# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_I
_audit_block_doi                 10.5517/ccz3q2v
_database_code_depnum_ccdc_archive 'CCDC 897297'
_audit_update_record             
;
2012-08-21 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
#TrackingRef 'Dinesh -1a-ccdc_deposit.cif'


_audit_creation_date             2012-08-20T09:27:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
3-(2-(4-fluorobenzyl)-6-p-tolylpyrimidin-4-yl)-2H-chromen-2-one
;
_chemical_formula_sum            'C27 H19 F N2 O2'
_chemical_formula_weight         422.44

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0072(3)
_cell_length_b                   10.1043(4)
_cell_length_c                   13.2110(5)
_cell_angle_alpha                100.264(2)
_cell_angle_beta                 90.006(2)
_cell_angle_gamma                93.327(3)
_cell_volume                     1049.93(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_number            12040
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         23.64
_diffrn_reflns_theta_full        23.64
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             3127
_reflns_number_gt                2458
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0865P)²+0.1338P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.009(3)
_refine_ls_number_reflns         3127
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.047
_refine_ls_wR_factor_ref         0.1472
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_restrained_S_all      1.07
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.7866(3) 0.1243(2) 0.49321(12) 0.1726(10) Uani 1 1 d . . .
O2 O 0.93813(17) 0.80366(12) 0.98952(10) 0.0638(4) Uani 1 1 d . . .
O3 O 0.80510(19) 0.74700(14) 1.12113(11) 0.0756(5) Uani 1 1 d . . .
N4 N 0.5307(2) 0.25470(14) 1.06110(11) 0.0560(4) Uani 1 1 d . . .
N5 N 0.7030(2) 0.35088(14) 0.94376(11) 0.0552(4) Uani 1 1 d . . .
C6 C 0.8502(2) 0.70883(19) 1.03431(15) 0.0558(5) Uani 1 1 d . . .
C7 C 0.8210(2) 0.57545(17) 0.97205(13) 0.0465(4) Uani 1 1 d . . .
C8 C 0.8873(2) 0.54981(18) 0.87739(13) 0.0495(5) Uani 1 1 d . . .
H8 H 0.8708 0.4636 0.8388 0.059 Uiso 1 1 calc R . .
C9 C 0.9814(2) 0.64905(18) 0.83403(14) 0.0500(5) Uani 1 1 d . . .
C10 C 1.0034(2) 0.77691(19) 0.89249(15) 0.0545(5) Uani 1 1 d . . .
C11 C 1.0909(3) 0.8797(2) 0.85594(18) 0.0713(6) Uani 1 1 d . . .
H11 H 1.1044 0.9654 0.8958 0.086 Uiso 1 1 calc R . .
C12 C 1.1577(3) 0.8529(2) 0.75945(18) 0.0771(7) Uani 1 1 d . . .
H12 H 1.2169 0.9215 0.7339 0.092 Uiso 1 1 calc R . .
C13 C 1.1391(3) 0.7264(2) 0.69951(17) 0.0711(6) Uani 1 1 d . . .
H13 H 1.1857 0.7099 0.6343 0.085 Uiso 1 1 calc R . .
C14 C 1.0517(2) 0.6257(2) 0.73665(15) 0.0620(5) Uani 1 1 d . . .
H14 H 1.0389 0.5403 0.6963 0.074 Uiso 1 1 calc R . .
C15 C 0.7195(2) 0.46734(16) 1.01173(13) 0.0451(4) Uani 1 1 d . . .
C16 C 0.6092(2) 0.25123(17) 0.97192(14) 0.0562(5) Uani 1 1 d . . .
C17 C 0.5487(2) 0.36964(17) 1.12944(13) 0.0471(4) Uani 1 1 d . . .
C18 C 0.6442(2) 0.47982(17) 1.10601(13) 0.0474(5) Uani 1 1 d . . .
H18 H 0.6565 0.56 1.1532 0.057 Uiso 1 1 calc R . .
