N,N'-Bis(3-hydroxy­phenyl)-1,8:4,5-naphthalene­tetra­carbox­imide di­methyl sulfoxide disolvate

The structure of the title compound, C₂₆H₁₄N₂O₆·2C₂H₆OS, shows the essentially planar mol­ecule to be centrosymmetric and hydrogen-bonded via the phenolic H atom to DMSO mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.105
• Data-to-parameter ratio = 17.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: COLLECT (Nonius, 1997–2002); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Bis-N,N'-(3-hydroxyphenyl)-1,4,5,8-naphthalenetetracarboxylic diimide

Crystal data

C26H14N2O6·2C2H6OS	F(000) = 632
Mr = 606.65	Dx = 1.477 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19123 reflections
a = 14.1659 (2) Å	θ = 2.9–28.3°
b = 7.9501 (1) Å	µ = 0.25 mm^−1
c = 12.3307 (2) Å	T = 123 K
β = 100.850 (1)°	Acicular, yellow-brown
V = 1363.86 (3) Å^3	0.28 × 0.10 × 0.07 mm
Z = 2

Data collection

KappaCCD diffractometer	2478 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
Horizonally mounted graphite crystal monochromator	θmax = 28°, θmin = 3.0°
Detector resolution: 9 pixels mm^-1	h = −18→18
CCD rotation images, thick slices scans	k = −10→10
19123 measured reflections	l = −16→16
3375 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0549P)^2 + 0.1051P] where P = (Fo^2 + 2Fc^2)/3
3375 reflections	(Δ/σ)max = 0.002
193 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3

Special details

Experimental. ¹H n.m.r. (300 MHz, d₆-DMSO): δ 9.71, (s, 2H, OH), 8.74, (s, 4H, NDI-H), 7.39, (t, J=8.12 Hz, 2H, ArH), 6.91, (m, 6H, ArH).

¹³C n.m.r. (50 MHz, d₆-DMSO): 162.8, 157.8, 136.4, 130.3, 129.5, 126.9, 126.3, 119.4, 116.1, 115.4.

Mass spectrum (-ive ESI): m/z 450.0 ([M]^-).

