1,3,5-Tris(2H-tetra-zol-5-ylmeth-oxy)-benzene.

The title compound, C(12)H(12)N(12)O(3), was obtained by the hydro-thermal reaction of 1,3,5-tricyano-methoxy-benzene and (CH(3))(3)SiN(3). The mol-ecule is almost planar, with an r.m.s. deviation of 0.0976 Å from the plane through all atoms in the mol-ecule. The three tetra-zole rings make dihedral angles of 13.09 (19), 2.01 (19) and 11.56 (18)° with one another and corresponding angles of 8.66 (17), 5.44 (16) and 3.51 (17)° with the central benzene ring. In the crystal structure, inter-molecular N-H⋯N hydrogen bonds form well separated one-dimensional planar sheets.

Related literature

For the use of tetra­zole derivatives in coordination chemisty, see: Arp et al. (2000 ▶); Hu et al. (2007 ▶); Wang et al. (2005 ▶); Xiong et al. (2002 ▶).

Experimental

Crystal data

C12H12N12O3

M = 372.34

Triclinic,

a = 4.9851 (4) Å

b = 11.8822 (7) Å

c = 14.1349 (13) Å

α = 99.60 (3)°

β = 92.87 (2)°

γ = 100.943 (15)°

V = 807.64 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 293 (2) K

0.25 × 0.2 × 0.12 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.891, T max = 1 (expected range = 0.879–0.986)

8398 measured reflections

3686 independent reflections

2653 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.149

S = 1.05

3686 reflections

256 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 1999 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062733/sj2442sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062733/sj2442Isup2.hkl

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

C12H12N12O3	Z = 2
Mr = 372.34	F000 = 384
Triclinic, P1	Dx = 1.531 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 4.9851 (4) Å	Cell parameters from 1880 reflections
b = 11.8822 (7) Å	θ = 3.1–27.5º
c = 14.1349 (13) Å	µ = 0.12 mm−1
α = 99.60 (3)º	T = 293 (2) K
β = 92.87 (2)º	Block, colorless
γ = 100.943 (15)º	0.25 × 0.2 × 0.12 mm
V = 807.64 (11) Å3

Rigaku Mercury2 (2 × 2 bin mode) diffractometer	3686 independent reflections
Radiation source: fine-focus sealed tube	2653 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.036
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.1º
ω scans	h = −6→6
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −15→15
Tmin = 0.891, Tmax = 1	l = −18→18
8398 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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.149	w = 1/[σ2(Fo2) + (0.0711P)2 + 0.2604P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3686 reflections	Δρmax = 0.53 e Å−3
256 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
O1	0.4944 (3)	0.29164 (13)	0.81580 (10)	0.0364 (4)
O2	0.0878 (3)	0.18419 (13)	0.49413 (10)	0.0343 (4)
O3	−0.1336 (3)	0.50558 (12)	0.70463 (9)	0.0309 (4)
N1	0.8441 (5)	0.23109 (18)	0.93683 (14)	0.0450 (6)
N2	1.0188 (5)	0.21973 (19)	1.00837 (15)	0.0543 (6)
N3	1.0297 (4)	0.30962 (18)	1.07529 (13)	0.0435 (5)
N4	0.8662 (4)	0.38061 (17)	1.04861 (13)	0.0419 (5)
N5	0.0149 (4)	0.07285 (16)	0.31051 (12)	0.0338 (4)
N6	0.0071 (4)	0.00274 (18)	0.22479 (13)	0.0433 (5)
N7	0.1856 (4)	−0.06057 (17)	0.23524 (13)	0.0426 (5)
N8	0.3127 (4)	−0.03434 (16)	0.32650 (12)	0.0369 (5)
N9	−0.6125 (4)	0.66664 (15)	0.62247 (12)	0.0329 (4)
N10	−0.6780 (4)	0.75385 (16)	0.68837 (13)	0.0363 (5)
N11	−0.5411 (4)	0.76527 (16)	0.77066 (13)	0.0381 (5)
N12	−0.3816 (4)	0.68545 (16)	0.75912 (13)	0.0318 (4)
C1	0.3201 (4)	0.31401 (17)	0.74592 (14)	0.0260 (4)
C2	0.3001 (4)	0.23846 (17)	0.65792 (14)	0.0276 (5)
H2A	0.3999	0.1794	0.6492	0.033*
C3	0.1271 (4)	0.25444 (17)	0.58426 (13)	0.0248 (4)
C4	−0.0233 (4)	0.34265 (17)	0.59459 (13)	0.0251 (4)
H4A	−0.1373	0.3525	0.5438	0.030*
C5	0.0037 (4)	0.41535 (16)	0.68380 (13)	0.0235 (4)
C6	0.1764 (4)	0.40318 (17)	0.76073 (13)	0.0262 (4)
H6A	0.1941	0.4533	0.8197	0.031*
C7	0.5606 (5)	0.37403 (19)	0.90189 (14)	0.0337 (5)
H7B	0.3966	0.3825	0.9342	0.040*
H7C	0.6471	0.4494	0.8885	0.040*
C8	0.7525 (4)	0.32884 (18)	0.96283 (14)	0.0304 (5)
C9	0.2734 (4)	0.10828 (18)	0.47337 (14)	0.0288 (5)
H9B	0.2553	0.0514	0.5158	0.035*
H9C	0.4608	0.1520	0.4819	0.035*
C10	0.2012 (4)	0.04925 (17)	0.37119 (14)	0.0271 (4)
C11	−0.2956 (4)	0.52921 (18)	0.62784 (14)	0.0278 (5)
H11A	−0.4333	0.4607	0.6002	0.033*
H11B	−0.1816	0.5516	0.5777	0.033*
C12	−0.4281 (4)	0.62620 (17)	0.66905 (14)	0.0256 (4)
H12A	−0.268 (5)	0.681 (2)	0.8099 (19)	0.048 (7)*
H5A	−0.090 (7)	0.126 (3)	0.318 (2)	0.077 (10)*
H1A	0.808 (6)	0.176 (3)	0.882 (2)	0.064 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0490 (9)	0.0375 (8)	0.0236 (7)	0.0275 (7)	−0.0165 (7)	−0.0079 (6)
O2	0.0413 (9)	0.0390 (8)	0.0234 (7)	0.0269 (7)	−0.0091 (6)	−0.0103 (6)
O3	0.0391 (8)	0.0347 (8)	0.0221 (7)	0.0253 (7)	−0.0067 (6)	−0.0033 (6)
N1	0.0618 (14)	0.0433 (11)	0.0291 (10)	0.0286 (10)	−0.0201 (9)	−0.0090 (9)
N2	0.0733 (16)	0.0548 (13)	0.0368 (11)	0.0376 (12)	−0.0231 (11)	−0.0061 (10)
N3	0.0542 (13)	0.0512 (12)	0.0267 (10)	0.0262 (10)	−0.0139 (9)	−0.0014 (9)
N4	0.0558 (13)	0.0448 (11)	0.0241 (9)	0.0238 (10)	−0.0154 (9)	−0.0069 (8)
N5	0.0411 (11)	0.0361 (10)	0.0257 (9)	0.0227 (9)	−0.0054 (8)	−0.0046 (8)
N6	0.0566 (13)	0.0449 (11)	0.0283 (10)	0.0256 (10)	−0.0070 (9)	−0.0086 (8)
N7	0.0576 (13)	0.0404 (11)	0.0303 (10)	0.0252 (10)	−0.0025 (9)	−0.0078 (8)
N8	0.0483 (12)	0.0362 (10)	0.0279 (9)	0.0245 (9)	−0.0041 (8)	−0.0051 (8)
N9	0.0360 (10)	0.0357 (10)	0.0305 (9)	0.0208 (8)	−0.0076 (8)	0.0030 (8)
N10	0.0386 (11)	0.0351 (10)	0.0391 (10)	0.0221 (8)	−0.0043 (8)	0.0034 (8)
N11	0.0452 (11)	0.0385 (10)	0.0338 (10)	0.0251 (9)	−0.0039 (8)	−0.0009 (8)
N12	0.0381 (10)	0.0347 (10)	0.0258 (9)	0.0218 (8)	−0.0064 (8)	0.0002 (7)
C1	0.0287 (10)	0.0285 (10)	0.0215 (9)	0.0131 (8)	−0.0066 (8)	0.0010 (8)
C2	0.0317 (11)	0.0266 (10)	0.0254 (10)	0.0161 (8)	−0.0037 (8)	−0.0026 (8)
C3	0.0275 (10)	0.0260 (10)	0.0194 (9)	0.0097 (8)	−0.0031 (8)	−0.0032 (8)
C4	0.0262 (10)	0.0293 (10)	0.0205 (9)	0.0127 (8)	−0.0050 (8)	0.0011 (8)
C5	0.0241 (10)	0.0246 (10)	0.0238 (9)	0.0131 (8)	0.0004 (8)	0.0013 (8)
C6	0.0314 (11)	0.0290 (10)	0.0183 (9)	0.0136 (8)	−0.0053 (8)	−0.0022 (8)
C7	0.0420 (12)	0.0352 (12)	0.0234 (10)	0.0191 (10)	−0.0117 (9)	−0.0048 (9)
C8	0.0375 (12)	0.0319 (11)	0.0219 (10)	0.0158 (9)	−0.0064 (9)	−0.0028 (8)
C9	0.0341 (11)	0.0279 (10)	0.0254 (10)	0.0156 (9)	−0.0024 (8)	−0.0020 (8)
C10	0.0317 (11)	0.0247 (10)	0.0261 (10)	0.0122 (8)	−0.0013 (8)	0.0015 (8)
C11	0.0313 (11)	0.0333 (11)	0.0216 (10)	0.0176 (9)	−0.0044 (8)	0.0017 (8)
C12	0.0272 (10)	0.0269 (10)	0.0235 (9)	0.0099 (8)	−0.0036 (8)	0.0032 (8)

O1—C1	1.375 (2)	N11—N12	1.344 (2)
O1—C7	1.410 (2)	N12—C12	1.334 (3)
O2—C3	1.384 (2)	N12—H12A	0.91 (3)
O2—C9	1.418 (2)	C1—C6	1.382 (3)
O3—C5	1.378 (2)	C1—C2	1.394 (3)
O3—C11	1.417 (2)	C2—C3	1.379 (3)
N1—C8	1.330 (3)	C2—H2A	0.9300
N1—N2	1.342 (3)	C3—C4	1.393 (3)
N1—H1A	0.92 (3)	C4—C5	1.389 (3)
N2—N3	1.294 (3)	C4—H4A	0.9300
N3—N4	1.362 (3)	C5—C6	1.397 (3)
N4—C8	1.312 (3)	C6—H6A	0.9300
N5—C10	1.333 (3)	C7—C8	1.488 (3)
N5—N6	1.345 (2)	C7—H7B	0.9700
N5—H5A	0.89 (3)	C7—H7C	0.9700
N6—N7	1.288 (3)	C9—C10	1.490 (3)
N7—N8	1.368 (2)	C9—H9B	0.9700
N8—C10	1.315 (3)	C9—H9C	0.9700
N9—C12	1.312 (2)	C11—C12	1.486 (3)
N9—N10	1.373 (2)	C11—H11A	0.9700
N10—N11	1.292 (3)	C11—H11B	0.9700
C1—O1—C7	117.89 (15)	O3—C5—C4	123.76 (16)
C3—O2—C9	116.70 (15)	O3—C5—C6	113.94 (16)
C5—O3—C11	117.10 (15)	C4—C5—C6	122.29 (17)
C8—N1—N2	108.52 (18)	C1—C6—C5	117.55 (17)
C8—N1—H1A	131.7 (18)	C1—C6—H6A	121.2
N2—N1—H1A	119.7 (18)	C5—C6—H6A	121.2
N3—N2—N1	106.11 (18)	O1—C7—C8	106.33 (16)
N2—N3—N4	110.95 (17)	O1—C7—H7B	110.5
C8—N4—N3	105.18 (17)	C8—C7—H7B	110.5
C10—N5—N6	108.75 (17)	O1—C7—H7C	110.5
C10—N5—H5A	131 (2)	C8—C7—H7C	110.5
N6—N5—H5A	120 (2)	H7B—C7—H7C	108.7
N7—N6—N5	105.78 (17)	N4—C8—N1	109.23 (18)
N6—N7—N8	111.65 (17)	N4—C8—C7	125.76 (18)
C10—N8—N7	104.66 (17)	N1—C8—C7	124.96 (17)
C12—N9—N10	105.02 (16)	O2—C9—C10	106.34 (16)
N11—N10—N9	111.16 (16)	O2—C9—H9B	110.5
N10—N11—N12	105.82 (17)	C10—C9—H9B	110.5
C12—N12—N11	109.01 (16)	O2—C9—H9C	110.5
C12—N12—H12A	132.7 (17)	C10—C9—H9C	110.5
N11—N12—H12A	118.2 (17)	H9B—C9—H9C	108.7
O1—C1—C6	123.45 (17)	N8—C10—N5	109.17 (17)
O1—C1—C2	114.07 (16)	N8—C10—C9	125.23 (18)
C6—C1—C2	122.48 (17)	N5—C10—C9	125.60 (17)
C3—C2—C1	117.63 (17)	O3—C11—C12	106.70 (15)
C3—C2—H2A	121.2	O3—C11—H11A	110.4
C1—C2—H2A	121.2	C12—C11—H11A	110.4
C2—C3—O2	122.91 (17)	O3—C11—H11B	110.4
C2—C3—C4	122.66 (17)	C12—C11—H11B	110.4
O2—C3—C4	114.43 (16)	H11A—C11—H11B	108.6
C5—C4—C3	117.38 (17)	N9—C12—N12	108.99 (17)
C5—C4—H4A	121.3	N9—C12—C11	125.19 (17)
C3—C4—H4A	121.3	N12—C12—C11	125.81 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N7i	0.92 (3)	1.97 (3)	2.872 (3)	168 (3)
N5—H5A···N10ii	0.89 (3)	2.01 (3)	2.892 (2)	171 (3)
N12—H12A···N3iii	0.91 (3)	1.94 (3)	2.840 (3)	174 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N7i	0.92 (3)	1.97 (3)	2.872 (3)	168 (3)
N5—H5A⋯N10ii	0.89 (3)	2.01 (3)	2.892 (2)	171 (3)
N12—H12A⋯N3iii	0.91 (3)	1.94 (3)	2.840 (3)	174 (2)

Symmetry codes: (i) ; (ii) ; (iii) .