Download citation
Download citation
link to html
The title compound, C10H13NO4, which exists as the E isomer, crystallizes with two independent mol­ecules in the asymmetric unit. The bond lengths and angles in both mol­ecules are normal. The crystal structure is stabilized by inter­molecular O—H...O hydrogen bonds, which link the mol­ecules into cyclic tetra­mers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048677/hg2134sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048677/hg2134Isup2.hkl
Contains datablock I

CCDC reference: 629912

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.035
  • wR factor = 0.106
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C10 H13 N O4
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(E)-2,4,5-Trimethoxybenzaldehyde oxime top
Crystal data top
C10H13NO4Z = 4
Mr = 211.21F(000) = 448
Triclinic, P1Dx = 1.298 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4428 (1) ÅCell parameters from 1528 reflections
b = 10.7189 (1) Åθ = 2.4–22.4°
c = 14.0290 (2) ŵ = 0.10 mm1
α = 87.583 (1)°T = 293 K
β = 88.451 (1)°Block, colorless
γ = 75.214 (1)°0.36 × 0.30 × 0.22 mm
V = 1081.04 (2) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3805 independent reflections
Radiation source: fine-focus sealed tube3079 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.965, Tmax = 0.978k = 1212
12599 measured reflectionsl = 1616
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)] = 0.035H-atom parameters constrained
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0542P)2 + 0.1378P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3805 reflectionsΔρmax = 0.15 e Å3
272 parametersΔρmin = 0.11 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0058 (13)
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
O10.23909 (16)0.53280 (10)0.20946 (8)0.0714 (3)
O20.28464 (15)0.53983 (10)0.42574 (8)0.0684 (3)
O30.25307 (18)0.82962 (12)0.66363 (8)0.0877 (4)
H3A0.20400.86540.70210.131*
O40.32536 (14)0.70961 (10)0.30188 (7)0.0669 (3)
O50.45656 (15)1.38071 (10)0.87482 (8)0.0751 (3)
H5A0.54041.38220.83600.113*
O60.07741 (15)1.28758 (11)1.01755 (8)0.0744 (3)
O70.21573 (14)0.95086 (10)0.83293 (7)0.0685 (3)
O80.05978 (15)0.95249 (10)0.72070 (8)0.0719 (3)
N10.13484 (19)0.79793 (12)0.58378 (9)0.0673 (3)
N20.36896 (17)1.28563 (11)0.85149 (9)0.0614 (3)
C10.08491 (19)0.67322 (12)0.44599 (10)0.0521 (3)
C20.13221 (19)0.57914 (12)0.39329 (10)0.0534 (3)
