# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mpt9849_0m
_database_code_depnum_ccdc_archive 'CCDC 1528351'
_audit_update_record             
;
2017-01-18 deposited with the CCDC.
2017-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1,3-di-tert-butyl-5-(1-(4-chlorophenyl)-3-oxo-3-(p-tolyl)propyl)pyrimidine-2,4,6(1H,3H,5H)-trione
_chemical_name_common            
1,3-di-tert-butyl-5-(1-(4-chlorophenyl)-3-oxo-3-(p-tolyl)propyl)pyrimidine-2,4,6(1H,3H,5H)-trione
_chemical_melting_point          140.6
_chemical_absolute_configuration ad
_chemical_formula_moiety         497.03
_chemical_formula_sum            'C28 H33 Cl N2 O4'
_chemical_formula_weight         497.01

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'
Cl Cl 0.1484 0.1585 '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

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

_cell_length_a                   10.660(4)
_cell_length_b                   9.536(4)
_cell_length_c                   13.873(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.324(7)
_cell_angle_gamma                90.00
_cell_volume                     1346.2(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2340
_cell_measurement_theta_max      18.517
_cell_measurement_theta_min      2.632

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9279
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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 Smart APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13894
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4455
_reflns_number_gt                3422
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0249P)²+1.0523P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(15)
_refine_ls_number_reflns         4455
_refine_ls_number_parameters     323
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_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
Cl1 Cl 0.62698(19) 0.3184(3) 0.62212(11) 0.1340(8) Uani 1 1 d . . .
O1 O 0.3150(3) 0.4481(3) 0.1150(3) 0.0657(9) Uani 1 1 d . . .
O2 O 0.8246(3) 0.5416(3) 0.1927(2) 0.0637(8) Uani 1 1 d . . .
O3 O 0.9559(3) 0.1800(3) 0.3935(2) 0.0754(10) Uani 1 1 d . . .
O4 O 0.6285(3) 0.0979(3) 0.1208(2) 0.0595(8) Uani 1 1 d . . .
N1 N 0.9312(3) 0.3476(3) 0.2713(2) 0.0411(7) Uani 1 1 d . . .
N2 N 0.8312(3) 0.1206(3) 0.2339(2) 0.0432(8) Uani 1 1 d . . .
C1 C 0.1622(5) 1.1081(5) 0.0612(4) 0.0690(14) Uani 1 1 d . . .
H1A H 0.1317 1.1287 -0.0097 0.104 Uiso 1 1 calc R . .
H1B H 0.2274 1.1756 0.0947 0.104 Uiso 1 1 calc R . .
H1C H 0.0897 1.1121 0.0888 0.104 Uiso 1 1 calc R . .
C2 C 0.2218(4) 0.9622(4) 0.0768(3) 0.0489(10) Uani 1 1 d . . .
C3 C 0.1446(4) 0.8435(5) 0.0554(3) 0.0548(11) Uani 1 1 d . . .
H3 H 0.0538 0.8529 0.0310 0.066 Uiso 1 1 calc R . .
C4 C 0.1992(4) 0.7110(4) 0.0696(3) 0.0508(10) Uani 1 1 d . . .
H4 H 0.1446 0.6328 0.0554 0.061 Uiso 1 1 calc R . .
C5 C 0.3347(4) 0.6930(4) 0.1049(3) 0.0405(9) Uani 1 1 d . . .
C6 C 0.4116(4) 0.8111(4) 0.1240(3) 0.0479(10) Uani 1 1 d . . .
H6 H 0.5026 0.8017 0.1463 0.058 Uiso 1 1 calc R . .
C7 C 0.3564(4) 0.9447(4) 0.1108(3) 0.0531(11) Uani 1 1 d . . .
H7 H 0.4108 1.0230 0.1251 0.064 Uiso 1 1 calc R . .
C8 C 0.3878(4) 0.5479(5) 0.1191(3) 0.0467(10) Uani 1 1 d . . .
C9 C 0.5336(4) 0.5248(4) 0.1363(3) 0.0516(10) Uani 1 1 d . . .
H9A H 0.5827 0.5956 0.1825 0.062 Uiso 1 1 calc R . .
H9B H 0.5531 0.5355 0.0727 0.062 Uiso 1 1 calc R . .
C10 C 0.5777(4) 0.3793(4) 0.1797(3) 0.0445(9) Uani 1 1 d . . .
H10 H 0.5084 0.3137 0.1446 0.053 Uiso 1 1 calc R . .
C11 C 0.5912(4) 0.3670(4) 0.2916(3) 0.0457(10) Uani 1 1 d . . .
C12 C 0.6540(5) 0.4651(6) 0.3617(3) 0.0706(13) Uani 1 1 d . . .
H12 H 0.6896 0.5441 0.3404 0.085 Uiso 1 1 calc R . .
C13 C 0.6659(5) 0.4500(7) 0.4629(4) 0.0832(16) Uani 1 1 d . . .
H13 H 0.7093 0.5179 0.5089 0.100 Uiso 1 1 calc R . .
C14 C 0.6143(5) 0.3359(7) 0.4949(4) 0.0797(15) Uani 1 1 d . . .
C15 C 0.5528(6) 0.2336(6) 0.4290(4) 0.0861(17) Uani 1 1 d . . .
H15 H 0.5186 0.1547 0.4516 0.103 Uiso 1 1 calc R . .
C16 C 0.5424(5) 0.2496(5) 0.3271(3) 0.0681(13) Uani 1 1 d . . .
H16 H 0.5017 0.1798 0.2818 0.082 Uiso 1 1 calc R . .
C17 C 0.7181(4) 0.1723(4) 0.1682(3) 0.0441(9) Uani 1 1 d . . .
C18 C 0.7060(4) 0.3309(4) 0.1565(3) 0.0413(8) Uani 1 1 d . . .
H18 H 0.6899 0.3485 0.0843 0.050 Uiso 1 1 calc R . .
C19 C 0.8249(4) 0.4164(4) 0.2083(3) 0.0442(9) Uani 1 1 d . . .
C20 C 0.9083(4) 0.2130(4) 0.3071(3) 0.0493(10) Uani 1 1 d . . .
C21 C 0.8557(4) -0.0374(4) 0.2481(3) 0.0531(10) Uani 1 1 d . . .
C22 C 1.0021(5) -0.0639(5) 0.2996(4) 0.0816(16) Uani 1 1 d . . .
H22A H 1.0532 -0.0133 0.2646 0.122 Uiso 1 1 calc R . .
H22B H 1.0201 -0.1624 0.2981 0.122 Uiso 1 1 calc R . .
H22C H 1.0249 -0.0325 0.3685 0.122 Uiso 1 1 calc R . .
C23 C 0.8213(5) -0.1056(5) 0.1444(4) 0.0700(13) Uani 1 1 d . . .
H23A H 0.7276 -0.1081 0.1155 0.105 Uiso 1 1 calc R . .
H23B H 0.8554 -0.1995 0.1508 0.105 Uiso 1 1 calc R . .
H23C H 0.8594 -0.0523 0.1014 0.105 Uiso 1 1 calc R . .
C24 C 0.7719(5) -0.0958(5) 0.3104(3) 0.0692(14) Uani 1 1 d . . .
H24A H 0.7943 -0.0494 0.3747 0.104 Uiso 1 1 calc R . .
H24B H 0.7877 -0.1946 0.3203 0.104 Uiso 1 1 calc R . .
H24C H 0.6807 -0.0801 0.2753 0.104 Uiso 1 1 calc R . .
C25 C 1.0581(4) 0.4249(4) 0.3230(3) 0.0500(10) Uani 1 1 d . . .
C26 C 1.1683(4) 0.3211(6) 0.3680(4) 0.0910(18) Uani 1 1 d . . .
H26A H 1.1522 0.2744 0.4245 0.137 Uiso 1 1 calc R . .
H26B H 1.2505 0.3703 0.3902 0.137 Uiso 1 1 calc R . .
H26C H 1.1718 0.2532 0.3178 0.137 Uiso 1 1 calc R . .
C27 C 1.0969(5) 0.5077(5) 0.2414(4) 0.0708(14) Uani 1 1 d . . .
H27A H 1.1070 0.4443 0.1904 0.106 Uiso 1 1 calc R . .
H27B H 1.1784 0.5557 0.2714 0.106 Uiso 1 1 calc R . .
H27C H 1.0295 0.5748 0.2113 0.106 Uiso 1 1 calc R . .
C28 C 1.0378(5) 0.5213(5) 0.4035(3) 0.0736(14) Uani 1 1 d . . .
H28A H 0.9691 0.5870 0.3733 0.110 Uiso 1 1 calc R . .
H28B H 1.1178 0.5712 0.4348 0.110 Uiso 1 1 calc R . .
