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The crystal structure of the title compound, C11H11NO4, forms an extended inter­digitated hydrogen-bonded array via O—H...O inter­actions parallel to the c axis. The oxime adopts a Z configuration.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047738/hg2130sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047738/hg2130Isup2.hkl
Contains datablock I

CCDC reference: 629911

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.082
  • Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact O2 .. C2 .. 2.84 Ang.
Alert level C STRVA01_ALERT_2_C Chirality of atom sites is inverted? From the CIF: _refine_ls_abs_structure_Flack 1.000 From the CIF: _refine_ls_abs_structure_Flack_su 1.100 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 1.10 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 1.00
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 29.95 From the CIF: _reflns_number_total 1646 Count of symmetry unique reflns 1649 Completeness (_total/calc) 99.82% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 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 3 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: Bruker Apex2 (Bruker ASX, 2005); cell refinement: Bruker Apex2; data reduction: Bruker Apex2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001) and POV-RAY (Cason, 2003); software used to prepare material for publication: SHELXL97.

(Z)-benzyl 2-(hydroxyimino)acetoacetate top
Crystal data top
C11H11NO4F(000) = 464
Mr = 221.21Dx = 1.372 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 22998 reflections
a = 10.464 (2) Åθ = 2.7–30.0°
b = 11.191 (2) ŵ = 0.11 mm1
c = 9.1463 (18) ÅT = 123 K
V = 1071.0 (4) Å3Prism, colourless
Z = 40.25 × 0.13 × 0.13 mm
Data collection top
Bruker X8 APEX KAPPA CCD
diffractometer
1646 independent reflections
Radiation source: fine-focus sealed tube1539 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker ASX, 2005)
h = 1413
Tmin = 0.964, Tmax = 0.986k = 1515
22998 measured reflectionsl = 1211
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0342P)2 + 0.219P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max < 0.001
1646 reflectionsΔρmax = 0.16 e Å3
150 parametersΔρmin = 0.21 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 1.0 (11)
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
xyzUiso*/Ueq
O10.74196 (14)0.26037 (10)0.01600 (18)0.0267 (3)
O20.81791 (13)0.42542 (11)0.24191 (14)0.0240 (3)
O30.76939 (12)0.57521 (9)0.08534 (15)0.0208 (3)
O41.02693 (13)0.56878 (11)0.00456 (17)0.0260 (3)
N10.99205 (15)0.45948 (13)0.06618 (19)0.0222 (3)
C10.9202 (2)0.23516 (16)0.1779 (2)0.0289 (4)
H1A0.87520.16270.20900.043*
H1B1.00390.21340.13790.043*
H1C0.93180.28830.26190.043*
C20.84357 (17)0.29767 (15)0.0630 (2)0.0215 (3)
C30.89246 (16)0.41515 (14)0.0056 (2)0.0185 (3)
C40.82298 (15)0.47153 (14)0.1220 (2)0.0187 (3)
C50.70592 (17)0.63933 (15)0.2049 (2)0.0234 (4)
H5A0.76450.64710.28930.028*
H5B0.62900.59500.23690.028*
C60.66875 (17)0.76132 (15)0.1491 (2)0.0215 (4)
C70.55461 (18)0.81278 (15)0.1968 (2)0.0247 (4)
H70.50000.76970.26090.030*
C80.5204 (2)0.92734 (16)0.1506 (2)0.0297 (4)
H80.44330.96260.18450.036*
