#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/59/2225924.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_2225924
loop_
_publ_author_name
'Elmuradov, Burkhon Zh'
'Turgunov, Kambarali'
'Tashkhodjaev, Bakhodir'
'Shakhidoyatov, Khusniddin M.'
_publ_section_title
;
 (E)-3-Propoxymethylidene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
 monohydrate
;
_journal_coeditor_code           LH5028
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1238
_journal_paper_doi               10.1107/S1600536810014303
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H16 N2 O2, H2 O'
_chemical_formula_moiety         'C15 H16 N2 O2, H2 O '
_chemical_formula_sum            'C15 H18 N2 O3'
_chemical_formula_weight         274.31
_chemical_name_systematic
;
(E)-3-Propoxymethylidene-2,3-dihydro-1H-
pyrrolo[2,1-b]quinazolin-9-one monohydrate
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 97.90(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.247(2)
_cell_length_b                   6.8760(10)
_cell_length_c                   10.950(2)
_cell_measurement_reflns_used    15
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      10
_cell_measurement_theta_min      5
_cell_volume                     689.6(2)
_computing_cell_refinement       'STADI4 (Stoe & Cie, 1997)'
_computing_data_collection       'STADI4 (Stoe & Cie, 1997)'
_computing_data_reduction        'X-RED  (Stoe & Cie, 1997)'
_computing_molecular_graphics    'XP (Bruker, 1998)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Stoe Stadi-4 four-circle'
_diffrn_measurement_device_type  'Stoe Stadi-4 four-circle'
_diffrn_measurement_method
; ;
Scan width (ω) = 1.56--1.68, scan ratio 2\q:\w = 1.00
I(Net) and σ(I) calculated according to Blessing (1987)
[Blessing, R. H. (1987). Cryst. Rev. 1, 3--58]
;
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1483
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.189
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0340P)²+0.5511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1439
_reflns_number_gt                1000
_reflns_number_total             1479
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            lh5028.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2225924
_cod_database_fobs_code          2225924
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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 0.7289(3) 0.2500 0.2635(2) 0.0522(8) Uani d S 1 . .
O O2 0.1375(3) 0.2500 0.5696(3) 0.0682(10) Uani d S 1 . .
N N1 0.5853(3) 0.2500 0.6240(3) 0.0390(8) Uani d S 1 . .
C C2 0.5055(4) 0.2500 0.5163(3) 0.0349(9) Uani d S 1 . .
N N3 0.3551(3) 0.2500 0.4988(3) 0.0370(8) Uani d S 1 . .
C C4 0.2711(4) 0.2500 0.5924(3) 0.0430(10) Uani d S 1 . .
C C4A 0.3567(4) 0.2500 0.7153(3) 0.0384(9) Uani d S 1 . .
C C5 0.2880(4) 0.2500 0.8207(4) 0.0493(11) Uani d S 1 . .
H H5A 0.1865 0.2500 0.8133 0.059 Uiso calc SR 1 . .
C C6 0.3684(4) 0.2500 0.9343(4) 0.0546(12) Uani d S 1 . .
H H6A 0.3215 0.2500 1.0043 0.066 Uiso calc SR 1 . .
C C7 0.5192(5) 0.2500 0.9468(4) 0.0531(11) Uani d S 1 . .
H H7A 0.5731 0.2500 1.0251 0.064 Uiso calc SR 1 . .
C C8 0.5901(4) 0.2500 0.8445(3) 0.0448(10) Uani d S 1 . .
H H8A 0.6916 0.2500 0.8539 0.054 Uiso calc SR 1 . .
C C8A 0.5102(4) 0.2500 0.7258(3) 0.0355(9) Uani d S 1 . .
C C9 0.5544(4) 0.2500 0.3964(3) 0.0384(9) Uani d S 1 . .
C C10 0.4244(4) 0.2500 0.2975(3) 0.0452(10) Uani d S 1 . .
H H10A 0.4243 0.1352 0.2460 0.054 Uiso calc PR 0.50 . .
H H10B 0.4243 0.3648 0.2460 0.054 Uiso calc PR 0.50 . .
C C11 0.2918(4) 0.2500 0.3684(3) 0.0472(10) Uani d S 1 . .
H H11A 0.2322 0.3648 0.3486 0.057 Uiso calc PR 0.50 . .
H H11B 0.2322 0.1352 0.3486 0.057 Uiso calc PR 0.50 . .
C C12 0.6934(4) 0.2500 0.3777(3) 0.0447(10) Uani d S 1 . .
H H12A 0.7667 0.2500 0.4449 0.054 Uiso calc SR 1 . .
C C13 0.8823(4) 0.2500 0.2525(4) 0.0586(13) Uani d S 1 . .
H H13A 0.9291 0.1354 0.2916 0.070 Uiso calc PR 0.50 . .
H H13B 0.9291 0.3646 0.2916 0.070 Uiso calc PR 0.50 . .
C C14 0.8937(5) 0.2500 0.1161(4) 0.0673(14) Uani d S 1 . .
