N-[(1,3-Benzodioxol-5-yl)meth-yl]-4-methyl-benzamide: an analogue of capsaicin.

In the title compound, C16H15NO3, the five-membered 1,3-dioxole ring is in an envelope conformation with the methyl-ene C atom as the flap atom [lying 0.202 (3) Å out of the plane formed by the other four atoms]. The benzene ring makes a dihedral angle of 84.65 (4)° with the best least-squares plane through the 1,3-benzodioxole fused-ring system, which substitutes the 2-methoxyphenol moiety in capsaicin. In the crystal, mol-ecules are connected into a zigzag supra-molecular chain along the c-axis direction by N-H⋯O hydrogen bonds. These chains are connected into a layer in the ac plane by C-H⋯π inter-actions.

Related literature

For the biological activity of capsaicin, see: Okamoto et al. (2011 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C16H15NO3

M = 269.29

Monoclinic,

a = 4.9810 (2) Å

b = 26.652 (1) Å

c = 10.0545 (3) Å

β = 92.139 (2)°

V = 1333.84 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 290 K

0.33 × 0.24 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: numerical (SADABS; Sheldrick, 1996 ▶) T min = 0.940, T max = 0.951

4550 measured reflections

2602 independent reflections

1698 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.149

S = 1.03

2602 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: Marvinsketch (Chemaxon, 2010 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813002201/tk5191sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002201/tk5191Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813002201/tk5191Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H15NO3	F(000) = 568
Mr = 269.29	Dx = 1.341 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5124 reflections
a = 4.9810 (2) Å	θ = 3.1–27.5°
b = 26.652 (1) Å	µ = 0.09 mm−1
c = 10.0545 (3) Å	T = 290 K
β = 92.139 (2)°	Prism, colourless
V = 1333.84 (8) Å3	0.33 × 0.24 × 0.16 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2602 independent reflections
Radiation source: fine-focus sealed tube	1698 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 0 pixels mm-1	θmax = 26.0°, θmin = 3.1°
φ and ω scans	h = −6→6
Absorption correction: numerical (SADABS; Sheldrick, 1996)	k = −32→30
Tmin = 0.940, Tmax = 0.951	l = −12→12
4550 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0859P)2 + 0.0674P] where P = (Fo2 + 2Fc2)/3
2602 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
O1	−0.0219 (3)	0.06137 (6)	0.88685 (15)	0.0754 (5)
O2	−0.0295 (3)	0.00662 (6)	0.71012 (17)	0.0797 (5)
O3	0.4080 (3)	0.24272 (5)	0.87268 (12)	0.0634 (4)
N1	0.4208 (3)	0.22490 (6)	0.65426 (14)	0.0496 (4)
H1N1	0.3768	0.2357	0.5702	0.060*
C1	0.1365 (4)	0.08000 (7)	0.78849 (19)	0.0525 (5)
C2	0.1354 (4)	0.04694 (8)	0.6838 (2)	0.0585 (5)
C3	0.2867 (5)	0.05485 (8)	0.5769 (2)	0.0733 (6)
H3	0.2878	0.0322	0.5065	0.088*
C4	0.4407 (4)	0.09851 (8)	0.5771 (2)	0.0649 (6)
H4	0.5483	0.1047	0.5053	0.078*
C5	0.4398 (3)	0.13305 (7)	0.68029 (18)	0.0503 (5)
C6	0.2825 (3)	0.12319 (7)	0.79020 (18)	0.0505 (5)
H6	0.2782	0.1453	0.8616	0.061*
C7	−0.1575 (5)	0.01955 (9)	0.8290 (2)	0.0740 (7)
H7A	−0.3444	0.0279	0.8094	0.089*
H7B	−0.1510	−0.0086	0.8903	0.089*
C8	0.5961 (4)	0.18139 (7)	0.6730 (2)	0.0556 (5)
H8A	0.7042	0.1856	0.7545	0.067*
H8B	0.7169	0.1795	0.5997	0.067*
C9	0.3359 (3)	0.25214 (7)	0.75640 (17)	0.0467 (5)
C10	0.1449 (3)	0.29384 (7)	0.72454 (16)	0.0440 (4)
C11	−0.0105 (4)	0.29652 (7)	0.60682 (19)	0.0547 (5)
H11	0.0065	0.2719	0.5422	0.066*
C12	−0.1888 (4)	0.33522 (8)	0.5853 (2)	0.0620 (6)
H12	−0.2918	0.3360	0.5062	0.074*
C13	−0.2198 (4)	0.37300 (7)	0.6775 (2)	0.0535 (5)
C14	−0.0639 (4)	0.37058 (8)	0.7936 (2)	0.0598 (5)
H14	−0.0779	0.3958	0.8570	0.072*
C15	0.1126 (4)	0.33142 (8)	0.81753 (18)	0.0576 (5)
H15	0.2117	0.3303	0.8977	0.069*
C16	−0.4161 (4)	0.41514 (8)	0.6534 (2)	0.0710 (6)
H16A	−0.3634	0.4345	0.5782	0.106*
H16B	−0.4180	0.4363	0.7307	0.106*
H16C	−0.5924	0.4016	0.6358	0.106*

	U11	U22	U33	U12	U13	U23
O1	0.0884 (10)	0.0677 (10)	0.0708 (10)	−0.0258 (8)	0.0130 (8)	−0.0058 (8)
O2	0.0972 (11)	0.0531 (9)	0.0875 (12)	−0.0117 (8)	−0.0135 (9)	−0.0127 (8)
O3	0.0857 (10)	0.0681 (10)	0.0363 (8)	0.0119 (8)	−0.0003 (6)	0.0050 (7)
N1	0.0628 (9)	0.0497 (9)	0.0366 (8)	0.0042 (7)	0.0049 (7)	0.0051 (7)
C1	0.0582 (11)	0.0506 (12)	0.0482 (11)	0.0027 (9)	−0.0053 (9)	−0.0010 (9)
C2	0.0697 (13)	0.0469 (11)	0.0577 (13)	0.0060 (10)	−0.0126 (10)	−0.0048 (10)
C3	0.1024 (17)	0.0590 (14)	0.0577 (14)	0.0133 (13)	−0.0077 (12)	−0.0177 (11)
C4	0.0821 (14)	0.0646 (14)	0.0486 (12)	0.0180 (11)	0.0101 (10)	−0.0022 (10)
C5	0.0545 (11)	0.0504 (11)	0.0459 (11)	0.0121 (9)	0.0000 (8)	0.0027 (9)
C6	0.0592 (11)	0.0481 (11)	0.0440 (11)	0.0028 (9)	0.0003 (8)	−0.0066 (9)
C7	0.0766 (14)	0.0614 (14)	0.0827 (17)	−0.0153 (12)	−0.0136 (13)	−0.0005 (12)
C8	0.0553 (11)	0.0590 (12)	0.0530 (11)	0.0067 (10)	0.0089 (8)	0.0053 (9)
C9	0.0559 (10)	0.0482 (11)	0.0361 (10)	−0.0035 (8)	0.0040 (8)	0.0042 (8)
C10	0.0507 (10)	0.0452 (10)	0.0365 (9)	−0.0044 (8)	0.0069 (7)	0.0020 (8)
C11	0.0632 (11)	0.0533 (12)	0.0474 (11)	0.0016 (9)	−0.0009 (9)	−0.0075 (9)
C12	0.0610 (12)	0.0660 (14)	0.0582 (13)	0.0061 (11)	−0.0090 (9)	−0.0025 (11)
C13	0.0481 (10)	0.0524 (12)	0.0605 (12)	−0.0026 (9)	0.0088 (9)	0.0040 (10)
C14	0.0707 (13)	0.0547 (13)	0.0544 (12)	0.0039 (10)	0.0093 (10)	−0.0095 (10)
C15	0.0712 (13)	0.0598 (13)	0.0417 (11)	0.0020 (10)	−0.0008 (9)	−0.0037 (9)
C16	0.0593 (13)	0.0664 (14)	0.0879 (17)	0.0101 (11)	0.0121 (11)	0.0065 (12)

O1—C1	1.380 (2)	C7—H7B	0.9700
O1—C7	1.417 (3)	C8—H8A	0.9700
O2—C2	1.384 (2)	C8—H8B	0.9700
O2—C7	1.418 (3)	C9—C10	1.490 (3)
O3—C9	1.2358 (19)	C10—C15	1.384 (3)
N1—C9	1.339 (2)	C10—C11	1.392 (3)
N1—C8	1.459 (2)	C11—C12	1.373 (3)
N1—H1N1	0.9124	C11—H11	0.9300
C1—C6	1.361 (3)	C12—C13	1.382 (3)
C1—C2	1.372 (3)	C12—H12	0.9300
C2—C3	1.352 (3)	C13—C14	1.380 (3)
C3—C4	1.394 (3)	C13—C16	1.503 (3)
C3—H3	0.9300	C14—C15	1.380 (3)
C4—C5	1.387 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.403 (3)	C16—H16A	0.9600
C5—C8	1.508 (3)	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
C7—H7A	0.9700
C1—O1—C7	105.39 (16)	C5—C8—H8A	109.2
C2—O2—C7	105.13 (16)	N1—C8—H8B	109.2
C9—N1—C8	122.43 (15)	C5—C8—H8B	109.2
C9—N1—H1N1	117.9	H8A—C8—H8B	107.9
C8—N1—H1N1	119.5	O3—C9—N1	121.77 (17)
C6—C1—C2	122.7 (2)	O3—C9—C10	121.03 (16)
C6—C1—O1	127.92 (18)	N1—C9—C10	117.19 (15)
C2—C1—O1	109.40 (18)	C15—C10—C11	117.55 (17)
C3—C2—C1	121.5 (2)	C15—C10—C9	118.96 (16)
C3—C2—O2	128.7 (2)	C11—C10—C9	123.47 (17)
C1—C2—O2	109.73 (19)	C12—C11—C10	120.57 (18)
C2—C3—C4	116.89 (19)	C12—C11—H11	119.7
C2—C3—H3	121.6	C10—C11—H11	119.7
C4—C3—H3	121.6	C11—C12—C13	121.98 (18)
C5—C4—C3	122.5 (2)	C11—C12—H12	119.0
C5—C4—H4	118.7	C13—C12—H12	119.0
C3—C4—H4	118.7	C14—C13—C12	117.42 (18)
C4—C5—C6	118.83 (19)	C14—C13—C16	120.94 (19)
C4—C5—C8	120.96 (17)	C12—C13—C16	121.64 (18)
C6—C5—C8	120.17 (17)	C13—C14—C15	121.17 (18)
C1—C6—C5	117.52 (17)	C13—C14—H14	119.4
C1—C6—H6	121.2	C15—C14—H14	119.4
C5—C6—H6	121.2	C14—C15—C10	121.30 (17)
O1—C7—O2	108.35 (18)	C14—C15—H15	119.4
O1—C7—H7A	110.0	C10—C15—H15	119.4
O2—C7—H7A	110.0	C13—C16—H16A	109.5
O1—C7—H7B	110.0	C13—C16—H16B	109.5
O2—C7—H7B	110.0	H16A—C16—H16B	109.5
H7A—C7—H7B	108.4	C13—C16—H16C	109.5
N1—C8—C5	112.19 (14)	H16A—C16—H16C	109.5
N1—C8—H8A	109.2	H16B—C16—H16C	109.5
C7—O1—C1—C6	172.16 (19)	C9—N1—C8—C5	93.3 (2)
C7—O1—C1—C2	−9.7 (2)	C4—C5—C8—N1	108.75 (19)
C6—C1—C2—C3	1.8 (3)	C6—C5—C8—N1	−68.9 (2)
O1—C1—C2—C3	−176.41 (17)	C8—N1—C9—O3	2.1 (3)
C6—C1—C2—O2	179.79 (16)	C8—N1—C9—C10	−176.54 (15)
O1—C1—C2—O2	1.6 (2)	O3—C9—C10—C15	20.0 (3)
C7—O2—C2—C3	−174.9 (2)	N1—C9—C10—C15	−161.38 (17)
C7—O2—C2—C1	7.3 (2)	O3—C9—C10—C11	−158.13 (18)
C1—C2—C3—C4	−0.9 (3)	N1—C9—C10—C11	20.5 (3)
O2—C2—C3—C4	−178.44 (19)	C15—C10—C11—C12	−0.1 (3)
C2—C3—C4—C5	−0.7 (3)	C9—C10—C11—C12	178.03 (17)
C3—C4—C5—C6	1.5 (3)	C10—C11—C12—C13	0.6 (3)
C3—C4—C5—C8	−176.20 (18)	C11—C12—C13—C14	0.0 (3)
C2—C1—C6—C5	−1.0 (3)	C11—C12—C13—C16	−179.77 (18)
O1—C1—C6—C5	176.87 (17)	C12—C13—C14—C15	−1.1 (3)
C4—C5—C6—C1	−0.6 (3)	C16—C13—C14—C15	178.62 (18)
C8—C5—C6—C1	177.12 (16)	C13—C14—C15—C10	1.7 (3)
C1—O1—C7—O2	14.2 (2)	C11—C10—C15—C14	−1.1 (3)
C2—O2—C7—O1	−13.3 (2)	C9—C10—C15—C14	−179.27 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3i	0.91	2.08	2.958 (2)	162
C7—H7A···Cg1	0.97	2.74	3.603 (3)	149
C16—H16C···Cg2	0.96	2.96	3.829 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3i	0.91	2.08	2.958 (2)	162
C7—H7A⋯Cg1	0.97	2.74	3.603 (3)	149
C16—H16C⋯Cg2	0.96	2.96	3.829 (2)	151

Symmetry code: (i) .