##############################################################################
###                                                                        ###
###        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_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-10-28
_journal_date_accepted     2009-10-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     12
_journal_page_first     o2989
_journal_page_last     o2989
_journal_paper_category     QO
_journal_coeditor_code     BT5121
_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-(2-Aminoethyl)-2-anilinoquinazolin-4(3H)-one methanol hemisolvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Gao ,Tao'
;
Faculty of Chemistry and Life Science
Xianning University
Xianning 437100
People's Republic of China
;
    'Jiao, Yuan-Hong'
;
School of Chemistry and Material Engineering
Huangshi Institute of Technology
Huangshi 435003
People's Republic of China
;
    '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-(2-Aminoethyl)-2-anilinoquinazolin-4(3H)-one methanol hemisolvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H16 N4 O, 0.5(C H4 O)'
_chemical_formula_sum     'C16.50 H18 N4 O1.50'
_chemical_formula_iupac     'C16 H16 N4 O, 0.5C H4 O'
_chemical_formula_weight     296.35
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     19.5972(11)
_cell_length_b     12.2035(7)
_cell_length_c     12.8681(8)
_cell_angle_alpha     90.00
_cell_angle_beta     103.3010(10)
_cell_angle_gamma     90.00
_cell_volume     2994.9(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3816
_cell_measurement_theta_min     2.4
_cell_measurement_theta_max     25.9
_cell_measurement_temperature     295(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.314
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1256
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type     None
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     295(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 APEXII'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     14007
_diffrn_reflns_av_R_equivalents     0.0727
_diffrn_reflns_av_sigmaI/netI     0.0516
_diffrn_reflns_theta_min     1.98
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     25
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3399
_reflns_number_gt     2377
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0820
_refine_ls_R_factor_gt     0.0615
_refine_ls_wR_factor_gt     0.1718
_refine_ls_wR_factor_ref     0.1855
_refine_ls_goodness_of_fit_ref     1.093
_refine_ls_restrained_S_all     1.141
_refine_ls_number_reflns     3399
_refine_ls_number_parameters     210
_refine_ls_number_restraints     13
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1044P)²+0.1504P] 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     0.549
_refine_diff_density_min     -0.290
_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 0.68958(7) 0.41303(12) 0.81309(11) 0.0573(4) Uani d . 1 . .
    N N1 0.73674(8) 0.41620(12) 0.66714(11) 0.0424(4) Uani d . 1 . .
    N N2 0.84958(8) 0.34284(13) 0.67038(11) 0.0458(4) Uani d . 1 . .
    N N3 0.77752(9) 0.40366(13) 0.51241(12) 0.0498(4) Uani d D 1 . .
    H H31 0.7345 0.4239 0.4817 0.060 Uiso calc RD 1 . .
    N N4 0.63136(9) 0.37965(16) 0.44490(14) 0.0632(5) Uani d D 1 . .
    H H41 0.6131 0.4263 0.3939 0.076 Uiso calc RD 1 . .
    H H42 0.6131 0.3143 0.4284 0.076 Uiso calc RD 1 . .
    C C1 0.80430(10) 0.34133(14) 0.83148(13) 0.0414(4) Uani d . 1 . .
    C C2 0.81360(11) 0.31401(16) 0.93932(14) 0.0503(5) Uani d . 1 . .
    H H2 0.7782 0.3290 0.9746 0.060 Uiso calc R 1 . .
    C C3 0.87449(12) 0.26533(18) 0.99341(15) 0.0576(6) Uani d . 1 . .
    H H3 0.8804 0.2465 1.0650 0.069 Uiso calc R 1 . .
    C C4 0.92707(11) 0.24457(19) 0.94030(15) 0.0589(6) Uani d . 1 . .
    H H4 0.9684 0.2115 0.9767 0.071 Uiso calc R 1 . .
    C C5 0.91908(11) 0.27202(19) 0.83510(16) 0.0573(6) Uani d . 1 . .
    H H5 0.9552 0.2579 0.8011 0.069 Uiso calc R 1 . .
    C C6 0.85720(10) 0.32115(15) 0.77791(13) 0.0427(5) Uani d . 1 . .
    C C7 0.73916(10) 0.39143(15) 0.77321(14) 0.0437(5) Uani d . 1 . .
    C C8 0.79099(10) 0.38642(15) 0.61962(14) 0.0414(4) Uani d . 1 . .
    C C9 0.82431(10) 0.39287(14) 0.44502(14) 0.0426(5) Uani d . 1 . .
    C C10 0.79487(10) 0.36669(15) 0.33875(14) 0.0462(5) Uani d . 1 . .
    H H10 0.7472 0.3515 0.3175 0.055 Uiso calc R 1 . .
    C C11 0.83579(12) 0.36311(17) 0.26507(15) 0.0530(5) Uani d . 1 . .
