N-[4-(7-Meth-oxy-2-oxo-2H-chromen-8-yl)-2-methyl-butan-2-yl]propionamide.

In the crystal structure of the title osthol derivative, C(18)H(23)NO(4), mol-ecules are linked by N-H⋯O hydrogen bonds into an infinite chain running parallel to the c axis. The CH(3)CH(2)- atoms of the propionamide group are disordered over two sets of sites with refined occupancies of 0.689 (12) and 0.311 (12).

Related literature

For the synthesis of the title compound, see: Ritter & Minieri (1948 ▶). For the crystal structure of the parent compound osthol [systematic name: 7-meth­oxy-8-(3-methyl­but-2-en­yl)-2-chromenone], see: Borowiak & Wolska (1989 ▶). For biological applications of osthol and its derivatives, see: Liu et al. (1998 ▶, 2005 ▶); Okamoto et al. (2007 ▶); Huang et al. (1996 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H23NO4

M = 317.37

Monoclinic,

a = 11.3555 (11) Å

b = 15.5452 (15) Å

c = 9.7642 (10) Å

β = 95.617 (2)°

V = 1715.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 273 K

0.22 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.983

16205 measured reflections

3019 independent reflections

2537 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.136

S = 1.01

3019 reflections

234 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033149/kj2174sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033149/kj2174Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033149/kj2174Isup3.cml

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

C18H23NO4	F(000) = 680
Mr = 317.37	Dx = 1.229 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6500 reflections
a = 11.3555 (11) Å	θ = 1.8–28.0°
b = 15.5452 (15) Å	µ = 0.09 mm−1
c = 9.7642 (10) Å	T = 273 K
β = 95.617 (2)°	Rod, yellow
V = 1715.3 (3) Å3	0.22 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	3019 independent reflections
Radiation source: fine-focus sealed tube	2537 reflections with I > 2σ(I)
graphite	Rint = 0.019
ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.981, Tmax = 0.983	k = −18→18
16205 measured reflections	l = −11→11

