N-(2-Hy­droxy­benz­yl)adamantan-1-aminium chloride

Rong, T.

doi:10.1107/S1600536811020794

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1602

doi:10.1107/S1600536811020794

Open

access

N-(2-Hydroxybenzyl)adamantan-1-aminium chloride

Tao Rong ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: rongtao198806@163.com

(Received 23 April 2011; accepted 30 May 2011; online 11 June 2011)

The asymmetric unit of the title compound, C₁₇H₂₄NO⁺·Cl⁻, consists of a discrete N-(2-hydroxybenzyl)adamantan-1-aminium cation and a Cl⁻ anion. Intermolecular N—H⋯Cl and O—H⋯Cl hydrogen bonds occurring between the organic cation and the Cl⁻ anion generate a layered structure.

Related literature

For general background to ferroelectric organic frameworks, see: Ye et al. (2006 , 2009 ); Fu et al. (2007 ); Zhao et al. (2008 ). For phase transitions of ferroelectric materials, see: Zhang et al. (2008 ).

Experimental

Crystal data

C₁₇H₂₄NO⁺·Cl⁻
M_r = 293.82
Monoclinic, P 2₁ /c
a = 12.262 (3) Å
b = 10.202 (2) Å
c = 12.845 (3) Å
β = 98.43 (3)°
V = 1589.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.954, T_max = 0.954
15541 measured reflections
3632 independent reflections
2249 reflections with I > 2σ(I)
R_int = 0.088

Refinement

R[F² > 2σ(F²)] = 0.074
wR(F²) = 0.217
S = 1.06
3632 reflections
204 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1ⁱ	0.90	2.58	3.260 (2)	133
N1—H1C⋯Cl1ⁱⁱ	0.90	2.38	3.118 (2)	139
O1—H1B⋯Cl1ⁱⁱⁱ	0.85	2.27	3.049 (2)	152
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x, -y+2, -z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020794/kp2325sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020794/kp2325Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020794/kp2325Isup3.cml

checkCIF report

Comment top

The study of ferroelectric materials has received much attention. Some materials have predominantly dielectric-ferroelectric performances.The title compound was studied as part of our work to obtain potential ferroelectric phase-change materials (Ye et al., 2006; Fu et al., 2007; Zhao et al. 2008; Zhang et al., 2008; Ye et al., 2009). Unluckily, the compound has no dielectric anomalies in the temperature range 93–453 K, suggesting that it might be only a paraelectric. The title compound (Fig. 1), consists of protonated N-(2-hydroxybenzyl)–1–adamantylammonium cation and Cl^- anion. In the crystal structure, the N—H···Cl and O—H···Cl hydrogen bonds between the organic cations and the Cl^- anions stabilise crystal packing. In the cation, the groups NH₂⁺ and OH are proton donors to Cl^- forming hydrogen bonds (Table 1, Fig. 2).

Related literature top

For general background to ferroelectric organic frameworks, see: Ye et al. (2006, 2009); Fu et al. (2007); Zhao et al. (2008). For phase transitions of ferroelectric materials, see: Zhang et al. (2008).

Experimental top

KOH (20 mmol)and salicylaldehyde (20 mmol) were added into a solution of amantadine hydrochloride (20 mmol) in ethanol. Then a little of anhydrous magnesium sulfate was added into the mixture, after 6 h the yellow precipitate came out. The yellow solid of amantadine shrink Yang Schiff was obtained by filtration, collection and drying.

NaBH₄(3.78 g) was added into a solution of amantadine shrink Yang Schiff (25 mmol) in anhydrous methanol(120 mL). After 5 h reaction, a white solid 2-(adamantane-1-aminomethyl)phenol was obtained by reduced pressure distillation, extraction and drying.

