Naphthalene-2,6-dicarb-oxy-lic acid-1-methyl-pyrrolidin-2-one (1/2).

The asymmetric unit of the title compound, C(12)H(8)O(4)·2C(5)H(9)NO, contains one half-mol-ecule of naphthalene-2,6-dicarb-oxy-lic acid (NDA) and one mol-ecule of 1-methyl-pyrrolidin-2-one (NMP): the NDA molecules lie on the crystallographic twofold rotation axes. In the crystal, the components are linked by strong O-H⋯O hydrogen bonds and C-H⋯O inter-actions.

Related literature

For the crystal structure of naphthalene-2,6-dicarb­oxy­lic acid (NDA), see: Kaduk & Golab (1999 ▶). For the crystal structure of N-methyl-2-Pyrrolidone (NMP), see: Müller et al. (1996 ▶). For the purification of NDA, see: Nagase et al. (2004 ▶). For related structures, see: Guo et al. (2009 ▶); Dale & Elsegood (2004 ▶).

Experimental

Crystal data

C12H8O4·2C5H9NO

M = 414.45

Orthorhombic,

a = 19.7306 (11) Å

b = 28.7632 (19) Å

c = 7.1906 (4) Å

V = 4080.8 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 120 K

0.30 × 0.11 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.987, T max = 0.990

3255 measured reflections

1017 independent reflections

847 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.087

S = 1.05

1017 reflections

138 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 12008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052396/su2234sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052396/su2234Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H8O4·2C5H9NO	F(000) = 1760
Mr = 414.45	Dx = 1.349 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 1127 reflections
a = 19.7306 (11) Å	θ = 3.1–29.2°
b = 28.7632 (19) Å	µ = 0.10 mm−1
c = 7.1906 (4) Å	T = 120 K
V = 4080.8 (4) Å3	Needle, colourless
Z = 8	0.30 × 0.11 × 0.10 mm

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	1017 independent reflections
Radiation source: fine-focus sealed tube	847 reflections with I > 2σ(I)
graphite	Rint = 0.037
Detector resolution: 10.3592 pixels mm-1	θmax = 25.4°, θmin = 3.1°
ω scans	h = −23→19
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −22→34
Tmin = 0.987, Tmax = 0.990	l = −8→7
3255 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0405P)2 + 1.8717P] where P = (Fo2 + 2Fc2)/3
1017 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.20 e Å−3

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm; CrysAlis PRO (Oxford Diffraction, 2009).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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.

	x	y	z	Uiso*/Ueq
O1	0.24703 (10)	0.09264 (7)	0.7871 (3)	0.0278 (7)
O2	0.13547 (10)	0.10088 (8)	0.7582 (4)	0.0385 (8)
C1	0.27857 (13)	0.23501 (10)	0.7441 (4)	0.0168 (8)
C2	0.26776 (13)	0.18651 (10)	0.7497 (4)	0.0180 (8)
C3	0.20359 (13)	0.16856 (10)	0.7495 (4)	0.0177 (8)
C4	0.14695 (13)	0.19829 (10)	0.7411 (4)	0.0200 (9)
C5	0.15563 (13)	0.24549 (10)	0.7410 (4)	0.0191 (9)
C6	0.19144 (14)	0.11756 (10)	0.7638 (4)	0.0200 (8)
O3	0.23717 (10)	0.00444 (7)	0.8202 (3)	0.0252 (7)
N1	0.18459 (12)	−0.06402 (9)	0.8830 (4)	0.0223 (7)
C7	0.18914 (15)	−0.01786 (11)	0.8877 (4)	0.0219 (9)
C8	0.12795 (15)	0.00109 (11)	0.9868 (5)	0.0252 (9)
C9	0.07849 (14)	−0.03970 (11)	0.9918 (5)	0.0259 (10)
C10	0.12448 (14)	−0.08267 (11)	0.9734 (5)	0.0256 (10)
C11	0.23599 (16)	−0.09402 (11)	0.8060 (5)	0.0294 (10)
H1	0.23680	0.06520	0.80000	0.0420*
H2	0.30480	0.16650	0.75370	0.0220*
H4	0.10350	0.18580	0.73570	0.0240*
H5	0.11800	0.26490	0.73890	0.0230*
H8A	0.10880	0.02720	0.91940	0.0300*
H8B	0.13950	0.01110	1.11160	0.0300*
H9A	0.04650	−0.03800	0.88950	0.0310*
H9B	0.05360	−0.04030	1.10810	0.0310*
H10A	0.10330	−0.10650	0.89760	0.0310*
H10B	0.13540	−0.09560	1.09430	0.0310*
H11A	0.21610	−0.11380	0.71350	0.0440*
H11B	0.27090	−0.07550	0.75000	0.0440*
H11C	0.25520	−0.11270	0.90320	0.0440*

