1,4-Bis[4-(meth­oxy­carbon­yl)benz­yl]-1H-1,2,4-triazol-4-ium bromide

Guo, W.-J.; Huang, H.-R.; Du, Z.-Y.; Fang, Y.-X.; Zhang, K.

doi:10.1107/S1600536812016728

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1553

doi:10.1107/S1600536812016728

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1,4-Bis[4-(methoxycarbonyl)benzyl]-1H-1,2,4-triazol-4-ium bromide

Wen-Jiao Guo,^a Hua-Rong Huang,^a ^* Zhi-Yun Du,^a Yan-Xiong Fang ^a and Kun Zhang ^a

^aGuangdong University of Technology, Faculty of Chemical Engineering and Light Industry, Guangzhou 510006, Guangdong, People's Republic of China
^*Correspondence e-mail: coreyhr@yahoo.cn

(Received 11 April 2012; accepted 17 April 2012; online 28 April 2012)

In the title salt, C₂₀H₂₀N₃O₄⁺·Br⁻, the dihedral angle between the benzene rings is 8.69 (16)°, and those between the benzene rings and the triazole ring are 69.98 (18) and 72.17 (18)°. In the crystal, C—H⋯Br hydrogen bonds link the cations and anions into chains along the c axis.

Related literature

For general background to triazole derivatives, see: Zanardi et al. (2011). For a related structure, see: Huang et al. (2010 ).

Experimental

Crystal data

C₂₀H₂₀N₃O₄⁺·Br⁻
M_r = 446.30
Orthorhombic, P c a 2₁
a = 33.6880 (15) Å
b = 4.7962 (3) Å
c = 12.3337 (6) Å
V = 1992.81 (18) Å³
Z = 4
Cu Kα radiation
μ = 3.08 mm⁻¹
T = 173 K
0.40 × 0.32 × 0.31 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini Ultra diffractometer
Absorption correction: multi-scan (ABSPACK in CrysAlis PRO; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd., Abingdon, England.]$ ) T_min = 0.372, T_max = 0.449
6375 measured reflections
2709 independent reflections
2541 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.069
S = 1.05
2709 reflections
255 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 840 Friedel pairs
Flack parameter: 0.021 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Br1	0.95	2.61	3.461 (3)	149
C3—H3A⋯Br1	0.99	2.91	3.795 (4)	149
C2—H2⋯Br1ⁱ	0.95	2.75	3.657 (3)	161
Symmetry code: (i) $[-x+1, -y+1, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd., Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812016728/ng5263sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016728/ng5263Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812016728/ng5263Isup3.cml

checkCIF report

Comment top

1H-1,2,4-Triazole, like imidazole and benzimidazole, can be N-alkylated to form N-heterocyclic carbine (Zanardi et al., 2011).

In an earlier report, we presented a N-heterocyclic benzimidazole derivative. The crystal structure consists of infinite chains connected via C—H···Br and C—H···O hydrogen bonds; it also shows π···π stacking interactions (Huang et al., 2010).

In this work, we report the structure of a triazole-based N-heterocyclic carbene, 1,4-bis[4-(methoxycarbonyl)benzyl]-1H-1,2,4-triazolium bromide (Fig. 1).

In the crystal structure, the dihedral angles between the triazole ring system and the two (C4–C9) and (C13–C18) benzene rings are 69.98 (18) ° and 72.17 (18) °, respectively; the dihedral angle between the two benzene rings is 8.69 (16) °.

The bromide anions and cations form infinite hydrogen bonding chains along the c-axis via C—H···Br hydrogen bonds between the bromide anions and carbineen atoms of triazole ring and ethylene linkage (Fig. 2, Table 1).

Related literature top

For general background to triazole derivatives, see: Zanardi et al. (2011). For a related structure, see: Huang et al. (2010).

Experimental top

4-(Methoxycarbonyl)benzyl bromide (2.28 g, 10.0 mmol) was slowly added to a solution of 1H-1,2,4-triazole (0.35 g, 5.0 mmol) in acetonitrile (25 ml) and the resulting mixture was stirred under reflux for 8 h.

