2-(4-Hydro­xy­phenyl)­ethyl­ammonium picrate

In the crystal structure of the title salt, C₈H₁₂NO⁺·C₆H₂N₃O₇^-, the aromatic rings of the anions and cations are stacked alternately to form one-dimensional columns. These columns are linked to each other via hydrogen bonds, making a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 250 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.143
• Data-to-parameter ratio = 11.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           75.00
         From the CIF: _reflns_number_total               3050
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         3217
         Completeness (_total/calc)             94.81%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

Solid-state photoreactivities of some donor–acceptor crystals have been investigated by one of the authors (YI) (Ito et al., 1998). The structure of (I) has been determined to study the packing mode of the molecules in the crystal.

The title crystal, (I), consists of ammonium cations and phenolate anions (Fig. 1 and Table 1). The aromatic rings of the anions and cations are stacked alternatively along c to form one-dimensional columns (Fig. 2). The columns are linked with each other by N—H···O and O—H···O hydrogen bonds (Table 2), forming a three-dimensional network.

S2. Experimental

Crystals of (I) were grown by slow evaporation from an aqueous methanol solution of a mixture of 2-(4-hydroxyphenyl)ethylamine and picric acid (1:1).

S3. Refinement

The relatively low completeness of data collection (0.948 for θ_max = 75°) is a result of the blind region of the low-temperature apparatus. There is a rotational disorder of one of the nitro groups. It was assumed that nitro-O atoms are disordered over two sites, the O7/O8 and O9/O10 atoms, with 50% probabilities each. The hydroxyl and ammonium H atoms were located from difference syntheses and refined isotropically. The O—H bond length is 0.78 (3) Å, and the N—H lengths 0.89 (2)–0.93 (3) Å. The other H atoms were positioned geometrically and fixed with U_iso(H) = 1.2U_eq(parent atom).

Computing details

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures

	Fig. 1. The molecular structure of (I), with displacement ellipsoids at the 50% probability level. The disordered O9/O10 atoms bonded to N14 have been omitted for clarity.
	Fig. 2. The projection of the crystal structure of (I) along c.

(I)

Crystal data

C8H12NO^+·C6H2N3O7^−	Z = 2
Mr = 366.29	F(000) = 380
Triclinic, P1	Dx = 1.556 Mg m^−3
a = 8.9692 (6) Å	Cu Kα radiation, λ = 1.5418 Å
b = 12.312 (1) Å	Cell parameters from 25 reflections
c = 7.3832 (6) Å	θ = 25.4–29.6°
α = 104.391 (6)°	µ = 1.13 mm^−1
β = 96.502 (6)°	T = 250 K
γ = 83.654 (6)°	Plate, yellow
V = 781.8 (1) Å^3	0.5 × 0.4 × 0.2 mm

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.047
θ–2θ scans	θmax = 75.0°, θmin = 2.5°
Absorption correction: integration (Coppens et al., 1965)	h = −11→11
Tmin = 0.626, Tmax = 0.809	k = −15→15
3422 measured reflections	l = −9→0
3050 independent reflections	3 standard reflections every 150 reflections
2939 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0858P)^2 + 0.2511P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.049	(Δ/σ)max = 0.001
wR(F^2) = 0.143	Δρmax = 0.34 e Å^−3
S = 1.08	Δρmin = −0.24 e Å^−3
3050 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
270 parameters	Extinction coefficient: 0.020 (2)
H atoms treated by a mixture of independent and constrained refinement

