(E)-1-([1,1′-Biphen­yl]-4-yl)-2-(1,3,3-tri­methylindolin-2-yl­idene)ethanone

Vázquez-Vuelvas, O.F.; Pineda-Contreras, A.; Morales-Morales, D.; Hernández-Ortega, S.; Tlenkopatchev, M.

doi:10.1107/S1600536811045168

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3223

https://doi.org/10.1107/S1600536811045168

Open

access

(E)-1-([1,1′-Biphenyl]-4-yl)-2-(1,3,3-trimethylindolin-2-ylidene)ethanone

Oscar F. Vázquez-Vuelvas,^a ^* Armando Pineda-Contreras,^a ‡ David Morales-Morales,^b Simón Hernández-Ortega ^b and Mikhail Tlenkopatchev ^c

^aFacultad de Ciencias Químicas, Universidad de Colima, km 9 Carr. Colima-Coquimatlán s/n, Coquimatlán, Colima 28400, Mexico, ^bInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México D.F. 04510, Mexico, and ^cInstituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México D.F. 04510, Mexico
^*Correspondence e-mail: oscar_vazquez@ucol.mx

(Received 3 August 2011; accepted 27 October 2011; online 9 November 2011)

The title compound, C₂₅H₂₃NO, consists of a biphenyl-4-carbonyl unit attached to an exocyclic double bond group at position 2 of an indole unit, which presents methyl groups as substituents at positions 1 and 3. The molecular conformation is s-cis with an E configuration, supported by weak intramolecular C—H⋯O contacts involving the methyl groups and the carbonyl function. The rings of the biphenyl group are twisted by 37.13 (5)°. In the crystal, C—H⋯O and C—H⋯π interactions link the molecules.

Related literature

For background to the Fisher base (2,3-dihydro-1H-1,3,3-trimethyl-2-methyleneindole), see: Minkin (2004 ); Przhiyalgovskaya et al. (1987 ). For applications of derivatives of the Fisher base in materials and organic synthesis, see: Corns et al. (2009 ); Shimkin et al. (2006 ); Song et al. (2005 ); Tarshits et al. (2005 ); Cui & Kim (2004 ).

Experimental

Crystal data

C₂₅H₂₃NO
M_r = 353.44
Monoclinic, P 2₁ /c
a = 12.3274 (13) Å
b = 15.7586 (16) Å
c = 10.3848 (11) Å
β = 104.719 (2)°
V = 1951.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.36 × 0.28 × 0.26 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
15883 measured reflections
3584 independent reflections
2585 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.106
S = 0.97
3584 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C21–C26, C12–C17 and C4–C9 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19B⋯O1	0.96	2.36	3.112 (2)	135
C20—H20B⋯O1	0.96	2.31	3.078 (2)	137
C24—H24⋯O1ⁱ	0.93	2.54	3.465 (2)	171
C7—H7⋯Cg1ⁱⁱ	0.93	2.74	3.5436 (16)	145
C20—H20C⋯Cg2ⁱⁱⁱ	0.96	2.81	3.7562 (17)	167
C26—H26⋯Cg3ⁱⁱⁱ	0.93	2.89	3.7700 (17)	158
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x-1, y, z-1; (iii) -x, -y, -z+1.

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811045168/bh2373sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045168/bh2373Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811045168/bh2373Isup3.cml

checkCIF report

Comment top

The compound 2,3-dihydro-1H-1,3,3-trimethyl-2-methyleneindole, well known as the Fischer base, has been widely used in organic synthesis as precursor of different types of chemical switches (Minkin, 2004; Przhiyalgovskaya et al., 1987). Products with different skills to work as switches have been used in optoelectronics (Shimkin et al., 2006), as organic electroluminescent materials (Cui & Kim, 2004) and dyes (Song et al., 2005). Moreover, the enaminoketone derivatives of the Fischer base, like the title compound, are important intermediates for the synthesis of spiropyrans and spirooxazines (Corns et al., 2009), as well as for the preparation of acetylenic products via enaminoketone fragmentation (Tarshits et al., 2005).