The solvent was evaporated under reduced pressure. The solid residue was recrystallized in methanol, and colorless block crystals were obtained after few days, yield 1.42 g, 63.5%.

Elemental analysis, calcd (%) for C₂₀H₂₀N₃BrO₄: C 53.82, H 4.52, N 9.42; found(%): C 53.80, H 4.60, N 9.41.

The FAB mass spectrum showed tje ions at 447.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO (Oxford Diffraction, 2006); data reduction: CrysAlis PRO (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Perspective view showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Crystal packing of the title compound. Dashed lines indicate hydrogen bonds. Symmetry: I = -x + 1, -y + 1, z + 1/2; II = -x + 1, -y + 2, z + 1/2. H atoms not involved in the hydrogen bond interactions have been omitted.

1,4-Bis[4-(methoxycarbonyl)benzyl]-1H-1,2,4-triazol-4-ium bromide top

Crystal data top

C₂₀H₂₀N₃O₄⁺·Br⁻	D_x = 1.488 Mg m⁻³
M_r = 446.30	Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, Pca2₁	Cell parameters from 3691 reflections
a = 33.6880 (15) Å	θ = 3.6–66.9°
b = 4.7962 (3) Å	µ = 3.08 mm⁻¹
c = 12.3337 (6) Å	T = 173 K
V = 1992.81 (18) Å³	Block, colorless
Z = 4	0.40 × 0.32 × 0.31 mm
F(000) = 912

Data collection top

Oxford Diffraction Xcalibur Atlas Gemini Ultra diffractometer	2709 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2541 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.027
Detector resolution: 10.5058 pixels mm^-1	θ_max = 66.9°, θ_min = 4.4°
ϕ and ω scans	h = −40→39
Absorption correction: multi-scan (ABSPACK in CrysAlis PRO; Oxford Diffraction, 2006)	k = −5→4
T_min = 0.372, T_max = 0.449	l = −11→14
6375 measured reflections

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)] = 0.027	H-atom parameters constrained
wR(F²) = 0.069	w = 1/[σ²(F_o²) + (0.0373P)² + 0.0837P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2709 reflections	Δρ_max = 0.37 e Å⁻³
255 parameters	Δρ_min = −0.24 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 840 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.021 (18)

Crystal data top

C₂₀H₂₀N₃O₄⁺·Br⁻	V = 1992.81 (18) Å³
M_r = 446.30	Z = 4
Orthorhombic, Pca2₁	Cu Kα radiation
a = 33.6880 (15) Å	µ = 3.08 mm⁻¹
b = 4.7962 (3) Å	T = 173 K
c = 12.3337 (6) Å	0.40 × 0.32 × 0.31 mm

