# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 
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data_sa3436
_database_code_depnum_ccdc_archive 'CCDC 1448790'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.	2023-04-10 downloaded from the CCDC.
;
_audit_creation_date             2014-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H12 F4 N4 O3'
_chemical_formula_sum            'C19 H12 F4 N4 O3'
_chemical_formula_weight         420.33
_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'

_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                   6.925(3)
_cell_length_b                   27.776(11)
_cell_length_c                   9.963(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.46(3)
_cell_angle_gamma                90
_cell_volume                     1837.8(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4906
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4814
_cell_measurement_theta_min      1.4663
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            "light yellow'"
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14246
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.197
_diffrn_reflns_theta_min         1.466
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             4254
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0213
_diffrn_orient_matrix_UB_12      0.1376
_diffrn_orient_matrix_UB_13      0.0572
_diffrn_orient_matrix_UB_21      0.0356
_diffrn_orient_matrix_UB_22      -0.0052
_diffrn_orient_matrix_UB_23      -0.0007
_diffrn_orient_matrix_UB_31      0.0079
_diffrn_orient_matrix_UB_32      0.0651
_diffrn_orient_matrix_UB_33      -0.0815
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2795
_reflns_number_total             3293
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0869
_refine_ls_restrained_S_all      1.192
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0838P)²+1.6573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2070
_refine_ls_wR_factor_ref         0.2163
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C16(H16), C17(H17)
2.c :
 C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_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
F1 F 0.2742(5) 0.49756(9) 0.9483(3) 0.0803(8) Uani 1 1 d . . . . .
F2 F 0.3986(5) 0.56794(10) 1.1317(3) 0.0799(8) Uani 1 1 d . . . . .
F3 F 0.3618(4) 0.67633(9) 0.7591(3) 0.0736(8) Uani 1 1 d . . . . .
F4 F 0.2458(4) 0.60520(10) 0.5785(3) 0.0771(8) Uani 1 1 d . . . . .
O1 O 0.5466(5) 0.70092(12) 1.0310(4) 0.0816(10) Uani 1 1 d . . . . .
O2 O 0.3741(4) 0.66347(10) 1.1594(3) 0.0616(8) Uani 1 1 d . . . . .
O3 O 0.0133(5) 0.75769(11) 1.4939(3) 0.0652(8) Uani 1 1 d . . . . .
N1 N 0.1307(10) 0.43325(19) 0.6875(7) 0.127(2) Uani 1 1 d . . . . .
N2 N 0.1642(7) 0.47323(19) 0.6804(5) 0.0844(13) Uani 1 1 d . . . . .
N3 N 0.1909(6) 0.51590(16) 0.6489(4) 0.0731(11) Uani 1 1 d . . . . .
N4 N 0.0047(5) 0.73299(12) 1.2789(3) 0.0471(8) Uani 1 1 d . . . . .
C1 C 0.2580(6) 0.54920(15) 0.7572(4) 0.0562(10) Uani 1 1 d . . . . .
C2 C 0.2966(6) 0.54198(14) 0.9004(5) 0.0574(10) Uani 1 1 d . . . . .
C3 C 0.3602(6) 0.57925(16) 0.9943(4) 0.0569(10) Uani 1 1 d . . . . .
C4 C 0.3849(6) 0.62565(14) 0.9534(4) 0.0526(10) Uani 1 1 d . . . . .
C5 C 0.3453(6) 0.63199(15) 0.8113(4) 0.0531(10) Uani 1 1 d . . . . .
C6 C 0.2843(6) 0.59573(15) 0.7160(4) 0.0530(10) Uani 1 1 d . . . . .
C7 C 0.4476(6) 0.66750(16) 1.0522(5) 0.0610(11) Uani 1 1 d . . . . .
C8 C 0.4190(7) 0.70276(16) 1.2601(5) 0.0625(11) Uani 1 1 d . . . . .
H8A H 0.3631 0.7327 1.2155 0.075 Uiso 1 1 calc R . . . .
H8B H 0.5635 0.7066 1.2981 0.075 Uiso 1 1 calc R . . . .
C9 C 0.3260(6) 0.69012(16) 1.3744(4) 0.0602(11) Uani 1 1 d . . . . .
H9A H 0.3653 0.7142 1.4477 0.072 Uiso 1 1 calc R . . . .
H9B H 0.3799 0.6594 1.4145 0.072 Uiso 1 1 calc R . . . .
