1-(2,3-Di-hydroxy-prop-yl)-4-{2-[4-(di-methyl-amino)-phen-yl]vin-yl}pyridinium chloride.

The title compound, C18H23N2O2 (+)·Cl(-), crystallizes with two independent cations and anions per cell. Each cation has twofold rotational disorder about the linking vinyl groups but with unequal occupancies [0.963 (5):0.037 (5) and 0.860 (8):0.140 (8)]. The two independent cations are close to being related by an inversion centre but the data does not support the expected centrosymmetric space-group assignment. The conclusion is that the differing rotational disorder has lead to an overall non-centrosymmetric lattice. In the crystal, the mol-ecules pack in layers parallel to (133) and (-13-3), chain-linked with motif C (1) 2(7) by the di-hydroxy-propyl O-H⋯Cl⋯H-O hydrogen bonds. Other lattice binding is provided by O-H⋯Cl, C-H⋯Cl and C-H⋯N inter-actions.

Related literature

For applications of organic push–pull chromophores, see: Kay et al. (2004 ▶); Bass et al. (2001 ▶); Prasad et al. (1988 ▶). For a related example of rotational disorder, see: Moreno-Fuquen et al. (2009 ▶). For details of the synthesis, see: Kay et al. (2001 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H23N2O2 +·Cl−

M = 334.83

Monoclinic,

a = 8.4452 (3) Å

b = 13.2433 (5) Å

c = 15.3649 (6) Å

β = 100.077 (3)°

V = 1691.94 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 123 K

0.55 × 0.10 × 0.09 mm

Data collection

Bruker–Nonius APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.651, T max = 0.746

38193 measured reflections

7581 independent reflections

5545 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.096

S = 1.02

7581 reflections

474 parameters

13 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack parameter determined using 2152 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▶)

Absolute structure parameter: 0.07 (4)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and Mercury.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813033254/sj5376sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033254/sj5376Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033254/sj5376Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H23N2O2+·Cl−	F(000) = 712
Mr = 334.83	Dx = 1.314 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.4452 (3) Å	Cell parameters from 4999 reflections
b = 13.2433 (5) Å	θ = 2.7–23.4°
c = 15.3649 (6) Å	µ = 0.24 mm−1
β = 100.077 (3)°	T = 123 K
V = 1691.94 (11) Å3	Needle, red
Z = 4	0.55 × 0.10 × 0.09 mm

Bruker–Nonius APEXII CCD area-detector diffractometer	7581 independent reflections
Radiation source: fine-focus sealed tube	5545 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
Detector resolution: 8.333 pixels mm-1	θmax = 27.3°, θmin = 2.6°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (Blessing, 1995)	k = −17→17
Tmin = 0.651, Tmax = 0.746	l = −19→19
38193 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.0362P)2 + 0.2405P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.18 e Å−3
7581 reflections	Δρmin = −0.20 e Å−3
474 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
13 restraints	Extinction coefficient: 0.0039 (10)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack parameter determined using 2152 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.07 (4)

