4-Meth­oxy­anilinium nitrate

Rahmouni, H.; Smirani Sta, W.; Al-Deyab, S.S.; Rzaigui, M.

doi:10.1107/S1600536811031862

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2334

doi:10.1107/S1600536811031862

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4-Methoxyanilinium nitrate

Hajer Rahmouni,^a Wajda Smirani Sta,^a S. Salem Al-Deyab ^b and Mohamed Rzaigui ^a ^*

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia, and ^bPetrochemical Research Chair, College of Science, King Saud University, Riyadh, Saudi Arabia
^*Correspondence e-mail: wajda_sta@yahoo.fr

(Received 12 July 2011; accepted 6 August 2011; online 17 August 2011)

The title compound, C₇H₁₀NO⁺·NO₃⁻, crystallized with two p-ansidinium cations and two nitrate anions in the asymmetric unit. As well as Columbic and van der Waals forces, moleucles interact via multiple bifurcated N—H⋯O hydrogen bonds that help consolidate the crystal packing, resulting in a three-dimensional network.

Related literature

For background to anisidine, see: Li et al. (2001 ). For applications of nitrates, see: Kapoor et al. (2008 ). Association of both entities could lead to new molecular salts with interesting physical and chemical properties, see: Wilkes et al. (1985 ). For related structures, see: Ben Amor et al. (1995 ); Liu et al. (2011 ).

Experimental

Crystal data

C₇H₁₀NO⁺·NO₃⁻
M_r = 186.17
Monoclinic, P 2₁ /n
a = 14.724 (2) Å
b = 7.304 (3) Å
c = 17.509 (2) Å
β = 112.84 (2)°
V = 1735.3 (8) Å³
Z = 8
Ag Kα radiation
λ = 0.56085 Å
μ = 0.07 mm⁻¹
T = 293 K
0.35 × 0.25 × 0.20 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer
12462 measured reflections
8244 independent reflections
2756 reflections with I > 2σ(I)
R_int = 0.033
2 standard reflections every 120 min intensity decay: 5%

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.219
S = 0.93
8244 reflections
235 parameters
H-atom parameters not refined
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4ⁱ	0.89	2.25	2.823 (3)	122
N1—H1A⋯O7ⁱⁱ	0.89	2.52	2.979 (3)	113
N1—H1B⋯O6ⁱⁱⁱ	0.89	2.26	2.843 (3)	123
N1—H1B⋯O5^iv	0.89	2.12	2.903 (3)	146
N1—H1C⋯O7^v	0.89	2.14	2.935 (3)	148
N2—H2A⋯O3ⁱ	0.89	2.08	2.967 (3)	177
N2—H2A⋯O4ⁱ	0.89	2.55	3.187 (3)	129
N2—H2B⋯O6^vi	0.89	2.46	3.070 (3)	127
N2—H2B⋯O7^vi	0.89	2.22	3.083 (3)	163
N2—H2C⋯O3	0.89	2.07	2.891 (2)	152
C9—H9⋯O8^v	0.93	2.48	3.223 (3)	137
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) -x+1, -y+1, -z+1; (iv) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (v) -x+1, -y, -z+1; (vi) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811031862/fl2352sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031862/fl2352Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811031862/fl2352Isup3.cml

checkCIF report

Comment top

Anisidine is used in various areas such as the production of polymers of high solubility which are interesting materials in electroconductivity and thermostability (Li et al., 2001). Nitrates also have many applications such as explosives and pyrotechnics and they can be powerful oxidizers (Kapoor et al., 2008). Association of both entities could lead to novel hybrid compounds with interesting physical and chemical properties (Wilkes et al., 1985). The exploitation of these materials requires knowledge of not only their electronic properties but also of their atomic arrangements.

In this paper, we report crystal structure of the interaction product of [p-ANI] and nitric acid (I). As shown in Fig.1, the asymmetric unit of (I) contains two nitrate anions and two [p-ANIH]⁺ cations interconnected by N—H···O and C—H···O hydrogen bonds (Table 1)). Geometrical characteristics of the two independent nitrate anions are slightly different. In one the N—O distances (N₃/O₃/O₄/O₅) range from 1.202 (3) to 1.268 (2) Å while in the other one the N—O distances (N₄/O₆/O₇/O₈) range from 1.177 (3) to 1.268 (2) Å. Examination of the [p-ANIH]⁺ cations shows that the bond distances and angles show no significant difference from those obtained in other structures involving the same organic groups (Ben Amor et al., 1995). The phenyl rings of these cations are planar with a maximum atomic deviation of ±0.00027 Å and a dihedral angle between them of 8.17°.

