# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_E-ARF2
_database_code_depnum_ccdc_archive 'CCDC 2075638'
loop_
_audit_author_name
_audit_author_address
'Manas Panda'
;Jadavpur University, Department of Chemistry
India
;
_audit_update_record             
;
2021-04-06 deposited with the CCDC.	2021-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        E-ArF2
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 F2 N2 O'
_chemical_formula_weight         298.29

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   3.8711(3)
_cell_length_b                   11.1490(10)
_cell_length_c                   32.557(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1405.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9997
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      26.94

_exptl_crystal_description       Acicular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'multi scan'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48393
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.931
_diffrn_reflns_theta_max         26.989
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3029
_reflns_number_gt                2945
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.997

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0788P)²+0.2887P] 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_abs_structure_details 
;
 Flack x determined using 1125 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.24(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3029
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1410
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_restrained_S_all      1.196
_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
F2 F -0.0300(7) 0.27257(19) 0.46568(6) 0.0749(7) Uani 1 1 d . . . . .
F1 F 0.3301(9) 0.6461(2) 0.51358(6) 0.0873(9) Uani 1 1 d . . . . .
O2 O 0.8084(10) 0.6821(2) 0.15187(7) 0.0745(9) Uani 1 1 d . . . . .
N1 N 0.9558(7) 0.49546(19) 0.17322(7) 0.0431(5) Uani 1 1 d . . . . .
H1 H 1.0501 0.4301 0.1648 0.052 Uiso 1 1 calc R U . . .
N2 N 0.6548(12) 0.7693(3) 0.35770(9) 0.0759(11) Uani 1 1 d . . . . .
C1 C 1.0718(13) 0.5517(3) 0.10307(9) 0.0708(11) Uani 1 1 d . . . . .
H1A H 0.8893 0.5554 0.0832 0.106 Uiso 1 1 calc R U . . .
H1B H 1.1648 0.4720 0.1039 0.106 Uiso 1 1 calc R U . . .
H1C H 1.2508 0.6073 0.0956 0.106 Uiso 1 1 calc R U . . .
C2 C 0.9315(9) 0.5841(3) 0.14478(8) 0.0496(7) Uani 1 1 d . . . . .
C3 C 0.8484(6) 0.4956(2) 0.21446(7) 0.0345(5) Uani 1 1 d . . . . .
C4 C 0.6829(7) 0.5924(2) 0.23321(7) 0.0376(5) Uani 1 1 d . . . . .
H4 H 0.6377 0.6618 0.2183 0.045 Uiso 1 1 calc R U . . .
C5 C 0.5866(7) 0.5846(2) 0.27400(8) 0.0369(5) Uani 1 1 d . . . . .
H5 H 0.4768 0.6496 0.2863 0.044 Uiso 1 1 calc R U . . .
C6 C 0.6498(6) 0.4815(2) 0.29734(8) 0.0355(5) Uani 1 1 d . . . . .
C7 C 0.5448(7) 0.4662(2) 0.33992(8) 0.0383(5) Uani 1 1 d . . . . .
H7 H 0.5081 0.3871 0.3479 0.046 Uiso 1 1 calc R U . . .
C8 C 0.4923(7) 0.5485(2) 0.36961(7) 0.0360(5) Uani 1 1 d . . . . .
C9 C 0.3691(6) 0.5190(2) 0.41161(7) 0.0365(5) Uani 1 1 d . . . . .
C10 C 0.2213(7) 0.4070(2) 0.41914(8) 0.0422(6) Uani 1 1 d . . . . .
H10 H 0.1954 0.3513 0.3981 0.051 Uiso 1 1 calc R U . . .
C11 C 0.1144(8) 0.3807(3) 0.45852(8) 0.0473(7) Uani 1 1 d . . . . .
C12 C 0.1454(9) 0.4582(3) 0.49085(8) 0.0521(7) Uani 1 1 d . . . . .
H12 H 0.0731 0.4378 0.5172 0.062 Uiso 1 1 calc R U . . .
C13 C 0.5782(9) 0.6721(3) 0.36228(8) 0.0482(7) Uani 1 1 d . . . . .
C14 C 0.4008(8) 0.6008(3) 0.44353(8) 0.0458(6) Uani 1 1 d . . . . .
H14 H 0.4953 0.6764 0.4390 0.055 Uiso 1 1 calc R U . . .
C15 C 0.2887(10) 0.5673(3) 0.48222(8) 0.0528(7) Uani 1 1 d . . . . .
C16 C 0.8099(7) 0.3847(2) 0.27768(8) 0.0385(5) Uani 1 1 d . . . . .
H16 H 0.8498 0.3144 0.2923 0.046 Uiso 1 1 calc R U . . .
C17 C 0.9095(7) 0.3916(2) 0.23714(8) 0.0394(6) Uani 1 1 d . . . . .
H17 H 1.0181 0.3265 0.2248 0.047 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
F2 C11 1.349(4) . ?
F1 C15 1.356(3) . ?
O2 C2 1.214(4) . ?
N1 C2 1.358(3) . ?
N1 C3 1.405(3) . ?
N1 H1 0.8600 . ?
N2 C13 1.134(4) . ?
C1 C2 1.507(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 C17 1.395(3) . ?
C3 C4 1.396(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9300 . ?
C6 C16 1.399(3) . ?
C6 C7 1.455(3) . ?
C7 C8 1.349(4) . ?
C7 H7 0.9300 . ?
C8 C13 1.437(4) . ?
C8 C9 1.485(3) . ?
C9 C14 1.388(4) . ?
C9 C10 1.395(4) . ?
C10 C11 1.379(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(4) . ?
C12 C15 1.366(5) . ?
C12 H12 0.9300 . ?
C14 C15 1.384(4) . ?
C14 H14 0.9300 . ?
C16 C17 1.377(4) . ?
C16 H16 0.9300 . ?
C17 H17 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
C2 N1 C3 129.1(2) . . ?
C2 N1 H1 115.5 . . ?
C3 N1 H1 115.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 N1 123.6(3) . . ?
O2 C2 C1 121.9(3) . . ?
N1 C2 C1 114.5(3) . . ?
C17 C3 C4 119.3(2) . . ?
C17 C3 N1 117.1(2) . . ?
C4 C3 N1 123.7(2) . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C16 117.5(2) . . ?
C5 C6 C7 124.4(2) . . ?
C16 C6 C7 118.0(2) . . ?
C8 C7 C6 130.2(2) . . ?
C8 C7 H7 114.9 . . ?
C6 C7 H7 114.9 . . ?
C7 C8 C13 119.9(2) . . ?
C7 C8 C9 123.8(2) . . ?
C13 C8 C9 116.1(2) . . ?
C14 C9 C10 119.5(2) . . ?
C14 C9 C8 121.0(2) . . ?
C10 C9 C8 119.5(2) . . ?
C11 C10 C9 118.4(3) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
F2 C11 C12 117.9(2) . . ?
F2 C11 C10 118.3(3) . . ?
C12 C11 C10 123.8(3) . . ?
C15 C12 C11 116.1(2) . . ?
C15 C12 H12 122.0 . . ?
C11 C12 H12 122.0 . . ?
N2 C13 C8 177.4(4) . . ?
C15 C14 C9 118.4(3) . . ?
C15 C14 H14 120.8 . . ?
C9 C14 H14 120.8 . . ?
F1 C15 C12 118.0(3) . . ?
F1 C15 C14 118.3(3) . . ?
C12 C15 C14 123.7(3) . . ?
C17 C16 C6 121.3(2) . . ?
C17 C16 H16 119.4 . . ?
C6 C16 H16 119.4 . . ?
C16 C17 C3 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C3 C17 H17 119.8 . . ?

