The relative stereochemistry of methyl 6-oxo-5-(5-phenyltetrazol-2-yl)piperidine-2-carboxylate, C
14H
15N
5O
3, has been determined. It confirms the
cis configuration of the piperidine ring as well as the position of the substituent on the tetrazole ring. The packing of the molecules is influenced by N—H
O and C—H
N hydrogen bonds.
Supporting information
CCDC reference: 242340
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.108
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C13
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: KappaCCD Server Software (Nonius, 1998); data reduction: DENZO (Otwinowski & Miror, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farugia, 1999).
6-oxo-5-(5-phenyltetrazol-2-yl)piperidine-2-carboxylate
top
Crystal data top
C14H15N5O3 | Z = 4 |
Mr = 301.31 | F(000) = 632 |
Monoclinic, P21/c | Dx = 1.356 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71069 Å |
a = 12.7980 (6) Å | µ = 0.10 mm−1 |
b = 10.8334 (3) Å | T = 296 K |
c = 10.9142 (3) Å | Needle, colourless |
β = 102.796 (1)° | 0.1 × 0.08 × 0.05 mm |
V = 1475.63 (9) Å3 | |
Data collection top
Nonius KappaCCD diffractometer | 1777 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 25.0°, θmin = 3.8° |
ω scans | h = −15→14 |
5170 measured reflections | k = 0→12 |
2563 independent reflections | l = 0→12 |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0438P)2 + 0.1856P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.044 | (Δ/σ)max = 0.001 |
wR(F2) = 0.108 | Δρmax = 0.16 e Å−3 |
S = 1.04 | Δρmin = −0.15 e Å−3 |
2563 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
204 parameters | Extinction coefficient: 0.026 (4) |
0 restraints | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.52361 (14) | 0.15788 (16) | 0.06580 (15) | 0.0462 (5) | |
H1N | 0.5552 (19) | 0.097 (2) | 0.032 (2) | 0.076 (8)* | |
N2 | 0.29820 (13) | 0.18081 (13) | 0.21242 (13) | 0.0378 (4) | |
N3 | 0.19857 (13) | 0.14531 (14) | 0.16191 (13) | 0.0416 (4) | |
N4 | 0.24570 (14) | 0.10269 (16) | 0.36540 (14) | 0.0518 (5) | |
N5 | 0.32864 (14) | 0.15610 (15) | 0.33375 (14) | 0.0487 (5) | |
O1 | 0.76028 (12) | 0.28508 (14) | 0.24956 (13) | 0.0665 (5) | |
O2 | 0.65052 (14) | 0.15029 (16) | 0.30919 (15) | 0.0822 (6) | |
O3 | 0.38084 (12) | 0.03380 (13) | 0.05594 (13) | 0.0579 (4) | |
C1 | 0.59129 (16) | 0.26183 (17) | 0.11582 (16) | 0.0445 (5) | |
H1 | 0.6323 | 0.2865 | 0.0539 | 0.053* | |