C30.0261 (2)0.53020 (13)0.31383 (10)0.0561 (4)
H3B0.05820.46720.27920.067*
C40.1262 (2)0.57440 (13)0.28594 (10)0.0547 (3)
C50.17403 (19)0.67067 (13)0.33734 (10)0.0534 (3)
C60.06951 (19)0.71753 (13)0.41549 (10)0.0532 (3)
H6A0.10170.78090.44960.064*
C70.2067 (3)0.43219 (17)0.15608 (13)0.0851 (5)
H7A0.29680.41330.10500.128*
H7B0.08410.45840.13020.128*
H7C0.21710.35650.19680.128*
C80.3396 (2)0.44414 (16)0.37522 (13)0.0767 (5)
H8A0.44750.42590.40580.115*
H8B0.24020.36680.37490.115*
H8C0.36830.47500.31080.115*
C90.3825 (2)0.80356 (16)0.35333 (13)0.0743 (5)
H9A0.48860.82330.32190.111*
H9B0.41470.77040.41700.111*
H9C0.28280.88050.35600.111*
C100.1882 (2)0.72105 (14)0.53203 (10)0.0603 (4)
H10A0.29470.69480.54920.072*
C110.10658 (18)1.20356 (13)0.88569 (9)0.0517 (3)
C120.04554 (19)1.20229 (13)0.94502 (10)0.0548 (3)
C130.15600 (19)1.11856 (13)0.92964 (10)0.0562 (3)
H13A0.25721.11810.96990.067*
C140.11571 (19)1.03619 (13)0.85480 (10)0.0540 (3)
C150.03646 (19)1.03652 (13)0.79381 (10)0.0543 (3)
C160.14478 (19)1.11883 (13)0.80975 (10)0.0538 (3)
H16A0.24611.11870.76940.065*
C170.3738 (2)0.94619 (16)0.88956 (12)0.0688 (4)
H17A0.43070.88310.86560.103*
H17B0.46111.02940.88730.103*
H17C0.33720.92280.95430.103*
C180.2106 (2)0.94858 (17)0.65644 (12)0.0784 (5)
H18A0.21140.88670.60880.118*
H18B0.32500.92410.69070.118*
H18C0.19781.03230.62620.118*
C190.2338 (3)1.29425 (17)1.07812 (12)0.0799 (5)
H19A0.23881.35781.12500.120*
H19B0.22441.21161.10960.120*
H19C0.34471.31781.04100.120*
C200.2216 (2)1.29233 (13)0.90017 (10)0.0574 (3)
H20A0.18611.35480.94580.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0785 (7)0.0749 (7)0.0666 (7)0.0280 (5)0.0117 (5)0.0234 (5)
O20.0684 (7)0.0716 (6)0.0743 (7)0.0334 (5)0.0032 (5)0.0119 (5)
O30.1007 (9)0.1009 (9)0.0711 (8)0.0413 (7)0.0224 (6)0.0313 (6)
O40.0692 (6)0.0722 (6)0.0674 (7)0.0322 (5)0.0070 (5)0.0136 (5)
O50.0758 (7)0.0735 (7)0.0845 (8)0.0332 (6)0.0078 (6)0.0170 (6)
O60.0785 (7)0.0868 (7)0.0632 (7)0.0277 (6)0.0178 (5)0.0333 (6)
O70.0691 (7)0.0759 (7)0.0681 (7)0.0307 (5)0.0150 (5)0.0224 (5)
O80.0769 (7)0.0809 (7)0.0649 (7)0.0306 (6)0.0205 (5)0.0315 (5)
N10.0783 (9)0.0682 (8)0.0585 (8)0.0238 (6)0.0100 (6)0.0138 (6)
N20.0610 (7)0.0590 (7)0.0666 (8)0.0187 (6)0.0001 (6)0.0095 (6)
C10.0562 (8)0.0511 (7)0.0495 (8)0.0139 (6)0.0078 (6)0.0007 (6)
C20.0559 (8)0.0509 (7)0.0549 (8)0.0164 (6)0.0088 (6)0.0025 (6)
C30.0650 (9)0.0501 (7)0.0564 (8)0.0188 (6)0.0086 (7)0.0079 (6)
C40.0607 (8)0.0521 (7)0.0507 (8)0.0127 (6)0.0039 (6)0.0044 (6)
