N,N'-(4,5-Dimethyl-1,2-phenyl-ene)bis-(pyridine-2-carboxamide).

In the title compound, C(20)H(18)N(4)O(2), the dihedral angles between the central benzene ring and the pyridine rings are 57.55 (6) and 22.05 (8)°. The mol-ecular conformation is stabilized by intra-molecular N-H⋯N inter-actions and in the crystal structure an inter-molecular asymmetric cyclic hydrogen-bonding association involving both amide N-H donors and a common amide O-atom acceptor gives a chain extending along the c axis.

Related literature

For related structures, see: Jain et al. (2004 ▶); Lin et al. (2001 ▶); Roodt et al. (2011 ▶); Schutte et al. (2011 ▶); Van der Berg et al. (2011 ▶).

Experimental

Crystal data

C20H18N4O2

M = 346.38

Monoclinic,

a = 12.1299 (8) Å

b = 18.9418 (8) Å

c = 7.7549 (4) Å

β = 100.375 (4)°

V = 1752.65 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.78 × 0.08 × 0.07 mm

Data collection

Bruker X8 APEXII KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.990, T max = 0.994

15674 measured reflections

3860 independent reflections

3529 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.090

S = 1.04

3860 reflections

237 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035064/zs2225sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035064/zs2225Isup2.hkl

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

C20H18N4O2	F(000) = 728
Mr = 346.38	Dx = 1.313 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5487 reflections
a = 12.1299 (8) Å	θ = 3.1–28.3°
b = 18.9418 (8) Å	µ = 0.09 mm−1
c = 7.7549 (4) Å	T = 100 K
β = 100.375 (4)°	Needle, colourless
V = 1752.65 (17) Å3	0.78 × 0.08 × 0.07 mm
Z = 4

Bruker X8 APEXII KappaCCD diffractometer	3860 independent reflections
Radiation source: sealed tube	3529 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 28°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −16→16
Tmin = 0.990, Tmax = 0.994	k = −24→24
15674 measured reflections	l = −10→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0456P)2 + 0.7043P] where P = (Fo2 + 2Fc2)/3
3860 reflections	(Δ/σ)max = 0.001
237 parameters	Δρmax = 0.26 e Å−3
2 restraints	Δρmin = −0.20 e Å−3

