# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_No1
_database_code_depnum_ccdc_archive 'CCDC 1868522'
_audit_update_record             
;
2018-09-19 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXTL
_chemical_name_systematic        
(R)-1-(4-bromobutan-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H13 Br N2 O2'
_chemical_formula_sum            'C9 H13 Br N2 O2'
_chemical_formula_weight         261.12
_chemical_absolute_configuration ad

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(1)
_symmetry_space_group_name_Hall  'P 4w'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   11.1159(3)
_cell_length_b                   11.1159(3)
_cell_length_c                   18.9404(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2340.34(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9981
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      21.07

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    3.492
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5721
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(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  '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            100569
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         28.33
_reflns_number_total             5811
_reflns_number_gt                3608
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1111P)²+5.1138P] 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   0.02(2)
_refine_ls_number_reflns         5811
_refine_ls_number_parameters     257
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1324
_refine_ls_R_factor_gt           0.0814
_refine_ls_wR_factor_ref         0.2452
_refine_ls_wR_factor_gt          0.2077
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.5261(5) 0.8025(5) 0.0348(3) 0.0352(12) Uani 1 1 d . . .
O1 O 0.4568(4) 0.8722(4) 0.0039(2) 0.0469(11) Uani 1 1 d . . .
N1 N 0.5380(4) 0.8064(4) 0.1068(3) 0.0335(10) Uani 1 1 d . . .
H1 H 0.4936 0.8588 0.1289 0.040 Uiso 1 1 calc R . .
C2 C 0.6106(5) 0.7384(5) 0.1472(3) 0.0305(11) Uani 1 1 d . . .
O2 O 0.6148(4) 0.7520(4) 0.2118(2) 0.0427(10) Uani 1 1 d . . .
N2 N 0.6797(5) 0.6554(4) 0.1127(3) 0.0382(11) Uani 1 1 d . . .
C3 C 0.6726(6) 0.6466(6) 0.0384(3) 0.0434(15) Uani 1 1 d . . .
H3 H 0.7216 0.5897 0.0156 0.052 Uiso 1 1 calc R . .
C4 C 0.6003(6) 0.7145(6) -0.0012(3) 0.0435(15) Uani 1 1 d . . .
C5 C 0.5887(10) 0.7042(9) -0.0803(4) 0.076(3) Uani 1 1 d . . .
H5A H 0.6538 0.6551 -0.0985 0.114 Uiso 1 1 calc R . .
H5B H 0.5926 0.7837 -0.1012 0.114 Uiso 1 1 calc R . .
H5C H 0.5122 0.6671 -0.0919 0.114 Uiso 1 1 calc R . .
C6 C 0.7709(7) 0.5847(6) 0.1519(3) 0.0488(16) Uani 1 1 d . . .
H6 H 0.7561 0.5974 0.2029 0.059 Uiso 1 1 calc R . .
C7 C 0.8973(8) 0.6315(10) 0.1358(6) 0.076(2) Uani 1 1 d . . .
H7A H 0.9092 0.6341 0.0851 0.114 Uiso 1 1 calc R . .
H7B H 0.9564 0.5784 0.1569 0.114 Uiso 1 1 calc R . .
H7C H 0.9064 0.7118 0.1552 0.114 Uiso 1 1 calc R . .
C8 C 0.7589(9) 0.4523(7) 0.1377(4) 0.065(2) Uani 1 1 d . . .
H8A H 0.7756 0.4380 0.0876 0.078 Uiso 1 1 calc R . .
H8B H 0.8207 0.4099 0.1650 0.078 Uiso 1 1 calc R . .
C9 C 0.6389(13) 0.3981(9) 0.1550(7) 0.098(4) Uani 1 1 d . . .
H9A H 0.6387 0.3134 0.1407 0.118 Uiso 1 1 calc R . .
H9B H 0.5764 0.4397 0.1279 0.118 Uiso 1 1 calc R . .
Br1 Br 0.60083(19) 0.40864(13) 0.25502(11) 0.1514(9) Uani 1 1 d . . .
C10 C 0.3269(6) 0.0474(6) 0.1464(3) 0.0454(15) Uani 1 1 d . . .
O3 O 0.3997(5) -0.0185(5) 0.1781(3) 0.0620(15) Uani 1 1 d . . .
N3 N 0.3146(4) 0.0401(5) 0.0748(3) 0.0383(11) Uani 1 1 d . . .
H3A H 0.3638 -0.0085 0.0532 0.046 Uiso 1 1 calc R . .
C11 C 0.2332(5) 0.1007(5) 0.0323(3) 0.0366(13) Uani 1 1 d . . .
O4 O 0.2272(4) 0.0847(4) -0.0303(2) 0.0476(11) Uani 1 1 d . . .
N4 N 0.1589(4) 0.1786(4) 0.0693(2) 0.0349(10) Uani 1 1 d . . .
C12 C 0.1706(6) 0.1942(6) 0.1415(3) 0.0413(14) Uani 1 1 d . . .
H12 H 0.1201 0.2506 0.1637 0.050 Uiso 1 1 calc R . .
C13 C 0.2494(6) 0.1340(6) 0.1816(3) 0.0448(15) Uani 1 1 d . . .
C14 C 0.2594(9) 0.1504(10) 0.2599(4) 0.077(3) Uani 1 1 d . . .
H14A H 0.3370 0.1854 0.2712 0.116 Uiso 1 1 calc R . .
H14B H 0.2518 0.0730 0.2831 0.116 Uiso 1 1 calc R . .
H14C H 0.1959 0.2035 0.2761 0.116 Uiso 1 1 calc R . .
C15 C 0.0620(5) 0.2412(6) 0.0298(3) 0.0407(14) Uani 1 1 d . . .
H15 H 0.0777 0.2297 -0.0212 0.049 Uiso 1 1 calc R . .
C16 C 0.0623(7) 0.3740(6) 0.0442(5) 0.062(2) Uani 1 1 d . . .
H16A H 0.0470 0.3880 0.0939 0.093 Uiso 1 1 calc R . .
H16B H 0.0001 0.4126 0.0163 0.093 Uiso 1 1 calc R . .
H16C H 0.1401 0.4074 0.0317 0.093 Uiso 1 1 calc R . .
C17 C -0.0605(6) 0.1818(7) 0.0469(4) 0.0531(16) Uani 1 1 d . . .
H17A H -0.0787 0.1949 0.0969 0.064 Uiso 1 1 calc R . .
H17B H -0.1232 0.2220 0.0192 0.064 Uiso 1 1 calc R . .
C18 C -0.0654(9) 0.0547(9) 0.0326(7) 0.090(3) Uani 1 1 d . . .
H18A H 0.0006 0.0144 0.0574 0.108 Uiso 1 1 calc R . .
H18B H -0.0544 0.0412 -0.0181 0.108 Uiso 1 1 calc R . .
Br2 Br -0.21671(15) -0.01554(16) 0.06198(11) 0.1415(8) 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 O1 1.240(7) . ?
C1 N1 1.371(8) . ?
C1 C4 1.450(8) . ?
N1 C2 1.344(8) . ?
N1 H1 0.8700 . ?
C2 O2 1.233(7) . ?
C2 N2 1.367(7) . ?
N2 C3 1.412(8) . ?
N2 C6 1.483(8) . ?
C3 C4 1.335(8) . ?
C3 H3 0.9400 . ?
C4 C5 1.507(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 C8 1.502(11) . ?
C6 C7 1.529(12) . ?
C6 H6 0.9900 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 C9 1.500(16) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 Br1 1.944(13) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 O3 1.247(8) . ?
C10 N3 1.366(8) . ?
C10 C13 1.454(8) . ?
N3 C11 1.385(8) . ?
N3 H3A 0.8700 . ?
C11 O4 1.201(7) . ?
C11 N4 1.387(7) . ?
N4 C12 1.385(8) . ?
N4 C15 1.484(7) . ?
C12 C13 1.339(9) . ?
C12 H12 0.9400 . ?
C13 C14 1.498(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 C16 1.502(10) . ?
C15 C17 1.548(10) . ?
C15 H15 0.9900 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 C18 1.440(12) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 Br2 1.936(10) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?