C2 | 0.42661 (16) | 0.13289 (18) | 0.08577 (16) | 0.0407 (5) | |
C3 | 0.36943 (15) | 0.23592 (16) | 0.14012 (15) | 0.0393 (5) | |
H3 | 0.3240 | 0.2790 | 0.0689 | 0.047* | |
C4 | 0.44307 (17) | 0.33169 (17) | 0.21531 (19) | 0.0510 (6) | |
H4A | 0.4798 | 0.2971 | 0.2952 | 0.061* | |
H4B | 0.4018 | 0.4025 | 0.2316 | 0.061* | |
C5 | 0.52385 (18) | 0.37085 (18) | 0.1399 (2) | 0.0541 (6) | |
H5A | 0.5702 | 0.4343 | 0.1855 | 0.065* | |
H5B | 0.4864 | 0.4055 | 0.0604 | 0.065* | |
C6 | 0.16740 (16) | 0.09652 (16) | 0.25988 (16) | 0.0404 (5) | |
C7 | 0.06222 (16) | 0.04183 (17) | 0.25248 (17) | 0.0448 (5) | |
C8 | 0.0422 (2) | −0.0313 (2) | 0.34883 (19) | 0.0605 (6) | |
H8 | 0.0957 | −0.0438 | 0.4207 | 0.073* | |
C9 | −0.0567 (2) | −0.0855 (2) | 0.3385 (2) | 0.0747 (7) | |
H9 | −0.0695 | −0.1345 | 0.4036 | 0.090* | |
C10 | −0.1362 (2) | −0.0680 (2) | 0.2333 (3) | 0.0740 (7) | |
H10 | −0.2027 | −0.1051 | 0.2270 | 0.089* | |
C11 | −0.11774 (19) | 0.0041 (2) | 0.1370 (2) | 0.0663 (7) | |
H11 | −0.1717 | 0.0161 | 0.0655 | 0.080* | |
C12 | −0.01924 (18) | 0.0589 (2) | 0.14638 (19) | 0.0571 (6) | |
H12 | −0.0071 | 0.1079 | 0.0809 | 0.068* | |
C13 | 0.66901 (17) | 0.22383 (19) | 0.23538 (18) | 0.0483 (5) | |
C14 | 0.8408 (2) | 0.2597 (2) | 0.3625 (2) | 0.0866 (9) | |
H14A | 0.9030 | 0.3093 | 0.3632 | 0.130* | |
H14B | 0.8601 | 0.1739 | 0.3644 | 0.130* | |
H14C | 0.8127 | 0.2789 | 0.4349 | 0.130* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0395 (11) | 0.0531 (11) | 0.0485 (9) | −0.0062 (9) | 0.0151 (8) | −0.0137 (8) |
N2 | 0.0363 (10) | 0.0424 (9) | 0.0343 (8) | 0.0044 (7) | 0.0068 (7) | −0.0022 (6) |
N3 | 0.0382 (11) | 0.0476 (10) | 0.0385 (8) | −0.0007 (8) | 0.0076 (7) | −0.0027 (7) |
N4 | 0.0505 (12) | 0.0628 (11) | 0.0415 (9) | −0.0051 (9) | 0.0090 (8) | 0.0044 (8) |
N5 | 0.0476 (11) | 0.0584 (11) | 0.0382 (9) | 0.0005 (9) | 0.0055 (8) | 0.0018 (7) |
O1 | 0.0529 (11) | 0.0703 (10) | 0.0679 (9) | −0.0196 (8) | −0.0050 (7) | 0.0094 (8) |
O2 | 0.0743 (13) | 0.0927 (13) | 0.0733 (11) | −0.0205 (10) | 0.0026 (9) | 0.0309 (9) |
O3 | 0.0467 (10) | 0.0556 (9) | 0.0762 (10) | −0.0121 (7) | 0.0238 (7) | −0.0268 (7) |
C1 | 0.0434 (13) | 0.0492 (12) | 0.0422 (10) | −0.0108 (10) | 0.0122 (9) | −0.0003 (9) |
C2 | 0.0382 (13) | 0.0473 (12) | 0.0367 (10) | −0.0011 (10) | 0.0086 (8) | −0.0056 (8) |
C3 | 0.0389 (12) | 0.0416 (11) | 0.0381 (9) | 0.0005 (9) | 0.0099 (8) | 0.0022 (8) |