C90.5995 (2)0.99010 (16)0.0546 (2)0.0325 (4)
H90.57591.06770.02240.039*
C100.7124 (2)0.93891 (16)0.0065 (3)0.0326 (5)
H100.76600.98150.05920.039*
C110.7478 (2)0.82501 (15)0.0540 (2)0.0273 (4)
H110.82590.79080.02150.033*
H11.095 (3)0.590 (2)0.056 (3)0.049 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0291 (6)0.0236 (6)0.0275 (7)0.0044 (5)0.0008 (6)0.0009 (6)
O20.0289 (7)0.0250 (6)0.0180 (6)0.0001 (5)0.0006 (5)0.0030 (5)
O30.0255 (6)0.0203 (5)0.0167 (6)0.0033 (4)0.0026 (6)0.0001 (5)
O40.0223 (6)0.0239 (6)0.0319 (8)0.0042 (5)0.0004 (6)0.0003 (6)
N10.0218 (7)0.0203 (7)0.0246 (8)0.0016 (6)0.0014 (6)0.0014 (6)
C10.0364 (10)0.0241 (8)0.0262 (9)0.0064 (7)0.0022 (9)0.0025 (8)
C20.0265 (8)0.0184 (7)0.0196 (9)0.0023 (6)0.0022 (8)0.0033 (7)
C30.0183 (8)0.0199 (7)0.0174 (8)0.0028 (6)0.0014 (7)0.0025 (6)
C40.0176 (7)0.0183 (7)0.0201 (8)0.0023 (6)0.0023 (6)0.0003 (6)
C50.0303 (9)0.0228 (8)0.0170 (9)0.0026 (6)0.0049 (7)0.0005 (7)
C60.0252 (8)0.0190 (7)0.0203 (9)0.0031 (6)0.0005 (7)0.0021 (7)
C70.0276 (9)0.0236 (8)0.0231 (9)0.0009 (6)0.0014 (8)0.0020 (7)
C80.0367 (10)0.0240 (9)0.0285 (10)0.0068 (7)0.0032 (9)0.0063 (8)
C90.0480 (11)0.0178 (7)0.0318 (10)0.0002 (8)0.0097 (10)0.0016 (8)
C100.0429 (12)0.0242 (8)0.0307 (11)0.0104 (8)0.0007 (9)0.0036 (8)
C110.0282 (8)0.0252 (8)0.0285 (10)0.0038 (7)0.0015 (8)0.0011 (8)
Geometric parameters (Å, º) top
O1—C21.221 (2)C5—H5A0.9900
O2—C41.213 (2)C5—H5B0.9900
O3—C41.3316 (19)C6—C71.396 (3)
O3—C51.467 (2)C6—C111.396 (3)
O4—N11.395 (2)C7—C81.397 (2)
O4—H10.89 (3)C7—H70.9500
N1—C31.280 (2)C8—C91.396 (3)
C1—C21.495 (3)C8—H80.9500
C1—H1A0.9800C9—C101.385 (3)
C1—H1B0.9800C9—H90.9500
C1—H1C0.9800C10—C111.397 (3)
C2—C31.505 (2)C10—H100.9500
C3—C41.513 (2)C11—H110.9500
C5—C61.508 (2)
C4—O3—C5115.43 (14)O3—C5—H5B110.1
N1—O4—H1103.0 (18)C6—C5—H5B110.1
C3—N1—O4112.20 (15)H5A—C5—H5B108.4
C2—C1—H1A109.5C7—C6—C11119.43 (16)
C2—C1—H1B109.5C7—C6—C5119.23 (16)
H1A—C1—H1B109.5C11—C6—C5121.32 (16)
C2—C1—H1C109.5C6—C7—C8120.25 (18)
H1A—C1—H1C109.5C6—C7—H7119.9
H1B—C1—H1C109.5C8—C7—H7119.9
O1—C2—C1123.69 (16)C9—C8—C7119.98 (19)
O1—C2—C3118.16 (16)C9—C8—H8120.0
C1—C2—C3118.12 (15)C7—C8—H8120.0
N1—C3—C2117.66 (16)C10—C9—C8119.84 (18)
N1—C3—C4124.29 (15)C10—C9—H9120.1
C2—C3—C4118.03 (14)C8—C9—H9120.1
O2—C4—O3125.43 (16)C9—C10—C11120.4 (2)
O2—C4—C3122.75 (15)C9—C10—H10119.8
O3—C4—C3111.82 (15)C11—C10—H10119.8
O3—C5—C6107.91 (14)C6—C11—C10120.14 (19)
O3—C5—H5A110.1C6—C11—H11119.9
C6—C5—H5A110.1C10—C11—H11119.9
O4—N1—C3—C2179.33 (13)C4—O3—C5—C6171.70 (13)
O4—N1—C3—C42.3 (2)O3—C5—C6—C7144.05 (16)
O1—C2—C3—N1172.98 (17)O3—C5—C6—C1137.7 (2)
C1—C2—C3—N15.1 (2)C11—C6—C7—C80.5 (3)
O1—C2—C3—C48.5 (2)C5—C6—C7—C8177.77 (17)
C1—C2—C3—C4173.36 (16)C6—C7—C8—C91.0 (3)
C5—O3—C4—O23.5 (2)C7—C8—C9—C100.6 (3)
C5—O3—C4—C3176.76 (14)C8—C9—C10—C110.3 (3)
N1—C3—C4—O2114.4 (2)C7—C6—C11—C100.4 (3)
C2—C3—C4—O264.0 (2)C5—C6—C11—C10178.60 (18)
N1—C3—C4—O365.9 (2)C9—C10—C11—C60.8 (3)
C2—C3—C4—O3115.72 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H1···O2i0.89 (3)2.06 (3)2.831 (2)144 (2)
O4—H1···O1ii0.89 (3)2.30 (3)2.9545 (19)130 (2)
Symmetry codes: (i) x+2, y+1, z1/2; (ii) x+1/2, y+1, z.
 

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