N,N′-Di-2-naphthyl­pyridine-2,6-dicarbox­amide

Qi, J.-Y.; Zhou, Z.-Y.; Chan, A.S.C.

doi:10.1107/S1600536801012028

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N,N'-Di-2-naphthylpyridine-2,6-dicarboxamide

J.-Y. Qi, Z.-Y. Zhou and A. S. C. Chan

The title tridentate ligand, C₂₇H₁₉N₃O₂, is essentially planar.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801012028/bt6064sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801012028/bt6064Isup2.hkl Contains datablock I

CCDC reference: 170915

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
R factor = 0.044
wR factor = 0.105
Data-to-parameter ratio = 16.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



GOODF_01  Alert C The least squares goodness of fit parameter lies
          outside the range 0.80 <> 2.00
          Goodness of fit given =      0.753


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

A series of metal Cu^II, Fe^III, Co^III and Ni^II complexes of ligands containing pyridine-2,6-dicarboxamide moieties have been synthesized in recent years (Chavez et al., 1996, 1998; Marlin et al., 1999; Hiratani, et al., 1990). It has been well documented that amidate ligands have the ability to stabilize the high formal oxidation states of metal ions due to the good σ-donor properties of the deprotonated N atom (Patra & Mukherjee, 1999).

In order ot develop further the coordination chemistry of pyridine–amide ligands toward metal ions, we synthesized the title ligand, (I), with a naphthyl instead of a phenyl group connected to the amide N atom. It is estimated that the conjugation effect of the naphthyl ring is in favor of the coordination of the deprotonated nitrogen but the steric effect of the bulk aromatic ring will hinder the coordination. In the process of forming a complex, the naphthyl ring will probably rotate to another position where it is far away from the inside of the molecule, so that the amide N atom can easily coordinate with a metal ion.

Experimental top

The title compound was synthesized according to the procedure of Ray et al. (1997). The crystal used for data collection was obtained by slow evaporation from a saturated DMF–water (10:1) solution at room temperature.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART (Siemens, 1995); data reduction: SHELXTL-NT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

Figures top

Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids (Siemens, 1995).

N,N'-Di-2-naphthylpyridine-2,6-dicarboxamide top

Crystal data top

C₂₇H₁₉N₃O₂	? # Insert any comments here.
M_r = 417.45	D_x = 1.360 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.816 (3) Å	Cell parameters from 8732 reflections
b = 14.965 (4) Å	θ = 1–27.5°
c = 15.936 (5) Å	µ = 0.09 mm⁻¹
β = 104.122 (6)°	T = 294 K
V = 2039.0 (10) Å³	Prism, colorless
Z = 4	0.28 × 0.10 × 0.06 mm
F(000) = 872

Data collection top

Bruker CCD area-detector diffractometer	4710 independent reflections
Radiation source: fine-focus sealed tube	1538 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
ϕ and ω scans	θ_max = 27.6°, θ_min = 1.9°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.976, T_max = 0.995	k = −16→19
13601 measured reflections	l = −17→20

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.044	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.105	(Δ/σ)_max < 0.001
S = 0.75	Δρ_max = 0.18 e Å⁻³
4710 reflections	Δρ_min = −0.16 e Å⁻³
290 parameters	Extinction correction: SHELXTL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0050 (4)

Crystal data top

C₂₇H₁₉N₃O₂	V = 2039.0 (10) Å³
M_r = 417.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.816 (3) Å	µ = 0.09 mm⁻¹
b = 14.965 (4) Å	T = 294 K
c = 15.936 (5) Å	0.28 × 0.10 × 0.06 mm
β = 104.122 (6)°

Data collection top

Bruker CCD area-detector diffractometer	4710 independent reflections
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	1538 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.995	R_int = 0.090
13601 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.105	H-atom parameters constrained
S = 0.75	Δρ_max = 0.18 e Å⁻³
4710 reflections	Δρ_min = −0.16 e Å⁻³
290 parameters

Special details top

Experimental. ? #Insert any special details here.