H H14A 0.8438 0.1361 0.0788 0.081 Uiso calc PR 0.50 . .
H H14B 0.8438 0.3639 0.0788 0.081 Uiso calc PR 0.50 . .
C C15 1.0456(5) 0.2500 0.0877(5) 0.096(2) Uani d S 1 . .
H H15A 1.0448 0.2500 -0.0001 0.144 Uiso calc SR 1 . .
H H15B 1.0953 0.1360 0.1224 0.144 Uiso calc PR 0.50 . .
H H15C 1.0953 0.3640 0.1224 0.144 Uiso calc PR 0.50 . .
O O1W 0.9030(4) 0.2500 0.7141(4) 0.1047(17) Uani d S 1 . .
H H2 0.975(8) 0.2500 0.665(6) 0.15(3) Uiso d S 1 . .
H H1 0.816(8) 0.2500 0.676(7) 0.17(3) Uiso d S 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O1 C13 . . 116.8(3) ?
C2 N1 C8A . . 116.3(3) ?
N1 C2 N3 . . 124.2(3) ?
N1 C2 C9 . . 127.8(3) ?
N3 C2 C9 . . 108.0(3) ?
C4 N3 C2 . . 124.2(3) ?
C4 N3 C11 . . 122.5(3) ?
C2 N3 C11 . . 113.3(3) ?
O2 C4 N3 . . 120.4(4) ?
O2 C4 C4A . . 126.2(3) ?
N3 C4 C4A . . 113.4(3) ?
C5 C4A C8A . . 120.2(3) ?
C5 C4A C4 . . 120.7(3) ?
C8A C4A C4 . . 119.1(3) ?
C6 C5 C4A . . 120.3(4) ?
C6 C5 H5A . . 119.9 ?
C4A C5 H5A . . 119.9 ?
C5 C6 C7 . . 120.6(4) ?
C5 C6 H6A . . 119.7 ?
C7 C6 H6A . . 119.7 ?
C8 C7 C6 . . 120.5(4) ?
C8 C7 H7A . . 119.8 ?
C6 C7 H7A . . 119.8 ?
C7 C8 C8A . . 120.4(4) ?
C7 C8 H8A . . 119.8 ?
C8A C8 H8A . . 119.8 ?
N1 C8A C8 . . 119.0(3) ?
N1 C8A C4A . . 122.9(3) ?
C8 C8A C4A . . 118.2(3) ?
C12 C9 C2 . . 124.7(3) ?
C12 C9 C10 . . 125.7(3) ?
C2 C9 C10 . . 109.6(3) ?
C9 C10 C11 . . 104.5(3) ?
C9 C10 H10A . . 110.8 ?
C11 C10 H10A . . 110.8 ?
C9 C10 H10B . . 110.8 ?
C11 C10 H10B . . 110.8 ?
H10A C10 H10B . . 108.9 ?
N3 C11 C10 . . 104.6(3) ?
N3 C11 H11A . . 110.8 ?
C10 C11 H11A . . 110.8 ?
N3 C11 H11B . . 110.8 ?
C10 C11 H11B . . 110.8 ?
H11A C11 H11B . . 108.9 ?
C9 C12 O1 . . 120.8(3) ?
C9 C12 H12A . . 119.6 ?
O1 C12 H12A . . 119.6 ?
O1 C13 C14 . . 106.6(3) ?
O1 C13 H13A . . 110.4 ?
C14 C13 H13A . . 110.4 ?
O1 C13 H13B . . 110.4 ?
C14 C13 H13B . . 110.4 ?
H13A C13 H13B . . 108.6 ?
C15 C14 C13 . . 113.9(4) ?
C15 C14 H14A . . 108.8 ?
C13 C14 H14A . . 108.8 ?
C15 C14 H14B . . 108.8 ?
C13 C14 H14B . . 108.8 ?
H14A C14 H14B . . 107.7 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
H2 O1W H1 . . 115(6) ?
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 C12 . 1.336(4) ?
O1 C13 . 1.439(4) ?
O2 C4 . 1.226(4) ?
N1 C2 . 1.302(4) ?
N1 C8A . 1.391(4) ?
C2 N3 . 1.377(4) ?
C2 C9 . 1.447(5) ?
N3 C4 . 1.369(4) ?
N3 C11 . 1.467(4) ?
C4 C4A . 1.464(5) ?
C4A C5 . 1.392(5) ?
C4A C8A . 1.408(5) ?
C5 C6 . 1.359(5) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.383(5) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.374(5) ?
C7 H7A . 0.9300 ?
C8 C8A . 1.404(5) ?
C8 H8A . 0.9300 ?
C9 C12 . 1.329(5) ?
C9 C10 . 1.502(5) ?
C10 C11 . 1.539(5) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9300 ?
C13 C14 . 1.512(5) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.479(6) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
O1W H2 . 0.91(7) ?
O1W H1 . 0.85(8) ?
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
O1w H1 N1 1_555 0.85(7) 2.14(8) 2.968(5) 165(7) y
O1w H2 O2 1_655 0.90(7) 1.95(7) 2.855(5) 176(6) y
