1-(2-Ureidoeth­yl)quinolinium tetra­phenyl­borate

Dong, Z.-Y.; Yang, Y.; Gao, G.-H.

doi:10.1107/S1600536811027218

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2031

doi:10.1107/S1600536811027218

Open

access

1-(2-Ureidoethyl)quinolinium tetraphenylborate

Zhi-Yun Dong,^a Yu Yang ^a and Guo-Hua Gao ^a ^*

^aShanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062, People's Republic of China
^*Correspondence e-mail: ghgao@chem.ecnu.edu.cn

(Received 28 June 2011; accepted 7 July 2011; online 13 July 2011)

In the cation of the title salt, C₁₂H₁₄N₃O⁺·C₂₄H₂₀B⁻, the dihedral angle between the quinoline ring and the mean plane of the urea fragment is 61.51 (5)°. In the crystal, the cations interact through weak C—H⋯O hydrogen bonding, forming a zigzag chain along the c-axis direction; the cations and anions are involved in weak intermolecular C—H⋯π and N—H⋯π interactions as donors and acceptors, respectively.

Related literature

For applications of ionic liquids, see: Zhao & Malhotra (2002 ); Chauvin & Olivier-Bourbigou (1995 ); Seddon (2001 ); Hapiot & Lagros (2008 ); Blaster & Studer (2003 ). For a related structure, see: Youngme et al. (2006 ).

Experimental

Crystal data

C₁₂H₁₄N₃O⁺·C₂₄H₂₀B⁻
M_r = 535.47
Orthorhombic, A b a 2
a = 25.5434 (11) Å
b = 18.7954 (8) Å
c = 12.0837 (5) Å
V = 5801.4 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 173 K
0.40 × 0.18 × 0.13 mm

Data collection

Rigaku Saturn CCD diffractometer
32920 measured reflections
2700 independent reflections
2428 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.070
S = 1.06
2700 reflections
370 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C30—H30A⋯O1ⁱ	0.95	2.30	3.173 (3)	153
N2—H2B⋯Cg2ⁱⁱ	0.88	2.62	3.483 (2)	168
C26—H26A⋯Cg1ⁱⁱⁱ	0.95	2.61	3.438 (3)	146
C27—H27A⋯Cg2^iv	0.95	2.68	3.572 (3)	157
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Data collection: CrystalClear (Rigaku, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811027218/xu5255sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027218/xu5255Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811027218/xu5255Isup3.cml

checkCIF report

Comment top

Ionic liquids (ILs) are widely used as new and designable green chemical materials in organic, organometallic and enzymatic catalyses as solvents (Zhao & Malhotra, 2002; Chauvin & Olivier-Bourbigou, 1995; Seddon, 2001) and nano- and electrochemistry (Hapiot & Lagros, 2008; Blaster & Studer, 2003).

In the title salt (Fig. 1), the 1-(2-ureidoethyl)quinolinium cation consists of urea and quinoline ring connected to each other via ethylidene. The dihedral angle between the quinoline ring and mean plane of urea is 61.51 (5)°. The 1-(2-ureidoethyl)quinolinium cations interact through a weak C—H···O interaction, forming a zidzag chain along the C direction (Fig. 2). The 1-(2-ureidoethyl)quinolinium cation is situated between three [BPh₄]^- anions and this orientation is further stabilized via C—H···π and N—H···π interaction (Table 1 and Fig. 3), similar to that found in the structure of tetraphenylborate anion [BPh₄]^- (Youngme et al., 2006).

Related literature top

For applications of ionic liquids, see: Zhao & Malhotra (2002); Chauvin & Olivier-Bourbigou (1995); Seddon (2001); Hapiot & Lagros (2008); Blaster & Studer (2003). For a related structure, see: Youngme et al. (2006).

Experimental top

All chemicals were obtained from commercial sources and used without further purification. A solution of quinoline (0.65 g, 5 mmol) and 2-chloroethylurea (0.61 g, 5 mmol) in ethanol(10 ml) was heated at 353 K with stirring for 72 h under N₂. After the reaction mixture cooled to room temperature, the purple precipitate was collected and dissolved in water (0.34 g, 40 ml) and treated with a saturated solution of sodium tetraphenylborate (10 ml). The title compound was separated and recrystallized from ethanol. Colourless single crystals were grown from methanol by slow evaporation at ambient room temperature over a period of 18 d.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50%.
	Fig. 2. A view of the H-bonds between cations.
	Fig. 3. A detailed view of the interactions between cations and anions involves H-bonds, C—H···π and N—H···π, some H atoms have been omitted for clarity.

