2-(2-Hydroxy­ethyl)-6-[(2-hydroxy­ethyl)amino]-5-nitro-1H-benzo[de]­isoquinoline-1,3(2H)-dione

Qin, W.; Zhang, Y.; Wang, H.-S.; Zhang, Y.

doi:10.1107/S160053680704295X

Buy article online - an online subscription or single-article purchase is required to access this article.

2-(2-Hydroxyethyl)-6-[(2-hydroxyethyl)amino]-5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione

W. Qin, Y. Zhang, H.-S. Wang and Y. Zhang

The title compound, C₁₆H₁₅N₃O₆, exhibits weak intermolecular C—H

O and O—H

O hydrogen bonds, which stabilize the structure. π–π stacking interactions are also found, the centroid-to-centroid distance within the stacks being 3.4401 Å. The title compound represents a new derivative of 1, 8-naphthalimides.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704295X/pv2026sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680704295X/pv2026Isup2.hkl Contains datablock I

CCDC reference: 636032

checkCIF report

Key indicators

Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.005 Å
R factor = 0.038
wR factor = 0.086
Data-to-parameter ratio = 5.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT089_ALERT_3_B Poor Data / Parameter Ratio (Zmax .LT. 18) .....       5.76

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT411_ALERT_2_C Short Inter H...H Contact  H13B   ..  H14A    ..       2.12 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3     ..  N2      ..       2.64 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.35
           From the CIF: _reflns_number_total               1318
           Count of symmetry unique reflns         1333
           Completeness (_total/calc)             98.87%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The structure of 1,8-naphthalic anhydride is used as a source of fine chemicals. The use of its N-substituted derivatives as important dyes (Konstantinova et al., 2000), fluorescent tapes (Mitchell et al., 1998) and photochemical DNA cleaving reagents (Xu et al., 2004), prompted us to the synthesis of the title copound which is being reported in this article..

The molecular structure of the title compound is shown in Fig. 1. Its overall geometry is comparable to that found for 2-(3',3'-dimethylallyl)-1H-benz[de]iso-quindine-1,3(2H)-dione (Tao & Qian), apart from the hydroxyethyl, the hydroxyethylamino and nitro groups substituting in 1,8-naphthalimide moiety.2-(2-Hydroxyethyl)-6-[(2-hydroxyethyl)amino]-5-nitro- 1H-benzo[de]isoquinoline-1,3(2H)-dione All the atoms in 1,8-naphthalimide moiety are almost coplanar.

In the crystal packing (Fig. 2), there are weak intermolecular C—H···O and O—H···O hydrogen bonds, which stabilize the structure. The π-π stacking interactions are also found while the intermolecular distance within the stacks is 3.440 Å. These contacts also partially take part in the stabilization of the structure.

Related literature top

For related literature, see: Konstantinova et al. (2000); Mitchell et al. (1998); Xu et al. (2004); Tao & Qian (1999).

Experimental top

The mixture of 3-nitro-1,8-naphthalic anhydride (0.32 g, 1 mmol) and hydroxyethyl amine (0.122 g, 2.0 mmol) was refluxed in ethanol (30 ml) for about 6 h, and cooled to afford the yellow powder of the title compound. Upon recrystallization from N,N-dimethylformamide, light-brown crystls were obtained (Yield 50%, m.p. 514–516 K)

Structure description top

For related literature, see: Konstantinova et al. (2000); Mitchell et al. (1998); Xu et al. (2004); Tao & Qian (1999).

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalStructure (Rigaku/MSC, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2000) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The structure of the title copmpound showing 50% probability displacement ellipsoids and the atom labelling scheme. H atoms are represented by small spheres of arbitrary radius.
	Fig. 2. Packing diagram showing a plane of molecules with H bonds indicated by dashed lines.

