5-Hydr­oxy-4-(4-methyl­benzo­yl)-1,3-diphenyl-1H-pyrazole

Liu, G.-F.; Peng, B.-H.; Liu, L.; Jia, D.-Z.; Yu, K.-B.

doi:10.1107/S1600536805039401

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5-Hydroxy-4-(4-methylbenzoyl)-1,3-diphenyl-1H-pyrazole

G.-F. Liu, B.-H. Peng, L. Liu, D.-Z. Jia and K.-B. Yu

The crystal structure of the title compound, C₂₃H₁₈N₂O₂, contains an intramolecular hydrogen bond that links the ketone and hydroxyl groups.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039401/ww6392sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039401/ww6392Isup2.hkl Contains datablock I

CCDC reference: 296697

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.002 Å
R factor = 0.036
wR factor = 0.096
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =      17.35
            Cell volume su given      =      21.00
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Pyrazol-5-one and its derivatives are widely used as biologically active compounds, metal extractants, dyes etc. (Ono et al., 1997). The tautomeric structures of these compounds have been extensively studied (Kataeva et al., 2002; Akama et al., 1996; Katritzky et al., 1964). For 4-acyl-substituted pyrazol-5-ones, two forms are stable in the solid state. These are the OH-form (A), stabilized by an intramolecular hydrogen bond, and the NH-form (B), stabilized by an intermolecular hydrogen bond (see scheme) (Kataeva et al., 2002). The X-ray crystal structure analysis of the title compound, (I), was undertaken in order to study its stereochemistry and crystal packing.

The present X-ray single-crystal study of compound (I) shows (Fig. 1) that it exists in the OH-tautomeric form.

Experimental top

The title compound was synthesized according to the method proposed by Jensen (1959) (yield 86%, m.p. 465–466 K). Analysis, required for C₂₃H₁₈N₂O₂: C 77.95, H 5.12, N 7.90%; found: C 77.62, H 5.34, N 7.92%. Plate-like single crystals of (I) were grown from a mixed solution of methanol and dichloromethane (Ratio?) by slow evaporation.

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. A view of the molecule of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram for (I), showing the dimers.

5-Hydroxy-4-(4-methylbenzoyl)-1,3-diphenyl-1H-pyrazole top

Crystal data top

C₂₃H₁₈N₂O₂	Z = 2
M_r = 354.39	F(000) = 372
Triclinic, P1	D_x = 1.278 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.705 (1) Å	Cell parameters from 28 reflections
b = 10.0821 (9) Å	θ = 3.9–15.0°
c = 10.746 (1) Å	µ = 0.08 mm⁻¹
α = 115.284 (8)°	T = 294 K
β = 102.13 (1)°	Plate, colourless
γ = 91.61 (1)°	0.30 × 0.28 × 0.26 mm
V = 921.2 (2) Å³

Data collection top

Siemens P4 diffractometer	R_int = 0.009
Radiation source: normal-focus sealed tube	θ_max = 25.3°, θ_min = 2.2°
Graphite monochromator	h = 0→11
ω scans	k = −11→11
4049 measured reflections	l = −12→12
3307 independent reflections	3 standard reflections every 97 reflections
2233 reflections with I > 2σ(I)	intensity decay: 4.8%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0522P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
3307 reflections	Δρ_max = 0.16 e Å⁻³
249 parameters	Δρ_min = −0.12 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.045 (4)

Crystal data top

C₂₃H₁₈N₂O₂	γ = 91.61 (1)°
M_r = 354.39	V = 921.2 (2) Å³
Triclinic, P1	Z = 2
a = 9.705 (1) Å	Mo Kα radiation
b = 10.0821 (9) Å	µ = 0.08 mm⁻¹
c = 10.746 (1) Å	T = 294 K
α = 115.284 (8)°	0.30 × 0.28 × 0.26 mm
β = 102.13 (1)°

Data collection top

Siemens P4 diffractometer	R_int = 0.009
4049 measured reflections	3 standard reflections every 97 reflections
3307 independent reflections	intensity decay: 4.8%
2233 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.037	2 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.16 e Å⁻³
3307 reflections	Δρ_min = −0.12 e Å⁻³
249 parameters