The crystal packing shows how each nitrate anion is connected to three [p-ANIH]⁺ cations by N—H···O hydrogen bonding interactions (Table 1, Fig.2). It is noteworthy that the oxygen atom of the shortest bond (N₄—O₈: 1.177 (3) Å) does not participate to the hydrogen bonding network. A similar situation was observed in C₃₆H₄₀N₅O₆NO₃.2C₂H₅OH (Liu et al., 2011), where the N—O bond length is 1.186 (8) Å.

Related literature top

For background to anisidine, see: Li et al. (2001). For applications of nitrates, see: Kapoor et al. (2008). Association of both entities could lead to novel hybrid compounds with interesting physical and chemical properties, see: Wilkes et al. (1985). For related structures, see: Ben Amor et al. (1995); Liu et al. (2011).

Experimental top

An ethanolic solution of p-anisidine [p-ANI] (10 mmol, in 10 ml) was added drop wise to a magnetically stirred aqueous solution of nitric acid HNO₃ (10 mmol, 20 ml). The resultant solution was then slowly evaporated at room temperature (295 K). After a few days, colorless crystals ofn(I) appeared that were suitable for X– ray diffraction measurements.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The assymetric unit of the title compound, with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small sphere of arbitrary radii.
	Fig. 2. Projection of the crystal packing along the b axis.

4-Methoxyanilinium nitrate top

Crystal data top

C₇H₁₀NO⁺·NO₃⁻	F(000) = 784
M_r = 186.17	D_x = 1.425 Mg m⁻³
Monoclinic, P2₁/n	Ag Kα radiation, λ = 0.56085 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 14.724 (2) Å	θ = 9–11°
b = 7.304 (3) Å	µ = 0.07 mm⁻¹
c = 17.509 (2) Å	T = 293 K
β = 112.84 (2)°	Block, brown
V = 1735.3 (8) Å³	0.35 × 0.25 × 0.20 mm
Z = 8

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	R_int = 0.033
Radiation source: fine-focus sealed tube	θ_max = 28.0°, θ_min = 2.4°
Graphite monochromator	h = −24→23
non–profiled ω scans	k = −3→12
12462 measured reflections	l = −2→29
8244 independent reflections	2 standard reflections every 120 min
2756 reflections with I > 2σ(I)	intensity decay: 5%

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.219	H-atom parameters not refined
S = 0.93	w = 1/[σ²(F_o²) + (0.0981P)²] where P = (F_o² + 2F_c²)/3
8244 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₇H₁₀NO⁺·NO₃⁻	V = 1735.3 (8) Å³
M_r = 186.17	Z = 8
Monoclinic, P2₁/n	Ag Kα radiation, λ = 0.56085 Å
a = 14.724 (2) Å	µ = 0.07 mm⁻¹
b = 7.304 (3) Å	T = 293 K
c = 17.509 (2) Å	0.35 × 0.25 × 0.20 mm
β = 112.84 (2)°

