# 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_shelxl
_audit_block_doi                 10.5517/cc1jpcrb
_database_code_depnum_ccdc_archive 'CCDC 1420722'
_audit_update_record             
;
2015-08-26 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
3-amino-1-(4-chlorophenyl)-1',3'-dimethyl-2',4',6'-trioxo-2',3',4',6,6',7,8,8a-octahydro-1H,1'H-spiro[naphthalene-2,5'-pyrimidine]-4-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H21 Cl N4 O3'
_chemical_formula_sum            'C22 H21 Cl N4 O3'
_chemical_formula_weight         424.88

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   'I 2/a'
_symmetry_space_group_name_HALL  '-I 2ya'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   22.6632(11)
_cell_length_b                   10.9979(3)
_cell_length_c                   17.6446(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.416(5)
_cell_angle_gamma                90.00
_cell_volume                     4121.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24129
_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3623
_reflns_number_gt                1959
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1027P)²+0.7708P] 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         3623
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0761
_refine_ls_wR_factor_ref         0.2198
_refine_ls_wR_factor_gt          0.1816
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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
Cl1 Cl 0.66266(6) 0.51154(11) -0.07510(8) 0.0785(5) Uani 1 1 d . . .
O1 O 0.67130(15) 0.1640(3) 0.26751(18) 0.0651(9) Uani 1 1 d . . .
O2 O 0.47789(15) 0.0978(3) 0.0569(2) 0.0771(10) Uani 1 1 d . . .
N5 N 0.5282(2) 0.0273(5) 0.2377(3) 0.0762(14) Uani 1 1 d . . .
N1 N 0.51544(16) 0.2858(3) 0.0919(2) 0.0594(10) Uani 1 1 d . . .
N3 N 0.5626(3) -0.2706(4) 0.2810(3) 0.1098(18) Uani 1 1 d . . .
O3 O 0.54652(19) 0.4737(3) 0.1417(2) 0.1007(13) Uani 1 1 d . . .
N2 N 0.60578(18) 0.3174(3) 0.2089(2) 0.0590(10) Uani 1 1 d . . .
C8 C 0.6704(2) -0.0237(4) 0.1345(3) 0.0545(11) Uani 1 1 d . . .
H8 H 0.7016 0.0187 0.1798 0.065 Uiso 1 1 calc R . .
C14 C 0.5985(2) -0.1066(4) 0.2034(3) 0.0523(11) Uani 1 1 d . . .
C3 C 0.6816(2) 0.2496(4) 0.0864(3) 0.0579(12) Uani 1 1 d . . .
H3 H 0.7093 0.2313 0.1380 0.069 Uiso 1 1 calc R . .
C4 C 0.63169(19) 0.1715(4) 0.0500(2) 0.0500(11) Uani 1 1 d . . .
C16 C 0.58211(18) 0.1085(3) 0.1528(2) 0.0450(10) Uani 1 1 d . . .
C13 C 0.64584(19) -0.1312(4) 0.1673(2) 0.0520(11) Uani 1 1 d . . .
C15 C 0.5688(2) 0.0018(4) 0.1994(2) 0.0505(11) Uani 1 1 d . . .
C5 C 0.5927(2) 0.1993(4) -0.0282(3) 0.0594(12) Uani 1 1 d . . .
H5 H 0.5596 0.1476 -0.0553 0.071 Uiso 1 1 calc R . .
C7 C 0.61588(19) 0.0646(4) 0.0930(3) 0.0491(11) Uani 1 1 d . . .
H7 H 0.5845 0.0170 0.0511 0.059 Uiso 1 1 calc R . .
C2 C 0.6915(2) 0.3529(4) 0.0488(3) 0.0601(12) Uani 1 1 d . . .
H2 H 0.7251 0.4042 0.0750 0.072 Uiso 1 1 calc R . .
C40 C 0.5797(3) -0.2000(5) 0.2459(3) 0.0724(14) Uani 1 1 d . . .
C18 C 0.5554(2) 0.3656(4) 0.1467(3) 0.0636(13) Uani 1 1 d . . .
C17 C 0.6244(2) 0.1967(4) 0.2155(3) 0.0509(11) Uani 1 1 d . . .
C19 C 0.5202(2) 0.1628(4) 0.0977(3) 0.0558(11) Uani 1 1 d . . .
C6 C 0.6027(2) 0.3029(5) -0.0658(3) 0.0651(13) Uani 1 1 d . . .
H6 H 0.5760 0.3210 -0.1180 0.078 Uiso 1 1 calc R . .
C1 C 0.6515(2) 0.3796(4) -0.0274(3) 0.0579(12) Uani 1 1 d . . .
C9 C 0.7025(2) -0.0654(5) 0.0756(3) 0.0715(14) Uani 1 1 d . . .
H9A H 0.6709 -0.0928 0.0256 0.086 Uiso 1 1 calc R . .
H9B H 0.7249 0.0024 0.0630 0.086 Uiso 1 1 calc R . .
C12 C 0.6664(2) -0.2445(4) 0.1630(3) 0.0691(14) Uani 1 1 d . . .
H12 H 0.6490 -0.3069 0.1840 0.083 Uiso 1 1 calc R . .
C11 C 0.7144(3) -0.2785(5) 0.1276(3) 0.0805(16) Uani 1 1 d . . .
H11A H 0.6942 -0.3209 0.0769 0.097 Uiso 1 1 calc R . .
H11B H 0.7446 -0.3336 0.1640 0.097 Uiso 1 1 calc R . .
C10 C 0.7487(2) -0.1690(5) 0.1125(4) 0.0857(16) Uani 1 1 d . . .
