l-Nebiviololinium chloride dihydrate.

The hydro-chloride salt of chiral l-nebivolol {systematic name: (+)-(R,S,S,S)-bis-[2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxy-ethyl]ammonium chloride dihydrate}, C(22)H(26)F(2)NO(4) (+)·Cl(-)·2H(2)O, was obtained by chiral liquid chromatography as a dihydrate. The pyran rings adopt half-chair conformations. Hydrogen bonds between the cation, anions and water mol-ecules contribute to the formation of layers parallel to the ac plane.

Related literature

For related literature, see: Cini et al. (1990 ▶); van Lommen et al. (1990 ▶); Peeters et al. (1993 ▶); Tuchalski et al. (2006 ▶).

Experimental

Crystal data

C22H26F2NO4 +·Cl−·2H2O

M = 477.92

Orthorhombic,

a = 4.8026 (4) Å

b = 14.5781 (12) Å

c = 33.261 (3) Å

V = 2328.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 291 (2) K

0.60 × 0.12 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.865, T max = 0.981

26222 measured reflections

3401 independent reflections

2857 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.05

3401 reflections

301 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 608 Friedel pairs

Flack parameter: −0.04 (12)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXTL (Bruker, 2001 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807061831/hb2656sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061831/hb2656Isup2.hkl

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

C22H26F2NO4+·Cl–·2H2O	F000 = 1008
Mr = 477.92	Dx = 1.363 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 120 reflections
a = 4.8026 (4) Å	θ = 1.2–25.4º
b = 14.5781 (12) Å	µ = 0.22 mm−1
c = 33.261 (3) Å	T = 291 (2) K
V = 2328.7 (3) Å3	Needle, colourless
Z = 4	0.60 × 0.12 × 0.09 mm

APEX CCD area-detector diffractometer	3401 independent reflections
Radiation source: fine-focus sealed tube	2857 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.054
T = 292(2) K	θmax = 26.4º
ω–scan	θmin = 1.2º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −6→6
Tmin = 0.865, Tmax = 0.981	k = −18→18
26222 measured reflections	l = −41→41

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)] = 0.041	w = 1/[σ2(Fo2) + (0.0545P)2 + 0.978P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113	(Δ/σ)max = 0.004
S = 1.05	Δρmax = 0.33 e Å−3
3401 reflections	Δρmin = −0.24 e Å−3
301 parameters	Extinction correction: none
6 restraints	Absolute structure: Flack (1983), xx Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.04 (12)
Secondary atom site location: difference Fourier map

