) 0.0346(9) Uani 1 1 d . . . . .
N2 N 0.7210(5) 0.6825(3) 0.8061(3) 0.0392(10) Uani 1 1 d . . . . .
F2 F -0.0288(7) 0.9928(3) 0.7382(4) 0.1114(19) Uani 1 1 d . . . . .
C2 C 0.8302(7) 0.5704(3) 0.4831(5) 0.0517(15) Uani 1 1 d . . . . .
H2 H 0.823607 0.540137 0.424579 0.062 Uiso 1 1 calc R U . . .
C3 C 0.9592(7) 0.6023(4) 0.5191(6) 0.0565(16) Uani 1 1 d . . . . .
H3 H 1.041342 0.593695 0.485890 0.068 Uiso 1 1 calc R U . . .
N3 N 0.5408(5) 0.5556(2) 0.7865(4) 0.0420(10) Uani 1 1 d . . . . .
F3 F 0.0939(7) 0.9425(4) 0.6203(5) 0.135(3) Uani 1 1 d . . . . .
N4 N 0.3851(5) 0.6773(3) 0.7980(3) 0.0410(10) Uani 1 1 d . . . . .
F4 F -0.0364(7) 0.8400(2) 0.6218(4) 0.113(2) Uani 1 1 d . . . . .
C4 C 0.9657(6) 0.6473(3) 0.6049(5) 0.0491(14) Uani 1 1 d . . . . .
H4 H 1.052630 0.669142 0.631245 0.059 Uiso 1 1 calc R U . . .
C9 C 0.6414(6) 0.5685(4) 0.8846(5) 0.0517(15) Uani 1 1 d . . . . .
H9A H 0.590878 0.595314 0.934607 0.062 Uiso 1 1 calc R U . . .
H9AB H 0.672834 0.521493 0.915177 0.062 Uiso 1 1 calc R U . . .
C8 C 0.7708(6) 0.6124(4) 0.8596(4) 0.0492(14) Uani 1 1 d . . . . .
H8A H 0.832305 0.623634 0.923261 0.059 Uiso 1 1 calc R U . . .
H8AB H 0.826700 0.583603 0.815022 0.059 Uiso 1 1 calc R U . . .
C7 C 0.6977(8) 0.7406(4) 0.8830(5) 0.0602(17) Uani 1 1 d . . . . .
H7A H 0.659212 0.784034 0.847412 0.090 Uiso 1 1 calc R U . . .
H7B H 0.788217 0.752365 0.922793 0.090 Uiso 1 1 calc R U . . .
H7C H 0.630703 0.723031 0.928779 0.090 Uiso 1 1 calc R U . . .
C6 C 0.8350(6) 0.7090(3) 0.7435(4) 0.0469(14) Uani 1 1 d . . . . .
H6A H 0.927986 0.708878 0.785698 0.056 Uiso 1 1 calc R U . . .
H6AB H 0.813822 0.759207 0.720299 0.056 Uiso 1 1 calc R U . . .
F6 F -0.1385(8) 0.9455(5) 0.5955(5) 0.155(3) Uani 1 1 d . . . . .
N5 N 0.5317(8) 0.7526(4) 0.6390(6) 0.0520(16) Uani 1 1 d . . . . .
F5 F -0.1528(8) 0.8926(4) 0.7455(6) 0.156(3) Uani 1 1 d . . . . .
C5 C 0.8404(5) 0.6596(3) 0.6520(4) 0.0398(11) Uani 1 1 d . . . . .
C10 C 0.5856(7) 0.4880(3) 0.7356(5) 0.0571(16) Uani 1 1 d . . . . .
H10A H 0.529969 0.482805 0.668843 0.086 Uiso 1 1 calc R U . . .
H10B H 0.569441 0.445903 0.777976 0.086 Uiso 1 1 calc R U . . .
H10C H 0.686502 0.491177 0.726602 0.086 Uiso 1 1 calc R U . . .
C11 C 0.3924(6) 0.5459(3) 0.8154(5) 0.0505(14) Uani 1 1 d . . . . .
H11A H 0.393570 0.511563 0.872995 0.061 Uiso 1 1 calc R U . . .
H11B H 0.330403 0.525747 0.756874 0.061 Uiso 1 1 calc R U . . .
C12 C 0.3351(6) 0.6184(3) 0.8455(4) 0.0453(13) Uani 1 1 d . . . . .
C13 C 0.2361(7) 0.6254(4) 0.9175(5) 0.0592(17) Uani 1 1 d . . . . .
H13 H 0.203334 0.583773 0.949981 0.071 Uiso 1 1 calc R U . . .
C14 C 0.1872(7) 0.6940(5) 0.9403(5) 0.0642(19) Uani 1 1 d . . . . .
H14 H 0.122965 0.699758 0.989991 0.077 Uiso 1 1 calc R U . . .
C15 C 0.2340(7) 0.7543(4) 0.8889(5) 0.0621(17) Uani 1 1 d . . . . .
H15 H 0.199557 0.801335 0.901747 0.075 Uiso 1 1 calc R U . . .
C16 C 0.3331(7) 0.7443(4) 0.8179(5) 0.0536(15) Uani 1 1 d . . . . .
H16 H 0.364367 0.785178 0.782899 0.064 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
Cr1 N5 1.883(7) . ?
Cr1 N4 2.077(4) . ?
Cr1 N1 2.092(4) . ?
