4,4'-[Propane-1,2-diyl-bis(nitrilo-methyl-idyne)]-dibenzo-nitrile-4,4'-[ethane-1,2-diylbis(nitrilo-methyl-idyne)]dibenzonitrile [0.796 (2)/0.204 (2)].

The title cocrystal, 0.796C(19)H(16)N(4)·0.204C(18)H(14)N(4), is a disordered mixture of two potentially bidentate Schiff base ligands. The difference in the two components of the cocrystal is the replacement of the methyl group in the linkage between the imine N atoms in the major component of the Schiff base ligand by an H atom. The imino (C=N) functional groups are coplanar with the benzene rings (only the major component) and extend in opposite directions (both components). Inter-molecular π-π inter-actions with a centroid-to-centroid distance of 3.7371 (8) Å are observed in the crystal packing.

Related literature

For values of bond lengths, see: Allen et al. (1987 ▶). For related structures, see, for example: Li et al. (2005 ▶); Bomfim et al. (2005 ▶); Glidewell et al. (2005 ▶, 2006 ▶); Sun et al. (2004 ▶); Fun, Kia & Kargar (2008 ▶); Fun, Kargar & Kia (2008 ▶).

Experimental

Crystal data

0.796C19H16N4·0.204C18H14N4

M = 297.68

Triclinic,

a = 9.2370 (2) Å

b = 9.7769 (2) Å

c = 9.8169 (2) Å

α = 81.846 (1)°

β = 75.098 (1)°

γ = 67.421 (1)°

V = 790.15 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100.0 (1) K

0.39 × 0.38 × 0.27 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.890, T max = 0.979

17295 measured reflections

4628 independent reflections

3746 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.182

S = 1.04

4628 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031097/ez2140sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031097/ez2140Isup2.hkl

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

0.796C19H16N4·0.204C18H14N4	Z = 2
Mr = 297.68	F(000) = 313
Triclinic, P1	Dx = 1.251 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2370 (2) Å	Cell parameters from 6569 reflections
b = 9.7769 (2) Å	θ = 3.2–30.8°
c = 9.8169 (2) Å	µ = 0.08 mm−1
α = 81.846 (1)°	T = 100 K
β = 75.098 (1)°	Block, colourless
γ = 67.421 (1)°	0.39 × 0.38 × 0.27 mm
V = 790.15 (3) Å3

Bruker SMART APEXII CCD area-detector diffractometer	4628 independent reflections
Radiation source: fine-focus sealed tube	3746 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 30.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.890, Tmax = 0.979	k = −13→13
17295 measured reflections	l = −13→13

