##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1411448'
_audit_creation_method     SHELXL-2013
_chemical_name_systematic
;
3-Amino-2-propylquinazolin-4(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H13 N3 O'
_chemical_formula_sum     'C11 H13 N3 O'
_chemical_formula_iupac     'C11 H13 N3 O'
_chemical_formula_weight     203.24
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     trigonal
_space_group_name_H-M_alt     'R -3:H'
_space_group_name_Hall     '-R 3'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-y, x-y, z'
    '-x+y, -x, z'
    'x+2/3, y+1/3, z+1/3'
    '-y+2/3, x-y+1/3, z+1/3'
    '-x+y+2/3, -x+1/3, z+1/3'
    'x+1/3, y+2/3, z+2/3'
    '-y+1/3, x-y+2/3, z+2/3'
    '-x+y+1/3, -x+2/3, z+2/3'
    '-x, -y, -z'
    'y, -x+y, -z'
    'x-y, x, -z'
    '-x+2/3, -y+1/3, -z+1/3'
    'y+2/3, -x+y+1/3, -z+1/3'
    'x-y+2/3, x+1/3, -z+1/3'
    '-x+1/3, -y+2/3, -z+2/3'
    'y+1/3, -x+y+2/3, -z+2/3'
    'x-y+1/3, x+2/3, -z+2/3'
_cell_length_a     24.1525(5)
_cell_length_b     24.1525(5)
_cell_length_c     9.6500(2)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     120
_cell_volume     4875.1(2)
_cell_formula_units_Z     18
_cell_measurement_reflns_used     2040
_cell_measurement_theta_min     5.0190
_cell_measurement_theta_max     74.0740
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.338
_exptl_crystal_size_mid     0.249
_exptl_crystal_size_min     0.192
_exptl_crystal_density_diffrn     1.246
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1944
_exptl_absorpt_coefficient_mu     0.672
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_shelx_estimated_absorpt_T_min     0.805
_shelx_estimated_absorpt_T_max     0.882
_exptl_absorpt_correction_T_min     0.975
_exptl_absorpt_correction_T_max     0.984
_exptl_special_details     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type
           'Agilent SuperNova Dual Source diffractometer with an Atlas detector'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3734
_diffrn_reflns_av_R_equivalents     0.0128
_diffrn_reflns_theta_min     3.660
_diffrn_reflns_theta_max     74.049
_diffrn_reflns_theta_full     67.684
_diffrn_measured_fraction_theta_max     0.970
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -21
_diffrn_reflns_limit_h_max     30
_diffrn_reflns_limit_k_min     -26
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     2136
_reflns_number_gt     1913
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0437
_refine_ls_R_factor_gt     0.0399
_refine_ls_wR_factor_gt     0.1138
_refine_ls_wR_factor_ref     0.1202
_refine_ls_goodness_of_fit_ref     1.056
_refine_ls_restrained_S_all     1.056
_refine_ls_number_reflns     2136
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0637P)²+1.4157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.170
_refine_diff_density_min     -0.148
_refine_ls_extinction_method
;
SHELXL2013 (Sheldrick, 2015)
;
_refine_ls_extinction_coef     0.00114(10)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft,
2001)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.23343(6) 0.11120(6) 0.00970(12) 0.0453(3) Uani d 1 . .
    C C2 0.28221(6) 0.06090(5) 0.14259(13) 0.0457(3) Uani d 1 . .
    C C3 0.27352(5) 0.09197(5) 0.26270(12) 0.0440(3) Uani d 1 . .
    C C4 0.24674(6) 0.13113(6) 0.24439(12) 0.0450(3) Uani d 1 . .
    C C5 0.29168(6) 0.08293(7) 0.39466(14) 0.0535(3) Uani d 1 . .
    H H5 0.3089 0.0563 0.4064 0.064 Uiso calc 1 . .
    C C6 0.28403(7) 0.11345(8) 0.50654(14) 0.0618(4) Uani d 1 . .
    H H6 0.2958 0.1074 0.5946 0.074 Uiso calc 1 . .
    C C7 0.25865(8) 0.15367(8) 0.48822(14) 0.0630(4) Uani d 1 . .
    H H7 0.2544 0.1749 0.5643 0.076 Uiso calc 1 . .
    C C8 0.23997(7) 0.16241(7) 0.36013(14) 0.0567(3) Uani d 1 . .
    H H8 0.2228 0.1891 0.3498 0.068 Uiso calc 1 . .
