5-Mesylmeth­oxy-1-(4-nitro­phen­yl)tetra­zole

The title compound, C₉H₉N₅O₅S, was prepared by the reaction of 5-mesyl-1-(4-nitro­phen­yl)tetra­zole with formaldehyde in a solution of acetonitrile and triethyl­amine. In the crystal structure, mol­ecules are linked together by a complex set of hydrogen bonds, forming polymeric sheets parallel to the bc plane, with van der Waals inter­actions between them.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.119
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

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Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N12

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: R3m Software (Nicolet, 1980); cell refinement: R3m Software; data reduction: R3m Software; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

5-Mesylmethoxy-1-(4-nitrophenyl)tetrazole

Crystal data

C9H9N5O5S	F(000) = 616
Mr = 299.27	Dx = 1.582 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 12.413 (3) Å	θ = 14.8–18.6°
b = 8.093 (3) Å	µ = 0.29 mm^−1
c = 12.770 (3) Å	T = 292 K
β = 101.696 (17)°	Prism, colourless
V = 1256.2 (6) Å^3	0.50 × 0.30 × 0.25 mm
Z = 4

Data collection

Nicolet R3m four-circle diffractometer	2333 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
Graphite monochromator	θmax = 27.6°, θmin = 1.7°
ω/2θ scans	h = 0→16
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.885, Tmax = 0.933	l = −16→16
3053 measured reflections	3 standard reflections every 100 reflections
2920 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: difference Fourier map
wR(F^2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.06P)^2 + 0.3301P] where P = (Fo^2 + 2Fc^2)/3
2920 reflections	(Δ/σ)max = 0.001
206 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	1.01559 (4)	0.12883 (6)	0.85348 (4)	0.05077 (16)
O3	1.07668 (11)	−0.00527 (18)	0.91067 (11)	0.0608 (4)
O4	1.04308 (14)	0.1843 (2)	0.75575 (13)	0.0746 (5)
N1	0.72002 (12)	0.29950 (19)	0.60690 (11)	0.0466 (3)
N2	0.70247 (15)	0.2471 (2)	0.50318 (12)	0.0630 (5)
N3	0.74825 (17)	0.1049 (3)	0.50404 (14)	0.0702 (5)
N4	0.79718 (15)	0.0583 (2)	0.60541 (13)	0.0620 (4)
C5	0.77867 (14)	0.1804 (2)	0.66563 (14)	0.0480 (4)
O5	0.80806 (11)	0.19224 (17)	0.77134 (9)	0.0560 (3)
C6	0.68264 (13)	0.4576 (2)	0.63270 (13)	0.0442 (4)
C7	0.63760 (17)	0.5621 (3)	0.54982 (14)	0.0564 (5)
H7	0.6277 (19)	0.523 (3)	0.477 (2)	0.079 (7)*
C8	0.60233 (18)	0.7163 (3)	0.57186 (15)	0.0568 (5)
H8	0.574 (2)	0.788 (3)	0.522 (2)	0.079 (7)*
C9	0.61311 (14)	0.7642 (2)	0.67681 (13)	0.0476 (4)
C10	0.65693 (17)	0.6613 (3)	0.75983 (14)	0.0564 (5)
H10	0.657 (2)	0.696 (3)	0.8309 (19)	0.073 (7)*
C11	0.69095 (17)	0.5053 (3)	0.73805 (14)	0.0561 (5)
H11	0.7224 (19)	0.429 (3)	0.7972 (19)	0.075 (7)*
N12	0.57836 (14)	0.9301 (2)	0.69993 (13)	0.0590 (4)
O1	0.53584 (15)	1.0187 (2)	0.62637 (13)	0.0787 (5)
O2	0.59597 (19)	0.9764 (3)	0.79146 (13)	0.1055 (8)
C13	0.87550 (15)	0.0626 (2)	0.82517 (15)	0.0498 (4)
H13A	0.8734 (18)	−0.036 (3)	0.7837 (18)	0.064 (6)*
H13B	0.8529 (17)	0.043 (3)	0.8935 (18)	0.063 (6)*
C14	1.0160 (2)	0.2969 (3)	0.9394 (2)	0.0701 (6)
H14A	0.9914	0.2616	1.0024	0.105*
H14B	0.9676	0.3811	0.9038	0.105*
H14C	1.0892	0.3405	0.9592	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0525 (3)	0.0515 (3)	0.0495 (3)	0.00377 (19)	0.01306 (19)	0.00956 (19)
O3	0.0522 (7)	0.0650 (9)	0.0645 (8)	0.0140 (6)	0.0104 (6)	0.0135 (7)
O4	0.0824 (10)	0.0855 (11)	0.0625 (9)	0.0017 (9)	0.0307 (8)	0.0207 (8)
N1	0.0493 (8)	0.0556 (9)	0.0340 (7)	0.0055 (7)	0.0059 (6)	0.0022 (6)
N2	0.0777 (11)	0.0713 (11)	0.0369 (8)	0.0115 (9)	0.0044 (7)	−0.0056 (7)
N3	0.0866 (13)	0.0756 (12)	0.0453 (9)	0.0173 (10)	0.0058 (8)	−0.0079 (8)
N4	0.0706 (11)	0.0648 (10)	0.0487 (9)	0.0156 (9)	0.0079 (8)	−0.0046 (8)
C5	0.0459 (9)	0.0569 (10)	0.0409 (8)	0.0065 (8)	0.0078 (7)	0.0010 (7)
O5	0.0631 (8)	0.0624 (8)	0.0392 (6)	0.0214 (6)	0.0023 (5)	0.0031 (6)
C6	0.0418 (8)	0.0541 (10)	0.0362 (8)	0.0038 (7)	0.0069 (6)	0.0041 (7)
C7	0.0684 (12)	0.0667 (12)	0.0307 (8)	0.0115 (10)	0.0023 (8)	0.0035 (8)
C8	0.0678 (12)	0.0620 (12)	0.0372 (9)	0.0132 (10)	0.0028 (8)	0.0103 (8)
C9	0.0463 (9)	0.0541 (10)	0.0412 (8)	0.0054 (8)	0.0064 (7)	0.0045 (7)
C10	0.0669 (12)	0.0678 (12)	0.0334 (8)	0.0157 (10)	0.0078 (8)	0.0031 (8)
C11	0.0694 (12)	0.0639 (12)	0.0342 (8)	0.0197 (10)	0.0085 (8)	0.0091 (8)
N12	0.0628 (10)	0.0623 (10)	0.0497 (9)	0.0131 (8)	0.0062 (7)	0.0019 (8)
O1	0.0987 (12)	0.0729 (10)	0.0635 (9)	0.0335 (9)	0.0141 (8)	0.0160 (8)
O2	0.160 (2)	0.0893 (13)	0.0538 (9)	0.0487 (13)	−0.0100 (11)	−0.0178 (9)
C13	0.0526 (10)	0.0482 (10)	0.0464 (9)	0.0083 (8)	0.0049 (8)	0.0079 (8)
C14	0.0819 (15)	0.0546 (12)	0.0757 (14)	−0.0133 (11)	0.0202 (12)	−0.0037 (11)

Geometric parameters (Å, º)

S1—O4	1.4312 (15)	C7—H7	0.96 (3)
S1—O3	1.4358 (14)	C8—C9	1.375 (2)
S1—C14	1.747 (2)	C8—H8	0.88 (3)
S1—C13	1.785 (2)	C9—C10	1.371 (3)
N1—C5	1.342 (2)	C9—N12	1.459 (3)
N1—N2	1.366 (2)	C10—C11	1.377 (3)
N1—C6	1.422 (2)	C10—H10	0.95 (2)
N2—N3	1.282 (3)	C11—H11	0.99 (2)
N3—N4	1.367 (2)	N12—O2	1.204 (2)
N4—C5	1.301 (2)	N12—O1	1.214 (2)
C5—O5	1.328 (2)	C13—H13A	0.96 (2)
O5—C13	1.428 (2)	C13—H13B	0.98 (2)
C6—C7	1.381 (2)	C14—H14A	0.9600
C6—C11	1.383 (2)	C14—H14B	0.9600
C7—C8	1.370 (3)	C14—H14C	0.9600
O4—S1—O3	119.08 (10)	C10—C9—C8	121.81 (18)
O4—S1—C14	109.41 (11)	C10—C9—N12	119.34 (16)
O3—S1—C14	109.59 (11)	C8—C9—N12	118.84 (16)
O4—S1—C13	108.19 (10)	C9—C10—C11	119.37 (17)
O3—S1—C13	105.57 (9)	C9—C10—H10	118.6 (15)
C14—S1—C13	103.86 (11)	C11—C10—H10	121.8 (15)
C5—N1—N2	106.30 (15)	C10—C11—C6	119.14 (17)
C5—N1—C6	133.03 (15)	C10—C11—H11	120.5 (14)
N2—N1—C6	120.59 (14)	C6—C11—H11	120.4 (14)
N3—N2—N1	106.70 (15)	O2—N12—O1	122.15 (19)
N2—N3—N4	111.52 (16)	O2—N12—C9	118.66 (17)
C5—N4—N3	104.61 (16)	O1—N12—C9	119.15 (17)
N4—C5—O5	127.63 (17)	O5—C13—S1	109.20 (13)
N4—C5—N1	110.86 (16)	O5—C13—H13A	113.6 (13)
O5—C5—N1	121.48 (16)	S1—C13—H13A	106.2 (13)
C5—O5—C13	116.71 (15)	O5—C13—H13B	107.7 (13)
C7—C6—C11	120.86 (18)	S1—C13—H13B	108.2 (12)
C7—C6—N1	118.27 (15)	H13A—C13—H13B	111.9 (18)
C11—C6—N1	120.87 (15)	S1—C14—H14A	109.5
C8—C7—C6	119.78 (17)	S1—C14—H14B	109.5
C8—C7—H7	120.9 (15)	H14A—C14—H14B	109.5
C6—C7—H7	119.2 (15)	S1—C14—H14C	109.5
C7—C8—C9	119.00 (17)	H14A—C14—H14C	109.5
C7—C8—H8	123.1 (17)	H14B—C14—H14C	109.5
C9—C8—H8	117.9 (17)
C5—N1—N2—N3	0.5 (2)	N1—C6—C7—C8	−179.00 (18)
C6—N1—N2—N3	177.57 (17)	C6—C7—C8—C9	0.3 (3)
N1—N2—N3—N4	−0.2 (3)	C7—C8—C9—C10	−0.8 (3)
N2—N3—N4—C5	−0.2 (3)	C7—C8—C9—N12	178.27 (18)
N3—N4—C5—O5	178.54 (19)	C8—C9—C10—C11	−0.2 (3)
N3—N4—C5—N1	0.5 (2)	N12—C9—C10—C11	−179.23 (19)
N2—N1—C5—N4	−0.7 (2)	C9—C10—C11—C6	1.6 (3)
C6—N1—C5—N4	−177.19 (18)	C7—C6—C11—C10	−2.1 (3)
N2—N1—C5—O5	−178.83 (17)	N1—C6—C11—C10	178.04 (18)
C6—N1—C5—O5	4.7 (3)	C10—C9—N12—O2	5.0 (3)
N4—C5—O5—C13	5.5 (3)	C8—C9—N12—O2	−174.1 (2)
N1—C5—O5—C13	−176.64 (16)	C10—C9—N12—O1	−177.3 (2)
C5—N1—C6—C7	170.18 (19)	C8—C9—N12—O1	3.6 (3)
N2—N1—C6—C7	−5.9 (2)	C5—O5—C13—S1	99.22 (17)
C5—N1—C6—C11	−10.0 (3)	O4—S1—C13—O5	−53.57 (16)
N2—N1—C6—C11	173.94 (18)	O3—S1—C13—O5	177.92 (12)
C11—C6—C7—C8	1.1 (3)	C14—S1—C13—O5	62.62 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2^i	0.96 (3)	2.33 (3)	3.249 (3)	161 (2)
C11—H11···N3^ii	0.99 (2)	2.61 (2)	3.444 (3)	141.6 (18)
C13—H13A···O4^iii	0.96 (2)	2.58 (2)	3.448 (3)	150.9 (17)
C13—H13B···O3^iv	0.98 (2)	2.49 (2)	3.337 (2)	143.6 (16)
C14—H14A···O3^iv	0.96	2.58	3.385 (3)	142
C14—H14C···N4^v	0.96	2.50	3.274 (3)	138
C11—H11···O5	0.99 (2)	2.25 (2)	2.909 (2)	123.0 (18)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+2, y−1/2, −z+3/2; (iv) −x+2, −y, −z+2; (v) −x+2, y+1/2, −z+3/2.