Download citation
Download citation
link to html
In the crystal structure of the title compound, C15H12N4O·H2O, mol­ecules are linked by N—H...O hydrogen bonds and π–π and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011949/hg2023sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011949/hg2023Isup2.hkl
Contains datablock I

CCDC reference: 608346

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.051
  • wR factor = 0.149
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

4-Benzoylhydrazono-1,4-dihydroquinazoline monohydrate top
Crystal data top
C15H12N4O·H2OF(000) = 1184
Mr = 282.30Dx = 1.384 Mg m3
Monoclinic, C2/cMelting point: 519 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 16.9865 (14) ÅCell parameters from 7181 reflections
b = 7.2085 (6) Åθ = 1.8–27.5°
c = 22.1444 (18) ŵ = 0.10 mm1
β = 92.022 (1)°T = 292 K
V = 2709.8 (4) Å3Block, yellow
Z = 80.20 × 0.20 × 0.10 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3091 independent reflections
Radiation source: fine focus sealed Siemens Mo tube2643 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
0.3° wide ω exposures scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2221
Tmin = 0.972, Tmax = 0.981k = 99
15045 measured reflectionsl = 2828
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0936P)2 + 0.5569P]
where P = (Fo2 + 2Fc2)/3
3091 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.31 e Å3
4 restraintsΔρmin = 0.32 e Å3
Special details top

Experimental. IR (KBr, ν cm-1): 3326, 1658, 1607, 1544, 1381, 1096, 757,685; 1H NMR (DMSO-d6): δ 10.708 (m, 1H), 8.010–8.195 (s, 2H), 7.907–7.924 (s, 2H), 7.714 (s, 1H), 7.624–7.523 (s, 6H).

