Crystal structure of 1-nitro-4-(tri­methyl­silylethyn­yl)naphthalene

Du, J.; Moxey, G.J.

doi:10.1107/S2056989015007173

organic compounds

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ISSN: 2056-9890

Volume 71| Part 5| May 2015| Pages o311-o312

https://doi.org/10.1107/S2056989015007173

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Crystal structure of 1-nitro-4-(trimethylsilylethynyl)naphthalene

Jun Du ^a and Graeme J. Moxey ^a,^b ^*

^aSchool of Chemical and Material Engineering, Jiangnan University, Wuxi, 214122, People's Republic of China, and ^bResearch School of Chemistry, Australian National University, Canberra, ACT 2601, Australia
^*Correspondence e-mail: Graeme.Moxey@anu.edu.au

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 31 March 2015; accepted 10 April 2015; online 15 April 2015)

In the title compound, C₁₅H₁₅NO₂Si, the dihedral angle between the nitro group and the mean plane of the naphthalene system is 22.04 (11)°. In the crystal, π–π interactions generate supramolecular chains propagating along the a-axis direction; the centroid-to-centroid distances range from 3.5590 (12) to 3.8535 (12) Å.

Keywords: crystal structure; trialkylsilylacetylene; nitroarene; π–π interactions.

CCDC reference: 1058939

1. Related literature

For the syntheses of arylalkynes by Sonogashira coupling, see: Takahashi et al. (1980 ). For desilylation of the related 1-nitro-4-(trimethylsilylethynyl)benzene and its use in the construction of metal alkynyl complexes with enhanced non-linear optical properties, see: McDonagh et al. (1996a ,b , 2003 ); Garcia et al. (2002 ). For related structures, see: Squadrito et al. (1990 ); Khan et al. (2004 ).

2. Experimental

2.1. Crystal data

C₁₅H₁₅NO₂Si
M_r = 269.37
Triclinic, $[P \overline 1]$
a = 6.9679 (9) Å
b = 9.2425 (12) Å
c = 11.799 (1) Å
α = 100.242 (9)°
β = 99.698 (9)°
γ = 107.127 (12)°
V = 694.62 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 150 K
0.23 × 0.07 × 0.04 mm

2.2. Data collection

Agilent SuperNova (Dual, Cu at zero, EosS2) diffractometer
Absorption correction: analytical [CrysAlis PRO (Agilent, 2014 ), based on expressions derived by Clark & Reid (1995 )] T_min = 0.986, T_max = 0.996
4695 measured reflections
3112 independent reflections
2621 reflections with I > 2σ(I)
R_int = 0.021

2.3. Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.114
S = 1.07
3112 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1058939

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015007173/xu5846sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015007173/xu5846Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015007173/xu5846Isup3.cml

checkCIF report

Synthesis and crystallization top

1-Iodo-4-nitronaphthalene (1.196 g, 4.00 mmol) was added to triethylamine (30 mL) and the mixture deoxygenated and charged with nitrogen. PdCl₂(PPh₃)₂ (12 mg, 0.016 mmol), CuI (6 mg, 0.03 mmol) and trimethylsilylacetylene (0.7 mL, 5.00 mmol) were added and the reaction heated to 35 °C overnight. The solution was filtered through filter paper, washing with triethylamine (10 mL), and the solvent was removed from the filtrate. The residue was then passed through a short pad of silica, eluting with 4:1 petrol:CH₂Cl₂. Reduction in volume of the eluate afforded the product as a yellow solid (1.034 g, 96%). Anal. Calc. for C₁₅H₁₅NO₂Si: C, 66.88; H, 5.61; N, 5.20. Found: C, 66.67; H, 5.68; N, 5.28%. ¹H NMR (δ, 400 MHz, CDCl₃): 8.55 (d, J_HH = 8.0 Hz, 1H, H₈), 8.47 (d, J_HH = 8.0 Hz, 1H, H₅), 8.15 (d, J_HH = 8.0 Hz, 1H, H₁₁), 7.79 – 7.65 (m, 3H, H₄, H₉, H₁₀), 0.36 (s, 9H, Me); ¹³C NMR (δ, 101 MHz, CDCl₃): 146.3 (C₆), 134.4 (C₁₂), 129.8 (C₉), 128.9 (C₄), 128.2 (C₁₁), 127.7 (C₃), 127.1 (C₁₀), 125.1 (C₇), 123.5 (C₈), 123.3 (C₅), 105.1 (C₂), 101.4 (C₁), 0.1 (s, Me); IR (ATR, cm^-1): 2956, 2156, 1507, 1323. Bright yellow crystals of the title compound were obtained by diffusion of methanol into a dichloromethane solution.

