# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_CS1_in_P21
_database_code_depnum_ccdc_archive 'CCDC 1451677'
_audit_update_record             
;
2016-02-03 deposited with the CCDC.
2016-02-15 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H18 F N3 O'
_chemical_formula_moiety         'C23 H18 F N3 O'
_chemical_formula_weight         371.41
_chemical_melting_point          372.15-374.15

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.0737(6)
_cell_length_b                   18.0810(11)
_cell_length_c                   12.2682(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 111.185(4)
_cell_angle_gamma                90.0000
_cell_volume                     1876.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14165
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      27.57
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.310
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776.00
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.579
_exptl_absorpt_correction_T_max  0.973

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.849
_diffrn_reflns_number            18720
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4287
_reflns_number_gt                2666
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1792
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4287
_refine_ls_number_parameters     257
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
F1 F -0.0040(3) 0.07528(12) 0.18388(13) 0.1278(8) Uani 1.0 4 d . . .
O1 O 0.51695(17) -0.01412(7) 0.84947(11) 0.0578(4) Uani 1.0 4 d . . .
N1 N 0.3358(2) 0.04703(10) 0.90018(14) 0.0511(5) Uani 1.0 4 d . . .
N2 N 0.36453(18) 0.07260(8) 0.72396(12) 0.0424(4) Uani 1.0 4 d . . .
N3 N 0.4573(2) 0.31695(9) 0.67032(14) 0.0579(5) Uani 1.0 4 d . . .
C1 C 0.4119(3) 0.03326(10) 0.82530(15) 0.0437(5) Uani 1.0 4 d . . .
C2 C 0.2086(2) 0.09545(11) 0.87741(15) 0.0454(5) Uani 1.0 4 d . . .
C3 C 0.1181(3) 0.09451(13) 0.94720(18) 0.0596(6) Uani 1.0 4 d . . .
C4 C -0.0066(3) 0.14212(16) 0.9239(2) 0.0743(7) Uani 1.0 4 d . . .
C5 C -0.0412(3) 0.19113(16) 0.8312(3) 0.0792(8) Uani 1.0 4 d . . .
C6 C 0.0500(3) 0.19159(12) 0.76232(18) 0.0587(6) Uani 1.0 4 d . . .
C7 C 0.1751(2) 0.14329(10) 0.78391(15) 0.0431(5) Uani 1.0 4 d . . .
C8 C 0.2722(2) 0.14186(9) 0.70620(14) 0.0415(5) Uani 1.0 4 d . . .
C9 C 0.3716(3) 0.20955(9) 0.71636(15) 0.0421(5) Uani 1.0 4 d . . .
C10 C 0.5026(2) 0.23454(10) 0.81557(15) 0.0427(5) Uani 1.0 4 d . . .
C11 C 0.5804(3) 0.20806(11) 0.92936(16) 0.0499(5) Uani 1.0 4 d . . .
C12 C 0.7017(3) 0.24884(12) 1.0045(2) 0.0638(6) Uani 1.0 4 d . . .
C13 C 0.7507(3) 0.31488(13) 0.9695(3) 0.0743(8) Uani 1.0 4 d . . .
C14 C 0.6784(3) 0.34169(12) 0.8592(3) 0.0663(7) Uani 1.0 4 d . . .
C15 C 0.5533(3) 0.30191(10) 0.78302(18) 0.0499(5) Uani 1.0 4 d . . .
C16 C 0.3497(3) 0.26163(11) 0.63160(17) 0.0532(6) Uani 1.0 4 d . . .
C17 C 0.4417(3) 0.05900(11) 0.63936(16) 0.0521(5) Uani 1.0 4 d . . .
C18 C 0.3254(3) 0.06175(9) 0.51575(15) 0.0478(5) Uani 1.0 4 d . . .
C19 C 0.1968(4) 0.01513(14) 0.4778(2) 0.0970(11) Uani 1.0 4 d . . .
C20 C 0.0864(5) 0.01967(17) 0.3662(3) 0.1195(14) Uani 1.0 4 d . . .
C21 C 0.1064(4) 0.07028(15) 0.29321(19) 0.0779(8) Uani 1.0 4 d . . .
