Bis(2-methyl-1H-benzimidazol-3-ium) naphthalene-1,5-disulfonate

Wei, S.-S.; Jin, S.-W.; Dong, Q.; Cao, X.-C.; Yu, Z.-Y.

doi:10.1107/S1600536812039396

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2964

https://doi.org/10.1107/S1600536812039396

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Bis(2-methyl-1H-benzimidazol-3-ium) naphthalene-1,5-disulfonate

Shuai-Shuai Wei,^a Shou-Wen Jin,^a ^* Qiong Dong,^b Xin-Chao Cao ^a and Ze-Yun Yu ^a

^aTianmu College of ZheJiang A & F University, Lin'An 311300, People's Republic of China, and ^bFaculty of Science, ZheJiang A & F University, Lin'An 311300, People's Republic of China
^*Correspondence e-mail: shouwenjin@yahoo.cn

(Received 6 September 2012; accepted 15 September 2012; online 22 September 2012)

The asymmetric unit of the title compound, 2C₈H₉N₂⁺·C₁₀H₆O₆S₂²⁻, contains a 2-methylbenzimidazolium cation and one half of a naphthalene-1,5-disulfonate anion. The formula unit is generated by an inversion center. In the crystal, N—H⋯O hydrogen bonds link the components into chains along [001]. In addition, weak C—H⋯O hydrogen bonds and weak C—H⋯π interactions are observed. The methyl H atoms were refined as disordered over two sets of sites with equal occupancy.

Related literature

For general background to organic acids, see: Jin et al. (2012 ); Elder et al. (2010 ); Voogt & Blanch (2005 ); Wang et al. (2005 ); Zhang et al. (2005 ).

Experimental

Crystal data

2C₈H₉N₂⁺·C₁₀H₆O₆S₂²⁻
M_r = 552.61
Triclinic, $[P \overline 1]$
a = 8.0360 (7) Å
b = 9.3969 (8) Å
c = 9.5101 (9) Å
α = 105.789 (1)°
β = 103.303 (1)°
γ = 106.497 (2)°
V = 624.75 (10) Å³
Z = 1
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 298 K
0.45 × 0.41 × 0.19 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.888, T_max = 0.951
3137 measured reflections
2169 independent reflections
1694 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.119
S = 1.05
2169 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C9–C11/C11ⁱ/C12ⁱ/C13ⁱ and C11–C13/C9ⁱ/C10ⁱ/C11ⁱ rings, respectively [symmetry code: (i) −x, −y + 1, −z + 1].

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱⁱ	0.86	1.86	2.704 (3)	165
N2—H2⋯O1	0.86	1.88	2.684 (3)	155
C8—H8E⋯O3ⁱⁱⁱ	0.96	2.32	3.230 (4)	158
C4—H4⋯Cg1^iv	0.93	2.61	3.468 (3)	154
C4—H4⋯Cg2^v	0.93	2.61	3.468 (3)	154
Symmetry codes: (ii) x, y, z-1; (iii) -x+1, -y+1, -z+1; (iv) -x, -y, -z; (v) x, y-1, z-1.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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/S1600536812039396/lh5531sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039396/lh5531Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812039396/lh5531Isup3.cml

checkCIF report

Comment top

Sulfonic acids are important compounds, which have been widely used in various fields as coordination chemistry (Wang et al., 2005), pharmaceutical chemistry (Elder et al., 2010), and supramolecular chemistry (Voogt & Blanch, 2005). Recently the main focus for sulfonic acids has been in crystal engineering via hydrogen bonded assembly of sulfonic acid and organic base (Zhang et al., 2005). As an extension of our study concentrating on hydrogen bonded assemblies of organic acids and organic bases (Jin et al., 2012) herein we report the crystal structure of the title compound (I).

The molecular structure of (I) is shown in Fig. 1. The anion lies across an inversion center. In the crystal, N—H···O hydrogen bonds link the components into chains along [001] (Fig. 2). In addition, weak C—H···O hydrogen bonds and weak C—H···π interactions are observed.

