1-(3-Phenyl-isoxazol-5-yl)cyclo-hexane-1,2-diol.

In the title compound, C(15)H(17)NO(3), there are two mol-ecules in the asymmetric unit wherein the isoxazole rings make dihedral angles of 16.16 (15) and 16.79 (13)° with the benzene rings, and the cyclo-hexane rings adopt chair conformations. In both mol-ecules, the hydroxyl groups of the diol fragments are cis oriented, the O-C-C-O torsion angles being 60.76 (12) and -55.86 (11)°. The two mol-ecules are linked by a strong O-H⋯N hydrogen bond and the crystal packing is stabilized by one O-H⋯N and two O-H⋯O hydrogen bonds. An intra-molecular O-H⋯O hydrogen bond is observed in one of the mol-ecules.

Related literature

For the uses of potassium permanganate in functional group inter­conversion inorganic chemistry, see: Singh & Lee (2001 ▶). For the use of permanganate in the preparation of natural products, see: Brown et al. (2008 ▶); Morris et al. (2009 ▶). For isoxazoles as versatile building blocks in organic synthesis, see: Melo (2005 ▶). For the synthesis, see: Hansen et al. (2005 ▶). For a related structure, see: Vallejos et al. (2009 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C15H17NO3

M = 259.3

Triclinic,

a = 9.4894 (17) Å

b = 11.5593 (15) Å

c = 14.0083 (13) Å

α = 73.02 (2)°

β = 81.62 (4)°

γ = 66.71 (5)°

V = 1349.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.21 × 0.10 × 0.09 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: none

10826 measured reflections

5863 independent reflections

4447 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.168

S = 1.14

5863 reflections

347 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020947/pv2162sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020947/pv2162Isup2.hkl

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

C15H17NO3	Z = 4
Mr = 259.3	F(000) = 552
Triclinic, P1	Dx = 1.277 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.4894 (17) Å	Cell parameters from 5863 reflections
b = 11.5593 (15) Å	θ = 1.9–27.1°
c = 14.0083 (13) Å	µ = 0.09 mm−1
α = 73.02 (2)°	T = 298 K
β = 81.62 (4)°	Block, yellow
γ = 66.71 (5)°	0.21 × 0.10 × 0.09 mm
V = 1349.0 (3) Å3

Nonius KappaCCD area-detector diffractometer	4447 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.074
graphite	θmax = 27.1°, θmin = 2.0°
φ scans, and ω scans with κ offsets	h = 0→12
10826 measured reflections	k = −13→14
5863 independent reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0709P)2 + 0.2904P] where P = (Fo2 + 2Fc2)/3
5863 reflections	(Δ/σ)max < 0.001
347 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. Melting points were recorded on an Electrothermal 9100 instrument and are uncorrected; IR spectra were obtained on a Nicolet Nexus 470-FTIR spectrometer as potassium bromide pellets and are reported in wavenumbers (cm-1). 1H and 13CNMR spectra were measured on a Bruker AM-400 spectrometer (400 MHz), using CDCl3 as solvent. TMS was used as an internal standard. Chemical shifts (d) and J values are reported in p.p.m. and Hz, respectively. Reaction progress was monitored by means of thin-layer chromatography using Merck Kieselgel 60 (230–240 mesh). All reagents were purchased from Merck, Sigma and Aldrich Chemical Co. and used without further purification. Solvents were dried and distilled prior to use.5-Cyclohex-1-enyl-3-phenylisoxazole1: mp 361 (2) K. RMN-1H (CDCl3, 400 MHz, δ): 7,82 (2H, dd, J: 8,0 and 4,0); 7,45 (1H, m); 7,45 (2H, m); 6,67 (1H, br.s); 6,39 (1H, s); 2,40 (2H, m); 2,28 (2H, m); 1,80 (2H, m); 1,70 (2H, m). RMN-13C (CDCl3, 100 MHz, δ): 171.65, 162.44, 130.22, 129.79, 129.49, 128.85, 128.85, 126.77, 126.77, 125.41, 96.18, 25.44, 25.24, 22.12, 21.74.The title compound (II): mp 418 (2) K. RMN-1H (CDCl3, 400 MHz, δ): 7,93 (2H, m); 7,59 (3H, m); 6,82 (1H, s); 4,13 (1H, dd, J = 12 and 4); 1,97 (8H, m). RMN-13C (CDCl3,100 MHz, δ): 177.83, 161.86, 129.48, 128.42, 128.35, 128.35, 126.17, 126.17, 99.13, 73.28, 71.94, 35.11, 28.96, 23.26, 19.60. FT–IR (KBr pellet, cm-1): ν 3395, 2940, 2863, 1598, 1468, 1404.