C22 C 0.2278(3) 0.11764(14) 0.32587(19) 0.0727(7) Uani 1.0 4 d . . .
C23 C 0.3386(3) 0.11300(13) 0.43780(18) 0.0626(6) Uani 1.0 4 d . . .
H1 H 0.367(3) 0.0244(14) 0.968(3) 0.085(8) Uiso 1.0 4 d . . .
H3 H 0.4640 0.3551 0.6306 0.0695 Uiso 1.0 4 calc R . .
H3A H 0.1419 0.0617 1.0096 0.0715 Uiso 1.0 4 calc R . .
H4 H -0.0683 0.1416 0.9702 0.0892 Uiso 1.0 4 calc R . .
H5 H -0.1257 0.2237 0.8155 0.0950 Uiso 1.0 4 calc R . .
H6 H 0.0269 0.2249 0.7006 0.0705 Uiso 1.0 4 calc R . .
H8 H 0.1966 0.1407 0.6255 0.0498 Uiso 1.0 4 calc R . .
H11 H 0.5502 0.1636 0.9533 0.0598 Uiso 1.0 4 calc R . .
H12 H 0.7527 0.2321 1.0806 0.0766 Uiso 1.0 4 calc R . .
H13 H 0.8342 0.3411 1.0224 0.0892 Uiso 1.0 4 calc R . .
H14 H 0.7122 0.3854 0.8358 0.0795 Uiso 1.0 4 calc R . .
H16 H 0.2717 0.2596 0.5574 0.0639 Uiso 1.0 4 calc R . .
H17A H 0.4921 0.0108 0.6542 0.0625 Uiso 1.0 4 calc R . .
H17B H 0.5232 0.0959 0.6494 0.0625 Uiso 1.0 4 calc R . .
H19 H 0.1842 -0.0203 0.5288 0.1164 Uiso 1.0 4 calc R . .
H20 H -0.0004 -0.0118 0.3420 0.1434 Uiso 1.0 4 calc R . .
H22 H 0.2374 0.1532 0.2740 0.0872 Uiso 1.0 4 calc R . .
H23 H 0.4239 0.1454 0.4607 0.0751 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
F1 C21 1.357(3) yes . .
O1 C1 1.235(3) yes . .
N1 C1 1.357(3) yes . .
N1 C2 1.394(3) yes . .
N2 C1 1.360(3) yes . .
N2 C8 1.478(3) yes . .
N2 C17 1.468(3) yes . .
N3 C15 1.369(3) yes . .
N3 C16 1.358(3) yes . .
C2 C3 1.385(4) yes . .
C2 C7 1.380(3) yes . .
C3 C4 1.367(4) yes . .
C4 C5 1.385(4) yes . .
C5 C6 1.380(4) yes . .
C6 C7 1.380(3) yes . .
C7 C8 1.514(3) yes . .
C8 C9 1.499(3) yes . .
C9 C10 1.433(3) yes . .
C9 C16 1.363(3) yes . .
C10 C11 1.401(3) yes . .
C10 C15 1.410(3) yes . .
C11 C12 1.368(3) yes . .
C12 C13 1.395(4) yes . .
C13 C14 1.362(4) yes . .
C14 C15 1.383(3) yes . .
C17 C18 1.503(3) yes . .
C18 C19 1.377(4) yes . .
C18 C23 1.368(3) yes . .
C19 C20 1.375(4) yes . .
C20 C21 1.338(5) yes . .
C21 C22 1.337(4) yes . .
C22 C23 1.380(3) yes . .
N1 H1 0.88(3) no . .
N3 H3 0.860 no . .
C3 H3A 0.930 no . .
C4 H4 0.930 no . .
C5 H5 0.930 no . .
C6 H6 0.930 no . .
C8 H8 0.980 no . .
C11 H11 0.930 no . .
C12 H12 0.930 no . .
C13 H13 0.930 no . .
C14 H14 0.930 no . .
C16 H16 0.930 no . .
C17 H17A 0.970 no . .
C17 H17B 0.970 no . .
C19 H19 0.930 no . .
C20 H20 0.930 no . .
C22 H22 0.930 no . .
C23 H23 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N1 C2 124.51(17) yes . . .