Special details top

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 > 2σ(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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.53443 (13)	0.68831 (13)	0.19927 (11)	0.0623 (3)
O2	0.35647 (13)	0.83941 (13)	0.32274 (12)	0.0708 (4)
N1	0.68695 (13)	0.61547 (14)	0.35100 (12)	0.0520 (3)
N2	0.71040 (13)	0.63278 (14)	0.48968 (12)	0.0528 (3)
C1	0.73782 (19)	0.4586 (2)	0.12434 (16)	0.0664 (5)
H1	0.6424	0.4467	0.0789	0.080*
C2	0.8348 (2)	0.3901 (2)	0.04805 (18)	0.0799 (6)
H2	0.8045	0.3329	−0.0496	0.096*
C3	0.9750 (2)	0.4057 (2)	0.1150 (2)	0.0844 (6)
H3	1.0395	0.3585	0.0632	0.101*
C4	1.0197 (2)	0.4910 (2)	0.2582 (2)	0.0901 (7)
H4	1.1150	0.5016	0.3036	0.108*
C5	0.92513 (19)	0.5617 (2)	0.33635 (19)	0.0746 (5)
H5	0.9561	0.6201	0.4338	0.090*
C6	0.78463 (17)	0.54439 (17)	0.26812 (15)	0.0533 (4)
C7	0.57692 (16)	0.68320 (16)	0.32192 (14)	0.0478 (4)
C8	0.51969 (15)	0.74366 (15)	0.44019 (14)	0.0452 (4)
C9	0.61152 (16)	0.70866 (16)	0.54247 (14)	0.0451 (4)
C10	0.61703 (14)	0.75032 (16)	0.69331 (14)	0.0439 (4)
C11	0.62524 (16)	0.64372 (18)	0.74239 (16)	0.0539 (4)
H11	0.6222	0.5451	0.6791	0.065*
C12	0.63783 (18)	0.6819 (2)	0.88412 (18)	0.0654 (5)
H12	0.6422	0.6091	0.9157	0.079*
C13	0.64387 (18)	0.8269 (2)	0.97814 (17)	0.0688 (5)
H13	0.6525	0.8529	1.0738	0.083*
C14	0.63716 (19)	0.9340 (2)	0.93079 (16)	0.0659 (5)
H14	0.6426	1.0327	0.9950	0.079*
C15	0.62256 (17)	0.89636 (18)	0.78947 (16)	0.0549 (4)
H15	0.6164	0.9695	0.7583	0.066*
C16	0.39436 (16)	0.81483 (16)	0.43021 (15)	0.0497 (4)
C17	0.30364 (15)	0.85520 (16)	0.53170 (15)	0.0476 (4)
C18	0.22801 (17)	0.97470 (18)	0.54930 (17)	0.0582 (4)
H18	0.2398	1.0306	0.5014	0.070*
C19	0.13562 (19)	1.0110 (2)	0.63714 (19)	0.0676 (5)
H19	0.0887	1.0934	0.6503	0.081*
C20	0.11181 (17)	0.9268 (2)	0.70582 (17)	0.0654 (5)
C21	0.18616 (18)	0.8073 (2)	0.68691 (17)	0.0625 (5)
H21	0.1715	0.7494	0.7323	0.075*
C22	0.28165 (16)	0.77185 (18)	0.60216 (15)	0.0534 (4)
H22	0.3314	0.6919	0.5923	0.064*
C23	0.0065 (2)	0.9634 (3)	0.7970 (2)	0.0995 (7)
H23A	−0.0344	1.0492	0.7977	0.119*	0.50
H23B	0.0543	0.9830	0.8921	0.119*	0.50
H23C	−0.0673	0.8812	0.7592	0.119*	0.50
H23D	0.0028	0.8931	0.8349	0.119*	0.50
H23E	−0.0859	0.9592	0.7405	0.119*	0.50
H23F	0.0357	1.0611	0.8735	0.119*	0.50
H1O	0.4642 (18)	0.745 (2)	0.2034 (16)	0.113 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0720 (8)	0.0786 (8)	0.0433 (6)	0.0150 (7)	0.0137 (5)	0.0332 (6)
O2	0.0825 (9)	0.0894 (9)	0.0601 (7)	0.0301 (7)	0.0193 (6)	0.0493 (7)
N1	0.0530 (8)	0.0657 (9)	0.0365 (7)	0.0106 (7)	0.0114 (6)	0.0215 (6)
N2	0.0536 (8)	0.0665 (9)	0.0376 (7)	0.0124 (7)	0.0115 (6)	0.0220 (6)
C1	0.0585 (11)	0.0902 (13)	0.0456 (9)	0.0132 (10)	0.0147 (8)	0.0247 (9)
C2	0.0768 (14)	0.1062 (16)	0.0491 (10)	0.0182 (12)	0.0259 (10)	0.0223 (10)
C3	0.0682 (14)	0.1074 (16)	0.0739 (13)	0.0190 (12)	0.0368 (11)	0.0275 (12)
C4	0.0496 (11)	0.1121 (17)	0.0800 (14)	0.0084 (11)	0.0164 (10)	0.0160 (12)
C5	0.0542 (11)	0.0875 (13)	0.0556 (10)	0.0065 (10)	0.0102 (9)	0.0090 (9)
C6	0.0519 (10)	0.0623 (10)	0.0441 (9)	0.0069 (8)	0.0165 (7)	0.0200 (8)
C7	0.0511 (9)	0.0542 (9)	0.0387 (8)	0.0028 (7)	0.0076 (7)	0.0230 (7)
C8	0.0485 (9)	0.0480 (9)	0.0379 (8)	0.0030 (7)	0.0076 (7)	0.0196 (7)
C9	0.0443 (9)	0.0485 (9)	0.0392 (8)	0.0021 (7)	0.0075 (7)	0.0179 (7)
C10	0.0381 (8)	0.0549 (9)	0.0381 (8)	0.0051 (7)	0.0066 (6)	0.0214 (7)
C11	0.0543 (10)	0.0581 (10)	0.0501 (9)	0.0042 (8)	0.0080 (7)	0.0271 (8)
C12	0.0637 (11)	0.0855 (13)	0.0586 (11)	0.0021 (10)	0.0099 (9)	0.0453 (10)
C13	0.0633 (11)	0.0999 (15)	0.0393 (9)	−0.0029 (10)	0.0083 (8)	0.0300 (10)
C14	0.0725 (12)	0.0688 (12)	0.0443 (9)	0.0037 (9)	0.0164 (8)	0.0133 (9)
C15	0.0610 (10)	0.0574 (10)	0.0468 (9)	0.0093 (8)	0.0145 (8)	0.0229 (8)
C16	0.0529 (10)	0.0495 (9)	0.0451 (8)	0.0032 (7)	0.0066 (7)	0.0223 (7)
C17	0.0422 (9)	0.0501 (9)	0.0438 (8)	0.0034 (7)	0.0024 (7)	0.0185 (7)
C18	0.0528 (10)	0.0579 (10)	0.0588 (10)	0.0080 (8)	0.0054 (8)	0.0249 (8)
C19	0.0540 (11)	0.0664 (11)	0.0664 (11)	0.0162 (9)	0.0073 (9)	0.0176 (9)
C20	0.0457 (10)	0.0814 (13)	0.0515 (10)	0.0044 (9)	0.0071 (8)	0.0156 (9)
C21	0.0532 (10)	0.0774 (12)	0.0566 (10)	0.0012 (9)	0.0131 (8)	0.0299 (9)
C22	0.0483 (9)	0.0594 (10)	0.0511 (9)	0.0062 (8)	0.0079 (7)	0.0253 (8)
C23	0.0721 (14)	0.1312 (19)	0.0836 (14)	0.0186 (13)	0.0345 (12)	0.0298 (14)