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0996P)2 + 0.2311P] where P = (Fo2 + 2Fc2)/3
4628 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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)
N1A	0.44472 (19)	0.58449 (16)	0.76563 (18)	0.0277 (3)	0.796 (2)
N2A	0.31537 (17)	0.28586 (16)	0.96983 (15)	0.0294 (3)	0.796 (2)
C8A	0.41965 (19)	0.44248 (17)	0.78683 (17)	0.0276 (3)	0.796 (2)
H8AA	0.5235	0.3602	0.7675	0.033*	0.796 (2)
C9A	0.3328 (2)	0.42957 (19)	0.93985 (17)	0.0311 (4)	0.796 (2)
H9AA	0.3933	0.4409	1.0021	0.037*	0.796 (2)
H9AB	0.2275	0.5079	0.9569	0.037*	0.796 (2)
C19A	0.3162 (2)	0.44326 (18)	0.68371 (15)	0.0302 (4)	0.796 (2)
H19A	0.3770	0.4426	0.5883	0.045*	0.796 (2)
H19B	0.2204	0.5308	0.6954	0.045*	0.796 (2)
H19C	0.2873	0.3569	0.7039	0.045*	0.796 (2)
N1B	0.4751 (7)	0.5817 (7)	0.8069 (6)	0.0236 (13)*	0.204 (2)
N2B	0.2894 (7)	0.2948 (6)	0.8959 (6)	0.0294 (3)	0.204 (2)
C8B	0.4619 (7)	0.4375 (6)	0.8536 (6)	0.0225 (11)*	0.204 (2)
H8BA	0.4726	0.4144	0.9508	0.027*	0.204 (2)
H8BB	0.5478	0.3612	0.7959	0.027*	0.204 (2)
C9B	0.2974 (6)	0.4397 (6)	0.8414 (6)	0.0203 (10)	0.204 (2)
H9BA	0.2106	0.5179	0.8962	0.024*	0.204 (2)
H9BB	0.2881	0.4571	0.7437	0.024*	0.204 (2)
N3	0.77232 (14)	1.20704 (14)	0.53274 (13)	0.0356 (3)
N4	0.04293 (17)	−0.36229 (15)	1.22228 (16)	0.0481 (4)
C1	0.77783 (15)	0.70764 (15)	0.59144 (14)	0.0310 (3)
H1A	0.8552	0.6156	0.5652	0.037*
C2	0.81727 (15)	0.83368 (15)	0.55783 (13)	0.0301 (3)
H2A	0.9207	0.8263	0.5101	0.036*
C3	0.70001 (14)	0.97147 (14)	0.59648 (12)	0.0250 (2)
C4	0.54475 (14)	0.98285 (14)	0.66949 (13)	0.0281 (3)
H4A	0.4671	1.0749	0.6957	0.034*
C5	0.50763 (14)	0.85626 (14)	0.70243 (13)	0.0274 (3)
H5A	0.4043	0.8635	0.7507	0.033*
C6	0.62345 (14)	0.71778 (14)	0.66410 (12)	0.0248 (2)
C7	0.58542 (16)	0.58172 (14)	0.69901 (14)	0.0302 (3)
H7A	0.6682	0.4882	0.6713	0.036*	0.796 (2)
H7B	0.6427	0.4971	0.6419	0.036*	0.204 (2)
C10	0.18277 (17)	0.28390 (16)	1.04041 (17)	0.0379 (3)
H10A	0.0979	0.3754	1.0711	0.045*	0.796 (2)
H10B	0.1389	0.3631	1.1042	0.045*	0.204 (2)
C11	0.15451 (14)	0.14439 (14)	1.07915 (13)	0.0269 (3)
C12	0.00891 (15)	0.14545 (14)	1.16669 (14)	0.0309 (3)
H12A	−0.0691	0.2345	1.2005	0.037*
C13	−0.02034 (15)	0.01501 (14)	1.20368 (13)	0.0285 (3)