Data collection top

Oxford Diffraction Xcalibur Atlas Gemini Ultra diffractometer	2709 independent reflections
Absorption correction: multi-scan (ABSPACK in CrysAlis PRO; Oxford Diffraction, 2006)	2541 reflections with I > 2σ(I)
T_min = 0.372, T_max = 0.449	R_int = 0.027
6375 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.069	Δρ_max = 0.37 e Å⁻³
S = 1.05	Δρ_min = −0.24 e Å⁻³
2709 reflections	Absolute structure: Flack (1983), 840 Friedel pairs
255 parameters	Absolute structure parameter: 0.021 (18)
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	0.47864 (8)	0.6564 (6)	0.2417 (3)	0.0375 (7)
H1	0.4887	0.7596	0.1819	0.045*
C2	0.47240 (9)	0.3718 (7)	0.3756 (3)	0.0452 (7)
H2	0.4788	0.2350	0.4285	0.054*
C3	0.40894 (9)	0.8422 (7)	0.2458 (3)	0.0480 (8)
H3A	0.4184	0.9793	0.1917	0.058*
H3B	0.3980	0.9465	0.3083	0.058*
C4	0.37667 (8)	0.6644 (6)	0.1961 (3)	0.0441 (7)
C5	0.34867 (10)	0.5364 (9)	0.2611 (3)	0.0554 (9)
H5	0.3490	0.5665	0.3373	0.067*
C6	0.32036 (11)	0.3655 (9)	0.2160 (3)	0.0599 (10)
H6	0.3017	0.2741	0.2616	0.072*
C7	0.31867 (9)	0.3249 (7)	0.1051 (3)	0.0450 (7)
C8	0.34607 (8)	0.4583 (7)	0.0390 (4)	0.0538 (7)
H8	0.3449	0.4351	−0.0374	0.065*
C9	0.37509 (10)	0.6255 (8)	0.0851 (3)	0.0533 (9)
H9	0.3941	0.7143	0.0399	0.064*
C10	0.28761 (9)	0.1331 (7)	0.0608 (4)	0.0518 (10)
C11	0.26013 (14)	−0.0757 (11)	−0.0946 (4)	0.0807 (13)
H11A	0.2335	−0.0263	−0.0690	0.121*
H11B	0.2662	−0.2681	−0.0735	0.121*
H11C	0.2612	−0.0592	−0.1737	0.121*
C12	0.53934 (10)	0.3639 (7)	0.2875 (3)	0.0456 (8)
H12A	0.5389	0.2054	0.2361	0.055*
H12B	0.5492	0.2936	0.3580	0.055*
C13	0.56784 (9)	0.5850 (7)	0.2453 (3)	0.0389 (7)
C14	0.59021 (9)	0.7440 (7)	0.3159 (3)	0.0421 (7)
H14	0.5868	0.7241	0.3919	0.051*
C15	0.61770 (9)	0.9330 (7)	0.2758 (3)	0.0454 (7)
H15	0.6334	1.0398	0.3246	0.054*
C16	0.62246 (8)	0.9668 (7)	0.1643 (3)	0.0428 (7)
C17	0.59997 (10)	0.8069 (8)	0.0951 (3)	0.0521 (8)
H17	0.6030	0.8288	0.0190	0.063*
C18	0.57294 (9)	0.6139 (8)	0.1348 (3)	0.0475 (7)
H18	0.5580	0.5021	0.0861	0.057*
C19	0.65221 (11)	1.1610 (8)	0.1181 (4)	0.0541 (10)
C20	0.70101 (11)	1.5049 (8)	0.1569 (5)	0.0781 (14)
H20A	0.7055	1.6461	0.2130	0.117*
H20B	0.6921	1.5960	0.0901	0.117*
H20C	0.7258	1.4045	0.1429	0.117*
N1	0.44256 (8)	0.6675 (5)	0.2823 (2)	0.0398 (6)
N2	0.43770 (8)	0.4859 (7)	0.3659 (2)	0.0497 (8)
N3	0.49824 (8)	0.4702 (6)	0.3018 (2)	0.0345 (5)
