N-[2-(4-Methoxy­phen­oxy)eth­yl]­acetamide

Shang, Z.-H.; Lv, H.-J.; Gao, J.-L.

doi:10.1107/S1600536807022726

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N-[2-(4-Methoxyphenoxy)ethyl]acetamide

Z.-H. Shang, H.-J. Lv and J.-L. Gao

The title compound, C₁₁H₁₅NO₃, was synthesized from 4-methoxyphenol and 2-methyl-4,5-dihydrooxazole under nitrogen. There are two independent molecules in the asymmetric unit, which are connected into one-dimensional chains via intermolecular N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022726/lh2385sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022726/lh2385Isup2.hkl Contains datablock I

CCDC reference: 651774

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
R factor = 0.056
wR factor = 0.090
Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   0 ALERT type 5 Informative message, check

Comment top

Nefazodone is a type of antidepressive drug (Madding, 1986). The title compound, which can be hydrolized to 2-(4-methoxyphenoxy)ethanamine, was obtained in order to attempt to synthesize compounds analogous to Nefazodone. N-(2-(4-methoxyphenoxy)ethyl)acetamide was synthesized from 4-methoxyphenol and 2-methyl-4,5-dihydrooxazole under reflux under N₂. The crystal structure is stabilized mainly through intermolecular N—H···O hydrogen bonds.

Related literature top

Our interest in nefazodone, which is a type of antidepressive (Madding, 1986), prompted us to synthesize and determine the crystal structure of the title compound.

Experimental top

The mixture of 4-bromophenol 12.4 g (0.10 mol) and 2-methyl-4,5-dihydrooxazole 1.2 g(0.12 mol) was slowly heated to reflux under nitrogen and maintained for 7 h while monitored by TLC. After completion of the reaction, excess 2-methyl-4,5-dihydrooxazole was recovered by distillation and the residue was cooled to room temperature and added 50 ml NaOH solution(10%). The product was filtered and purifed by by column chromatography. 50 mg of the title compound was dissolved in 20 ml me thanol; the solution was kept at room temperature for 20 d by natural evaporation to give colorless single crystals of (I), suitable for X-Ray analysis.

Structure description top

Our interest in nefazodone, which is a type of antidepressive (Madding, 1986), prompted us to synthesize and determine the crystal structure of the title compound.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids.
	Fig. 2. The reaction scheme for the formation of the title compound.

N-[2-(4-Methoxyphenoxy)ethyl]acetamide top

Crystal data top

C₁₁H₁₅NO₃	F(000) = 896
M_r = 209.24	D_x = 1.238 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 496–498 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.0861 (13) Å	Cell parameters from 2481 reflections
b = 49.81 (1) Å	θ = 2045–23.0°
c = 7.4043 (15) Å	µ = 0.09 mm⁻¹
β = 90.386 (4)°	T = 294 K
V = 2244.6 (8) Å³	Block, colorless
Z = 8	0.26 × 0.24 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	4592 independent reflections
Radiation source: fine-focus sealed tube	2442 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
φ and ω scans	θ_max = 26.4°, θ_min = 0.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −7→7
T_min = 0.977, T_max = 0.982	k = −41→62
12862 measured reflections	l = −8→9

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.056	H-atom parameters constrained
wR(F²) = 0.090	w = 1/[σ²(F_o²) + (0.0796P)² + 0.1165P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4592 reflections	Δρ_max = 0.17 e Å⁻³
275 parameters	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₁H₁₅NO₃	V = 2244.6 (8) Å³
M_r = 209.24	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.0861 (13) Å	µ = 0.09 mm⁻¹
b = 49.81 (1) Å	T = 294 K
c = 7.4043 (15) Å	0.26 × 0.24 × 0.20 mm
β = 90.386 (4)°

