The pyran ring in the title compound, C
17H
16N
2O
5, adopts a boat conformation. The crystal packing is stabilized by intermolecular N—H
O and N—H
N hydrogen bonds.
Supporting information
CCDC reference: 234912
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.108
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C6 = 5.51 su
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C16
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
2 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: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Methyl
6-amino-5-cyano-2-methoxycarbonylmethyl-4-phenyl-4
H-pyran-3-carboxylate
top
Crystal data top
C17H16N2O5 | Z = 2 |
Mr = 328.32 | F(000) = 344 |
Triclinic, P1 | Dx = 1.390 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1635 (8) Å | Cell parameters from 8916 reflections |
b = 10.0366 (9) Å | θ = 2.1–27.0° |
c = 10.6641 (10) Å | µ = 0.10 mm−1 |
α = 67.340 (7)° | T = 293 K |
β = 87.008 (8)° | Prism, colorless |
γ = 76.740 (7)° | 0.40 × 0.33 × 0.27 mm |
V = 784.17 (14) Å3 | |
Data collection top
Stoe IPDS-II diffractometer | 3065 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2265 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.024 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.1° |
ω rotation scans | h = −10→10 |
Absorption correction: integration STOE X-RED (Stoe & Cie, 2002) | k = −12→12 |
Tmin = 0.968, Tmax = 0.981 | l = −13→13 |
11291 measured reflections | |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0681P)2] where P = (Fo2 + 2Fc2)/3 |
3065 reflections | (Δ/σ)max < 0.001 |
225 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR
and all goodnesses of fit S are based on F2,
conventional R-factors R are based on F, with F
set to zero for negative F2. The observed criterion of F2 >
σ(F2) is used only for calculating -R-factor-obs
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 | |
O1 | 0.40695 (11) | 0.52636 (10) | 0.81210 (10) | 0.0438 (3) | |
O2 | 0.97587 (14) | 0.55060 (13) | 0.83954 (14) | 0.0647 (5) | |
O3 | 0.78344 (14) | 0.76208 (12) | 0.77532 (13) | 0.0583 (4) | |
O4 | 0.50094 (15) | 0.75340 (12) | 0.52865 (11) | 0.0559 (4) | |
O5 | 0.3118 (2) | 0.94787 (16) | 0.53574 (14) | 0.0937 (6) | |
N1 | 0.68042 (19) | 0.01653 (16) | 1.01444 (19) | 0.0731 (6) | |
N2 | 0.30759 (17) | 0.32262 (17) | 0.88770 (15) | 0.0528 (5) | |
C1 | 0.53023 (17) | 0.60543 (15) | 0.79822 (13) | 0.0375 (4) | |
C2 | 0.69315 (16) | 0.53912 (14) | 0.82513 (13) | 0.0366 (4) | |
C3 | 0.75493 (16) | 0.37375 (15) | 0.86413 (13) | 0.0373 (4) | |