    C C9 0.20961(7) 0.11882(6) -0.12831(14) 0.0546(3) Uani d 1 . .
    H H9A 0.2357 0.1157 -0.2009 0.066 Uiso calc 1 . .
    H H9B 0.2141 0.1610 -0.1337 0.066 Uiso calc 1 . .
    C C10 0.13977(8) 0.06846(8) -0.15299(18) 0.0697(4) Uani d 1 . .
    H H10A 0.1359 0.0265 -0.1554 0.084 Uiso calc 1 . .
    H H10B 0.1141 0.0691 -0.0763 0.084 Uiso calc 1 . .
    C C11 0.11417(10) 0.07946(12) -0.2869(2) 0.0996(7) Uani d 1 . .
    H H11A 0.1222 0.1226 -0.2894 0.149 Uiso calc 1 . .
    H H11B 0.0690 0.0503 -0.2924 0.149 Uiso calc 1 . .
    H H11C 0.1351 0.0724 -0.3639 0.149 Uiso calc 1 . .
    N N1 0.25905(5) 0.07168(5) 0.01918(10) 0.0447(3) Uani d 1 . .
    N N2 0.22710(5) 0.14035(5) 0.11608(11) 0.0486(3) Uani d 1 . .
    N N3 0.26483(7) 0.04247(6) -0.10370(12) 0.0550(3) Uani d 1 . .
    O O1 0.30729(5) 0.02780(5) 0.14300(11) 0.0625(3) Uani d 1 . .
    H H3A 0.2287(9) 0.0033(10) -0.1045(18) 0.069(5) Uiso d 1 . .
    H H3B 0.2972(10) 0.0370(9) -0.087(2) 0.069(5) Uiso d 1 . .
_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
    C1 N2 . 1.2963(16) ?
    C1 N1 . 1.3760(16) ?
    C1 C9 . 1.4981(17) ?
    C2 O1 . 1.2209(15) ?
    C2 N1 . 1.3945(16) ?
    C2 C3 . 1.4520(17) ?
    C3 C4 . 1.3984(18) ?
    C3 C5 . 1.3991(18) ?
    C4 N2 . 1.3832(16) ?
    C4 C8 . 1.4032(18) ?
    C5 C6 . 1.371(2) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.395(2) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.368(2) ?
    C7 H7 . 0.9300 ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.526(2) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 C11 . 1.512(2) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    N1 N3 . 1.4219(14) ?
    N3 H3A . 0.91(2) ?
    N3 H3B . 0.87(2) ?
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
    N2 C1 N1 . . 122.69(11) ?
    N2 C1 C9 . . 118.73(11) ?
    N1 C1 C9 . . 118.53(11) ?
    O1 C2 N1 . . 120.11(11) ?
    O1 C2 C3 . . 125.67(12) ?
    N1 C2 C3 . . 114.21(10) ?
    C4 C3 C5 . . 120.51(12) ?
    C4 C3 C2 . . 118.94(11) ?
    C5 C3 C2 . . 120.55(11) ?
    N2 C4 C3 . . 122.27(11) ?
    N2 C4 C8 . . 118.95(12) ?
    C3 C4 C8 . . 118.78(12) ?
    C6 C5 C3 . . 119.73(13) ?
    C6 C5 H5 . . 120.1 ?
    C3 C5 H5 . . 120.1 ?
    C5 C6 C7 . . 119.93(13) ?
    C5 C6 H6 . . 120.0 ?
    C7 C6 H6 . . 120.0 ?
    C8 C7 C6 . . 121.04(13) ?
    C8 C7 H7 . . 119.5 ?
    C6 C7 H7 . . 119.5 ?
    C7 C8 C4 . . 119.99(13) ?
    C7 C8 H8 . . 120.0 ?
    C4 C8 H8 . . 120.0 ?
    C1 C9 C10 . . 112.34(12) ?
    C1 C9 H9A . . 109.1 ?
    C10 C9 H9A . . 109.1 ?
    C1 C9 H9B . . 109.1 ?
    C10 C9 H9B . . 109.1 ?
    H9A C9 H9B . . 107.9 ?
    C11 C10 C9 . . 112.30(15) ?
    C11 C10 H10A . . 109.1 ?
    C9 C10 H10A . . 109.1 ?
    C11 C10 H10B . . 109.1 ?
    C9 C10 H10B . . 109.1 ?
    H10A C10 H10B . . 107.9 ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C1 N1 C2 . . 123.22(10) ?
