o-Nitro­benzoic acid anhydride

The title compound, C₁₄H₈N₂O₇, is a symmetrically substituted acyclic anhydride. The nitro groups are twisted with respect to the benzene rings; these are almost coplanar, with a dihedral angle of 9.07 (9)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.048
• wR factor = 0.130
• Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N21

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

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

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Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.

o-Nitrobenzoic acid anhydride

Crystal data

C14H8N2O7	F(000) = 648
Mr = 316.22	Dx = 1.531 Mg m^−3
Monoclinic, P21/c	Melting point = 405–406 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.9365 (10) Å	Cell parameters from 85 reflections
b = 16.1757 (14) Å	θ = 4.7–12.5°
c = 11.0023 (8) Å	µ = 0.13 mm^−1
β = 103.798 (7)°	T = 296 K
V = 1371.7 (2) Å^3	Prism, colourless
Z = 4	0.60 × 0.44 × 0.28 mm

Data collection

Siemens P4 diffractometer	Rint = 0.029
Radiation source: fine-focus sealed tube, FN4	θmax = 30.0°, θmin = 2.3°
Graphite monochromator	h = −11→6
ω scans	k = −1→22
7531 measured reflections	l = −15→15
3994 independent reflections	3 standard reflections every 97 reflections
2935 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0542P)^2 + 0.2914P] where P = (Fo^2 + 2Fc^2)/3
3994 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.24894 (11)	0.58378 (6)	0.39785 (9)	0.0387 (2)
C2	0.09787 (16)	0.57999 (8)	0.30530 (12)	0.0364 (3)
O3	−0.00984 (15)	0.63229 (7)	0.28553 (12)	0.0589 (3)
C4	0.09360 (16)	0.50375 (8)	0.22881 (11)	0.0339 (3)
C5	0.23826 (18)	0.47882 (9)	0.18863 (14)	0.0416 (3)
H5A	0.3442	0.5050	0.2194	0.050*
C6	0.2260 (2)	0.41500 (10)	0.10265 (15)	0.0507 (4)
H6A	0.3237	0.3987	0.0760	0.061*
C7	0.0700 (2)	0.37575 (11)	0.05673 (15)	0.0562 (4)
H7A	0.0628	0.3334	−0.0014	0.067*
C8	−0.0761 (2)	0.39873 (11)	0.09618 (14)	0.0509 (4)
H8A	−0.1815	0.3721	0.0657	0.061*
C9	−0.06163 (17)	0.46206 (9)	0.18165 (12)	0.0392 (3)
N10	−0.21612 (17)	0.48223 (9)	0.22704 (15)	0.0550 (3)
O11	−0.1987 (2)	0.49045 (11)	0.33896 (14)	0.0780 (4)
O12	−0.35384 (18)	0.48700 (13)	0.14957 (18)	0.1003 (6)
C13	0.27554 (17)	0.64721 (9)	0.48530 (13)	0.0387 (3)
O14	0.16167 (14)	0.68366 (9)	0.51471 (13)	0.0676 (4)
C15	0.46336 (16)	0.66157 (8)	0.53712 (12)	0.0336 (3)
C16	0.59048 (17)	0.62448 (9)	0.48733 (13)	0.0408 (3)
H16A	0.5586	0.5858	0.4234	0.049*
C17	0.76400 (18)	0.64463 (10)	0.53228 (14)	0.0461 (3)
H17A	0.8476	0.6194	0.4983	0.055*
C18	0.81354 (18)	0.70195 (10)	0.62712 (14)	0.0451 (3)
H18A	0.9301	0.7155	0.6561	0.054*
C19	0.69033 (19)	0.73923 (9)	0.67909 (14)	0.0438 (3)
H19A	0.7229	0.7777	0.7432	0.053*
C20	0.51868 (17)	0.71829 (8)	0.63426 (12)	0.0358 (3)
N21	0.39428 (17)	0.75813 (9)	0.69675 (12)	0.0480 (3)
O22	0.3534 (2)	0.82906 (9)	0.66836 (16)	0.0834 (5)
O23	0.3474 (2)	0.71963 (11)	0.77679 (15)	0.0847 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0303 (5)	0.0401 (5)	0.0430 (5)	0.0023 (4)	0.0034 (4)	−0.0080 (4)
C2	0.0291 (6)	0.0368 (6)	0.0422 (6)	0.0002 (5)	0.0065 (5)	−0.0006 (5)
O3	0.0462 (6)	0.0478 (6)	0.0726 (8)	0.0153 (5)	−0.0057 (5)	−0.0088 (5)
C4	0.0310 (6)	0.0352 (6)	0.0343 (6)	−0.0002 (5)	0.0054 (5)	0.0016 (5)
C5	0.0341 (7)	0.0424 (7)	0.0491 (7)	0.0011 (5)	0.0116 (6)	0.0010 (6)
C6	0.0529 (9)	0.0531 (9)	0.0510 (8)	0.0088 (7)	0.0224 (7)	−0.0024 (7)
C7	0.0689 (11)	0.0547 (9)	0.0450 (8)	0.0006 (8)	0.0136 (8)	−0.0136 (7)
C8	0.0486 (8)	0.0530 (9)	0.0472 (8)	−0.0096 (7)	0.0037 (6)	−0.0101 (7)
C9	0.0330 (6)	0.0453 (7)	0.0383 (6)	−0.0024 (5)	0.0067 (5)	−0.0017 (6)
N10	0.0376 (7)	0.0602 (8)	0.0704 (9)	−0.0099 (6)	0.0192 (6)	−0.0084 (7)
O11	0.0770 (10)	0.0975 (11)	0.0725 (9)	−0.0078 (8)	0.0437 (8)	−0.0154 (8)
O12	0.0313 (7)	0.1512 (17)	0.1128 (13)	0.0003 (8)	0.0060 (7)	−0.0193 (12)
C13	0.0314 (6)	0.0418 (7)	0.0442 (7)	−0.0022 (5)	0.0116 (5)	−0.0086 (5)
O14	0.0324 (5)	0.0861 (9)	0.0857 (9)	−0.0021 (6)	0.0168 (5)	−0.0437 (7)
C15	0.0286 (6)	0.0354 (6)	0.0370 (6)	−0.0003 (5)	0.0083 (5)	−0.0018 (5)
C16	0.0334 (7)	0.0482 (8)	0.0415 (7)	0.0009 (6)	0.0103 (5)	−0.0070 (6)
C17	0.0317 (7)	0.0584 (9)	0.0504 (8)	0.0027 (6)	0.0141 (6)	−0.0017 (7)
C18	0.0312 (6)	0.0532 (8)	0.0494 (8)	−0.0077 (6)	0.0067 (6)	0.0047 (6)
C19	0.0409 (7)	0.0437 (7)	0.0451 (7)	−0.0088 (6)	0.0066 (6)	−0.0053 (6)
C20	0.0346 (6)	0.0347 (6)	0.0390 (6)	−0.0004 (5)	0.0105 (5)	−0.0020 (5)
N21	0.0430 (7)	0.0514 (7)	0.0496 (7)	0.0007 (6)	0.0109 (5)	−0.0156 (6)
O22	0.0912 (11)	0.0575 (8)	0.1053 (12)	0.0259 (8)	0.0313 (9)	−0.0118 (8)
O23	0.0953 (11)	0.0980 (11)	0.0798 (9)	0.0075 (9)	0.0583 (9)	0.0018 (9)

