4-Nitro-2-{[(tricyclo­[3.3.1.13,7]decan-1-yl)iminium­yl]meth­yl}phenolate

Ha, K.

doi:10.1107/S1600536812012597

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1221

doi:10.1107/S1600536812012597

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4-Nitro-2-{[(tricyclo[3.3.1.1^3,7]decan-1-yl)iminiumyl]methyl}phenolate

Kwang Ha ^a ^*

^aSchool of Applied Chemical Engineering, The Research Institute of Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea
^*Correspondence e-mail: hakwang@chonnam.ac.kr

(Received 21 March 2012; accepted 22 March 2012; online 28 March 2012)

The title compound, C₁₇H₂₀N₂O₃, is a Schiff base, which is found as a zwitterion in the solid state. The geometry around the iminium N atom indicates sp²-hybridization. The zwitterion shows a strong intramolecular N—H⋯O hydrogen-bond interaction between the iminium N atom and the phenolate O atom.

Related literature

For the crystal structure of 2-[(tricyclo[3.3.1.1^3,7]decan-1-ylimino)methyl]phenol, see: Fernández-G et al. (2001 ).

Experimental

Crystal data

C₁₇H₂₀N₂O₃
M_r = 300.35
Triclinic, $[P \overline 1]$
a = 6.3531 (5) Å
b = 11.0617 (10) Å
c = 12.1576 (11) Å
α = 62.995 (2)°
β = 76.446 (2)°
γ = 75.487 (2)°
V = 729.71 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 200 K
0.26 × 0.25 × 0.15 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.897, T_max = 1.000
4583 measured reflections
2822 independent reflections
1457 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.146
S = 0.95
2822 reflections
202 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.95 (3)	1.79 (3)	2.597 (3)	140 (2)

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812012597/fk2057sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812012597/fk2057Isup2.hkl

checkCIF report

Comment top

The title compound, C₁₇H₂₀N₂O₃, is a Schiff base, which can act as a monobasic bidentate ligand, that is, the N,O donor atoms can coordinate to a metal ion. In the crystal structure, the Schiff base is found as a zwitterion (Fig. 1), whereas the closely related compound IDOHIS 2-[(tricyclo[3.3.1.1^3,7]decan-1-ylimino)methyl]phenol with similar molecular geometry is in the phenol-imine form (Fernández-G et al., 2001).

Related literature top

For the crystal structure of 2-[(tricyclo[3.3.1.1^3,7]decan-1-ylimino)methyl]phenol, see: Fernández-G et al. (2001).

Experimental top

1-Adamantylamine (0.4556 g, 3.012 mmol) and 5-nitrosalicylaldehyde (0.5040 g, 3.016 mmol) in acetone (20 ml) were stirred for 3 h at room temparature. After addition of pentane (50 ml) to the reaction mixture, the formed precipitate was separated by filtration, washed with pentane, and dried at 50 °C, to give a yellow powder (0.8312 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from a CH₃CN solution at room temparature.

Structure description top

For the crystal structure of 2-[(tricyclo[3.3.1.1^3,7]decan-1-ylimino)methyl]phenol, see: Fernández-G et al. (2001).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound, with atom numbering. Displacement ellipsoids are drawn at the 40% probability level for non-H atoms.

4-Nitro-2-[(tricyclo[3.3.1.1^3,7]decan-1-yliminiumyl)methyl]phenolate top

Crystal data top

C₁₇H₂₀N₂O₃	Z = 2
M_r = 300.35	F(000) = 320
Triclinic, P1	D_x = 1.367 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3531 (5) Å	Cell parameters from 1063 reflections
b = 11.0617 (10) Å	θ = 3.4–24.9°
c = 12.1576 (11) Å	µ = 0.09 mm⁻¹
α = 62.995 (2)°	T = 200 K
β = 76.446 (2)°	Block, yellow
γ = 75.487 (2)°	0.26 × 0.25 × 0.15 mm
V = 729.71 (11) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	2822 independent reflections
Radiation source: fine-focus sealed tube	1457 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→6
T_min = 0.897, T_max = 1.000	k = −13→13
4583 measured reflections	l = −13→14

