# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1401827'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
5-(4-fluorophenyl)-8-methyl-4-(phenylamino)pyrano[3',4':5,6]pyrano[2,3-d]pyrimidin-6(5H)-one
_chemical_name_common            ?
_chemical_melting_point          558-560
_chemical_formula_moiety         'C23 H16 F N3 O3'
_chemical_formula_sum            'C23 H16 F N3 O3'
_chemical_formula_weight         401.39

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   12.6990(4)
_cell_length_b                   9.0798(3)
_cell_length_c                   16.4608(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.3230(10)
_cell_angle_gamma                90.00
_cell_volume                     1861.06(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4421
_cell_measurement_theta_min      4.507
_cell_measurement_theta_max      51.788

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9646
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20635
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         28.30
_reflns_number_total             4583
_reflns_number_gt                3101
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0781P)²+0.0927P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4583
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1442
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_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
F1 F 0.15842(10) 0.35224(12) 0.67717(7) 0.0659(4) Uani 1 1 d . . .
O1 O 0.03740(9) 1.02587(13) 0.89461(8) 0.0449(3) Uani 1 1 d . . .
O2 O -0.22535(9) 0.76021(15) 0.85382(7) 0.0479(3) Uani 1 1 d . . .
O3 O -0.13405(9) 0.56861(14) 0.91330(8) 0.0463(3) Uani 1 1 d . . .
N1 N 0.28862(10) 0.66960(14) 1.03512(8) 0.0374(3) Uani 1 1 d . . .
H1 H 0.2379 0.6055 1.0307 0.045 Uiso 1 1 calc R . .
N2 N 0.33444(11) 0.91182(15) 1.01869(9) 0.0387(3) Uani 1 1 d . . .
N3 N 0.20708(12) 1.08631(16) 0.95019(9) 0.0448(4) Uani 1 1 d . . .
C1 C -0.34415(16) 0.9470(3) 0.79079(13) 0.0688(6) Uani 1 1 d . . .
H1A H -0.3490 1.0521 0.7849 0.103 Uiso 1 1 calc R . .
H1B H -0.3939 0.9138 0.8239 0.103 Uiso 1 1 calc R . .
H1C H -0.3612 0.9018 0.7371 0.103 Uiso 1 1 calc R . .
C2 C -0.23300(14) 0.9057(2) 0.83192(11) 0.0466(4) Uani 1 1 d . . .
C3 C -0.14720(14) 0.9923(2) 0.84717(11) 0.0452(4) Uani 1 1 d . . .
H3 H -0.1529 1.0920 0.8342 0.054 Uiso 1 1 calc R . .
C4 C -0.04616(13) 0.92965(19) 0.88377(10) 0.0366(4) Uani 1 1 d . . .
C5 C -0.03554(12) 0.78596(18) 0.90468(9) 0.0330(3) Uani 1 1 d . . .
C6 C 0.07190(11) 0.71302(16) 0.93435(9) 0.0302(3) Uani 1 1 d . . .
H6 H 0.0682 0.6528 0.9831 0.036 Uiso 1 1 calc R . .
C7 C 0.15498(12) 0.83245(16) 0.95884(9) 0.0299(3) Uani 1 1 d . . .
C8 C 0.26030(12) 0.80503(16) 1.00384(9) 0.0314(3) Uani 1 1 d . . .
C9 C 0.39237(12) 0.62149(17) 1.07438(10) 0.0338(3) Uani 1 1 d . . .
C10 C 0.39918(14) 0.5169(2) 1.13592(11) 0.0473(4) Uani 1 1 d . . .
H10 H 0.3374 0.4870 1.1537 0.057 Uiso 1 1 calc R . .
C11 C 0.49683(15) 0.4566(2) 1.17109(13) 0.0552(5) Uani 1 1 d . . .
H11 H 0.5005 0.3850 1.2119 0.066 Uiso 1 1 calc R . .
C12 C 0.58891(14) 0.5013(2) 1.14641(13) 0.0519(5) Uani 1 1 d . . .
H12 H 0.6549 0.4604 1.1703 0.062 Uiso 1 1 calc R . .
C13 C 0.13833(13) 0.43861(19) 0.73988(11) 0.0398(4) Uani 1 1 d . . .
C14 C 0.12614(14) 0.58611(19) 0.72645(11) 0.0438(4) Uani 1 1 d . . .
H14 H 0.1313 0.6269 0.6756 0.053 Uiso 1 1 calc R . .
C15 C 0.10596(13) 0.67363(17) 0.79023(10) 0.0387(4) Uani 1 1 d . . .
H15 H 0.0976 0.7746 0.7821 0.046 Uiso 1 1 calc R . .
C16 C 0.09791(11) 0.61363(16) 0.86609(9) 0.0297(3) Uani 1 1 d . . .
C17 C 0.58242(13) 0.6070(2) 1.08609(12) 0.0472(5) Uani 1 1 d . . .
H17 H 0.6448 0.6386 1.0699 0.057 Uiso 1 1 calc R . .
C18 C 0.48499(12) 0.66714(18) 1.04906(11) 0.0397(4) Uani 1 1 d . . .
H18 H 0.4815 0.7375 1.0076 0.048 Uiso 1 1 calc R . .
C19 C 0.30302(14) 1.04408(19) 0.99014(12) 0.0452(4) Uani 1 1 d . . .
H19 H 0.3553 1.1171 0.9994 0.054 Uiso 1 1 calc R . .
C20 C 0.13629(13) 0.97635(17) 0.93602(10) 0.0347(4) Uani 1 1 d . . .
C21 C -0.12991(12) 0.6961(2) 0.89315(9) 0.0370(4) Uani 1 1 d . . .
C22 C 0.11083(13) 0.46316(17) 0.87677(10) 0.0359(4) Uani 1 1 d . . .
H22 H 0.1053 0.4211 0.9273 0.043 Uiso 1 1 calc R . .
C23 C 0.13177(13) 0.37435(18) 0.81363(11) 0.0407(4) Uani 1 1 d . . .
H23 H 0.1411 0.2734 0.8212 0.049 Uiso 1 1 calc R . .


