Cytenamide-1,4-dioxane (2/1).

IN THE CRYSTAL STRUCTURE OF THE TITLE COMPOUND [SYSTEMATIC NAME: 5H-dibenzo[a,d]cyclo-hepta-triene-5-carboxamide-1,4-dioxane (2/1)], 2C(16)H(13)NO·C(4)H(8)O(2), the cytenamide mol-ecules form a hydrogen-bonded R(2) (2)(8) dimer. The solvent mol-ecule is located between two adjacent cytenamide dimers and forms N-H⋯O hydrogen bonds with one cytenamide mol-ecule from each dimer.

Related literature

For details on experimental methods used to obtain this form, see: Davis et al. (1964 ▶); Florence et al. (2003 ▶); Florence, Johnston, Fernandes et al. (2006 ▶). For related literature on cytenamide, see: Florence, Bedford et al. (2008 ▶). For literature on related mol­ecules, see: 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 ▶).

Experimental

Crystal data

2C16H13NO·C4H8O2

M = 558.68

Monoclinic,

a = 24.0888 (7) Å

b = 5.6066 (2) Å

c = 21.1050 (6) Å

β = 90.313 (3)°

V = 2850.32 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 160 K

0.48 × 0.09 × 0.03 mm

Data collection

Oxford Diffraction Gemini S diffractometer

Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2007 ▶) T min = 0.84, T max = 1.00 (expected range = 0.838–0.997)

23004 measured reflections

5125 independent reflections

3677 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.121

S = 1.08

5125 reflections

380 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.42 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: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018709/tk2275sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018709/tk2275Isup2.hkl

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

2C16H13NO·C4H8O2	F000 = 1184
Mr = 558.68	Dx = 1.302 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4484 reflections
a = 24.0888 (7) Å	θ = 3–27º
b = 5.6066 (2) Å	µ = 0.09 mm−1
c = 21.1050 (6) Å	T = 160 K
β = 90.313 (3)º	Plate, colourless
V = 2850.32 (15) Å3	0.48 × 0.09 × 0.03 mm
Z = 4

Area diffractometer	5125 independent reflections
Monochromator: graphite	3677 reflections with I > 2σ(I)
Detector resolution: 15.9745 pixels mm-1	Rint = 0.057
T = 160 K	θmax = 25.2º
ω scans	θmin = 2.6º
Absorption correction: multi-scan(ABSPACK; Oxford Diffraction, 2007)	h = −28→28
Tmin = 0.84, Tmax = 1.00	k = 0→6
23004 measured reflections	l = 0→25

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.068	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.03P)2 + 2.31P], where P = [max(Fo2,0) + 2Fc2]/3
wR(F2) = 0.121	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.47 e Å−3
5125 reflections	Δρmin = −0.42 e Å−3
380 parameters	Extinction correction: None
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
C1	0.30658 (11)	0.7244 (5)	0.22235 (12)	0.0230
C2	0.34609 (11)	0.5089 (5)	0.22501 (12)	0.0212
C3	0.38005 (11)	0.4805 (5)	0.16566 (12)	0.0223
C4	0.36884 (12)	0.2923 (5)	0.12509 (12)	0.0258
C5	0.39561 (13)	0.2692 (6)	0.06774 (13)	0.0325
C6	0.43397 (12)	0.4386 (6)	0.04947 (14)	0.0345
C7	0.44599 (12)	0.6265 (6)	0.08979 (13)	0.0319
C8	0.42064 (11)	0.6495 (5)	0.14882 (12)	0.0236
C9	0.43795 (11)	0.8470 (5)	0.18941 (13)	0.0273
C10	0.43627 (11)	0.8646 (5)	0.25275 (13)	0.0278
C11	0.41740 (11)	0.6923 (5)	0.29951 (12)	0.0248
C12	0.43986 (12)	0.7061 (6)	0.36058 (13)	0.0312
C13	0.42709 (13)	0.5401 (6)	0.40640 (14)	0.0363
C14	0.39126 (14)	0.3563 (6)	0.39233 (13)	0.0362
C15	0.36716 (12)	0.3447 (5)	0.33299 (13)	0.0291
C16	0.37863 (11)	0.5125 (5)	0.28643 (12)	0.0225
C17	0.19387 (11)	0.2237 (5)	0.72423 (12)	0.0211
C18	0.15359 (11)	0.0105 (5)	0.72796 (11)	0.0217
C19	0.11962 (11)	0.0120 (5)	0.78837 (12)	0.0227
C20	0.13026 (12)	−0.1573 (5)	0.83494 (12)	0.0281
C21	0.10561 (13)	−0.1443 (6)	0.89365 (13)	0.0342
C22	0.07002 (13)	0.0420 (6)	0.90707 (14)	0.0361
C23	0.05789 (12)	0.2069 (6)	0.86079 (13)	0.0305
C24	0.08117 (11)	0.1940 (5)	0.80018 (12)	0.0241
C25	0.06348 (11)	0.3688 (5)	0.75313 (13)	0.0270
C26	0.06267 (11)	0.3504 (5)	0.68996 (13)	0.0277
C27	0.08061 (11)	0.1544 (5)	0.64959 (12)	0.0235
C28	0.05571 (11)	0.1337 (6)	0.58956 (13)	0.0301
C29	0.06815 (12)	−0.0532 (6)	0.54957 (13)	0.0341
C30	0.10567 (12)	−0.2249 (6)	0.56844 (13)	0.0300
C31	0.13153 (12)	−0.2035 (5)	0.62664 (12)	0.0262
C32	0.12027 (11)	−0.0156 (5)	0.66747 (12)	0.0221
C33	0.24356 (17)	1.1206 (7)	0.52906 (16)	0.0547
C34	0.20870 (16)	1.1411 (8)	0.47152 (17)	0.0612
C35	0.26150 (18)	0.8437 (9)	0.42284 (16)	0.0654
C36	0.29643 (16)	0.8250 (8)	0.47959 (16)	0.0576
O2	0.20878 (8)	0.3034 (4)	0.67272 (9)	0.0319
O1	0.29456 (9)	0.8317 (4)	0.27135 (9)	0.0416
N1	0.28447 (10)	0.7810 (4)	0.16701 (10)	0.0276
O4	0.26727 (11)	0.8892 (5)	0.53470 (11)	0.0601
N2	0.21372 (10)	0.3049 (4)	0.77846 (10)	0.0301
O3	0.23813 (13)	1.0729 (6)	0.41616 (11)	0.0766
H12	0.2929	0.7005	0.1331	0.0337*
H13	0.2388	0.4167	0.7778	0.0346*
H14	0.2014	0.2492	0.8143	0.0341*
H11	0.2604	0.8928	0.1658	0.0335*
H21	0.3220	0.3680	0.2272	0.0227*
H41	0.3422	0.1772	0.1371	0.0304*
H51	0.3877	0.1358	0.0418	0.0373*
H61	0.4516	0.4256	0.0100	0.0391*
H71	0.4724	0.7421	0.0774	0.0366*
H91	0.4521	0.9769	0.1669	0.0320*
H101	0.4495	1.0070	0.2695	0.0308*
H121	0.4646	0.8312	0.3704	0.0366*
H131	0.4420	0.5553	0.4466	0.0428*
H141	0.3833	0.2408	0.4229	0.0431*
H151	0.3430	0.2207	0.3235	0.0324*
H181	0.1771	−0.1295	0.7304	0.0252*
H201	0.1550	−0.2818	0.8256	0.0321*
H211	0.1138	−0.2613	0.9244	0.0401*
H221	0.0540	0.0580	0.9478	0.0424*
H231	0.0330	0.3320	0.8699	0.0339*
H251	0.0491	0.5142	0.7700	0.0313*
H261	0.0473	0.4794	0.6683	0.0327*
H281	0.0308	0.2494	0.5766	0.0346*
H291	0.0505	−0.0629	0.5088	0.0391*
H301	0.1144	−0.3536	0.5422	0.0347*
H311	0.1579	−0.3182	0.6393	0.0303*
H331	0.2732	1.2396	0.5258	0.0635*
H332	0.2202	1.1544	0.5657	0.0653*
H341	0.1959	1.3056	0.4670	0.0711*
H342	0.1775	1.0333	0.4757	0.0712*
H351	0.2822	0.8002	0.3857	0.0752*
H352	0.2310	0.7296	0.4268	0.0756*
H361	0.3290	0.9332	0.4750	0.0676*
H362	0.3100	0.6606	0.4851	0.0684*