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0736P)2 + 0.2891P] where P = (Fo2 + 2Fc2)/3
3019 reflections	(Δ/σ)max = 0.007
234 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.50266 (14)	0.38430 (10)	0.50309 (19)	0.0668 (4)
C2	0.40239 (14)	0.37094 (10)	0.41396 (19)	0.0670 (4)
C3	0.49068 (17)	0.37660 (11)	0.6435 (2)	0.0781 (5)
C4	0.29202 (14)	0.35187 (11)	0.4587 (2)	0.0768 (5)
C5	0.3822 (2)	0.35721 (13)	0.6915 (2)	0.0911 (6)
H5	0.3758	0.3524	0.7854	0.109*
C6	0.28580 (19)	0.34547 (12)	0.5993 (3)	0.0904 (6)
H6	0.2134	0.3327	0.6317	0.108*
C7	0.80188 (12)	0.36325 (10)	0.33969 (14)	0.0560 (4)
C8	0.69360 (12)	0.33546 (10)	0.41152 (16)	0.0604 (4)
H8A	0.6452	0.2972	0.3510	0.072*
H8B	0.7203	0.3035	0.4941	0.072*
C9	0.61786 (13)	0.41122 (10)	0.4504 (2)	0.0728 (5)
H9A	0.6629	0.4451	0.5207	0.087*
H9B	0.6006	0.4477	0.3703	0.087*
C10	0.5809 (3)	0.4006 (2)	0.8721 (3)	0.1361 (10)
H10A	0.5271	0.4466	0.8866	0.204*
H10B	0.6573	0.4135	0.9186	0.204*
H10C	0.5518	0.3480	0.9078	0.204*
C11	0.19411 (17)	0.34260 (14)	0.3580 (3)	0.0988 (7)
H11	0.1200	0.3300	0.3858	0.119*
C12	0.3184 (2)	0.37156 (14)	0.1768 (3)	0.0996 (6)
C13	0.76340 (19)	0.40583 (15)	0.20249 (19)	0.0922 (6)
H13A	0.8313	0.4153	0.1532	0.138*
H13B	0.7262	0.4599	0.2182	0.138*
H13C	0.7083	0.3692	0.1494	0.138*
C14	0.88212 (14)	0.42377 (11)	0.42793 (19)	0.0723 (4)
H14A	0.9062	0.3968	0.5146	0.108*
H14B	0.8402	0.4760	0.4433	0.108*
H14C	0.9507	0.4368	0.3816	0.108*
C15	0.2058 (2)	0.35152 (16)	0.2258 (3)	0.1089 (8)
H15	0.1397	0.3447	0.1625	0.131*
C16	0.92284 (12)	0.22894 (10)	0.39309 (13)	0.0563 (4)
O1	0.41391 (11)	0.37975 (8)	0.27610 (13)	0.0811 (4)
O3	0.3391 (2)	0.38160 (14)	0.0601 (2)	0.1400 (7)
O2	0.59071 (14)	0.39123 (11)	0.72856 (16)	0.1065 (5)
O4	0.92528 (10)	0.23463 (8)	0.51856 (9)	0.0719 (3)
N1	0.86888 (10)	0.28549 (8)	0.30587 (12)	0.0572 (3)
H1N	0.8755 (14)	0.2776 (11)	0.2195 (19)	0.069 (5)*
C18A	0.9166 (6)	0.0731 (2)	0.3336 (6)	0.106 (2)	0.689 (12)
H18A	0.9576	0.0272	0.2928	0.159*	0.689 (12)
H18B	0.8408	0.0816	0.2826	0.159*	0.689 (12)
H18C	0.9056	0.0586	0.4271	0.159*	0.689 (12)
C17A	0.9890 (10)	0.1556 (8)	0.3311 (7)	0.0664 (16)	0.689 (12)
H17A	1.0653	0.1475	0.3833	0.080*	0.689 (12)
H17B	1.0023	0.1696	0.2370	0.080*	0.689 (12)
C17B	0.962 (2)	0.1530 (19)	0.316 (2)	0.094 (7)	0.311 (12)
H17C	0.8942	0.1293	0.2609	0.112*	0.311 (12)
H17D	1.0179	0.1725	0.2533	0.112*	0.311 (12)
C18B	1.013 (3)	0.0901 (11)	0.3947 (12)	0.217 (12)	0.311 (12)
H18D	1.0485	0.0490	0.3376	0.326*	0.311 (12)
H18E	0.9547	0.0620	0.4433	0.326*	0.311 (12)
H18F	1.0734	0.1142	0.4596	0.326*	0.311 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0561 (9)	0.0560 (9)	0.0928 (11)	0.0061 (7)	0.0297 (8)	0.0001 (7)
C2	0.0595 (9)	0.0552 (9)	0.0911 (11)	0.0046 (7)	0.0312 (8)	−0.0009 (8)
C3	0.0759 (11)	0.0680 (10)	0.0935 (13)	0.0148 (8)	0.0243 (10)	0.0045 (9)
C4	0.0552 (9)	0.0590 (9)	0.1213 (15)	0.0010 (7)	0.0339 (9)	−0.0018 (9)
C5	0.0998 (15)	0.0776 (12)	0.1041 (15)	0.0141 (11)	0.0519 (13)	0.0157 (10)
C6	0.0769 (12)	0.0717 (11)	0.1323 (18)	0.0023 (9)	0.0591 (13)	0.0095 (11)
C7	0.0524 (7)	0.0659 (9)	0.0521 (8)	0.0066 (6)	0.0162 (6)	0.0041 (6)
C8	0.0505 (8)	0.0604 (9)	0.0728 (9)	−0.0003 (6)	0.0185 (6)	−0.0053 (7)
C9	0.0539 (8)	0.0630 (9)	0.1058 (13)	−0.0010 (7)	0.0306 (8)	−0.0077 (9)
C10	0.178 (3)	0.138 (2)	0.0892 (16)	0.026 (2)	0.0005 (17)	0.0000 (15)
C11	0.0605 (11)	0.0806 (13)	0.158 (2)	−0.0012 (9)	0.0242 (13)	−0.0194 (14)
C12	0.1143 (18)	0.0812 (14)	0.1025 (17)	0.0039 (12)	0.0068 (14)	−0.0089 (11)
C13	0.1019 (14)	0.1103 (15)	0.0671 (10)	0.0359 (12)	0.0217 (9)	0.0226 (10)
C14	0.0611 (9)	0.0663 (10)	0.0919 (12)	−0.0056 (7)	0.0205 (8)	−0.0035 (8)
C15	0.0800 (14)	0.0943 (16)	0.149 (2)	0.0048 (11)	−0.0057 (15)	−0.0210 (15)
C16	0.0574 (8)	0.0676 (9)	0.0459 (7)	0.0040 (7)	0.0158 (6)	0.0000 (6)
O1	0.0775 (8)	0.0793 (8)	0.0902 (9)	−0.0017 (6)	0.0264 (7)	−0.0045 (6)
O3	0.179 (2)	0.1423 (16)	0.0978 (12)	−0.0107 (14)	0.0076 (12)	−0.0032 (11)
O2	0.0973 (11)	0.1188 (12)	0.1031 (11)	0.0189 (9)	0.0086 (8)	−0.0041 (9)
O4	0.0924 (8)	0.0822 (8)	0.0434 (6)	0.0163 (6)	0.0180 (5)	0.0032 (5)
N1	0.0585 (7)	0.0747 (8)	0.0404 (6)	0.0101 (6)	0.0143 (5)	−0.0015 (5)
C18A	0.156 (4)	0.071 (2)	0.100 (3)	0.010 (2)	0.064 (3)	−0.0056 (19)
C17A	0.065 (3)	0.089 (3)	0.0471 (18)	0.026 (2)	0.017 (2)	0.0018 (19)
C17B	0.106 (16)	0.082 (8)	0.093 (10)	0.020 (9)	0.012 (7)	−0.009 (6)
C18B	0.37 (3)	0.181 (13)	0.092 (7)	0.187 (18)	−0.003 (11)	−0.013 (7)

