Redetermination of the salt hexa­methyl­ene­tetra­minium fumarate

Lemmerer, A.

doi:10.1107/S1600536810052700

organic compounds

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Volume 67| Part 1| January 2011| Page o214

https://doi.org/10.1107/S1600536810052700

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Redetermination of the salt hexamethylenetetraminium fumarate

Andreas Lemmerer ^a ^*

^aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag 3, PO WITS, 2050 Johannesburg, South Africa
^*Correspondence e-mail: andreas.lemmerer@wits.ac.za

(Received 14 December 2010; accepted 15 December 2010; online 24 December 2010)

The crystal structure of the title compound [systematic name: 3,5,7-triaza-1-azoniatricyclo[3.3.1.1^3,7]decane (E)-3-carboxyprop-2-enoate], C₆H₁₃N₄⁺·C₄H₃O₄⁻, had been determined previously by Bowes et al. [Acta Cryst. (2003), B59, 100–117]. Their structure contained an approximately 3:1 ratio of fumarate and succinate monoanions disordered over the same position. The succinate anion component forms a similar structural role to the fumarate anion and came about due to an impurity in the starting material, fumaric acid. In this work, the crystal structure of the pure salt is presented, which is identical, apart from the lack of disorder of the anions, to the previous structure. In the crystal, the ions assemble in the solid state, forming chains via N⁺—H⋯O⁻ and O—H⋯O⁻ hydrogen bonds, which are linked into a three-dimensional network by C—H⋯O interactions.

Related literature

For the previous synthesis and structure determination, see: Bowes et al. (2003 ). For graph-set nomenclature of hydrogen bonds, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₆H₁₃N₄⁺·C₄H₃O₄⁻
M_r = 256.27
Monoclinic, P 2₁ /c
a = 6.3020 (3) Å
b = 16.0828 (8) Å
c = 11.2205 (6) Å
β = 95.930 (2)°
V = 1131.15 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 173 K
0.4 × 0.26 × 0.1 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: integration (XPREP; Bruker, 2004 ) T_min = 0.936, T_max = 0.989
12032 measured reflections
2733 independent reflections
2263 reflections with I > 2σ(I)
R_int = 0.114

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.128
S = 1.04
2733 reflections
169 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.845 (19)	2.094 (19)	2.8704 (14)	153 (2)
O3—H3⋯O1ⁱ	1.034 (18)	1.458 (18)	2.4877 (13)	174 (2)
C1—H1A⋯O3ⁱⁱ	0.99	2.46	3.2708 (16)	138
C3—H3B⋯O4ⁱⁱⁱ	0.99	2.55	3.4629 (18)	154
C4—H4B⋯O4^iv	0.99	2.48	3.3668 (17)	149
C6—H6A⋯O4^iv	0.99	2.43	3.3352 (18)	152
Symmetry codes: (i) x+1, y, z; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810052700/bt5439sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810052700/bt5439Isup2.hkl

checkCIF report

Comment top

The fumarate anions forms a C(7) chain (Graph Set notation; Bernstein et al., 1995) along the a axis by unit cell translations only. The chain is formed by O—H···O^- hydrogen bonds. The hexamethylenetramanium cation is pendant to the chains, and linked to them by N⁺—H···O^- hydrogen bonds (Fig. 2). Fig. 3 shows the relative packing of the chains down the a axis.

Related literature top

For previous the synthesis and structure determination, see: Bowes et al. (2003). For graph-set nomenclature of hydrogen bonds, see: Bernstein et al. (1995).

Experimental top

Crystals where grown by slow evaporation at ambient conditions of a methanol solution containing a stoichiometric quantity of hexamethylenetetramine and fumaric acid.

Structure description top

For previous the synthesis and structure determination, see: Bowes et al. (2003). For graph-set nomenclature of hydrogen bonds, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of (I) (50% probability displacement ellipsoids)
	Fig. 2. Hydrogen bonding chain of (I) using N⁺—H···O^- and O—H···O^- hydrogen bonds (red dashed lines), generated by translation along the a axis.
	Fig. 3. Packing diagram of the four C(7) chains in the unit cell.

