2-Amino-4,5-dimethoxy­benzonitrile

Sarojini, B.K.; Narayana, B.; Mayekar, A.N.; Yathirajan, H.S.; Bolte, M.

doi:10.1107/S1600536807054827

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2-Amino-4,5-dimethoxybenzonitrile

B. K. Sarojini, B. Narayana, A. N. Mayekar, H. S. Yathirajan and M. Bolte

The geometric parameters of the title compound, C₉H₁₀N₂O₂, which crystallizes with two molecules in the asymmetric unit, are in the usual ranges. The molecules are essentially planar (r.m.s. deviations for all non-H atoms are 0.084 and 0.110 Å for the two molecules in the asymmetric unit). The crystal packing is stabilized by N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054827/at2463sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054827/at2463Isup2.hkl Contains datablock I

CCDC reference: 674077

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R factor = 0.036
wR factor = 0.097
Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C2     -   C7      ..       7.14 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C2A    -   C7A     ..       7.58 su

Alert level C
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2     -   C7     ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2A    -   C7A    ...       1.44 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1A    -   H1C    ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1C    ..  N2A     ..       2.74 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Nitriles are close relatives of azoles and hydrazones and are parent compounds for the preparation of various functional organic materials having triazole, imidazole or thidiazole moieties (İkizler & Sancak, 1992; 1995; 1998). The synthesis of new azoles has been a very active area of research and an important aspect is the incorporation of functional units such as, cyanomethyl group in ravuconazol (Urbina et al., 2001). Nitrile derivatives have many industrial applications. For example, phthalonitriles have been used as starting materials for phthalocyanines (Jin et al., 1994), which are important components for dyes, pigments, gas sensors, optical limiters and liquid crystals. They are also used in medicine as singlet oxygen photosensitizers for photodynamic therapy (Brewis et al., 2003). Some related crystal structures, viz., (2-cyanomethoxy-6-methoxyphenoxy)acetonitrile (Sancak, 2005), p-decylphenyl isocyanide and p-decylbenzonitrile: isomorphous isonitrile/nitrile isomers (Britton et al., 2004) and 2-[2-(cyanomethoxy)phenoxy]acetonitrile (Ustabaş et al., 2004) have been reported. A new nitrile derivative was obtained from the industry as a gift sample and its structure is reported.

Geometric parameters of the title compound, which crystallizes with two molecules in the asymmetric unit, are in the usual ranges. The molecules are essentially planar (r.m.s. deviation for all non-H atoms 0.084 Å and 0.110 Å for the two molecules in the asymmetric unit). The crystal packing is stabilized by N—H···O hydrogen bonds.

Related literature top

For related literature, see: Brewis et al. (2003); Britton et al. (2004); İkizler & Sancak (1992, 1995, 1998); Jin et al. (1994); Sancak (2005); Urbina et al. (2001); Ustabaş et al. (2004).

Experimental top

2-Amino-4,5-dimethoxybenzonitrile was obtained as a gift sample from SeQuent Scientific Limited, Mangalore and was recrystallized from methanol by slow evaporation technique [m.p: 369–374 K]).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.

2-Amino-4,5-dimethoxybenzonitrile top

Crystal data top

C₉H₁₀N₂O₂	F(000) = 752
M_r = 178.19	D_x = 1.322 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 21499 reflections
a = 13.2649 (9) Å	θ = 3.6–26.8°
b = 17.0653 (9) Å	µ = 0.10 mm⁻¹
c = 7.9635 (5) Å	T = 173 K
β = 96.769 (5)°	Block, colourless
V = 1790.13 (19) Å³	0.33 × 0.29 × 0.24 mm
Z = 8

Data collection top

STOE IPDS II two-circle- diffractometer	3163 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.038
Graphite monochromator	θ_max = 26.7°, θ_min = 3.5°
ω scans	h = −16→16
23314 measured reflections	k = −21→21
3722 independent reflections	l = −10→9

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.060P)² + 0.2526P] where P = (F_o² + 2F_c²)/3
3722 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₉H₁₀N₂O₂	V = 1790.13 (19) Å³
M_r = 178.19	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.2649 (9) Å	µ = 0.10 mm⁻¹
b = 17.0653 (9) Å	T = 173 K
c = 7.9635 (5) Å	0.33 × 0.29 × 0.24 mm
β = 96.769 (5)°