	U11	U22	U33	U12	U13	U23
O1	0.0248 (11)	0.0165 (11)	0.0421 (14)	−0.0012 (9)	0.0016 (10)	0.0040 (11)
O2	0.0264 (12)	0.0216 (12)	0.0675 (17)	−0.0061 (10)	−0.0131 (13)	0.0029 (13)
C1	0.0178 (13)	0.0197 (15)	0.0130 (13)	−0.0010 (12)	0.0015 (13)	0.0011 (14)
C2	0.0217 (14)	0.0186 (15)	0.0138 (14)	0.0029 (12)	0.0002 (13)	−0.0012 (14)
C3	0.0199 (15)	0.0193 (15)	0.0138 (14)	−0.0001 (13)	−0.0024 (12)	−0.0009 (14)
C4	0.0165 (14)	0.0266 (18)	0.0170 (14)	−0.0037 (13)	−0.0015 (14)	0.0019 (14)
C5	0.0178 (14)	0.0213 (17)	0.0183 (14)	0.0027 (12)	−0.0011 (13)	0.0007 (14)
C6	0.0214 (14)	0.0187 (15)	0.0200 (15)	−0.0002 (14)	−0.0025 (13)	0.0012 (14)
O3	0.0240 (12)	0.0195 (11)	0.0322 (13)	−0.0027 (10)	0.0047 (10)	0.0025 (11)
N1	0.0213 (12)	0.0209 (13)	0.0247 (13)	0.0002 (12)	0.0021 (11)	0.0037 (12)
C7	0.0235 (15)	0.0213 (16)	0.0209 (15)	0.0002 (15)	−0.0058 (13)	0.0006 (14)
C8	0.0256 (15)	0.0263 (17)	0.0238 (16)	0.0049 (14)	0.0001 (13)	−0.0018 (17)
C9	0.0229 (15)	0.0301 (19)	0.0246 (16)	0.0012 (14)	0.0011 (15)	0.0034 (16)
C10	0.0250 (16)	0.0281 (18)	0.0237 (17)	−0.0052 (15)	0.0004 (13)	0.0065 (15)
C11	0.0313 (18)	0.0259 (18)	0.0309 (17)	0.0064 (15)	0.0019 (15)	0.0017 (16)

O1—C6	1.321 (3)	C4—H4	0.9300
O2—C6	1.205 (3)	C5—H5	0.9300
O1—H1	0.8200	C7—C8	1.504 (4)
O3—C7	1.243 (4)	C8—C9	1.527 (4)
N1—C7	1.331 (4)	C9—C10	1.539 (4)
N1—C10	1.455 (4)	C8—H8A	0.9700
N1—C11	1.442 (4)	C8—H8B	0.9700
C1—C5i	1.414 (4)	C9—H9A	0.9700
C1—C1i	1.419 (4)	C9—H9B	0.9700
C1—C2	1.412 (4)	C10—H10A	0.9700
C2—C3	1.367 (4)	C10—H10B	0.9700
C3—C6	1.490 (4)	C11—H11A	0.9600
C3—C4	1.409 (4)	C11—H11B	0.9600
C4—C5	1.368 (4)	C11—H11C	0.9600
C2—H2	0.9300
C6—O1—H1	109.00	C7—C8—C9	104.2 (3)
C10—N1—C11	121.6 (3)	C8—C9—C10	103.8 (2)
C7—N1—C10	114.3 (2)	N1—C10—C9	102.9 (2)
C7—N1—C11	124.0 (3)	C7—C8—H8A	111.00
C2—C1—C5i	122.1 (2)	C7—C8—H8B	111.00
C1i—C1—C5i	119.2 (3)	C9—C8—H8A	111.00
C1i—C1—C2	118.7 (2)	C9—C8—H8B	111.00
C1—C2—C3	120.9 (2)	H8A—C8—H8B	109.00
C4—C3—C6	118.2 (2)	C8—C9—H9A	111.00
C2—C3—C6	121.4 (2)	C8—C9—H9B	111.00
C2—C3—C4	120.4 (3)	C10—C9—H9A	111.00
C3—C4—C5	120.2 (2)	C10—C9—H9B	111.00
C1i—C5—C4	120.6 (2)	H9A—C9—H9B	109.00
O1—C6—O2	123.3 (3)	N1—C10—H10A	111.00
O2—C6—C3	122.5 (3)	N1—C10—H10B	111.00
O1—C6—C3	114.2 (2)	C9—C10—H10A	111.00
C3—C2—H2	120.00	C9—C10—H10B	111.00
C1—C2—H2	120.00	H10A—C10—H10B	109.00
C3—C4—H4	120.00	N1—C11—H11A	109.00
C5—C4—H4	120.00	N1—C11—H11B	110.00
C4—C5—H5	120.00	N1—C11—H11C	109.00
C1i—C5—H5	120.00	H11A—C11—H11B	109.00
O3—C7—N1	123.8 (3)	H11A—C11—H11C	110.00
O3—C7—C8	127.6 (3)	H11B—C11—H11C	109.00
N1—C7—C8	108.6 (3)
C10—N1—C7—O3	179.0 (3)	C1—C2—C3—C4	0.9 (4)
C10—N1—C7—C8	−0.7 (4)	C2—C3—C6—O1	3.7 (4)
C11—N1—C7—O3	2.7 (5)	C2—C3—C4—C5	−2.8 (4)
C11—N1—C7—C8	−177.1 (3)	C6—C3—C4—C5	175.4 (3)
C7—N1—C10—C9	15.8 (4)	C4—C3—C6—O2	4.1 (4)
C11—N1—C10—C9	−167.8 (3)	C2—C3—C6—O2	−177.7 (3)
C2—C1—C5i—C4i	−178.1 (3)	C4—C3—C6—O1	−174.5 (3)
C2—C1—C1i—C5	−2.9 (4)	C3—C4—C5—C1i	1.8 (4)
C1i—C1—C2—C3	1.9 (4)	O3—C7—C8—C9	165.4 (3)
C5i—C1—C2—C3	−178.9 (3)	N1—C7—C8—C9	−14.9 (3)
C2—C1—C1i—C2i	176.3 (3)	C7—C8—C9—C10	23.5 (3)
C5i—C1—C1i—C5	177.9 (3)	C8—C9—C10—N1	−23.5 (3)
C1—C2—C3—C6	−177.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.82	1.75	2.556 (3)	165
C2—H2···O2ii	0.93	2.48	3.163 (4)	131
C8—H8A···O2	0.97	2.47	3.311 (4)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.82	1.75	2.556 (3)	165
C2—H2⋯O2i	0.93	2.48	3.163 (4)	131
C8—H8A⋯O2	0.97	2.47	3.311 (4)	145

Symmetry code: (i) .