3-(4-Fluoro­phen­yl)-1,5-di-2-pyridyl­pentane-1,5-dione

Shao, Q.-Q.; Chen, D.-Q.; Shi, F.

doi:10.1107/S1600536807026530

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3-(4-Fluorophenyl)-1,5-di-2-pyridylpentane-1,5-dione

Q.-Q. Shao, D.-Q. Chen and F. Shi

The title compound, C₂₁H₁₇FN₂O₂, was prepared by the reaction of 4-fluorobenzaldehyde and 2-acetylpridine in N,N-dimethylformamide under microwave irradiation. In the molecular conformation, there are three planes: a benzene plane and two pyridine planes. The dihedral angles between the benzene plane and the pyridine planes are 88.38 (15) and 83.27 (13)°, and the dihedral angle between the two pyridine planes is 8.05 (10)°. There is an intramolecular C—H

N hydrogen bond. In the crystal structure, a supramolecular structure is constructed by the dimeration of two molecules via an intermolecular C—H

O hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026530/gw2012sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026530/gw2012Isup2.hkl Contains datablock I

CCDC reference: 655595

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R factor = 0.047
wR factor = 0.118
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.69 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    F1     -   C19     ..       5.72 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 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
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Kröhnke type pyridines (Kröhnke, 1976) and other substituted pyridines (Neve et al., 1997; MacGillivray et al., 2000; Olenyuk et al., 1999) were prominent building blocks in organic chemistry and substituted pyridines ligands have attracted widespread attention due to their ability to form complexes with transition metals, so substituted pyridines are applied extensively in coordinate chemistry (Li et al., 2004; Jantunen et al. 2006; Raehm et al., 2000). Also, the applications of pyridine derivatives have been found in various fields such as supramolecular chemistry (Lehn, 1995), asymmetric catalysis (Chelucci, 2002), photosensitization (Islam et al., 2003) and antitumor compounds (Clarke et al., 2003). In this paper we report the crystal structure of the title compound, (I).

In (I), there are three planes. They are benzene ring(C16—C21) and two pyridine planes. The dihedral angle between the C7/C8/C10/N1 plane and the C16—C21 benzene ring is 88.380 (146)°. The dihedral angle between the C12/C13/C15/N2 plane and the C16—C21 benzene ring is 83.267 (132)°. And the dihedral angle between the two pyridine planes is 8.049 (98)°. There is an intramolecular C(2)–H(2 A).·N(1) hydrogen bond. Besides, in the crystal structure, the supramolecular structure is constructed by the the dimeration of two molecules via a intermolecular C(12)–H(12).. O(2) hydrogen bond.

Related literature top

For related literature, see: Chelucci & Thummel (2002); Clarke (2003); Islam et al. (2003); Jantunen & Scott (2006); Kröhnke (1976); Lehn (1995); Li et al. (2004); MacGillivray et al. (2000); Neve et al. (1997); Olenyuk et al. (1999); Raehm & Hamann (2000).

Experimental top

The title compound, (I), was prepared by the reaction of 4-fluorobenzaldehyde(0.5 mmol,0.06 g) and 2-acetylpridine (1 mmol,0.12 g) in N,N-dimethylformamide(DMF)(1.5 ml) under microwave irradiation for 5 min. (microwave oven is EmrysTM Creator from Personal Chemistry, Uppsala, Sweden). Upon completion monitored by TLC, the reaction mixture was cooled to room temperature and then poured into cold water. The solid product was filtered, washed with water and EtOH (95%), and subsequently dried and recrystallized from EtOH (95%) to give the pure product(0.11 g). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a 95% aqueous ethanol solution (yield 63%; m.p. 428–430 K). IR (cm^-1): 1698 (CO); ¹H NMR (DMSO-d₆): 8.70 (d, 2H, J = 4.4 Hz, ArH), 7.97 (t, 2H, ArH, J = 8.0 Hz), 7.86 (d, 2H, J = 7.2 Hz, ArH), 7.65 (t, 2H, ArH, J = 5.6 Hz), 7.38–7.34 (m, 2H, ArH), 7.04 (t, 2H, ArH, J = 8.8 Hz), 3.98–3.94 (m, 1H, CH), 3.78–3.71 (m, 2H, CH2), 3.58–3.50 (m, 2H, CH2)

Structure description top

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids.
	Fig. 2. A packing diagram of (I) projected along the b axis.