Data collection top

STOE IPDS II two-circle- diffractometer	3163 reflections with I > 2σ(I)
23314 measured reflections	R_int = 0.038
3722 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.15 e Å⁻³
3722 reflections	Δρ_min = −0.21 e Å⁻³
255 parameters

Special details top

Experimental. ;

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	0.07571 (6)	0.74641 (5)	0.29441 (12)	0.0305 (2)
O2	0.06985 (6)	0.59747 (5)	0.23025 (10)	0.02477 (19)
N1	0.38490 (8)	0.54952 (7)	0.58981 (14)	0.0286 (2)
H1A	0.3905 (12)	0.5060 (10)	0.526 (2)	0.038 (4)*
H1B	0.4457 (12)	0.5714 (9)	0.632 (2)	0.034 (4)*
N2	0.46025 (9)	0.73153 (8)	0.77100 (17)	0.0435 (3)
C1	0.31110 (8)	0.60122 (7)	0.51816 (14)	0.0211 (2)
C2	0.31248 (8)	0.68144 (7)	0.55662 (15)	0.0233 (2)
C3	0.23499 (8)	0.73219 (7)	0.48324 (15)	0.0251 (2)
H3	0.2378	0.7865	0.5099	0.030*
C4	0.15563 (8)	0.70339 (6)	0.37346 (14)	0.0225 (2)
C5	0.15205 (8)	0.62171 (7)	0.33777 (14)	0.0204 (2)
C6	0.22811 (8)	0.57221 (6)	0.40866 (14)	0.0214 (2)
H6	0.2244	0.5178	0.3832	0.026*
C7	0.39404 (9)	0.71128 (7)	0.67434 (16)	0.0286 (3)
C8	0.08316 (10)	0.83018 (7)	0.30592 (17)	0.0319 (3)
H8A	0.0823	0.8464	0.4238	0.048*
H8B	0.0256	0.8540	0.2358	0.048*
H8C	0.1467	0.8474	0.2660	0.048*
C9	0.05401 (9)	0.51431 (7)	0.21645 (17)	0.0286 (3)
H9A	0.1075	0.4908	0.1579	0.043*
H9B	−0.0123	0.5039	0.1523	0.043*
H9C	0.0560	0.4915	0.3298	0.043*
O1A	0.58742 (6)	0.49611 (5)	0.81914 (11)	0.0304 (2)
O2A	0.63026 (6)	0.61035 (5)	0.62874 (10)	0.0270 (2)
N1A	0.88591 (8)	0.71281 (6)	1.06092 (15)	0.0286 (2)
H1C	0.9030 (12)	0.7465 (10)	0.986 (2)	0.038 (4)*
H1D	0.9361 (12)	0.6981 (10)	1.139 (2)	0.038 (4)*
N2A	0.87001 (9)	0.59744 (7)	1.42142 (14)	0.0371 (3)
C1A	0.81333 (8)	0.65744 (6)	1.00388 (14)	0.0220 (2)
C2A	0.78575 (8)	0.59755 (7)	1.11092 (14)	0.0226 (2)
C3A	0.71054 (8)	0.54145 (7)	1.05269 (15)	0.0246 (2)
H3A	0.6942	0.5004	1.1254	0.030*
C4A	0.66133 (8)	0.54648 (6)	0.89099 (15)	0.0229 (2)
C5A	0.68523 (8)	0.60922 (6)	0.78508 (14)	0.0217 (2)
C6A	0.76065 (8)	0.66260 (6)	0.83953 (14)	0.0224 (2)
H6A	0.7771	0.7031	0.7656	0.027*
C7A	0.83205 (9)	0.59568 (7)	1.28329 (15)	0.0266 (3)
C8A	0.57605 (10)	0.42399 (8)	0.9070 (2)	0.0380 (3)
