# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_333
_audit_block_doi                 10.5517/ccdc.csd.cc23grx8
_database_code_depnum_ccdc_archive 'CCDC 1950610'
loop_
_audit_author_name
_audit_author_address
'Shengmei Guo'
;anhui university
China
;
_audit_update_record             
;
2019-08-31 deposited with the CCDC.	2020-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 F N3'
_chemical_formula_weight         359.44
_chemical_absolute_configuration ab

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8960(12)
_cell_length_b                   8.9130(18)
_cell_length_c                   36.162(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1900.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5328
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      20.52

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9838
_exptl_absorpt_correction_T_max  0.9854
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26548
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3342
_reflns_number_gt                2653
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0190P)²+1.0336P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0059(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(18)
_refine_ls_number_reflns         3342
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.007
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C12 C 0.0231(5) 0.2570(3) 0.09173(8) 0.0486(7) Uani 1 1 d . . .
C9 C 0.0311(6) 0.1123(3) 0.18052(8) 0.0530(8) Uani 1 1 d . . .
C22 C -0.3702(6) -0.2346(4) 0.04659(8) 0.0584(9) Uani 1 1 d . . .
C8 C 0.1377(5) 0.1105(3) 0.21676(8) 0.0545(8) Uani 1 1 d . . .
C18 C -0.1210(5) -0.1380(3) 0.09174(9) 0.0575(8) Uani 1 1 d . . .
H18 H 0.0188 -0.1394 0.1037 0.069 Uiso 1 1 calc R . .
C20 C -0.4925(5) -0.0369(4) 0.08479(8) 0.0558(8) Uani 1 1 d . . .
H20 H -0.6048 0.0303 0.0920 0.067 Uiso 1 1 calc R . .
C6 C 0.3221(6) 0.2018(4) 0.22544(8) 0.0616(9) Uani 1 1 d . . .
H6 H 0.3819 0.2641 0.2073 0.074 Uiso 1 1 calc R . .
C16 C -0.0715(7) 0.3487(4) 0.03112(9) 0.0693(10) Uani 1 1 d . . .
H16 H -0.1737 0.3539 0.0116 0.083 Uiso 1 1 calc R . .
C19 C -0.2824(5) -0.0346(3) 0.10222(7) 0.0460(7) Uani 1 1 d . . .
C11 C -0.2294(5) 0.0838(3) 0.13062(8) 0.0540(8) Uani 1 1 d . . .
H11 H -0.3548 0.1558 0.1317 0.065 Uiso 1 1 calc R . .
C13 C 0.2262(5) 0.3372(4) 0.08919(9) 0.0613(8) Uani 1 1 d . . .
H13 H 0.3280 0.3359 0.1088 0.074 Uiso 1 1 calc R . .
C7 C 0.0552(6) 0.0190(4) 0.24491(9) 0.0649(9) Uani 1 1 d . . .
H7 H -0.0669 -0.0442 0.2401 0.078 Uiso 1 1 calc R . .
C21 C -0.5352(6) -0.1386(4) 0.05675(9) 0.0619(9) Uani 1 1 d . . .
H21 H -0.6757 -0.1407 0.0451 0.074 Uiso 1 1 calc R . .
C15 C 0.1308(7) 0.4238(4) 0.02867(9) 0.0660(9) Uani 1 1 d . . .
H15 H 0.1682 0.4777 0.0075 0.079 Uiso 1 1 calc R . .
C3 C 0.3329(6) 0.1128(4) 0.28852(9) 0.0642(9) Uani 1 1 d . . .
C23 C -0.1637(6) -0.2395(4) 0.06386(9) 0.0664(9) Uani 1 1 d . . .
H23 H -0.0548 -0.3095 0.0569 0.080 Uiso 1 1 calc R . .
C10 C -0.1796(6) 0.0258(4) 0.16988(8) 0.0616(9) Uani 1 1 d . . .
H10A H -0.3042 0.0475 0.1866 0.074 Uiso 1 1 calc R . .
H10B H -0.1514 -0.0814 0.1698 0.074 Uiso 1 1 calc R . .
C17 C -0.1269(6) 0.2650(4) 0.06226(8) 0.0616(9) Uani 1 1 d . . .
H17 H -0.2646 0.2143 0.0633 0.074 Uiso 1 1 calc R . .
C4 C 0.1506(7) 0.0200(4) 0.27987(9) 0.0724(10) Uani 1 1 d . . .