3,5,7-Triaza-1-azoniatricyclo[3.3.1.13,7]decane (E)-3-carboxyprop-2-enoate top

Crystal data top

C₆H₁₃N₄⁺·C₄H₃O₄⁻	F(000) = 544
M_r = 256.27	D_x = 1.505 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4463 reflections
a = 6.3020 (3) Å	θ = 2.2–28.3°
b = 16.0828 (8) Å	µ = 0.12 mm⁻¹
c = 11.2205 (6) Å	T = 173 K
β = 95.930 (2)°	Block, colourless
V = 1131.15 (10) Å³	0.4 × 0.26 × 0.1 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2263 reflections with I > 2σ(I)
ω scans	R_int = 0.114
Absorption correction: integration (XPREP; Bruker, 2004)	θ_max = 28.0°, θ_min = 2.2°
T_min = 0.936, T_max = 0.989	h = −8→8
12032 measured reflections	k = −21→21
2733 independent reflections	l = −11→14

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.045	w = 1/[σ²(F_o²) + (0.0679P)² + 0.1146P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.128	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.36 e Å⁻³
2733 reflections	Δρ_min = −0.26 e Å⁻³
169 parameters

Crystal data top

C₆H₁₃N₄⁺·C₄H₃O₄⁻	V = 1131.15 (10) Å³
M_r = 256.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.3020 (3) Å	µ = 0.12 mm⁻¹
b = 16.0828 (8) Å	T = 173 K
c = 11.2205 (6) Å	0.4 × 0.26 × 0.1 mm
β = 95.930 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2733 independent reflections
Absorption correction: integration (XPREP; Bruker, 2004)	2263 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.989	R_int = 0.114
12032 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.36 e Å⁻³
2733 reflections	Δρ_min = −0.26 e Å⁻³
169 parameters

Special details top

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004)

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

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

	x	y	z	U_iso*/U_eq
C1	0.5255 (2)	0.82554 (8)	0.61723 (12)	0.0247 (3)
H1A	0.5118	0.8385	0.7024	0.03*
H1B	0.6756	0.81	0.6098	0.03*
C2	0.2451 (2)	0.91915 (8)	0.55450 (13)	0.0272 (3)
H2A	0.207	0.9693	0.5057	0.033*
H2B	0.2281	0.9326	0.6391	0.033*
C3	0.1515 (2)	0.77886 (9)	0.58785 (13)	0.0262 (3)
H3A	0.0546	0.7325	0.5615	0.031*
H3B	0.1334	0.7915	0.6726	0.031*
C4	0.4040 (2)	0.73544 (8)	0.44620 (12)	0.0232 (3)
H4A	0.5531	0.7191	0.4376	0.028*
H4B	0.3097	0.6886	0.4182	0.028*
C5	0.4895 (2)	0.87723 (9)	0.41791 (12)	0.0271 (3)
H5A	0.4544	0.927	0.3678	0.033*
H5B	0.6394	0.8619	0.4096	0.033*
C6	0.1277 (2)	0.83150 (9)	0.38914 (12)	0.0266 (3)
H6A	0.0318	0.7851	0.3616	0.032*
H6B	0.087	0.8805	0.3384	0.032*
N1	0.37969 (18)	0.75391 (7)	0.57675 (10)	0.0208 (3)
H1	0.409 (3)	0.7097 (12)	0.6156 (16)	0.031*
N2	0.46828 (19)	0.89757 (7)	0.54400 (10)	0.0243 (3)
N3	0.09872 (18)	0.85121 (7)	0.51461 (10)	0.0244 (3)
N4	0.34884 (19)	0.80830 (7)	0.37423 (10)	0.0239 (3)
C7	0.6729 (2)	0.58907 (8)	0.63638 (11)	0.0176 (3)
C8	0.7983 (2)	0.50985 (8)	0.64094 (11)	0.0182 (3)
H8	0.7237	0.4585	0.6406	0.022*
C9	1.00774 (19)	0.50863 (8)	0.64536 (11)	0.0173 (3)
H9	1.0825	0.5599	0.6451	0.021*
C10	1.1315 (2)	0.42962 (8)	0.65074 (11)	0.0180 (3)
O1	0.46931 (14)	0.58179 (6)	0.62743 (8)	0.0214 (2)
O2	0.76697 (15)	0.65634 (6)	0.64178 (10)	0.0281 (3)
O3	1.33649 (14)	0.43696 (6)	0.64341 (9)	0.0220 (2)
H3	1.382 (3)	0.4983 (12)	0.6347 (15)	0.033*
O4	1.04798 (15)	0.36217 (6)	0.66187 (10)	0.0305 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0283 (7)	0.0205 (7)	0.0229 (6)	−0.0018 (5)	−0.0083 (5)	−0.0022 (5)
C2	0.0381 (8)	0.0157 (6)	0.0269 (7)	0.0061 (5)	−0.0004 (6)	−0.0016 (5)
C3	0.0258 (7)	0.0238 (7)	0.0294 (7)	0.0016 (5)	0.0045 (6)	0.0065 (5)
C4	0.0275 (7)	0.0174 (6)	0.0238 (7)	0.0009 (5)	−0.0016 (5)	−0.0051 (5)
C5	0.0326 (7)	0.0241 (7)	0.0246 (7)	−0.0079 (6)	0.0028 (6)	0.0021 (5)
C6	0.0297 (7)	0.0230 (7)	0.0245 (7)	0.0008 (5)	−0.0093 (6)	0.0024 (5)
N1	0.0259 (6)	0.0135 (5)	0.0216 (5)	0.0013 (4)	−0.0040 (4)	0.0035 (4)
N2	0.0315 (6)	0.0164 (5)	0.0236 (6)	−0.0032 (4)	−0.0034 (5)	−0.0009 (4)
N3	0.0254 (6)	0.0204 (6)	0.0267 (6)	0.0041 (4)	−0.0007 (5)	0.0032 (4)
N4	0.0308 (6)	0.0209 (6)	0.0191 (5)	−0.0019 (5)	−0.0022 (4)	−0.0016 (4)
C7	0.0189 (6)	0.0172 (6)	0.0160 (6)	0.0009 (5)	−0.0015 (4)	0.0007 (4)
C8	0.0200 (6)	0.0152 (6)	0.0185 (6)	−0.0005 (5)	−0.0028 (5)	0.0013 (4)
C9	0.0195 (6)	0.0144 (6)	0.0173 (5)	−0.0013 (4)	−0.0021 (4)	0.0004 (4)
C10	0.0188 (6)	0.0165 (6)	0.0175 (6)	−0.0002 (5)	−0.0037 (4)	0.0005 (4)
O1	0.0167 (4)	0.0185 (5)	0.0284 (5)	0.0017 (3)	0.0000 (4)	0.0021 (4)
O2	0.0241 (5)	0.0155 (5)	0.0428 (6)	−0.0015 (4)	−0.0049 (4)	0.0005 (4)
O3	0.0168 (4)	0.0175 (5)	0.0307 (5)	0.0012 (3)	−0.0020 (4)	0.0028 (4)
O4	0.0253 (5)	0.0167 (5)	0.0484 (7)	−0.0031 (4)	−0.0018 (4)	0.0038 (4)

Geometric parameters (Å, º) top

C1—N2	1.4442 (17)	C5—H5A	0.99
C1—N1	1.5139 (17)	C5—H5B	0.99
C1—H1A	0.99	C6—N4	1.4691 (19)
C1—H1B	0.99	C6—N3	1.4727 (18)
C2—N2	1.4654 (19)	C6—H6A	0.99
C2—N3	1.4695 (18)	C6—H6B	0.99
C2—H2A	0.99	N1—H1	0.845 (19)
C2—H2B	0.99	C7—O2	1.2320 (15)
C3—N3	1.4435 (17)	C7—O1	1.2821 (15)
C3—N1	1.5105 (17)	C7—C8	1.4971 (17)
C3—H3A	0.99	C8—C9	1.3161 (17)
C3—H3B	0.99	C8—H8	0.95
C4—N4	1.4451 (17)	C9—C10	1.4889 (17)
C4—N1	1.5179 (17)	C9—H9	0.95
C4—H4A	0.99	C10—O4	1.2179 (16)
C4—H4B	0.99	C10—O3	1.3081 (15)
C5—N4	1.4715 (18)	O3—H3	1.034 (18)
C5—N2	1.4717 (18)

N2—C1—N1	109.36 (10)	N3—C6—H6A	109.2
N2—C1—H1A	109.8	N4—C6—H6B	109.2
N1—C1—H1A	109.8	N3—C6—H6B	109.2
N2—C1—H1B	109.8	H6A—C6—H6B	107.9
N1—C1—H1B	109.8	C3—N1—C1	109.07 (11)
H1A—C1—H1B	108.3	C3—N1—C4	108.88 (10)
N2—C2—N3	112.14 (11)	C1—N1—C4	108.65 (10)
N2—C2—H2A	109.2	C3—N1—H1	109.9 (12)
N3—C2—H2A	109.2	C1—N1—H1	113.1 (12)
N2—C2—H2B	109.2	C4—N1—H1	107.1 (12)
N3—C2—H2B	109.2	C1—N2—C2	109.24 (11)
H2A—C2—H2B	107.9	C1—N2—C5	109.06 (11)
N3—C3—N1	109.42 (11)	C2—N2—C5	108.26 (11)
N3—C3—H3A	109.8	C3—N3—C2	109.00 (11)
N1—C3—H3A	109.8	C3—N3—C6	109.07 (11)
N3—C3—H3B	109.8	C2—N3—C6	108.38 (11)
N1—C3—H3B	109.8	C4—N4—C6	108.59 (11)
H3A—C3—H3B	108.2	C4—N4—C5	108.84 (10)
N4—C4—N1	109.76 (10)	C6—N4—C5	108.47 (11)
N4—C4—H4A	109.7	O2—C7—O1	123.81 (12)
N1—C4—H4A	109.7	O2—C7—C8	119.76 (11)
N4—C4—H4B	109.7	O1—C7—C8	116.43 (11)
N1—C4—H4B	109.7	C9—C8—C7	122.51 (12)
H4A—C4—H4B	108.2	C9—C8—H8	118.7
N4—C5—N2	112.09 (11)	C7—C8—H8	118.7
N4—C5—H5A	109.2	C8—C9—C10	122.25 (12)
N2—C5—H5A	109.2	C8—C9—H9	118.9
N4—C5—H5B	109.2	C10—C9—H9	118.9
N2—C5—H5B	109.2	O4—C10—O3	121.80 (11)
H5A—C5—H5B	107.9	O4—C10—C9	122.28 (12)
N4—C6—N3	112.10 (11)	O3—C10—C9	115.92 (11)
N4—C6—H6A	109.2	C10—O3—H3	112.0 (9)

N3—C3—N1—C1	59.36 (14)	N2—C2—N3—C6	−58.33 (14)
N3—C3—N1—C4	−59.05 (14)	N4—C6—N3—C3	−60.71 (15)
N2—C1—N1—C3	−59.07 (14)	N4—C6—N3—C2	57.83 (14)
N2—C1—N1—C4	59.49 (14)	N1—C4—N4—C6	−59.03 (13)
N4—C4—N1—C3	59.28 (13)	N1—C4—N4—C5	58.87 (14)
N4—C4—N1—C1	−59.39 (13)	N3—C6—N4—C4	60.45 (14)
N1—C1—N2—C2	58.69 (14)	N3—C6—N4—C5	−57.68 (14)
N1—C1—N2—C5	−59.46 (14)	N2—C5—N4—C4	−60.05 (15)
N3—C2—N2—C1	−60.15 (14)	N2—C5—N4—C6	57.93 (14)
N3—C2—N2—C5	58.50 (14)	O2—C7—C8—C9	−3.04 (19)
N4—C5—N2—C1	60.51 (15)	O1—C7—C8—C9	177.28 (11)
N4—C5—N2—C2	−58.25 (15)	C7—C8—C9—C10	179.56 (11)
N1—C3—N3—C2	−59.05 (14)	C8—C9—C10—O4	−6.5 (2)
N1—C3—N3—C6	59.11 (14)	C8—C9—C10—O3	173.79 (11)
N2—C2—N3—C3	60.25 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.845 (19)	2.094 (19)	2.8704 (14)	153 (2)
O3—H3···O1ⁱ	1.034 (18)	1.458 (18)	2.4877 (13)	174 (2)
C1—H1A···O3ⁱⁱ	0.99	2.46	3.2708 (16)	138
C3—H3B···O4ⁱⁱⁱ	0.99	2.55	3.4629 (18)	154
C4—H4B···O4^iv	0.99	2.48	3.3668 (17)	149
C6—H6A···O4^iv	0.99	2.43	3.3352 (18)	152

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

Experimental details

Crystal data
Chemical formula	C₆H₁₃N₄⁺·C₄H₃O₄⁻
M_r	256.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	6.3020 (3), 16.0828 (8), 11.2205 (6)
β (°)	95.930 (2)
V (Å³)	1131.15 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.4 × 0.26 × 0.1

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Integration (XPREP; Bruker, 2004)
T_min, T_max	0.936, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	12032, 2733, 2263
R_int	0.114
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.128, 1.04
No. of reflections	2733
No. of parameters	169
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.26

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.845 (19)	2.094 (19)	2.8704 (14)	153 (2)
O3—H3···O1ⁱ	1.034 (18)	1.458 (18)	2.4877 (13)	174 (2)
C1—H1A···O3ⁱⁱ	0.99	2.46	3.2708 (16)	138
C3—H3B···O4ⁱⁱⁱ	0.99	2.55	3.4629 (18)	154
C4—H4B···O4^iv	0.99	2.48	3.3668 (17)	149
C6—H6A···O4^iv	0.99	2.43	3.3352 (18)	152

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

Acknowledgements

The University of the Witwatersrand and the Molecular Sciences Institute are thanked for providing the infrastructure and financial support to do this work.

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