3-(4-Fluorophenyl)-1,5-di-2-pyridylpentane-1,5-dione top

Crystal data top

C₂₁H₁₇FN₂O₂	F(000) = 364
M_r = 348.37	D_x = 1.320 Mg m⁻³
Triclinic, P1	Melting point = 428–430 K
a = 8.6219 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4637 (18) Å	Cell parameters from 1181 reflections
c = 10.7870 (19) Å	θ = 2.9–25.3°
α = 94.045 (2)°	µ = 0.09 mm⁻¹
β = 112.017 (3)°	T = 298 K
γ = 100.632 (2)°	Prism, colourless
V = 876.2 (3) Å³	0.40 × 0.37 × 0.12 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3037 independent reflections
Radiation source: fine-focus sealed tube	1696 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→8
T_min = 0.964, T_max = 0.989	k = −10→12
4527 measured reflections	l = −11→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0395P)² + 0.2087P] where P = (F_o² + 2F_c²)/3
3037 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₁H₁₇FN₂O₂	γ = 100.632 (2)°
M_r = 348.37	V = 876.2 (3) Å³
Triclinic, P1	Z = 2
a = 8.6219 (15) Å	Mo Kα radiation
b = 10.4637 (18) Å	µ = 0.09 mm⁻¹
c = 10.7870 (19) Å	T = 298 K
α = 94.045 (2)°	0.40 × 0.37 × 0.12 mm
β = 112.017 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3037 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1696 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.989	R_int = 0.017
4527 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.01	Δρ_max = 0.15 e Å⁻³
3037 reflections	Δρ_min = −0.15 e Å⁻³
235 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
F1	0.4049 (2)	0.88118 (15)	0.11670 (16)	0.0739 (5)
N1	0.9292 (3)	0.8183 (2)	−0.2819 (2)	0.0730 (7)
N2	1.3438 (3)	0.8341 (2)	0.4885 (2)	0.0597 (6)
O1	0.7475 (2)	0.54540 (17)	−0.17159 (16)	0.0652 (6)
O2	0.9876 (2)	0.57115 (19)	0.31977 (17)	0.0739 (6)
C1	0.8471 (3)	0.6455 (2)	−0.1666 (2)	0.0442 (6)
C2	0.9899 (3)	0.7149 (2)	−0.0360 (2)	0.0478 (6)
H2A	1.0058	0.8091	−0.0358	0.057*
H2B	1.0956	0.6911	−0.0305	0.057*
C3	0.9560 (3)	0.6814 (2)	0.0888 (2)	0.0426 (6)
H3	0.9223	0.5854	0.0792	0.051*
C4	1.1168 (3)	0.7286 (2)	0.2194 (2)	0.0467 (6)
H4A	1.2145	0.7077	0.2051	0.056*
H4B	1.1389	0.8235	0.2412	0.056*
C5	1.1003 (3)	0.6672 (2)	0.3365 (2)	0.0483 (6)
C6	0.8302 (3)	0.7014 (2)	−0.2937 (2)	0.0450 (6)
C7	0.7154 (4)	0.6316 (3)	−0.4166 (2)	0.0640 (8)
H7	0.6484	0.5494	−0.4211	0.077*
C8	0.7003 (4)	0.6838 (3)	−0.5324 (3)	0.0811 (10)
H8	0.6235	0.6376	−0.6166	0.097*
C9	0.7988 (4)	0.8034 (3)	−0.5219 (3)	0.0909 (11)
H9	0.7911	0.8418	−0.5985	0.109*
C10	0.9099 (5)	0.8666 (3)	−0.3965 (3)	0.1043 (13)
H10	0.9770	0.9492	−0.3904	0.125*
C11	1.2313 (3)	0.7229 (2)	0.4757 (2)	0.0469 (6)
C12	1.2336 (4)	0.6589 (3)	0.5833 (3)	0.0662 (8)
H12	1.1515	0.5825	0.5712	0.079*