H13A	−0.1174	0.0161	1.2625	0.034*
C14	0.09638 (15)	−0.11766 (14)	1.15229 (13)	0.0269 (3)
C15	0.24291 (15)	−0.12015 (15)	1.06462 (14)	0.0316 (3)
H15A	0.3205	−0.2092	1.0303	0.038*
C16	0.27163 (14)	0.01010 (14)	1.02930 (13)	0.0283 (3)
H16A	0.3695	0.0086	0.9720	0.034*
C17	0.73983 (15)	1.10277 (15)	0.56153 (13)	0.0281 (3)
C18	0.06622 (17)	−0.25355 (16)	1.19090 (15)	0.0348 (3)

	U11	U22	U33	U12	U13	U23
N1A	0.0290 (7)	0.0270 (7)	0.0282 (7)	−0.0139 (5)	−0.0013 (6)	−0.0031 (5)
N2A	0.0304 (6)	0.0287 (6)	0.0298 (7)	−0.0149 (5)	−0.0010 (5)	−0.0024 (5)
C8A	0.0276 (7)	0.0234 (7)	0.0311 (8)	−0.0119 (6)	−0.0002 (6)	−0.0034 (6)
C9A	0.0340 (8)	0.0303 (8)	0.0313 (8)	−0.0176 (6)	0.0008 (6)	−0.0062 (6)
C19A	0.0537 (10)	0.0276 (7)	0.0222 (7)	−0.0273 (7)	−0.0126 (6)	0.0023 (5)
N2B	0.0304 (6)	0.0287 (6)	0.0298 (7)	−0.0149 (5)	−0.0010 (5)	−0.0024 (5)
C9B	0.024 (2)	0.016 (2)	0.021 (2)	−0.0076 (19)	−0.0053 (18)	0.0005 (18)
N3	0.0337 (6)	0.0363 (6)	0.0387 (6)	−0.0187 (5)	0.0002 (5)	−0.0055 (5)
N4	0.0457 (7)	0.0340 (7)	0.0585 (8)	−0.0165 (6)	0.0000 (6)	0.0008 (6)
C1	0.0258 (6)	0.0283 (6)	0.0341 (6)	−0.0090 (5)	0.0027 (5)	−0.0060 (5)
C2	0.0239 (5)	0.0335 (7)	0.0312 (6)	−0.0127 (5)	0.0020 (4)	−0.0046 (5)
C3	0.0253 (5)	0.0294 (6)	0.0229 (5)	−0.0134 (5)	−0.0033 (4)	−0.0031 (4)
C4	0.0235 (5)	0.0265 (6)	0.0325 (6)	−0.0096 (4)	−0.0006 (4)	−0.0051 (5)
C5	0.0225 (5)	0.0294 (6)	0.0298 (6)	−0.0116 (5)	−0.0006 (4)	−0.0036 (5)
C6	0.0252 (5)	0.0268 (6)	0.0219 (5)	−0.0112 (4)	−0.0011 (4)	−0.0029 (4)
C7	0.0304 (6)	0.0258 (6)	0.0308 (6)	−0.0108 (5)	0.0010 (5)	−0.0025 (5)
C10	0.0293 (6)	0.0273 (6)	0.0558 (9)	−0.0129 (5)	0.0018 (6)	−0.0112 (6)
C11	0.0248 (5)	0.0261 (6)	0.0312 (6)	−0.0105 (4)	−0.0043 (4)	−0.0055 (4)
C12	0.0260 (6)	0.0257 (6)	0.0360 (6)	−0.0066 (5)	0.0000 (5)	−0.0066 (5)
C13	0.0236 (5)	0.0305 (6)	0.0283 (6)	−0.0094 (5)	−0.0015 (4)	−0.0008 (5)
C14	0.0269 (6)	0.0263 (6)	0.0263 (5)	−0.0094 (5)	−0.0046 (4)	−0.0005 (4)
C15	0.0271 (6)	0.0265 (6)	0.0358 (6)	−0.0072 (5)	0.0004 (5)	−0.0057 (5)
C16	0.0232 (5)	0.0299 (6)	0.0303 (6)	−0.0100 (5)	−0.0006 (4)	−0.0054 (5)
C17	0.0256 (5)	0.0330 (6)	0.0269 (6)	−0.0134 (5)	−0.0013 (4)	−0.0054 (5)
C18	0.0326 (6)	0.0304 (7)	0.0372 (7)	−0.0113 (5)	−0.0012 (5)	−0.0005 (5)