2-(2-Hydroxyethyl)-6-[(2-hydroxyethyl)amino]-5-nitro- 1H-benzo[de]isoquinoline-1,3(2H)-dione top

Crystal data top

C₁₆H₁₅N₃O₆	Z = 1
M_r = 345.31	F(000) = 180
Triclinic, P1	D_x = 1.584 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71070 Å
a = 4.7125 (12) Å	Cell parameters from 1321 reflections
b = 8.032 (2) Å	θ = 3.1–25.3°
c = 9.997 (3) Å	µ = 0.12 mm⁻¹
α = 80.490 (15)°	T = 193 K
β = 81.977 (15)°	Block, light-brown
γ = 77.324 (14)°	0.30 × 0.18 × 0.15 mm
V = 361.98 (17) Å³

Data collection top

Rigaku Mercury diffractometer	1318 independent reflections
Radiation source: fine-focus sealed tube	1107 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.4°, θ_min = 3.1°
ω scans	h = −5→5
Absorption correction: multi-scan (Jacobson, 1998)	k = −9→8
T_min = 0.964, T_max = 0.982	l = −12→12
3566 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.048P)²] where P = (F_o² + 2F_c²)/3
1318 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.18 e Å⁻³
3 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₆H₁₅N₃O₆	γ = 77.324 (14)°
M_r = 345.31	V = 361.98 (17) Å³
Triclinic, P1	Z = 1
a = 4.7125 (12) Å	Mo Kα radiation
b = 8.032 (2) Å	µ = 0.12 mm⁻¹
c = 9.997 (3) Å	T = 193 K
α = 80.490 (15)°	0.30 × 0.18 × 0.15 mm
β = 81.977 (15)°

Data collection top

Rigaku Mercury diffractometer	1318 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	1107 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.982	R_int = 0.034
3566 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	3 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.05	Δρ_max = 0.18 e Å⁻³
1318 reflections	Δρ_min = −0.18 e Å⁻³
229 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	0.0483 (6)	0.6442 (3)	0.4925 (3)	0.0350 (6)
O2	−0.4438 (5)	0.2532 (3)	0.4083 (2)	0.0310 (6)
O3	−0.1177 (6)	0.6283 (3)	0.0831 (3)	0.0369 (7)
H3	−0.2257	0.5893	0.0411	0.055*
O4	0.5170 (6)	0.5645 (3)	0.8901 (3)	0.0352 (7)
O5	0.5728 (5)	0.3339 (3)	1.0369 (2)	0.0302 (6)
O6	0.4894 (5)	−0.0077 (3)	1.2695 (3)	0.0327 (6)
H6	0.4856	0.0642	1.3223	0.049*
N1	−0.1985 (6)	0.4477 (3)	0.4497 (3)	0.0223 (6)
N2	0.4703 (6)	0.4170 (4)	0.9316 (3)	0.0254 (7)
N3	0.2847 (6)	0.0970 (4)	1.0246 (3)	0.0268 (7)
H3A	0.4202	0.1329	1.0579	0.032*
C1	−0.0264 (7)	0.5052 (4)	0.5296 (4)	0.0239 (8)
C2	0.0537 (7)	0.3942 (4)	0.6543 (3)	0.0204 (8)
C3	−0.0248 (7)	0.2296 (4)	0.6918 (3)	0.0199 (8)
C4	−0.1870 (8)	0.1753 (4)	0.6044 (4)	0.0224 (8)
C5	−0.2869 (7)	0.2916 (4)	0.4813 (3)	0.0225 (8)
C6	0.2177 (7)	0.4469 (4)	0.7355 (3)	0.0203 (7)
H6A	0.2746	0.5550	0.7094	0.024*
C7	0.3036 (7)	0.3451 (4)	0.8560 (3)	0.0212 (8)
C8	0.2187 (7)	0.1832 (4)	0.9034 (3)	0.0213 (8)
C9	0.0624 (7)	0.1209 (4)	0.8121 (3)	0.0209 (8)
C10	−0.0009 (8)	−0.0452 (4)	0.8333 (4)	0.0256 (8)
H10	0.0634	−0.1235	0.9104	0.031*
C11	−0.1535 (8)	−0.0975 (4)	0.7455 (4)	0.0299 (9)
H11	−0.1930	−0.2105	0.7631	0.036*
C12	−0.2508 (7)	0.0134 (4)	0.6310 (4)	0.0273 (8)
H12	−0.3600	−0.0226	0.5721	0.033*
C13	−0.2808 (8)	0.5604 (5)	0.3226 (4)	0.0271 (8)
H13A	−0.2958	0.6823	0.3338	0.033*
H13B	−0.4741	0.5465	0.3034	0.033*
C14	−0.0527 (8)	0.5139 (5)	0.2042 (4)	0.0324 (9)
H14A	0.1427	0.5197	0.2266	0.039*
H14B	−0.0475	0.3944	0.1894	0.039*
C15	0.1779 (8)	−0.0454 (4)	1.1135 (4)	0.0268 (8)
H15A	0.2988	−0.1572	1.0924	0.032*
H15B	−0.0274	−0.0427	1.1002	0.032*
C16	0.1987 (8)	−0.0229 (5)	1.2586 (4)	0.0298 (8)
H16A	0.0589	0.0819	1.2829	0.036*
H16B	0.1493	−0.1234	1.3220	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0485 (16)	0.0283 (14)	0.0310 (16)	−0.0174 (12)	−0.0105 (12)	0.0057 (11)
O2	0.0355 (14)	0.0332 (14)	0.0283 (15)	−0.0107 (11)	−0.0100 (12)	−0.0053 (11)
O3	0.0543 (19)	0.0443 (17)	0.0191 (15)	−0.0272 (14)	−0.0125 (13)	0.0061 (12)
O4	0.0468 (17)	0.0327 (15)	0.0326 (15)	−0.0215 (13)	−0.0102 (12)	−0.0004 (11)
O5	0.0357 (15)	0.0341 (14)	0.0240 (15)	−0.0108 (11)	−0.0122 (12)	−0.0001 (11)
O6	0.0351 (15)	0.0335 (14)	0.0320 (17)	−0.0054 (12)	−0.0121 (12)	−0.0065 (11)
N1	0.0257 (15)	0.0229 (15)	0.0178 (16)	−0.0048 (12)	−0.0050 (12)	0.0007 (11)
N2	0.0271 (17)	0.0287 (17)	0.0234 (18)	−0.0114 (14)	−0.0015 (14)	−0.0051 (13)
N3	0.0280 (17)	0.0281 (15)	0.0258 (18)	−0.0092 (13)	−0.0064 (13)	0.0000 (13)
C1	0.0228 (19)	0.027 (2)	0.022 (2)	−0.0060 (16)	−0.0024 (15)	−0.0040 (15)
C2	0.0190 (18)	0.0206 (18)	0.021 (2)	−0.0047 (14)	0.0021 (15)	−0.0034 (14)
C3	0.0185 (18)	0.0219 (18)	0.019 (2)	−0.0046 (15)	0.0004 (15)	−0.0040 (14)
C4	0.0233 (18)	0.0199 (18)	0.024 (2)	−0.0046 (14)	0.0022 (15)	−0.0056 (14)
C5	0.0243 (19)	0.026 (2)	0.018 (2)	−0.0075 (16)	−0.0031 (16)	−0.0030 (15)
C6	0.0188 (17)	0.0230 (18)	0.019 (2)	−0.0073 (14)	0.0005 (14)	−0.0011 (13)
C7	0.0196 (18)	0.0215 (19)	0.024 (2)	−0.0065 (15)	0.0005 (15)	−0.0065 (15)
C8	0.0196 (18)	0.0272 (19)	0.017 (2)	−0.0056 (15)	−0.0015 (15)	−0.0027 (15)
C9	0.0186 (17)	0.0212 (18)	0.022 (2)	−0.0041 (14)	0.0028 (15)	−0.0036 (14)
C10	0.031 (2)	0.0255 (19)	0.020 (2)	−0.0068 (16)	−0.0031 (15)	0.0001 (14)
C11	0.037 (2)	0.0217 (17)	0.034 (2)	−0.0101 (16)	−0.0050 (17)	−0.0049 (15)
C12	0.028 (2)	0.032 (2)	0.026 (2)	−0.0112 (16)	−0.0066 (16)	−0.0046 (16)
C13	0.0290 (19)	0.0309 (19)	0.021 (2)	−0.0071 (16)	−0.0092 (15)	0.0046 (14)
C14	0.030 (2)	0.048 (2)	0.020 (2)	−0.0107 (18)	−0.0049 (16)	−0.0004 (16)
C15	0.029 (2)	0.0255 (18)	0.026 (2)	−0.0083 (16)	−0.0032 (16)	0.0009 (15)
C16	0.034 (2)	0.0304 (18)	0.026 (2)	−0.0132 (16)	−0.0049 (16)	0.0033 (15)