Data collection top

Bruker SMART CCD diffractometer	4592 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2442 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.982	R_int = 0.043
12862 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.03	Δρ_max = 0.17 e Å⁻³
4592 reflections	Δρ_min = −0.17 e Å⁻³
275 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
O1	0.1801 (3)	0.21713 (3)	0.4769 (2)	0.0560 (5)
O2	0.4970 (3)	0.11353 (3)	0.4256 (2)	0.0540 (5)
O3	0.7789 (4)	0.04205 (5)	0.1509 (3)	0.1111 (10)
O4	0.6768 (3)	0.21834 (3)	0.9432 (2)	0.0559 (5)
O5	0.9966 (3)	0.11483 (3)	0.9755 (2)	0.0490 (5)
O6	1.3017 (4)	0.05180 (5)	0.6685 (3)	0.1050 (9)
N1	0.6282 (4)	0.05968 (4)	0.3971 (3)	0.0567 (6)
H1	0.5282	0.0583	0.4781	0.068*
N2	1.1293 (4)	0.06004 (4)	0.9255 (3)	0.0544 (6)
H2	1.0231	0.0558	0.9959	0.065*
C1	−0.0118 (5)	0.22455 (6)	0.3806 (5)	0.0744 (9)
H1A	0.0125	0.2224	0.2535	0.112*
H1B	−0.0464	0.2430	0.4058	0.112*
H1C	−0.1318	0.2133	0.4171	0.112*
C2	0.2497 (4)	0.19099 (5)	0.4623 (3)	0.0396 (6)
C3	0.1409 (4)	0.17102 (5)	0.3673 (3)	0.0430 (6)
H3	0.0100	0.1748	0.3070	0.052*
C4	0.2280 (4)	0.14543 (5)	0.3624 (3)	0.0415 (6)
H4	0.1543	0.1320	0.2988	0.050*
C5	0.4219 (4)	0.13936 (5)	0.4501 (3)	0.0387 (6)
C6	0.5288 (4)	0.15904 (5)	0.5493 (3)	0.0435 (6)
H6	0.6575	0.1551	0.6121	0.052*
C7	0.4420 (4)	0.18470 (5)	0.5540 (3)	0.0435 (6)
H7	0.5141	0.1980	0.6200	0.052*
C8	0.6947 (4)	0.10513 (5)	0.5113 (4)	0.0567 (7)
H8A	0.6660	0.1000	0.6352	0.068*
H8B	0.8006	0.1197	0.5122	0.068*
C9	0.7836 (5)	0.08171 (5)	0.4081 (5)	0.0672 (9)
H9A	0.8207	0.0875	0.2870	0.081*
H9B	0.9174	0.0755	0.4664	0.081*
C10	0.6358 (5)	0.04167 (6)	0.2659 (4)	0.0626 (8)
C11	0.4603 (5)	0.02066 (6)	0.2641 (4)	0.0761 (9)
H11A	0.3950	0.0197	0.1458	0.114*
H11B	0.3498	0.0252	0.3508	0.114*
H11C	0.5235	0.0036	0.2944	0.114*
C12	0.4858 (5)	0.22556 (6)	1.0413 (5)	0.0761 (10)
H12A	0.3651	0.2144	1.0039	0.114*
H12B	0.4507	0.2440	1.0181	0.114*
H12C	0.5127	0.2231	1.1681	0.114*
C13	0.7487 (4)	0.19226 (5)	0.9541 (3)	0.0403 (6)
C14	0.6415 (4)	0.17188 (5)	1.0475 (3)	0.0417 (6)
H14	0.5115	0.1755	1.1083	0.050*
C15	0.7294 (4)	0.14637 (5)	1.0494 (3)	0.0409 (6)
H15	0.6585	0.1328	1.1128	0.049*
C16	0.9212 (4)	0.14067 (5)	0.9585 (3)	0.0362 (6)
C17	1.0268 (4)	0.16081 (5)	0.8639 (3)	0.0425 (6)
H17	1.1557	0.1571	0.8018	0.051*
C18	0.9391 (4)	0.18638 (5)	0.8624 (3)	0.0430 (6)
H18	1.0099	0.1999	0.7985	0.052*
C19	1.2056 (4)	0.10835 (5)	0.9008 (4)	0.0509 (7)
H19A	1.3123	0.1221	0.9320	0.061*
H19B	1.1950	0.1073	0.7702	0.061*
C20	1.2753 (5)	0.08168 (5)	0.9779 (4)	0.0595 (8)
H20A	1.4227	0.0776	0.9372	0.071*
