1-[5-(Dimethyl­amino)-1-naphthylsulfon­yl]imidazolidine-2-thione

Zhang, Y.; Teng, L.

doi:10.1107/S1600536810029788

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2181

https://doi.org/10.1107/S1600536810029788

Open

access

1-[5-(Dimethylamino)-1-naphthylsulfonyl]imidazolidine-2-thione

Yong Zhang ^a ^* and Lei Teng ^a

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

(Received 21 July 2010; accepted 27 July 2010; online 31 July 2010)

In the title molecule, C₁₅H₁₇N₃O₂S₂, the dihedral angle between the naphthalene ring system and the imidazole ring is 89.63 (2)°. The crystal structure is stablized by weak intermolecuar C—H⋯π and N—H⋯π interactions.

Related literature

For the applications of compounds containing a 5-(dimethylamino)naphthalene-1-sulfonyl group, see: Corradini et al. (1996 , 1997 ); Christoforou et al. (2006 ). For a related structure, see: Zhang et al. (2009 ). For the synthetic procedure, see: Corradini et al. (1996).

Experimental

Crystal data

C₁₅H₁₇N₃O₂S₂
M_r = 335.44
Monoclinic, P 2₁ /n
a = 15.364 (4) Å
b = 6.9814 (18) Å
c = 15.470 (4) Å
β = 113.967 (4)°
V = 1516.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 298 K
0.33 × 0.32 × 0.28 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.955, T_max = 0.965
8935 measured reflections
3302 independent reflections
2605 reflections with I > 2σ(I)
R_int = 0.104

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.145
S = 1.04
3302 reflections
204 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C5/C10 and C5–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg1ⁱ	0.93	2.88	3.667 (3)	143
N3—H3A⋯Cg2ⁱⁱ	0.88 (3)	2.58 (3)	3.433 (3)	165 (2)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+2.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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: https://doi.org/10.1107/S1600536810029788/lh5094sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810029788/lh5094Isup2.hkl

checkCIF report

Comment top

The dansyl (5-(dimethylamino)naphthalene-1-sulfonyl) group has been widely used as a fluorophore due to its good fluorescent properties. Recently many dansyl derivatives have been reported (Corradini et al., 1996,1997; Christoforou et al., 2006). We show great interest in preparing fluorescent probes that are expected to bind to hydrophobic sites in proteins or membranes and have recently published a structure reslted to the title compound (Zhang et al., 2009). With this in mind, the title compound, (I), was prepared and we report herein the crystal stucture.

In the molecular structure (Fig. 1), the dihedral angle between the naphthalene ring and five-membered heterocyclic ring is 89.63 (2)°. The crystal structure is stablized by weak intermolecuar C—H···π and N—H···π interactions.

Related literature top

For the applications of compounds containing a 5-(dimethylamino)naphthalene-1-sulfonyl group, see: Corradini et al. (1996, 1997); Christoforou et al. (2006). For a related structure, see: Zhang et al. (2009). For the synthetic procedure, see: Corradini et al. (1996).

Experimental top

The intermediate N-(2-Aminoethyl)-5-(dimethylamino)naphthalene-1-sulfonamide was synthesized according to a literature procedure (Corradini et al., 1996). Carbon bisulfide (0.76 g, 10 mmol) and sodium hydroxide(0.40 g, 10 mmol) were added into a stirred solution of the above intermediate (1.47 g, 5 mmol) in dry methanol (20 ml).The reaction mixture was allowed to stir for 24 hr at 293 K. The progress of the reaction was monitored by TLC, untill the completion of reaction. The solvent was evaporated and the residue was purified by column chromatography (dichloromethane-ethyl acetate,1:8 v/v) to afford the title compound as a yellow solid. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in dichloromethane at room temperature.

Structure description top

For the applications of compounds containing a 5-(dimethylamino)naphthalene-1-sulfonyl group, see: Corradini et al. (1996, 1997); Christoforou et al. (2006). For a related structure, see: Zhang et al. (2009). For the synthetic procedure, see: Corradini et al. (1996).