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
O1 C1 N1 120.7(5) . . ?
O1 C1 C4 123.5(5) . . ?
N1 C1 C4 115.8(5) . . ?
C2 N1 C1 127.3(5) . . ?
C2 N1 H1 116.4 . . ?
C1 N1 H1 116.4 . . ?
O2 C2 N1 121.2(5) . . ?
O2 C2 N2 122.4(5) . . ?
N1 C2 N2 116.4(5) . . ?
C2 N2 C3 119.4(5) . . ?
C2 N2 C6 120.2(5) . . ?
C3 N2 C6 120.0(5) . . ?
C4 C3 N2 123.7(6) . . ?
C4 C3 H3 118.1 . . ?
N2 C3 H3 118.1 . . ?
C3 C4 C1 117.3(5) . . ?
C3 C4 C5 124.6(6) . . ?
C1 C4 C5 118.1(5) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C8 111.6(6) . . ?
N2 C6 C7 110.4(6) . . ?
C8 C6 C7 112.3(7) . . ?
N2 C6 H6 107.4 . . ?
C8 C6 H6 107.4 . . ?
C7 C6 H6 107.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C6 115.7(7) . . ?
C9 C8 H8A 108.4 . . ?
C6 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C6 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
C8 C9 Br1 112.5(8) . . ?
C8 C9 H9A 109.1 . . ?
Br1 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
Br1 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
O3 C10 N3 120.5(6) . . ?
O3 C10 C13 123.6(6) . . ?
N3 C10 C13 115.9(5) . . ?
C10 N3 C11 127.8(5) . . ?
C10 N3 H3A 116.1 . . ?
C11 N3 H3A 116.1 . . ?
O4 C11 N3 122.5(5) . . ?
O4 C11 N4 123.8(5) . . ?
N3 C11 N4 113.6(5) . . ?
C12 N4 C11 121.4(5) . . ?
C12 N4 C15 120.4(5) . . ?
C11 N4 C15 118.1(5) . . ?
C13 C12 N4 124.0(5) . . ?
C13 C12 H12 118.0 . . ?
N4 C12 H12 118.0 . . ?
C12 C13 C10 117.3(5) . . ?
C12 C13 C14 123.4(6) . . ?
C10 C13 C14 119.4(6) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 C16 111.6(6) . . ?
N4 C15 C17 109.5(5) . . ?
C16 C15 C17 112.6(6) . . ?
N4 C15 H15 107.7 . . ?
C16 C15 H15 107.7 . . ?
C17 C15 H15 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C15 114.4(7) . . ?
C18 C17 H17A 108.7 . . ?
C15 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C15 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 Br2 112.0(8) . . ?
C17 C18 H18A 109.2 . . ?
Br2 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
Br2 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?