H20B	1.2794	0.0829	1.1086	0.071*
C21	1.1539 (5)	0.04652 (6)	0.7719 (4)	0.0614 (8)
C22	0.9902 (5)	0.02469 (6)	0.7364 (4)	0.0813 (10)
H22A	0.9622	0.0234	0.6089	0.122*
H22B	0.8558	0.0287	0.7978	0.122*
H22C	1.0477	0.0079	0.7796	0.122*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0594 (12)	0.0379 (10)	0.0706 (13)	0.0045 (9)	−0.0100 (10)	−0.0026 (9)
O2	0.0517 (12)	0.0447 (11)	0.0654 (12)	0.0068 (9)	−0.0082 (9)	−0.0054 (9)
O3	0.131 (2)	0.0875 (18)	0.116 (2)	−0.0183 (15)	0.0837 (19)	−0.0161 (15)
O4	0.0582 (12)	0.0401 (11)	0.0696 (12)	0.0060 (9)	0.0087 (10)	0.0064 (9)
O5	0.0467 (11)	0.0416 (11)	0.0587 (11)	0.0002 (8)	0.0091 (8)	0.0024 (8)
O6	0.122 (2)	0.1002 (19)	0.0933 (18)	−0.0285 (15)	0.0700 (17)	−0.0220 (14)
N1	0.0571 (15)	0.0468 (14)	0.0665 (16)	0.0042 (11)	0.0239 (12)	0.0071 (12)
N2	0.0595 (15)	0.0455 (13)	0.0585 (15)	0.0018 (11)	0.0219 (11)	0.0006 (12)
C1	0.066 (2)	0.059 (2)	0.098 (2)	0.0161 (16)	−0.0107 (19)	−0.0002 (18)
C2	0.0437 (15)	0.0364 (14)	0.0388 (14)	−0.0035 (11)	0.0023 (11)	0.0026 (11)
C3	0.0379 (15)	0.0461 (16)	0.0448 (15)	0.0005 (12)	−0.0062 (11)	−0.0030 (12)
C4	0.0387 (14)	0.0426 (15)	0.0432 (15)	−0.0080 (11)	−0.0006 (11)	−0.0080 (11)
C5	0.0393 (15)	0.0356 (14)	0.0412 (14)	−0.0017 (11)	0.0051 (11)	0.0003 (11)
C6	0.0399 (15)	0.0464 (16)	0.0439 (15)	−0.0019 (12)	−0.0074 (11)	0.0023 (12)
C7	0.0435 (15)	0.0437 (15)	0.0431 (15)	−0.0102 (12)	−0.0050 (12)	−0.0028 (12)
C8	0.0513 (17)	0.0485 (17)	0.0701 (19)	0.0042 (14)	−0.0048 (14)	0.0037 (14)
C9	0.0546 (18)	0.0528 (18)	0.095 (2)	0.0047 (15)	0.0157 (16)	0.0065 (17)
C10	0.071 (2)	0.0522 (18)	0.0645 (19)	0.0085 (15)	0.0244 (16)	0.0095 (16)
C11	0.088 (2)	0.064 (2)	0.076 (2)	−0.0072 (18)	0.0158 (18)	−0.0042 (17)
C12	0.067 (2)	0.0541 (19)	0.107 (3)	0.0160 (16)	0.0101 (19)	0.0039 (18)
C13	0.0418 (15)	0.0380 (14)	0.0410 (14)	−0.0040 (11)	−0.0065 (11)	0.0020 (11)
C14	0.0365 (14)	0.0447 (16)	0.0438 (15)	−0.0014 (11)	0.0039 (11)	0.0019 (12)
C15	0.0384 (14)	0.0415 (14)	0.0429 (14)	−0.0084 (11)	0.0022 (11)	0.0063 (11)
C16	0.0361 (14)	0.0357 (14)	0.0366 (13)	−0.0033 (11)	−0.0021 (11)	−0.0003 (11)
C17	0.0360 (14)	0.0510 (16)	0.0407 (14)	−0.0059 (12)	0.0062 (11)	0.0011 (12)
C18	0.0446 (15)	0.0425 (15)	0.0419 (14)	−0.0068 (12)	0.0024 (12)	0.0044 (12)
C19	0.0412 (15)	0.0460 (15)	0.0654 (17)	−0.0024 (12)	0.0050 (13)	−0.0037 (14)
C20	0.0557 (18)	0.0529 (18)	0.0700 (19)	0.0070 (15)	−0.0026 (15)	−0.0022 (15)
C21	0.075 (2)	0.0455 (17)	0.0634 (19)	0.0015 (15)	0.0222 (16)	−0.0028 (15)
C22	0.098 (3)	0.056 (2)	0.089 (2)	−0.0116 (18)	0.013 (2)	−0.0147 (18)

