3-Hydr­oxy-N′-[phen­yl(2-pyrid­yl)methyl­ene]-2-naphthohydrazide

Kang, W.-J.; Dou, J.-M.; Li, D.-C.; Wang, D.-Q.

doi:10.1107/S160053680703036X

3-Hydroxy-N′-[phenyl(2-pyridyl)methylene]-2-naphthohydrazide

W.-J. Kang, J.-M. Dou, D.-C. Li and D.-Q. Wang

In the title molecule, C₂₃H₁₇N₃O₂, intramolecular O—H

O and N—H

N hydrogen bonds influence the molecular conformation. In the crystal structure, π–π interactions, with a distance of 3.611 (5) Å between the centroids of rings in neighbouring naphthalene rings, link the molecules into centrosymmetric dimers, and C—H

π interactions link the dimers into chains running in the [101] direction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703036X/cv2265sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680703036X/cv2265Isup2.hkl Contains datablock I

CCDC reference: 634512

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.045
wR factor = 0.152
Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The chemistry of aroylhydrazones has gained a special attraction due to their coordination abilities to metal ions (Bai et al., 2005) and their biological activities (Mostafa & Haifaa, 2007). As an extension of our work on the structural characterization of aroylhydrazone derivatives (Liu et al., 2005), the title compound, (I), was synthesized and characterized.

In the title compound, the C1—O1 bond length is 1.228 (3) Å, indicating that the molecule is in the keto form. The bond distances and angles in (I) are normal. The three mean planes - naphthalene bicycle (A), benzene ring (B) and pyridine ring (C), make the following dihedral angles - A/B 75.7 (1)°, B/C 57.5 (1)° and A/C 25.1 (1)°. There are two intramolecular O2—H···O1 and N1—H···N3 hydrogen bonds (Table 1 and Fig. 1).

The π···π interactions - proved by short distance Cg1···Cg2ⁱ of 3.611 (5) Å - link the molecules into centrosymmetric dimers [Cg1 and Cg2 are centroids of C2—C7 and C6—C11, respectively; symmetry code: (i) 1 - x, 1 - y, 2 - z]. The C—H···π interactions - C23—H23···Cg3ⁱⁱ 2.63 Å, 149°; Cg3 is a centroid of N3/C13—C17 [symmetry code: (ii) -x, 1 - y, 1 - z] - link dimers into chains running in direction [101] (Fig. 2).

Related literature top

For the crystal structure of a Ni complex with a related aroylhydrazone derivative, see: Liu et al. (2005). For general background, see Bai et al. (2005); for the specific biological activities of aroylhydrazones, see Mostafa & Haifaa (2007).

Experimental top

A solution of 2-benzoylpyridine (2.56 g, 14 mmol) in ethanol (10 ml) was added to a solution of 2-hydroxy-3-naphthoylhydrazine (2.02 g, 10 mmol) in ethanol (10 ml). The mixture was refluxed for 3 h, and then the precipitate was collected, washed several times with ethanol and dried in vacuo (yield 80%). A dichloromethane solution of the title compound was slowly evaporated and yellow crystal for X-ray diffraction was obtained after two weeks (m.p. 475–476 K). Analysis calculated for C₂₃H₁₇N₃O₂: C 75.19, H 4.67, N 11.44%; found: C 75.01, H 4.49, N 11.31%.

Structure description top

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT? (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Crystal packing of the title compound.

3-Hydroxy-N'-[phenyl(2-pyridyl)methylene]-2-naphthohydrazide top

Crystal data top

C₂₃H₁₇N₃O₂	F(000) = 768
M_r = 367.40	D_x = 1.350 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.9214 (18) Å	Cell parameters from 1775 reflections
b = 17.238 (2) Å	θ = 2.4–22.8°
c = 7.7751 (16) Å	µ = 0.09 mm⁻¹
β = 104.294 (2)°	T = 293 K
V = 1808.0 (5) Å³	Block, yellow
Z = 4	0.38 × 0.30 × 0.28 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3185 independent reflections
Radiation source: fine-focus sealed tube	1695 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→13
T_min = 0.967, T_max = 0.976	k = −20→19
9307 measured reflections	l = −8→9