Experimental. The intensity data was collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 30 s/frame. A total of 1895 frames was collected with a frame width of 0.5° covering up to θ = 28.29° with 99.9% completeness accomplished.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)
C6	0.77131 (13)	0.70520 (9)	0.3849 (2)	0.0204 (3)
C10	0.34827 (15)	0.64314 (11)	0.4195 (3)	0.0336 (4)
H10A	0.2857	0.6104	0.4193	0.050*	0.5
H10B	0.3246	0.6815	0.3361	0.050*	0.5
H10C	0.3713	0.6629	0.5373	0.050*	0.5
H10D	0.3688	0.6927	0.4424	0.050*	0.5
H10E	0.3298	0.6217	0.5257	0.050*	0.5
H10F	0.2831	0.6403	0.3245	0.050*	0.5
C11	0.33503 (15)	0.48994 (11)	0.3373 (3)	0.0313 (4)
H11A	0.3459	0.4411	0.3025	0.047*	0.5
H11B	0.2703	0.5102	0.2592	0.047*	0.5
H11C	0.3218	0.4908	0.4583	0.047*	0.5
H11D	0.2794	0.5204	0.3775	0.047*	0.5
H11E	0.355	0.4512	0.4208	0.047*	0.5
H11F	0.3035	0.4706	0.2217	0.047*	0.5
C15	0.77150 (13)	0.44582 (8)	0.2917 (2)	0.0202 (2)
N2	0.73461 (11)	0.64533 (7)	0.2985 (2)	0.0221 (3)
N3	0.72056 (11)	0.50299 (7)	0.21172 (19)	0.0190 (3)
O1	0.72183 (10)	0.73844 (7)	0.48200 (17)	0.0277 (3)
O2	0.74071 (9)	0.41395 (6)	0.41242 (15)	0.0202 (2)
H2'	0.7803 (17)	0.6283 (10)	0.237 (3)	0.027 (5)*
H3'	0.7438 (16)	0.5199 (10)	0.122 (3)	0.024 (5)*
C1	1.03548 (14)	0.71236 (10)	0.2222 (2)	0.0283 (4)
H1	1.0731	0.6853	0.1474	0.034*
C2	1.08852 (15)	0.77174 (10)	0.3009 (2)	0.0293 (4)
H2	1.1603	0.7852	0.2795	0.035*
C3	1.03552 (16)	0.81103 (10)	0.4107 (2)	0.0289 (4)
H3	1.07	0.8521	0.4668	0.035*
C4	0.93064 (15)	0.78956 (9)	0.4380 (2)	0.0249 (4)
H4	0.8918	0.8154	0.5134	0.03*
C5	0.88403 (13)	0.72965 (9)	0.3529 (2)	0.0197 (3)
C7	0.63512 (12)	0.60847 (8)	0.3093 (2)	0.0192 (3)
C8	0.54288 (15)	0.64111 (9)	0.3586 (2)	0.0241 (3)
H8	0.5468	0.6899	0.3874	0.029*
C9	0.44549 (13)	0.60415 (9)	0.3667 (2)	0.0243 (4)
C12	0.43827 (14)	0.53253 (9)	0.3249 (2)	0.0235 (3)
C13	0.53017 (14)	0.50011 (9)	0.2728 (2)	0.0215 (3)
H13	0.5258	0.4515	0.2421	0.026*
C14	0.62761 (12)	0.53699 (8)	0.2646 (2)	0.0189 (3)
C16	0.87530 (13)	0.42368 (9)	0.2250 (2)	0.0189 (3)
C17	0.93911 (15)	0.36937 (9)	0.3085 (2)	0.0255 (4)
H17	0.9157	0.344	0.4012	0.031*
C18	1.03894 (15)	0.35268 (10)	0.2530 (3)	0.0295 (4)