C1 N2 C8 123.56(17) yes . . .
C1 N2 C17 118.99(16) yes . . .
C8 N2 C17 115.31(15) yes . . .
C15 N3 C16 108.76(17) yes . . .
O1 C1 N1 120.13(17) yes . . .
O1 C1 N2 122.9(2) yes . . .
N1 C1 N2 116.92(17) yes . . .
N1 C2 C3 120.12(18) yes . . .
N1 C2 C7 118.5(2) yes . . .
C3 C2 C7 121.34(19) yes . . .
C2 C3 C4 119.6(3) yes . . .
C3 C4 C5 119.9(3) yes . . .
C4 C5 C6 119.9(3) yes . . .
C5 C6 C7 120.8(2) yes . . .
C2 C7 C6 118.4(2) yes . . .
C2 C7 C8 120.61(17) yes . . .
C6 C7 C8 121.02(17) yes . . .
N2 C8 C7 110.44(15) yes . . .
N2 C8 C9 112.80(16) yes . . .
C7 C8 C9 113.79(16) yes . . .
C8 C9 C10 128.16(16) yes . . .
C8 C9 C16 125.66(15) yes . . .
C10 C9 C16 106.14(16) yes . . .
C9 C10 C11 134.68(18) yes . . .
C9 C10 C15 106.69(15) yes . . .
C11 C10 C15 118.61(16) yes . . .
C10 C11 C12 118.7(2) yes . . .
C11 C12 C13 121.5(2) yes . . .
C12 C13 C14 121.2(2) yes . . .
C13 C14 C15 118.0(3) yes . . .
N3 C15 C10 107.70(16) yes . . .
N3 C15 C14 130.3(2) yes . . .
C10 C15 C14 122.02(19) yes . . .
N3 C16 C9 110.70(16) yes . . .
N2 C17 C18 111.53(18) yes . . .
C17 C18 C19 121.43(19) yes . . .
C17 C18 C23 121.38(18) yes . . .
C19 C18 C23 117.12(18) yes . . .
C18 C19 C20 121.5(3) yes . . .
C19 C20 C21 118.8(3) yes . . .
F1 C21 C20 118.5(3) yes . . .
F1 C21 C22 119.2(3) yes . . .
C20 C21 C22 122.3(3) yes . . .
C21 C22 C23 119.0(3) yes . . .
C18 C23 C22 121.4(3) yes . . .
C1 N1 H1 119(2) no . . .
C2 N1 H1 116(2) no . . .
C15 N3 H3 125.615 no . . .
C16 N3 H3 125.623 no . . .
C2 C3 H3A 120.195 no . . .
C4 C3 H3A 120.185 no . . .
C3 C4 H4 120.035 no . . .
C5 C4 H4 120.030 no . . .
C4 C5 H5 120.050 no . . .
C6 C5 H5 120.031 no . . .
C5 C6 H6 119.586 no . . .
C7 C6 H6 119.599 no . . .
N2 C8 H8 106.414 no . . .
C7 C8 H8 106.408 no . . .
C9 C8 H8 106.416 no . . .
C10 C11 H11 120.661 no . . .
C12 C11 H11 120.658 no . . .
C11 C12 H12 119.245 no . . .
C13 C12 H12 119.260 no . . .
C12 C13 H13 119.400 no . . .
C14 C13 H13 119.403 no . . .
C13 C14 H14 121.012 no . . .
C15 C14 H14 121.013 no . . .
N3 C16 H16 124.656 no . . .
C9 C16 H16 124.640 no . . .
N2 C17 H17A 109.315 no . . .
N2 C17 H17B 109.326 no . . .
C18 C17 H17A 109.316 no . . .
C18 C17 H17B 109.317 no . . .
H17A C17 H17B 107.963 no . . .
C18 C19 H19 119.229 no . . .
C20 C19 H19 119.229 no . . .
C19 C20 H20 120.623 no . . .
C21 C20 H20 120.621 no . . .
C21 C22 H22 120.528 no . . .
C23 C22 H22 120.518 no . . .
C18 C23 H23 119.325 no . . .
C22 C23 H23 119.317 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N1 C2 C3 166.49(16) no . . . .