H8A1	0.6417	0.3971	0.9254	0.057*
H8A2	0.5267	0.3906	0.8393	0.057*
H8A3	0.5520	0.4350	1.0163	0.057*
C9A	0.64180 (10)	0.67832 (8)	0.52425 (16)	0.0313 (3)
H9A1	0.6245	0.7257	0.5844	0.047*
H9A2	0.5964	0.6736	0.4183	0.047*
H9A3	0.7122	0.6818	0.4992	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0276 (4)	0.0193 (4)	0.0418 (5)	0.0027 (3)	−0.0070 (4)	0.0019 (3)
O2	0.0227 (4)	0.0215 (4)	0.0277 (4)	0.0003 (3)	−0.0073 (3)	0.0001 (3)
N1	0.0231 (5)	0.0303 (5)	0.0301 (6)	0.0035 (4)	−0.0061 (4)	−0.0019 (4)
N2	0.0316 (6)	0.0483 (7)	0.0477 (7)	−0.0039 (5)	−0.0069 (5)	−0.0177 (6)
C1	0.0193 (5)	0.0258 (5)	0.0183 (5)	0.0003 (4)	0.0018 (4)	0.0006 (4)
C2	0.0196 (5)	0.0272 (6)	0.0228 (6)	−0.0038 (4)	0.0013 (4)	−0.0024 (4)
C3	0.0250 (5)	0.0204 (5)	0.0299 (6)	−0.0035 (4)	0.0037 (5)	−0.0021 (4)
C4	0.0214 (5)	0.0212 (5)	0.0246 (6)	0.0011 (4)	0.0012 (4)	0.0026 (4)
C5	0.0192 (5)	0.0232 (5)	0.0182 (5)	−0.0015 (4)	0.0000 (4)	−0.0001 (4)
C6	0.0222 (5)	0.0200 (5)	0.0214 (5)	0.0007 (4)	0.0004 (4)	−0.0014 (4)
C7	0.0244 (5)	0.0293 (6)	0.0318 (7)	−0.0009 (5)	0.0019 (5)	−0.0062 (5)
C8	0.0365 (6)	0.0188 (6)	0.0400 (7)	0.0044 (5)	0.0036 (5)	−0.0002 (5)
C9	0.0282 (6)	0.0218 (6)	0.0328 (6)	0.0001 (4)	−0.0094 (5)	−0.0058 (5)
O1A	0.0284 (4)	0.0273 (4)	0.0339 (5)	−0.0062 (3)	−0.0030 (4)	0.0005 (4)
O2A	0.0282 (4)	0.0269 (4)	0.0238 (4)	0.0015 (3)	−0.0061 (3)	0.0025 (3)
N1A	0.0261 (5)	0.0265 (5)	0.0313 (6)	−0.0031 (4)	−0.0052 (4)	0.0020 (4)
N2A	0.0396 (6)	0.0458 (7)	0.0245 (6)	0.0030 (5)	−0.0018 (5)	0.0021 (5)
C1A	0.0192 (5)	0.0210 (5)	0.0254 (6)	0.0041 (4)	0.0009 (4)	−0.0014 (4)
C2A	0.0213 (5)	0.0257 (6)	0.0203 (5)	0.0047 (4)	0.0003 (4)	−0.0002 (4)
C3A	0.0252 (5)	0.0241 (5)	0.0248 (6)	0.0015 (4)	0.0041 (4)	0.0037 (4)
C4A	0.0198 (5)	0.0217 (5)	0.0269 (6)	0.0004 (4)	0.0014 (4)	−0.0019 (4)
C5A	0.0208 (5)	0.0230 (5)	0.0207 (5)	0.0061 (4)	−0.0001 (4)	−0.0010 (4)
C6A	0.0226 (5)	0.0208 (5)	0.0235 (6)	0.0029 (4)	0.0015 (4)	0.0028 (4)
C7A	0.0258 (5)	0.0293 (6)	0.0249 (6)	0.0037 (4)	0.0035 (5)	0.0016 (5)
C8A	0.0356 (7)	0.0248 (6)	0.0523 (9)	−0.0058 (5)	−0.0001 (6)	0.0031 (6)
C9A	0.0339 (6)	0.0328 (6)	0.0254 (6)	0.0046 (5)	−0.0041 (5)	0.0079 (5)