Geometric parameters (Å, º) top

O1—C7	1.3193 (16)	C12—C13	1.367 (2)
O1—H1O	0.898 (19)	C12—H12	0.9300
O2—C16	1.2655 (17)	C13—C14	1.374 (2)
N1—C7	1.3369 (19)	C13—H13	0.9300
N1—N2	1.3915 (16)	C14—C15	1.373 (2)
N1—C6	1.4330 (19)	C14—H14	0.9300
N2—C9	1.3142 (18)	C15—H15	0.9300
C1—C6	1.372 (2)	C16—C17	1.475 (2)
C1—C2	1.383 (2)	C17—C22	1.388 (2)
C1—H1	0.9300	C17—C18	1.393 (2)
C2—C3	1.368 (3)	C18—C19	1.381 (2)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.365 (3)	C19—C20	1.384 (3)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.380 (2)	C20—C21	1.384 (2)
C4—H4	0.9300	C20—C23	1.508 (2)
C5—C6	1.373 (2)	C21—C22	1.382 (2)
C5—H5	0.9300	C21—H21	0.9300
C7—C8	1.3962 (19)	C22—H22	0.9300
C8—C9	1.4366 (19)	C23—H23A	0.9600
C8—C16	1.437 (2)	C23—H23B	0.9600
C9—C10	1.4791 (18)	C23—H23C	0.9600
C10—C11	1.382 (2)	C23—H23D	0.9600
C10—C15	1.383 (2)	C23—H23E	0.9600
C11—C12	1.379 (2)	C23—H23F	0.9600
C11—H11	0.9300

