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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-03-02
_journal_date_accepted     2009-03-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      4
_journal_page_first     o704
_journal_page_last     o704
_journal_paper_category     QO
_journal_coeditor_code     HB2922
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
3-Nitrophenyl pyrimidin-2-yl ether
;
loop_
    _publ_author_name
    _publ_author_address
    'Shah Bakhtiar, Nasir'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Abdullah, Zanariah'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Ng, Seik Weng'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-Nitrophenyl pyrimidin-2-yl ether
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H7 N3 O3'
_chemical_formula_sum     'C10 H7 N3 O3'
_chemical_formula_iupac     'C10 H7 N3 O3'
_chemical_formula_weight     217.19
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P b c n'
_symmetry_space_group_name_Hall     '-P 2n 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y+1/2, z+1/2'
    '-x, y, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y-1/2, -z-1/2'
    'x, -y, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     18.1360(3)
_cell_length_b     7.33550(10)
_cell_length_c     14.5986(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1942.15(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4130
_cell_measurement_theta_min     2.8
_cell_measurement_theta_max     28.2
_cell_measurement_temperature     118(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'Faint brown'
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.486
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     896
_exptl_absorpt_coefficient_mu     0.114
_exptl_absorpt_correction_type     None
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12785
_diffrn_reflns_av_R_equivalents     0.0294
_diffrn_reflns_av_sigmaI/netI     0.0195
_diffrn_reflns_theta_min     2.25
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -23
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     2242
_reflns_number_gt     1890
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0454
_refine_ls_R_factor_gt     0.0372
_refine_ls_wR_factor_gt     0.0953
_refine_ls_wR_factor_ref     0.1021
_refine_ls_goodness_of_fit_ref     1.021
_refine_ls_restrained_S_all     1.021
_refine_ls_number_reflns     2242
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0556P)²+0.7122P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.268
_refine_diff_density_min     -0.286
_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'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2009)'
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
    O O1 0.46423(5) 0.52259(12) 0.36904(6) 0.0222(2) Uani d . 1 . .
    O O2 0.34305(5) 0.73218(14) 0.08352(6) 0.0291(2) Uani d . 1 . .
    O O3 0.22956(6) 0.7828(2) 0.12079(7) 0.0467(3) Uani d . 1 . .
    N N1 0.42087(6) 0.22878(14) 0.35641(8) 0.0228(2) Uani d . 1 . .
    N N2 0.54579(6) 0.29874(15) 0.39501(8) 0.0234(3) Uani d . 1 . .
    N N3 0.29278(6) 0.73707(16) 0.13953(7) 0.0238(3) Uani d . 1 . .
    C C1 0.43734(8) 0.05109(18) 0.36142(10) 0.0280(3) Uani d . 1 . .
    H H1 0.3994 -0.0355 0.3502 0.034 Uiso calc R 1 . .
    C C2 0.50707(8) -0.01134(18) 0.38219(10) 0.0284(3) Uani d . 1 . .
    H H2 0.5182 -0.1378 0.3850 0.034 Uiso calc R 1 . .
    C C3 0.56002(7) 0.12058(19) 0.39866(10) 0.0267(3) Uani d . 1 . .
    H H3 0.6087 0.0824 0.4132 0.032 Uiso calc R 1 . .
    C C4 0.47660(7) 0.33980(16) 0.37377(8) 0.0180(3) Uani d . 1 . .
    C C5 0.39288(6) 0.58007(15) 0.34572(8) 0.0179(3) Uani d . 1 . .
    C C6 0.34150(7) 0.60883(16) 0.41443(8) 0.0205(3) Uani d . 1 . .
    H H6 0.3532 0.5820 0.4764 0.025 Uiso calc R 1 . .
    C C7 0.27269(7) 0.67742(17) 0.39132(9) 0.0218(3) Uani d . 1 . .
    H H7 0.2369 0.6965 0.4378 0.026 Uiso calc R 1 . .
    C C8 0.25564(7) 0.71852(17) 0.30078(8) 0.0202(3) Uani d . 1 . .
    H H8 0.2086 0.7655 0.2845 0.024 Uiso calc R 1 . .
    C C9 0.30919(7) 0.68896(16) 0.23527(8) 0.0181(3) Uani d . 1 . .
    C C10 0.37846(6) 0.61910(15) 0.25487(8) 0.0180(2) Uani d . 1 . .
    H H10 0.4141 0.5991 0.2083 0.022 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
    O1 0.0150(4) 0.0171(4) 0.0344(5) -0.0013(3) -0.0053(4) 0.0031(4)
    O2 0.0272(5) 0.0406(6) 0.0196(5) -0.0023(4) 0.0039(4) 0.0012(4)
    O3 0.0262(6) 0.0873(10) 0.0266(6) 0.0152(6) -0.0062(4) 0.0083(6)
    N1 0.0197(5) 0.0192(5) 0.0295(6) -0.0015(4) -0.0035(4) -0.0006(4)
    N2 0.0175(5) 0.0233(6) 0.0294(6) 0.0008(4) -0.0015(4) 0.0036(4)
    N3 0.0215(5) 0.0300(6) 0.0199(5) 0.0000(4) -0.0019(4) 0.0000(4)
    C1 0.0278(7) 0.0187(6) 0.0375(8) -0.0030(5) -0.0046(6) -0.0024(5)
    C2 0.0300(7) 0.0199(6) 0.0352(7) 0.0038(5) -0.0011(6) -0.0005(5)
    C3 0.0209(6) 0.0265(7) 0.0326(7) 0.0050(5) -0.0013(5) 0.0033(5)
    C4 0.0183(6) 0.0186(6) 0.0173(6) -0.0010(4) 0.0003(4) 0.0019(4)
    C5 0.0150(5) 0.0133(5) 0.0255(6) -0.0016(4) -0.0025(5) 0.0005(4)
    C6 0.0237(6) 0.0193(6) 0.0186(6) -0.0031(5) -0.0010(5) 0.0015(4)
    C7 0.0215(6) 0.0224(6) 0.0214(6) 0.0007(5) 0.0046(5) -0.0013(5)
    C8 0.0154(5) 0.0213(6) 0.0240(6) 0.0022(4) 0.0007(5) -0.0010(5)
    C9 0.0185(6) 0.0182(5) 0.0175(6) -0.0013(4) -0.0012(4) -0.0005(4)
    C10 0.0152(5) 0.0173(5) 0.0214(6) -0.0010(4) 0.0023(4) -0.0021(4)
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
    O1 C4 . 1.3613(15) ?
    O1 C5 . 1.4029(14) ?
    O2 N3 . 1.2252(14) ?
    O3 N3 . 1.2256(15) ?
    N1 C4 . 1.3225(16) ?
    N1 C1 . 1.3392(17) ?
    N2 C4 . 1.3273(16) ?
    N2 C3 . 1.3332(17) ?
    N3 C9 . 1.4720(16) ?
    C1 C2 . 1.379(2) ?
    C1 H1 . 0.9500 ?
    C2 C3 . 1.384(2) ?
    C2 H2 . 0.9500 ?
    C3 H3 . 0.9500 ?
    C5 C10 . 1.3819(17) ?
    C5 C6 . 1.3852(17) ?
    C6 C7 . 1.3872(18) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.3907(18) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.3801(17) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.3867(17) ?
    C10 H10 . 0.9500 ?
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
    C4 O1 C5 . . 117.41(9) ?
    C4 N1 C1 . . 114.73(11) ?
    C4 N2 C3 . . 114.50(11) ?
    O2 N3 O3 . . 123.73(11) ?
    O2 N3 C9 . . 118.44(11) ?
    O3 N3 C9 . . 117.82(11) ?
    N1 C1 C2 . . 122.68(13) ?
    N1 C1 H1 . . 118.7 ?
    C2 C1 H1 . . 118.7 ?
    C1 C2 C3 . . 116.25(12) ?
    C1 C2 H2 . . 121.9 ?
    C3 C2 H2 . . 121.9 ?
    N2 C3 C2 . . 122.96(12) ?
    N2 C3 H3 . . 118.5 ?
    C2 C3 H3 . . 118.5 ?
    N1 C4 N2 . . 128.87(12) ?
    N1 C4 O1 . . 118.10(11) ?
    N2 C4 O1 . . 113.03(10) ?
    C10 C5 C6 . . 122.42(11) ?
    C10 C5 O1 . . 118.01(10) ?
    C6 C5 O1 . . 119.37(11) ?
    C5 C6 C7 . . 118.97(11) ?
    C5 C6 H6 . . 120.5 ?
    C7 C6 H6 . . 120.5 ?
    C6 C7 C8 . . 120.65(11) ?
    C6 C7 H7 . . 119.7 ?
    C8 C7 H7 . . 119.7 ?
    C9 C8 C7 . . 117.91(11) ?
    C9 C8 H8 . . 121.0 ?
    C7 C8 H8 . . 121.0 ?
    C8 C9 C10 . . 123.55(11) ?
    C8 C9 N3 . . 118.55(11) ?
    C10 C9 N3 . . 117.88(11) ?
    C5 C10 C9 . . 116.49(11) ?
    C5 C10 H10 . . 121.8 ?
    C9 C10 H10 . . 121.8 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C4 N1 C1 C2 . . . . -0.6(2) ?
    N1 C1 C2 C3 . . . . 0.5(2) ?
    C4 N2 C3 C2 . . . . -0.3(2) ?
    C1 C2 C3 N2 . . . . 0.0(2) ?
    C1 N1 C4 N2 . . . . 0.2(2) ?
    C1 N1 C4 O1 . . . . 179.32(11) ?
    C3 N2 C4 N1 . . . . 0.3(2) ?
    C3 N2 C4 O1 . . . . -178.92(11) ?
    C5 O1 C4 N1 . . . . -0.16(16) ?
    C5 O1 C4 N2 . . . . 179.13(10) ?
    C4 O1 C5 C10 . . . . -94.96(13) ?
    C4 O1 C5 C6 . . . . 89.88(13) ?
    C10 C5 C6 C7 . . . . 0.74(18) ?
    O1 C5 C6 C7 . . . . 175.68(10) ?
    C5 C6 C7 C8 . . . . -0.65(18) ?
    C6 C7 C8 C9 . . . . -0.02(18) ?
    C7 C8 C9 C10 . . . . 0.66(18) ?
    C7 C8 C9 N3 . . . . -178.15(11) ?
    O2 N3 C9 C8 . . . . 171.09(11) ?
    O3 N3 C9 C8 . . . . -7.71(18) ?
    O2 N3 C9 C10 . . . . -7.78(17) ?
    O3 N3 C9 C10 . . . . 173.41(13) ?
    C6 C5 C10 C9 . . . . -0.15(17) ?
    O1 C5 C10 C9 . . . . -175.15(10) ?
    C8 C9 C10 C5 . . . . -0.57(18) ?
    N3 C9 C10 C5 . . . . 178.25(10) ?