C19 C 0.4638(2) 0.37140(17) 1.22882(13) 0.0482(5) Uani 1 1 d . . .
C20 C 0.4099(3) 0.25179(19) 1.25882(15) 0.0595(5) Uani 1 1 d . . .
H20 H 0.4279 0.1706 1.2158 0.071 Uiso 1 1 calc R . .
C21 C 0.3303(3) 0.2502(2) 1.35075(15) 0.0641(6) Uani 1 1 d . . .
H21 H 0.2965 0.1681 1.3689 0.077 Uiso 1 1 calc R . .
C22 C 0.2996(2) 0.3684(2) 1.41675(14) 0.0601(5) Uani 1 1 d . . .
C23 C 0.3535(3) 0.4878(2) 1.38706(15) 0.0672(6) Uani 1 1 d . . .
H23 H 0.3358 0.5689 1.4304 0.081 Uiso 1 1 calc R . .
C24 C 0.4328(2) 0.48981(19) 1.29477(14) 0.0591(5) Uani 1 1 d . . .
H24 H 0.4661 0.572 1.2765 0.071 Uiso 1 1 calc R . .
C25 C 0.2087(3) 0.3659(3) 1.51604(17) 0.0849(7) Uani 1 1 d . . .
H25A H 0.1986 0.4565 1.5517 0.127 Uiso 1 1 calc R . .
H25B H 0.2702 0.3171 1.5582 0.127 Uiso 1 1 calc R . .
H25C H 0.0992 0.3226 1.5016 0.127 Uiso 1 1 calc R . .
C26 C 0.5914(4) 0.1187(2) 0.89789(16) 0.0838(8) Uani 1 1 d . . .
H26A H 0.657 0.0543 0.9242 0.101 Uiso 1 1 calc R . .
H26B H 0.4752 0.0854 0.8967 0.101 Uiso 1 1 calc R . .
C27 C 0.6438(3) 0.12287(17) 0.78966(15) 0.0588(5) Uani 1 1 d . . .
C28 C 0.8087(3) 0.1194(2) 0.76218(17) 0.0741(6) Uani 1 1 d . . .
H28 H 0.8894 0.1162 0.8122 0.089 Uiso 1 1 calc R . .
C29 C 0.8576(4) 0.1207(3) 0.6632(2) 0.0964(9) Uani 1 1 d . . .
H29 H 0.9701 0.1184 0.6457 0.116 Uiso 1 1 calc R . .
C30 C 0.7396(5) 0.1253(2) 0.59173(19) 0.0939(9) Uani 1 1 d . . .
C31 C 0.5763(4) 0.1309(2) 0.6147(2) 0.0924(8) Uani 1 1 d . . .
H31 H 0.4975 0.1358 0.5639 0.111 Uiso 1 1 calc R . .
C32 C 0.5273(3) 0.1294(2) 0.71451(19) 0.0744(6) Uani 1 1 d . . .
H32 H 0.4146 0.1328 0.7312 0.089 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C30 1.354(3) . ?
O2 C10 1.372(2) . ?
O2 C6 1.374(2) . ?
O3 C6 1.206(2) . ?
N4 C16 1.331(2) . ?
N4 C17 1.338(2) . ?
N5 C16 1.327(2) . ?
N5 C15 1.347(2) . ?
C6 C7 1.455(2) . ?
C7 C8 1.347(2) . ?
C7 C15 1.493(2) . ?
C8 C9 1.421(2) . ?
C8 H8 0.93 . ?
C9 C10 1.384(3) . ?
C9 C14 1.391(2) . ?
C10 C11 1.378(3) . ?
C11 C12 1.370(3) . ?
C11 H11 0.93 . ?
C12 C13 1.378(3) . ?
C12 H12 0.93 . ?
C13 C14 1.365(3) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C18 1.373(2) . ?
C16 C26 1.510(3) . ?
C17 C18 1.394(2) . ?
C17 C19 1.477(2) . ?
C18 H18 0.93 . ?
C19 C20 1.384(3) . ?
C19 C24 1.384(2) . ?