C7—O1—H1O	109.5 (9)	C13—C14—H14	119.7
C7—N1—N2	110.47 (11)	C14—C15—C10	120.34 (15)
C7—N1—C6	130.20 (12)	C14—C15—H15	119.8
N2—N1—C6	119.06 (12)	C10—C15—H15	119.8
C9—N2—N1	106.01 (12)	O2—C16—C8	117.03 (13)
C6—C1—C2	118.97 (16)	O2—C16—C17	117.74 (13)
C6—C1—H1	120.5	C8—C16—C17	125.17 (13)
C2—C1—H1	120.5	C22—C17—C18	118.39 (15)
C3—C2—C1	120.61 (17)	C22—C17—C16	122.59 (14)
C3—C2—H2	119.7	C18—C17—C16	118.82 (14)
C1—C2—H2	119.7	C19—C18—C17	120.69 (16)
C4—C3—C2	119.67 (17)	C19—C18—H18	119.7
C4—C3—H3	120.2	C17—C18—H18	119.7
C2—C3—H3	120.2	C18—C19—C20	121.03 (16)
C3—C4—C5	120.78 (18)	C18—C19—H19	119.5
C3—C4—H4	119.6	C20—C19—H19	119.5
C5—C4—H4	119.6	C21—C20—C19	118.04 (16)
C6—C5—C4	119.00 (17)	C21—C20—C23	121.15 (19)
C6—C5—H5	120.5	C19—C20—C23	120.80 (18)
C4—C5—H5	120.5	C22—C21—C20	121.54 (17)
C1—C6—C5	120.96 (15)	C22—C21—H21	119.2
C1—C6—N1	120.57 (14)	C20—C21—H21	119.2
C5—C6—N1	118.46 (14)	C21—C22—C17	120.27 (15)
O1—C7—N1	123.18 (13)	C21—C22—H22	119.9
O1—C7—C8	128.05 (14)	C17—C22—H22	119.9
N1—C7—C8	108.77 (12)	C20—C23—H23A	109.5
C7—C8—C9	103.31 (13)	C20—C23—H23B	109.5
C7—C8—C16	118.56 (13)	H23A—C23—H23B	109.5
C9—C8—C16	138.11 (13)	C20—C23—H23C	109.5
N2—C9—C8	111.39 (12)	H23A—C23—H23C	109.5
N2—C9—C10	117.21 (12)	H23B—C23—H23C	109.5
C8—C9—C10	131.29 (13)	C20—C23—H23D	109.5
C11—C10—C15	118.62 (13)	H23A—C23—H23D	141.1
C11—C10—C9	120.08 (13)	H23B—C23—H23D	56.3
C15—C10—C9	121.19 (13)	H23C—C23—H23D	56.3
C12—C11—C10	120.79 (15)	C20—C23—H23E	109.5
C12—C11—H11	119.6	H23A—C23—H23E	56.3
C10—C11—H11	119.6	H23B—C23—H23E	141.1
C13—C12—C11	119.95 (16)	H23C—C23—H23E	56.3
C13—C12—H12	120.0	H23D—C23—H23E	109.5
C11—C12—H12	120.0	C20—C23—H23F	109.5
C12—C13—C14	119.78 (15)	H23A—C23—H23F	56.3
C12—C13—H13	120.1	H23B—C23—H23F	56.3
C14—C13—H13	120.1	H23C—C23—H23F	141.1
C15—C14—C13	120.51 (16)	H23D—C23—H23F	109.5
C15—C14—H14	119.7	H23E—C23—H23F	109.5