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.

1-[5-(Dimethylamino)-1-naphthylsulfonyl]imidazolidine-2-thione top

Crystal data top

C₁₅H₁₇N₃O₂S₂	F(000) = 700
M_r = 335.44	D_x = 1.465 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2682 reflections
a = 15.364 (4) Å	θ = 2.4–28.1°
b = 6.9814 (18) Å	µ = 0.36 mm⁻¹
c = 15.470 (4) Å	T = 298 K
β = 113.967 (4)°	Block, yellow
V = 1516.3 (7) Å³	0.33 × 0.32 × 0.28 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3302 independent reflections
Radiation source: fine-focus sealed tube	2605 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.104
φ and ω scans	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −17→19
T_min = 0.955, T_max = 0.965	k = −8→8
8935 measured reflections	l = −19→19

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.071P)²] where P = (F_o² + 2F_c²)/3
3302 reflections	(Δ/σ)_max = 0.001
204 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₅H₁₇N₃O₂S₂	V = 1516.3 (7) Å³
M_r = 335.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.364 (4) Å	µ = 0.36 mm⁻¹
b = 6.9814 (18) Å	T = 298 K
c = 15.470 (4) Å	0.33 × 0.32 × 0.28 mm
β = 113.967 (4)°

Data collection top

Bruker SMART CCD diffractometer	3302 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	2605 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.965	R_int = 0.104
8935 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.50 e Å⁻³
3302 reflections	Δρ_min = −0.35 e Å⁻³
204 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
C1	0.61885 (15)	0.6070 (3)	0.72722 (15)	0.0306 (5)
C2	0.68621 (19)	0.7474 (3)	0.76019 (18)	0.0379 (6)
H2	0.6868	0.8466	0.7203	0.045*
C3	0.75453 (19)	0.7430 (3)	0.85392 (19)	0.0434 (6)
H3	0.8011	0.8375	0.8746	0.052*
C4	0.75429 (17)	0.6051 (3)	0.91479 (17)	0.0384 (6)
H4	0.7983	0.6099	0.9774	0.046*
C5	0.68768 (15)	0.4529 (3)	0.88431 (15)	0.0271 (5)
C6	0.68432 (16)	0.2951 (3)	0.94243 (16)	0.0299 (5)
C7	0.62594 (17)	0.1403 (3)	0.90561 (16)	0.0342 (5)
H7	0.6253	0.0398	0.9448	0.041*
C8	0.56701 (17)	0.1343 (3)	0.80839 (17)	0.0370 (6)
H8	0.5298	0.0267	0.7828	0.044*
C9	0.56426 (17)	0.2841 (3)	0.75203 (17)	0.0336 (5)
H9	0.5235	0.2792	0.6883	0.040*
C10	0.62191 (14)	0.4484 (3)	0.78765 (15)	0.0271 (5)
C11	0.45077 (18)	0.6337 (5)	0.6290 (2)	0.0536 (7)
H11A	0.4425	0.5578	0.6769	0.080*
H11B	0.4051	0.5953	0.5678	0.080*
H11C	0.4416	0.7665	0.6391	0.080*
C12	0.5635 (2)	0.7304 (4)	0.5667 (2)	0.0576 (8)
H12A	0.5604	0.8616	0.5837	0.086*