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.152	w = 1/[σ²(F_o²) + (0.0657P)² + 0.3761P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3185 reflections	Δρ_max = 0.22 e Å⁻³
254 parameters	Δρ_min = −0.20 e Å⁻³
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0079 (14)

Crystal data top

C₂₃H₁₇N₃O₂	V = 1808.0 (5) Å³
M_r = 367.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.9214 (18) Å	µ = 0.09 mm⁻¹
b = 17.238 (2) Å	T = 293 K
c = 7.7751 (16) Å	0.38 × 0.30 × 0.28 mm
β = 104.294 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3185 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1695 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.976	R_int = 0.040
9307 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	1 restraint
wR(F²) = 0.152	H-atom parameters constrained
S = 1.01	Δρ_max = 0.22 e Å⁻³
3185 reflections	Δρ_min = −0.20 e Å⁻³
254 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 > 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

	x	y	z	U_iso*/U_eq
N1	0.12667 (15)	0.45180 (13)	0.8333 (3)	0.0502 (7)
H1	0.1275	0.5007	0.8551	0.060*
N2	0.04182 (16)	0.41633 (12)	0.7402 (3)	0.0475 (6)
N3	0.01643 (16)	0.57354 (13)	0.8659 (3)	0.0506 (6)
O1	0.21182 (14)	0.33844 (12)	0.8614 (3)	0.0826 (8)
O2	0.35617 (16)	0.32793 (12)	1.1398 (4)	0.0933 (9)
H2	0.3047	0.3140	1.0702	0.140*
C1	0.2092 (2)	0.40821 (17)	0.8904 (4)	0.0546 (8)
C2	0.3136 (2)	0.52678 (16)	0.9791 (4)	0.0520 (8)
H2A	0.2677	0.5553	0.8956	0.062*
C3	0.29691 (18)	0.44932 (16)	0.9980 (4)	0.0494 (8)
C4	0.3682 (2)	0.40554 (17)	1.1233 (5)	0.0624 (9)
C5	0.4488 (2)	0.44150 (19)	1.2260 (5)	0.0668 (10)
H5	0.4941	0.4125	1.3092	0.080*
C6	0.4661 (2)	0.52093 (18)	1.2106 (4)	0.0554 (8)
C7	0.39797 (19)	0.56455 (16)	1.0821 (4)	0.0505 (8)
C8	0.4168 (2)	0.64417 (17)	1.0631 (5)	0.0625 (9)
H8	0.3729	0.6732	0.9778	0.075*
C9	0.4980 (2)	0.6791 (2)	1.1672 (5)	0.0734 (11)
H9	0.5092	0.7317	1.1530	0.088*
C10	0.5644 (2)	0.6364 (2)	1.2949 (5)	0.0806 (12)
H10	0.6196	0.6608	1.3664	0.097*
C11	0.5499 (2)	0.5599 (2)	1.3165 (5)	0.0748 (11)
H11	0.5955	0.5323	1.4023	0.090*
C12	−0.0393 (2)	0.45569 (15)	0.6996 (4)	0.0440 (7)
C13	−0.05324 (19)	0.53912 (15)	0.7360 (4)	0.0449 (7)
C14	−0.1321 (2)	0.58120 (17)	0.6364 (4)	0.0568 (8)
H14	−0.1795	0.5569	0.5474	0.068*
C15	−0.1403 (2)	0.65894 (18)	0.6692 (5)	0.0677 (10)
H15	−0.1927	0.6877	0.6018	0.081*
C16	−0.0705 (2)	0.69346 (17)	0.8019 (5)	0.0641 (9)
H16	−0.0748	0.7459	0.8270	0.077*
C17	0.0057 (2)	0.64892 (16)	0.8969 (4)	0.0571 (8)
H17	0.0526	0.6724	0.9881	0.069*
C18	−0.1255 (2)	0.40909 (15)	0.6010 (4)	0.0463 (7)