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	R_int = 0.033
12462 measured reflections	2 standard reflections every 120 min
8244 independent reflections	intensity decay: 5%
2756 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.219	H-atom parameters not refined
S = 0.93	Δρ_max = 0.53 e Å⁻³
8244 reflections	Δρ_min = −0.25 e Å⁻³
235 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N4	0.45826 (13)	−0.1031 (3)	0.55952 (10)	0.0482 (4)
O7	0.42497 (16)	−0.2382 (2)	0.51123 (13)	0.0797 (6)
O8	0.53055 (17)	−0.0919 (6)	0.61993 (13)	0.1391 (13)
C8	0.32040 (12)	0.3581 (2)	0.13224 (11)	0.0384 (4)
N2	0.23464 (11)	0.4351 (2)	0.14327 (10)	0.0439 (4)
H2A	0.2350	0.4003	0.1921	0.066*
H2B	0.1798	0.3952	0.1030	0.066*
H2C	0.2369	0.5567	0.1414	0.066*
O2	0.56519 (10)	0.1375 (2)	0.10671 (9)	0.0554 (4)
C9	0.38580 (13)	0.2496 (3)	0.19357 (12)	0.0425 (4)
H9	0.3755	0.2252	0.2418	0.051*
C10	0.46634 (14)	0.1778 (3)	0.18263 (12)	0.0460 (4)
H10	0.5105	0.1038	0.2235	0.055*
C11	0.48208 (13)	0.2150 (3)	0.11122 (11)	0.0411 (4)
C12	0.41615 (15)	0.3222 (3)	0.04975 (12)	0.0518 (5)
H12	0.4260	0.3461	0.0014	0.062*
C13	0.33478 (15)	0.3940 (3)	0.06103 (12)	0.0503 (5)
H13	0.2900	0.4667	0.0200	0.060*
C14	0.58718 (17)	0.1818 (4)	0.03694 (15)	0.0594 (6)
H14A	0.6462	0.1195	0.0409	0.089*
H14B	0.5966	0.3116	0.0354	0.089*
H14C	0.5336	0.1444	−0.0127	0.089*
O1	0.67037 (11)	0.5777 (2)	0.15815 (8)	0.0509 (4)
C1	0.56621 (13)	0.5870 (2)	0.34540 (11)	0.0381 (4)
C4	0.63880 (13)	0.5719 (3)	0.22190 (11)	0.0396 (4)
C5	0.68716 (14)	0.4806 (3)	0.29573 (12)	0.0422 (4)
H5	0.7438	0.4135	0.3038	0.051*
N1	0.53081 (12)	0.6024 (3)	0.41235 (11)	0.0482 (4)
H1A	0.4758	0.6687	0.3952	0.072*
H1B	0.5766	0.6567	0.4558	0.072*
H1C	0.5185	0.4912	0.4268	0.072*
C2	0.51623 (14)	0.6757 (3)	0.27082 (12)	0.0459 (5)
H2	0.4588	0.7405	0.2625	0.055*
C6	0.65044 (14)	0.4896 (3)	0.35843 (12)	0.0426 (4)
H6	0.6831	0.4298	0.4086	0.051*
C3	0.55199 (14)	0.6674 (3)	0.20970 (12)	0.0467 (5)
H3	0.5182	0.7258	0.1594	0.056*
C7	0.76321 (18)	0.4981 (4)	0.17243 (15)	0.0588 (6)
H7A	0.7774	0.5105	0.1236	0.088*
H7B	0.7619	0.3706	0.1854	0.088*
H7C	0.8133	0.5591	0.2180	0.088*
N3	0.21447 (12)	0.9114 (2)	0.14231 (11)	0.0462 (4)
O3	0.27158 (11)	0.8115 (2)	0.19742 (10)	0.0577 (4)
O4	0.17418 (11)	1.0419 (2)	0.16528 (12)	0.0642 (5)
O5	0.19753 (18)	0.8822 (3)	0.07051 (12)	0.0925 (7)
O6	0.40423 (13)	0.0358 (3)	0.53394 (14)	0.0787 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N4	0.0599 (10)	0.0482 (10)	0.0424 (9)	0.0005 (9)	0.0262 (8)	0.0083 (8)
O7	0.1130 (15)	0.0479 (10)	0.0942 (14)	−0.0030 (10)	0.0575 (12)	−0.0063 (10)
O8	0.0827 (14)	0.259 (4)	0.0518 (11)	0.0282 (18)	0.0007 (11)	0.0389 (16)
C8	0.0372 (8)	0.0337 (9)	0.0392 (9)	−0.0009 (7)	0.0092 (7)	−0.0012 (7)
N2	0.0417 (8)	0.0402 (9)	0.0448 (8)	0.0024 (7)	0.0112 (7)	0.0001 (7)
O2	0.0528 (8)	0.0581 (10)	0.0563 (9)	0.0137 (7)	0.0223 (7)	0.0056 (7)
C9	0.0422 (9)	0.0421 (10)	0.0370 (9)	−0.0007 (8)	0.0085 (7)	0.0054 (8)
C10	0.0465 (10)	0.0422 (10)	0.0438 (10)	0.0081 (8)	0.0116 (8)	0.0084 (9)
C11	0.0403 (9)	0.0370 (10)	0.0427 (9)	0.0024 (7)	0.0124 (8)	0.0001 (8)
C12	0.0546 (11)	0.0610 (13)	0.0405 (10)	0.0101 (10)	0.0191 (9)	0.0117 (10)
C13	0.0478 (10)	0.0547 (12)	0.0419 (10)	0.0105 (9)	0.0104 (8)	0.0142 (9)
C14	0.0585 (12)	0.0624 (14)	0.0642 (13)	0.0047 (11)	0.0312 (11)	−0.0008 (12)
O1	0.0584 (8)	0.0552 (9)	0.0418 (7)	0.0062 (7)	0.0221 (6)	0.0036 (6)
C1	0.0399 (8)	0.0334 (9)	0.0393 (8)	−0.0047 (7)	0.0136 (7)	−0.0037 (7)
C4	0.0445 (9)	0.0329 (9)	0.0389 (9)	−0.0022 (7)	0.0134 (7)	−0.0021 (7)
C5	0.0430 (9)	0.0385 (10)	0.0444 (10)	0.0074 (8)	0.0161 (8)	0.0035 (8)
N1	0.0446 (8)	0.0523 (10)	0.0484 (9)	−0.0010 (7)	0.0189 (7)	−0.0013 (8)
C2	0.0388 (9)	0.0430 (10)	0.0501 (10)	0.0058 (8)	0.0107 (8)	0.0016 (9)
C6	0.0457 (9)	0.0372 (9)	0.0411 (9)	0.0049 (8)	0.0125 (8)	0.0055 (8)
C3	0.0475 (10)	0.0457 (11)	0.0400 (9)	0.0037 (9)	0.0095 (8)	0.0046 (8)
C7	0.0598 (12)	0.0687 (15)	0.0520 (12)	0.0045 (11)	0.0261 (10)	−0.0026 (11)
N3	0.0418 (8)	0.0362 (8)	0.0506 (9)	−0.0026 (7)	0.0070 (7)	0.0007 (7)
O3	0.0564 (8)	0.0490 (8)	0.0568 (9)	0.0122 (7)	0.0100 (7)	0.0069 (7)
O4	0.0537 (8)	0.0401 (8)	0.0936 (12)	0.0076 (7)	0.0230 (8)	−0.0016 (8)
O5	0.1142 (16)	0.0904 (15)	0.0516 (10)	−0.0027 (13)	0.0089 (10)	−0.0085 (10)
O6	0.0653 (10)	0.0539 (10)	0.1067 (14)	0.0002 (8)	0.0223 (10)	−0.0067 (10)

