Literature DB >> 24098196

1-(4-{[(1,3,3-Tri-methyl-indolin-2-yl-idene)meth-yl]diazen-yl}phen-yl)ethanone.

Graeme J Gainsford¹, Mohamed Ashraf, M Delower H Bhuiyan, Andrew J Kay.

Abstract

The title compound, C20H21N3O, has crystallographic mirror symmetry with all non-H atoms apart from the methyl C atom of the CMe2 group lying on the mirror plane. Mol-ecules are linked into planar sheets parallel to (010) by phen-yl-azo C-H⋯N and phen-yl-ethanone C-H⋯O inter-actions. Methyl C-H⋯π inter-actions provide crosslinking between the planes.

Entities: CellLine Chemical Disease Species

Year: 2013 PMID： 24098196 PMCID： PMC3790374 DOI： 10.1107/S1600536813024124

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For general background to NLO chromophores, see: Dalton et al. (2011 ▶); Marder et al. (1994 ▶); Cheng et al. (1991 ▶); Mashraqui et al. (2004 ▶); Moylan et al. (1993 ▶); Zhang et al. (1997 ▶); Prim et al. (1994 ▶). For related structures, see: Odabasoglu et al. (2005 ▶); Simunek et al. (2003 ▶); Bhuiyan et al. (2011 ▶); Ashraf et al. (2013 ▶). For analysis of the structures, see: Spek (2009 ▶); Bernstein et al. (1995 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C20H21N3O M = 319.40 Monoclinic, a = 14.8688 (2) Å b = 6.89500 (12) Å c = 16.3546 (3) Å β = 99.5834 (16)° V = 1653.27 (5) Å3 Z = 4 Cu Kα radiation μ = 0.64 mm−1 T = 120 K 0.19 × 0.15 × 0.09 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer Absorption correction: gaussian (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.804, T max = 1.000 9379 measured reflections 1803 independent reflections 1634 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.098 S = 1.07 1803 reflections 153 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.27 e Å−3 Δρmin = −0.21 e Å−3 Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2012 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL2012, PLATON (Spek, 2009 ▶) and Mercury. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813024124/tk5249sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024124/tk5249Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813024124/tk5249Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₀H₂₁N₃O	F(000) = 680
M_r = 319.40	D_x = 1.283 Mg m⁻³
Monoclinic, C2/m	Cu Kα radiation, λ = 1.5418 Å
a = 14.8688 (2) Å	Cell parameters from 4498 reflections
b = 6.89500 (12) Å	θ = 5.5–73.9°
c = 16.3546 (3) Å	µ = 0.64 mm⁻¹
β = 99.5834 (16)°	T = 120 K
V = 1653.27 (5) Å³	Block, red
Z = 4	0.19 × 0.15 × 0.09 mm

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	1803 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1634 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.026
Detector resolution: 10.6501 pixels mm^-1	θ_max = 73.8°, θ_min = 2.7°
ω scans	h = −17→18
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2013)	k = −8→8
T_min = 0.804, T_max = 1.000	l = −20→19
9379 measured reflections