Geometry. 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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.01271 (8)0.76695 (16)0.54526 (5)0.0402 (3)
C20.04039 (9)0.7314 (2)0.59353 (6)0.0507 (3)
H20.09020.68490.58610.061*
C30.01926 (11)0.7648 (2)0.65209 (6)0.0607 (4)
H30.05490.74120.68400.073*
C40.05509 (11)0.8338 (2)0.66345 (6)0.0605 (4)
H40.06900.85500.70310.073*
C50.10820 (9)0.8710 (2)0.61699 (6)0.0537 (4)
H50.15780.91780.62490.064*
C60.08689 (8)0.83750 (17)0.55756 (5)0.0426 (3)
C70.11905 (8)0.8363 (2)0.45326 (6)0.0484 (3)
H70.15630.86200.42260.058*
C80.00526 (7)0.73457 (16)0.48192 (5)0.0383 (3)
C90.15188 (7)0.60618 (18)0.38440 (6)0.0425 (3)
C100.15355 (7)0.59668 (17)0.31693 (5)0.0411 (3)
C110.21050 (10)0.4885 (2)0.29155 (7)0.0653 (4)
H110.24560.42180.31630.078*
C120.21590 (12)0.4785 (3)0.22961 (7)0.0740 (5)
H120.25380.40260.21310.089*
C130.16653 (10)0.5782 (2)0.19231 (6)0.0583 (4)
H130.17060.57000.15060.070*
C140.11058 (8)0.6913 (3)0.21669 (6)0.0593 (4)
H140.07760.76240.19150.071*
C150.10353 (8)0.6992 (2)0.27877 (6)0.0519 (3)
H150.06500.77370.29510.062*
N10.13933 (7)0.87264 (17)0.50960 (5)0.0486 (3)
H10.1835 (7)0.925 (2)0.5166 (7)0.058*
N20.05223 (7)0.76851 (16)0.43716 (5)0.0457 (3)
N30.07481 (6)0.67618 (15)0.46866 (4)0.0424 (3)
N40.08316 (6)0.65468 (16)0.40703 (4)0.0431 (3)
H4A0.0415 (7)0.672 (2)0.3847 (6)0.052*
O10.21111 (6)0.57352 (18)0.41654 (5)0.0630 (3)
O20.27510 (6)0.93264 (17)0.45235 (5)0.0568 (3)
H2A0.3074 (10)0.918 (3)0.4807 (7)0.085*
H2B0.2599 (13)0.8263 (17)0.4433 (10)0.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0480 (7)0.0376 (6)0.0352 (6)0.0010 (5)0.0035 (5)0.0019 (4)
C20.0590 (8)0.0552 (8)0.0376 (6)0.0106 (6)0.0005 (5)0.0028 (5)
C30.0817 (11)0.0643 (9)0.0356 (7)0.0165 (7)0.0048 (7)0.0025 (6)
C40.0871 (11)0.0604 (9)0.0346 (6)0.0125 (8)0.0117 (7)0.0030 (6)
C50.0626 (8)0.0541 (8)0.0453 (7)0.0078 (6)0.0140 (6)0.0028 (6)
C60.0490 (7)0.0392 (6)0.0400 (6)0.0012 (5)0.0053 (5)0.0016 (5)
C70.0453 (7)0.0565 (8)0.0432 (7)0.0002 (6)0.0036 (5)0.0027 (5)
C80.0438 (6)0.0377 (6)0.0333 (6)0.0031 (4)0.0014 (5)0.0013 (4)
C90.0414 (6)0.0469 (6)0.0391 (6)0.0003 (5)0.0002 (5)0.0030 (5)
C100.0401 (6)0.0452 (6)0.0382 (6)0.0037 (5)0.0053 (5)0.0032 (4)
C110.0774 (10)0.0648 (9)0.0549 (8)0.0297 (8)0.0184 (7)0.0097 (7)
C120.0954 (13)0.0691 (10)0.0595 (9)0.0282 (9)0.0314 (9)0.0003 (8)
C130.0698 (9)0.0666 (9)0.0394 (7)0.0149 (7)0.0139 (6)0.0098 (6)
C140.0429 (7)0.0936 (11)0.0411 (7)0.0038 (7)0.0031 (5)0.0002 (7)
C150.0356 (6)0.0777 (9)0.0424 (7)0.0049 (6)0.0016 (5)0.0046 (6)
N10.0422 (6)0.0566 (7)0.0471 (6)0.0050 (5)0.0035 (5)0.0044 (5)
N20.0466 (6)0.0555 (6)0.0350 (5)0.0005 (5)0.0002 (4)0.0020 (4)
N30.0457 (6)0.0500 (6)0.0317 (5)0.0003 (4)0.0023 (4)0.0020 (4)
N40.0417 (6)0.0559 (6)0.0316 (5)0.0012 (5)0.0018 (4)0.0021 (4)
O10.0495 (6)0.0924 (8)0.0464 (6)0.0154 (5)0.0059 (4)0.0063 (5)
