2-[(5'-Chloro-1,1':3',1''-terphenyl-4'-yl)imino]-acenaphthylen-1(2H)-one.

The title compound, C30H18ClNO, is a product of the condensation reaction of acenaphthyl-ene-1,2-dione and 5'-chloro-1,1':3',1''-terphenyl-4'-amine. The acenaphthyl-ene fragment and two terminal phenyl rings are rotated relative to the central benzene ring by 72.2 (3), 43.2 (3) and 41.2 (3)°, respectively. This mol-ecular conformation is supported by weak C-H⋯π inter-actions. In the crystal, mol-ecules form centrosymmetric dimers by the stacking inter-actions between two neighboring acenaphthyl-ene fragments, with an inter-planar distance of 3.365 (3) Å. The dimers are bound to each other by weak C-H⋯N and C-H⋯π inter-actions, forming a three-dimensional framework.

Related literature

For background to applications of Schiff bases, see: Lozier et al. (1975 ▶); Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For related structures, see: Higuchi et al. (2001 ▶); Manseong et al. (2006 ▶); Vitor et al. (2008 ▶).

Experimental

Crystal data

C30H18ClNO

M = 443.90

Monoclinic,

a = 12.4929 (6) Å

b = 10.8699 (7) Å

c = 16.0758 (8) Å

β = 91.864 (5)°

V = 2181.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.32 × 0.28 × 0.25 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.866, T max = 1.000

8827 measured reflections

4461 independent reflections

3151 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.121

S = 1.09

4461 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008015/kq2002sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008015/kq2002Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008015/kq2002Isup3.cml

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

C30H18ClNO	F(000) = 920
Mr = 443.90	Dx = 1.351 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
a = 12.4929 (6) Å	Cell parameters from 2796 reflections
b = 10.8699 (7) Å	θ = 3.1–28.4°
c = 16.0758 (8) Å	µ = 0.20 mm−1
β = 91.864 (5)°	T = 100 K
V = 2181.9 (2) Å3	Block, clear light-yellow
Z = 4	0.32 × 0.28 × 0.25 mm

