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Crystals of the title compound, C13H15NO6, were obtained from the modified Knoevenagel condensation reaction of 3,4-dihydroxy­benzaldehyde and mono-2-methyl-2-nitro­propyl malonate. The mol­ecule is the E isomer with the usual bond lengths and angles. The crystal packing is stabilized by inter­molecular O—H...O and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033192/cv6584sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033192/cv6584Isup2.hkl
Contains datablock I

CCDC reference: 290011

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.135
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C11 .. 6.28 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C10 - C11 .. 5.36 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.19 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C13 H15 N O6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4, PSI and EAC (Enraf–Nonius, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999); software used to prepare material for publication: SHELXL97.

2-Methyl-2-nitropropyl 3-(3,4-dihydroxyphenyl)prop-2-enoate top
Crystal data top
C13H15NO6F(000) = 592
Mr = 281.26Dx = 1.392 Mg m3
Monoclinic, P21/cMelting point = 417–420 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 5.739 (4) ÅCell parameters from 25 reflections
b = 10.7660 (17) Åθ = 10.2–12.6°
c = 22.112 (5) ŵ = 0.11 mm1
β = 100.73 (4)°T = 295 K
V = 1342.3 (11) Å3Plate, light brown
Z = 40.40 × 0.35 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1319 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.014
Graphite monochromatorθmax = 25.2°, θmin = 1.9°
ω/2θ scansh = 06
Absorption correction: empirical (using intensity measurements)
(North et al., 1968)
k = 121
Tmin = 0.958, Tmax = 0.987l = 2625
2960 measured reflections3 standard reflections every 60 min
2406 independent reflections intensity decay: 0.3%
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)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.135 w = 1/[σ2(Fo2) + (0.0573P)2 + 0.3869P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2406 reflectionsΔρmax = 0.21 e Å3
192 parametersΔρmin = 0.15 e Å3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0107 (18)
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
O10.3313 (4)1.37014 (19)0.00007 (10)0.0785 (7)
H1X0.236 (5)1.348 (3)0.0213 (14)0.109 (12)*
O20.7019 (4)1.4027 (2)0.05916 (12)0.0854 (7)
H2X0.668 (6)1.450 (3)0.0331 (12)0.089 (12)*
O30.0262 (4)0.7172 (2)0.07424 (9)0.0908 (8)
O40.1810 (3)0.64476 (16)0.14333 (8)0.0622 (5)
O50.0245 (5)0.6416 (3)0.29729 (11)0.1135 (10)
O60.1490 (4)0.4713 (3)0.26910 (12)0.1111 (9)
N10.0086 (4)0.5529 (3)0.26387 (11)0.0675 (7)
C10.3612 (4)1.0617 (2)0.07067 (10)0.0478 (6)
C20.2869 (4)1.1586 (2)0.03775 (11)0.0525 (7)
H20.15841.14630.01830.063*
C30.3964 (5)1.2717 (2)0.03298 (11)0.0528 (7)
C40.5887 (5)1.2915 (2)0.06213 (12)0.0561 (7)
C50.6654 (5)1.1961 (2)0.09488 (12)0.0589 (7)
H50.79361.20910.11440.071*
C60.5563 (4)1.0823 (2)0.09926 (11)0.0528 (7)
H60.61181.01860.12120.063*
C70.2349 (4)0.9431 (2)0.07435 (11)0.0548 (7)
H70.10850.93950.05350.066*
C80.2762 (5)0.8409 (2)0.10323 (11)0.0567 (7)
H80.40380.83870.12370.068*
C90.1276 (5)0.7312 (3)0.10401 (11)0.0605 (7)
C100.0405 (5)0.5326 (2)0.15310 (13)0.0619 (7)
H10A0.14390.46180.15450.074*
H10B0.04210.52070.11910.074*
C110.1374 (4)0.5402 (2)0.21257 (11)0.0498 (6)
C120.2713 (5)0.4182 (2)0.22434 (13)0.0669 (8)
H12A0.37130.42040.26430.100*
H12B0.16020.35110.22260.100*
H12C0.36690.40610.19350.100*
C130.3040 (5)0.6492 (3)0.21551 (15)0.0779 (9)
H13A0.21400.72480.21000.117*
H13B0.40820.65050.25490.117*
H13C0.39580.64170.18360.117*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0897 (15)0.0644 (13)0.0994 (16)0.0283 (11)0.0641 (13)0.0215 (11)