C20 C21 1.374(3) . ?
C20 H20 0.93 . ?
C21 C22 1.382(3) . ?
C21 H21 0.93 . ?
C22 C23 1.380(3) . ?
C22 C25 1.504(3) . ?
C23 C24 1.378(3) . ?
C23 H23 0.93 . ?
C24 H24 0.93 . ?
C25 H25A 0.96 . ?
C25 H25B 0.96 . ?
C25 H25C 0.96 . ?
C26 C27 1.497(3) . ?
C26 H26A 0.97 . ?
C26 H26B 0.97 . ?
C27 C28 1.370(3) . ?
C27 C32 1.375(3) . ?
C28 C29 1.367(3) . ?
C28 H28 0.93 . ?
C29 C30 1.344(4) . ?
C29 H29 0.93 . ?
C30 C31 1.344(4) . ?
C31 C32 1.379(3) . ?
C31 H31 0.93 . ?
C32 H32 0.93 . ?

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
C10 O2 C6 123.48(14) . . ?
C16 N4 C17 116.89(15) . . ?
C16 N5 C15 116.87(15) . . ?
O3 C6 O2 115.55(16) . . ?
O3 C6 C7 127.59(17) . . ?
O2 C6 C7 116.86(16) . . ?
C8 C7 C6 119.12(16) . . ?
C8 C7 C15 119.89(15) . . ?
C6 C7 C15 120.99(15) . . ?
C7 C8 C9 122.72(16) . . ?
C7 C8 H8 118.6 . . ?
C9 C8 H8 118.6 . . ?
C10 C9 C14 118.26(17) . . ?
C10 C9 C8 117.67(17) . . ?
C14 C9 C8 124.07(17) . . ?
O2 C10 C11 118.37(17) . . ?
O2 C10 C9 120.07(16) . . ?
C11 C10 C9 121.56(18) . . ?
C12 C11 C10 118.5(2) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C13 121.46(19) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C9 120.84(19) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
N5 C15 C18 120.77(15) . . ?
N5 C15 C7 113.24(14) . . ?
C18 C15 C7 125.97(15) . . ?
N5 C16 N4 126.41(15) . . ?
N5 C16 C26 117.91(16) . . ?
N4 C16 C26 115.66(16) . . ?
N4 C17 C18 120.54(15) . . ?
N4 C17 C19 116.40(15) . . ?
C18 C17 C19 123.06(15) . . ?
C15 C18 C17 118.50(15) . . ?
C15 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C20 C19 C24 117.29(17) . . ?
C20 C19 C17 120.17(15) . . ?
C24 C19 C17 122.53(16) . . ?
C21 C20 C19 121.50(17) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C22 121.24(18) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 117.36(17) . . ?
C23 C22 C25 121.72(18) . . ?
C21 C22 C25 120.91(18) . . ?
C24 C23 C22 121.57(18) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C19 121.03(18) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C16 115.70(16) . . ?
C27 C26 H26A 108.4 . . ?
C16 C26 H26A 108.4 . . ?
C27 C26 H26B 108.4 . . ?
C16 C26 H26B 108.4 . . ?
H26A C26 H26B 107.4 . . ?
C28 C27 C32 117.9(2) . . ?
C28 C27 C26 121.2(2) . . ?
C32 C27 C26 120.9(2) . . ?
C29 C28 C27 121.7(2) . . ?
C29 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C30 C29 C28 118.5(3) . . ?
C30 C29 H29 120.7 . . ?
C28 C29 H29 120.7 . . ?
C31 C30 C29 122.3(2) . . ?
C31 C30 F1 118.8(3) . . ?
C29 C30 F1 118.9(3) . . ?
C30 C31 C32 119.0(3) . . ?
C30 C31 H31 120.5 . . ?
C32 C31 H31 120.5 . . ?
C27 C32 C31 120.5(2) . . ?
C27 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?

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
C10 O2 C6 O3 177.94(16) . . . . ?
C10 O2 C6 C7 -2.6(3) . . . . ?