The structure of the title compound [alternative name: (E)-2,3-dihydro-2-(biphenylacylidene)-1,3,3-trimethyl-1H-indol], C₂₅H₂₃NO, has monoclinic (P2₁/c) symmetry. The crystal structure exhibits C—H···O intramolecular contacts in a bifurcated fashion with C19 and C20 as the donor atoms and the O atom of carbonyl group O1 as the acceptor (Table 1, Fig. 1). Moreover, despite the molecule presents high conjugation degree, the molecule is not planar; the benzene group (C12···C17) is rotated with respect to indole group (N1···C9) with the dihedral angle of 33.19 (5)°, while the biphenyl rings presents rotation showed by the dihedral angle of 37.13 (5)°.

The intermolecular assembly presents an antiparallel arrangement in a head-to-tail stacking mode especially favored by edge-to-face weak C—H···π interaction between 2.739 to 2.891 Å (see Table 2). Moreover, the weak C—H···O interaction formed by C24–H24C···O1 propagates in the ac plane (Fig. 2).

Related literature top

For backgroung to the Fisher base (2,3-dihydro-1H-1,3,3-trimethyl-2-methyleneindole), see: Minkin (2004); Przhiyalgovskaya et al. (1987). For applications of derivatives of the Fisher base in materials and organic synthesis, see: Corns et al. (2009); Shimkin et al. (2006); Song et al. (2005); Tarshits et al. (2005); Cui & Kim (2004).

Experimental top

A mixture of 4-biphenylcarboxylic acid (9.59 g, 48.38 mmol) and thionyl chloride (1.5 eq., 8.63 g, 72.57 mmol) in 24 ml of dry benzene was refluxed for 1.5 h, afterward the solvent and the excess of thionyl chloride was evaporated under vacuum. For complete removal of the thionyl chloride, 24 ml of petroleum ether was added to the residue and then eliminated under vacuum. The 4-biphenyl-carbonyl chloride thus obtained was dissolved in 60 ml of dry benzene, then added to a mixture of the Fischer base 1,3,3-trimethyl-2-methyleneindoline (1 eq., 8.38 g, 48.38 mmol) and triethylamine (1.2 eq., 5.81 g, 58.04 mmol) in 60 ml of dry benzene. The reaction mixture was maintained at 40 °C for 2 h, after that it was allowed to stand overnight at room temperature. The final reaction mixture was first washed with water and the organic phase was separated and removed under vacuum. The resulting solid was washed successively with isopropyl alcohol. The crude product was purified using a column chromatography with chloroform as a mobile phase. Suitable crystals for X-ray diffraction were obtained from toluene by slow evaporation.

Structure description top

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids for non-H atom are drawn at the 30% of probability level.
	Fig. 2. The crystal packing of the title compound viewed down the a axis, showing the molecules intermolecularly connected by weak O—H···O interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted.

(E)-1-([1,1'-Biphenyl]-4-yl)-2-(1,3,3-trimethylindolin-2-ylidene)ethanone top

Crystal data top

C₂₅H₂₃NO	F(000) = 752
M_r = 353.44	D_x = 1.203 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7167 reflections
a = 12.3274 (13) Å	θ = 2.1–25.3°
b = 15.7586 (16) Å	µ = 0.07 mm⁻¹
c = 10.3848 (11) Å	T = 298 K
β = 104.719 (2)°	Prism, yellow
V = 1951.2 (4) Å³	0.36 × 0.28 × 0.26 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2585 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 25.4°, θ_min = 1.7°
Detector resolution: 0.83 pixels mm^-1	h = −14→14
ω scans	k = −18→19
15883 measured reflections	l = −12→12
3584 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.065P)²] where P = (F_o² + 2F_c²)/3
3584 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³
0 constraints

