# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Eur.J.Pharm.Sci.
_journal_coden_cambridge         1045
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
'Ferreira, Fabio F.'
;
Centro de Ciencias Naturais e Humanas (CCNH)
Universidade Federal do ABC (UFABC)
Rua Santa Adelia, 166, Bairro Bangu
CEP: 09210-170
Santo Andre, SP
Brazil
;
.
'Trindade, Antonio Carlos'
;
Instituto de Quimica e Biotecnologia Universidade Federal de Alagoas Campus A.
C. Simoes
BR 104, km 97,6, Tabuleiro do Martins
CEP: 57072-970
Maceio, AL
Brazil
;
.
'Antonio, Selma Gutierrez'
;
Instituto de Quimica
Depto. de Fisico-Quimica
Universidade Estadual Paulista
Caixa Postal 355
CEP: 14801-970
Araraquara, SP
Brazil
;
.
'Paiva-Santos, Carlos de Oliveira'
;
Instituto de Quimica
Depto. de Fisico-Quimica
Universidade Estadual Paulista
Caixa Postal 355
CEP: 14801-970
Araraquara, SP
Brazil
;
.
_publ_contact_author_address     
;
Centro de Ciencias Naturais e Humanas (CCNH)
Universidade Federal do ABC (UFABC)
Rua Santa Adelia, 166, Bairro Bangu
CEP: 09210-170
Santo Andre, SP
Brazil
;
_publ_contact_author_email       fabio.furlan@ufabc.edu.br
_publ_contact_author_fax         '+55 11 4996-0090'

_publ_contact_author_phone       '+55 11 4996-7960'

#####################################
# 1. SUBMISSION DETAILS AND AUTHORS #
#####################################

_publ_contact_author_name        'Fabio Furlan Ferreira'
_publ_section_title              
;
Crystal structure of 6-propyl-2-thiouracil (C7H10N2OS) used in the treatment of
hyperthyroidism
;

data_Template
_database_code_depnum_ccdc_archive 'CCDC 807160'
#TrackingRef '3709_web_deposit_cif_file_0_FabioFurlanFerreira_1294655882.cif'

_publ_section_acknowledgements   
;
(type here to add acknowledgements)
;
#Added by publCIF

_computing_data_reduction        SPECReaderCLX.exe
#Added by publCIF

_computing_cell_refinement       'Topas Academic v. 4.1'
#Added by publCIF

_computing_data_collection       SPEC
#Added by publCIF

_pd_proc_ls_profile_function     'Double-Voigt approach'
#Added by publCIF

_pd_proc_ls_pref_orient_corr     '8-term Spherical harmonics'
#Added by publCIF

_pd_proc_ls_background_function  Chebyschev
#Added by publCIF

_refine_ls_R_factor_all          ?
#Added by publCIF

_pd_proc_ls_prof_wR_expected     0.055
#Added by publCIF

_refine_ls_R_I_factor            0.0157
#Added by publCIF

_refine_ls_structure_factor_coef F
#Added by publCIF

_pd_spec_mounting                capillary
#Added by publCIF

_pd_proc_2theta_range_inc        0.005
#Added by publCIF

_pd_proc_2theta_range_max        37.465
#Added by publCIF

_pd_proc_2theta_range_min        8
#Added by publCIF

_pd_meas_scan_method             step
#Added by publCIF

_pd_spec_mount_mode              transmission
#Added by publCIF

_chemical_melting_point          491
#Added by publCIF

_audit_update_record             
;
2011-01-08 # Formatted by publCIF
;

_publ_section_abstract           
;
The crystal structure of propylthiouracil, a drug used in the treatment of
hyperthyroidism, was determined by means of high-resolution synchrotron X-ray
powder diffraction data. The Rietveld method was employed to refine the
structure. This drug crystallizes in an orthorhombic (<i>Pbca</i>) space
group, with unit-cell parameters <i>a</i> = 28.67338(23) \%A, <i>b</i> =
11.15287(6) \%A, <i>c</i> = 10.66821(5) \%A, V = 3411.59(4) \%A^3^, <i>Z</i> =
16, <i>Z'</i> = 2, M = 170.23 g mol^-1^, r~calc~ = 1.32575(1) g cm^-3^. The
goodness-of-fit and R-factors were, respectively: \c^2^ = 1.599,
<i>R~Bragg~</i> = 1.57%, <i>R~wp~</i> = 8.85% and <i>R~exp~</i> = 5.53%. Four
hydrogen bonds involving the atoms N(6)--H(12)...S(39), N(19)--H(21)...O(41),
N(27)--H(33)...S(18) and N(40)--H(42)...O(20) form a network of molecular
aggregates in propylthiouracil.
;

_publ_section_comment            
;
(type here to add)
;

_publ_section_references         
;
?
;

###################
# 2. EXPERIMENTAL #
###################

_publ_section_exptl_prep         
;
A powder pattern was recorded on a Huber 4 + 2 circles diffractometer at
D10B-XPD beamline of LNLS (synchrotron radiation, Si-111 monochromator,
transmission geometry).
;

_diffrn_measurement_device_type  'Huber 4+2 diffractometer'
_diffrn_radiation_polarisn_ratio 95
_diffrn_radiation_wavelength     1.23982
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  Si-111
_geom_special_details            Transmission
_cell_measurement_temperature    298(2)
_exptl_special_details           ?