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0616P)²] where P = (F_o² + 2F_c²)/3
2822 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₇H₂₀N₂O₃	γ = 75.487 (2)°
M_r = 300.35	V = 729.71 (11) Å³
Triclinic, P1	Z = 2
a = 6.3531 (5) Å	Mo Kα radiation
b = 11.0617 (10) Å	µ = 0.09 mm⁻¹
c = 12.1576 (11) Å	T = 200 K
α = 62.995 (2)°	0.26 × 0.25 × 0.15 mm
β = 76.446 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	2822 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1457 reflections with I > 2σ(I)
T_min = 0.897, T_max = 1.000	R_int = 0.029
4583 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.19 e Å⁻³
2822 reflections	Δρ_min = −0.24 e Å⁻³
202 parameters

Special details top

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.

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
O1	1.0883 (3)	0.7989 (2)	−0.01074 (18)	0.0579 (6)
O2	0.9391 (3)	0.5043 (2)	−0.3099 (2)	0.0681 (6)
O3	0.6210 (3)	0.5069 (2)	−0.19649 (19)	0.0616 (6)
N1	0.7093 (3)	0.7907 (2)	0.12908 (19)	0.0378 (6)
H1N	0.856 (5)	0.809 (3)	0.103 (2)	0.057*
N2	0.8088 (4)	0.5349 (2)	−0.2295 (2)	0.0487 (6)
C1	1.0215 (4)	0.7417 (3)	−0.0628 (2)	0.0423 (7)
C2	0.8046 (4)	0.7034 (2)	−0.0257 (2)	0.0357 (6)
C3	0.7394 (4)	0.6358 (2)	−0.0807 (2)	0.0374 (6)
H3	0.5980	0.6100	−0.0542	0.045*
C4	0.8786 (4)	0.6058 (2)	−0.1734 (2)	0.0382 (6)
C5	1.0878 (4)	0.6442 (3)	−0.2144 (2)	0.0438 (7)
H5	1.1823	0.6230	−0.2787	0.053*
C6	1.1554 (4)	0.7108 (3)	−0.1634 (2)	0.0463 (7)
H6	1.2956	0.7382	−0.1946	0.056*
C7	0.6570 (4)	0.7319 (2)	0.0713 (2)	0.0382 (6)
H7	0.5154	0.7067	0.0939	0.046*
C8	0.5734 (4)	0.8178 (2)	0.2350 (2)	0.0331 (6)
C9	0.6942 (4)	0.9009 (3)	0.2633 (2)	0.0422 (7)
H9A	0.8428	0.8495	0.2819	0.051*
H9B	0.7103	0.9894	0.1898	0.051*
C10	0.5661 (4)	0.9281 (3)	0.3747 (2)	0.0418 (7)
H10	0.6461	0.9825	0.3931	0.050*
C11	0.5428 (4)	0.7919 (3)	0.4882 (2)	0.0433 (7)
H11A	0.6899	0.7389	0.5086	0.052*
H11B	0.4611	0.8094	0.5610	0.052*
C12	0.4202 (4)	0.7097 (2)	0.4600 (2)	0.0378 (6)
H12	0.4043	0.6205	0.5345	0.045*
C13	0.1928 (4)	0.7910 (3)	0.4292 (2)	0.0424 (7)
H13A	0.1124	0.7370	0.4119	0.051*
H13B	0.1078	0.8091	0.5011	0.051*
C14	0.2172 (4)	0.9268 (2)	0.3153 (2)	0.0389 (7)
