2-Cyano-3-(2,3,6,7-tetra­hydro-1H,5H-benzo[ij]quinolizin-9-yl)prop-2-enoic acid dimethyl sulfoxide monosolvate

Yennawar, H.; He, G.; Rumble, C.; Maroncelli, M.

doi:10.1107/S1600536812043383

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages o3204-o3205

doi:10.1107/S1600536812043383

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2-Cyano-3-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)prop-2-enoic acid dimethyl sulfoxide monosolvate

Hemant Yennawar,^a ^* Gang He,^a Christopher Rumble ^a and Mark Maroncelli ^a

^aDepartment of Chemistry, Pennsylvania State University, University Park, PA 16802, USA
^*Correspondence e-mail: hpy1@psu.edu

(Received 10 October 2012; accepted 18 October 2012; online 24 October 2012)

In dimethyl sulfoxide solvated 9-(2-carboxy-2-cyanovinyl)julolidine, C₁₆H₁₆N₂O₂·C₂H₆OS, the essentially planar –CH=(CN)–CO₂H substituent (r.m.s. deviation = 0.014 Å) is almost coplanar with respect to the benzene ring, the dihedral angle between the two planes being 0.48 (2)°. The conformations of the fused, non-aromatic rings were found to be half-chair. In the crystal, the acid molecule forms a hydrogen bond to the O atom of the solvent molecule. The acid molecule is disordered over two positions with respect to the methylene C atoms in a 1:1 ratio. The crystal studied was found to be a racemic twin.

Related literature

For the synthesis of 9-(2-carboxy-2-cyanovinyl)julolidine, commonly known as CCVJ, see: Rumble et al. (2012 ). For a related molecule, see: Liang et al. (2009 ). For fluorescent-rotor probe studies of CCVJ, see: Sawada et al. (1992 ); Haidekker et al. (2001 ). For other applications, see: Iwaki et al. (1993 ); Haidekker et al. (2002 ); Tanaka et al. (2008 ); Hawe et al. (2010 ); Levitt et al. (2011 ), Dishari & Hickner (2012 ); Howell et al. (2012 ). For a mechanismic study, see: Rumble et al. (2012).

Experimental

Crystal data

C₁₆H₁₆N₂O₂·C₂H₆OS
M_r = 346.44
Monoclinic, P 2₁
a = 10.215 (3) Å
b = 7.4588 (19) Å
c = 11.819 (3) Å
β = 100.170 (5)°
V = 886.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 298 K
0.20 × 0.16 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.961, T_max = 0.971
5962 measured reflections
3443 independent reflections
2520 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.146
S = 1.02
3443 reflections
239 parameters
45 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 1096 Friedel pairs
Flack parameter: 0.51 (15)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.85 (3)	1.83 (3)	2.609 (2)	153 (4)

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812043383/ng5301sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812043383/ng5301Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812043383/ng5301Isup3.cml

checkCIF report

Comment top

9-(2-carboxy-2-cyanovinyl)julolidine, commonly known as CCVJ, is a fluorescent rotor probe (Sawada et al., 1992; Haidekker et al., 2001) whose fluorescence intensity is strongly modulated by the fluidity of its surroundings. As such, it has been used for studying local fluidity in a variety of contexts (Iwaki et al., 1993; Haidekker et al., 2002; Tanaka et al., 2008; Hawe et al., 2010; Levitt et al., 2011; Dishari & Hickner, 2012; Howell et al., 2012). We have recently studied the rotatory mechanism behind CCVJ's environmental sensitivity, which we showed is an excited-state isomerization (Rumble et al., 2012). Herein we report the crystal structure of CCVJ which we determined in support of this photochemical study.

Related literature top

For the synthesis of 9-(2-carboxy-2-cyanovinyl)julolidine, commonly known as CCVJ, see: Rumble et al. (2012). For a related molecule, see: Liang et al. (2009). For fluorescent-rotor probe studies of CCVJ, see: Sawada et al. (1992); Haidekker et al. (2001). For other applications, see: Iwaki et al. (1993); Haidekker et al. (2002); Tanaka et al. (2008); Hawe et al. (2010); Levitt et al. (2011), Dishari & Hickner (2012); Howell et al. (2012). For a mechanismic study, see: Rumble et al. (2012).

