# 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 931519'
_audit_update_record             
;
2015-03-03 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'4,6-dimethyl-9-phenyl-8,12-dioxa-4,6-diazatetracyclo[8.8.0.02,7.013,18]octadeca-2(7),13,15, 17-tetraene-3,5,11-trione'
_chemical_name_common            'coumarinopyran pyrimidinedione'
_chemical_melting_point          '238-240 C'
_chemical_formula_moiety         C22H18N2O5
_chemical_formula_sum            'C22 H18 N2 O5'
_chemical_formula_weight         390.38

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   15.2039(8)
_cell_length_b                   12.3888(6)
_cell_length_c                   9.8162(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.113(2)
_cell_angle_gamma                90.00
_cell_volume                     1830.46(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4875
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      23.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9001
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_process_details   'SADABS (Bruker 1999)'

_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  '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            14679
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         24.19
_reflns_number_total             2932
_reflns_number_gt                2173
_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 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PLATON (Spek, 2003)'

_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)+(0.0878P)²+0.8077P] 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         2932
_refine_ls_number_parameters     264
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1326
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.136
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.12185(19) 0.0779(2) 0.3702(3) 0.0522(7) Uani 1 1 d . . .
C2 C 0.13453(18) 0.2647(2) 0.3120(3) 0.0504(7) Uani 1 1 d . . .
C3 C 0.0885(2) 0.3484(3) 0.2449(3) 0.0606(8) Uani 1 1 d . . .
H3 H 0.0275 0.3433 0.2184 0.073 Uiso 1 1 calc R . .
C4 C 0.1333(2) 0.4401(3) 0.2169(3) 0.0610(8) Uani 1 1 d . . .
H4 H 0.1027 0.4977 0.1716 0.073 Uiso 1 1 calc R . .
C5 C 0.2235(2) 0.4467(2) 0.2560(3) 0.0578(8) Uani 1 1 d . . .
H5 H 0.2542 0.5086 0.2368 0.069 Uiso 1 1 calc R . .
C6 C 0.26860(18) 0.3612(2) 0.3239(3) 0.0489(7) Uani 1 1 d . . .
H6 H 0.3297 0.3665 0.3501 0.059 Uiso 1 1 calc R . .
C7 C 0.22544(16) 0.2685(2) 0.3539(3) 0.0408(6) Uani 1 1 d . . .
C8 C 0.27015(16) 0.1716(2) 0.4279(3) 0.0412(6) Uani 1 1 d . . .
H8 H 0.2656 0.1790 0.5260 0.049 Uiso 1 1 calc R . .
C9 C 0.22135(17) 0.0686(2) 0.3762(3) 0.0478(7) Uani 1 1 d . . .
H9 H 0.2422 0.0096 0.4391 0.057 Uiso 1 1 calc R . .
C10 C 0.24454(18) 0.0413(2) 0.2341(3) 0.0504(7) Uani 1 1 d . . .
H10 H 0.2336 0.1046 0.1742 0.060 Uiso 1 1 calc R . .
C11 C 0.19643(19) -0.0543(2) 0.1650(3) 0.0532(7) Uani 1 1 d U . .
C12 C 0.1358(3) -0.0392(3) 0.0517(3) 0.0800(11) Uani 1 1 d U . .
H12 H 0.1253 0.0297 0.0155 0.096 Uiso 1 1 calc R . .
C13 C 0.0893(3) -0.1269(4) -0.0105(4) 0.1019(13) Uani 1 1 d U . .
H13 H 0.0468 -0.1159 -0.0871 0.122 Uiso 1 1 calc R . .
C14 C 0.1051(3) -0.2284(4) 0.0392(5) 0.0930(12) Uani 1 1 d U . .
H14 H 0.0769 -0.2872 -0.0069 0.112 Uiso 1 1 calc R . .
C15 C 0.1617(3) -0.2430(3) 0.1555(6) 0.1090(14) Uani 1 1 d U . .
H15 H 0.1704 -0.3116 0.1934 0.131 Uiso 1 1 calc R . .
C16 C 0.2072(3) -0.1554(3) 0.2189(5) 0.0975(13) Uani 1 1 d U . .
H16 H 0.2459 -0.1660 0.3000 0.117 Uiso 1 1 calc R . .
C17 C 0.36679(16) 0.1574(2) 0.4137(3) 0.0393(6) Uani 1 1 d . . .
C18 C 0.43285(17) 0.2197(2) 0.4966(3) 0.0477(7) Uani 1 1 d . . .
C19 C 0.54782(18) 0.1186(2) 0.3978(3) 0.0539(8) Uani 1 1 d . . .
C20 C 0.39278(16) 0.0805(2) 0.3319(3) 0.0415(6) Uani 1 1 d . . .
C21 C 0.5913(2) 0.2662(3) 0.5544(4) 0.0746(10) Uani 1 1 d . . .