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	Uiso*/Ueq	Occ. (<1)
Cl1	0.46974 (12)	0.13741 (8)	0.18879 (7)	0.0391 (3)
O1	0.8050 (3)	0.2226 (2)	0.20024 (17)	0.0340 (6)
H1O	0.716 (4)	0.196 (3)	0.200 (3)	0.041*
O2	1.1625 (3)	0.2328 (2)	0.2362 (2)	0.0367 (8)
H2O	1.241 (4)	0.211 (4)	0.216 (3)	0.044*
N1	0.8014 (4)	0.2692 (2)	0.3860 (2)	0.0238 (8)
N2	−0.2944 (4)	0.4615 (3)	0.6126 (2)	0.0267 (8)
C1	0.9463 (5)	0.2493 (3)	0.3480 (3)	0.0283 (10)
H1A	1.0312	0.2210	0.3942	0.034*
H1B	0.9866	0.3135	0.3272	0.034*
C2	0.6990 (6)	0.3426 (3)	0.3522 (3)	0.0291 (10)
H2	0.7222	0.3826	0.3046	0.035*
C3A	0.5613 (6)	0.3606 (4)	0.3857 (3)	0.0273 (11)	0.963 (5)
H3A	0.4895	0.4122	0.3606	0.033*	0.963 (5)
C4A	0.5256 (6)	0.3031 (4)	0.4569 (3)	0.0224 (10)	0.963 (5)
C5A	0.6362 (6)	0.2279 (4)	0.4900 (3)	0.0272 (12)	0.963 (5)
H5A	0.6177	0.1873	0.5382	0.033*	0.963 (5)
C6	0.7688 (5)	0.2128 (3)	0.4541 (3)	0.0306 (10)
H6	0.8417	0.1608	0.4773	0.037*
C7	0.9110 (4)	0.1751 (3)	0.2706 (2)	0.0257 (9)
H7	0.8584	0.1133	0.2898	0.031*
C8	1.0658 (5)	0.1459 (3)	0.2410 (3)	0.0298 (10)
H8A	1.1251	0.0969	0.2833	0.036*
H8B	1.0416	0.1132	0.1822	0.036*
C9A	0.3844 (5)	0.3174 (3)	0.4975 (3)	0.0274 (11)	0.963 (5)
H9A	0.3703	0.2733	0.5444	0.033*	0.963 (5)
C10A	0.2722 (5)	0.3887 (3)	0.4733 (3)	0.0243 (11)	0.963 (5)
H10A	0.2872	0.4319	0.4261	0.029*	0.963 (5)
C11A	0.1307 (5)	0.4060 (4)	0.5123 (3)	0.0221 (10)	0.963 (5)
C12A	0.0194 (6)	0.4797 (4)	0.4758 (3)	0.0262 (11)	0.963 (5)
H12A	0.0398	0.5175	0.4264	0.031*	0.963 (5)
C13	−0.1171 (5)	0.4989 (3)	0.5090 (3)	0.0257 (10)
H13	−0.1878	0.5506	0.4829	0.031*
C14	−0.1560 (5)	0.4442 (3)	0.5807 (3)	0.0239 (9)
C15	−0.0453 (5)	0.3693 (3)	0.6177 (3)	0.0287 (10)
H15	−0.0666	0.3308	0.6665	0.034*
C16	0.0916 (5)	0.3513 (3)	0.5845 (3)	0.0288 (10)
H16	0.1632	0.3002	0.6109	0.035*
C17	−0.3366 (5)	0.4042 (3)	0.6852 (3)	0.0317 (10)
H17A	−0.3928	0.3423	0.6624	0.038*
H17B	−0.4070	0.4447	0.7157	0.038*
H17C	−0.2387	0.3865	0.7266	0.038*
C18	−0.3998 (5)	0.5442 (3)	0.5770 (3)	0.0305 (10)
H18A	−0.3436	0.6085	0.5903	0.037*
H18B	−0.4968	0.5432	0.6038	0.037*
H18C	−0.4300	0.5363	0.5128	0.037*
Cl2	0.52229 (11)	0.62109 (8)	0.32090 (6)	0.0353 (3)
O1'	0.1812 (3)	0.67503 (19)	0.22476 (18)	0.0358 (6)
H1O'	0.276 (3)	0.668 (3)	0.251 (2)	0.043*
O2'	−0.1666 (4)	0.5388 (2)	0.2646 (2)	0.0375 (8)
H2O'	−0.256 (4)	0.558 (3)	0.273 (3)	0.045*
N1'	0.1959 (4)	0.5059 (2)	0.1129 (2)	0.0265 (8)
N2'	1.2916 (4)	0.3085 (3)	−0.1111 (2)	0.0301 (9)
C1'	0.0508 (5)	0.5298 (4)	0.1502 (3)	0.0315 (10)
H1C	−0.0047	0.4663	0.1606	0.038*
H1D	−0.0237	0.5705	0.1070	0.038*
C2'	0.2335 (5)	0.5609 (3)	0.0466 (3)	0.0299 (10)
H2'	0.1642	0.6153	0.0250	0.036*
C3'A	0.3618 (6)	0.5448 (5)	0.0084 (4)	0.0272 (14)	0.860 (8)
H3'A	0.3782	0.5843	−0.0409	0.033*	0.860 (8)
C4'A	0.4716 (6)	0.4694 (5)	0.0416 (4)	0.0255 (13)	0.860 (8)
C5'A	0.4347 (7)	0.4125 (5)	0.1115 (4)	0.0289 (13)	0.860 (8)