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.67225 (11)	0.41014 (18)	0.56052 (13)	0.0170 (3)
H1	0.7386	0.3854	0.5662	0.020*
C2	0.62059 (11)	0.47256 (18)	0.46345 (13)	0.0144 (3)
C3	0.52265 (10)	0.51410 (17)	0.45456 (12)	0.0129 (3)
C4	0.46894 (11)	0.58290 (18)	0.35624 (12)	0.0142 (3)
C5	0.37254 (11)	0.61746 (19)	0.34825 (13)	0.0168 (3)
H5	0.3363	0.6599	0.2812	0.020*
C6	0.66720 (11)	0.49043 (19)	0.36587 (12)	0.0156 (3)
C7	0.51696 (11)	0.62054 (18)	0.26212 (13)	0.0153 (3)
C8	0.66108 (11)	0.60128 (19)	0.17955 (13)	0.0156 (3)
C9	0.74015 (11)	0.70758 (18)	0.19485 (13)	0.0163 (3)
H9	0.7598	0.7647	0.2630	0.020*
C10	0.79029 (11)	0.72945 (19)	0.10910 (13)	0.0183 (3)
C11	0.76008 (12)	0.6482 (2)	0.00910 (13)	0.0208 (4)
H11	0.7945	0.6627	−0.0493	0.025*
C12	0.67956 (12)	0.5458 (2)	−0.00548 (14)	0.0218 (4)
H12	0.6585	0.4917	−0.0745	0.026*
C13	0.62911 (11)	0.52130 (19)	0.07994 (13)	0.0190 (3)
H13	0.5739	0.4511	0.0699	0.023*
C14	1.04150 (16)	0.7148 (3)	0.46244 (18)	0.0400 (5)
H14A	0.9955	0.7136	0.5127	0.060*
H14B	1.1069	0.7026	0.5050	0.060*
H14C	1.0274	0.6215	0.4099	0.060*
C15	1.10562 (12)	0.8565 (2)	0.29133 (14)	0.0254 (4)
H15A	1.0827	0.7516	0.2536	0.038*
H15B	1.1723	0.8422	0.3297	0.038*
H15C	1.1023	0.9473	0.2370	0.038*
N1	0.61350 (9)	0.57187 (15)	0.27276 (10)	0.0152 (3)
O1	0.74746 (8)	0.43824 (15)	0.36473 (9)	0.0242 (3)
O2	0.47564 (8)	0.69060 (14)	0.17886 (9)	0.0212 (3)
O3	0.86970 (8)	0.82908 (16)	0.12004 (10)	0.0261 (3)
H3	0.8873	0.8562	0.1866	0.039*
O4	0.93028 (9)	0.91972 (18)	0.32553 (10)	0.0336 (3)
S1	1.03178 (3)	0.90837 (5)	0.38922 (3)	0.02034 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0118 (7)	0.0201 (8)	0.0197 (8)	0.0013 (6)	0.0045 (6)	0.0020 (6)
C2	0.0137 (8)	0.0126 (7)	0.0176 (8)	−0.0007 (6)	0.0050 (6)	−0.0006 (6)
C3	0.0120 (7)	0.0115 (7)	0.0155 (8)	−0.0013 (5)	0.0031 (6)	−0.0008 (6)
C4	0.0146 (8)	0.0127 (7)	0.0159 (8)	−0.0003 (6)	0.0039 (6)	−0.0001 (6)
C5	0.0159 (8)	0.0177 (8)	0.0165 (8)	0.0017 (6)	0.0020 (6)	0.0036 (6)
C6	0.0150 (8)	0.0171 (8)	0.0152 (8)	0.0004 (6)	0.0040 (6)	0.0019 (6)
C7	0.0152 (8)	0.0143 (7)	0.0168 (8)	−0.0008 (6)	0.0040 (6)	−0.0004 (6)
C8	0.0142 (8)	0.0185 (8)	0.0150 (8)	0.0032 (6)	0.0055 (6)	0.0032 (6)
C9	0.0170 (8)	0.0175 (7)	0.0149 (8)	0.0001 (6)	0.0045 (6)	0.0003 (6)
C10	0.0158 (8)	0.0209 (8)	0.0186 (8)	0.0006 (6)	0.0047 (7)	0.0043 (6)
C11	0.0224 (9)	0.0277 (9)	0.0140 (8)	0.0049 (7)	0.0075 (7)	0.0034 (7)
C12	0.0226 (9)	0.0268 (9)	0.0152 (8)	0.0030 (7)	0.0020 (7)	−0.0021 (7)
C13	0.0177 (8)	0.0192 (8)	0.0194 (8)	−0.0005 (6)	0.0017 (7)	0.0002 (6)
C14	0.0456 (13)	0.0399 (12)	0.0429 (12)	0.0136 (9)	0.0297 (10)	0.0156 (9)
C15	0.0219 (9)	0.0355 (10)	0.0214 (9)	−0.0033 (7)	0.0106 (7)	−0.0025 (7)
N1	0.0131 (6)	0.0186 (7)	0.0152 (7)	0.0008 (5)	0.0056 (5)	0.0028 (5)
O1	0.0165 (6)	0.0366 (7)	0.0214 (6)	0.0091 (5)	0.0084 (5)	0.0079 (5)
O2	0.0182 (6)	0.0269 (6)	0.0192 (6)	0.0039 (5)	0.0054 (5)	0.0084 (5)
O3	0.0232 (6)	0.0360 (7)	0.0210 (6)	−0.0109 (5)	0.0090 (5)	0.0001 (5)
O4	0.0179 (7)	0.0578 (9)	0.0243 (7)	0.0020 (6)	0.0021 (5)	−0.0034 (6)
S1	0.0173 (2)	0.0254 (2)	0.0190 (2)	−0.00052 (16)	0.00539 (17)	−0.00250 (16)

Geometric parameters (Å, º)

C1—C2	1.373 (2)	C9—H9	0.9500
C1—C5^i	1.409 (2)	C10—O3	1.3616 (19)
C1—H1	0.9500	C10—C11	1.386 (2)
C2—C3	1.410 (2)	C11—C12	1.385 (2)
C2—C6	1.484 (2)	C11—H11	0.9500
C3—C3^i	1.410 (3)	C12—C13	1.393 (2)
C3—C4	1.414 (2)	C12—H12	0.9500
C4—C5	1.378 (2)	C13—H13	0.9500
C4—C7	1.482 (2)	C14—S1	1.7761 (19)
C5—C1^i	1.409 (2)	C14—H14A	0.9800
C5—H5	0.9500	C14—H14B	0.9800
C6—O1	1.2128 (18)	C14—H14C	0.9800
C6—N1	1.4097 (19)	C15—S1	1.7879 (16)
C7—O2	1.2168 (18)	C15—H15A	0.9800
C7—N1	1.403 (2)	C15—H15B	0.9800
C8—C13	1.382 (2)	C15—H15C	0.9800
C8—C9	1.387 (2)	O3—H3	0.8400
C8—N1	1.4567 (19)	O4—S1	1.5058 (13)
C9—C10	1.391 (2)
C2—C1—C5^i	120.41 (14)	C11—C10—C9	120.09 (14)
C2—C1—H1	119.8	C12—C11—C10	119.88 (15)
C5^i—C1—H1	119.8	C12—C11—H11	120.1
C1—C2—C3	120.50 (14)	C10—C11—H11	120.1
C1—C2—C6	119.73 (14)	C11—C12—C13	120.73 (15)
C3—C2—C6	119.73 (13)	C11—C12—H12	119.6
C3^i—C3—C2	119.29 (17)	C13—C12—H12	119.6
C3^i—C3—C4	119.39 (17)	C8—C13—C12	118.60 (14)
C2—C3—C4	121.31 (13)	C8—C13—H13	120.7
C5—C4—C3	120.28 (14)	C12—C13—H13	120.7
C5—C4—C7	119.90 (14)	S1—C14—H14A	109.5
C3—C4—C7	119.82 (14)	S1—C14—H14B	109.5
C4—C5—C1^i	120.07 (15)	H14A—C14—H14B	109.5
C4—C5—H5	120.0	S1—C14—H14C	109.5
C1^i—C5—H5	120.0	H14A—C14—H14C	109.5
O1—C6—N1	120.73 (14)	H14B—C14—H14C	109.5
O1—C6—C2	122.52 (14)	S1—C15—H15A	109.5
N1—C6—C2	116.74 (13)	S1—C15—H15B	109.5
O2—C7—N1	120.71 (14)	H15A—C15—H15B	109.5
O2—C7—C4	122.30 (14)	S1—C15—H15C	109.5
N1—C7—C4	117.00 (13)	H15A—C15—H15C	109.5
C13—C8—C9	121.50 (14)	H15B—C15—H15C	109.5
C13—C8—N1	120.31 (14)	C7—N1—C6	124.73 (13)
C9—C8—N1	118.17 (14)	C7—N1—C8	118.00 (12)
C8—C9—C10	119.17 (14)	C6—N1—C8	117.22 (12)
C8—C9—H9	120.4	C10—O3—H3	109.5
C10—C9—H9	120.4	O4—S1—C14	106.98 (10)
O3—C10—C11	118.05 (14)	O4—S1—C15	106.51 (8)
O3—C10—C9	121.86 (14)	C14—S1—C15	98.29 (9)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.84	1.78	2.6186 (17)	177