1-[2-(carbamoylamino)ethyl]quinolinium tetraphenylboranuide top

Crystal data top

C₁₂H₁₄N₃O⁺·C₂₄H₂₀B⁻	F(000) = 2272
M_r = 535.47	D_x = 1.226 Mg m⁻³
Orthorhombic, Aba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2ac	Cell parameters from 5127 reflections
a = 25.5434 (11) Å	θ = 1.6–25.0°
b = 18.7954 (8) Å	µ = 0.07 mm⁻¹
c = 12.0837 (5) Å	T = 173 K
V = 5801.4 (4) Å³	Block, colorless
Z = 8	0.40 × 0.18 × 0.13 mm

Data collection top

Rigaku Saturn CCD diffractometer	2428 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 25.0°, θ_min = 1.6°
ω scans	h = −29→30
32920 measured reflections	k = −21→22
2700 independent reflections	l = −14→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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0339P)² + 1.8667P] where P = (F_o² + 2F_c²)/3
2700 reflections	(Δ/σ)_max < 0.001
370 parameters	Δρ_max = 0.17 e Å⁻³
1 restraint	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₂H₁₄N₃O⁺·C₂₄H₂₀B⁻	V = 5801.4 (4) Å³
M_r = 535.47	Z = 8
Orthorhombic, Aba2	Mo Kα radiation
a = 25.5434 (11) Å	µ = 0.07 mm⁻¹
b = 18.7954 (8) Å	T = 173 K
c = 12.0837 (5) Å	0.40 × 0.18 × 0.13 mm

Data collection top

Rigaku Saturn CCD diffractometer	2428 reflections with I > 2σ(I)
32920 measured reflections	R_int = 0.039
2700 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	1 restraint
wR(F²) = 0.070	H-atom parameters constrained
S = 1.06	Δρ_max = 0.17 e Å⁻³
2700 reflections	Δρ_min = −0.13 e Å⁻³
370 parameters

Special details top

Experimental. ¹H NMR (Bruker Avance DRX 500 F T NMR spectrometer, DMSO-d₆ solvent, ambient temperature): 3.59 (t, J = 5.5 Hz, 2 H), 5.05 (t, J = 5.5 Hz, 2H), 5.59 (s, 2 H), 6.16 (s, 1 H), 6.79 (t, J = 7.5 Hz, 4 H), 6.92 (t, J = 7.5 Hz, 8 H), 7.18 (s, 8H), 8.04 (t, J = 7.5 Hz, 1 H), 8.14–8.17 (m, 1 H), 8.27 (t, J = 4.5 Hz, 1 H), 8.46 (d, J = 8.0 Hz, 1 H), 8.68 (d, J = 9.0 Hz, 1 H), 9.26 (d, J = 8.5 Hz, 1 H), 9.30 (d, J = 5.5 Hz, 1 H).