Related literature top

For general background to organic [sulfonic?] acids, see: Jin et al. (2012); Elder et al. (2010); Voogt & Blanch (2005); Wang et al. (2005); Zhang et al. (2005).

Experimental top

2-Methyl-1H-benzimidazole (24.0 mg, 0.20 mmol) was dissolved in 10 ml of methanol, and naphthalene-1,5-disulfonic acid tetrahydrate (36 mg, 0.1 mmol) was added. The solution was stirred for 1 h, and then filtered into a test tube. The solution was left standing at room temperature for about one week whereupon colorless block crystals were obtained.

Structure description top

For general background to organic [sulfonic?] acids, see: Jin et al. (2012); Elder et al. (2010); Voogt & Blanch (2005); Wang et al. (2005); Zhang et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 the title compound with displacement ellipsoids drawn at the 30% probability level. Only the symmetry unique cation is shown and in the anion unlabeled atoms are related by the symmetry operator (-x, -y + 1, -z + 1).
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines. H atoms not involved in the hydrogen bonds have been omitted for clarity.

Bis(2-methyl-1H-benzimidazol-3-ium) naphthalene-1,5-disulfonate top

Crystal data top

2C₈H₉N₂⁺·C₁₀H₆O₆S₂²⁻	Z = 1
M_r = 552.61	F(000) = 288
Triclinic, P1	D_x = 1.469 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0360 (7) Å	Cell parameters from 1471 reflections
b = 9.3969 (8) Å	θ = 2.4–28.0°
c = 9.5101 (9) Å	µ = 0.26 mm⁻¹
α = 105.789 (1)°	T = 298 K
β = 103.303 (1)°	Block, colourless
γ = 106.497 (2)°	0.45 × 0.41 × 0.19 mm
V = 624.75 (10) Å³

Data collection top

Bruker SMART CCD diffractometer	2169 independent reflections
Radiation source: fine-focus sealed tube	1694 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
φ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
T_min = 0.888, T_max = 0.951	k = −8→11
3137 measured reflections	l = −10→11

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)] = 0.043	H-atom parameters constrained
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0583P)² + 0.1477P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2169 reflections	Δρ_max = 0.28 e Å⁻³
173 parameters	Δρ_min = −0.37 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.043 (6)

Crystal data top

2C₈H₉N₂⁺·C₁₀H₆O₆S₂²⁻	γ = 106.497 (2)°
M_r = 552.61	V = 624.75 (10) Å³
Triclinic, P1	Z = 1
a = 8.0360 (7) Å	Mo Kα radiation
b = 9.3969 (8) Å	µ = 0.26 mm⁻¹
c = 9.5101 (9) Å	T = 298 K
α = 105.789 (1)°	0.45 × 0.41 × 0.19 mm
β = 103.303 (1)°