H10A H 0.7706 -0.1908 0.0760 0.103 Uiso 1 1 calc R . .
H10B H 0.7798 -0.1422 0.1630 0.103 Uiso 1 1 calc R . .
C21 C 0.6471(3) 0.4027(5) 0.2672(4) 0.098(2) Uani 1 1 d . . .
H21A H 0.6293 0.4828 0.2570 0.147 Uiso 1 1 calc R . .
H21B H 0.6878 0.4030 0.2617 0.147 Uiso 1 1 calc R . .
H21C H 0.6513 0.3781 0.3210 0.147 Uiso 1 1 calc R . .
C20 C 0.4609(2) 0.3386(5) 0.0268(3) 0.0957(19) Uani 1 1 d . . .
H20A H 0.4631 0.4257 0.0299 0.144 Uiso 1 1 calc R . .
H20B H 0.4226 0.3116 0.0331 0.144 Uiso 1 1 calc R . .
H20C H 0.4616 0.3126 -0.0248 0.144 Uiso 1 1 calc R . .
H15 H 0.519(2) -0.022(4) 0.267(3) 0.065(17) Uiso 1 1 d . . .
H25 H 0.502(3) 0.088(5) 0.227(3) 0.09(2) 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
Cl1 C1 1.740(4) . ?
O1 C17 1.192(4) . ?
O2 C19 1.212(5) . ?
N5 C15 1.348(6) . ?
N5 H15 0.82(5) . ?
N5 H25 0.88(5) . ?
N1 C19 1.358(5) . ?
N1 C18 1.383(5) . ?
N1 C20 1.481(6) . ?
N3 C40 1.142(6) . ?
O3 C18 1.204(5) . ?
N2 C18 1.384(6) . ?
N2 C17 1.385(5) . ?
N2 C21 1.464(5) . ?
C8 C13 1.506(6) . ?
C8 C9 1.532(6) . ?
C8 C7 1.541(6) . ?
C8 H8 0.9800 . ?
C14 C15 1.359(6) . ?
C14 C40 1.423(6) . ?
C14 C13 1.451(6) . ?
C3 C2 1.373(6) . ?
C3 C4 1.387(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(5) . ?
C4 C7 1.510(6) . ?
C16 C19 1.523(6) . ?
C16 C15 1.523(6) . ?
C16 C17 1.531(5) . ?
C16 C7 1.579(6) . ?
C13 C12 1.342(6) . ?
C5 C6 1.377(6) . ?
C5 H5 0.9300 . ?
C7 H7 0.9800 . ?
C2 C1 1.366(6) . ?
C2 H2 0.9300 . ?
C6 C1 1.368(6) . ?
C6 H6 0.9300 . ?
C9 C10 1.531(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C12 C11 1.479(7) . ?
C12 H12 0.9300 . ?
C11 C10 1.507(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C15 N5 H15 123(3) . . ?
C15 N5 H25 126(4) . . ?
H15 N5 H25 110(5) . . ?
C19 N1 C18 124.3(4) . . ?
C19 N1 C20 118.1(4) . . ?
C18 N1 C20 117.3(4) . . ?
C18 N2 C17 125.2(4) . . ?
C18 N2 C21 117.4(4) . . ?
C17 N2 C21 117.0(4) . . ?
C13 C8 C9 110.6(4) . . ?
C13 C8 C7 109.5(3) . . ?
C9 C8 C7 111.0(4) . . ?
C13 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C15 C14 C40 115.2(4) . . ?
C15 C14 C13 124.7(4) . . ?
C40 C14 C13 120.0(4) . . ?
C2 C3 C4 122.2(4) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 117.3(4) . . ?
C3 C4 C7 123.2(4) . . ?
C5 C4 C7 119.4(4) . . ?
C19 C16 C15 109.6(3) . . ?
C19 C16 C17 114.7(4) . . ?
C15 C16 C17 106.9(3) . . ?
C19 C16 C7 104.3(3) . . ?
C15 C16 C7 111.0(3) . . ?
C17 C16 C7 110.5(3) . . ?
C12 C13 C14 121.5(4) . . ?
C12 C13 C8 121.6(4) . . ?
C14 C13 C8 116.8(4) . . ?
C14 C15 N5 124.7(4) . . ?
C14 C15 C16 121.1(4) . . ?
N5 C15 C16 114.1(4) . . ?
C6 C5 C4 120.5(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C4 C7 C8 115.9(3) . . ?
C4 C7 C16 110.7(3) . . ?
C8 C7 C16 111.8(3) . . ?
C4 C7 H7 105.9 . . ?
C8 C7 H7 105.9 . . ?
C16 C7 H7 105.9 . . ?
C1 C2 C3 119.3(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
N3 C40 C14 176.4(6) . . ?
O3 C18 N2 120.5(5) . . ?
O3 C18 N1 121.6(5) . . ?
N2 C18 N1 118.0(4) . . ?
O1 C17 N2 121.1(4) . . ?
O1 C17 C16 122.1(4) . . ?
N2 C17 C16 116.8(4) . . ?
O2 C19 N1 121.2(4) . . ?
O2 C19 C16 120.7(4) . . ?
N1 C19 C16 118.0(4) . . ?
C1 C6 C5 120.7(4) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C2 C1 C6 120.0(4) . . ?
C2 C1 Cl1 119.8(4) . . ?
C6 C1 Cl1 120.2(4) . . ?
C10 C9 C8 110.5(4) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C13 C12 C11 125.4(5) . . ?
C13 C12 H12 117.3 . . ?
C11 C12 H12 117.3 . . ?
C12 C11 C10 112.0(4) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C10 C9 110.5(4) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.048
_chemical_compound_source        'Layering Method at low temperature'
