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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804000327/na6283sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804000327/na6283Isup2.hkl
Contains datablock I

CCDC reference: 234859

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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
C4H6N2O3Dx = 1.507 Mg m3
Mr = 130.11Melting point: 388-389 K K
Orthorhombic, P212121Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 6.6521 (11) Åθ = 13–30°
b = 7.948 (2) ŵ = 1.13 mm1
c = 10.848 (2) ÅT = 293 K
V = 573.5 (2) Å3Prism, yellow
Z = 40.4 × 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 tubeθmax = 67.8°, θmin = 6.9°
Graphite monochromatorh = 70
ω/2θ scansk = 90
1160 measured reflectionsl = 1212
630 independent reflections3 standard reflections every 100 reflections
586 reflections with I > 2σ(I) intensity decay: <1.5%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: difference Fourier map
wR(F2) = 0.100H-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 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.15 e Å3
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
xyzUiso*/Ueq
O10.8442 (3)0.7297 (2)0.53813 (13)0.0642 (5)
O20.8536 (3)0.5374 (2)0.38881 (14)0.0613 (5)
H2O0.85020.46940.44920.074*
O30.6429 (3)0.6975 (2)0.05219 (13)0.0567 (5)
N10.7527 (3)0.7920 (2)0.22005 (14)0.0466 (5)
N20.7704 (3)0.6787 (2)0.13624 (15)0.0508 (5)
C10.8738 (3)0.8222 (2)0.33104 (18)0.0458 (5)
H111.01360.83990.31340.055*
C20.7521 (4)0.9866 (3)0.3482 (2)0.0517 (6)
H210.83531.08490.34170.062*
H220.67620.98900.42350.062*
C30.6247 (4)0.9412 (3)0.2340 (2)0.0544 (6)
H310.48640.92540.25630.065*
H320.62941.00780.16010.065*
C40.8530 (4)0.6919 (3)0.43120 (19)0.0456 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0947 (13)0.0598 (9)0.0382 (9)0.0087 (11)0.0002 (9)0.0040 (8)
O20.0956 (12)0.0463 (8)0.0418 (9)0.0022 (10)0.0016 (9)0.0010 (7)
O30.0713 (10)0.0529 (8)0.0460 (9)0.0021 (9)0.0076 (8)0.0003 (7)
N10.0590 (10)0.0428 (8)0.0379 (9)0.0026 (9)0.0010 (8)0.0025 (8)
N20.0632 (10)0.0489 (10)0.0404 (9)0.0032 (9)0.0007 (8)0.0039 (8)
C10.0484 (11)0.0473 (10)0.0417 (11)0.0006 (10)0.0008 (9)0.0014 (10)
C20.0616 (11)0.0394 (9)0.0542 (12)0.0007 (9)0.0024 (12)0.0046 (10)
C30.0690 (14)0.0446 (11)0.0497 (13)0.0088 (12)0.0024 (11)0.0036 (10)
C40.0462 (10)0.0478 (11)0.0428 (11)0.0017 (11)0.0025 (9)0.0017 (10)
Geometric parameters (Å, º) top
O1—C41.200 (2)C1—C21.548 (3)
O2—C41.311 (3)C1—H110.96
O2—H2O0.85C2—C31.544 (3)
O3—N21.254 (2)C2—H210.96
N1—N21.285 (2)C2—H220.96
N1—C31.468 (3)C3—H310.96
N1—C11.468 (3)C3—H320.96
C1—C41.507 (3)
C4—O2—H2O109.0C1—C2—H21112.1
N2—N1—C3133.81 (18)C3—C2—H22113.5
N2—N1—C1130.13 (18)C1—C2—H22113.2
C3—N1—C195.83 (16)H21—C2—H22110.5
O3—N2—N1111.61 (18)N1—C3—C287.31 (16)
N1—C1—C4115.36 (17)N1—C3—H31118.4
N1—C1—C287.14 (16)C2—C3—H31110.7
C4—C1—C2116.42 (18)N1—C3—H32109.9
N1—C1—H11113.1C2—C3—H32121.5
C4—C1—H11109.4H31—C3—H32108.3
C2—C1—H11114.0O1—C4—O2125.0 (2)
C3—C2—C189.60 (16)O1—C4—C1122.0 (2)
C3—C2—H21116.6O2—C4—C1112.97 (18)
C3—N1—N2—O34.1 (3)N2—N1—C3—C2172.0 (2)
C1—N1—N2—O3177.16 (19)C1—N1—C3—C22.69 (17)
N2—N1—C1—C469.7 (3)C1—C2—C3—N12.54 (16)
C3—N1—C1—C4115.3 (2)N1—C1—C4—O1139.2 (2)
N2—N1—C1—C2172.3 (2)C2—C1—C4—O139.2 (3)
C3—N1—C1—C22.68 (17)N1—C1—C4—O243.2 (3)
N1—C1—C2—C32.54 (16)C2—C1—C4—O2143.3 (2)
C4—C1—C2—C3114.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O3i0.851.732.575 (2)169
C3—H32···O1ii0.962.483.376 (3)156
Symmetry codes: (i) x+3/2, y+1, z+1/2; (ii) x+3/2, y+2, z1/2.
 

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