Data collection top

Bruker SMART CCD diffractometer	2169 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1694 reflections with I > 2σ(I)
T_min = 0.888, T_max = 0.951	R_int = 0.030
3137 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.05	Δρ_max = 0.28 e Å⁻³
2169 reflections	Δρ_min = −0.37 e Å⁻³
173 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	Occ. (<1)
N1	0.2089 (3)	0.0991 (2)	−0.0901 (2)	0.0390 (5)
H1	0.1838	0.1027	−0.1817	0.047*
N2	0.2562 (3)	0.1632 (2)	0.1561 (2)	0.0404 (5)
H2	0.2664	0.2148	0.2495	0.048*
O1	0.3057 (3)	0.2484 (2)	0.4604 (2)	0.0530 (6)
O2	0.1946 (3)	0.1418 (2)	0.6381 (2)	0.0447 (5)
O3	0.4010 (3)	0.4162 (2)	0.7288 (2)	0.0524 (5)
S1	0.25771 (8)	0.28337 (7)	0.60043 (6)	0.0330 (2)
C1	0.2166 (4)	0.2092 (3)	0.0356 (3)	0.0383 (6)
C2	0.2784 (3)	0.0185 (3)	0.1067 (3)	0.0354 (6)
C3	0.2475 (3)	−0.0230 (3)	−0.0511 (3)	0.0354 (6)
C4	0.2607 (4)	−0.1614 (3)	−0.1376 (3)	0.0436 (7)
H4	0.2379	−0.1902	−0.2438	0.052*
C5	0.3095 (4)	−0.2543 (3)	−0.0584 (3)	0.0495 (7)
H5	0.3195	−0.3484	−0.1125	0.059*
C6	0.3443 (4)	−0.2105 (3)	0.1010 (3)	0.0497 (7)
H6	0.3796	−0.2751	0.1506	0.060*
C7	0.3281 (4)	−0.0747 (3)	0.1870 (3)	0.0455 (7)
H7	0.3493	−0.0467	0.2929	0.055*
C8	0.1861 (4)	0.3582 (3)	0.0410 (4)	0.0552 (8)
H8A	0.1993	0.4176	0.1452	0.083*	0.50
H8B	0.0643	0.3332	−0.0263	0.083*	0.50
H8C	0.2749	0.4206	0.0077	0.083*	0.50
H8D	0.1597	0.3633	−0.0608	0.083*	0.50
H8E	0.2947	0.4477	0.1106	0.083*	0.50
H8F	0.0841	0.3603	0.0767	0.083*	0.50
C9	−0.0943 (3)	0.2568 (3)	0.5733 (3)	0.0356 (6)
H9	−0.1013	0.1681	0.6009	0.043*
C10	0.0652 (3)	0.3429 (3)	0.5591 (2)	0.0284 (5)
C11	0.0793 (3)	0.4782 (3)	0.5137 (2)	0.0275 (5)
C12	0.2405 (3)	0.5702 (3)	0.4963 (3)	0.0336 (6)
H12	0.3438	0.5427	0.5143	0.040*
C13	0.2477 (3)	0.6986 (3)	0.4535 (3)	0.0388 (6)
H13	0.3552	0.7570	0.4421	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0449 (13)	0.0439 (13)	0.0288 (11)	0.0159 (11)	0.0095 (10)	0.0171 (10)
N2	0.0476 (14)	0.0419 (13)	0.0294 (11)	0.0160 (11)	0.0130 (10)	0.0101 (10)
O1	0.0700 (14)	0.0829 (15)	0.0407 (11)	0.0547 (12)	0.0338 (10)	0.0335 (10)
O2	0.0573 (12)	0.0481 (11)	0.0447 (10)	0.0312 (10)	0.0162 (9)	0.0290 (9)
O3	0.0407 (11)	0.0512 (12)	0.0517 (12)	0.0217 (10)	−0.0051 (9)	0.0104 (9)
S1	0.0378 (4)	0.0441 (4)	0.0266 (3)	0.0251 (3)	0.0108 (3)	0.0166 (3)
C1	0.0355 (14)	0.0395 (15)	0.0375 (14)	0.0113 (12)	0.0089 (11)	0.0155 (12)
C2	0.0355 (14)	0.0385 (14)	0.0301 (13)	0.0099 (11)	0.0107 (11)	0.0136 (11)
C3	0.0368 (14)	0.0395 (14)	0.0319 (13)	0.0130 (12)	0.0118 (11)	0.0166 (11)
C4	0.0476 (17)	0.0448 (16)	0.0327 (13)	0.0148 (13)	0.0114 (12)	0.0095 (12)
C5	0.0500 (17)	0.0393 (16)	0.0580 (18)	0.0182 (14)	0.0170 (15)	0.0149 (14)
C6	0.0512 (18)	0.0452 (17)	0.0570 (18)	0.0174 (14)	0.0127 (14)	0.0298 (15)
C7	0.0518 (17)	0.0488 (17)	0.0369 (14)	0.0144 (14)	0.0125 (13)	0.0235 (13)
C8	0.0558 (19)	0.0448 (17)	0.0609 (19)	0.0220 (15)	0.0107 (16)	0.0169 (15)
C9	0.0424 (15)	0.0397 (14)	0.0350 (13)	0.0185 (12)	0.0167 (12)	0.0221 (12)
C10	0.0315 (13)	0.0366 (13)	0.0225 (11)	0.0181 (11)	0.0092 (10)	0.0126 (10)
C11	0.0318 (13)	0.0336 (13)	0.0214 (11)	0.0162 (11)	0.0100 (10)	0.0112 (10)
C12	0.0286 (13)	0.0467 (15)	0.0353 (13)	0.0211 (12)	0.0137 (11)	0.0194 (12)
C13	0.0329 (14)	0.0477 (15)	0.0463 (15)	0.0160 (12)	0.0194 (12)	0.0261 (13)