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	0.7060 (2)	0.96561 (9)	0.28493 (3)	0.0826 (4)
O1W	0.2063 (8)	1.0846 (2)	0.24528 (8)	0.0899 (10)
H1A	0.348 (7)	0.866 (3)	0.2722 (19)	0.135*
H1B	0.348 (8)	1.075 (3)	0.2618 (13)	0.135*
O2W	0.2154 (7)	0.8243 (2)	0.26894 (9)	0.0772 (8)
H2A	0.064 (6)	0.858 (3)	0.2719 (18)	0.116*
H2B	0.191 (10)	1.0312 (17)	0.2332 (13)	0.116*
N1	0.7326 (6)	0.57169 (17)	0.33807 (7)	0.0461 (7)
H1	0.8475	0.5622	0.3171	0.069*
H2	0.5829	0.6026	0.3290	0.069*
C2'	0.8776 (7)	0.6276 (2)	0.36873 (9)	0.0435 (8)
H3	1.0288	0.5918	0.3800	0.052*
H4	0.7484	0.6414	0.3903	0.052*
C2	0.6415 (7)	0.4814 (2)	0.35470 (9)	0.0397 (8)
H5	0.5196	0.4920	0.3775	0.048*
H6	0.8035	0.4483	0.3643	0.048*
C3	0.4905 (7)	0.4230 (2)	0.32411 (9)	0.0390 (8)
H7	0.6169	0.4092	0.3018	0.058*
C3'	0.9940 (7)	0.7165 (2)	0.35241 (9)	0.0403 (8)
H8	0.8498	0.7478	0.3367	0.048*
O4	0.2600 (5)	0.47447 (14)	0.30934 (6)	0.0449 (5)
H9	0.1744	0.4437	0.2928	0.067*
O4'	1.2211 (5)	0.69428 (15)	0.32678 (6)	0.0508 (6)
H10	1.2871	0.7415	0.3174	0.076*
C5	0.3984 (7)	0.3337 (2)	0.34381 (9)	0.0403 (8)
H11	0.5645	0.3008	0.3530	0.060*
C5'	1.0904 (7)	0.7793 (2)	0.38644 (9)	0.0390 (8)
H12	1.2551	0.7521	0.3991	0.047*
O6	0.2381 (5)	0.36036 (13)	0.37856 (6)	0.0455 (6)
O6'	0.8676 (5)	0.78023 (15)	0.41512 (6)	0.0473 (6)
C7	0.0810 (7)	0.2942 (2)	0.39725 (9)	0.0421 (8)
C7'	0.8967 (7)	0.8404 (2)	0.44712 (9)	0.0411 (8)
C8	0.0283 (7)	0.2085 (2)	0.37968 (11)	0.0457 (9)
C8'	1.0804 (7)	0.9139 (2)	0.44601 (10)	0.0431 (8)
C9	0.1485 (8)	0.1844 (2)	0.33954 (11)	0.0571 (10)
H13	0.0117	0.1508	0.3239	0.069*
H14	0.3097	0.1452	0.3432	0.069*
C9'	1.2565 (8)	0.9325 (2)	0.40927 (9)	0.0461 (8)
H15	1.4495	0.9183	0.4152	0.055*
H16	1.2451	0.9971	0.4025	0.055*
C10	0.2340 (9)	0.2710 (2)	0.31677 (9)	0.0506 (9)
H17	0.3460	0.2543	0.2936	0.061*
H18	0.0692	0.3026	0.3072	0.061*
C10'	1.1607 (7)	0.8755 (2)	0.37343 (9)	0.0455 (8)
H19	0.9982	0.9038	0.3614	0.055*
H20	1.3072	0.8736	0.3534	0.055*
C11	−0.0325 (8)	0.3188 (3)	0.43371 (10)	0.0527 (9)
H21	0.0097	0.3756	0.4449	0.063*
C11'	0.7255 (8)	0.8244 (2)	0.47963 (9)	0.0499 (9)
H22	0.6006	0.7757	0.4791	0.060*
C12	−0.2092 (9)	0.2592 (3)	0.45375 (12)	0.0668 (11)
H23	−0.2908	0.2753	0.4781	0.080*
C12'	0.7387 (9)	0.8806 (3)	0.51317 (10)	0.0578 (10)
H24	0.6242	0.8707	0.5353	0.069*
C13	−0.2590 (9)	0.1757 (3)	0.43632 (13)	0.0660 (11)
C13'	0.9266 (9)	0.9516 (3)	0.51263 (10)	0.0581 (10)
C14	−0.1492 (8)	0.1495 (3)	0.40030 (13)	0.0615 (11)
H25	−0.1928	0.0924	0.3895	0.092*
C14'	1.0930 (8)	0.9700 (3)	0.48011 (10)	0.0551 (9)
H26	1.2141	1.0198	0.4807	0.066*
F1	−0.4347 (6)	0.11636 (19)	0.45634 (9)	0.1020 (9)
F1'	0.9452 (7)	1.00610 (18)	0.54589 (7)	0.0957 (9)