##########################################
# 3. OVERALL SOLUTION/REFINEMENT DETAILS #
##########################################

_refine_special_details          
;
A Rietveld refinement was performed with the TOPAS package using the modified
Thomson-Cox-Hastings pseudo-Voigt approach as reflection profiles. The peak
asymmetry was fitted by the simple axial divergence model of Cheary and
Coelho. The peak profiles were modeled by the Double-Voigt approach with
anisotropic peak profiles adjusted using spherical harmonics as well as
preferred orientation of the crystals. The according
parameters were allowed to refine freely.
;

_computing_molecular_graphics    'Diamond V. 3.2'
_computing_publication_material  'TOPAS ACADEMIC 4.1'
_audit_creation_method           'TOPAS ACADEMIC 4.1 + PLATON'
_pd_calc_method                  'Rietveld Refinement'
_computing_structure_solution    DASH
_computing_structure_refinement  'TOPAS ACADEMIC 4.1'

_refine_ls_shift/su_mean         0.00
_refine_ls_shift/su_max          0.00
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_constraints    21
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_all   1.60
_pd_proc_ls_prof_R_factor        0.06881
_pd_proc_ls_prof_wR_factor       0.08847
_pd_proc_ls_prof_R_expected      0.05532
_refine_ls_R_Fsqd_factor         0.01572

_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     calc
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
# if regions of the data are excluded, the reason(s) are supplied here:
_pd_proc_info_excluded_regions   ?

#####################
# 4. SAMPLE DETAILS #
#####################

_pd_char_colour                  white
_pd_char_particle_morphology     powder

_chemical_name_systematic        
;
6-propyl-2-thiouracil
;
_chemical_name_common            Propylthiouracil
_chemical_formula_moiety         'C7 H10 N2 O S'
_chemical_formula_sum            'C7 H10 N2 O S'
_chemical_formula_analytical     'C7 H10 N2 O S'

_chemical_formula_weight         170.233

_exptl_crystal_F_000             1440
_exptl_crystal_density_diffrn    1.3258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

_cell_special_details            
;
none
;

_exptl_absorpt_coefficient_mu    1.567
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
TOPAS:
capillary_diameter_mm 0.68
capillary_u_cm_inv !absc 15.67 '(in 1_on_cm)
capillary_parallel_beam
;

_pd_meas_number_of_points        5893
_pd_proc_number_of_points        5893

_reflns_number_total             256
_reflns_limit_h_min              0
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              5
_reflns_limit_l_min              0
_reflns_limit_l_max              5
_reflns_d_resolution_high        8.559
_reflns_d_resolution_low         1.934

###################
# 5. CRYSTAL DATA #
###################

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

_cell_length_a                   28.67338(23)
_cell_length_b                   11.152871(61)
_cell_length_c                   10.668212(55)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3411.593(37)
_cell_formula_units_Z            16
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a b'
_symmetry_space_group_name_Hall  '-P 2bc 2ac'
_symmetry_Int_Tables_number      61

# PLATON
loop_
_atom_type_symbol
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 112.0 0.012 0.006 2.31000 20.8439 1.02000 10.2075 1.58860 0.56870 0.86500
51.6512 0.21560 International_Tables_Vol_C
H 160.0 0.000 0.000 0.49300 10.5109 0.32291 26.1257 0.14019 3.14236 0.04081
57.7997 0.00304 International_Tables_Vol_C
N 32.0 0.021 0.011 12.2126 0.00570 3.13220 9.89330 2.01250 28.9975 1.16630
0.58260 -11.529 International_Tables_Vol_C
S 16.0 0.268 0.369 6.90530 1.46790 5.20340 22.2151 1.43790 0.25360 1.58630
56.1720 0.86690 International_Tables_Vol_C
O 16.0 0.034 0.020 3.04850 13.2771 2.28680 5.70110 1.54630 0.32390 0.86700
32.9089 0.25080 International_Tables_Vol_C