C13	1.3599 (4)	0.7104 (3)	0.7090 (3)	0.0773 (9)
H13	1.3657	0.6683	0.7832	0.093*
C14	1.4757 (4)	0.8230 (3)	0.7239 (3)	0.0723 (9)
H14	1.5620	0.8597	0.8081	0.087*
C15	1.4632 (4)	0.8816 (3)	0.6124 (3)	0.0747 (9)
H15	1.5426	0.9594	0.6236	0.090*
C16	0.8086 (3)	0.7357 (2)	0.0964 (2)	0.0387 (6)
C17	0.8156 (3)	0.8697 (2)	0.1086 (2)	0.0471 (6)
H17	0.9134	0.9275	0.1118	0.057*
C18	0.6816 (3)	0.9198 (2)	0.1161 (2)	0.0507 (7)
H18	0.6881	1.0099	0.1246	0.061*
C19	0.5394 (3)	0.8333 (3)	0.1107 (2)	0.0475 (6)
C20	0.5258 (3)	0.7011 (2)	0.1006 (2)	0.0475 (6)
H20	0.4277	0.6446	0.0985	0.057*
C21	0.6610 (3)	0.6531 (2)	0.0937 (2)	0.0436 (6)
H21	0.6534	0.5629	0.0869	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0651 (11)	0.0743 (11)	0.0899 (12)	0.0198 (9)	0.0376 (10)	0.0114 (9)
N1	0.0879 (18)	0.0666 (16)	0.0426 (13)	−0.0198 (13)	0.0190 (13)	0.0088 (11)
N2	0.0621 (15)	0.0574 (14)	0.0433 (13)	0.0006 (12)	0.0089 (12)	0.0077 (11)
O1	0.0736 (13)	0.0579 (12)	0.0498 (11)	−0.0143 (10)	0.0235 (10)	0.0022 (9)
O2	0.0670 (13)	0.0792 (14)	0.0534 (12)	−0.0155 (11)	0.0115 (10)	0.0255 (10)
C1	0.0440 (15)	0.0461 (15)	0.0401 (14)	0.0021 (12)	0.0189 (12)	0.0002 (11)
C2	0.0435 (15)	0.0565 (16)	0.0386 (14)	0.0005 (12)	0.0163 (12)	0.0047 (12)
C3	0.0432 (15)	0.0462 (14)	0.0335 (13)	0.0009 (12)	0.0142 (12)	0.0063 (11)
C4	0.0429 (15)	0.0559 (16)	0.0382 (14)	0.0045 (12)	0.0148 (12)	0.0126 (11)
C5	0.0436 (15)	0.0529 (16)	0.0456 (15)	0.0056 (13)	0.0158 (13)	0.0150 (12)
C6	0.0479 (15)	0.0471 (15)	0.0366 (14)	0.0032 (12)	0.0173 (12)	0.0018 (11)
C7	0.072 (2)	0.0620 (18)	0.0429 (16)	−0.0031 (15)	0.0161 (15)	0.0021 (13)
C8	0.094 (3)	0.092 (2)	0.0354 (17)	0.001 (2)	0.0127 (17)	0.0048 (16)
C9	0.114 (3)	0.100 (3)	0.0432 (18)	−0.003 (2)	0.0237 (19)	0.0252 (17)
C10	0.131 (3)	0.090 (2)	0.054 (2)	−0.037 (2)	0.022 (2)	0.0215 (18)
C11	0.0496 (16)	0.0526 (16)	0.0393 (14)	0.0111 (13)	0.0179 (13)	0.0116 (12)
C12	0.073 (2)	0.0723 (19)	0.0450 (17)	0.0033 (16)	0.0184 (16)	0.0177 (14)
C13	0.105 (3)	0.081 (2)	0.0402 (17)	0.024 (2)	0.0193 (18)	0.0189 (15)
C14	0.089 (2)	0.073 (2)	0.0371 (17)	0.0196 (18)	0.0057 (16)	−0.0004 (15)
C15	0.080 (2)	0.0667 (19)	0.0498 (18)	−0.0024 (16)	0.0058 (17)	0.0012 (15)
C16	0.0415 (14)	0.0411 (14)	0.0254 (12)	−0.0007 (11)	0.0088 (11)	0.0045 (10)
C17	0.0458 (16)	0.0465 (16)	0.0426 (15)	−0.0034 (12)	0.0162 (13)	0.0102 (11)
C18	0.0562 (17)	0.0425 (15)	0.0504 (16)	0.0055 (13)	0.0199 (14)	0.0105 (12)
C19	0.0432 (16)	0.0578 (18)	0.0421 (15)	0.0103 (13)	0.0184 (13)	0.0065 (12)
C20	0.0414 (16)	0.0505 (17)	0.0447 (15)	−0.0035 (12)	0.0177 (13)	0.0029 (12)
C21	0.0447 (15)	0.0390 (14)	0.0393 (14)	−0.0026 (12)	0.0145 (12)	0.0005 (11)