	U11	U22	U33	U12	U13	U23
Cl1	0.0593 (7)	0.1298 (10)	0.0587 (6)	−0.0099 (7)	−0.0044 (5)	0.0150 (6)
O1W	0.098 (3)	0.120 (3)	0.0524 (17)	0.013 (2)	−0.0059 (17)	−0.0197 (17)
O2W	0.0740 (19)	0.095 (2)	0.0626 (16)	−0.0110 (18)	0.0067 (18)	0.0175 (16)
N1	0.0506 (17)	0.0464 (15)	0.0414 (14)	−0.0137 (15)	0.0035 (14)	−0.0038 (13)
C2'	0.0459 (19)	0.0432 (19)	0.0414 (18)	−0.0070 (16)	−0.0018 (16)	−0.0028 (15)
C2	0.0390 (18)	0.0357 (17)	0.0444 (17)	−0.0061 (15)	0.0004 (15)	0.0030 (14)
C3	0.0357 (18)	0.0401 (17)	0.0411 (17)	0.0007 (16)	0.0039 (15)	−0.0046 (15)
C3'	0.0384 (18)	0.0422 (18)	0.0403 (17)	−0.0039 (16)	0.0044 (15)	0.0003 (15)
O4	0.0432 (12)	0.0465 (13)	0.0450 (12)	0.0013 (13)	−0.0060 (12)	−0.0019 (10)
O4'	0.0512 (14)	0.0442 (12)	0.0569 (13)	−0.0016 (12)	0.0125 (13)	−0.0022 (11)
C5	0.0404 (18)	0.0349 (17)	0.0456 (18)	0.0003 (15)	0.0008 (17)	−0.0006 (15)
C5'	0.0348 (17)	0.0430 (19)	0.0393 (17)	−0.0010 (15)	−0.0008 (15)	0.0007 (15)
O6	0.0562 (14)	0.0394 (12)	0.0410 (11)	−0.0112 (12)	0.0060 (12)	−0.0027 (10)
O6'	0.0437 (13)	0.0532 (14)	0.0449 (12)	−0.0116 (11)	0.0076 (11)	−0.0069 (11)
C7	0.0403 (18)	0.044 (2)	0.0424 (19)	−0.0079 (17)	−0.0072 (16)	0.0112 (16)
C7'	0.0400 (19)	0.0469 (19)	0.0365 (17)	0.0051 (17)	−0.0033 (16)	−0.0046 (15)
C8	0.0412 (19)	0.0370 (18)	0.059 (2)	−0.0038 (17)	−0.0063 (17)	0.0082 (17)
C8'	0.0386 (19)	0.0441 (19)	0.0467 (19)	0.0081 (17)	−0.0071 (16)	−0.0029 (16)
C9	0.060 (3)	0.0351 (18)	0.076 (3)	−0.0089 (18)	0.005 (2)	−0.0075 (18)
C9'	0.0445 (19)	0.0416 (18)	0.0522 (19)	−0.0056 (18)	−0.0005 (18)	0.0015 (16)
C10	0.056 (2)	0.046 (2)	0.0500 (19)	−0.008 (2)	0.003 (2)	−0.0102 (16)
C10'	0.049 (2)	0.0463 (19)	0.0408 (18)	−0.0076 (16)	−0.0002 (16)	0.0044 (15)
C11	0.058 (2)	0.055 (2)	0.045 (2)	−0.012 (2)	0.0019 (19)	0.0034 (18)
C11'	0.051 (2)	0.055 (2)	0.0446 (19)	0.0013 (19)	0.0068 (18)	0.0017 (16)
C12	0.060 (3)	0.078 (3)	0.062 (2)	−0.011 (2)	0.007 (2)	0.016 (2)
C12'	0.058 (2)	0.072 (2)	0.0435 (19)	0.016 (2)	0.0081 (19)	0.0023 (19)
C13	0.055 (2)	0.060 (2)	0.084 (3)	−0.020 (2)	0.001 (2)	0.027 (2)
C13'	0.068 (3)	0.065 (3)	0.041 (2)	0.008 (2)	−0.001 (2)	−0.0143 (19)
C14	0.054 (2)	0.048 (2)	0.082 (3)	−0.0118 (19)	−0.008 (2)	0.009 (2)
C14'	0.059 (2)	0.051 (2)	0.056 (2)	−0.002 (2)	−0.007 (2)	−0.0113 (18)
F1	0.090 (2)	0.0920 (18)	0.124 (2)	−0.0404 (17)	0.0217 (17)	0.0312 (17)
F1'	0.124 (2)	0.1009 (19)	0.0617 (14)	−0.0078 (18)	0.0089 (15)	−0.0367 (14)

O1W—H1B	0.89 (4)	C7—C8	1.402 (5)
O1W—H2B	0.88 (3)	C7'—C11'	1.378 (5)
O2W—H1A	0.89 (4)	C7'—C8'	1.388 (5)
O2W—H2A	0.92 (5)	C8—C14	1.391 (5)
N1—C2'	1.479 (4)	C8—C9	1.496 (5)
N1—C2	1.493 (4)	C8'—C14'	1.400 (5)
N1—H1	0.9000	C8'—C9'	1.511 (5)
N1—H2	0.9000	C9—C10	1.528 (5)
C2'—C3'	1.512 (4)	C9—H13	0.9700
C2'—H3	0.9700	C9—H14	0.9700
C2'—H4	0.9700	C9'—C10'	1.525 (4)
C2—C3	1.512 (4)	C9'—H15	0.9700
C2—H5	0.9700	C9'—H16	0.9700
C2—H6	0.9700	C10—H17	0.9700
C3—O4	1.424 (4)	C10—H18	0.9700
C3—C5	1.524 (4)	C10'—H19	0.9700
C3—H7	0.9800	C10'—H20	0.9700
C3'—O4'	1.422 (4)	C11—C12	1.385 (5)
C3'—C5'	1.528 (4)	C11—H21	0.9300
C3'—H8	0.9800	C11'—C12'	1.386 (5)
O4—H9	0.8200	C11'—H22	0.9300
O4'—H10	0.8200	C12—C13	1.370 (6)
C5—O6	1.442 (4)	C12—H23	0.9300
C5—C10	1.506 (5)	C12'—C13'	1.372 (5)
C5—H11	0.9800	C12'—H24	0.9300
C5'—O6'	1.434 (4)	C13—C14	1.363 (6)
C5'—C10'	1.505 (4)	C13—F1	1.379 (4)
C5'—H12	0.9800	C13'—C14'	1.371 (5)
O6—C7	1.373 (4)	C13'—F1'	1.365 (4)
O6'—C7'	1.386 (4)	C14—H25	0.9300
C7—C11	1.377 (5)	C14'—H26	0.9300
H1B—O1W—H2B	102 (4)	C14—C8—C7	117.1 (3)
H1A—O2W—H2A	101 (4)	C14—C8—C9	122.1 (3)
C2'—N1—C2	111.6 (2)	C7—C8—C9	120.7 (3)
C2'—N1—H1	109.3	C7'—C8'—C14'	117.2 (3)
C2—N1—H1	109.3	C7'—C8'—C9'	121.1 (3)
C2'—N1—H2	109.3	C14'—C8'—C9'	121.7 (3)
C2—N1—H2	109.3	C8—C9—C10	110.6 (3)
H1—N1—H2	108.0	C8—C9—H13	109.5
N1—C2'—C3'	113.5 (3)	C10—C9—H13	109.5
N1—C2'—H3	108.9	C8—C9—H14	109.5
C3'—C2'—H3	108.9	C10—C9—H14	109.5
N1—C2'—H4	108.9	H13—C9—H14	108.1
C3'—C2'—H4	108.9	C8'—C9'—C10'	111.4 (3)
H3—C2'—H4	107.7	C8'—C9'—H15	109.3
N1—C2—C3	112.8 (2)	C10'—C9'—H15	109.3
N1—C2—H5	109.0	C8'—C9'—H16	109.3
C3—C2—H5	109.0	C10'—C9'—H16	109.3
N1—C2—H6	109.0	H15—C9'—H16	108.0
C3—C2—H6	109.0	C5—C10—C9	110.3 (3)
H5—C2—H6	107.8	C5—C10—H17	109.6
O4—C3—C2	108.0 (2)	C9—C10—H17	109.6
O4—C3—C5	111.9 (3)	C5—C10—H18	109.6
C2—C3—C5	109.3 (2)	C9—C10—H18	109.6
O4—C3—H7	109.2	H17—C10—H18	108.1
C2—C3—H7	109.2	C5'—C10'—C9'	110.5 (3)