Crystal data top

C₂₅H₂₃NO	V = 1951.2 (4) Å³
M_r = 353.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3274 (13) Å	µ = 0.07 mm⁻¹
b = 15.7586 (16) Å	T = 298 K
c = 10.3848 (11) Å	0.36 × 0.28 × 0.26 mm
β = 104.719 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2585 reflections with I > 2σ(I)
15883 measured reflections	R_int = 0.033
3584 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 0.97	Δρ_max = 0.18 e Å⁻³
3584 reflections	Δρ_min = −0.18 e Å⁻³
247 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.11145 (9)	0.15214 (6)	0.45956 (10)	0.0720 (3)
N1	−0.10316 (9)	0.01690 (6)	0.12145 (10)	0.0495 (3)
C2	−0.04032 (10)	0.06729 (8)	0.22033 (12)	0.0443 (3)
C3	−0.09068 (10)	0.15640 (7)	0.20258 (12)	0.0429 (3)
C4	−0.26386 (11)	0.20310 (9)	0.01194 (13)	0.0520 (3)
H4	−0.2620	0.2591	0.0405	0.062*
C5	−0.34517 (11)	0.17673 (10)	−0.09918 (14)	0.0577 (4)
H5	−0.3978	0.2153	−0.1458	0.069*
C6	−0.34813 (11)	0.09381 (10)	−0.14058 (14)	0.0579 (4)
H6	−0.4032	0.0770	−0.2153	0.069*
C7	−0.27119 (12)	0.03476 (9)	−0.07375 (13)	0.0555 (4)
H7	−0.2736	−0.0214	−0.1017	0.067*
C8	−0.19038 (10)	0.06262 (8)	0.03644 (12)	0.0447 (3)
C9	−0.18599 (10)	0.14580 (8)	0.07967 (12)	0.0424 (3)
C10	0.04982 (11)	0.03623 (8)	0.31302 (13)	0.0527 (4)
H10	0.0659	−0.0207	0.3034	0.063*
C11	0.12365 (11)	0.07890 (9)	0.42363 (13)	0.0523 (4)
C12	0.22233 (11)	0.02928 (8)	0.50225 (13)	0.0472 (3)
C13	0.26762 (11)	0.04889 (9)	0.63521 (13)	0.0530 (4)
H13	0.2360	0.0924	0.6741	0.064*
C14	0.35843 (11)	0.00524 (9)	0.71096 (13)	0.0528 (4)
H14	0.3854	0.0185	0.8007	0.063*
C15	0.41041 (10)	−0.05831 (8)	0.65561 (12)	0.0447 (3)
C16	0.36776 (10)	−0.07546 (8)	0.52088 (13)	0.0490 (3)
H16	0.4028	−0.1160	0.4802	0.059*
C17	0.27469 (11)	−0.03366 (8)	0.44639 (13)	0.0504 (3)
H17	0.2465	−0.0478	0.3572	0.060*
C18	−0.08214 (14)	−0.07245 (9)	0.10425 (17)	0.0717 (5)
H18A	−0.0069	−0.0797	0.0960	0.107*
H18B	−0.1341	−0.0931	0.0253	0.107*
H18C	−0.0916	−0.1036	0.1801	0.107*
C19	−0.00644 (11)	0.22263 (9)	0.17900 (15)	0.0586 (4)
H19A	0.0231	0.2048	0.1063	0.088*
H19B	0.0537	0.2282	0.2580	0.088*
H19C	−0.0435	0.2763	0.1579	0.088*
C20	−0.13763 (13)	0.18132 (10)	0.32054 (13)	0.0621 (4)
H20A	−0.1736	0.2357	0.3036	0.093*
H20B	−0.0775	0.1843	0.4000	0.093*
H20C	−0.1912	0.1396	0.3319	0.093*
C21	0.50510 (10)	−0.10866 (8)	0.73665 (13)	0.0483 (3)
C22	0.59153 (11)	−0.13759 (9)	0.68482 (15)	0.0555 (4)