H5'A	0.5061	0.3603	0.1359	0.035*	0.860 (8)
C6'	0.2939 (5)	0.4303 (3)	0.1473 (3)	0.0344 (11)
H6'	0.2691	0.3900	0.1943	0.041*
C7'	0.0910 (5)	0.5876 (3)	0.2360 (3)	0.0240 (9)
H7'	0.1530	0.5435	0.2828	0.029*
C8'	−0.0630 (5)	0.6221 (3)	0.2639 (2)	0.0292 (9)
H8C	−0.0390	0.6525	0.3236	0.035*
H8D	−0.1158	0.6740	0.2223	0.035*
C9'A	0.6120 (6)	0.4533 (4)	0.0014 (3)	0.0262 (13)	0.860 (8)
H9'A	0.6234	0.4949	−0.0475	0.031*	0.860 (8)
C0'A	0.7267 (6)	0.3854 (4)	0.0271 (3)	0.0277 (14)	0.860 (8)
H0'A	0.7135	0.3442	0.0759	0.033*	0.860 (8)
C1A'	0.8693 (7)	0.3668 (5)	−0.0108 (4)	0.0274 (16)	0.860 (8)
C12'	0.9755 (5)	0.2958 (4)	0.0236 (3)	0.0329 (11)
H12'	0.9535	0.2580	0.0727	0.040*
C13'	1.1137 (5)	0.2746 (3)	−0.0080 (3)	0.0300 (10)
H13'	1.1835	0.2230	0.0192	0.036*
C14'	1.1537 (5)	0.3282 (3)	−0.0805 (3)	0.0237 (9)
C15'	1.0459 (5)	0.4038 (3)	−0.1190 (3)	0.0294 (10)
H15'	1.0693	0.4419	−0.1675	0.035*
C16'	0.9064 (5)	0.4225 (4)	−0.0862 (3)	0.0333 (11)
H16'	0.8336	0.4726	−0.1134	0.040*
C17'	1.3372 (5)	0.3656 (4)	−0.1837 (3)	0.0383 (12)
H17D	1.2600	0.3524	−0.2380	0.046*
H17E	1.4450	0.3451	−0.1921	0.046*
H17F	1.3372	0.4379	−0.1700	0.046*
C18'	1.3947 (5)	0.2250 (4)	−0.0766 (3)	0.0368 (11)
H18D	1.4419	0.2383	−0.0148	0.044*
H18E	1.4807	0.2174	−0.1115	0.044*
H18F	1.3311	0.1627	−0.0803	0.044*
C3'B	0.410 (4)	0.524 (2)	0.0343 (17)	0.006 (3)*	0.140 (8)
H3'B	0.4688	0.5617	−0.0024	0.008*	0.140 (8)
C4'B	0.479 (3)	0.439 (3)	0.077 (2)	0.006 (3)*	0.140 (8)
C5'B	0.413 (3)	0.3892 (19)	0.1394 (17)	0.006 (3)*	0.140 (8)
H5'B	0.4545	0.3292	0.1725	0.008*	0.140 (8)
C9'B	0.628 (2)	0.3994 (16)	0.0562 (14)	0.006 (3)*	0.140 (8)
H9'B	0.6753	0.3443	0.0912	0.008*	0.140 (8)
C0'B	0.709 (3)	0.4332 (18)	−0.0095 (16)	0.006 (3)*	0.140 (8)
H0'B	0.6634	0.4898	−0.0426	0.008*	0.140 (8)
C1B'	0.863 (4)	0.391 (2)	−0.035 (2)	0.006 (3)*	0.140 (8)
C3B	0.597 (12)	0.347 (7)	0.348 (6)	0.006 (3)*	0.037 (5)
H3B	0.5409	0.3627	0.2911	0.008*	0.037 (5)
C4B	0.505 (9)	0.332 (8)	0.418 (8)	0.006 (3)*	0.037 (5)
C5B	0.600 (15)	0.265 (9)	0.478 (7)	0.006 (3)*	0.037 (5)
H5B	0.5642	0.2460	0.5297	0.008*	0.037 (5)
C9B	0.351 (8)	0.361 (6)	0.440 (4)	0.006 (3)*	0.037 (5)
H9B	0.2787	0.3887	0.3921	0.008*	0.037 (5)
C10B	0.290 (9)	0.355 (6)	0.515 (5)	0.006 (3)*	0.037 (5)
H10B	0.3700	0.3428	0.5658	0.008*	0.037 (5)
C11B	0.130 (8)	0.364 (7)	0.537 (7)	0.006 (3)*	0.037 (5)
C12B	0.072 (12)	0.456 (7)	0.501 (6)	0.006 (3)*	0.037 (5)
H12B	0.1379	0.4973	0.4707	0.008*	0.037 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0256 (6)	0.0416 (7)	0.0534 (7)	−0.0007 (5)	0.0158 (5)	−0.0082 (6)
O1	0.0258 (14)	0.0429 (15)	0.0330 (15)	−0.0025 (12)	0.0042 (11)	0.0092 (12)
O2	0.0278 (17)	0.0325 (17)	0.055 (2)	−0.0010 (15)	0.0217 (15)	−0.0060 (16)
N1	0.0173 (18)	0.0271 (19)	0.029 (2)	−0.0026 (15)	0.0086 (14)	−0.0003 (16)
N2	0.0214 (19)	0.0282 (19)	0.031 (2)	0.0049 (16)	0.0057 (15)	0.0031 (17)