Experimental top

CCVJ was synthesized by reaction of 9-formyljulolidine and cyanoacetic acid as described by Rumble et al. (2012) and purified by silica gel flash chromatography. Orange colored crystals were obtained by slow evaporation of its solution in toluene with a small quantity of DMSO added to increase the solubility, at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) showing 50% probability displacement ellipsoids; the disorder is not shown.

2-Cyano-3-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin- 9-yl)prop-2-enoic acid dimethyl sulfoxide monosolvate top

Crystal data top

C₁₆H₁₆N₂O₂·C₂H₆OS	F(000) = 368
M_r = 346.44	D_x = 1.298 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1427 reflections
a = 10.215 (3) Å	θ = 2.4–26.3°
b = 7.4588 (19) Å	µ = 0.20 mm⁻¹
c = 11.819 (3) Å	T = 298 K
β = 100.170 (5)°	Pyramid, orange
V = 886.4 (4) Å³	0.20 × 0.16 × 0.15 mm
Z = 2

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3443 independent reflections
Radiation source: fine-focus sealed tube	2520 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→13
T_min = 0.961, T_max = 0.971	k = −9→8
5962 measured reflections	l = −15→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0864P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
3443 reflections	Δρ_max = 0.25 e Å⁻³
239 parameters	Δρ_min = −0.23 e Å⁻³
45 restraints	Absolute structure: Flack (1983), 1096 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.51 (15)

Crystal data top

C₁₆H₁₆N₂O₂·C₂H₆OS	V = 886.4 (4) Å³
M_r = 346.44	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.215 (3) Å	µ = 0.20 mm⁻¹
b = 7.4588 (19) Å	T = 298 K
c = 11.819 (3) Å	0.20 × 0.16 × 0.15 mm
β = 100.170 (5)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3443 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2520 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.971	R_int = 0.017
5962 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.146	Δρ_max = 0.25 e Å⁻³
S = 1.02	Δρ_min = −0.23 e Å⁻³
3443 reflections	Absolute structure: Flack (1983), 1096 Friedel pairs
239 parameters	Absolute structure parameter: 0.51 (15)
45 restraints