    C1 N1 N3 . . 118.60(10) ?
    C2 N1 N3 . . 118.13(10) ?
    C1 N2 C4 . . 118.58(11) ?
    N1 N3 H3A . . 104.0(11) ?
    N1 N3 H3B . . 103.8(13) ?
    H3A N3 H3B . . 108.1(17) ?
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
    O1 C2 C3 C4 . . . . 176.78(12) ?
    N1 C2 C3 C4 . . . . -3.10(16) ?
    O1 C2 C3 C5 . . . . -3.2(2) ?
    N1 C2 C3 C5 . . . . 176.95(11) ?
    C5 C3 C4 N2 . . . . -178.79(11) ?
    C2 C3 C4 N2 . . . . 1.26(17) ?
    C5 C3 C4 C8 . . . . 1.61(18) ?
    C2 C3 C4 C8 . . . . -178.34(11) ?
    C4 C3 C5 C6 . . . . -0.98(19) ?
    C2 C3 C5 C6 . . . . 178.97(12) ?
    C3 C5 C6 C7 . . . . -0.4(2) ?
    C5 C6 C7 C8 . . . . 1.2(2) ?
    C6 C7 C8 C4 . . . . -0.6(2) ?
    N2 C4 C8 C7 . . . . 179.55(13) ?
    C3 C4 C8 C7 . . . . -0.8(2) ?
    N2 C1 C9 C10 . . . . -89.31(15) ?
    N1 C1 C9 C10 . . . . 88.39(15) ?
    C1 C9 C10 C11 . . . . 175.23(16) ?
    N2 C1 N1 C2 . . . . -1.99(18) ?
    C9 C1 N1 C2 . . . . -179.59(11) ?
    N2 C1 N1 N3 . . . . -179.17(11) ?
    C9 C1 N1 N3 . . . . 3.23(16) ?
    O1 C2 N1 C1 . . . . -176.35(11) ?
    C3 C2 N1 C1 . . . . 3.54(16) ?
    O1 C2 N1 N3 . . . . 0.84(17) ?
    C3 C2 N1 N3 . . . . -179.27(10) ?
    N1 C1 N2 C4 . . . . -0.22(18) ?
    C9 C1 N2 C4 . . . . 177.38(11) ?
    C3 C4 N2 C1 . . . . 0.51(18) ?
    C8 C4 N2 C1 . . . . -179.89(12) ?
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
    N3 H3A N2 11 0.91(2) 2.16(2) 3.0677(17) 176.1(16)
    N3 H3B O1 8_544 0.87(2) 2.51(2) 3.0599(16) 122.0(15)
    C5 H5 O1 6 0.93 2.44 3.3163(16) 157.2
_shelxl_version_number         .2013
data_New_Global_Publ_Block
_journal_date_recd_electronic     2015-07-02
_journal_date_accepted     2015-07-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      8
_journal_page_first     o590
_journal_page_last     o591
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989015013134
_journal_coeditor_code     CV5493
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'Gamal A. El-Hiti'
;
Cornea Research Chair
Department of Optometry
College of Applied Medical Sciences
King Saud University
PO Box 10219
Riyadh 11433
Saudi Arabia
;
 gelhiti@ksu.edu.sa
    'Kariuki, Benson M.'
;
School of Chemistry
Cardiff University
Main Building
Park Place
Cardiff CF10 3AT
Wales
;
 kariukib@cardiff.ac.uk
_publ_contact_author_fax     '00966114693536'
_publ_contact_author_phone     '009661149693778'
_publ_section_title
;
Crystal structure of 3-amino-2-propylquinazolin-4(3H)-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'El-Hiti, Gamal A.' .
;
Cornea Research Chair
Department of Optometry
College of Applied Medical Sciences
King Saud University
PO Box 10219
Riyadh 11433
Saudi Arabia
;
    'Smith, Keith' .
;
School of Chemistry
Cardiff University
Main Building
Park Place
Cardiff CF10 3AT
Wales
;
    'Hegazy, Amany S.' .
;
School of Chemistry
Cardiff University
Main Building
Park Place
Cardiff CF10 3AT
Wales
;
    'Alanazi, Saud A.' .
;
Cornea Research Chair
Department of Optometry
College of Applied Medical Sciences
King Saud University
PO Box 10219
Riyadh 11433
Saudi Arabia
;
    'Kariuki, Benson M.' .
;
School of Chemistry
Cardiff University
Main Building
Park Place
Cardiff CF10 3AT
Wales
;
