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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Oct 24;68(Pt 11):o3204–o3205. doi: 10.1107/S1600536812043383

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, Mark Maroncelli a
PMCID: PMC3515293  PMID: 23284513

Abstract

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 ▶). graphic file with name e-68-o3204-scheme1.jpg

Experimental  

Crystal data  

  • C16H16N2O2·C2H6OS

  • M r = 346.44

  • Monoclinic, Inline graphic

  • 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[F 2 > 2σ(F 2)] = 0.051

  • wR(F 2) = 0.146

  • S = 1.02

  • 3443 reflections

  • 239 parameters

  • 45 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.23 e Å−3

  • Absolute structure: Flack (1983 ▶), 1096 Friedel pairs

  • Flack parameter: 0.51 (15)

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 ▶).

Supplementary Material

Click here for additional data file. (30.4KB, cif)

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812043383/ng5301sup1.cif

e-68-o3204-sup1.cif (30.4KB, cif)
Click here for additional data file. (168.8KB, hkl)

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

e-68-o3204-Isup2.hkl (168.8KB, hkl)
Click here for additional data file. (6KB, cml)

Supplementary material file. DOI: 10.1107/S1600536812043383/ng5301Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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)
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Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

Hydrogen atoms were placed in calculated positions with C—H 0.93 and 0.97 Å in a riding-model approximation. The acid hydrogen was located in a difference Fourier map and was freely refined.

The acid is disordered over two positions in respect of the five methylene carbons. The occupancy could not be refined so that the disorder was assumed to be a 1:1 type of disorder. Pairs of 1,2-related C–C distances were restrained to within 0.01 Å of each other, and the temperature factors of the primed atoms were set to those of the unprimed ones. Additionally, the anisotropic temperature factors were tightly restrained to be nearly isotropic.

The Flack parameter, refined on 1096 Friedel pairs, was 0.5, which implied that the crystal studied is a racemic twin that crystallizes in a polar space group. The racemic nature also supported the 1:1 type of disorder.

Figures

Fig. 1.

Fig. 1.

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

Crystal data

C16H16N2O2·C2H6OS F(000) = 368
Mr = 346.44 Dx = 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
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Data collection

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

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(Fo2) + (0.0864P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02 (Δ/σ)max = 0.001
3443 reflections Δρmax = 0.25 e Å−3
239 parameters Δρmin = −0.23 e Å−3
45 restraints Absolute structure: Flack (1983), 1096 Friedel pairs
Primary atom site location: structure-invariant direct methods Flack parameter: 0.51 (15)
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq 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*
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, º)

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)
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Hydrogen-bond geometry (Å, º)

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)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5301).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Click here for additional data file. (30.4KB, cif)

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812043383/ng5301sup1.cif

e-68-o3204-sup1.cif (30.4KB, cif)
Click here for additional data file. (168.8KB, hkl)

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

e-68-o3204-Isup2.hkl (168.8KB, hkl)
Click here for additional data file. (6KB, cml)

Supplementary material file. DOI: 10.1107/S1600536812043383/ng5301Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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