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
B1	0.36506 (9)	0.28381 (12)	0.1753 (2)	0.0305 (5)
N3	0.19822 (8)	−0.07125 (10)	0.54551 (19)	0.0488 (5)
H3A	0.2089	−0.0718	0.6147	0.059*
H3B	0.1739	−0.1013	0.5234	0.059*
C1	0.38950 (7)	0.20251 (10)	0.18152 (17)	0.0280 (4)
C2	0.44354 (8)	0.19105 (10)	0.19212 (17)	0.0325 (5)
H2A	0.4658	0.2313	0.1985	0.039*
C3	0.46596 (9)	0.12399 (11)	0.19376 (18)	0.0364 (5)
H3C	0.5029	0.1191	0.1999	0.044*
C4	0.43460 (9)	0.06419 (11)	0.18648 (19)	0.0367 (5)
H4A	0.4496	0.0180	0.1879	0.044*
C5	0.38123 (9)	0.07275 (11)	0.1771 (2)	0.0373 (5)
H5A	0.3592	0.0322	0.1723	0.045*
C6	0.35952 (8)	0.14047 (11)	0.17453 (18)	0.0317 (5)
H6A	0.3226	0.1448	0.1677	0.038*
C7	0.39097 (8)	0.33034 (11)	0.27733 (18)	0.0314 (5)
C8	0.40921 (8)	0.40028 (11)	0.2654 (2)	0.0367 (5)
H8A	0.4063	0.4228	0.1953	0.044*
C9	0.43147 (9)	0.43786 (13)	0.3533 (2)	0.0471 (6)
H9A	0.4434	0.4851	0.3418	0.057*
C10	0.43627 (9)	0.40757 (15)	0.4555 (2)	0.0494 (7)
H10A	0.4510	0.4337	0.5151	0.059*
C11	0.41931 (10)	0.33815 (15)	0.4710 (2)	0.0481 (6)
H11A	0.4230	0.3160	0.5412	0.058*
C12	0.39687 (9)	0.30122 (12)	0.38328 (19)	0.0402 (5)
H12A	0.3850	0.2540	0.3958	0.048*
C13	0.37940 (8)	0.32221 (10)	0.05635 (18)	0.0299 (4)
C14	0.35195 (9)	0.38272 (11)	0.02078 (19)	0.0369 (5)
H14A	0.3247	0.4007	0.0663	0.044*
C15	0.36284 (10)	0.41740 (12)	−0.0777 (2)	0.0437 (6)
H15A	0.3437	0.4588	−0.0976	0.052*
C16	0.40143 (10)	0.39196 (13)	−0.1469 (2)	0.0491 (6)
H16A	0.4085	0.4148	−0.2155	0.059*
C17	0.42949 (10)	0.33316 (13)	−0.1151 (2)	0.0481 (6)
H17A	0.4563	0.3151	−0.1619	0.058*
C18	0.41890 (8)	0.29986 (11)	−0.0149 (2)	0.0363 (5)
H18A	0.4396	0.2600	0.0059	0.044*
C19	0.30087 (8)	0.27991 (10)	0.18398 (19)	0.0300 (4)
C20	0.27153 (8)	0.29676 (11)	0.27789 (19)	0.0360 (5)
H20A	0.2893	0.3118	0.3428	0.043*
C21	0.21687 (9)	0.29227 (12)	0.2799 (2)	0.0429 (6)
H21A	0.1983	0.3047	0.3452	0.051*
C22	0.18979 (9)	0.27008 (12)	0.1880 (2)	0.0438 (6)
H22A	0.1527	0.2673	0.1891	0.053*
C23	0.21741 (9)	0.25180 (12)	0.0939 (2)	0.0412 (6)
H23A	0.1993	0.2358	0.0299	0.049*
C24	0.27154 (8)	0.25679 (11)	0.09271 (19)	0.0347 (5)
H24A	0.2896	0.2439	0.0270	0.042*
C25	0.13503 (10)	0.11765 (11)	0.38478 (19)	0.0393 (5)
H25A	0.1572	0.1149	0.4477	0.047*
C26	0.08270 (10)	0.13228 (11)	0.3999 (2)	0.0426 (6)
H26A	0.0689	0.1380	0.4723	0.051*
C27	0.05106 (10)	0.13850 (11)	0.3102 (2)	0.0392 (5)
H27A	0.0153	0.1512	0.3196	0.047*
C28	0.07092 (8)	0.12627 (11)	0.20353 (18)	0.0325 (5)
C29	0.12449 (8)	0.10883 (10)	0.19089 (18)	0.0317 (5)
C30	0.14452 (10)	0.09501 (13)	0.08501 (19)	0.0427 (6)
H30A	0.1803	0.0829	0.0756	0.051*
C31	0.11207 (11)	0.09919 (14)	−0.0041 (2)	0.0529 (7)
H31A	0.1258	0.0900	−0.0758	0.063*
C32	0.05902 (11)	0.11660 (15)	0.0070 (2)	0.0524 (7)
H32A	0.0372	0.1192	−0.0566	0.063*
C33	0.03888 (10)	0.12971 (13)	0.1085 (2)	0.0448 (6)
H33A	0.0029	0.1413	0.1159	0.054*
C34	0.21205 (9)	0.09099 (14)	0.2790 (2)	0.0498 (6)
H34A	0.2300	0.1128	0.3432	0.060*
H34B	0.2269	0.1122	0.2109	0.060*
C35	0.22221 (10)	0.01157 (14)	0.2788 (2)	0.0515 (6)
H35A	0.2089	−0.0087	0.2086	0.062*
H35B	0.2605	0.0035	0.2808	0.062*
C36	0.21909 (8)	−0.02431 (11)	0.4730 (2)	0.0358 (5)
N1	0.15554 (7)	0.10719 (9)	0.28474 (15)	0.0349 (4)
N2	0.19846 (7)	−0.02603 (10)	0.36987 (17)	0.0423 (5)