Geometric parameters (Å, º) top

O1—C4	1.3790 (13)	O1A—C4A	1.3767 (14)
O1—C8	1.4353 (14)	O1A—C8A	1.4323 (16)
O2—C5	1.3686 (13)	O2A—C5A	1.3668 (13)
O2—C9	1.4369 (14)	O2A—C9A	1.4461 (15)
N1—C1	1.3895 (15)	N1A—C1A	1.3867 (15)
N1—H1A	0.907 (17)	N1A—H1C	0.876 (18)
N1—H1B	0.916 (16)	N1A—H1D	0.894 (17)
N2—C7	1.1506 (17)	N2A—C7A	1.1549 (16)
C1—C2	1.4023 (16)	C1A—C2A	1.4067 (16)
C1—C6	1.4110 (15)	C1A—C6A	1.4118 (15)
C2—C3	1.4165 (16)	C2A—C3A	1.4205 (16)
C2—C7	1.4387 (16)	C2A—C7A	1.4365 (16)
C3—C4	1.3774 (16)	C3A—C4A	1.3761 (16)
C3—H3	0.9500	C3A—H3A	0.9500
C4—C5	1.4222 (16)	C4A—C5A	1.4217 (16)
C5—C6	1.3841 (15)	C5A—C6A	1.3844 (16)
C6—H6	0.9500	C6A—H6A	0.9500
C8—H8A	0.9800	C8A—H8A1	0.9800
C8—H8B	0.9800	C8A—H8A2	0.9800
C8—H8C	0.9800	C8A—H8A3	0.9800
C9—H9A	0.9800	C9A—H9A1	0.9800
C9—H9B	0.9800	C9A—H9A2	0.9800
C9—H9C	0.9800	C9A—H9A3	0.9800

C4—O1—C8	117.24 (9)	C4A—O1A—C8A	116.39 (10)
C5—O2—C9	116.42 (8)	C5A—O2A—C9A	117.02 (9)
C1—N1—H1A	113.0 (10)	C1A—N1A—H1C	116.8 (10)
C1—N1—H1B	116.0 (10)	C1A—N1A—H1D	118.0 (11)
H1A—N1—H1B	114.4 (14)	H1C—N1A—H1D	115.3 (14)
N1—C1—C2	122.66 (10)	N1A—C1A—C2A	121.11 (10)
N1—C1—C6	119.44 (10)	N1A—C1A—C6A	120.65 (10)
C2—C1—C6	117.82 (10)	C2A—C1A—C6A	118.13 (10)
C1—C2—C3	121.10 (10)	C1A—C2A—C3A	120.98 (10)
C1—C2—C7	118.51 (10)	C1A—C2A—C7A	118.86 (10)
C3—C2—C7	120.38 (10)	C3A—C2A—C7A	120.11 (10)
C4—C3—C2	120.45 (10)	C4A—C3A—C2A	120.06 (10)
C4—C3—H3	119.8	C4A—C3A—H3A	120.0
C2—C3—H3	119.8	C2A—C3A—H3A	120.0
C3—C4—O1	126.07 (10)	C3A—C4A—O1A	125.87 (10)
C3—C4—C5	118.79 (10)	C3A—C4A—C5A	119.20 (10)
O1—C4—C5	115.14 (9)	O1A—C4A—C5A	114.92 (10)
O2—C5—C6	124.01 (10)	O2A—C5A—C6A	124.35 (10)
O2—C5—C4	115.25 (9)	O2A—C5A—C4A	114.76 (10)
C6—C5—C4	120.74 (10)	C6A—C5A—C4A	120.87 (10)
C5—C6—C1	121.06 (10)	C5A—C6A—C1A	120.65 (10)
C5—C6—H6	119.5	C5A—C6A—H6A	119.7
C1—C6—H6	119.5	C1A—C6A—H6A	119.7
N2—C7—C2	176.72 (14)	N2A—C7A—C2A	177.18 (13)
O1—C8—H8A	109.5	O1A—C8A—H8A1	109.5
O1—C8—H8B	109.5	O1A—C8A—H8A2	109.5
H8A—C8—H8B	109.5	H8A1—C8A—H8A2	109.5
O1—C8—H8C	109.5	O1A—C8A—H8A3	109.5
H8A—C8—H8C	109.5	H8A1—C8A—H8A3	109.5
H8B—C8—H8C	109.5	H8A2—C8A—H8A3	109.5
O2—C9—H9A	109.5	O2A—C9A—H9A1	109.5
O2—C9—H9B	109.5	O2A—C9A—H9A2	109.5
H9A—C9—H9B	109.5	H9A1—C9A—H9A2	109.5
O2—C9—H9C	109.5	O2A—C9A—H9A3	109.5
H9A—C9—H9C	109.5	H9A1—C9A—H9A3	109.5
H9B—C9—H9C	109.5	H9A2—C9A—H9A3	109.5

