1,4-Bis[4-(meth-oxy-carbon-yl)benz-yl]-1H-1,2,4-triazol-4-ium bromide.

In the title salt, C(20)H(20)N(3)O(4) (+)·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 = 446.30

Orthorhombic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.069

S = 1.05

2709 reflections

255 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 840 Friedel pairs

Flack parameter: 0.021 (18)

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016728/ng5263sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812016728/ng5263Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H20N3O4+·Br−	Dx = 1.488 Mg m−3
Mr = 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

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	Rint = 0.027
Detector resolution: 10.5058 pixels mm-1	θmax = 66.9°, θmin = 4.4°
φ and ω scans	h = −40→39
Absorption correction: multi-scan (ABSPACK in CrysAlis PRO; Oxford Diffraction, 2006)	k = −5→4
Tmin = 0.372, Tmax = 0.449	l = −11→14
6375 measured reflections

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(Fo2) + (0.0373P)2 + 0.0837P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2709 reflections	Δρmax = 0.37 e Å−3
255 parameters	Δρmin = −0.24 e Å−3
1 restraint	Absolute structure: Flack (1983), 840 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.021 (18)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .