# 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 2020

####################################################################### 
# 
# 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_compound1+
_audit_block_doi                 10.5517/ccdc.csd.cc23w68h
_database_code_depnum_ccdc_archive 'CCDC 1962556'
loop_
_audit_author_name
_audit_author_address
'Vedichi Madhu'
;Department of Chemistry, Karunya University
India
;
_audit_update_record             
;
2020-05-26 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_compound1+          
;
RESPONSE:Due to poor diffraction from the crystal, the data sets collected at higher angle was too weak even after several attempts.
;
# start Validation Reply Form
_vrf_PLAT029_compound1+          
;
RESPONSE:Due to reflections collected at higher angle was too weak or missing due to poor crystal quality.
;
# start Validation Reply Form
_vrf_PLAT088_compound1+          
;
RESPONSE:The reflections to parameters ratio is low due to the very large number of refined parameters and the very weakly diffracting nature of the crystals
;
# start Validation Reply Form
_vrf_PLAT306_compound1+          
;
RESPONSE:Due to thermal ellipsoids of the crystal while collection data. 
;
# start Validation Reply Form
_vrf_PLAT911_compound1+          
;
RESPONSE:These reflections were probably affected by unexpected deviations in their intensities for symmetry equivalent measurements and omitted during initial data reduction.
;
# end Validation Reply Form
_audit_creation_date             2020-05-19
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(F6 P), C23 H16 N7 O, 2(O)'
_chemical_formula_sum            'C23 H16 F12 N7 O3 P2'
_chemical_formula_weight         728.37
_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'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.633(4)
_cell_length_b                   12.422(6)
_cell_length_c                   13.653(6)
_cell_angle_alpha                87.328(8)
_cell_angle_beta                 89.110(7)
_cell_angle_gamma                79.874(8)
_cell_volume                     1439.9(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1817
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             730
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_av_unetI/netI     0.1208
_diffrn_reflns_Laue_measured_fraction_full 0.894
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9540
_diffrn_reflns_point_group_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        22.497
_diffrn_reflns_theta_max         22.497
_diffrn_reflns_theta_min         2.833
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.894
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_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                1817
_reflns_number_total             3377
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         3377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1513
_refine_ls_R_factor_gt           0.0809
_refine_ls_restrained_S_all      0.989
_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)+(0.1198P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1874
_refine_ls_wR_factor_ref         0.2247
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C16(H16), C8(H8), C10(H10), C3(H3), C17(H17), C15(H15),
 C4(H4), C14(H14), C1(H1), C20(H20), C23(H23), C2(H2), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
P1 P 0.2934(2) 0.04133(18) 0.66893(15) 0.0512(7) Uani 1 1 d . . . . .
F6 F 0.4708(6) -0.0087(4) 0.6953(5) 0.0966(19) Uani 1 1 d . . . . .
F3 F 0.3108(7) 0.1449(5) 0.7270(5) 0.109(2) Uani 1 1 d . . . . .
F2 F 0.2788(8) -0.0604(5) 0.6076(5) 0.117(2) Uani 1 1 d . . . . .
F5 F 0.1180(6) 0.0900(5) 0.6438(5) 0.107(2) Uani 1 1 d . . . . .
F4 F 0.3497(8) 0.1019(6) 0.5749(4) 0.120(2) Uani 1 1 d . . . . .
F1 F 0.2420(8) -0.0240(7) 0.7605(5) 0.141(3) Uani 1 1 d . . . . .
P2 P 0.0279(3) 0.6999(2) 0.06025(19) 0.0784(9) Uani 1 1 d . . . . .
F10 F 0.096(2) 0.7099(17) 0.1545(8) 0.324(11) Uani 1 1 d . . . . .
F8 F -0.0239(10) 0.5931(7) 0.1004(6) 0.148(3) Uani 1 1 d . . . . .
F12 F -0.0647(10) 0.7022(9) -0.0318(5) 0.164(4) Uani 1 1 d . . . . .
F7 F 0.0817(13) 0.8050(7) 0.0192(8) 0.215(6) Uani 1 1 d . . . . .