Refinement top

Crystal data, data collection and structure refinement details are summarized below.

Related literature top

For the syntheses of arylalkynes by Sonogashira coupling, see: Takahashi et al. (1980). For desilylation of the related 1-nitro-4-(trimethylsilylethynyl)benzene and its use in the construction of metal alkynyl complexes with enhanced non-linear optical properties, see: McDonagh et al. (1996a,b, 2003); Garcia et al. (2002). For related structures, see: Squadrito et al. (1990); Khan et al. (2004).

Structure description top

For the syntheses of arylalkynes by Sonogashira coupling, see: Takahashi et al. (1980). For desilylation of the related 1-nitro-4-(trimethylsilylethynyl)benzene and its use in the construction of metal alkynyl complexes with enhanced non-linear optical properties, see: McDonagh et al. (1996a,b, 2003); Garcia et al. (2002). For related structures, see: Squadrito et al. (1990); Khan et al. (2004).

Synthesis and crystallization top

Refinement details top

Crystal data, data collection and structure refinement details are summarized below.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. Molecular structure of 1-nitro-4-(trimethylsilylethynyl)naphthalene, with displacement ellipsoids set at the 40% probability level.
	Fig. 2. Atom numbering scheme of 1-nitro-4-(trimethylsilylethynyl)naphthalene for ¹H and ¹³C NMR assignments.

1-Nitro-4-(trimethylsilylethynyl)naphthalene top

Crystal data top

C₁₅H₁₅NO₂Si	Z = 2
M_r = 269.37	F(000) = 284
Triclinic, P1	D_x = 1.288 Mg m⁻³
a = 6.9679 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2425 (12) Å	Cell parameters from 1967 reflections
c = 11.799 (1) Å	θ = 2.6–28.3°
α = 100.242 (9)°	µ = 0.17 mm⁻¹
β = 99.698 (9)°	T = 150 K
γ = 107.127 (12)°	Needle, yellow
V = 694.62 (15) Å³	0.23 × 0.07 × 0.04 mm

Data collection top

Agilent SuperNova (Dual, Cu at zero, EosS2) diffractometer	3112 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2621 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.021
Detector resolution: 8.1297 pixels mm^-1	θ_max = 29.2°, θ_min = 1.8°
ω scans	h = −6→9
Absorption correction: analytical [CrysAlis PRO (Agilent, 2014), based on expressions derived by Clark & Reid (1995)]	k = −11→12
T_min = 0.986, T_max = 0.996	l = −15→15
4695 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0415P)² + 0.3469P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3112 reflections	Δρ_max = 0.36 e Å⁻³
175 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints

Crystal data top

C₁₅H₁₅NO₂Si	γ = 107.127 (12)°
M_r = 269.37	V = 694.62 (15) Å³
Triclinic, P1	Z = 2
a = 6.9679 (9) Å	Mo Kα radiation
b = 9.2425 (12) Å	µ = 0.17 mm⁻¹
c = 11.799 (1) Å	T = 150 K
α = 100.242 (9)°	0.23 × 0.07 × 0.04 mm
β = 99.698 (9)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, EosS2) diffractometer	3112 independent reflections
Absorption correction: analytical [CrysAlis PRO (Agilent, 2014), based on expressions derived by Clark & Reid (1995)]	2621 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.996	R_int = 0.021
4695 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.07	Δρ_max = 0.36 e Å⁻³
3112 reflections	Δρ_min = −0.23 e Å⁻³
175 parameters