_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 C13 1.3598(19) . ?
O1 C4 1.359(2) . ?
O1 C20 1.3812(19) . ?
O2 C2 1.368(2) . ?
O2 C21 1.3850(19) . ?
O3 C21 1.209(2) . ?
N1 C8 1.3543(19) . ?
N1 C9 1.4176(19) . ?
N1 H1 0.8600 . ?
N2 C19 1.322(2) . ?
N2 C8 1.3401(19) . ?
N3 C19 1.322(2) . ?
N3 C20 1.333(2) . ?
C1 C2 1.489(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.327(3) . ?
C3 C4 1.424(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.349(2) . ?
C5 C21 1.431(2) . ?
C5 C6 1.509(2) . ?
C6 C7 1.512(2) . ?
C6 C16 1.527(2) . ?
C6 H6 0.9800 . ?
C7 C20 1.367(2) . ?
C7 C8 1.418(2) . ?
C9 C10 1.379(2) . ?
C9 C18 1.386(2) . ?
C10 C11 1.375(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(3) . ?
C11 H11 0.9300 . ?
C12 C17 1.372(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(2) . ?
C13 C23 1.364(2) . ?
C14 C15 1.380(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(2) . ?
C15 H15 0.9300 . ?
C16 C22 1.383(2) . ?
C17 C18 1.380(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C22 C23 1.382(2) . ?
C22 H22 0.9300 . ?
C23 H23 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
C4 O1 C20 117.80(12) . . ?
C2 O2 C21 122.63(14) . . ?
C8 N1 C9 127.36(13) . . ?
C8 N1 H1 116.3 . . ?
C9 N1 H1 116.3 . . ?
C19 N2 C8 116.11(14) . . ?
C19 N3 C20 113.18(15) . . ?
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 . . ?
C3 C2 O2 120.60(15) . . ?
C3 C2 C1 127.37(19) . . ?
O2 C2 C1 112.03(17) . . ?
C2 C3 C4 118.79(17) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 O1 123.48(14) . . ?
C5 C4 C3 122.04(16) . . ?
O1 C4 C3 114.47(15) . . ?
C4 C5 C21 118.56(14) . . ?
C4 C5 C6 123.08(14) . . ?
C21 C5 C6 118.24(14) . . ?
C5 C6 C7 108.11(12) . . ?
C5 C6 C16 109.49(12) . . ?
C7 C6 C16 112.31(12) . . ?
C5 C6 H6 109.0 . . ?
C7 C6 H6 109.0 . . ?
C16 C6 H6 109.0 . . ?
C20 C7 C8 113.98(14) . . ?
C20 C7 C6 122.54(13) . . ?
C8 C7 C6 123.42(13) . . ?
N2 C8 N1 117.58(14) . . ?
N2 C8 C7 121.67(14) . . ?
N1 C8 C7 120.73(13) . . ?
C10 C9 C18 119.49(15) . . ?
C10 C9 N1 117.76(14) . . ?
C18 C9 N1 122.57(15) . . ?
C11 C10 C9 120.32(17) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 120.54(18) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C17 C12 C11 119.17(16) . . ?
C17 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
F1 C13 C14 118.45(15) . . ?
F1 C13 C23 118.83(15) . . ?
C14 C13 C23 122.72(16) . . ?
C13 C14 C15 118.36(15) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C14 C15 C16 121.14(15) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C22 C16 C15 118.38(14) . . ?
C22 C16 C6 121.85(13) . . ?
C15 C16 C6 119.74(13) . . ?
C12 C17 C18 121.20(17) . . ?
C12 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C9 119.26(16) . . ?
C17 C18 H18 120.4 . . ?
C9 C18 H18 120.4 . . ?
N2 C19 N3 128.62(16) . . ?
N2 C19 H19 115.7 . . ?
N3 C19 H19 115.7 . . ?
N3 C20 C7 126.36(15) . . ?
N3 C20 O1 111.04(14) . . ?
C7 C20 O1 122.59(14) . . ?
O3 C21 O2 116.71(15) . . ?
O3 C21 C5 126.16(15) . . ?
O2 C21 C5 117.11(15) . . ?
C23 C22 C16 121.09(15) . . ?
C23 C22 H22 119.5 . . ?
C16 C22 H22 119.5 . . ?
C13 C23 C22 118.30(15) . . ?
C13 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.066
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Mixture of chloroform and acetonitrile'