H4 H 0.0917 -0.0429 0.2980 0.087 Uiso 1 1 calc R . .
C5 C 0.4182(6) 0.2024(4) 0.26000(9) 0.0656(10) Uani 1 1 d . . .
H5 H 0.5427 0.2637 0.2645 0.079 Uiso 1 1 calc R . .
C14 C 0.2764(6) 0.4175(4) 0.05805(10) 0.0694(10) Uani 1 1 d . . .
H14 H 0.4132 0.4692 0.0568 0.083 Uiso 1 1 calc R . .
C1 C 0.3229(8) 0.0296(5) 0.35272(9) 0.1009(16) Uani 1 1 d . . .
H1A H 0.1632 0.0500 0.3539 0.151 Uiso 1 1 calc R . .
H1B H 0.3924 0.0551 0.3759 0.151 Uiso 1 1 calc R . .
H1C H 0.3463 -0.0750 0.3477 0.151 Uiso 1 1 calc R . .
C2 C 0.6291(7) 0.1970(6) 0.33117(11) 0.1033(15) Uani 1 1 d . . .
H2A H 0.7464 0.1616 0.3150 0.155 Uiso 1 1 calc R . .
H2B H 0.6734 0.1805 0.3564 0.155 Uiso 1 1 calc R . .
H2C H 0.6056 0.3024 0.3272 0.155 Uiso 1 1 calc R . .
N2 N 0.1166(4) 0.1868(3) 0.15349(7) 0.0570(7) Uani 1 1 d . . .
N3 N -0.0155(4) 0.1650(3) 0.12229(7) 0.0608(7) Uani 1 1 d . . .
N1 N 0.4229(6) 0.1174(4) 0.32373(8) 0.0894(11) Uani 1 1 d . . .
F1 F -0.4091(4) -0.3309(2) 0.01795(5) 0.0828(7) 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
C12 C17 1.387(4) . ?
C12 C13 1.397(4) . ?
C12 N3 1.395(4) . ?
C9 N2 1.285(4) . ?
C9 C8 1.454(4) . ?
C9 C10 1.512(4) . ?
C22 C21 1.347(4) . ?
C22 F1 1.365(3) . ?
C22 C23 1.369(5) . ?
C8 C7 1.392(4) . ?
C8 C6 1.394(4) . ?
C18 C23 1.377(4) . ?
C18 C19 1.378(4) . ?
C20 C21 1.383(4) . ?
C20 C19 1.390(4) . ?
C6 C5 1.372(4) . ?
C16 C15 1.370(5) . ?
C16 C17 1.390(4) . ?
C19 C11 1.505(4) . ?
C11 N3 1.485(4) . ?
C11 C10 1.539(4) . ?
C13 C14 1.366(4) . ?
C7 C4 1.384(4) . ?
C15 C14 1.367(5) . ?
C3 N1 1.380(4) . ?
C3 C4 1.392(5) . ?
C3 C5 1.398(5) . ?
C1 N1 1.435(5) . ?
C2 N1 1.433(5) . ?
N2 N3 1.385(3) . ?

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
C17 C12 C13 118.0(3) . . ?
C17 C12 N3 122.3(3) . . ?
C13 C12 N3 119.5(3) . . ?
N2 C9 C8 121.5(3) . . ?
N2 C9 C10 113.1(3) . . ?
C8 C9 C10 125.4(3) . . ?
C21 C22 F1 119.0(3) . . ?
C21 C22 C23 122.5(3) . . ?
F1 C22 C23 118.4(3) . . ?
C7 C8 C6 116.8(3) . . ?
C7 C8 C9 120.9(3) . . ?
C6 C8 C9 122.3(3) . . ?
C23 C18 C19 121.0(3) . . ?
C21 C20 C19 120.3(3) . . ?
C5 C6 C8 122.0(3) . . ?
C15 C16 C17 121.3(3) . . ?
C18 C19 C20 118.7(3) . . ?
C18 C19 C11 120.9(3) . . ?
C20 C19 C11 120.3(3) . . ?
N3 C11 C19 112.3(2) . . ?
N3 C11 C10 100.9(2) . . ?
C19 C11 C10 115.7(3) . . ?
C14 C13 C12 120.5(3) . . ?
C4 C7 C8 121.5(3) . . ?
C22 C21 C20 119.0(3) . . ?
C14 C15 C16 118.4(3) . . ?