A solution of hydrochloric acid (10 mmol) was added to a solution of 2-(adamantane-1-aminomethyl)phenol (10 mmol) in ethanol (20 mL). Crystals suitable for structure determination were grown by slow evaporation of the mixture at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atomic numbering scheme.
	Fig. 2. A view of the packing of the title compound, showing hydrogen-bonded helices along the axis b.

N-(2-Hydroxybenzyl)adamantan-1-aminium chloride top

Crystal data top

C₁₇H₂₄NO⁺·Cl⁻	Z = 4
M_r = 293.82	F(000) = 632
Monoclinic, P2₁/c	D_x = 1.228 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.262 (3) Å	θ = 3.0–27.5°
b = 10.202 (2) Å	µ = 0.24 mm⁻¹
c = 12.845 (3) Å	T = 293 K
β = 98.43 (3)°	Prism, colourless
V = 1589.5 (6) Å³	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	3632 independent reflections
Radiation source: fine-focus sealed tube	2249 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.088
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
CCD_Profile_fitting scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
T_min = 0.954, T_max = 0.954	l = −16→16
15541 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.217	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0986P)² + 0.3244P] where P = (F_o² + 2F_c²)/3
3632 reflections	(Δ/σ)_max < 0.001
204 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₁₇H₂₄NO⁺·Cl⁻	V = 1589.5 (6) Å³
M_r = 293.82	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.262 (3) Å	µ = 0.24 mm⁻¹
b = 10.202 (2) Å	T = 293 K
c = 12.845 (3) Å	0.20 × 0.20 × 0.20 mm
β = 98.43 (3)°

Data collection top

Rigaku SCXmini diffractometer	3632 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2249 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.954	R_int = 0.088
15541 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	0 restraints
wR(F²) = 0.217	H-atom parameters constrained
S = 1.06	Δρ_max = 0.35 e Å⁻³
3632 reflections	Δρ_min = −0.48 e Å⁻³
204 parameters

Special details top

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.04801 (8)	0.97166 (8)	0.33131 (6)	0.0627 (3)
O1	−0.01490 (19)	0.8664 (2)	−0.12965 (18)	0.0641 (7)
H1B	−0.0321	0.8850	−0.1947	0.15 (2)*
N1	0.07621 (18)	0.6830 (2)	0.05578 (17)	0.0391 (5)
H1C	0.0596	0.6471	0.1155	0.047*
H1A	0.0400	0.6179	0.0181	0.23 (3)*
C18	0.3843 (3)	0.7592 (5)	0.0829 (4)	0.0832 (12)
H18A	0.4245	0.8220	0.0479	0.113 (16)*
C19	0.4046 (3)	0.7838 (4)	0.1997 (4)	0.0854 (13)
H19A	0.4819	0.7749	0.2250	0.093 (13)*
H19B	0.3827	0.8715	0.2141	0.086 (12)*
C20	0.3412 (3)	0.6858 (4)	0.2566 (3)	0.0709 (11)
H20A	0.3543	0.7027	0.3309	0.089 (12)*
C21	0.3796 (3)	0.5474 (4)	0.2345 (3)	0.0752 (11)
H21A	0.4562	0.5379	0.2621	0.072 (11)*
H21B	0.3384	0.4840	0.2679	0.100 (15)*
C22	0.2176 (3)	0.7000 (4)	0.2164 (2)	0.0604 (9)
H22A	0.1762	0.6394	0.2523	0.086 (13)*
H22B	0.1938	0.7873	0.2297	0.079 (12)*
C23	0.3609 (3)	0.5257 (4)	0.1154 (3)	0.0704 (11)
H23A	0.3858	0.4396	0.0999	0.095 (13)*
C24	0.2618 (3)	0.7734 (4)	0.0421 (3)	0.0679 (10)
H24A	0.2377	0.8606	0.0551	0.111 (16)*
H24B	0.2479	0.7574	−0.0323	0.103 (15)*
C25	0.4232 (3)	0.6267 (5)	0.0625 (4)	0.0852 (13)
H25A	0.4139	0.6101	−0.0119	0.130 (19)*
H25B	0.5004	0.6207	0.0892	0.093 (13)*
C26	0.2374 (3)	0.5371 (3)	0.0762 (3)	0.0639 (10)
H26A	0.2226	0.5201	0.0020	0.087 (13)*
H26B	0.1981	0.4737	0.1116	0.052 (9)*
C27	0.1979 (2)	0.6736 (3)	0.0991 (2)	0.0409 (6)
C28	0.0184 (3)	0.8077 (3)	0.0800 (2)	0.0500 (7)
H28A	0.0613	0.8815	0.0634	0.082 (12)*
H28B	0.0135	0.8109	0.1539	0.043 (8)*
C29	−0.0946 (2)	0.8170 (3)	0.0198 (2)	0.0437 (7)
C30	−0.1871 (3)	0.8027 (3)	0.0692 (3)	0.0625 (9)
H30A	−0.1780	0.7829	0.1430	0.082 (12)*
C31	−0.2914 (3)	0.8181 (4)	0.0146 (4)	0.0774 (11)
H31A	−0.3550	0.8068	0.0493	0.100 (15)*
C32	−0.3042 (3)	0.8490 (4)	−0.0905 (4)	0.0794 (12)
H32A	−0.3770	0.8604	−0.1288	0.105 (14)*
C33	−0.2136 (3)	0.8645 (3)	−0.1424 (3)	0.0653 (10)
H33A	−0.2225	0.8857	−0.2160	0.101 (14)*
C34	−0.1099 (3)	0.8494 (3)	−0.0868 (2)	0.0492 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1004 (7)	0.0557 (5)	0.0339 (4)	0.0196 (4)	0.0159 (4)	0.0021 (3)
O1	0.0775 (16)	0.0677 (16)	0.0505 (14)	0.0146 (12)	0.0211 (11)	0.0142 (11)
N1	0.0488 (14)	0.0375 (12)	0.0313 (11)	0.0016 (10)	0.0073 (10)	0.0006 (9)
C18	0.056 (2)	0.090 (3)	0.107 (3)	−0.010 (2)	0.022 (2)	0.016 (3)
C19	0.055 (2)	0.062 (3)	0.133 (4)	−0.0044 (18)	−0.008 (2)	−0.019 (2)
C20	0.059 (2)	0.101 (3)	0.0477 (19)	0.014 (2)	−0.0074 (16)	−0.0226 (19)
C21	0.057 (2)	0.078 (3)	0.086 (3)	0.0117 (19)	−0.007 (2)	0.014 (2)
C22	0.061 (2)	0.083 (3)	0.0361 (16)	0.0120 (18)	0.0050 (15)	−0.0123 (16)
C23	0.067 (2)	0.055 (2)	0.085 (3)	0.0188 (17)	−0.003 (2)	−0.0219 (19)
C24	0.057 (2)	0.076 (3)	0.073 (3)	−0.0042 (18)	0.0178 (18)	0.017 (2)
C25	0.059 (3)	0.113 (4)	0.087 (3)	0.006 (2)	0.022 (2)	−0.006 (3)
C26	0.068 (2)	0.0471 (19)	0.073 (2)	0.0063 (16)	−0.0012 (18)	−0.0148 (17)
C27	0.0461 (16)	0.0396 (15)	0.0379 (14)	−0.0007 (12)	0.0091 (12)	−0.0024 (11)
C28	0.0632 (19)	0.0418 (17)	0.0436 (16)	0.0065 (14)	0.0024 (14)	−0.0075 (13)
C29	0.0478 (16)	0.0352 (14)	0.0481 (16)	0.0033 (12)	0.0072 (13)	0.0004 (12)
C30	0.067 (2)	0.059 (2)	0.066 (2)	0.0046 (16)	0.0223 (18)	0.0098 (17)
C31	0.053 (2)	0.070 (3)	0.112 (4)	−0.0011 (18)	0.020 (2)	0.005 (2)
C32	0.053 (2)	0.062 (2)	0.114 (4)	0.0038 (17)	−0.016 (2)	−0.006 (2)
C33	0.076 (2)	0.054 (2)	0.060 (2)	0.0130 (17)	−0.0111 (18)	−0.0020 (16)
C34	0.0628 (19)	0.0361 (15)	0.0481 (17)	0.0059 (13)	0.0058 (15)	−0.0010 (12)