H21A H 0.6025 0.2427 0.6484 0.112 Uiso 1 1 calc R . .
H21B H 0.5725 0.3402 0.5511 0.112 Uiso 1 1 calc R . .
H21C H 0.6448 0.2596 0.5133 0.112 Uiso 1 1 calc R . .
C22 C 0.5057(2) -0.0241(3) 0.2303(4) 0.0692(9) Uani 1 1 d . . .
H22A H 0.5693 -0.0306 0.2413 0.104 Uiso 1 1 calc R . .
H22B H 0.4841 -0.0032 0.1375 0.104 Uiso 1 1 calc R . .
H22C H 0.4802 -0.0923 0.2499 0.104 Uiso 1 1 calc R . .
N1 N 0.52144(14) 0.19906(19) 0.4785(2) 0.0518(6) Uani 1 1 d . . .
N2 N 0.48081(14) 0.05776(18) 0.3254(2) 0.0487(6) Uani 1 1 d . . .
O1 O 0.08393(12) 0.17489(17) 0.3380(2) 0.0653(6) Uani 1 1 d . . .
O2 O 0.07525(13) 0.00462(18) 0.3916(2) 0.0682(7) Uani 1 1 d . . .
O3 O 0.33947(12) 0.01443(15) 0.2508(2) 0.0503(5) Uani 1 1 d . . .
O4 O 0.41781(13) 0.28943(18) 0.5785(2) 0.0660(6) Uani 1 1 d . . .
O5 O 0.62572(13) 0.10056(19) 0.3908(3) 0.0773(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
C1 O2 1.188(3) . ?
C1 O1 1.351(4) . ?
C1 C9 1.510(4) . ?
C2 C3 1.368(4) . ?
C2 C7 1.386(4) . ?
C2 O1 1.397(3) . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.514(4) . ?
C8 C17 1.506(3) . ?
C8 C9 1.526(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.525(4) . ?
C9 H9 0.9800 . ?
C10 O3 1.468(3) . ?
C10 C11 1.502(4) . ?
C10 H10 0.9800 . ?
C11 C12 1.354(5) . ?
C11 C16 1.361(5) . ?
C12 C13 1.390(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.358(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.341(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C20 1.340(4) . ?
C17 C18 1.427(4) . ?
C18 O4 1.224(3) . ?
C18 N1 1.407(3) . ?
C19 O5 1.217(3) . ?
C19 N1 1.368(4) . ?
C19 N2 1.381(4) . ?
C20 O3 1.334(3) . ?
C20 N2 1.378(3) . ?
C21 N1 1.467(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 N2 1.464(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
O2 C1 O1 118.4(3) . . ?
O2 C1 C9 123.6(3) . . ?
O1 C1 C9 118.0(2) . . ?
C3 C2 C7 122.6(3) . . ?
C3 C2 O1 115.8(3) . . ?
C7 C2 O1 121.7(3) . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 121.7(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C2 116.8(3) . . ?
C6 C7 C8 124.7(2) . . ?
C2 C7 C8 118.5(2) . . ?
C17 C8 C7 115.2(2) . . ?
C17 C8 C9 107.9(2) . . ?
C7 C8 C9 109.8(2) . . ?
C17 C8 H8 107.9 . . ?
C7 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
C1 C9 C10 110.0(2) . . ?
C1 C9 C8 112.8(2) . . ?
C10 C9 C8 109.0(2) . . ?
C1 C9 H9 108.3 . . ?
C10 C9 H9 108.3 . . ?
C8 C9 H9 108.3 . . ?
O3 C10 C11 106.3(2) . . ?
O3 C10 C9 107.4(2) . . ?
C11 C10 C9 115.3(2) . . ?
O3 C10 H10 109.3 . . ?
C11 C10 H10 109.3 . . ?
C9 C10 H10 109.3 . . ?
C12 C11 C16 118.5(3) . . ?
C12 C11 C10 119.6(3) . . ?
C16 C11 C10 121.8(3) . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.9(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 119.4(4) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 119.7(4) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 121.4(4) . . ?
C11 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C20 C17 C18 118.9(2) . . ?
C20 C17 C8 120.8(2) . . ?
C18 C17 C8 120.1(2) . . ?
O4 C18 N1 118.8(3) . . ?
O4 C18 C17 125.1(3) . . ?
N1 C18 C17 116.0(2) . . ?
O5 C19 N1 122.2(3) . . ?
O5 C19 N2 121.6(3) . . ?
N1 C19 N2 116.1(2) . . ?
O3 C20 C17 126.0(2) . . ?
O3 C20 N2 111.0(2) . . ?
C17 C20 N2 122.9(2) . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 N1 C18 124.7(2) . . ?
C19 N1 C21 117.2(2) . . ?
C18 N1 C21 118.1(3) . . ?
C19 N2 C20 121.0(2) . . ?