H18	1.0859	0.316	0.3079	0.035*
C19	1.06792 (15)	0.39063 (10)	0.1168 (2)	0.0283 (4)
H19	1.1357	0.3806	0.0764	0.034*
C20	0.99767 (15)	0.44332 (10)	0.0395 (3)	0.0301 (4)
H20	1.0181	0.4685	−0.056	0.036*
N1	0.93415 (12)	0.69083 (8)	0.2456 (2)	0.0248 (3)
N4	0.90251 (12)	0.46069 (8)	0.09200 (19)	0.0245 (3)

	U11	U22	U33	U12	U13	U23
C6	0.0205 (7)	0.0210 (8)	0.0200 (8)	0.0032 (6)	0.0050 (6)	0.0032 (6)
C10	0.0211 (8)	0.0387 (10)	0.0437 (12)	0.0041 (7)	0.0132 (8)	−0.0001 (9)
C11	0.0227 (8)	0.0378 (10)	0.0351 (10)	−0.0060 (7)	0.0102 (8)	−0.0020 (8)
C15	0.0209 (4)	0.0201 (5)	0.0205 (4)	−0.0022 (3)	0.0064 (4)	−0.0014 (4)
N2	0.0184 (7)	0.0206 (7)	0.0304 (8)	0.0008 (5)	0.0124 (6)	−0.0027 (6)
N3	0.0181 (6)	0.0214 (7)	0.0192 (7)	−0.0007 (5)	0.0081 (5)	0.0004 (6)
O1	0.0252 (6)	0.0322 (7)	0.0283 (7)	0.0007 (5)	0.0117 (5)	−0.0061 (6)
O2	0.0209 (4)	0.0201 (5)	0.0205 (4)	−0.0022 (3)	0.0064 (4)	−0.0014 (4)
C1	0.0238 (8)	0.0362 (10)	0.0265 (9)	−0.0018 (7)	0.0088 (7)	−0.0063 (8)
C2	0.0253 (9)	0.0384 (11)	0.0253 (9)	−0.0092 (7)	0.0078 (7)	0.0008 (8)
C3	0.0343 (10)	0.0279 (9)	0.0243 (9)	−0.0102 (7)	0.0043 (8)	−0.0031 (8)
C4	0.0291 (9)	0.0253 (8)	0.0215 (8)	−0.0022 (7)	0.0079 (7)	−0.0008 (7)
C5	0.0196 (7)	0.0191 (8)	0.0213 (8)	0.0005 (6)	0.0061 (6)	0.0034 (6)
C7	0.0168 (7)	0.0215 (8)	0.0202 (8)	−0.0008 (6)	0.0060 (6)	0.0027 (6)
C8	0.0212 (7)	0.0253 (8)	0.0268 (9)	0.0037 (7)	0.0072 (7)	0.0020 (7)
C9	0.0196 (8)	0.0314 (9)	0.0232 (8)	0.0047 (7)	0.0070 (7)	0.0027 (7)
C12	0.0174 (7)	0.0329 (9)	0.0205 (8)	−0.0024 (7)	0.0041 (6)	0.0035 (7)
C13	0.0217 (7)	0.0238 (8)	0.0196 (8)	−0.0022 (6)	0.0055 (6)	−0.0005 (6)
C14	0.0173 (7)	0.0240 (8)	0.0158 (8)	0.0020 (6)	0.0044 (6)	0.0014 (6)
C16	0.0188 (7)	0.0188 (7)	0.0190 (7)	−0.0015 (6)	0.0035 (6)	−0.0040 (6)
C17	0.0262 (8)	0.0248 (8)	0.0274 (9)	0.0022 (7)	0.0097 (7)	0.0020 (7)
C18	0.0271 (9)	0.0278 (9)	0.0346 (10)	0.0079 (7)	0.0079 (8)	0.0012 (8)
C19	0.0210 (8)	0.0356 (10)	0.0302 (9)	0.0049 (7)	0.0096 (7)	−0.0046 (8)
C20	0.0274 (9)	0.0375 (10)	0.0282 (9)	0.0030 (7)	0.0128 (8)	0.0046 (8)
N1	0.0218 (7)	0.0269 (7)	0.0275 (8)	−0.0029 (6)	0.0089 (6)	−0.0051 (6)
N4	0.0231 (7)	0.0290 (8)	0.0227 (7)	0.0031 (6)	0.0080 (6)	0.0027 (6)

