Methyl 6-amino-5-cyano-2-methoxy­carbonyl­methyl-4-phenyl-4H-pyran-3-carboxyl­ate

Öztürk, S.; Akkurt, M.; Stoyanov, E.; Büyükgüngör, O.; Heber, D.

doi:10.1107/S1600536804001497

Methyl 6-amino-5-cyano-2-methoxycarbonylmethyl-4-phenyl-4H-pyran-3-carboxylate

S. Öztürk, M. Akkurt, E. Stoyanov, O. Büyükgüngör and D. Heber

The pyran ring in the title compound, C₁₇H₁₆N₂O₅, adopts a boat conformation. The crystal packing is stabilized by intermolecular N—H

O and N—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001497/cv6267sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001497/cv6267Isup2.hkl Contains datablock I

CCDC reference: 234912

checkCIF report

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

Computing details top

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-4H-pyran-3-carboxylate top

Crystal data top

C₁₇H₁₆N₂O₅	Z = 2
M_r = 328.32	F(000) = 344
Triclinic, P1	D_x = 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	R_int = 0.024
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 2.1°
ω rotation scans	h = −10→10
Absorption correction: integration STOE X-RED (Stoe & Cie, 2002)	k = −12→12
T_min = 0.968, T_max = 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(F_o²) + (0.0681P)²] where P = (F_o² + 2F_c²)/3
3065 reflections	(Δ/σ)_max < 0.001
225 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −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 F^{2 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 F^{2. The observed criterion of} ^F2 > σ(F^{2) 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	U_iso*/U_eq
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···C8^ix	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···H17A^ix	3.0179
O4···O1	3.1892 (15)	C6···H15B^viii	3.0575
O4···C2	3.2885 (17)	C6···H2B	2.654 (17)
O5···C16ⁱⁱⁱ	3.394 (2)	C8···H17C^ix	2.9286
O2···H14C	2.6401	C9···H17C^ix	3.0578
O2···H14B	2.6012	C11···H14A^xi	2.9489
O2···H3	2.5373	C13···H15A	2.8548
O2···H2Aⁱ	2.186 (19)	C14···H10^x	3.0114
O3···H15A	2.1595	H2A···O2^vii	2.186 (19)
O4···H8	2.6026	H2B···C6	2.654 (17)
O5···H10^iv	2.8465	H2B···N1^v	2.24 (2)
O5···H17B	2.6388	H3···O2	2.5373
O5···H17C	2.6235	H3···H12	2.3665
O5···H11^iv	2.8198	H3···H14Cⁱⁱ	2.4823
O5···H17Bⁱⁱⁱ	2.8966	H8···O4	2.6026
N1···N1^v	3.083 (2)	H8···C1	2.9946
N1···N2^v	3.132 (2)	H8···C2	2.6720
N1···C6^v	3.360 (2)	H10···O5^xiii	2.8465
N1···C12^vi	3.369 (2)	H10···C14^x	3.0114
N2···N1^v	3.132 (2)	H10···H14B^x	2.3905
N2···O2^vii	3.038 (2)	H11···O5^xiii	2.8198
N1···H12^vi	2.6952	H12···H3	2.3665
N1···H2B^v	2.24 (2)	H12···N1^vi	2.6952
C1···C8	3.576 (2)	H14A···C11^xii	2.9489
C2···O4	3.2885 (17)	H14A···H17Cⁱⁱⁱ	2.5054
C4···C15^viii	3.573 (2)	H14B···O2	2.6012
C6···C12	3.328 (2)	H14B···H10^x	2.3905
C6···N1^v	3.360 (2)	H14C···O2	2.6401
C6···C15^viii	3.559 (2)	H14C···H3ⁱⁱ	2.4823
C7···O2	3.057 (2)	H15A···O3	2.1595
C8···C17^ix	3.580 (3)	H15A···C13	2.8548
C8···C1	3.576 (2)	H15A···H17Bⁱⁱⁱ	2.4939
C8···C13	3.499 (2)	H15B···C6^viii	3.0575
C9···C9^x	3.465 (3)	H17A···C5^ix	3.0179
C11···C14^xi	3.559 (3)	H17B···O5	2.6388
C12···C6	3.328 (2)	H17B···O5ⁱⁱⁱ	2.8966
C12···N1^vi	3.369 (2)	H17B···H15Aⁱⁱⁱ	2.4939
C13···C8	3.499 (2)	H17C···O5	2.6235
C14···C11^xii	3.559 (3)	H17C···C8^ix	2.9286
C15···O3	2.8059 (19)	H17C···C9^ix	3.0578
C15···C4^viii	3.573 (2)	H17C···H14Aⁱⁱⁱ	2.5054
C15···C6^viii	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···O2^vii	0.853 (19)	2.186 (19)	3.038 (2)	176.8 (15)
N2—H2B···N1^v	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.

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Methyl 6-amino-5-cyano-2-methoxy­carbonyl­methyl-4-phenyl-4H-pyran-3-carboxyl­ate

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Methyl 6-amino-5-cyano-2-methoxycarbonylmethyl-4-phenyl-4H-pyran-3-carboxylate