C1 N1 C2 C7 -13.0(3) no . . . .
C2 N1 C1 O1 -175.28(16) no . . . .
C2 N1 C1 N2 3.4(3) no . . . .
C1 N2 C8 C7 -27.0(2) no . . . .
C1 N2 C8 C9 101.62(19) no . . . .
C8 N2 C1 O1 -163.11(15) no . . . .
C8 N2 C1 N1 18.2(3) no . . . .
C1 N2 C17 C18 141.44(15) no . . . .
C17 N2 C1 O1 -0.5(3) no . . . .
C17 N2 C1 N1 -179.19(14) no . . . .
C8 N2 C17 C18 -54.56(19) no . . . .
C17 N2 C8 C7 169.86(12) no . . . .
C17 N2 C8 C9 -61.56(17) no . . . .
C15 N3 C16 C9 -0.0(3) no . . . .
C16 N3 C15 C10 -0.2(3) no . . . .
C16 N3 C15 C14 -179.5(3) no . . . .
N1 C2 C3 C4 -179.84(15) no . . . .
N1 C2 C7 C6 -179.41(14) no . . . .
N1 C2 C7 C8 1.4(3) no . . . .
C3 C2 C7 C6 1.1(3) no . . . .
C3 C2 C7 C8 -178.03(15) no . . . .
C7 C2 C3 C4 -0.4(3) no . . . .
C2 C3 C4 C5 -0.3(4) no . . . .
C3 C4 C5 C6 0.3(4) no . . . .
C4 C5 C6 C7 0.5(4) no . . . .
C5 C6 C7 C2 -1.2(3) no . . . .
C5 C6 C7 C8 177.99(17) no . . . .
C2 C7 C8 N2 16.3(2) no . . . .
C2 C7 C8 C9 -111.78(17) no . . . .
C6 C7 C8 N2 -162.88(15) no . . . .
C6 C7 C8 C9 69.07(19) no . . . .
N2 C8 C9 C10 -61.2(3) no . . . .
N2 C8 C9 C16 121.43(18) no . . . .
C7 C8 C9 C10 65.6(3) no . . . .
C7 C8 C9 C16 -111.74(19) no . . . .
C8 C9 C10 C11 0.2(4) no . . . .
C8 C9 C10 C15 -178.13(18) no . . . .
C8 C9 C16 N3 178.09(18) no . . . .
C10 C9 C16 N3 0.2(3) no . . . .
C16 C9 C10 C11 178.0(2) no . . . .
C16 C9 C10 C15 -0.3(3) no . . . .
C9 C10 C11 C12 -177.8(2) no . . . .
C9 C10 C15 N3 0.3(3) no . . . .
C9 C10 C15 C14 179.68(19) no . . . .
C11 C10 C15 N3 -178.29(18) no . . . .
C11 C10 C15 C14 1.0(4) no . . . .
C15 C10 C11 C12 0.4(3) no . . . .
C10 C11 C12 C13 -1.2(4) no . . . .
C11 C12 C13 C14 0.6(4) no . . . .
C12 C13 C14 C15 0.8(4) no . . . .
C13 C14 C15 N3 177.5(3) no . . . .
C13 C14 C15 C10 -1.6(4) no . . . .
N2 C17 C18 C19 -58.7(3) no . . . .
N2 C17 C18 C23 118.2(2) no . . . .
C17 C18 C19 C20 177.2(2) no . . . .
C17 C18 C23 C22 -177.08(19) no . . . .
C19 C18 C23 C22 -0.1(4) no . . . .
C23 C18 C19 C20 0.2(4) no . . . .
C18 C19 C20 C21 0.6(5) no . . . .
C19 C20 C21 F1 -179.0(3) no . . . .
C19 C20 C21 C22 -1.6(5) no . . . .
F1 C21 C22 C23 179.1(3) no . . . .
C20 C21 C22 C23 1.7(5) no . . . .
C21 C22 C23 C18 -0.8(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F1 C19 3.571(3) no . .
F1 C23 3.582(3) no . .
O1 C2 3.544(3) no . .
O1 C17 2.754(3) no . .
N1 C8 2.818(3) no . .