Geometric parameters (Å, º) top

O1—C34	1.370 (4)	C23—C26	1.529 (5)
O1—H1B	0.8530	C23—H23A	0.9600
N1—C28	1.511 (3)	C24—C27	1.535 (4)
N1—C27	1.517 (3)	C24—H24A	0.9601
N1—H1C	0.9000	C24—H24B	0.9600
N1—H1A	0.9001	C25—H25A	0.9600
C18—C25	1.470 (6)	C25—H25B	0.9600
C18—C19	1.505 (6)	C26—C27	1.517 (4)
C18—C24	1.524 (5)	C26—H26A	0.9601
C18—H18A	0.9599	C26—H26B	0.9601
C19—C20	1.518 (6)	C28—C29	1.488 (4)
C19—H19A	0.9600	C28—H28A	0.9601
C19—H19B	0.9599	C28—H28B	0.9600
C20—C21	1.528 (5)	C29—C30	1.386 (4)
C20—C22	1.534 (4)	C29—C34	1.394 (4)
C20—H20A	0.9600	C30—C31	1.375 (5)
C21—C23	1.529 (6)	C30—H30A	0.9600
C21—H21A	0.9600	C31—C32	1.373 (6)
C21—H21B	0.9599	C31—H31A	0.9601
C22—C27	1.515 (4)	C32—C33	1.386 (6)
C22—H22A	0.9599	C32—H32A	0.9602
C22—H22B	0.9600	C33—C34	1.373 (5)
C23—C25	1.504 (6)	C33—H33A	0.9598