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer	4461 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3151 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.041
Detector resolution: 16.0733 pixels mm-1	θmax = 26.4°, θmin = 3.2°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −13→11
Tmin = 0.866, Tmax = 1.000	l = −19→20
8827 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.031P)2 + 0.7817P] where P = (Fo2 + 2Fc2)/3
4461 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.28 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
Cl1	0.04696 (5)	0.31870 (6)	0.48276 (4)	0.02604 (18)
O1	0.41337 (15)	0.16285 (19)	0.45458 (12)	0.0333 (5)
N2	0.23922 (15)	0.29536 (19)	0.37546 (11)	0.0179 (5)
C1	0.29301 (19)	0.4619 (3)	0.47857 (15)	0.0226 (6)
C2	0.2362 (2)	0.5671 (3)	0.46784 (16)	0.0255 (6)
H2	0.1824	0.5737	0.4267	0.031*
C3	0.2617 (2)	0.6671 (3)	0.52178 (18)	0.0335 (7)
H3	0.2249	0.7408	0.5143	0.040*
C4	0.3393 (2)	0.6593 (3)	0.58509 (17)	0.0334 (7)
H4	0.3515	0.7262	0.6201	0.040*
C5	0.3989 (2)	0.5525 (3)	0.59681 (16)	0.0276 (7)
C6	0.4832 (2)	0.5294 (3)	0.65685 (16)	0.0330 (7)
H6	0.5019	0.5901	0.6954	0.040*
C7	0.5368 (2)	0.4199 (3)	0.65874 (16)	0.0352 (8)
H7	0.5911	0.4087	0.6990	0.042*
C8	0.5140 (2)	0.3233 (3)	0.60276 (15)	0.0317 (7)
H8	0.5527	0.2502	0.6045	0.038*
C9	0.4309 (2)	0.3422 (3)	0.54485 (15)	0.0249 (6)
C10	0.3752 (2)	0.4534 (3)	0.54261 (15)	0.0250 (6)
C11	0.3865 (2)	0.2656 (3)	0.47682 (15)	0.0247 (6)
C12	0.29469 (18)	0.3418 (2)	0.43510 (14)	0.0186 (6)
C13	0.15077 (18)	0.3582 (2)	0.33866 (14)	0.0176 (5)
C14	0.05499 (19)	0.3719 (2)	0.38076 (14)	0.0195 (6)
C15	−0.03509 (19)	0.4241 (2)	0.34434 (15)	0.0213 (6)
H15	−0.0974	0.4306	0.3741	0.026*
C16	−0.03305 (19)	0.4674 (2)	0.26273 (15)	0.0208 (6)
C17	0.06207 (18)	0.4559 (2)	0.22035 (15)	0.0195 (6)
H17	0.0645	0.4862	0.1663	0.023*
C18	0.15357 (18)	0.4010 (2)	0.25532 (14)	0.0169 (5)
C19	0.25352 (18)	0.3931 (2)	0.20691 (14)	0.0176 (5)
C20	0.31803 (19)	0.2884 (2)	0.20722 (14)	0.0211 (6)
H20	0.2982	0.2193	0.2372	0.025*
C21	0.4119 (2)	0.2865 (3)	0.16287 (15)	0.0250 (6)
H21	0.4542	0.2160	0.1632	0.030*
C22	0.4425 (2)	0.3883 (3)	0.11853 (15)	0.0265 (6)
H22	0.5062	0.3874	0.0902	0.032*
C23	0.3783 (2)	0.4918 (3)	0.11635 (15)	0.0247 (6)
H23	0.3984	0.5603	0.0859	0.030*
C24	0.28386 (19)	0.4937 (2)	0.15946 (14)	0.0209 (6)
H24	0.2403	0.5631	0.1566	0.025*
C25	−0.1326 (2)	0.5199 (3)	0.22308 (17)	0.0258 (6)
C26	−0.2001 (2)	0.5956 (3)	0.26780 (18)	0.0335 (7)
H26	−0.1807	0.6176	0.3221	0.040*
C27	−0.2959 (2)	0.6385 (3)	0.2324 (2)	0.0415 (8)
H27	−0.3399	0.6897	0.2625	0.050*
C28	−0.3251 (2)	0.6047 (3)	0.1522 (2)	0.0447 (9)
H28	−0.3900	0.6316	0.1287	0.054*
C29	−0.2592 (2)	0.5316 (3)	0.1070 (2)	0.0434 (9)
H29	−0.2794	0.5096	0.0529	0.052*
C30	−0.1619 (2)	0.4899 (3)	0.14165 (18)	0.0338 (7)
H30	−0.1167	0.4420	0.1101	0.041*