F9 F -0.1225(15) 0.7391(13) 0.1120(10) 0.266(7) Uani 1 1 d . . . . .
F11 F 0.1854(13) 0.6449(9) 0.048(2) 0.435(18) Uani 1 1 d . . . . .
N6 N 0.2226(6) 0.9557(4) 0.2760(4) 0.0394(14) Uani 1 1 d . . . . .
N3 N 0.4996(7) 0.6650(5) 0.2198(4) 0.0451(15) Uani 1 1 d . . . . .
N4 N 0.3498(6) 0.7825(5) 0.3342(4) 0.0416(15) Uani 1 1 d . . . . .
O1 O 0.4909(6) 0.6183(4) 0.3823(3) 0.0583(15) Uani 1 1 d . . . . .
N2 N 0.5043(6) 0.7237(4) 0.0541(4) 0.0367(14) Uani 1 1 d . . . . .
N5 N 0.3706(6) 0.8415(5) 0.1658(4) 0.0416(15) Uani 1 1 d . . . . .
C11 C 0.3218(7) 0.8525(6) 0.2602(5) 0.0399(18) Uani 1 1 d . . . . .
C13 C 0.4573(8) 0.7420(6) 0.1554(5) 0.0413(18) Uani 1 1 d . . . . .
C9 C 0.1439(8) 1.0152(5) 0.2012(5) 0.0407(18) Uani 1 1 d . . . . .
H9 H 0.152838 0.989323 0.138196 0.049 Uiso 1 1 calc R . . . .
C6 C 0.0333(8) 1.1566(6) 0.3108(5) 0.0448(19) Uani 1 1 d . . . . .
C7 C 0.1172(8) 1.0928(6) 0.3869(5) 0.0437(18) Uani 1 1 d . . . . .
H7 H 0.109100 1.118407 0.449992 0.052 Uiso 1 1 calc R . . . .
C16 C 0.6296(9) 0.6030(6) -0.0628(6) 0.056(2) Uani 1 1 d . . . . .
H16 H 0.684589 0.533940 -0.076358 0.068 Uiso 1 1 calc R . . . .
C8 C 0.2116(8) 0.9926(6) 0.3705(5) 0.0429(18) Uani 1 1 d . . . . .
H8 H 0.266158 0.951333 0.421673 0.052 Uiso 1 1 calc R . . . .
C10 C 0.0528(8) 1.1119(6) 0.2181(5) 0.0478(19) Uani 1 1 d . . . . .
H10 H -0.000239 1.151354 0.165506 0.057 Uiso 1 1 calc R . . . .
C19 C 0.6374(8) 0.6559(6) -0.2423(5) 0.0433(18) Uani 1 1 d . . . . .
N7 N -0.2802(7) 1.4478(5) 0.3603(5) 0.0520(16) Uani 1 1 d . . . . .
C3 C -0.1493(9) 1.2775(7) 0.4195(5) 0.052(2) Uani 1 1 d . . . . .
H3 H -0.128620 1.226974 0.472081 0.063 Uiso 1 1 calc R . . . .
C18 C 0.5893(8) 0.6799(6) -0.1378(5) 0.0419(18) Uani 1 1 d . . . . .
N1 N 0.7319(10) 0.6201(8) -0.4358(5) 0.077(2) Uani 1 1 d . . . . .
C5 C -0.0731(7) 1.2571(5) 0.3304(5) 0.0341(16) Uani 1 1 d . . . . .
C17 C 0.5050(12) 0.7803(7) -0.1136(5) 0.076(3) Uani 1 1 d . . . . .
H17 H 0.473931 0.834624 -0.161990 0.091 Uiso 1 1 calc R . . . .
C15 C 0.5894(9) 0.6274(6) 0.0312(5) 0.055(2) Uani 1 1 d . . . . .
H15 H 0.622163 0.575464 0.081216 0.066 Uiso 1 1 calc R . . . .
C4 C -0.1042(9) 1.3424(6) 0.2589(6) 0.058(2) Uani 1 1 d . . . . .
H4 H -0.052708 1.334384 0.198596 0.070 Uiso 1 1 calc R . . . .