O3 C6 C7 C8 -177.35(19) . . . . ?
O2 C6 C7 C8 3.3(3) . . . . ?
O3 C6 C7 C15 2.5(3) . . . . ?
O2 C6 C7 C15 -176.92(15) . . . . ?
C6 C7 C8 C9 -1.8(3) . . . . ?
C15 C7 C8 C9 178.36(15) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C7 C8 C9 C14 179.91(17) . . . . ?
C6 O2 C10 C11 -179.33(17) . . . . ?
C6 O2 C10 C9 0.4(3) . . . . ?
C14 C9 C10 O2 -179.11(16) . . . . ?
C8 C9 C10 O2 1.2(3) . . . . ?
C14 C9 C10 C11 0.6(3) . . . . ?
C8 C9 C10 C11 -179.07(18) . . . . ?
O2 C10 C11 C12 179.36(18) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C9 0.0(3) . . . . ?
C10 C9 C14 C13 -0.4(3) . . . . ?
C8 C9 C14 C13 179.26(18) . . . . ?
C16 N5 C15 C18 1.0(3) . . . . ?
C16 N5 C15 C7 -177.58(16) . . . . ?
C8 C7 C15 N5 -1.1(2) . . . . ?
C6 C7 C15 N5 179.13(16) . . . . ?
C8 C7 C15 C18 -179.58(16) . . . . ?
C6 C7 C15 C18 0.6(3) . . . . ?
C15 N5 C16 N4 -0.5(3) . . . . ?
C15 N5 C16 C26 -178.84(18) . . . . ?
C17 N4 C16 N5 -0.4(3) . . . . ?
C17 N4 C16 C26 177.96(18) . . . . ?
C16 N4 C17 C18 0.8(3) . . . . ?
C16 N4 C17 C19 -178.86(15) . . . . ?
N5 C15 C18 C17 -0.6(3) . . . . ?
C7 C15 C18 C17 177.78(16) . . . . ?
N4 C17 C18 C15 -0.3(3) . . . . ?
C19 C17 C18 C15 179.33(15) . . . . ?
N4 C17 C19 C20 17.1(3) . . . . ?
C18 C17 C19 C20 -162.53(17) . . . . ?
N4 C17 C19 C24 -162.12(18) . . . . ?
C18 C17 C19 C24 18.2(3) . . . . ?
C24 C19 C20 C21 -0.6(3) . . . . ?
C17 C19 C20 C21 -179.93(17) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C20 C21 C22 C23 -0.6(3) . . . . ?
C20 C21 C22 C25 178.5(2) . . . . ?
C21 C22 C23 C24 0.8(3) . . . . ?
C25 C22 C23 C24 -178.24(19) . . . . ?
C22 C23 C24 C19 -1.0(3) . . . . ?
C20 C19 C24 C23 0.9(3) . . . . ?
C17 C19 C24 C23 -179.88(18) . . . . ?
N5 C16 C26 C27 -15.3(3) . . . . ?
N4 C16 C26 C27 166.2(2) . . . . ?
C16 C26 C27 C28 81.3(3) . . . . ?
C16 C26 C27 C32 -99.2(2) . . . . ?
C32 C27 C28 C29 -0.8(3) . . . . ?
C26 C27 C28 C29 178.8(2) . . . . ?
C27 C28 C29 C30 -0.1(4) . . . . ?
C28 C29 C30 C31 1.1(4) . . . . ?
C28 C29 C30 F1 -178.9(2) . . . . ?
C29 C30 C31 C32 -1.3(4) . . . . ?
F1 C30 C31 C32 178.78(19) . . . . ?
C28 C27 C32 C31 0.7(3) . . . . ?
C26 C27 C32 C31 -178.91(17) . . . . ?
C30 C31 C32 C27 0.3(3) . . . . ?