C5—C3—H7	109.2	C5'—C10'—H19	109.5
O4'—C3'—C2'	107.7 (3)	C9'—C10'—H19	109.5
O4'—C3'—C5'	110.4 (3)	C5'—C10'—H20	109.5
C2'—C3'—C5'	111.1 (2)	C9'—C10'—H20	109.5
O4'—C3'—H8	109.2	H19—C10'—H20	108.1
C2'—C3'—H8	109.2	C7—C11—C12	120.2 (3)
C5'—C3'—H8	109.2	C7—C11—H21	119.9
C3—O4—H9	109.5	C12—C11—H21	119.9
C3'—O4'—H10	109.5	C7'—C11'—C12'	120.3 (4)
O6—C5—C10	111.3 (3)	C7'—C11'—H22	119.9
O6—C5—C3	105.6 (2)	C12'—C11'—H22	119.9
C10—C5—C3	114.5 (3)	C13—C12—C11	117.5 (4)
O6—C5—H11	108.4	C13—C12—H23	121.3
C10—C5—H11	108.4	C11—C12—H23	121.3
C3—C5—H11	108.4	C13'—C12'—C11'	117.7 (4)
O6'—C5'—C10'	110.5 (3)	C13'—C12'—H24	121.1
O6'—C5'—C3'	105.8 (2)	C11'—C12'—H24	121.1
C10'—C5'—C3'	114.4 (3)	C14—C13—C12	123.5 (4)
O6'—C5'—H12	108.7	C14—C13—F1	119.1 (4)
C10'—C5'—H12	108.7	C12—C13—F1	117.4 (4)
C3'—C5'—H12	108.7	C14'—C13'—F1'	119.1 (4)
C7—O6—C5	117.8 (2)	C14'—C13'—C12'	122.7 (3)
C7'—O6'—C5'	116.2 (2)	F1'—C13'—C12'	118.1 (3)
O6—C7—C11	115.7 (3)	C13—C14—C8	119.9 (4)
O6—C7—C8	122.4 (3)	C13—C14—H25	120.1
C11—C7—C8	121.8 (3)	C8—C14—H25	120.1
C11'—C7'—O6'	115.8 (3)	C13'—C14'—C8'	120.0 (4)
C11'—C7'—C8'	122.0 (3)	C13'—C14'—H26	120.0
O6'—C7'—C8'	122.1 (3)	C8'—C14'—H26	120.0
C2—N1—C2'—C3'	175.4 (3)	O6'—C7'—C8'—C9'	0.8 (5)
C2'—N1—C2—C3	179.6 (3)	C14—C8—C9—C10	157.4 (4)
N1—C2—C3—O4	−56.6 (3)	C7—C8—C9—C10	−19.6 (5)
N1—C2—C3—C5	−178.5 (3)	C7'—C8'—C9'—C10'	11.8 (4)
N1—C2'—C3'—O4'	−70.0 (4)	C14'—C8'—C9'—C10'	−167.6 (3)
N1—C2'—C3'—C5'	169.0 (3)	O6—C5—C10—C9	−59.5 (4)
O4—C3—C5—O6	−64.8 (3)	C3—C5—C10—C9	−179.1 (3)
C2—C3—C5—O6	54.8 (3)	C8—C9—C10—C5	47.3 (4)
O4—C3—C5—C10	58.0 (4)	O6'—C5'—C10'—C9'	61.2 (4)
C2—C3—C5—C10	177.5 (3)	C3'—C5'—C10'—C9'	−179.6 (3)
O4'—C3'—C5'—O6'	−167.0 (2)	C8'—C9'—C10'—C5'	−41.4 (4)
C2'—C3'—C5'—O6'	−47.6 (3)	O6—C7—C11—C12	175.8 (3)
O4'—C3'—C5'—C10'	71.1 (4)	C8—C7—C11—C12	−1.5 (5)
C2'—C3'—C5'—C10'	−169.5 (3)	O6'—C7'—C11'—C12'	179.9 (3)
C10—C5—O6—C7	41.9 (4)	C8'—C7'—C11'—C12'	−2.0 (5)
C3—C5—O6—C7	166.7 (3)	C7—C11—C12—C13	1.5 (6)
C10'—C5'—O6'—C7'	−49.5 (4)	C7'—C11'—C12'—C13'	−0.1 (5)
C3'—C5'—O6'—C7'	−173.9 (2)	C11—C12—C13—C14	−1.4 (7)
C5—O6—C7—C11	170.0 (3)	C11—C12—C13—F1	179.9 (3)
C5—O6—C7—C8	−12.7 (4)	C11'—C12'—C13'—C14'	1.9 (6)
C5'—O6'—C7'—C11'	−163.3 (3)	C11'—C12'—C13'—F1'	−178.6 (3)
C5'—O6'—C7'—C8'	18.7 (4)	C12—C13—C14—C8	1.3 (7)
O6—C7—C8—C14	−175.8 (3)	F1—C13—C14—C8	180.0 (3)
C11—C7—C8—C14	1.3 (5)	C7—C8—C14—C13	−1.2 (5)
O6—C7—C8—C9	1.4 (5)	C9—C8—C14—C13	−178.3 (4)
C11—C7—C8—C9	178.5 (3)	F1'—C13'—C14'—C8'	178.8 (3)
C11'—C7'—C8'—C14'	2.2 (5)	C12'—C13'—C14'—C8'	−1.7 (6)
O6'—C7'—C8'—C14'	−179.8 (3)	C7'—C8'—C14'—C13'	−0.4 (5)
C11'—C7'—C8'—C9'	−177.2 (3)	C9'—C8'—C14'—C13'	179.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1Wi	0.90	2.12	2.794 (3)	131
N1—H1···O4ii	0.90	2.37	3.056 (4)	133
N1—H2···O4'iii	0.90	2.19	3.061 (4)	162
O4—H9···Cl1i	0.82	2.67	3.142 (2)	118
O4'—H10···O2Wii	0.82	2.04	2.701 (4)	137
O1W—H1B···Cl1	0.89 (4)	2.47 (4)	3.242 (2)	146 (4)
O1W—H2B···N1iv	0.88 (3)	2.47 (4)	2.794 (3)	102 (3)
O2W—H1A···Cl1	0.89 (4)	2.29 (4)	3.175 (3)	175 (3)
O2W—H2A···Cl1iii	0.88 (4)	2.37 (4)	3.242 (3)	171 (3)
C2'—H4···O6'	0.97	2.26	2.708 (4)	107
C2—H5···O6	0.97	2.35	2.738 (4)	103
C2—H6···O6ii	0.97	2.49	3.457 (4)	172
C14'—H26···F1v	0.93	2.34	3.213 (5)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1Wi	0.90	2.12	2.794 (3)	131
N1—H1⋯O4ii	0.90	2.37	3.056 (4)	133
N1—H2⋯O4′iii	0.90	2.19	3.061 (4)	162
O4—H9⋯Cl1i	0.82	2.67	3.142 (2)	118
O4′—H10⋯O2Wii	0.82	2.04	2.701 (4)	137
O1W—H1B⋯Cl1	0.89 (4)	2.47 (4)	3.242 (2)	146 (4)
O1W—H2B⋯N1iv	0.88 (3)	2.47 (4)	2.794 (3)	102 (3)
O2W—H1A⋯Cl1	0.89 (4)	2.29 (4)	3.175 (3)	175 (3)
O2W—H2A⋯Cl1iii	0.88 (4)	2.37 (4)	3.242 (3)	171 (3)
C2′—H4⋯O6′	0.97	2.26	2.708 (4)	107
C2—H5⋯O6	0.97	2.35	2.738 (4)	103
C2—H6⋯O6ii	0.97	2.49	3.457 (4)	172
C14′—H26⋯F1v	0.93	2.34	3.213 (5)	156

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