Geometric parameters (Å, º) top

O1—C1	1.227 (4)	C4—C5	1.482 (5)
O2—C5	1.225 (4)	C6—C7	1.396 (5)
O3—C14	1.420 (4)	C6—H6A	0.9500
O3—H3	0.8400	C7—C8	1.431 (4)
O4—N2	1.245 (4)	C8—C9	1.458 (5)
O5—N2	1.248 (4)	C9—C10	1.406 (5)
O6—C16	1.423 (4)	C10—C11	1.376 (5)
O6—H6	0.8400	C10—H10	0.9500
N1—C5	1.381 (4)	C11—C12	1.394 (5)
N1—C1	1.405 (4)	C11—H11	0.9500
N1—C13	1.479 (5)	C12—H12	0.9500
N2—C7	1.425 (4)	C13—C14	1.520 (5)
N3—C8	1.333 (4)	C13—H13A	0.9900
N3—C15	1.464 (4)	C13—H13B	0.9900
N3—H3A	0.8800	C14—H14A	0.9900
C1—C2	1.452 (5)	C14—H14B	0.9900
C2—C6	1.367 (5)	C15—C16	1.510 (5)
C2—C3	1.428 (4)	C15—H15A	0.9900
C3—C4	1.413 (5)	C15—H15B	0.9900
C3—C9	1.419 (5)	C16—H16A	0.9900
C4—C12	1.374 (5)	C16—H16B	0.9900

C14—O3—H3	109.5	C10—C9—C8	123.9 (3)
C16—O6—H6	109.5	C3—C9—C8	119.3 (3)
C5—N1—C1	123.9 (3)	C11—C10—C9	121.9 (3)
C5—N1—C13	118.8 (3)	C11—C10—H10	119.1
C1—N1—C13	117.3 (3)	C9—C10—H10	119.1
O4—N2—O5	119.8 (3)	C10—C11—C12	120.8 (3)
O4—N2—C7	119.1 (3)	C10—C11—H11	119.6
O5—N2—C7	121.1 (3)	C12—C11—H11	119.6
C8—N3—C15	133.1 (3)	C4—C12—C11	119.3 (3)
C8—N3—H3A	113.4	C4—C12—H12	120.4
C15—N3—H3A	113.4	C11—C12—H12	120.4
O1—C1—N1	119.7 (3)	N1—C13—C14	110.0 (3)
O1—C1—C2	123.2 (3)	N1—C13—H13A	109.7
N1—C1—C2	117.1 (3)	C14—C13—H13A	109.7
C6—C2—C3	119.2 (3)	N1—C13—H13B	109.7
C6—C2—C1	118.8 (3)	C14—C13—H13B	109.7
C3—C2—C1	122.0 (3)	H13A—C13—H13B	108.2
C4—C3—C9	120.5 (3)	O3—C14—C13	110.8 (3)
C4—C3—C2	118.4 (3)	O3—C14—H14A	109.5
C9—C3—C2	121.2 (3)	C13—C14—H14A	109.5
C12—C4—C3	120.6 (3)	O3—C14—H14B	109.5
C12—C4—C5	119.0 (3)	C13—C14—H14B	109.5
C3—C4—C5	120.3 (3)	H14A—C14—H14B	108.1
O2—C5—N1	119.8 (3)	N3—C15—C16	107.1 (3)
O2—C5—C4	122.1 (3)	N3—C15—H15A	110.3
N1—C5—C4	118.1 (3)	C16—C15—H15A	110.3
C2—C6—C7	121.4 (3)	N3—C15—H15B	110.3
C2—C6—H6A	119.3	C16—C15—H15B	110.3
C7—C6—H6A	119.3	H15A—C15—H15B	108.5
C6—C7—N2	115.4 (3)	O6—C16—C15	108.5 (3)
C6—C7—C8	122.2 (3)	O6—C16—H16A	110.0
N2—C7—C8	122.3 (3)	C15—C16—H16A	110.0
N3—C8—C7	120.2 (3)	O6—C16—H16B	110.0
N3—C8—C9	123.4 (3)	C15—C16—H16B	110.0
C7—C8—C9	116.4 (3)	H16A—C16—H16B	108.4
C10—C9—C3	116.8 (3)