H2B	0.1698	−0.0508	0.3581	0.051*
O1	0.25263 (7)	0.01830 (9)	0.49865 (15)	0.0523 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0317 (12)	0.0293 (11)	0.0305 (12)	−0.0016 (9)	0.0020 (11)	−0.0061 (10)
N3	0.0510 (12)	0.0388 (11)	0.0567 (13)	−0.0044 (9)	−0.0027 (11)	0.0042 (10)
C1	0.0339 (11)	0.0305 (10)	0.0198 (9)	−0.0010 (8)	−0.0008 (9)	−0.0021 (8)
C2	0.0361 (11)	0.0311 (10)	0.0303 (11)	−0.0021 (9)	−0.0042 (10)	−0.0058 (9)
C3	0.0392 (12)	0.0388 (12)	0.0313 (11)	0.0054 (10)	−0.0085 (10)	−0.0054 (10)
C4	0.0505 (14)	0.0287 (10)	0.0310 (11)	0.0063 (9)	−0.0019 (11)	−0.0008 (9)
C5	0.0472 (13)	0.0281 (10)	0.0367 (12)	−0.0068 (9)	0.0037 (11)	0.0002 (10)
C6	0.0318 (11)	0.0337 (11)	0.0297 (11)	−0.0028 (8)	0.0026 (10)	0.0003 (9)
C7	0.0251 (10)	0.0325 (11)	0.0367 (12)	0.0046 (8)	0.0024 (10)	−0.0071 (10)
C8	0.0295 (11)	0.0322 (11)	0.0485 (14)	0.0030 (9)	−0.0020 (10)	−0.0101 (10)
C9	0.0387 (13)	0.0372 (12)	0.0654 (18)	0.0026 (10)	−0.0062 (12)	−0.0195 (13)
C10	0.0390 (14)	0.0581 (16)	0.0510 (16)	0.0010 (12)	−0.0057 (12)	−0.0307 (13)
C11	0.0438 (14)	0.0663 (17)	0.0341 (12)	0.0024 (12)	0.0000 (11)	−0.0136 (12)
C12	0.0431 (14)	0.0433 (13)	0.0341 (12)	−0.0043 (10)	0.0023 (11)	−0.0084 (10)
C13	0.0302 (11)	0.0258 (10)	0.0337 (11)	−0.0061 (8)	−0.0016 (9)	−0.0035 (8)
C14	0.0380 (12)	0.0328 (11)	0.0398 (12)	0.0009 (9)	0.0024 (11)	−0.0003 (10)
C15	0.0471 (14)	0.0304 (11)	0.0536 (15)	−0.0015 (10)	−0.0040 (12)	0.0072 (10)
C16	0.0521 (15)	0.0429 (14)	0.0524 (16)	−0.0081 (12)	0.0094 (13)	0.0182 (12)
C17	0.0470 (14)	0.0451 (14)	0.0522 (15)	−0.0009 (11)	0.0196 (12)	0.0081 (12)
C18	0.0372 (12)	0.0290 (11)	0.0426 (13)	−0.0033 (9)	0.0052 (11)	0.0027 (10)
C19	0.0347 (11)	0.0245 (9)	0.0309 (10)	0.0006 (8)	−0.0015 (10)	0.0020 (9)
C20	0.0397 (12)	0.0339 (11)	0.0344 (11)	0.0017 (9)	0.0018 (10)	−0.0018 (9)
C21	0.0388 (13)	0.0423 (12)	0.0474 (14)	0.0070 (10)	0.0102 (11)	0.0066 (11)
C22	0.0298 (11)	0.0444 (12)	0.0571 (15)	0.0001 (10)	0.0001 (12)	0.0149 (12)
C23	0.0390 (13)	0.0403 (12)	0.0444 (13)	−0.0063 (10)	−0.0105 (11)	0.0105 (11)
C24	0.0366 (12)	0.0351 (11)	0.0324 (11)	−0.0027 (9)	−0.0002 (10)	0.0023 (9)
C25	0.0558 (15)	0.0320 (11)	0.0302 (12)	−0.0027 (11)	−0.0017 (11)	−0.0008 (9)
C26	0.0628 (17)	0.0329 (12)	0.0321 (12)	0.0024 (11)	0.0103 (12)	−0.0025 (10)
C27	0.0398 (13)	0.0314 (12)	0.0464 (14)	0.0040 (10)	0.0141 (11)	0.0019 (9)
C28	0.0351 (11)	0.0263 (10)	0.0360 (12)	0.0017 (8)	0.0037 (9)	0.0013 (9)
C29	0.0373 (12)	0.0277 (10)	0.0301 (11)	−0.0001 (8)	0.0011 (10)	0.0015 (9)
C30	0.0440 (14)	0.0484 (13)	0.0356 (13)	0.0138 (11)	0.0100 (11)	0.0040 (10)
C31	0.0748 (19)	0.0552 (16)	0.0286 (12)	0.0153 (13)	0.0067 (13)	−0.0004 (11)
C32	0.0581 (17)	0.0593 (16)	0.0399 (14)	0.0076 (13)	−0.0145 (13)	−0.0013 (12)
C33	0.0384 (13)	0.0471 (13)	0.0489 (14)	0.0042 (11)	−0.0052 (11)	0.0010 (12)
C34	0.0319 (12)	0.0661 (16)	0.0513 (16)	−0.0020 (11)	−0.0030 (12)	0.0160 (13)
C35	0.0414 (14)	0.0718 (18)	0.0413 (14)	0.0180 (12)	−0.0050 (11)	−0.0021 (13)
C36	0.0296 (11)	0.0303 (11)	0.0473 (13)	0.0057 (9)	−0.0065 (10)	−0.0056 (10)
N1	0.0359 (10)	0.0342 (9)	0.0345 (10)	−0.0017 (8)	−0.0021 (9)	0.0041 (8)
N2	0.0372 (10)	0.0397 (10)	0.0499 (12)	−0.0010 (8)	−0.0130 (10)	−0.0058 (9)
O1	0.0484 (9)	0.0545 (10)	0.0540 (10)	−0.0165 (9)	−0.0176 (9)	0.0039 (8)

