# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_BD97
_database_code_depnum_ccdc_archive 'CCDC 1514723'
_audit_update_record             
;
2016-11-03 deposited with the CCDC.
2016-12-22 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4-((1-(2-Fluorophenyl)vinyl)oxy)-2-phenylquinazoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H15 F N2 O'
_chemical_formula_sum            'C22 H15 F N2 O'
_chemical_formula_weight         342.36

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   38.444(4)
_cell_length_b                   6.2239(6)
_cell_length_c                   14.5234(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.834(3)
_cell_angle_gamma                90
_cell_volume                     3450.4(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6005
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      28.12

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   0.966
_exptl_transmission_factor_max   0.982
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19058
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.134
_diffrn_reflns_theta_max         28.258
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4173
_reflns_number_gt                3100
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0680P)²+0.9153P] 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_number_reflns         4173
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1325
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
C1 C 0.06355(3) 0.49716(17) 0.09843(8) 0.0392(3) Uani 1 1 d . . . . .
C2 C 0.03581(3) 0.6284(2) 0.12063(8) 0.0468(3) Uani 1 1 d . . . . .
H2 H 0.0128 0.5946 0.0982 0.056 Uiso 1 1 calc R U . . .
C3 C 0.04298(4) 0.8054(2) 0.17535(9) 0.0526(3) Uani 1 1 d . . . . .
H3 H 0.0246 0.8907 0.1902 0.063 Uiso 1 1 calc R U . . .
C4 C 0.07731(4) 0.8613(2) 0.20955(9) 0.0531(3) Uani 1 1 d . . . . .
H4 H 0.0815 0.9819 0.2470 0.064 Uiso 1 1 calc R U . . .
C5 C 0.10461(4) 0.7399(2) 0.18822(9) 0.0501(3) Uani 1 1 d . . . . .
H5 H 0.1275 0.7776 0.2104 0.060 Uiso 1 1 calc R U . . .
C6 C 0.09793(3) 0.55607(19) 0.13211(8) 0.0413(3) Uani 1 1 d . . . . .
C7 C 0.12418(3) 0.4223(2) 0.10223(8) 0.0453(3) Uani 1 1 d . . . . .
C8 C 0.08342(3) 0.20650(18) 0.02394(8) 0.0385(3) Uani 1 1 d . . . . .
C9 C 0.07684(3) 0.01190(17) -0.03486(7) 0.0400(3) Uani 1 1 d . . . . .
C10 C 0.04303(3) -0.0401(2) -0.07216(9) 0.0483(3) Uani 1 1 d . . . . .
H10 H 0.0245 0.0474 -0.0604 0.058 Uiso 1 1 calc R U . . .
C11 C 0.03665(4) -0.2213(2) -0.12685(9) 0.0580(4) Uani 1 1 d . . . . .
H11 H 0.0139 -0.2540 -0.1521 0.070 Uiso 1 1 calc R U . . .
C12 C 0.06376(4) -0.3528(2) -0.14396(9) 0.0603(4) Uani 1 1 d . . . . .
H12 H 0.0594 -0.4748 -0.1805 0.072 Uiso 1 1 calc R U . . .
C13 C 0.09740(4) -0.3042(2) -0.10714(10) 0.0579(4) Uani 1 1 d . . . . .
H13 H 0.1158 -0.3937 -0.1187 0.069 Uiso 1 1 calc R U . . .
C14 C 0.10416(4) -0.1220(2) -0.05275(9) 0.0488(3) Uani 1 1 d . . . . .
H14 H 0.1270 -0.0895 -0.0283 0.059 Uiso 1 1 calc R U . . .
C15 C 0.18468(3) 0.3494(3) 0.10553(11) 0.0587(4) Uani 1 1 d . . . . .
C16 C 0.20197(5) 0.4123(3) 0.03814(13) 0.0805(5) Uani 1 1 d . . . . .
H16A H 0.1962 0.5412 0.0078 0.097 Uiso 1 1 calc R U . . .
H16B H 0.2200 0.3281 0.0206 0.097 Uiso 1 1 calc R U . . .
C17 C 0.19222(3) 0.1695(3) 0.17005(10) 0.0559(4) Uani 1 1 d . . . . .
C18 C 0.18078(4) 0.1701(3) 0.25741(12) 0.0780(5) Uani 1 1 d . . . . .
H18 H 0.1673 0.2846 0.2741 0.094 Uiso 1 1 calc R U . . .
C19 C 0.18883(5) 0.0055(4) 0.31997(14) 0.0946(7) Uani 1 1 d . . . . .
H19 H 0.1807 0.0102 0.3777 0.114 Uiso 1 1 calc R U . . .
C20 C 0.20874(5) -0.1645(4) 0.29755(14) 0.0883(6) Uani 1 1 d . . . . .
H20 H 0.2144 -0.2739 0.3403 0.106 Uiso 1 1 calc R U . . .
C21 C 0.22021(4) -0.1731(3) 0.21232(13) 0.0766(5) Uani 1 1 d . . . . .
H21 H 0.2336 -0.2887 0.1961 0.092 Uiso 1 1 calc R U . . .
C22 C 0.21175(4) -0.0088(3) 0.15089(11) 0.0632(4) Uani 1 1 d . . . . .
F1 F 0.22346(3) -0.02401(18) 0.06698(8) 0.0944(4) Uani 1 1 d . . . . .
N1 N 0.05650(2) 0.31867(15) 0.04404(7) 0.0411(2) Uani 1 1 d . . . . .
N2 N 0.11796(3) 0.25265(16) 0.05092(7) 0.0445(3) Uani 1 1 d . . . . .
O1 O 0.15768(2) 0.48429(17) 0.12858(8) 0.0648(3) 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
C1 N1 1.3714(14) . ?
C1 C6 1.4025(16) . ?
C1 C2 1.4105(16) . ?
C2 C3 1.3674(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3585(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.4105(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.4155(17) . ?
C7 N2 1.2982(15) . ?
C7 O1 1.3550(14) . ?
C8 N1 1.3098(15) . ?
C8 N2 1.3695(15) . ?
C8 C9 1.4862(15) . ?
C9 C10 1.3856(17) . ?
C9 C14 1.3893(17) . ?
C10 C11 1.3843(18) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.3887(18) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.307(2) . ?
C15 O1 1.4062(16) . ?
C15 C17 1.467(2) . ?
C16 H16A 0.9300 . ?
C16 H16B 0.9300 . ?
C17 C22 1.386(2) . ?
C17 C18 1.391(2) . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.363(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(2) . ?
C21 H21 0.9300 . ?
C22 F1 1.3517(18) . ?

