9-O-Butyl­berberrubinium bromide

Chen, Z.; Li, X.-G.; Xie, Y.-S.; Ye, X.-L.

doi:10.1107/S1600536809018388

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1370

doi:10.1107/S1600536809018388

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9-O-Butylberberrubinium bromide

Zhu Chen,^a Xue-Gang Li,^a Yong-Sheng Xie ^b and Xiao-Li Ye ^c ^*

^aCollege of Pharmaceutical Sciences, Southwest University, Chongqing 400715, People's Republic of China, ^bSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China, and ^cCollege of Life Sciences, Southwest University, Chongqing 400715, People's Republic of China
^*Correspondence e-mail: yexiaoli@swu.edu.cn

(Received 14 April 2009; accepted 15 May 2009; online 23 May 2009)

In the title compound, C₂₃H₂₄NO₄⁺·Br⁻, the butyl chain is disordered between two conformations; the occupancies refined to 0.735 (7) and 0.265 (7). The dihedral angle between the naphthalene ring system and the phenyl ring is 11.6 (2)°. In the crystal structure, the cations are packed via π–π interactions into stacks propagating in the [010] direction. Weak intermolecular C—H⋯O and C—H⋯Br hydrogen bonds contribute further to the crystal packing stability.

Related literature

For the bioactivity of berberine, see: Jiang et al. (1998 ); Kupeli et al.. (2002 ). For the bioactivity of 9-O-butyl-berberrubine bromide, see Ye & Li (2007 ).

Experimental

Crystal data

C₂₃H₂₄NO₄⁺·Br⁻
M_r = 458.34
Monoclinic, P 2₁ /n
a = 9.716 (4) Å
b = 7.623 (3) Å
c = 27.443 (11) Å
β = 92.983 (8)°
V = 2029.9 (14) Å³
Z = 4
Mo Kα radiation
μ = 2.06 mm⁻¹
T = 295 K
0.12 × 0.10 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2005 ) T_min = 0.791, T_max = 0.887
10394 measured reflections
3592 independent reflections
1965 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.161
S = 1.08
3592 reflections
276 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Centroid-to-centroid distances (Å)

Cg1⋯Cg3ⁱ	3.780 (4)
Cg2⋯Cg3ⁱⁱ	3.775 (4)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1. Cg1, Cg2 and Cg3 are the centroids of the N1/C13/C12/C9/C10/C14, C5–C10 and C15/C19–C22/C16 rings, respectively.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Br1	0.93	2.77	3.658 (5)	161
C2—H2A⋯O2ⁱⁱⁱ	0.97	2.64	3.404 (14)	136
Symmetry code: (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018388/cv2550sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809018388/cv2550Isup2.hkl

checkCIF report

Comment top

Berberine is a main compound presented in the rhizome of Coptis chinensis Franch. Berberine and its derivatives are used for treating diarrhoea (Kupeli et al., 2002) and anti-inflammatory (Jiang et al., 1998). Herewith we report the crystal structure of the title compound (I), which exhibits an excellent antibacterial activity (Ye & Li, 2007).

In (I) (Fig. 1), the dihedral angles formed by the benzene rings C5–C10 and C15/C19/C20/C21/C22/C16 with the pyridine ring are 2.2 (3) and 12.8 (3)°, respectively. The six-membered heterocyclic ring (C13/C15/C16/C17/C18/N1) adopts screw-boat conformation. In the crystal structure, weak intermolecular C—H···O and C—H···Br hydrogen bonds (Table 2) link the molecules. The aromatic rings in the cations are involved in π–π interactions (Table 1). The cations are packed via π–π interactions into stacks propagated in direction [010].

Related literature top

For the bioactivity of berberine, see: Jiang et al. (1998); Kupeli et al.. (2002). For the bioactivity of 9-O-butyl-berberrubine bromide, see Ye & Li (2007).

Experimental top

Berberrubine was obtained from berberine by pyrolysis at 180 °C for 1 h. Then dried berberrubine (10 mmol) was dissolved in DMF (200 ml) and incubated with n-butyl bromide (11 mmol) for 5 h at 100 °C to give the corresponding crude 9-O-butyl-berberrubine bromide. The product was purified by recrystallization from methanol at -18 °C. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid dissolved in methanol at room temperature for 15 d.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound showing the atom-labeling scheme and 30% probability displacement ellipsoids.

9-O-Butylberberrubinium bromide top

Crystal data top

C₂₃H₂₄NO₄⁺·Br⁻	F(000) = 944
M_r = 458.34	D_x = 1.500 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1163 reflections
a = 9.716 (4) Å	θ = 2.8–19.6°
b = 7.623 (3) Å	µ = 2.06 mm⁻¹
c = 27.443 (11) Å	T = 295 K
β = 92.983 (8)°	Block, yellow
V = 2029.9 (14) Å³	0.12 × 0.10 × 0.06 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3592 independent reflections
Radiation source: fine-focus sealed tube	1965 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker 2005)	h = −11→11
T_min = 0.791, T_max = 0.887	k = −7→9
10394 measured reflections	l = −32→32

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)] = 0.060	H-atom parameters constrained
wR(F²) = 0.161	w = 1/[σ²(F_o²) + (0.0623P)² + 1.1441P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
3592 reflections	Δρ_max = 0.58 e Å⁻³
276 parameters	Δρ_min = −0.55 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: 0.0020 (7)

Crystal data top

C₂₃H₂₄NO₄⁺·Br⁻	V = 2029.9 (14) Å³
M_r = 458.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.716 (4) Å	µ = 2.06 mm⁻¹
b = 7.623 (3) Å	T = 295 K
c = 27.443 (11) Å	0.12 × 0.10 × 0.06 mm
β = 92.983 (8)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3592 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2005)	1965 reflections with I > 2σ(I)
T_min = 0.791, T_max = 0.887	R_int = 0.069
10394 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.08	Δρ_max = 0.58 e Å⁻³
3592 reflections	Δρ_min = −0.55 e Å⁻³
276 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)
Br1	0.19113 (6)	0.34507 (10)	0.58534 (2)	0.0683 (3)
O1	0.4605 (4)	0.4269 (6)	0.31978 (15)	0.0691 (13)
O2	0.8340 (4)	−0.0249 (7)	0.66220 (16)	0.0802 (14)
O3	0.5968 (4)	0.0055 (6)	0.66073 (16)	0.0708 (12)
O4	0.1935 (4)	0.5291 (6)	0.31514 (15)	0.0741 (13)
N1	0.6413 (4)	0.2391 (6)	0.44906 (17)	0.0469 (12)
C1'	0.5253 (10)	0.5997 (11)	0.3125 (3)	0.073 (2)	0.735 (7)
H1'1	0.5814	0.6382	0.3407	0.088*	0.735 (7)
H1'2	0.4589	0.6897	0.3027	0.088*	0.735 (7)
C1	0.4509 (12)	0.5865 (18)	0.2933 (5)	0.073 (2)	0.265 (7)
H1A	0.4497	0.6807	0.3170	0.088*	0.265 (7)
H1B	0.3617	0.5872	0.2757	0.088*	0.265 (7)
C2	0.5550 (11)	0.6342 (14)	0.2577 (4)	0.107 (3)	0.735 (7)
H2A	0.5042	0.6720	0.2282	0.128*	0.735 (7)
