##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
i>N</i>-(4-Methoxyphenyl)-<i>N</i>'-(5-nitro-1,3-thiazol-2-yl)urea
;
_chemical_name_common     GL4-1046
_chemical_formula_moiety     'C11 H10 N4 O4 S'
_chemical_formula_sum     'C11 H10 N4 O4 S'
_chemical_formula_iupac     'C11 H10 N4 O4 S'
_chemical_formula_weight     294.29
_chemical_melting_point     454
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     6.8740(3)
_cell_length_b     12.5840(7)
_cell_length_c     14.6861(5)
_cell_angle_alpha     90.00
_cell_angle_beta     101.622(3)
_cell_angle_gamma     90.00
_cell_volume     1244.34(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3592
_cell_measurement_theta_min     2.6
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     150.0(10)
_exptl_crystal_description     block
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.28
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.571
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     608
_exptl_absorpt_coefficient_mu     0.281
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SORTAV; Blessing, 1995)'
_exptl_absorpt_correction_T_min     0.718
_exptl_absorpt_correction_T_max     0.948
_exptl_special_details
;
;
_diffrn_ambient_temperature     150.0(10)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD'
_diffrn_measurement_method     '\f scans and \w scans with \k offsets'
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     8106
_diffrn_reflns_av_R_equivalents     0.0526
_diffrn_reflns_av_sigmaI/netI     0.0586
_diffrn_reflns_theta_min     2.83
_diffrn_reflns_theta_max     27.47
_diffrn_reflns_theta_full     27.47
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     19
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expr ession of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     2825
_reflns_number_gt     1979
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0877
_refine_ls_R_factor_gt     0.0504
_refine_ls_wR_factor_gt     0.1223
_refine_ls_wR_factor_ref     0.1448
_refine_ls_goodness_of_fit_ref     1.070
_refine_ls_restrained_S_all     1.070
_refine_ls_number_reflns     2825
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[\s^2^(Fo^2^)+(0.0755P)^2^+0.3053P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.380
_refine_diff_density_min     -0.511
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 2002)'
_computing_cell_refinement     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR92 (Altomare <i>et al.</i>, 1994)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'SHELXTL (Version 6.1; Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.12900(8) 0.68571(5) 0.41433(3) 0.0246(2) Uani d . 1 . .
    O O1 0.2254(2) 0.48461(14) 0.47569(10) 0.0306(4) Uani d . 1 . .
    O O2 0.5006(3) 0.00530(13) 0.62455(11) 0.0340(4) Uani d . 1 . .
    O O3 -0.0126(3) 0.97318(14) 0.33409(11) 0.0347(4) Uani d . 1 . .
    O O4 0.0063(3) 0.82488(15) 0.25900(11) 0.0367(5) Uani d . 1 . .
    N N1 0.2026(3) 0.79137(16) 0.57084(12) 0.0277(5) Uani d . 1 . .
    N N2 0.2668(3) 0.61085(16) 0.58904(13) 0.0268(5) Uani d . 1 . .
    H H2N 0.327(4) 0.627(2) 0.6449(19) 0.042(8) Uiso d . 1 . .
    N N3 0.3514(3) 0.44014(16) 0.62860(13) 0.0253(5) Uani d . 1 . .
    H H3N 0.380(4) 0.466(2) 0.6845(19) 0.037(8) Uiso d . 1 . .
    N N4 0.0257(3) 0.87648(16) 0.33258(13) 0.0270(5) Uani d . 1 . .
    C C1 0.0930(3) 0.82155(19) 0.41566(14) 0.0232(5) Uani d . 1 . .
    C C2 0.1399(3) 0.8632(2) 0.50308(15) 0.0267(5) Uani d . 1 . .
    H H2A 0.1292 0.9369 0.5153 0.032 Uiso calc R 1 . .
    C C3 0.2033(3) 0.69504(18) 0.53334(15) 0.0224(5) Uani d . 1 . .
    C C4 0.2790(3) 0.50759(19) 0.55815(15) 0.0243(5) Uani d . 1 . .
    C C5 0.3832(3) 0.32879(18) 0.62462(15) 0.0223(5) Uani d . 1 . .
    C C6 0.3583(3) 0.2717(2) 0.54193(15) 0.0245(5) Uani d . 1 . .
    H H6A 0.3153 0.3064 0.4839 0.029 Uiso calc R 1 . .
    C C7 0.3970(3) 0.1640(2) 0.54544(15) 0.0258(5) Uani d . 1 . .
    H H7A 0.3791 0.1245 0.4892 0.031 Uiso calc R 1 . .