Special details

Refinement. Refinement was based on F² against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F², and conventional R-factor (R) was calculated on F, with F set to zero for negative F². The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.9168 (1)	1.3109 (1)	0.5128 (2)	0.0544 (4)
O2	0.3729 (1)	0.89420 (9)	0.2564 (2)	0.0409 (3)
O3	0.6149 (2)	0.7937 (1)	0.0780 (2)	0.0586 (4)
O4	0.6160 (2)	0.6138 (1)	−0.0171 (3)	0.0743 (5)
O5	0.1662 (2)	0.4609 (1)	−0.3155 (2)	0.0674 (4)
O6	−0.0469 (2)	0.5304 (1)	−0.2084 (2)	0.0627 (4)
O7	−0.0798 (9)	0.895 (1)	0.195 (2)	0.077 (3)	0.50
O8	0.0967 (3)	1.0013 (2)	0.2337 (7)	0.077 (1)	0.50
O9	−0.095 (1)	0.9054 (10)	0.159 (1)	0.068 (2)	0.50
O10	0.0857 (4)	0.9643 (3)	0.3591 (6)	0.074 (1)	0.50
N11	0.3180 (2)	1.0848 (1)	0.5540 (2)	0.0380 (3)
N12	0.5501 (2)	0.7071 (1)	0.0343 (2)	0.0443 (4)
N13	0.0895 (2)	0.5334 (1)	−0.2113 (2)	0.0473 (4)
N14	0.0451 (2)	0.9035 (1)	0.2023 (2)	0.0535 (4)
C15	0.5876 (2)	1.1617 (1)	0.3102 (2)	0.0423 (4)
C16	0.7369 (2)	1.1865 (1)	0.3571 (2)	0.0420 (4)
C17	0.7689 (2)	1.2892 (1)	0.4755 (2)	0.0398 (4)
C18	0.6534 (2)	1.3660 (1)	0.5497 (2)	0.0427 (4)
C19	0.5052 (2)	1.3396 (1)	0.5029 (3)	0.0446 (4)
C20	0.4701 (2)	1.2373 (1)	0.3827 (2)	0.0415 (4)
C21	0.3076 (2)	1.2105 (2)	0.3360 (3)	0.0512 (4)
C22	0.2384 (2)	1.1864 (1)	0.4982 (3)	0.0437 (4)
C23	0.3080 (2)	0.8150 (1)	0.1459 (2)	0.0348 (3)
C24	0.3867 (2)	0.7152 (1)	0.0351 (2)	0.0359 (3)
C25	0.3173 (2)	0.6250 (1)	−0.0759 (2)	0.0390 (4)
C26	0.1617 (2)	0.6270 (1)	−0.0888 (2)	0.0393 (4)
C27	0.0751 (2)	0.7186 (1)	0.0055 (2)	0.0389 (4)
C28	0.1455 (2)	0.8096 (1)	0.1154 (2)	0.0375 (4)
H1	0.914 (4)	1.371 (3)	0.579 (5)	0.1052 (1)*
H11A	0.410 (3)	1.099 (2)	0.608 (3)	0.06100 (8)*
H11B	0.320 (2)	1.025 (2)	0.454 (3)	0.04512 (6)*
H11C	0.263 (2)	1.069 (2)	0.642 (3)	0.04951 (7)*
H15	0.5658	1.0919	0.2271	0.0507*
H16	0.8162	1.1333	0.3082	0.0503*
H18	0.6755	1.4361	0.6318	0.0512*
H19	0.4262	1.3922	0.5539	0.0535*
H21A	0.2506	1.2730	0.3008	0.0613*
H21B	0.3028	1.1463	0.2336	0.0613*
H22A	0.2453	1.2495	0.6024	0.0525*
H22B	0.1356	1.1738	0.4617	0.0525*
