N-Cinnamoyl-l-valine methyl ester

Bornaghi, L.F.; Poulsen, S.-A.; Healy, P.C.; White, A.R.

doi:10.1107/S1600536806050355

N-Cinnamoyl-L-valine methyl ester

L. F. Bornaghi, S.-A. Poulsen, P. C. Healy and A. R. White

The crystal structure of the title compound, C₁₅H₁₉NO₃, shows that the overall molecular conformation, which is approximately planar, is stabilized by intermolecular N—H

O hydrogen-bonding interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050355/tk2109sup1.cif Contains datablocks global, 2
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050355/tk21092sup2.hkl Contains datablock 2

CCDC reference: 634064

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.008 Å
R factor = 0.048
wR factor = 0.160
Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               1510
           Count of symmetry unique reflns         1511
           Completeness (_total/calc)             99.93%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: MSC/AFC7 Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON.

N-Cinnamoyl-L-valine methyl ester top

Crystal data top

C₁₅H₁₉NO₃	F(000) = 560
M_r = 261.31	D_x = 1.175 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 9.979 (2) Å	θ = 10.3–12.8°
b = 17.899 (3) Å	µ = 0.08 mm⁻¹
c = 8.2712 (14) Å	T = 295 K
V = 1477.4 (5) Å³	Prism, colorless
Z = 4	0.35 × 0.35 × 0.25 mm

Data collection top

Rigaku AFC-7R diffractometer	R_int = 0.024
Radiation source: Rigaku rotating anode	θ_max = 25.0°, θ_min = 2.7°
Graphite monochromator	h = −5→11
ω–2θ scans	k = 0→21
1950 measured reflections	l = −4→9
1510 independent reflections	3 standard reflections every 150 reflections
871 reflections with I > 2σ(I)	intensity decay: 0.3%

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0838P)² + 0.1628P] where P = (F_o² + 2F_c²)/3
1510 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Special details top

Experimental. The scan width was (1.84 + 0.30tanθ)° with an ω scan speed of 32° per minute (up to 5 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