H28C H 1.0136 0.4670 0.4534 0.110 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
Cl1 C14 1.738(5) . ?
O1 C8 1.218(5) . ?
O2 C19 1.214(5) . ?
O3 C20 1.196(5) . ?
O4 C17 1.214(4) . ?
N1 C19 1.373(5) . ?
N1 C20 1.423(5) . ?
N1 C25 1.520(5) . ?
N2 C17 1.369(5) . ?
N2 C20 1.409(5) . ?
N2 C21 1.532(5) . ?
C1 C2 1.518(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.379(6) . ?
C2 C7 1.380(5) . ?
C3 C4 1.380(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(5) . ?
C5 C8 1.486(5) . ?
C6 C7 1.392(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.516(5) . ?
C9 C10 1.530(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.520(5) . ?
C10 C18 1.565(5) . ?
C10 H10 0.9800 . ?
C11 C12 1.372(6) . ?
C11 C16 1.385(6) . ?
C12 C13 1.378(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.352(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(8) . ?
C15 C16 1.393(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.522(5) . ?
C18 C19 1.498(5) . ?
C18 H18 0.9800 . ?
C21 C24 1.521(6) . ?
C21 C23 1.521(6) . ?
C21 C22 1.532(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C28 1.511(6) . ?
C25 C26 1.520(6) . ?
C25 C27 1.535(6) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
C19 N1 C20 117.3(3) . . ?
C19 N1 C25 121.2(3) . . ?
C20 N1 C25 119.5(3) . . ?
C17 N2 C20 117.6(3) . . ?
C17 N2 C21 121.5(3) . . ?
C20 N2 C21 118.8(3) . . ?
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 C7 117.8(4) . . ?
C3 C2 C1 121.6(4) . . ?
C7 C2 C1 120.6(4) . . ?
C2 C3 C4 121.4(4) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 117.7(4) . . ?
C6 C5 C8 123.8(3) . . ?
C4 C5 C8 118.5(4) . . ?
C5 C6 C7 121.4(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C2 C7 C6 120.8(4) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
O1 C8 C5 120.5(3) . . ?
O1 C8 C9 120.2(4) . . ?
C5 C8 C9 119.2(4) . . ?
C8 C9 C10 112.0(3) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 113.3(3) . . ?
C11 C10 C18 111.4(3) . . ?
C9 C10 C18 111.8(3) . . ?
C11 C10 H10 106.6 . . ?
C9 C10 H10 106.6 . . ?
C18 C10 H10 106.6 . . ?
C12 C11 C16 117.1(4) . . ?
C12 C11 C10 123.3(4) . . ?
C16 C11 C10 119.6(4) . . ?
C11 C12 C13 121.9(5) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 119.7(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.1(5) . . ?
C13 C14 Cl1 119.6(5) . . ?
C15 C14 Cl1 119.3(5) . . ?
C14 C15 C16 118.6(5) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C11 C16 C15 121.6(5) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
O4 C17 N2 123.0(3) . . ?
O4 C17 C18 119.7(4) . . ?
N2 C17 C18 117.3(3) . . ?
C19 C18 C17 117.2(3) . . ?
C19 C18 C10 114.1(3) . . ?
C17 C18 C10 108.8(3) . . ?
C19 C18 H18 105.2 . . ?
C17 C18 H18 105.2 . . ?
C10 C18 H18 105.2 . . ?
O2 C19 N1 122.8(4) . . ?
O2 C19 C18 119.5(4) . . ?
N1 C19 C18 117.7(3) . . ?
O3 C20 N2 122.7(4) . . ?
O3 C20 N1 121.4(4) . . ?
N2 C20 N1 115.9(3) . . ?
C24 C21 C23 111.3(4) . . ?
C24 C21 N2 109.1(3) . . ?
C23 C21 N2 108.3(3) . . ?
C24 C21 C22 111.3(4) . . ?
C23 C21 C22 107.2(4) . . ?
N2 C21 C22 109.5(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C28 C25 N1 109.9(3) . . ?
C28 C25 C26 110.8(4) . . ?
N1 C25 C26 110.4(3) . . ?
C28 C25 C27 111.2(4) . . ?
N1 C25 C27 107.4(3) . . ?
C26 C25 C27 107.0(4) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.040
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
_chemical_compound_source        
1,3-di-tert-butylpyrimidine-2,4,6(1H,3H,5H)-trione/3-(4-chlorophenyl)-1-(p-tolyl)propan-1-one
