catena-Poly[(μ-anilido)(μ-1,2-dimeth­oxy­ethane-κ3-O,O′:O)sodium]

Liebing, P.; Wagner, C.; Merzweiler, K.

doi:10.1107/S1600536812040500

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page m1315

https://doi.org/10.1107/S1600536812040500

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catena-Poly[(μ-anilido)(μ-1,2-dimethoxyethane-κ³-O,O′:O)sodium]

Phil Liebing,^a Christoph Wagner ^a and Kurt Merzweiler ^a ^*

^aInstitut für Chemie, Naturwissenschaftliche Fakultät II, Martin-Luther-Universität Halle-Wittenberg, Kurt-Mothes-Str. 2, 06120 Halle, Germany
^*Correspondence e-mail: kurt.merzweiler@chemie.uni-halle.de

(Received 10 September 2012; accepted 25 September 2012; online 29 September 2012)

In the title compound, [Na(C₆H₅NH)(C₄H₁₀O₂)], the Na⁺ cation is coordinated by the N atoms of two anilide anions, two O atoms of a chelating 1,2-dimethoxyethane (dme) ligand and one O atom of an adjacent dme ligand. The coordination polyhedron around Na⁺ corresponds to a distorted square pyramid with the N atoms of the anilide groups and the O atoms of the chelating dme unit at the base and a third O atom at the apical position. The anilide anions act as μ-bridging ligands and the 1,2-dimethoxyethane molecules display a μ₂-κ³-O,O′ coordination mode. As a result of this connectivity, a polymeric chain structure parallel to [100] is formed, consisting of Na₂O₂ and Na₂N₂ four-membered rings. It should be noted that the remaining H atom of the anilide NH group is not involved in hydrogen bonding.

Related literature

For the crystal structure of a sodium anilide complex, see: Barr et al. (1995 ) and for the crystal structures of sodium compounds with μ-bridging 1,2-dimethoxyethane ligands, see: Bock et al. (1999 , 2000 ); Rothenberger et al. (2007 ); Tirla et al. (2002 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

[Na(C₆H₆N)(C₄H₁₀O₂)]
M_r = 205.23
Monoclinic, P 2₁ /c
a = 7.0450 (7) Å
b = 13.1609 (14) Å
c = 12.5545 (12) Å
β = 101.153 (8)°
V = 1142.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 200 K
0.40 × 0.24 × 0.24 mm

Data collection

Stoe IPDS2T diffractometer
5398 measured reflections
2206 independent reflections
1450 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.078
S = 0.85
2206 reflections
131 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2009 ); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536812040500/wm2683sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812040500/wm2683Isup2.hkl

checkCIF report

Comment top

In the title compound,[Na(C₆H₅NH)(C₄H₁₀O₂)] or [Na(PhNH)(dme)], the Na⁺ cations are linked by bridging anilide (PhNH^-) groups and µ₂-κ³-O,O' coordinating 1,2-dimethoxyethane (dme) ligands to give a coordination polymer which extends parallel to [100]. The coordination around Na⁺ is distorted square pyramidal with two N atoms of the PhNH groups and two O atoms of the chelating dme ligands at the base of the square pyramid and a third O atom from an adjacing dme ligand at its apex (Fig.1). The Na—N distances of 2.4069 (14) and 2.4095 (11) Å are similar to the values that have been observed in the dimeric complex [{(pmdeta)Na(NHPh)}₂] (2.390 (5) and 2.444 (5) Å, pmdeta = pentamethyldiethylenetriamine) (Barr et al., 1995). Like in the case of the pmdeta derivative, the Na⁺ cations are linked by the PhNH groups to give planar Na₂N₂ rings with the phenyl groups in a trans arragement. The Na₂N₂ ring exhibits a rhombus shape with both the N—Na—N angle (93.22 (4)°) and the Na—N—Na angle (86.78 (4)°) close to 90°. A similar shaped Na₂N₂ ring has been observed in the pmdeta derivative (N—Na—N: 92.6°; Na—N—Na: 87.4°). The phenyl rings display a nearly perpedicular orientation with respect to the Na₂N₂ plane (82.16 (5)°). In the case of the pmdeta derivate a larger tilting (65°) due to the steric requirements of the pmdeta ligands is observed. In addition to the µ-bridging PhNH units, the Na⁺ cations are linked by µ₂-κ³-O,O' coordinating dme ligands. The chelate ring formed by the atoms Na, O1, C8, C9 and O2 adopts an envelope conformation with the carbon atom C9 at the flap position. The Na—O distances within the chelate ring are 2.4103 (10) and 2.6800 (12) Å and the Na—O distance to the neighbouring Na⁺ cation amounts to 2.4849 (12) Å. Sodium complexes with similar µ-bridging dme ligands are known, e.g. with CCDC (Allen, 2002) reference code JAXQUU (Na—O: 2.348–2.461 Å; Bock et al., 1999), WOTWAD (Na—O: 2.290–2.438 Å; Bock et al., 2000), HUPZOH (Na—O: 2.371–2.668 Å; Tirla et al., 2002) and QIBKIW (Na—O: 2.345–2.516 Å; Rothenberger et al., 2007). Due to the µ-bridging mode of the dme molecules four membered Na₂O₂ rings possessing crystallographic 1 symmetry are formed. The Na₂N₂ and Na₂O₂ rings are linked by corner sharing to give an infinite chain parallel to [100]. The tilt angle between the Na₂N₂ and Na₂O₂ rings is 72.33 (4)°. Using a polyhedral model, the chain structure can be described by edge-sharing NaO₃N₂ square pyramids (Fig. 2). Interestingly, the H atom of the anilide NH group is not involved in hydrogen bonding.