N1—C1—C2—C3	−178.93 (11)	N1A—C1A—C2A—C3A	179.28 (10)
C6—C1—C2—C3	−2.21 (16)	C6A—C1A—C2A—C3A	3.07 (16)
N1—C1—C2—C7	0.37 (17)	N1A—C1A—C2A—C7A	1.77 (16)
C6—C1—C2—C7	177.09 (10)	C6A—C1A—C2A—C7A	−174.44 (10)
C1—C2—C3—C4	0.76 (17)	C1A—C2A—C3A—C4A	−1.89 (16)
C7—C2—C3—C4	−178.52 (11)	C7A—C2A—C3A—C4A	175.59 (10)
C2—C3—C4—O1	179.78 (11)	C2A—C3A—C4A—O1A	179.91 (10)
C2—C3—C4—C5	1.13 (17)	C2A—C3A—C4A—C5A	−1.31 (16)
C8—O1—C4—C3	10.31 (17)	C8A—O1A—C4A—C3A	−13.65 (17)
C8—O1—C4—C5	−171.00 (10)	C8A—O1A—C4A—C5A	167.52 (10)
C9—O2—C5—C6	11.52 (16)	C9A—O2A—C5A—C6A	−9.50 (15)
C9—O2—C5—C4	−168.80 (10)	C9A—O2A—C5A—C4A	172.09 (10)
C3—C4—C5—O2	178.75 (10)	C3A—C4A—C5A—O2A	−178.21 (10)
O1—C4—C5—O2	−0.04 (14)	O1A—C4A—C5A—O2A	0.71 (14)
C3—C4—C5—C6	−1.55 (16)	C3A—C4A—C5A—C6A	3.32 (16)
O1—C4—C5—C6	179.66 (10)	O1A—C4A—C5A—C6A	−177.76 (10)
O2—C5—C6—C1	179.73 (10)	O2A—C5A—C6A—C1A	179.57 (10)
C4—C5—C6—C1	0.06 (17)	C4A—C5A—C6A—C1A	−2.12 (16)
N1—C1—C6—C5	178.63 (10)	N1A—C1A—C6A—C5A	−177.29 (10)
C2—C1—C6—C5	1.79 (16)	C2A—C1A—C6A—C5A	−1.06 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2Aⁱ	0.907 (17)	2.336 (17)	3.2296 (14)	168.1 (14)
N1—H1B···O2A	0.916 (16)	2.540 (16)	3.3954 (13)	155.7 (13)
N1—H1B···O1A	0.916 (16)	2.597 (15)	3.1979 (13)	123.7 (12)
N1A—H1C···N2Aⁱⁱ	0.876 (18)	2.738 (18)	3.4217 (17)	135.9 (14)
N1A—H1D···O1ⁱⁱⁱ	0.894 (17)	2.257 (17)	3.0036 (13)	140.9 (14)
N1A—H1D···O2ⁱⁱⁱ	0.894 (17)	2.514 (17)	3.2971 (13)	146.7 (14)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula	C₉H₁₀N₂O₂
M_r	178.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	13.2649 (9), 17.0653 (9), 7.9635 (5)
β (°)	96.769 (5)
V (Å³)	1790.13 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.33 × 0.29 × 0.24

Data collection
Diffractometer	STOE IPDS II two-circle- diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	23314, 3722, 3163
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.632

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.097, 1.02
No. of reflections	3722
No. of parameters	255
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.21

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2Aⁱ	0.907 (17)	2.336 (17)	3.2296 (14)	168.1 (14)
N1—H1B···O2A	0.916 (16)	2.540 (16)	3.3954 (13)	155.7 (13)
N1—H1B···O1A	0.916 (16)	2.597 (15)	3.1979 (13)	123.7 (12)
N1A—H1C···N2Aⁱⁱ	0.876 (18)	2.738 (18)	3.4217 (17)	135.9 (14)
N1A—H1D···O1ⁱⁱⁱ	0.894 (17)	2.257 (17)	3.0036 (13)	140.9 (14)
N1A—H1D···O2ⁱⁱⁱ	0.894 (17)	2.514 (17)	3.2971 (13)	146.7 (14)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x+1, y, z+1.

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