Geometric parameters (Å, º) top

B1—C19	1.645 (3)	C19—C24	1.402 (3)
B1—C1	1.652 (3)	C19—C20	1.396 (3)
B1—C7	1.650 (3)	C20—C21	1.399 (3)
B1—C13	1.649 (3)	C20—H20A	0.9500
N3—C36	1.353 (3)	C21—C22	1.373 (4)
N3—H3A	0.8800	C21—H21A	0.9500
N3—H3B	0.8800	C22—C23	1.382 (4)
C1—C6	1.398 (3)	C22—H22A	0.9500
C1—C2	1.403 (3)	C23—C24	1.386 (3)
C2—C3	1.385 (3)	C23—H23A	0.9500
C2—H2A	0.9500	C24—H24A	0.9500
C3—C4	1.383 (3)	C25—N1	1.332 (3)
C3—H3C	0.9500	C25—C26	1.377 (3)
C4—C5	1.377 (3)	C25—H25A	0.9500
C4—H4A	0.9500	C26—C27	1.357 (3)
C5—C6	1.389 (3)	C26—H26A	0.9500
C5—H5A	0.9500	C27—C28	1.404 (3)
C6—H6A	0.9500	C27—H27A	0.9500
C7—C12	1.400 (3)	C28—C29	1.415 (3)
C7—C8	1.402 (3)	C28—C33	1.411 (3)
C8—C9	1.396 (3)	C29—N1	1.384 (3)
C8—H8A	0.9500	C29—C30	1.402 (3)
C9—C10	1.365 (4)	C30—C31	1.361 (4)
C9—H9A	0.9500	C30—H30A	0.9500
C10—C11	1.388 (4)	C31—C32	1.400 (4)
C10—H10A	0.9500	C31—H31A	0.9500
C11—C12	1.391 (3)	C32—C33	1.353 (4)
C11—H11A	0.9500	C32—H32A	0.9500
C12—H12A	0.9500	C33—H33A	0.9500
C13—C18	1.391 (3)	C34—N1	1.477 (3)
C13—C14	1.404 (3)	C34—C35	1.515 (4)
C14—C15	1.385 (3)	C34—H34A	0.9900
C14—H14A	0.9500	C34—H34B	0.9900
C15—C16	1.378 (4)	C35—N2	1.442 (3)
C15—H15A	0.9500	C35—H35A	0.9900
C16—C17	1.372 (3)	C35—H35B	0.9900
C16—H16A	0.9500	C36—O1	1.213 (3)
C17—C18	1.390 (3)	C36—N2	1.354 (3)
C17—H17A	0.9500	N2—H2B	0.8800
C18—H18A	0.9500

C19—B1—C1	109.42 (16)	C20—C19—B1	125.24 (19)
C19—B1—C7	112.06 (17)	C19—C20—C21	122.4 (2)
C1—B1—C7	107.72 (17)	C19—C20—H20A	118.8
C19—B1—C13	107.26 (17)	C21—C20—H20A	118.8
C1—B1—C13	111.14 (17)	C22—C21—C20	120.5 (2)
C7—B1—C13	109.28 (16)	C22—C21—H21A	119.8
C36—N3—H3A	120.0	C20—C21—H21A	119.8
C36—N3—H3B	120.0	C21—C22—C23	118.9 (2)
H3A—N3—H3B	120.0	C21—C22—H22A	120.5
C6—C1—C2	114.62 (18)	C23—C22—H22A	120.5
C6—C1—B1	124.18 (17)	C22—C23—C24	120.1 (2)
C2—C1—B1	121.19 (17)	C22—C23—H23A	120.0
C3—C2—C1	123.23 (19)	C24—C23—H23A	120.0
C3—C2—H2A	118.4	C19—C24—C23	123.1 (2)
C1—C2—H2A	118.4	C19—C24—H24A	118.4
C2—C3—C4	120.0 (2)	C23—C24—H24A	118.4
C2—C3—H3C	120.0	N1—C25—C26	122.1 (2)
C4—C3—H3C	120.0	N1—C25—H25A	118.9
C5—C4—C3	118.91 (19)	C26—C25—H25A	118.9
C5—C4—H4A	120.5	C27—C26—C25	119.3 (2)
C3—C4—H4A	120.5	C27—C26—H26A	120.3
C4—C5—C6	120.28 (19)	C25—C26—H26A	120.3
C4—C5—H5A	119.9	C26—C27—C28	120.2 (2)
C6—C5—H5A	119.9	C26—C27—H27A	119.9
C1—C6—C5	123.0 (2)	C28—C27—H27A	119.9
C1—C6—H6A	118.5	C29—C28—C27	119.1 (2)
C5—C6—H6A	118.5	C29—C28—C33	118.9 (2)
C12—C7—C8	115.1 (2)	C27—C28—C33	122.0 (2)
C12—C7—B1	121.28 (19)	N1—C29—C30	122.30 (19)
C8—C7—B1	123.6 (2)	N1—C29—C28	118.08 (19)
C9—C8—C7	122.1 (2)	C30—C29—C28	119.6 (2)
C9—C8—H8A	118.9	C31—C30—C29	119.3 (2)
C7—C8—H8A	118.9	C31—C30—H30A	120.4
C8—C9—C10	120.9 (2)	C29—C30—H30A	120.4
C8—C9—H9A	119.6	C30—C31—C32	121.8 (2)
C10—C9—H9A	119.6	C30—C31—H31A	119.1
C11—C10—C9	119.1 (2)	C32—C31—H31A	119.1
C11—C10—H10A	120.4	C33—C32—C31	119.8 (2)
C9—C10—H10A	120.4	C33—C32—H32A	120.1
C10—C11—C12	119.6 (2)	C31—C32—H32A	120.1
C10—C11—H11A	120.2	C32—C33—C28	120.6 (2)
C12—C11—H11A	120.2	C32—C33—H33A	119.7
C11—C12—C7	123.1 (2)	C28—C33—H33A	119.7
C11—C12—H12A	118.4	N1—C34—C35	111.8 (2)
C7—C12—H12A	118.4	N1—C34—H34A	109.3
C18—C13—C14	114.7 (2)	C35—C34—H34A	109.3
C18—C13—B1	124.62 (18)	N1—C34—H34B	109.3
C14—C13—B1	120.70 (18)	C35—C34—H34B	109.3
C15—C14—C13	123.0 (2)	H34A—C34—H34B	107.9
C15—C14—H14A	118.5	N2—C35—C34	114.2 (2)
C13—C14—H14A	118.5	N2—C35—H35A	108.7
C16—C15—C14	120.1 (2)	C34—C35—H35A	108.7
C16—C15—H15A	119.9	N2—C35—H35B	108.7
C14—C15—H15A	119.9	C34—C35—H35B	108.7
C15—C16—C17	118.9 (2)	H35A—C35—H35B	107.6
C15—C16—H16A	120.5	O1—C36—N2	121.7 (2)
C17—C16—H16A	120.5	O1—C36—N3	123.0 (2)
C18—C17—C16	120.3 (2)	N2—C36—N3	115.3 (2)
C18—C17—H17A	119.8	C25—N1—C29	120.98 (19)
C16—C17—H17A	119.8	C25—N1—C34	117.2 (2)
C17—C18—C13	123.0 (2)	C29—N1—C34	121.74 (19)
C17—C18—H18A	118.5	C36—N2—C35	121.83 (19)
C13—C18—H18A	118.5	C36—N2—H2B	119.1
C24—C19—C20	115.00 (19)	C35—N2—H2B	119.1
C24—C19—B1	119.75 (19)