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	U_iso*/U_eq
O1	0.6219 (3)	0.2490 (2)	0.4807 (5)	0.0667 (13)
O2	0.3099 (3)	0.43836 (18)	0.4459 (4)	0.0615 (11)
O3	0.4655 (4)	0.48115 (19)	0.2745 (5)	0.0700 (14)
N1	0.4160 (3)	0.2966 (2)	0.4293 (5)	0.0497 (14)
C1	0.4399 (4)	0.0623 (3)	0.7233 (5)	0.0480 (16)
C2	0.5006 (6)	−0.0065 (3)	0.7075 (6)	0.0617 (19)
C3	0.4465 (6)	−0.0705 (3)	0.7726 (7)	0.072 (2)
C4	0.3306 (7)	−0.0638 (4)	0.8631 (9)	0.087 (3)
C5	0.2714 (6)	0.0030 (5)	0.8856 (7)	0.089 (3)
C6	0.3243 (5)	0.0669 (3)	0.8185 (7)	0.072 (2)
C7	0.4956 (4)	0.1273 (3)	0.6391 (5)	0.0457 (16)
C8	0.4327 (4)	0.1895 (3)	0.6002 (5)	0.0470 (16)
C9	0.4999 (4)	0.2473 (3)	0.5013 (6)	0.0487 (16)
C10	0.4639 (4)	0.3528 (3)	0.3188 (6)	0.0503 (17)
C11	0.4392 (6)	0.3336 (3)	0.1387 (7)	0.0650 (17)
C12	0.5052 (9)	0.2594 (4)	0.1002 (9)	0.110 (3)
C13	0.2956 (7)	0.3324 (5)	0.0988 (8)	0.098 (3)
C14	0.4023 (4)	0.4275 (3)	0.3573 (6)	0.0487 (17)
C15	0.4187 (7)	0.5574 (3)	0.2971 (9)	0.088 (3)
H1	0.32470	0.29640	0.46610	0.0530*
H2	0.58200	−0.00910	0.64950	0.0720*
H3	0.48720	−0.11700	0.75790	0.0850*
H4	0.29210	−0.10760	0.90850	0.1000*
H5	0.19190	0.00580	0.94960	0.1030*
H6	0.28060	0.11410	0.83500	0.0830*
H7	0.58700	0.12360	0.60820	0.0530*
H8	0.34190	0.19760	0.63490	0.0530*
H10	0.55720	0.35690	0.33360	0.0590*
H11	0.48030	0.37100	0.07470	0.0780*
H12A	0.44770	0.22900	0.03840	0.1270*
H12B	0.58640	0.26810	0.04160	0.1270*
H12C	0.52750	0.23430	0.19900	0.1270*
H13A	0.24340	0.33340	0.19520	0.1140*
H13B	0.27330	0.37550	0.03530	0.1140*
H13C	0.27400	0.28880	0.03850	0.1140*
H15A	0.41160	0.56760	0.40810	0.1030*
H15B	0.47690	0.59050	0.24530	0.1030*
H15C	0.33070	0.56110	0.24860	0.1030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0332 (15)	0.057 (2)	0.110 (3)	0.0000 (17)	−0.0041 (19)	0.022 (2)
O2	0.0544 (19)	0.056 (2)	0.074 (2)	0.0062 (19)	0.004 (2)	−0.0024 (19)
O3	0.078 (3)	0.046 (2)	0.086 (2)	−0.0043 (19)	0.020 (2)	0.0089 (19)
N1	0.037 (2)	0.046 (2)	0.066 (3)	0.0026 (18)	0.0022 (19)	0.005 (2)
C1	0.041 (2)	0.056 (3)	0.047 (3)	0.004 (3)	−0.010 (2)	0.009 (2)
C2	0.054 (3)	0.063 (4)	0.068 (3)	0.000 (3)	0.001 (3)	0.016 (3)
C3	0.077 (4)	0.063 (4)	0.077 (4)	0.001 (3)	−0.007 (3)	0.022 (3)
C4	0.075 (4)	0.095 (5)	0.092 (5)	−0.019 (4)	−0.015 (4)	0.050 (4)
C5	0.058 (4)	0.126 (6)	0.083 (5)	0.000 (4)	0.017 (3)	0.046 (5)
C6	0.058 (3)	0.091 (4)	0.066 (4)	0.009 (3)	0.011 (3)	0.024 (3)
C7	0.033 (2)	0.048 (3)	0.056 (3)	0.000 (2)	−0.002 (2)	0.003 (2)
C8	0.032 (2)	0.057 (3)	0.052 (3)	0.000 (2)	−0.002 (2)	0.002 (2)
C9	0.033 (2)	0.049 (3)	0.064 (3)	0.007 (3)	−0.006 (2)	−0.001 (2)
C10	0.041 (3)	0.046 (3)	0.064 (3)	0.001 (2)	0.002 (2)	0.003 (2)
C11	0.071 (3)	0.063 (3)	0.061 (3)	0.005 (3)	0.008 (3)	−0.006 (3)
C12	0.159 (7)	0.101 (5)	0.071 (4)	0.052 (5)	0.001 (5)	−0.026 (4)
C13	0.093 (4)	0.121 (6)	0.081 (4)	0.004 (5)	−0.028 (4)	−0.027 (4)
C14	0.041 (3)	0.050 (3)	0.055 (3)	0.001 (2)	−0.004 (2)	0.000 (3)
C15	0.119 (5)	0.041 (3)	0.105 (5)	−0.005 (3)	0.017 (5)	0.007 (3)

Geometric parameters (Å, º) top

O1—C9	1.230 (5)	C11—C13	1.471 (9)
O2—C14	1.194 (5)	C2—H2	0.9400
O3—C14	1.338 (6)	C3—H3	0.9300
O3—C15	1.455 (7)	C4—H4	0.9500
N1—C9	1.354 (6)	C5—H5	0.9600
N1—C10	1.441 (6)	C6—H6	0.9600
N1—H1	0.9600	C7—H7	0.9500
C1—C6	1.399 (7)	C8—H8	0.9600
C1—C7	1.466 (7)	C10—H10	0.9400
C1—C2	1.379 (8)	C11—H11	0.9500
C2—C3	1.376 (8)	C12—H12A	0.9400
C3—C4	1.383 (9)	C12—H12B	0.9600
C4—C5	1.347 (11)	C12—H12C	0.9600
C5—C6	1.377 (10)	C13—H13A	0.9500
C7—C8	1.318 (7)	C13—H13B	0.9600
C8—C9	1.480 (7)	C13—H13C	0.9500
C10—C11	1.549 (8)	C15—H15A	0.9400
C10—C14	1.506 (7)	C15—H15B	0.9300
C11—C12	1.516 (9)	C15—H15C	0.9700