N1 C11 3.599(3) no . .
N2 C2 2.764(3) no . .
N2 C10 3.223(3) no . .
N2 C11 3.552(3) no . .
N2 C16 3.588(3) no . .
N2 C19 3.033(3) no . .
N2 C23 3.509(3) no . .
N3 C11 3.558(3) no . .
C1 C7 2.836(3) no . .
C1 C9 3.424(3) no . .
C1 C11 3.542(3) no . .
C2 C5 2.743(4) no . .
C2 C9 3.530(3) no . .
C3 C6 2.756(3) no . .
C4 C7 2.778(4) no . .
C6 C9 3.182(4) no . .
C7 C10 3.297(3) no . .
C7 C16 3.566(4) no . .
C8 C11 3.349(3) no . .
C8 C18 2.933(3) no . .
C8 C19 3.491(3) no . .
C8 C23 3.593(4) no . .
C9 C17 3.023(3) no . .
C9 C18 3.554(3) no . .
C10 C13 2.770(3) no . .
C11 C14 2.815(4) no . .
C12 C15 2.733(3) no . .
C14 C16 3.574(3) no . .
C16 C23 3.565(4) no . .
C18 C21 2.739(3) no . .
C19 C22 2.714(4) no . .
C20 C23 2.720(5) no . .
F1 N1 3.574(3) no . 3_556
F1 C2 3.540(3) no . 3_556
F1 C3 3.479(4) no . 1_554
F1 C3 3.447(3) no . 3_556
F1 C4 3.403(4) no . 1_554
O1 N1 2.934(2) no . 3_657
O1 N3 3.080(2) no . 2_646
N1 F1 3.574(3) no . 3_556
N1 O1 2.934(2) no . 3_657
N1 N1 3.534(3) no . 3_657
N3 O1 3.080(2) no . 2_656
N3 C11 3.547(3) no . 4_554
N3 C22 3.500(4) no . 4_555
C2 F1 3.540(3) no . 3_556
C3 F1 3.479(4) no . 1_556
C3 F1 3.447(3) no . 3_556
C3 C16 3.587(3) no . 4_555
C4 F1 3.403(4) no . 1_556
C11 N3 3.547(3) no . 4_555
C15 C22 3.499(4) no . 4_555
C15 C23 3.527(4) no . 4_555
C16 C3 3.587(3) no . 4_554
C22 N3 3.500(4) no . 4_554
C22 C15 3.499(4) no . 4_554
C23 C15 3.527(4) no . 4_554
F1 H20 2.4897 no . .
F1 H22 2.5006 no . .
O1 H1 2.42(4) no . .
O1 H11 3.4305 no . .
O1 H17A 2.3670 no . .
O1 H17B 3.1756 no . .
N1 H3A 2.5833 no . .
N1 H8 3.5694 no . .
N1 H11 2.7815 no . .
N2 H1 3.11(3) no . .
N2 H11 3.1687 no . .
N2 H19 2.8981 no . .
N3 H14 2.7585 no . .
C1 H8 3.1835 no . .
C1 H11 2.8592 no . .
C1 H17A 2.4908 no . .
C1 H17B 2.9209 no . .
C2 H4 3.2204 no . .
C2 H6 3.2118 no . .
C2 H8 3.1604 no . .
C2 H11 3.1474 no . .
C3 H1 2.52(3) no . .
C3 H5 3.2212 no . .
C4 H6 3.2310 no . .
C5 H3A 3.2244 no . .
C6 H4 3.2329 no . .
C6 H8 2.6549 no . .
C7 H1 3.15(3) no . .
C7 H3A 3.2457 no . .
C7 H5 3.2369 no . .
C7 H11 3.3051 no . .
C8 H6 2.6650 no . .
C8 H11 3.1909 no . .
C8 H16 2.8024 no . .
C8 H17A 3.3049 no . .
C8 H17B 2.7397 no . .
C8 H19 3.5654 no . .
C9 H3 3.0622 no . .
C9 H6 3.0761 no . .
C9 H11 2.8916 no . .
C9 H17B 2.7571 no . .
C9 H23 3.5338 no . .
C10 H3 3.0746 no . .
C10 H8 3.3686 no . .