####################################################################### 
# 
# 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_Ia
_audit_block_doi                 10.5517/ccz3q3w
_database_code_depnum_ccdc_archive 'CCDC 897298'
_audit_update_record             
;
2012-08-21 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
#TrackingRef 'Dinesh- 1b-ccdc_deposit.cif'


_audit_creation_date             2012-08-20T09:03:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
3-(2-(4-fluorobenzyl)-6-(4-methoxyphenyl)pyrimidin-4-yl)-2H-chromen-2-one
;
_chemical_formula_sum            'C27 H19 F N2 O3'
_chemical_formula_weight         438.44

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1330(2)
_cell_length_b                   10.2945(2)
_cell_length_c                   12.7544(3)
_cell_angle_alpha                101.1920(10)
_cell_angle_beta                 90.3440(10)
_cell_angle_gamma                95.4990(10)
_cell_volume                     1042.40(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_number            17307
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3656
_reflns_number_gt                3036
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0576P)²+0.1330P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3656
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.29852(16) 0.57836(12) -0.51580(7) 0.1023(4) Uani 1 1 d . . .
O2 O 0.44489(13) 1.30511(9) -0.00621(8) 0.0581(3) Uani 1 1 d . . .
O3 O 0.30648(15) 1.25194(10) 0.12785(8) 0.0740(3) Uani 1 1 d . . .
O4 O -0.28759(16) 0.91129(11) 0.52642(9) 0.0790(4) Uani 1 1 d . . .
N5 N 0.02512(15) 0.76412(11) 0.06938(8) 0.0519(3) Uani 1 1 d . . .
N6 N 0.19990(14) 0.85324(10) -0.05386(8) 0.0501(3) Uani 1 1 d . . .
C7 C 0.35284(17) 1.21221(14) 0.03901(11) 0.0520(3) Uani 1 1 d . . .
C8 C 0.32221(15) 1.07790(12) -0.02585(10) 0.0440(3) Uani 1 1 d . . .
C9 C 0.38842(16) 1.05192(13) -0.12347(10) 0.0471(3) Uani 1 1 d . . .
H9 H 0.3698 0.9662 -0.164 0.056 Uiso 1 1 calc R . .
C10 C 0.48556(16) 1.15004(13) -0.16723(10) 0.0463(3) Uani 1 1 d . . .
C11 C 0.51143(16) 1.27716(13) -0.10591(10) 0.0492(3) Uani 1 1 d . . .
C12 C 0.60326(19) 1.37906(15) -0.14133(12) 0.0620(4) Uani 1 1 d . . .
H12 H 0.6184 1.4639 -0.099 0.074 Uiso 1 1 calc R . .
C13 C 0.6719(2) 1.35281(17) -0.24036(13) 0.0667(4) Uani 1 1 d . . .
H13 H 0.7346 1.4205 -0.2651 0.08 Uiso 1 1 calc R . .
C14 C 0.6490(2) 1.22717(17) -0.30358(12) 0.0655(4) Uani 1 1 d . . .
H14 H 0.6963 1.2105 -0.3704 0.079 Uiso 1 1 calc R . .
C15 C 0.55649(19) 1.12704(15) -0.26787(11) 0.0579(4) Uani 1 1 d . . .
H15 H 0.5407 1.0428 -0.311 0.07 Uiso 1 1 calc R . .
C16 C 0.21846(15) 0.97192(12) 0.01456(9) 0.0432(3) Uani 1 1 d . . .
C17 C 0.10492(18) 0.75655(13) -0.02270(10) 0.0512(3) Uani 1 1 d . . .
C18 C 0.04545(16) 0.88087(13) 0.13797(10) 0.0454(3) Uani 1 1 d . . .
C19 C 0.14338(16) 0.98853(13) 0.11228(10) 0.0466(3) Uani 1 1 d . . .
H19 H 0.1577 1.0697 0.16 0.056 Uiso 1 1 calc R . .
C20 C 0.0810(2) 0.62139(14) -0.09551(11) 0.0705(5) Uani 1 1 d . . .
H20A H 0.1373 0.5597 -0.063 0.085 Uiso 1 1 calc R . .
