In the title compound, C
14H
15NO
5, the 1,3-dioxane-4,6-dione ring exhibits a half-chair conformation. The amino H atom has one intra- and one intermolecular contact to carbonyl O atoms, with O
H distances of 2.11 (2) and 2.31 (2) Å.
Supporting information
CCDC reference: 293834
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.111
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact O10 .. O10 .. 2.80 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
0 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
1 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4-PC (Enraf–Nonius, 1993); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
5-[(4-Methoxyphenylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione
top
Crystal data top
C14H15NO5 | F(000) = 584 |
Mr = 277.27 | Dx = 1.377 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 13.007 (3) Å | θ = 5.1–18.6° |
b = 7.1317 (14) Å | µ = 0.11 mm−1 |
c = 14.743 (3) Å | T = 193 K |
β = 102.14 (3)° | Irregular block, colorless |
V = 1337.0 (5) Å3 | 0.43 × 0.33 × 0.20 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.022 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 1.6° |
Graphite monochromator | h = −15→15 |
ω–2θ scans | k = −8→0 |
2464 measured reflections | l = −17→0 |
2362 independent reflections | 3 standard reflections every 200 reflections |
1615 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0509P)2 + 0.2139P] where P = (Fo2 + 2Fc2)/3 |
2362 reflections | (Δ/σ)max < 0.001 |
185 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.64037 (14) | 0.2051 (3) | 0.72232 (14) | 0.0459 (5) | |
H1 | 0.6592 | 0.2110 | 0.6649 | 0.055* | |
C2 | 0.71734 (15) | 0.2175 (3) | 0.80264 (14) | 0.0473 (5) | |
H2 | 0.7875 | 0.2312 | 0.7991 | 0.057* | |
C3 | 0.69000 (14) | 0.2094 (3) | 0.88763 (13) | 0.0412 (5) | |
C4 | 0.58520 (15) | 0.1879 (3) | 0.89192 (14) | 0.0460 (5) | |
H4 | 0.5664 | 0.1823 | 0.9493 | 0.055* | |
C5 | 0.50883 (14) | 0.1750 (3) | 0.81190 (13) | 0.0435 (5) | |
H5 | 0.4388 | 0.1600 | 0.8155 | 0.052* | |
C6 | 0.53598 (14) | 0.1843 (3) | 0.72628 (13) | 0.0383 (5) | |
N7 | 0.45964 (12) | 0.1681 (2) | 0.64159 (11) | 0.0407 (4) | |
H7 | 0.4827 (16) | 0.122 (3) | 0.5958 (14) | 0.056 (7)* | |
C8 | 0.36062 (14) | 0.2173 (3) | 0.62892 (13) | 0.0389 (5) | |
H8 | 0.3389 | 0.2718 | 0.6791 | 0.047* | |
C9 | 0.28496 (14) | 0.1960 (3) | 0.54782 (12) | 0.0373 (4) | |
C10 | 0.31047 (14) | 0.1131 (3) | 0.46705 (13) | 0.0401 (5) | |
O10 | 0.39665 (10) | 0.0548 (2) | 0.46166 (9) | 0.0547 (4) | |
O11 | 0.23087 (10) | 0.0924 (2) | 0.39120 (8) | 0.0469 (4) | |
C12 | 0.14263 (14) | 0.2167 (3) | 0.38175 (12) | 0.0420 (5) | |
O13 | 0.10672 (9) | 0.2278 (2) | 0.46761 (8) | 0.0466 (4) | |
C14 | 0.17755 (14) | 0.2433 (3) | 0.54971 (13) | 0.0401 (5) | |
O14 | 0.14437 (11) | 0.2872 (2) | 0.61739 (9) | 0.0565 (4) | |
O31 | 0.75957 (10) | 0.2186 (2) | 0.97116 (9) | 0.0543 (4) | |
C32 | 0.86867 (15) | 0.2428 (3) | 0.96947 (16) | 0.0571 (6) | |
H32A | 0.9092 | 0.2470 | 1.0319 | 0.086* | |
H32B | 0.8778 | 0.3578 | 0.9383 | 0.086* | |
H32C | 0.8919 | 0.1396 | 0.9371 | 0.086* | |
C121 | 0.17341 (18) | 0.4077 (3) | 0.35325 (15) | 0.0598 (6) | |
H12A | 0.1144 | 0.4911 | 0.3469 | 0.090* | |
H12B | 0.1950 | 0.3986 | 0.2950 | 0.090* | |
H12C | 0.2305 | 0.4554 | 0.3996 | 0.090* | |
C122 | 0.05544 (16) | 0.1271 (4) | 0.31222 (14) | 0.0567 (6) | |
H12D | −0.0059 | 0.2055 | 0.3031 | 0.085* | |
H12E | 0.0392 | 0.0067 | 0.3348 | 0.085* | |
H12F | 0.0772 | 0.1118 | 0.2543 | 0.085* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0377 (10) | 0.0562 (13) | 0.0421 (11) | 0.0010 (10) | 0.0047 (9) | −0.0053 (10) |
C2 | 0.0319 (10) | 0.0574 (14) | 0.0498 (12) | −0.0005 (10) | 0.0021 (9) | −0.0044 (10) |
C3 | 0.0367 (10) | 0.0385 (11) | 0.0430 (11) | 0.0009 (9) | −0.0035 (9) | −0.0027 (9) |
C4 | 0.0394 (11) | 0.0579 (13) | 0.0386 (11) | −0.0005 (10) | 0.0032 (9) | −0.0001 (10) |
C5 | 0.0304 (10) | 0.0520 (12) | 0.0454 (12) | 0.0008 (9) | 0.0025 (9) | −0.0005 (10) |
C6 | 0.0356 (10) | 0.0353 (10) | 0.0394 (11) | 0.0030 (8) | −0.0023 (8) | −0.0040 (8) |
N7 | 0.0323 (9) | 0.0490 (11) | 0.0365 (9) | 0.0040 (8) | −0.0026 (7) | −0.0066 (8) |
C8 | 0.0377 (10) | 0.0401 (11) | 0.0364 (10) | 0.0045 (9) | 0.0019 (8) | −0.0012 (8) |
C9 | 0.0337 (10) | 0.0417 (11) | 0.0343 (10) | 0.0039 (8) | 0.0022 (8) | −0.0002 (9) |
C10 | 0.0313 (10) | 0.0488 (12) | 0.0381 (10) | 0.0042 (9) | 0.0026 (8) | 0.0018 (9) |
O10 | 0.0342 (7) | 0.0829 (11) | 0.0453 (8) | 0.0133 (7) | 0.0045 (6) | −0.0092 (8) |
O11 | 0.0377 (7) | 0.0642 (10) | 0.0345 (7) | 0.0112 (7) | −0.0018 (6) | −0.0081 (6) |
C12 | 0.0320 (10) | 0.0587 (13) | 0.0329 (10) | 0.0077 (9) | 0.0013 (8) | −0.0015 (9) |
O13 | 0.0301 (7) | 0.0740 (10) | 0.0330 (7) | 0.0080 (7) | 0.0009 (5) | −0.0017 (7) |
C14 | 0.0377 (10) | 0.0482 (12) | 0.0323 (10) | 0.0039 (9) | 0.0024 (8) | 0.0016 (9) |
O14 | 0.0459 (8) | 0.0877 (12) | 0.0370 (8) | 0.0142 (8) | 0.0108 (6) | −0.0048 (7) |
O31 | 0.0384 (8) | 0.0739 (11) | 0.0431 (8) | −0.0027 (7) | −0.0087 (6) | −0.0022 (7) |
C32 | 0.0383 (11) | 0.0624 (15) | 0.0610 (14) | −0.0077 (11) | −0.0112 (10) | −0.0019 (11) |
C121 | 0.0658 (14) | 0.0653 (16) | 0.0444 (12) | 0.0024 (13) | 0.0030 (11) | 0.0075 (11) |
C122 | 0.0424 (11) | 0.0827 (17) | 0.0397 (11) | 0.0001 (12) | −0.0032 (9) | −0.0045 (11) |
Geometric parameters (Å, º) top
C1—C6 | 1.379 (3) | C10—O10 | 1.214 (2) |
C1—C2 | 1.383 (3) | C10—O11 | 1.363 (2) |
C1—H1 | 0.9300 | O11—C12 | 1.434 (2) |
C2—C3 | 1.374 (3) | C12—O13 | 1.441 (2) |
C2—H2 | 0.9300 | C12—C122 | 1.502 (3) |
C3—O31 | 1.368 (2) | C12—C121 | 1.505 (3) |
C3—C4 | 1.386 (3) | O13—C14 | 1.363 (2) |
C4—C5 | 1.376 (3) | C14—O14 | 1.209 (2) |
C4—H4 | 0.9300 | O31—C32 | 1.435 (2) |
C5—C6 | 1.382 (3) | C32—H32A | 0.9600 |
C5—H5 | 0.9300 | C32—H32B | 0.9600 |
C6—N7 | 1.427 (2) | C32—H32C | 0.9600 |