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.42289 (19)	0.64870 (11)	0.51159 (11)	0.0655 (6)
O2	1.02797 (19)	0.47412 (10)	0.35185 (11)	0.0582 (5)
N1	0.6185 (2)	0.57073 (12)	0.60226 (13)	0.0428 (5)
H1B	0.7037	0.5417	0.6049	0.051*
N2	0.7370 (2)	0.53763 (12)	0.45660 (12)	0.0415 (5)
N3	0.9069 (2)	0.38820 (12)	0.43442 (12)	0.0423 (5)
H3B	0.8333	0.3887	0.4613	0.051*
C1	0.4704 (3)	0.64270 (15)	0.69148 (17)	0.0522 (7)
H1A	0.4490	0.6894	0.6519	0.063*
C2	0.4076 (3)	0.64404 (18)	0.7639 (2)	0.0650 (8)
H2A	0.3436	0.6913	0.7713	0.078*
C3	0.4382 (3)	0.5780 (2)	0.82317 (19)	0.0647 (8)
H3A	0.3925	0.5789	0.8700	0.078*
C4	0.5394 (3)	0.50735 (17)	0.81437 (17)	0.0481 (7)
C5	0.5792 (3)	0.43953 (19)	0.87699 (18)	0.0604 (8)
H5A	0.5333	0.4398	0.9237	0.072*
C6	0.6814 (3)	0.37418 (18)	0.87151 (18)	0.0625 (8)
H6A	0.7058	0.3303	0.9140	0.075*
C7	0.7504 (3)	0.37299 (16)	0.80159 (18)	0.0582 (8)
H7A	0.8239	0.3293	0.7987	0.070*
C8	0.7115 (3)	0.43510 (15)	0.73756 (17)	0.0478 (7)
H8A	0.7559	0.4317	0.6904	0.057*
C9	0.6048 (3)	0.50483 (15)	0.74129 (16)	0.0385 (6)
C10	0.5625 (3)	0.57390 (15)	0.67828 (16)	0.0395 (6)
C11	0.5492 (3)	0.60964 (16)	0.52578 (17)	0.0458 (7)
C12	0.6362 (3)	0.60541 (15)	0.45593 (16)	0.0402 (6)
C13	0.6071 (3)	0.67141 (15)	0.39369 (17)	0.0502 (7)
H13A	0.5348	0.7163	0.3953	0.060*
C14	0.6860 (3)	0.67011 (16)	0.32947 (18)	0.0583 (8)
H14A	0.6699	0.7144	0.2873	0.070*
C15	0.7898 (3)	0.60155 (16)	0.32898 (16)	0.0496 (7)
H15A	0.8449	0.5987	0.2862	0.059*
C16	0.8110 (3)	0.53723 (15)	0.39254 (16)	0.0402 (6)
C17	0.9253 (3)	0.46335 (16)	0.39130 (16)	0.0435 (7)
C18	0.9959 (3)	0.30812 (15)	0.44035 (16)	0.0395 (6)
C19	1.0810 (3)	0.28806 (16)	0.38148 (16)	0.0491 (7)
H19A	1.0819	0.3273	0.3364	0.059*
C20	1.1672 (3)	0.20807 (18)	0.38929 (19)	0.0623 (8)
H20A	1.2269	0.1957	0.3500	0.075*
C21	1.1645 (3)	0.14912 (18)	0.45281 (19)	0.0661 (9)
H21A	1.2208	0.0961	0.4559	0.079*
C22	1.0784 (3)	0.16631 (16)	0.51439 (17)	0.0476 (7)
C23	1.0743 (3)	0.10582 (18)	0.5811 (2)	0.0679 (9)
H23A	1.1270	0.0517	0.5834	0.081*
C24	0.9961 (3)	0.12411 (18)	0.64190 (19)	0.0710 (9)
H24A	0.9948	0.0830	0.6855	0.085*
C25	0.9166 (3)	0.20564 (18)	0.63888 (19)	0.0626 (8)
H25A	0.8647	0.2189	0.6816	0.075*
C26	0.9142 (3)	0.26565 (15)	0.57460 (16)	0.0467 (7)
H26A	0.8591	0.3188	0.5734	0.056*
C27	0.9941 (2)	0.24833 (15)	0.50973 (15)	0.0392 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0415 (11)	0.0866 (13)	0.0671 (14)	0.0190 (10)	0.0104 (10)	0.0194 (11)