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 > 2σ(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	0.62628 (16)	0.34815 (14)	−0.02283 (11)	0.0506 (4)
O2	0.93980 (15)	0.08165 (12)	0.11711 (11)	0.0402 (4)
H2	1.0099	0.109	0.1025	0.06*
O3	0.91802 (15)	0.33990 (12)	0.08949 (10)	0.0389 (4)
H3	0.9214	0.4003	0.1072	0.058*
O4	0.26135 (18)	0.12795 (13)	−0.00370 (11)	0.0484 (4)
O5	−0.00749 (16)	0.44685 (13)	−0.11911 (10)	0.0426 (4)
H5	−0.0304	0.4079	−0.064	0.064*
O6	0.29277 (15)	0.42716 (11)	−0.16284 (10)	0.0360 (3)
H6	0.3837	0.4082	−0.1543	0.054*
N1	0.6074 (2)	0.38177 (19)	−0.12650 (14)	0.0529 (5)
N2	0.2639 (2)	0.08580 (17)	0.10155 (13)	0.0482 (5)
C1	0.7962 (2)	0.18899 (17)	0.10844 (14)	0.0323 (4)
C2	0.6772 (3)	0.1367 (2)	0.17032 (16)	0.0455 (5)
H2A	0.576	0.2048	0.1596	0.055*
H2B	0.6781	0.0648	0.1476	0.055*
C3	0.7075 (3)	0.0904 (2)	0.28125 (18)	0.0549 (6)
H3A	0.6256	0.0639	0.3177	0.066*
H3B	0.803	0.0152	0.2933	0.066*
C4	0.7175 (3)	0.1971 (3)	0.31908 (18)	0.0616 (7)
H4A	0.7444	0.1631	0.3887	0.074*
H4B	0.6182	0.2681	0.3145	0.074*
C5	0.8374 (3)	0.2482 (2)	0.25845 (16)	0.0486 (6)
H5A	0.8385	0.3189	0.2819	0.058*
H5B	0.9382	0.1791	0.268	0.058*
C6	0.8032 (2)	0.29647 (17)	0.14842 (14)	0.0334 (4)
H6A	0.7037	0.3694	0.1392	0.04*
C7	0.7557 (2)	0.24037 (17)	0.00041 (15)	0.0331 (4)
C8	0.8209 (2)	0.20197 (17)	−0.08249 (14)	0.0346 (4)
H8	0.9095	0.1303	−0.0875	0.042*
C9	0.7250 (2)	0.29443 (19)	−0.16047 (15)	0.0378 (5)
C10	0.7449 (2)	0.3044 (2)	−0.26858 (16)	0.0437 (5)
C11	0.8477 (3)	0.2006 (3)	−0.30373 (18)	0.0608 (7)
H11	0.9012	0.1227	−0.2588	0.073*