Geometric parameters (Å, º) top

N4—O8	1.177 (3)	O1—C4	1.366 (2)
N4—O6	1.259 (3)	O1—C7	1.416 (3)
N4—O7	1.268 (2)	C1—C6	1.370 (3)
C8—C13	1.369 (3)	C1—C2	1.386 (3)
C8—C9	1.381 (2)	C1—N1	1.460 (3)
C8—N2	1.462 (2)	C4—C5	1.381 (3)
N2—H2A	0.8900	C4—C3	1.398 (3)
N2—H2B	0.8900	C5—C6	1.401 (3)
N2—H2C	0.8900	C5—H5	0.9300
O2—C11	1.378 (2)	N1—H1A	0.8900
O2—C14	1.417 (3)	N1—H1B	0.8900
C9—C10	1.376 (3)	N1—H1C	0.8900
C9—H9	0.9300	C2—C3	1.365 (3)
C10—C11	1.384 (3)	C2—H2	0.9300
C10—H10	0.9300	C6—H6	0.9300
C11—C12	1.379 (3)	C3—H3	0.9300
C12—C13	1.390 (3)	C7—H7A	0.9600
C12—H12	0.9300	C7—H7B	0.9600
C13—H13	0.9300	C7—H7C	0.9600
C14—H14A	0.9600	N3—O5	1.202 (3)
C14—H14B	0.9600	N3—O3	1.241 (2)
C14—H14C	0.9600	N3—O4	1.268 (2)

