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

In dimethyl sulfoxide solvated 9-(2-carb-oxy-2-cyano-vin-yl)julolidine, C(16)H(16)N(2)O(2)·C(2)H(6)OS, the essentially planar -CH=(CN)-CO(2)H 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 mol-ecule. The acid mol-ecule is disordered over two positions with respect to the methyl-ene 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 = 346.44

Monoclinic,

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 ▶).

Click here for additional data file.

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

Click here for additional data file.

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

Click here for additional data file.

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

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

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

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

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)

	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*

	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)

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)

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)

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)