C5—N1—C1—O1	178.4 (3)	O5—N2—C7—C6	−176.0 (3)
C13—N1—C1—O1	0.2 (5)	O4—N2—C7—C8	−174.3 (3)
C5—N1—C1—C2	−1.8 (4)	O5—N2—C7—C8	6.7 (4)
C13—N1—C1—C2	179.9 (3)	C15—N3—C8—C7	163.9 (3)
O1—C1—C2—C6	0.6 (5)	C15—N3—C8—C9	−16.7 (6)
N1—C1—C2—C6	−179.2 (3)	C6—C7—C8—N3	−174.4 (3)
O1—C1—C2—C3	−177.1 (3)	N2—C7—C8—N3	2.7 (5)
N1—C1—C2—C3	3.1 (4)	C6—C7—C8—C9	6.2 (4)
C6—C2—C3—C4	−178.1 (3)	N2—C7—C8—C9	−176.7 (3)
C1—C2—C3—C4	−0.4 (4)	C4—C3—C9—C10	4.7 (4)
C6—C2—C3—C9	0.5 (4)	C2—C3—C9—C10	−174.0 (3)
C1—C2—C3—C9	178.2 (3)	C4—C3—C9—C8	−177.4 (3)
C9—C3—C4—C12	−3.1 (5)	C2—C3—C9—C8	4.0 (4)
C2—C3—C4—C12	175.5 (3)	N3—C8—C9—C10	−8.7 (5)
C9—C3—C4—C5	177.8 (3)	C7—C8—C9—C10	170.7 (3)
C2—C3—C4—C5	−3.5 (4)	N3—C8—C9—C3	173.5 (3)
C1—N1—C5—O2	178.0 (3)	C7—C8—C9—C3	−7.1 (4)
C13—N1—C5—O2	−3.9 (5)	C3—C9—C10—C11	−3.2 (5)
C1—N1—C5—C4	−2.0 (5)	C8—C9—C10—C11	178.9 (3)
C13—N1—C5—C4	176.2 (3)	C9—C10—C11—C12	0.2 (5)
C12—C4—C5—O2	5.8 (5)	C3—C4—C12—C11	0.0 (5)
C3—C4—C5—O2	−175.2 (3)	C5—C4—C12—C11	179.0 (3)
C12—C4—C5—N1	−174.3 (3)	C10—C11—C12—C4	1.5 (5)
C3—C4—C5—N1	4.8 (5)	C5—N1—C13—C14	−87.6 (4)
C3—C2—C6—C7	−1.7 (4)	C1—N1—C13—C14	90.7 (4)
C1—C2—C6—C7	−179.4 (3)	N1—C13—C14—O3	−176.1 (3)
C2—C6—C7—N2	−179.1 (3)	C8—N3—C15—C16	−149.0 (4)
C2—C6—C7—C8	−1.8 (5)	N3—C15—C16—O6	−53.4 (4)
O4—N2—C7—C6	3.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.84	2.12	2.931 (3)	161
O3—H3···O5ⁱ	0.84	2.45	3.161 (3)	143
O3—H3···N2ⁱ	0.84	2.64	3.472 (4)	171
O6—H6···O2ⁱⁱ	0.84	1.97	2.790 (3)	165
N3—H3A···O5	0.88	1.88	2.595 (4)	138
N3—H3A···O6	0.88	2.26	2.693 (4)	110
C11—H11···O4ⁱⁱⁱ	0.95	2.57	3.435 (4)	152
C13—H13A···O6^iv	0.99	2.49	3.376 (5)	149

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅N₃O₆
M_r	345.31
Crystal system, space group	Triclinic, P1
Temperature (K)	193
a, b, c (Å)	4.7125 (12), 8.032 (2), 9.997 (3)
α, β, γ (°)	80.490 (15), 81.977 (15), 77.324 (14)
V (Å³)	361.98 (17)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.30 × 0.18 × 0.15

Data collection
Diffractometer	Rigaku Mercury
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.964, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	3566, 1318, 1107
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.086, 1.05
No. of reflections	1318
No. of parameters	229
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: CrystalClear (Rigaku, 1999), CrystalStructure (Rigaku/MSC, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2000) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.84	2.12	2.931 (3)	161.2
O3—H3···O5ⁱ	0.84	2.45	3.161 (3)	142.8
O3—H3···N2ⁱ	0.84	2.64	3.472 (4)	170.6
O6—H6···O2ⁱⁱ	0.84	1.97	2.790 (3)	164.7
N3—H3A···O5	0.88	1.88	2.595 (4)	137.7
N3—H3A···O6	0.88	2.26	2.693 (4)	110.4
C11—H11···O4ⁱⁱⁱ	0.95	2.57	3.435 (4)	152.2
C13—H13A···O6^iv	0.99	2.49	3.376 (5)	149.2

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

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page