O8—N4—O6	119.3 (3)	C4—O1—C7	117.01 (16)
O8—N4—O7	129.4 (3)	C6—C1—C2	121.00 (18)
O6—N4—O7	111.25 (18)	C6—C1—N1	119.25 (16)
C13—C8—C9	120.71 (18)	C2—C1—N1	119.72 (17)
C13—C8—N2	119.57 (16)	O1—C4—C5	124.37 (17)
C9—C8—N2	119.72 (17)	O1—C4—C3	116.13 (17)
C8—N2—H2A	109.5	C5—C4—C3	119.50 (18)
C8—N2—H2B	109.5	C4—C5—C6	119.69 (17)
H2A—N2—H2B	109.5	C4—C5—H5	120.2
C8—N2—H2C	109.5	C6—C5—H5	120.2
H2A—N2—H2C	109.5	C1—N1—H1A	109.5
H2B—N2—H2C	109.5	C1—N1—H1B	109.5
C11—O2—C14	117.42 (16)	H1A—N1—H1B	109.5
C10—C9—C8	119.27 (18)	C1—N1—H1C	109.5
C10—C9—H9	120.4	H1A—N1—H1C	109.5
C8—C9—H9	120.4	H1B—N1—H1C	109.5
C9—C10—C11	120.42 (17)	C3—C2—C1	119.49 (17)
C9—C10—H10	119.8	C3—C2—H2	120.3
C11—C10—H10	119.8	C1—C2—H2	120.3
O2—C11—C12	124.06 (18)	C1—C6—C5	119.58 (17)
O2—C11—C10	115.76 (17)	C1—C6—H6	120.2
C12—C11—C10	120.17 (18)	C5—C6—H6	120.2
C11—C12—C13	119.17 (18)	C2—C3—C4	120.71 (18)
C11—C12—H12	120.4	C2—C3—H3	119.6
C13—C12—H12	120.4	C4—C3—H3	119.6
C8—C13—C12	120.25 (18)	O1—C7—H7A	109.5
C8—C13—H13	119.9	O1—C7—H7B	109.5
C12—C13—H13	119.9	H7A—C7—H7B	109.5
O2—C14—H14A	109.5	O1—C7—H7C	109.5
O2—C14—H14B	109.5	H7A—C7—H7C	109.5
H14A—C14—H14B	109.5	H7B—C7—H7C	109.5
O2—C14—H14C	109.5	O5—N3—O3	120.8 (2)
H14A—C14—H14C	109.5	O5—N3—O4	122.17 (19)
H14B—C14—H14C	109.5	O3—N3—O4	117.03 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.89	2.25	2.823 (3)	122
N1—H1A···O7ⁱⁱ	0.89	2.52	2.979 (3)	113
N1—H1B···O6ⁱⁱⁱ	0.89	2.26	2.843 (3)	123
N1—H1B···O5^iv	0.89	2.12	2.903 (3)	146
N1—H1C···O7^v	0.89	2.14	2.935 (3)	148
N2—H2A···O3ⁱ	0.89	2.08	2.967 (3)	177
N2—H2A···O4ⁱ	0.89	2.55	3.187 (3)	129
N2—H2B···O6^vi	0.89	2.46	3.070 (3)	127
N2—H2B···O7^vi	0.89	2.22	3.083 (3)	163
N2—H2C···O3	0.89	2.07	2.891 (2)	152
C9—H9···O8^v	0.93	2.48	3.223 (3)	137

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

Experimental details

Crystal data
Chemical formula	C₇H₁₀NO⁺·NO₃⁻
M_r	186.17
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	14.724 (2), 7.304 (3), 17.509 (2)
β (°)	112.84 (2)
V (Å³)	1735.3 (8)
Z	8
Radiation type	Ag Kα, λ = 0.56085 Å
µ (mm⁻¹)	0.07
Crystal size (mm)	0.35 × 0.25 × 0.20

Data collection
Diffractometer	Enraf–Nonius TurboCAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12462, 8244, 2756
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.836

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.219, 0.93
No. of reflections	8244
No. of parameters	235
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.25

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.89	2.25	2.823 (3)	122
N1—H1A···O7ⁱⁱ	0.89	2.52	2.979 (3)	113
N1—H1B···O6ⁱⁱⁱ	0.89	2.26	2.843 (3)	123
N1—H1B···O5^iv	0.89	2.12	2.903 (3)	146
N1—H1C···O7^v	0.89	2.14	2.935 (3)	148
N2—H2A···O3ⁱ	0.89	2.08	2.967 (3)	177
N2—H2A···O4ⁱ	0.89	2.55	3.187 (3)	129
N2—H2B···O6^vi	0.89	2.46	3.070 (3)	127
N2—H2B···O7^vi	0.89	2.22	3.083 (3)	163
N2—H2C···O3	0.89	2.07	2.891 (2)	152
C9—H9···O8^v	0.93	2.48	3.223 (3)	137

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

References

Ben Amor, F., Soumhi, E. H., Ould Abdellahi, M. & Jouini, T. (1995). Acta Cryst. C51, 933–935. CSD CrossRef CAS IUCr Journals Google Scholar
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Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
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Volume 67| Part 9| September 2011| Page o2334

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