N,N′-Bis(2-pyrid­yl)naphthalene-1,4-carboxamide

The title compound, C₂₂H₁₆N₄O₂, crystallizes in an anti C=O conformation. The two amide groups are twisted away from the attached ring by 69.94 (6) and 62.99 (7)°. The crystal packing is stabilized by N—H...N and C—H...O hydrogen bonds, and also by C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.047
• wR factor = 0.168
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

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Computing details

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

N,N'-Bis(2-pyridyl)naphthalene-1,4-carboxamide

Crystal data

C22H16N4O2	F(000) = 768
Mr = 368.39	Dx = 1.393 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25355 reflections
a = 13.6987 (3) Å	θ = 3.2–27.5°
b = 9.2100 (2) Å	µ = 0.09 mm^−1
c = 15.1404 (4) Å	T = 153 K
β = 113.091 (1)°	Block, colourless
V = 1757.15 (7) Å^3	0.54 × 0.46 × 0.43 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	3685 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.019
Graphite monochromator	θmax = 27.5°, θmin = 3.2°
ω scans	h = −17→17
26983 measured reflections	k = −11→11
4020 independent reflections	l = −19→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.168	w = 1/[σ^2(Fo^2) + (0.0892P)^2 + 1.7P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
4020 reflections	Δρmax = 0.33 e Å^−3
262 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (2)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.92098 (11)	0.59251 (15)	0.58509 (12)	0.0356 (4)
O2	0.41888 (11)	0.20414 (17)	0.34590 (15)	0.0466 (5)
N1	0.79102 (12)	0.76025 (16)	0.51107 (11)	0.0231 (3)
N2	0.78213 (12)	1.00389 (16)	0.53998 (11)	0.0245 (3)
N3	0.54890 (12)	0.03184 (16)	0.40203 (12)	0.0236 (3)
N4	0.55586 (12)	−0.20997 (16)	0.36907 (11)	0.0221 (3)
C1	0.74703 (13)	0.50672 (18)	0.49263 (13)	0.0203 (4)
C2	0.66885 (14)	0.48926 (19)	0.52696 (13)	0.0231 (4)
H2	0.6655	0.5526	0.5752	0.028*
C3	0.59342 (14)	0.37737 (19)	0.49063 (13)	0.0231 (4)
H3	0.5398	0.3654	0.5151	0.028*
C4	0.59643 (13)	0.28569 (18)	0.42053 (12)	0.0201 (3)
C5	0.67934 (14)	0.21432 (19)	0.30583 (13)	0.0237 (4)
H5	0.6288	0.1388	0.2802	0.028*
C6	0.75560 (15)	0.2370 (2)	0.26971 (14)	0.0280 (4)
H6	0.7564	0.1788	0.2182	0.034*
C7	0.83281 (15)	0.3461 (2)	0.30847 (14)	0.0273 (4)
H7	0.8857	0.3602	0.2833	0.033*
C8	0.83222 (13)	0.43183 (19)	0.38186 (13)	0.0232 (4)
H8	0.8855	0.5038	0.4082	0.028*
C9	0.75265 (13)	0.41414 (17)	0.41912 (12)	0.0190 (3)
C10	0.67526 (12)	0.30262 (18)	0.38118 (12)	0.0191 (3)
C11	0.82987 (13)	0.62299 (19)	0.53493 (13)	0.0221 (4)
C12	0.84619 (14)	0.89075 (19)	0.54630 (12)	0.0217 (4)
C13	0.95671 (15)	0.9002 (2)	0.58408 (14)	0.0271 (4)
H13	0.9992	0.8183	0.5850	0.032*
C14	1.00237 (16)	1.0332 (2)	0.62015 (15)	0.0323 (4)
H14	1.0774	1.0438	0.6464	0.039*