C19	−0.2175 (2)	0.41381 (17)	0.6401 (4)	0.0575 (8)
H19	−0.2266	0.4482	0.7269	0.069*
C20	−0.2955 (2)	0.3681 (2)	0.5517 (5)	0.0666 (10)
H20	−0.3564	0.3710	0.5805	0.080*
C21	−0.2828 (3)	0.31836 (19)	0.4211 (5)	0.0687 (10)
H21	−0.3359	0.2888	0.3588	0.082*
C22	−0.1918 (2)	0.31210 (17)	0.3818 (4)	0.0632 (9)
H22	−0.1831	0.2777	0.2948	0.076*
C23	−0.1137 (2)	0.35729 (16)	0.4726 (4)	0.0519 (8)
H23	−0.0522	0.3527	0.4467	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0443 (14)	0.0329 (13)	0.0666 (17)	−0.0022 (11)	0.0006 (12)	−0.0055 (11)
N2	0.0420 (13)	0.0396 (13)	0.0570 (16)	−0.0049 (11)	0.0047 (12)	−0.0039 (11)
N3	0.0577 (15)	0.0356 (14)	0.0547 (16)	−0.0026 (11)	0.0069 (12)	−0.0014 (11)
O1	0.0583 (14)	0.0381 (13)	0.139 (2)	0.0034 (10)	0.0011 (14)	−0.0161 (13)
O2	0.0683 (15)	0.0448 (14)	0.148 (3)	0.0037 (11)	−0.0087 (16)	0.0215 (14)
C1	0.0452 (17)	0.0375 (17)	0.077 (2)	0.0031 (14)	0.0072 (16)	−0.0013 (15)
C2	0.0454 (17)	0.0410 (17)	0.064 (2)	0.0032 (13)	0.0027 (15)	−0.0027 (14)
C3	0.0398 (16)	0.0376 (16)	0.066 (2)	0.0041 (13)	0.0041 (15)	−0.0038 (14)
C4	0.0448 (17)	0.0416 (18)	0.094 (3)	0.0037 (14)	0.0048 (17)	0.0046 (17)
C5	0.0468 (18)	0.058 (2)	0.085 (3)	0.0122 (16)	−0.0047 (17)	0.0078 (18)
C6	0.0415 (17)	0.0525 (19)	0.068 (2)	0.0050 (14)	0.0054 (16)	−0.0070 (16)
C7	0.0421 (16)	0.0421 (17)	0.065 (2)	0.0011 (14)	0.0092 (15)	−0.0101 (15)
C8	0.057 (2)	0.0463 (19)	0.079 (2)	−0.0025 (15)	0.0065 (18)	−0.0070 (17)
C9	0.058 (2)	0.053 (2)	0.107 (3)	−0.0092 (17)	0.016 (2)	−0.022 (2)
C10	0.048 (2)	0.073 (3)	0.110 (3)	−0.0059 (19)	0.000 (2)	−0.033 (2)
C11	0.0466 (19)	0.076 (3)	0.091 (3)	0.0047 (17)	−0.0037 (18)	−0.017 (2)
C12	0.0446 (16)	0.0376 (16)	0.0476 (18)	−0.0017 (13)	0.0075 (14)	0.0010 (13)
C13	0.0437 (16)	0.0380 (16)	0.0522 (19)	0.0011 (13)	0.0102 (14)	0.0019 (13)
C14	0.0504 (17)	0.0480 (19)	0.068 (2)	0.0001 (15)	0.0065 (16)	0.0015 (15)
C15	0.058 (2)	0.051 (2)	0.087 (3)	0.0103 (16)	0.0052 (19)	0.0064 (18)
C16	0.071 (2)	0.0383 (17)	0.085 (3)	0.0091 (16)	0.023 (2)	−0.0006 (17)
C17	0.068 (2)	0.0374 (17)	0.062 (2)	−0.0037 (15)	0.0086 (17)	−0.0045 (15)
C18	0.0444 (17)	0.0389 (16)	0.0519 (19)	−0.0017 (13)	0.0049 (14)	0.0041 (14)
C19	0.0470 (18)	0.058 (2)	0.065 (2)	−0.0032 (15)	0.0102 (16)	−0.0014 (16)
C20	0.0471 (19)	0.072 (2)	0.078 (3)	−0.0076 (17)	0.0105 (18)	0.010 (2)
C21	0.061 (2)	0.060 (2)	0.072 (3)	−0.0209 (17)	−0.0093 (19)	0.0147 (19)
C22	0.075 (2)	0.0451 (19)	0.060 (2)	−0.0087 (16)	−0.0004 (18)	−0.0025 (15)
C23	0.0524 (18)	0.0420 (17)	0.058 (2)	−0.0021 (14)	0.0076 (15)	−0.0015 (15)