Geometric parameters (Å, º) top

F1—C19	1.366 (3)	C8—H8	0.9300
N1—C6	1.323 (3)	C9—C10	1.361 (4)
N1—C10	1.333 (3)	C9—H9	0.9300
N2—C11	1.331 (3)	C10—H10	0.9300
N2—C15	1.334 (3)	C11—C12	1.376 (3)
O1—C1	1.209 (2)	C12—C13	1.374 (4)
O2—C5	1.212 (3)	C12—H12	0.9300
C1—C6	1.497 (3)	C13—C14	1.353 (4)
C1—C2	1.501 (3)	C13—H13	0.9300
C2—C3	1.531 (3)	C14—C15	1.365 (4)
C2—H2A	0.9700	C14—H14	0.9300
C2—H2B	0.9700	C15—H15	0.9300
C3—C16	1.510 (3)	C16—C17	1.388 (3)
C3—C4	1.528 (3)	C16—C21	1.388 (3)
C3—H3	0.9800	C17—C18	1.379 (3)
C4—C5	1.498 (3)	C17—H17	0.9300
C4—H4A	0.9700	C18—C19	1.362 (3)
C4—H4B	0.9700	C18—H18	0.9300
C5—C11	1.494 (3)	C19—C20	1.359 (3)
C6—C7	1.372 (3)	C20—C21	1.376 (3)
C7—C8	1.370 (3)	C20—H20	0.9300
C7—H7	0.9300	C21—H21	0.9300
C8—C9	1.347 (4)

C6—N1—C10	116.3 (2)	C10—C9—H9	120.8
C11—N2—C15	116.6 (2)	N1—C10—C9	124.5 (3)
O1—C1—C6	119.6 (2)	N1—C10—H10	117.7
O1—C1—C2	121.7 (2)	C9—C10—H10	117.7
C6—C1—C2	118.68 (19)	N2—C11—C12	122.9 (2)
C1—C2—C3	113.06 (18)	N2—C11—C5	116.9 (2)
C1—C2—H2A	109.0	C12—C11—C5	120.2 (2)
C3—C2—H2A	109.0	C13—C12—C11	118.6 (3)
C1—C2—H2B	109.0	C13—C12—H12	120.7
C3—C2—H2B	109.0	C11—C12—H12	120.7
H2A—C2—H2B	107.8	C14—C13—C12	119.3 (3)
C16—C3—C4	111.00 (19)	C14—C13—H13	120.3
C16—C3—C2	111.1 (2)	C12—C13—H13	120.3
C4—C3—C2	112.02 (18)	C13—C14—C15	118.5 (3)
C16—C3—H3	107.5	C13—C14—H14	120.7
C4—C3—H3	107.5	C15—C14—H14	120.7
C2—C3—H3	107.5	N2—C15—C14	124.0 (3)
C5—C4—C3	112.65 (19)	N2—C15—H15	118.0
C5—C4—H4A	109.1	C14—C15—H15	118.0
C3—C4—H4A	109.1	C17—C16—C21	117.1 (2)
C5—C4—H4B	109.1	C17—C16—C3	121.7 (2)
C3—C4—H4B	109.1	C21—C16—C3	121.2 (2)
H4A—C4—H4B	107.8	C18—C17—C16	121.9 (2)
O2—C5—C11	119.9 (2)	C18—C17—H17	119.0
O2—C5—C4	121.4 (2)	C16—C17—H17	119.0
C11—C5—C4	118.6 (2)	C19—C18—C17	118.0 (2)
N1—C6—C7	122.6 (2)	C19—C18—H18	121.0
N1—C6—C1	117.5 (2)	C17—C18—H18	121.0
C7—C6—C1	119.9 (2)	C20—C19—C18	122.9 (3)
C8—C7—C6	119.5 (3)	C20—C19—F1	118.4 (2)
C8—C7—H7	120.2	C18—C19—F1	118.7 (2)
C6—C7—H7	120.2	C19—C20—C21	118.3 (2)
C9—C8—C7	118.6 (3)	C19—C20—H20	120.9
C9—C8—H8	120.7	C21—C20—H20	120.9
C7—C8—H8	120.7	C20—C21—C16	121.8 (2)
C8—C9—C10	118.5 (3)	C20—C21—H21	119.1
C8—C9—H9	120.8	C16—C21—H21	119.1

O1—C1—C2—C3	−22.3 (3)	C4—C5—C11—N2	7.6 (3)
C6—C1—C2—C3	158.6 (2)	O2—C5—C11—C12	5.8 (4)
C1—C2—C3—C16	−67.6 (3)	C4—C5—C11—C12	−171.5 (2)
C1—C2—C3—C4	167.7 (2)	N2—C11—C12—C13	−1.5 (4)
C16—C3—C4—C5	70.4 (3)	C5—C11—C12—C13	177.6 (3)
C2—C3—C4—C5	−164.8 (2)	C11—C12—C13—C14	1.2 (5)
C3—C4—C5—O2	14.9 (4)	C12—C13—C14—C15	−0.2 (5)
C3—C4—C5—C11	−167.9 (2)	C11—N2—C15—C14	0.3 (4)
C10—N1—C6—C7	1.0 (4)	C13—C14—C15—N2	−0.6 (5)
C10—N1—C6—C1	−179.1 (3)	C4—C3—C16—C17	63.5 (3)
O1—C1—C6—N1	172.6 (2)	C2—C3—C16—C17	−61.8 (3)
C2—C1—C6—N1	−8.2 (3)	C4—C3—C16—C21	−115.4 (2)
O1—C1—C6—C7	−7.5 (4)	C2—C3—C16—C21	119.3 (2)
C2—C1—C6—C7	171.7 (2)	C21—C16—C17—C18	−0.8 (3)
N1—C6—C7—C8	−0.4 (4)	C3—C16—C17—C18	−179.7 (2)
C1—C6—C7—C8	179.7 (3)	C16—C17—C18—C19	−0.2 (4)
C6—C7—C8—C9	−0.3 (5)	C17—C18—C19—C20	1.1 (4)
C7—C8—C9—C10	0.4 (5)	C17—C18—C19—F1	−179.4 (2)
C6—N1—C10—C9	−0.9 (6)	C18—C19—C20—C21	−0.9 (4)
C8—C9—C10—N1	0.2 (6)	F1—C19—C20—C21	179.5 (2)
C15—N2—C11—C12	0.7 (4)	C19—C20—C21—C16	−0.2 (3)
C15—N2—C11—C5	−178.3 (2)	C17—C16—C21—C20	1.0 (3)
O2—C5—C11—N2	−175.1 (2)	C3—C16—C21—C20	179.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N1	0.97	2.50	2.838 (3)	100
C12—H12···O2ⁱ	0.93	2.45	3.269 (3)	146

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₇FN₂O₂
M_r	348.37
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.6219 (15), 10.4637 (18), 10.7870 (19)
α, β, γ (°)	94.045 (2), 112.017 (3), 100.632 (2)
V (Å³)	876.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.37 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.964, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	4527, 3037, 1696
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.118, 1.01
No. of reflections	3037
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.15

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N1	0.97	2.50	2.838 (3)	100.4
C12—H12···O2ⁱ	0.93	2.45	3.269 (3)	146.4

Symmetry code: (i) −x+2, −y+1, −z+1.

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