    C C8 0.4620(3) 0.11186(19) 0.63008(15) 0.0253(5) Uani d . 1 . .
    C C9 0.4842(4) 0.1688(2) 0.71214(16) 0.0281(6) Uani d . 1 . .
    H H9A 0.5265 0.1342 0.7702 0.034 Uiso calc R 1 . .
    C C10 0.4439(4) 0.2773(2) 0.70889(16) 0.0277(5) Uani d . 1 . .
    H H10A 0.4583 0.3164 0.7651 0.033 Uiso calc R 1 . .
    C C11 0.5519(4) -0.0525(2) 0.70992(17) 0.0360(6) Uani d . 1 . .
    H H11A 0.5715 -0.1276 0.6965 0.054 Uiso calc R 1 . .
    H H11B 0.4446 -0.0460 0.7445 0.054 Uiso calc R 1 . .
    H H11C 0.6749 -0.0236 0.7472 0.054 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0269(3) 0.0260(4) 0.0198(3) 0.0001(2) 0.0024(2) -0.0017(2)
    O1 0.0405(10) 0.0273(10) 0.0225(9) 0.0016(8) 0.0028(7) -0.0024(7)
    O2 0.0482(11) 0.0242(9) 0.0304(9) 0.0047(8) 0.0097(8) 0.0018(7)
    O3 0.0418(11) 0.0279(10) 0.0335(10) 0.0046(8) 0.0057(8) 0.0080(8)
    O4 0.0450(11) 0.0437(12) 0.0193(8) 0.0073(9) 0.0015(7) -0.0019(8)
    N1 0.0368(12) 0.0251(11) 0.0214(10) 0.0020(9) 0.0059(8) -0.0009(8)
    N2 0.0352(12) 0.0240(11) 0.0205(10) 0.0011(9) 0.0040(8) -0.0033(9)
    N3 0.0315(11) 0.0238(11) 0.0204(10) 0.0003(9) 0.0048(8) -0.0014(9)
    N4 0.0239(11) 0.0318(12) 0.0250(10) 0.0008(9) 0.0041(8) 0.0044(9)
    C1 0.0226(12) 0.0249(13) 0.0223(11) 0.0005(10) 0.0049(9) 0.0036(10)
    C2 0.0310(13) 0.0242(13) 0.0246(12) 0.0003(10) 0.0046(9) -0.0005(10)
    C3 0.0241(12) 0.0231(13) 0.0206(11) -0.0022(9) 0.0063(8) -0.0015(9)
    C4 0.0243(12) 0.0251(13) 0.0247(12) -0.0007(10) 0.0079(9) -0.0009(10)
    C5 0.0206(11) 0.0247(13) 0.0226(11) -0.0003(9) 0.0070(8) 0.0002(10)
    C6 0.0233(12) 0.0285(14) 0.0219(11) 0.0006(10) 0.0051(9) 0.0007(10)
    C7 0.0253(12) 0.0293(14) 0.0233(11) -0.0025(10) 0.0063(9) -0.0030(10)
    C8 0.0257(12) 0.0214(12) 0.0309(12) 0.0006(10) 0.0105(9) 0.0002(10)
    C9 0.0310(13) 0.0314(14) 0.0231(11) 0.0006(11) 0.0087(9) 0.0044(10)
    C10 0.0338(14) 0.0273(13) 0.0235(12) 0.0006(11) 0.0097(10) -0.0020(10)
    C11 0.0477(16) 0.0261(14) 0.0345(14) 0.0045(12) 0.0089(11) 0.0074(11)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C3 . 1.723(2) ?
    S1 C1 . 1.728(2) ?
    O1 C4 . 1.227(3) ?
    O2 C8 . 1.373(3) ?
    O2 C11 . 1.431(3) ?
    O3 N4 . 1.246(3) ?
    O4 N4 . 1.245(2) ?
    N1 C3 . 1.332(3) ?
    N1 C2 . 1.349(3) ?
    N2 C3 . 1.356(3) ?
    N2 C4 . 1.384(3) ?
    N2 H2N . 0.86(3) ?
    N3 C4 . 1.353(3) ?
    N3 C5 . 1.421(3) ?
    N3 H3N . 0.87(3) ?
    N4 C1 . 1.398(3) ?
    C1 C2 . 1.364(3) ?
    C2 H2A . 0.9500 ?
    C5 C10 . 1.385(3) ?
    C5 C6 . 1.391(3) ?
    C6 C7 . 1.381(3) ?
    C6 H6A . 0.9500 ?
    C7 C8 . 1.397(3) ?