C10 H12 3.2235 no . .
C10 H14 3.2832 no . .
C10 H16 3.1350 no . .
C10 H17B 3.2781 no . .
C11 H13 3.2391 no . .
C12 H14 3.2452 no . .
C13 H11 3.2507 no . .
C14 H3 2.7867 no . .
C14 H12 3.2300 no . .
C15 H11 3.2648 no . .
C15 H13 3.1961 no . .
C15 H16 3.1087 no . .
C16 H6 3.3953 no . .
C16 H8 2.5774 no . .
C16 H17B 3.3548 no . .
C16 H23 3.2080 no . .
C17 H8 2.6234 no . .
C17 H19 2.6577 no . .
C17 H23 2.6489 no . .
C18 H8 2.5198 no . .
C18 H20 3.2401 no . .
C18 H22 3.2331 no . .
C19 H8 2.9048 no . .
C19 H17A 2.7716 no . .
C19 H17B 3.2913 no . .
C19 H23 3.1865 no . .
C20 H22 3.1780 no . .
C21 H19 3.1707 no . .
C21 H23 3.1761 no . .
C22 H20 3.1784 no . .
C23 H8 3.0585 no . .
C23 H16 3.1919 no . .
C23 H17A 3.1193 no . .
C23 H17B 2.5493 no . .
C23 H19 3.1845 no . .
H1 H3A 2.3774 no . .
H1 H11 3.0553 no . .
H3 H14 2.7588 no . .
H3 H16 2.3888 no . .
H3A H4 2.3004 no . .
H4 H5 2.3161 no . .
H5 H6 2.3050 no . .
H6 H8 2.5621 no . .
H6 H16 3.3512 no . .
H8 H16 2.4887 no . .
H8 H17A 3.4846 no . .
H8 H17B 2.9817 no . .
H8 H19 3.1288 no . .
H8 H23 3.3714 no . .
H11 H12 2.2968 no . .
H12 H13 2.3059 no . .
H13 H14 2.2977 no . .
H16 H23 2.9607 no . .
H17A H19 2.7173 no . .
H17A H23 3.2984 no . .
H17B H19 3.5739 no . .
H17B H23 2.3381 no . .
H19 H20 2.3032 no . .
H22 H23 2.3082 no . .
F1 H3A 2.9043 no . 1_554
F1 H3A 3.3444 no . 3_556
F1 H4 2.7468 no . 1_554
F1 H12 3.5354 no . 1_454
O1 H1 2.11(3) no . 3_657
O1 H3 2.3764 no . 2_646
O1 H3A 3.0727 no . 3_657
O1 H14 3.0614 no . 2_646
N1 H1 2.90(3) no . 3_657
N1 H3 3.1774 no . 4_555
N1 H20 3.4582 no . 3_556
N2 H14 3.4796 no . 2_646
N2 H20 3.2933 no . 3_556
N3 H3A 3.5796 no . 4_554
N3 H11 3.0888 no . 4_554
N3 H12 3.3644 no . 4_554
N3 H22 2.7798 no . 4_555
C1 H1 2.80(3) no . 3_657
C1 H3 3.3899 no . 2_646
C1 H14 3.2727 no . 2_646
C1 H20 3.5730 no . 3_556
C2 H3 3.2578 no . 4_555
C2 H16 3.3413 no . 4_555
C2 H20 3.0698 no . 3_556
C3 H3 3.2618 no . 4_555
C3 H16 3.0612 no . 4_555
C4 H16 3.0384 no . 4_555
C5 H12 3.2744 no . 4_454
C5 H13 3.5881 no . 4_454
C5 H16 3.2954 no . 4_555
C6 H12 3.1309 no . 4_454
C6 H13 2.9461 no . 4_454
C6 H16 3.5595 no . 4_555
C6 H20 3.4620 no . 3_556
C6 H22 3.2578 no . 4_555
C7 H13 3.5731 no . 4_454
C7 H20 2.9627 no . 3_556
C8 H20 3.3022 no . 3_556
C9 H22 2.9614 no . 4_555
C10 H5 3.3791 no . 1_655
C10 H22 3.0477 no . 4_555
C10 H23 3.0511 no . 4_555
C11 H3 3.2250 no . 4_555
C11 H4 3.2716 no . 1_655
