2,2'-[(1S,2S)-1,2-Bis(2-hy-droxy-phen-yl)ethane-1,2-di-yl]bis(isoindoline-1,3-dione) ethanol monosolvate hemihydrate.

In the title compound, C30H20N2O6·C2H6O·0.5H2O, the solvent water mol-ecule lies on a twofold rotation axis. The dihedral angle between the essentially planar isoindole ring systems [maximum deviations = 0.028 (1) and 0.022 (1) Å] is 47.12 (5)°. The dihedral angle between the benzene rings is 81.32 (7)°. In the crystal, the components are linked into a three-dimensional network via O-H⋯O hydrogen bonds.

Related literature

For the use of chiral bis­phenolic ligands in stereoselective catalysis, see: Noyori et al. (1984 ▶); Takaya et al. (1989 ▶); Liu & Ding (2005 ▶); Xu et al. (2011 ▶); Yamaguchi et al. (2009 ▶); Van den Berg et al. (2002 ▶); So et al. (2012 ▶); Kim, Nguyen et al. (2008 ▶); Kim, So et al. (2008 ▶); For related structures, see: Li et al. (2011 ▶); Liu et al. (2011 ▶). For analysis of the absolute configration, see: Hooft et al. (2008 ▶).

Experimental

Crystal data

C30H20N2O6·C2H6O·0.5H2O

M = 559.56

Tetragonal,

a = 10.6848 (3) Å

c = 47.9935 (17) Å

V = 5479.2 (3) Å3

Z = 8

Cu Kα radiation

μ = 0.81 mm−1

T = 147 K

0.29 × 0.18 × 0.18 mm

Data collection

Bruker Kappa APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.696, T max = 0.753

35250 measured reflections

4786 independent reflections

4756 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.075

S = 1.12

4786 reflections

391 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1895 Friedel pairs

Flack parameter: 0.03 (13)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); 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/S1600536813003978/aa2082sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003978/aa2082Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003978/aa2082Isup3.cml

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

C30H20N2O6·C2H6O·0.5H2O	Dx = 1.357 Mg m−3
Mr = 559.56	Cu Kα radiation, λ = 1.54178 Å
Tetragonal, P41212	Cell parameters from 9692 reflections
Hall symbol: P 4abw 2nw	θ = 3.7–66.5°
a = 10.6848 (3) Å	µ = 0.81 mm−1
c = 47.9935 (17) Å	T = 147 K
V = 5479.2 (3) Å3	Needle, pale yellow
Z = 8	0.29 × 0.18 × 0.18 mm
F(000) = 2344

Bruker Kappa APEX DUO CCD diffractometer	4786 independent reflections
Radiation source: Bruker ImuS	4756 reflections with I > 2σ(I)
Multi-layer optics monochromator	Rint = 0.035
φ and ω scans	θmax = 66.6°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→12
Tmin = 0.696, Tmax = 0.753	k = −12→12
35250 measured reflections	l = −53→56