O2	0.0465 (11)	0.0672 (12)	0.0661 (14)	−0.0013 (9)	0.0237 (11)	0.0135 (10)
N1	0.0367 (12)	0.0464 (12)	0.0460 (15)	0.0086 (10)	0.0111 (12)	0.0060 (11)
N2	0.0331 (12)	0.0452 (13)	0.0436 (14)	−0.0034 (10)	0.0041 (11)	0.0008 (10)
N3	0.0391 (12)	0.0439 (13)	0.0464 (14)	−0.0010 (10)	0.0151 (11)	0.0034 (11)
C1	0.0503 (17)	0.0481 (17)	0.060 (2)	0.0075 (13)	0.0162 (16)	−0.0032 (14)
C2	0.061 (2)	0.066 (2)	0.073 (2)	0.0172 (16)	0.0257 (18)	−0.0098 (18)
C3	0.061 (2)	0.080 (2)	0.060 (2)	0.0039 (17)	0.0274 (17)	−0.0075 (18)
C4	0.0469 (16)	0.0521 (17)	0.0464 (19)	−0.0060 (14)	0.0137 (15)	−0.0043 (15)
C5	0.0578 (19)	0.075 (2)	0.049 (2)	−0.0089 (16)	0.0134 (16)	0.0005 (17)
C6	0.067 (2)	0.061 (2)	0.055 (2)	−0.0085 (16)	0.0057 (17)	0.0134 (16)
C7	0.0579 (19)	0.0478 (18)	0.063 (2)	0.0088 (14)	0.0039 (17)	0.0068 (16)
C8	0.0451 (16)	0.0453 (16)	0.055 (2)	0.0002 (13)	0.0150 (15)	−0.0016 (15)
C9	0.0316 (14)	0.0392 (15)	0.0435 (17)	−0.0041 (11)	0.0070 (13)	−0.0023 (13)
C10	0.0355 (14)	0.0411 (15)	0.0445 (17)	−0.0017 (12)	0.0147 (13)	−0.0034 (13)
C11	0.0335 (16)	0.0498 (16)	0.052 (2)	0.0010 (13)	0.0066 (14)	0.0054 (14)
C12	0.0346 (15)	0.0413 (15)	0.0418 (17)	−0.0073 (12)	0.0035 (13)	0.0030 (13)
C13	0.0469 (16)	0.0461 (16)	0.0537 (19)	0.0020 (13)	0.0049 (15)	0.0071 (15)
C14	0.0645 (19)	0.0501 (17)	0.061 (2)	0.0052 (15)	0.0160 (17)	0.0194 (15)
C15	0.0550 (18)	0.0534 (17)	0.0407 (18)	−0.0040 (14)	0.0126 (14)	0.0102 (15)
C16	0.0355 (14)	0.0458 (16)	0.0385 (17)	−0.0030 (12)	0.0075 (13)	0.0023 (13)
C17	0.0348 (15)	0.0529 (17)	0.0405 (18)	−0.0077 (13)	0.0047 (13)	−0.0003 (14)
C18	0.0338 (14)	0.0433 (15)	0.0410 (17)	−0.0032 (12)	0.0083 (13)	−0.0060 (13)
C19	0.0541 (17)	0.0530 (17)	0.0437 (18)	−0.0061 (14)	0.0184 (15)	−0.0081 (13)
C20	0.066 (2)	0.069 (2)	0.060 (2)	−0.0006 (16)	0.0305 (18)	−0.0181 (17)
C21	0.066 (2)	0.063 (2)	0.074 (2)	0.0151 (16)	0.0260 (19)	−0.0079 (18)
C22	0.0441 (16)	0.0499 (17)	0.0493 (19)	0.0066 (13)	0.0126 (14)	−0.0013 (15)
C23	0.072 (2)	0.0574 (19)	0.074 (2)	0.0188 (16)	0.0179 (19)	0.0099 (18)
C24	0.080 (2)	0.066 (2)	0.068 (2)	0.0110 (17)	0.0202 (19)	0.0204 (17)
C25	0.064 (2)	0.0673 (19)	0.063 (2)	0.0071 (16)	0.0291 (17)	0.0086 (17)
C26	0.0426 (16)	0.0515 (17)	0.0477 (18)	0.0034 (13)	0.0145 (14)	0.0063 (14)
C27	0.0348 (14)	0.0425 (15)	0.0400 (17)	−0.0011 (12)	0.0086 (13)	−0.0040 (13)

