# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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 1026056'

_audit_update_record             
;
2014-09-24 deposited with the CCDC.
2014-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Diethyl 2-(2-oxo-1,2,3,4-tetrahydroquinazolin-4-yl)malonate'
_chemical_name_common            ?
_chemical_melting_point          390-395
_chemical_formula_moiety         'C15 H18 N2 O5'
_chemical_formula_sum            'C15 H18 N2 O5'
_chemical_formula_weight         306.31

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.5151(2)
_cell_length_b                   8.3328(2)
_cell_length_c                   13.0372(4)
_cell_angle_alpha                88.341(2)
_cell_angle_beta                 76.984(2)
_cell_angle_gamma                67.4070(10)
_cell_volume                     732.89(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    4960
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      190(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  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4676
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3297
_reflns_number_gt                2778
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'HKL Denzo (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_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)+(0.0520P)²+0.2708P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3297
_refine_ls_number_parameters     228
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.031
_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
O1 O 0.24374(14) 0.53012(12) 0.48544(8) 0.0269(2) Uani 1 1 d . . .
N1 N 0.45123(17) 0.32301(15) 0.56833(9) 0.0230(3) Uani 1 1 d . . .
O3 O 0.15365(16) 0.49663(13) 0.78773(9) 0.0338(3) Uani 1 1 d . . .
O4 O 0.68857(18) -0.00834(15) 0.79865(10) 0.0432(3) Uani 1 1 d . . .
C3 C 0.1974(2) 0.15418(17) 0.60345(10) 0.0226(3) Uani 1 1 d . . .
N2 N 0.14987(17) 0.31798(15) 0.56148(9) 0.0248(3) Uani 1 1 d . . .
C7 C 0.4196(2) -0.08707(18) 0.67539(11) 0.0285(3) Uani 1 1 d . . .
H1A H 0.5365 -0.1395 0.6981 0.034 Uiso 1 1 calc R . .
O2 O 0.18494(18) 0.26112(15) 0.88087(9) 0.0449(3) Uani 1 1 d . . .
C8 C 0.36908(19) 0.08067(17) 0.64048(10) 0.0218(3) Uani 1 1 d . . .
C10 C 0.2536(2) 0.33884(17) 0.81586(10) 0.0247(3) Uani 1 1 d . . .
C1 C 0.49352(19) 0.18607(16) 0.64217(10) 0.0212(3) Uani 1 1 d . . .
H4 H 0.6329 0.1077 0.6180 0.025 Uiso 1 1 calc R . .
C6 C 0.2973(3) -0.17667(19) 0.67661(12) 0.0340(3) Uani 1 1 d . . .
H5 H 0.3323 -0.2886 0.7002 0.041 Uiso 1 1 calc R . .
C9 C 0.4674(2) 0.26817(17) 0.75378(11) 0.0236(3) Uani 1 1 d . . .
H6 H 0.5091 0.3665 0.7431 0.028 Uiso 1 1 calc R . .
C5 C 0.1236(2) -0.0999(2) 0.64279(12) 0.0338(3) Uani 1 1 d . . .
H7 H 0.0404 -0.1593 0.6450 0.041 Uiso 1 1 calc R . .
O5 O 0.5900(3) 0.22797(17) 0.90528(12) 0.0654(5) Uani 1 1 d D . .
C4 C 0.0733(2) 0.06487(19) 0.60567(11) 0.0291(3) Uani 1 1 d . . .
H9 H -0.0429 0.1161 0.5822 0.035 Uiso 1 1 calc R . .
C2 C 0.28074(19) 0.39679(17) 0.53679(10) 0.0215(3) Uani 1 1 d . . .
C13 C 0.5943(2) 0.14302(19) 0.82042(12) 0.0313(3) Uani 1 1 d . A .
C11 C -0.0559(2) 0.5799(2) 0.84143(14) 0.0426(4) Uani 1 1 d . . .