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
C3 N1 C2 O2 0.8(6) . . . . ?
C3 N1 C2 C1 -179.4(3) . . . . ?
C2 N1 C3 C17 -179.2(3) . . . . ?
C2 N1 C3 C4 1.6(5) . . . . ?
C17 C3 C4 C5 0.9(4) . . . . ?
N1 C3 C4 C5 -179.9(2) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C16 -1.1(4) . . . . ?
C4 C5 C6 C7 -177.8(3) . . . . ?
C5 C6 C7 C8 -27.2(4) . . . . ?
C16 C6 C7 C8 156.1(3) . . . . ?
C6 C7 C8 C13 -7.0(4) . . . . ?
C6 C7 C8 C9 177.2(3) . . . . ?
C7 C8 C9 C14 163.8(3) . . . . ?
C13 C8 C9 C14 -12.1(4) . . . . ?
C7 C8 C9 C10 -15.8(4) . . . . ?
C13 C8 C9 C10 168.3(3) . . . . ?
C14 C9 C10 C11 -0.8(4) . . . . ?
C8 C9 C10 C11 178.9(3) . . . . ?
C9 C10 C11 F2 179.7(3) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
F2 C11 C12 C15 -179.2(3) . . . . ?
C10 C11 C12 C15 0.6(5) . . . . ?
C10 C9 C14 C15 1.0(4) . . . . ?
C8 C9 C14 C15 -178.6(3) . . . . ?
C11 C12 C15 F1 -178.8(3) . . . . ?
C11 C12 C15 C14 -0.3(5) . . . . ?
C9 C14 C15 F1 178.0(3) . . . . ?
C9 C14 C15 C12 -0.5(5) . . . . ?
C5 C6 C16 C17 1.6(4) . . . . ?
C7 C6 C16 C17 178.5(2) . . . . ?
C6 C16 C17 C3 -0.8(4) . . . . ?
C4 C3 C17 C16 -0.5(4) . . . . ?
N1 C3 C17 C16 -179.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.163