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.0389P)2 + 1.2163P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.001
4786 reflections	Δρmax = 0.26 e Å−3
391 parameters	Δρmin = −0.18 e Å−3
0 restraints	Absolute structure: Flack (1983), 1895 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (13)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O1	−0.12757 (12)	0.57392 (11)	0.02270 (2)	0.0380 (3)
O2	−0.27045 (11)	0.13393 (10)	0.10646 (2)	0.0335 (3)
O3	0.16202 (10)	0.49860 (10)	0.05562 (2)	0.0337 (3)
O4	0.03625 (10)	0.10133 (9)	0.03340 (2)	0.0285 (2)
O5	−0.05120 (10)	0.50131 (9)	0.11171 (2)	0.0276 (2)
O6	0.05013 (10)	0.09166 (9)	0.09551 (2)	0.0295 (2)
N1	0.06521 (10)	0.31129 (11)	0.04480 (2)	0.0198 (2)
N2	−0.02832 (11)	0.29340 (11)	0.09907 (2)	0.0206 (2)
C1	−0.06345 (12)	0.35618 (13)	0.05051 (3)	0.0202 (3)
H1A	−0.0559	0.4460	0.0561	0.024*
C2	−0.11822 (12)	0.28568 (13)	0.07582 (3)	0.0201 (3)
H2A	−0.1259	0.1955	0.0705	0.024*
C3	−0.14501 (13)	0.35352 (14)	0.02451 (3)	0.0232 (3)
C4	−0.19143 (13)	0.24298 (15)	0.01311 (3)	0.0264 (3)
H4A	−0.1747	0.1657	0.0222	0.032*
C5	−0.26174 (15)	0.24368 (17)	−0.01123 (3)	0.0336 (4)
H5A	−0.2908	0.1673	−0.0190	0.040*
C6	−0.28897 (16)	0.35578 (18)	−0.02399 (3)	0.0371 (4)
H6A	−0.3377	0.3567	−0.0405	0.045*
C7	−0.24576 (17)	0.46746 (17)	−0.01282 (3)	0.0365 (4)
H7A	−0.2656	0.5446	−0.0216	0.044*
C8	−0.17327 (15)	0.46656 (15)	0.01131 (3)	0.0288 (3)
C9	−0.24683 (13)	0.33031 (13)	0.08481 (3)	0.0212 (3)
C10	−0.29333 (14)	0.44909 (14)	0.07941 (3)	0.0249 (3)
H10A	−0.2441	0.5064	0.0690	0.030*
C11	−0.41034 (14)	0.48579 (14)	0.08892 (3)	0.0284 (3)
H11A	−0.4406	0.5676	0.0851	0.034*
C12	−0.48290 (14)	0.40203 (15)	0.10405 (3)	0.0290 (3)
H12A	−0.5633	0.4264	0.1105	0.035*
C13	−0.43858 (14)	0.28366 (15)	0.10968 (3)	0.0285 (3)
H13A	−0.4887	0.2263	0.1199	0.034*
C14	−0.32052 (14)	0.24807 (14)	0.10041 (3)	0.0248 (3)
C15	0.16844 (13)	0.39132 (13)	0.04779 (3)	0.0230 (3)
C16	0.28018 (13)	0.31660 (14)	0.04040 (3)	0.0237 (3)
C17	0.40449 (15)	0.35044 (16)	0.03946 (3)	0.0331 (4)
H17A	0.4304	0.4338	0.0432	0.040*
C18	0.49035 (15)	0.25736 (19)	0.03282 (4)	0.0397 (4)
H18A	0.5770	0.2772	0.0322	0.048*
C19	0.45225 (15)	0.13664 (18)	0.02712 (3)	0.0367 (4)