C14 C 0.4671(12) 0.7992(7) -0.0155(6) 0.080(3) Uani 1 1 d . . . . .
H14 H 0.413582 0.867710 0.000932 0.095 Uiso 1 1 calc R . . . .
C1 C -0.2549(9) 1.3720(6) 0.4297(6) 0.054(2) Uani 1 1 d . . . . .
H1 H -0.310420 1.382383 0.488442 0.065 Uiso 1 1 calc R . . . .
C20 C 0.5705(9) 0.7258(6) -0.3204(6) 0.055(2) Uani 1 1 d . . . . .
H20 H 0.492192 0.785696 -0.309143 0.066 Uiso 1 1 calc R . . . .
C23 C 0.7511(10) 0.5690(7) -0.2661(6) 0.067(2) Uani 1 1 d . . . . .
H23 H 0.798334 0.520157 -0.217129 0.081 Uiso 1 1 calc R . . . .
C2 C -0.2063(11) 1.4359(7) 0.2743(6) 0.068(2) Uani 1 1 d . . . . .
H2 H -0.224656 1.491199 0.225327 0.081 Uiso 1 1 calc R . . . .
C21 C 0.6242(12) 0.7031(8) -0.4141(6) 0.071(3) Uani 1 1 d . . . . .
H21 H 0.580558 0.750096 -0.465325 0.085 Uiso 1 1 calc R . . . .
C22 C 0.7942(11) 0.5547(8) -0.3612(8) 0.079(3) Uani 1 1 d . . . . .
H22 H 0.872211 0.495578 -0.375188 0.095 Uiso 1 1 calc R . . . .
C25 C 0.4498(8) 0.6840(6) 0.3176(6) 0.0448(18) Uani 1 1 d . . . . .
O0AA O 0.0913(10) 0.3586(7) 0.6198(6) 0.130(3) Uani 1 1 d . . . . .
O2 O 0.280(2) 0.0360(10) 0.9611(9) 0.249(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 F6 1.589(5) . ?
P1 F3 1.573(6) . ?
P1 F2 1.572(6) . ?
P1 F5 1.565(6) . ?
P1 F4 1.571(6) . ?
P1 F1 1.560(6) . ?
P2 F10 1.444(9) . ?
P2 F8 1.548(7) . ?
P2 F12 1.496(7) . ?
P2 F7 1.539(8) . ?
P2 F9 1.484(10) . ?
P2 F11 1.422(9) . ?
N6 C11 1.435(9) . ?
N6 C9 1.351(8) . ?
N6 C8 1.386(9) . ?
N3 C13 1.276(8) . ?
N3 C25 1.414(9) . ?
N4 C11 1.299(8) . ?
N4 C25 1.393(9) . ?
O1 C25 1.188(8) . ?
N2 C13 1.452(8) . ?
N2 C15 1.336(9) . ?
N2 C14 1.306(10) . ?
N5 C11 1.354(8) . ?
N5 C13 1.341(9) . ?
C9 C10 1.342(9) . ?
C6 C7 1.406(10) . ?
C6 C10 1.401(10) . ?
C6 C5 1.447(10) . ?
C7 C8 1.388(10) . ?
C16 C18 1.373(10) . ?
C16 C15 1.358(10) . ?
C19 C18 1.508(9) . ?
C19 C20 1.408(10) . ?
C19 C23 1.372(10) . ?
N7 C1 1.299(9) . ?
N7 C2 1.329(9) . ?
C3 C5 1.386(9) . ?
C3 C1 1.365(11) . ?
C18 C17 1.381(10) . ?
N1 C21 1.302(12) . ?
N1 C22 1.331(12) . ?
C5 C4 1.400(10) . ?
C17 C14 1.394(11) . ?
C4 C2 1.353(10) . ?
C20 C21 1.378(11) . ?
C23 C22 1.357(12) . ?

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
F3 P1 F6 88.5(3) . . ?
F2 P1 F6 91.2(3) . . ?
F2 P1 F3 177.9(4) . . ?
F5 P1 F6 179.5(4) . . ?
F5 P1 F3 91.5(3) . . ?
F5 P1 F2 88.8(4) . . ?
F5 P1 F4 90.2(4) . . ?
F4 P1 F6 90.3(3) . . ?
F4 P1 F3 87.5(4) . . ?
F4 P1 F2 90.4(4) . . ?
F1 P1 F6 88.1(4) . . ?
F1 P1 F3 94.6(4) . . ?
F1 P1 F2 87.4(4) . . ?
F1 P1 F5 91.4(4) . . ?
F1 P1 F4 177.3(5) . . ?
F10 P2 F8 88.7(6) . . ?
F10 P2 F12 171.0(10) . . ?
F10 P2 F7 91.6(6) . . ?
F10 P2 F9 83.6(10) . . ?
F12 P2 F8 92.6(4) . . ?
F12 P2 F7 87.3(5) . . ?
F7 P2 F8 179.0(7) . . ?
F9 P2 F8 76.4(7) . . ?
F9 P2 F12 88.0(7) . . ?
F9 P2 F7 104.6(8) . . ?
F11 P2 F10 77.5(14) . . ?
F11 P2 F8 91.3(6) . . ?
F11 P2 F12 111.3(13) . . ?
F11 P2 F7 87.8(6) . . ?
F11 P2 F9 157.8(12) . . ?
C9 N6 C11 121.1(6) . . ?
C9 N6 C8 121.2(6) . . ?
C8 N6 C11 117.6(6) . . ?
C13 N3 C25 117.4(6) . . ?
C11 N4 C25 117.1(6) . . ?
C15 N2 C13 119.4(6) . . ?
C14 N2 C13 121.8(6) . . ?
C14 N2 C15 118.8(6) . . ?
C13 N5 C11 109.9(6) . . ?
N4 C11 N6 118.2(6) . . ?
N4 C11 N5 128.8(6) . . ?
N5 C11 N6 113.0(6) . . ?
N3 C13 N2 118.5(6) . . ?
N3 C13 N5 129.5(6) . . ?
N5 C13 N2 112.0(6) . . ?
C10 C9 N6 119.8(7) . . ?
C7 C6 C5 121.1(7) . . ?
C10 C6 C7 115.2(7) . . ?
C10 C6 C5 123.6(7) . . ?
C8 C7 C6 121.9(7) . . ?
C15 C16 C18 120.3(7) . . ?
N6 C8 C7 118.3(6) . . ?
C9 C10 C6 123.6(7) . . ?
C20 C19 C18 120.5(7) . . ?
C23 C19 C18 122.6(7) . . ?
C23 C19 C20 116.8(7) . . ?
C1 N7 C2 121.3(7) . . ?
C1 C3 C5 119.8(7) . . ?
C16 C18 C19 121.2(6) . . ?
C16 C18 C17 117.3(7) . . ?
C17 C18 C19 121.5(7) . . ?
C21 N1 C22 116.7(7) . . ?
C3 C5 C6 123.8(7) . . ?
C3 C5 C4 115.1(6) . . ?
C4 C5 C6 121.1(6) . . ?
C18 C17 C14 119.1(8) . . ?
N2 C15 C16 122.2(7) . . ?
C2 C4 C5 122.4(7) . . ?
N2 C14 C17 122.1(8) . . ?
N7 C1 C3 122.2(7) . . ?
C21 C20 C19 118.2(8) . . ?
C22 C23 C19 119.7(9) . . ?
N7 C2 C4 119.1(8) . . ?
N1 C21 C20 124.4(8) . . ?
N1 C22 C23 124.1(9) . . ?
N4 C25 N3 116.9(7) . . ?
O1 C25 N3 121.2(6) . . ?
O1 C25 N4 121.8(6) . . ?