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	1.57938 (6)	0.5022 (3)	0.08482 (5)	0.0703 (3)
O1	1.23541 (15)	0.4978 (8)	0.16187 (12)	0.0620 (5)
H1	1.301 (3)	0.535 (6)	0.134 (3)	0.082 (11)*
O2	1.37748 (15)	0.5038 (7)	0.32895 (12)	0.0644 (5)
O3	1.43031 (17)	0.5070 (9)	0.04602 (13)	0.0831 (7)
N1	0.80423 (18)	0.5001 (7)	0.76083 (14)	0.0546 (5)
N2	0.9202 (2)	0.5020 (10)	0.19413 (15)	0.0694 (7)
C1	0.8895 (2)	0.5020 (8)	0.68381 (15)	0.0433 (5)
C2	1.0286 (2)	0.4971 (8)	0.72132 (16)	0.0483 (5)
C3	1.0773 (10)	0.478 (2)	0.8505 (5)	0.057 (2)	0.50
H3A	1.1499	0.3929	0.8628	0.069*	0.50
H3B	1.1126	0.5931	0.8802	0.069*	0.50
C4	0.9831 (10)	0.4241 (15)	0.9135 (7)	0.0588 (12)	0.50
H4A	1.0186	0.4433	0.9943	0.071*	0.50
H4B	0.9694	0.2962	0.9024	0.071*	0.50
C5	0.8488 (13)	0.516 (3)	0.8856 (6)	0.061 (2)	0.50
H5A	0.7857	0.4593	0.9265	0.073*	0.50
H5B	0.8568	0.6416	0.9079	0.073*	0.50
C6	0.6611 (6)	0.517 (3)	0.7224 (12)	0.063 (2)	0.50
H6A	0.6365	0.6430	0.7196	0.076*	0.50
H6B	0.6146	0.4578	0.7767	0.076*	0.50
C7	0.6201 (10)	0.4346 (16)	0.6046 (9)	0.0591 (13)	0.50
H7A	0.5245	0.4417	0.5799	0.071*	0.50
H7B	0.6470	0.3099	0.6049	0.071*	0.50
C8	0.6920 (6)	0.5454 (16)	0.5261 (10)	0.0564 (12)	0.50
H8A	0.6774	0.6726	0.5359	0.068*	0.50
H8B	0.6619	0.5138	0.4461	0.068*	0.50
C3'	1.0888 (10)	0.534 (2)	0.8468 (5)	0.057 (2)	0.50
H3'A	1.1476	0.4356	0.8752	0.069*	0.50
H3'B	1.1426	0.6418	0.8502	0.069*	0.50
C4'	0.9974 (9)	0.5554 (15)	0.9189 (6)	0.0588 (12)	0.50
H4'A	0.9893	0.6829	0.9321	0.071*	0.50
H4'B	1.0353	0.5020	0.9922	0.071*	0.50
C5'	0.8576 (13)	0.481 (3)	0.8843 (6)	0.061 (2)	0.50
H5'A	0.8580	0.3550	0.9047	0.073*	0.50
H5'B	0.7990	0.5427	0.9277	0.073*	0.50
C6'	0.6599 (6)	0.488 (3)	0.7296 (11)	0.063 (2)	0.50
H6'A	0.6197	0.5661	0.7792	0.076*	0.50
H6'B	0.6327	0.3658	0.7426	0.076*	0.50
C7'	0.6091 (9)	0.5376 (16)	0.6058 (8)	0.0591 (13)	0.50
H7'A	0.6101	0.6671	0.5983	0.071*	0.50
H7'B	0.5176	0.4977	0.5844	0.071*	0.50
C8'	0.6919 (6)	0.4551 (16)	0.5238 (10)	0.0564 (12)	0.50
H8'A	0.6790	0.3262	0.5207	0.068*	0.50
H8'B	0.6633	0.5028	0.4470	0.068*	0.50
C9	0.8385 (2)	0.4974 (10)	0.56447 (17)	0.0531 (6)
C10	0.9249 (2)	0.4991 (9)	0.48771 (16)	0.0521 (6)
H10	0.8901	0.4997	0.4095	0.062*
C11	1.06346 (19)	0.5000 (9)	0.52212 (15)	0.0432 (5)
C12	1.1110 (2)	0.4975 (9)	0.64131 (16)	0.0478 (5)
H12	1.2024	0.4961	0.6671	0.057*
C13	1.15899 (19)	0.4997 (8)	0.44699 (15)	0.0441 (5)
H13	1.2469	0.4996	0.4849	0.053*
C14	1.14494 (19)	0.4994 (8)	0.32993 (15)	0.0422 (5)
C15	1.0203 (2)	0.4995 (9)	0.25512 (16)	0.0456 (5)