C15	0.93785 (17)	1.1509 (2)	0.61772 (15)	0.0330 (4)
H15	0.9675	1.2423	0.6436	0.040*
C16	0.82909 (16)	1.1306 (2)	0.57649 (14)	0.0293 (4)
H16	0.7849	1.2114	0.5739	0.035*
C17	0.51177 (14)	0.1708 (2)	0.38475 (14)	0.0245 (4)
C18	0.49261 (14)	−0.09578 (19)	0.36216 (12)	0.0220 (4)
C19	0.38190 (15)	−0.1027 (2)	0.31845 (15)	0.0298 (4)
H19	0.3394	−0.0207	0.3173	0.036*
C20	0.33623 (15)	−0.2329 (2)	0.27684 (15)	0.0312 (4)
H20	0.2612	−0.2414	0.2463	0.037*
C21	0.40045 (16)	−0.3508 (2)	0.28001 (13)	0.0281 (4)
H21	0.3707	−0.4404	0.2507	0.034*
C22	0.50892 (15)	−0.3344 (2)	0.32702 (13)	0.0251 (4)
H22	0.5529	−0.4155	0.3298	0.030*
H1N	0.717 (2)	0.770 (3)	0.4730 (18)	0.034 (6)*
H3N	0.622 (2)	0.021 (3)	0.4368 (19)	0.037 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0218 (7)	0.0241 (7)	0.0504 (9)	0.0020 (5)	0.0030 (6)	−0.0028 (6)
O2	0.0180 (7)	0.0261 (8)	0.0795 (13)	0.0024 (5)	0.0018 (7)	0.0011 (8)
N1	0.0188 (7)	0.0179 (7)	0.0291 (8)	−0.0017 (5)	0.0057 (6)	−0.0021 (6)
N2	0.0258 (8)	0.0177 (7)	0.0247 (7)	−0.0009 (6)	0.0043 (6)	0.0001 (6)
N3	0.0161 (7)	0.0174 (7)	0.0330 (8)	−0.0015 (5)	0.0048 (6)	0.0005 (6)
N4	0.0233 (7)	0.0195 (7)	0.0232 (7)	−0.0036 (6)	0.0089 (6)	−0.0012 (6)
C1	0.0198 (8)	0.0143 (7)	0.0253 (8)	0.0013 (6)	0.0071 (7)	−0.0003 (6)
C2	0.0237 (8)	0.0205 (8)	0.0253 (8)	0.0015 (6)	0.0097 (7)	−0.0026 (6)
C3	0.0209 (8)	0.0209 (8)	0.0298 (9)	0.0014 (6)	0.0123 (7)	0.0023 (7)
C4	0.0157 (7)	0.0152 (7)	0.0266 (8)	0.0012 (6)	0.0052 (6)	0.0019 (6)
C5	0.0216 (8)	0.0205 (8)	0.0262 (8)	0.0017 (6)	0.0062 (7)	−0.0034 (7)
C6	0.0286 (9)	0.0282 (10)	0.0283 (9)	0.0029 (7)	0.0125 (8)	−0.0057 (7)
C7	0.0243 (9)	0.0292 (9)	0.0313 (9)	0.0025 (7)	0.0142 (7)	−0.0001 (7)
C8	0.0190 (8)	0.0204 (8)	0.0301 (9)	0.0013 (6)	0.0094 (7)	0.0016 (7)
C9	0.0174 (7)	0.0144 (7)	0.0238 (8)	0.0031 (6)	0.0065 (6)	0.0020 (6)
C10	0.0165 (7)	0.0157 (7)	0.0227 (8)	0.0028 (6)	0.0051 (6)	0.0017 (6)
C11	0.0203 (8)	0.0189 (8)	0.0268 (8)	−0.0008 (6)	0.0088 (7)	−0.0039 (6)
C12	0.0230 (8)	0.0192 (8)	0.0207 (8)	−0.0033 (6)	0.0063 (7)	0.0005 (6)
C13	0.0234 (9)	0.0260 (9)	0.0304 (9)	−0.0031 (7)	0.0091 (7)	0.0003 (7)
C14	0.0260 (9)	0.0315 (10)	0.0343 (10)	−0.0090 (8)	0.0064 (8)	−0.0004 (8)
C15	0.0346 (10)	0.0240 (9)	0.0323 (10)	−0.0089 (8)	0.0043 (8)	−0.0008 (8)
C16	0.0327 (10)	0.0193 (9)	0.0286 (9)	−0.0013 (7)	0.0042 (8)	−0.0005 (7)
C17	0.0177 (8)	0.0202 (8)	0.0327 (9)	−0.0004 (6)	0.0067 (7)	−0.0002 (7)
C18	0.0209 (8)	0.0211 (8)	0.0229 (8)	−0.0041 (6)	0.0073 (7)	0.0005 (6)
C19	0.0198 (9)	0.0276 (9)	0.0380 (11)	−0.0030 (7)	0.0071 (8)	0.0010 (8)
C20	0.0225 (9)	0.0349 (10)	0.0303 (9)	−0.0090 (8)	0.0039 (7)	0.0004 (8)
C21	0.0324 (10)	0.0273 (9)	0.0225 (8)	−0.0110 (7)	0.0084 (7)	−0.0044 (7)
C22	0.0302 (9)	0.0213 (8)	0.0250 (8)	−0.0039 (7)	0.0119 (7)	−0.0024 (7)