C10 C 0.0979(6) 0.68683(15) 1.3273(4) 0.0530(10) Uani 1 1 d . . . . .
H10A H 0.0571 0.6635 1.2522 0.064 Uiso 1 1 calc R . . . .
H10B H 0.0507 0.6756 1.4046 0.064 Uiso 1 1 calc R . . . .
C11 C -0.0268(5) 0.76598(14) 1.3663(4) 0.0461(9) Uani 1 1 d . . . . .
C12 C -0.1061(5) 0.81415(14) 1.3103(3) 0.0433(8) Uani 1 1 d . . . . .
C13 C -0.1088(5) 0.85033(15) 1.4064(4) 0.0515(10) Uani 1 1 d . . . . .
H13 H -0.0720 0.8430 1.5013 0.062 Uiso 1 1 calc R . . . .
C14 C -0.1641(6) 0.89643(15) 1.3645(4) 0.0527(10) Uani 1 1 d . . . . .
H14 H -0.1645 0.9199 1.4309 0.063 Uiso 1 1 calc R . . . .
C15 C -0.2198(5) 0.90838(15) 1.2230(4) 0.0520(9) Uani 1 1 d . . . . .
C16 C -0.2227(6) 0.87195(15) 1.1253(4) 0.0546(10) Uani 1 1 d . . . . .
H16 H -0.2630 0.8793 1.0303 0.065 Uiso 1 1 calc R . . . .
C17 C -0.1672(5) 0.82550(14) 1.1671(4) 0.0493(9) Uani 1 1 d . . . . .
H17 H -0.1701 0.8017 1.1008 0.059 Uiso 1 1 calc R . . . .
C18 C -0.2737(6) 0.95699(18) 1.1777(4) 0.0609(11) Uani 1 1 d . . . . .
C19 C -0.3115(8) 0.99763(18) 1.1441(5) 0.0708(13) Uani 1 1 d . . . . .
H19 H -0.3411 1.0295 1.1177 0.085 Uiso 1 1 calc R . . . .
H4 H -0.014(6) 0.7392(14) 1.204(4) 0.044(11) Uiso 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
F1 C2 1.348(5) . ?
F2 C3 1.355(5) . ?
F3 C5 1.354(5) . ?
F4 C6 1.345(5) . ?
O1 C7 1.208(5) . ?
O2 C7 1.311(5) . ?
O2 C8 1.455(5) . ?
O3 C11 1.244(4) . ?
N1 N2 1.141(6) . ?
N2 N3 1.253(6) . ?
N3 C1 1.397(6) . ?
N4 C10 1.455(5) . ?
N4 C11 1.324(5) . ?
C1 C2 1.390(6) . ?
C1 C6 1.384(6) . ?
C2 C3 1.381(6) . ?
C3 C4 1.377(6) . ?
C4 C5 1.375(6) . ?
C4 C7 1.506(6) . ?
C5 C6 1.366(6) . ?
C8 C9 1.500(6) . ?
C9 C10 1.518(6) . ?
C11 C12 1.493(5) . ?
C12 C13 1.391(5) . ?
C12 C17 1.404(5) . ?
C13 C14 1.368(6) . ?
C14 C15 1.392(5) . ?
C15 C16 1.400(6) . ?
C15 C18 1.439(6) . ?
C16 C17 1.377(6) . ?
C18 C19 1.185(6) . ?

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
C7 O2 C8 116.2(3) . . ?
N1 N2 N3 169.5(6) . . ?
N2 N3 C1 118.2(4) . . ?
C11 N4 C10 122.2(3) . . ?
C2 C1 N3 128.5(4) . . ?
C6 C1 N3 115.6(4) . . ?
C6 C1 C2 115.9(4) . . ?
F1 C2 C1 119.2(4) . . ?
F1 C2 C3 119.5(4) . . ?
C3 C2 C1 121.3(4) . . ?
F2 C3 C2 116.3(4) . . ?
F2 C3 C4 120.7(4) . . ?
C4 C3 C2 122.9(4) . . ?
C3 C4 C7 124.4(4) . . ?
C5 C4 C3 114.8(4) . . ?
C5 C4 C7 120.7(4) . . ?
F3 C5 C4 119.9(4) . . ?
F3 C5 C6 116.5(4) . . ?
C6 C5 C4 123.6(4) . . ?
F4 C6 C1 118.7(4) . . ?