C16	1.2650 (2)	0.5071 (8)	0.27592 (16)	0.0446 (5)
C17	1.6110 (5)	0.6841 (7)	0.1863 (4)	0.0650 (14)
H17A	1.5939	0.7962	0.1465	0.098*
H17B	1.7022	0.6802	0.2243	0.098*
H17C	1.5539	0.6728	0.2423	0.098*
C18	1.6183 (6)	0.3239 (8)	0.1791 (5)	0.0809 (18)
H18A	1.6065	0.2132	0.1371	0.121*
H18B	1.5608	0.3257	0.2352	0.121*
H18C	1.7091	0.3341	0.2172	0.121*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0427 (3)	0.1230 (6)	0.0511 (3)	0.0016 (10)	0.0244 (3)	0.0008 (10)
O1	0.0391 (8)	0.1122 (15)	0.0383 (7)	0.008 (3)	0.0162 (6)	0.002 (2)
O2	0.0385 (8)	0.1109 (14)	0.0454 (8)	−0.009 (3)	0.0118 (6)	−0.004 (3)
O3	0.0439 (9)	0.164 (2)	0.0435 (8)	−0.004 (3)	0.0133 (7)	0.016 (3)
N1	0.0482 (10)	0.0773 (13)	0.0434 (9)	−0.007 (3)	0.0220 (8)	−0.010 (3)
N2	0.0437 (11)	0.121 (2)	0.0445 (10)	−0.016 (3)	0.0112 (8)	0.008 (3)
C1	0.0485 (11)	0.0469 (11)	0.0388 (9)	0.004 (3)	0.0192 (8)	0.002 (3)
C2	0.0487 (12)	0.0634 (13)	0.0344 (9)	−0.001 (3)	0.0120 (8)	0.004 (3)
C3	0.056 (2)	0.080 (7)	0.0357 (11)	−0.017 (4)	0.0096 (11)	−0.016 (4)
C4	0.075 (3)	0.072 (3)	0.0313 (13)	−0.003 (4)	0.0137 (14)	0.016 (3)
C5	0.066 (2)	0.082 (6)	0.0405 (11)	0.005 (5)	0.0258 (11)	−0.013 (3)
C6	0.0490 (13)	0.082 (5)	0.0656 (19)	0.009 (4)	0.0303 (11)	0.002 (4)
C7	0.0405 (18)	0.065 (4)	0.0741 (18)	0.005 (4)	0.0173 (14)	0.002 (5)
C8	0.0441 (14)	0.071 (4)	0.0548 (14)	−0.001 (6)	0.0105 (11)	−0.014 (6)
C3'	0.056 (2)	0.080 (7)	0.0357 (11)	−0.017 (4)	0.0096 (11)	−0.016 (4)
C4'	0.075 (3)	0.072 (3)	0.0313 (13)	−0.003 (4)	0.0137 (14)	0.016 (3)
C5'	0.066 (2)	0.082 (6)	0.0405 (11)	0.005 (5)	0.0258 (11)	−0.013 (3)
C6'	0.0490 (13)	0.082 (5)	0.0656 (19)	0.009 (4)	0.0303 (11)	0.002 (4)
C7'	0.0405 (18)	0.065 (4)	0.0741 (18)	0.005 (4)	0.0173 (14)	0.002 (5)
C8'	0.0441 (14)	0.071 (4)	0.0548 (14)	−0.001 (6)	0.0105 (11)	−0.014 (6)
C9	0.0401 (11)	0.0803 (16)	0.0406 (10)	−0.003 (3)	0.0118 (9)	−0.014 (3)
C10	0.0436 (11)	0.0809 (16)	0.0331 (9)	−0.003 (3)	0.0107 (8)	0.016 (3)
C11	0.0419 (11)	0.0534 (12)	0.0368 (9)	−0.005 (3)	0.0134 (8)	0.009 (2)
C12	0.0394 (10)	0.0665 (14)	0.0383 (9)	−0.008 (3)	0.0092 (8)	0.006 (3)
C13	0.0383 (10)	0.0566 (12)	0.0390 (9)	0.005 (3)	0.0110 (8)	0.003 (3)
C14	0.0365 (10)	0.0542 (12)	0.0382 (9)	−0.008 (3)	0.0128 (7)	0.003 (3)
C15	0.0395 (11)	0.0657 (14)	0.0351 (9)	−0.007 (3)	0.0164 (8)	0.004 (3)
C16	0.0391 (11)	0.0596 (14)	0.0373 (9)	0.005 (3)	0.0130 (8)	0.005 (3)
C17	0.041 (3)	0.089 (4)	0.066 (3)	−0.003 (2)	0.013 (2)	−0.006 (2)
C18	0.065 (4)	0.079 (3)	0.103 (4)	−0.011 (3)	0.025 (3)	−0.034 (3)

Geometric parameters (Å, º) top

S1—O3	1.5112 (18)	C3'—C4'	1.380 (7)
S1—C18	1.736 (6)	C3'—H3'A	0.9700
S1—C17	1.802 (5)	C3'—H3'B	0.9700
O1—C16	1.330 (2)	C4'—C5'	1.520 (11)
O1—H1	0.85 (3)	C4'—H4'A	0.9700
O2—C16	1.208 (2)	C4'—H4'B	0.9700
N1—C1	1.366 (2)	C5'—H5'A	0.9700
N1—C6'	1.458 (6)	C5'—H5'B	0.9700
N1—C6	1.458 (6)	C6'—C7'	1.511 (10)
N1—C5	1.470 (6)	C6'—H6'A	0.9700
N1—C5'	1.472 (6)	C6'—H6'B	0.9700
N2—C15	1.142 (3)	C7'—C8'	1.525 (6)
C1—C2	1.412 (3)	C7'—H7'A	0.9700
C1—C9	1.415 (3)	C7'—H7'B	0.9700
C2—C12	1.373 (3)	C8'—C9	1.522 (6)
C2—C3'	1.527 (6)	C8'—H8'A	0.9700
C2—C3	1.527 (6)	C8'—H8'B	0.9700
C3—C4	1.377 (7)	C9—C10	1.374 (3)
C3—H3A	0.9700	C10—C11	1.402 (3)
C3—H3B	0.9700	C10—H10	0.9300
C4—C5	1.518 (11)	C11—C12	1.407 (3)
C4—H4A	0.9700	C11—C13	1.431 (2)
C4—H4B	0.9700	C12—H12	0.9300
C5—H5A	0.9700	C13—C14	1.366 (2)
C5—H5B	0.9700	C13—H13	0.9300
C6—C7	1.513 (10)	C14—C15	1.416 (3)
C6—H6A	0.9700	C14—C16	1.480 (3)
C6—H6B	0.9700	C17—H17A	0.9600
C7—C8	1.525 (7)	C17—H17B	0.9600
C7—H7A	0.9700	C17—H17C	0.9600
C7—H7B	0.9700	C18—H18A	0.9600
C8—C9	1.528 (6)	C18—H18B	0.9600
C8—H8A	0.9700	C18—H18C	0.9600
C8—H8B	0.9700