H19A	0.5133	0.0752	0.0227	0.044*
C20	0.32610 (15)	0.10254 (15)	0.02776 (3)	0.0281 (3)
H20A	0.2997	0.0196	0.0237	0.034*
C21	0.24159 (13)	0.19577 (14)	0.03461 (3)	0.0218 (3)
C22	0.10333 (13)	0.19047 (13)	0.03709 (3)	0.0208 (3)
C23	−0.00112 (13)	0.40013 (13)	0.11452 (3)	0.0210 (3)
C24	0.10131 (13)	0.36512 (13)	0.13406 (3)	0.0229 (3)
C25	0.16348 (15)	0.43582 (14)	0.15371 (3)	0.0273 (3)
H25A	0.1404	0.5201	0.1573	0.033*
C26	0.26124 (16)	0.37874 (15)	0.16801 (3)	0.0305 (3)
H26A	0.3067	0.4254	0.1815	0.037*
C27	0.29385 (14)	0.25485 (15)	0.16298 (3)	0.0289 (3)
H27A	0.3613	0.2184	0.1730	0.035*
C28	0.22891 (14)	0.18341 (15)	0.14344 (3)	0.0269 (3)
H28A	0.2497	0.0982	0.1402	0.032*
C29	0.13328 (13)	0.24133 (13)	0.12906 (3)	0.0229 (3)
C30	0.05112 (13)	0.19354 (13)	0.10641 (3)	0.0225 (3)
O1S	−0.15257 (14)	−0.07024 (14)	0.04583 (3)	0.0540 (4)
C1S	−0.1589 (2)	−0.1315 (2)	0.07221 (4)	0.0479 (5)
H1SA	−0.1368	−0.0721	0.0872	0.057*
H1SB	−0.0987	−0.2020	0.0727	0.057*
C2S	−0.2877 (2)	−0.1788 (2)	0.07646 (4)	0.0545 (5)
H2SA	−0.2932	−0.2205	0.0946	0.082*
H2SB	−0.3085	−0.2386	0.0617	0.082*
H2SC	−0.3467	−0.1087	0.0759	0.082*
O1W	−0.20559 (11)	0.79441 (11)	0.0000	0.0348 (4)
H1O	−0.153 (2)	0.636 (2)	0.0128 (5)	0.052 (6)*
H2O	−0.324 (2)	0.093 (2)	0.1168 (4)	0.046 (6)*
H1SO	−0.068 (3)	−0.019 (3)	0.0430 (7)	0.111 (11)*
H1W	−0.178 (3)	0.853 (3)	0.0165 (6)	0.095 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0515 (7)	0.0252 (6)	0.0372 (6)	0.0009 (5)	−0.0126 (5)	0.0079 (5)
O2	0.0345 (6)	0.0240 (5)	0.0420 (6)	0.0025 (5)	0.0136 (5)	0.0098 (5)
O3	0.0308 (6)	0.0229 (5)	0.0475 (6)	−0.0061 (5)	0.0054 (5)	−0.0099 (5)
O4	0.0265 (5)	0.0237 (5)	0.0352 (6)	−0.0050 (4)	0.0041 (4)	−0.0052 (4)
O5	0.0318 (5)	0.0214 (5)	0.0297 (5)	0.0065 (4)	0.0021 (4)	−0.0017 (4)
O6	0.0371 (6)	0.0197 (5)	0.0316 (5)	0.0062 (4)	−0.0032 (5)	−0.0038 (4)
N1	0.0175 (6)	0.0203 (6)	0.0215 (5)	−0.0006 (4)	0.0016 (4)	−0.0012 (5)
N2	0.0233 (6)	0.0192 (6)	0.0195 (5)	0.0015 (5)	0.0010 (5)	−0.0009 (4)
C1	0.0182 (6)	0.0199 (7)	0.0224 (6)	0.0005 (5)	0.0030 (5)	0.0008 (5)
C2	0.0208 (7)	0.0195 (7)	0.0201 (6)	−0.0001 (5)	0.0020 (5)	−0.0009 (5)
C3	0.0189 (6)	0.0292 (7)	0.0214 (7)	0.0014 (6)	0.0037 (5)	0.0007 (6)