Geometric parameters (Å, º) top

O1—C2	1.374 (3)	C8—H8A	0.9700
O1—C1	1.413 (3)	C8—H8B	0.9700
O2—C5	1.378 (3)	C9—H9A	0.9700
O2—C8	1.420 (3)	C9—H9B	0.9700
O3—C10	1.222 (3)	C10—C11	1.496 (4)
O4—C13	1.373 (3)	C11—H11A	0.9600
O4—C12	1.421 (3)	C11—H11B	0.9600
O5—C16	1.372 (3)	C11—H11C	0.9600
O5—C19	1.428 (3)	C12—H12A	0.9600
O6—C21	1.214 (3)	C12—H12B	0.9600
N1—C10	1.323 (4)	C12—H12C	0.9600
N1—C9	1.451 (3)	C13—C18	1.379 (3)
N1—H1	0.8600	C13—C14	1.393 (3)
N2—C21	1.331 (3)	C14—C15	1.378 (3)
N2—C20	1.448 (3)	C14—H14	0.9300
N2—H2	0.8600	C15—C16	1.381 (3)
C1—H1A	0.9600	C15—H15	0.9300
C1—H1B	0.9600	C16—C17	1.384 (3)
C1—H1C	0.9600	C17—C18	1.381 (3)
C2—C3	1.385 (3)	C17—H17	0.9300
C2—C7	1.385 (3)	C18—H18	0.9300
C3—C4	1.381 (3)	C19—C20	1.506 (3)
C3—H3	0.9300	C19—H19A	0.9700
C4—C5	1.376 (3)	C19—H19B	0.9700
C4—H4	0.9300	C20—H20A	0.9700
C5—C6	1.385 (3)	C20—H20B	0.9700
C6—C7	1.384 (3)	C21—C22	1.497 (4)
C6—H6	0.9300	C22—H22A	0.9600
C7—H7	0.9300	C22—H22B	0.9600
C8—C9	1.497 (4)	C22—H22C	0.9600

C2—O1—C1	117.6 (2)	C10—C11—H11B	109.5
C5—O2—C8	119.83 (19)	H11A—C11—H11B	109.5
C13—O4—C12	118.1 (2)	C10—C11—H11C	109.5
C16—O5—C19	118.35 (18)	H11A—C11—H11C	109.5
C10—N1—C9	121.9 (2)	H11B—C11—H11C	109.5
C10—N1—H1	119.1	O4—C12—H12A	109.5
C9—N1—H1	119.1	O4—C12—H12B	109.5
C21—N2—C20	122.2 (2)	H12A—C12—H12B	109.5
C21—N2—H2	118.9	O4—C12—H12C	109.5
C20—N2—H2	118.9	H12A—C12—H12C	109.5
O1—C1—H1A	109.5	H12B—C12—H12C	109.5
O1—C1—H1B	109.5	O4—C13—C18	116.2 (2)
H1A—C1—H1B	109.5	O4—C13—C14	124.7 (2)
O1—C1—H1C	109.5	C18—C13—C14	119.2 (2)
H1A—C1—H1C	109.5	C15—C14—C13	119.6 (2)
H1B—C1—H1C	109.5	C15—C14—H14	120.2
O1—C2—C3	125.0 (2)	C13—C14—H14	120.2
O1—C2—C7	115.8 (2)	C14—C15—C16	120.9 (2)
C3—C2—C7	119.1 (2)	C14—C15—H15	119.6
C4—C3—C2	119.6 (2)	C16—C15—H15	119.6
C4—C3—H3	120.2	O5—C16—C15	115.6 (2)
C2—C3—H3	120.2	O5—C16—C17	124.7 (2)
C5—C4—C3	121.2 (2)	C15—C16—C17	119.7 (2)
C5—C4—H4	119.4	C18—C17—C16	119.4 (2)
C3—C4—H4	119.4	C18—C17—H17	120.3
C4—C5—O2	115.3 (2)	C16—C17—H17	120.3
C4—C5—C6	119.5 (2)	C13—C18—C17	121.2 (2)
O2—C5—C6	125.2 (2)	C13—C18—H18	119.4
C7—C6—C5	119.3 (2)	C17—C18—H18	119.4
C7—C6—H6	120.3	O5—C19—C20	107.6 (2)
C5—C6—H6	120.3	O5—C19—H19A	110.2
C6—C7—C2	121.2 (2)	C20—C19—H19A	110.2
C6—C7—H7	119.4	O5—C19—H19B	110.2
C2—C7—H7	119.4	C20—C19—H19B	110.2
O2—C8—C9	108.0 (2)	H19A—C19—H19B	108.5
O2—C8—H8A	110.1	N2—C20—C19	112.6 (2)
C9—C8—H8A	110.1	N2—C20—H20A	109.1
O2—C8—H8B	110.1	C19—C20—H20A	109.1
C9—C8—H8B	110.1	N2—C20—H20B	109.1
H8A—C8—H8B	108.4	C19—C20—H20B	109.1
N1—C9—C8	112.4 (2)	H20A—C20—H20B	107.8
N1—C9—H9A	109.1	O6—C21—N2	121.1 (3)
C8—C9—H9A	109.1	O6—C21—C22	122.8 (3)
N1—C9—H9B	109.1	N2—C21—C22	116.1 (3)
C8—C9—H9B	109.1	C21—C22—H22A	109.5
H9A—C9—H9B	107.9	C21—C22—H22B	109.5
O3—C10—N1	122.0 (3)	H22A—C22—H22B	109.5
O3—C10—C11	121.1 (3)	C21—C22—H22C	109.5
N1—C10—C11	116.9 (3)	H22A—C22—H22C	109.5
C10—C11—H11A	109.5	H22B—C22—H22C	109.5