C50.0553 (8)0.0526 (7)0.0538 (8)0.0163 (6)0.0055 (6)0.0011 (6)
C60.0607 (8)0.0513 (7)0.0507 (8)0.0184 (6)0.0080 (6)0.0051 (6)
C70.0970 (13)0.0802 (11)0.0828 (12)0.0274 (10)0.0125 (10)0.0352 (9)
C80.0742 (10)0.0722 (10)0.0940 (13)0.0358 (8)0.0065 (9)0.0101 (9)
C90.0771 (11)0.0763 (10)0.0804 (11)0.0380 (9)0.0052 (8)0.0165 (8)
C100.0617 (9)0.0654 (9)0.0582 (9)0.0234 (7)0.0019 (7)0.0057 (7)
C110.0521 (8)0.0549 (7)0.0458 (7)0.0087 (6)0.0037 (6)0.0049 (6)
C120.0578 (8)0.0576 (8)0.0458 (8)0.0074 (6)0.0010 (6)0.0091 (6)
C130.0528 (8)0.0638 (8)0.0500 (8)0.0107 (6)0.0060 (6)0.0081 (6)
C140.0539 (8)0.0561 (8)0.0513 (8)0.0121 (6)0.0007 (6)0.0060 (6)
C150.0576 (8)0.0570 (8)0.0467 (8)0.0104 (6)0.0026 (6)0.0124 (6)
C160.0501 (8)0.0613 (8)0.0480 (8)0.0103 (6)0.0046 (6)0.0070 (6)
C170.0624 (9)0.0731 (10)0.0738 (10)0.0225 (8)0.0109 (8)0.0096 (8)
C180.0836 (11)0.0821 (11)0.0716 (11)0.0235 (9)0.0262 (9)0.0299 (9)
C190.0876 (12)0.0836 (11)0.0673 (10)0.0180 (9)0.0226 (9)0.0280 (9)
C200.0618 (9)0.0579 (8)0.0511 (8)0.0117 (6)0.0010 (7)0.0093 (6)
Geometric parameters (Å, º) top
O1—C41.3625 (17)C7—H7B0.9600
O1—C71.4117 (18)C7—H7C0.9600
O2—C21.3681 (17)C8—H8A0.9600
O2—C81.4187 (17)C8—H8B0.9600
O3—N11.4039 (16)C8—H8C0.9600
O3—H3A0.8200C9—H9A0.9600
O4—C51.3721 (17)C9—H9B0.9600
O4—C91.4186 (17)C9—H9C0.9600
O5—N21.3964 (15)C10—H10A0.9300
O5—H5A0.8200C11—C121.3896 (19)
O6—C121.3719 (16)C11—C161.4050 (18)
O6—C191.4114 (19)C11—C201.4563 (19)
O7—C141.3669 (17)C12—C131.389 (2)
O7—C171.4124 (17)C13—C141.3775 (19)
O8—C151.3718 (16)C13—H13A0.9300
O8—C181.4137 (18)C14—C151.402 (2)
N1—C101.2636 (18)C15—C161.3667 (19)
N2—C201.2642 (18)C16—H16A0.9300
C1—C21.3949 (18)C17—H17A0.9600
C1—C61.4016 (19)C17—H17B0.9600
C1—C101.453 (2)C17—H17C0.9600
C2—C31.390 (2)C18—H18A0.9600
C3—C41.378 (2)C18—H18B0.9600
C3—H3B0.9300C18—H18C0.9600
C4—C51.4056 (19)C19—H19A0.9600
C5—C61.364 (2)C19—H19B0.9600
C6—H6A0.9300C19—H19C0.9600
C7—H7A0.9600C20—H20A0.9300
C4—O1—C7118.94 (13)H9A—C9—H9C109.5
C2—O2—C8118.43 (12)H9B—C9—H9C109.5
N1—O3—H3A109.5N1—C10—C1120.78 (14)
C5—O4—C9116.97 (11)N1—C10—H10A119.6
N2—O5—H5A109.5C1—C10—H10A119.6
C12—O6—C19118.65 (12)C12—C11—C16118.35 (13)
C14—O7—C17118.66 (11)C12—C11—C20121.07 (12)
C15—O8—C18117.58 (12)C16—C11—C20120.56 (13)
C10—N1—O3111.06 (13)O6—C12—C13123.45 (13)
C20—N2—O5111.93 (12)O6—C12—C11115.97 (13)
C2—C1—C6118.12 (13)C13—C12—C11120.58 (12)
C2—C1—C10121.22 (13)C14—C13—C12120.05 (13)
