The crystal structure determination of the title compound, C4H6N2O3, reveals that the N-nitrosamine moiety adopts the E conformation. The azetidine N atom is slightly pyramidalized, as evidenced by its displacement from the plane containing the three attached atoms by 0.038 (2) Å.
Supporting information
CCDC reference: 234859
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.035
- wR factor = 0.100
- Data-to-parameter ratio = 7.7
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for N1 - N2 = 8.78 su
Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.68
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 67.83
From the CIF: _reflns_number_total 630
Count of symmetry unique reflns 629
Completeness (_total/calc) 100.16%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1
Fraction of Friedel pairs measured 0.002
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
1 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
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Cell refinement: KM-4 Software (Kuma, 1991); data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989); software used to prepare material for publication: SHELXL97.
(
S)-Nitrosoazetidine-2-carboxylic acid
top
Crystal data top
C4H6N2O3 | Dx = 1.507 Mg m−3 |
Mr = 130.11 | Melting point: 388-389 K K |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 6.6521 (11) Å | θ = 13–30° |
b = 7.948 (2) Å | µ = 1.13 mm−1 |
c = 10.848 (2) Å | T = 293 K |
V = 573.5 (2) Å3 | Prism, yellow |
Z = 4 | 0.4 × 0.2 × 0.2 mm |
F(000) = 272 | |
Data collection top
Kuma KM-4 four-circle diffractometer | Rint = 0.034 |
Radiation source: fine-focus sealed tube | θmax = 67.8°, θmin = 6.9° |
Graphite monochromator | h = −7→0 |
ω/2θ scans | k = −9→0 |
1160 measured reflections | l = −12→12 |
630 independent reflections | 3 standard reflections every 100 reflections |
586 reflections with I > 2σ(I) | intensity decay: <1.5% |
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)] = 0.035 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0623P)2 + 0.0432P] where P = (Fo2 + 2Fc2)/3 |
630 reflections | (Δ/σ)max < 0.001 |
82 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.15 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.8442 (3) | 0.7297 (2) | 0.53813 (13) | 0.0642 (5) | |
O2 | 0.8536 (3) | 0.5374 (2) | 0.38881 (14) | 0.0613 (5) | |
H2O | 0.8502 | 0.4694 | 0.4492 | 0.074* | |
O3 | 0.6429 (3) | 0.6975 (2) | 0.05219 (13) | 0.0567 (5) | |
N1 | 0.7527 (3) | 0.7920 (2) | 0.22005 (14) | 0.0466 (5) | |
N2 | 0.7704 (3) | 0.6787 (2) | 0.13624 (15) | 0.0508 (5) | |
C1 | 0.8738 (3) | 0.8222 (2) | 0.33104 (18) | 0.0458 (5) | |
H11 | 1.0136 | 0.8399 | 0.3134 | 0.055* | |
C2 | 0.7521 (4) | 0.9866 (3) | 0.3482 (2) | 0.0517 (6) | |
H21 | 0.8353 | 1.0849 | 0.3417 | 0.062* | |
H22 | 0.6762 | 0.9890 | 0.4235 | 0.062* | |
C3 | 0.6247 (4) | 0.9412 (3) | 0.2340 (2) | 0.0544 (6) | |
H31 | 0.4864 | 0.9254 | 0.2563 | 0.065* | |
H32 | 0.6294 | 1.0078 | 0.1601 | 0.065* | |
C4 | 0.8530 (4) | 0.6919 (3) | 0.43120 (19) | 0.0456 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0947 (13) | 0.0598 (9) | 0.0382 (9) | 0.0087 (11) | −0.0002 (9) | −0.0040 (8) |
O2 | 0.0956 (12) | 0.0463 (8) | 0.0418 (9) | −0.0022 (10) | −0.0016 (9) | 0.0010 (7) |
O3 | 0.0713 (10) | 0.0529 (8) | 0.0460 (9) | −0.0021 (9) | −0.0076 (8) | −0.0003 (7) |
N1 | 0.0590 (10) | 0.0428 (8) | 0.0379 (9) | 0.0026 (9) | 0.0010 (8) | −0.0025 (8) |
N2 | 0.0632 (10) | 0.0489 (10) | 0.0404 (9) | −0.0032 (9) | 0.0007 (8) | 0.0039 (8) |
C1 | 0.0484 (11) | 0.0473 (10) | 0.0417 (11) | −0.0006 (10) | 0.0008 (9) | −0.0014 (10) |
C2 | 0.0616 (11) | 0.0394 (9) | 0.0542 (12) | −0.0007 (9) | 0.0024 (12) | −0.0046 (10) |
C3 | 0.0690 (14) | 0.0446 (11) | 0.0497 (13) | 0.0088 (12) | −0.0024 (11) | 0.0036 (10) |
C4 | 0.0462 (10) | 0.0478 (11) | 0.0428 (11) | 0.0017 (11) | −0.0025 (9) | −0.0017 (10) |
Geometric parameters (Å, º) top
O1—C4 | 1.200 (2) | C1—C2 | 1.548 (3) |
O2—C4 | 1.311 (3) | C1—H11 | 0.96 |
O2—H2O | 0.85 | C2—C3 | 1.544 (3) |
O3—N2 | 1.254 (2) | C2—H21 | 0.96 |
N1—N2 | 1.285 (2) | C2—H22 | 0.96 |
N1—C3 | 1.468 (3) | C3—H31 | 0.96 |
N1—C1 | 1.468 (3) | C3—H32 | 0.96 |
C1—C4 | 1.507 (3) | | |
| | | |
C4—O2—H2O | 109.0 | C1—C2—H21 | 112.1 |
N2—N1—C3 | 133.81 (18) | C3—C2—H22 | 113.5 |
N2—N1—C1 | 130.13 (18) | C1—C2—H22 | 113.2 |
C3—N1—C1 | 95.83 (16) | H21—C2—H22 | 110.5 |
O3—N2—N1 | 111.61 (18) | N1—C3—C2 | 87.31 (16) |
N1—C1—C4 | 115.36 (17) | N1—C3—H31 | 118.4 |
N1—C1—C2 | 87.14 (16) | C2—C3—H31 | 110.7 |
C4—C1—C2 | 116.42 (18) | N1—C3—H32 | 109.9 |
N1—C1—H11 | 113.1 | C2—C3—H32 | 121.5 |
C4—C1—H11 | 109.4 | H31—C3—H32 | 108.3 |
C2—C1—H11 | 114.0 | O1—C4—O2 | 125.0 (2) |
C3—C2—C1 | 89.60 (16) | O1—C4—C1 | 122.0 (2) |
C3—C2—H21 | 116.6 | O2—C4—C1 | 112.97 (18) |
| | | |
C3—N1—N2—O3 | −4.1 (3) | N2—N1—C3—C2 | −172.0 (2) |
C1—N1—N2—O3 | −177.16 (19) | C1—N1—C3—C2 | 2.69 (17) |
N2—N1—C1—C4 | −69.7 (3) | C1—C2—C3—N1 | −2.54 (16) |
C3—N1—C1—C4 | 115.3 (2) | N1—C1—C4—O1 | −139.2 (2) |
N2—N1—C1—C2 | 172.3 (2) | C2—C1—C4—O1 | −39.2 (3) |
C3—N1—C1—C2 | −2.68 (17) | N1—C1—C4—O2 | 43.2 (3) |
N1—C1—C2—C3 | 2.54 (16) | C2—C1—C4—O2 | 143.3 (2) |
C4—C1—C2—C3 | −114.5 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···O3i | 0.85 | 1.73 | 2.575 (2) | 169 |
C3—H32···O1ii | 0.96 | 2.48 | 3.376 (3) | 156 |
Symmetry codes: (i) −x+3/2, −y+1, z+1/2; (ii) −x+3/2, −y+2, z−1/2. |