Cr1 N2 2.123(4) . ?
Cr1 N3 2.169(4) . ?
Cr1 Cl1 2.3130(17) . ?
O1 N5 0.826(9) . ?
F1 P1 1.490(7) . ?
P1 F3 1.532(5) . ?
P1 F6 1.550(6) . ?
P1 F5 1.555(5) . ?
P1 F2 1.567(5) . ?
P1 F4 1.581(5) . ?
C1 N1 1.344(7) . ?
C1 C2 1.359(8) . ?
C1 H1 0.9300 . ?
N1 C5 1.346(6) . ?
N2 C7 1.480(7) . ?
N2 C6 1.482(7) . ?
N2 C8 1.494(7) . ?
C2 C3 1.365(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(9) . ?
C3 H3 0.9300 . ?
N3 C10 1.471(8) . ?
N3 C11 1.479(7) . ?
N3 C9 1.508(7) . ?
N4 C12 1.339(7) . ?
N4 C16 1.340(7) . ?
C4 C5 1.391(7) . ?
C4 H4 0.9300 . ?
C9 C8 1.506(8) . ?
C9 H9A 0.9700 . ?
C9 H9AB 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 C5 1.488(8) . ?
C6 H6A 0.9700 . ?
C6 H6AB 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.484(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.386(8) . ?
C13 C14 1.364(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(9) . ?
C15 H15 0.9300 . ?
C16 H16 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
N5 Cr1 N4 95.2(3) . . ?
N5 Cr1 N1 91.9(2) . . ?
N4 Cr1 N1 170.54(17) . . ?
N5 Cr1 N2 93.5(3) . . ?
N4 Cr1 N2 95.73(17) . . ?
N1 Cr1 N2 77.57(16) . . ?
N5 Cr1 N3 171.0(3) . . ?
N4 Cr1 N3 77.15(18) . . ?
N1 Cr1 N3 95.22(17) . . ?
N2 Cr1 N3 82.73(17) . . ?
N5 Cr1 Cl1 95.7(2) . . ?
N4 Cr1 Cl1 91.52(13) . . ?
N1 Cr1 Cl1 93.99(12) . . ?
N2 Cr1 Cl1 167.72(14) . . ?
N3 Cr1 Cl1 89.27(13) . . ?
F1 P1 F3 94.1(6) . . ?
F1 P1 F6 177.1(5) . . ?
F3 P1 F6 88.4(5) . . ?
F1 P1 F5 88.3(6) . . ?
F3 P1 F5 176.7(4) . . ?
F6 P1 F5 89.1(5) . . ?
F1 P1 F2 89.8(5) . . ?
F3 P1 F2 90.4(3) . . ?
F6 P1 F2 88.8(4) . . ?
F5 P1 F2 87.3(3) . . ?
F1 P1 F4 95.0(5) . . ?
F3 P1 F4 90.8(3) . . ?
F6 P1 F4 86.3(4) . . ?
F5 P1 F4 91.2(3) . . ?
F2 P1 F4 174.9(4) . . ?
N1 C1 C2 122.8(5) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 N1 C5 117.8(5) . . ?
C1 N1 Cr1 127.6(4) . . ?
C5 N1 Cr1 114.5(3) . . ?
C7 N2 C6 107.7(4) . . ?
C7 N2 C8 110.6(5) . . ?
C6 N2 C8 108.9(4) . . ?
C7 N2 Cr1 115.8(4) . . ?
C6 N2 Cr1 105.7(3) . . ?
C8 N2 Cr1 107.9(3) . . ?
C1 C2 C3 119.7(6) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 119.0(5) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C10 N3 C11 109.4(5) . . ?
C10 N3 C9 109.0(5) . . ?
C11 N3 C9 108.4(4) . . ?
C10 N3 Cr1 116.8(4) . . ?
C11 N3 Cr1 106.5(3) . . ?
C9 N3 Cr1 106.4(3) . . ?
C12 N4 C16 118.7(5) . . ?
C12 N4 Cr1 116.6(4) . . ?
C16 N4 Cr1 124.7(4) . . ?
C3 C4 C5 119.0(5) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C8 C9 N3 109.7(4) . . ?
C8 C9 H9A 109.7 . . ?
N3 C9 H9A 109.7 . . ?
C8 C9 H9AB 109.7 . . ?
N3 C9 H9AB 109.7 . . ?
H9A C9 H9AB 108.2 . . ?
N2 C8 C9 109.4(4) . . ?
N2 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N2 C8 H8AB 109.8 . . ?
C9 C8 H8AB 109.8 . . ?
H8A C8 H8AB 108.2 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C6 C5 109.2(4) . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6AB 109.8 . . ?
C5 C6 H6AB 109.8 . . ?
H6A C6 H6AB 108.3 . . ?
O1 N5 Cr1 174.0(11) . . ?
N1 C5 C4 121.6(5) . . ?
N1 C5 C6 115.1(4) . . ?
C4 C5 C6 123.3(5) . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C12 109.5(5) . . ?
N3 C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
N3 C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
N4 C12 C13 121.7(6) . . ?
N4 C12 C11 115.4(5) . . ?
C13 C12 C11 122.8(6) . . ?
C14 C13 C12 119.4(6) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 119.1(6) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C16 119.2(6) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
N4 C16 C15 121.8(6) . . ?
N4 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?

_refine_diff_density_max         1.006
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.100



