# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_niper-5
_database_code_depnum_ccdc_archive 'CCDC 1828789'
loop_
_audit_author_name
_audit_author_address
'subash chandra Sahoo'
;Panjab university Chandigarh, Chandigarh
India
;
_audit_update_record             
;
2018-05-12 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;
_audit_creation_date             2018-05-11
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_chemical_formula_moiety         'C15 H11 F2 N5'
_chemical_formula_sum            'C15 H11 F2 N5'
_chemical_compound_source        synthesized
_chemical_formula_weight         299.28
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'
_chemical_absolute_configuration ?
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y,-z
3 -x,-y,-z
4 x-1/2,-y,z
5 x+1/2,y+1/2,z+1/2
6 -x+1,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z+1/2
8 x,-y+1/2,z+1/2
_cell_length_a                   25.282(2)
_cell_length_b                   3.7619(2)
_cell_length_c                   35.085(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.481(7)
_cell_angle_gamma                90
_cell_volume                     3333.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2948
_cell_measurement_theta_max      20.1920
_cell_measurement_theta_min      3.3670
_cell_measurement_temperature    293
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.1925
_exptl_crystal_F_000             1232.6371
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_av_unetI/netI     0.1281
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            19238
_diffrn_reflns_theta_full        27.05
_diffrn_reflns_theta_max         27.052
_diffrn_reflns_theta_min         3.23
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  -8.00   0.50   50.00    --  -10.10 113.00 -83.00   84
  2  ω     25.00  50.00   0.50   50.00    --   10.38-113.00-175.00   50
  3  ω     34.00  59.00   0.50   50.00    --  -10.10  19.00  60.00   50
  4  ω    -22.00   9.00   0.50   50.00    --  -10.10  19.00  90.00   62
  5  ω    -57.00 -31.00   0.50   50.00    --  -10.10 125.00-150.00   52
  6  ω    -18.00  11.00   0.50   50.00    --  -10.10  19.00  60.00   58
  7  ω    -79.00 -19.00   0.50   50.00    --  -10.10 -19.00 -90.00  120
  8  ω     15.00  40.00   0.50   50.00    --  -10.10  19.00  90.00   50
  9  ω    -50.00  16.00   0.50   50.00    --   10.38 -38.00-120.00  132
 10  ω    -12.00  74.00   0.50   50.00    --   10.38  77.00  90.00  172
 11  ω    -29.00  -3.00   0.50   50.00    --   10.38 -38.00  90.00   52
 12  ω    -32.00  -4.00   0.50   50.00    --   10.38 124.00-102.62   56
 13  ω      3.00  57.00   0.50   50.00    --   10.38-125.00 -90.00  108
 14  ω     23.00  56.00   0.50   50.00    --   10.38-125.00  30.00   66
 15  ω      6.00  72.00   0.50   50.00    --   10.38  38.00-180.00  132
 16  ω      6.00  31.00   0.50   50.00    --   10.38  57.00 150.00   50
 17  ω    -18.00  18.00   0.50   50.00    --   10.38 -99.00-150.00   72
 18  ω    -29.00  -4.00   0.50   50.00    --   10.38 127.00 104.87   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              32
_reflns_limit_h_min              0
_reflns_limit_k_max              4
_reflns_limit_k_min              0
_reflns_limit_l_max              44
_reflns_limit_l_min              -44
_reflns_number_gt                1166
_reflns_number_total             3650
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.4869
_refine_diff_density_min         -0.5001
_refine_diff_density_rms         0.1046
_refine_ls_d_res_high            0.7687
_refine_ls_d_res_low             6.3146
_refine_ls_goodness_of_fit_ref   0.9196
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2008
_refine_ls_R_factor_gt           0.0700
_refine_ls_restrained_S_all      0.9196
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0919P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.2208
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00M(H00M)
2.b X=CH2 refined with riding coordinates:
 N00B(H00b,H00c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
F001 F 0.41294(9) 0.7071(6) 0.74640(6) 0.1188(9) Uani 1.000000 .