    H H11 0.8154 0.3462 0.1942 0.064 Uiso calc R 1 . .
    C C12 0.90627(13) 0.38417(19) 0.29508(18) 0.0614(6) Uani d . 1 . .
    H H12 0.9338 0.3820 0.2451 0.074 Uiso calc R 1 . .
    C C13 0.93592(12) 0.40868(19) 0.40098(18) 0.0616(6) Uani d . 1 . .
    H H13 0.9838 0.4225 0.4220 0.074 Uiso calc R 1 . .
    C C14 0.89551(11) 0.41293(17) 0.47595(16) 0.0534(5) Uani d . 1 . .
    H H14 0.9161 0.4292 0.5468 0.064 Uiso calc R 1 . .
    C C15 0.67613(10) 0.48235(17) 0.61029(15) 0.0516(5) Uani d . 1 . .
    H H15A 0.6922 0.5335 0.5634 0.062 Uiso calc R 1 . .
    H H15B 0.6587 0.5248 0.6624 0.062 Uiso calc R 1 . .
    C C16 0.61626(11) 0.41579(18) 0.54480(17) 0.0586(6) Uani d . 1 . .
    H H16A 0.6080 0.3524 0.5857 0.070 Uiso calc R 1 . .
    H H16B 0.5739 0.4599 0.5298 0.070 Uiso calc R 1 . .
    O O2 0.5495(3) 0.4637(6) 0.7850(7) 0.176(3) Uani d PDU 0.50 A -1
    H H2O 0.5856 0.4244 0.8006 0.211 Uiso calc PR 0.50 A -1
    C C17 0.4883(4) 0.3949(6) 0.7344(11) 0.101(3) Uani d PDU 0.50 A -1
    H H17A 0.4553 0.3937 0.7792 0.152 Uiso calc PR 0.50 A -1
    H H17B 0.5037 0.3216 0.7254 0.152 Uiso calc PR 0.50 A -1
    H H17C 0.4662 0.4250 0.6660 0.152 Uiso calc PR 0.50 A -1
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 C7 . 1.227(2) ?
    N1 C7 . 1.388(2) ?
    N1 C8 . 1.391(2) ?
    N1 C15 . 1.482(2) ?
    N2 C8 . 1.297(2) ?
    N2 C6 . 1.383(2) ?
    N3 C8 . 1.360(2) ?
    N3 C9 . 1.406(2) ?
    N3 H31 . 0.8800 ?
    N4 C16 . 1.453(3) ?
    N4 H41 . 0.8800 ?
    N4 H42 . 0.8800 ?
    C1 C6 . 1.393(3) ?
    C1 C2 . 1.398(2) ?
    C1 C7 . 1.458(3) ?
    C2 C3 . 1.371(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.385(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.368(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.400(3) ?
    C5 H5 . 0.9300 ?
    C9 C14 . 1.382(3) ?
    C9 C10 . 1.394(2) ?
    C10 C11 . 1.376(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.370(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.386(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.383(3) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.514(3) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    O2 C17 . 1.486(2) ?
    O2 H2O . 0.8400 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
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
    C7 N1 C8 . . 121.23(15) ?
    C7 N1 C15 . . 116.50(15) ?
    C8 N1 C15 . . 122.13(15) ?
    C8 N2 C6 . . 117.49(16) ?
    C8 N3 C9 . . 127.54(17) ?
    C8 N3 H31 . . 116.2 ?
    C9 N3 H31 . . 116.2 ?
    C16 N4 H41 . . 109.5 ?
    C16 N4 H42 . . 109.5 ?
    H41 N4 H42 . . 109.5 ?
    C6 C1 C2 . . 120.49(17) ?
    C6 C1 C7 . . 118.89(16) ?
    C2 C1 C7 . . 120.62(18) ?
    C3 C2 C1 . . 120.45(19) ?
    C3 C2 H2 . . 119.8 ?
    C1 C2 H2 . . 119.8 ?
    C2 C3 C4 . . 119.24(17) ?
    C2 C3 H3 . . 120.4 ?
    C4 C3 H3 . . 120.4 ?
    C5 C4 C3 . . 120.99(19) ?
    C5 C4 H4 . . 119.5 ?
    C3 C4 H4 . . 119.5 ?
    C4 C5 C6 . . 120.9(2) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 H5 . . 119.6 ?
    N2 C6 C1 . . 122.70(17) ?
    N2 C6 C5 . . 119.27(17) ?
    C1 C6 C5 . . 117.96(16) ?
    O1 C7 N1 . . 120.87(17) ?
    O1 C7 C1 . . 123.97(17) ?
    N1 C7 C1 . . 115.15(16) ?
    N2 C8 N3 . . 121.13(18) ?
    N2 C8 N1 . . 124.28(16) ?
