(S,E)-3-[(2-Hy-droxy-benzyl-idene)amino]-2-(2-hy-droxy-phen-yl)-2,3-dihydro-quinazolin-4(1H)-one.

In the title compound, C(21)H(17)N(3)O(3), the dihydro-quinazoline ring adopts a screw-boat conformation and its stereogenic C atom has an S configuration. The dihedral angle between the mean planes of the two hy-droxy-phenyl rings is 86.61 (12)°. The amino H atom forms an intra-molecular hydrogen bond with a phenol O atom, while the hydrazine N atom acts as an acceptor for the H atom of the other phenol group. In the crystal, O-H⋯N and O-H⋯O hydrogen bonds and weak C-H⋯centroid(π-ring) inter-molecular inter-actions are observed, forming chains along [1-10] and [110].

Related literature

For related structures and their biological properties, see: Rádl et al. (2000 ▶); Andries et al. (2005 ▶); Alagarsamy et al. (2006 ▶); Ghorab et al. (2007 ▶); El-Azab et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For determination of the absolute configuration, see: Flack (1983 ▶); Hooft et al. (2008 ▶).

Experimental

Crystal data

C21H17N3O3

M = 359.38

Orthorhombic,

a = 13.344 (15) Å

b = 10.693 (14) Å

c = 23.537 (13) Å

V = 3358 (6) Å3

Z = 8

Cu Kα radiation

μ = 0.79 mm−1

T = 193 K

0.41 × 0.34 × 0.16 mm

Data collection

Rigaku RAPID II R-AXIS conversion diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.720, T max = 0.889

15117 measured reflections

2947 independent reflections

2758 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.07

2947 reflections

250 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), with 1258 Friedel pairs

Flack parameter: 0.0 (2)

Data collection: CrystalClear-SM Expert (Rigaku, 2009 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) interfaced by CRYSTALBUILDER (Welter, 2006 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812030012/jj2144sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030012/jj2144Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030012/jj2144Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H17N3O3	F(000) = 1504
Mr = 359.38	Dx = 1.422 Mg m−3
Orthorhombic, C2221	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: C 2c 2	Cell parameters from 7031 reflections
a = 13.344 (15) Å	θ = 1.9–68.2°
b = 10.693 (14) Å	µ = 0.79 mm−1
c = 23.537 (13) Å	T = 193 K
V = 3358 (6) Å3	Block, colourless
Z = 8	0.41 × 0.34 × 0.16 mm

Rigaku RAPID II R-AXIS conversion diffractometer	2947 independent reflections
Radiation source: fine-focus rotating anode	2758 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
profile data from ω scans	θmax = 68.2°, θmin = 3.8°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −16→16
Tmin = 0.720, Tmax = 0.889	k = −12→11
15117 measured reflections	l = −28→27

Refinement on F2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.056P)2 + 1.1889P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.18 e Å−3
2947 reflections	Δρmin = −0.21 e Å−3
250 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.00069 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 1258 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.0 (2)

Experimental. Selected IR data (cm-1, KBr pellet): 3400, 3216, 1730, 1650, 1582, 1458, 764.

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.