H25	0.3753	0.5616	−0.1434	0.0467*
H27	−0.0316	0.7191	−0.0052	0.0466*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0380 (7)	0.0483 (8)	0.0704 (9)	−0.0052 (5)	0.0008 (6)	0.0034 (7)
O2	0.0396 (6)	0.0350 (6)	0.0417 (6)	−0.0063 (4)	0.0030 (4)	−0.0037 (5)
O3	0.0447 (7)	0.0721 (9)	0.0493 (7)	−0.0193 (6)	0.0102 (5)	−0.0124 (6)
O4	0.0477 (8)	0.0597 (9)	0.110 (1)	0.0138 (7)	0.0133 (8)	0.0156 (9)
O5	0.0649 (9)	0.0429 (7)	0.0745 (10)	−0.0019 (6)	0.0057 (7)	−0.0220 (7)
O6	0.0534 (8)	0.0525 (8)	0.0719 (10)	−0.0179 (6)	0.0052 (7)	−0.0105 (7)
O7	0.036 (3)	0.071 (4)	0.116 (6)	−0.006 (3)	0.042 (4)	−0.010 (4)
O8	0.044 (2)	0.034 (1)	0.132 (3)	−0.001 (1)	0.002 (2)	−0.015 (2)
O9	0.044 (3)	0.059 (3)	0.076 (3)	0.003 (2)	−0.008 (2)	−0.023 (3)
O10	0.050 (2)	0.062 (2)	0.078 (2)	0.002 (1)	0.001 (2)	−0.037 (2)
N11	0.0354 (7)	0.0309 (7)	0.0425 (7)	−0.0012 (5)	0.0061 (6)	−0.0013 (6)
N12	0.0394 (7)	0.0531 (9)	0.0366 (7)	0.0000 (6)	0.0041 (5)	0.0051 (6)
N13	0.0507 (9)	0.0353 (7)	0.0492 (8)	−0.0074 (6)	0.0013 (6)	−0.0029 (6)
N14	0.0402 (9)	0.0437 (8)	0.0605 (10)	−0.0001 (6)	0.0005 (7)	−0.0144 (7)
C15	0.0501 (9)	0.0327 (8)	0.0428 (9)	−0.0073 (7)	−0.0002 (7)	0.0065 (6)
C16	0.0461 (9)	0.0334 (8)	0.0448 (9)	0.0012 (6)	0.0052 (7)	0.0075 (7)
C17	0.0386 (8)	0.0361 (8)	0.0442 (9)	−0.0037 (6)	0.0007 (6)	0.0099 (7)
C18	0.0464 (9)	0.0325 (8)	0.0460 (9)	−0.0040 (6)	0.0031 (7)	0.0036 (6)
C19	0.0429 (9)	0.0389 (9)	0.0504 (9)	0.0019 (7)	0.0073 (7)	0.0085 (7)
C20	0.0415 (9)	0.0405 (8)	0.0441 (9)	−0.0055 (7)	−0.0001 (7)	0.0141 (7)
C21	0.0436 (9)	0.055 (1)	0.057 (1)	−0.0097 (8)	−0.0076 (8)	0.0193 (9)
C22	0.0347 (8)	0.0347 (8)	0.0570 (10)	0.0014 (6)	0.0044 (7)	0.0037 (7)
C23	0.0395 (8)	0.0318 (7)	0.0317 (7)	−0.0049 (6)	0.0037 (6)	0.0037 (6)
C24	0.0372 (8)	0.0356 (8)	0.0327 (7)	−0.0022 (6)	0.0038 (6)	0.0044 (6)
C25	0.0442 (9)	0.0327 (8)	0.0359 (8)	0.0005 (6)	0.0051 (6)	0.0013 (6)
C26	0.0460 (9)	0.0308 (8)	0.0373 (8)	−0.0074 (6)	0.0030 (6)	−0.0005 (6)
C27	0.0386 (8)	0.0378 (8)	0.0379 (8)	−0.0072 (6)	0.0047 (6)	0.0023 (6)
C28	0.0390 (8)	0.0323 (8)	0.0365 (8)	−0.0023 (6)	0.0056 (6)	−0.0013 (6)