C4 | 0.60800 (17) | 0.29921 (15) | 0.90446 (13) | 0.0386 (4) | |
C5 | 0.44668 (17) | 0.37541 (14) | 0.87126 (13) | 0.0382 (4) | |
C6 | 0.64477 (18) | 0.14331 (17) | 0.96493 (16) | 0.0472 (5) | |
C7 | 0.84903 (16) | 0.33496 (15) | 0.75112 (14) | 0.0396 (4) | |
C8 | 0.7997 (2) | 0.41403 (19) | 0.61622 (16) | 0.0562 (5) | |
C9 | 0.8832 (3) | 0.3707 (2) | 0.51613 (19) | 0.0720 (7) | |
C10 | 1.0151 (3) | 0.2483 (2) | 0.5523 (2) | 0.0715 (8) | |
C11 | 1.0642 (2) | 0.1694 (2) | 0.6855 (2) | 0.0644 (7) | |
C12 | 0.98263 (18) | 0.21245 (17) | 0.78493 (18) | 0.0500 (5) | |
C13 | 0.83082 (18) | 0.61600 (16) | 0.81460 (14) | 0.0413 (4) | |
C14 | 0.9121 (2) | 0.8413 (2) | 0.7708 (2) | 0.0688 (7) | |
C15 | 0.44315 (18) | 0.76588 (15) | 0.74352 (15) | 0.0428 (4) | |
C16 | 0.40986 (19) | 0.83295 (16) | 0.59188 (16) | 0.0475 (5) | |
C17 | 0.4819 (3) | 0.8124 (2) | 0.38221 (18) | 0.0719 (7) | |
H2A | 0.213 (2) | 0.385 (2) | 0.8723 (18) | 0.058 (5)* | |
H2B | 0.314 (2) | 0.226 (2) | 0.9154 (19) | 0.066 (5)* | |
H3 | 0.83270 | 0.33540 | 0.94350 | 0.0450* | |
H8 | 0.71020 | 0.49670 | 0.59190 | 0.0670* | |
H9 | 0.84990 | 0.42450 | 0.42510 | 0.0860* | |
H10 | 1.07100 | 0.21930 | 0.48560 | 0.0860* | |
H11 | 1.15300 | 0.08630 | 0.70950 | 0.0770* | |
H12 | 1.01770 | 0.15860 | 0.87560 | 0.0600* | |
H14A | 0.86210 | 0.94550 | 0.74100 | 0.1030* | |
H14B | 0.99580 | 0.82470 | 0.70860 | 0.1030* | |
H14C | 0.96380 | 0.80660 | 0.85990 | 0.1030* | |
H15A | 0.51150 | 0.82060 | 0.76730 | 0.0510* | |
H15B | 0.33670 | 0.77740 | 0.78740 | 0.0510* | |
H17A | 0.55400 | 0.74510 | 0.34790 | 0.1080* | |
H17B | 0.51210 | 0.90670 | 0.34520 | 0.1080* | |
H17C | 0.36690 | 0.82450 | 0.35620 | 0.1080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0351 (5) | 0.0316 (5) | 0.0559 (6) | −0.0019 (4) | −0.0016 (4) | −0.0100 (4) |
O2 | 0.0395 (6) | 0.0531 (7) | 0.0992 (10) | −0.0033 (5) | −0.0083 (6) | −0.0295 (7) |
O3 | 0.0497 (6) | 0.0382 (6) | 0.0831 (8) | −0.0118 (5) | −0.0031 (6) | −0.0173 (6) |
O4 | 0.0648 (7) | 0.0469 (6) | 0.0482 (6) | −0.0001 (5) | 0.0006 (5) | −0.0168 (5) |
O5 | 0.1145 (12) | 0.0620 (9) | 0.0697 (9) | 0.0377 (8) | −0.0180 (8) | −0.0175 (7) |
N1 | 0.0519 (8) | 0.0367 (8) | 0.1083 (13) | −0.0038 (6) | −0.0055 (8) | −0.0062 (8) |
N2 | 0.0384 (7) | 0.0380 (8) | 0.0746 (10) | −0.0071 (6) | 0.0042 (6) | −0.0148 (7) |
C1 | 0.0401 (7) | 0.0326 (7) | 0.0374 (7) | −0.0049 (6) | 0.0027 (6) | −0.0130 (6) |
C2 | 0.0388 (7) | 0.0336 (7) | 0.0347 (7) | −0.0035 (6) | 0.0015 (5) | −0.0128 (6) |
C3 | 0.0355 (7) | 0.0324 (7) | 0.0377 (7) | −0.0008 (5) | −0.0024 (5) | −0.0100 (6) |
