N-(2-Amino­ethyl)-5-(dimethyl­amino)naphthalene-1-sulfonamide

Zhang, S.; Zhao, B.; Su, Z.; Xia, X.; Zhang, Y.

doi:10.1107/S160053680901962X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1452

doi:10.1107/S160053680901962X

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N-(2-Aminoethyl)-5-(dimethylamino)naphthalene-1-sulfonamide

Shi-lei Zhang,^a ^* Bi-lin Zhao,^a Zhen-hong Su,^b Xian-you Xia ^a and Yong Zhang ^a

^aSchool of Chemical and Materials Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China, and ^bMedical School, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China
^*Correspondence e-mail: zy0340907@yahoo.com.cn

(Received 4 May 2009; accepted 23 May 2009; online 29 May 2009)

In the title compound, C₁₄H₁₉N₃O₂S, the N atom of the dimethylamino group and the S atom are displaced by 0.078 (2) and 0.084 (2) Å, respectively, from the naphthalene ring plane. The 2-aminoethyl group has a coiled conformation with an N—C—C—NH₂ torsion angle of 53.6 (4)°. In the crystal structure, intermolecular N—H⋯N and weak C—H⋯O hydrogen bonds link molecules into chains along [001].

Related literature

For applications of ligands containing the 5-(dimethylamino)naphthalene-1-sulfonyl (dansyl) group, see: Corradini et al. (1996 , 1997 ); Christoforou et al. (2006 ).

Experimental

Crystal data

C₁₄H₁₉N₃O₂S
M_r = 293.38
Orthorhombic, P n a 2₁
a = 15.5221 (15) Å
b = 11.5423 (11) Å
c = 8.1360 (8) Å
V = 1457.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.956, T_max = 0.956
7478 measured reflections
3140 independent reflections
3012 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.107
S = 1.11
3140 reflections
192 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 1332 Friedel pairs
Flack parameter: −0.03 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.93	2.48	3.093 (3)	123
N3—H3A⋯N2	0.88 (5)	2.52 (6)	2.972 (4)	113 (4)
C11—H11⋯O1ⁱ	0.93	2.49	3.146 (3)	128
N2—H2D⋯N3ⁱⁱ	0.87 (3)	2.02 (4)	2.869 (4)	163 (3)
Symmetry codes: (i) x, y, z+1; (ii) $[-x+2, -y+1, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901962X/lh2821sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901962X/lh2821Isup2.hkl

checkCIF report

Comment top

The dansyl (5-(dimethylamino)naphthalene-1-sulfonyl) group has been widely used as a fluorophore in the design of fluorescent probes. Recently many fluorescent ligands bearing dansyl group have been reported (Corradini et al., 1996,1997; Christoforou et al., 2006). We are interested in preparing fluorescent ligands that are expected to bind to hydrophobic sites in proteins or membranes. With this mind, the title compound, (I), was prepared and we report the crystal stucture herein.

In the molecule (Fig. 1), atoms N1 and S1 are located approximately in the naphthalene ring plane with their deviations being 0.078 and 0.084 Å, respectively. The N2—C14—C15—N3 torsion angle of -53.6 (4)° indicates a coiled conformation for the aminoethyl group. In the crystal structure (Fig.2), intermolecular N—H···N and weak C-H···O hydrogen bonds link molecules into one-dimensional chains along [001].

Related literature top

For the applications of ligands containing the 5-(dimethylamino)naphthalene-1-sulfonyl (dansyl) group, see: Corradini et al. (1996, 1997); Christoforou et al. (2006).

Experimental top

Compound (I) was synthesized according to a literature procedure (Corradini et al., 1996). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a dichloromethane solution of (I) at room temperature.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of (I) showing weak hydrogen bonds as dashed lines. Only H atoms involved in hydrogen bonds are shown.

N-(2-Aminoethyl)-5-(dimethylamino)naphthalene-1-sulfonamide top

Crystal data top

C₁₄H₁₉N₃O₂S	F(000) = 624
M_r = 293.38	D_x = 1.337 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4085 reflections
a = 15.5221 (15) Å	θ = 2.2–28.0°
b = 11.5423 (11) Å	µ = 0.23 mm⁻¹
c = 8.1360 (8) Å	T = 298 K
V = 1457.7 (2) Å³	Block, colorless
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	3140 independent reflections
Radiation source: fine-focus sealed tube	3012 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −19→13
T_min = 0.956, T_max = 0.956	k = −14→14
7478 measured reflections	l = −10→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0621P)² + 0.0989P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
3140 reflections	Δρ_max = 0.24 e Å⁻³
192 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1332 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (8)