C1	0.021 (2)	0.036 (2)	0.030 (2)	−0.0027 (18)	0.0100 (18)	−0.0025 (19)
C2	0.031 (3)	0.022 (2)	0.034 (3)	0.0003 (19)	0.008 (2)	0.0018 (19)
C3A	0.024 (3)	0.027 (3)	0.031 (3)	0.003 (2)	0.005 (2)	−0.003 (2)
C4A	0.017 (2)	0.024 (3)	0.026 (3)	−0.001 (2)	0.0025 (19)	−0.003 (2)
C5A	0.026 (3)	0.024 (3)	0.033 (3)	0.000 (2)	0.008 (2)	0.002 (2)
C6	0.028 (2)	0.029 (2)	0.036 (3)	−0.0018 (19)	0.0085 (19)	0.001 (2)
C7	0.022 (2)	0.027 (2)	0.027 (2)	−0.0044 (18)	0.0031 (16)	0.0017 (18)
C8	0.029 (2)	0.029 (2)	0.033 (2)	0.0012 (19)	0.0091 (17)	0.002 (2)
C9A	0.028 (3)	0.026 (3)	0.029 (3)	−0.006 (2)	0.009 (2)	−0.004 (2)
C10A	0.027 (3)	0.023 (2)	0.022 (2)	−0.0025 (19)	0.0033 (19)	−0.001 (2)
C11A	0.018 (2)	0.021 (3)	0.028 (3)	−0.0019 (19)	0.0045 (19)	−0.003 (2)
C12A	0.023 (2)	0.029 (3)	0.024 (3)	0.0009 (19)	−0.0015 (19)	0.004 (2)
C13	0.023 (2)	0.027 (2)	0.025 (2)	0.0041 (18)	−0.0002 (18)	0.0015 (19)
C14	0.022 (2)	0.022 (2)	0.027 (2)	−0.0022 (17)	0.0044 (18)	−0.0050 (18)
C15	0.030 (2)	0.028 (2)	0.028 (2)	−0.0022 (19)	0.0061 (19)	0.002 (2)
C16	0.028 (2)	0.031 (2)	0.028 (2)	0.0039 (19)	0.006 (2)	−0.003 (2)
C17	0.029 (2)	0.032 (2)	0.037 (3)	0.004 (2)	0.011 (2)	0.005 (2)
C18	0.026 (2)	0.032 (2)	0.034 (3)	0.006 (2)	0.0063 (19)	−0.001 (2)
Cl2	0.0285 (5)	0.0390 (6)	0.0390 (6)	0.0064 (5)	0.0072 (4)	−0.0030 (5)
O1'	0.0276 (14)	0.0284 (14)	0.0486 (17)	−0.0042 (11)	−0.0008 (12)	0.0010 (12)
O2'	0.0325 (18)	0.0292 (17)	0.057 (2)	0.0004 (15)	0.0247 (16)	0.0018 (16)
N1'	0.0205 (18)	0.0269 (19)	0.033 (2)	−0.0015 (15)	0.0066 (15)	−0.0085 (17)
N2'	0.028 (2)	0.029 (2)	0.037 (2)	0.0055 (17)	0.0158 (17)	0.0049 (17)
C1'	0.018 (2)	0.042 (3)	0.036 (3)	−0.0042 (19)	0.0101 (18)	−0.009 (2)
C2'	0.032 (2)	0.027 (2)	0.031 (2)	−0.0012 (19)	0.0052 (19)	0.000 (2)
C3'A	0.019 (3)	0.031 (3)	0.030 (3)	−0.001 (2)	0.001 (2)	0.000 (2)
C4'A	0.022 (3)	0.025 (3)	0.030 (3)	−0.010 (2)	0.004 (2)	−0.006 (2)
C5'A	0.034 (3)	0.024 (3)	0.030 (4)	0.003 (2)	0.010 (3)	0.003 (2)
C6'	0.040 (3)	0.027 (2)	0.035 (3)	−0.001 (2)	0.002 (2)	−0.002 (2)
C7'	0.028 (2)	0.020 (2)	0.025 (2)	0.0014 (17)	0.0051 (17)	0.0024 (16)
C8'	0.033 (2)	0.025 (2)	0.030 (2)	0.001 (2)	0.0088 (17)	−0.002 (2)
C9'A	0.022 (3)	0.030 (3)	0.026 (3)	−0.002 (2)	0.002 (2)	−0.001 (2)
C0'A	0.026 (3)	0.032 (3)	0.025 (3)	−0.004 (2)	0.002 (2)	−0.003 (3)
C1A'	0.028 (3)	0.036 (4)	0.018 (3)	−0.007 (3)	0.004 (3)	−0.005 (3)
C12'	0.031 (3)	0.043 (3)	0.027 (2)	−0.012 (2)	0.012 (2)	−0.010 (2)
C13'	0.032 (3)	0.029 (2)	0.029 (2)	−0.007 (2)	0.005 (2)	−0.002 (2)
C14'	0.020 (2)	0.026 (2)	0.026 (2)	−0.0038 (17)	0.0037 (18)	−0.0053 (18)
C15'	0.027 (2)	0.033 (2)	0.029 (2)	0.0047 (19)	0.0053 (19)	0.000 (2)
C16'	0.022 (2)	0.034 (3)	0.041 (3)	0.0056 (19)	−0.004 (2)	−0.006 (2)
C17'	0.034 (3)	0.048 (3)	0.037 (3)	0.000 (2)	0.017 (2)	0.000 (2)
C18'	0.028 (2)	0.034 (3)	0.049 (3)	0.008 (2)	0.007 (2)	0.001 (2)