F4 C6 C5 119.8(4) . . ?
C5 C6 C1 121.6(4) . . ?
O1 C7 O2 125.4(4) . . ?
O1 C7 C4 123.5(4) . . ?
O2 C7 C4 111.1(4) . . ?
O2 C8 C9 107.1(3) . . ?
C8 C9 C10 114.3(3) . . ?
N4 C10 C9 112.0(3) . . ?
O3 C11 N4 120.9(4) . . ?
O3 C11 C12 120.0(3) . . ?
N4 C11 C12 119.1(3) . . ?
C13 C12 C11 117.7(3) . . ?
C13 C12 C17 118.5(4) . . ?
C17 C12 C11 123.6(3) . . ?
C14 C13 C12 121.6(4) . . ?
C13 C14 C15 120.4(4) . . ?
C14 C15 C16 118.5(4) . . ?
C14 C15 C18 120.9(4) . . ?
C16 C15 C18 120.6(4) . . ?
C17 C16 C15 121.3(4) . . ?
C16 C17 C12 119.7(4) . . ?
C19 C18 C15 177.4(5) . . ?

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
N4 H4 O3 0.74(4) 2.16(4) 2.869(4) 162(4) 4_575

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
F1 C2 C3 F2 0.7(6) . . . . ?
F1 C2 C3 C4 -179.4(4) . . . . ?
F2 C3 C4 C5 178.6(3) . . . . ?
F2 C3 C4 C7 -2.2(6) . . . . ?
F3 C5 C6 F4 0.5(5) . . . . ?
F3 C5 C6 C1 -178.5(3) . . . . ?
O2 C8 C9 C10 -64.1(5) . . . . ?
O3 C11 C12 C13 7.9(5) . . . . ?
O3 C11 C12 C17 -175.8(3) . . . . ?
N1 N2 N3 C1 179(3) . . . . ?
N2 N3 C1 C2 -1.7(7) . . . . ?
N2 N3 C1 C6 -179.9(4) . . . . ?
N3 C1 C2 F1 1.8(6) . . . . ?
N3 C1 C2 C3 -179.1(4) . . . . ?
N3 C1 C6 F4 -0.4(5) . . . . ?
N3 C1 C6 C5 178.6(4) . . . . ?
N4 C11 C12 C13 -170.4(3) . . . . ?
N4 C11 C12 C17 5.9(5) . . . . ?
C1 C2 C3 F2 -178.3(3) . . . . ?
C1 C2 C3 C4 1.5(6) . . . . ?
C2 C1 C6 F4 -178.9(3) . . . . ?
C2 C1 C6 C5 0.2(6) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
C2 C3 C4 C7 178.0(4) . . . . ?
C3 C4 C5 F3 179.0(3) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C3 C4 C7 O1 148.1(5) . . . . ?
C3 C4 C7 O2 -34.4(5) . . . . ?
C4 C5 C6 F4 179.0(3) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C5 C4 C7 O1 -32.8(6) . . . . ?
C5 C4 C7 O2 144.8(4) . . . . ?
C6 C1 C2 F1 -180.0(3) . . . . ?
C6 C1 C2 C3 -0.9(6) . . . . ?
C7 O2 C8 C9 -178.5(4) . . . . ?
C7 C4 C5 F3 -0.3(5) . . . . ?
C7 C4 C5 C6 -178.7(3) . . . . ?
C8 O2 C7 O1 -0.5(7) . . . . ?
C8 O2 C7 C4 -178.0(3) . . . . ?
C8 C9 C10 N4 -64.3(5) . . . . ?
C10 N4 C11 O3 -3.8(5) . . . . ?
C10 N4 C11 C12 174.5(3) . . . . ?
C11 N4 C10 C9 -83.1(4) . . . . ?
C11 C12 C13 C14 174.8(3) . . . . ?
C11 C12 C17 C16 -174.6(3) . . . . ?
C12 C13 C14 C15 0.0(6) . . . . ?
C13 C12 C17 C16 1.7(5) . . . . ?
C13 C14 C15 C16 1.6(5) . . . . ?
C13 C14 C15 C18 -178.5(4) . . . . ?
C14 C15 C16 C17 -1.6(6) . . . . ?
C15 C16 C17 C12 0.0(6) . . . . ?
C17 C12 C13 C14 -1.7(5) . . . . ?
C18 C15 C16 C17 178.5(4) . . . . ?

