(2,6-Diphenyl­piperidin-4-yl­idene)(phenyl)acetonitrile

Thiruvalluvar, A.; Balamurugan, S.; Manimekalai, A.; Balamurugan, A.

doi:10.1107/S1600536807022386

Buy article online - an online subscription or single-article purchase is required to access this article.

(2,6-Diphenylpiperidin-4-ylidene)(phenyl)acetonitrile

A. Thiruvalluvar, S. Balamurugan, A. Manimekalai and A. Balamurugan

In the title molecule, C₂₅H₂₂N₂, the piperidine ring adopts a chair conformation. The two phenyl rings attached to the piperidine ring have equatorial orientations and make a dihedral angle of 17.9 (1)°. The phenylacetonitrile group has a bisectional orientation. Molecules are linked by intramolecular C—H

N interactions, and by N—H

π and C—H

π interactions.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022386/ww2085sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022386/ww2085Isup2.hkl Contains datablock I

CCDC reference: 651438

checkCIF report

Key indicators

Single-crystal X-ray study
T = 160 K
Mean (C-C) = 0.003 Å
R factor = 0.052
wR factor = 0.144
Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C41    -   C42    ...       1.44 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C6     = ...          R

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   0 ALERT type 5 Informative message, check

Comment top

In the title compound, (I), (Fig. 1), piperidine ring adopts a chair conformation. Two phenyl rings attached to the piperidine ring in positions 2 and 6 have equatorial orientations and make a dihedral angle of 17.9 (1)°. The phenyl-acetonitrile group at position 4 has a bisectional orientation. Molecules are linked by C22—H22···N1, C66—H66···N1 intramolecular and intermolecular hydrogen bonds: N1—H1···π (1 - x, 1 - y, 2 - z) involving the phenyl ring at position 6 and C62—H62···π (1 - x, -y, 2 - z) involving the phenyl ring at C41.

Related literature top

For related literature, see: Lavagnino & Shepard (1957); Balamurugan et al. (2006, 2007). Balamurugan et al. (2006, 2007) have reported crystal structures of di-2-furylpiperidin-4-one derivatives, wherein the piperidine ring adopts chair and twist–boat conformations, respectively.

Experimental top

The title compound was prepared following the general procedure reported by Lavagnino & Shepard (1957). A mixture of r(2),c(6)-diphenylpiperidin-4-one (2.51 g, 0.01 mol), benzylcyanide (1.15 ml, 0.01 mol) and potassium hydroxide (0.66 g, 0.01 mol) in 50 ml of absolute ethanol. The solution was heated on water bath for 2 days. Then diluted with 25 ml water and chilled in an ice bath. The solid mass which separated was filtered off, dried and recrystallized from ethanol. The yield of the isolated product was 2.09 g (60%).

Structure description top

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

Fig. 1. View of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

(2,6-Diphenylpiperidin-4-ylidene)(phenyl)acetonitrile top

Crystal data top

C₂₅H₂₂N₂	Z = 2
M_r = 350.45	F(000) = 372
Triclinic, P1	D_x = 1.214 Mg m⁻³
Hall symbol: -P 1	Melting point: 441(1) K
a = 7.5687 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3610 (5) Å	Cell parameters from 3245 reflections
c = 12.1481 (5) Å	θ = 2.0–25.0°
α = 111.318 (2)°	µ = 0.07 mm⁻¹
β = 92.757 (2)°	T = 160 K
γ = 97.920 (2)°	Plate-like, yellow
V = 958.36 (7) Å³	0.28 × 0.28 × 0.18 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	2742 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generator	R_int = 0.055
Horizontally mounted graphite crystal monochromator	θ_max = 25.0°, θ_min = 2.1°
Detector resolution: 9 pixels mm^-1	h = −8→8
ω scans with κ offsets	k = −13→13
12846 measured reflections	l = −14→14
3338 independent reflections

Refinement top

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0746P)² + 0.3813P] where P = (F_o² + 2F_c²)/3
3338 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₅H₂₂N₂	γ = 97.920 (2)°
M_r = 350.45	V = 958.36 (7) Å³
Triclinic, P1	Z = 2
a = 7.5687 (3) Å	Mo Kα radiation
b = 11.3610 (5) Å	µ = 0.07 mm⁻¹
c = 12.1481 (5) Å	T = 160 K
α = 111.318 (2)°	0.28 × 0.28 × 0.18 mm
β = 92.757 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	2742 reflections with I > 2σ(I)
12846 measured reflections	R_int = 0.055
3338 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.27 e Å⁻³
3338 reflections	Δρ_min = −0.24 e Å⁻³
248 parameters

Special details top

Experimental. Solvent used: ethanol Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.483 (2) Frames collected: 193 Seconds exposure per frame: 38 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
N1	0.2897 (2)	0.28665 (14)	0.85699 (12)	0.0234 (5)
N43	0.2792 (2)	−0.07061 (15)	1.11208 (13)	0.0337 (5)
C2	0.3019 (2)	0.16655 (15)	0.75950 (14)	0.0221 (5)
C3	0.1698 (2)	0.05895 (16)	0.77310 (15)	0.0245 (5)
C4	0.2102 (2)	0.04948 (16)	0.89088 (15)	0.0247 (5)
C5	0.2147 (3)	0.17506 (16)	0.99182 (15)	0.0259 (5)
C6	0.3418 (2)	0.28366 (16)	0.97355 (14)	0.0228 (5)
C21	0.2547 (2)	0.17135 (16)	0.63899 (15)	0.0231 (5)
C22	0.1527 (3)	0.25663 (17)	0.62196 (16)	0.0305 (6)
C23	0.1094 (3)	0.25267 (18)	0.50784 (17)	0.0351 (6)
C24	0.1656 (3)	0.16411 (19)	0.41083 (16)	0.0334 (6)
C25	0.2624 (3)	0.07576 (19)	0.42646 (16)	0.0326 (6)
C26	0.3064 (3)	0.08000 (18)	0.53961 (15)	0.0289 (6)
C41	0.2409 (2)	−0.05984 (16)	0.90312 (14)	0.0224 (5)
C42	0.2639 (2)	−0.06391 (16)	1.02001 (15)	0.0229 (5)
C61	0.3303 (2)	0.40939 (15)	1.07285 (15)	0.0229 (5)
C62	0.4168 (3)	0.43681 (17)	1.18522 (16)	0.0294 (6)
C63	0.4012 (3)	0.54702 (18)	1.27961 (16)	0.0332 (6)
C64	0.3011 (3)	0.63333 (18)	1.26372 (17)	0.0339 (6)
C65	0.2169 (3)	0.60898 (18)	1.15273 (17)	0.0353 (6)
C66	0.2303 (3)	0.49737 (17)	1.05758 (17)	0.0297 (6)
C411	0.2472 (2)	−0.18250 (16)	0.80123 (14)	0.0219 (5)
C412	0.3720 (2)	−0.18561 (17)	0.72031 (15)	0.0262 (5)
C413	0.3729 (3)	−0.29637 (17)	0.62162 (15)	0.0282 (6)
C414	0.2500 (3)	−0.40591 (17)	0.60354 (16)	0.0280 (5)
C415	0.1280 (3)	−0.40399 (17)	0.68462 (16)	0.0292 (6)
C416	0.1269 (3)	−0.29380 (16)	0.78340 (16)	0.0268 (6)
H1	0.369 (3)	0.349 (2)	0.8489 (18)	0.032 (5)*
H2	0.42655	0.14747	0.76422	0.0265*
H3A	0.04586	0.07614	0.76593	0.0294*
H3B	0.17785	−0.02350	0.70878	0.0294*
H5A	0.25571	0.16749	1.06722	0.0310*
H5B	0.09216	0.19647	0.99775	0.0310*
H6	0.46768	0.26643	0.97639	0.0273*
H22	0.11217	0.31797	0.68822	0.0366*
H23	0.04009	0.31198	0.49694	0.0421*
H24	0.13807	0.16362	0.33352	0.0401*
H25	0.29848	0.01237	0.35966	0.0391*
H26	0.37339	0.01920	0.54979	0.0346*
H62	0.48774	0.37882	1.19713	0.0353*
H63	0.45969	0.56346	1.35593	0.0399*
H64	0.29037	0.70903	1.32881	0.0407*
H65	0.14914	0.66877	1.14112	0.0424*
H66	0.17080	0.48112	0.98158	0.0356*
H412	0.45739	−0.11123	0.73267	0.0314*
H413	0.45778	−0.29715	0.56637	0.0338*
H414	0.24992	−0.48166	0.53582	0.0336*
H415	0.04390	−0.47891	0.67264	0.0351*
H416	0.04356	−0.29416	0.83935	0.0322*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0313 (9)	0.0161 (8)	0.0203 (8)	0.0036 (6)	0.0011 (6)	0.0044 (6)
N43	0.0441 (10)	0.0307 (9)	0.0234 (9)	0.0011 (7)	0.0014 (7)	0.0088 (7)
C2	0.0261 (9)	0.0177 (9)	0.0196 (9)	0.0061 (7)	0.0003 (7)	0.0031 (7)
C3	0.0293 (10)	0.0179 (9)	0.0223 (9)	0.0030 (7)	−0.0005 (7)	0.0036 (7)
C4	0.0291 (10)	0.0202 (9)	0.0214 (9)	0.0004 (7)	0.0026 (7)	0.0053 (7)
C5	0.0338 (10)	0.0213 (9)	0.0200 (9)	0.0040 (7)	0.0045 (7)	0.0047 (7)
C6	0.0271 (9)	0.0194 (9)	0.0193 (9)	0.0058 (7)	0.0022 (7)	0.0037 (7)
C21	0.0265 (9)	0.0182 (9)	0.0227 (9)	0.0010 (7)	0.0001 (7)	0.0069 (7)
C22	0.0407 (11)	0.0204 (9)	0.0279 (10)	0.0066 (8)	−0.0028 (8)	0.0064 (8)
C23	0.0438 (12)	0.0251 (10)	0.0355 (11)	0.0032 (8)	−0.0125 (9)	0.0133 (9)
C24	0.0385 (11)	0.0355 (11)	0.0243 (10)	−0.0091 (9)	−0.0092 (8)	0.0158 (9)
C25	0.0358 (11)	0.0370 (11)	0.0217 (9)	0.0019 (8)	0.0029 (8)	0.0087 (8)
C26	0.0329 (10)	0.0312 (10)	0.0240 (9)	0.0099 (8)	0.0053 (8)	0.0102 (8)
C41	0.0272 (9)	0.0183 (9)	0.0191 (8)	0.0010 (7)	0.0028 (7)	0.0051 (7)
C42	0.0269 (9)	0.0172 (9)	0.0208 (9)	0.0005 (7)	0.0028 (7)	0.0038 (7)
C61	0.0257 (9)	0.0161 (9)	0.0231 (9)	0.0010 (7)	0.0028 (7)	0.0039 (7)
C62	0.0361 (11)	0.0243 (10)	0.0248 (9)	0.0077 (8)	0.0007 (8)	0.0049 (8)
C63	0.0380 (11)	0.0312 (10)	0.0220 (9)	0.0036 (8)	0.0011 (8)	0.0011 (8)
C64	0.0356 (11)	0.0223 (10)	0.0305 (10)	0.0025 (8)	0.0063 (8)	−0.0052 (8)
C65	0.0367 (11)	0.0238 (10)	0.0399 (12)	0.0121 (8)	0.0017 (9)	0.0032 (8)
C66	0.0321 (10)	0.0230 (9)	0.0288 (10)	0.0065 (8)	−0.0021 (8)	0.0037 (8)
C411	0.0288 (10)	0.0173 (9)	0.0183 (8)	0.0039 (7)	0.0007 (7)	0.0053 (7)
C412	0.0310 (10)	0.0220 (9)	0.0215 (9)	−0.0007 (7)	0.0017 (7)	0.0054 (7)
C413	0.0334 (10)	0.0284 (10)	0.0199 (9)	0.0050 (8)	0.0060 (7)	0.0055 (7)
C414	0.0363 (10)	0.0199 (9)	0.0232 (9)	0.0084 (8)	−0.0015 (8)	0.0019 (7)
C415	0.0332 (10)	0.0166 (9)	0.0348 (10)	−0.0001 (7)	0.0002 (8)	0.0079 (8)
C416	0.0312 (10)	0.0211 (9)	0.0288 (10)	0.0052 (7)	0.0079 (8)	0.0092 (8)

Geometric parameters (Å, º) top

N1—C2	1.464 (2)	C3—H3A	0.9900
N1—C6	1.465 (2)	C3—H3B	0.9900
N43—C42	1.150 (2)	C5—H5B	0.9900
N1—H1	0.90 (2)	C5—H5A	0.9900
C2—C3	1.532 (3)	C6—H6	1.0000
C2—C21	1.512 (2)	C22—H22	0.9500
C3—C4	1.494 (2)	C23—H23	0.9500
C4—C5	1.500 (3)	C24—H24	0.9500
C4—C41	1.352 (3)	C25—H25	0.9500
C5—C6	1.546 (3)	C26—H26	0.9500
C6—C61	1.515 (2)	C62—H62	0.9500
C21—C22	1.384 (3)	C63—H63	0.9500
C21—C26	1.391 (3)	C64—H64	0.9500
C22—C23	1.392 (3)	C65—H65	0.9500
C23—C24	1.373 (3)	C66—H66	0.9500
C24—C25	1.381 (3)	C411—C416	1.393 (3)
C25—C26	1.381 (3)	C411—C412	1.390 (2)
C41—C411	1.499 (2)	C412—C413	1.388 (3)
C41—C42	1.441 (2)	C413—C414	1.387 (3)
C61—C62	1.392 (3)	C414—C415	1.379 (3)
C61—C66	1.392 (3)	C415—C416	1.385 (3)
C62—C63	1.381 (3)	C412—H412	0.9500
C63—C64	1.379 (3)	C413—H413	0.9500
C64—C65	1.378 (3)	C414—H414	0.9500
C65—C66	1.391 (3)	C415—H415	0.9500
C2—H2	1.0000	C416—H416	0.9500

N1···H22	2.5600	H3A···C25^v	3.0500
N1···H66	2.5000	H3B···C26	2.8600
N43···H25ⁱ	2.8000	H3B···C411	2.5500
N43···H3Aⁱⁱ	2.9400	H3B···C412	2.5500
N43···H412ⁱⁱⁱ	2.7300	H3B···H412	2.5100
C2···C64^iv	3.598 (3)	H3B···C24^v	2.8700
C3···C412	3.232 (3)	H3B···H24^v	2.6000
C3···C24^v	3.380 (3)	H5A···C42	2.4900
C24···C3^v	3.380 (3)	H5A···C62	2.9200
C64···C2^iv	3.598 (3)	H5B···C42ⁱⁱ	2.8600
C3···H412	3.0500	H5B···H416ⁱⁱ	2.2600
C3···H24^v	3.0300	H6···H2	2.4200
C4···H412	3.0400	H6···H62	2.5000
C5···H416ⁱⁱ	2.9900	H22···N1	2.5600
C22···H1	2.89 (2)	H22···H1	2.5800
C22···H415^vi	3.0800	H22···H415^vi	2.5000
C23···H414^vi	2.9500	H23···H414^vi	2.5200
C24···H3B^v	2.8700	H23···H415^vi	2.5500
C24···H413^vii	2.9900	H23···C414^v	2.9600
C24···H3A^v	2.9700	H23···C415^v	3.0600
C25···H3A^v	3.0500	H24···C3^v	3.0300
C25···H413^vii	3.0300	H24···H3B^v	2.6000
C25···H412^vii	3.0200	H25···N43^viii	2.8000
C26···H3B	2.8600	H25···H412^vii	2.5500
C26···H26^vii	2.9100	H26···H2	2.4600
C42···H416	2.9500	H26···C26^vii	2.9100
C42···H5Bⁱⁱ	2.8600	H26···H26^vii	2.3200
C42···H5A	2.4900	H62···H6	2.5000
C62···H1^iv	2.90 (2)	H62···C412ⁱⁱⁱ	3.0200
C62···H5A	2.9200	H62···C413ⁱⁱⁱ	2.9000
C63···H1^iv	2.81 (2)	H62···C414ⁱⁱⁱ	2.9500
C64···H1^iv	2.92 (2)	H63···H413^ix	2.4700
C66···H1	2.83 (2)	H66···N1	2.5000
C412···C3	3.232 (3)	H66···H1	2.4900
C411···H3B	2.5500	H412···C3	3.0500
C412···H3B	2.5500	H412···C4	3.0400
C412···H62ⁱⁱⁱ	3.0200	H412···H3B	2.5100
C413···H62ⁱⁱⁱ	2.9000	H412···N43ⁱⁱⁱ	2.7300
C414···H23^v	2.9600	H412···C25^vii	3.0200
C414···H62ⁱⁱⁱ	2.9500	H412···H25^vii	2.5500
C415···H23^v	3.0600	H413···H63^x	2.4700
H1···C22	2.89 (2)	H413···C24^vii	2.9900
H1···C66	2.83 (2)	H413···C25^vii	3.0300
H1···H22	2.5800	H414···C23^xi	2.9500
H1···H66	2.4900	H414···H23^xi	2.5200
H1···C62^iv	2.90 (2)	H415···C22^xi	3.0800
H1···C63^iv	2.81 (2)	H415···H22^xi	2.5000
H1···C64^iv	2.92 (2)	H415···H23^xi	2.5500
H2···H6	2.4200	H416···C42	2.9500
H2···H26	2.4600	H416···C5ⁱⁱ	2.9900
H3A···N43ⁱⁱ	2.9400	H416···H5Bⁱⁱ	2.2600
H3A···C24^v	2.9700

C2—N1—C6	112.35 (14)	C6—C5—H5A	109.00
C2—N1—H1	107.7 (14)	C6—C5—H5B	109.00
C6—N1—H1	106.2 (13)	H5A—C5—H5B	108.00
N1—C2—C3	108.33 (13)	C61—C6—H6	109.00
C3—C2—C21	108.25 (13)	N1—C6—H6	109.00
N1—C2—C21	112.35 (15)	C5—C6—H6	109.00
C2—C3—C4	110.66 (14)	C21—C22—H22	120.00
C3—C4—C5	111.94 (16)	C23—C22—H22	120.00
C3—C4—C41	123.22 (16)	C24—C23—H23	120.00
C5—C4—C41	124.83 (16)	C22—C23—H23	120.00
C4—C5—C6	111.10 (15)	C25—C24—H24	120.00
C5—C6—C61	108.78 (13)	C23—C24—H24	120.00
N1—C6—C61	111.40 (15)	C26—C25—H25	120.00
N1—C6—C5	109.03 (14)	C24—C25—H25	120.00
C2—C21—C26	118.25 (16)	C21—C26—H26	119.00
C22—C21—C26	118.37 (17)	C25—C26—H26	119.00
C2—C21—C22	123.24 (15)	C63—C62—H62	119.00
C21—C22—C23	120.08 (18)	C61—C62—H62	119.00
C22—C23—C24	120.8 (2)	C62—C63—H63	120.00
C23—C24—C25	119.54 (18)	C64—C63—H63	120.00
C24—C25—C26	119.69 (18)	C65—C64—H64	120.00
C21—C26—C25	121.4 (2)	C63—C64—H64	120.00
C4—C41—C411	124.24 (15)	C64—C65—H65	120.00
C4—C41—C42	119.75 (16)	C66—C65—H65	120.00
C42—C41—C411	115.97 (16)	C65—C66—H66	120.00
N43—C42—C41	178.0 (2)	C61—C66—H66	120.00
C6—C61—C62	119.30 (16)	C41—C411—C412	119.85 (16)
C62—C61—C66	118.17 (17)	C41—C411—C416	121.41 (15)
C6—C61—C66	122.48 (15)	C412—C411—C416	118.71 (17)
C61—C62—C63	121.02 (19)	C411—C412—C413	120.62 (18)
C62—C63—C64	120.37 (18)	C412—C413—C414	120.12 (18)
C63—C64—C65	119.49 (19)	C413—C414—C415	119.49 (18)
C64—C65—C66	120.4 (2)	C414—C415—C416	120.60 (19)
C61—C66—C65	120.51 (18)	C411—C416—C415	120.43 (18)
N1—C2—H2	109.00	C411—C412—H412	120.00
C3—C2—H2	109.00	C413—C412—H412	120.00
C21—C2—H2	109.00	C412—C413—H413	120.00
C4—C3—H3A	109.00	C414—C413—H413	120.00
C2—C3—H3A	110.00	C413—C414—H414	120.00
C2—C3—H3B	110.00	C415—C414—H414	120.00
C4—C3—H3B	110.00	C414—C415—H415	120.00
H3A—C3—H3B	108.00	C416—C415—H415	120.00
C4—C5—H5A	109.00	C411—C416—H416	120.00
C4—C5—H5B	109.00	C415—C416—H416	120.00