C4	0.0204 (7)	0.0315 (8)	0.0271 (7)	−0.0018 (6)	0.0035 (6)	−0.0016 (6)
C5	0.0251 (8)	0.0449 (9)	0.0307 (8)	−0.0020 (7)	−0.0015 (6)	−0.0087 (7)
C6	0.0294 (8)	0.0562 (11)	0.0257 (8)	0.0048 (8)	−0.0051 (6)	−0.0040 (7)
C7	0.0395 (9)	0.0432 (9)	0.0268 (7)	0.0073 (7)	−0.0034 (7)	0.0067 (7)
C8	0.0283 (8)	0.0326 (8)	0.0254 (7)	0.0010 (6)	0.0021 (6)	0.0014 (6)
C9	0.0200 (7)	0.0232 (7)	0.0204 (6)	−0.0008 (5)	0.0018 (5)	−0.0021 (5)
C10	0.0247 (7)	0.0235 (7)	0.0265 (7)	−0.0008 (6)	0.0028 (6)	0.0004 (6)
C11	0.0255 (7)	0.0261 (7)	0.0336 (8)	0.0060 (6)	0.0006 (6)	−0.0020 (6)
C12	0.0214 (7)	0.0344 (8)	0.0312 (8)	0.0009 (6)	0.0055 (6)	−0.0051 (6)
C13	0.0257 (7)	0.0306 (8)	0.0291 (7)	−0.0030 (6)	0.0080 (6)	0.0010 (6)
C14	0.0269 (7)	0.0238 (7)	0.0238 (7)	−0.0003 (6)	0.0038 (6)	−0.0006 (6)
C15	0.0238 (7)	0.0237 (7)	0.0215 (7)	−0.0039 (6)	0.0024 (5)	0.0005 (6)
C16	0.0211 (7)	0.0297 (7)	0.0204 (6)	−0.0025 (6)	0.0014 (5)	0.0000 (6)
C17	0.0235 (8)	0.0395 (9)	0.0364 (8)	−0.0064 (6)	0.0008 (6)	−0.0073 (7)
C18	0.0204 (7)	0.0592 (11)	0.0396 (9)	−0.0008 (7)	0.0015 (7)	−0.0090 (8)
C19	0.0258 (8)	0.0504 (10)	0.0340 (8)	0.0102 (8)	0.0022 (7)	−0.0047 (7)
C20	0.0293 (8)	0.0325 (8)	0.0224 (7)	0.0061 (6)	0.0009 (6)	−0.0020 (6)
C21	0.0212 (7)	0.0278 (7)	0.0163 (6)	0.0004 (6)	0.0006 (5)	0.0005 (5)
C22	0.0216 (7)	0.0223 (7)	0.0186 (6)	0.0010 (6)	0.0021 (5)	0.0011 (5)
C23	0.0233 (7)	0.0208 (7)	0.0188 (6)	−0.0004 (5)	0.0055 (5)	−0.0006 (5)
C24	0.0263 (7)	0.0221 (7)	0.0204 (6)	0.0000 (6)	0.0043 (6)	0.0016 (6)
C25	0.0328 (8)	0.0248 (7)	0.0245 (7)	−0.0027 (6)	0.0020 (6)	0.0004 (6)
C26	0.0343 (8)	0.0327 (8)	0.0246 (7)	−0.0109 (7)	−0.0022 (6)	0.0018 (6)
C27	0.0259 (7)	0.0333 (8)	0.0275 (7)	−0.0028 (6)	−0.0004 (6)	0.0075 (6)
C28	0.0276 (8)	0.0266 (7)	0.0266 (7)	0.0024 (6)	0.0021 (6)	0.0041 (6)
C29	0.0227 (7)	0.0242 (7)	0.0218 (7)	0.0011 (6)	0.0034 (5)	0.0010 (6)
C30	0.0232 (7)	0.0221 (7)	0.0223 (6)	0.0020 (6)	0.0042 (5)	0.0011 (6)
O1S	0.0582 (9)	0.0541 (8)	0.0497 (8)	−0.0259 (7)	−0.0012 (7)	0.0048 (7)
C1S	0.0512 (11)	0.0473 (11)	0.0453 (10)	−0.0082 (9)	−0.0092 (9)	0.0008 (8)
C2S	0.0588 (13)	0.0618 (13)	0.0430 (10)	−0.0186 (10)	−0.0028 (9)	0.0056 (9)
O1W	0.0324 (5)	0.0324 (5)	0.0394 (9)	−0.0010 (7)	−0.0075 (5)	0.0075 (5)

O1—C8	1.361 (2)	C12—H12A	0.9500
O1—H1O	0.86 (2)	C13—C14	1.391 (2)
O2—C14	1.3630 (19)	C13—H13A	0.9500
O2—H2O	0.88 (2)	C15—C16	1.479 (2)
O3—C15	1.2082 (18)	C16—C17	1.377 (2)
O4—C22	1.2050 (18)	C16—C21	1.383 (2)
O5—C23	1.2137 (17)	C17—C18	1.390 (2)
O6—C30	1.2078 (18)	C17—H17A	0.9500
N1—C15	1.4030 (18)	C18—C19	1.380 (3)
N1—C22	1.4033 (18)	C18—H18A	0.9500
N1—C1	1.4815 (17)	C19—C20	1.397 (2)
N2—C23	1.3909 (18)	C19—H19A	0.9500
N2—C30	1.4081 (18)	C20—C21	1.384 (2)
N2—C2	1.4749 (18)	C20—H20A	0.9500
C1—C3	1.5222 (19)	C21—C22	1.4832 (19)
C1—C2	1.5444 (18)	C23—C24	1.489 (2)
C1—H1A	1.0000	C24—C25	1.379 (2)
C2—C9	1.5173 (19)	C24—C29	1.387 (2)
C2—H2A	1.0000	C25—C26	1.391 (2)
C3—C4	1.393 (2)	C25—H25A	0.9500
C3—C8	1.397 (2)	C26—C27	1.390 (2)
C4—C5	1.389 (2)	C26—H26A	0.9500
C4—H4A	0.9500	C27—C28	1.394 (2)
C5—C6	1.376 (3)	C27—H27A	0.9500
C5—H5A	0.9500	C28—C29	1.380 (2)
C6—C7	1.387 (3)	C28—H28A	0.9500
C6—H6A	0.9500	C29—C30	1.488 (2)
C7—C8	1.393 (2)	O1S—C1S	1.427 (2)
C7—H7A	0.9500	O1S—H1SO	1.06 (4)
C9—C10	1.387 (2)	C1S—C2S	1.481 (3)
C9—C14	1.397 (2)	C1S—H1SA	0.9900
C10—C11	1.388 (2)	C1S—H1SB	0.9900
C10—H10A	0.9500	C2S—H2SA	0.9800
C11—C12	1.389 (2)	C2S—H2SB	0.9800
C11—H11A	0.9500	C2S—H2SC	0.9800
C12—C13	1.377 (2)	O1W—H1W	1.06 (3)
C8—O1—H1O	108.3 (15)	C17—C16—C21	121.72 (14)
C14—O2—H2O	108.4 (14)	C17—C16—C15	130.12 (14)
C15—N1—C22	111.07 (11)	C21—C16—C15	108.13 (12)
C15—N1—C1	120.88 (11)	C16—C17—C18	117.14 (16)
C22—N1—C1	128.01 (11)	C16—C17—H17A	121.4
C23—N2—C30	111.23 (11)	C18—C17—H17A	121.4
C23—N2—C2	125.82 (11)	C19—C18—C17	121.30 (16)
C30—N2—C2	122.64 (11)	C19—C18—H18A	119.4
N1—C1—C3	111.94 (11)	C17—C18—H18A	119.4
N1—C1—C2	109.82 (11)	C18—C19—C20	121.61 (15)
C3—C1—C2	114.75 (11)	C18—C19—H19A	119.2
N1—C1—H1A	106.6	C20—C19—H19A	119.2
C3—C1—H1A	106.6	C21—C20—C19	116.56 (15)
C2—C1—H1A	106.6	C21—C20—H20A	121.7
N2—C2—C9	110.91 (10)	C19—C20—H20A	121.7
N2—C2—C1	108.73 (11)	C16—C21—C20	121.66 (14)
C9—C2—C1	114.44 (11)	C16—C21—C22	108.45 (13)
N2—C2—H2A	107.5	C20—C21—C22	129.89 (14)
C9—C2—H2A	107.5	O4—C22—N1	126.39 (12)
C1—C2—H2A	107.5	O4—C22—C21	127.65 (13)
C4—C3—C8	118.56 (13)	N1—C22—C21	105.96 (12)
C4—C3—C1	122.80 (13)	O5—C23—N2	125.38 (13)
C8—C3—C1	118.64 (13)	O5—C23—C24	128.16 (13)