	U11	U22	U33	U12	U13	U23
C1	0.0193 (15)	0.0282 (17)	0.0216 (15)	−0.0031 (12)	0.0011 (12)	−0.0002 (13)
C2	0.0250 (16)	0.0174 (14)	0.0214 (14)	−0.0029 (12)	0.0021 (11)	0.0015 (12)
C3	0.0228 (16)	0.0243 (16)	0.0199 (14)	0.0055 (12)	−0.0029 (11)	0.0048 (12)
C4	0.0286 (17)	0.0256 (16)	0.0232 (15)	0.0019 (13)	−0.0001 (12)	0.0003 (13)
C5	0.0371 (19)	0.0352 (19)	0.0250 (16)	0.0071 (15)	−0.0039 (13)	−0.0070 (14)
C6	0.0273 (17)	0.055 (2)	0.0216 (15)	0.0101 (16)	0.0024 (12)	−0.0003 (15)
C7	0.0238 (16)	0.043 (2)	0.0288 (16)	−0.0002 (14)	0.0043 (13)	0.0074 (15)
C8	0.0194 (15)	0.0283 (17)	0.0232 (15)	0.0031 (13)	−0.0003 (11)	0.0045 (13)
C9	0.0250 (16)	0.0251 (17)	0.0317 (17)	−0.0027 (13)	0.0000 (12)	0.0041 (14)
C10	0.0270 (16)	0.0234 (17)	0.0330 (17)	−0.0035 (13)	−0.0029 (13)	−0.0060 (14)
C11	0.0219 (15)	0.0273 (17)	0.0251 (15)	0.0055 (13)	0.0005 (12)	−0.0048 (13)
C12	0.0288 (17)	0.0322 (18)	0.0325 (17)	0.0017 (14)	−0.0046 (13)	−0.0073 (15)
C13	0.0364 (19)	0.048 (2)	0.0246 (16)	0.0080 (16)	−0.0066 (13)	−0.0019 (16)
C14	0.049 (2)	0.039 (2)	0.0212 (16)	0.0063 (16)	−0.0025 (14)	0.0051 (14)
C15	0.0314 (17)	0.0287 (18)	0.0274 (16)	−0.0003 (14)	0.0018 (12)	−0.0007 (14)
C16	0.0264 (16)	0.0234 (16)	0.0178 (14)	0.0052 (13)	0.0015 (11)	−0.0037 (12)
C17	0.0189 (15)	0.0242 (16)	0.0203 (15)	0.0013 (12)	−0.0009 (11)	−0.0041 (13)
C18	0.0228 (15)	0.0232 (16)	0.0190 (14)	0.0038 (12)	−0.0011 (11)	0.0007 (12)
C19	0.0216 (15)	0.0259 (16)	0.0207 (14)	−0.0044 (12)	−0.0013 (11)	−0.0032 (13)
C20	0.0337 (17)	0.0283 (17)	0.0224 (15)	0.0004 (14)	−0.0002 (12)	0.0015 (14)
C21	0.0423 (19)	0.040 (2)	0.0199 (15)	−0.0100 (16)	0.0002 (13)	0.0071 (14)
C22	0.0344 (18)	0.049 (2)	0.0244 (16)	−0.0085 (16)	0.0078 (13)	−0.0044 (16)
C23	0.0261 (17)	0.0343 (18)	0.0313 (17)	−0.0009 (14)	0.0046 (13)	−0.0086 (15)
C24	0.0242 (16)	0.0266 (16)	0.0215 (15)	−0.0038 (13)	0.0022 (12)	−0.0040 (13)
C25	0.0235 (16)	0.0228 (16)	0.0347 (17)	−0.0001 (12)	0.0048 (12)	−0.0026 (14)
C26	0.0268 (16)	0.0253 (17)	0.0310 (17)	0.0042 (13)	−0.0026 (13)	0.0048 (14)
C27	0.0221 (15)	0.0254 (17)	0.0231 (15)	−0.0036 (13)	0.0001 (11)	0.0018 (13)
C28	0.0227 (16)	0.0399 (19)	0.0277 (16)	−0.0010 (14)	−0.0035 (12)	0.0099 (15)
C29	0.0321 (18)	0.049 (2)	0.0207 (15)	−0.0079 (16)	−0.0020 (13)	−0.0008 (15)
C30	0.0341 (18)	0.0319 (18)	0.0241 (15)	−0.0064 (14)	0.0025 (13)	−0.0048 (13)
C31	0.0289 (17)	0.0266 (16)	0.0231 (15)	−0.0003 (13)	−0.0010 (12)	0.0017 (13)
C32	0.0195 (15)	0.0243 (16)	0.0225 (15)	−0.0037 (12)	0.0033 (11)	0.0039 (13)
C33	0.072 (3)	0.060 (3)	0.0321 (19)	−0.001 (2)	−0.0018 (18)	−0.0009 (19)
C34	0.059 (3)	0.075 (3)	0.049 (2)	−0.005 (2)	−0.0066 (19)	0.007 (2)
C35	0.069 (3)	0.097 (4)	0.031 (2)	0.008 (3)	−0.0032 (18)	−0.009 (2)
C36	0.057 (3)	0.070 (3)	0.046 (2)	−0.009 (2)	0.0046 (18)	0.002 (2)
O2	0.0365 (13)	0.0357 (12)	0.0235 (11)	−0.0099 (10)	0.0011 (9)	0.0034 (10)
O1	0.0443 (14)	0.0513 (15)	0.0292 (12)	0.0234 (12)	−0.0061 (10)	−0.0082 (11)
N1	0.0272 (14)	0.0302 (14)	0.0256 (13)	0.0092 (11)	−0.0009 (10)	−0.0014 (11)
O4	0.0769 (19)	0.073 (2)	0.0303 (13)	0.0053 (16)	−0.0001 (12)	0.0113 (13)
N2	0.0307 (14)	0.0366 (15)	0.0231 (13)	−0.0155 (12)	0.0048 (10)	−0.0024 (11)
O3	0.088 (2)	0.109 (3)	0.0327 (15)	0.010 (2)	−0.0051 (14)	0.0206 (16)