C19 N2 C22 117.9(2) . . ?
C20 N2 C22 120.8(2) . . ?
C1 O1 C2 121.6(2) . . ?
C20 O3 C10 115.6(2) . . ?

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
C7 C2 C3 C4 0.2(5) . . . . ?
O1 C2 C3 C4 179.2(3) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C5 C6 C7 C2 0.4(4) . . . . ?
C5 C6 C7 C8 180.0(3) . . . . ?
C3 C2 C7 C6 -0.5(4) . . . . ?
O1 C2 C7 C6 -179.5(2) . . . . ?
C3 C2 C7 C8 179.9(3) . . . . ?
O1 C2 C7 C8 0.9(4) . . . . ?
C6 C7 C8 C17 -26.3(4) . . . . ?
C2 C7 C8 C17 153.3(2) . . . . ?
C6 C7 C8 C9 -148.3(3) . . . . ?
C2 C7 C8 C9 31.3(3) . . . . ?
O2 C1 C9 C10 91.7(3) . . . . ?
O1 C1 C9 C10 -87.9(3) . . . . ?
O2 C1 C9 C8 -146.4(3) . . . . ?
O1 C1 C9 C8 34.0(4) . . . . ?
C17 C8 C9 C1 -173.5(2) . . . . ?
C7 C8 C9 C1 -47.2(3) . . . . ?
C17 C8 C9 C10 -51.1(3) . . . . ?
C7 C8 C9 C10 75.2(3) . . . . ?
C1 C9 C10 O3 -170.1(2) . . . . ?
C8 C9 C10 O3 65.9(3) . . . . ?
C1 C9 C10 C11 -51.9(3) . . . . ?
C8 C9 C10 C11 -175.9(2) . . . . ?
O3 C10 C11 C12 -129.4(3) . . . . ?
C9 C10 C11 C12 111.8(3) . . . . ?
O3 C10 C11 C16 55.5(4) . . . . ?
C9 C10 C11 C16 -63.3(4) . . . . ?
C16 C11 C12 C13 -3.0(6) . . . . ?
C10 C11 C12 C13 -178.2(3) . . . . ?
C11 C12 C13 C14 -1.4(7) . . . . ?
C12 C13 C14 C15 4.8(7) . . . . ?
C13 C14 C15 C16 -3.7(8) . . . . ?
C12 C11 C16 C15 4.0(7) . . . . ?
C10 C11 C16 C15 179.2(4) . . . . ?
C14 C15 C16 C11 -0.7(8) . . . . ?
C7 C8 C17 C20 -105.6(3) . . . . ?
C9 C8 C17 C20 17.5(3) . . . . ?
C7 C8 C17 C18 79.9(3) . . . . ?
C9 C8 C17 C18 -157.0(2) . . . . ?
C20 C17 C18 O4 -177.5(3) . . . . ?
C8 C17 C18 O4 -2.8(4) . . . . ?
C20 C17 C18 N1 3.9(4) . . . . ?
C8 C17 C18 N1 178.6(2) . . . . ?
C18 C17 C20 O3 178.6(2) . . . . ?
C8 C17 C20 O3 4.0(4) . . . . ?
C18 C17 C20 N2 0.8(4) . . . . ?
C8 C17 C20 N2 -173.8(2) . . . . ?
O5 C19 N1 C18 -176.2(3) . . . . ?
N2 C19 N1 C18 3.1(4) . . . . ?
O5 C19 N1 C21 1.8(4) . . . . ?
N2 C19 N1 C21 -178.8(3) . . . . ?
O4 C18 N1 C19 175.2(3) . . . . ?
C17 C18 N1 C19 -6.1(4) . . . . ?
O4 C18 N1 C21 -2.8(4) . . . . ?
C17 C18 N1 C21 175.9(3) . . . . ?
O5 C19 N2 C20 -178.6(3) . . . . ?
N1 C19 N2 C20 2.1(4) . . . . ?
O5 C19 N2 C22 -4.9(4) . . . . ?
N1 C19 N2 C22 175.8(3) . . . . ?
O3 C20 N2 C19 177.9(2) . . . . ?
C17 C20 N2 C19 -4.1(4) . . . . ?
O3 C20 N2 C22 4.4(4) . . . . ?
C17 C20 N2 C22 -177.6(3) . . . . ?
O2 C1 O1 C2 179.8(3) . . . . ?
C9 C1 O1 C2 -0.5(4) . . . . ?
C3 C2 O1 C1 162.7(3) . . . . ?
C7 C2 O1 C1 -18.3(4) . . . . ?
C17 C20 O3 C10 10.6(4) . . . . ?
N2 C20 O3 C10 -171.4(2) . . . . ?
C11 C10 O3 C20 -168.5(2) . . . . ?
C9 C10 O3 C20 -44.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.19
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.050
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane, Ethyl acetate'