Special details top

Experimental. Absorption correction: CrysAlis Pro (Agilent Technologies, 2014) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark & Reid, 1995). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2485 (3)	0.6318 (2)	0.44838 (15)	0.0204 (4)
C2	0.1929 (2)	0.4663 (2)	0.41137 (15)	0.0188 (4)
C3	0.1112 (3)	0.3754 (2)	0.29263 (16)	0.0247 (4)
H3	0.0875	0.4239	0.2316	0.030*
C4	0.0675 (3)	0.2178 (2)	0.26757 (17)	0.0293 (4)
H4	0.0147	0.1606	0.1893	0.035*
C5	0.1001 (3)	0.1400 (2)	0.35659 (18)	0.0293 (4)
H5	0.0661	0.0321	0.3376	0.035*
C6	0.1819 (3)	0.2230 (2)	0.47120 (17)	0.0234 (4)
H6	0.2048	0.1711	0.5301	0.028*
C7	0.2324 (2)	0.3874 (2)	0.50191 (15)	0.0182 (4)
C8	0.3257 (3)	0.4749 (2)	0.62159 (15)	0.0187 (4)
C9	0.3745 (3)	0.6352 (2)	0.65052 (15)	0.0220 (4)
H9	0.4329	0.6912	0.7288	0.026*
C10	0.3369 (3)	0.7131 (2)	0.56329 (16)	0.0225 (4)
H10	0.3720	0.8211	0.5832	0.027*
C11	0.3756 (3)	0.3974 (2)	0.71220 (15)	0.0215 (4)
C12	0.4216 (3)	0.3354 (2)	0.78877 (16)	0.0235 (4)
C13	0.4757 (3)	0.0381 (2)	0.83030 (17)	0.0300 (4)
H13A	0.3530	−0.0142	0.7682	0.045*
H13B	0.4823	−0.0237	0.8873	0.045*
H13C	0.5949	0.0523	0.7973	0.045*
C14	0.2518 (3)	0.2089 (3)	0.97894 (19)	0.0361 (5)
H14A	0.1234	0.1699	0.9203	0.054*
H14B	0.2647	0.3083	1.0269	0.054*
H14C	0.2547	0.1369	1.0281	0.054*
C15	0.7217 (3)	0.3443 (2)	1.00937 (18)	0.0327 (5)
H15A	0.7507	0.2860	1.0658	0.049*
H15B	0.7161	0.4421	1.0501	0.049*
H15C	0.8287	0.3633	0.9667	0.049*
N1	0.2165 (3)	0.7285 (2)	0.36481 (15)	0.0275 (4)
O1	0.0903 (2)	0.6698 (2)	0.27072 (14)	0.0437 (4)
O2	0.3213 (3)	0.86743 (19)	0.39546 (15)	0.0532 (5)
Si1	0.47002 (8)	0.23164 (6)	0.90416 (4)	0.02062 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0176 (8)	0.0279 (10)	0.0240 (9)	0.0126 (7)	0.0093 (7)	0.0138 (7)
C2	0.0125 (7)	0.0262 (9)	0.0212 (8)	0.0085 (7)	0.0063 (7)	0.0086 (7)
C3	0.0193 (9)	0.0349 (11)	0.0191 (9)	0.0081 (8)	0.0036 (7)	0.0076 (8)
C4	0.0228 (9)	0.0372 (12)	0.0213 (9)	0.0066 (8)	0.0030 (8)	−0.0012 (8)
C5	0.0256 (10)	0.0240 (10)	0.0350 (11)	0.0071 (8)	0.0065 (8)	0.0016 (8)
C6	0.0211 (9)	0.0239 (10)	0.0280 (9)	0.0093 (7)	0.0067 (8)	0.0093 (8)
C7	0.0123 (7)	0.0238 (9)	0.0212 (8)	0.0077 (7)	0.0064 (7)	0.0074 (7)
C8	0.0160 (8)	0.0264 (9)	0.0199 (8)	0.0114 (7)	0.0078 (7)	0.0100 (7)
C9	0.0217 (9)	0.0262 (10)	0.0193 (8)	0.0103 (7)	0.0065 (7)	0.0033 (7)
C10	0.0233 (9)	0.0229 (9)	0.0267 (9)	0.0124 (8)	0.0105 (8)	0.0073 (7)
C11	0.0196 (8)	0.0267 (10)	0.0208 (9)	0.0105 (7)	0.0070 (7)	0.0054 (7)
C12	0.0248 (9)	0.0274 (10)	0.0217 (9)	0.0110 (8)	0.0078 (7)	0.0083 (7)
C13	0.0396 (11)	0.0241 (10)	0.0272 (10)	0.0113 (9)	0.0099 (9)	0.0058 (8)
C14	0.0410 (12)	0.0438 (13)	0.0373 (11)	0.0215 (10)	0.0217 (10)	0.0197 (10)
C15	0.0364 (11)	0.0296 (11)	0.0282 (10)	0.0100 (9)	−0.0004 (9)	0.0066 (8)
N1	0.0294 (9)	0.0352 (10)	0.0313 (9)	0.0193 (8)	0.0158 (7)	0.0186 (8)
O1	0.0390 (9)	0.0558 (11)	0.0400 (9)	0.0167 (8)	−0.0007 (7)	0.0290 (8)
O2	0.0889 (14)	0.0287 (9)	0.0447 (10)	0.0188 (9)	0.0129 (9)	0.0198 (8)
Si1	0.0252 (3)	0.0222 (3)	0.0169 (2)	0.0097 (2)	0.00518 (19)	0.00766 (19)