C1—C2	1.539 (4)	C20—H201	0.940
C1—O1	1.232 (3)	C21—C22	1.382 (4)
C1—N1	1.320 (3)	C21—H211	0.944
C2—C3	1.508 (4)	C22—C23	1.375 (4)
C2—C16	1.511 (4)	C22—H221	0.948
C2—H21	0.981	C23—C24	1.401 (4)
C3—C4	1.385 (4)	C23—H231	0.944
C3—C8	1.408 (4)	C24—C25	1.457 (4)
C4—C5	1.381 (4)	C25—C26	1.337 (4)
C4—H41	0.946	C25—H251	0.955
C5—C6	1.382 (4)	C26—C27	1.457 (4)
C5—H51	0.945	C26—H261	0.932
C6—C7	1.384 (4)	C27—C28	1.404 (4)
C6—H61	0.940	C27—C32	1.400 (4)
C7—C8	1.397 (4)	C28—C29	1.379 (4)
C7—H71	0.946	C28—H281	0.924
C8—C9	1.460 (4)	C29—C30	1.378 (4)
C9—C10	1.341 (4)	C29—H291	0.959
C9—H91	0.935	C30—C31	1.379 (4)
C10—C11	1.456 (4)	C30—H301	0.934
C10—H101	0.929	C31—C32	1.389 (4)
C11—C12	1.397 (4)	C31—H311	0.942
C11—C16	1.400 (4)	C33—C34	1.477 (5)
C12—C13	1.378 (4)	C33—O4	1.423 (4)
C12—H121	0.943	C33—H331	0.980
C13—C14	1.376 (4)	C33—H332	0.977
C13—H131	0.924	C34—O3	1.422 (4)
C14—C15	1.379 (4)	C34—H341	0.976
C14—H141	0.934	C34—H342	0.969
C15—C16	1.389 (4)	C35—C36	1.464 (5)
C15—H151	0.928	C35—O3	1.410 (5)
C17—C18	1.542 (4)	C35—H351	0.963
C17—O2	1.231 (3)	C35—H352	0.979
C17—N2	1.319 (3)	C36—O4	1.409 (4)
C18—C19	1.519 (4)	C36—H361	0.997
C18—C32	1.511 (3)	C36—H362	0.984
C18—H181	0.969	N1—H12	0.871
C19—C20	1.389 (4)	N1—H11	0.855
C19—C24	1.401 (4)	N2—H13	0.870
C20—C21	1.379 (4)	N2—H14	0.873
C2—C1—O1	120.0 (2)	C20—C21—H211	119.5
C2—C1—N1	117.9 (2)	C22—C21—H211	120.8
O1—C1—N1	122.0 (3)	C21—C22—C23	119.5 (3)
C1—C2—C3	113.0 (2)	C21—C22—H221	120.9
C1—C2—C16	109.8 (2)	C23—C22—H221	119.6
C3—C2—C16	115.6 (2)	C22—C23—C24	122.0 (3)
C1—C2—H21	105.5	C22—C23—H231	119.2
C3—C2—H21	106.1	C24—C23—H231	118.9
C16—C2—H21	106.0	C19—C24—C23	117.9 (3)
C2—C3—C4	119.3 (3)	C19—C24—C25	124.0 (2)
C2—C3—C8	121.3 (2)	C23—C24—C25	118.0 (3)
C4—C3—C8	119.3 (2)	C24—C25—C26	129.0 (3)
C3—C4—C5	121.5 (3)	C24—C25—H251	115.1
C3—C4—H41	119.0	C26—C25—H251	115.8
C5—C4—H41	119.5	C25—C26—C27	129.7 (3)
C4—C5—C6	119.8 (3)	C25—C26—H261	115.7
C4—C5—H51	119.2	C27—C26—H261	114.6
C6—C5—H51	121.0	C26—C27—C28	117.6 (3)
C5—C6—C7	119.3 (3)	C26—C27—C32	124.0 (2)
C5—C6—H61	120.0	C28—C27—C32	118.3 (3)
C7—C6—H61	120.7	C27—C28—C29	121.5 (3)
C6—C7—C8	121.9 (3)	C27—C28—H281	118.9
C6—C7—H71	119.4	C29—C28—H281	119.7
