m-Cyano­phenol

m-Cyano­phenol, NC—C₆H₄—OH or C₇H₅NO, crystallizes as chains of mol­ecules held together by O—H...NC hydrogen bonds, with an O...N distance of 2.847 (2) Å.

Key indicators

• Single-crystal X-ray study
• T = 174 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.107
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C7      ..       6.04 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C3     -   C7     ...       1.45 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   2 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: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

m-Cyanophenol

Crystal data

C7H5NO	Z = 2
Mr = 119.12	F(000) = 124
Triclinic, P1	Dx = 1.286 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.828 (2) Å	Cell parameters from 2621 reflections
b = 7.197 (3) Å	θ = 2.4–27.4°
c = 7.384 (3) Å	µ = 0.09 mm^−1
α = 70.22 (1)°	T = 174 K
β = 74.28 (1)°	Elongated prism, colorless
γ = 65.70 (1)°	0.50 × 0.40 × 0.35 mm
V = 307.5 (2) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	1172 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 27.0°, θmin = 3.0°
ω scans	h = −8→8
3440 measured reflections	k = −9→9
1329 independent reflections	l = −9→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: constr
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.052P)^2 + 0.044P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.010
1329 reflections	Δρmax = 0.23 e Å^−3
87 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.12 (2)

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

	x	y	z	Uiso*/Ueq
C1	0.28353 (17)	0.53033 (16)	0.27995 (15)	0.0306 (3)
C2	0.28883 (16)	0.40026 (16)	0.46863 (14)	0.0306 (3)
H2	0.3216	0.4366	0.5664	0.037*
C3	0.24526 (16)	0.21581 (16)	0.51161 (15)	0.0306 (3)
C4	0.19854 (19)	0.15803 (18)	0.37015 (17)	0.0368 (3)
H4	0.1700	0.0313	0.4014	0.044*
C5	0.1948 (2)	0.28971 (19)	0.18331 (17)	0.0398 (3)
H5	0.1630	0.2529	0.0854	0.048*
C6	0.23679 (18)	0.47466 (18)	0.13712 (15)	0.0350 (3)
H6	0.2338	0.5634	0.0083	0.042*
C7	0.24849 (17)	0.08155 (17)	0.70798 (16)	0.0359 (3)
N8	0.25062 (18)	−0.02469 (16)	0.86373 (15)	0.0477 (3)
O9	0.32617 (15)	0.71001 (13)	0.24286 (12)	0.0436 (3)
H9	0.306 (3)	0.789 (3)	0.114 (3)	0.075 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0331 (5)	0.0268 (5)	0.0268 (5)	−0.0093 (4)	−0.0059 (4)	−0.0015 (4)
C2	0.0344 (5)	0.0303 (5)	0.0244 (5)	−0.0105 (4)	−0.0067 (4)	−0.0034 (4)
C3	0.0283 (5)	0.0273 (5)	0.0273 (5)	−0.0065 (4)	−0.0026 (4)	−0.0018 (4)
C4	0.0399 (6)	0.0313 (6)	0.0397 (6)	−0.0150 (5)	−0.0042 (5)	−0.0081 (5)
C5	0.0456 (7)	0.0437 (7)	0.0350 (6)	−0.0158 (5)	−0.0098 (5)	−0.0132 (5)
C6	0.0392 (6)	0.0363 (6)	0.0238 (5)	−0.0103 (5)	−0.0086 (4)	−0.0018 (4)
C7	0.0358 (6)	0.0281 (5)	0.0340 (6)	−0.0092 (4)	−0.0014 (4)	−0.0017 (5)
N8	0.0539 (7)	0.0365 (6)	0.0357 (6)	−0.0138 (5)	−0.0024 (4)	0.0051 (4)
O9	0.0679 (6)	0.0332 (5)	0.0323 (5)	−0.0264 (4)	−0.0136 (4)	0.0037 (3)

Geometric parameters (Å, º)

C1—O9	1.3635 (14)	C4—C5	1.3843 (17)
C1—C2	1.3911 (15)	C4—H4	0.9500
C1—C6	1.3958 (16)	C5—C6	1.3872 (17)
C2—C3	1.3929 (15)	C5—H5	0.9500
C2—H2	0.9500	C6—H6	0.9500
C3—C4	1.3962 (16)	C7—N8	1.1455 (15)
C3—C7	1.4451 (15)	O9—H9	0.94 (2)
O9—C1—C2	117.33 (10)	C5—C4—H4	120.8
O9—C1—C6	122.55 (10)	C3—C4—H4	120.8
C2—C1—C6	120.12 (11)	C4—C5—C6	120.91 (10)
C1—C2—C3	118.79 (10)	C4—C5—H5	119.5
C1—C2—H2	120.6	C6—C5—H5	119.5
C3—C2—H2	120.6	C5—C6—C1	120.02 (10)
C2—C3—C4	121.70 (10)	C5—C6—H6	120.0
C2—C3—C7	118.89 (10)	C1—C6—H6	120.0
C4—C3—C7	119.41 (10)	N8—C7—C3	179.86 (15)
C5—C4—C3	118.46 (11)	C1—O9—H9	109.0 (11)