C5—C4—C3	121.22 (15)	N2—C23—C24	106.45 (11)
C5—C4—H4A	119.4	C25—C24—C29	121.47 (14)
C3—C4—H4A	119.4	C25—C24—C23	130.33 (13)
C6—C5—C4	119.56 (15)	C29—C24—C23	108.16 (12)
C6—C5—H5A	120.2	C24—C25—C26	117.33 (14)
C4—C5—H5A	120.2	C24—C25—H25A	121.3
C5—C6—C7	120.41 (14)	C26—C25—H25A	121.3
C5—C6—H6A	119.8	C27—C26—C25	121.36 (14)
C7—C6—H6A	119.8	C27—C26—H26A	119.3
C6—C7—C8	120.02 (16)	C25—C26—H26A	119.3
C6—C7—H7A	120.0	C26—C27—C28	120.89 (14)
C8—C7—H7A	120.0	C26—C27—H27A	119.6
O1—C8—C7	121.83 (14)	C28—C27—H27A	119.6
O1—C8—C3	117.96 (13)	C29—C28—C27	117.36 (14)
C7—C8—C3	120.21 (15)	C29—C28—H28A	121.3
C10—C9—C14	118.27 (13)	C27—C28—H28A	121.3
C10—C9—C2	123.96 (12)	C28—C29—C24	121.58 (14)
C14—C9—C2	117.72 (12)	C28—C29—C30	130.44 (13)
C9—C10—C11	121.31 (13)	C24—C29—C30	107.96 (12)
C9—C10—H10A	119.3	O6—C30—N2	124.71 (13)
C11—C10—H10A	119.3	O6—C30—C29	129.13 (13)
C10—C11—C12	119.53 (14)	N2—C30—C29	106.16 (12)
C10—C11—H11A	120.2	C1S—O1S—H1SO	112.9 (17)
C12—C11—H11A	120.2	O1S—C1S—C2S	108.83 (16)
C13—C12—C11	120.16 (14)	O1S—C1S—H1SA	109.9
C13—C12—H12A	119.9	C2S—C1S—H1SA	109.9
C11—C12—H12A	119.9	O1S—C1S—H1SB	109.9
C12—C13—C14	120.01 (14)	C2S—C1S—H1SB	109.9
C12—C13—H13A	120.0	H1SA—C1S—H1SB	108.3
C14—C13—H13A	120.0	C1S—C2S—H2SA	109.5
O2—C14—C13	122.18 (13)	C1S—C2S—H2SB	109.5
O2—C14—C9	117.10 (13)	H2SA—C2S—H2SB	109.5
C13—C14—C9	120.71 (14)	C1S—C2S—H2SC	109.5
O3—C15—N1	124.43 (14)	H2SA—C2S—H2SC	109.5
O3—C15—C16	129.23 (13)	H2SB—C2S—H2SC	109.5
N1—C15—C16	106.32 (11)
C15—N1—C1—C3	116.36 (13)	O3—C15—C16—C21	175.63 (15)
C22—N1—C1—C3	−65.99 (17)	N1—C15—C16—C21	−2.64 (15)
C15—N1—C1—C2	−114.96 (13)	C21—C16—C17—C18	−0.9 (2)
C22—N1—C1—C2	62.69 (17)	C15—C16—C17—C18	177.31 (15)
C23—N2—C2—C9	−55.50 (17)	C16—C17—C18—C19	0.7 (3)
C30—N2—C2—C9	131.43 (13)	C17—C18—C19—C20	0.0 (3)
C23—N2—C2—C1	71.16 (16)	C18—C19—C20—C21	−0.5 (2)
C30—N2—C2—C1	−101.91 (14)	C17—C16—C21—C20	0.4 (2)
N1—C1—C2—N2	51.45 (13)	C15—C16—C21—C20	−178.14 (12)
C3—C1—C2—N2	178.57 (11)	C17—C16—C21—C22	−179.33 (14)
N1—C1—C2—C9	176.06 (10)	C15—C16—C21—C22	2.09 (15)
C3—C1—C2—C9	−56.82 (15)	C19—C20—C21—C16	0.3 (2)
N1—C1—C3—C4	73.68 (16)	C19—C20—C21—C22	180.00 (15)
C2—C1—C3—C4	−52.35 (18)	C15—N1—C22—O4	178.83 (13)