	x	y	z	Uiso*/Ueq
O1	0.49079 (10)	0.40376 (14)	0.35557 (7)	0.0471 (4)
O2	0.15925 (9)	0.01452 (15)	0.36712 (6)	0.0432 (4)
H2O	0.1100	−0.0300	0.3621	0.052*
O3	0.3763 (2)	0.6657 (2)	0.43629 (9)	0.0793 (7)
H3O	0.3861	0.5928	0.4270	0.119*
N1	0.34660 (10)	0.08134 (15)	0.39518 (6)	0.0305 (3)
H1N	0.3110 (16)	0.005 (2)	0.3973 (9)	0.037*
N2	0.35606 (10)	0.31007 (15)	0.38330 (7)	0.0320 (4)
N3	0.32933 (12)	0.43142 (16)	0.40226 (7)	0.0372 (4)
C1	0.29276 (12)	0.19782 (16)	0.38113 (8)	0.0288 (4)
H1	0.2401	0.2085	0.4098	0.035*
C2	0.42664 (12)	0.06210 (18)	0.36295 (8)	0.0314 (4)
C3	0.46168 (13)	−0.06173 (19)	0.35216 (9)	0.0382 (5)
H3	0.4282	−0.1310	0.3667	0.046*
C4	0.54310 (14)	−0.0748 (2)	0.32088 (9)	0.0458 (5)
H4	0.5682	−0.1535	0.3120	0.055*
C5	0.59031 (15)	0.0343 (2)	0.30160 (10)	0.0480 (6)
H5	0.6475	0.0251	0.2794	0.058*
C6	0.55737 (14)	0.1572 (2)	0.31343 (9)	0.0415 (5)
H6	0.5928	0.2260	0.2999	0.050*
C7	0.47477 (13)	0.17286 (19)	0.34431 (8)	0.0345 (4)
C8	0.44402 (13)	0.30414 (18)	0.36033 (8)	0.0341 (4)
C9	0.24182 (11)	0.18717 (17)	0.32475 (8)	0.0281 (4)
C10	0.25851 (13)	0.26696 (18)	0.27833 (8)	0.0326 (4)
H10	0.3038	0.3326	0.2821	0.039*
C11	0.21035 (14)	0.2508 (2)	0.22803 (8)	0.0385 (5)
H11	0.2223	0.3039	0.1975	0.046*
C12	0.14367 (14)	0.1541 (2)	0.22371 (9)	0.0405 (5)
H12	0.1100	0.1411	0.1896	0.049*
C13	0.12505 (13)	0.0739 (2)	0.26992 (8)	0.0355 (4)
H13	0.0793	0.0089	0.2660	0.043*
C14	0.17329 (12)	0.09045 (18)	0.32014 (8)	0.0313 (4)
C15	0.24436 (16)	0.45674 (19)	0.41379 (8)	0.0398 (5)
H15	0.1938	0.3979	0.4086	0.048*
C16	0.2200 (2)	0.5842 (2)	0.43671 (9)	0.0511 (6)
C17	0.1267 (2)	0.6088 (3)	0.44981 (11)	0.0760 (10)
H17	0.0772	0.5493	0.4430	0.091*
C18	0.1004 (4)	0.7261 (5)	0.47435 (13)	0.1121 (18)
H18	0.0330	0.7395	0.4825	0.135*
C19	0.1639 (5)	0.8182 (4)	0.48665 (14)	0.119 (2)
H19	0.1430	0.8919	0.5040	0.143*
C20	0.2560 (4)	0.7988 (3)	0.47299 (11)	0.0920 (13)
H20	0.3041	0.8603	0.4791	0.110*
C21	0.2836 (3)	0.6810 (3)	0.44825 (10)	0.0665 (8)

	U11	U22	U33	U12	U13	U23
O1	0.0269 (6)	0.0451 (8)	0.0693 (10)	−0.0139 (6)	−0.0023 (6)	0.0087 (8)
O2	0.0262 (7)	0.0524 (9)	0.0510 (8)	−0.0173 (6)	−0.0047 (6)	0.0142 (7)
O3	0.1221 (19)	0.0582 (12)	0.0577 (12)	−0.0448 (12)	0.0036 (12)	−0.0071 (10)
N1	0.0215 (7)	0.0338 (9)	0.0362 (8)	−0.0038 (6)	−0.0006 (6)	0.0028 (7)
N2	0.0227 (7)	0.0335 (9)	0.0399 (8)	−0.0067 (6)	−0.0011 (6)	−0.0027 (7)
N3	0.0384 (9)	0.0357 (9)	0.0374 (8)	−0.0059 (7)	−0.0025 (7)	−0.0016 (7)
C1	0.0215 (7)	0.0305 (10)	0.0344 (9)	−0.0040 (7)	0.0027 (7)	0.0000 (8)
C2	0.0199 (8)	0.0429 (11)	0.0314 (9)	−0.0012 (7)	−0.0019 (7)	0.0001 (8)
C3	0.0260 (9)	0.0424 (11)	0.0461 (11)	−0.0003 (8)	−0.0039 (8)	0.0030 (10)
C4	0.0293 (9)	0.0570 (14)	0.0513 (12)	0.0113 (9)	−0.0021 (8)	−0.0075 (11)
C5	0.0242 (9)	0.0714 (16)	0.0483 (12)	0.0063 (9)	0.0037 (8)	0.0000 (12)
C6	0.0205 (9)	0.0598 (13)	0.0443 (12)	−0.0021 (8)	0.0015 (8)	0.0080 (10)
C7	0.0223 (8)	0.0452 (11)	0.0360 (10)	−0.0027 (8)	−0.0042 (7)	0.0052 (9)
C8	0.0239 (8)	0.0406 (11)	0.0378 (10)	−0.0070 (8)	−0.0051 (7)	0.0051 (9)
C9	0.0164 (7)	0.0310 (9)	0.0370 (9)	0.0018 (6)	0.0015 (7)	−0.0023 (8)
C10	0.0217 (8)	0.0348 (10)	0.0413 (10)	0.0003 (7)	0.0035 (7)	0.0021 (8)
C11	0.0283 (8)	0.0512 (12)	0.0360 (10)	0.0040 (9)	0.0030 (8)	0.0087 (9)
C12	0.0287 (9)	0.0524 (13)	0.0405 (10)	0.0083 (9)	−0.0070 (8)	−0.0051 (9)
C13	0.0229 (8)	0.0360 (10)	0.0477 (11)	0.0001 (7)	−0.0068 (8)	−0.0056 (9)
C14	0.0212 (8)	0.0309 (10)	0.0416 (10)	−0.0005 (7)	0.0009 (7)	0.0006 (8)
C15	0.0427 (11)	0.0393 (11)	0.0376 (10)	0.0027 (9)	−0.0060 (9)	−0.0039 (8)
C16	0.0797 (16)	0.0419 (13)	0.0317 (10)	0.0166 (12)	−0.0107 (10)	−0.0029 (9)
C17	0.088 (2)	0.093 (2)	0.0472 (14)	0.0530 (18)	−0.0220 (14)	−0.0189 (14)
C18	0.158 (4)	0.125 (3)	0.0533 (17)	0.105 (3)	−0.035 (2)	−0.033 (2)
C19	0.239 (6)	0.072 (3)	0.0467 (18)	0.086 (3)	−0.030 (3)	−0.0183 (17)
C20	0.198 (4)	0.0386 (17)	0.0398 (14)	0.003 (2)	−0.017 (2)	−0.0004 (12)
C21	0.120 (3)	0.0441 (15)	0.0353 (12)	−0.0033 (16)	−0.0030 (14)	0.0052 (10)

