Bis(4-nitro­phen­yl) succinate

The title compound, C₁₆H₁₂N₂O₈, was prepared by the reaction of succinyl dichloride with 4-nitro­phenol. The mol­ecule is centrosymmetric and the two benzene rings are coplanar.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.062
• wR factor = 0.196
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

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Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

As part of our ongoing studies, we synthesized the title compound, (I), and report herein its synthesis and crystal structure.

In the molecule of (I), (Fig. 1) the bond lengths and angles are within normal ranges (Allen et al., 1987). It is centrosymmetric. Ring A (C1—C6) is, of course, planar and the two symmetry related phenyl rings are coplanar. However in the similar structure, 1,4-Bis(3-pyridylaminomethyl)benzene (Zhu et al., 2007), the dihedral angle between the pyridyl ring and the central benzene ring is 63.6 (2)°.

Related literature

For a related structure, see: Zhu et al. (2007). For bond-length data, see: Allen et al. (1987).

S2. Experimental

For the preparation of the title compound, a solution of the appropriate succinyl dichloride (10 mmol) in pyridine (0.5 ml) was added to a solution of 4-nitro-phenol (20 mmol) in dry acetonitrile (30 ml) and the mixture was heated under reflux for 5–6 h. The moisture was excluded by using a calcium chloride guard tube on the reflux condenser. On cooling, the precipitates were collected, dried and recrystallized from chloroform-acetonitrile to give the title compond. Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetone solution.

S3. Refinement

H atoms were positioned geometrically, with C—H = 0.93 and 0.97 Å for aromatic and methylene H, respectively, and constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are omitted for clarity.

Bis(4-nitrophenyl) succinate

Crystal data

C16H12N2O8	F(000) = 744
Mr = 360.28	Dx = 1.490 Mg m^−3
Monoclinic, C2/c	Melting point: 445 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 13.539 (13) Å	Cell parameters from 851 reflections
b = 9.049 (9) Å	θ = 3.1–26.3°
c = 14.662 (14) Å	µ = 0.12 mm^−1
β = 116.609 (15)°	T = 294 K
V = 1606 (3) Å^3	Prism, colorless
Z = 4	0.20 × 0.18 × 0.14 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer	1415 independent reflections
Radiation source: fine-focus sealed tube	698 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
ϕ and ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→14
Tmin = 0.976, Tmax = 0.983	k = −6→10
3797 measured reflections	l = −17→17

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.196	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0987P)^2 + 0.291P] where P = (Fo^2 + 2Fc^2)/3
1415 reflections	(Δ/σ)max = 0.001
118 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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
O1	−0.0763 (4)	−0.1228 (5)	0.3236 (4)	0.1213 (16)
O2	−0.1973 (3)	−0.0053 (4)	0.1964 (3)	0.1081 (14)
O3	0.0744 (2)	0.5257 (3)	0.4503 (2)	0.0595 (9)
O4	0.2214 (2)	0.4987 (3)	0.4210 (2)	0.0615 (9)
N1	−0.1159 (4)	−0.0091 (5)	0.2796 (4)	0.0771 (12)
C1	0.0807 (3)	0.2616 (4)	0.4553 (3)	0.0543 (11)
H1	0.1474	0.2637	0.5144	0.065*
C2	0.0313 (3)	0.1298 (4)	0.4138 (3)	0.0530 (11)
H2	0.0635	0.0408	0.4444	0.064*
C3	−0.0665 (3)	0.1317 (4)	0.3262 (3)	0.0505 (10)
C4	−0.1169 (3)	0.2599 (5)	0.2803 (3)	0.0553 (11)
H4	−0.1838	0.2582	0.2215	0.066*
C5	−0.0677 (3)	0.3909 (5)	0.3219 (3)	0.0523 (11)
H5	−0.1003	0.4800	0.2919	0.063*
C6	0.0305 (3)	0.3890 (4)	0.4087 (3)	0.0458 (10)
C7	0.1701 (3)	0.5718 (4)	0.4517 (3)	0.0426 (9)
C8	0.1953 (3)	0.7226 (4)	0.4931 (3)	0.0526 (11)
H8A	0.1934	0.7249	0.5585	0.063*
H8B	0.1383	0.7889	0.4474	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.116 (4)	0.071 (3)	0.144 (4)	−0.024 (2)	0.030 (3)	−0.024 (3)
O2	0.072 (3)	0.140 (4)	0.092 (3)	−0.050 (2)	0.019 (2)	−0.041 (2)
O3	0.0515 (18)	0.0563 (18)	0.078 (2)	−0.0078 (14)	0.0353 (16)	−0.0143 (14)
O4	0.0440 (17)	0.0658 (19)	0.072 (2)	−0.0064 (14)	0.0239 (16)	−0.0237 (14)
N1	0.054 (3)	0.091 (4)	0.084 (3)	−0.028 (3)	0.029 (3)	−0.025 (3)
C1	0.039 (2)	0.062 (3)	0.047 (3)	0.002 (2)	0.006 (2)	−0.004 (2)
C2	0.043 (2)	0.056 (3)	0.055 (3)	0.000 (2)	0.017 (2)	0.000 (2)
C3	0.035 (2)	0.065 (3)	0.054 (3)	−0.014 (2)	0.022 (2)	−0.013 (2)
C4	0.029 (2)	0.082 (3)	0.046 (2)	−0.003 (2)	0.0089 (19)	−0.001 (2)
C5	0.040 (2)	0.064 (3)	0.052 (3)	0.006 (2)	0.020 (2)	0.009 (2)
C6	0.036 (2)	0.051 (2)	0.052 (2)	−0.0056 (19)	0.022 (2)	−0.0077 (19)
C7	0.031 (2)	0.054 (2)	0.033 (2)	0.0016 (18)	0.0053 (17)	0.0022 (17)
C8	0.047 (2)	0.043 (2)	0.065 (3)	−0.0007 (18)	0.023 (2)	−0.0063 (19)

Geometric parameters (Å, º)

O1—N1	1.206 (5)	C2—H2	0.9300
O2—N1	1.224 (5)	C3—C4	1.362 (5)
O3—C7	1.352 (4)	C4—C5	1.362 (5)
O3—C6	1.389 (4)	C4—H4	0.9300
O4—C7	1.186 (4)	C5—C6	1.368 (5)
N1—C3	1.458 (5)	C5—H5	0.9300
C1—C6	1.357 (5)	C7—C8	1.470 (5)
C1—C2	1.369 (5)	C8—C8^i	1.488 (7)
C1—H1	0.9300	C8—H8A	0.9700
C2—C3	1.371 (6)	C8—H8B	0.9700
C7—O3—C6	120.1 (3)	C4—C5—C6	118.8 (4)
O1—N1—O2	122.9 (5)	C4—C5—H5	120.6
O1—N1—C3	119.6 (5)	C6—C5—H5	120.6
O2—N1—C3	117.5 (5)	C1—C6—C5	122.5 (4)
C6—C1—C2	118.7 (4)	C1—C6—O3	121.1 (4)
C6—C1—H1	120.6	C5—C6—O3	116.3 (4)
C2—C1—H1	120.6	O4—C7—O3	122.9 (3)
C1—C2—C3	118.7 (4)	O4—C7—C8	127.4 (3)
C1—C2—H2	120.6	O3—C7—C8	109.7 (3)
C3—C2—H2	120.6	C7—C8—C8^i	113.5 (4)
C4—C3—C2	122.2 (4)	C7—C8—H8A	108.9
C4—C3—N1	119.3 (4)	C8^i—C8—H8A	108.9
C2—C3—N1	118.4 (4)	C7—C8—H8B	108.9
C3—C4—C5	118.9 (4)	C8^i—C8—H8B	108.9
C3—C4—H4	120.5	H8A—C8—H8B	107.7
C5—C4—H4	120.5
C6—C1—C2—C3	0.6 (5)	C2—C1—C6—C5	0.1 (5)
C1—C2—C3—C4	−1.2 (6)	C2—C1—C6—O3	177.0 (3)
C1—C2—C3—N1	177.1 (3)	C4—C5—C6—C1	−0.2 (5)
O1—N1—C3—C4	−174.5 (4)	C4—C5—C6—O3	−177.3 (3)
O2—N1—C3—C4	5.2 (6)	C7—O3—C6—C1	69.0 (4)
O1—N1—C3—C2	7.1 (6)	C7—O3—C6—C5	−113.9 (4)
O2—N1—C3—C2	−173.1 (4)	C6—O3—C7—O4	−1.9 (5)
C2—C3—C4—C5	1.0 (5)	C6—O3—C7—C8	176.4 (3)
N1—C3—C4—C5	−177.2 (3)	O4—C7—C8—C8^i	−7.3 (7)
C3—C4—C5—C6	−0.3 (5)	O3—C7—C8—C8^i	174.5 (4)

Symmetry code: (i) −x+1/2, −y+3/2, −z+1.