C19—B1—C1—C6	10.8 (3)	C1—B1—C19—C24	−74.9 (2)
C7—B1—C1—C6	132.9 (2)	C7—B1—C19—C24	165.72 (18)
C13—B1—C1—C6	−107.5 (2)	C13—B1—C19—C24	45.8 (2)
C19—B1—C1—C2	−170.64 (19)	C1—B1—C19—C20	103.8 (2)
C7—B1—C1—C2	−48.6 (3)	C7—B1—C19—C20	−15.6 (3)
C13—B1—C1—C2	71.1 (2)	C13—B1—C19—C20	−135.6 (2)
C6—C1—C2—C3	1.0 (3)	C24—C19—C20—C21	−1.3 (3)
B1—C1—C2—C3	−177.6 (2)	B1—C19—C20—C21	−180.0 (2)
C1—C2—C3—C4	−1.0 (3)	C19—C20—C21—C22	0.6 (3)
C2—C3—C4—C5	0.3 (3)	C20—C21—C22—C23	0.4 (3)
C3—C4—C5—C6	0.3 (3)	C21—C22—C23—C24	−0.8 (3)
C2—C1—C6—C5	−0.4 (3)	C20—C19—C24—C23	0.9 (3)
B1—C1—C6—C5	178.2 (2)	B1—C19—C24—C23	179.7 (2)
C4—C5—C6—C1	−0.2 (3)	C22—C23—C24—C19	0.0 (3)
C19—B1—C7—C12	78.1 (3)	N1—C25—C26—C27	−2.1 (3)
C1—B1—C7—C12	−42.3 (3)	C25—C26—C27—C28	3.5 (3)
C13—B1—C7—C12	−163.18 (19)	C26—C27—C28—C29	−1.3 (3)
C19—B1—C7—C8	−102.9 (2)	C26—C27—C28—C33	177.7 (2)
C1—B1—C7—C8	136.7 (2)	C27—C28—C29—N1	−2.4 (3)
C13—B1—C7—C8	15.9 (3)	C33—C28—C29—N1	178.66 (19)
C12—C7—C8—C9	−0.1 (3)	C27—C28—C29—C30	178.6 (2)
B1—C7—C8—C9	−179.3 (2)	C33—C28—C29—C30	−0.3 (3)
C7—C8—C9—C10	−0.2 (4)	N1—C29—C30—C31	−178.4 (2)
C8—C9—C10—C11	0.9 (4)	C28—C29—C30—C31	0.5 (3)
C9—C10—C11—C12	−1.3 (4)	C29—C30—C31—C32	−0.3 (4)
C10—C11—C12—C7	1.0 (4)	C30—C31—C32—C33	−0.1 (4)
C8—C7—C12—C11	−0.3 (3)	C31—C32—C33—C28	0.2 (4)
B1—C7—C12—C11	178.9 (2)	C29—C28—C33—C32	0.0 (3)
C19—B1—C13—C18	−137.6 (2)	C27—C28—C33—C32	−179.0 (2)
C1—B1—C13—C18	−18.1 (3)	N1—C34—C35—N2	−54.0 (3)
C7—B1—C13—C18	100.7 (2)	C26—C25—N1—C29	−1.7 (3)
C19—B1—C13—C14	43.7 (2)	C26—C25—N1—C34	−179.3 (2)
C1—B1—C13—C14	163.26 (18)	C30—C29—N1—C25	−177.2 (2)
C7—B1—C13—C14	−78.0 (2)	C28—C29—N1—C25	3.8 (3)
C18—C13—C14—C15	0.5 (3)	C30—C29—N1—C34	0.3 (3)
B1—C13—C14—C15	179.3 (2)	C28—C29—N1—C34	−178.71 (19)
C13—C14—C15—C16	1.3 (4)	C35—C34—N1—C25	93.1 (3)
C14—C15—C16—C17	−1.6 (4)	C35—C34—N1—C29	−84.5 (3)
C15—C16—C17—C18	0.2 (4)	O1—C36—N2—C35	13.3 (3)
C16—C17—C18—C13	1.7 (4)	N3—C36—N2—C35	−169.2 (2)
C14—C13—C18—C17	−2.0 (3)	C34—C35—N2—C36	−77.0 (3)
B1—C13—C18—C17	179.3 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30A···O1ⁱ	0.95	2.30	3.173 (3)	153
N2—H2B···Cg2ⁱⁱ	0.88	2.62	3.483 (2)	168
C26—H26A···Cg1ⁱⁱⁱ	0.95	2.61	3.438 (3)	146
C27—H27A···Cg2^iv	0.95	2.68	3.572 (3)	157