	U11	U22	U33	U12	U13	U23
Cl1	0.0262 (3)	0.0333 (4)	0.0187 (3)	−0.0013 (3)	0.0026 (2)	0.0074 (3)
O1	0.0344 (11)	0.0298 (12)	0.0354 (11)	0.0085 (10)	−0.0043 (8)	0.0040 (9)
N2	0.0197 (10)	0.0197 (12)	0.0139 (10)	−0.0025 (10)	−0.0030 (8)	0.0026 (9)
C1	0.0201 (12)	0.0284 (16)	0.0193 (13)	−0.0087 (13)	0.0024 (10)	−0.0033 (11)
C2	0.0239 (13)	0.0242 (16)	0.0285 (14)	−0.0040 (13)	0.0047 (11)	−0.0062 (12)
C3	0.0247 (14)	0.0299 (18)	0.0461 (18)	−0.0004 (14)	0.0070 (12)	−0.0112 (14)
C4	0.0246 (14)	0.041 (2)	0.0352 (16)	−0.0075 (15)	0.0095 (12)	−0.0183 (14)
C5	0.0208 (13)	0.0387 (19)	0.0235 (14)	−0.0099 (14)	0.0055 (11)	−0.0036 (13)
C6	0.0295 (15)	0.050 (2)	0.0195 (14)	−0.0194 (16)	0.0031 (11)	−0.0103 (14)
C7	0.0259 (15)	0.058 (2)	0.0209 (14)	−0.0123 (16)	−0.0051 (11)	0.0032 (14)
C8	0.0264 (14)	0.048 (2)	0.0201 (13)	−0.0138 (15)	−0.0022 (10)	0.0100 (13)
C9	0.0231 (13)	0.0350 (18)	0.0165 (12)	−0.0062 (14)	−0.0005 (10)	0.0046 (12)
C10	0.0212 (13)	0.0396 (18)	0.0145 (12)	−0.0137 (14)	0.0059 (10)	−0.0023 (12)
C11	0.0251 (14)	0.0293 (17)	0.0197 (13)	−0.0020 (14)	0.0009 (10)	0.0075 (12)
C12	0.0188 (12)	0.0219 (15)	0.0150 (12)	−0.0035 (12)	0.0013 (9)	0.0020 (11)
C13	0.0212 (12)	0.0141 (13)	0.0170 (12)	−0.0008 (11)	−0.0048 (9)	−0.0020 (10)
C14	0.0250 (13)	0.0184 (15)	0.0150 (12)	−0.0048 (12)	−0.0005 (10)	0.0031 (10)
C15	0.0174 (12)	0.0217 (15)	0.0248 (13)	−0.0032 (12)	0.0014 (10)	0.0031 (11)
C16	0.0165 (12)	0.0186 (15)	0.0268 (14)	−0.0040 (12)	−0.0043 (10)	0.0020 (11)
C17	0.0235 (13)	0.0180 (14)	0.0167 (12)	−0.0036 (12)	−0.0039 (10)	0.0014 (11)
C18	0.0201 (12)	0.0135 (13)	0.0168 (12)	−0.0033 (11)	−0.0028 (9)	−0.0026 (10)
C19	0.0186 (12)	0.0204 (14)	0.0134 (11)	−0.0007 (12)	−0.0050 (9)	−0.0044 (10)
C20	0.0266 (13)	0.0191 (15)	0.0174 (12)	−0.0025 (12)	−0.0036 (10)	−0.0020 (11)
C21	0.0273 (14)	0.0236 (16)	0.0239 (14)	0.0030 (13)	−0.0003 (11)	−0.0086 (12)
C22	0.0242 (14)	0.0339 (18)	0.0218 (14)	−0.0070 (14)	0.0071 (11)	−0.0105 (12)
C23	0.0313 (14)	0.0247 (16)	0.0183 (13)	−0.0079 (14)	0.0039 (10)	−0.0023 (11)
C24	0.0269 (13)	0.0205 (15)	0.0151 (12)	−0.0011 (12)	−0.0037 (10)	−0.0019 (11)
C25	0.0197 (13)	0.0257 (16)	0.0318 (15)	−0.0054 (13)	−0.0030 (11)	0.0104 (12)
C26	0.0249 (14)	0.0405 (19)	0.0354 (16)	0.0011 (15)	0.0070 (12)	0.0145 (14)
C27	0.0211 (14)	0.047 (2)	0.058 (2)	0.0073 (15)	0.0114 (14)	0.0223 (17)
C28	0.0195 (14)	0.045 (2)	0.069 (2)	−0.0037 (16)	−0.0114 (15)	0.0275 (19)
C29	0.0426 (18)	0.033 (2)	0.052 (2)	−0.0058 (17)	−0.0250 (15)	0.0092 (16)
C30	0.0345 (16)	0.0253 (17)	0.0405 (17)	−0.0008 (15)	−0.0146 (13)	0.0026 (14)