O1—C7	1.424 (4)	C1'—C7'	1.511 (5)
O1—H1O	0.83 (3)	C1'—H1C	0.9900
O2—C8	1.420 (5)	C1'—H1D	0.9900
O2—H2O	0.83 (3)	C2'—C3'A	1.336 (6)
N1—C2	1.344 (5)	C2'—H2'	0.9500
N1—C6	1.352 (5)	C3'A—C4'A	1.397 (8)
N1—C1	1.469 (5)	C3'A—H3'A	0.9500
N2—C14	1.365 (5)	C4'A—C5'A	1.392 (7)
N2—C17	1.444 (5)	C4'A—C9'A	1.444 (7)
N2—C18	1.456 (5)	C5'A—C6'	1.414 (7)
C1—C7	1.531 (6)	C5'A—H5'A	0.9500
C1—H1A	0.9900	C6'—H6'	0.9500
C1—H1B	0.9900	C7'—C8'	1.510 (5)
C2—C3A	1.372 (6)	C7'—H7'	1.0000
C2—H2	0.9500	C8'—H8C	0.9900
C3A—C4A	1.409 (6)	C8'—H8D	0.9900
C3A—H3A	0.9500	C9'A—C0'A	1.331 (7)
C4A—C5A	1.398 (6)	C9'A—H9'A	0.9500
C4A—C9A	1.452 (6)	C0'A—C1A'	1.447 (8)
C5A—C6	1.348 (6)	C0'A—H0'A	0.9500
C5A—H5A	0.9500	C1A'—C12'	1.343 (8)
C6—H6	0.9500	C1A'—C16'	1.454 (7)
C7—C8	1.507 (5)	C12'—C13'	1.369 (6)
C7—H7	1.0000	C12'—H12'	0.9500
C8—H8A	0.9900	C13'—C14'	1.410 (6)
C8—H8B	0.9900	C13'—H13'	0.9500
C9A—C10A	1.344 (6)	C14'—C15'	1.411 (6)
C9A—H9A	0.9500	C15'—C16'	1.382 (6)
C10A—C11A	1.445 (6)	C15'—H15'	0.9500
C10A—H10A	0.9500	C16'—H16'	0.9500
C11A—C12A	1.402 (6)	C17'—H17D	0.9800
C11A—C16	1.412 (6)	C17'—H17E	0.9800
C12A—C13	1.363 (6)	C17'—H17F	0.9800
C12A—H12A	0.9500	C18'—H18D	0.9800
C13—C14	1.405 (5)	C18'—H18E	0.9800
C13—H13	0.9500	C18'—H18F	0.9800
C14—C15	1.412 (5)	C3'B—C4'B	1.38 (4)
C15—C16	1.364 (6)	C3'B—H3'B	0.95 (3)
C15—H15	0.9500	C4'B—C5'B	1.36 (4)
C16—H16	0.9500	C4'B—C9'B	1.45 (2)
C17—H17A	0.9800	C5'B—H5'B	0.98 (2)
C17—H17B	0.9800	C9'B—C0'B	1.39 (3)
C17—H17C	0.9800	C9'B—H9'B	0.9500
C18—H18A	0.9800	C0'B—C1B'	1.53 (4)
C18—H18B	0.9800	C0'B—H0'B	0.9500
C18—H18C	0.9800	C3B—C4B	1.44 (12)
O1'—C7'	1.413 (5)	C3B—H3B	0.94 (9)
O1'—H1O'	0.84 (3)	C4B—C5B	1.42 (14)
O2'—C8'	1.409 (5)	C4B—C9B	1.45 (3)
O2'—H2O'	0.83 (3)	C5B—H5B	0.93 (10)
N1'—C2'	1.336 (5)	C9B—C10B	1.35 (3)
N1'—C6'	1.347 (5)	C9B—H9B	0.9500
N1'—C1'	1.475 (5)	C10B—C11B	1.45 (3)
N2'—C14'	1.356 (5)	C10B—H10B	0.9500
N2'—C18'	1.449 (5)	C11B—C12B	1.39 (3)
N2'—C17'	1.455 (5)	C12B—H12B	0.95 (9)
C7—O1—H1O	105 (3)	C7'—C1'—H1D	109.2
C8—O2—H2O	104 (3)	H1C—C1'—H1D	107.9
C2—N1—C6	119.6 (4)	N1'—C2'—C3'A	124.6 (5)
C2—N1—C1	120.0 (3)	N1'—C2'—H2'	117.7
C6—N1—C1	120.3 (4)	C3'A—C2'—H2'	117.7
