Cytenamide-butyric acid (1/1).

Cytenamide forms a 1:1 solvate with butyric acid [systematic name: 5H-dibenzo[a,d]cyclo-hepta-triene-5-carboxamide-butanoic acid (1/1)], C(16)H(13)NO·C(4)H(8)O(2). The title compound crystallizes with one mol-ecule of cytenamide and one of butyric acid in the asymmetric unit; these mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds to form an R(2) (2)(8) heterodimer motif. Pairs of adjacent motifs are further connected via N-H⋯O inter-actions to form a discrete centrosymmetric assembly.

Related literature

For details on experimental methods used to obtain the title solvate, see: Davis et al. (1964 ▶); Florence et al. (2003 ▶); Florence, Johnston, Fernandes et al. (2006 ▶). For literature on cytenamide and related mol­ecules, see: Florence, Bedford et al. (2008 ▶); Cyr et al. (1987 ▶); Fleischman et al. (2003 ▶); Florence, Johnston, Price et al. (2006 ▶); Florence, Leech et al. (2006 ▶); Bandoli et al. (1992 ▶); Harrison et al. (2006 ▶); Leech et al. (2007 ▶); Florence, Shankland et al. (2008 ▶). For other related literature, see: Etter (1990 ▶) ; Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C16H13NO·C4H8O2

M = 323.39

Monoclinic,

a = 5.9351 (2) Å

b = 16.3595 (5) Å

c = 17.6738 (4) Å

β = 98.046 (2)°

V = 1699.15 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 160 K

0.35 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.91, T max = 0.99

18979 measured reflections

4069 independent reflections

2928 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.088

S = 0.95

4069 reflections

226 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED and SORTAV (Blessing, 1997 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶) and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018059/gk2147sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018059/gk2147Isup2.hkl

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

C16H13NO·C4H8O2	F000 = 688
Mr = 323.39	Dx = 1.264 Mg m−3
Monoclinic, P21/n	Melting point: 216.2 K
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71073 Å
a = 5.9351 (2) Å	Cell parameters from 6486 reflections
b = 16.3595 (5) Å	θ = 3–29º
c = 17.6738 (4) Å	µ = 0.09 mm−1
β = 98.046 (2)º	T = 160 K
V = 1699.15 (9) Å3	Block, colourless
Z = 4	0.35 × 0.15 × 0.12 mm

Oxford Diffraction Gemini diffractometer	4069 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2928 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
Detector resolution: 15.9745 pixels mm-1	θmax = 28.7º
T = 160 K	θmin = 2.6º
ω scans	h = −7→7
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	k = 0→21
Tmin = 0.91, Tmax = 0.99	l = 0→23
18979 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: geom+difmap
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.03P)2 + 0.5P], where P = [max(Fo2,0) + 2Fc2]/3
S = 0.95	(Δ/σ)max = 0.001
4069 reflections	Δρmax = 0.38 e Å−3
226 parameters	Δρmin = −0.27 e Å−3
3 restraints	Extinction correction: none