Geometric parameters (Å, º)

O1—C17	1.366 (2)	C16—C17	1.386 (2)
O1—H1	0.78 (3)	C16—H16	0.950
O2—C23	1.256 (2)	C17—C18	1.386 (2)
O3—N12	1.226 (2)	C18—C19	1.388 (3)
O4—N12	1.223 (2)	C18—H18	0.950
O5—N13	1.227 (2)	C19—C20	1.393 (2)
O6—N13	1.231 (2)	C19—H19	0.950
O7—N14	1.131 (8)	C20—C21	1.513 (3)
O8—N14	1.296 (4)	C21—C22	1.514 (3)
O9—N14	1.259 (9)	C21—H21A	0.950
O10—N14	1.252 (4)	C21—H21B	0.950
N11—C22	1.495 (2)	C22—H22A	0.950
N11—H11A	0.89 (2)	C22—H22B	0.950
N11—H11B	0.90 (2)	C23—C24	1.455 (2)
N11—H11C	0.93 (3)	C23—C28	1.456 (2)
N12—C24	1.458 (2)	C24—C25	1.371 (2)
N13—C26	1.442 (2)	C25—C26	1.386 (2)
N14—C28	1.445 (2)	C25—H25	0.950
C15—C16	1.392 (3)	C26—C27	1.378 (2)
C15—C20	1.388 (2)	C27—C28	1.379 (2)
C15—H15	0.950	C27—H27	0.950
C17—O1—H1	103 (3)	C15—C20—C19	118.2 (2)
C22—N11—H11A	110 (2)	C15—C20—C21	121.7 (1)
C22—N11—H11B	110 (1)	C19—C20—C21	120.1 (1)
C22—N11—H11C	107 (1)	C20—C21—C22	113.3 (2)
H11A—N11—H11B	112 (2)	C20—C21—H21A	108.5
H11A—N11—H11C	108 (2)	C20—C21—H21B	108.5
H11B—N11—H11C	108 (2)	C22—C21—H21A	108.5
O3—N12—O4	122.8 (2)	C22—C21—H21B	108.5
O3—N12—C24	118.9 (1)	H21A—C21—H21B	109.5
O4—N12—C24	118.2 (1)	N11—C22—C21	111.2 (1)
O5—N13—O6	122.8 (1)	N11—C22—H22A	109.0
O5—N13—C26	118.6 (2)	N11—C22—H22B	109.0
O6—N13—C26	118.6 (1)	C21—C22—H22A	109.0
O7—N14—O8	121.1 (6)	C21—C22—H22B	109.0
O7—N14—C28	120.4 (6)	H22A—C22—H22B	109.5
O8—N14—C28	115.1 (2)	O2—C23—C24	124.0 (1)
O9—N14—O10	115.6 (5)	O2—C23—C28	124.7 (1)
O9—N14—C28	121.0 (5)	C24—C23—C28	111.3 (1)
O10—N14—C28	119.5 (2)	N12—C24—C23	120.3 (1)
C16—C15—C20	121.2 (1)	N12—C24—C25	115.3 (1)
C16—C15—H15	119.4	C23—C24—C25	124.4 (1)
C20—C15—H15	119.4	C24—C25—C26	119.4 (1)
C15—C16—C17	119.5 (1)	C24—C25—H25	120.3
C15—C16—H16	120.2	C26—C25—H25	120.3
C17—C16—H16	120.2	N13—C26—C25	118.9 (1)
O1—C17—C16	117.3 (1)	N13—C26—C27	119.6 (1)
O1—C17—C18	122.4 (1)	C25—C26—C27	121.4 (1)
C16—C17—C18	120.3 (2)	C26—C27—C28	119.0 (1)
C17—C18—C19	119.4 (1)	C26—C27—H27	120.5
C17—C18—H18	120.3	C28—C27—H27	120.5
C19—C18—H18	120.3	N14—C28—C23	120.6 (1)
C18—C19—C20	121.3 (1)	N14—C28—C27	114.9 (1)
C18—C19—H19	119.3	C23—C28—C27	124.5 (1)
C20—C19—H19	119.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5^i	0.78 (3)	2.59 (4)	3.022 (2)	117 (2)
O1—H1···O6^i	0.78 (3)	2.22 (3)	2.988 (2)	168 (3)
N11—H11B···O2	0.90 (2)	1.94 (2)	2.829 (2)	167 (2)
N11—H11A···O2^ii	0.89 (2)	2.08 (2)	2.969 (2)	170 (2)
N11—H11A···O3^ii	0.89 (2)	2.39 (2)	2.791 (2)	108 (2)
N11—H11C···O7^iii	0.93 (3)	2.09 (2)	2.93 (1)	151 (2)
N11—H11B···O8	0.90 (2)	2.42 (2)	2.961 (4)	118 (2)
N11—H11C···O9^iii	0.93 (3)	2.16 (3)	3.05 (1)	158 (2)
N11—H11B···O10	0.90 (2)	2.28 (2)	2.748 (4)	112 (2)

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