O20.0471 (6)0.0758 (7)0.0470 (5)0.0051 (5)0.0043 (4)0.0063 (5)
Geometric parameters (Å, º) top
C1—C61.3946 (18)C9—N41.3331 (17)
C1—C21.3977 (18)C9—C101.4969 (17)
C1—C81.4646 (16)C10—C111.3777 (19)
C2—C31.3789 (19)C10—C151.3897 (19)
C2—H20.9300C11—C121.380 (2)
C3—C41.388 (2)C11—H110.9300
C3—H30.9300C12—C131.361 (2)
C4—C51.371 (2)C12—H120.9300
C4—H40.9300C13—C141.377 (2)
C5—C61.3980 (18)C13—H130.9300
C5—H50.9300C14—C151.3851 (19)
C6—N11.3853 (17)C14—H140.9300
C7—N21.2972 (18)C15—H150.9300
C7—N11.3320 (17)N1—H10.859 (9)
C7—H70.9300N3—N41.3858 (14)
C8—N31.2976 (16)N4—H4A0.858 (9)
C8—N21.3885 (16)O2—H2A0.826 (10)
C9—O11.2344 (16)O2—H2B0.831 (10)
C6—C1—C2118.73 (11)C11—C10—C15118.40 (12)
C6—C1—C8117.74 (11)C11—C10—C9118.13 (12)
C2—C1—C8123.53 (12)C15—C10—C9123.37 (11)
C3—C2—C1120.31 (14)C10—C11—C12120.50 (14)
C3—C2—H2119.8C10—C11—H11119.8
C1—C2—H2119.8C12—C11—H11119.8
C2—C3—C4120.11 (14)C13—C12—C11120.96 (14)
C2—C3—H3119.9C13—C12—H12119.5
C4—C3—H3119.9C11—C12—H12119.5
C5—C4—C3120.84 (13)C12—C13—C14119.58 (13)
C5—C4—H4119.6C12—C13—H13120.2
C3—C4—H4119.6C14—C13—H13120.2
C4—C5—C6119.17 (14)C13—C14—C15119.89 (14)
C4—C5—H5120.4C13—C14—H14120.1
C6—C5—H5120.4C15—C14—H14120.1
N1—C6—C1118.55 (11)C14—C15—C10120.63 (13)
N1—C6—C5120.61 (12)C14—C15—H15119.7
C1—C6—C5120.83 (12)C10—C15—H15119.7
N2—C7—N1126.10 (12)C7—N1—C6120.11 (11)
N2—C7—H7117.0C7—N1—H1120.8 (11)
N1—C7—H7117.0C6—N1—H1119.0 (11)
N3—C8—N2121.24 (10)C7—N2—C8118.06 (11)
N3—C8—C1119.38 (11)C8—N3—N4112.63 (10)
N2—C8—C1119.38 (11)C9—N4—N3121.38 (10)
O1—C9—N4122.68 (12)C9—N4—H4A122.5 (11)
O1—C9—C10121.54 (11)N3—N4—H4A116.1 (11)
N4—C9—C10115.77 (11)H2A—O2—H2B105 (2)
C6—C1—C2—C30.3 (2)C15—C10—C11—C121.9 (2)
C8—C1—C2—C3179.83 (13)C9—C10—C11—C12178.39 (15)
C1—C2—C3—C40.2 (2)C10—C11—C12—C131.6 (3)
C2—C3—C4—C50.5 (3)C11—C12—C13—C140.3 (3)
C3—C4—C5—C60.4 (2)C12—C13—C14—C151.7 (2)
C2—C1—C6—N1179.98 (12)C13—C14—C15—C101.3 (2)
C8—C1—C6—N10.12 (17)C11—C10—C15—C140.5 (2)
C2—C1—C6—C50.5 (2)C9—C10—C15—C14176.75 (13)
C8—C1—C6—C5179.69 (11)N2—C7—N1—C60.1 (2)
C4—C5—C6—N1179.66 (13)C1—C6—N1—C71.09 (19)
C4—C5—C6—C10.1 (2)C5—C6—N1—C7178.48 (13)
C6—C1—C8—N3177.21 (11)N1—C7—N2—C82.0 (2)
C2—C1—C8—N32.64 (19)N3—C8—N2—C7176.30 (12)
C6—C1—C8—N22.22 (18)C1—C8—N2—C73.13 (18)
C2—C1—C8—N2177.93 (12)N2—C8—N3—N40.29 (17)
O1—C9—C10—C1123.6 (2)C1—C8—N3—N4179.13 (10)
N4—C9—C10—C11157.47 (14)O1—C9—N4—N31.7 (2)
O1—C9—C10—C15152.75 (14)C10—C9—N4—N3177.22 (10)
N4—C9—C10—C1526.23 (18)C8—N3—N4—C9176.05 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···N20.86 (1)2.12 (2)2.5526 (15)111 (1)
O2—H2B···O10.83 (1)2.08 (1)2.9071 (18)174 (2)
O2—H2A···N3i0.83 (1)2.36 (1)3.1400 (15)158 (2)
O2—H2A···O1i0.83 (1)2.31 (2)2.9048 (15)130 (2)
N1—H1···O2ii0.86 (1)2.01 (1)2.8524 (16)168 (2)
C12—H12···Cg1iii0.932.783.522 (2)138
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x, y+2, z+1; (iii) x, y1, z1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds