3-Nitro­benzo­nitrile

The crystal structure of 3-nitrobenzonitrile, C₇H₄N₂O₂, was elucidated by low-temperature single-crystal X-ray diffraction. The compound crystallizes in the Sohncke space group P2₁ and features two mol­ecules in the unit cell. Aromatic π–π stacking leads to stacks of mol­ecules in the [100] direction. The absolute structure was established from anomalous dispersion.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.024
• wR factor = 0.069
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       6.44 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report

Alert level G
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00005 Ang.
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing ..............    0.00009 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO 1.171.42.92a (Rigaku OD, 2023); cell refinement: CrysAlis PRO 1.171.42.92a (Rigaku OD, 2023); data reduction: CrysAlis PRO 1.171.42.92a (Rigaku OD, 2023); program(s) used to solve structure: olex2.solve (Dolomanov et al., 2009); program(s) used to refine structure: SHELXL2019/3 (Sheldrick, 2015); molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

3-Nitrobenzonitrile

Crystal data

C7H4N2O2	F(000) = 152
Mr = 148.12	Dx = 1.479 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 3.73339 (4) Å	Cell parameters from 9014 reflections
b = 6.97307 (5) Å	θ = 3.5–75.7°
c = 12.87327 (9) Å	µ = 0.95 mm^−1
β = 97.1579 (8)°	T = 100 K
V = 332.52 (1) Å^3	Needle, colourless
Z = 2	0.28 × 0.06 × 0.04 mm

Data collection

XtaLAB Synergy-S, Dualflex, Eiger2 R CdTe 1M diffractometer	1360 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	1353 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.025
Detector resolution: 13.3333 pixels mm^-1	θmax = 75.9°, θmin = 3.5°
ω scans	h = −4→4
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2023)	k = −8→8
Tmin = 0.565, Tmax = 1.000	l = −16→16
10190 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.024	w = 1/[σ^2(Fo^2) + (0.0472P)^2 + 0.0377P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.069	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.17 e Å^−3
1360 reflections	Δρmin = −0.17 e Å^−3
116 parameters	Absolute structure: Flack x determined using 611 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.02 (5)
Primary atom site location: iterative

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	0.2952 (4)	0.11413 (19)	0.94632 (9)	0.0316 (3)
O2	0.5449 (3)	0.03136 (17)	0.81028 (9)	0.0294 (3)
N1	0.2525 (4)	0.5665 (2)	0.45848 (11)	0.0323 (4)
N2	0.3724 (3)	0.14375 (19)	0.85792 (10)	0.0199 (3)
C1	0.1823 (4)	0.5195 (2)	0.65436 (11)	0.0192 (3)
C2	0.2895 (4)	0.3452 (2)	0.70086 (12)	0.0179 (3)
C3	0.2551 (4)	0.3250 (2)	0.80620 (11)	0.0171 (3)
C4	0.1192 (4)	0.4678 (2)	0.86529 (12)	0.0195 (3)
C5	0.0164 (4)	0.6403 (2)	0.81697 (12)	0.0215 (3)
C6	0.0461 (4)	0.6674 (2)	0.71128 (13)	0.0218 (3)
C7	0.2185 (4)	0.5471 (3)	0.54475 (12)	0.0236 (3)
H2	0.387 (6)	0.249 (4)	0.6661 (17)	0.031 (6)*
H4	0.108 (5)	0.445 (3)	0.9361 (16)	0.018 (5)*
H6	−0.009 (5)	0.790 (4)	0.6782 (15)	0.024 (5)*
H5	−0.071 (6)	0.738 (4)	0.8528 (17)	0.028 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0389 (7)	0.0334 (7)	0.0230 (5)	0.0024 (5)	0.0053 (5)	0.0092 (5)
O2	0.0321 (6)	0.0201 (6)	0.0368 (6)	0.0076 (5)	0.0073 (5)	0.0018 (5)
N1	0.0338 (8)	0.0387 (9)	0.0252 (6)	−0.0019 (6)	0.0064 (6)	0.0066 (6)
N2	0.0181 (6)	0.0192 (6)	0.0220 (6)	−0.0006 (5)	0.0014 (4)	0.0019 (5)
C1	0.0167 (6)	0.0217 (8)	0.0192 (6)	−0.0029 (5)	0.0016 (5)	0.0008 (6)
C2	0.0151 (7)	0.0184 (7)	0.0206 (6)	−0.0003 (5)	0.0034 (5)	−0.0018 (6)
C3	0.0148 (6)	0.0165 (7)	0.0199 (6)	−0.0017 (5)	0.0018 (5)	0.0006 (5)
C4	0.0165 (7)	0.0231 (7)	0.0190 (7)	−0.0010 (6)	0.0021 (5)	−0.0023 (6)
C5	0.0183 (7)	0.0202 (7)	0.0258 (7)	0.0016 (6)	0.0020 (5)	−0.0070 (6)
C6	0.0181 (7)	0.0190 (8)	0.0275 (7)	0.0005 (6)	−0.0004 (5)	0.0013 (6)
C7	0.0214 (7)	0.0246 (7)	0.0247 (7)	−0.0022 (6)	0.0027 (6)	0.0029 (6)

Geometric parameters (Å, º)

O1—N2	1.2258 (17)	C2—H2	0.91 (3)
O2—N2	1.2262 (18)	C3—C4	1.387 (2)
N1—C7	1.141 (2)	C4—C5	1.386 (2)
N2—C3	1.4697 (19)	C4—H4	0.93 (2)
C1—C2	1.392 (2)	C5—C6	1.392 (2)
C1—C6	1.397 (2)	C5—H5	0.91 (2)
C1—C7	1.447 (2)	C6—H6	0.96 (2)
C2—C3	1.3851 (19)
O1—N2—O2	123.75 (13)	C4—C3—N2	118.53 (12)
O1—N2—C3	118.31 (12)	C3—C4—H4	118.7 (12)
O2—N2—C3	117.93 (12)	C5—C4—C3	118.46 (13)
C2—C1—C6	121.55 (14)	C5—C4—H4	122.8 (12)
C2—C1—C7	118.61 (14)	C4—C5—C6	120.34 (14)
C6—C1—C7	119.84 (14)	C4—C5—H5	121.5 (14)
C1—C2—H2	123.1 (14)	C6—C5—H5	118.1 (14)
C3—C2—C1	116.93 (13)	C1—C6—H6	119.6 (12)
C3—C2—H2	119.9 (14)	C5—C6—C1	119.42 (14)
C2—C3—N2	118.16 (12)	C5—C6—H6	120.9 (12)
C2—C3—C4	123.30 (13)	N1—C7—C1	178.69 (17)
O1—N2—C3—C2	−169.59 (13)	C2—C1—C6—C5	0.0 (2)
O1—N2—C3—C4	11.0 (2)	C2—C3—C4—C5	−0.8 (2)
O2—N2—C3—C2	11.01 (19)	C3—C4—C5—C6	0.7 (2)
O2—N2—C3—C4	−168.36 (13)	C4—C5—C6—C1	−0.3 (2)
N2—C3—C4—C5	178.55 (12)	C6—C1—C2—C3	0.0 (2)
C1—C2—C3—N2	−178.92 (13)	C7—C1—C2—C3	179.18 (13)
C1—C2—C3—C4	0.4 (2)	C7—C1—C6—C5	−179.21 (13)