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0502P)² + 0.9765P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
1803 reflections	Δρ_max = 0.27 e Å⁻³
153 parameters	Δρ_min = −0.21 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
O1	0.93789 (7)	0.0000	0.21729 (7)	0.0256 (3)
N1	0.24599 (8)	0.0000	0.25969 (8)	0.0192 (3)
N2	0.46957 (8)	0.0000	0.19967 (7)	0.0186 (3)
N3	0.50012 (8)	0.0000	0.13053 (8)	0.0204 (3)
C1	0.22453 (9)	0.0000	0.34038 (9)	0.0187 (3)
C2	0.13956 (10)	0.0000	0.36490 (10)	0.0227 (3)
H2	0.0848	0.0000	0.3256	0.027*
C3	0.13841 (11)	0.0000	0.44990 (11)	0.0255 (3)
H3	0.0814	0.0000	0.4690	0.031*
C4	0.21825 (11)	0.0000	0.50739 (10)	0.0245 (3)
H4	0.2153	0.0000	0.5650	0.029*
C5	0.30291 (10)	0.0000	0.48133 (9)	0.0216 (3)
H5	0.3577	0.0000	0.5206	0.026*
C6	0.30564 (9)	0.0000	0.39733 (9)	0.0185 (3)
C7	0.38604 (9)	0.0000	0.35149 (9)	0.0177 (3)
C8	0.44476 (7)	0.18267 (16)	0.37151 (6)	0.0217 (2)
H8A	0.4685	0.1868	0.4311	0.033*
H8B	0.4075	0.2981	0.3557	0.033*
H8C	0.4958	0.1796	0.3405	0.033*
C10	0.33759 (9)	0.0000	0.26123 (9)	0.0176 (3)
C11	0.17867 (10)	0.0000	0.18420 (10)	0.0232 (3)
H11A	0.1863 (9)	0.114 (2)	0.1498 (9)	0.035*
H11B	0.1170 (14)	0.0000	0.1982 (13)	0.035*
C12	0.37724 (10)	0.0000	0.19120 (9)	0.0191 (3)
H12	0.3407	0.0000	0.1377	0.023*
C13	0.59616 (10)	0.0000	0.14061 (9)	0.0188 (3)
C14	0.63291 (10)	0.0000	0.06719 (9)	0.0215 (3)
H14	0.5933	0.0000	0.0152	0.026*
C15	0.72657 (10)	0.0000	0.06964 (9)	0.0222 (3)
H15	0.7505	0.0000	0.0193	0.027*
C16	0.78629 (10)	0.0000	0.14535 (9)	0.0196 (3)
C17	0.74891 (10)	0.0000	0.21879 (9)	0.0201 (3)
H17	0.7886	0.0000	0.2707	0.024*
C18	0.65596 (10)	0.0000	0.21732 (9)	0.0208 (3)
H18	0.6322	0.0000	0.2678	0.025*
C19	0.88757 (10)	0.0000	0.15055 (10)	0.0214 (3)
C20	0.92658 (11)	0.0000	0.07131 (11)	0.0316 (4)
H20A	0.9913 (16)	0.0000	0.0818 (15)	0.047*
H20B	0.9057 (10)	0.113 (2)	0.0369 (10)	0.047*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0193 (5)	0.0339 (6)	0.0220 (6)	0.000	−0.0014 (4)	0.000
N1	0.0140 (6)	0.0235 (6)	0.0189 (6)	0.000	−0.0007 (5)	0.000
N2	0.0185 (6)	0.0208 (6)	0.0164 (6)	0.000	0.0026 (5)	0.000
N3	0.0186 (6)	0.0259 (6)	0.0160 (6)	0.000	0.0010 (5)	0.000
C1	0.0176 (7)	0.0177 (7)	0.0205 (7)	0.000	0.0024 (6)	0.000
C2	0.0164 (7)	0.0220 (7)	0.0295 (8)	0.000	0.0036 (6)	0.000
C3	0.0216 (7)	0.0235 (7)	0.0338 (9)	0.000	0.0115 (6)	0.000
C4	0.0301 (8)	0.0229 (7)	0.0223 (8)	0.000	0.0100 (6)	0.000
C5	0.0225 (7)	0.0219 (7)	0.0201 (7)	0.000	0.0029 (6)	0.000
C6	0.0173 (7)	0.0176 (7)	0.0206 (7)	0.000	0.0031 (5)	0.000
C7	0.0150 (6)	0.0227 (7)	0.0146 (7)	0.000	0.0000 (5)	0.000
C8	0.0196 (5)	0.0265 (5)	0.0180 (5)	−0.0039 (4)	0.0002 (4)	−0.0018 (4)
C10	0.0155 (6)	0.0179 (7)	0.0179 (7)	0.000	−0.0014 (5)	0.000
C11	0.0167 (7)	0.0286 (8)	0.0217 (8)	0.000	−0.0038 (6)	0.000
C12	0.0171 (7)	0.0231 (7)	0.0156 (7)	0.000	−0.0017 (5)	0.000
C13	0.0176 (7)	0.0198 (7)	0.0184 (7)	0.000	0.0012 (5)	0.000
C14	0.0204 (7)	0.0281 (8)	0.0146 (7)	0.000	−0.0012 (5)	0.000
C15	0.0216 (7)	0.0289 (8)	0.0162 (7)	0.000	0.0035 (6)	0.000
C16	0.0188 (7)	0.0204 (7)	0.0189 (7)	0.000	0.0011 (5)	0.000
C17	0.0204 (7)	0.0227 (7)	0.0154 (7)	0.000	−0.0019 (5)	0.000
C18	0.0216 (7)	0.0255 (7)	0.0152 (7)	0.000	0.0026 (6)	0.000
C19	0.0203 (7)	0.0216 (7)	0.0218 (8)	0.000	0.0018 (6)	0.000
C20	0.0187 (7)	0.0527 (11)	0.0234 (8)	0.000	0.0037 (6)	0.000

O1—C19	1.2163 (19)	C8—H8A	0.9800
N1—C10	1.3580 (18)	C8—H8B	0.9800
N1—C1	1.4084 (19)	C8—H8C	0.9800
N1—C11	1.4541 (19)	C10—C12	1.373 (2)
N2—N3	1.2868 (18)	C11—H11A	0.983 (15)
N2—C12	1.3567 (18)	C11—H11B	0.98 (2)
N3—C13	1.4101 (18)	C12—H12	0.9500
C1—C2	1.388 (2)	C13—C14	1.400 (2)
C1—C6	1.396 (2)	C13—C18	1.412 (2)
C2—C3	1.393 (2)	C14—C15	1.386 (2)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.386 (2)	C15—C16	1.398 (2)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.395 (2)	C16—C17	1.405 (2)
C4—H4	0.9500	C16—C19	1.494 (2)
C5—C6	1.381 (2)	C17—C18	1.378 (2)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.5132 (19)	C18—H18	0.9500
C7—C10	1.5310 (19)	C19—C20	1.505 (2)
C7—C8ⁱ	1.5365 (13)	C20—H20A	0.95 (2)
C7—C8	1.5365 (13)	C20—H20B	0.983 (17)

C10—N1—C1	111.44 (12)	H8B—C8—H8C	109.5
C10—N1—C11	124.21 (13)	N1—C10—C12	123.59 (13)
C1—N1—C11	124.35 (12)	N1—C10—C7	109.11 (12)
N3—N2—C12	114.17 (12)	C12—C10—C7	127.30 (13)
N2—N3—C13	113.32 (12)	N1—C11—H11A	110.9 (8)
C2—C1—C6	122.29 (14)	N1—C11—H11B	109.8 (12)
C2—C1—N1	129.04 (14)	H11A—C11—H11B	109.6 (10)
C6—C1—N1	108.67 (12)	N2—C12—C10	118.86 (13)
C1—C2—C3	116.83 (14)	N2—C12—H12	120.6
C1—C2—H2	121.6	C10—C12—H12	120.6
C3—C2—H2	121.6	C14—C13—N3	115.60 (13)
C4—C3—C2	121.70 (14)	C14—C13—C18	118.97 (13)
C4—C3—H3	119.2	N3—C13—C18	125.43 (13)
C2—C3—H3	119.2	C15—C14—C13	120.59 (13)
C3—C4—C5	120.48 (14)	C15—C14—H14	119.7
C3—C4—H4	119.8	C13—C14—H14	119.7
C5—C4—H4	119.8	C14—C15—C16	120.81 (14)
C6—C5—C4	118.79 (14)	C14—C15—H15	119.6
C6—C5—H5	120.6	C16—C15—H15	119.6
C4—C5—H5	120.6	C15—C16—C17	118.28 (13)
C5—C6—C1	119.91 (13)	C15—C16—C19	122.40 (13)
C5—C6—C7	130.49 (13)	C17—C16—C19	119.33 (13)
C1—C6—C7	109.60 (13)	C18—C17—C16	121.56 (13)
C6—C7—C10	101.19 (11)	C18—C17—H17	119.2
C6—C7—C8ⁱ	111.23 (8)	C16—C17—H17	119.2
C10—C7—C8ⁱ	111.41 (8)	C17—C18—C13	119.79 (14)
C6—C7—C8	111.24 (8)	C17—C18—H18	120.1
C10—C7—C8	111.41 (8)	C13—C18—H18	120.1
C8ⁱ—C7—C8	110.12 (12)	O1—C19—C16	120.98 (14)
C7—C8—H8A	109.5	O1—C19—C20	120.33 (14)
C7—C8—H8B	109.5	C16—C19—C20	118.70 (13)
H8A—C8—H8B	109.5	C19—C20—H20A	111.7 (14)
C7—C8—H8C	109.5	C19—C20—H20B	111.3 (9)
H8A—C8—H8C	109.5	H20A—C20—H20B	108.5 (12)

C12—N2—N3—C13	180.0	C6—C7—C10—N1	0.000 (1)
C10—N1—C1—C2	180.000 (1)	C8ⁱ—C7—C10—N1	118.30 (8)
C11—N1—C1—C2	0.000 (1)	C8—C7—C10—N1	−118.30 (8)
C10—N1—C1—C6	0.000 (1)	C6—C7—C10—C12	180.000 (1)
C11—N1—C1—C6	180.000 (1)	C8ⁱ—C7—C10—C12	−61.70 (8)
C6—C1—C2—C3	0.000 (1)	C8—C7—C10—C12	61.70 (8)
N1—C1—C2—C3	180.000 (1)	N3—N2—C12—C10	180.000 (1)
C1—C2—C3—C4	0.000 (1)	N1—C10—C12—N2	180.000 (1)
C2—C3—C4—C5	0.000 (1)	C7—C10—C12—N2	0.000 (1)
C3—C4—C5—C6	0.000 (1)	N2—N3—C13—C14	180.0
C4—C5—C6—C1	0.000 (1)	N2—N3—C13—C18	0.000 (1)
C4—C5—C6—C7	180.000 (1)	N3—C13—C14—C15	180.0
C2—C1—C6—C5	0.000 (1)	C18—C13—C14—C15	0.000 (1)
N1—C1—C6—C5	180.000 (1)	C13—C14—C15—C16	0.0
C2—C1—C6—C7	180.000 (1)	C14—C15—C16—C17	0.000 (1)
N1—C1—C6—C7	0.000 (1)	C14—C15—C16—C19	180.0
C5—C6—C7—C10	180.000 (1)	C15—C16—C17—C18	0.000 (1)
C1—C6—C7—C10	0.000 (1)	C19—C16—C17—C18	180.000 (1)
C5—C6—C7—C8ⁱ	61.57 (8)	C16—C17—C18—C13	0.000 (1)
C1—C6—C7—C8ⁱ	−118.43 (8)	C14—C13—C18—C17	0.000 (1)
C5—C6—C7—C8	−61.58 (8)	N3—C13—C18—C17	180.000 (1)
C1—C6—C7—C8	118.42 (8)	C15—C16—C19—O1	180.0
C1—N1—C10—C12	180.000 (1)	C17—C16—C19—O1	0.000 (1)
C11—N1—C10—C12	0.000 (1)	C15—C16—C19—C20	0.000 (1)
C1—N1—C10—C7	0.000 (1)	C17—C16—C19—C20	180.0
C11—N1—C10—C7	180.000 (1)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱⁱ	0.95	2.57	3.5227 (19)	179
C14—H14···N3ⁱⁱⁱ	0.95	2.55	3.4985 (19)	175
C11—H11A···Cg3^iv	0.981 (15)	2.665 (14)	3.5230 (4)	145.8 (11)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.95	2.57	3.5227 (19)	179
C14—H14⋯N3ⁱⁱ	0.95	2.55	3.4985 (19)	175
C11—H11A⋯Cg3ⁱⁱⁱ	0.981 (15)	2.665 (14)	3.5230 (4)	145.8 (11)

Symmetry codes: (i) ; (ii) ; (iii) .

5 in total

4. An NMR and X-ray study of the structure of the azo coupling product of 4-dimethylaminopent-3-en-2-one and benzenediazonium-tetrafluoroborate.

Authors: Petr Simůnek; Valerio Bertolasi; Antonín Lycka; Vladimir Machácek
Journal: Org Biomol Chem Date: 2003-09-21 Impact factor: 3.876

5. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20