C12	0.8715 (4)	0.2119 (4)	−0.4055 (2)	0.0849 (9)
H12	0.9409	0.1421	−0.429	0.102*
C13	0.7913 (5)	0.3277 (4)	−0.4720 (2)	0.0929 (11)
H13	0.8073	0.3359	−0.5403	0.111*
C14	0.6878 (4)	0.4311 (4)	−0.4375 (2)	0.0854 (10)
H14	0.6336	0.5085	−0.4826	0.102*
C15	0.6643 (3)	0.4202 (3)	−0.3370 (2)	0.0629 (7)
H15	0.5942	0.4904	−0.3142	0.075*
C16	0.2624 (2)	0.31090 (16)	−0.14292 (14)	0.0303 (4)
C17	0.0942 (2)	0.35473 (18)	−0.17172 (14)	0.0343 (4)
H17	0.0657	0.2781	−0.1537	0.041*
C18	0.0737 (2)	0.4167 (2)	−0.28265 (15)	0.0412 (5)
H18A	0.0924	0.4972	−0.3002	0.049*
H18B	−0.0314	0.438	−0.2984	0.049*
C19	0.1827 (3)	0.3262 (2)	−0.34394 (17)	0.0520 (6)
H19A	0.1708	0.3705	−0.4144	0.062*
H19B	0.1567	0.2498	−0.3318	0.062*
C20	0.3488 (3)	0.2838 (2)	−0.31744 (16)	0.0493 (6)
H20A	0.378	0.3592	−0.336	0.059*
H20B	0.415	0.2227	−0.355	0.059*
C21	0.3705 (2)	0.22007 (19)	−0.20610 (15)	0.0407 (5)
H21A	0.4761	0.1977	−0.1908	0.049*
H21B	0.3508	0.1401	−0.1889	0.049*
C22	0.2762 (2)	0.24539 (17)	−0.03319 (14)	0.0329 (4)
C23	0.2892 (2)	0.28088 (18)	0.04736 (14)	0.0347 (4)
H23	0.301	0.3566	0.0485	0.042*
C24	0.2811 (2)	0.17773 (18)	0.13034 (15)	0.0353 (4)
C25	0.2852 (2)	0.16502 (19)	0.23812 (15)	0.0379 (5)
C26	0.2603 (3)	0.2727 (2)	0.27237 (17)	0.0526 (6)
H26	0.2419	0.3537	0.2273	0.063*
C27	0.2626 (3)	0.2598 (3)	0.37386 (18)	0.0667 (7)
H27	0.2458	0.3324	0.3965	0.08*
C28	0.2896 (3)	0.1406 (3)	0.44105 (18)	0.0661 (7)
H28	0.2912	0.1325	0.509	0.079*
C29	0.3143 (3)	0.0333 (3)	0.40761 (18)	0.0659 (7)
H29	0.3331	−0.0476	0.453	0.079*
C30	0.3113 (3)	0.0452 (2)	0.30692 (17)	0.0509 (6)
H30	0.327	−0.0277	0.285	0.061*