_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_compound12+
_audit_block_doi                 10.5517/ccdc.csd.cc23w6bk
_database_code_depnum_ccdc_archive 'CCDC 1962558'
loop_
_audit_author_name
_audit_author_address
'Vedichi Madhu'
;Department of Chemistry, Karunya University
India
;
_audit_update_record             
;
2020-05-26 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;
_audit_creation_date             2020-05-18
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 P, C23 H16 N7 O'
_chemical_formula_sum            'C23 H16 F6 N7 O P'
_chemical_formula_weight         551.40
_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'
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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   5.036(2)
_cell_length_b                   19.412(9)
_cell_length_c                   23.741(10)
_cell_angle_alpha                90
_cell_angle_beta                 87.874(10)
_cell_angle_gamma                90
_cell_volume                     2319.2(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1711
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      2.27
_cell_measurement_theta_min      27.94
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1317
_diffrn_reflns_av_unetI/netI     0.1288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14864
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.355
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_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                2007
_reflns_number_total             4044
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4044
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1620
_refine_ls_R_factor_gt           0.0683
_refine_ls_restrained_S_all      0.972
_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)+(0.0697P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1747
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C6(H6), C4(H4), C16(H16), C11(H11), C14(H14), C15(H15),
 C22(H22), C18(H18), C20(H20), C12(H12), C13(H13), C21(H21), C10(H10), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
P1 P 0.3005(2) 0.68791(7) 0.29784(7) 0.0573(5) Uani 1 1 d . . . . .
F1 F 0.1888(5) 0.62577(14) 0.33532(15) 0.0888(11) Uani 1 1 d . . . . .
F3 F 0.4603(7) 0.63556(15) 0.26020(17) 0.1086(13) Uani 1 1 d . . . . .
F4 F 0.4154(6) 0.74976(15) 0.26189(16) 0.0991(12) Uani 1 1 d . . . . .
F6 F 0.1352(7) 0.73961(15) 0.33630(17) 0.1061(13) Uani 1 1 d . . . . .
F2 F 0.5420(6) 0.69367(19) 0.33658(19) 0.1170(14) Uani 1 1 d . . . . .
F5 F 0.0600(6) 0.6804(2) 0.25990(19) 0.1279(15) Uani 1 1 d . . . . .
N4 N 0.4591(6) 0.09452(16) 0.05095(15) 0.0378(9) Uani 1 1 d . . . . .
N2 N 0.7315(6) 0.00009(18) 0.06884(16) 0.0439(10) Uani 1 1 d . . . . .
O1 O 0.9801(5) -0.09367(15) 0.09162(14) 0.0555(9) Uani 1 1 d . . . . .
N6 N 0.2578(6) -0.03931(17) 0.20850(16) 0.0413(10) Uani 1 1 d . . . . .
N3 N 0.3607(6) 0.02671(17) 0.12970(16) 0.0407(10) Uani 1 1 d . . . . .
N1 N 0.6280(6) -0.06959(17) 0.15108(16) 0.0487(11) Uani 1 1 d . . . . .
C2 C 0.5274(8) 0.03515(19) 0.08569(19) 0.0373(11) Uani 1 1 d . . . . .
C7 C 0.5376(8) 0.1653(2) -0.0284(2) 0.0457(13) Uani 1 1 d . . . . .
H7 H 0.640320 0.175538 -0.060720 0.055 Uiso 1 1 calc R . . . .
C8 C 0.3205(8) 0.2064(2) -0.0140(2) 0.0442(12) Uani 1 1 d . . . . .
C5 C 0.2495(8) 0.1343(2) 0.0672(2) 0.0464(13) Uani 1 1 d . . . . .
H5 H 0.151605 0.123751 0.100044 0.056 Uiso 1 1 calc R . . . .
C9 C 0.2357(9) 0.2641(2) -0.0492(2) 0.0497(13) Uani 1 1 d . . . . .
C17 C -0.0886(8) -0.0603(2) 0.2998(2) 0.0437(12) Uani 1 1 d . . . . .
C3 C 0.4320(8) -0.0275(2) 0.1590(2) 0.0400(12) Uani 1 1 d . . . . .
C1 C 0.7899(8) -0.0563(2) 0.1032(2) 0.0438(12) Uani 1 1 d . . . . .
C6 C 0.1812(8) 0.1895(2) 0.0359(2) 0.0480(13) Uani 1 1 d . . . . .
H6 H 0.038015 0.216658 0.047922 0.058 Uiso 1 1 calc R . . . .