C6—O1	1.219 (2)	C1—H1	0.95
C6—N2	1.351 (2)	C2—C3	1.375 (3)
C6—C5	1.506 (2)	C2—H2	0.95
C10—C9	1.509 (2)	C3—C4	1.388 (2)
C10—H10A	0.98	C3—H3	0.95
C10—H10B	0.98	C4—C5	1.381 (2)
C10—H10C	0.98	C4—H4	0.95
C10—H10D	0.98	C5—N1	1.336 (2)
C10—H10E	0.98	C7—C8	1.391 (2)
C10—H10F	0.98	C7—C14	1.397 (2)
C11—C12	1.507 (2)	C8—C9	1.384 (2)
C11—H11A	0.98	C8—H8	0.95
C11—H11B	0.98	C9—C12	1.394 (2)
C11—H11C	0.98	C12—C13	1.395 (2)
C11—H11D	0.98	C13—C14	1.384 (2)
C11—H11E	0.98	C13—H13	0.95
C11—H11F	0.98	C16—N4	1.336 (2)
C15—O2	1.2274 (19)	C16—C17	1.377 (2)
C15—N3	1.342 (2)	C17—C18	1.392 (2)
C15—C16	1.505 (2)	C17—H17	0.95
N2—C7	1.410 (2)	C18—C19	1.374 (3)
N2—H2'	0.86 (2)	C18—H18	0.95
N3—C14	1.421 (2)	C19—C20	1.378 (3)
N3—H3'	0.86 (2)	C19—H19	0.95
C1—N1	1.338 (2)	C20—N4	1.333 (2)
C1—C2	1.382 (3)	C20—H20	0.95
O1—C6—N2	125.78 (16)	C15—N3—H3'	119.0 (13)
O1—C6—C5	120.35 (15)	C14—N3—H3'	117.3 (13)
N2—C6—C5	113.87 (14)	N1—C1—C2	123.65 (17)
C9—C10—H10A	109.5	N1—C1—H1	118.2
C9—C10—H10B	109.5	C2—C1—H1	118.2
H10A—C10—H10B	109.5	C3—C2—C1	118.80 (16)
C9—C10—H10C	109.5	C3—C2—H2	120.6
H10A—C10—H10C	109.5	C1—C2—H2	120.6
H10B—C10—H10C	109.5	C2—C3—C4	118.66 (16)
C9—C10—H10D	109.5	C2—C3—H3	120.7
H10A—C10—H10D	141.1	C4—C3—H3	120.7
H10B—C10—H10D	56.3	C5—C4—C3	118.40 (16)
H10C—C10—H10D	56.3	C5—C4—H4	120.8
C9—C10—H10E	109.5	C3—C4—H4	120.8
H10A—C10—H10E	56.3	N1—C5—C4	123.82 (14)
H10B—C10—H10E	141.1	N1—C5—C6	117.49 (14)
H10C—C10—H10E	56.3	C4—C5—C6	118.67 (15)
H10D—C10—H10E	109.5	C8—C7—C14	118.66 (14)
C9—C10—H10F	109.5	C8—C7—N2	122.39 (15)
H10A—C10—H10F	56.3	C14—C7—N2	118.93 (14)
H10B—C10—H10F	56.3	C9—C8—C7	121.53 (15)
H10C—C10—H10F	141.1	C9—C8—H8	119.2
H10D—C10—H10F	109.5	C7—C8—H8	119.2
H10E—C10—H10F	109.5	C8—C9—C12	120.01 (15)
C12—C11—H11A	109.5	C8—C9—C10	118.66 (16)
C12—C11—H11B	109.5	C12—C9—C10	121.33 (16)
H11A—C11—H11B	109.5	C9—C12—C13	118.41 (15)
C12—C11—H11C	109.5	C9—C12—C11	121.62 (16)
H11A—C11—H11C	109.5	C13—C12—C11	119.96 (16)
H11B—C11—H11C	109.5	C14—C13—C12	121.65 (15)
C12—C11—H11D	109.5	C14—C13—H13	119.2
H11A—C11—H11D	141.1	C12—C13—H13	119.2
H11B—C11—H11D	56.3	C13—C14—C7	119.73 (14)
H11C—C11—H11D	56.3	C13—C14—N3	120.85 (14)
C12—C11—H11E	109.5	C7—C14—N3	119.42 (13)
H11A—C11—H11E	56.3	N4—C16—C17	123.97 (15)
H11B—C11—H11E	141.1	N4—C16—C15	117.22 (14)
H11C—C11—H11E	56.3	C17—C16—C15	118.74 (14)
H11D—C11—H11E	109.5	C16—C17—C18	118.08 (16)
C12—C11—H11F	109.5	C16—C17—H17	121
H11A—C11—H11F	56.3	C18—C17—H17	121
H11B—C11—H11F	56.3	C19—C18—C17	118.40 (17)
H11C—C11—H11F	141.1	C19—C18—H18	120.8
H11D—C11—H11F	109.5	C17—C18—H18	120.8
H11E—C11—H11F	109.5	C18—C19—C20	119.32 (16)
O2—C15—N3	124.85 (15)	C18—C19—H19	120.3
O2—C15—C16	120.91 (14)	C20—C19—H19	120.3
N3—C15—C16	114.22 (14)	N4—C20—C19	123.20 (17)
C6—N2—C7	126.56 (14)	N4—C20—H20	118.4
C6—N2—H2'	113.8 (13)	C19—C20—H20	118.4
C7—N2—H2'	119.5 (13)	C5—N1—C1	116.67 (14)
C15—N3—C14	123.74 (14)	C20—N4—C16	117.01 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2′···N1	0.86 (2)	2.20 (2)	2.6698 (19)	114.2 (16)
N2—H2′···N3	0.86 (2)	2.48 (2)	2.777 (2)	101.2 (15)
N2—H2′···O2i	0.86 (2)	2.60 (2)	3.2112 (19)	129.0 (17)
N3—H3′···O2i	0.86 (2)	2.05 (2)	2.8508 (19)	155.5 (18)
N3—H3′···N4	0.86 (2)	2.28 (2)	2.6670 (19)	107.8 (15)
C8—H8···O1	0.95	2.31	2.877 (2)	118
C2—H2···O1ii	0.95	2.59	3.195 (2)	122
C3—H3···O2iii	0.95	2.48	3.160 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2′⋯N1	0.86 (2)	2.20 (2)	2.6698 (19)	114.2 (16)
N2—H2′⋯N3	0.86 (2)	2.48 (2)	2.777 (2)	101.2 (15)
N2—H2′⋯O2i	0.86 (2)	2.60 (2)	3.2112 (19)	129.0 (17)
N3—H3′⋯O2i	0.86 (2)	2.05 (2)	2.8508 (19)	155.5 (18)
N3—H3′⋯N4	0.86 (2)	2.28 (2)	2.6670 (19)	107.8 (15)

Symmetry code: (i) .