	U11	U22	U33	U12	U13	U23
O1	0.0387 (8)	0.0564 (9)	0.0423 (10)	0.0013 (7)	−0.0070 (7)	−0.0159 (7)
O2	0.0374 (8)	0.0297 (7)	0.0493 (9)	−0.0067 (6)	−0.0041 (7)	−0.0111 (6)
O3	0.0488 (8)	0.0377 (7)	0.0382 (8)	−0.0244 (7)	0.0061 (6)	−0.0136 (6)
O4	0.0746 (11)	0.0373 (8)	0.0361 (9)	−0.0270 (7)	−0.0048 (7)	−0.0037 (6)
O5	0.0376 (8)	0.0449 (8)	0.0347 (9)	−0.0076 (6)	0.0039 (6)	−0.0083 (6)
O6	0.0363 (7)	0.0292 (7)	0.0428 (9)	−0.0127 (6)	−0.0061 (6)	−0.0066 (6)
N1	0.0414 (11)	0.0634 (12)	0.0424 (12)	−0.0062 (9)	−0.0125 (9)	−0.0105 (9)
N2	0.0678 (13)	0.0428 (10)	0.0324 (10)	−0.0244 (9)	−0.0056 (9)	−0.0002 (8)
C1	0.0316 (10)	0.0282 (9)	0.0366 (11)	−0.0097 (8)	−0.0005 (8)	−0.0096 (8)
C2	0.0449 (12)	0.0450 (11)	0.0502 (14)	−0.0237 (10)	−0.0007 (10)	−0.0080 (10)
C3	0.0565 (14)	0.0565 (13)	0.0504 (15)	−0.0330 (12)	0.0049 (11)	0.0019 (11)
C4	0.0812 (18)	0.0710 (16)	0.0356 (14)	−0.0389 (14)	0.0104 (12)	−0.0091 (12)
C5	0.0709 (15)	0.0504 (12)	0.0323 (12)	−0.0313 (12)	−0.0010 (10)	−0.0102 (10)
C6	0.0379 (11)	0.0331 (9)	0.0303 (11)	−0.0153 (8)	0.0044 (8)	−0.0095 (8)
C7	0.0317 (10)	0.0306 (9)	0.0384 (12)	−0.0113 (8)	−0.0046 (8)	−0.0099 (8)
C8	0.0367 (11)	0.0319 (9)	0.0360 (12)	−0.0120 (8)	−0.0031 (9)	−0.0100 (8)
C9	0.0345 (11)	0.0415 (11)	0.0413 (12)	−0.0184 (9)	−0.0049 (9)	−0.0090 (9)
C10	0.0466 (12)	0.0580 (13)	0.0354 (12)	−0.0322 (11)	−0.0065 (10)	−0.0048 (10)
C11	0.0778 (18)	0.0710 (16)	0.0418 (15)	−0.0347 (14)	−0.0020 (12)	−0.0168 (12)
C12	0.116 (3)	0.112 (3)	0.0461 (18)	−0.058 (2)	0.0105 (17)	−0.0336 (18)
C13	0.138 (3)	0.140 (3)	0.0335 (17)	−0.094 (3)	−0.0026 (19)	−0.012 (2)
C14	0.111 (3)	0.106 (2)	0.0452 (18)	−0.064 (2)	−0.0234 (17)	0.0146 (17)
C15	0.0673 (17)	0.0697 (16)	0.0512 (16)	−0.0345 (14)	−0.0148 (13)	0.0040 (13)
C16	0.0343 (10)	0.0267 (9)	0.0299 (11)	−0.0122 (8)	−0.0009 (8)	−0.0060 (8)
C17	0.0353 (10)	0.0364 (10)	0.0326 (11)	−0.0153 (8)	0.0002 (8)	−0.0086 (8)
C18	0.0408 (12)	0.0500 (12)	0.0346 (12)	−0.0195 (10)	−0.0085 (9)	−0.0066 (9)
C19	0.0661 (16)	0.0640 (14)	0.0348 (13)	−0.0294 (12)	−0.0014 (11)	−0.0185 (11)
C20	0.0551 (14)	0.0544 (13)	0.0376 (13)	−0.0178 (11)	0.0100 (10)	−0.0198 (11)
C21	0.0422 (12)	0.0364 (10)	0.0413 (13)	−0.0113 (9)	0.0041 (9)	−0.0142 (9)
C22	0.0319 (10)	0.0275 (9)	0.0352 (11)	−0.0086 (8)	−0.0029 (8)	−0.0047 (8)
C23	0.0356 (11)	0.0332 (10)	0.0335 (11)	−0.0119 (8)	−0.0040 (8)	−0.0056 (8)
C24	0.0278 (10)	0.0364 (10)	0.0352 (12)	−0.0080 (8)	−0.0015 (8)	−0.0052 (8)
C25	0.0303 (10)	0.0426 (11)	0.0320 (12)	−0.0088 (9)	−0.0005 (8)	−0.0038 (9)
C26	0.0677 (16)	0.0437 (12)	0.0361 (13)	−0.0136 (11)	−0.0033 (11)	−0.0046 (10)
C27	0.095 (2)	0.0624 (15)	0.0375 (15)	−0.0225 (15)	−0.0020 (13)	−0.0152 (12)
C28	0.0800 (19)	0.0768 (18)	0.0289 (13)	−0.0212 (15)	−0.0005 (12)	−0.0077 (12)
C29	0.0844 (19)	0.0591 (15)	0.0358 (14)	−0.0216 (14)	0.0008 (13)	0.0058 (11)
C30	0.0589 (15)	0.0455 (12)	0.0404 (14)	−0.0171 (11)	−0.0002 (11)	−0.0037 (10)