C4 | 0.0519 (14) | 0.0400 (11) | 0.0636 (13) | −0.0007 (10) | 0.0186 (11) | −0.0099 (9) |
C5 | 0.0575 (15) | 0.0416 (12) | 0.0619 (12) | −0.0061 (10) | 0.0105 (11) | 0.0039 (9) |
C6 | 0.0444 (13) | 0.0401 (10) | 0.0374 (10) | 0.0023 (9) | 0.0103 (9) | −0.0022 (8) |
C7 | 0.0475 (14) | 0.0432 (11) | 0.0465 (11) | −0.0038 (10) | 0.0162 (10) | −0.0043 (9) |
C8 | 0.0666 (17) | 0.0591 (14) | 0.0573 (13) | −0.0082 (12) | 0.0173 (11) | 0.0074 (10) |
C9 | 0.084 (2) | 0.0669 (16) | 0.0809 (17) | −0.0203 (15) | 0.0339 (16) | 0.0103 (13) |
C10 | 0.0661 (19) | 0.0659 (16) | 0.0950 (19) | −0.0236 (14) | 0.0285 (16) | −0.0046 (14) |
C11 | 0.0482 (16) | 0.0754 (16) | 0.0726 (15) | −0.0137 (13) | 0.0078 (12) | −0.0067 (12) |
C12 | 0.0527 (15) | 0.0653 (14) | 0.0538 (13) | −0.0100 (12) | 0.0131 (11) | 0.0010 (10) |
C13 | 0.0460 (14) | 0.0471 (12) | 0.0521 (12) | −0.0073 (10) | 0.0112 (10) | 0.0003 (10) |
C14 | 0.0674 (19) | 0.0917 (19) | 0.0819 (16) | −0.0154 (15) | −0.0240 (14) | 0.0081 (14) |
Geometric parameters (Å, º) top
N1—C2 | 1.335 (2) | C4—H4A | 0.9700 |
N1—C1 | 1.452 (2) | C4—H4B | 0.9700 |
N1—H1N | 0.89 (2) | C5—H5A | 0.9700 |
N2—N5 | 1.3224 (19) | C5—H5B | 0.9700 |
N2—N3 | 1.329 (2) | C6—C7 | 1.456 (3) |
N2—C3 | 1.459 (2) | C7—C8 | 1.385 (3) |
N3—C6 | 1.331 (2) | C7—C12 | 1.388 (3) |
N4—N5 | 1.320 (2) | C8—C9 | 1.377 (3) |
N4—C6 | 1.350 (2) | C8—H8 | 0.9300 |
O1—C13 | 1.322 (2) | C9—C10 | 1.369 (3) |
O1—C14 | 1.447 (3) | C9—H9 | 0.9300 |
O2—C13 | 1.193 (2) | C10—C11 | 1.371 (3) |
O3—C2 | 1.232 (2) | C10—H10 | 0.9300 |
C1—C13 | 1.512 (3) | C11—C12 | 1.377 (3) |
C1—C5 | 1.520 (3) | C11—H11 | 0.9300 |
C1—H1 | 0.9800 | C12—H12 | 0.9300 |
C2—C3 | 1.525 (3) | C14—H14A | 0.9600 |
C3—C4 | 1.515 (2) | C14—H14B | 0.9600 |
C3—H3 | 0.9800 | C14—H14C | 0.9600 |
C4—C5 | 1.517 (3) | | |
| | | |
C2—N1—C1 | 126.51 (17) | C4—C5—H5B | 109.4 |
C2—N1—H1N | 116.2 (16) | C1—C5—H5B | 109.4 |
C1—N1—H1N | 115.9 (16) | H5A—C5—H5B | 108.0 |
N5—N2—N3 | 113.55 (15) | N3—C6—N4 | 111.57 (17) |
N5—N2—C3 | 122.94 (15) | N3—C6—C7 | 123.70 (16) |
N3—N2—C3 | 123.44 (13) | N4—C6—C7 | 124.72 (16) |
N2—N3—C6 | 102.27 (14) | C8—C7—C12 | 118.6 (2) |
N5—N4—C6 | 106.64 (15) | C8—C7—C6 | 120.97 (19) |
N4—N5—N2 | 105.97 (15) | C12—C7—C6 | 120.41 (17) |
C13—O1—C14 | 116.62 (17) | C9—C8—C7 | 120.2 (2) |
N1—C1—C13 | 109.70 (15) | C9—C8—H8 | 119.9 |
N1—C1—C5 | 110.71 (17) | C7—C8—H8 | 119.9 |