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_thermal_displace_type
_atom_site_B_iso_or_equiv
C1 C 8 0.50517(17) 0.26711(41) 0.15388(48) 1 Biso 4.77(17)
C2 C 8 0.46718(17) 0.17863(43) 0.12904(94) 1 Biso 4.77(17)
C3 C 8 0.54065(17) 0.21598(42) 0.24220(45) 1 Biso 4.77(17)
H4 H 8 0.49019(92) 0.3484(19) 0.1970(20) 1 Biso 5.72(20)
H5 H 8 0.52267(90) 0.2911(16) 0.0652(23) 1 Biso 5.72(20)
N6 N 8 0.42344(16) 0.22581(40) 0.11745(93) 1 Biso 4.77(17)
C7 C 8 0.47230(18) 0.05852(42) 0.1241(10) 1 Biso 4.77(17)
C8 C 8 0.57594(17) 0.31019(41) 0.26850(45) 1 Biso 4.77(17)
H9 H 8 0.55894(84) 0.1388(19) 0.1976(21) 1 Biso 5.72(20)
H10 H 8 0.52347(89) 0.1888(17) 0.3318(21) 1 Biso 5.72(20)
C11 C 8 0.38514(17) 0.15606(47) 0.0957(12) 1 Biso 4.77(17)
H12 H 8 0.41876(88) 0.3166(17) 0.1321(22) 1 Biso 5.72(20)
C13 C 8 0.43411(18) -0.01832(43) 0.0955(13) 1 Biso 4.77(17)
H14 H 8 0.50295(96) 0.0182(17) 0.1671(19) 1 Biso 5.72(20)
H15 H 8 0.56837(83) 0.3506(18) 0.3626(21) 1 Biso 5.72(20)
H16 H 8 0.57333(86) 0.3794(20) 0.1939(20) 1 Biso 5.72(20)
H17 H 8 0.61169(95) 0.2692(16) 0.2680(31) 1 Biso 5.72(20)
S18 S 8 0.33196(17) 0.21553(30) 0.07864(63) 1 Biso 4.77(17)
N19 N 8 0.39118(16) 0.03414(41) 0.08856(90) 1 Biso 4.77(17)
O20 O 8 0.43639(26) -0.12829(54) 0.0987(11) 1 Biso 4.77(17)
H21 H 8 0.36274(88) -0.0196(16) 0.0813(23) 1 Biso 5.72(20)
C22 C 8 0.75248(17) 0.52642(43) 0.85965(47) 1 Biso 4.77(17)
C23 C 8 0.71259(17) 0.43874(42) 0.87912(94) 1 Biso 4.77(17)
C24 C 8 0.78884(17) 0.47801(42) 0.77115(44) 1 Biso 4.77(17)
H25 H 8 0.76912(88) 0.5471(16) 0.9512(20) 1 Biso 5.72(20)
H26 H 8 0.73797(91) 0.6100(18) 0.8187(22) 1 Biso 5.72(20)
N27 N 8 0.66876(17) 0.48602(40) 0.89091(95) 1 Biso 4.77(17)
C28 C 8 0.71867(17) 0.31781(42) 0.8915(12) 1 Biso 4.77(17)
C29 C 8 0.82309(17) 0.57668(43) 0.73990(45) 1 Biso 4.77(17)
H30 H 8 0.77173(88) 0.4470(17) 0.6834(21) 1 Biso 5.72(20)
H31 H 8 0.80790(86) 0.4030(18) 0.8166(20) 1 Biso 5.72(20)
C32 C 8 0.63077(17) 0.41614(46) 0.9143(12) 1 Biso 4.77(17)
H33 H 8 0.66452(85) 0.5792(17) 0.8833(35) 1 Biso 5.72(20)
C34 C 8 0.67938(18) 0.23881(42) 0.9049(12) 1 Biso 4.77(17)
H35 H 8 0.75155(98) 0.2777(15) 0.8617(23) 1 Biso 5.72(20)
H36 H 8 0.84774(91) 0.5455(17) 0.6657(19) 1 Biso 5.72(20)
H37 H 8 0.84317(87) 0.6024(20) 0.8252(19) 1 Biso 5.72(20)
H38 H 8 0.80280(86) 0.6548(18) 0.7044(21) 1 Biso 5.72(20)
S39 S 8 0.57794(16) 0.47715(38) 0.93031(54) 1 Biso 4.77(17)
N40 N 8 0.63681(16) 0.29417(41) 0.92004(95) 1 Biso 4.77(17)
O41 O 8 0.68120(28) 0.12665(53) 0.90063(95) 1 Biso 4.77(17)
H42 H 8 0.60854(88) 0.2417(15) 0.9329(24) 1 Biso 5.72(20)

#######################
# 6. BONDS AND ANGLES #
#######################

# PLATON
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(18) C(11) 1.673(7) . 1_555 n
O(20) C(13) 1.229(7) . 1_555 n
N(6) C(2) 1.366(7) . 1_555 n
N(6) C(11) 1.365(7) . 1_555 n
N(19) C(11) 1.374(7) . 1_555 n
N(19) C(13) 1.365(7) . 1_555 n
C(1) C(2) 1.494(7) . 1_555 n
C(1) C(3) 1.499(7) . 1_555 n
C(2) C(7) 1.349(6) . 1_555 n
C(3) C(8) 1.485(7) . 1_555 n
C(7) C(13) 1.423(8) . 1_555 n
N(6) H(12) 1.03(2) . 1_555 n
N(19) H(21) 1.02(2) . 1_555 n
C(1) H(4) 1.10(2) . 1_555 n
C(1) H(5) 1.11(2) . 1_555 n
C(3) H(9) 1.11(2) . 1_555 n
C(3) H(10) 1.12(2) . 1_555 n
C(7) H(14) 1.09(3) . 1_555 n
C(8) H(15) 1.13(2) . 1_555 n
C(8) H(16) 1.11(2) . 1_555 n
C(8) H(17) 1.12(3) . 1_555 n
S(39) C(32) 1.670(7) . 1_555 n
O(41) C(34) 1.252(7) . 1_555 n
N(27) C(23) 1.369(7) . 1_555 n
N(27) C(32) 1.363(8) . 1_555 n
N(40) C(32) 1.372(7) . 1_555 n
N(40) C(34) 1.378(7) . 1_555 n
C(22) C(23) 1.519(7) . 1_555 n
C(22) C(24) 1.507(7) . 1_555 n
C(23) C(28) 1.366(6) . 1_555 n
C(24) C(29) 1.513(7) . 1_555 n
C(28) C(34) 1.437(7) . 1_555 n
N(27) H(33) 1.05(2) . 1_555 n
N(40) H(42) 1.01(2) . 1_555 n
C(22) H(25) 1.11(2) . 1_555 n
C(22) H(26) 1.11(2) . 1_555 n
C(24) H(30) 1.12(2) . 1_555 n
C(24) H(31) 1.11(2) . 1_555 n
C(28) H(35) 1.09(3) . 1_555 n
C(29) H(36) 1.12(2) . 1_555 n
C(29) H(37) 1.11(2) . 1_555 n
C(29) H(38) 1.12(2) . 1_555 n

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 N27 C32 122.0(4) 1_555 . 1_555 n
C32 N40 C34 123.5(5) 1_555 . 1_555 n
C23 C22 C24 112.1(4) 1_555 . 1_555 n
N27 C23 C22 117.1(4) 1_555 . 1_555 n
N27 C23 C28 119.3(5) 1_555 . 1_555 n
C22 C23 C28 123.6(4) 1_555 . 1_555 n
C22 C24 C29 109.1(4) 1_555 . 1_555 n
C23 C28 C34 121.0(4) 1_555 . 1_555 n
S39 C32 N27 120.7(4) 1_555 . 1_555 n
S39 C32 N40 121.0(4) 1_555 . 1_555 n
N27 C32 N40 118.3(5) 1_555 . 1_555 n
O41 C34 N40 119.3(6) 1_555 . 1_555 n
O41 C34 C28 125.2(6) 1_555 . 1_555 n
N40 C34 C28 115.5(4) 1_555 . 1_555 n
C23 N27 H33 118.8(15) 1_555 . 1_555 n
C32 N27 H33 119.2(15) 1_555 . 1_555 n
C32 N40 H42 118.6(12) 1_555 . 1_555 n
C34 N40 H42 117.9(12) 1_555 . 1_555 n
C23 C22 H25 109.8(12) 1_555 . 1_555 n
C23 C22 H26 108.2(14) 1_555 . 1_555 n
C24 C22 H25 109.1(13) 1_555 . 1_555 n
C24 C22 H26 108.4(13) 1_555 . 1_555 n
H25 C22 H26 109.3(15) 1_555 . 1_555 n
C22 C24 H30 109.5(13) 1_555 . 1_555 n
C22 C24 H31 109.5(12) 1_555 . 1_555 n
C29 C24 H30 109.0(12) 1_555 . 1_555 n
C29 C24 H31 109.0(13) 1_555 . 1_555 n
H30 C24 H31 110.7(16) 1_555 . 1_555 n
C23 C28 H35 119.2(11) 1_555 . 1_555 n
C34 C28 H35 117.1(11) 1_555 . 1_555 n
C24 C29 H36 109.9(11) 1_555 . 1_555 n
C24 C29 H37 109.9(12) 1_555 . 1_555 n
C24 C29 H38 107.8(13) 1_555 . 1_555 n
H36 C29 H37 109.3(18) 1_555 . 1_555 n
H36 C29 H38 109.3(16) 1_555 . 1_555 n
H37 C29 H38 110.7(17) 1_555 . 1_555 n

#End of data_Template
#TrackingRef '3709_web_deposit_cif_file_0_FabioFurlanFerreira_1294655882.cif'