	x	y	z	Uiso*/Ueq
C1	0.3604 (2)	0.32253 (7)	0.41898 (7)	0.0261
C2	0.1718 (2)	0.36489 (8)	0.38294 (7)	0.0323
C3	0.1256 (2)	0.36854 (9)	0.30423 (8)	0.0391
C4	0.2687 (2)	0.33058 (9)	0.25996 (7)	0.0392
C5	0.4591 (2)	0.28990 (8)	0.29445 (7)	0.0344
C6	0.5061 (2)	0.28359 (7)	0.37441 (7)	0.0279
C7	0.6996 (2)	0.23388 (8)	0.40716 (7)	0.0304
C8	0.7115 (2)	0.18488 (8)	0.46816 (7)	0.0301
C9	0.5383 (2)	0.17092 (8)	0.51782 (6)	0.0269
C10	0.5251 (2)	0.09343 (8)	0.55037 (7)	0.0341
C11	0.3603 (2)	0.07491 (9)	0.59538 (8)	0.0398
C12	0.2069 (2)	0.13407 (9)	0.61005 (8)	0.0389
C13	0.2205 (2)	0.21186 (8)	0.58012 (7)	0.0321
C14	0.3844 (2)	0.23123 (7)	0.53434 (6)	0.0258
C15	0.4034 (2)	0.31760 (7)	0.50530 (6)	0.0257
C16	0.6242 (2)	0.35710 (7)	0.54306 (7)	0.0276
C17	0.3158 (3)	0.57421 (11)	0.16558 (9)	0.0568
C18	0.5184 (3)	0.60108 (10)	0.22080 (8)	0.0455
C19	0.5957 (2)	0.53835 (9)	0.28103 (8)	0.0371
C20	0.8040 (2)	0.56040 (8)	0.33497 (7)	0.0295
O1	0.70946 (16)	0.33413 (6)	0.60746 (5)	0.0369
O2	0.84351 (15)	0.53413 (6)	0.39986 (5)	0.0346
N1	0.7091 (2)	0.41860 (7)	0.50777 (6)	0.0335
O3	0.94149 (17)	0.61035 (6)	0.30567 (5)	0.0435
H151	0.2828	0.3488	0.5249	0.0293*
H21	0.0713	0.3916	0.4145	0.0377*
H81	0.8456	0.1498	0.4786	0.0333*
H71	0.8293	0.2332	0.3790	0.0372*
H191	0.4766	0.5266	0.3115	0.0486*
H192	0.6295	0.4889	0.2564	0.0473*
H131	0.1155	0.2536	0.5914	0.0383*
H101	0.6291	0.0526	0.5389	0.0392*
H41	0.2338	0.3317	0.2057	0.0465*
H121	0.0935	0.1222	0.6419	0.0464*
H51	0.5637	0.2636	0.2641	0.0395*
H111	0.3507	0.0214	0.6150	0.0470*
H182	0.4770	0.6515	0.2459	0.0609*
H181	0.6503	0.6120	0.1946	0.0611*
H31	−0.0099	0.3971	0.2794	0.0463*
H172	0.2712	0.6162	0.1279	0.0868*
H173	0.1858	0.5625	0.1933	0.0867*
H171	0.3504	0.5240	0.1402	0.0875*
H12	0.834 (2)	0.4432 (9)	0.5320 (8)	0.0446*
H11	0.652 (2)	0.4352 (9)	0.4630 (8)	0.0433*
H311	1.058 (3)	0.6243 (11)	0.3395 (9)	0.0689*

	U11	U22	U33	U12	U13	U23
C1	0.0283 (6)	0.0234 (6)	0.0265 (6)	−0.0013 (5)	0.0032 (5)	−0.0008 (5)
C2	0.0315 (7)	0.0305 (7)	0.0348 (7)	0.0030 (5)	0.0040 (5)	0.0027 (5)
C3	0.0366 (8)	0.0396 (8)	0.0383 (7)	0.0032 (6)	−0.0041 (6)	0.0075 (6)
C4	0.0476 (8)	0.0422 (8)	0.0259 (6)	−0.0032 (7)	−0.0010 (6)	0.0030 (6)
C5	0.0414 (8)	0.0345 (8)	0.0279 (6)	−0.0020 (6)	0.0075 (6)	−0.0025 (5)
C6	0.0297 (6)	0.0258 (7)	0.0279 (6)	−0.0019 (5)	0.0031 (5)	−0.0021 (5)
C7	0.0287 (6)	0.0318 (7)	0.0315 (6)	0.0018 (5)	0.0065 (5)	−0.0068 (5)
C8	0.0270 (6)	0.0295 (7)	0.0321 (6)	0.0056 (5)	−0.0016 (5)	−0.0067 (5)
C9	0.0273 (6)	0.0284 (7)	0.0227 (6)	−0.0004 (5)	−0.0051 (5)	−0.0026 (5)
C10	0.0388 (7)	0.0291 (7)	0.0313 (6)	0.0021 (6)	−0.0057 (6)	−0.0015 (5)
C11	0.0507 (9)	0.0310 (8)	0.0347 (7)	−0.0078 (6)	−0.0051 (6)	0.0073 (6)
C12	0.0384 (8)	0.0448 (9)	0.0327 (7)	−0.0111 (7)	0.0021 (6)	0.0063 (6)
C13	0.0298 (7)	0.0379 (8)	0.0275 (6)	−0.0022 (6)	0.0010 (5)	−0.0008 (5)
C14	0.0264 (6)	0.0277 (7)	0.0215 (5)	−0.0016 (5)	−0.0027 (5)	−0.0024 (5)
C15	0.0270 (6)	0.0256 (7)	0.0252 (6)	0.0034 (5)	0.0055 (5)	−0.0028 (5)
C16	0.0334 (7)	0.0245 (6)	0.0252 (6)	0.0009 (5)	0.0059 (5)	−0.0041 (5)
C17	0.0518 (10)	0.0666 (12)	0.0470 (9)	0.0033 (8)	−0.0109 (7)	−0.0040 (8)
C18	0.0467 (9)	0.0430 (9)	0.0435 (8)	−0.0033 (7)	−0.0052 (7)	0.0042 (7)
C19	0.0398 (8)	0.0347 (8)	0.0361 (7)	−0.0062 (6)	0.0026 (6)	−0.0017 (6)
C20	0.0366 (7)	0.0246 (7)	0.0279 (6)	−0.0004 (5)	0.0066 (5)	−0.0014 (5)
O2	0.0421 (5)	0.0326 (5)	0.0290 (5)	−0.0029 (4)	0.0045 (4)	0.0035 (4)
N1	0.0402 (7)	0.0304 (6)	0.0291 (5)	−0.0056 (5)	0.0024 (5)	0.0018 (5)
O3	0.0457 (6)	0.0529 (7)	0.0297 (5)	−0.0205 (5)	−0.0027 (4)	0.0077 (4)
O1	0.0441 (5)	0.0373 (5)	0.0271 (4)	−0.0124 (4)	−0.0027 (4)	0.0021 (4)