    N3 C8 N1 . . 114.57(16) ?
    C14 C9 C10 . . 119.07(18) ?
    C14 C9 N3 . . 124.37(17) ?
    C10 C9 N3 . . 116.44(17) ?
    C11 C10 C9 . . 120.53(19) ?
    C11 C10 H10 . . 119.7 ?
    C9 C10 H10 . . 119.7 ?
    C12 C11 C10 . . 120.61(19) ?
    C12 C11 H11 . . 119.7 ?
    C10 C11 H11 . . 119.7 ?
    C11 C12 C13 . . 119.0(2) ?
    C11 C12 H12 . . 120.5 ?
    C13 C12 H12 . . 120.5 ?
    C14 C13 C12 . . 121.1(2) ?
    C14 C13 H13 . . 119.5 ?
    C12 C13 H13 . . 119.5 ?
    C9 C14 C13 . . 119.66(19) ?
    C9 C14 H14 . . 120.2 ?
    C13 C14 H14 . . 120.2 ?
    N1 C15 C16 . . 114.39(17) ?
    N1 C15 H15A . . 108.7 ?
    C16 C15 H15A . . 108.7 ?
    N1 C15 H15B . . 108.7 ?
    C16 C15 H15B . . 108.7 ?
    H15A C15 H15B . . 107.6 ?
    N4 C16 C15 . . 111.46(19) ?
    N4 C16 H16A . . 109.3 ?
    C15 C16 H16A . . 109.3 ?
    N4 C16 H16B . . 109.3 ?
    C15 C16 H16B . . 109.3 ?
    H16A C16 H16B . . 108.0 ?
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
    C6 C1 C2 C3 . . . . -1.1(3) ?
    C7 C1 C2 C3 . . . . 178.97(17) ?
    C1 C2 C3 C4 . . . . 0.7(3) ?
    C2 C3 C4 C5 . . . . 0.1(3) ?
    C3 C4 C5 C6 . . . . -0.5(4) ?
    C8 N2 C6 C1 . . . . 1.8(3) ?
    C8 N2 C6 C5 . . . . 178.68(18) ?
    C2 C1 C6 N2 . . . . 177.50(16) ?
    C7 C1 C6 N2 . . . . -2.5(3) ?
    C2 C1 C6 C5 . . . . 0.6(3) ?
    C7 C1 C6 C5 . . . . -179.41(17) ?
    C4 C5 C6 N2 . . . . -176.84(19) ?
    C4 C5 C6 C1 . . . . 0.2(3) ?
    C8 N1 C7 O1 . . . . -176.29(16) ?
    C15 N1 C7 O1 . . . . 7.9(3) ?
    C8 N1 C7 C1 . . . . 4.9(2) ?
    C15 N1 C7 C1 . . . . -170.91(15) ?
    C6 C1 C7 O1 . . . . -179.64(17) ?
    C2 C1 C7 O1 . . . . 0.3(3) ?
    C6 C1 C7 N1 . . . . -0.9(2) ?
    C2 C1 C7 N1 . . . . 179.07(16) ?
    C6 N2 C8 N3 . . . . -175.64(16) ?
    C6 N2 C8 N1 . . . . 2.5(3) ?
    C9 N3 C8 N2 . . . . -9.1(3) ?
    C9 N3 C8 N1 . . . . 172.63(16) ?
    C7 N1 C8 N2 . . . . -6.1(3) ?
    C15 N1 C8 N2 . . . . 169.49(18) ?
    C7 N1 C8 N3 . . . . 172.12(15) ?
    C15 N1 C8 N3 . . . . -12.3(2) ?
    C8 N3 C9 C14 . . . . -31.8(3) ?
    C8 N3 C9 C10 . . . . 152.29(18) ?
    C14 C9 C10 C11 . . . . -1.4(3) ?
    N3 C9 C10 C11 . . . . 174.75(17) ?
    C9 C10 C11 C12 . . . . 0.6(3) ?
    C10 C11 C12 C13 . . . . 0.3(3) ?
    C11 C12 C13 C14 . . . . -0.5(3) ?
    C10 C9 C14 C13 . . . . 1.2(3) ?
    N3 C9 C14 C13 . . . . -174.6(2) ?
    C12 C13 C14 C9 . . . . -0.3(3) ?
    C7 N1 C15 C16 . . . . -96.6(2) ?
    C8 N1 C15 C16 . . . . 87.6(2) ?
    N1 C15 C16 N4 . . . . -77.5(2) ?
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
    _geom_hbond_publ_flag
    N3 H31 N4 . 0.88 2.04 2.811(3) 146 yes
    N4 H41 O2 6_565 0.88 2.13 2.990(6) 168 yes
    O2 H2O O1 . 0.84 2.01 2.755(6) 147 yes