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
N1 C1 C6 121.73(10) . . ?
N1 C1 C2 119.86(11) . . ?
C6 C1 C2 118.41(11) . . ?
C3 C2 C1 119.59(12) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.57(12) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.20(12) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.36(12) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 120.86(11) . . ?
C1 C6 C7 114.59(10) . . ?
C5 C6 C7 124.51(11) . . ?
N2 C7 O1 119.83(11) . . ?
N2 C7 C6 124.41(11) . . ?
O1 C7 C6 115.74(11) . . ?
N1 C8 N2 126.11(10) . . ?
N1 C8 C9 118.51(10) . . ?
N2 C8 C9 115.37(10) . . ?
C10 C9 C14 118.78(11) . . ?
C10 C9 C8 120.19(11) . . ?
C14 C9 C8 121.02(11) . . ?
C11 C10 C9 120.58(13) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 120.24(13) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.93(12) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.36(13) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 120.11(13) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C16 C15 O1 117.08(16) . . ?
C16 C15 C17 128.88(14) . . ?
O1 C15 C17 113.52(13) . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C22 C17 C18 115.01(16) . . ?
C22 C17 C15 123.59(13) . . ?
C18 C17 C15 121.37(14) . . ?
C19 C18 C17 121.88(17) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C20 C19 C18 120.36(18) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 119.81(19) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 118.97(18) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
F1 C22 C21 117.11(15) . . ?
F1 C22 C17 118.92(15) . . ?
C21 C22 C17 123.96(15) . . ?
C8 N1 C1 116.94(10) . . ?
C7 N2 C8 116.16(10) . . ?
C7 O1 C15 117.82(10) . . ?

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
N1 C1 C2 C3 179.62(11) . . . . ?
C6 C1 C2 C3 -1.28(17) . . . . ?
C1 C2 C3 C4 0.50(19) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
N1 C1 C6 C5 -179.79(10) . . . . ?
C2 C1 C6 C5 1.13(17) . . . . ?
N1 C1 C6 C7 2.46(16) . . . . ?
C2 C1 C6 C7 -176.62(10) . . . . ?
C4 C5 C6 C1 -0.17(19) . . . . ?
C4 C5 C6 C7 177.35(12) . . . . ?
C1 C6 C7 N2 -2.68(18) . . . . ?
C5 C6 C7 N2 179.67(12) . . . . ?
C1 C6 C7 O1 175.66(10) . . . . ?
C5 C6 C7 O1 -2.00(19) . . . . ?
N1 C8 C9 C10 4.15(16) . . . . ?
N2 C8 C9 C10 -174.86(10) . . . . ?
N1 C8 C9 C14 -175.20(10) . . . . ?
N2 C8 C9 C14 5.78(16) . . . . ?
C14 C9 C10 C11 -0.50(18) . . . . ?
C8 C9 C10 C11 -179.86(11) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C12 C13 C14 C9 0.31(19) . . . . ?
C10 C9 C14 C13 0.02(18) . . . . ?
C8 C9 C14 C13 179.38(11) . . . . ?
C16 C15 C17 C22 -23.7(2) . . . . ?
O1 C15 C17 C22 164.96(12) . . . . ?
C16 C15 C17 C18 154.42(17) . . . . ?
O1 C15 C17 C18 -16.95(18) . . . . ?
C22 C17 C18 C19 0.7(2) . . . . ?
C15 C17 C18 C19 -177.53(16) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C18 C19 C20 C21 -1.1(3) . . . . ?
C19 C20 C21 C22 0.7(3) . . . . ?
C20 C21 C22 F1 -179.64(15) . . . . ?
C20 C21 C22 C17 0.5(2) . . . . ?
C18 C17 C22 F1 178.98(13) . . . . ?
C15 C17 C22 F1 -2.8(2) . . . . ?
C18 C17 C22 C21 -1.2(2) . . . . ?
C15 C17 C22 C21 177.03(14) . . . . ?
N2 C8 N1 C1 -1.11(17) . . . . ?
C9 C8 N1 C1 179.99(9) . . . . ?
C6 C1 N1 C8 -0.76(16) . . . . ?
C2 C1 N1 C8 178.31(10) . . . . ?
O1 C7 N2 C8 -177.20(11) . . . . ?
C6 C7 N2 C8 1.07(18) . . . . ?
N1 C8 N2 C7 0.98(17) . . . . ?
C9 C8 N2 C7 179.91(10) . . . . ?
N2 C7 O1 C15 -5.49(19) . . . . ?
C6 C7 O1 C15 176.10(12) . . . . ?
C16 C15 O1 C7 105.63(16) . . . . ?
C17 C15 O1 C7 -81.91(15) . . . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.038