H20B H -0.036 0.591 -0.0994 0.085 Uiso 1 1 calc R . .
C21 C 0.14088(19) 0.61416(12) -0.20766(11) 0.0532(4) Uani 1 1 d . . .
C22 C 0.3008(2) 0.58834(15) -0.23301(12) 0.0643(4) Uani 1 1 d . . .
H22 H 0.3734 0.5784 -0.1792 0.077 Uiso 1 1 calc R . .
C23 C 0.3553(2) 0.57696(17) -0.33603(13) 0.0700(4) Uani 1 1 d . . .
H23 H 0.4631 0.5588 -0.3524 0.084 Uiso 1 1 calc R . .
C24 C 0.2475(2) 0.59300(15) -0.41306(11) 0.0642(4) Uani 1 1 d . . .
C25 C 0.0902(2) 0.62076(15) -0.39195(12) 0.0662(4) Uani 1 1 d . . .
H25 H 0.0195 0.6327 -0.4461 0.079 Uiso 1 1 calc R . .
C26 C 0.0371(2) 0.63090(14) -0.28846(12) 0.0602(4) Uani 1 1 d . . .
H26 H -0.0709 0.6494 -0.2731 0.072 Uiso 1 1 calc R . .
C27 C -0.04030(16) 0.88843(13) 0.24029(10) 0.0465(3) Uani 1 1 d . . .
C28 C -0.09607(18) 0.77306(14) 0.27514(11) 0.0555(4) Uani 1 1 d . . .
H28 H -0.078 0.6912 0.2335 0.067 Uiso 1 1 calc R . .
C29 C -0.17779(19) 0.77627(14) 0.37014(11) 0.0590(4) Uani 1 1 d . . .
H29 H -0.2134 0.6974 0.392 0.071 Uiso 1 1 calc R . .
C30 C -0.20627(18) 0.89671(15) 0.43221(11) 0.0568(4) Uani 1 1 d . . .
C31 C -0.1534(2) 1.01294(15) 0.39802(12) 0.0654(4) Uani 1 1 d . . .
H31 H -0.1739 1.0946 0.4391 0.079 Uiso 1 1 calc R . .
C32 C -0.07113(19) 1.00873(14) 0.30398(11) 0.0580(4) Uani 1 1 d . . .
H32 H -0.0354 1.0878 0.2825 0.07 Uiso 1 1 calc R . .
C33 C -0.3454(3) 0.7942(2) 0.56325(16) 0.0952(6) Uani 1 1 d . . .
H33A H -0.4 0.8178 0.6298 0.143 Uiso 1 1 calc R . .
H33B H -0.2536 0.7455 0.5736 0.143 Uiso 1 1 calc R . .
H33C H -0.4217 0.7399 0.5113 0.143 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C24 1.3615(16) . ?
O2 C11 1.3743(16) . ?
O2 C7 1.3748(17) . ?
O3 C7 1.2033(16) . ?
O4 C30 1.3647(16) . ?
O4 C33 1.417(2) . ?
N5 C17 1.3378(16) . ?
N5 C18 1.3377(16) . ?
N6 C17 1.3249(17) . ?
N6 C16 1.3514(16) . ?
C7 C8 1.4648(18) . ?
C8 C9 1.3484(17) . ?
C8 C16 1.4883(17) . ?
C9 C10 1.4238(18) . ?
C9 H9 0.93 . ?
C10 C11 1.3843(19) . ?
C10 C15 1.3976(18) . ?
C11 C12 1.3785(19) . ?
C12 C13 1.373(2) . ?
C12 H12 0.93 . ?
C13 C14 1.380(2) . ?
C13 H13 0.93 . ?
C14 C15 1.369(2) . ?
C14 H14 0.93 . ?
C15 H15 0.93 . ?
C16 C19 1.3791(17) . ?
C17 C20 1.5102(18) . ?
C18 C19 1.3946(18) . ?
C18 C27 1.4757(17) . ?
C19 H19 0.93 . ?