C7—N1—N2—C9	1.36 (17)	C8—C9—C10—C11	132.21 (16)
C6—N1—N2—C9	176.03 (13)	N2—C9—C10—C15	124.20 (16)
C6—C1—C2—C3	0.9 (3)	C8—C9—C10—C15	−51.6 (2)
C1—C2—C3—C4	−0.7 (3)	C15—C10—C11—C12	0.4 (2)
C2—C3—C4—C5	0.1 (4)	C9—C10—C11—C12	176.64 (14)
C3—C4—C5—C6	0.4 (3)	C10—C11—C12—C13	−0.7 (2)
C2—C1—C6—C5	−0.5 (3)	C11—C12—C13—C14	0.1 (3)
C2—C1—C6—N1	−179.15 (15)	C12—C13—C14—C15	0.9 (3)
C4—C5—C6—C1	−0.1 (3)	C13—C14—C15—C10	−1.2 (3)
C4—C5—C6—N1	178.55 (17)	C11—C10—C15—C14	0.6 (2)
C7—N1—C6—C1	−40.2 (3)	C9—C10—C15—C14	−175.65 (15)
N2—N1—C6—C1	146.30 (15)	C7—C8—C16—O2	−11.0 (2)
C7—N1—C6—C5	141.11 (18)	C9—C8—C16—O2	171.10 (16)
N2—N1—C6—C5	−32.4 (2)	C7—C8—C16—C17	166.13 (14)
N2—N1—C7—O1	177.74 (13)	C9—C8—C16—C17	−11.7 (3)
C6—N1—C7—O1	3.8 (3)	O2—C16—C17—C22	143.95 (15)
N2—N1—C7—C8	−2.25 (17)	C8—C16—C17—C22	−33.2 (2)
C6—N1—C7—C8	−176.15 (14)	O2—C16—C17—C18	−30.8 (2)
O1—C7—C8—C9	−177.86 (15)	C8—C16—C17—C18	152.03 (14)
N1—C7—C8—C9	2.12 (16)	C22—C17—C18—C19	1.3 (2)
O1—C7—C8—C16	3.6 (2)	C16—C17—C18—C19	176.29 (14)
N1—C7—C8—C16	−176.40 (13)	C17—C18—C19—C20	−2.4 (2)
N1—N2—C9—C8	0.05 (16)	C18—C19—C20—C21	1.7 (2)
N1—N2—C9—C10	−176.59 (12)	C18—C19—C20—C23	−177.57 (16)
C7—C8—C9—N2	−1.33 (16)	C19—C20—C21—C22	0.0 (2)
C16—C8—C9—N2	176.73 (17)	C23—C20—C21—C22	179.23 (16)
C7—C8—C9—C10	174.70 (15)	C20—C21—C22—C17	−1.0 (2)
C16—C8—C9—C10	−7.2 (3)	C18—C17—C22—C21	0.3 (2)
N2—C9—C10—C11	−51.95 (19)	C16—C17—C22—C21	−174.45 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.90 (2)	1.79 (1)	2.5394 (16)	139 (1)
C15—H15···O2ⁱ	0.93	2.46	3.378 (2)	170

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈N₂O₂
M_r	354.39
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	9.705 (1), 10.0821 (9), 10.746 (1)
α, β, γ (°)	115.284 (8), 102.13 (1), 91.61 (1)
V (Å³)	921.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.28 × 0.26

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4049, 3307, 2233
R_int	0.009
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.096, 0.97
No. of reflections	3307
No. of parameters	249
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.12

Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXTL (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top

O1—C7	1.3193 (16)	N2—C9	1.3142 (18)
O2—C16	1.2655 (17)	C7—C8	1.3962 (19)
N1—C7	1.3369 (19)	C8—C9	1.4366 (19)
N1—N2	1.3915 (16)

C7—N1—N2	110.47 (11)	C7—C8—C9	103.31 (13)
C9—N2—N1	106.01 (12)	C7—C8—C16	118.56 (13)
O1—C7—N1	123.18 (13)	N2—C9—C8	111.39 (12)
O1—C7—C8	128.05 (14)	O2—C16—C8	117.03 (13)
N1—C7—C8	108.77 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.898 (19)	1.794 (14)	2.5394 (16)	138.7 (12)
C15—H15···O2ⁱ	0.93	2.46	3.378 (2)	170

Symmetry code: (i) −x+1, −y+2, −z+1.

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