O1—C7	1.355 (2)	C12—C13	1.382 (5)
O1—N1	1.408 (2)	C12—H12	0.93
O2—C1	1.426 (2)	C13—C14	1.377 (5)
O2—H2	0.82	C13—H13	0.93
O3—C6	1.432 (2)	C14—C15	1.369 (4)
O3—H3	0.82	C14—H14	0.93
O4—C22	1.356 (2)	C15—H15	0.93
O4—N2	1.412 (2)	C16—C22	1.501 (3)
O5—C17	1.431 (2)	C16—C21	1.538 (3)
O5—H5	0.82	C16—C17	1.547 (3)
O6—C16	1.425 (2)	C17—C18	1.515 (3)
O6—H6	0.82	C17—H17	0.98
N1—C9	1.314 (3)	C18—C19	1.521 (3)
N2—C24	1.314 (3)	C18—H18A	0.97
C1—C7	1.501 (3)	C18—H18B	0.97
C1—C2	1.530 (3)	C19—C20	1.522 (3)
C1—C6	1.531 (2)	C19—H19A	0.97
C2—C3	1.519 (3)	C19—H19B	0.97
C2—H2A	0.97	C20—C21	1.523 (3)
C2—H2B	0.97	C20—H20A	0.97
C3—C4	1.517 (3)	C20—H20B	0.97
C3—H3A	0.97	C21—H21A	0.97
C3—H3B	0.97	C21—H21B	0.97
C4—C5	1.524 (3)	C22—C23	1.345 (3)
C4—H4A	0.97	C23—C24	1.420 (3)
C4—H4B	0.97	C23—H23	0.93
C5—C6	1.514 (3)	C24—C25	1.478 (3)
C5—H5A	0.97	C25—C26	1.385 (3)
C5—H5B	0.97	C25—C30	1.388 (3)
C6—H6A	0.98	C26—C27	1.388 (3)
C7—C8	1.343 (3)	C26—H26	0.93
C8—C9	1.415 (3)	C27—C28	1.372 (4)
C8—H8	0.93	C27—H27	0.93
C9—C10	1.475 (3)	C28—C29	1.376 (4)
C10—C11	1.383 (3)	C28—H28	0.93
C10—C15	1.397 (3)	C29—C30	1.380 (3)
C11—C12	1.386 (4)	C29—H29	0.93
C11—H11	0.93	C30—H30	0.93
C7—O1—N1	108.43 (15)	C13—C14—H14	119.9
C1—O2—H2	109.5	C14—C15—C10	120.4 (3)
C6—O3—H3	109.5	C14—C15—H15	119.8
C22—O4—N2	108.55 (14)	C10—C15—H15	119.8
C17—O5—H5	109.5	O6—C16—C22	109.15 (14)
C16—O6—H6	109.5	O6—C16—C21	110.93 (15)
C9—N1—O1	105.42 (17)	C22—C16—C21	111.75 (15)
C24—N2—O4	105.51 (15)	O6—C16—C17	106.02 (14)
O2—C1—C7	108.33 (15)	C22—C16—C17	109.02 (15)
O2—C1—C2	107.01 (15)	C21—C16—C17	109.80 (15)
C7—C1—C2	110.19 (16)	O5—C17—C18	108.31 (16)
O2—C1—C6	111.29 (15)	O5—C17—C16	110.79 (15)
C7—C1—C6	110.53 (15)	C18—C17—C16	111.75 (16)
C2—C1—C6	109.43 (16)	O5—C17—H17	108.6
C3—C2—C1	112.45 (17)	C18—C17—H17	108.6
C3—C2—H2A	109.1	C16—C17—H17	108.6
C1—C2—H2A	109.1	C17—C18—C19	111.44 (18)
C3—C2—H2B	109.1	C17—C18—H18A	109.3
C1—C2—H2B	109.1	C19—C18—H18A	109.3
H2A—C2—H2B	107.8	C17—C18—H18B	109.3
C4—C3—C2	111.14 (18)	C19—C18—H18B	109.3
C4—C3—H3A	109.4	H18A—C18—H18B	108
C2—C3—H3A	109.4	C18—C19—C20	111.25 (17)
C4—C3—H3B	109.4	C18—C19—H19A	109.4
C2—C3—H3B	109.4	C20—C19—H19A	109.4
H3A—C3—H3B	108	C18—C19—H19B	109.4
C3—C4—C5	110.92 (19)	C20—C19—H19B	109.4
C3—C4—H4A	109.5	H19A—C19—H19B	108
C5—C4—H4A	109.5	C19—C20—C21	111.04 (18)
C3—C4—H4B	109.5	C19—C20—H20A	109.4
C5—C4—H4B	109.5	C21—C20—H20A	109.4
H4A—C4—H4B	108	C19—C20—H20B	109.4
C6—C5—C4	110.94 (19)	C21—C20—H20B	109.4
C6—C5—H5A	109.5	H20A—C20—H20B	108
C4—C5—H5A	109.5	C20—C21—C16	111.55 (16)
C6—C5—H5B	109.5	C20—C21—H21A	109.3
C4—C5—H5B	109.5	C16—C21—H21A	109.3
H5A—C5—H5B	108	C20—C21—H21B	109.3
O3—C6—C5	111.89 (16)	C16—C21—H21B	109.3
O3—C6—C1	107.13 (14)	H21A—C21—H21B	108
C5—C6—C1	111.39 (15)	C23—C22—O4	109.57 (17)
O3—C6—H6A	108.8	C23—C22—C16	134.23 (16)
C5—C6—H6A	108.8	O4—C22—C16	115.99 (15)
C1—C6—H6A	108.8	C22—C23—C24	105.08 (16)
C8—C7—O1	109.78 (17)	C22—C23—H23	127.5
C8—C7—C1	133.69 (17)	C24—C23—H23	127.5
O1—C7—C1	116.53 (16)	N2—C24—C23	111.28 (17)
C7—C8—C9	104.88 (17)	N2—C24—C25	119.46 (17)
C7—C8—H8	127.6	C23—C24—C25	129.24 (17)
C9—C8—H8	127.6	C26—C25—C30	118.9 (2)
N1—C9—C8	111.47 (19)	C26—C25—C24	120.66 (18)
N1—C9—C10	119.76 (19)	C30—C25—C24	120.47 (18)
C8—C9—C10	128.74 (19)	C25—C26—C27	120.1 (2)
C11—C10—C15	119.1 (2)	C25—C26—H26	119.9
C11—C10—C9	120.4 (2)	C27—C26—H26	119.9
C15—C10—C9	120.5 (2)	C28—C27—C26	120.4 (2)
C10—C11—C12	120.4 (3)	C28—C27—H27	119.8
C10—C11—H11	119.8	C26—C27—H27	119.8
C12—C11—H11	119.8	C27—C28—C29	119.8 (2)
C13—C12—C11	119.6 (3)	C27—C28—H28	120.1
C13—C12—H12	120.2	C29—C28—H28	120.1
C11—C12—H12	120.2	C28—C29—C30	120.2 (2)
C14—C13—C12	120.4 (3)	C28—C29—H29	119.9
C14—C13—H13	119.8	C30—C29—H29	119.9
C12—C13—H13	119.8	C29—C30—C25	120.6 (2)
C15—C14—C13	120.2 (3)	C29—C30—H30	119.7
C15—C14—H14	119.9	C25—C30—H30	119.7
C7—O1—N1—C9	−0.3 (2)	C9—C10—C15—C14	177.2 (2)
C22—O4—N2—C24	−0.5 (2)	O6—C16—C17—O5	−55.87 (18)
O2—C1—C2—C3	65.7 (2)	C22—C16—C17—O5	61.51 (18)
C7—C1—C2—C3	−176.76 (16)	C21—C16—C17—O5	−175.77 (14)
C6—C1—C2—C3	−55.0 (2)	O6—C16—C17—C18	65.02 (18)
C1—C2—C3—C4	55.1 (3)	C22—C16—C17—C18	−177.60 (14)
C2—C3—C4—C5	−55.0 (3)	C21—C16—C17—C18	−54.87 (19)
C3—C4—C5—C6	56.5 (3)	O5—C17—C18—C19	177.89 (16)