N1A—C7	1.2878 (18)	C2—C3	1.3947 (18)
N1A—C8A	1.4714 (19)	C2—H2A	0.9300
N2A—C10	1.2484 (18)	C3—C4	1.3979 (16)
N2A—C9A	1.455 (2)	C3—C17	1.4400 (16)
C8A—C9A	1.523 (2)	C4—C5	1.3818 (16)
C8A—C19A	1.558 (2)	C4—H4A	0.9300
C8A—H8AA	0.9800	C5—C6	1.3944 (17)
C9A—H9AA	0.9700	C5—H5A	0.9300
C9A—H9AB	0.9700	C6—C7	1.4758 (16)
C19A—H19A	0.9600	C7—H7A	0.9600
C19A—H19B	0.9600	C7—H7B	0.9600
C19A—H19C	0.9600	C10—C11	1.4658 (17)
N1B—C7	1.267 (6)	C10—H10A	0.9600
N1B—C8B	1.460 (8)	C10—H10B	0.9600
N2B—C9B	1.464 (7)	C11—C12	1.3945 (17)
N2B—C10	1.521 (6)	C11—C16	1.3975 (17)
C8B—C9B	1.546 (8)	C12—C13	1.3834 (17)
C8B—H8BA	0.9700	C12—H12A	0.9300
C8B—H8BB	0.9700	C13—C14	1.3897 (17)
C9B—H9BA	0.9700	C13—H13A	0.9300
C9B—H9BB	0.9700	C14—C15	1.3982 (17)
N3—C17	1.1484 (17)	C14—C18	1.4400 (18)
N4—C18	1.1489 (19)	C15—C16	1.3781 (17)
C1—C2	1.3883 (17)	C15—H15A	0.9300
C1—C6	1.3930 (16)	C16—H16A	0.9300
C1—H1A	0.9300
C7—N1A—C8A	116.77 (13)	C1—C6—C5	119.43 (11)
C10—N2A—C9A	117.17 (13)	C1—C6—C7	119.38 (11)
N1A—C8A—C9A	107.68 (13)	C5—C6—C7	121.19 (10)
N1A—C8A—C19A	108.24 (13)	N1B—C7—N1A	24.5 (2)
C9A—C8A—C19A	111.02 (13)	N1B—C7—C6	117.3 (3)
N1A—C8A—H8AA	110.0	N1A—C7—C6	122.07 (12)
C9A—C8A—H8AA	110.0	N1B—C7—H7A	117.8
C19A—C8A—H8AA	110.0	N1A—C7—H7A	119.0
N2A—C9A—C8A	110.09 (13)	C6—C7—H7A	119.0
N2A—C9A—H9AA	109.6	N1B—C7—H7B	121.9
C8A—C9A—H9AA	109.6	N1A—C7—H7B	111.9
N2A—C9A—H9AB	109.6	C6—C7—H7B	120.8
C8A—C9A—H9AB	109.6	H7A—C7—H7B	23.9
H9AA—C9A—H9AB	108.2	N2A—C10—C11	121.33 (13)
C7—N1B—C8B	115.5 (5)	N2A—C10—N2B	31.9 (2)
C9B—N2B—C10	118.6 (4)	C11—C10—N2B	116.6 (2)
N1B—C8B—C9B	110.0 (5)	N2A—C10—H10A	119.5
N1B—C8B—H8BA	109.7	C11—C10—H10A	119.2
C9B—C8B—H8BA	109.7	N2B—C10—H10A	114.8
N1B—C8B—H8BB	109.7	N2A—C10—H10B	107.4
C9B—C8B—H8BB	109.7	C11—C10—H10B	121.7
H8BA—C8B—H8BB	108.2	N2B—C10—H10B	121.8
N2B—C9B—C8B	107.0 (4)	H10A—C10—H10B	32.0
N2B—C9B—H9BA	110.3	C12—C11—C16	119.49 (11)
C8B—C9B—H9BA	110.3	C12—C11—C10	119.68 (11)
N2B—C9B—H9BB	110.3	C16—C11—C10	120.83 (11)
C8B—C9B—H9BB	110.3	C13—C12—C11	120.51 (11)
H9BA—C9B—H9BB	108.6	C13—C12—H12A	119.7
C2—C1—C6	120.64 (11)	C11—C12—H12A	119.7
C2—C1—H1A	119.7	C12—C13—C14	119.49 (11)
C6—C1—H1A	119.7	C12—C13—H13A	120.3
C1—C2—C3	119.28 (11)	C14—C13—H13A	120.3
C1—C2—H2A	120.4	C13—C14—C15	120.52 (12)
C3—C2—H2A	120.4	C13—C14—C18	119.56 (11)
C2—C3—C4	120.53 (11)	C15—C14—C18	119.92 (11)
C2—C3—C17	119.61 (10)	C16—C15—C14	119.61 (11)
C4—C3—C17	119.86 (11)	C16—C15—H15A	120.2
C5—C4—C3	119.44 (11)	C14—C15—H15A	120.2
C5—C4—H4A	120.3	C15—C16—C11	120.37 (11)
C3—C4—H4A	120.3	C15—C16—H16A	119.8
C4—C5—C6	120.68 (11)	C11—C16—H16A	119.8
C4—C5—H5A	119.7	N3—C17—C3	179.50 (14)
C6—C5—H5A	119.7	N4—C18—C14	179.53 (16)
C7—N1A—C8A—C9A	134.28 (16)	C1—C6—C7—N1B	152.5 (3)
C7—N1A—C8A—C19A	−105.62 (18)	C5—C6—C7—N1B	−27.5 (4)
C10—N2A—C9A—C8A	−136.91 (16)	C1—C6—C7—N1A	−179.80 (14)
N1A—C8A—C9A—N2A	−175.76 (13)	C5—C6—C7—N1A	0.2 (2)
C19A—C8A—C9A—N2A	65.92 (17)	C9A—N2A—C10—C11	−178.46 (13)
C7—N1B—C8B—C9B	−116.7 (5)	C9A—N2A—C10—N2B	90.8 (4)
C10—N2B—C9B—C8B	105.6 (5)	C9B—N2B—C10—N2A	−83.9 (6)
N1B—C8B—C9B—N2B	−177.4 (5)	C9B—N2B—C10—C11	168.8 (4)
C6—C1—C2—C3	−0.6 (2)	N2A—C10—C11—C12	175.33 (15)
C1—C2—C3—C4	0.61 (19)	N2B—C10—C11—C12	−148.5 (3)
C1—C2—C3—C17	−179.77 (11)	N2A—C10—C11—C16	−4.8 (2)
C2—C3—C4—C5	−0.45 (19)	N2B—C10—C11—C16	31.4 (3)
C17—C3—C4—C5	179.94 (11)	C16—C11—C12—C13	−0.31 (19)
C3—C4—C5—C6	0.25 (19)	C10—C11—C12—C13	179.60 (12)
C2—C1—C6—C5	0.38 (19)	C11—C12—C13—C14	−0.35 (19)
C2—C1—C6—C7	−179.66 (11)	C12—C13—C14—C15	0.44 (19)
C4—C5—C6—C1	−0.22 (19)	C12—C13—C14—C18	179.89 (12)
C4—C5—C6—C7	179.83 (11)	C13—C14—C15—C16	0.1 (2)
C8B—N1B—C7—N1A	83.2 (8)	C18—C14—C15—C16	−179.31 (12)
C8B—N1B—C7—C6	−168.7 (4)	C14—C15—C16—C11	−0.8 (2)
C8A—N1A—C7—N1B	−97.6 (8)	C12—C11—C16—C15	0.90 (19)
C8A—N1A—C7—C6	176.59 (13)	C10—C11—C16—C15	−179.01 (12)