Geometric parameters (Å, º) top

C1—C2	1.427 (3)	C10—H10	0.9300
C1—C10	1.366 (3)	C11—C12	1.201 (2)
C1—N1	1.476 (2)	C12—Si1	1.8403 (19)
C2—C3	1.422 (3)	C13—H13A	0.9600
C2—C7	1.430 (2)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C3—C4	1.363 (3)	C13—Si1	1.860 (2)
C4—H4	0.9300	C14—H14A	0.9600
C4—C5	1.399 (3)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C5—C6	1.362 (3)	C14—Si1	1.862 (2)
C6—H6	0.9300	C15—H15A	0.9600
C6—C7	1.418 (3)	C15—H15B	0.9600
C7—C8	1.430 (2)	C15—H15C	0.9600
C8—C9	1.382 (3)	C15—Si1	1.853 (2)
C8—C11	1.439 (2)	N1—O1	1.215 (2)
C9—H9	0.9300	N1—O2	1.228 (2)
C9—C10	1.390 (2)

C2—C1—N1	122.38 (16)	C12—C11—C8	178.5 (2)
C10—C1—C2	122.82 (16)	C11—C12—Si1	175.42 (17)
C10—C1—N1	114.80 (16)	H13A—C13—H13B	109.5
C1—C2—C7	116.38 (15)	H13A—C13—H13C	109.5
C3—C2—C1	125.72 (16)	H13B—C13—H13C	109.5
C3—C2—C7	117.84 (17)	Si1—C13—H13A	109.5
C2—C3—H3	119.7	Si1—C13—H13B	109.5
C4—C3—C2	120.51 (17)	Si1—C13—H13C	109.5
C4—C3—H3	119.7	H14A—C14—H14B	109.5
C3—C4—H4	119.2	H14A—C14—H14C	109.5
C3—C4—C5	121.65 (18)	H14B—C14—H14C	109.5
C5—C4—H4	119.2	Si1—C14—H14A	109.5
C4—C5—H5	120.1	Si1—C14—H14B	109.5
C6—C5—C4	119.74 (18)	Si1—C14—H14C	109.5
C6—C5—H5	120.1	H15A—C15—H15B	109.5
C5—C6—H6	119.6	H15A—C15—H15C	109.5
C5—C6—C7	120.89 (17)	H15B—C15—H15C	109.5
C7—C6—H6	119.6	Si1—C15—H15A	109.5
C2—C7—C8	119.87 (16)	Si1—C15—H15B	109.5
C6—C7—C2	119.33 (16)	Si1—C15—H15C	109.5
C6—C7—C8	120.79 (16)	O1—N1—C1	119.96 (17)
C7—C8—C11	120.25 (16)	O1—N1—O2	123.02 (17)
C9—C8—C7	120.30 (16)	O2—N1—C1	117.02 (17)
C9—C8—C11	119.42 (16)	C12—Si1—C13	107.97 (9)
C8—C9—H9	119.8	C12—Si1—C14	106.63 (9)
C8—C9—C10	120.33 (16)	C12—Si1—C15	109.92 (9)
C10—C9—H9	119.8	C13—Si1—C14	110.88 (10)
C1—C10—C9	120.29 (17)	C15—Si1—C13	109.63 (10)
C1—C10—H10	119.9	C15—Si1—C14	111.70 (10)
C9—C10—H10	119.9

C1—C2—C3—C4	178.69 (16)	C5—C6—C7—C8	−177.53 (16)
C1—C2—C7—C6	−179.69 (14)	C6—C7—C8—C9	179.94 (15)
C1—C2—C7—C8	−0.9 (2)	C6—C7—C8—C11	1.9 (2)
C2—C1—C10—C9	−0.7 (3)	C7—C2—C3—C4	1.7 (2)