C6—C1—C10120.63 (12)C14—C13—H13A120.0
O2—C2—C3123.94 (12)C12—C13—H13A120.0
O2—C2—C1115.77 (13)O7—C14—C13124.81 (13)
C3—C2—C1120.29 (13)O7—C14—C15114.94 (12)
C4—C3—C2120.45 (12)C13—C14—C15120.25 (13)
C4—C3—H3B119.8C16—C15—O8125.86 (13)
C2—C3—H3B119.8C16—C15—C14119.29 (12)
O1—C4—C3125.05 (12)O8—C15—C14114.85 (12)
O1—C4—C5114.96 (13)C15—C16—C11121.48 (13)
C3—C4—C5119.99 (13)C15—C16—H16A119.3
C6—C5—O4125.92 (12)C11—C16—H16A119.3
C6—C5—C4119.06 (13)O7—C17—H17A109.5
O4—C5—C4115.02 (12)O7—C17—H17B109.5
C5—C6—C1122.09 (13)H17A—C17—H17B109.5
C5—C6—H6A119.0O7—C17—H17C109.5
C1—C6—H6A119.0H17A—C17—H17C109.5
O1—C7—H7A109.5H17B—C17—H17C109.5
O1—C7—H7B109.5O8—C18—H18A109.5
H7A—C7—H7B109.5O8—C18—H18B109.5
O1—C7—H7C109.5H18A—C18—H18B109.5
H7A—C7—H7C109.5O8—C18—H18C109.5
H7B—C7—H7C109.5H18A—C18—H18C109.5
O2—C8—H8A109.5H18B—C18—H18C109.5
O2—C8—H8B109.5O6—C19—H19A109.5
H8A—C8—H8B109.5O6—C19—H19B109.5
O2—C8—H8C109.5H19A—C19—H19B109.5
H8A—C8—H8C109.5O6—C19—H19C109.5
H8B—C8—H8C109.5H19A—C19—H19C109.5
O4—C9—H9A109.5H19B—C19—H19C109.5
O4—C9—H9B109.5N2—C20—C11120.87 (13)
H9A—C9—H9B109.5N2—C20—H20A119.6
O4—C9—H9C109.5C11—C20—H20A119.6
C8—O2—C2—C30.5 (2)C19—O6—C12—C132.2 (2)
C8—O2—C2—C1179.91 (13)C19—O6—C12—C11177.70 (13)
C6—C1—C2—O2179.61 (11)C16—C11—C12—O6179.51 (12)
C10—C1—C2—O22.53 (19)C20—C11—C12—O60.88 (19)
C6—C1—C2—C30.98 (19)C16—C11—C12—C130.4 (2)
C10—C1—C2—C3176.87 (12)C20—C11—C12—C13179.00 (12)
O2—C2—C3—C4179.66 (12)O6—C12—C13—C14179.58 (13)
C1—C2—C3—C40.3 (2)C11—C12—C13—C140.3 (2)
C7—O1—C4—C33.4 (2)C17—O7—C14—C130.8 (2)
C7—O1—C4—C5177.23 (14)C17—O7—C14—C15178.66 (13)
C2—C3—C4—O1179.92 (13)C12—C13—C14—O7179.51 (13)
C2—C3—C4—C50.7 (2)C12—C13—C14—C150.1 (2)
C9—O4—C5—C62.6 (2)C18—O8—C15—C161.0 (2)
C9—O4—C5—C4177.95 (12)C18—O8—C15—C14179.79 (13)
O1—C4—C5—C6179.54 (12)O7—C14—C15—C16179.85 (12)
C3—C4—C5—C61.0 (2)C13—C14—C15—C160.4 (2)
O1—C4—C5—O40.97 (17)O7—C14—C15—O80.94 (18)
C3—C4—C5—O4178.45 (12)C13—C14—C15—O8178.54 (12)
O4—C5—C6—C1179.09 (12)O8—C15—C16—C11178.50 (13)
C4—C5—C6—C10.3 (2)C14—C15—C16—C110.3 (2)
C2—C1—C6—C50.7 (2)C12—C11—C16—C150.1 (2)
C10—C1—C6—C5177.21 (13)C20—C11—C16—C15178.72 (13)
O3—N1—C10—C1179.00 (12)O5—N2—C20—C11178.73 (11)
C2—C1—C10—N1173.87 (14)C12—C11—C20—N2173.75 (13)
C6—C1—C10—N13.9 (2)C16—C11—C20—N27.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O1i0.822.142.8676 (15)148
O5—H5A···O4i0.822.292.9832 (15)142
Symmetry code: (i) x+1, y+2, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds