(Z)-Benzyl 2-(hydroxy­imino)acetoacetate

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.

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

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Computing details

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

Crystal data

C11H11NO4	F(000) = 464
Mr = 221.21	Dx = 1.372 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 22998 reflections
a = 10.464 (2) Å	θ = 2.7–30.0°
b = 11.191 (2) Å	µ = 0.11 mm^−1
c = 9.1463 (18) Å	T = 123 K
V = 1071.0 (4) Å^3	Prism, colourless
Z = 4	0.25 × 0.13 × 0.13 mm

Data collection

Bruker X8 APEX KAPPA CCD diffractometer	1646 independent reflections
Radiation source: fine-focus sealed tube	1539 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker ASX, 2005)	h = −14→13
Tmin = 0.964, Tmax = 0.986	k = −15→15
22998 measured reflections	l = −12→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.0342P)^2 + 0.219P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
1646 reflections	Δρmax = 0.16 e Å^−3
150 parameters	Δρmin = −0.21 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 1.0 (11)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.74196 (14)	0.26037 (10)	−0.01600 (18)	0.0267 (3)
O2	0.81791 (13)	0.42542 (11)	0.24191 (14)	0.0240 (3)
O3	0.76939 (12)	0.57521 (9)	0.08534 (15)	0.0208 (3)
O4	1.02693 (13)	0.56878 (11)	−0.00456 (17)	0.0260 (3)
N1	0.99205 (15)	0.45948 (13)	−0.06618 (19)	0.0222 (3)
C1	0.9202 (2)	0.23516 (16)	−0.1779 (2)	0.0289 (4)
H1A	0.8752	0.1627	−0.2090	0.043*
H1B	1.0039	0.2134	−0.1379	0.043*
H1C	0.9318	0.2883	−0.2619	0.043*
C2	0.84357 (17)	0.29767 (15)	−0.0630 (2)	0.0215 (3)
C3	0.89246 (16)	0.41515 (14)	−0.0056 (2)	0.0185 (3)
C4	0.82298 (15)	0.47153 (14)	0.1220 (2)	0.0187 (3)
C5	0.70592 (17)	0.63933 (15)	0.2049 (2)	0.0234 (4)
H5A	0.7645	0.6471	0.2893	0.028*
H5B	0.6290	0.5950	0.2369	0.028*
C6	0.66875 (17)	0.76132 (15)	0.1491 (2)	0.0215 (4)
C7	0.55461 (18)	0.81278 (15)	0.1968 (2)	0.0247 (4)
H7	0.5000	0.7697	0.2609	0.030*
C8	0.5204 (2)	0.92734 (16)	0.1506 (2)	0.0297 (4)
H8	0.4433	0.9626	0.1845	0.036*
C9	0.5995 (2)	0.99010 (16)	0.0546 (2)	0.0325 (4)
H9	0.5759	1.0677	0.0224	0.039*
C10	0.7124 (2)	0.93891 (16)	0.0065 (3)	0.0326 (5)
H10	0.7660	0.9815	−0.0592	0.039*
C11	0.7478 (2)	0.82501 (15)	0.0540 (2)	0.0273 (4)
H11	0.8259	0.7908	0.0215	0.033*
H1	1.095 (3)	0.590 (2)	−0.056 (3)	0.049 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0291 (6)	0.0236 (6)	0.0275 (7)	−0.0044 (5)	0.0008 (6)	0.0009 (6)
O2	0.0289 (7)	0.0250 (6)	0.0180 (6)	0.0001 (5)	−0.0006 (5)	0.0030 (5)
O3	0.0255 (6)	0.0203 (5)	0.0167 (6)	0.0033 (4)	0.0026 (6)	0.0001 (5)
O4	0.0223 (6)	0.0239 (6)	0.0319 (8)	−0.0042 (5)	0.0004 (6)	0.0003 (6)
N1	0.0218 (7)	0.0203 (7)	0.0246 (8)	0.0016 (6)	−0.0014 (6)	0.0014 (6)
C1	0.0364 (10)	0.0241 (8)	0.0262 (9)	0.0064 (7)	0.0022 (9)	−0.0025 (8)
C2	0.0265 (8)	0.0184 (7)	0.0196 (9)	0.0023 (6)	−0.0022 (8)	0.0033 (7)
C3	0.0183 (8)	0.0199 (7)	0.0174 (8)	0.0028 (6)	−0.0014 (7)	0.0025 (6)
C4	0.0176 (7)	0.0183 (7)	0.0201 (8)	−0.0023 (6)	−0.0023 (6)	0.0003 (6)
C5	0.0303 (9)	0.0228 (8)	0.0170 (9)	0.0026 (6)	0.0049 (7)	−0.0005 (7)
C6	0.0252 (8)	0.0190 (7)	0.0203 (9)	−0.0031 (6)	−0.0005 (7)	−0.0021 (7)
C7	0.0276 (9)	0.0236 (8)	0.0231 (9)	−0.0009 (6)	0.0014 (8)	−0.0020 (7)
C8	0.0367 (10)	0.0240 (9)	0.0285 (10)	0.0068 (7)	−0.0032 (9)	−0.0063 (8)
C9	0.0480 (11)	0.0178 (7)	0.0318 (10)	0.0002 (8)	−0.0097 (10)	−0.0016 (8)
C10	0.0429 (12)	0.0242 (8)	0.0307 (11)	−0.0104 (8)	−0.0007 (9)	0.0036 (8)
C11	0.0282 (8)	0.0252 (8)	0.0285 (10)	−0.0038 (7)	0.0015 (8)	−0.0011 (8)

Geometric parameters (Å, º)

O1—C2	1.221 (2)	C5—H5A	0.9900
O2—C4	1.213 (2)	C5—H5B	0.9900
O3—C4	1.3316 (19)	C6—C7	1.396 (3)
O3—C5	1.467 (2)	C6—C11	1.396 (3)
O4—N1	1.395 (2)	C7—C8	1.397 (2)
O4—H1	0.89 (3)	C7—H7	0.9500
N1—C3	1.280 (2)	C8—C9	1.396 (3)
C1—C2	1.495 (3)	C8—H8	0.9500
C1—H1A	0.9800	C9—C10	1.385 (3)
C1—H1B	0.9800	C9—H9	0.9500
C1—H1C	0.9800	C10—C11	1.397 (3)
C2—C3	1.505 (2)	C10—H10	0.9500
C3—C4	1.513 (2)	C11—H11	0.9500
C5—C6	1.508 (2)
C4—O3—C5	115.43 (14)	O3—C5—H5B	110.1
N1—O4—H1	103.0 (18)	C6—C5—H5B	110.1
C3—N1—O4	112.20 (15)	H5A—C5—H5B	108.4
C2—C1—H1A	109.5	C7—C6—C11	119.43 (16)
C2—C1—H1B	109.5	C7—C6—C5	119.23 (16)
H1A—C1—H1B	109.5	C11—C6—C5	121.32 (16)
C2—C1—H1C	109.5	C6—C7—C8	120.25 (18)
H1A—C1—H1C	109.5	C6—C7—H7	119.9
H1B—C1—H1C	109.5	C8—C7—H7	119.9
O1—C2—C1	123.69 (16)	C9—C8—C7	119.98 (19)
O1—C2—C3	118.16 (16)	C9—C8—H8	120.0
C1—C2—C3	118.12 (15)	C7—C8—H8	120.0
N1—C3—C2	117.66 (16)	C10—C9—C8	119.84 (18)
N1—C3—C4	124.29 (15)	C10—C9—H9	120.1
C2—C3—C4	118.03 (14)	C8—C9—H9	120.1
O2—C4—O3	125.43 (16)	C9—C10—C11	120.4 (2)
O2—C4—C3	122.75 (15)	C9—C10—H10	119.8
O3—C4—C3	111.82 (15)	C11—C10—H10	119.8
O3—C5—C6	107.91 (14)	C6—C11—C10	120.14 (19)
O3—C5—H5A	110.1	C6—C11—H11	119.9
C6—C5—H5A	110.1	C10—C11—H11	119.9
O4—N1—C3—C2	179.33 (13)	C4—O3—C5—C6	171.70 (13)
O4—N1—C3—C4	−2.3 (2)	O3—C5—C6—C7	144.05 (16)
O1—C2—C3—N1	−172.98 (17)	O3—C5—C6—C11	−37.7 (2)
C1—C2—C3—N1	5.1 (2)	C11—C6—C7—C8	−0.5 (3)
O1—C2—C3—C4	8.5 (2)	C5—C6—C7—C8	177.77 (17)
C1—C2—C3—C4	−173.36 (16)	C6—C7—C8—C9	1.0 (3)
C5—O3—C4—O2	3.5 (2)	C7—C8—C9—C10	−0.6 (3)
C5—O3—C4—C3	−176.76 (14)	C8—C9—C10—C11	−0.3 (3)
N1—C3—C4—O2	−114.4 (2)	C7—C6—C11—C10	−0.4 (3)
C2—C3—C4—O2	64.0 (2)	C5—C6—C11—C10	−178.60 (18)
N1—C3—C4—O3	65.9 (2)	C9—C10—C11—C6	0.8 (3)
C2—C3—C4—O3	−115.72 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1···O2^i	0.89 (3)	2.06 (3)	2.831 (2)	144 (2)
O4—H1···O1^ii	0.89 (3)	2.30 (3)	2.9545 (19)	130 (2)

Symmetry codes: (i) −x+2, −y+1, z−1/2; (ii) x+1/2, −y+1, z.