(E,E)-N,N'-Bis(1-phenyl­ethyl­idene)ethyl­enediamine

The essentially planar title compound, C₁₈H₂₀N₂, is disposed about a center of inversion located at the mid-point of the ethyl­ene bond and features an E configuration about each C=N bond.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.117
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

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Alert level A
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

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

   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(E,E)—N,N'-Bis(1-phenylethylidene)ethylenediamine

Crystal data

C18H20N2	F(000) = 284
Mr = 264.36	Dx = 1.211 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 29 reflections
a = 5.4713 (7) Å	θ = 3.6–27.5°
b = 14.1328 (17) Å	µ = 0.07 mm^−1
c = 9.7392 (13) Å	T = 113 K
β = 105.7130 (5)°	Prism, colorless
V = 724.94 (16) Å^3	0.51 × 0.40 × 0.22 mm
Z = 2

Data collection

Rigaku R-AXIS SPIDER diffractometer	1666 independent reflections
Radiation source: fine-focus sealed tube	1617 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: numerical (Katayama, 1986; Paturle & Coppens, 1988)	h = −7→7
Tmin = 0.978, Tmax = 0.992	k = −18→18
9051 measured reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0589P)^2 + 0.2225P] where P = (Fo^2 + 2Fc^2)/3
1666 reflections	(Δ/σ)max < 0.001
92 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

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
N1	0.46963 (17)	0.45029 (6)	0.17131 (9)	0.0209 (2)
C1	0.34532 (19)	0.45979 (7)	0.26415 (10)	0.0180 (2)
C2	0.1569 (2)	0.53757 (7)	0.26674 (11)	0.0226 (3)
H2A	0.1540	0.5829	0.1902	0.034*
H2B	0.2071	0.5701	0.3590	0.034*
H2C	−0.0126	0.5101	0.2527	0.034*
C3	0.4324 (2)	0.51817 (8)	0.05352 (11)	0.0226 (3)
H3A	0.5020	0.5806	0.0905	0.027*
H3B	0.2489	0.5257	0.0066	0.027*
C4	0.38798 (18)	0.38664 (7)	0.37980 (10)	0.0181 (2)
C5	0.5753 (2)	0.31716 (7)	0.39142 (11)	0.0218 (2)
H5	0.6782	0.3177	0.3270	0.026*
C6	0.6125 (2)	0.24755 (8)	0.49584 (12)	0.0249 (3)
H6	0.7413	0.2013	0.5028	0.030*
C7	0.4617 (2)	0.24538 (8)	0.59016 (12)	0.0257 (3)
H7	0.4855	0.1973	0.6607	0.031*
C8	0.2767 (2)	0.31386 (9)	0.58056 (12)	0.0282 (3)
H8	0.1740	0.3129	0.6451	0.034*
C9	0.2405 (2)	0.38420 (8)	0.47661 (11)	0.0239 (3)
H9	0.1139	0.4311	0.4715	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0242 (5)	0.0214 (4)	0.0186 (4)	−0.0016 (3)	0.0085 (3)	0.0007 (3)
C1	0.0185 (5)	0.0188 (5)	0.0165 (5)	−0.0027 (3)	0.0043 (4)	−0.0019 (3)
C2	0.0263 (5)	0.0231 (5)	0.0199 (5)	0.0040 (4)	0.0086 (4)	0.0027 (4)
C3	0.0277 (5)	0.0222 (5)	0.0201 (5)	0.0001 (4)	0.0104 (4)	0.0020 (4)
C4	0.0188 (5)	0.0188 (5)	0.0168 (5)	−0.0020 (4)	0.0049 (4)	−0.0013 (4)
C5	0.0243 (5)	0.0220 (5)	0.0213 (5)	0.0010 (4)	0.0099 (4)	−0.0014 (4)
C6	0.0271 (6)	0.0211 (5)	0.0273 (5)	0.0044 (4)	0.0086 (4)	0.0006 (4)
C7	0.0286 (6)	0.0240 (5)	0.0248 (5)	0.0006 (4)	0.0077 (4)	0.0075 (4)
C8	0.0280 (6)	0.0332 (6)	0.0280 (6)	0.0038 (4)	0.0152 (4)	0.0086 (4)
C9	0.0229 (5)	0.0267 (5)	0.0247 (5)	0.0057 (4)	0.0109 (4)	0.0051 (4)

Geometric parameters (Å, º)

N1—C1	1.2772 (13)	C4—C9	1.3976 (14)
N1—C3	1.4668 (13)	C5—C6	1.3897 (15)
C1—C2	1.5120 (14)	C5—H5	0.9500
C1—C4	1.4999 (14)	C6—C7	1.3915 (15)
C2—H2A	0.9800	C6—H6	0.9500
C2—H2B	0.9800	C7—C8	1.3850 (16)
C2—H2C	0.9800	C7—H7	0.9500
C3—C3^i	1.521 (2)	C8—C9	1.3942 (15)
C3—H3A	0.9900	C8—H8	0.9500
C3—H3B	0.9900	C9—H9	0.9500
C4—C5	1.4016 (14)
C1—N1—C3	119.82 (9)	C5—C4—C1	120.35 (9)
N1—C1—C2	125.77 (9)	C9—C4—C1	121.52 (9)
N1—C1—C4	117.05 (9)	C6—C5—C4	120.94 (9)
C2—C1—C4	117.18 (8)	C6—C5—H5	119.5
C1—C2—H2A	109.5	C4—C5—H5	119.5
C1—C2—H2B	109.5	C5—C6—C7	120.20 (10)
H2A—C2—H2B	109.5	C5—C6—H6	119.9
C1—C2—H2C	109.5	C7—C6—H6	119.9
H2A—C2—H2C	109.5	C8—C7—C6	119.55 (10)
H2B—C2—H2C	109.5	C8—C7—H7	120.2
N1—C3—C3^i	108.95 (11)	C6—C7—H7	120.2
N1—C3—H3A	109.9	C7—C8—C9	120.32 (10)
C3^i—C3—H3A	109.9	C7—C8—H8	119.8
N1—C3—H3B	109.9	C9—C8—H8	119.8
C3^i—C3—H3B	109.9	C8—C9—C4	120.86 (10)
H3A—C3—H3B	108.3	C8—C9—H9	119.6
C5—C4—C9	118.12 (9)	C4—C9—H9	119.6

Symmetry code: (i) −x+1, −y+1, −z.