C11 H5 3.4406 no . 1_655
C11 H23 3.0949 no . 4_555
C12 H4 2.9878 no . 1_655
C12 H5 3.2649 no . 1_655
C12 H5 3.5969 no . 4_655
C12 H6 3.0964 no . 4_655
C12 H23 3.0530 no . 4_555
C13 H4 3.5363 no . 1_655
C13 H5 3.0130 no . 1_655
C13 H6 3.1144 no . 4_655
C13 H19 3.0375 no . 2_656
C13 H23 3.0144 no . 4_555
C14 H5 2.9474 no . 1_655
C14 H17A 3.4045 no . 2_656
C14 H19 2.9046 no . 2_656
C14 H23 3.0024 no . 4_555
C15 H5 3.1314 no . 1_655
C15 H22 2.9429 no . 4_555
C15 H23 2.9805 no . 4_555
C16 H11 3.5768 no . 4_554
C16 H22 2.7841 no . 4_555
C17 H14 3.4931 no . 2_646
C18 H17A 3.3626 no . 3_656
C19 H13 3.1595 no . 2_646
C19 H14 3.1700 no . 2_646
C19 H19 3.4299 no . 3_556
C19 H20 3.3039 no . 3_556
C20 H13 3.4786 no . 2_646
C20 H19 3.1590 no . 3_556
C22 H6 3.4305 no . 4_554
C22 H17A 3.3861 no . 3_656
C23 H17A 3.1463 no . 3_656
H1 O1 2.11(3) no . 3_657
H1 N1 2.90(3) no . 3_657
H1 C1 2.80(3) no . 3_657
H1 H1 2.41(4) no . 3_657
H1 H3 2.8666 no . 4_555
H1 H11 3.5398 no . 3_657
H3 O1 2.3764 no . 2_656
H3 N1 3.1774 no . 4_554
H3 C1 3.3899 no . 2_656
H3 C2 3.2578 no . 4_554
H3 C3 3.2618 no . 4_554
H3 C11 3.2250 no . 4_554
H3 H1 2.8666 no . 4_554
H3 H3A 3.1417 no . 4_554
H3 H11 2.5853 no . 4_554
H3 H12 3.3002 no . 4_554
H3 H22 3.1565 no . 4_555
H3A F1 2.9043 no . 1_556
H3A F1 3.3444 no . 3_556
H3A O1 3.0727 no . 3_657
H3A N3 3.5796 no . 4_555
H3A H3 3.1417 no . 4_555
H3A H3A 3.3511 no . 3_557
H3A H16 3.4171 no . 4_555
H3A H22 3.4612 no . 1_556
H4 F1 2.7468 no . 1_556
H4 C11 3.2716 no . 1_455
H4 C12 2.9878 no . 1_455
H4 C13 3.5363 no . 1_455
H4 H6 3.5777 no . 4_555
H4 H11 3.4164 no . 1_455
H4 H12 2.9568 no . 1_455
H4 H16 3.3863 no . 4_555
H5 C10 3.3791 no . 1_455
H5 C11 3.4406 no . 1_455
H5 C12 3.2649 no . 1_455
H5 C12 3.5969 no . 4_454
H5 C13 3.0130 no . 1_455
H5 C14 2.9474 no . 1_455
H5 C15 3.1314 no . 1_455
H5 H12 2.8036 no . 4_454
H5 H13 3.4280 no . 1_455
H5 H14 3.3229 no . 1_455
H6 C12 3.0964 no . 4_454
H6 C13 3.1144 no . 4_454
H6 C22 3.4305 no . 4_555
H6 H4 3.5777 no . 4_554
H6 H12 2.5124 no . 4_454
H6 H13 2.5481 no . 4_454
H6 H22 2.8424 no . 4_555
H8 H13 3.0847 no . 4_454
H8 H20 3.0442 no . 3_556
H11 N3 3.0888 no . 4_555
H11 C16 3.5768 no . 4_555
H11 H1 3.5398 no . 3_657
H11 H3 2.5853 no . 4_555
H11 H4 3.4164 no . 1_655
H11 H16 3.5038 no . 4_555
H12 F1 3.5354 no . 1_656
H12 N3 3.3644 no . 4_555
H12 C5 3.2744 no . 4_655
H12 C6 3.1309 no . 4_655