C20 C21 1.5043(18) . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
C21 C26 1.375(2) . ?
C21 C22 1.380(2) . ?
C22 C23 1.376(2) . ?
C22 H22 0.93 . ?
C23 C24 1.357(2) . ?
C23 H23 0.93 . ?
C24 C25 1.355(2) . ?
C25 C26 1.379(2) . ?
C25 H25 0.93 . ?
C26 H26 0.93 . ?
C27 C28 1.3849(19) . ?
C27 C32 1.3884(19) . ?
C28 C29 1.3817(19) . ?
C28 H28 0.93 . ?
C29 C30 1.376(2) . ?
C29 H29 0.93 . ?
C30 C31 1.383(2) . ?
C31 C32 1.3724(19) . ?
C31 H31 0.93 . ?
C32 H32 0.93 . ?
C33 H33A 0.96 . ?
C33 H33B 0.96 . ?
C33 H33C 0.96 . ?

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
C11 O2 C7 123.61(10) . . ?
C30 O4 C33 117.65(13) . . ?
C17 N5 C18 116.63(11) . . ?
C17 N6 C16 116.65(11) . . ?
O3 C7 O2 115.43(12) . . ?
O3 C7 C8 127.77(13) . . ?
O2 C7 C8 116.80(11) . . ?
C9 C8 C7 118.90(12) . . ?
C9 C8 C16 120.37(11) . . ?
C7 C8 C16 120.73(11) . . ?
C8 C9 C10 122.84(12) . . ?
C8 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C11 C10 C15 117.69(12) . . ?
C11 C10 C9 117.74(12) . . ?
C15 C10 C9 124.57(12) . . ?
O2 C11 C12 117.81(12) . . ?
O2 C11 C10 120.08(12) . . ?
C12 C11 C10 122.11(13) . . ?
C13 C12 C11 118.67(14) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 120.79(14) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 120.00(14) . . ?
C15 C14 H14 120 . . ?
C13 C14 H14 120 . . ?
C14 C15 C10 120.74(14) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
N6 C16 C19 120.68(11) . . ?
N6 C16 C8 114.35(11) . . ?
C19 C16 C8 124.96(11) . . ?
N6 C17 N5 126.82(11) . . ?
N6 C17 C20 118.96(12) . . ?
N5 C17 C20 114.21(11) . . ?
N5 C18 C19 120.70(11) . . ?
N5 C18 C27 116.60(11) . . ?
C19 C18 C27 122.71(11) . . ?
C16 C19 C18 118.50(11) . . ?
C16 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C21 C20 C17 116.17(11) . . ?
C21 C20 H20A 108.2 . . ?
C17 C20 H20A 108.2 . . ?
C21 C20 H20B 108.2 . . ?
C17 C20 H20B 108.2 . . ?
H20A C20 H20B 107.4 . . ?
C26 C21 C22 117.95(13) . . ?
C26 C21 C20 120.97(15) . . ?
C22 C21 C20 121.08(15) . . ?
C23 C22 C21 121.59(15) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C24 C23 C22 118.16(16) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
C25 C24 C23 122.52(14) . . ?
C25 C24 F1 118.72(16) . . ?
C23 C24 F1 118.75(16) . . ?
C24 C25 C26 118.62(15) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
C21 C26 C25 121.15(15) . . ?
C21 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C28 C27 C32 117.48(12) . . ?
C28 C27 C18 120.18(12) . . ?
C32 C27 C18 122.32(12) . . ?
C29 C28 C27 121.79(13) . . ?
C29 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C30 C29 C28 119.69(13) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
O4 C30 C29 124.55(13) . . ?
O4 C30 C31 116.09(13) . . ?
C29 C30 C31 119.35(13) . . ?
C32 C31 C30 120.50(13) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C31 C32 C27 121.17(13) . . ?
C31 C32 H32 119.4 . . ?
C27 C32 H32 119.4 . . ?
O4 C33 H33A 109.5 . . ?
O4 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O4 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

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
C11 O2 C7 O3 178.43(12) . . . . ?