C1—O1—C2—C3	−3.2 (3)	C12—O4—C13—C18	−177.6 (2)
C1—O1—C2—C7	178.0 (2)	C12—O4—C13—C14	3.4 (4)
O1—C2—C3—C4	179.9 (2)	O4—C13—C14—C15	−179.9 (2)
C7—C2—C3—C4	−1.3 (3)	C18—C13—C14—C15	1.1 (4)
C2—C3—C4—C5	−0.2 (4)	C13—C14—C15—C16	−0.6 (4)
C3—C4—C5—O2	−176.3 (2)	C19—O5—C16—C15	−173.5 (2)
C3—C4—C5—C6	1.9 (4)	C19—O5—C16—C17	4.2 (3)
C8—O2—C5—C4	−179.5 (2)	C14—C15—C16—O5	177.8 (2)
C8—O2—C5—C6	2.5 (3)	C14—C15—C16—C17	−0.1 (4)
C4—C5—C6—C7	−1.9 (3)	O5—C16—C17—C18	−177.4 (2)
O2—C5—C6—C7	176.0 (2)	C15—C16—C17—C18	0.3 (3)
C5—C6—C7—C2	0.4 (4)	O4—C13—C18—C17	180.0 (2)
O1—C2—C7—C6	−179.9 (2)	C14—C13—C18—C17	−0.9 (4)
C3—C2—C7—C6	1.2 (4)	C16—C17—C18—C13	0.2 (4)
C5—O2—C8—C9	−157.5 (2)	C16—O5—C19—C20	165.5 (2)
C10—N1—C9—C8	155.8 (3)	C21—N2—C20—C19	86.4 (3)
O2—C8—C9—N1	−57.7 (3)	O5—C19—C20—N2	63.7 (3)
C9—N1—C10—O3	2.8 (5)	C20—N2—C21—O6	0.1 (4)
C9—N1—C10—C11	−177.2 (3)	C20—N2—C21—C22	180.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6ⁱ	0.86	2.00	2.863 (3)	175
N2—H2···O3ⁱⁱ	0.86	2.00	2.861 (3)	174

Symmetry codes: (i) x−1, y, z; (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₅NO₃
M_r	209.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	6.0861 (13), 49.81 (1), 7.4043 (15)
β (°)	90.386 (4)
V (Å³)	2244.6 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.26 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.977, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	12862, 4592, 2442
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.090, 1.03
No. of reflections	4592
No. of parameters	275
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6ⁱ	0.86	2.00	2.863 (3)	175.3
N2—H2···O3ⁱⁱ	0.86	2.00	2.861 (3)	174.2

Symmetry codes: (i) x−1, y, z; (ii) x, y, z+1.

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