H14	0.0683	0.9802	0.2954	0.047*
C15	0.3463 (4)	0.8987 (3)	0.2030 (2)	0.0388 (7)
H15A	0.2676	0.8451	0.1841	0.047*
H15B	0.3608	0.9867	0.1287	0.047*
C16	0.5489 (4)	0.6809 (2)	0.3483 (2)	0.0386 (6)
H16A	0.6957	0.6266	0.3679	0.046*
H16B	0.4699	0.6270	0.3300	0.046*
C17	0.3388 (4)	1.0100 (3)	0.3438 (3)	0.0437 (7)
H17A	0.2547	1.0292	0.4153	0.052*
H17B	0.3536	1.0989	0.2707	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0459 (12)	0.0837 (15)	0.0525 (13)	−0.0252 (10)	0.0053 (9)	−0.0343 (12)
O2	0.0599 (14)	0.0838 (16)	0.0720 (16)	−0.0015 (11)	0.0120 (11)	−0.0577 (13)
O3	0.0535 (14)	0.0717 (14)	0.0720 (15)	−0.0210 (11)	0.0125 (11)	−0.0453 (12)
N1	0.0337 (13)	0.0449 (13)	0.0311 (13)	−0.0116 (10)	0.0008 (10)	−0.0128 (11)
N2	0.0498 (16)	0.0414 (14)	0.0502 (16)	−0.0020 (12)	0.0023 (12)	−0.0224 (12)
C1	0.0354 (16)	0.0461 (16)	0.0335 (16)	−0.0065 (12)	−0.0019 (12)	−0.0080 (14)
C2	0.0353 (15)	0.0344 (14)	0.0263 (14)	−0.0051 (11)	0.0020 (11)	−0.0065 (12)
C3	0.0347 (15)	0.0345 (14)	0.0338 (16)	−0.0010 (11)	0.0005 (12)	−0.0115 (12)
C4	0.0378 (16)	0.0325 (14)	0.0356 (16)	0.0018 (11)	−0.0004 (12)	−0.0130 (12)
C5	0.0367 (16)	0.0440 (16)	0.0353 (16)	0.0019 (12)	0.0052 (12)	−0.0129 (14)
C6	0.0382 (16)	0.0509 (17)	0.0373 (17)	−0.0085 (13)	0.0054 (13)	−0.0124 (14)
C7	0.0371 (15)	0.0360 (15)	0.0346 (16)	−0.0095 (11)	0.0000 (12)	−0.0096 (13)
C8	0.0311 (14)	0.0408 (15)	0.0273 (14)	−0.0089 (11)	0.0017 (11)	−0.0155 (12)
C9	0.0396 (16)	0.0473 (16)	0.0404 (17)	−0.0125 (12)	−0.0057 (12)	−0.0164 (13)
C10	0.0446 (17)	0.0484 (16)	0.0400 (17)	−0.0156 (13)	−0.0026 (12)	−0.0226 (14)
C11	0.0367 (16)	0.0543 (17)	0.0354 (16)	0.0017 (12)	−0.0083 (12)	−0.0191 (14)
C12	0.0383 (15)	0.0339 (14)	0.0304 (15)	−0.0048 (11)	0.0036 (11)	−0.0088 (12)
C13	0.0364 (16)	0.0469 (16)	0.0432 (17)	−0.0091 (12)	0.0015 (12)	−0.0207 (14)
C14	0.0328 (15)	0.0409 (15)	0.0434 (17)	0.0017 (11)	−0.0094 (12)	−0.0201 (13)
C15	0.0423 (16)	0.0393 (15)	0.0335 (15)	−0.0058 (12)	−0.0080 (12)	−0.0133 (13)
C16	0.0373 (15)	0.0362 (15)	0.0352 (16)	−0.0042 (11)	0.0004 (12)	−0.0125 (13)
C17	0.0523 (18)	0.0364 (15)	0.0411 (17)	−0.0026 (12)	−0.0065 (13)	−0.0177 (13)