Geometric parameters (Å, º) top

N1—C1	1.352 (3)	C10—C11	1.351 (5)
N1—N2	1.368 (3)	C10—H10	0.9300
N1—H1	0.8600	C11—H11	0.9300
N2—C12	1.288 (3)	C12—C13	1.488 (4)
N3—C17	1.337 (3)	C12—C18	1.489 (4)
N3—C13	1.353 (3)	C13—C14	1.382 (4)
O1—C1	1.226 (3)	C14—C15	1.374 (4)
O2—C4	1.358 (3)	C14—H14	0.9300
O2—H2	0.8200	C15—C16	1.366 (4)
C1—C3	1.480 (4)	C15—H15	0.9300
C2—C3	1.369 (4)	C16—C17	1.369 (4)
C2—C7	1.408 (4)	C16—H16	0.9300
C2—H2A	0.9300	C17—H17	0.9300
C3—C4	1.423 (4)	C18—C23	1.379 (4)
C4—C5	1.356 (4)	C18—C19	1.389 (4)
C5—C6	1.400 (4)	C19—C20	1.380 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.412 (4)	C20—C21	1.374 (5)
C6—C11	1.420 (4)	C20—H20	0.9300
C7—C8	1.412 (4)	C21—C22	1.378 (4)
C8—C9	1.358 (4)	C21—H21	0.9300
C8—H8	0.9300	C22—C23	1.382 (4)
C9—C10	1.389 (5)	C22—H22	0.9300
C9—H9	0.9300	C23—H23	0.9300

C1—N1—N2	118.5 (2)	C6—C11—H11	119.5
C1—N1—H1	120.7	N2—C12—C13	127.6 (2)
N2—N1—H1	120.7	N2—C12—C18	112.9 (2)
C12—N2—N1	119.0 (2)	C13—C12—C18	119.5 (2)
C17—N3—C13	118.0 (2)	N3—C13—C14	120.8 (3)
C4—O2—H2	109.5	N3—C13—C12	117.6 (2)
O1—C1—N1	123.1 (3)	C14—C13—C12	121.6 (3)
O1—C1—C3	121.0 (2)	C15—C14—C13	119.9 (3)
N1—C1—C3	115.8 (2)	C15—C14—H14	120.0
C3—C2—C7	122.0 (3)	C13—C14—H14	120.0
C3—C2—H2A	119.0	C16—C15—C14	119.3 (3)
C7—C2—H2A	119.0	C16—C15—H15	120.4
C2—C3—C4	118.9 (3)	C14—C15—H15	120.4
C2—C3—C1	123.0 (2)	C15—C16—C17	118.4 (3)
C4—C3—C1	118.1 (3)	C15—C16—H16	120.8
C5—C4—O2	119.9 (3)	C17—C16—H16	120.8
C5—C4—C3	119.8 (3)	N3—C17—C16	123.6 (3)
O2—C4—C3	120.4 (3)	N3—C17—H17	118.2
C4—C5—C6	122.1 (3)	C16—C17—H17	118.2
C4—C5—H5	119.0	C23—C18—C19	118.5 (3)
C6—C5—H5	119.0	C23—C18—C12	119.8 (3)
C5—C6—C7	118.8 (3)	C19—C18—C12	121.7 (3)
C5—C6—C11	123.1 (3)	C20—C19—C18	120.8 (3)
C7—C6—C11	118.1 (3)	C20—C19—H19	119.6
C2—C7—C8	122.7 (3)	C18—C19—H19	119.6
C2—C7—C6	118.5 (3)	C21—C20—C19	119.7 (3)
C8—C7—C6	118.8 (3)	C21—C20—H20	120.1
C9—C8—C7	121.2 (3)	C19—C20—H20	120.1
C9—C8—H8	119.4	C20—C21—C22	120.3 (3)
C7—C8—H8	119.4	C20—C21—H21	119.8
C8—C9—C10	120.0 (3)	C22—C21—H21	119.8
C8—C9—H9	120.0	C21—C22—C23	119.6 (3)
C10—C9—H9	120.0	C21—C22—H22	120.2
C11—C10—C9	120.9 (3)	C23—C22—H22	120.2
C11—C10—H10	119.6	C18—C23—C22	121.0 (3)
C9—C10—H10	119.6	C18—C23—H23	119.5
C10—C11—C6	121.1 (3)	C22—C23—H23	119.5
C10—C11—H11	119.5