O1	0.26382 (8)	0.0139 (6)	0.1165 (3)	0.0724 (8)
O2	0.28892 (9)	0.1106 (6)	−0.0466 (3)	0.0679 (7)
O3	0.65877 (9)	1.1836 (7)	0.0219 (3)	0.0767 (10)
O4	0.67098 (7)	1.3101 (5)	0.1933 (3)	0.0648 (7)
Br1	0.479859 (9)	1.16298 (6)	0.04187 (3)	0.04923 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0373 (15)	0.0360 (17)	0.0391 (17)	−0.0023 (11)	0.0009 (12)	0.0032 (13)
C2	0.0461 (17)	0.051 (2)	0.0381 (17)	−0.0054 (13)	−0.0026 (13)	0.0080 (14)
C3	0.0408 (15)	0.0435 (19)	0.060 (2)	0.0051 (13)	−0.0021 (15)	−0.0033 (15)
C4	0.0349 (14)	0.0423 (18)	0.0550 (19)	0.0042 (11)	−0.0035 (14)	−0.0035 (15)
C5	0.0490 (18)	0.073 (3)	0.0444 (19)	−0.0087 (16)	0.0028 (15)	−0.0006 (17)
C6	0.0504 (18)	0.080 (3)	0.050 (2)	−0.0217 (17)	0.0059 (16)	0.0001 (18)
C7	0.0335 (14)	0.049 (2)	0.0527 (19)	0.0010 (12)	0.0005 (13)	−0.0019 (15)
C8	0.0473 (15)	0.070 (2)	0.0442 (15)	−0.0054 (13)	0.006 (2)	−0.003 (2)
C9	0.0431 (16)	0.066 (2)	0.0507 (18)	−0.0115 (15)	0.0083 (14)	0.0001 (16)
C10	0.0411 (14)	0.0516 (18)	0.063 (3)	0.0008 (13)	−0.0052 (17)	−0.0019 (19)
C11	0.083 (3)	0.087 (3)	0.072 (3)	−0.020 (2)	−0.022 (3)	−0.009 (3)
C12	0.0394 (16)	0.0411 (18)	0.056 (2)	0.0024 (13)	−0.0035 (16)	0.0029 (15)
C13	0.0333 (14)	0.0384 (17)	0.0450 (18)	0.0048 (12)	−0.0016 (13)	0.0034 (15)
C14	0.0405 (15)	0.0466 (17)	0.0392 (16)	0.0031 (12)	−0.0009 (13)	0.0001 (14)
C15	0.0393 (15)	0.0486 (19)	0.0483 (18)	−0.0006 (12)	−0.0026 (13)	−0.0061 (15)
C16	0.0367 (14)	0.0421 (18)	0.0494 (17)	0.0055 (12)	0.0017 (13)	0.0057 (14)
C17	0.0513 (18)	0.066 (3)	0.0386 (16)	−0.0032 (16)	−0.0007 (15)	0.0064 (16)
C18	0.0474 (17)	0.055 (2)	0.0405 (17)	−0.0066 (13)	−0.0061 (14)	−0.0029 (15)
C19	0.0439 (17)	0.051 (2)	0.068 (3)	0.0036 (14)	0.0061 (18)	0.0162 (19)
C20	0.0489 (19)	0.049 (2)	0.137 (4)	−0.0081 (16)	0.016 (2)	0.009 (2)
N1	0.0370 (12)	0.0420 (16)	0.0402 (14)	−0.0050 (10)	−0.0018 (12)	−0.0007 (11)
N2	0.0437 (14)	0.064 (2)	0.0408 (16)	−0.0075 (13)	0.0009 (12)	0.0105 (14)
N3	0.0365 (11)	0.0365 (14)	0.0304 (12)	−0.0044 (9)	0.0003 (9)	0.0020 (11)
O1	0.0623 (16)	0.082 (2)	0.0729 (19)	−0.0267 (15)	0.0071 (14)	−0.0048 (16)
O2	0.0654 (16)	0.0780 (19)	0.0603 (16)	−0.0199 (14)	−0.0075 (14)	−0.0071 (15)
O3	0.0720 (17)	0.087 (2)	0.071 (3)	−0.0134 (14)	0.0174 (17)	0.0213 (16)
O4	0.0499 (13)	0.0555 (16)	0.089 (2)	−0.0115 (10)	0.0067 (14)	0.0025 (15)
Br1	0.06480 (19)	0.04233 (17)	0.04057 (16)	−0.00337 (13)	−0.0031 (2)	0.0041 (2)

Geometric parameters (Å, º) top

C1—N1	1.316 (4)	C11—H11B	0.9800
C1—N3	1.335 (4)	C11—H11C	0.9800
C1—H1	0.9500	C12—N3	1.486 (5)
C2—N2	1.296 (4)	C12—C13	1.522 (5)
C2—N3	1.345 (4)	C12—H12A	0.9900
C2—H2	0.9500	C12—H12B	0.9900
C3—N1	1.479 (4)	C13—C18	1.381 (5)
C3—C4	1.512 (4)	C13—C14	1.381 (5)
C3—H3A	0.9900	C14—C15	1.387 (5)
C3—H3B	0.9900	C14—H14	0.9500
C4—C5	1.382 (5)	C15—C16	1.394 (5)
C4—C9	1.383 (5)	C15—H15	0.9500
C5—C6	1.376 (5)	C16—C17	1.376 (5)
C5—H5	0.9500	C16—C19	1.482 (5)
C6—C7	1.382 (5)	C17—C18	1.388 (5)
C6—H6	0.9500	C17—H17	0.9500
C7—C8	1.388 (5)	C18—H18	0.9500
C7—C10	1.497 (5)	C19—O3	1.212 (6)
C8—C9	1.386 (5)	C19—O4	1.331 (5)
C8—H8	0.9500	C20—O4	1.449 (4)
C9—H9	0.9500	C20—H20A	0.9800
C10—O1	1.200 (5)	C20—H20B	0.9800
C10—O2	1.331 (6)	C20—H20C	0.9800
C11—O2	1.445 (5)	N1—N2	1.359 (4)
C11—H11A	0.9800

N1—C1—N3	105.8 (3)	C13—C12—H12A	109.0
N1—C1—H1	127.1	N3—C12—H12B	109.0
N3—C1—H1	127.1	C13—C12—H12B	109.0
N2—C2—N3	111.9 (3)	H12A—C12—H12B	107.8
N2—C2—H2	124.1	C18—C13—C14	119.9 (3)
N3—C2—H2	124.1	C18—C13—C12	119.1 (3)
N1—C3—C4	110.8 (3)	C14—C13—C12	120.9 (3)
N1—C3—H3A	109.5	C13—C14—C15	120.1 (3)
C4—C3—H3A	109.5	C13—C14—H14	120.0
N1—C3—H3B	109.5	C15—C14—H14	120.0
C4—C3—H3B	109.5	C14—C15—C16	120.3 (3)
H3A—C3—H3B	108.1	C14—C15—H15	119.9
C5—C4—C9	119.3 (3)	C16—C15—H15	119.9
C5—C4—C3	120.4 (3)	C17—C16—C15	119.0 (3)
C9—C4—C3	120.3 (3)	C17—C16—C19	118.9 (3)
C6—C5—C4	120.2 (3)	C15—C16—C19	122.0 (3)
C6—C5—H5	119.9	C16—C17—C18	120.9 (3)
C4—C5—H5	119.9	C16—C17—H17	119.5
C5—C6—C7	120.9 (3)	C18—C17—H17	119.5
C5—C6—H6	119.6	C13—C18—C17	119.8 (3)
C7—C6—H6	119.6	C13—C18—H18	120.1
C6—C7—C8	119.3 (3)	C17—C18—H18	120.1
C6—C7—C10	118.4 (3)	O3—C19—O4	123.2 (4)
C8—C7—C10	122.3 (3)	O3—C19—C16	123.8 (4)
C9—C8—C7	119.7 (4)	O4—C19—C16	113.0 (3)
C9—C8—H8	120.2	O4—C20—H20A	109.5
C7—C8—H8	120.2	O4—C20—H20B	109.5
C4—C9—C8	120.7 (3)	H20A—C20—H20B	109.5
C4—C9—H9	119.6	O4—C20—H20C	109.5
C8—C9—H9	119.6	H20A—C20—H20C	109.5
O1—C10—O2	123.6 (4)	H20B—C20—H20C	109.5
O1—C10—C7	123.4 (4)	C1—N1—N2	112.0 (3)
O2—C10—C7	113.0 (3)	C1—N1—C3	127.9 (3)
O2—C11—H11A	109.5	N2—N1—C3	120.1 (3)
O2—C11—H11B	109.5	C2—N2—N1	103.4 (3)
H11A—C11—H11B	109.5	C1—N3—C2	106.9 (3)
O2—C11—H11C	109.5	C1—N3—C12	128.6 (3)
H11A—C11—H11C	109.5	C2—N3—C12	124.2 (3)
H11B—C11—H11C	109.5	C10—O2—C11	115.8 (4)
N3—C12—C13	112.9 (3)	C19—O4—C20	117.5 (4)
N3—C12—H12A	109.0

N1—C3—C4—C5	84.0 (4)	C14—C13—C18—C17	−1.3 (5)
N1—C3—C4—C9	−95.3 (4)	C12—C13—C18—C17	−177.5 (3)
C9—C4—C5—C6	2.0 (6)	C16—C17—C18—C13	1.3 (5)
C3—C4—C5—C6	−177.3 (3)	C17—C16—C19—O3	−1.9 (6)
C4—C5—C6—C7	−1.8 (6)	C15—C16—C19—O3	175.5 (4)
C5—C6—C7—C8	0.2 (6)	C17—C16—C19—O4	177.8 (3)
C5—C6—C7—C10	179.1 (3)	C15—C16—C19—O4	−4.9 (5)
C6—C7—C8—C9	1.2 (5)	N3—C1—N1—N2	−1.9 (4)
C10—C7—C8—C9	−177.6 (3)	N3—C1—N1—C3	179.8 (3)
C5—C4—C9—C8	−0.6 (6)	C4—C3—N1—C1	111.4 (4)
C3—C4—C9—C8	178.7 (3)	C4—C3—N1—N2	−66.8 (4)
C7—C8—C9—C4	−1.0 (5)	N3—C2—N2—N1	−0.8 (4)
C6—C7—C10—O1	0.6 (5)	C1—N1—N2—C2	1.7 (4)
C8—C7—C10—O1	179.4 (3)	C3—N1—N2—C2	−179.8 (3)
C6—C7—C10—O2	−180.0 (4)	N1—C1—N3—C2	1.3 (4)
C8—C7—C10—O2	−1.1 (5)	N1—C1—N3—C12	175.9 (3)
N3—C12—C13—C18	−90.6 (4)	N2—C2—N3—C1	−0.3 (4)
N3—C12—C13—C14	93.2 (4)	N2—C2—N3—C12	−175.2 (3)
C18—C13—C14—C15	0.1 (5)	C13—C12—N3—C1	35.4 (5)
C12—C13—C14—C15	176.2 (3)	C13—C12—N3—C2	−150.9 (3)
C13—C14—C15—C16	1.1 (5)	O1—C10—O2—C11	−1.6 (6)
C14—C15—C16—C17	−1.1 (5)	C7—C10—O2—C11	178.9 (3)
C14—C15—C16—C19	−178.4 (3)	O3—C19—O4—C20	−0.9 (5)
C15—C16—C17—C18	−0.1 (5)	C16—C19—O4—C20	179.4 (3)
C19—C16—C17—C18	177.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br1	0.95	2.61	3.461 (3)	149
C3—H3A···Br1	0.99	2.91	3.795 (4)	149
C2—H2···Br1ⁱ	0.95	2.75	3.657 (3)	161

Symmetry code: (i) −x+1, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀N₃O₄⁺·Br⁻
M_r	446.30
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	173
a, b, c (Å)	33.6880 (15), 4.7962 (3), 12.3337 (6)
V (Å³)	1992.81 (18)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.08
Crystal size (mm)	0.40 × 0.32 × 0.31

Data collection
Diffractometer	Oxford Diffraction Xcalibur Atlas Gemini Ultra diffractometer
Absorption correction	Multi-scan (ABSPACK in CrysAlis PRO; Oxford Diffraction, 2006)
T_min, T_max	0.372, 0.449
No. of measured, independent and observed [I > 2σ(I)] reflections	6375, 2709, 2541
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.069, 1.05
No. of reflections	2709
No. of parameters	255
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.24
Absolute structure	Flack (1983), 840 Friedel pairs
Absolute structure parameter	0.021 (18)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br1	0.95	2.61	3.461 (3)	149.2
C3—H3A···Br1	0.99	2.91	3.795 (4)	149.2
C2—H2···Br1ⁱ	0.95	2.75	3.657 (3)	160.9

Symmetry code: (i) −x+1, −y+1, z+1/2.

Acknowledgements

This work was funded by the 211 Project of Guangdong Province.

References

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