O1···C12	3.361 (9)	H1···O2	2.5500
O1···N1ⁱ	3.136 (4)	H1···H8	2.2600
O1···C8ⁱ	3.358 (5)	H1···H13A	2.4700
O2···N1	2.753 (5)	H1···O1^iv	2.2200
O2···C3ⁱⁱ	3.370 (7)	H2···H7	2.4000
O3···C5ⁱ	3.340 (7)	H2···O2ⁱ	2.7200
O1···H7	2.5000	H4···O1^v	2.8600
O1···H8ⁱ	2.5800	H5···C1^ix	2.8900
O1···H4ⁱⁱ	2.8600	H5···C2^ix	2.8700
O1···H12C	2.5300	H6···C8	2.8100
O1···H10	2.3700	H6···H8	2.3100
O1···H1ⁱ	2.2200	H7···O1	2.5000
O2···H13A	2.8800	H7···H2	2.4000
O2···H15C	2.7400	H7···O2ⁱ	2.5300
O2···H15Cⁱⁱⁱ	2.8700	H7···H13Aⁱ	2.3800
O2···H2^iv	2.7200	H8···C6	2.7900
O2···H7^iv	2.5300	H8···H1	2.2600
O2···H1	2.5500	H8···H6	2.3100
O2···H15A	2.5500	H8···O1^iv	2.5800
O3···H11	2.5800	H10···O1	2.3700
N1···O2	2.753 (5)	H10···H12C	2.4800
N1···O1^iv	3.136 (4)	H10···C4ⁱⁱ	3.0900
N1···H12C	2.4700	H11···O3	2.5800
N1···H13A	2.6700	H12A···H13C	2.0400
C3···C14^v	3.413 (8)	H12B···C13^vii	2.9900
C3···O2^v	3.370 (7)	H12B···H13C^vii	2.2300
C4···C14^v	3.532 (8)	H12C···O1	2.5300
C5···O3^iv	3.340 (7)	H12C···N1	2.4700
C8···O1^iv	3.358 (5)	H12C···C9	2.5300
C9···C12	3.325 (9)	H12C···H10	2.4800
C12···C9	3.325 (9)	H13A···O2	2.8800
C12···O1	3.361 (9)	H13A···N1	2.6700
C14···C4ⁱⁱ	3.532 (8)	H13A···C14	2.6700
C14···C3ⁱⁱ	3.413 (8)	H13A···H1	2.4700
C1···H5^vi	2.8900	H13A···C7^iv	2.9100
C2···H5^vi	2.8700	H13A···H7^iv	2.3800
C4···H10^v	3.0900	H13B···C15^x	3.0000
C6···H8	2.7900	H13B···H15A^x	2.3600
C7···H13Aⁱ	2.9100	H13C···H12A	2.0400
C8···H6	2.8100	H13C···C12^viii	3.0400
C9···H12C	2.5300	H13C···H12B^viii	2.2300
C12···H13C^vii	3.0400	H15A···O2	2.5500
C13···H12B^viii	2.9900	H15A···H13Bⁱⁱⁱ	2.3600
C14···H13A	2.6700	H15C···O2	2.7400
C15···H13Bⁱⁱⁱ	3.0000	H15C···O2^x	2.8700