O3—S1—C18	108.5 (3)	C5'—C4'—H4'A	107.3
O3—S1—C17	103.7 (3)	C3'—C4'—H4'B	107.3
C18—S1—C17	98.95 (13)	C5'—C4'—H4'B	107.3
C16—O1—H1	109 (2)	H4'A—C4'—H4'B	106.9
C1—N1—C6'	124.5 (6)	N1—C5'—C4'	113.4 (10)
C1—N1—C6	120.9 (6)	N1—C5'—H5'A	108.9
C1—N1—C5	123.1 (6)	C4'—C5'—H5'A	108.9
C6'—N1—C5	112.3 (8)	N1—C5'—H5'B	108.9
C6—N1—C5	114.9 (8)	C4'—C5'—H5'B	108.9
C1—N1—C5'	119.6 (6)	H5'A—C5'—H5'B	107.7
C6'—N1—C5'	115.2 (8)	N1—C6'—C7'	112.9 (10)
C6—N1—C5'	119.5 (8)	N1—C6'—H6'A	109.0
N1—C1—C2	120.98 (17)	C7'—C6'—H6'A	109.0
N1—C1—C9	119.88 (19)	N1—C6'—H6'B	109.0
C2—C1—C9	119.02 (16)	C7'—C6'—H6'B	109.0
C12—C2—C1	119.30 (17)	H6'A—C6'—H6'B	107.8
C12—C2—C3'	118.5 (4)	C6'—C7'—C8'	112.4 (12)
C1—C2—C3'	120.7 (4)	C6'—C7'—H7'A	109.1
C12—C2—C3	123.9 (4)	C8'—C7'—H7'A	109.1
C1—C2—C3	116.6 (4)	C6'—C7'—H7'B	109.1
C4—C3—C2	115.6 (7)	C8'—C7'—H7'B	109.1
C4—C3—H3A	108.4	H7'A—C7'—H7'B	107.8
C2—C3—H3A	108.4	C9—C8'—C7'	109.9 (6)
C4—C3—H3B	108.4	C9—C8'—H8'A	109.7
C2—C3—H3B	108.4	C7'—C8'—H8'A	109.7
H3A—C3—H3B	107.4	C9—C8'—H8'B	109.7
C3—C4—C5	116.1 (12)	C7'—C8'—H8'B	109.7
C3—C4—H4A	108.3	H8'A—C8'—H8'B	108.2
C5—C4—H4A	108.3	C10—C9—C1	119.46 (19)
C3—C4—H4B	108.3	C10—C9—C8'	120.3 (5)
C5—C4—H4B	108.3	C1—C9—C8'	119.2 (5)
H4A—C4—H4B	107.4	C10—C9—C8	120.8 (5)
N1—C5—C4	106.8 (9)	C1—C9—C8	117.3 (5)
N1—C5—H5A	110.4	C9—C10—C11	122.84 (17)
C4—C5—H5A	110.4	C9—C10—H10	118.6
N1—C5—H5B	110.4	C11—C10—H10	118.6
C4—C5—H5B	110.4	C10—C11—C12	116.29 (16)
H5A—C5—H5B	108.6	C10—C11—C13	125.74 (17)
N1—C6—C7	110.5 (10)	C12—C11—C13	117.96 (18)
N1—C6—H6A	109.5	C2—C12—C11	122.99 (19)
C7—C6—H6A	109.5	C2—C12—H12	118.5
N1—C6—H6B	109.5	C11—C12—H12	118.5
C7—C6—H6B	109.5	C14—C13—C11	131.90 (19)
H6A—C6—H6B	108.1	C14—C13—H13	114.1
C6—C7—C8	104.7 (13)	C11—C13—H13	114.1
C6—C7—H7A	110.8	C13—C14—C15	123.68 (17)
C8—C7—H7A	110.8	C13—C14—C16	119.35 (18)
C6—C7—H7B	110.8	C15—C14—C16	116.93 (16)
C8—C7—H7B	110.8	N2—C15—C14	179.0 (6)
H7A—C7—H7B	108.9	O2—C16—O1	123.34 (18)
C7—C8—C9	104.1 (7)	O2—C16—C14	124.06 (17)
C7—C8—H8A	110.9	O1—C16—C14	112.20 (18)
C9—C8—H8A	110.9	S1—C17—H17A	109.5
C7—C8—H8B	110.9	S1—C17—H17B	109.5
C9—C8—H8B	110.9	H17A—C17—H17B	109.5
H8A—C8—H8B	108.9	S1—C17—H17C	109.5
C4'—C3'—C2	114.8 (7)	H17A—C17—H17C	109.5
C4'—C3'—H3'A	108.6	H17B—C17—H17C	109.5
C2—C3'—H3'A	108.6	S1—C18—H18A	109.5
C4'—C3'—H3'B	108.6	S1—C18—H18B	109.5
C2—C3'—H3'B	108.6	H18A—C18—H18B	109.5
H3'A—C3'—H3'B	107.5	S1—C18—H18C	109.5
C3'—C4'—C5'	119.9 (9)	H18A—C18—H18C	109.5
C3'—C4'—H4'A	107.3	H18B—C18—H18C	109.5