C14—N2—C17	122.1 (3)	C2'—C3'A—C4'A	119.5 (5)
C14—N2—C18	119.8 (3)	C2'—C3'A—H3'A	120.3
C17—N2—C18	118.0 (3)	C4'A—C3'A—H3'A	120.3
N1—C1—C7	111.2 (3)	C5'A—C4'A—C3'A	116.4 (5)
N1—C1—H1A	109.4	C5'A—C4'A—C9'A	124.2 (6)
C7—C1—H1A	109.4	C3'A—C4'A—C9'A	119.4 (5)
N1—C1—H1B	109.4	C4'A—C5'A—C6'	121.8 (5)
C7—C1—H1B	109.4	C4'A—C5'A—H5'A	119.1
H1A—C1—H1B	108.0	C6'—C5'A—H5'A	119.1
N1—C2—C3A	120.7 (4)	N1'—C6'—C5'A	118.2 (5)
N1—C2—H2	119.6	N1'—C6'—H6'	120.9
C3A—C2—H2	119.6	C5'A—C6'—H6'	120.9
C2—C3A—C4A	120.6 (4)	O1'—C7'—C8'	107.3 (3)
C2—C3A—H3A	119.7	O1'—C7'—C1'	110.6 (3)
C4A—C3A—H3A	119.7	C8'—C7'—C1'	109.1 (3)
C5A—C4A—C3A	116.6 (4)	O1'—C7'—H7'	109.9
C5A—C4A—C9A	118.9 (5)	C8'—C7'—H7'	109.9
C3A—C4A—C9A	124.5 (5)	C1'—C7'—H7'	109.9
C6—C5A—C4A	120.4 (4)	O2'—C8'—C7'	109.4 (3)
C6—C5A—H5A	119.8	O2'—C8'—H8C	109.8
C4A—C5A—H5A	119.8	C7'—C8'—H8C	109.8
C5A—C6—N1	122.1 (4)	O2'—C8'—H8D	109.8
C5A—C6—H6	119.0	C7'—C8'—H8D	109.8
N1—C6—H6	119.0	H8C—C8'—H8D	108.2
O1—C7—C8	110.3 (3)	C0'A—C9'A—C4'A	125.6 (5)
O1—C7—C1	108.5 (3)	C0'A—C9'A—H9'A	117.2
C8—C7—C1	109.7 (3)	C4'A—C9'A—H9'A	117.2
O1—C7—H7	109.4	C9'A—C0'A—C1A'	127.6 (6)
C8—C7—H7	109.4	C9'A—C0'A—H0'A	116.2
C1—C7—H7	109.4	C1A'—C0'A—H0'A	116.2
O2—C8—C7	110.2 (3)	C12'—C1A'—C0'A	120.5 (5)
O2—C8—H8A	109.6	C12'—C1A'—C16'	116.5 (5)
C7—C8—H8A	109.6	C0'A—C1A'—C16'	123.0 (6)
O2—C8—H8B	109.6	C1A'—C12'—C13'	123.8 (5)
C7—C8—H8B	109.6	C1A'—C12'—H12'	118.1
H8A—C8—H8B	108.1	C13'—C12'—H12'	118.1
C10A—C9A—C4A	124.4 (5)	C12'—C13'—C14'	120.9 (4)
C10A—C9A—H9A	117.8	C12'—C13'—H13'	119.6
C4A—C9A—H9A	117.8	C14'—C13'—H13'	119.6
C9A—C10A—C11A	126.2 (5)	N2'—C14'—C15'	121.4 (4)
C9A—C10A—H10A	116.9	N2'—C14'—C13'	121.1 (4)
C11A—C10A—H10A	116.9	C15'—C14'—C13'	117.5 (4)
C12A—C11A—C16	116.0 (4)	C16'—C15'—C14'	120.2 (4)
C12A—C11A—C10A	119.3 (5)	C16'—C15'—H15'	119.9
C16—C11A—C10A	124.6 (5)	C14'—C15'—H15'	119.9
C13—C12A—C11A	122.1 (4)	C15'—C16'—C1A'	121.0 (4)
C13—C12A—H12A	118.9	C15'—C16'—H16'	119.5
C11A—C12A—H12A	118.9	C1A'—C16'—H16'	119.5
C12A—C13—C14	121.7 (4)	N2'—C17'—H17D	109.5
C12A—C13—H13	119.1	N2'—C17'—H17E	109.5
C14—C13—H13	119.1	H17D—C17'—H17E	109.5
N2—C14—C13	121.9 (4)	N2'—C17'—H17F	109.5