Geometric parameters (Å, º) top

O1—C11	1.228 (2)	C11—C12	1.500 (3)
O2—C17	1.232 (2)	C12—C13	1.379 (3)
N1—C11	1.355 (3)	C13—C14	1.371 (3)
N1—C10	1.417 (3)	C13—H13A	0.9300
N1—H1B	0.8600	C14—C15	1.376 (3)
N2—C16	1.339 (3)	C14—H14A	0.9300
N2—C12	1.346 (3)	C15—C16	1.377 (3)
N3—C17	1.348 (2)	C15—H15A	0.9300
N3—C18	1.423 (2)	C16—C17	1.499 (3)
N3—H3B	0.8600	C18—C19	1.370 (3)
C1—C10	1.359 (3)	C18—C27	1.425 (3)
C1—C2	1.397 (3)	C19—C20	1.407 (3)
C1—H1A	0.9300	C19—H19A	0.9300
C2—C3	1.348 (3)	C20—C21	1.347 (3)
C2—H2A	0.9300	C20—H20A	0.9300
C3—C4	1.412 (3)	C21—C22	1.403 (3)
C3—H3A	0.9300	C21—H21A	0.9300
C4—C5	1.407 (3)	C22—C23	1.403 (3)
C4—C9	1.420 (3)	C22—C27	1.427 (3)
C5—C6	1.347 (3)	C23—C24	1.347 (3)
C5—H5A	0.9300	C23—H23A	0.9300
C6—C7	1.394 (3)	C24—C25	1.402 (3)
C6—H6A	0.9300	C24—H24A	0.9300
C7—C8	1.361 (3)	C25—C26	1.359 (3)
C7—H7A	0.9300	C25—H25A	0.9300
C8—C9	1.415 (3)	C26—C27	1.410 (3)
C8—H8A	0.9300	C26—H26A	0.9300
C9—C10	1.426 (3)

C11—N1—C10	125.4 (2)	C14—C13—H13A	120.4
C11—N1—H1B	117.3	C12—C13—H13A	120.4
C10—N1—H1B	117.3	C13—C14—C15	118.3 (2)
C16—N2—C12	116.1 (2)	C13—C14—H14A	120.9
C17—N3—C18	127.09 (19)	C15—C14—H14A	120.9
C17—N3—H3B	116.5	C14—C15—C16	119.3 (2)
C18—N3—H3B	116.5	C14—C15—H15A	120.4
C10—C1—C2	120.7 (2)	C16—C15—H15A	120.4
C10—C1—H1A	119.6	N2—C16—C15	123.6 (2)
C2—C1—H1A	119.6	N2—C16—C17	117.9 (2)
C3—C2—C1	121.1 (3)	C15—C16—C17	118.5 (2)
C3—C2—H2A	119.5	O2—C17—N3	124.4 (2)
C1—C2—H2A	119.5	O2—C17—C16	119.3 (2)
C2—C3—C4	120.1 (3)	N3—C17—C16	116.3 (2)
C2—C3—H3A	119.9	C19—C18—N3	121.6 (2)
C4—C3—H3A	119.9	C19—C18—C27	120.3 (2)
C5—C4—C3	121.6 (3)	N3—C18—C27	118.0 (2)
C5—C4—C9	118.8 (2)	C18—C19—C20	120.0 (2)
C3—C4—C9	119.6 (3)	C18—C19—H19A	120.0
C6—C5—C4	122.2 (3)	C20—C19—H19A	120.0
C6—C5—H5A	118.9	C21—C20—C19	121.0 (2)
C4—C5—H5A	118.9	C21—C20—H20A	119.5
C5—C6—C7	119.4 (3)	C19—C20—H20A	119.5
C5—C6—H6A	120.3	C20—C21—C22	121.1 (3)
C7—C6—H6A	120.3	C20—C21—H21A	119.4
C8—C7—C6	120.8 (3)	C22—C21—H21A	119.4
C8—C7—H7A	119.6	C21—C22—C23	122.0 (3)
C6—C7—H7A	119.6	C21—C22—C27	119.0 (2)
C7—C8—C9	121.4 (2)	C23—C22—C27	119.0 (2)
C7—C8—H8A	119.3	C24—C23—C22	121.7 (3)
C9—C8—H8A	119.3	C24—C23—H23A	119.1
C8—C9—C4	117.4 (2)	C22—C23—H23A	119.1
C8—C9—C10	124.6 (2)	C23—C24—C25	119.4 (3)
C4—C9—C10	118.0 (2)	C23—C24—H24A	120.3
C1—C10—N1	120.3 (2)	C25—C24—H24A	120.3
C1—C10—C9	120.3 (2)	C26—C25—C24	121.1 (3)
N1—C10—C9	119.5 (2)	C26—C25—H25A	119.4
O1—C11—N1	124.1 (2)	C24—C25—H25A	119.4
O1—C11—C12	119.2 (2)	C25—C26—C27	120.8 (2)
N1—C11—C12	116.7 (2)	C25—C26—H26A	119.6
N2—C12—C13	123.5 (2)	C27—C26—H26A	119.6
N2—C12—C11	118.8 (2)	C26—C27—C18	123.7 (2)
C13—C12—C11	117.7 (2)	C26—C27—C22	117.8 (2)
C14—C13—C12	119.2 (2)	C18—C27—C22	118.4 (2)