C34—O1—H1B	108.6	C18—C24—H24B	110.4
C28—N1—C27	116.3 (2)	C27—C24—H24B	109.5
C28—N1—H1C	89.7	H24A—C24—H24B	108.4
C27—N1—H1C	89.7	C18—C25—C23	110.5 (3)
C28—N1—H1A	121.6	C18—C25—H25A	110.2
C27—N1—H1A	122.1	C23—C25—H25A	109.6
H1C—N1—H1A	90.2	C18—C25—H25B	108.9
C25—C18—C19	108.7 (4)	C23—C25—H25B	109.5
C25—C18—C24	110.8 (4)	H25A—C25—H25B	108.1
C19—C18—C24	109.8 (3)	C27—C26—C23	109.6 (3)
C25—C18—H18A	109.1	C27—C26—H26A	109.8
C19—C18—H18A	109.5	C23—C26—H26A	110.3
C24—C18—H18A	108.9	C27—C26—H26B	109.2
C18—C19—C20	110.4 (3)	C23—C26—H26B	109.5
C18—C19—H19A	109.5	H26A—C26—H26B	108.3
C20—C19—H19A	109.0	C22—C27—N1	111.0 (2)
C18—C19—H19B	109.7	C22—C27—C26	110.3 (3)
C20—C19—H19B	110.1	N1—C27—C26	108.2 (2)
H19A—C19—H19B	108.3	C22—C27—C24	109.7 (3)
C19—C20—C21	109.0 (3)	N1—C27—C24	109.1 (2)
C19—C20—C22	109.1 (3)	C26—C27—C24	108.5 (3)
C21—C20—C22	109.9 (3)	C29—C28—N1	112.1 (2)
C19—C20—H20A	109.7	C29—C28—H28A	109.4
C21—C20—H20A	109.9	N1—C28—H28A	109.0
C22—C20—H20A	109.3	C29—C28—H28B	108.8
C20—C21—C23	108.4 (3)	N1—C28—H28B	109.4
C20—C21—H21A	109.6	H28A—C28—H28B	108.0
C23—C21—H21A	110.5	C30—C29—C34	118.3 (3)
C20—C21—H21B	110.1	C30—C29—C28	121.2 (3)
C23—C21—H21B	109.8	C34—C29—C28	120.4 (3)
H21A—C21—H21B	108.5	C31—C30—C29	121.1 (3)
C27—C22—C20	108.9 (3)	C31—C30—H30A	119.5
C27—C22—H22A	110.2	C29—C30—H30A	119.4
C20—C22—H22A	110.1	C32—C31—C30	119.4 (4)
C27—C22—H22B	109.5	C32—C31—H31A	120.1
C20—C22—H22B	109.8	C30—C31—H31A	120.5
H22A—C22—H22B	108.4	C31—C32—C33	121.0 (3)
C25—C23—C21	110.0 (3)	C31—C32—H32A	119.6
C25—C23—C26	110.1 (3)	C33—C32—H32A	119.4
C21—C23—C26	108.3 (3)	C34—C33—C32	119.0 (4)
C25—C23—H23A	109.6	C34—C33—H33A	120.0
C21—C23—H23A	109.6	C32—C33—H33A	121.1
C26—C23—H23A	109.3	O1—C34—C33	123.7 (3)
C18—C24—C27	108.6 (3)	O1—C34—C29	115.1 (3)
C18—C24—H24A	110.0	C33—C34—C29	121.2 (3)
C27—C24—H24A	109.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱ	0.90	2.58	3.260 (2)	133
N1—H1C···Cl1ⁱⁱ	0.90	2.38	3.118 (2)	139
O1—H1B···Cl1ⁱⁱⁱ	0.85	2.27	3.049 (2)	152

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₄NO⁺·Cl⁻
M_r	293.82
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.262 (3), 10.202 (2), 12.845 (3)
β (°)	98.43 (3)
V (Å³)	1589.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.954, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	15541, 3632, 2249
R_int	0.088
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.217, 1.06
No. of reflections	3632
No. of parameters	204
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.48

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱ	0.90	2.58	3.260 (2)	132.7
N1—H1C···Cl1ⁱⁱ	0.90	2.38	3.118 (2)	138.9
O1—H1B···Cl1ⁱⁱⁱ	0.85	2.27	3.049 (2)	151.8

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

Acknowledgements

The authors are grateful to the Starter Fund of Southeast University, Nanjing, People's Republic of China.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Fu, D.-W., Song, Y.-M., Wang, G.-X., Ye, Q., Xiong, R.-G., Akutagawa, T., Nakamura, T., Chan, P. W. H. & Huang, S. D. (2007). J. Am. Chem. Soc. 129, 5346–5347. Web of Science CSD CrossRef PubMed CAS Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ye, H.-Y., Fu, D.-W., Zhang, Y., Zhang, W., Xiong, R.-G. & Huang, S. D. (2009). J. Am. Chem. Soc. 131, 42–43. Web of Science CSD CrossRef PubMed CAS Google Scholar
Ye, Q., Song, Y.-M., Wang, G.-X., Fu, D.-W. & Xiong, R.-G. (2006). J. Am. Chem. Soc. 128, 6554–6555. Web of Science CSD CrossRef PubMed CAS Google Scholar
Zhang, W., Xiong, R.-G. & Huang, S.-P. D. (2008). J. Am. Chem. Soc. 130, 10468–10469. Web of Science CSD CrossRef PubMed CAS Google Scholar
Zhao, H., Qu, Z.-R., Ye, H.-Y. & Xiong, R.-G. (2008). Chem. Soc. Rev. 37, 84–100. Web of Science CrossRef PubMed Google Scholar