C4 C 0.6034(8) 0.1100(2) 0.0039(2) 0.0426(12) Uani 1 1 d . . . . .
H4 H 0.748905 0.082826 -0.006794 0.051 Uiso 1 1 calc R . . . .
C16 C -0.0339(8) 0.0049(2) 0.2792(2) 0.0545(14) Uani 1 1 d . . . . .
H16 H -0.112695 0.043023 0.296660 0.065 Uiso 1 1 calc R . . . .
C11 C 0.0864(9) 0.3179(2) -0.0268(2) 0.0664(16) Uani 1 1 d . . . . .
H11 H 0.044283 0.319471 0.011687 0.080 Uiso 1 1 calc R . . . .
C14 C 0.2149(10) -0.1026(2) 0.2278(2) 0.0686(17) Uani 1 1 d . . . . .
H14 H 0.303512 -0.139468 0.210657 0.082 Uiso 1 1 calc R . . . .
C15 C 0.1355(8) 0.0140(2) 0.2332(2) 0.0498(13) Uani 1 1 d . . . . .
H15 H 0.165218 0.058092 0.219091 0.060 Uiso 1 1 calc R . . . .
C19 C -0.2789(8) -0.0716(2) 0.3476(2) 0.0478(13) Uani 1 1 d . . . . .
N7 N -0.6457(9) -0.0924(3) 0.4376(2) 0.0886(17) Uani 1 1 d . . . . .
C22 C -0.5362(11) -0.1432(3) 0.4092(3) 0.085(2) Uani 1 1 d . . . . .
H22 H -0.584089 -0.187734 0.419765 0.102 Uiso 1 1 calc R . . . .
C18 C 0.0419(9) -0.1144(2) 0.2726(2) 0.0658(17) Uani 1 1 d . . . . .
H18 H 0.011636 -0.159259 0.284990 0.079 Uiso 1 1 calc R . . . .
N5 N 0.0526(11) 0.3716(2) -0.1166(2) 0.0958(18) Uani 1 1 d . . . . .
C20 C -0.3552(9) -0.1358(3) 0.3647(2) 0.0666(16) Uani 1 1 d . . . . .
H20 H -0.285518 -0.174433 0.346336 0.080 Uiso 1 1 calc R . . . .
C12 C 0.0005(12) 0.3690(3) -0.0618(3) 0.090(2) Uani 1 1 d . . . . .
H12 H -0.101670 0.404282 -0.045702 0.108 Uiso 1 1 calc R . . . .
C13 C 0.1976(13) 0.3201(3) -0.1377(3) 0.103(2) Uani 1 1 d . . . . .
H13 H 0.240782 0.320395 -0.176117 0.123 Uiso 1 1 calc R . . . .
C21 C -0.3931(11) -0.0179(3) 0.3775(3) 0.089(2) Uani 1 1 d . . . . .
H21 H -0.348715 0.027270 0.368000 0.107 Uiso 1 1 calc R . . . .
C10 C 0.2883(11) 0.2660(3) -0.1060(3) 0.083(2) Uani 1 1 d . . . . .
H10 H 0.385612 0.230678 -0.123392 0.099 Uiso 1 1 calc R . . . .
C23 C -0.5711(13) -0.0306(3) 0.4208(3) 0.111(3) Uani 1 1 d . . . . .
H23 H -0.644993 0.007110 0.439854 0.133 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 F1 1.589(3) . ?
P1 F3 1.558(3) . ?
P1 F4 1.571(3) . ?
P1 F6 1.574(3) . ?
P1 F2 1.556(4) . ?
P1 F5 1.543(4) . ?
N4 C2 1.466(5) . ?
N4 C5 1.353(5) . ?
N4 C4 1.344(5) . ?
N2 C2 1.284(5) . ?
N2 C1 1.404(5) . ?
O1 C1 1.224(4) . ?
N6 C3 1.458(5) . ?
N6 C14 1.326(5) . ?
N6 C15 1.329(5) . ?
N3 C2 1.326(5) . ?
N3 C3 1.319(5) . ?
N1 C3 1.290(5) . ?