C8—C7—H71	118.8	C28—C29—C30	119.9 (3)
C3—C8—C7	118.1 (3)	C28—C29—H291	119.7
C3—C8—C9	124.0 (2)	C30—C29—H291	120.4
C7—C8—C9	118.0 (3)	C29—C30—C31	119.3 (3)
C8—C9—C10	129.1 (3)	C29—C30—H301	121.2
C8—C9—H91	113.3	C31—C30—H301	119.6
C10—C9—H91	117.6	C30—C31—C32	122.0 (3)
C9—C10—C11	129.7 (3)	C30—C31—H311	119.5
C9—C10—H101	115.4	C32—C31—H311	118.5
C11—C10—H101	114.9	C18—C32—C27	121.4 (2)
C10—C11—C12	117.9 (3)	C18—C32—C31	119.5 (2)
C10—C11—C16	123.7 (2)	C27—C32—C31	119.0 (2)
C12—C11—C16	118.4 (3)	C34—C33—O4	111.5 (3)
C11—C12—C13	121.5 (3)	C34—C33—H331	107.5
C11—C12—H121	119.0	O4—C33—H331	109.5
C13—C12—H121	119.4	C34—C33—H332	107.9
C12—C13—C14	119.8 (3)	O4—C33—H332	110.1
C12—C13—H131	119.7	H331—C33—H332	110.3
C14—C13—H131	120.5	C33—C34—O3	111.8 (3)
C13—C14—C15	119.5 (3)	C33—C34—H341	109.3
C13—C14—H141	120.1	O3—C34—H341	109.4
C15—C14—H141	120.4	C33—C34—H342	108.3
C14—C15—C16	121.7 (3)	O3—C34—H342	107.3
C14—C15—H151	119.5	H341—C34—H342	110.8
C16—C15—H151	118.8	C36—C35—O3	112.0 (3)
C2—C16—C11	121.4 (2)	C36—C35—H351	110.5
C2—C16—C15	119.6 (3)	O3—C35—H351	111.0
C11—C16—C15	118.9 (2)	C36—C35—H352	108.2
C18—C17—O2	120.9 (2)	O3—C35—H352	107.7
C18—C17—N2	116.7 (2)	H351—C35—H352	107.2
O2—C17—N2	122.3 (3)	C35—C36—O4	111.7 (3)
C17—C18—C19	112.4 (2)	C35—C36—H361	109.1
C17—C18—C32	111.3 (2)	O4—C36—H361	108.7
C19—C18—C32	115.1 (2)	C35—C36—H362	110.6
C17—C18—H181	105.2	O4—C36—H362	108.0
C19—C18—H181	106.1	H361—C36—H362	108.7
C32—C18—H181	105.9	C1—N1—H12	120.5
C18—C19—C20	119.5 (3)	C1—N1—H11	118.2
C18—C19—C24	120.9 (2)	H12—N1—H11	121.2
C20—C19—C24	119.4 (2)	C33—O4—C36	111.5 (3)
C19—C20—C21	121.4 (3)	C17—N2—H13	118.9
C19—C20—H201	118.2	C17—N2—H14	120.4
C21—C20—H201	120.4	H13—N2—H14	120.7
C20—C21—C22	119.7 (3)	C34—O3—C35	111.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O2i	0.85	2.11	2.962 (3)	171
N1—H12···O4i	0.87	2.22	2.978 (3)	145
N2—H13···O1ii	0.87	1.95	2.823 (3)	177
N2—H14···O3ii	0.87	2.53	3.040 (3)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯O2i	0.85	2.11	2.962 (3)	171
N1—H12⋯O4i	0.87	2.22	2.978 (3)	145
N2—H13⋯O1ii	0.87	1.95	2.823 (3)	177
N2—H14⋯O3ii	0.87	2.53	3.040 (3)	119

Symmetry codes: (i) ; (ii) .