H22	0.5925	−0.1234	0.5982	0.067*
C23	0.67627 (12)	−0.18739 (9)	0.76088 (17)	0.0687 (5)
H23	0.7339	−0.2061	0.7251	0.082*
C24	0.67611 (15)	−0.20941 (10)	0.88879 (19)	0.0773 (5)
H24	0.7326	−0.2437	0.9391	0.093*
C25	0.59186 (15)	−0.18033 (11)	0.94158 (17)	0.0782 (5)
H25	0.5919	−0.1944	1.0286	0.094*
C26	0.50713 (12)	−0.13039 (10)	0.86699 (15)	0.0640 (4)
H26	0.4507	−0.1110	0.9043	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0676 (7)	0.0569 (7)	0.0752 (7)	0.0108 (5)	−0.0118 (6)	−0.0149 (5)
N1	0.0500 (6)	0.0393 (6)	0.0520 (6)	0.0035 (5)	−0.0001 (5)	−0.0079 (5)
C2	0.0436 (7)	0.0426 (7)	0.0450 (7)	−0.0015 (6)	0.0081 (6)	−0.0031 (6)
C3	0.0419 (7)	0.0388 (7)	0.0466 (7)	0.0005 (5)	0.0089 (6)	−0.0039 (6)
C4	0.0483 (8)	0.0471 (8)	0.0605 (9)	0.0028 (6)	0.0138 (7)	0.0052 (6)
C5	0.0444 (8)	0.0685 (10)	0.0574 (9)	0.0055 (7)	0.0075 (7)	0.0158 (8)
C6	0.0464 (8)	0.0744 (11)	0.0476 (8)	−0.0038 (7)	0.0024 (6)	0.0030 (7)
C7	0.0546 (8)	0.0565 (8)	0.0512 (8)	−0.0033 (7)	0.0058 (7)	−0.0082 (7)
C8	0.0421 (7)	0.0478 (8)	0.0433 (7)	0.0000 (6)	0.0092 (6)	−0.0010 (6)
C9	0.0403 (7)	0.0438 (7)	0.0436 (7)	−0.0009 (5)	0.0116 (6)	0.0013 (6)
C10	0.0513 (8)	0.0421 (7)	0.0575 (9)	0.0042 (6)	0.0004 (7)	−0.0033 (6)
C11	0.0502 (8)	0.0483 (8)	0.0536 (8)	0.0014 (6)	0.0044 (7)	−0.0017 (7)
C12	0.0445 (7)	0.0486 (8)	0.0454 (7)	−0.0028 (6)	0.0058 (6)	0.0012 (6)
C13	0.0490 (8)	0.0539 (8)	0.0535 (8)	0.0030 (6)	0.0080 (7)	−0.0059 (6)
C14	0.0498 (8)	0.0616 (9)	0.0428 (7)	−0.0012 (7)	0.0040 (6)	−0.0036 (7)
C15	0.0385 (7)	0.0461 (7)	0.0476 (7)	−0.0050 (6)	0.0074 (6)	0.0036 (6)
C16	0.0455 (7)	0.0496 (8)	0.0512 (8)	0.0011 (6)	0.0111 (6)	−0.0014 (6)
C17	0.0503 (8)	0.0555 (8)	0.0419 (7)	−0.0009 (6)	0.0052 (6)	−0.0018 (6)
C18	0.0715 (10)	0.0470 (9)	0.0850 (11)	0.0077 (7)	−0.0012 (9)	−0.0164 (8)
C19	0.0524 (8)	0.0474 (8)	0.0721 (10)	−0.0047 (6)	0.0088 (7)	0.0017 (7)
C20	0.0611 (9)	0.0707 (10)	0.0547 (9)	0.0088 (8)	0.0151 (7)	−0.0113 (7)
C21	0.0423 (7)	0.0448 (7)	0.0542 (8)	−0.0062 (6)	0.0059 (6)	0.0023 (6)
C22	0.0464 (8)	0.0543 (8)	0.0618 (9)	−0.0025 (6)	0.0061 (7)	−0.0063 (7)
C23	0.0493 (9)	0.0616 (10)	0.0860 (12)	0.0067 (7)	0.0001 (8)	−0.0153 (9)
C24	0.0683 (11)	0.0556 (10)	0.0896 (13)	0.0104 (8)	−0.0137 (10)	0.0073 (9)
C25	0.0781 (12)	0.0776 (11)	0.0711 (11)	0.0085 (10)	0.0042 (9)	0.0251 (9)
C26	0.0575 (9)	0.0707 (10)	0.0617 (10)	0.0040 (7)	0.0114 (8)	0.0175 (8)