H2B	0.6033	0.7367	0.2708	0.128*	0.735 (7)
C3	0.6599 (11)	0.5126 (15)	0.2427 (4)	0.117 (3)	0.735 (7)
H3A	0.6196	0.3962	0.2410	0.140*	0.735 (7)
H3B	0.7335	0.5103	0.2679	0.140*	0.735 (7)
C4	0.7234 (15)	0.5492 (18)	0.1943 (4)	0.120 (4)	0.735 (7)
H4A	0.7620	0.4430	0.1822	0.180*	0.735 (7)
H4B	0.7948	0.6357	0.1990	0.180*	0.735 (7)
H4C	0.6537	0.5922	0.1713	0.180*	0.735 (7)
C2'	0.611 (3)	0.540 (3)	0.2709 (9)	0.107 (3)	0.265 (7)
H2'1	0.6905	0.4764	0.2843	0.128*	0.265 (7)
H2'2	0.5562	0.4586	0.2506	0.128*	0.265 (7)
C3'	0.659 (3)	0.687 (3)	0.2392 (8)	0.117 (3)	0.265 (7)
H3'1	0.7435	0.7352	0.2543	0.140*	0.265 (7)
H3'2	0.5904	0.7792	0.2382	0.140*	0.265 (7)
C4'	0.686 (5)	0.633 (5)	0.1874 (8)	0.120 (4)	0.265 (7)
H4'1	0.7240	0.7304	0.1705	0.180*	0.265 (7)
H4'2	0.6009	0.5976	0.1709	0.180*	0.265 (7)
H4'3	0.7498	0.5369	0.1880	0.180*	0.265 (7)
C5	0.3838 (6)	0.4217 (8)	0.3608 (2)	0.0544 (14)
C6	0.2479 (6)	0.4712 (8)	0.3590 (2)	0.0570 (15)
C7	0.1715 (6)	0.4554 (8)	0.4011 (2)	0.0592 (16)
H7	0.0792	0.4880	0.3995	0.071*
C8	0.2291 (6)	0.3941 (8)	0.4439 (2)	0.0533 (15)
H8	0.1758	0.3835	0.4710	0.064*
C9	0.3696 (5)	0.3464 (8)	0.4475 (2)	0.0482 (13)
C10	0.4459 (5)	0.3590 (8)	0.4044 (2)	0.0479 (13)
C11	0.0506 (6)	0.5753 (10)	0.3118 (2)	0.080 (2)
H11A	−0.0039	0.4744	0.3190	0.121*
H11B	0.0260	0.6157	0.2794	0.121*
H11C	0.0339	0.6668	0.3348	0.121*
C12	0.4368 (5)	0.2854 (7)	0.4901 (2)	0.0482 (14)
H12	0.3883	0.2809	0.5184	0.058*
C13	0.5723 (5)	0.2312 (7)	0.4923 (2)	0.0460 (13)
C14	0.5833 (5)	0.3019 (7)	0.4082 (2)	0.0488 (14)
H14	0.6356	0.3086	0.3808	0.059*
C15	0.6459 (5)	0.1642 (7)	0.5359 (2)	0.0476 (13)
C16	0.7894 (5)	0.1470 (8)	0.5374 (2)	0.0507 (14)
C17	0.8631 (6)	0.2081 (8)	0.4940 (2)	0.0573 (16)
H17A	0.8781	0.3337	0.4964	0.069*
H17B	0.9524	0.1514	0.4938	0.069*
C18	0.7835 (5)	0.1681 (8)	0.4478 (2)	0.0567 (15)
H18A	0.7797	0.0421	0.4429	0.068*
H18B	0.8292	0.2195	0.4206	0.068*
C19	0.5729 (6)	0.1186 (7)	0.5774 (2)	0.0508 (14)
H19	0.4775	0.1284	0.5772	0.061*
C20	0.6445 (6)	0.0617 (8)	0.6165 (2)	0.0532 (15)
C21	0.7863 (6)	0.0423 (8)	0.6182 (2)	0.0597 (15)
C22	0.8615 (6)	0.0853 (8)	0.5790 (2)	0.0580 (15)
H22	0.9569	0.0738	0.5803	0.070*
C23	0.7160 (7)	−0.0309 (10)	0.6915 (2)	0.0759 (19)
H23A	0.7082	−0.1461	0.7061	0.091*