C6—N1—C2—C3	62.57 (17)	C2—C21—C26—C25	177.69 (19)
C6—N1—C2—C21	−177.90 (13)	C22—C21—C26—C25	1.9 (3)
C2—N1—C6—C5	−60.63 (18)	C21—C22—C23—C24	0.5 (3)
C2—N1—C6—C61	179.31 (13)	C22—C23—C24—C25	1.7 (3)
N1—C2—C3—C4	−58.01 (17)	C23—C24—C25—C26	−2.0 (3)
C21—C2—C3—C4	179.91 (13)	C24—C25—C26—C21	0.3 (3)
N1—C2—C21—C22	−21.6 (2)	C4—C41—C411—C412	59.5 (2)
N1—C2—C21—C26	162.77 (16)	C4—C41—C411—C416	−118.7 (2)
C3—C2—C21—C22	98.0 (2)	C42—C41—C411—C412	−122.58 (17)
C3—C2—C21—C26	−77.65 (19)	C42—C41—C411—C416	59.2 (2)
C2—C3—C4—C5	54.50 (19)	C6—C61—C62—C63	−176.33 (18)
C2—C3—C4—C41	−124.73 (17)	C66—C61—C62—C63	1.2 (3)
C3—C4—C5—C6	−52.5 (2)	C6—C61—C66—C65	177.04 (18)
C41—C4—C5—C6	126.76 (17)	C62—C61—C66—C65	−0.4 (3)
C3—C4—C41—C42	−174.76 (14)	C61—C62—C63—C64	−0.9 (3)
C3—C4—C41—C411	3.1 (3)	C62—C63—C64—C65	−0.2 (3)
C5—C4—C41—C42	6.1 (3)	C63—C64—C65—C66	0.9 (3)
C5—C4—C41—C411	−176.04 (16)	C64—C65—C66—C61	−0.6 (3)
C4—C5—C6—N1	54.1 (2)	C41—C411—C412—C413	−176.23 (17)
C4—C5—C6—C61	175.76 (14)	C416—C411—C412—C413	2.0 (3)
N1—C6—C61—C62	−163.58 (16)	C41—C411—C416—C415	176.03 (18)
N1—C6—C61—C66	19.0 (2)	C412—C411—C416—C415	−2.2 (3)
C5—C6—C61—C62	76.2 (2)	C411—C412—C413—C414	−0.8 (3)
C5—C6—C61—C66	−101.3 (2)	C412—C413—C414—C415	−0.4 (3)
C2—C21—C22—C23	−177.83 (18)	C413—C414—C415—C416	0.2 (3)
C26—C21—C22—C23	−2.2 (3)	C414—C415—C416—C411	1.1 (3)

Symmetry codes: (i) x, y, z+1; (ii) −x, −y, −z+2; (iii) −x+1, −y, −z+2; (iv) −x+1, −y+1, −z+2; (v) −x, −y, −z+1; (vi) x, y+1, z; (vii) −x+1, −y, −z+1; (viii) x, y, z−1; (ix) x, y+1, z+1; (x) x, y−1, z−1; (xi) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···N1	0.95	2.56	2.873 (2)	100
C66—H66···N1	0.95	2.50	2.834 (2)	101
N1—H1···Cg^iv	0.90 (2)	2.68 (2)	3.537 (2)	159.4 (2)
C62—H62···Cgⁱⁱⁱ	0.95	2.74	3.639	159

Symmetry codes: (iii) −x+1, −y, −z+2; (iv) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₂N₂
M_r	350.45
Crystal system, space group	Triclinic, P1
Temperature (K)	160
a, b, c (Å)	7.5687 (3), 11.3610 (5), 12.1481 (5)
α, β, γ (°)	111.318 (2), 92.757 (2), 97.920 (2)
V (Å³)	958.36 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.28 × 0.28 × 0.18

Data collection
Diffractometer	Nonius KappaCCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12846, 3338, 2742
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.144, 1.05
No. of reflections	3338
No. of parameters	248
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.24

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···N1	0.95	2.56	2.873 (2)	100
C66—H66···N1	0.95	2.50	2.834 (2)	101
N1—H1···Cgⁱ	0.90 (2)	2.68 (2)	3.537 (2)	159.4 (2)
C62—H62···Cgⁱⁱ	0.95	2.74	3.639	159

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

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page