H12B	0.5157	0.7072	0.5043	0.086*
H12C	0.6253	0.7046	0.5677	0.086*
C13	0.7299 (2)	0.6395 (4)	1.1372 (2)	0.0589 (8)
H13A	0.7391	0.7055	1.0863	0.071*
H13B	0.7896	0.6394	1.1929	0.071*
C14	0.6522 (2)	0.7308 (4)	1.1575 (2)	0.0515 (7)
H14A	0.6764	0.7806	1.2216	0.062*
H14B	0.6223	0.8341	1.1135	0.062*
C15	0.60716 (16)	0.4138 (3)	1.11357 (15)	0.0336 (5)
N1	0.54715 (14)	0.6055 (3)	0.63401 (13)	0.0381 (5)
N2	0.69536 (13)	0.4434 (3)	1.10932 (13)	0.0328 (4)
N3	0.58699 (18)	0.5772 (3)	1.14554 (17)	0.0496 (6)
H3A	0.534 (2)	0.590 (4)	1.154 (2)	0.059*
O1	0.74468 (12)	0.1037 (2)	1.09977 (12)	0.0422 (4)
O2	0.84230 (11)	0.3748 (3)	1.09114 (11)	0.0414 (4)
S1	0.75069 (4)	0.29031 (8)	1.06638 (4)	0.03206 (19)
S2	0.53971 (5)	0.22082 (10)	1.08475 (6)	0.0524 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0297 (12)	0.0365 (13)	0.0286 (12)	0.0012 (10)	0.0150 (9)	0.0006 (9)
C2	0.0425 (14)	0.0352 (13)	0.0384 (13)	−0.0015 (10)	0.0190 (11)	0.0049 (10)
C3	0.0452 (16)	0.0396 (14)	0.0437 (15)	−0.0167 (11)	0.0165 (12)	−0.0017 (11)
C4	0.0372 (14)	0.0423 (14)	0.0316 (12)	−0.0092 (11)	0.0097 (10)	−0.0028 (10)
C5	0.0263 (11)	0.0309 (11)	0.0263 (11)	0.0000 (9)	0.0129 (8)	−0.0013 (9)
C6	0.0266 (11)	0.0343 (12)	0.0291 (11)	0.0026 (9)	0.0118 (9)	0.0001 (9)
C7	0.0402 (13)	0.0308 (12)	0.0339 (12)	−0.0022 (10)	0.0173 (10)	−0.0006 (10)
C8	0.0413 (14)	0.0339 (13)	0.0393 (13)	−0.0111 (11)	0.0200 (11)	−0.0103 (10)
C9	0.0303 (12)	0.0416 (13)	0.0295 (12)	−0.0041 (10)	0.0126 (9)	−0.0060 (10)
C10	0.0232 (10)	0.0328 (12)	0.0280 (11)	0.0021 (9)	0.0130 (9)	−0.0015 (9)
C11	0.0345 (15)	0.072 (2)	0.0477 (16)	0.0080 (14)	0.0092 (12)	0.0107 (14)
C12	0.0583 (19)	0.073 (2)	0.0356 (15)	−0.0115 (15)	0.0130 (13)	0.0146 (13)
C13	0.0640 (19)	0.0383 (15)	0.083 (2)	−0.0096 (14)	0.0386 (17)	−0.0153 (15)
C14	0.070 (2)	0.0387 (15)	0.0469 (16)	0.0002 (13)	0.0246 (15)	−0.0069 (12)
C15	0.0395 (13)	0.0371 (13)	0.0266 (11)	0.0071 (10)	0.0158 (10)	0.0067 (10)
N1	0.0322 (11)	0.0490 (12)	0.0302 (10)	0.0000 (9)	0.0099 (8)	0.0070 (9)
N2	0.0342 (11)	0.0307 (10)	0.0343 (11)	−0.0012 (8)	0.0145 (8)	−0.0036 (8)
N3	0.0595 (15)	0.0440 (13)	0.0595 (15)	0.0068 (11)	0.0389 (13)	−0.0025 (11)
O1	0.0509 (11)	0.0343 (9)	0.0399 (10)	0.0105 (8)	0.0169 (8)	0.0090 (7)
O2	0.0284 (9)	0.0521 (11)	0.0391 (10)	0.0026 (8)	0.0092 (7)	0.0035 (8)
S1	0.0314 (3)	0.0339 (3)	0.0303 (3)	0.0052 (2)	0.0119 (2)	0.0030 (2)
S2	0.0465 (4)	0.0484 (4)	0.0687 (5)	−0.0096 (3)	0.0300 (4)	0.0000 (3)