H23B	0.7252	0.0554	0.7174	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0502 (4)	0.0849 (6)	0.0714 (5)	−0.0009 (4)	0.0186 (3)	0.0016 (4)
O1	0.066 (3)	0.088 (3)	0.055 (3)	0.020 (2)	0.017 (2)	−0.005 (2)
O2	0.069 (3)	0.111 (4)	0.060 (3)	0.010 (3)	−0.007 (3)	0.011 (3)
O3	0.067 (3)	0.088 (3)	0.058 (3)	0.000 (3)	0.006 (2)	0.010 (2)
O4	0.051 (3)	0.116 (4)	0.056 (3)	0.018 (3)	0.003 (2)	−0.001 (3)
N1	0.039 (2)	0.056 (3)	0.047 (3)	0.002 (2)	0.010 (2)	0.000 (2)
C1'	0.077 (4)	0.080 (4)	0.064 (4)	0.002 (4)	0.020 (4)	0.015 (4)
C1	0.077 (4)	0.080 (4)	0.064 (4)	0.002 (4)	0.020 (4)	0.015 (4)
C2	0.117 (6)	0.108 (6)	0.098 (5)	0.002 (5)	0.034 (5)	0.020 (5)
C3	0.133 (6)	0.114 (6)	0.107 (6)	0.002 (6)	0.039 (5)	0.015 (5)
C4	0.140 (9)	0.132 (10)	0.092 (7)	−0.003 (8)	0.061 (6)	0.002 (7)
C2'	0.117 (6)	0.108 (6)	0.098 (5)	0.002 (5)	0.034 (5)	0.020 (5)
C3'	0.133 (6)	0.114 (6)	0.107 (6)	0.002 (6)	0.039 (5)	0.015 (5)
C4'	0.140 (9)	0.132 (10)	0.092 (7)	−0.003 (8)	0.061 (6)	0.002 (7)
C5	0.052 (3)	0.059 (3)	0.054 (3)	0.005 (3)	0.016 (3)	−0.002 (3)
C6	0.051 (3)	0.071 (4)	0.049 (3)	0.004 (3)	0.004 (3)	−0.002 (3)
C7	0.044 (3)	0.074 (4)	0.060 (4)	0.007 (3)	0.005 (3)	−0.005 (3)
C8	0.041 (3)	0.066 (4)	0.054 (3)	0.003 (3)	0.010 (3)	−0.003 (3)
C9	0.044 (3)	0.052 (3)	0.049 (3)	−0.001 (3)	0.011 (3)	−0.008 (3)
C10	0.043 (3)	0.051 (3)	0.050 (3)	0.005 (3)	0.008 (3)	−0.002 (3)
C11	0.061 (4)	0.114 (6)	0.065 (5)	0.016 (4)	−0.003 (4)	0.005 (4)
C12	0.044 (3)	0.055 (3)	0.047 (3)	0.001 (3)	0.012 (3)	0.000 (3)
C13	0.040 (3)	0.049 (3)	0.049 (3)	−0.004 (2)	0.010 (3)	−0.005 (3)
C14	0.043 (3)	0.058 (3)	0.047 (3)	−0.001 (3)	0.014 (3)	−0.004 (3)
C15	0.043 (3)	0.046 (3)	0.055 (3)	−0.003 (3)	0.006 (3)	0.001 (3)
C16	0.044 (3)	0.053 (3)	0.056 (3)	0.001 (3)	0.007 (3)	−0.004 (3)
C17	0.041 (3)	0.064 (4)	0.068 (4)	0.007 (3)	0.011 (3)	−0.001 (3)
C18	0.043 (3)	0.066 (4)	0.062 (4)	0.011 (3)	0.014 (3)	−0.001 (3)
C19	0.041 (3)	0.055 (3)	0.057 (3)	−0.005 (3)	0.007 (3)	−0.006 (3)
C20	0.048 (3)	0.058 (4)	0.053 (4)	−0.003 (3)	0.004 (3)	−0.010 (3)
C21	0.053 (3)	0.066 (4)	0.059 (4)	0.001 (3)	−0.006 (3)	0.001 (3)
C22	0.044 (3)	0.068 (4)	0.063 (4)	0.003 (3)	0.003 (3)	−0.004 (3)
C23	0.074 (4)	0.094 (5)	0.060 (4)	0.005 (4)	0.005 (4)	−0.001 (4)

