#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2224130.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224130
loop_
_publ_author_name
'Gao, Tao'
'Jiao, Yuan-Hong'
'Ng, Seik Weng'
_publ_section_title
;
 3-(2-Aminoethyl)-2-anilinoquinazolin-4(3<i>H</i>)-one methanol
 hemisolvate
;
_journal_coeditor_code           BT5121
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2989
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H16 N4 O, 0.5C H4 O'
_chemical_formula_moiety         'C16 H16 N4 O, 0.5(C H4 O)'
_chemical_formula_sum            'C16.5 H18 N4 O1.5'
_chemical_formula_weight         296.35
_chemical_name_systematic
;
3-(2-Aminoethyl)-2-anilinoquinazolin-4(3<i>H</i>)-one methanol hemisolvate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.3010(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.5972(11)
_cell_length_b                   12.2035(7)
_cell_length_c                   12.8681(8)
_cell_measurement_reflns_used    3816
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      2.4
_cell_volume                     2994.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14007
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3399
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1044P)^2^+0.1504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.1855
_reflns_number_gt                2377
_reflns_number_total             3399
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bt5121.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_[local]_cod_chemical_formula_sum_orig 'C16.50 H18 N4 O1.50'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224130
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'
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_
_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 0.0468(8) 0.0701(10) 0.0607(8) 0.0019(7) 0.0243(7) -0.0043(6)
N1 0.0402(9) 0.0437(9) 0.0438(8) 0.0002(7) 0.0110(7) -0.0028(6)
N2 0.0417(9) 0.0570(10) 0.0402(8) 0.0011(7) 0.0130(7) -0.0002(6)
N3 0.0430(9) 0.0665(11) 0.0405(8) 0.0019(8) 0.0107(7) 0.0053(7)
N4 0.0614(12) 0.0661(12) 0.0558(10) 0.0053(9) 0.0006(9) -0.0015(8)
C1 0.0435(10) 0.0412(10) 0.0411(9) -0.0070(8) 0.0128(8) -0.0050(7)
C2 0.0578(13) 0.0540(12) 0.0437(10) -0.0063(10) 0.0214(9) -0.0038(8)
C3 0.0697(14) 0.0649(13) 0.0384(9) -0.0019(11) 0.0128(10) 0.0028(9)
C4 0.0490(12) 0.0744(15) 0.0494(11) 0.0035(11) 0.0035(10) 0.0062(9)
C5 0.0446(12) 0.0782(15) 0.0510(11) 0.0058(10) 0.0152(9) 0.0035(10)
C6 0.0424(10) 0.0490(11) 0.0378(9) -0.0038(8) 0.0112(8) -0.0014(7)
C7 0.0443(11) 0.0438(10) 0.0459(10) -0.0063(8) 0.0164(8) -0.0070(7)
C8 0.0413(10) 0.0424(10) 0.0415(9) -0.0040(8) 0.0112(8) -0.0027(7)
C9 0.0445(11) 0.0432(10) 0.0411(9) -0.0007(8) 0.0122(8) 0.0067(7)
C10 0.0482(11) 0.0448(11) 0.0440(9) -0.0001(8) 0.0072(8) 0.0011(7)
C11 0.0636(14) 0.0570(12) 0.0404(9) 0.0007(10) 0.0159(9) -0.0006(8)
C12 0.0654(15) 0.0711(15) 0.0554(12) 0.0043(11) 0.0293(11) 0.0041(10)
C13 0.0466(12) 0.0792(16) 0.0620(13) -0.0042(10) 0.0187(10) 0.0085(10)
C14 0.0490(12) 0.0683(14) 0.0423(10) -0.0097(10) 0.0091(9) 0.0032(9)
C15 0.0507(12) 0.0492(12) 0.0548(11) 0.0090(9) 0.0119(9) -0.0007(8)
C16 0.0445(12) 0.0671(14) 0.0618(13) 0.0074(10) 0.0071(10) 0.0025(10)
O2 0.109(4) 0.189(6) 0.231(6) -0.017(4) 0.043(4) -0.115(5)
C17 0.044(6) 0.143(5) 0.117(8) 0.021(4) 0.017(5) 0.021(5)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
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
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)