F002 F 0.78537(9) 0.0097(7) 0.71184(7) 0.1302(10) Uani 1.000000 .
N003 N 0.52864(13) 0.2742(8) 0.59194(10) 0.0762(9) Uani 1.000000 .
N004 N 0.56906(14) 0.2000(7) 0.61915(9) 0.0767(9) Uani 1.000000 .
N005 N 0.44620(13) 0.3310(8) 0.57204(11) 0.0948(10) Uani 1.000000 .
N006 N 0.47592(16) 0.2211(9) 0.54113(9) 0.1042(11) Uani 1.000000 .
C007 C 0.49665(14) 0.6147(9) 0.66719(11) 0.0716(10) Uani 1.000000 .
H007 H 0.53119(14) 0.6666(9) 0.66097(11) 0.0859(12) Uiso 1.000000 R
C008 C 0.46274(15) 0.4550(9) 0.64048(11) 0.0675(10) Uani 1.000000 .
C009 C 0.65969(15) 0.2044(8) 0.63732(12) 0.0693(10) Uani 1.000000 .
C00A C 0.61592(18) 0.2774(9) 0.61060(10) 0.0773(11) Uani 1.000000 .
H00A H 0.62211(18) 0.3811(9) 0.58715(10) 0.0927(13) Uiso 1.000000 R
N00B N 0.56424(13) 0.0491(10) 0.53407(9) 0.1160(12) Uani 1.000000 .
H00b H 0.59465(13) 0.0122(10) 0.54530(9) 0.1392(15) Uiso 1.000000 R
H00c H 0.55926(13) -0.0012(10) 0.51027(9) 0.1392(15) Uiso 1.000000 R
C00C C 0.4289(2) 0.6244(10) 0.71108(12) 0.0829(11) Uani 1.000000 .
C00D C 0.47817(16) 0.3561(9) 0.60205(12) 0.0754(10) Uani 1.000000 .
C00E C 0.47999(17) 0.6977(9) 0.70278(11) 0.0791(11) Uani 1.000000 .
H00E H 0.50305(17) 0.8017(9) 0.72090(11) 0.0949(13) Uiso 1.000000 R
C00F C 0.65208(16) 0.0890(9) 0.67381(12) 0.0780(11) Uani 1.000000 .
H00F H 0.61771(16) 0.0544(9) 0.68149(12) 0.0935(13) Uiso 1.000000 R
C00G C 0.41092(16) 0.3829(9) 0.64974(12) 0.0820(11) Uani 1.000000 .
H00G H 0.38772(16) 0.2764(9) 0.63189(12) 0.0984(13) Uiso 1.000000 R
C00H C 0.39388(16) 0.4696(11) 0.68548(14) 0.0883(12) Uani 1.000000 .
H00H H 0.35926(16) 0.4232(11) 0.69193(14) 0.1060(14) Uiso 1.000000 R
C00I C 0.71108(18) 0.2543(9) 0.62675(12) 0.0867(12) Uani 1.000000 .
H00I H 0.71718(18) 0.3364(9) 0.60233(12) 0.1040(14) Uiso 1.000000 R
C00J C 0.69352(18) 0.0232(10) 0.69924(12) 0.0863(12) Uani 1.000000 .
H00J H 0.68785(18) -0.0533(10) 0.72394(12) 0.1036(14) Uiso 1.000000 R
C00K C 0.52454(19) 0.1850(11) 0.55367(13) 0.0882(12) Uani 1.000000 .
C00L C 0.7435(2) 0.0742(11) 0.68698(16) 0.0939(13) Uani 1.000000 .
C00M C 0.75367(17) 0.1850(11) 0.65163(17) 0.0968(13) Uani 1.000000 .
H00M H 0.78826(17) 0.2141(11) 0.64416(17) 0.1162(15) Uiso 1.000000 R


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
F001 C00C 1.356(4) . ?
F002 C00L 1.364(4) . ?
N003 N004 1.396(4) . ?
N003 C00D 1.374(4) . ?
N003 C00K 1.384(4) . ?