C4 | 0.0387 (7) | 0.0324 (7) | 0.0374 (7) | −0.0021 (6) | 0.0028 (6) | −0.0092 (6) |
C5 | 0.0408 (7) | 0.0319 (7) | 0.0370 (7) | −0.0045 (6) | 0.0035 (6) | −0.0102 (6) |
C6 | 0.0385 (7) | 0.0386 (9) | 0.0554 (9) | −0.0051 (6) | 0.0027 (6) | −0.0104 (7) |
C7 | 0.0350 (7) | 0.0347 (7) | 0.0495 (8) | −0.0084 (6) | 0.0064 (6) | −0.0169 (6) |
C8 | 0.0595 (9) | 0.0513 (9) | 0.0495 (9) | −0.0011 (8) | 0.0090 (8) | −0.0179 (8) |
C9 | 0.0893 (14) | 0.0732 (13) | 0.0540 (10) | −0.0172 (11) | 0.0196 (10) | −0.0277 (9) |
C10 | 0.0751 (12) | 0.0702 (13) | 0.0867 (14) | −0.0212 (10) | 0.0363 (11) | −0.0503 (11) |
C11 | 0.0521 (9) | 0.0539 (10) | 0.0934 (15) | −0.0084 (8) | 0.0217 (9) | −0.0394 (10) |
C12 | 0.0391 (7) | 0.0414 (8) | 0.0681 (10) | −0.0038 (6) | 0.0055 (7) | −0.0231 (7) |
C13 | 0.0426 (8) | 0.0385 (8) | 0.0404 (7) | −0.0046 (6) | 0.0006 (6) | −0.0152 (6) |
C14 | 0.0645 (11) | 0.0520 (11) | 0.0927 (14) | −0.0245 (9) | −0.0065 (10) | −0.0232 (10) |
C15 | 0.0403 (7) | 0.0333 (7) | 0.0514 (8) | −0.0006 (6) | 0.0008 (6) | −0.0168 (6) |
C16 | 0.0473 (8) | 0.0329 (8) | 0.0557 (9) | −0.0005 (6) | −0.0008 (7) | −0.0143 (7) |
C17 | 0.0969 (15) | 0.0673 (12) | 0.0478 (10) | −0.0164 (11) | 0.0035 (9) | −0.0195 (9) |
Geometric parameters (Å, º) top
O1—C1 | 1.3874 (18) | C7—C8 | 1.377 (2) |
O1—C5 | 1.3631 (18) | C8—C9 | 1.392 (3) |
O2—C13 | 1.202 (2) | C9—C10 | 1.374 (3) |
O3—C13 | 1.326 (2) | C10—C11 | 1.361 (3) |
O3—C14 | 1.444 (2) | C11—C12 | 1.379 (3) |
O4—C16 | 1.317 (2) | C15—C16 | 1.505 (2) |
O4—C17 | 1.444 (2) | C3—H3 | 0.9801 |
O5—C16 | 1.193 (2) | C8—H8 | 0.9303 |
N1—C6 | 1.145 (2) | C9—H9 | 0.9296 |
N2—C5 | 1.336 (2) | C10—H10 | 0.9293 |
N2—H2A | 0.853 (19) | C11—H11 | 0.9296 |
N2—H2B | 0.89 (2) | C12—H12 | 0.9296 |
C1—C15 | 1.494 (2) | C14—H14A | 0.9607 |
C1—C2 | 1.335 (2) | C14—H14B | 0.9593 |
C2—C13 | 1.480 (2) | C14—H14C | 0.9601 |
C2—C3 | 1.513 (2) | C15—H15A | 0.9695 |
C3—C4 | 1.514 (2) | C15—H15B | 0.9699 |
C3—C7 | 1.524 (2) | C17—H17A | 0.9603 |
C4—C6 | 1.408 (2) | C17—H17B | 0.9599 |
C4—C5 | 1.350 (2) | C17—H17C | 0.9602 |
C7—C12 | 1.384 (2) | | |
| | | |
O1···O4 | 3.1892 (15) | C16···O5iii | 3.394 (2) |
O2···N2i | 3.038 (2) | C17···C8ix | 3.580 (3) |
O2···C7 | 3.057 (2) | C1···H8 | 2.9946 |
O2···O2ii | 3.190 (2) | C2···H8 | 2.6720 |
O3···C15 | 2.8059 (19) | C5···H17Aix | 3.0179 |
O4···O1 | 3.1892 (15) | C6···H15Bviii | 3.0575 |
O4···C2 | 3.2885 (17) | C6···H2B | 2.654 (17) |
O5···C16iii | 3.394 (2) | C8···H17Cix | 2.9286 |
O2···H14C | 2.6401 | C9···H17Cix | 3.0578 |