O20.0982 (16)0.0606 (13)0.1177 (19)0.0321 (12)0.0728 (15)0.0164 (13)
O30.1126 (17)0.0939 (16)0.0839 (14)0.0548 (14)0.0653 (14)0.0351 (12)
O40.0639 (11)0.0640 (12)0.0637 (11)0.0208 (10)0.0244 (9)0.0160 (10)
O50.153 (3)0.112 (2)0.0845 (17)0.0419 (19)0.0464 (17)0.0140 (15)
O60.0833 (17)0.141 (2)0.122 (2)0.0106 (17)0.0538 (15)0.0299 (17)
N10.0630 (16)0.0785 (18)0.0653 (16)0.0234 (14)0.0230 (13)0.0148 (14)
C10.0473 (14)0.0561 (15)0.0410 (13)0.0116 (13)0.0110 (11)0.0013 (12)
C20.0464 (14)0.0643 (17)0.0518 (15)0.0133 (13)0.0221 (12)0.0010 (12)
C30.0543 (15)0.0531 (16)0.0567 (15)0.0110 (13)0.0249 (12)0.0023 (12)
C40.0577 (16)0.0549 (16)0.0626 (16)0.0144 (13)0.0289 (13)0.0022 (13)
C50.0554 (16)0.0627 (18)0.0669 (17)0.0096 (14)0.0330 (13)0.0048 (14)
C60.0513 (15)0.0553 (16)0.0550 (15)0.0036 (13)0.0182 (12)0.0008 (12)
C70.0552 (15)0.0649 (17)0.0482 (14)0.0183 (14)0.0192 (12)0.0058 (13)
C80.0572 (16)0.0653 (18)0.0513 (15)0.0199 (14)0.0202 (12)0.0058 (13)
C90.0672 (18)0.0718 (19)0.0470 (14)0.0237 (15)0.0225 (13)0.0122 (14)
C100.0696 (18)0.0506 (16)0.0690 (18)0.0166 (15)0.0216 (15)0.0065 (13)
C110.0491 (14)0.0488 (14)0.0567 (15)0.0122 (12)0.0233 (12)0.0042 (12)
C120.0638 (18)0.0585 (18)0.083 (2)0.0164 (14)0.0243 (15)0.0083 (14)
C130.0672 (19)0.0607 (19)0.107 (2)0.0036 (16)0.0202 (18)0.0070 (17)
Geometric parameters (Å, º) top
O1—C31.376 (3)C5—H50.9300
O1—H1X0.822 (18)C6—H60.9300
O2—C41.358 (3)C7—C81.316 (3)
O2—H2X0.821 (18)C7—H70.9300
O3—C91.205 (3)C8—C91.455 (3)
O4—C91.347 (3)C8—H80.9300
O4—C101.445 (3)C10—C111.510 (4)
O5—N11.201 (3)C10—H10A0.9700
O6—N11.212 (3)C10—H10B0.9700
N1—C111.537 (3)C11—C131.507 (4)
C1—C21.384 (3)C11—C121.519 (3)
C1—C61.402 (3)C12—H12A0.9599
C1—C71.463 (3)C12—H12B0.9599
C2—C31.366 (3)C12—H12C0.9599
C2—H20.9300C13—H13A0.9599
C3—C41.394 (3)C13—H13B0.9599
C4—C51.375 (3)C13—H13C0.9599
C5—C61.372 (3)
C3—O1—H1X111 (2)C9—C8—H8119.1
C4—O2—H2X114 (2)O3—C9—O4123.0 (2)
C9—O4—C10119.1 (2)O3—C9—C8125.6 (2)
O5—N1—O6123.3 (3)O4—C9—C8111.4 (2)
O5—N1—C11118.6 (3)O4—C10—C11110.7 (2)
O6—N1—C11118.0 (3)O4—C10—H10A109.5
C2—C1—C6117.9 (2)C11—C10—H10A109.5
C2—C1—C7119.3 (2)O4—C10—H10B109.5
C6—C1—C7122.8 (2)C11—C10—H10B109.5
C3—C2—C1122.0 (2)H10A—C10—H10B108.1
C3—C2—H2119.0C13—C11—C10113.6 (2)
C1—C2—H2119.0C13—C11—C12111.7 (2)
C2—C3—O1124.1 (2)C10—C11—C12109.9 (2)
C2—C3—C4119.6 (2)C13—C11—N1109.1 (2)
O1—C3—C4116.3 (2)C10—C11—N1105.9 (2)
O2—C4—C5119.1 (2)C12—C11—N1106.1 (2)
O2—C4—C3121.7 (2)C11—C12—H12A109.5
C5—C4—C3119.2 (2)C11—C12—H12B109.5
C6—C5—C4121.1 (2)H12A—C12—H12B109.5
C6—C5—H5119.4C11—C12—H12C109.5
C4—C5—H5119.4H12A—C12—H12C109.5
C5—C6—C1120.1 (2)H12B—C12—H12C109.5
C5—C6—H6119.9C11—C13—H13A109.5
C1—C6—H6119.9C11—C13—H13B109.5
C8—C7—C1128.7 (2)H13A—C13—H13B109.5
C8—C7—H7115.7C11—C13—H13C109.5
C1—C7—H7115.7H13A—C13—H13C109.5
C7—C8—C9121.8 (2)H13B—C13—H13C109.5
C7—C8—H8119.1
C6—C1—C2—C30.4 (4)C1—C7—C8—C9177.9 (2)
C7—C1—C2—C3179.6 (2)C10—O4—C9—O33.4 (4)
C1—C2—C3—O1179.0 (2)C10—O4—C9—C8176.0 (2)
C1—C2—C3—C40.2 (4)C7—C8—C9—O38.4 (5)
C2—C3—C4—O2179.4 (3)C7—C8—C9—O4171.0 (3)
O1—C3—C4—O21.3 (4)C9—O4—C10—C11100.9 (3)
C2—C3—C4—C50.4 (4)O4—C10—C11—C1358.1 (3)
O1—C3—C4—C5178.9 (2)O4—C10—C11—C12176.0 (2)
O2—C4—C5—C6179.9 (3)O4—C10—C11—N161.7 (3)
C3—C4—C5—C60.0 (4)O5—N1—C11—C130.3 (3)
C4—C5—C6—C10.7 (4)O6—N1—C11—C13178.5 (3)
C2—C1—C6—C50.9 (4)O5—N1—C11—C10122.3 (3)
C7—C1—C6—C5179.1 (2)O6—N1—C11—C1058.8 (3)
C2—C1—C7—C8179.7 (3)O5—N1—C11—C12120.8 (3)
C6—C1—C7—C80.3 (4)O6—N1—C11—C1258.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1X···O3i0.82 (2)1.96 (2)2.779 (3)175 (4)
C10—H10B···O2ii0.972.503.399 (3)154
C12—H12B···O5iii0.962.503.417 (4)161
Symmetry codes: (i) x, y2, z; (ii) x1, y+1, z; (iii) x, y+1/2, z1/2.
 

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