O1—C8	1.240 (3)	C7—C8	1.510 (3)
O2—C14	1.385 (2)	C9—C14	1.385 (3)
O2—H2O	0.8200	C9—C10	1.404 (3)
O3—C21	1.280 (4)	C10—C11	1.358 (3)
O3—H3O	0.8200	C10—H10	0.9300
N1—C2	1.326 (3)	C11—C12	1.368 (3)
N1—C1	1.475 (3)	C11—H11	0.9300
N1—H1N	0.95 (2)	C12—C13	1.407 (3)
N2—C8	1.294 (3)	C12—H12	0.9300
N2—N3	1.418 (3)	C13—C14	1.358 (3)
N2—C1	1.469 (3)	C13—H13	0.9300
N3—C15	1.197 (3)	C15—C16	1.501 (3)
C1—C9	1.495 (3)	C15—H15	0.9300
C1—H1	0.9800	C16—C17	1.310 (4)
C2—C7	1.417 (3)	C16—C21	1.365 (4)
C2—C3	1.427 (3)	C17—C18	1.425 (5)
C3—C4	1.320 (3)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.331 (7)
C4—C5	1.401 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.288 (6)
C5—C6	1.414 (4)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.436 (5)
C6—C7	1.331 (3)	C20—H20	0.9300
C6—H6	0.9300
C14—O2—H2O	109.5	C10—C9—C1	124.91 (16)
C21—O3—H3O	109.5	C11—C10—C9	121.75 (18)
C2—N1—C1	113.27 (15)	C11—C10—H10	119.1
C2—N1—H1N	107.5 (13)	C9—C10—H10	119.1
C1—N1—H1N	119.7 (12)	C10—C11—C12	117.93 (19)
C8—N2—N3	113.87 (15)	C10—C11—H11	121.0
C8—N2—C1	117.86 (16)	C12—C11—H11	121.0
N3—N2—C1	127.89 (15)	C11—C12—C13	121.21 (18)
C15—N3—N2	121.12 (17)	C11—C12—H12	119.4
N2—C1—N1	113.71 (16)	C13—C12—H12	119.4
N2—C1—C9	110.76 (15)	C14—C13—C12	120.64 (18)
N1—C1—C9	110.85 (14)	C14—C13—H13	119.7
N2—C1—H1	107.1	C12—C13—H13	119.7
N1—C1—H1	107.1	C13—C14—O2	123.69 (17)
C9—C1—H1	107.1	C13—C14—C9	118.61 (18)
N1—C2—C7	114.36 (18)	O2—C14—C9	117.69 (16)
N1—C2—C3	120.64 (17)	N3—C15—C16	119.5 (2)
C7—C2—C3	124.88 (17)	N3—C15—H15	120.3
C4—C3—C2	117.8 (2)	C16—C15—H15	120.3
C4—C3—H3	121.1	C17—C16—C21	113.1 (3)
C2—C3—H3	121.1	C17—C16—C15	118.2 (3)
C3—C4—C5	117.6 (2)	C21—C16—C15	128.7 (3)
C3—C4—H4	121.2	C16—C17—C18	120.4 (4)
C5—C4—H4	121.2	C16—C17—H17	119.8
C4—C5—C6	124.8 (2)	C18—C17—H17	119.8
C4—C5—H5	117.6	C19—C18—C17	125.6 (4)
C6—C5—H5	117.6	C19—C18—H18	117.2
C7—C6—C5	118.8 (2)	C17—C18—H18	117.2
C7—C6—H6	120.6	C20—C19—C18	115.8 (3)
C5—C6—H6	120.6	C20—C19—H19	122.1
C6—C7—C2	116.1 (2)	C18—C19—H19	122.1
C6—C7—C8	118.56 (18)	C19—C20—C21	119.1 (4)
C2—C7—C8	125.20 (17)	C19—C20—H20	120.4
O1—C8—N2	116.90 (19)	C21—C20—H20	120.4
O1—C8—C7	129.74 (18)	O3—C21—C16	117.4 (3)
N2—C8—C7	113.35 (16)	O3—C21—C20	116.6 (3)
C14—C9—C10	119.84 (17)	C16—C21—C20	125.9 (4)
C14—C9—C1	115.25 (16)
C8—N2—N3—C15	164.97 (18)	N2—C1—C9—C14	−174.44 (14)
C1—N2—N3—C15	−7.7 (3)	N1—C1—C9—C14	58.4 (2)
C8—N2—C1—N1	44.5 (2)	N2—C1—C9—C10	5.2 (2)
N3—N2—C1—N1	−143.08 (16)	N1—C1—C9—C10	−122.02 (19)
C8—N2—C1—C9	−81.11 (19)	C14—C9—C10—C11	−1.2 (3)
N3—N2—C1—C9	91.3 (2)	C1—C9—C10—C11	179.20 (17)
C2—N1—C1—N2	−55.6 (2)	C9—C10—C11—C12	0.4 (3)
C2—N1—C1—C9	69.98 (19)	C10—C11—C12—C13	0.3 (3)
C1—N1—C2—C7	31.0 (2)	C11—C12—C13—C14	−0.2 (3)
C1—N1—C2—C3	−152.58 (17)	C12—C13—C14—O2	−179.43 (16)
N1—C2—C3—C4	−178.41 (17)	C12—C13—C14—C9	−0.6 (3)
C7—C2—C3—C4	−2.4 (3)	C10—C9—C14—C13	1.3 (3)
C2—C3—C4—C5	1.3 (3)	C1—C9—C14—C13	−179.12 (16)
C3—C4—C5—C6	0.3 (3)	C10—C9—C14—O2	−179.83 (16)
C4—C5—C6—C7	−1.1 (3)	C1—C9—C14—O2	−0.2 (2)
C5—C6—C7—C2	0.1 (3)	N2—N3—C15—C16	176.71 (16)
C5—C6—C7—C8	175.72 (17)	N3—C15—C16—C17	−179.0 (2)
N1—C2—C7—C6	177.84 (17)	N3—C15—C16—C21	−1.5 (3)
C3—C2—C7—C6	1.6 (3)	C21—C16—C17—C18	−1.0 (4)
N1—C2—C7—C8	2.6 (3)	C15—C16—C17—C18	176.9 (2)
C3—C2—C7—C8	−173.65 (18)	C16—C17—C18—C19	−0.7 (5)
N3—N2—C8—O1	−3.1 (2)	C17—C18—C19—C20	2.5 (5)
C1—N2—C8—O1	170.36 (16)	C18—C19—C20—C21	−2.3 (5)
N3—N2—C8—C7	175.68 (14)	C17—C16—C21—O3	−179.4 (2)
C1—N2—C8—C7	−10.8 (2)	C15—C16—C21—O3	3.1 (4)
C6—C7—C8—O1	−10.5 (3)	C17—C16—C21—C20	1.0 (4)
C2—C7—C8—O1	164.6 (2)	C15—C16—C21—C20	−176.6 (2)
C6—C7—C8—N2	170.89 (17)	C19—C20—C21—O3	−178.9 (3)
C2—C7—C8—N2	−14.0 (3)	C19—C20—C21—C16	0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···N3	0.84	1.95	2.704 (4)	148
O2—H2O···O1i	0.84	1.73	2.555 (3)	168
C4—H4···Cg3ii	0.93	2.64	3.546 (5)	160
C5—H5···Cg3iii	0.93	2.91	3.705 (5)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C16–C21 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯N3	0.84	1.95	2.704 (4)	148
O2—H2O⋯O1i	0.84	1.73	2.555 (3)	168
C4—H4⋯Cg3ii	0.93	2.64	3.546 (5)	160
C5—H5⋯Cg3iii	0.93	2.91	3.705 (5)	141

Symmetry codes: (i) ; (ii) ; (iii) .