Geometric parameters (Å, º) top

C1—C2	1.365 (3)	C11—H11B	0.9600
C1—N1	1.415 (3)	C11—H11C	0.9600
C1—C10	1.437 (3)	C12—N1	1.456 (3)
C2—C3	1.403 (4)	C12—H12A	0.9600
C2—H2	0.9300	C12—H12B	0.9600
C3—C4	1.348 (3)	C12—H12C	0.9600
C3—H3	0.9300	C13—N2	1.468 (3)
C4—C5	1.417 (3)	C13—C14	1.496 (4)
C4—H4	0.9300	C13—H13A	0.9700
C5—C10	1.425 (3)	C13—H13B	0.9700
C5—C6	1.436 (3)	C14—N3	1.428 (3)
C6—C7	1.372 (3)	C14—H14A	0.9700
C6—S1	1.769 (2)	C14—H14B	0.9700
C7—C8	1.406 (3)	C15—N3	1.329 (3)
C7—H7	0.9300	C15—N2	1.398 (3)
C8—C9	1.351 (3)	C15—S2	1.647 (2)
C8—H8	0.9300	N2—S1	1.6628 (19)
C9—C10	1.417 (3)	N3—H3A	0.88 (3)
C9—H9	0.9300	O1—S1	1.4182 (17)
C11—N1	1.464 (3)	O2—S1	1.4275 (17)
C11—H11A	0.9600

C2—C1—N1	123.0 (2)	N1—C12—H12A	109.5
C2—C1—C10	119.4 (2)	N1—C12—H12B	109.5
N1—C1—C10	117.6 (2)	H12A—C12—H12B	109.5
C1—C2—C3	120.4 (2)	N1—C12—H12C	109.5
C1—C2—H2	119.8	H12A—C12—H12C	109.5
C3—C2—H2	119.8	H12B—C12—H12C	109.5
C4—C3—C2	121.7 (2)	N2—C13—C14	103.6 (2)
C4—C3—H3	119.2	N2—C13—H13A	111.0
C2—C3—H3	119.2	C14—C13—H13A	111.0
C3—C4—C5	120.7 (2)	N2—C13—H13B	111.0
C3—C4—H4	119.7	C14—C13—H13B	111.0
C5—C4—H4	119.7	H13A—C13—H13B	109.0
C4—C5—C10	118.31 (19)	N3—C14—C13	103.3 (2)
C4—C5—C6	124.9 (2)	N3—C14—H14A	111.1
C10—C5—C6	116.72 (19)	C13—C14—H14A	111.1
C7—C6—C5	121.9 (2)	N3—C14—H14B	111.1
C7—C6—S1	115.27 (17)	C13—C14—H14B	111.1
C5—C6—S1	122.80 (17)	H14A—C14—H14B	109.1
C6—C7—C8	119.7 (2)	N3—C15—N2	105.5 (2)
C6—C7—H7	120.1	N3—C15—S2	125.9 (2)
C8—C7—H7	120.1	N2—C15—S2	128.54 (17)
C9—C8—C7	120.3 (2)	C1—N1—C12	115.8 (2)
C9—C8—H8	119.8	C1—N1—C11	113.87 (19)
C7—C8—H8	119.8	C12—N1—C11	110.3 (2)
C8—C9—C10	121.7 (2)	C15—N2—C13	111.46 (19)
C8—C9—H9	119.2	C15—N2—S1	125.90 (16)
C10—C9—H9	119.2	C13—N2—S1	122.26 (17)
C9—C10—C5	119.38 (19)	C15—N3—C14	115.8 (2)
C9—C10—C1	121.37 (19)	C15—N3—H3A	121 (2)
C5—C10—C1	119.17 (19)	C14—N3—H3A	123.1 (19)
N1—C11—H11A	109.5	O1—S1—O2	119.00 (10)
N1—C11—H11B	109.5	O1—S1—N2	108.99 (10)
H11A—C11—H11B	109.5	O2—S1—N2	103.62 (10)
N1—C11—H11C	109.5	O1—S1—C6	108.55 (11)
H11A—C11—H11C	109.5	O2—S1—C6	110.75 (10)
H11B—C11—H11C	109.5	N2—S1—C6	104.94 (10)