C1—C2	1.3924 (17)	C12—H121	0.956
C1—C6	1.4018 (17)	C13—C14	1.3860 (17)
C1—C15	1.5133 (15)	C13—H131	0.965
C2—C3	1.3811 (18)	C14—C15	1.5129 (17)
C2—H21	0.975	C15—C16	1.5282 (17)
C3—C4	1.380 (2)	C15—H151	0.981
C3—H31	0.980	C16—N1	1.3204 (16)
C4—C5	1.378 (2)	C16—O1	1.2376 (14)
C4—H41	0.952	C17—C18	1.504 (2)
C5—C6	1.4054 (17)	C17—H172	0.968
C5—H51	0.976	C17—H173	0.988
C6—C7	1.4591 (17)	C17—H171	0.971
C7—C8	1.3373 (18)	C18—C19	1.5034 (19)
C7—H71	0.974	C18—H182	0.984
C8—C9	1.4601 (18)	C18—H181	0.980
C8—H81	0.977	C19—C20	1.4956 (18)
C9—C10	1.3988 (18)	C19—H191	0.967
C9—C14	1.4026 (17)	C19—H192	0.954
C10—C11	1.3778 (19)	C20—O2	1.2165 (14)
C10—H101	0.950	C20—O3	1.3114 (15)
C11—C12	1.378 (2)	N1—H12	0.899 (14)
C11—H111	0.946	N1—H11	0.860 (14)
C12—C13	1.3848 (19)	O3—H311	0.880 (14)
C2—C1—C6	119.25 (11)	C14—C13—H131	119.0
C2—C1—C15	119.95 (11)	C9—C14—C13	119.42 (12)
C6—C1—C15	120.79 (10)	C9—C14—C15	120.31 (11)
C1—C2—C3	121.06 (12)	C13—C14—C15	120.22 (11)
C1—C2—H21	118.6	C1—C15—C14	112.44 (10)
C3—C2—H21	120.4	C1—C15—C16	115.54 (10)
C2—C3—C4	120.03 (13)	C14—C15—C16	110.29 (10)
C2—C3—H31	120.5	C1—C15—H151	107.5
C4—C3—H31	119.5	C14—C15—H151	105.8
C3—C4—C5	119.87 (12)	C16—C15—H151	104.4
C3—C4—H41	119.9	C15—C16—N1	118.47 (11)
C5—C4—H41	120.2	C15—C16—O1	119.24 (11)
C4—C5—C6	121.01 (12)	N1—C16—O1	122.14 (12)
C4—C5—H51	121.0	C18—C17—H172	110.8
C6—C5—H51	118.0	C18—C17—H173	110.1
C5—C6—C1	118.72 (11)	H172—C17—H173	108.7
C5—C6—C7	118.30 (11)	C18—C17—H171	110.2
C1—C6—C7	122.92 (11)	H172—C17—H171	109.7
C6—C7—C8	127.14 (12)	H173—C17—H171	107.2
C6—C7—H71	116.0	C17—C18—C19	113.39 (13)
C8—C7—H71	116.7	C17—C18—H182	108.1
C7—C8—C9	128.04 (12)	C19—C18—H182	108.9
C7—C8—H81	117.0	C17—C18—H181	111.4
C9—C8—H81	114.7	C19—C18—H181	105.9
C8—C9—C10	118.27 (11)	H182—C18—H181	109.0
C8—C9—C14	123.29 (11)	C18—C19—C20	115.46 (11)
C10—C9—C14	118.45 (11)	C18—C19—H191	110.9
C9—C10—C11	121.46 (13)	C20—C19—H191	107.3