Cl1—C14	1.745 (2)	C15—C16	1.395 (3)
O1—C11	1.223 (3)	C16—C17	1.394 (3)
N2—C12	1.269 (3)	C16—C25	1.492 (3)
N2—C13	1.412 (3)	C17—H17	0.9300
C1—C2	1.354 (4)	C17—C18	1.392 (3)
C1—C10	1.433 (3)	C18—C19	1.495 (3)
C1—C12	1.481 (4)	C19—C20	1.395 (3)
C2—H2	0.9300	C19—C24	1.393 (3)
C2—C3	1.420 (4)	C20—H20	0.9300
C3—H3	0.9300	C20—C21	1.392 (3)
C3—C4	1.385 (4)	C21—H21	0.9300
C4—H4	0.9300	C21—C22	1.378 (4)
C4—C5	1.389 (4)	C22—H22	0.9300
C5—C6	1.427 (4)	C22—C23	1.381 (4)
C5—C10	1.411 (4)	C23—H23	0.9300
C6—H6	0.9300	C23—C24	1.388 (3)
C6—C7	1.366 (4)	C24—H24	0.9300
C7—H7	0.9300	C25—C26	1.394 (4)
C7—C8	1.407 (4)	C25—C30	1.387 (4)
C8—H8	0.9300	C26—H26	0.9300
C8—C9	1.387 (3)	C26—C27	1.389 (4)
C9—C10	1.394 (4)	C27—H27	0.9300
C9—C11	1.469 (4)	C27—C28	1.378 (5)
C11—C12	1.550 (4)	C28—H28	0.9300
C13—C14	1.402 (3)	C28—C29	1.370 (5)
C13—C18	1.420 (3)	C29—H29	0.9300
C14—C15	1.374 (3)	C29—C30	1.396 (4)
C15—H15	0.9300	C30—H30	0.9300
C12—N2—C13	121.6 (2)	C15—C16—C25	119.4 (2)
C2—C1—C10	120.5 (2)	C17—C16—C15	118.1 (2)
C2—C1—C12	134.4 (2)	C17—C16—C25	122.5 (2)
C10—C1—C12	105.1 (2)	C16—C17—H17	118.6
C1—C2—H2	121.2	C18—C17—C16	122.9 (2)
C1—C2—C3	117.5 (2)	C18—C17—H17	118.6
C3—C2—H2	121.2	C13—C18—C19	121.3 (2)
C2—C3—H3	118.7	C17—C18—C13	118.4 (2)
C4—C3—C2	122.7 (3)	C17—C18—C19	120.2 (2)
C4—C3—H3	118.7	C20—C19—C18	122.5 (2)
C3—C4—H4	119.6	C24—C19—C18	119.1 (2)
C3—C4—C5	120.7 (3)	C24—C19—C20	118.4 (2)
C5—C4—H4	119.6	C19—C20—H20	119.8
C4—C5—C6	128.3 (3)	C21—C20—C19	120.4 (2)
C4—C5—C10	117.0 (2)	C21—C20—H20	119.8
C10—C5—C6	114.8 (3)	C20—C21—H21	119.8
C5—C6—H6	119.4	C22—C21—C20	120.4 (3)
C7—C6—C5	121.3 (3)	C22—C21—H21	119.8
C7—C6—H6	119.4	C21—C22—H22	120.1
C6—C7—H7	118.4	C21—C22—C23	119.8 (2)
C6—C7—C8	123.2 (3)	C23—C22—H22	120.1
C8—C7—H7	118.4	C22—C23—H23	119.9
C7—C8—H8	121.6	C22—C23—C24	120.2 (3)
C9—C8—C7	116.8 (3)	C24—C23—H23	119.9
C9—C8—H8	121.6	C19—C24—H24	119.6
C8—C9—C10	120.5 (3)	C23—C24—C19	120.8 (3)
C8—C9—C11	132.2 (3)	C23—C24—H24	119.6
C10—C9—C11	107.2 (2)	C26—C25—C16	121.0 (2)
C5—C10—C1	121.7 (3)	C30—C25—C16	120.3 (3)
C9—C10—C1	114.8 (2)	C30—C25—C26	118.7 (3)
C9—C10—C5	123.5 (2)	C25—C26—H26	119.5
O1—C11—C9	129.4 (3)	C27—C26—C25	120.9 (3)
O1—C11—C12	124.6 (2)	C27—C26—H26	119.5
C9—C11—C12	106.0 (2)	C26—C27—H27	120.2
N2—C12—C1	133.7 (2)	C28—C27—C26	119.5 (3)
N2—C12—C11	119.5 (2)	C28—C27—H27	120.2
C1—C12—C11	106.8 (2)	C27—C28—H28	119.8
N2—C13—C18	120.7 (2)	C29—C28—C27	120.3 (3)
C14—C13—N2	121.2 (2)	C29—C28—H28	119.8
C14—C13—C18	117.9 (2)	C28—C29—H29	119.8
C13—C14—Cl1	119.65 (18)	C28—C29—C30	120.5 (3)