Crystal data top

C₁₄H₁₉N₃O₂S	V = 1457.7 (2) Å³
M_r = 293.38	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 15.5221 (15) Å	µ = 0.23 mm⁻¹
b = 11.5423 (11) Å	T = 298 K
c = 8.1360 (8) Å	0.20 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	3140 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	3012 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.956	R_int = 0.029
7478 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	Δρ_max = 0.24 e Å⁻³
S = 1.11	Δρ_min = −0.25 e Å⁻³
3140 reflections	Absolute structure: Flack (1983), 1332 Friedel pairs
192 parameters	Absolute structure parameter: −0.03 (8)
1 restraint

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
C1	0.6783 (2)	0.2592 (3)	1.2600 (5)	0.0711 (9)
H1A	0.6195	0.2620	1.2236	0.107*
H1B	0.6797	0.2519	1.3775	0.107*
H1C	0.7065	0.1937	1.2111	0.107*
C2	0.67195 (17)	0.4676 (3)	1.2579 (4)	0.0615 (7)
H2A	0.7030	0.5368	1.2300	0.092*
H2B	0.6616	0.4659	1.3742	0.092*
H2C	0.6180	0.4665	1.2004	0.092*
C3	0.75553 (12)	0.36601 (19)	1.0498 (3)	0.0381 (5)
C4	0.72410 (14)	0.43583 (19)	0.9255 (3)	0.0451 (5)
H4	0.6796	0.4874	0.9477	0.054*
C5	0.75833 (15)	0.4299 (2)	0.7670 (3)	0.0480 (6)
H5	0.7350	0.4767	0.6853	0.058*
C6	0.82454 (15)	0.3580 (2)	0.7281 (3)	0.0445 (5)
H6	0.8451	0.3547	0.6208	0.053*
C7	0.86251 (12)	0.28748 (17)	0.8530 (3)	0.0323 (4)
C8	0.93538 (13)	0.21356 (16)	0.8264 (3)	0.0309 (4)
C9	0.96977 (14)	0.14947 (18)	0.9519 (3)	0.0366 (4)
H9	1.0158	0.0999	0.9311	0.044*
C10	0.93643 (14)	0.15783 (18)	1.1106 (3)	0.0379 (4)
H10	0.9610	0.1151	1.1954	0.045*
C11	0.86816 (12)	0.22823 (16)	1.1418 (3)	0.0363 (4)
H11	0.8473	0.2345	1.2486	0.044*
C12	0.82814 (12)	0.29230 (16)	1.0143 (3)	0.0322 (4)
C14	1.10343 (19)	0.3731 (3)	0.6827 (4)	0.0689 (9)
H14A	1.1354	0.4225	0.6080	0.083*
H14B	1.1400	0.3079	0.7107	0.083*
C15	1.0839 (2)	0.4406 (3)	0.8375 (5)	0.0833 (11)
H15A	1.0609	0.3874	0.9188	0.100*
H15B	1.1375	0.4712	0.8805	0.100*
N1	0.72278 (13)	0.36630 (17)	1.2108 (3)	0.0467 (5)
O1	0.92413 (13)	0.18510 (17)	0.5084 (2)	0.0558 (5)
O2	1.05529 (12)	0.12231 (15)	0.6510 (2)	0.0553 (4)
N2	1.02722 (14)	0.33007 (18)	0.5987 (3)	0.0495 (5)
H2D	1.0054 (19)	0.358 (3)	0.508 (5)	0.059*
N3	1.0237 (3)	0.5358 (3)	0.8182 (5)	0.0993 (13)
H3A	0.980 (3)	0.499 (5)	0.773 (8)	0.119*
H3B	1.044 (3)	0.588 (4)	0.752 (7)	0.119*
S1	0.98740 (3)	0.20448 (4)	0.63277 (8)	0.03840 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0693 (17)	0.0655 (18)	0.079 (2)	0.0010 (15)	0.0311 (15)	0.0156 (17)
C2	0.0547 (14)	0.0663 (17)	0.0635 (18)	0.0210 (13)	0.0108 (12)	−0.0083 (14)
C3	0.0340 (10)	0.0365 (11)	0.0439 (12)	0.0001 (8)	−0.0005 (9)	−0.0006 (9)
C4	0.0377 (10)	0.0406 (12)	0.0570 (14)	0.0071 (9)	−0.0008 (10)	0.0082 (11)
C5	0.0472 (12)	0.0486 (13)	0.0482 (14)	0.0062 (10)	−0.0097 (10)	0.0171 (11)
C6	0.0533 (12)	0.0461 (12)	0.0343 (11)	−0.0003 (10)	−0.0053 (9)	0.0120 (10)
C7	0.0331 (9)	0.0315 (9)	0.0323 (10)	−0.0037 (7)	−0.0041 (8)	0.0023 (8)
C8	0.0369 (10)	0.0294 (9)	0.0264 (10)	−0.0018 (8)	0.0014 (8)	−0.0008 (8)
C9	0.0418 (10)	0.0344 (11)	0.0336 (10)	0.0061 (8)	−0.0015 (9)	0.0015 (8)
C10	0.0450 (10)	0.0387 (10)	0.0299 (11)	0.0066 (8)	−0.0045 (8)	0.0077 (8)
C11	0.0434 (10)	0.0367 (9)	0.0286 (9)	0.0018 (7)	0.0003 (9)	0.0037 (9)
C12	0.0328 (9)	0.0303 (10)	0.0335 (10)	−0.0049 (7)	−0.0015 (8)	0.0030 (8)
C14	0.0647 (16)	0.0609 (16)	0.081 (3)	−0.0208 (14)	0.0173 (15)	−0.0189 (15)
C15	0.099 (2)	0.077 (2)	0.075 (2)	−0.034 (2)	0.012 (2)	−0.0264 (19)
N1	0.0462 (10)	0.0458 (11)	0.0482 (11)	0.0089 (9)	0.0133 (9)	0.0015 (9)
O1	0.0778 (12)	0.0595 (11)	0.0302 (8)	−0.0089 (9)	−0.0003 (8)	−0.0045 (8)
O2	0.0729 (10)	0.0498 (9)	0.0432 (9)	0.0162 (8)	0.0174 (9)	−0.0028 (8)
N2	0.0641 (13)	0.0425 (10)	0.0420 (14)	−0.0092 (9)	0.0122 (9)	0.0037 (9)
N3	0.158 (4)	0.0527 (18)	0.087 (2)	−0.0261 (19)	0.036 (2)	−0.0248 (16)
S1	0.0538 (3)	0.0341 (2)	0.0274 (2)	−0.00129 (19)	0.0066 (3)	−0.0034 (3)

Geometric parameters (Å, º) top

C1—N1	1.472 (3)	C8—S1	1.773 (2)
C1—H1A	0.9600	C9—C10	1.395 (3)
C1—H1B	0.9600	C9—H9	0.9300
C1—H1C	0.9600	C10—C11	1.359 (3)
C2—N1	1.461 (3)	C10—H10	0.9300
C2—H2A	0.9600	C11—C12	1.417 (3)
C2—H2B	0.9600	C11—H11	0.9300
C2—H2C	0.9600	C14—N2	1.454 (4)
C3—C4	1.382 (3)	C14—C15	1.511 (5)
C3—N1	1.405 (3)	C14—H14A	0.9700
C3—C12	1.441 (3)	C14—H14B	0.9700
C4—C5	1.396 (3)	C15—N3	1.450 (5)
C4—H4	0.9300	C15—H15A	0.9700
C5—C6	1.358 (3)	C15—H15B	0.9700
C5—H5	0.9300	O1—S1	1.4278 (19)
C6—C7	1.429 (3)	O2—S1	1.4255 (18)
C6—H6	0.9300	N2—S1	1.600 (2)
C7—C12	1.417 (3)	N2—H2D	0.87 (3)
C7—C8	1.433 (3)	N3—H3A	0.88 (5)
C8—C9	1.369 (3)	N3—H3B	0.87 (5)

N1—C1—H1A	109.5	C9—C10—H10	119.9
N1—C1—H1B	109.5	C10—C11—C12	121.1 (2)
H1A—C1—H1B	109.5	C10—C11—H11	119.4
N1—C1—H1C	109.5	C12—C11—H11	119.4
H1A—C1—H1C	109.5	C11—C12—C7	119.47 (18)
H1B—C1—H1C	109.5	C11—C12—C3	120.3 (2)
N1—C2—H2A	109.5	C7—C12—C3	120.20 (18)
N1—C2—H2B	109.5	N2—C14—C15	113.9 (3)
H2A—C2—H2B	109.5	N2—C14—H14A	108.8
N1—C2—H2C	109.5	C15—C14—H14A	108.8
H2A—C2—H2C	109.5	N2—C14—H14B	108.8
H2B—C2—H2C	109.5	C15—C14—H14B	108.8
C4—C3—N1	123.6 (2)	H14A—C14—H14B	107.7
C4—C3—C12	118.3 (2)	N3—C15—C14	115.5 (3)
N1—C3—C12	118.11 (19)	N3—C15—H15A	108.4
C3—C4—C5	120.8 (2)	C14—C15—H15A	108.4
C3—C4—H4	119.6	N3—C15—H15B	108.4
C5—C4—H4	119.6	C14—C15—H15B	108.4
C6—C5—C4	122.3 (2)	H15A—C15—H15B	107.5
C6—C5—H5	118.9	C3—N1—C2	116.2 (2)
C4—C5—H5	118.9	C3—N1—C1	114.9 (2)
C5—C6—C7	119.6 (2)	C2—N1—C1	110.3 (2)
C5—C6—H6	120.2	C14—N2—S1	122.8 (2)
C7—C6—H6	120.2	C14—N2—H2D	126 (2)
C12—C7—C6	118.73 (19)	S1—N2—H2D	109 (2)
C12—C7—C8	117.42 (17)	C15—N3—H3A	100 (3)
C6—C7—C8	123.8 (2)	C15—N3—H3B	111 (3)
C9—C8—C7	121.08 (19)	H3A—N3—H3B	111 (5)
C9—C8—S1	116.94 (16)	O2—S1—O1	118.56 (12)
C7—C8—S1	121.94 (15)	O2—S1—N2	109.58 (12)
C8—C9—C10	120.57 (19)	O1—S1—N2	106.55 (12)
C8—C9—H9	119.7	O2—S1—C8	106.46 (10)
C10—C9—H9	119.7	O1—S1—C8	109.01 (10)
C11—C10—C9	120.2 (2)	N2—S1—C8	106.04 (10)
C11—C10—H10	119.9

N1—C3—C4—C5	−178.7 (2)	C4—C3—C12—C11	173.49 (19)
C12—C3—C4—C5	3.9 (3)	N1—C3—C12—C11	−4.0 (3)
C3—C4—C5—C6	−1.4 (4)	C4—C3—C12—C7	−3.6 (3)
C4—C5—C6—C7	−1.5 (4)	N1—C3—C12—C7	178.89 (18)
C5—C6—C7—C12	1.7 (3)	N2—C14—C15—N3	−53.6 (4)
C5—C6—C7—C8	−176.60 (19)	C4—C3—N1—C2	−18.4 (3)
C12—C7—C8—C9	0.6 (3)	C12—C3—N1—C2	159.0 (2)
C6—C7—C8—C9	178.9 (2)	C4—C3—N1—C1	112.6 (3)
C12—C7—C8—S1	−177.20 (14)	C12—C3—N1—C1	−70.0 (3)
C6—C7—C8—S1	1.1 (3)	C15—C14—N2—S1	−91.9 (3)
C7—C8—C9—C10	−2.3 (3)	C14—N2—S1—O2	−40.1 (2)
S1—C8—C9—C10	175.56 (16)	C14—N2—S1—O1	−169.58 (19)
C8—C9—C10—C11	1.3 (3)	C14—N2—S1—C8	74.4 (2)
C9—C10—C11—C12	1.5 (3)	C9—C8—S1—O2	3.06 (19)
C10—C11—C12—C7	−3.2 (3)	C7—C8—S1—O2	−179.09 (16)
C10—C11—C12—C3	179.68 (19)	C9—C8—S1—O1	132.05 (17)
C6—C7—C12—C11	−176.28 (19)	C7—C8—S1—O1	−50.11 (19)
C8—C7—C12—C11	2.1 (3)	C9—C8—S1—N2	−113.59 (18)
C6—C7—C12—C3	0.8 (3)	C7—C8—S1—N2	64.25 (19)
C8—C7—C12—C3	179.24 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.48	3.093 (3)	123
N3—H3A···N2	0.88 (5)	2.52 (6)	2.972 (4)	113 (4)
C11—H11···O1ⁱ	0.93	2.49	3.146 (3)	128
N2—H2D···N3ⁱⁱ	0.87 (3)	2.02 (4)	2.869 (4)	163 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₉N₃O₂S
M_r	293.38
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	15.5221 (15), 11.5423 (11), 8.1360 (8)
V (Å³)	1457.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.956, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	7478, 3140, 3012
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.107, 1.11
No. of reflections	3140
No. of parameters	192
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.25
Absolute structure	Flack (1983), 1332 Friedel pairs
Absolute structure parameter	−0.03 (8)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.48	3.093 (3)	123
N3—H3A···N2	0.88 (5)	2.52 (6)	2.972 (4)	113 (4)
C11—H11···O1ⁱ	0.93	2.49	3.146 (3)	128
N2—H2D···N3ⁱⁱ	0.87 (3)	2.02 (4)	2.869 (4)	163 (3)

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

References

Bruker (2007). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Christoforou, A. M., Marzilli, P. A. & Marzilli, L. G. (2006). Inorg. Chem. 45, 6771–6781. Web of Science CrossRef PubMed CAS Google Scholar
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Corradini, R., Dossena, A., Marchelli, R., Panagia, A., Sartor, G., Saviano, M., Lombardi, A. & Pavone, V. (1996). Chem. Eur. J. 2, 373–381. CrossRef CAS Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 6| June 2009| Page o1452

doi:10.1107/S160053680901962X

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