C13—C1—C5 | 110.63 (15) | C10—C9—C8 | 120.6 (2) |
N1—C1—H1 | 108.6 | C10—C9—H9 | 119.7 |
C13—C1—H1 | 108.6 | C8—C9—H9 | 119.7 |
C5—C1—H1 | 108.6 | C9—C10—C11 | 120.0 (2) |
O3—C2—N1 | 122.59 (17) | C9—C10—H10 | 120.0 |
O3—C2—C3 | 119.98 (17) | C11—C10—H10 | 120.0 |
N1—C2—C3 | 117.31 (17) | C10—C11—C12 | 120.0 (2) |
N2—C3—C4 | 112.06 (14) | C10—C11—H11 | 120.0 |
N2—C3—C2 | 108.78 (14) | C12—C11—H11 | 120.0 |
C4—C3—C2 | 114.67 (16) | C11—C12—C7 | 120.7 (2) |
N2—C3—H3 | 107.0 | C11—C12—H12 | 119.6 |
C4—C3—H3 | 107.0 | C7—C12—H12 | 119.6 |
C2—C3—H3 | 107.0 | O2—C13—O1 | 123.92 (19) |
C3—C4—C5 | 108.33 (16) | O2—C13—C1 | 124.99 (19) |
C3—C4—H4A | 110.0 | O1—C13—C1 | 111.07 (17) |
C5—C4—H4A | 110.0 | O1—C14—H14A | 109.5 |
C3—C4—H4B | 110.0 | O1—C14—H14B | 109.5 |
C5—C4—H4B | 110.0 | H14A—C14—H14B | 109.5 |
H4A—C4—H4B | 108.4 | O1—C14—H14C | 109.5 |
C4—C5—C1 | 110.97 (16) | H14A—C14—H14C | 109.5 |
C4—C5—H5A | 109.4 | H14B—C14—H14C | 109.5 |
C1—C5—H5A | 109.4 | | |
| | | |
N5—N2—N3—C6 | 0.22 (19) | N2—N3—C6—N4 | 0.02 (19) |
C3—N2—N3—C6 | 177.19 (15) | N2—N3—C6—C7 | −179.08 (16) |
C6—N4—N5—N2 | 0.37 (19) | N5—N4—C6—N3 | −0.3 (2) |
N3—N2—N5—N4 | −0.39 (19) | N5—N4—C6—C7 | 178.84 (17) |
C3—N2—N5—N4 | −177.37 (15) | N3—C6—C7—C8 | 165.45 (18) |
C2—N1—C1—C13 | 94.6 (2) | N4—C6—C7—C8 | −13.5 (3) |
C2—N1—C1—C5 | −27.7 (2) | N3—C6—C7—C12 | −12.5 (3) |
C1—N1—C2—O3 | −168.83 (17) | N4—C6—C7—C12 | 168.56 (18) |
C1—N1—C2—C3 | 15.1 (3) | C12—C7—C8—C9 | 0.0 (3) |
N5—N2—C3—C4 | −37.4 (2) | C6—C7—C8—C9 | −177.9 (2) |
N3—N2—C3—C4 | 145.91 (16) | C7—C8—C9—C10 | 0.1 (4) |
N5—N2—C3—C2 | 90.43 (18) | C8—C9—C10—C11 | −0.1 (4) |
N3—N2—C3—C2 | −86.25 (19) | C9—C10—C11—C12 | 0.0 (4) |
O3—C2—C3—N2 | 32.4 (2) | C10—C11—C12—C7 | 0.1 (3) |
N1—C2—C3—N2 | −151.41 (16) | C8—C7—C12—C11 | −0.1 (3) |
O3—C2—C3—C4 | 158.79 (17) | C6—C7—C12—C11 | 177.84 (19) |
N1—C2—C3—C4 | −25.1 (2) | C14—O1—C13—O2 | −0.2 (3) |
N2—C3—C4—C5 | 172.31 (15) | C14—O1—C13—C1 | 178.35 (18) |
C2—C3—C4—C5 | 47.7 (2) | N1—C1—C13—O2 | −32.8 (3) |
C3—C4—C5—C1 | −61.0 (2) | C5—C1—C13—O2 | 89.6 (2) |
N1—C1—C5—C4 | 50.0 (2) | N1—C1—C13—O1 | 148.64 (17) |
C13—C1—C5—C4 | −71.8 (2) | C5—C1—C13—O1 | −88.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3i | 0.90 (2) | 1.99 (2) | 2.880 (2) | 175 |
C3—H3···N4ii | 0.98 | 2.57 | 3.528 (2) | 167 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x, −y+1/2, z−1/2. |