C15—C14—Cl1	117.78 (19)	C30—C29—H29	119.8
C15—C14—C13	122.6 (2)	C25—C30—C29	120.0 (3)
C14—C15—H15	120.0	C25—C30—H30	120.0
C14—C15—C16	120.0 (2)	C29—C30—H30	120.0
C16—C15—H15	120.0
Cl1—C14—C15—C16	−179.6 (2)	C12—C1—C2—C3	−177.2 (3)
O1—C11—C12—N2	2.8 (4)	C12—C1—C10—C5	178.9 (2)
O1—C11—C12—C1	−177.2 (2)	C12—C1—C10—C9	0.9 (3)
N2—C13—C14—Cl1	3.9 (3)	C13—N2—C12—C1	−3.7 (4)
N2—C13—C14—C15	−174.9 (2)	C13—N2—C12—C11	176.2 (2)
N2—C13—C18—C17	176.2 (2)	C13—C14—C15—C16	−0.8 (4)
N2—C13—C18—C19	−6.6 (4)	C13—C18—C19—C20	44.1 (3)
C1—C2—C3—C4	−1.8 (4)	C13—C18—C19—C24	−136.0 (2)
C2—C1—C10—C5	0.7 (4)	C14—C13—C18—C17	1.0 (4)
C2—C1—C10—C9	−177.3 (2)	C14—C13—C18—C19	178.2 (2)
C2—C1—C12—N2	−4.2 (5)	C14—C15—C16—C17	0.0 (4)
C2—C1—C12—C11	175.8 (3)	C14—C15—C16—C25	177.9 (2)
C2—C3—C4—C5	2.3 (4)	C15—C16—C17—C18	1.4 (4)
C3—C4—C5—C6	178.2 (3)	C15—C16—C25—C26	40.5 (4)
C3—C4—C5—C10	−1.2 (4)	C15—C16—C25—C30	−136.8 (3)
C4—C5—C6—C7	−177.9 (3)	C16—C17—C18—C13	−1.9 (4)
C4—C5—C10—C1	−0.3 (4)	C16—C17—C18—C19	−179.1 (2)
C4—C5—C10—C9	177.6 (2)	C16—C25—C26—C27	−176.2 (3)
C5—C6—C7—C8	0.1 (4)	C16—C25—C30—C29	175.0 (3)
C6—C5—C10—C1	−179.7 (2)	C17—C16—C25—C26	−141.7 (3)
C6—C5—C10—C9	−1.9 (4)	C17—C16—C25—C30	41.0 (4)
C6—C7—C8—C9	−1.4 (4)	C17—C18—C19—C20	−138.7 (2)
C7—C8—C9—C10	1.1 (4)	C17—C18—C19—C24	41.2 (3)
C7—C8—C9—C11	178.4 (3)	C18—C13—C14—Cl1	179.04 (18)
C8—C9—C10—C1	178.6 (2)	C18—C13—C14—C15	0.3 (4)
C8—C9—C10—C5	0.6 (4)	C18—C19—C20—C21	−178.3 (2)
C8—C9—C11—O1	0.2 (5)	C18—C19—C24—C23	177.4 (2)
C8—C9—C11—C12	−179.5 (3)	C19—C20—C21—C22	0.4 (4)
C9—C11—C12—N2	−177.5 (2)	C20—C19—C24—C23	−2.7 (3)
C9—C11—C12—C1	2.4 (2)	C20—C21—C22—C23	−1.7 (4)
C10—C1—C2—C3	0.3 (4)	C21—C22—C23—C24	0.8 (4)
C10—C1—C12—N2	178.0 (3)	C22—C23—C24—C19	1.4 (4)
C10—C1—C12—C11	−2.0 (2)	C24—C19—C20—C21	1.8 (3)
C10—C5—C6—C7	1.5 (4)	C25—C16—C17—C18	−176.4 (2)
C10—C9—C11—O1	177.7 (3)	C25—C26—C27—C28	0.7 (4)
C10—C9—C11—C12	−1.9 (3)	C26—C25—C30—C29	−2.3 (4)
C11—C9—C10—C1	0.7 (3)	C26—C27—C28—C29	−1.5 (5)
C11—C9—C10—C5	−177.3 (2)	C27—C28—C29—C30	0.4 (5)
C12—N2—C13—C14	−72.0 (3)	C28—C29—C30—C25	1.6 (5)
C12—N2—C13—C18	112.9 (3)	C30—C25—C26—C27	1.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···N2	0.93	2.50	2.909 (3)	107
C24—H24···N2i	0.93	2.59	3.338 (3)	138
C4—H4···Cg1ii	0.93	2.74	3.551 (3)	147
C6—H6···Cg2iii	0.93	2.92	3.647 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C25–C30 and C19–C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24⋯N2i	0.93	2.59	3.338 (3)	138
C4—H4⋯Cg1ii	0.93	2.74	3.551 (3)	147
C6—H6⋯Cg2iii	0.93	2.92	3.647 (3)	136

Symmetry codes: (i) ; (ii) ; (iii) .