N7—C8 | 1.310 (2) | C121—H12A | 0.9600 |
N7—H7 | 0.86 (2) | C121—H12B | 0.9600 |
C8—C9 | 1.388 (2) | C121—H12C | 0.9600 |
C8—H8 | 0.9300 | C122—H12D | 0.9600 |
C9—C10 | 1.429 (3) | C122—H12E | 0.9600 |
C9—C14 | 1.443 (2) | C122—H12F | 0.9600 |
| | | |
C6—C1—C2 | 120.82 (19) | C10—O11—C12 | 117.84 (15) |
C6—C1—H1 | 119.6 | O11—C12—O13 | 110.46 (14) |
C2—C1—H1 | 119.6 | O11—C12—C122 | 106.10 (17) |
C3—C2—C1 | 119.90 (19) | O13—C12—C122 | 106.57 (16) |
C3—C2—H2 | 120.0 | O11—C12—C121 | 109.42 (16) |
C1—C2—H2 | 120.1 | O13—C12—C121 | 110.48 (17) |
O31—C3—C2 | 124.75 (18) | C122—C12—C121 | 113.68 (17) |
O31—C3—C4 | 115.77 (18) | C14—O13—C12 | 120.08 (14) |
C2—C3—C4 | 119.47 (18) | O14—C14—O13 | 117.52 (17) |
C5—C4—C3 | 120.51 (19) | O14—C14—C9 | 126.27 (17) |
C5—C4—H4 | 119.7 | O13—C14—C9 | 116.13 (16) |
C3—C4—H4 | 119.7 | C3—O31—C32 | 117.35 (16) |
C4—C5—C6 | 120.18 (18) | O31—C32—H32A | 109.5 |
C4—C5—H5 | 119.9 | O31—C32—H32B | 109.5 |
C6—C5—H5 | 119.9 | H32A—C32—H32B | 109.5 |
C1—C6—C5 | 119.13 (17) | O31—C32—H32C | 109.5 |
C1—C6—N7 | 118.80 (18) | H32A—C32—H32C | 109.5 |
C5—C6—N7 | 122.06 (18) | H32B—C32—H32C | 109.5 |
C8—N7—C6 | 125.84 (18) | C12—C121—H12A | 109.5 |
C8—N7—H7 | 119.0 (14) | C12—C121—H12B | 109.5 |
C6—N7—H7 | 115.1 (14) | H12A—C121—H12B | 109.5 |
N7—C8—C9 | 126.25 (19) | C12—C121—H12C | 109.5 |
N7—C8—H8 | 116.9 | H12A—C121—H12C | 109.5 |
C9—C8—H8 | 116.9 | H12B—C121—H12C | 109.5 |
C8—C9—C10 | 121.07 (17) | C12—C122—H12D | 109.5 |
C8—C9—C14 | 118.15 (17) | C12—C122—H12E | 109.5 |
C10—C9—C14 | 120.52 (16) | H12D—C122—H12E | 109.5 |
O10—C10—O11 | 117.49 (17) | C12—C122—H12F | 109.5 |
O10—C10—C9 | 125.14 (17) | H12D—C122—H12F | 109.5 |
O11—C10—C9 | 117.33 (16) | H12E—C122—H12F | 109.5 |
| | | |
C6—C1—C2—C3 | −0.1 (3) | C14—C9—C10—O11 | 4.0 (3) |
C1—C2—C3—O31 | 179.44 (19) | O10—C10—O11—C12 | −156.90 (18) |
C1—C2—C3—C4 | 0.3 (3) | C9—C10—O11—C12 | 25.3 (3) |
O31—C3—C4—C5 | −179.28 (18) | C10—O11—C12—O13 | −47.5 (2) |
C2—C3—C4—C5 | −0.1 (3) | C10—O11—C12—C122 | −162.65 (16) |
C3—C4—C5—C6 | −0.3 (3) | C10—O11—C12—C121 | 74.3 (2) |
C2—C1—C6—C5 | −0.3 (3) | O11—C12—O13—C14 | 43.3 (2) |
C2—C1—C6—N7 | −178.67 (18) | C122—C12—O13—C14 | 158.18 (18) |
C4—C5—C6—C1 | 0.5 (3) | C121—C12—O13—C14 | −77.9 (2) |
C4—C5—C6—N7 | 178.86 (18) | C12—O13—C14—O14 | 166.44 (18) |
C1—C6—N7—C8 | −152.5 (2) | C12—O13—C14—C9 | −16.5 (3) |
C5—C6—N7—C8 | 29.1 (3) | C8—C9—C14—O14 | −6.0 (3) |
C6—N7—C8—C9 | −177.53 (18) | C10—C9—C14—O14 | 168.3 (2) |
N7—C8—C9—C10 | 0.3 (3) | C8—C9—C14—O13 | 177.29 (17) |
N7—C8—C9—C14 | 174.47 (19) | C10—C9—C14—O13 | −8.5 (3) |
C8—C9—C10—O10 | 0.5 (3) | C2—C3—O31—C32 | 1.5 (3) |
C14—C9—C10—O10 | −173.6 (2) | C4—C3—O31—C32 | −179.37 (18) |
C8—C9—C10—O11 | 178.10 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7···O10 | 0.86 (2) | 2.11 (2) | 2.729 (2) | 128.2 (18) |
N7—H7···O10i | 0.86 (2) | 2.31 (2) | 3.088 (2) | 150.9 (19) |
Symmetry code: (i) −x+1, −y, −z+1. |