Geometric parameters (Å, º) top

O1—C5	1.382 (6)	C4'—H4'3	0.9600
O1—C1	1.418 (12)	C5—C6	1.372 (8)
O1—C1'	1.477 (8)	C5—C10	1.397 (8)
O2—C21	1.370 (7)	C6—C7	1.412 (8)
O2—C23	1.434 (7)	C7—C8	1.358 (8)
O3—C20	1.389 (7)	C7—H7	0.9300
O3—C23	1.424 (7)	C8—C9	1.412 (7)
O4—C6	1.361 (7)	C8—H8	0.9300
O4—C11	1.430 (7)	C9—C12	1.389 (7)
N1—C14	1.319 (7)	C9—C10	1.431 (7)
N1—C13	1.393 (6)	C10—C14	1.403 (7)
N1—C18	1.486 (6)	C11—H11A	0.9600
C1'—C2'	1.517 (8)	C11—H11B	0.9600
C1'—H1'1	0.9700	C11—H11C	0.9600
C1'—H1'2	0.9700	C12—C13	1.378 (7)
C1—C2	1.487 (7)	C12—H12	0.9300
C1—H1A	0.9700	C13—C15	1.456 (8)
C1—H1B	0.9700	C14—H14	0.9300
C2—C3	1.454 (7)	C15—C16	1.399 (7)
C2—H2A	0.9700	C15—C19	1.416 (7)
C2—H2B	0.9700	C16—C22	1.391 (8)
C3—C4	1.517 (7)	C16—C17	1.497 (7)
C3—H3A	0.9700	C17—C18	1.483 (8)
C3—H3B	0.9700	C17—H17A	0.9700
C4—H4A	0.9600	C17—H17B	0.9700
C4—H4B	0.9600	C18—H18A	0.9700
C4—H4C	0.9600	C18—H18B	0.9700
C2'—C3'	1.510 (8)	C19—C20	1.321 (8)
C2'—H2'1	0.9700	C19—H19	0.9300
C2'—H2'2	0.9700	C20—C21	1.384 (8)
C3'—C4'	1.516 (8)	C21—C22	1.370 (8)
C3'—H3'1	0.9700	C22—H22	0.9300
C3'—H3'2	0.9700	C23—H23A	0.9700
C4'—H4'1	0.9600	C23—H23B	0.9700
C4'—H4'2	0.9600

Cg1···Cg3ⁱ	3.780 (4)	Cg2···Cg3ⁱⁱ	3.775 (4)

C5—O1—C1	114.8 (6)	C8—C7—H7	119.0
C5—O1—C1'	112.8 (5)	C6—C7—H7	119.0
C21—O2—C23	105.2 (5)	C7—C8—C9	120.1 (5)
C20—O3—C23	106.2 (5)	C7—C8—H8	119.9
C6—O4—C11	117.9 (5)	C9—C8—H8	119.9
C14—N1—C13	122.5 (5)	C12—C9—C8	123.7 (5)
C14—N1—C18	117.9 (4)	C12—C9—C10	118.5 (5)
C13—N1—C18	119.6 (5)	C8—C9—C10	117.8 (5)
O1—C1'—C2'	95.0 (10)	C5—C10—C14	122.4 (5)
O1—C1'—H1'1	112.7	C5—C10—C9	120.8 (5)
C2'—C1'—H1'1	112.7	C14—C10—C9	116.7 (5)
O1—C1'—H1'2	112.7	O4—C11—H11A	109.5
C2'—C1'—H1'2	112.7	O4—C11—H11B	109.5
H1'1—C1'—H1'2	110.2	H11A—C11—H11B	109.5
O1—C1—C2	121.2 (9)	O4—C11—H11C	109.5
O1—C1—H1A	107.0	H11A—C11—H11C	109.5
C2—C1—H1A	107.0	H11B—C11—H11C	109.5
O1—C1—H1B	107.0	C13—C12—C9	122.8 (5)
C2—C1—H1B	107.0	C13—C12—H12	118.6
H1A—C1—H1B	106.8	C9—C12—H12	118.6
C3—C2—C1	122.8 (8)	C12—C13—N1	116.9 (5)
C3—C2—H2A	106.6	C12—C13—C15	124.6 (5)
C1—C2—H2A	106.6	N1—C13—C15	118.6 (5)
C3—C2—H2B	106.6	N1—C14—C10	122.5 (5)
C1—C2—H2B	106.6	N1—C14—H14	118.7
H2A—C2—H2B	106.6	C10—C14—H14	118.7
C2—C3—C4	117.0 (8)	C16—C15—C19	119.6 (5)
C2—C3—H3A	108.0	C16—C15—C13	120.2 (5)
C4—C3—H3A	108.0	C19—C15—C13	120.2 (5)
C2—C3—H3B	108.0	C22—C16—C15	121.0 (5)
C4—C3—H3B	108.0	C22—C16—C17	121.2 (5)
H3A—C3—H3B	107.3	C15—C16—C17	117.7 (5)
C3—C4—H4A	109.5	C18—C17—C16	111.6 (5)
C3—C4—H4B	109.5	C18—C17—H17A	109.3
H4A—C4—H4B	109.5	C16—C17—H17A	109.3
C3—C4—H4C	109.5	C18—C17—H17B	109.3
H4A—C4—H4C	109.5	C16—C17—H17B	109.3
H4B—C4—H4C	109.5	H17A—C17—H17B	108.0
C3'—C2'—C1'	114.1 (9)	C17—C18—N1	110.4 (5)
C3'—C2'—H2'1	108.7	C17—C18—H18A	109.6
C1'—C2'—H2'1	108.7	N1—C18—H18A	109.6
C3'—C2'—H2'2	108.7	C17—C18—H18B	109.6
C1'—C2'—H2'2	108.7	N1—C18—H18B	109.6
H2'1—C2'—H2'2	107.6	H18A—C18—H18B	108.1
C2'—C3'—C4'	114.3 (10)	C20—C19—C15	118.0 (5)
C2'—C3'—H3'1	108.7	C20—C19—H19	121.0
C4'—C3'—H3'1	108.7	C15—C19—H19	121.0
C2'—C3'—H3'2	108.7	C19—C20—C21	123.0 (6)
C4'—C3'—H3'2	108.7	C19—C20—O3	128.7 (5)
H3'1—C3'—H3'2	107.6	C21—C20—O3	108.3 (6)
C3'—C4'—H4'1	109.5	O2—C21—C22	127.7 (6)
C3'—C4'—H4'2	109.5	O2—C21—C20	111.1 (6)
H4'1—C4'—H4'2	109.5	C22—C21—C20	121.2 (6)
C3'—C4'—H4'3	109.5	C21—C22—C16	117.3 (5)
H4'1—C4'—H4'3	109.5	C21—C22—H22	121.3
H4'2—C4'—H4'3	109.5	C16—C22—H22	121.3
C6—C5—O1	121.4 (6)	O3—C23—O2	108.1 (5)
C6—C5—C10	119.8 (5)	O3—C23—H23A	110.1
O1—C5—C10	118.8 (5)	O2—C23—H23A	110.1
O4—C6—C5	116.8 (5)	O3—C23—H23B	110.1
O4—C6—C7	123.7 (5)	O2—C23—H23B	110.1
C5—C6—C7	119.5 (6)	H23A—C23—H23B	108.4
C8—C7—C6	121.9 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Br1	0.93	2.77	3.658 (5)	161
C2—H2A···O2ⁱⁱⁱ	0.97	2.64	3.404 (14)	136

Symmetry code: (iii) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₄NO₄⁺·Br⁻
M_r	458.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	9.716 (4), 7.623 (3), 27.443 (11)
β (°)	92.983 (8)
V (Å³)	2029.9 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.06
Crystal size (mm)	0.12 × 0.10 × 0.06

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 2005)
T_min, T_max	0.791, 0.887
No. of measured, independent and observed [I > 2σ(I)] reflections	10394, 3592, 1965
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.161, 1.08
No. of reflections	3592
No. of parameters	276
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.55

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Selected interatomic distances (Å) top

Cg1···Cg3ⁱ

3.780 (4)

Cg2···Cg3ⁱⁱ

3.775 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Br1	0.93	2.77	3.658 (5)	161.3
C2—H2A···O2ⁱⁱⁱ	0.97	2.64	3.404 (14)	136.1

Symmetry code: (iii) x−1/2, −y+1/2, z−1/2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 20673084), the Natural Science Foundation Project of CQ CSTC (grant No. 2008BB5257) and the Major Technologies R & D Program of CQ CSTC (grant No. 2008AA5021).

References

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Kupeli, E., Kosar, M., Yesilada, E., Husnu, K. & Baser, C. (2002). Life Sci. 72, 645–657. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ye, X. L. & Li, X. G. (2007). Chinese Patent No. 200710078505.X. Google Scholar