N1 C1 1.398(5) . ?
C7 C8 1.386(5) . ?
C7 C4 1.368(6) . ?
C8 C9 1.471(6) . ?
C8 C6 1.392(6) . ?
C5 C6 1.356(6) . ?
C9 C11 1.381(6) . ?
C9 C10 1.366(7) . ?
C17 C16 1.381(6) . ?
C17 C19 1.475(6) . ?
C17 C18 1.384(6) . ?
C16 C15 1.372(6) . ?
C11 C12 1.375(7) . ?
C14 C18 1.370(6) . ?
C19 C20 1.361(6) . ?
C19 C21 1.374(6) . ?
N7 C22 1.305(7) . ?
N7 C23 1.316(6) . ?
C22 C20 1.377(7) . ?
N5 C12 1.319(7) . ?
N5 C13 1.326(6) . ?
C13 C10 1.379(7) . ?
C21 C23 1.362(7) . ?

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
F3 P1 F1 89.45(17) . . ?
F3 P1 F4 90.84(18) . . ?
F3 P1 F6 178.86(19) . . ?
F4 P1 F1 178.7(2) . . ?
F4 P1 F6 90.24(17) . . ?
F6 P1 F1 89.47(18) . . ?
F2 P1 F1 89.5(2) . . ?
F2 P1 F3 89.3(2) . . ?
F2 P1 F4 89.2(2) . . ?
F2 P1 F6 91.1(2) . . ?
F5 P1 F1 89.2(2) . . ?
F5 P1 F3 90.2(2) . . ?
F5 P1 F4 92.1(2) . . ?
F5 P1 F6 89.4(2) . . ?
F5 P1 F2 178.6(2) . . ?
C5 N4 C2 119.1(3) . . ?
C4 N4 C2 120.8(3) . . ?
C4 N4 C5 120.1(4) . . ?
C2 N2 C1 114.5(3) . . ?
C14 N6 C3 120.7(3) . . ?
C14 N6 C15 120.1(4) . . ?
C15 N6 C3 119.2(3) . . ?
C3 N3 C2 109.7(3) . . ?
C3 N1 C1 115.0(4) . . ?
N2 C2 N4 116.3(4) . . ?
N2 C2 N3 131.0(4) . . ?
N3 C2 N4 112.7(3) . . ?
C4 C7 C8 121.2(4) . . ?
C7 C8 C9 122.7(4) . . ?
C7 C8 C6 116.3(4) . . ?
C6 C8 C9 121.0(4) . . ?
N4 C5 C6 120.4(4) . . ?
C11 C9 C8 121.5(5) . . ?
C10 C9 C8 122.2(4) . . ?
C10 C9 C11 116.3(5) . . ?
C16 C17 C19 121.6(4) . . ?
C16 C17 C18 116.4(4) . . ?
C18 C17 C19 122.0(4) . . ?
N3 C3 N6 112.5(3) . . ?
N1 C3 N6 116.9(4) . . ?
N1 C3 N3 130.5(4) . . ?
O1 C1 N2 120.7(4) . . ?
O1 C1 N1 120.1(4) . . ?
N1 C1 N2 119.2(3) . . ?
C5 C6 C8 121.5(4) . . ?
N4 C4 C7 120.5(4) . . ?
C15 C16 C17 120.6(4) . . ?
C12 C11 C9 119.4(5) . . ?
N6 C14 C18 121.0(4) . . ?
N6 C15 C16 121.1(4) . . ?
C20 C19 C17 122.2(4) . . ?
C20 C19 C21 115.7(4) . . ?
C21 C19 C17 122.1(4) . . ?
C22 N7 C23 114.9(5) . . ?
N7 C22 C20 125.0(5) . . ?
C14 C18 C17 120.8(4) . . ?
C12 N5 C13 115.5(5) . . ?
C19 C20 C22 119.7(5) . . ?
N5 C12 C11 124.7(5) . . ?
N5 C13 C10 123.9(6) . . ?
C23 C21 C19 120.2(5) . . ?
C9 C10 C13 120.2(5) . . ?
N7 C23 C21 124.5(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