C14—O3—C15	117.2 (4)	C4—C5—H5	119.00
C9—N1—C10	121.9 (3)	C6—C5—H5	120.00
C9—N1—H1	116.00	C1—C6—H6	120.00
C10—N1—H1	121.00	C5—C6—H6	120.00
C6—C1—C7	122.2 (5)	C1—C7—H7	116.00
C2—C1—C6	117.9 (5)	C8—C7—H7	117.00
C2—C1—C7	119.8 (4)	C7—C8—H8	120.00
C1—C2—C3	122.3 (5)	C9—C8—H8	119.00
C2—C3—C4	117.9 (5)	N1—C10—H10	107.00
C3—C4—C5	121.3 (6)	C11—C10—H10	107.00
C4—C5—C6	120.9 (6)	C14—C10—H10	108.00
C1—C6—C5	119.6 (5)	C10—C11—H11	108.00
C1—C7—C8	127.3 (4)	C12—C11—H11	108.00
C7—C8—C9	120.7 (4)	C13—C11—H11	108.00
O1—C9—C8	122.9 (4)	C11—C12—H12A	111.00
O1—C9—N1	122.3 (5)	C11—C12—H12B	109.00
N1—C9—C8	114.7 (3)	C11—C12—H12C	109.00
N1—C10—C14	110.5 (4)	H12A—C12—H12B	110.00
N1—C10—C11	113.7 (4)	H12A—C12—H12C	109.00
C11—C10—C14	109.6 (4)	H12B—C12—H12C	108.00
C10—C11—C13	112.0 (5)	C11—C13—H13A	110.00
C12—C11—C13	111.3 (6)	C11—C13—H13B	110.00
C10—C11—C12	109.1 (5)	C11—C13—H13C	111.00
O3—C14—C10	109.7 (4)	H13A—C13—H13B	108.00
O2—C14—O3	124.2 (5)	H13A—C13—H13C	109.00
O2—C14—C10	126.1 (5)	H13B—C13—H13C	109.00
C1—C2—H2	118.00	O3—C15—H15A	109.00
C3—C2—H2	120.00	O3—C15—H15B	110.00
C2—C3—H3	121.00	O3—C15—H15C	108.00
C4—C3—H3	121.00	H15A—C15—H15B	112.00
C3—C4—H4	119.00	H15A—C15—H15C	109.00
C5—C4—H4	120.00	H15B—C15—H15C	109.00

C15—O3—C14—O2	1.0 (7)	C3—C4—C5—C6	0.2 (10)
C15—O3—C14—C10	180.0 (4)	C4—C5—C6—C1	1.1 (9)
C10—N1—C9—O1	2.3 (8)	C1—C7—C8—C9	−174.2 (4)
C10—N1—C9—C8	−175.1 (4)	C7—C8—C9—O1	−16.4 (7)
C9—N1—C10—C11	102.2 (5)	C7—C8—C9—N1	161.0 (4)
C9—N1—C10—C14	−134.1 (4)	N1—C10—C11—C12	−57.4 (6)
C6—C1—C2—C3	4.4 (8)	N1—C10—C11—C13	66.3 (6)
C7—C1—C2—C3	−174.5 (5)	C14—C10—C11—C12	178.3 (5)
C2—C1—C6—C5	−3.3 (7)	C14—C10—C11—C13	−58.0 (6)
C7—C1—C6—C5	175.5 (5)	N1—C10—C14—O2	−12.4 (6)
C2—C1—C7—C8	157.9 (5)	N1—C10—C14—O3	168.6 (4)
C6—C1—C7—C8	−21.0 (7)	C11—C10—C14—O2	113.7 (5)
C1—C2—C3—C4	−3.2 (9)	C11—C10—C14—O3	−65.3 (5)
C2—C3—C4—C5	0.7 (10)

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1/2, −y+1, z+1/2; (iv) x−1/2, −y+1/2, −z+1; (v) −x+1, y−1/2, −z+3/2; (vi) −x+1/2, −y, z−1/2; (vii) x+1/2, −y+1/2, −z; (viii) x−1/2, −y+1/2, −z; (ix) −x+1/2, −y, z+1/2; (x) −x+1/2, −y+1, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^iv	0.96	2.22	3.136 (4)	158
C7—H7···O1	0.95	2.50	2.837 (6)	101
C7—H7···O2ⁱ	0.95	2.53	3.422 (5)	158
C8—H8···O1^iv	0.96	2.58	3.358 (5)	138
C10—H10···O1	0.94	2.37	2.781 (6)	106
C12—H12C···O1	0.96	2.53	3.361 (9)	145
C12—H12C···N1	0.96	2.47	2.940 (9)	110

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (iv) x−1/2, −y+1/2, −z+1.

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