N1 C3 C4 121.5(3) . . ?
N1 C3 C5 121.7(3) . . ?
C4 C3 C5 116.8(3) . . ?
C22 C23 C18 118.4(3) . . ?
C9 C10 C11 102.7(2) . . ?
C12 C17 C16 120.0(3) . . ?
C7 C4 C3 121.5(3) . . ?
C6 C5 C3 121.4(3) . . ?
C13 C14 C15 121.8(3) . . ?
C9 N2 N3 109.1(2) . . ?
N2 N3 C12 118.1(2) . . ?
N2 N3 C11 112.3(2) . . ?
C12 N3 C11 125.9(2) . . ?
C3 N1 C1 120.0(4) . . ?
C3 N1 C2 121.0(4) . . ?
C1 N1 C2 118.8(3) . . ?

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
N2 C9 C8 C7 -174.2(3) . . . . ?
C10 C9 C8 C7 3.2(5) . . . . ?
N2 C9 C8 C6 7.4(5) . . . . ?
C10 C9 C8 C6 -175.1(3) . . . . ?
C7 C8 C6 C5 -0.2(5) . . . . ?
C9 C8 C6 C5 178.2(3) . . . . ?
C23 C18 C19 C20 1.7(4) . . . . ?
C23 C18 C19 C11 -175.2(3) . . . . ?
C21 C20 C19 C18 -1.8(4) . . . . ?
C21 C20 C19 C11 175.2(3) . . . . ?
C18 C19 C11 N3 50.0(4) . . . . ?
C20 C19 C11 N3 -127.0(3) . . . . ?
C18 C19 C11 C10 -65.1(4) . . . . ?
C20 C19 C11 C10 117.9(3) . . . . ?
C17 C12 C13 C14 -1.7(5) . . . . ?
N3 C12 C13 C14 174.2(3) . . . . ?
C6 C8 C7 C4 0.6(5) . . . . ?
C9 C8 C7 C4 -177.8(3) . . . . ?
F1 C22 C21 C20 -177.4(3) . . . . ?
C23 C22 C21 C20 2.5(5) . . . . ?
C19 C20 C21 C22 -0.2(5) . . . . ?
C17 C16 C15 C14 -1.5(5) . . . . ?
C21 C22 C23 C18 -2.6(5) . . . . ?
F1 C22 C23 C18 177.3(3) . . . . ?
C19 C18 C23 C22 0.4(5) . . . . ?
N2 C9 C10 C11 -8.7(4) . . . . ?
C8 C9 C10 C11 173.6(3) . . . . ?
N3 C11 C10 C9 12.2(3) . . . . ?
C19 C11 C10 C9 133.6(3) . . . . ?
C13 C12 C17 C16 1.1(5) . . . . ?
N3 C12 C17 C16 -174.6(3) . . . . ?
C15 C16 C17 C12 0.4(5) . . . . ?
C8 C7 C4 C3 0.2(5) . . . . ?
N1 C3 C4 C7 177.7(4) . . . . ?
C5 C3 C4 C7 -1.4(5) . . . . ?
C8 C6 C5 C3 -1.1(5) . . . . ?
N1 C3 C5 C6 -177.3(3) . . . . ?
C4 C3 C5 C6 1.9(5) . . . . ?
C12 C13 C14 C15 0.7(5) . . . . ?
C16 C15 C14 C13 0.9(5) . . . . ?
C8 C9 N2 N3 178.3(3) . . . . ?
C10 C9 N2 N3 0.5(4) . . . . ?
C9 N2 N3 C12 168.4(3) . . . . ?
C9 N2 N3 C11 8.6(4) . . . . ?
C17 C12 N3 N2 -166.9(3) . . . . ?
C13 C12 N3 N2 17.4(4) . . . . ?
C17 C12 N3 C11 -10.1(5) . . . . ?
C13 C12 N3 C11 174.2(3) . . . . ?
C19 C11 N3 N2 -137.1(3) . . . . ?
C10 C11 N3 N2 -13.3(3) . . . . ?
C19 C11 N3 C12 65.0(4) . . . . ?
C10 C11 N3 C12 -171.2(3) . . . . ?
C4 C3 N1 C1 -2.4(5) . . . . ?
C5 C3 N1 C1 176.7(4) . . . . ?
C4 C3 N1 C2 171.3(4) . . . . ?
C5 C3 N1 C2 -9.6(6) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.032
