2-Hy­droxy­benzenaminium acetate

In the title molecular salt, C₆H₈NO⁺·C₂H₃O₂⁻, the cations and anions are linked by O—H...O and N—H...O hydrogen bonds, generating a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.038
• wR factor = 0.109
• Data-to-parameter ratio = 25.5

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         91 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

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

   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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2-Hydroxybenzenaminium acetate

Crystal data

C6H8NO^+·C2H3O2^−	F(000) = 360
Mr = 169.18	Dx = 1.322 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.9150 (2) Å	Cell parameters from 52927 reflections
b = 7.2523 (2) Å	θ = 3.3–33.0°
c = 11.9573 (3) Å	µ = 0.10 mm^−1
β = 98.558 (2)°	T = 100 K
V = 850.23 (4) Å^3	Prism, yellow
Z = 4	0.1 × 0.1 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 CCD diffractometer	2736 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.038
Absorption correction: integration (ABSORB; DeTitta, 1985)	θmax = 33.0°, θmin = 3.3°
Tmin = 0.966, Tmax = 0.991	h = −15→15
52913 measured reflections	k = −11→11
3105 independent reflections	l = −17→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0542P)^2 + 0.320P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3105 reflections	Δρmax = 0.49 e Å^−3
122 parameters	Δρmin = −0.27 e Å^−3
0 restraints

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.

Refinement. The hydrogen atoms of the NH₃ and hydroxyl groups were localized in the difference-Fourier map and refined with U_iso(H) set to 1.5U_eq(O) or 1.2U_eq(N). All the other hydrogen atoms were placed in calculated positions with C—H = 0.95 Å for aromatic CH and C—H = 0.96 Å for CH₃ and refined using a riding model with fixed isotropic displacement parameters [U_iso(H) = 1.2U_eq(C-aromatic) and U_iso(H) = 1.5U_eq(C-methyl)].

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

	x	y	z	Uiso*/Ueq
O1	0.12872 (6)	0.83288 (9)	0.65994 (5)	0.01629 (13)
H1	0.1381 (14)	0.928 (2)	0.6142 (12)	0.024*
O2	0.09592 (7)	0.29888 (8)	0.65411 (5)	0.01686 (13)
O3	0.15033 (7)	0.10731 (8)	0.52349 (5)	0.01664 (13)
N1	0.12133 (7)	0.56570 (9)	0.81635 (5)	0.01242 (13)
H1A	0.1133 (12)	0.4870 (19)	0.7543 (10)	0.015*
H1B	0.0461 (12)	0.6407 (18)	0.8160 (10)	0.015*
H1C	0.1280 (12)	0.4909 (18)	0.8806 (10)	0.015*
C3	0.35594 (9)	0.93249 (12)	0.74235 (7)	0.01774 (16)
H3	0.358215	1.025256	0.686567	0.021*
C5	0.46510 (9)	0.77468 (13)	0.90970 (8)	0.01994 (17)
H5	0.540747	0.760726	0.967953	0.024*
C4	0.46648 (9)	0.91021 (13)	0.82754 (8)	0.02042 (17)
H4	0.543738	0.988327	0.829677	0.025*
C2	0.24139 (8)	0.81883 (11)	0.73847 (6)	0.01328 (14)
C6	0.35205 (8)	0.65957 (12)	0.90596 (7)	0.01606 (15)
H6	0.350402	0.566114	0.961414	0.019*
C1	0.24197 (8)	0.68208 (10)	0.82091 (6)	0.01217 (14)
C8	0.13683 (8)	0.26870 (11)	0.56096 (6)	0.01288 (14)
C7	0.16938 (9)	0.42886 (12)	0.48900 (8)	0.01940 (16)
H7A	0.096016	0.443787	0.425025	0.029*
H7B	0.255531	0.405118	0.460661	0.029*
H7C	0.177717	0.541719	0.534587	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0172 (3)	0.0157 (3)	0.0153 (3)	−0.0014 (2)	0.0001 (2)	0.0046 (2)
O2	0.0220 (3)	0.0142 (3)	0.0157 (3)	−0.0024 (2)	0.0073 (2)	−0.0030 (2)
O3	0.0255 (3)	0.0124 (3)	0.0124 (2)	0.0019 (2)	0.0041 (2)	−0.00051 (19)
N1	0.0147 (3)	0.0109 (3)	0.0120 (3)	−0.0006 (2)	0.0030 (2)	0.0005 (2)
C3	0.0180 (3)	0.0161 (3)	0.0198 (4)	−0.0030 (3)	0.0053 (3)	0.0024 (3)
C5	0.0150 (3)	0.0222 (4)	0.0217 (4)	−0.0007 (3)	−0.0003 (3)	0.0001 (3)
C4	0.0154 (3)	0.0212 (4)	0.0248 (4)	−0.0040 (3)	0.0036 (3)	0.0000 (3)
C2	0.0149 (3)	0.0121 (3)	0.0131 (3)	0.0002 (2)	0.0032 (2)	0.0005 (2)
C6	0.0162 (3)	0.0160 (3)	0.0157 (3)	0.0013 (3)	0.0015 (3)	0.0011 (3)
C1	0.0133 (3)	0.0110 (3)	0.0126 (3)	−0.0001 (2)	0.0033 (2)	0.0000 (2)
C8	0.0128 (3)	0.0123 (3)	0.0135 (3)	0.0001 (2)	0.0019 (2)	0.0007 (2)
C7	0.0213 (4)	0.0154 (3)	0.0229 (4)	0.0008 (3)	0.0078 (3)	0.0063 (3)

Geometric parameters (Å, º)

O1—H1	0.892 (14)	C5—H5	0.9500
O1—C2	1.3520 (9)	C5—C4	1.3912 (13)
O2—C8	1.2600 (9)	C5—C6	1.3930 (12)
O3—C8	1.2675 (9)	C4—H4	0.9500
N1—H1A	0.930 (13)	C2—C1	1.3978 (11)
N1—H1B	0.922 (13)	C6—H6	0.9500
N1—H1C	0.935 (12)	C6—C1	1.3863 (11)
N1—C1	1.4583 (10)	C8—C7	1.5087 (11)
C3—H3	0.9500	C7—H7A	0.9800
C3—C4	1.3903 (12)	C7—H7B	0.9800
C3—C2	1.3985 (11)	C7—H7C	0.9800
C2—O1—H1	109.4 (9)	O1—C2—C1	117.36 (7)
H1A—N1—H1B	112.7 (11)	C1—C2—C3	118.48 (7)
H1A—N1—H1C	106.7 (11)	C5—C6—H6	120.2
H1B—N1—H1C	107.7 (10)	C1—C6—C5	119.66 (8)
C1—N1—H1A	110.9 (8)	C1—C6—H6	120.2
C1—N1—H1B	108.5 (8)	C2—C1—N1	117.84 (7)
C1—N1—H1C	110.3 (7)	C6—C1—N1	120.74 (7)
C4—C3—H3	119.9	C6—C1—C2	121.40 (7)
C4—C3—C2	120.24 (8)	O2—C8—O3	122.53 (7)
C2—C3—H3	119.9	O2—C8—C7	119.65 (7)
C4—C5—H5	120.2	O3—C8—C7	117.81 (7)
C4—C5—C6	119.55 (8)	C8—C7—H7A	109.5
C6—C5—H5	120.2	C8—C7—H7B	109.5
C3—C4—C5	120.66 (8)	C8—C7—H7C	109.5
C3—C4—H4	119.7	H7A—C7—H7B	109.5
C5—C4—H4	119.7	H7A—C7—H7C	109.5
O1—C2—C3	124.17 (7)	H7B—C7—H7C	109.5
O1—C2—C1—N1	−0.22 (10)	C4—C3—C2—O1	178.84 (8)
O1—C2—C1—C6	−178.85 (7)	C4—C3—C2—C1	−0.83 (12)
C3—C2—C1—N1	179.48 (7)	C4—C5—C6—C1	−0.39 (13)
C3—C2—C1—C6	0.85 (12)	C2—C3—C4—C5	0.22 (13)
C5—C6—C1—N1	−178.83 (7)	C6—C5—C4—C3	0.40 (14)
C5—C6—C1—C2	−0.24 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^i	0.894 (14)	1.709 (14)	2.6025 (9)	177.8 (16)
N1—H1A···O2	0.930 (13)	1.807 (13)	2.7251 (9)	168.7 (12)
N1—H1B···O2^ii	0.923 (12)	1.891 (12)	2.8019 (9)	168.8 (11)
N1—H1C···O3^iii	0.935 (12)	1.834 (12)	2.7531 (8)	167.2 (12)
C6—H6···O3^iii	0.95	2.55	3.2493 (11)	131

Symmetry codes: (i) x, y+1, z; (ii) −x, y+1/2, −z+3/2; (iii) x, −y+1/2, z+1/2.