H12 H3 3.3002 no . 4_555
H12 H4 2.9568 no . 1_655
H12 H5 2.8036 no . 4_655
H12 H6 2.5124 no . 4_655
H12 H23 3.5772 no . 4_555
H13 C5 3.5881 no . 4_655
H13 C6 2.9461 no . 4_655
H13 C7 3.5731 no . 4_655
H13 C19 3.1595 no . 2_656
H13 C20 3.4786 no . 2_656
H13 H5 3.4280 no . 1_655
H13 H6 2.5481 no . 4_655
H13 H8 3.0847 no . 4_655
H13 H19 2.5754 no . 2_656
H13 H20 3.2092 no . 2_656
H13 H23 3.5290 no . 4_555
H14 O1 3.0614 no . 2_656
H14 N2 3.4796 no . 2_656
H14 C1 3.2727 no . 2_656
H14 C17 3.4931 no . 2_656
H14 C19 3.1700 no . 2_656
H14 H5 3.3229 no . 1_655
H14 H17A 2.9594 no . 2_656
H14 H19 2.3292 no . 2_656
H14 H20 3.4481 no . 4_655
H14 H23 3.5204 no . 4_555
H16 C2 3.3413 no . 4_554
H16 C3 3.0612 no . 4_554
H16 C4 3.0384 no . 4_554
H16 C5 3.2954 no . 4_554
H16 C6 3.5595 no . 4_554
H16 H3A 3.4171 no . 4_554
H16 H4 3.3863 no . 4_554
H16 H11 3.5038 no . 4_554
H16 H22 3.2008 no . 4_555
H17A C14 3.4045 no . 2_646
H17A C18 3.3626 no . 3_656
H17A C22 3.3861 no . 3_656
H17A C23 3.1463 no . 3_656
H17A H14 2.9594 no . 2_646
H17A H23 3.3643 no . 3_656
H19 C13 3.0375 no . 2_646
H19 C14 2.9046 no . 2_646
H19 C19 3.4299 no . 3_556
H19 C20 3.1590 no . 3_556
H19 H13 2.5754 no . 2_646
H19 H14 2.3292 no . 2_646
H19 H19 3.2409 no . 3_556
H19 H20 2.7468 no . 3_556
H20 N1 3.4582 no . 3_556
H20 N2 3.2933 no . 3_556
H20 C1 3.5730 no . 3_556
H20 C2 3.0698 no . 3_556
H20 C6 3.4620 no . 3_556
H20 C7 2.9627 no . 3_556
H20 C8 3.3022 no . 3_556
H20 C19 3.3039 no . 3_556
H20 H8 3.0442 no . 3_556
H20 H13 3.2092 no . 2_646
H20 H14 3.4481 no . 4_454
H20 H19 2.7468 no . 3_556
H22 N3 2.7798 no . 4_554
H22 C6 3.2578 no . 4_554
H22 C9 2.9614 no . 4_554
H22 C10 3.0477 no . 4_554
H22 C15 2.9429 no . 4_554
H22 C16 2.7841 no . 4_554
H22 H3 3.1565 no . 4_554
H22 H3A 3.4612 no . 1_554
H22 H6 2.8424 no . 4_554
H22 H16 3.2008 no . 4_554
H23 C10 3.0511 no . 4_554
H23 C11 3.0949 no . 4_554
H23 C12 3.0530 no . 4_554
H23 C13 3.0144 no . 4_554
H23 C14 3.0024 no . 4_554
H23 C15 2.9805 no . 4_554
H23 H12 3.5772 no . 4_554
H23 H13 3.5290 no . 4_554
H23 H14 3.5204 no . 4_554
H23 H17A 3.3643 no . 3_656

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 . . 3_657 2.934(2) 0.879 2.11(3) 156(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
3-(4-fluorobenzyl)-4-(1H-indol-3-yl)-3,4-dihydroquinazolin-2(1H)-one
_chemical_name_common            CS1-4FBA
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