C1—N1—N2—C12	173.6 (3)	C5—C6—C11—C10	178.8 (3)
N2—N1—C1—O1	0.6 (5)	C7—C6—C11—C10	−0.3 (5)
N2—N1—C1—C3	−177.0 (2)	N1—N2—C12—C13	2.5 (4)
C7—C2—C3—C4	−1.2 (5)	N1—N2—C12—C18	−179.1 (2)
C7—C2—C3—C1	−179.5 (3)	C17—N3—C13—C14	1.2 (4)
O1—C1—C3—C2	153.4 (3)	C17—N3—C13—C12	178.5 (3)
N1—C1—C3—C2	−28.9 (4)	N2—C12—C13—N3	−20.4 (4)
O1—C1—C3—C4	−24.9 (5)	C18—C12—C13—N3	161.4 (3)
N1—C1—C3—C4	152.8 (3)	N2—C12—C13—C14	157.0 (3)
C2—C3—C4—C5	2.5 (5)	C18—C12—C13—C14	−21.3 (4)
C1—C3—C4—C5	−179.1 (3)	N3—C13—C14—C15	−0.1 (4)
C2—C3—C4—O2	−177.0 (3)	C12—C13—C14—C15	−177.3 (3)
C1—C3—C4—O2	1.3 (5)	C13—C14—C15—C16	−0.7 (5)
O2—C4—C5—C6	178.1 (3)	C14—C15—C16—C17	0.4 (5)
C3—C4—C5—C6	−1.4 (5)	C13—N3—C17—C16	−1.6 (5)
C4—C5—C6—C7	−1.0 (5)	C15—C16—C17—N3	0.8 (5)
C4—C5—C6—C11	179.9 (3)	N2—C12—C18—C23	−40.3 (4)
C3—C2—C7—C8	179.3 (3)	C13—C12—C18—C23	138.2 (3)
C3—C2—C7—C6	−1.1 (4)	N2—C12—C18—C19	136.9 (3)
C5—C6—C7—C2	2.2 (4)	C13—C12—C18—C19	−44.6 (4)
C11—C6—C7—C2	−178.6 (3)	C23—C18—C19—C20	−0.4 (4)
C5—C6—C7—C8	−178.2 (3)	C12—C18—C19—C20	−177.6 (3)
C11—C6—C7—C8	0.9 (4)	C18—C19—C20—C21	−1.3 (5)
C2—C7—C8—C9	178.7 (3)	C19—C20—C21—C22	2.1 (5)
C6—C7—C8—C9	−0.9 (5)	C20—C21—C22—C23	−1.2 (5)
C7—C8—C9—C10	0.2 (5)	C19—C18—C23—C22	1.3 (4)
C8—C9—C10—C11	0.5 (6)	C12—C18—C23—C22	178.6 (3)
C9—C10—C11—C6	−0.4 (6)	C21—C22—C23—C18	−0.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.86	2.571 (3)	145
N1—H1···N3	0.86	2.01	2.648 (3)	130
C23—H23···Cgⁱ	0.93	2.63	3.460 (7)	147

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇N₃O₂
M_r	367.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.9214 (18), 17.238 (2), 7.7751 (16)
β (°)	104.294 (2)
V (Å³)	1808.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.38 × 0.30 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.967, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	9307, 3185, 1695
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.152, 1.01
No. of reflections	3185
No. of parameters	254
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.20

Computer programs: SMART (Siemens, 1996), SMART, SAINT? (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.