C6'—N1—C1—C2	−173.9 (13)	C3'—C4'—C5'—N1	−38 (2)
C6—N1—C1—C2	175.9 (12)	C1—N1—C6'—C7'	−19 (2)
C5—N1—C1—C2	8.1 (14)	C6—N1—C6'—C7'	51 (6)
C5'—N1—C1—C2	−3.9 (13)	C5—N1—C6'—C7'	159.2 (15)
C6'—N1—C1—C9	2.1 (15)	C5'—N1—C6'—C7'	170.7 (15)
C6—N1—C1—C9	−8.2 (15)	N1—C6'—C7'—C8'	44 (2)
C5—N1—C1—C9	−175.9 (12)	C6'—C7'—C8'—C9	−51.9 (15)
C5'—N1—C1—C9	172.0 (11)	N1—C1—C9—C10	−179.9 (6)
N1—C1—C2—C12	179.4 (6)	C2—C1—C9—C10	−3.9 (10)
C9—C1—C2—C12	3.4 (9)	N1—C1—C9—C8'	−11.4 (11)
N1—C1—C2—C3'	−14.6 (11)	C2—C1—C9—C8'	164.6 (7)
C9—C1—C2—C3'	169.4 (9)	N1—C1—C9—C8	17.6 (10)
N1—C1—C2—C3	3.6 (11)	C2—C1—C9—C8	−166.4 (7)
C9—C1—C2—C3	−172.4 (9)	C7'—C8'—C9—C10	−155.4 (9)
C12—C2—C3—C4	−160.1 (10)	C7'—C8'—C9—C1	36.2 (13)
C1—C2—C3—C4	15.5 (16)	C7'—C8'—C9—C8	−56.6 (13)
C3'—C2—C3—C4	124 (4)	C7—C8—C9—C10	149.4 (9)
C2—C3—C4—C5	−45.1 (18)	C7—C8—C9—C1	−48.3 (11)
C1—N1—C5—C4	−33.8 (19)	C7—C8—C9—C8'	52.9 (15)
C6'—N1—C5—C4	148.0 (15)	C1—C9—C10—C11	1.9 (10)
C6—N1—C5—C4	157.8 (14)	C8'—C9—C10—C11	−166.4 (8)
C5'—N1—C5—C4	40 (5)	C8—C9—C10—C11	163.8 (7)
C3—C4—C5—N1	52.5 (19)	C9—C10—C11—C12	0.5 (9)
C1—N1—C6—C7	32 (2)	C9—C10—C11—C13	179.2 (7)
C6'—N1—C6—C7	−84 (7)	C1—C2—C12—C11	−0.9 (9)
C5—N1—C6—C7	−159.6 (14)	C3'—C2—C12—C11	−167.3 (9)
C5'—N1—C6—C7	−148.5 (14)	C3—C2—C12—C11	174.6 (9)
N1—C6—C7—C8	−62.6 (16)	C10—C11—C12—C2	−1.0 (9)
C6—C7—C8—C9	68.9 (11)	C13—C11—C12—C2	−179.8 (6)
C12—C2—C3'—C4'	171.6 (9)	C10—C11—C13—C14	0.4 (10)
C1—C2—C3'—C4'	5.5 (15)	C12—C11—C13—C14	179.1 (6)
C3—C2—C3'—C4'	−75 (3)	C11—C13—C14—C15	0.0 (10)
C2—C3'—C4'—C5'	20.9 (17)	C11—C13—C14—C16	177.4 (7)
C1—N1—C5'—C4'	28.6 (19)	C13—C14—C16—O2	4.2 (10)
C6'—N1—C5'—C4'	−160.5 (15)	C15—C14—C16—O2	−178.3 (6)
C6—N1—C5'—C4'	−151.2 (15)	C13—C14—C16—O1	177.2 (6)
C5—N1—C5'—C4'	−83 (7)	C15—C14—C16—O1	−5.3 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.85 (3)	1.83 (3)	2.609 (2)	153 (4)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₂·C₂H₆OS
M_r	346.44
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	10.215 (3), 7.4588 (19), 11.819 (3)
β (°)	100.170 (5)
V (Å³)	886.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.20 × 0.16 × 0.15

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.961, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	5962, 3443, 2520
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.146, 1.02
No. of reflections	3443
No. of parameters	239
No. of restraints	45
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.23
Absolute structure	Flack (1983), 1096 Friedel pairs
Absolute structure parameter	0.51 (15)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.85 (3)	1.83 (3)	2.609 (2)	153 (4)

Acknowledgements

This work was supported by the Division of Chemical Sciences, Geosciences, and Biosciences, Office of Basic Energy Sciences of the US Department of Energy through grant DE–FG02-09ER16118. We also acknowledge NSF funding (CHEM-0131112) for the X-ray diffractometer.

References

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Volume 68| Part 11| November 2012| Pages o3204-o3205

doi:10.1107/S1600536812043383

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Cyano-3-(2,3,6,7-tetra­hydro-1H,5H-benzo[ij]quinolizin-9-yl)prop-2-enoic acid di­methyl sulfoxide monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Cyano-3-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)prop-2-enoic acid dimethyl sulfoxide monosolvate