N1—C1—C2—C3	178.9 (2)	C2—C1—N1—C12	16.4 (3)
C10—C1—C2—C3	−3.7 (4)	C10—C1—N1—C12	−161.2 (2)
C1—C2—C3—C4	−2.1 (4)	C2—C1—N1—C11	−113.0 (3)
C2—C3—C4—C5	3.6 (4)	C10—C1—N1—C11	69.5 (3)
C3—C4—C5—C10	0.7 (3)	N3—C15—N2—C13	−2.2 (3)
C3—C4—C5—C6	177.1 (2)	S2—C15—N2—C13	177.2 (2)
C4—C5—C6—C7	−171.7 (2)	N3—C15—N2—S1	−175.13 (17)
C10—C5—C6—C7	4.8 (3)	S2—C15—N2—S1	4.3 (3)
C4—C5—C6—S1	11.1 (3)	C14—C13—N2—C15	−1.1 (3)
C10—C5—C6—S1	−172.47 (15)	C14—C13—N2—S1	172.14 (18)
C5—C6—C7—C8	−0.3 (3)	N2—C15—N3—C14	5.0 (3)
S1—C6—C7—C8	177.21 (17)	S2—C15—N3—C14	−174.4 (2)
C6—C7—C8—C9	−3.2 (3)	C13—C14—N3—C15	−5.7 (3)
C7—C8—C9—C10	1.9 (4)	C15—N2—S1—O1	−44.0 (2)
C8—C9—C10—C5	2.9 (3)	C13—N2—S1—O1	143.8 (2)
C8—C9—C10—C1	179.8 (2)	C15—N2—S1—O2	−171.64 (17)
C4—C5—C10—C9	170.7 (2)	C13—N2—S1—O2	16.1 (2)
C6—C5—C10—C9	−6.0 (3)	C15—N2—S1—C6	72.1 (2)
C4—C5—C10—C1	−6.3 (3)	C13—N2—S1—C6	−100.1 (2)
C6—C5—C10—C1	177.01 (18)	C7—C6—S1—O1	12.6 (2)
C2—C1—C10—C9	−169.1 (2)	C5—C6—S1—O1	−169.92 (17)
N1—C1—C10—C9	8.5 (3)	C7—C6—S1—O2	145.02 (18)
C2—C1—C10—C5	7.8 (3)	C5—C6—S1—O2	−37.5 (2)
N1—C1—C10—C5	−174.59 (19)	C7—C6—S1—N2	−103.77 (18)
N2—C13—C14—N3	3.7 (3)	C5—C6—S1—N2	73.67 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C5/C10 and C5–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1ⁱ	0.93	2.88	3.667 (3)	143
N3—H3A···Cg2ⁱⁱ	0.88 (3)	2.58 (3)	3.433 (3)	165 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇N₃O₂S₂
M_r	335.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	15.364 (4), 6.9814 (18), 15.470 (4)
β (°)	113.967 (4)
V (Å³)	1516.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.33 × 0.32 × 0.28

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.955, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	8935, 3302, 2605
R_int	0.104
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.145, 1.04
No. of reflections	3302
No. of parameters	204
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.35

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

Cg1 and Cg2 are the centroids of the C1–C5/C10 and C5–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1ⁱ	0.93	2.88	3.667 (3)	143
N3—H3A···Cg2ⁱⁱ	0.88 (3)	2.58 (3)	3.433 (3)	165 (2)

Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+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
Corradini, R., Dossena, A., Galaverna, G., Marchelli, R., Panagia, A. & Sarto, G. (1997). J. Org. Chem. 62, 6283–6289. CrossRef CAS Web of Science Google Scholar
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
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
Zhang, Y., Qu, Y. & Liu, T. (2009). Acta Cryst. E65, o2752. Web of Science CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2181

https://doi.org/10.1107/S1600536810029788

Open

access