C10—C1—C2—C3	1.0 (4)	C13—C14—C15—C16	−0.2 (4)
C1—C2—C3—C4	2.2 (4)	C12—N2—C16—C15	0.6 (3)
C2—C3—C4—C5	177.2 (3)	C12—N2—C16—C17	179.46 (19)
C2—C3—C4—C9	−2.0 (4)	C14—C15—C16—N2	−0.7 (4)
C3—C4—C5—C6	−176.7 (3)	C14—C15—C16—C17	−179.6 (2)
C9—C4—C5—C6	2.5 (4)	C18—N3—C17—O2	−2.2 (4)
C4—C5—C6—C7	−0.2 (4)	C18—N3—C17—C16	177.6 (2)
C5—C6—C7—C8	−2.3 (4)	N2—C16—C17—O2	−158.1 (2)
C6—C7—C8—C9	2.5 (4)	C15—C16—C17—O2	20.9 (3)
C7—C8—C9—C4	−0.2 (4)	N2—C16—C17—N3	22.2 (3)
C7—C8—C9—C10	177.8 (2)	C15—C16—C17—N3	−158.9 (2)
C5—C4—C9—C8	−2.2 (3)	C17—N3—C18—C19	−20.3 (4)
C3—C4—C9—C8	177.0 (2)	C17—N3—C18—C27	159.8 (2)
C5—C4—C9—C10	179.6 (2)	N3—C18—C19—C20	−179.8 (2)
C3—C4—C9—C10	−1.1 (3)	C27—C18—C19—C20	0.1 (4)
C2—C1—C10—N1	176.5 (2)	C18—C19—C20—C21	1.7 (4)
C2—C1—C10—C9	−4.2 (4)	C19—C20—C21—C22	−1.3 (4)
C11—N1—C10—C1	−25.6 (3)	C20—C21—C22—C23	−179.9 (3)
C11—N1—C10—C9	155.1 (2)	C20—C21—C22—C27	−0.8 (4)
C8—C9—C10—C1	−173.8 (2)	C21—C22—C23—C24	177.5 (3)
C4—C9—C10—C1	4.2 (3)	C27—C22—C23—C24	−1.6 (4)
C8—C9—C10—N1	5.5 (3)	C22—C23—C24—C25	−0.1 (4)
C4—C9—C10—N1	−176.5 (2)	C23—C24—C25—C26	1.5 (4)
C10—N1—C11—O1	−4.3 (4)	C24—C25—C26—C27	−1.2 (4)
C10—N1—C11—C12	174.4 (2)	C25—C26—C27—C18	179.7 (2)
C16—N2—C12—C13	0.4 (3)	C25—C26—C27—C22	−0.5 (4)
C16—N2—C12—C11	179.9 (2)	C19—C18—C27—C26	177.6 (2)
O1—C11—C12—N2	−154.6 (2)	N3—C18—C27—C26	−2.5 (3)
N1—C11—C12—N2	26.7 (3)	C19—C18—C27—C22	−2.1 (3)
O1—C11—C12—C13	24.8 (3)	N3—C18—C27—C22	177.7 (2)
N1—C11—C12—C13	−153.9 (2)	C21—C22—C27—C26	−177.3 (2)
N2—C12—C13—C14	−1.3 (4)	C23—C22—C27—C26	1.9 (3)
C11—C12—C13—C14	179.3 (2)	C21—C22—C27—C18	2.5 (3)
C12—C13—C14—C15	1.1 (4)	C23—C22—C27—C18	−178.4 (2)

Experimental details

Crystal data
Chemical formula	C₂₇H₁₉N₃O₂
M_r	417.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	8.816 (3), 14.965 (4), 15.936 (5)
β (°)	104.122 (6)
V (Å³)	2039.0 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.10 × 0.06

Data collection
Diffractometer	Bruker CCD area-detector diffractometer
Absorption correction	Empirical (using intensity measurements) (SADABS; Sheldrick, 1996)
T_min, T_max	0.976, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	13601, 4710, 1538
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.105, 0.75
No. of reflections	4710
No. of parameters	290
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16

Computer programs: SMART (Siemens, 1995), SHELXTL-NT (Siemens, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-NT.

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N,N'-Di-2-naphthyl­pyridine-2,6-dicarbox­amide