N2—C14—C15	121.4 (4)	H17D—C17'—H17F	109.5
C13—C14—C15	116.7 (4)	H17E—C17'—H17F	109.5
C16—C15—C14	121.1 (4)	N2'—C18'—H18D	109.5
C16—C15—H15	119.5	N2'—C18'—H18E	109.5
C14—C15—H15	119.5	H18D—C18'—H18E	109.5
C15—C16—C11A	122.3 (4)	N2'—C18'—H18F	109.5
C15—C16—H16	118.8	H18D—C18'—H18F	109.5
C11A—C16—H16	118.8	H18E—C18'—H18F	109.5
N2—C17—H17A	109.5	C4'B—C3'B—H3'B	119 (3)
N2—C17—H17B	109.5	C5'B—C4'B—C3'B	123 (2)
H17A—C17—H17B	109.5	C5'B—C4'B—C9'B	117 (3)
N2—C17—H17C	109.5	C3'B—C4'B—C9'B	120 (3)
H17A—C17—H17C	109.5	C4'B—C5'B—H5'B	127 (3)
H17B—C17—H17C	109.5	C0'B—C9'B—C4'B	127 (2)
N2—C18—H18A	109.5	C0'B—C9'B—H9'B	116.5
N2—C18—H18B	109.5	C4'B—C9'B—H9'B	116.5
H18A—C18—H18B	109.5	C9'B—C0'B—C1B'	128 (2)
N2—C18—H18C	109.5	C9'B—C0'B—H0'B	115.8
H18A—C18—H18C	109.5	C1B'—C0'B—H0'B	115.8
H18B—C18—H18C	109.5	C4B—C3B—H3B	118 (10)
C7'—O1'—H1O'	110 (3)	C5B—C4B—C3B	105 (7)
C8'—O2'—H2O'	111 (3)	C5B—C4B—C9B	116 (10)
C2'—N1'—C6'	119.5 (4)	C3B—C4B—C9B	139 (10)
C2'—N1'—C1'	120.3 (4)	C4B—C5B—H5B	119 (10)
C6'—N1'—C1'	120.2 (4)	C10B—C9B—C4B	133 (8)
C14'—N2'—C18'	121.2 (4)	C10B—C9B—H9B	113.4
C14'—N2'—C17'	121.6 (4)	C4B—C9B—H9B	113.4
C18'—N2'—C17'	117.1 (3)	C9B—C10B—C11B	135 (8)
N1'—C1'—C7'	111.9 (3)	C9B—C10B—H10B	112.6
N1'—C1'—H1C	109.2	C11B—C10B—H10B	112.6
C7'—C1'—H1C	109.2	C12B—C11B—C10B	105 (8)
N1'—C1'—H1D	109.2	C11B—C12B—H12B	120 (10)
C2—N1—C1—C7	−87.1 (4)	N1'—C2'—C3'A—C4'A	−3.7 (8)
C6—N1—C1—C7	91.8 (4)	C2'—C3'A—C4'A—C5'A	2.5 (7)
C6—N1—C2—C3A	−0.4 (6)	C2'—C3'A—C4'A—C9'A	−178.7 (4)
C1—N1—C2—C3A	178.4 (4)	C3'A—C4'A—C5'A—C6'	−0.2 (7)
N1—C2—C3A—C4A	0.8 (7)	C9'A—C4'A—C5'A—C6'	−178.8 (5)
C2—C3A—C4A—C5A	−0.4 (6)	C2'—N1'—C6'—C5'A	0.4 (6)
C2—C3A—C4A—C9A	179.1 (4)	C1'—N1'—C6'—C5'A	−177.7 (4)
C3A—C4A—C5A—C6	−0.3 (7)	C4'A—C5'A—C6'—N1'	−1.3 (7)
C9A—C4A—C5A—C6	−179.8 (4)	N1'—C1'—C7'—O1'	54.5 (5)
C4A—C5A—C6—N1	0.6 (7)	N1'—C1'—C7'—C8'	172.2 (3)
C2—N1—C6—C5A	−0.3 (6)	O1'—C7'—C8'—O2'	172.2 (3)
C1—N1—C6—C5A	−179.2 (4)	C1'—C7'—C8'—O2'	52.4 (4)
N1—C1—C7—O1	66.8 (4)	C5'A—C4'A—C9'A—C0'A	−2.3 (8)
N1—C1—C7—C8	−172.6 (3)	C3'A—C4'A—C9'A—C0'A	179.0 (5)
O1—C7—C8—O2	75.1 (4)	C4'A—C9'A—C0'A—C1A'	−179.8 (5)
