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.
Supporting information
CCDC reference: 601102
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.119
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
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
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
top
Crystal data top
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) Å3 | 0.50 × 0.30 × 0.25 mm |
Z = 4 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.06P)2 + 0.3301P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O2i | 0.96 (3) | 2.33 (3) | 3.249 (3) | 161 (2) |
C11—H11···N3ii | 0.99 (2) | 2.61 (2) | 3.444 (3) | 141.6 (18) |
C13—H13A···O4iii | 0.96 (2) | 2.58 (2) | 3.448 (3) | 150.9 (17) |
C13—H13B···O3iv | 0.98 (2) | 2.49 (2) | 3.337 (2) | 143.6 (16) |
C14—H14A···O3iv | 0.96 | 2.58 | 3.385 (3) | 142 |
C14—H14C···N4v | 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. |