Geometric parameters (Å, º) top

O1—C11	1.2340 (16)	C14—H14	0.9300
N1—C2	1.3714 (15)	C15—C16	1.3904 (18)
N1—C8	1.4043 (15)	C15—C21	1.4836 (17)
N1—C18	1.4509 (17)	C16—C17	1.3775 (17)
C2—C10	1.3628 (17)	C16—H16	0.9300
C2—C3	1.5276 (17)	C17—H17	0.9300
C3—C9	1.5085 (17)	C18—H18A	0.9600
C3—C20	1.5329 (18)	C18—H18B	0.9600
C3—C19	1.5352 (18)	C18—H18C	0.9600
C4—C9	1.3742 (17)	C19—H19A	0.9600
C4—C5	1.3861 (19)	C19—H19B	0.9600
C4—H4	0.9300	C19—H19C	0.9600
C5—C6	1.373 (2)	C20—H20A	0.9600
C5—H5	0.9300	C20—H20B	0.9600
C6—C7	1.3830 (19)	C20—H20C	0.9600
C6—H6	0.9300	C21—C22	1.3871 (19)
C7—C8	1.3840 (17)	C21—C26	1.3902 (19)
C7—H7	0.9300	C22—C23	1.3826 (19)
C8—C9	1.3821 (18)	C22—H22	0.9300
C10—C11	1.4383 (17)	C23—C24	1.373 (2)
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.5010 (18)	C24—C25	1.371 (2)
C12—C13	1.3864 (17)	C24—H24	0.9300
C12—C17	1.3883 (18)	C25—C26	1.378 (2)
C13—C14	1.3775 (18)	C25—H25	0.9300
C13—H13	0.9300	C26—H26	0.9300
C14—C15	1.3897 (19)

C2—N1—C8	111.73 (10)	C14—C15—C16	117.39 (12)
C2—N1—C18	124.71 (11)	C14—C15—C21	121.99 (12)
C8—N1—C18	123.55 (11)	C16—C15—C21	120.58 (12)
C10—C2—N1	121.67 (12)	C17—C16—C15	121.35 (13)
C10—C2—C3	130.46 (11)	C17—C16—H16	119.3
N1—C2—C3	107.87 (10)	C15—C16—H16	119.3
C9—C3—C2	101.86 (9)	C16—C17—C12	121.08 (12)
C9—C3—C20	109.48 (10)	C16—C17—H17	119.5
C2—C3—C20	111.31 (11)	C12—C17—H17	119.5
C9—C3—C19	110.69 (11)	N1—C18—H18A	109.5
C2—C3—C19	111.94 (11)	N1—C18—H18B	109.5
C20—C3—C19	111.18 (11)	H18A—C18—H18B	109.5
C9—C4—C5	119.50 (13)	N1—C18—H18C	109.5
C9—C4—H4	120.2	H18A—C18—H18C	109.5
C5—C4—H4	120.2	H18B—C18—H18C	109.5
C6—C5—C4	120.13 (13)	C3—C19—H19A	109.5
C6—C5—H5	119.9	C3—C19—H19B	109.5
C4—C5—H5	119.9	H19A—C19—H19B	109.5
C5—C6—C7	121.52 (13)	C3—C19—H19C	109.5
C5—C6—H6	119.2	H19A—C19—H19C	109.5
C7—C6—H6	119.2	H19B—C19—H19C	109.5
C6—C7—C8	117.34 (13)	C3—C20—H20A	109.5
C6—C7—H7	121.3	C3—C20—H20B	109.5
C8—C7—H7	121.3	H20A—C20—H20B	109.5
C9—C8—C7	122.01 (12)	C3—C20—H20C	109.5
C9—C8—N1	108.77 (10)	H20A—C20—H20C	109.5
C7—C8—N1	129.22 (12)	H20B—C20—H20C	109.5
C4—C9—C8	119.49 (12)	C22—C21—C26	118.11 (13)
C4—C9—C3	130.76 (12)	C22—C21—C15	121.79 (12)
C8—C9—C3	109.74 (10)	C26—C21—C15	120.07 (13)
C2—C10—C11	129.28 (13)	C23—C22—C21	120.55 (14)
C2—C10—H10	115.4	C23—C22—H22	119.7
C11—C10—H10	115.4	C21—C22—H22	119.7
O1—C11—C10	125.30 (12)	C24—C23—C22	120.63 (16)
O1—C11—C12	117.83 (12)	C24—C23—H23	119.7
C10—C11—C12	116.86 (12)	C22—C23—H23	119.7
C13—C12—C17	117.59 (12)	C25—C24—C23	119.32 (15)
C13—C12—C11	119.42 (12)	C25—C24—H24	120.3
C17—C12—C11	122.92 (12)	C23—C24—H24	120.3
C14—C13—C12	121.37 (13)	C24—C25—C26	120.61 (16)
C14—C13—H13	119.3	C24—C25—H25	119.7
C12—C13—H13	119.3	C26—C25—H25	119.7
C13—C14—C15	121.13 (12)	C25—C26—C21	120.77 (15)
C13—C14—H14	119.4	C25—C26—H26	119.6
C15—C14—H14	119.4	C21—C26—H26	119.6