Geometric parameters (Å, º)

O1—C11	1.212 (2)	C6—C7	1.409 (3)
O2—C17	1.214 (2)	C6—H6	0.95
N1—C11	1.364 (2)	C7—C8	1.366 (3)
N1—C12	1.409 (2)	C7—H7	0.95
N1—H1N	0.96 (3)	C8—C9	1.419 (2)
N2—C12	1.341 (2)	C8—H8	0.95
N2—C16	1.343 (2)	C9—C10	1.425 (2)
N3—C17	1.364 (2)	C12—C13	1.396 (2)
N3—C18	1.406 (2)	C13—C14	1.386 (3)
N3—H3N	0.94 (3)	C13—H13	0.95
N4—C18	1.340 (2)	C14—C15	1.390 (3)
N4—C22	1.346 (2)	C14—H14	0.95
C1—C2	1.371 (2)	C15—C16	1.384 (3)
C1—C9	1.428 (2)	C15—H15	0.95
C1—C11	1.508 (2)	C16—H16	0.95
C2—C3	1.409 (2)	C18—C19	1.398 (2)
C2—H2	0.95	C19—C20	1.384 (3)
C3—C4	1.369 (2)	C19—H19	0.95
C3—H3	0.95	C20—C21	1.387 (3)
C4—C10	1.432 (2)	C20—H20	0.95
C4—C17	1.505 (2)	C21—C22	1.381 (3)
C5—C6	1.372 (3)	C21—H21	0.95
C5—C10	1.420 (2)	C22—H22	0.95
C5—H5	0.95
C11—N1—C12	126.50 (15)	C9—C10—C4	118.29 (15)
C11—N1—H1N	117.3 (15)	O1—C11—N1	125.40 (16)
C12—N1—H1N	115.7 (15)	O1—C11—C1	121.32 (16)
C12—N2—C16	116.85 (16)	N1—C11—C1	113.27 (14)
C17—N3—C18	126.99 (15)	N2—C12—C13	123.70 (16)
C17—N3—H3N	116.2 (16)	N2—C12—N1	113.40 (15)
C18—N3—H3N	116.1 (16)	C13—C12—N1	122.90 (16)
C18—N4—C22	117.18 (15)	C14—C13—C12	117.78 (18)
C2—C1—C9	120.96 (16)	C14—C13—H13	121.1
C2—C1—C11	119.46 (15)	C12—C13—H13	121.1
C9—C1—C11	119.56 (15)	C13—C14—C15	119.63 (18)
C1—C2—C3	120.00 (16)	C13—C14—H14	120.2
C1—C2—H2	120.0	C15—C14—H14	120.2
C3—C2—H2	120.0	C16—C15—C14	117.90 (18)
C4—C3—C2	120.86 (16)	C16—C15—H15	121.0
C4—C3—H3	119.6	C14—C15—H15	121.0
C2—C3—H3	119.6	N2—C16—C15	124.05 (18)
C3—C4—C10	120.81 (15)	N2—C16—H16	118.0
C3—C4—C17	117.35 (15)	C15—C16—H16	118.0
C10—C4—C17	121.81 (15)	O2—C17—N3	124.89 (17)
C6—C5—C10	120.59 (17)	O2—C17—C4	120.64 (17)
C6—C5—H5	119.7	N3—C17—C4	114.46 (15)
C10—C5—H5	119.7	N4—C18—C19	123.30 (16)
C5—C6—C7	120.49 (17)	N4—C18—N3	113.18 (15)
C5—C6—H6	119.8	C19—C18—N3	123.51 (17)
C7—C6—H6	119.8	C20—C19—C18	117.89 (18)
C8—C7—C6	120.52 (17)	C20—C19—H19	121.1
C8—C7—H7	119.7	C18—C19—H19	121.1
C6—C7—H7	119.7	C19—C20—C21	119.68 (17)
C7—C8—C9	120.50 (17)	C19—C20—H20	120.2
C7—C8—H8	119.7	C21—C20—H20	120.2