Related literature top

For the crystal structure of a sodium anilide complex, see: Barr et al. (1995) and for the crystal structures of sodium compounds with µ-bridging 1,2-dimethoxyethane ligands, see: Bock et al. (1999, 2000); Rothenberger et al. (2007); Tirla et al. (2002). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

0.7 ml (7.7 mmol) of aniline were added dropwise to a suspension of 0.29 g (7.5 mmol) of sodium amide in 10 ml of 1,2-dimethoxyethane. After one hour of stirring, the pale yellow reaction solution was reduced to 8 ml and afterwards layered with 20 ml of n-hexane. Colourless crystals of [Na(PhNH)(dme)] are formed at the phase boundary after one week. The product was filtered off and washed with n-pentane. Yield: 1.11 g (72%).

Structure description top

Computing details top

Data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-RED (Stoe & Cie, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The coordination around the Na⁺ cation in the structure of the title compound. The asymmetric unit is marked by filled bonds. Anisotropic displacement parameters are drawn at the 50% probability level. [Symmetry codes: i: 1 - x, -y, 1 - z; ii: 2 - x, -y, 1 - z]
	Fig. 2. Part of the chain structure extending parallel to [100].

catena-Poly[(µ-anilido)(µ-1,2-dimethoxyethane- κ³-O,O':O)sodium] top

Crystal data top

[Na(C₆H₆N)(C₄H₁₀O₂)]	F(000) = 440
M_r = 205.23	D_x = 1.194 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3804 reflections
a = 7.0450 (7) Å	θ = 4.0–29.2°
b = 13.1609 (14) Å	µ = 0.11 mm⁻¹
c = 12.5545 (12) Å	T = 200 K
β = 101.153 (8)°	Prism, colourless
V = 1142.1 (2) Å³	0.40 × 0.24 × 0.24 mm
Z = 4

Data collection top

Stoe IPDS2T diffractometer	1450 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.050
Graphite monochromator	θ_max = 26.0°, θ_min = 4.0°
Detector resolution: 6.67 pixels mm^-1	h = −8→8
phi rotation scans	k = −14→16
5398 measured reflections	l = −15→15
2206 independent 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ²(F_o²) + (0.0466P)²] where P = (F_o² + 2F_c²)/3
2206 reflections	(Δ/σ)_max < 0.001
131 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

[Na(C₆H₆N)(C₄H₁₀O₂)]	V = 1142.1 (2) Å³
M_r = 205.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.0450 (7) Å	µ = 0.11 mm⁻¹
b = 13.1609 (14) Å	T = 200 K
c = 12.5545 (12) Å	0.40 × 0.24 × 0.24 mm
β = 101.153 (8)°

Data collection top

Stoe IPDS2T diffractometer	1450 reflections with I > 2σ(I)
5398 measured reflections	R_int = 0.050
2206 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	Δρ_max = 0.14 e Å⁻³
2206 reflections	Δρ_min = −0.18 e Å⁻³
131 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
C1	0.53257 (15)	0.18227 (10)	0.39471 (10)	0.0352 (3)
C2	0.53896 (17)	0.23456 (11)	0.49422 (10)	0.0419 (3)
H2A	0.5200	0.1980	0.5547	0.050*
C3	0.5719 (2)	0.33670 (12)	0.50437 (11)	0.0496 (4)
H3A	0.5746	0.3676	0.5713	0.060*
C4	0.6015 (2)	0.39515 (12)	0.41776 (13)	0.0543 (4)
H4A	0.6253	0.4645	0.4255	0.065*
C5	0.5944 (2)	0.34720 (12)	0.31930 (11)	0.0511 (4)
H5A	0.6137	0.3851	0.2598	0.061*
C6	0.55974 (18)	0.24503 (11)	0.30740 (10)	0.0420 (3)
H6A	0.5538	0.2158	0.2394	0.050*
C7	0.9515 (3)	−0.05477 (18)	0.79319 (15)	0.0823 (6)
H7C	0.8362	−0.0954	0.7803	0.099*
H7B	0.9620	−0.0198	0.8612	0.099*
H7A	1.0623	−0.0978	0.7956	0.099*
C8	1.1104 (2)	0.08004 (15)	0.72251 (13)	0.0651 (5)
H8B	1.2216	0.0402	0.7127	0.078*
H8A	1.1365	0.1079	0.7954	0.078*
C9	1.0766 (2)	0.16376 (13)	0.64172 (14)	0.0637 (5)
H9B	0.9640	0.2027	0.6510	0.076*
H9A	1.1874	0.2090	0.6531	0.076*
C10	1.0256 (2)	0.20221 (14)	0.45538 (16)	0.0686 (5)
H10C	0.9439	0.2547	0.4747	0.082*
H10B	0.9684	0.1749	0.3856	0.082*
H10A	1.1504	0.2301	0.4523	0.082*
N	0.50434 (16)	0.08063 (9)	0.38965 (10)	0.0446 (3)
H1	0.505 (2)	0.0608 (12)	0.3207 (13)	0.046 (4)*
O1	1.04685 (14)	0.12315 (8)	0.53495 (8)	0.0527 (3)
O2	0.94293 (14)	0.01729 (9)	0.70809 (8)	0.0569 (3)
Na	0.73912 (7)	0.00248 (4)	0.53096 (4)	0.04248 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0227 (5)	0.0435 (8)	0.0375 (7)	0.0040 (5)	0.0011 (5)	0.0051 (6)
C2	0.0345 (6)	0.0553 (9)	0.0358 (7)	0.0019 (6)	0.0068 (5)	0.0052 (6)
C3	0.0462 (7)	0.0561 (10)	0.0462 (8)	0.0064 (7)	0.0082 (6)	−0.0075 (7)
C4	0.0522 (8)	0.0395 (9)	0.0696 (10)	0.0042 (6)	0.0075 (7)	0.0007 (7)
C5	0.0512 (8)	0.0512 (10)	0.0506 (8)	0.0071 (7)	0.0088 (6)	0.0175 (7)
C6	0.0411 (7)	0.0499 (9)	0.0338 (6)	0.0068 (6)	0.0039 (5)	0.0053 (6)
C7	0.0701 (11)	0.1031 (17)	0.0689 (11)	0.0194 (11)	0.0017 (9)	0.0246 (11)
C8	0.0443 (8)	0.0836 (13)	0.0606 (9)	0.0040 (8)	−0.0066 (7)	−0.0207 (9)
C9	0.0436 (8)	0.0558 (10)	0.0871 (12)	−0.0060 (7)	0.0009 (8)	−0.0263 (9)
C10	0.0407 (8)	0.0578 (10)	0.1068 (13)	0.0106 (7)	0.0134 (8)	0.0208 (10)
N	0.0407 (6)	0.0454 (7)	0.0454 (7)	0.0009 (5)	0.0028 (5)	0.0025 (6)
O1	0.0434 (5)	0.0450 (6)	0.0671 (6)	0.0064 (4)	0.0041 (4)	−0.0024 (5)
O2	0.0428 (5)	0.0686 (8)	0.0545 (6)	0.0079 (5)	−0.0025 (4)	0.0028 (5)
Na	0.0315 (2)	0.0423 (3)	0.0507 (3)	0.0027 (2)	0.0008 (2)	0.0036 (2)

Geometric parameters (Å, º) top

C1—N	1.3522 (18)	C8—C9	1.485 (3)
C1—C6	1.4147 (19)	C8—H8B	0.9700
C1—C2	1.4193 (19)	C8—H8A	0.9700
C1—Na	3.1112 (13)	C9—O1	1.4205 (19)
C2—C3	1.366 (2)	C9—H9B	0.9700
C2—H2A	0.9300	C9—H9A	0.9700
C3—C4	1.380 (2)	C10—O1	1.430 (2)
C3—H3A	0.9300	C10—H10C	0.9600
C4—C5	1.380 (2)	C10—H10B	0.9600
C4—H4A	0.9300	C10—H10A	0.9600
C5—C6	1.370 (2)	N—Naⁱ	2.4069 (14)
C5—H5A	0.9300	N—Na	2.4095 (11)
C6—H6A	0.9300	N—H1	0.905 (16)
C7—O2	1.421 (2)	O1—Naⁱⁱ	2.4849 (12)
C7—H7C	0.9600	O1—Na	2.6800 (12)
C7—H7B	0.9600	O2—Na	2.4103 (10)
C7—H7A	0.9600	Na—Nⁱ	2.4069 (14)
C8—O2	1.423 (2)	Na—O1ⁱⁱ	2.4849 (12)

N—C1—C6	125.59 (13)	H9B—C9—H9A	108.2
N—C1—C2	120.02 (13)	O1—C10—H10C	109.5
C6—C1—C2	114.39 (13)	O1—C10—H10B	109.5
N—C1—Na	47.33 (6)	H10C—C10—H10B	109.5
C6—C1—Na	138.68 (9)	O1—C10—H10A	109.5
C2—C1—Na	87.30 (7)	H10C—C10—H10A	109.5
C3—C2—C1	122.35 (13)	H10B—C10—H10A	109.5
C3—C2—H2A	118.8	C1—N—Naⁱ	122.70 (10)
C1—C2—H2A	118.8	C1—N—Na	108.29 (8)
C2—C3—C4	121.59 (14)	Naⁱ—N—Na	86.78 (4)
C2—C3—H3A	119.2	C1—N—H1	107.6 (10)
C4—C3—H3A	119.2	Naⁱ—N—H1	113.5 (10)
C3—C4—C5	117.78 (15)	Na—N—H1	116.9 (9)
C3—C4—H4A	121.1	C9—O1—C10	111.21 (13)
C5—C4—H4A	121.1	C9—O1—Naⁱⁱ	125.19 (8)
C6—C5—C4	121.41 (14)	C10—O1—Naⁱⁱ	103.87 (10)
C6—C5—H5A	119.3	C9—O1—Na	102.22 (9)
C4—C5—H5A	119.3	C10—O1—Na	116.31 (8)
C5—C6—C1	122.46 (13)	Naⁱⁱ—O1—Na	98.06 (4)
C5—C6—H6A	118.8	C7—O2—C8	112.21 (12)
C1—C6—H6A	118.8	C7—O2—Na	124.81 (11)
O2—C7—H7C	109.5	C8—O2—Na	119.72 (10)
O2—C7—H7B	109.5	Nⁱ—Na—N	93.22 (4)
H7C—C7—H7B	109.5	Nⁱ—Na—O2	89.99 (4)
O2—C7—H7A	109.5	N—Na—O2	147.82 (5)
H7C—C7—H7A	109.5	Nⁱ—Na—O1ⁱⁱ	111.25 (5)
H7B—C7—H7A	109.5	N—Na—O1ⁱⁱ	114.40 (4)
O2—C8—C9	108.92 (11)	O2—Na—O1ⁱⁱ	93.98 (4)
O2—C8—H8B	109.9	Nⁱ—Na—O1	154.19 (4)
C9—C8—H8B	109.9	N—Na—O1	101.45 (4)
O2—C8—H8A	109.9	O2—Na—O1	66.39 (4)
C9—C8—H8A	109.9	O1ⁱⁱ—Na—O1	81.94 (4)
H8B—C8—H8A	108.3	Nⁱ—Na—C1	106.16 (4)
O1—C9—C8	109.89 (13)	N—Na—C1	24.37 (4)
O1—C9—H9B	109.7	O2—Na—C1	125.28 (4)
C8—C9—H9B	109.7	O1ⁱⁱ—Na—C1	124.92 (4)
O1—C9—H9A	109.7	O1—Na—C1	81.39 (3)
C8—C9—H9A	109.7

N—C1—C2—C3	178.31 (12)	C8—O2—Na—O1ⁱⁱ	80.20 (11)
C6—C1—C2—C3	−1.05 (17)	C7—O2—Na—O1	−157.16 (14)
Na—C1—C2—C3	142.48 (12)	C8—O2—Na—O1	0.80 (11)
C1—C2—C3—C4	−0.1 (2)	C7—O2—Na—C1	143.47 (13)
C2—C3—C4—C5	0.7 (2)	C8—O2—Na—C1	−58.57 (12)
C3—C4—C5—C6	−0.1 (2)	C9—O1—Na—Nⁱ	−5.56 (14)
C4—C5—C6—C1	−1.1 (2)	C10—O1—Na—Nⁱ	−126.90 (13)
N—C1—C6—C5	−177.64 (12)	Naⁱⁱ—O1—Na—Nⁱ	123.21 (9)
C2—C1—C6—C5	1.67 (17)	C9—O1—Na—N	117.83 (9)
Na—C1—C6—C5	−114.27 (15)	C10—O1—Na—N	−3.51 (12)
O2—C8—C9—O1	−62.11 (17)	Naⁱⁱ—O1—Na—N	−113.40 (5)
C6—C1—N—Naⁱ	−135.23 (11)	C9—O1—Na—O2	−30.82 (8)
C2—C1—N—Naⁱ	45.50 (13)	C10—O1—Na—O2	−152.15 (12)
Na—C1—N—Naⁱ	98.16 (10)	Naⁱⁱ—O1—Na—O2	97.96 (4)
C6—C1—N—Na	126.61 (11)	C9—O1—Na—O1ⁱⁱ	−128.78 (9)
C2—C1—N—Na	−52.66 (13)	C10—O1—Na—O1ⁱⁱ	109.89 (12)
C8—C9—O1—C10	−176.45 (12)	Naⁱⁱ—O1—Na—O1ⁱⁱ	0.0
C8—C9—O1—Naⁱⁱ	−50.41 (17)	C9—O1—Na—C1	103.91 (9)
C8—C9—O1—Na	58.76 (13)	C10—O1—Na—C1	−17.43 (11)
C9—C8—O2—C7	−170.51 (15)	Naⁱⁱ—O1—Na—C1	−127.31 (4)
C9—C8—O2—Na	28.93 (17)	N—C1—Na—Nⁱ	−60.14 (12)
C1—N—Na—Nⁱ	123.46 (11)	C6—C1—Na—Nⁱ	−158.78 (13)
Naⁱ—N—Na—Nⁱ	0.0	C2—C1—Na—Nⁱ	76.30 (8)
C1—N—Na—O2	28.35 (15)	C6—C1—Na—N	−98.64 (18)
Naⁱ—N—Na—O2	−95.11 (9)	C2—C1—Na—N	136.44 (14)
C1—N—Na—O1ⁱⁱ	−121.44 (10)	N—C1—Na—O2	−161.95 (10)
Naⁱ—N—Na—O1ⁱⁱ	115.10 (5)	C6—C1—Na—O2	99.41 (14)
C1—N—Na—O1	−35.19 (10)	C2—C1—Na—O2	−25.52 (9)
Naⁱ—N—Na—O1	−158.65 (4)	N—C1—Na—O1ⁱⁱ	71.35 (11)
Naⁱ—N—Na—C1	−123.46 (11)	C6—C1—Na—O1ⁱⁱ	−27.29 (15)
C7—O2—Na—Nⁱ	33.55 (14)	C2—C1—Na—O1ⁱⁱ	−152.21 (7)
C8—O2—Na—Nⁱ	−168.50 (11)	N—C1—Na—O1	145.16 (10)
C7—O2—Na—N	129.58 (14)	C6—C1—Na—O1	46.52 (14)
C8—O2—Na—N	−72.46 (14)	C2—C1—Na—O1	−78.40 (7)
C7—O2—Na—O1ⁱⁱ	−77.75 (13)

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

Experimental details

Crystal data
Chemical formula	[Na(C₆H₆N)(C₄H₁₀O₂)]
M_r	205.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	7.0450 (7), 13.1609 (14), 12.5545 (12)
β (°)	101.153 (8)
V (Å³)	1142.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.40 × 0.24 × 0.24

Data collection
Diffractometer	Stoe IPDS2T
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5398, 2206, 1450
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.078, 0.85
No. of reflections	2206
No. of parameters	131
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.18

Computer programs: X-AREA (Stoe & Cie, 2009), X-RED (Stoe & Cie, 2009), SHELXS97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

References

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