C9—C10—H101	118.2	C18—C19—H192	108.6
C11—C10—H101	120.2	C20—C19—H192	106.7
C10—C11—C12	119.67 (13)	H191—C19—H192	107.6
C10—C11—H111	120.0	C19—C20—O2	123.28 (12)
C12—C11—H111	120.3	C19—C20—O3	113.77 (11)
C11—C12—C13	119.87 (13)	O2—C20—O3	122.95 (12)
C11—C12—H121	120.4	C16—N1—H12	117.5 (10)
C13—C12—H121	119.7	C16—N1—H11	123.2 (10)
C12—C13—C14	121.09 (13)	H12—N1—H11	119.3 (14)
C12—C13—H131	119.9	C20—O3—H311	111.5 (12)
C6—C1—C2—C3	0.48 (19)	C14—C9—C10—C11	2.43 (18)
C15—C1—C2—C3	−178.34 (12)	C8—C9—C14—C13	177.89 (11)
C2—C1—C6—C5	1.17 (17)	C8—C9—C14—C15	−4.73 (17)
C2—C1—C6—C7	−176.25 (11)	C10—C9—C14—C13	−1.96 (17)
C15—C1—C6—C5	180.00 (12)	C10—C9—C14—C15	175.42 (10)
C15—C1—C6—C7	2.57 (18)	C9—C10—C11—C12	−1.2 (2)
C2—C1—C15—C14	114.81 (12)	C10—C11—C12—C13	−0.6 (2)
C2—C1—C15—C16	−117.37 (12)	C11—C12—C13—C14	1.0 (2)
C6—C1—C15—C14	−63.99 (14)	C12—C13—C14—C9	0.28 (18)
C6—C1—C15—C16	63.83 (14)	C12—C13—C14—C15	−177.10 (11)
C1—C2—C3—C4	−0.7 (2)	C9—C14—C15—C1	64.61 (14)
C2—C3—C4—C5	−0.8 (2)	C9—C14—C15—C16	−65.93 (13)
C3—C4—C5—C6	2.5 (2)	C13—C14—C15—C1	−118.03 (12)
C4—C5—C6—C1	−2.67 (18)	C13—C14—C15—C16	111.43 (12)
C4—C5—C6—C7	174.87 (12)	C1—C15—C16—O1	−156.56 (11)
C1—C6—C7—C8	36.0 (2)	C1—C15—C16—N1	27.97 (15)
C5—C6—C7—C8	−141.46 (14)	C14—C15—C16—O1	−27.68 (15)
C6—C7—C8—C9	−1.9 (2)	C14—C15—C16—N1	156.85 (11)
C7—C8—C9—C10	147.22 (13)	C17—C18—C19—C20	177.01 (13)
C7—C8—C9—C14	−32.6 (2)	C18—C19—C20—O2	152.97 (13)
C8—C9—C10—C11	−177.43 (12)	C18—C19—C20—O3	−27.50 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O2	0.860 (14)	2.348 (14)	2.8761 (15)	120.0 (10)
N1—H12···O2i	0.898 (13)	2.146 (13)	3.0167 (15)	163.2 (13)
O3—H311···O1i	0.879 (17)	1.698 (17)	2.5658 (13)	168.8 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯O2	0.860 (14)	2.348 (14)	2.8761 (15)	120.0 (10)
N1—H12⋯O2i	0.898 (13)	2.146 (13)	3.0167 (15)	163.2 (13)
O3—H311⋯O1i	0.879 (17)	1.698 (17)	2.5658 (13)	168.8 (16)

Symmetry code: (i) .