Geometric parameters (Å, º) top

O1—C1	1.267 (3)	C9—H9B	0.9900
O2—N2	1.239 (3)	C10—C11	1.525 (3)
O3—N2	1.236 (3)	C10—C17	1.528 (3)
N1—C7	1.289 (3)	C10—H10	1.0000
N1—C8	1.481 (3)	C11—C12	1.520 (3)
N1—H1N	0.95 (3)	C11—H11A	0.9900
N2—C4	1.441 (3)	C11—H11B	0.9900
C1—C6	1.444 (4)	C12—C13	1.528 (3)
C1—C2	1.452 (3)	C12—C16	1.535 (3)
C2—C3	1.385 (3)	C12—H12	1.0000
C2—C7	1.428 (3)	C13—C14	1.525 (3)
C3—C4	1.374 (3)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
C4—C5	1.406 (3)	C14—C17	1.527 (3)
C5—C6	1.345 (4)	C14—C15	1.539 (3)
C5—H5	0.9500	C14—H14	1.0000
C6—H6	0.9500	C15—H15A	0.9900
C7—H7	0.9500	C15—H15B	0.9900
C8—C9	1.522 (3)	C16—H16A	0.9900
C8—C15	1.528 (3)	C16—H16B	0.9900
C8—C16	1.529 (3)	C17—H17A	0.9900
C9—C10	1.522 (4)	C17—H17B	0.9900
C9—H9A	0.9900

C7—N1—C8	126.4 (2)	C17—C10—H10	109.4
C7—N1—H1N	113.5 (16)	C12—C11—C10	109.2 (2)
C8—N1—H1N	119.8 (16)	C12—C11—H11A	109.8
O3—N2—O2	122.0 (3)	C10—C11—H11A	109.8
O3—N2—C4	119.2 (2)	C12—C11—H11B	109.8
O2—N2—C4	118.8 (2)	C10—C11—H11B	109.8
O1—C1—C6	122.3 (2)	H11A—C11—H11B	108.3
O1—C1—C2	122.3 (2)	C11—C12—C13	109.8 (2)
C6—C1—C2	115.4 (3)	C11—C12—C16	109.7 (2)
C3—C2—C7	118.9 (2)	C13—C12—C16	109.2 (2)
C3—C2—C1	121.0 (2)	C11—C12—H12	109.4
C7—C2—C1	120.1 (2)	C13—C12—H12	109.4
C4—C3—C2	120.3 (2)	C16—C12—H12	109.4
C4—C3—H3	119.9	C14—C13—C12	109.35 (19)
C2—C3—H3	119.9	C14—C13—H13A	109.8
C3—C4—C5	120.6 (3)	C12—C13—H13A	109.8
C3—C4—N2	119.7 (2)	C14—C13—H13B	109.8
C5—C4—N2	119.8 (2)	C12—C13—H13B	109.8
C6—C5—C4	120.6 (3)	H13A—C13—H13B	108.3
C6—C5—H5	119.7	C13—C14—C17	109.3 (2)
C4—C5—H5	119.7	C13—C14—C15	109.8 (2)
C5—C6—C1	122.1 (3)	C17—C14—C15	109.8 (2)
C5—C6—H6	119.0	C13—C14—H14	109.3
C1—C6—H6	119.0	C17—C14—H14	109.3
N1—C7—C2	122.2 (2)	C15—C14—H14	109.3
N1—C7—H7	118.9	C8—C15—C14	108.5 (2)
C2—C7—H7	118.9	C8—C15—H15A	110.0
N1—C8—C9	107.1 (2)	C14—C15—H15A	110.0
N1—C8—C15	111.4 (2)	C8—C15—H15B	110.0
C9—C8—C15	109.8 (2)	C14—C15—H15B	110.0
N1—C8—C16	109.2 (2)	H15A—C15—H15B	108.4
C9—C8—C16	109.9 (2)	C8—C16—C12	109.0 (2)
C15—C8—C16	109.45 (19)	C8—C16—H16A	109.9
C10—C9—C8	109.6 (2)	C12—C16—H16A	109.9
C10—C9—H9A	109.7	C8—C16—H16B	109.9
C8—C9—H9A	109.7	C12—C16—H16B	109.9
C10—C9—H9B	109.7	H16A—C16—H16B	108.3
C8—C9—H9B	109.7	C14—C17—C10	109.3 (2)
H9A—C9—H9B	108.2	C14—C17—H17A	109.8
C9—C10—C11	109.8 (2)	C10—C17—H17A	109.8
C9—C10—C17	109.2 (2)	C14—C17—H17B	109.8
C11—C10—C17	109.7 (2)	C10—C17—H17B	109.8
C9—C10—H10	109.4	H17A—C17—H17B	108.3
C11—C10—H10	109.4