C8—N1—C2—C10	−179.03 (12)	N1—C2—C10—C11	−179.06 (13)
C18—N1—C2—C10	0.1 (2)	C3—C2—C10—C11	1.0 (2)
C8—N1—C2—C3	0.94 (14)	C2—C10—C11—O1	6.0 (2)
C18—N1—C2—C3	−179.94 (13)	C2—C10—C11—C12	−174.96 (14)
C10—C2—C3—C9	178.67 (14)	O1—C11—C12—C13	26.4 (2)
N1—C2—C3—C9	−1.30 (13)	C10—C11—C12—C13	−152.73 (13)
C10—C2—C3—C20	−64.73 (18)	O1—C11—C12—C17	−150.53 (14)
N1—C2—C3—C20	115.30 (12)	C10—C11—C12—C17	30.35 (19)
C10—C2—C3—C19	60.39 (18)	C17—C12—C13—C14	−2.6 (2)
N1—C2—C3—C19	−119.58 (12)	C11—C12—C13—C14	−179.74 (12)
C9—C4—C5—C6	0.4 (2)	C12—C13—C14—C15	2.2 (2)
C4—C5—C6—C7	0.0 (2)	C13—C14—C15—C16	0.5 (2)
C5—C6—C7—C8	−0.3 (2)	C13—C14—C15—C21	−177.26 (12)
C6—C7—C8—C9	0.35 (19)	C14—C15—C16—C17	−2.71 (19)
C6—C7—C8—N1	−179.92 (13)	C21—C15—C16—C17	175.13 (12)
C2—N1—C8—C9	−0.12 (15)	C15—C16—C17—C12	2.2 (2)
C18—N1—C8—C9	−179.25 (13)	C13—C12—C17—C16	0.5 (2)
C2—N1—C8—C7	−179.88 (12)	C11—C12—C17—C16	177.46 (12)
C18—N1—C8—C7	1.0 (2)	C14—C15—C21—C22	−146.14 (14)
C5—C4—C9—C8	−0.41 (19)	C16—C15—C21—C22	36.12 (18)
C5—C4—C9—C3	−179.14 (12)	C14—C15—C21—C26	35.92 (18)
C7—C8—C9—C4	0.03 (19)	C16—C15—C21—C26	−141.81 (14)
N1—C8—C9—C4	−179.75 (11)	C26—C21—C22—C23	0.7 (2)
C7—C8—C9—C3	179.01 (12)	C15—C21—C22—C23	−177.27 (12)
N1—C8—C9—C3	−0.77 (14)	C21—C22—C23—C24	0.3 (2)
C2—C3—C9—C4	−179.92 (13)	C22—C23—C24—C25	−1.1 (2)
C20—C3—C9—C4	62.16 (18)	C23—C24—C25—C26	0.9 (3)
C19—C3—C9—C4	−60.75 (18)	C24—C25—C26—C21	0.2 (2)
C2—C3—C9—C8	1.25 (13)	C22—C21—C26—C25	−0.9 (2)
C20—C3—C9—C8	−116.67 (12)	C15—C21—C26—C25	177.07 (14)
C19—C3—C9—C8	120.42 (12)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C21–C26, C12–C17 and C4–C9 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19B···O1	0.96	2.36	3.112 (2)	135
C20—H20B···O1	0.96	2.31	3.078 (2)	137
C24—H24···O1ⁱ	0.93	2.54	3.465 (2)	171
C7—H7···Cg1ⁱⁱ	0.93	2.74	3.5436 (16)	145
C20—H20C···Cg2ⁱⁱⁱ	0.96	2.81	3.7562 (17)	167
C26—H26···Cg3ⁱⁱⁱ	0.93	2.89	3.7700 (17)	158