H12A H -0.0971 0.7055 0.8418 0.051 Uiso 1 1 calc R . .
H12B H -0.0738 0.5482 0.9141 0.051 Uiso 1 1 calc R . .
C12 C -0.1822(3) 0.5261(3) 0.78814(16) 0.0568(5) Uani 1 1 d . . .
H14A H -0.1670 0.5599 0.7167 0.085 Uiso 1 1 calc R . .
H14B H -0.3184 0.5817 0.8251 0.085 Uiso 1 1 calc R . .
H14C H -0.1423 0.4019 0.7883 0.085 Uiso 1 1 calc R . .
C14A C 0.7451(10) 0.1164(9) 0.9618(5) 0.0610(16) Uani 0.50 1 d PD A 1
H14D H 0.8724 0.0597 0.9128 0.073 Uiso 0.50 1 calc PR A 1
H14E H 0.7062 0.0285 0.9993 0.073 Uiso 0.50 1 calc PR A 1
C15A C 0.7529(11) 0.2486(14) 1.0389(5) 0.0420(16) Uani 0.50 1 d PD A 1
H15A H 0.8287 0.3111 1.0015 0.063 Uiso 0.50 1 calc PR A 1
H15B H 0.8142 0.1881 1.0935 0.063 Uiso 0.50 1 calc PR A 1
H15C H 0.6208 0.3291 1.0698 0.063 Uiso 0.50 1 calc PR A 1
C14B C 0.6557(8) 0.1338(8) 0.9979(4) 0.0468(13) Uani 0.50 1 d PD A 2
H14F H 0.5422 0.1386 1.0527 0.056 Uiso 0.50 1 calc PR A 2
H14G H 0.7399 0.0126 0.9771 0.056 Uiso 0.50 1 calc PR A 2
C15B C 0.7595(19) 0.217(2) 1.0338(9) 0.094(4) Uani 0.50 1 d PD A 2
H15D H 0.8688 0.2148 0.9781 0.141 Uiso 0.50 1 calc PR A 2
H15E H 0.8086 0.1591 1.0924 0.141 Uiso 0.50 1 calc PR A 2
H15F H 0.6733 0.3360 1.0560 0.141 Uiso 0.50 1 calc PR A 2
HN2 H 0.036(3) 0.367(2) 0.5435(14) 0.037(5) Uiso 1 1 d . . .
HN1 H 0.541(3) 0.367(2) 0.5500(13) 0.032(4) Uiso 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
O1 C2 1.2503(15) . ?
N1 C2 1.3439(17) . ?
N1 C1 1.4579(16) . ?
N1 HN1 0.870(18) . ?
O3 C10 1.3284(16) . ?
O3 C11 1.464(2) . ?
O4 C13 1.1904(19) . ?
C3 C8 1.3892(19) . ?
C3 C4 1.3939(18) . ?
C3 N2 1.4001(17) . ?
N2 C2 1.3578(17) . ?
N2 HN2 0.880(19) . ?
C7 C6 1.387(2) . ?
C7 C8 1.3922(18) . ?
C7 H1A 0.9300 . ?
O2 C10 1.1966(17) . ?
C8 C1 1.5126(17) . ?
C10 C9 1.516(2) . ?
C1 C9 1.5651(18) . ?
C1 H4 0.9800 . ?
C6 C5 1.382(2) . ?
C6 H5 0.9300 . ?
C9 C13 1.5192(18) . ?
C9 H6 0.9800 . ?
C5 C4 1.381(2) . ?
C5 H7 0.9300 . ?
O5 C13 1.318(2) . ?
O5 C14B 1.495(5) . ?
O5 C14A 1.510(6) . ?
C4 H9 0.9300 . ?
C11 C12 1.492(3) . ?
C11 H12A 0.9700 . ?
C11 H12B 0.9700 . ?
C12 H14A 0.9600 . ?
C12 H14B 0.9600 . ?
C12 H14C 0.9600 . ?
C14A C15A 1.539(11) . ?
C14A H14D 0.9700 . ?
C14A H14E 0.9700 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C14B C15B 1.383(13) . ?
C14B H14F 0.9700 . ?
C14B H14G 0.9700 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 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
C2 N1 C1 125.74(11) . . ?
C2 N1 HN1 118.9(11) . . ?
C1 N1 HN1 114.9(11) . . ?
C10 O3 C11 116.69(12) . . ?
C8 C3 C4 120.62(12) . . ?
C8 C3 N2 119.89(12) . . ?
C4 C3 N2 119.48(12) . . ?
C2 N2 C3 122.76(12) . . ?
C2 N2 HN2 118.2(12) . . ?
C3 N2 HN2 118.7(12) . . ?
C6 C7 C8 120.60(14) . . ?
C6 C7 H1A 119.7 . . ?
C8 C7 H1A 119.7 . . ?
C3 C8 C7 118.74(12) . . ?
C3 C8 C1 118.88(11) . . ?
C7 C8 C1 122.38(12) . . ?
O2 C10 O3 124.94(14) . . ?
O2 C10 C9 124.02(12) . . ?
O3 C10 C9 111.04(11) . . ?
N1 C1 C8 110.12(10) . . ?
N1 C1 C9 109.45(10) . . ?
C8 C1 C9 114.24(10) . . ?
N1 C1 H4 107.6 . . ?
C8 C1 H4 107.6 . . ?
C9 C1 H4 107.6 . . ?
C5 C6 C7 120.08(13) . . ?
C5 C6 H5 120.0 . . ?
C7 C6 H5 120.0 . . ?
C10 C9 C13 108.57(11) . . ?
C10 C9 C1 112.48(10) . . ?
C13 C9 C1 113.30(11) . . ?
C10 C9 H6 107.4 . . ?
C13 C9 H6 107.4 . . ?
C1 C9 H6 107.4 . . ?
C4 C5 C6 120.09(13) . . ?
C4 C5 H7 120.0 . . ?
C6 C5 H7 120.0 . . ?
C13 O5 C14B 121.3(3) . . ?
C13 O5 C14A 111.2(3) . . ?
C14B O5 C14A 26.7(2) . . ?
C5 C4 C3 119.80(14) . . ?
C5 C4 H9 120.1 . . ?
C3 C4 H9 120.1 . . ?
O1 C2 N1 122.22(12) . . ?
O1 C2 N2 120.83(12) . . ?
N1 C2 N2 116.94(11) . . ?
O4 C13 O5 124.50(14) . . ?
O4 C13 C9 125.61(14) . . ?
O5 C13 C9 109.86(12) . . ?
O3 C11 C12 111.16(14) . . ?
O3 C11 H12A 109.4 . . ?
C12 C11 H12A 109.4 . . ?
O3 C11 H12B 109.4 . . ?
C12 C11 H12B 109.4 . . ?
H12A C11 H12B 108.0 . . ?
C11 C12 H14A 109.5 . . ?
C11 C12 H14B 109.5 . . ?
H14A C12 H14B 109.5 . . ?
C11 C12 H14C 109.5 . . ?
H14A C12 H14C 109.5 . . ?
H14B C12 H14C 109.5 . . ?
O5 C14A C15A 103.1(6) . . ?
O5 C14A H14D 111.1 . . ?
C15A C14A H14D 111.1 . . ?
O5 C14A H14E 111.1 . . ?
C15A C14A H14E 111.1 . . ?
H14D C14A H14E 109.1 . . ?
C15B C14B O5 106.3(7) . . ?
C15B C14B H14F 110.5 . . ?
O5 C14B H14F 110.5 . . ?
C15B C14B H14G 110.5 . . ?
O5 C14B H14G 110.5 . . ?
H14F C14B H14G 108.7 . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.047

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
