N,N'-Bis(4-pyridylmethyl­ene)naphthalene-1,5-diamine

In the title compound, C₂₂H₁₆N₄, there are two crystallographically independent mol­ecules, both of which are centrosymmetric and adopt a non-planar conformation.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.108
• Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C22H16N4	Z = 2
Mr = 336.39	F(000) = 352
Triclinic, P1	Dx = 1.335 Mg m^−3
a = 7.6684 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2831 (9) Å	Cell parameters from 2932 reflections
c = 11.6172 (10) Å	θ = 2.8–25.0°
α = 102.895 (2)°	µ = 0.08 mm^−1
β = 102.286 (2)°	T = 150 K
γ = 102.822 (2)°	Block, green–brown
V = 836.89 (13) Å^3	0.22 × 0.18 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer	2357 reflections with I > 2σ(I)
ω scans	Rint = 0.031
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 25.0°, θmin = 1.9°
Tmin = 0.972, Tmax = 0.990	h = −9→9
6742 measured reflections	k = −12→12
2957 independent reflections	l = −13→13

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Only H-atom displacement parameters refined
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0491P)^2 + 0.1827P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.108	(Δ/σ)max = 0.001
S = 1.01	Δρmax = 0.17 e Å^−3
2957 reflections	Δρmin = −0.17 e Å^−3
251 parameters

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.

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

	x	y	z	Uiso*/Ueq
C1	0.1671 (3)	−0.04261 (19)	0.35757 (16)	0.0359 (5)
H1	0.1477	−0.1296	0.2998	0.036 (5)*
C2	0.2478 (2)	−0.02822 (18)	0.47912 (15)	0.0318 (4)
H2	0.2847	−0.1025	0.5037	0.039 (5)*
C3	0.2741 (2)	0.09733 (17)	0.56506 (15)	0.0262 (4)
C4	0.2165 (2)	0.20089 (18)	0.52301 (16)	0.0309 (4)
H4	0.2301	0.2878	0.579	0.035 (5)*
C5	0.1391 (2)	0.17648 (19)	0.39884 (16)	0.0341 (4)
H5	0.1015	0.249	0.3715	0.040 (5)*
C6	0.3610 (2)	0.12424 (18)	0.69684 (15)	0.0280 (4)
H6	0.373	0.2118	0.7512	0.031 (5)*
C7	0.5126 (2)	0.07344 (18)	0.86750 (14)	0.0277 (4)
C8	0.6641 (2)	0.18823 (19)	0.92185 (16)	0.0313 (4)
H8	0.7037	0.248	0.875	0.035 (5)*
C9	0.7608 (2)	0.21794 (19)	1.04607 (15)	0.0312 (4)
H9	0.8661	0.2971	1.0822	0.030 (5)*
C10	0.7056 (2)	0.13482 (18)	1.11511 (15)	0.0290 (4)
H10	0.7726	0.1562	1.199	0.023 (4)*
C11	0.5486 (2)	0.01620 (17)	1.06294 (14)	0.0260 (4)
C12	0.7575 (3)	0.5816 (2)	1.01613 (16)	0.0390 (5)
H12	0.7559	0.5015	1.0442	0.053 (6)*
C13	0.6407 (3)	0.56464 (19)	0.90322 (16)	0.0357 (4)
H13	0.5599	0.4755	0.8561	0.048 (6)*
C14	0.6418 (2)	0.67906 (18)	0.85863 (15)	0.0268 (4)
C15	0.7648 (2)	0.80512 (18)	0.93130 (15)	0.0288 (4)
H15	0.7742	0.8857	0.9032	0.026 (5)*
C16	0.8742 (2)	0.81266 (19)	1.04537 (16)	0.0317 (4)