C2—C1—N1—O1	21.6 (2)	C7—C8—C9—C10	−1.2 (2)
C2—C1—N1—O2	−158.72 (17)	C8—C9—C10—C1	0.9 (3)
C2—C3—C4—C5	0.2 (3)	C10—C1—C2—C3	−176.32 (16)
C2—C7—C8—C9	1.2 (2)	C10—C1—C2—C7	0.7 (2)
C2—C7—C8—C11	−176.86 (14)	C10—C1—N1—O1	−158.99 (17)
C3—C2—C7—C6	−2.4 (2)	C10—C1—N1—O2	20.7 (2)
C3—C2—C7—C8	176.36 (15)	C11—C8—C9—C10	176.88 (15)
C3—C4—C5—C6	−1.5 (3)	N1—C1—C2—C3	3.1 (3)
C4—C5—C6—C7	0.7 (3)	N1—C1—C2—C7	−179.89 (14)
C5—C6—C7—C2	1.2 (2)	N1—C1—C10—C9	179.83 (14)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO₂Si
M_r	269.37
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	6.9679 (9), 9.2425 (12), 11.799 (1)
α, β, γ (°)	100.242 (9), 99.698 (9), 107.127 (12)
V (Å³)	694.62 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.23 × 0.07 × 0.04

Data collection
Diffractometer	Agilent SuperNova (Dual, Cu at zero, EosS2)
Absorption correction	Analytical [CrysAlis PRO (Agilent, 2014), based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.986, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	4695, 3112, 2621
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.114, 1.07
No. of reflections	3112
No. of parameters	175
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.23

Computer programs: CrysAlis PRO (Agilent, 2014), SHELXS97 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2015), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

We gratefully acknowledge support from the Australian Research Council (LE130100057) to purchase Agilent Technologies SuperNova and XCalibur diffractometers. We thank Professors C. Zhang (Jiangnan University), M. P. Cifuentes (Australian National University) and M. G. Humphrey (Australian National University) for assistance.

References

Agilent Technologies (2014). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
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Volume 71| Part 5| May 2015| Pages o311-o312

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