Geometric parameters (Å, º) top

N1—C1	1.327 (3)	C6—H6	0.9300
N1—C3	1.390 (3)	C7—H7	0.9300
N1—H1	0.8600	C8—H8A	0.9600
N2—C1	1.335 (3)	C8—H8B	0.9600
N2—C2	1.389 (3)	C8—H8C	0.9600
N2—H2	0.8600	C8—H8D	0.9600
O1—S1	1.4491 (17)	C8—H8E	0.9600
O2—S1	1.4543 (17)	C8—H8F	0.9600
O3—S1	1.4427 (19)	C9—C10	1.366 (3)
S1—C10	1.786 (2)	C9—C13ⁱ	1.403 (4)
C1—C8	1.478 (4)	C9—H9	0.9300
C2—C3	1.386 (3)	C10—C11	1.433 (3)
C2—C7	1.390 (4)	C11—C12	1.413 (3)
C3—C4	1.384 (3)	C11—C11ⁱ	1.436 (4)
C4—C5	1.378 (4)	C12—C13	1.365 (3)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.395 (4)	C13—C9ⁱ	1.403 (4)
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.375 (4)

C1—N1—C3	109.56 (19)	H8A—C8—H8B	109.5
C1—N1—H1	125.2	C1—C8—H8C	109.5
C3—N1—H1	125.2	H8A—C8—H8C	109.5
C1—N2—C2	109.1 (2)	H8B—C8—H8C	109.5
C1—N2—H2	125.5	C1—C8—H8D	109.5
C2—N2—H2	125.5	H8A—C8—H8D	141.1
O3—S1—O1	112.92 (13)	H8B—C8—H8D	56.3
O3—S1—O2	113.16 (11)	H8C—C8—H8D	56.3
O1—S1—O2	111.54 (11)	C1—C8—H8E	109.5
O3—S1—C10	106.00 (11)	H8A—C8—H8E	56.3
O1—S1—C10	106.50 (10)	H8B—C8—H8E	141.1
O2—S1—C10	106.07 (11)	H8C—C8—H8E	56.3
N1—C1—N2	108.8 (2)	H8D—C8—H8E	109.5
N1—C1—C8	125.5 (2)	C1—C8—H8F	109.5
N2—C1—C8	125.7 (2)	H8A—C8—H8F	56.3
C3—C2—N2	106.4 (2)	H8B—C8—H8F	56.3
C3—C2—C7	121.8 (2)	H8C—C8—H8F	141.1
N2—C2—C7	131.7 (2)	H8D—C8—H8F	109.5
C4—C3—C2	121.7 (2)	H8E—C8—H8F	109.5
C4—C3—N1	132.2 (2)	C10—C9—C13ⁱ	120.3 (2)
C2—C3—N1	106.1 (2)	C10—C9—H9	119.8
C5—C4—C3	116.6 (2)	C13ⁱ—C9—H9	119.8
C5—C4—H4	121.7	C9—C10—C11	121.2 (2)
C3—C4—H4	121.7	C9—C10—S1	118.13 (18)
C4—C5—C6	121.5 (3)	C11—C10—S1	120.63 (17)
C4—C5—H5	119.2	C12—C11—C10	123.4 (2)
C6—C5—H5	119.2	C12—C11—C11ⁱ	118.9 (2)
C7—C6—C5	122.0 (3)	C10—C11—C11ⁱ	117.7 (3)
C7—C6—H6	119.0	C13—C12—C11	121.3 (2)
C5—C6—H6	119.0	C13—C12—H12	119.4
C6—C7—C2	116.2 (2)	C11—C12—H12	119.4
C6—C7—H7	121.9	C12—C13—C9ⁱ	120.5 (2)
C2—C7—H7	121.9	C12—C13—H13	119.7
C1—C8—H8A	109.5	C9ⁱ—C13—H13	119.7
C1—C8—H8B	109.5

