N,N'-Bis(pyridin-2-yl)benzene-1,4-diamine-naphthalene (2/1).

The asymmetric unit of the title compound, C(10)H(8)·2C(16)H(14)N(4), consists of one mol-ecule of N,N'-bis-(pyridin-2-yl)benzene-1,4-diamine (PDAB) and one half of the centrosymmetric naphthalene mol-ecule. The PDAB mol-ecule adopts a non-planar conformation with an E configuration at the two partially double exo C N bonds of the 2-pyridyl-amine units. In the crystal, N-H⋯N hydrogen bonds between the PDAB mol-ecules generate a cyclic R(2) (2)(8) motif, leading to the formation of PDAB tapes extending along [100]. The tapes are arranged into (010) layers and the naphthalene mol-ecules are enclosed in cavities formed between the PDAB layers.

Related literature

For the structures of polymorphic forms of N,N′-di(pyridin-2-yl)benzene-1,4-diamine, see: Bensemann et al. (2002 ▶); Wicher & Gdaniec (2011a ▶). For the structures of N,N′-di(pyridin-2-yl)benzene-1,4-diamine co-crystals with phenazine and quin­oxaline, see: Gdaniec et al. (2005 ▶); Wicher & Gdaniec (2011b ▶).

Experimental

Crystal data

C10H8·2C16H14N4

M = 652.78

Monoclinic,

a = 9.2224 (1) Å

b = 22.8371 (2) Å

c = 8.8760 (1) Å

β = 117.936 (2)°

V = 1651.56 (3) Å3

Z = 2

Cu Kα radiation

μ = 0.63 mm−1

T = 130 K

0.20 × 0.15 × 0.05 mm

Data collection

Oxford Diffraction SuperNova diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.931, T max = 1.000

9878 measured reflections

3020 independent reflections

2671 reflections with I > 2/s(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.091

S = 1.05

3020 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811047519/rz2666sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047519/rz2666Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047519/rz2666Isup3.cml

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

C10H8·2C16H14N4	F(000) = 688
Mr = 652.78	Dx = 1.313 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 7079 reflections
a = 9.2224 (1) Å	θ = 3.9–75.7°
b = 22.8371 (2) Å	µ = 0.63 mm−1
c = 8.8760 (1) Å	T = 130 K
β = 117.936 (2)°	Plate, colourless
V = 1651.56 (3) Å3	0.20 × 0.15 × 0.05 mm
Z = 2

Oxford Diffraction SuperNova diffractometer	3020 independent reflections
Radiation source: Nova Cu X-ray Source	2671 reflections with I > 2/s(I)
mirror	Rint = 0.019
ω scans	θmax = 68.2°, θmin = 6.7°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	h = −11→8
Tmin = 0.931, Tmax = 1.000	k = −27→20
9878 measured reflections	l = −9→10

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0529P)2 + 0.2963P] where P = (Fo2 + 2Fc2)/3
3020 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.19 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
N2	0.87262 (11)	0.11061 (4)	0.09736 (12)	0.0241 (2)
N7	0.66539 (11)	0.16648 (4)	0.09585 (12)	0.0245 (2)
H7N	0.7317	0.1969	0.1069	0.029*
N14	0.06413 (11)	0.21713 (4)	0.08789 (13)	0.0261 (2)
H14N	0.0015	0.1862	0.0829	0.031*
N16	−0.13109 (11)	0.27154 (4)	0.11442 (12)	0.0244 (2)
C1	0.73812 (12)	0.11242 (5)	0.11994 (13)	0.0210 (2)
C3	0.95160 (13)	0.05927 (5)	0.12410 (15)	0.0280 (3)
H3	1.0460	0.0578	0.1073	0.034*
C4	0.90549 (14)	0.00852 (5)	0.17415 (16)	0.0298 (3)
H4	0.9659	−0.0267	0.1916	0.036*
C5	0.76666 (14)	0.01096 (5)	0.19811 (14)	0.0266 (2)
H5	0.7314	−0.0229	0.2341	0.032*
C6	0.68089 (13)	0.06259 (5)	0.16949 (14)	0.0234 (2)
H6	0.5847	0.0646	0.1829	0.028*
C8	0.51516 (13)	0.17821 (4)	0.09628 (13)	0.0207 (2)
C9	0.37373 (13)	0.14622 (4)	−0.00512 (13)	0.0213 (2)
H9	0.3791	0.1146	−0.0719	0.026*
C10	0.22525 (13)	0.16003 (4)	−0.00954 (13)	0.0209 (2)
H10	0.1301	0.1378	−0.0795	0.025*
C11	0.21415 (13)	0.20611 (4)	0.08742 (13)	0.0212 (2)
C12	0.35601 (13)	0.23827 (5)	0.18907 (14)	0.0237 (2)
H12	0.3507	0.2698	0.2561	0.028*
C13	0.50413 (13)	0.22456 (5)	0.19288 (13)	0.0225 (2)
H13	0.5992	0.2470	0.2620	0.027*
C15	−0.00317 (13)	0.27123 (5)	0.08107 (13)	0.0218 (2)
C17	−0.20195 (13)	0.32340 (5)	0.10952 (15)	0.0273 (3)
H17	−0.2923	0.3238	0.1333	0.033*
C18	−0.15272 (14)	0.37602 (5)	0.07244 (15)	0.0271 (2)
H18	−0.2051	0.4117	0.0736	0.032*
C19	−0.02310 (14)	0.37485 (5)	0.03317 (14)	0.0260 (2)
H19	0.0130	0.4100	0.0041	0.031*
C20	0.05239 (13)	0.32251 (5)	0.03668 (14)	0.0247 (2)
H20	0.1405	0.3210	0.0096	0.030*
C21	0.49781 (18)	0.09257 (6)	0.65351 (19)	0.0418 (3)
H21	0.5113	0.1219	0.7348	0.050*
C22	0.41095 (17)	0.10534 (6)	0.4784 (2)	0.0407 (3)
H22	0.3659	0.1433	0.4418	0.049*
C23	0.39118 (14)	0.06342 (6)	0.36099 (16)	0.0338 (3)
H23	0.3327	0.0726	0.2430	0.041*
C24	0.45620 (13)	0.00641 (5)	0.41152 (14)	0.0260 (2)
C25	0.43734 (15)	−0.03839 (6)	0.29296 (16)	0.0347 (3)
H25	0.3784	−0.0304	0.1742	0.042*

	U11	U22	U33	U12	U13	U23
N2	0.0202 (4)	0.0227 (5)	0.0307 (5)	−0.0003 (3)	0.0131 (4)	−0.0019 (4)
N7	0.0202 (4)	0.0190 (4)	0.0381 (5)	−0.0005 (3)	0.0169 (4)	0.0010 (4)
N14	0.0216 (5)	0.0195 (4)	0.0415 (6)	−0.0003 (3)	0.0184 (4)	−0.0002 (4)
N16	0.0201 (4)	0.0214 (5)	0.0329 (5)	0.0005 (3)	0.0135 (4)	−0.0004 (4)
C1	0.0183 (5)	0.0210 (5)	0.0223 (5)	−0.0006 (4)	0.0084 (4)	−0.0027 (4)
C3	0.0220 (5)	0.0275 (6)	0.0365 (6)	0.0019 (4)	0.0154 (5)	−0.0039 (5)
C4	0.0278 (6)	0.0227 (6)	0.0369 (6)	0.0056 (4)	0.0135 (5)	−0.0008 (5)
C5	0.0275 (6)	0.0209 (5)	0.0287 (6)	−0.0019 (4)	0.0110 (5)	0.0001 (4)
C6	0.0208 (5)	0.0238 (5)	0.0266 (5)	−0.0013 (4)	0.0118 (4)	−0.0010 (4)
C8	0.0188 (5)	0.0189 (5)	0.0249 (5)	0.0023 (4)	0.0108 (4)	0.0042 (4)
C9	0.0236 (5)	0.0183 (5)	0.0236 (5)	0.0005 (4)	0.0123 (4)	−0.0003 (4)
C10	0.0191 (5)	0.0193 (5)	0.0227 (5)	−0.0016 (4)	0.0085 (4)	0.0015 (4)
C11	0.0197 (5)	0.0192 (5)	0.0258 (5)	0.0024 (4)	0.0115 (4)	0.0034 (4)
C12	0.0239 (5)	0.0211 (5)	0.0269 (5)	0.0013 (4)	0.0124 (4)	−0.0028 (4)
C13	0.0192 (5)	0.0209 (5)	0.0247 (5)	−0.0020 (4)	0.0081 (4)	−0.0011 (4)
C15	0.0177 (5)	0.0221 (5)	0.0236 (5)	0.0003 (4)	0.0078 (4)	−0.0012 (4)
C17	0.0216 (5)	0.0258 (6)	0.0364 (6)	0.0022 (4)	0.0151 (5)	−0.0016 (5)
C18	0.0248 (5)	0.0212 (5)	0.0313 (6)	0.0047 (4)	0.0098 (5)	−0.0005 (4)
C19	0.0250 (5)	0.0224 (5)	0.0255 (5)	−0.0019 (4)	0.0077 (4)	0.0019 (4)
C20	0.0213 (5)	0.0261 (5)	0.0276 (5)	−0.0002 (4)	0.0122 (4)	0.0015 (4)
C21	0.0534 (8)	0.0369 (7)	0.0546 (8)	−0.0155 (6)	0.0416 (7)	−0.0104 (6)
C22	0.0383 (7)	0.0321 (6)	0.0674 (9)	0.0032 (5)	0.0378 (7)	0.0111 (6)
C23	0.0219 (5)	0.0436 (7)	0.0356 (6)	0.0009 (5)	0.0132 (5)	0.0154 (5)
C24	0.0186 (5)	0.0352 (6)	0.0250 (6)	−0.0054 (4)	0.0108 (4)	0.0041 (4)
C25	0.0350 (6)	0.0458 (7)	0.0272 (6)	−0.0154 (5)	0.0178 (5)	−0.0032 (5)

N2—C3	1.3415 (14)	C11—C12	1.3996 (15)
N2—C1	1.3466 (14)	C12—C13	1.3864 (15)
N7—C1	1.3732 (13)	C12—H12	0.9500
N7—C8	1.4129 (13)	C13—H13	0.9500
N7—H7N	0.9001	C15—C20	1.4066 (15)
N14—C15	1.3711 (14)	C20—C19	1.3763 (16)
N14—C11	1.4081 (13)	C20—H20	0.9500
N14—H14N	0.8999	C19—C18	1.3934 (16)
N16—C17	1.3436 (14)	C19—H19	0.9500
N16—C15	1.3441 (14)	C18—C17	1.3778 (16)
C1—C6	1.4087 (15)	C18—H18	0.9500
C3—C4	1.3778 (17)	C17—H17	0.9500
C3—H3	0.9500	C21—C25i	1.359 (2)
C4—C5	1.3938 (16)	C21—C22	1.405 (2)
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.3756 (15)	C22—C23	1.363 (2)
C5—H5	0.9500	C22—H22	0.9500
C6—H6	0.9500	C23—C24	1.4155 (18)
C8—C9	1.3947 (15)	C23—H23	0.9500
C8—C13	1.3955 (15)	C24—C25	1.4188 (18)
C9—C10	1.3877 (15)	C24—C24i	1.420 (2)
C9—H9	0.9500	C25—C21i	1.359 (2)
C10—C11	1.3934 (15)	C25—H25	0.9500
C10—H10	0.9500
C3—N2—C1	117.53 (9)	C13—C12—H12	119.7
C1—N7—C8	125.32 (9)	C11—C12—H12	119.7
C1—N7—H7N	114.8	C12—C13—C8	120.73 (10)
C8—N7—H7N	118.1	C12—C13—H13	119.6
C15—N14—C11	125.87 (9)	C8—C13—H13	119.6
C15—N14—H14N	116.0	N16—C15—N14	114.89 (9)
C11—N14—H14N	117.9	N16—C15—C20	121.99 (10)
C17—N16—C15	117.47 (9)	N14—C15—C20	123.08 (10)
N2—C1—N7	114.91 (9)	C19—C20—C15	118.86 (10)
N2—C1—C6	121.85 (9)	C19—C20—H20	120.6
N7—C1—C6	123.22 (9)	C15—C20—H20	120.6
N2—C3—C4	124.62 (10)	C20—C19—C18	119.67 (10)
N2—C3—H3	117.7	C20—C19—H19	120.2
C4—C3—H3	117.7	C18—C19—H19	120.2
C3—C4—C5	117.38 (10)	C17—C18—C19	117.42 (10)
C3—C4—H4	121.3	C17—C18—H18	121.3
C5—C4—H4	121.3	C19—C18—H18	121.3
C6—C5—C4	119.73 (10)	N16—C17—C18	124.53 (10)
C6—C5—H5	120.1	N16—C17—H17	117.7
C4—C5—H5	120.1	C18—C17—H17	117.7
C5—C6—C1	118.88 (10)	C25i—C21—C22	120.32 (13)
C5—C6—H6	120.6	C25i—C21—H21	119.8
C1—C6—H6	120.6	C22—C21—H21	119.8
C9—C8—C13	118.59 (9)	C23—C22—C21	120.17 (12)
C9—C8—N7	121.38 (9)	C23—C22—H22	119.9
C13—C8—N7	119.95 (9)	C21—C22—H22	119.9
C10—C9—C8	120.75 (10)	C22—C23—C24	121.24 (12)
C10—C9—H9	119.6	C22—C23—H23	119.4
C8—C9—H9	119.6	C24—C23—H23	119.4
C9—C10—C11	120.75 (10)	C23—C24—C25	122.80 (11)
C9—C10—H10	119.6	C23—C24—C24i	118.50 (14)
C11—C10—H10	119.6	C25—C24—C24i	118.70 (14)
C10—C11—C12	118.52 (9)	C21i—C25—C24	121.07 (12)
C10—C11—N14	119.57 (9)	C21i—C25—H25	119.5
C12—C11—N14	121.83 (10)	C24—C25—H25	119.5
C13—C12—C11	120.67 (10)
C3—N2—C1—N7	178.10 (10)	N14—C11—C12—C13	176.65 (10)
C3—N2—C1—C6	−0.10 (15)	C11—C12—C13—C8	−0.39 (16)
C8—N7—C1—N2	173.65 (10)	C9—C8—C13—C12	0.44 (16)
C8—N7—C1—C6	−8.18 (17)	N7—C8—C13—C12	177.21 (10)
C1—N2—C3—C4	−0.51 (17)	C17—N16—C15—N14	−179.99 (10)
N2—C3—C4—C5	0.15 (18)	C17—N16—C15—C20	−2.18 (16)
C3—C4—C5—C6	0.83 (17)	C11—N14—C15—N16	−168.34 (10)
C4—C5—C6—C1	−1.40 (16)	C11—N14—C15—C20	13.88 (17)
N2—C1—C6—C5	1.05 (16)	N16—C15—C20—C19	2.30 (16)
N7—C1—C6—C5	−176.99 (10)	N14—C15—C20—C19	179.93 (10)
C1—N7—C8—C9	−51.81 (15)	C15—C20—C19—C18	−0.34 (16)
C1—N7—C8—C13	131.51 (11)	C20—C19—C18—C17	−1.53 (16)
C13—C8—C9—C10	−0.20 (15)	C15—N16—C17—C18	0.14 (17)
N7—C8—C9—C10	−176.92 (9)	C19—C18—C17—N16	1.71 (18)
C8—C9—C10—C11	−0.10 (16)	C25i—C21—C22—C23	−0.01 (19)
C9—C10—C11—C12	0.16 (15)	C21—C22—C23—C24	0.29 (18)
C9—C10—C11—N14	−176.49 (9)	C22—C23—C24—C25	179.68 (11)
C15—N14—C11—C10	−138.39 (11)	C22—C23—C24—C24i	−0.23 (19)
C15—N14—C11—C12	45.08 (16)	C23—C24—C25—C21i	179.73 (11)
C10—C11—C12—C13	0.08 (16)	C24i—C24—C25—C21i	−0.36 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7N···N16ii	0.90	2.11	3.0027 (13)	175
N14—H14N···N2iii	0.90	2.13	3.0305 (13)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7N⋯N16i	0.90	2.11	3.0027 (13)	175
N14—H14N⋯N2ii	0.90	2.13	3.0305 (13)	174

Symmetry codes: (i) ; (ii) .