C1—C2	1.379 (3)	C12—O3	1.196 (3)
C1—C3	1.396 (3)	C12—O1	1.388 (3)
C1—C9	1.511 (2)	C12—C15	1.443 (4)
C2—O1	1.372 (2)	C13—H13A	0.9600
C2—C4	1.399 (2)	C13—H13B	0.9600
C3—O2	1.359 (2)	C13—H13C	0.9600
C3—C5	1.393 (3)	C14—H14A	0.9600
C4—C6	1.385 (3)	C14—H14B	0.9600
C4—C11	1.418 (3)	C14—H14C	0.9600
C5—C6	1.360 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—O4	1.2260 (16)
C6—H6	0.9300	C16—N1	1.3310 (19)
C7—N1	1.4827 (19)	C16—C17B	1.49 (3)
C7—C14	1.518 (2)	C16—C17A	1.523 (10)
C7—C13	1.520 (2)	N1—H1N	0.863 (18)
C7—C8	1.5359 (19)	C18A—C17A	1.525 (13)
C8—C9	1.528 (2)	C18A—H18A	0.9600
C8—H8A	0.9700	C18A—H18B	0.9600
C8—H8B	0.9700	C18A—H18C	0.9600
C9—H9A	0.9700	C17A—H17A	0.9700
C9—H9B	0.9700	C17A—H17B	0.9700
C10—O2	1.424 (3)	C17B—C18B	1.34 (3)
C10—H10A	0.9600	C17B—H17C	0.9700
C10—H10B	0.9600	C17B—H17D	0.9700
C10—H10C	0.9600	C18B—H18D	0.9600
C11—C15	1.318 (3)	C18B—H18E	0.9600
C11—H11	0.9300	C18B—H18F	0.9600
C2—C1—C3	116.94 (15)	C7—C13—H13B	109.5
C2—C1—C9	121.03 (16)	H13A—C13—H13B	109.5
C3—C1—C9	121.94 (17)	C7—C13—H13C	109.5
O1—C2—C1	116.87 (14)	H13A—C13—H13C	109.5
O1—C2—C4	120.14 (17)	H13B—C13—H13C	109.5
C1—C2—C4	122.96 (17)	C7—C14—H14A	109.5
O2—C3—C5	123.00 (19)	C7—C14—H14B	109.5
O2—C3—C1	115.46 (16)	H14A—C14—H14B	109.5
C5—C3—C1	121.5 (2)	C7—C14—H14C	109.5
C6—C4—C2	117.33 (18)	H14A—C14—H14C	109.5
C6—C4—C11	124.59 (18)	H14B—C14—H14C	109.5
C2—C4—C11	118.1 (2)	C11—C15—C12	121.7 (2)
C6—C5—C3	119.19 (19)	C11—C15—H15	119.2
C6—C5—H5	120.4	C12—C15—H15	119.2
C3—C5—H5	120.4	O4—C16—N1	123.76 (13)
C5—C6—C4	122.04 (16)	O4—C16—C17B	125.6 (9)
C5—C6—H6	119.0	N1—C16—C17B	110.0 (10)
C4—C6—H6	119.0	O4—C16—C17A	119.2 (3)
N1—C7—C14	109.82 (12)	N1—C16—C17A	117.0 (3)
N1—C7—C13	105.56 (12)	C17B—C16—C17A	12.4 (15)
C14—C7—C13	109.59 (15)	C2—O1—C12	122.22 (16)
N1—C7—C8	108.88 (12)	C3—O2—C10	118.5 (2)
C14—C7—C8	112.21 (12)	C16—N1—C7	127.60 (11)
C13—C7—C8	110.56 (13)	C16—N1—H1N	116.9 (11)
C9—C8—C7	113.07 (12)	C7—N1—H1N	115.4 (11)
C9—C8—H8A	109.0	C17A—C18A—H18A	109.5
C7—C8—H8A	109.0	C17A—C18A—H18B	109.5
C9—C8—H8B	109.0	H18A—C18A—H18B	109.5
C7—C8—H8B	109.0	C17A—C18A—H18C	109.5
H8A—C8—H8B	107.8	H18A—C18A—H18C	109.5
C1—C9—C8	113.47 (13)	H18B—C18A—H18C	109.5
C1—C9—H9A	108.9	C16—C17A—C18A	109.6 (6)
C8—C9—H9A	108.9	C16—C17A—H17A	109.8
C1—C9—H9B	108.9	C18A—C17A—H17A	109.8
C8—C9—H9B	108.9	C16—C17A—H17B	109.8
H9A—C9—H9B	107.7	C18A—C17A—H17B	109.8
O2—C10—H10A	109.5	H17A—C17A—H17B	108.2
O2—C10—H10B	109.5	C18B—C17B—C16	115.0 (16)
H10A—C10—H10B	109.5	C18B—C17B—H17C	108.5
O2—C10—H10C	109.5	C16—C17B—H17C	108.5
H10A—C10—H10C	109.5	C18B—C17B—H17D	108.5
H10B—C10—H10C	109.5	C16—C17B—H17D	108.5
C15—C11—C4	121.4 (2)	H17C—C17B—H17D	107.5
C15—C11—H11	119.3	C17B—C18B—H18D	109.5
C4—C11—H11	119.3	C17B—C18B—H18E	109.5
O3—C12—O1	116.1 (2)	H18D—C18B—H18E	109.5
O3—C12—C15	127.4 (3)	C17B—C18B—H18F	109.5
O1—C12—C15	116.5 (2)	H18D—C18B—H18F	109.5
C7—C13—H13A	109.5	H18E—C18B—H18F	109.5
C3—C1—C2—O1	179.09 (13)	C6—C4—C11—C15	178.4 (2)
C9—C1—C2—O1	2.6 (2)	C2—C4—C11—C15	0.0 (3)
C3—C1—C2—C4	1.0 (2)	C4—C11—C15—C12	−0.3 (4)
C9—C1—C2—C4	−175.40 (14)	O3—C12—C15—C11	−179.5 (2)
C2—C1—C3—O2	−179.19 (14)	O1—C12—C15—C11	0.9 (3)
C9—C1—C3—O2	−2.8 (2)	C1—C2—O1—C12	−177.17 (15)
C2—C1—C3—C5	−0.7 (2)	C4—C2—O1—C12	0.9 (2)
C9—C1—C3—C5	175.75 (16)	O3—C12—O1—C2	179.15 (18)
O1—C2—C4—C6	−178.77 (15)	C15—C12—O1—C2	−1.2 (3)
C1—C2—C4—C6	−0.8 (2)	C5—C3—O2—C10	−10.2 (3)
O1—C2—C4—C11	−0.3 (2)	C1—C3—O2—C10	168.33 (18)
C1—C2—C4—C11	177.66 (16)	O4—C16—N1—C7	−0.9 (2)
O2—C3—C5—C6	178.46 (18)	C17B—C16—N1—C7	170.6 (12)
C1—C3—C5—C6	0.0 (3)	C17A—C16—N1—C7	−178.2 (5)
C3—C5—C6—C4	0.2 (3)	C14—C7—N1—C16	59.89 (19)
C2—C4—C6—C5	0.1 (3)	C13—C7—N1—C16	177.95 (16)
C11—C4—C6—C5	−178.22 (19)	C8—C7—N1—C16	−63.33 (18)
N1—C7—C8—C9	−179.76 (13)	O4—C16—C17A—C18A	78.8 (7)
C14—C7—C8—C9	58.45 (18)	N1—C16—C17A—C18A	−103.7 (5)
C13—C7—C8—C9	−64.23 (19)	C17B—C16—C17A—C18A	−46 (6)
C2—C1—C9—C8	−87.9 (2)	O4—C16—C17B—C18B	−6(3)
C3—C1—C9—C8	95.79 (19)	N1—C16—C17B—C18B	−177 (2)
C7—C8—C9—C1	172.05 (14)	C17A—C16—C17B—C18B	56 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4i	0.87 (2)	2.10 (2)	2.9546 (15)	169.1 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4i	0.87 (2)	2.10 (2)	2.9546 (15)	169.1 (15)

Symmetry code: (i) .