C3—N1—C1—N2	−1.0 (3)	C3—C2—C7—C6	−0.2 (4)
C3—N1—C1—C8	179.1 (3)	N2—C2—C7—C6	−177.4 (3)
C2—N2—C1—N1	1.1 (3)	C13ⁱ—C9—C10—C11	−1.3 (4)
C2—N2—C1—C8	−178.9 (3)	C13ⁱ—C9—C10—S1	178.19 (18)
C1—N2—C2—C3	−0.9 (3)	O3—S1—C10—C9	−118.6 (2)
C1—N2—C2—C7	176.6 (3)	O1—S1—C10—C9	120.9 (2)
N2—C2—C3—C4	179.3 (2)	O2—S1—C10—C9	2.0 (2)
C7—C2—C3—C4	1.5 (4)	O3—S1—C10—C11	60.9 (2)
N2—C2—C3—N1	0.3 (3)	O1—S1—C10—C11	−59.6 (2)
C7—C2—C3—N1	−177.5 (2)	O2—S1—C10—C11	−178.54 (17)
C1—N1—C3—C4	−178.4 (3)	C9—C10—C11—C12	−179.5 (2)
C1—N1—C3—C2	0.4 (3)	S1—C10—C11—C12	1.1 (3)
C2—C3—C4—C5	−1.2 (4)	C9—C10—C11—C11ⁱ	1.1 (4)
N1—C3—C4—C5	177.5 (3)	S1—C10—C11—C11ⁱ	−178.4 (2)
C3—C4—C5—C6	−0.2 (4)	C10—C11—C12—C13	−179.7 (2)
C4—C5—C6—C7	1.4 (5)	C11ⁱ—C11—C12—C13	−0.2 (4)
C5—C6—C7—C2	−1.2 (4)	C11—C12—C13—C9ⁱ	0.4 (4)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C9–C11/C11ⁱ/C12ⁱ/C13ⁱ and C11–C13/C9ⁱ/C10ⁱ/C11ⁱ rings, respectively [symmetry code: (i) -x, -y + 1, -z + 1]

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱⁱ	0.86	1.86	2.704 (3)	165
N2—H2···O1	0.86	1.88	2.684 (3)	155
C8—H8E···O3ⁱⁱⁱ	0.96	2.32	3.230 (4)	158
C4—H4···Cg1^iv	0.93	2.61	3.468 (3)	154
C4—H4···Cg2^v	0.93	2.61	3.468 (3)	154

Symmetry codes: (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) −x, −y, −z; (v) x, y−1, z−1.

Experimental details

Crystal data
Chemical formula	2C₈H₉N₂⁺·C₁₀H₆O₆S₂²⁻
M_r	552.61
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.0360 (7), 9.3969 (8), 9.5101 (9)
α, β, γ (°)	105.789 (1), 103.303 (1), 106.497 (2)
V (Å³)	624.75 (10)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.45 × 0.41 × 0.19

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.888, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	3137, 2169, 1694
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.119, 1.05
No. of reflections	2169
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.37

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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 C9–C11/C11ⁱ/C12ⁱ/C13ⁱ and C11–C13/C9ⁱ/C10ⁱ/C11ⁱ rings, respectively [symmetry code: (i) -x, -y + 1, -z + 1]

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	1.86	2.704 (3)	165
N2—H2···O1	0.86	1.88	2.684 (3)	155
C8—H8E···O3ⁱⁱ	0.96	2.32	3.230 (4)	158
C4—H4···Cg1ⁱⁱⁱ	0.93	2.61	3.468 (3)	154
C4—H4···Cg2^iv	0.93	2.61	3.468 (3)	154

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

Acknowledgements

The authors gratefully acknowledge financial support from the Education Office Foundation of Zhejiang Province (project No. Y201017321) and the Innovation Project of Zhejiang A & F University.

References

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