    C7 H7A . 0.9500 ?
    C8 C9 . 1.384(3) ?
    C9 C10 . 1.391(3) ?
    C9 H9A . 0.9500 ?
    C10 H10A . 0.9500 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C3 S1 C1 . . 86.27(11) ?
    C8 O2 C11 . . 117.49(19) ?
    C3 N1 C2 . . 109.40(18) ?
    C3 N2 C4 . . 124.68(19) ?
    C3 N2 H2N . . 115.2(19) ?
    C4 N2 H2N . . 118.6(19) ?
    C4 N3 C5 . . 128.5(2) ?
    C4 N3 H3N . . 117.8(18) ?
    C5 N3 H3N . . 113.6(18) ?
    O4 N4 O3 . . 122.61(19) ?
    O4 N4 C1 . . 117.3(2) ?
    O3 N4 C1 . . 120.09(19) ?
    C2 C1 N4 . . 127.3(2) ?
    C2 C1 S1 . . 112.58(17) ?
    N4 C1 S1 . . 120.16(17) ?
    N1 C2 C1 . . 114.6(2) ?
    N1 C2 H2A . . 122.7 ?
    C1 C2 H2A . . 122.7 ?
    N1 C3 N2 . . 119.29(19) ?
    N1 C3 S1 . . 117.15(17) ?
    N2 C3 S1 . . 123.53(17) ?
    O1 C4 N3 . . 126.7(2) ?
    O1 C4 N2 . . 121.2(2) ?
    N3 C4 N2 . . 112.05(19) ?
    C10 C5 C6 . . 120.0(2) ?
    C10 C5 N3 . . 116.5(2) ?
    C6 C5 N3 . . 123.5(2) ?
    C7 C6 C5 . . 119.0(2) ?
    C7 C6 H6A . . 120.5 ?
    C5 C6 H6A . . 120.5 ?
    C6 C7 C8 . . 121.3(2) ?
    C6 C7 H7A . . 119.4 ?
    C8 C7 H7A . . 119.4 ?
    O2 C8 C9 . . 124.7(2) ?
    O2 C8 C7 . . 115.9(2) ?
    C9 C8 C7 . . 119.4(2) ?
    C8 C9 C10 . . 119.5(2) ?
    C8 C9 H9A . . 120.3 ?
    C10 C9 H9A . . 120.3 ?
    C5 C10 C9 . . 120.8(2) ?
    C5 C10 H10A . . 119.6 ?
    C9 C10 H10A . . 119.6 ?
    O2 C11 H11A . . 109.5 ?
    O2 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    O2 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N2 H2N O4 4_676 0.86(3) 1.97(3) 2.817(3) 168(3)
    N3 H3N O3 4_676 0.87(3) 2.30(3) 3.168(2) 174(2)
data_global
_journal_date_recd_electronic     2010-08-10
_journal_date_accepted     2010-08-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      9
_journal_page_first     o2339
_journal_page_last     o2339
_journal_paper_category     QO
_journal_coeditor_code     SU2205
_publ_contact_author_name     'Dr Alan J. Lough'
_publ_contact_author_address
;
Department of Chemistry
University of Toronto
80 St George Street
Toronto
Ontario
Canada M5S 3H6
;
_publ_contact_author_email     alough@chem.utoronto.ca
_publ_contact_author_phone     416-978-6275
_publ_section_title
;
<i>N</i>-(4-Methoxyphenyl)-<i>N</i>'-(5-nitro-1,3-thiazol-2-yl)urea
;
loop_
    _publ_author_name
    _publ_author_address
    'Lough, Alan J.'
;
Department of Chemistry
University of Toronto
80 St George Street
Toronto
Ontario
Canada M5S 3H6
;
    'Hicks, Justin W.'
;
PET Centre
Centre for Addiction and Mental Health and Department of Psychiatry
University of Toronto
250 College Street
Toronto
Ontario
Canada M5T 1R8
;
    'Valliant, John F.'
;
Departments of Chemistry and Chemical Biology,
and Medical Physics and Applied Radiation Sciences
McMaster University
1280 Main Street West
Hamilton
Ontario
Canada L8S 4K1
;
    'Wilson, Alan A.'
;
PET Centre
Centre for Addiction and Mental Health and Department of Psychiatry
University of Toronto
250 College Street
Toronto
Ontario
Canada M5T 1R8
;
    'Vasdev, Neil'
;
PET Centre
Centre for Addiction and Mental Health and Department of Psychiatry
University of Toronto
250 College Street
Toronto
Ontario
Canada M5T 1R8
;