C4—C5—C6—O3	−177.55 (17)	C16—C17—C18—C19	55.6 (2)
C4—C5—C6—C1	−57.7 (2)	C17—C18—C19—C20	−55.8 (2)
O2—C1—C6—O3	60.75 (19)	C18—C19—C20—C21	56.1 (2)
C7—C1—C6—O3	−59.67 (19)	C19—C20—C21—C16	−56.4 (2)
C2—C1—C6—O3	178.80 (16)	O6—C16—C21—C20	−61.6 (2)
O2—C1—C6—C5	−61.9 (2)	C22—C16—C21—C20	176.34 (15)
C7—C1—C6—C5	177.67 (16)	C17—C16—C21—C20	55.2 (2)
C2—C1—C6—C5	56.1 (2)	N2—O4—C22—C23	0.4 (2)
N1—O1—C7—C8	−0.5 (2)	N2—O4—C22—C16	−174.98 (15)
N1—O1—C7—C1	179.87 (14)	O6—C16—C22—C23	10.7 (3)
O2—C1—C7—C8	4.2 (3)	C21—C16—C22—C23	133.8 (2)
C2—C1—C7—C8	−112.5 (2)	C17—C16—C22—C23	−104.7 (2)
C6—C1—C7—C8	126.4 (2)	O6—C16—C22—O4	−175.34 (15)
O2—C1—C7—O1	−176.22 (14)	C21—C16—C22—O4	−52.3 (2)
C2—C1—C7—O1	67.0 (2)	C17—C16—C22—O4	69.3 (2)
C6—C1—C7—O1	−54.0 (2)	O4—C22—C23—C24	−0.2 (2)
O1—C7—C8—C9	1.01 (19)	C16—C22—C23—C24	174.04 (19)
C1—C7—C8—C9	−179.40 (18)	O4—N2—C24—C23	0.4 (2)
O1—N1—C9—C8	1.0 (2)	O4—N2—C24—C25	178.74 (16)
O1—N1—C9—C10	−177.26 (15)	C22—C23—C24—N2	−0.1 (2)
C7—C8—C9—N1	−1.3 (2)	C22—C23—C24—C25	−178.28 (18)
C7—C8—C9—C10	176.78 (17)	N2—C24—C25—C26	−161.9 (2)
N1—C9—C10—C11	−166.5 (2)	C23—C24—C25—C26	16.1 (3)
C8—C9—C10—C11	15.6 (3)	N2—C24—C25—C30	16.9 (3)
N1—C9—C10—C15	15.8 (3)	C23—C24—C25—C30	−165.0 (2)
C8—C9—C10—C15	−162.2 (2)	C30—C25—C26—C27	0.4 (3)
C15—C10—C11—C12	0.7 (3)	C24—C25—C26—C27	179.3 (2)
C9—C10—C11—C12	−177.1 (2)	C25—C26—C27—C28	0.0 (4)
C10—C11—C12—C13	−0.2 (4)	C26—C27—C28—C29	−0.1 (4)
C11—C12—C13—C14	−0.4 (5)	C27—C28—C29—C30	−0.3 (4)
C12—C13—C14—C15	0.5 (5)	C28—C29—C30—C25	0.7 (4)
C13—C14—C15—C10	0.0 (4)	C26—C25—C30—C29	−0.8 (3)
C11—C10—C15—C14	−0.5 (3)	C24—C25—C30—C29	−179.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	2.42	2.822 (2)	111
O6—H6···N1	0.82	2.10	2.915 (3)	173
O2—H2···N2i	0.82	2.32	3.070 (3)	153
O3—H3···O5ii	0.82	2.27	3.054 (2)	159
O5—H5···O3iii	0.82	2.12	2.923 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82	2.42	2.822 (2)	111
O2—H2⋯N2i	0.82	2.32	3.070 (3)	153
O3—H3⋯O5ii	0.82	2.27	3.054 (2)	159
O5—H5⋯O3iii	0.82	2.12	2.923 (3)	167
O6—H6⋯N1	0.82	2.10	2.915 (3)	173

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