N004 C00A 1.268(4) . ?
N005 N006 1.408(4) . ?
N005 C00D 1.303(4) . ?
N006 C00K 1.295(5) . ?
C007 H007 0.9300 . ?
C007 C008 1.380(4) . ?
C007 C00E 1.371(4) . ?
C008 C00D 1.468(5) . ?
C008 C00G 1.390(4) . ?
C009 C00A 1.445(5) . ?
C009 C00F 1.373(5) . ?
C009 C00I 1.379(5) . ?
C00A H00A 0.9300 . ?
N00B H00b 0.8600 . ?
N00B H00c 0.8600 . ?
N00B C00K 1.342(4) . ?
C00C C00E 1.365(5) . ?
C00C C00H 1.364(5) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00J 1.369(5) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.382(5) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00M 1.381(5) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.366(5) . ?
C00L C00M 1.344(5) . ?
C00M H00M 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
C00D N003 N004 121.9(3) . . ?
C00K N003 N004 129.6(3) . . ?
C00K N003 C00D 105.9(3) . . ?
C00A N004 N003 117.1(3) . . ?
C00D N005 N006 108.1(3) . . ?
C00K N006 N005 107.4(3) . . ?
C008 C007 H007 119.6(2) . . ?
C00E C007 H007 119.6(2) . . ?
C00E C007 C008 120.8(4) . . ?
C00D C008 C007 123.5(4) . . ?
C00G C008 C007 119.4(4) . . ?
C00G C008 C00D 117.1(4) . . ?
C00F C009 C00A 122.1(4) . . ?
C00I C009 C00A 120.2(4) . . ?
C00I C009 C00F 117.7(4) . . ?
C009 C00A N004 120.0(4) . . ?
H00A C00A N004 120.0(2) . . ?
H00A C00A C009 120.0(2) . . ?
H00c N00B H00b 120.0 . . ?
C00K N00B H00b 120.0 . . ?
C00K N00B H00c 120.0 . . ?
C00E C00C F001 118.1(4) . . ?
C00H C00C F001 119.3(4) . . ?
C00H C00C C00E 122.6(4) . . ?
N005 C00D N003 109.0(4) . . ?
C008 C00D N003 125.5(4) . . ?
C008 C00D N005 125.5(4) . . ?
C00C C00E C007 118.6(4) . . ?
H00E C00E C007 120.7(2) . . ?
H00E C00E C00C 120.7(3) . . ?
H00F C00F C009 119.0(2) . . ?
C00J C00F C009 122.0(4) . . ?
C00J C00F H00F 119.0(2) . . ?
H00G C00G C008 120.0(2) . . ?
C00H C00G C008 120.0(4) . . ?
C00H C00G H00G 120.0(3) . . ?
C00G C00H C00C 118.6(4) . . ?
H00H C00H C00C 120.7(3) . . ?
H00H C00H C00G 120.7(3) . . ?
H00I C00I C009 119.3(3) . . ?
C00M C00I C009 121.5(4) . . ?
C00M C00I H00I 119.3(3) . . ?
H00J C00J C00F 121.2(2) . . ?
C00L C00J C00F 117.5(4) . . ?
C00L C00J H00J 121.2(3) . . ?
N006 C00K N003 109.5(4) . . ?
N00B C00K N003 124.3(4) . . ?
N00B C00K N006 125.9(4) . . ?
C00J C00L F002 118.5(5) . . ?
C00M C00L F002 118.1(5) . . ?
C00M C00L C00J 123.4(4) . . ?
C00L C00M C00I 117.8(4) . . ?
H00M C00M C00I 121.1(3) . . ?
H00M C00M C00L 121.1(3) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.250 -0.684 0.000 191.1 18.7 '1 water'
2 0.250 -0.724 0.500 191.1 18.7 '1 water'
3 0.750 -0.340 0.000 191.1 18.7 '1 water'
4 0.750 -0.973 0.500 191.1 18.7 '1 water'


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_recrystallization_method slowevaporation
_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293