O2···H14B | 2.6012 | C11···H14Axi | 2.9489 |
O2···H3 | 2.5373 | C13···H15A | 2.8548 |
O2···H2Ai | 2.186 (19) | C14···H10x | 3.0114 |
O3···H15A | 2.1595 | H2A···O2vii | 2.186 (19) |
O4···H8 | 2.6026 | H2B···C6 | 2.654 (17) |
O5···H10iv | 2.8465 | H2B···N1v | 2.24 (2) |
O5···H17B | 2.6388 | H3···O2 | 2.5373 |
O5···H17C | 2.6235 | H3···H12 | 2.3665 |
O5···H11iv | 2.8198 | H3···H14Cii | 2.4823 |
O5···H17Biii | 2.8966 | H8···O4 | 2.6026 |
N1···N1v | 3.083 (2) | H8···C1 | 2.9946 |
N1···N2v | 3.132 (2) | H8···C2 | 2.6720 |
N1···C6v | 3.360 (2) | H10···O5xiii | 2.8465 |
N1···C12vi | 3.369 (2) | H10···C14x | 3.0114 |
N2···N1v | 3.132 (2) | H10···H14Bx | 2.3905 |
N2···O2vii | 3.038 (2) | H11···O5xiii | 2.8198 |
N1···H12vi | 2.6952 | H12···H3 | 2.3665 |
N1···H2Bv | 2.24 (2) | H12···N1vi | 2.6952 |
C1···C8 | 3.576 (2) | H14A···C11xii | 2.9489 |
C2···O4 | 3.2885 (17) | H14A···H17Ciii | 2.5054 |
C4···C15viii | 3.573 (2) | H14B···O2 | 2.6012 |
C6···C12 | 3.328 (2) | H14B···H10x | 2.3905 |
C6···N1v | 3.360 (2) | H14C···O2 | 2.6401 |
C6···C15viii | 3.559 (2) | H14C···H3ii | 2.4823 |
C7···O2 | 3.057 (2) | H15A···O3 | 2.1595 |
C8···C17ix | 3.580 (3) | H15A···C13 | 2.8548 |
C8···C1 | 3.576 (2) | H15A···H17Biii | 2.4939 |
C8···C13 | 3.499 (2) | H15B···C6viii | 3.0575 |
C9···C9x | 3.465 (3) | H17A···C5ix | 3.0179 |
C11···C14xi | 3.559 (3) | H17B···O5 | 2.6388 |
C12···C6 | 3.328 (2) | H17B···O5iii | 2.8966 |
C12···N1vi | 3.369 (2) | H17B···H15Aiii | 2.4939 |
C13···C8 | 3.499 (2) | H17C···O5 | 2.6235 |
C14···C11xii | 3.559 (3) | H17C···C8ix | 2.9286 |
C15···O3 | 2.8059 (19) | H17C···C9ix | 3.0578 |
C15···C4viii | 3.573 (2) | H17C···H14Aiii | 2.5054 |
C15···C6viii | 3.559 (2) | | |
| | | |
C1—O1—C5 | 120.16 (11) | O4—C16—O5 | 124.03 (15) |
C13—O3—C14 | 117.52 (13) | O4—C16—C15 | 113.32 (14) |
C16—O4—C17 | 117.07 (14) | O5—C16—C15 | 122.65 (15) |
C5—N2—H2A | 117.5 (13) | C2—C3—H3 | 107.99 |
C5—N2—H2B | 120.9 (11) | C4—C3—H3 | 108.02 |
H2A—N2—H2B | 121.6 (17) | C7—C3—H3 | 107.99 |
C2—C1—C15 | 131.00 (14) | C7—C8—H8 | 119.84 |
O1—C1—C15 | 106.70 (12) | C9—C8—H8 | 119.90 |
O1—C1—C2 | 122.21 (14) | C8—C9—H9 | 120.08 |
C3—C2—C13 | 113.22 (12) | C10—C9—H9 | 120.11 |
C1—C2—C13 | 125.12 (14) | C9—C10—H10 | 119.90 |
C1—C2—C3 | 121.60 (13) | C11—C10—H10 | 119.87 |
C2—C3—C4 | 109.81 (12) | C10—C11—H11 | 119.91 |
C2—C3—C7 | 112.66 (11) | C12—C11—H11 | 119.92 |
C4—C3—C7 | 110.22 (12) | C7—C12—H12 | 119.66 |
C5—C4—C6 | 119.70 (14) | C11—C12—H12 | 119.66 |
C3—C4—C5 | 122.29 (13) | O3—C14—H14A | 109.47 |
C3—C4—C6 | 117.62 (13) | O3—C14—H14B | 109.54 |
O1—C5—N2 | 110.40 (13) | O3—C14—H14C | 109.47 |
O1—C5—C4 | 121.13 (13) | H14A—C14—H14B | 109.45 |
N2—C5—C4 | 128.47 (15) | H14A—C14—H14C | 109.40 |
N1—C6—C4 | 177.64 (17) | H14B—C14—H14C | 109.49 |
C8—C7—C12 | 118.84 (15) | C1—C15—H15A | 108.67 |
C3—C7—C8 | 121.82 (14) | C1—C15—H15B | 108.70 |
C3—C7—C12 | 119.25 (13) | C16—C15—H15A | 108.67 |
C7—C8—C9 | 120.26 (17) | C16—C15—H15B | 108.70 |
C8—C9—C10 | 119.81 (17) | H15A—C15—H15B | 107.64 |
C9—C10—C11 | 120.23 (19) | O4—C17—H17A | 109.46 |
C10—C11—C12 | 120.18 (19) | O4—C17—H17B | 109.47 |
C7—C12—C11 | 120.68 (16) | O4—C17—H17C | 109.45 |
O3—C13—C2 | 115.45 (13) | H17A—C17—H17B | 109.50 |
O2—C13—O3 | 122.24 (15) | H17A—C17—H17C | 109.43 |
O2—C13—C2 | 122.32 (15) | H17B—C17—H17C | 109.51 |
C1—C15—C16 | 114.26 (13) | | |
| | | |
C5—O1—C1—C2 | 8.69 (19) | C2—C3—C7—C12 | 145.84 (14) |
C5—O1—C1—C15 | −174.35 (11) | C4—C3—C7—C12 | −91.13 (16) |
C1—O1—C5—N2 | 173.34 (12) | C2—C3—C4—C5 | 17.44 (18) |
C1—O1—C5—C4 | −6.97 (19) | C7—C3—C4—C5 | −107.25 (15) |
C14—O3—C13—C2 | 176.63 (13) | C4—C3—C7—C8 | 85.57 (18) |
C14—O3—C13—O2 | −3.6 (2) | C7—C3—C4—C6 | 65.47 (16) |
C17—O4—C16—O5 | 1.4 (3) | C2—C3—C4—C6 | −169.85 (12) |
C17—O4—C16—C15 | −177.66 (15) | C2—C3—C7—C8 | −37.47 (19) |
C2—C1—C15—C16 | 94.67 (19) | C6—C4—C5—N2 | −0.1 (2) |
O1—C1—C2—C3 | 3.9 (2) | C3—C4—C5—N2 | 172.46 (14) |
O1—C1—C15—C16 | −81.92 (15) | C3—C4—C5—O1 | −7.2 (2) |
O1—C1—C2—C13 | −179.03 (12) | C6—C4—C5—O1 | −179.74 (13) |
C15—C1—C2—C3 | −172.22 (13) | C3—C7—C12—C11 | 176.26 (15) |
C15—C1—C2—C13 | 4.8 (2) | C12—C7—C8—C9 | 0.1 (3) |
C3—C2—C13—O3 | 177.41 (12) | C3—C7—C8—C9 | −176.61 (17) |
C13—C2—C3—C4 | 166.92 (11) | C8—C7—C12—C11 | −0.5 (2) |
C1—C2—C13—O3 | 0.1 (2) | C7—C8—C9—C10 | 0.2 (3) |
C1—C2—C3—C7 | 107.56 (15) | C8—C9—C10—C11 | 0.0 (3) |
C13—C2—C3—C7 | −69.82 (15) | C9—C10—C11—C12 | −0.5 (3) |
C3—C2—C13—O2 | −2.4 (2) | C10—C11—C12—C7 | 0.7 (3) |
C1—C2—C13—O2 | −179.64 (15) | C1—C15—C16—O5 | 163.51 (16) |
C1—C2—C3—C4 | −15.70 (17) | C1—C15—C16—O4 | −17.38 (19) |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z+2; (iii) −x+1, −y+2, −z+1; (iv) x−1, y+1, z; (v) −x+1, −y, −z+2; (vi) −x+2, −y, −z+2; (vii) x−1, y, z; (viii) −x+1, −y+1, −z+2; (ix) −x+1, −y+1, −z+1; (x) −x+2, −y+1, −z+1; (xi) x, y−1, z; (xii) x, y+1, z; (xiii) x+1, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2vii | 0.853 (19) | 2.186 (19) | 3.038 (2) | 176.8 (15) |
N2—H2B···N1v | 0.89 (2) | 2.24 (2) | 3.132 (2) | 177.8 (16) |
C15—H15A···O3 | 0.97 | 2.16 | 2.8059 (19) | 123 |
Symmetry codes: (v) −x+1, −y, −z+2; (vii) x−1, y, z. |