O1—C1—C2—C3	−177.2 (2)	C16—C8—C9—C10	−59.6 (3)
C6—C1—C2—C3	3.0 (3)	C8—C9—C10—C11	59.8 (3)
O1—C1—C2—C7	1.0 (4)	C8—C9—C10—C17	−60.5 (3)
C6—C1—C2—C7	−178.7 (2)	C9—C10—C11—C12	−60.2 (3)
C7—C2—C3—C4	−179.4 (2)	C17—C10—C11—C12	59.8 (3)
C1—C2—C3—C4	−1.2 (3)	C10—C11—C12—C13	−59.8 (3)
C2—C3—C4—C5	−0.5 (4)	C10—C11—C12—C16	60.3 (3)
C2—C3—C4—N2	179.8 (2)	C11—C12—C13—C14	60.2 (3)
O3—N2—C4—C3	2.7 (3)	C16—C12—C13—C14	−60.2 (3)
O2—N2—C4—C3	−177.5 (2)	C12—C13—C14—C17	−60.2 (3)
O3—N2—C4—C5	−176.9 (2)	C12—C13—C14—C15	60.3 (3)
O2—N2—C4—C5	2.9 (3)	N1—C8—C15—C14	−178.32 (19)
C3—C4—C5—C6	0.1 (4)	C9—C8—C15—C14	−59.9 (3)
N2—C4—C5—C6	179.8 (2)	C16—C8—C15—C14	60.8 (3)
C4—C5—C6—C1	2.0 (4)	C13—C14—C15—C8	−60.3 (3)
O1—C1—C6—C5	176.8 (2)	C17—C14—C15—C8	59.8 (2)
C2—C1—C6—C5	−3.5 (4)	N1—C8—C16—C12	176.50 (19)
C8—N1—C7—C2	−176.4 (2)	C9—C8—C16—C12	59.3 (3)
C3—C2—C7—N1	177.8 (2)	C15—C8—C16—C12	−61.3 (3)
C1—C2—C7—N1	−0.4 (4)	C11—C12—C16—C8	−59.8 (3)
C7—N1—C8—C9	−174.7 (2)	C13—C12—C16—C8	60.6 (3)
C7—N1—C8—C15	−54.6 (3)	C13—C14—C17—C10	60.2 (3)
C7—N1—C8—C16	66.4 (3)	C15—C14—C17—C10	−60.3 (3)
N1—C8—C9—C10	−178.11 (19)	C9—C10—C17—C14	60.2 (3)
C15—C8—C9—C10	60.9 (3)	C11—C10—C17—C14	−60.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.95 (3)	1.79 (3)	2.597 (3)	140 (2)

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀N₂O₃
M_r	300.35
Crystal system, space group	Triclinic, P1
Temperature (K)	200
a, b, c (Å)	6.3531 (5), 11.0617 (10), 12.1576 (11)
α, β, γ (°)	62.995 (2), 76.446 (2), 75.487 (2)
V (Å³)	729.71 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.26 × 0.25 × 0.15

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.897, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4583, 2822, 1457
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.146, 0.95
No. of reflections	2822
No. of parameters	202
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.24

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.95 (3)	1.79 (3)	2.597 (3)	140 (2)

Acknowledgements

This work was supported by the Priority Research Centers Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2011–0030747).

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Fernández-G, J. M., del Rio-Portilla, F., Quiroz-García, B., Toscano, R. A. & Salcedo, R. (2001). J. Mol. Struct. 561, 197–207. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar