# 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_xrout
_database_code_depnum_ccdc_archive 'CCDC 1876401'
loop_
_audit_author_name
_audit_author_address
'Surya Kanta Samanta'
;Indian Institute of Engineering Science and Technology, Shibpur
India
;
_audit_update_record             
;
2018-10-31 deposited with the CCDC.	2019-05-28 downloaded from the CCDC.
;
_audit_creation_date             2018-10-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 F N2'
_chemical_formula_sum            'C13 H9 F N2'
_chemical_formula_weight         212.22
_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'

_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                   11.6177(10)
_cell_length_b                   14.1889(12)
_cell_length_c                   6.2178(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.299(2)
_cell_angle_gamma                90
_cell_volume                     1024.69(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4583
_cell_measurement_temperature    293.0(2)
_cell_measurement_theta_max      23.84
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1639 before and 0.0908 after correction. The Ratio of minimum to maximum transmission is 0.6373. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            16438
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.124
_diffrn_reflns_theta_max         25.124
_diffrn_reflns_theta_min         2.266
_diffrn_ambient_temperature      293.0(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1245
_reflns_number_total             1824
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1824
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.033
_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)+(0.0502P)²+0.2538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1266
_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:
 C6(H6), C13(H13), C9(H9), C1(H1), C10(H10), C12(H12), C4(H4), C3(H3), C2(H2)
;
_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 0.68070(14) 0.64255(11) 0.3070(3) 0.0490(4) Uani 1 1 d . . . . .
N2 N 0.63394(15) 0.59716(12) 0.6386(3) 0.0541(5) Uani 1 1 d . . . . .
F1 F 0.10904(13) 0.61424(13) 0.9072(3) 0.1157(7) Uani 1 1 d . . . . .
C7 C 0.53730(16) 0.62661(12) 0.5270(3) 0.0436(5) Uani 1 1 d . . . . .
C8 C 0.42408(17) 0.62493(13) 0.6252(3) 0.0460(5) Uani 1 1 d . . . . .
C5 C 0.71941(17) 0.60700(14) 0.5041(3) 0.0504(5) Uani 1 1 d . . . . .
C6 C 0.56478(18) 0.65490(13) 0.3237(3) 0.0497(5) Uani 1 1 d . . . . .
H6 H 0.514349 0.677970 0.218029 0.060 Uiso 1 1 calc R . . . .
C13 C 0.4108(2) 0.58391(14) 0.8246(4) 0.0564(6) Uani 1 1 d . . . . .
H13 H 0.474952 0.558675 0.895887 0.068 Uiso 1 1 calc R . . . .
C9 C 0.32761(18) 0.66336(15) 0.5241(4) 0.0578(6) Uani 1 1 d . . . . .
H9 H 0.334581 0.691664 0.390121 0.069 Uiso 1 1 calc R . . . .
C1 C 0.7531(2) 0.65900(15) 0.1405(4) 0.0642(6) Uani 1 1 d . . . . .
H1 H 0.724437 0.682123 0.009934 0.077 Uiso 1 1 calc R . . . .
C10 C 0.2218(2) 0.66043(17) 0.6180(4) 0.0700(7) Uani 1 1 d . . . . .
H10 H 0.157467 0.686760 0.549605 0.084 Uiso 1 1 calc R . . . .
C12 C 0.3056(2) 0.57926(16) 0.9209(4) 0.0694(7) Uani 1 1 d . . . . .
H12 H 0.297716 0.550689 1.054332 0.083 Uiso 1 1 calc R . . . .
C4 C 0.8383(2) 0.58884(17) 0.5284(4) 0.0687(7) Uani 1 1 d . . . . .
H4 H 0.867897 0.564837 0.657409 0.082 Uiso 1 1 calc R . . . .
C11 C 0.2133(2) 0.61790(18) 0.8143(5) 0.0728(7) Uani 1 1 d . . . . .
C3 C 0.9088(2) 0.60640(18) 0.3642(5) 0.0774(8) Uani 1 1 d . . . . .
H3 H 0.987296 0.595147 0.381345 0.093 Uiso 1 1 calc R . . . .
C2 C 0.8654(2) 0.64138(18) 0.1680(5) 0.0769(8) Uani 1 1 d . . . . .
H2 H 0.915211 0.652449 0.055814 0.092 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
N1 C5 1.390(3) . ?
N1 C6 1.364(2) . ?
N1 C1 1.368(3) . ?
N2 C7 1.372(2) . ?
N2 C5 1.320(3) . ?
F1 C11 1.355(3) . ?
C7 C8 1.463(3) . ?
C7 C6 1.371(3) . ?
C8 C13 1.382(3) . ?
C8 C9 1.385(3) . ?
C5 C4 1.410(3) . ?
C6 H6 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.374(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.373(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.336(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.367(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.363(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.346(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.400(4) . ?
C2 H2 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
C6 N1 C5 106.23(16) . . ?
C6 N1 C1 131.31(19) . . ?
C1 N1 C5 122.46(18) . . ?
C5 N2 C7 105.41(17) . . ?
N2 C7 C8 121.13(17) . . ?
C6 C7 N2 110.53(18) . . ?
C6 C7 C8 128.33(17) . . ?
C13 C8 C7 120.09(18) . . ?
C13 C8 C9 117.9(2) . . ?
C9 C8 C7 122.02(18) . . ?
N1 C5 C4 117.2(2) . . ?
N2 C5 N1 111.35(17) . . ?
N2 C5 C4 131.4(2) . . ?
N1 C6 C7 106.48(17) . . ?
N1 C6 H6 126.8 . . ?
C7 C6 H6 126.8 . . ?
C8 C13 H13 119.0 . . ?
C12 C13 C8 122.0(2) . . ?
C12 C13 H13 119.0 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
N1 C1 H1 120.5 . . ?
C2 C1 N1 119.1(2) . . ?
C2 C1 H1 120.5 . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.4(2) . . ?
C11 C10 H10 120.8 . . ?
C13 C12 H12 121.1 . . ?
C11 C12 C13 117.8(2) . . ?
C11 C12 H12 121.1 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.1 . . ?
F1 C11 C10 118.8(3) . . ?
F1 C11 C12 118.6(3) . . ?
C12 C11 C10 122.7(2) . . ?
C4 C3 H3 119.6 . . ?
C4 C3 C2 120.9(2) . . ?
C2 C3 H3 119.6 . . ?
C1 C2 C3 120.6(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