Geometric parameters (Å, º)

O1—C2	1.3768 (15)	N10—O12	1.218 (2)
O1—C13	1.3878 (16)	C13—O14	1.1868 (17)
C2—O3	1.1854 (17)	C13—C15	1.4818 (18)
C2—C4	1.4889 (18)	C15—C16	1.3933 (18)
C4—C5	1.3850 (19)	C15—C20	1.3976 (18)
C4—C9	1.3917 (18)	C16—C17	1.3866 (19)
C5—C6	1.388 (2)	C16—H16A	0.9300
C5—H5A	0.9300	C17—C18	1.381 (2)
C6—C7	1.376 (2)	C17—H17A	0.9300
C6—H6A	0.9300	C18—C19	1.383 (2)
C7—C8	1.382 (2)	C18—H18A	0.9300
C7—H7A	0.9300	C19—C20	1.3760 (19)
C8—C9	1.377 (2)	C19—H19A	0.9300
C8—H8A	0.9300	C20—N21	1.4786 (18)
C9—N10	1.4667 (19)	N21—O23	1.2075 (19)
N10—O11	1.213 (2)	N21—O22	1.213 (2)
C2—O1—C13	120.48 (10)	O14—C13—O1	123.81 (12)
O3—C2—O1	124.52 (13)	O14—C13—C15	125.36 (13)
O3—C2—C4	124.70 (12)	O1—C13—C15	110.82 (11)
O1—C2—C4	110.69 (10)	C16—C15—C20	117.29 (12)
C5—C4—C9	117.86 (12)	C16—C15—C13	122.51 (12)
C5—C4—C2	120.85 (12)	C20—C15—C13	120.06 (11)
C9—C4—C2	120.72 (12)	C17—C16—C15	120.61 (13)
C4—C5—C6	120.37 (14)	C17—C16—H16A	119.7
C4—C5—H5A	119.8	C15—C16—H16A	119.7
C6—C5—H5A	119.8	C18—C17—C16	120.46 (14)
C7—C6—C5	120.28 (14)	C18—C17—H17A	119.8
C7—C6—H6A	119.9	C16—C17—H17A	119.8
C5—C6—H6A	119.9	C17—C18—C19	120.20 (13)
C6—C7—C8	120.61 (15)	C17—C18—H18A	119.9
C6—C7—H7A	119.7	C19—C18—H18A	119.9
C8—C7—H7A	119.7	C20—C19—C18	118.79 (13)
C9—C8—C7	118.37 (15)	C20—C19—H19A	120.6
C9—C8—H8A	120.8	C18—C19—H19A	120.6
C7—C8—H8A	120.8	C19—C20—C15	122.63 (13)
C8—C9—C4	122.50 (14)	C19—C20—N21	116.10 (12)
C8—C9—N10	117.25 (13)	C15—C20—N21	121.26 (11)
C4—C9—N10	120.19 (12)	O23—N21—O22	124.44 (16)
O11—N10—O12	124.73 (16)	O23—N21—C20	118.06 (14)
O11—N10—C9	117.88 (14)	O22—N21—C20	117.39 (14)
O12—N10—C9	117.35 (15)
C13—O1—C2—O3	7.5 (2)	C2—O1—C13—O14	25.9 (2)
C13—O1—C2—C4	−175.96 (11)	C2—O1—C13—C15	−154.97 (12)
O3—C2—C4—C5	132.16 (16)	O14—C13—C15—C16	−171.34 (16)
O1—C2—C4—C5	−44.38 (16)	O1—C13—C15—C16	9.59 (19)
O3—C2—C4—C9	−39.0 (2)	O14—C13—C15—C20	4.3 (2)
O1—C2—C4—C9	144.42 (12)	O1—C13—C15—C20	−174.77 (11)
C9—C4—C5—C6	0.9 (2)	C20—C15—C16—C17	−0.9 (2)
C2—C4—C5—C6	−170.53 (13)	C13—C15—C16—C17	174.87 (14)
C4—C5—C6—C7	−0.1 (2)	C15—C16—C17—C18	−0.1 (2)
C5—C6—C7—C8	−0.5 (3)	C16—C17—C18—C19	0.7 (2)
C6—C7—C8—C9	0.4 (3)	C17—C18—C19—C20	−0.2 (2)
C7—C8—C9—C4	0.4 (2)	C18—C19—C20—C15	−0.8 (2)
C7—C8—C9—N10	−176.79 (15)	C18—C19—C20—N21	177.94 (13)
C5—C4—C9—C8	−1.0 (2)	C16—C15—C20—C19	1.4 (2)
C2—C4—C9—C8	170.41 (14)	C13—C15—C20—C19	−174.50 (13)
C5—C4—C9—N10	176.04 (13)	C16—C15—C20—N21	−177.34 (13)
C2—C4—C9—N10	−12.5 (2)	C13—C15—C20—N21	6.8 (2)
C8—C9—N10—O11	132.56 (17)	C19—C20—N21—O23	−97.94 (18)
C4—C9—N10—O11	−44.7 (2)	C15—C20—N21—O23	80.84 (19)
C8—C9—N10—O12	−45.2 (2)	C19—C20—N21—O22	78.32 (18)
C4—C9—N10—O12	137.53 (17)	C15—C20—N21—O22	−102.90 (17)