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄N₃O⁺·C₂₄H₂₀B⁻
M_r	535.47
Crystal system, space group	Orthorhombic, Aba2
Temperature (K)	173
a, b, c (Å)	25.5434 (11), 18.7954 (8), 12.0837 (5)
V (Å³)	5801.4 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.40 × 0.18 × 0.13

Data collection
Diffractometer	Rigaku Saturn CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	32920, 2700, 2428
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.070, 1.06
No. of reflections	2700
No. of parameters	370
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.13

Computer programs: CrystalClear (Rigaku, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30A···O1ⁱ	0.95	2.30	3.173 (3)	153
N2—H2B···Cg2ⁱⁱ	0.88	2.62	3.483 (2)	168
C26—H26A···Cg1ⁱⁱⁱ	0.95	2.61	3.438 (3)	146
C27—H27A···Cg2^iv	0.95	2.68	3.572 (3)	157

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

Acknowledgements

We acknowledge the National Natural Science Foundation of China (grant Nos. 20873041 and 21072061) and the Shanghai Leading Academic Discipline Project (grant No. B409) for financial support.

References

Blaster, H. U. & Studer, M. (2003). Green Chem. 5, 112–117. Google Scholar
Chauvin, Y. & Olivier-Bourbigou, H. (1995). Chemtech, 25, 26–30. CAS Google Scholar
Hapiot, P. & Lagros, C. (2008). Chem. Rev. 108, 2238–2264. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Seddon, K. R. (2001). Chem. Commun. 23, 2399–2407. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Youngme, S., Wannarit, N. & Chaichit, N. (2006). Acta Cryst. E62, o5265–o5267. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhao, H. & Malhotra, S. V. (2002). Aldrichim. Acta, 35, 75–83. Web of Science CrossRef CAS 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 67| Part 8| August 2011| Page o2031

doi:10.1107/S1600536811027218

Open

access