H16	0.9545	0.9008	1.0953	0.033 (5)*
C17	0.5113 (2)	0.67066 (18)	0.74248 (15)	0.0282 (4)
H17	0.5253	0.7487	0.7108	0.027 (5)*
C18	0.2578 (2)	0.55852 (17)	0.57273 (15)	0.0264 (4)
C19	0.3207 (2)	0.59687 (18)	0.47999 (16)	0.0310 (4)
H19	0.4507	0.6304	0.4908	0.035 (5)*
C20	0.1948 (2)	0.58704 (19)	0.36893 (16)	0.0324 (4)
H20	0.2407	0.6149	0.3058	0.031 (5)*
C21	0.0077 (2)	0.53810 (17)	0.35062 (15)	0.0292 (4)
H21	−0.0757	0.5328	0.2753	0.023 (4)*
C22	−0.0627 (2)	0.49515 (17)	0.44361 (14)	0.0254 (4)
N1	0.1141 (2)	0.05685 (16)	0.31504 (13)	0.0355 (4)
N2	0.4206 (2)	0.03490 (15)	0.74067 (12)	0.0298 (4)
N3	0.8731 (2)	0.70300 (16)	1.08929 (13)	0.0370 (4)
N4	0.37974 (19)	0.56039 (14)	0.68375 (12)	0.0285 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0451 (11)	0.0323 (10)	0.0245 (10)	0.0099 (9)	0.0035 (8)	0.0035 (8)
C2	0.0371 (10)	0.0303 (10)	0.0267 (10)	0.0111 (8)	0.0043 (8)	0.0084 (8)
C3	0.0233 (9)	0.0295 (9)	0.0245 (9)	0.0057 (7)	0.0044 (7)	0.0091 (7)
C4	0.0326 (10)	0.0275 (10)	0.0279 (10)	0.0060 (8)	0.0030 (8)	0.0060 (8)
C5	0.0365 (10)	0.0331 (10)	0.0309 (10)	0.0081 (8)	0.0014 (8)	0.0151 (9)
C6	0.0313 (9)	0.0279 (9)	0.0221 (9)	0.0082 (8)	0.0050 (7)	0.0043 (8)
C7	0.0329 (10)	0.0328 (10)	0.0179 (8)	0.0153 (8)	0.0035 (7)	0.0053 (7)
C8	0.0351 (10)	0.0325 (10)	0.0271 (9)	0.0120 (8)	0.0063 (8)	0.0097 (8)
C9	0.0307 (10)	0.0309 (10)	0.0277 (10)	0.0093 (8)	0.0031 (8)	0.0036 (8)
C10	0.0307 (9)	0.0337 (10)	0.0192 (9)	0.0145 (8)	−0.0009 (7)	0.0028 (7)
C11	0.0298 (9)	0.0294 (9)	0.0199 (8)	0.0161 (8)	0.0040 (7)	0.0040 (7)
C12	0.0458 (12)	0.0345 (11)	0.0330 (11)	0.0108 (9)	0.0013 (9)	0.0121 (9)
C13	0.0377 (10)	0.0294 (10)	0.0311 (10)	0.0056 (8)	0.0000 (8)	0.0037 (8)
C14	0.0254 (9)	0.0304 (9)	0.0236 (9)	0.0101 (7)	0.0062 (7)	0.0041 (7)
C15	0.0273 (9)	0.0304 (10)	0.0267 (9)	0.0092 (8)	0.0050 (7)	0.0055 (8)
C16	0.0275 (9)	0.0322 (10)	0.0278 (10)	0.0054 (8)	0.0018 (7)	0.0024 (8)
C17	0.0296 (9)	0.0305 (10)	0.0244 (9)	0.0109 (8)	0.0063 (7)	0.0064 (8)
C18	0.0310 (9)	0.0233 (9)	0.0227 (9)	0.0118 (7)	0.0016 (7)	0.0037 (7)
C19	0.0274 (10)	0.0320 (10)	0.0302 (10)	0.0065 (8)	0.0056 (8)	0.0062 (8)
C20	0.0374 (11)	0.0365 (10)	0.0251 (10)	0.0112 (8)	0.0100 (8)	0.0104 (8)
C21	0.0325 (10)	0.0326 (10)	0.0197 (9)	0.0110 (8)	0.0010 (7)	0.0059 (7)
C22	0.0298 (9)	0.0209 (8)	0.0219 (8)	0.0089 (7)	0.0018 (7)	0.0025 (7)
N1	0.0390 (9)	0.0381 (9)	0.0249 (8)	0.0063 (7)	0.0023 (7)	0.0112 (7)
N2	0.0342 (8)	0.0338 (8)	0.0209 (8)	0.0112 (7)	0.0046 (6)	0.0081 (6)
N3	0.0365 (9)	0.0404 (9)	0.0270 (8)	0.0086 (7)	−0.0009 (7)	0.0072 (7)
N4	0.0274 (8)	0.0296 (8)	0.0231 (8)	0.0090 (6)	−0.0001 (6)	0.0029 (6)