C1—C7—C8—O2	−44.4 (5)	C9'A—C0'A—C1A'—C12'	179.2 (5)
C5A—C4A—C9A—C10A	178.0 (4)	C9'A—C0'A—C1A'—C16'	−0.6 (9)
C3A—C4A—C9A—C10A	−1.5 (7)	C0'A—C1A'—C12'—C13'	−179.4 (5)
C4A—C9A—C10A—C11A	−179.5 (4)	C16'—C1A'—C12'—C13'	0.4 (8)
C9A—C10A—C11A—C12A	−176.0 (4)	C1A'—C12'—C13'—C14'	0.3 (7)
C9A—C10A—C11A—C16	2.0 (7)	C18'—N2'—C14'—C15'	−174.4 (4)
C16—C11A—C12A—C13	1.2 (7)	C17'—N2'—C14'—C15'	1.3 (6)
C10A—C11A—C12A—C13	179.3 (4)	C18'—N2'—C14'—C13'	6.4 (6)
C11A—C12A—C13—C14	−1.4 (7)	C17'—N2'—C14'—C13'	−177.8 (4)
C17—N2—C14—C13	178.7 (4)	C12'—C13'—C14'—N2'	178.9 (4)
C18—N2—C14—C13	−5.1 (6)	C12'—C13'—C14'—C15'	−0.2 (6)
C17—N2—C14—C15	−0.6 (6)	N2'—C14'—C15'—C16'	−179.7 (4)
C18—N2—C14—C15	175.6 (3)	C13'—C14'—C15'—C16'	−0.6 (6)
C12A—C13—C14—N2	−178.4 (4)	C14'—C15'—C16'—C1A'	1.3 (7)
C12A—C13—C14—C15	0.9 (6)	C12'—C1A'—C16'—C15'	−1.2 (7)
N2—C14—C15—C16	178.9 (4)	C0'A—C1A'—C16'—C15'	178.5 (5)
C13—C14—C15—C16	−0.4 (6)	C5'B—C4'B—C9'B—C0'B	175 (2)
C14—C15—C16—C11A	0.2 (6)	C3'B—C4'B—C9'B—C0'B	−5 (4)
C12A—C11A—C16—C15	−0.6 (6)	C4'B—C9'B—C0'B—C1B'	−178 (3)
C10A—C11A—C16—C15	−178.6 (4)	C5B—C4B—C9B—C10B	17 (15)
C2'—N1'—C1'—C7'	−101.2 (5)	C3B—C4B—C9B—C10B	−167 (10)
C6'—N1'—C1'—C7'	76.9 (5)	C4B—C9B—C10B—C11B	−166 (10)
C6'—N1'—C2'—C3'A	2.2 (7)	C9B—C10B—C11B—C12B	−53 (13)
C1'—N1'—C2'—C3'A	−179.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Cl1	0.83 (3)	2.20 (3)	3.024 (3)	174 (4)
O2—H2O···Cl1i	0.83 (3)	2.27 (3)	3.086 (3)	169 (4)
C2—H2···O2′i	0.95	2.40	3.222 (5)	145
C5A—H5A···Cl2ii	0.95	2.78	3.687 (5)	159
C8—H8A···N2ii	0.99	2.65	3.637 (5)	176
O1′—H1O′···Cl2	0.84 (3)	2.25 (3)	3.083 (3)	171 (4)
O2′—H2O′···Cl2iii	0.83 (3)	2.29 (3)	3.104 (3)	169 (4)
C6′—H6′···O2iii	0.95	2.40	3.236 (6)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯Cl1	0.83 (3)	2.20 (3)	3.024 (3)	174 (4)
O2—H2O⋯Cl1i	0.83 (3)	2.27 (3)	3.086 (3)	169 (4)
C2—H2⋯O2′i	0.95	2.40	3.222 (5)	145
C5A—H5A⋯Cl2ii	0.95	2.78	3.687 (5)	159
C8—H8A⋯N2ii	0.99	2.65	3.637 (5)	176
O1′—H1O′⋯Cl2	0.84 (3)	2.25 (3)	3.083 (3)	171 (4)
O2′—H2O′⋯Cl2iii	0.83 (3)	2.29 (3)	3.104 (3)	169 (4)
C6′—H6′⋯O2iii	0.95	2.40	3.236 (6)	147

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