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
O1 C1 N1 C2 -178.8(5) . . . . ?
C4 C1 N1 C2 0.2(9) . . . . ?
C1 N1 C2 O2 178.7(6) . . . . ?
C1 N1 C2 N2 -0.5(8) . . . . ?
O2 C2 N2 C3 -178.4(6) . . . . ?
N1 C2 N2 C3 0.8(8) . . . . ?
O2 C2 N2 C6 -5.2(8) . . . . ?
N1 C2 N2 C6 174.0(6) . . . . ?
C2 N2 C3 C4 -0.9(10) . . . . ?
C6 N2 C3 C4 -174.1(7) . . . . ?
N2 C3 C4 C1 0.5(11) . . . . ?
N2 C3 C4 C5 -178.1(8) . . . . ?
O1 C1 C4 C3 178.8(7) . . . . ?
N1 C1 C4 C3 -0.2(9) . . . . ?
O1 C1 C4 C5 -2.5(11) . . . . ?
N1 C1 C4 C5 178.5(7) . . . . ?
C2 N2 C6 C8 129.6(6) . . . . ?
C3 N2 C6 C8 -57.3(8) . . . . ?
C2 N2 C6 C7 -104.8(7) . . . . ?
C3 N2 C6 C7 68.4(8) . . . . ?
N2 C6 C8 C9 -57.8(9) . . . . ?
C7 C6 C8 C9 177.6(8) . . . . ?
C6 C8 C9 Br1 -62.9(9) . . . . ?
O3 C10 N3 C11 175.5(7) . . . . ?
C13 C10 N3 C11 -3.5(10) . . . . ?
C10 N3 C11 O4 -177.5(7) . . . . ?
C10 N3 C11 N4 1.3(9) . . . . ?
O4 C11 N4 C12 -179.4(6) . . . . ?
N3 C11 N4 C12 1.8(8) . . . . ?
O4 C11 N4 C15 3.4(9) . . . . ?
N3 C11 N4 C15 -175.4(5) . . . . ?
C11 N4 C12 C13 -2.5(10) . . . . ?
C15 N4 C12 C13 174.6(7) . . . . ?
N4 C12 C13 C10 0.1(11) . . . . ?
N4 C12 C13 C14 -178.9(8) . . . . ?
O3 C10 C13 C12 -176.3(8) . . . . ?
N3 C10 C13 C12 2.7(10) . . . . ?
O3 C10 C13 C14 2.7(13) . . . . ?
N3 C10 C13 C14 -178.3(8) . . . . ?
C12 N4 C15 C16 52.4(8) . . . . ?
C11 N4 C15 C16 -130.4(6) . . . . ?
C12 N4 C15 C17 -72.9(7) . . . . ?
C11 N4 C15 C17 104.3(6) . . . . ?
N4 C15 C17 C18 -56.4(9) . . . . ?
C16 C15 C17 C18 178.9(8) . . . . ?
C15 C17 C18 Br2 175.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O1 0.87 1.92 2.789(6) 173.4 1_545
N1 H1 O3 0.87 1.95 2.823(6) 177.5 1_565

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.646
_refine_diff_density_min         -1.138
_refine_diff_density_rms         0.099
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/pentane'