C9—C8—H8	119.7	C22—C21—C20	118.14 (17)
C8—C9—C10	119.23 (15)	C22—C21—H21	120.9
C8—C9—C1	121.72 (15)	C20—C21—H21	120.9
C10—C9—C1	119.04 (15)	N4—C22—C21	123.71 (18)
C5—C10—C9	118.63 (15)	N4—C22—H22	118.1
C5—C10—C4	123.08 (16)	C21—C22—H22	118.1
C9—C1—C2—C3	0.9 (3)	C2—C1—C11—N1	−70.5 (2)
C11—C1—C2—C3	−177.54 (16)	C9—C1—C11—N1	111.02 (18)
C1—C2—C3—C4	−0.5 (3)	C16—N2—C12—C13	−3.1 (3)
C2—C3—C4—C10	−1.0 (3)	C16—N2—C12—N1	176.83 (16)
C2—C3—C4—C17	−179.03 (16)	C11—N1—C12—N2	−156.97 (17)
C10—C5—C6—C7	1.6 (3)	C11—N1—C12—C13	22.9 (3)
C5—C6—C7—C8	−0.7 (3)	N2—C12—C13—C14	2.4 (3)
C6—C7—C8—C9	−1.2 (3)	N1—C12—C13—C14	−177.46 (17)
C7—C8—C9—C10	2.0 (3)	C12—C13—C14—C15	0.1 (3)
C7—C8—C9—C1	−176.94 (17)	C13—C14—C15—C16	−1.7 (3)
C2—C1—C9—C8	179.17 (16)	C12—N2—C16—C15	1.3 (3)
C11—C1—C9—C8	−2.4 (2)	C14—C15—C16—N2	1.0 (3)
C2—C1—C9—C10	0.2 (2)	C18—N3—C17—O2	14.3 (3)
C11—C1—C9—C10	178.64 (15)	C18—N3—C17—C4	−167.19 (17)
C6—C5—C10—C9	−0.7 (3)	C3—C4—C17—O2	62.0 (3)
C6—C5—C10—C4	178.85 (17)	C10—C4—C17—O2	−116.0 (2)
C8—C9—C10—C5	−1.1 (2)	C3—C4—C17—N3	−116.59 (19)
C1—C9—C10—C5	177.88 (15)	C10—C4—C17—N3	65.4 (2)
C8—C9—C10—C4	179.33 (15)	C22—N4—C18—C19	3.5 (3)
C1—C9—C10—C4	−1.7 (2)	C22—N4—C18—N3	−175.66 (15)
C3—C4—C10—C5	−177.42 (16)	C17—N3—C18—N4	161.25 (18)
C17—C4—C10—C5	0.5 (3)	C17—N3—C18—C19	−17.9 (3)
C3—C4—C10—C9	2.1 (2)	N4—C18—C19—C20	−2.8 (3)
C17—C4—C10—C9	−179.99 (15)	N3—C18—C19—C20	176.23 (18)
C12—N1—C11—O1	−5.8 (3)	C18—C19—C20—C21	0.3 (3)
C12—N1—C11—C1	173.88 (16)	C19—C20—C21—C22	1.4 (3)
C2—C1—C11—O1	109.2 (2)	C18—N4—C22—C21	−1.7 (3)
C9—C1—C11—O1	−69.2 (2)	C20—C21—C22—N4	−0.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N4^i	0.96 (3)	2.16 (3)	3.105 (2)	172 (2)
N3—H3N···N2^ii	0.94 (3)	2.14 (3)	3.066 (2)	169 (2)
C20—H20···O2^iii	0.95	2.36	3.303 (2)	170
C3—H3···Cg2^iv	0.95	2.74	3.404 (2)	128
C16—H16···Cg3^i	0.95	2.51	3.296 (2)	140
C21—H21···Cg1^v	0.95	2.80	3.351 (2)	118
C22—H22···Cg3^ii	0.95	2.62	3.396 (2)	139

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x+1, −y, −z+1; (v) x−3/2, −y−1/2, z−3/2.