Geometric parameters (Å, º)

C1—N1	1.334 (2)	C12—N3	1.335 (2)
C1—C2	1.376 (2)	C12—C13	1.372 (2)
C1—H1	0.95	C12—H12	0.95
C2—C3	1.388 (2)	C13—C14	1.387 (2)
C2—H2	0.95	C13—H13	0.95
C3—C4	1.385 (2)	C14—C15	1.383 (2)
C3—C6	1.469 (2)	C14—C17	1.471 (2)
C4—C5	1.380 (2)	C15—C16	1.385 (2)
C4—H4	0.95	C15—H15	0.95
C5—N1	1.334 (2)	C16—N3	1.337 (2)
C5—H5	0.95	C16—H16	0.95
C6—N2	1.268 (2)	C17—N4	1.274 (2)
C6—H6	0.95	C17—H17	0.95
C7—C8	1.374 (2)	C18—C19	1.370 (2)
C7—N2	1.414 (2)	C18—N4	1.416 (2)
C7—C11^i	1.423 (2)	C18—C22^ii	1.430 (2)
C8—C9	1.405 (2)	C19—C20	1.405 (2)
C8—H8	0.95	C19—H19	0.95
C9—C10	1.358 (2)	C20—C21	1.364 (2)
C9—H9	0.95	C20—H20	0.95
C10—C11	1.419 (2)	C21—C22	1.417 (2)
C10—H10	0.95	C21—H21	0.95
C11—C11^i	1.419 (3)	C22—C22^ii	1.419 (3)
C11—C7^i	1.423 (2)	C22—C18^ii	1.430 (2)
N1—C1—C2	124.66 (17)	C13—C12—H12	117.8
N1—C1—H1	117.7	C12—C13—C14	119.23 (17)
C2—C1—H1	117.7	C12—C13—H13	120.4
C1—C2—C3	118.44 (17)	C14—C13—H13	120.4
C1—C2—H2	120.8	C15—C14—C13	117.24 (15)
C3—C2—H2	120.8	C15—C14—C17	120.48 (16)
C4—C3—C2	117.75 (15)	C13—C14—C17	122.19 (16)
C4—C3—C6	119.39 (15)	C14—C15—C16	119.34 (17)
C2—C3—C6	122.85 (15)	C14—C15—H15	120.3
C5—C4—C3	119.25 (16)	C16—C15—H15	120.3
C5—C4—H4	120.4	N3—C16—C15	123.74 (17)
C3—C4—H4	120.4	N3—C16—H16	118.1
N1—C5—C4	123.72 (17)	C15—C16—H16	118.1
N1—C5—H5	118.1	N4—C17—C14	121.07 (16)
C4—C5—H5	118.1	N4—C17—H17	119.5
N2—C6—C3	122.42 (15)	C14—C17—H17	119.5
N2—C6—H6	118.8	C19—C18—N4	122.49 (15)
C3—C6—H6	118.8	C19—C18—C22^ii	120.17 (15)
C8—C7—N2	121.94 (15)	N4—C18—C22^ii	117.19 (15)
C8—C7—C11^i	120.14 (15)	C18—C19—C20	120.62 (16)
N2—C7—C11^i	117.78 (15)	C18—C19—H19	119.7
C7—C8—C9	120.55 (17)	C20—C19—H19	119.7
C7—C8—H8	119.7	C21—C20—C19	120.86 (17)
C9—C8—H8	119.7	C21—C20—H20	119.6
C10—C9—C8	120.77 (17)	C19—C20—H20	119.6
C10—C9—H9	119.6	C20—C21—C22	120.19 (15)
C8—C9—H9	119.6	C20—C21—H21	119.9
C9—C10—C11	120.48 (15)	C22—C21—H21	119.9
C9—C10—H10	119.8	C21—C22—C22^ii	119.60 (19)
C11—C10—H10	119.8	C21—C22—C18^ii	121.86 (14)
C10—C11—C11^i	119.3 (2)	C22^ii—C22—C18^ii	118.54 (19)
C10—C11—C7^i	121.94 (14)	C5—N1—C1	116.15 (15)
C11^i—C11—C7^i	118.7 (2)	C6—N2—C7	118.28 (14)
N3—C12—C13	124.49 (18)	C12—N3—C16	115.92 (15)
N3—C12—H12	117.8	C17—N4—C18	118.59 (15)
N1—C1—C2—C3	1.1 (3)	C14—C15—C16—N3	2.3 (3)
C1—C2—C3—C4	0.2 (3)	C15—C14—C17—N4	−169.68 (16)
C1—C2—C3—C6	−179.22 (16)	C13—C14—C17—N4	6.8 (3)
C2—C3—C4—C5	−1.1 (3)	N4—C18—C19—C20	176.89 (16)
C6—C3—C4—C5	178.42 (16)	C22^ii—C18—C19—C20	1.4 (3)
C3—C4—C5—N1	0.6 (3)	C18—C19—C20—C21	−0.6 (3)
C4—C3—C6—N2	−178.32 (16)	C19—C20—C21—C22	−0.5 (3)
C2—C3—C6—N2	1.1 (3)	C20—C21—C22—C22^ii	0.7 (3)
N2—C7—C8—C9	−175.25 (15)	C20—C21—C22—C18^ii	−179.13 (16)
C11^i—C7—C8—C9	0.4 (3)	C4—C5—N1—C1	0.6 (3)
C7—C8—C9—C10	−0.7 (3)	C2—C1—N1—C5	−1.6 (3)
C8—C9—C10—C11	−0.1 (3)	C3—C6—N2—C7	176.10 (15)
C9—C10—C11—C11^i	1.1 (3)	C8—C7—N2—C6	−55.2 (2)
C9—C10—C11—C7^i	179.73 (16)	C11^i—C7—N2—C6	129.06 (17)
N3—C12—C13—C14	1.1 (3)	C13—C12—N3—C16	−1.4 (3)
C12—C13—C14—C15	0.9 (3)	C15—C16—N3—C12	−0.3 (3)
C12—C13—C14—C17	−175.59 (17)	C14—C17—N4—C18	179.71 (15)
C13—C14—C15—C16	−2.5 (2)	C19—C18—N4—C17	51.1 (2)
C17—C14—C15—C16	174.09 (15)	C22^ii—C18—N4—C17	−133.30 (16)

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y+1, −z+1.