C11 O2 C7 C8 -1.8(2) . . . . ?
O3 C7 C8 C9 -178.49(14) . . . . ?
O2 C7 C8 C9 1.77(19) . . . . ?
O3 C7 C8 C16 2.1(2) . . . . ?
O2 C7 C8 C16 -177.63(11) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C16 C8 C9 C10 178.58(11) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C8 C9 C10 C15 179.88(12) . . . . ?
C7 O2 C11 C12 -179.13(12) . . . . ?
C7 O2 C11 C10 0.8(2) . . . . ?
C15 C10 C11 O2 -179.81(12) . . . . ?
C9 C10 C11 O2 0.27(19) . . . . ?
C15 C10 C11 C12 0.1(2) . . . . ?
C9 C10 C11 C12 -179.81(13) . . . . ?
O2 C11 C12 C13 179.46(13) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C10 -0.5(2) . . . . ?
C11 C10 C15 C14 0.4(2) . . . . ?
C9 C10 C15 C14 -179.69(13) . . . . ?
C17 N6 C16 C19 1.07(18) . . . . ?
C17 N6 C16 C8 -178.27(11) . . . . ?
C9 C8 C16 N6 0.23(18) . . . . ?
C7 C8 C16 N6 179.63(12) . . . . ?
C9 C8 C16 C19 -179.07(12) . . . . ?
C7 C8 C16 C19 0.32(19) . . . . ?
C16 N6 C17 N5 0.1(2) . . . . ?
C16 N6 C17 C20 -179.45(13) . . . . ?
C18 N5 C17 N6 -1.2(2) . . . . ?
C18 N5 C17 C20 178.43(13) . . . . ?
C17 N5 C18 C19 1.00(19) . . . . ?
C17 N5 C18 C27 -178.98(11) . . . . ?
N6 C16 C19 C18 -1.19(19) . . . . ?
C8 C16 C19 C18 178.08(11) . . . . ?
N5 C18 C19 C16 0.10(19) . . . . ?
C27 C18 C19 C16 -179.91(11) . . . . ?
N6 C17 C20 C21 -11.4(2) . . . . ?
N5 C17 C20 C21 168.91(14) . . . . ?
C17 C20 C21 C26 -91.72(18) . . . . ?
C17 C20 C21 C22 89.37(18) . . . . ?
C26 C21 C22 C23 -1.2(2) . . . . ?
C20 C21 C22 C23 177.73(13) . . . . ?
C21 C22 C23 C24 0.6(2) . . . . ?
C22 C23 C24 C25 0.6(2) . . . . ?
C22 C23 C24 F1 -178.21(13) . . . . ?
C23 C24 C25 C26 -1.1(2) . . . . ?
F1 C24 C25 C26 177.75(13) . . . . ?
C22 C21 C26 C25 0.7(2) . . . . ?
C20 C21 C26 C25 -178.22(12) . . . . ?
C24 C25 C26 C21 0.4(2) . . . . ?
N5 C18 C27 C28 18.28(19) . . . . ?
C19 C18 C27 C28 -161.71(13) . . . . ?
N5 C18 C27 C32 -160.52(13) . . . . ?
C19 C18 C27 C32 19.5(2) . . . . ?
C32 C27 C28 C29 -0.7(2) . . . . ?
C18 C27 C28 C29 -179.57(13) . . . . ?
C27 C28 C29 C30 0.4(2) . . . . ?
C33 O4 C30 C29 0.6(3) . . . . ?
C33 O4 C30 C31 179.21(16) . . . . ?
C28 C29 C30 O4 179.03(14) . . . . ?
C28 C29 C30 C31 0.4(2) . . . . ?
O4 C30 C31 C32 -179.71(14) . . . . ?
C29 C30 C31 C32 -1.0(2) . . . . ?
C30 C31 C32 C27 0.7(2) . . . . ?
C28 C27 C32 C31 0.1(2) . . . . ?
C18 C27 C32 C31 178.97(14) . . . . ?