N1—C1—C3—C8	−105.50 (14)	C1—N1—C22—O4	1.0 (2)
C2—C1—C3—C8	128.47 (14)	C15—N1—C22—C21	−0.94 (15)
C8—C3—C4—C5	1.6 (2)	C1—N1—C22—C21	−178.78 (12)
C1—C3—C4—C5	−177.58 (13)	C16—C21—C22—O4	179.46 (14)
C3—C4—C5—C6	−1.7 (2)	C20—C21—C22—O4	−0.3 (2)
C4—C5—C6—C7	0.6 (2)	C16—C21—C22—N1	−0.78 (15)
C5—C6—C7—C8	0.6 (2)	C20—C21—C22—N1	179.48 (14)
C6—C7—C8—O1	179.03 (15)	C30—N2—C23—O5	176.69 (13)
C6—C7—C8—C3	−0.7 (2)	C2—N2—C23—O5	3.0 (2)
C4—C3—C8—O1	179.85 (13)	C30—N2—C23—C24	−1.99 (15)
C1—C3—C8—O1	−0.9 (2)	C2—N2—C23—C24	−175.74 (11)
C4—C3—C8—C7	−0.4 (2)	O5—C23—C24—C25	0.8 (2)
C1—C3—C8—C7	178.83 (14)	N2—C23—C24—C25	179.41 (14)
N2—C2—C9—C10	99.23 (15)	O5—C23—C24—C29	−177.04 (13)
C1—C2—C9—C10	−24.22 (18)	N2—C23—C24—C29	1.60 (15)
N2—C2—C9—C14	−78.18 (15)	C29—C24—C25—C26	1.1 (2)
C1—C2—C9—C14	158.37 (13)	C23—C24—C25—C26	−176.41 (14)
C14—C9—C10—C11	−0.6 (2)	C24—C25—C26—C27	−0.9 (2)
C2—C9—C10—C11	−177.99 (13)	C25—C26—C27—C28	−0.3 (2)
C9—C10—C11—C12	−0.3 (2)	C26—C27—C28—C29	1.2 (2)
C10—C11—C12—C13	0.4 (2)	C27—C28—C29—C24	−1.0 (2)
C11—C12—C13—C14	0.5 (2)	C27—C28—C29—C30	177.11 (14)
C12—C13—C14—O2	177.19 (14)	C25—C24—C29—C28	−0.2 (2)
C12—C13—C14—C9	−1.4 (2)	C23—C24—C29—C28	177.82 (13)
C10—C9—C14—O2	−177.22 (13)	C25—C24—C29—C30	−178.67 (13)
C2—C9—C14—O2	0.34 (19)	C23—C24—C29—C30	−0.63 (15)
C10—C9—C14—C13	1.5 (2)	C23—N2—C30—O6	−177.39 (13)
C2—C9—C14—C13	179.05 (13)	C2—N2—C30—O6	−3.4 (2)
C22—N1—C15—O3	−176.19 (14)	C23—N2—C30—C29	1.62 (15)
C1—N1—C15—O3	1.8 (2)	C2—N2—C30—C29	175.60 (11)
C22—N1—C15—C16	2.18 (15)	C28—C29—C30—O6	0.1 (3)
C1—N1—C15—C16	−179.80 (11)	C24—C29—C30—O6	178.40 (14)
O3—C15—C16—C17	−2.8 (3)	C28—C29—C30—N2	−178.82 (14)
N1—C15—C16—C17	178.95 (15)	C24—C29—C30—N2	−0.55 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O1W	0.86 (2)	1.89 (2)	2.7263 (13)	165 (2)
O2—H2O···O5i	0.88 (2)	1.95 (2)	2.8238 (15)	177 (2)
O1S—H1SO···O4	1.06 (4)	1.76 (4)	2.7905 (17)	161 (3)
O1W—H1W···O1Sii	1.06 (3)	1.65 (3)	2.6927 (16)	169 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O1W	0.86 (2)	1.89 (2)	2.7263 (13)	165 (2)
O2—H2O⋯O5i	0.88 (2)	1.95 (2)	2.8238 (15)	177 (2)
O1S—H1SO⋯O4	1.06 (4)	1.76 (4)	2.7905 (17)	161 (3)
O1W—H1W⋯O1S ii	1.06 (3)	1.65 (3)	2.6927 (16)	169 (3)

Symmetry codes: (i) ; (ii) .