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

Experimental details

Crystal data
Chemical formula	C₂₅H₂₃NO
M_r	353.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.3274 (13), 15.7586 (16), 10.3848 (11)
β (°)	104.719 (2)
V (Å³)	1951.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.36 × 0.28 × 0.26

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15883, 3584, 2585
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.106, 0.97
No. of reflections	3584
No. of parameters	247
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2002), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C21–C26, C12–C17 and C4–C9 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19B···O1	0.96	2.360	3.112 (2)	134.84
C20—H20B···O1	0.96	2.309	3.078 (2)	136.50
C24—H24···O1ⁱ	0.93	2.544	3.465 (2)	170.6
C7—H7···Cg1ⁱⁱ	0.93	2.74	3.5436 (16)	145
C20—H20C···Cg2ⁱⁱⁱ	0.96	2.81	3.7562 (17)	167
C26—H26···Cg3ⁱⁱⁱ	0.93	2.89	3.7700 (17)	158

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

Footnotes

‡Additional author for correspondence, e-mail: armandop@ucol.mx.

Acknowledgements

We are grateful for funding from CONACyT (project No. 52115-Y).

References

Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR. Bonn, Germany. Google Scholar
Bruker (1999). SMART and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Corns, S. N., Partington, S. M. & Towns, A. D. (2009). Color Technol. 125, 249–261. CAS Google Scholar
Cui, J. & Kim, S.-H. (2004). Chin. Sci. Bull. 49, 797–802. Web of Science CrossRef CAS Google Scholar
Minkin, V. I. (2004). Chem. Rev. 104, 2751–2776. Web of Science CrossRef PubMed CAS Google Scholar
Przhiyalgovskaya, N. M., Kon'kov, L. I., Tarshits, D. L., Salmina, S. V., Segizova, N. T. & Suvorov, N. N. (1987). Chem. Heterocycl. Compd, 23, 751–754. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shimkin, A. A., Shirinian, V. Z., Nikalin, D. M., Krayushkin, M. M., Pivina, T. S., Troitsky, N. A., Vorontsova, L. G. & Starikova, Z. A. (2006). Eur. J. Org. Chem. pp. 2087–2092. Web of Science CSD CrossRef Google Scholar
Song, H., Chen, K. & Tian, H. (2005). Dyes Pigments, 67, 1–7. CrossRef CAS Google Scholar
Tarshits, D. L., Tarasov, S. Y. & Buyanov, V. N. (2005). Russ. Chem. Bull. 54, 2586–2589. Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3223

https://doi.org/10.1107/S1600536811045168

Open

access