Crystal structure of natural phaeosphaeride A.

The asymmetric unit of the title compound, C15H23NO5, contains two independent mol-ecules. Phaeosphaeride A contains two primary sections, an alkyl chain consisting of five C atoms and a cyclic system consisting of fused five- and six-membered rings with attached substituents. In the crystal, the mol-ecules form layered structures. Nearly planar sheets, parallel to the (001) plane, form bilayers of two-dimensional hydrogen-bonded networks with the hy-droxy groups located on the inter-ior of the bilayer sheets. The network is constructed primarily of four O-H⋯O hydrogen bonds, which form a zigzag pattern in the (001) plane. The butyl chains inter-digitate with the butyl chains on adjacent sheets. The crystal was twinned by a twofold rotation about the c axis, with refined major-minor occupancy fractions of 0.718 (6):0.282 (6).

Related literature

For details of the extraction of natural phaeosphaeride A and a discussion of its biological activities, see: Maloney et al. (2006 ▸). For details of trials of the synthesis of natural phaeosphaeride A, see: Kobayashi et al. (2011 ▸); Chatzimpaloglou et al. (2012 ▸, 2014 ▸); Kobayashi et al. (2015 ▸). Ring-puckering parameters are as defined by Cremer & Pople (1975 ▸). Hydrogen bonding is described in detail by Desiraju & Steiner (1999 ▸) and by Arunan et al. (2011 ▸). The twin law was identified using TwinRotMat in PLATON (Spek, 2009 ▸). Criteria for absolute configuration determination are described by Flack (1983 ▸) and Parsons et al. (2013 ▸).

Experimental

Crystal data

C15H23NO5

M = 297.34

Monoclinic,

a = 10.14078 (18) Å

b = 9.10361 (14) Å

c = 17.5991 (3) Å

β = 100.1847 (16)°

V = 1599.11 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.77 mm−1

T = 100 K

0.35 × 0.35 × 0.05 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▸) T min = 0.824, T max = 1.000

6054 measured reflections

6054 independent reflections

5940 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.150

S = 1.10

6054 reflections

389 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack x determined using 2632 quotients [(I +) − (I −)]/[(I +) + (I −)] (Parsons et al., 2013 ▸)

Absolute structure parameter: 0.05 (8)

Data collection: CrysAlis PRO (Agilent, 2012 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S205698901501395X/pk2560sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901501395X/pk2560Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901501395X/pk2560Isup3.cml

Click here for additional data file.

et al. . DOI: 10.1107/S205698901501395X/pk2560fig1.tif

A view of mol­ecules I (left) and II (right) of phaeosphaeride A. The atom numbering scheme is that of Maloney et al. (2006). Displacement ellipsoids are shown at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S205698901501395X/pk2560fig2.tif

Projection of the layered crystal structure of phaeosphaeride A on the (100) plane. The dashed lines indicate the short contacts between mol­ecules of phaeosphaeride A (only hydrogen atoms forming hydrogen bonds are shown).

CCDC reference: 1412515

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

C15H23NO5	F(000) = 640
Mr = 297.34	Dx = 1.235 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 10.14078 (18) Å	Cell parameters from 14376 reflections
b = 9.10361 (14) Å	θ = 4.4–75.9°
c = 17.5991 (3) Å	µ = 0.77 mm−1
β = 100.1847 (16)°	T = 100 K
V = 1599.11 (5) Å3	Tabular, colourless
Z = 4	0.35 × 0.35 × 0.05 mm

Agilent SuperNova Dual Source diffractometer with an Atlas detector	6054 measured reflections
Radiation source: SuperNova (Cu) X-ray Source	6054 independent reflections
Mirror monochromator	5940 reflections with I > 2σ(I)
Detector resolution: 10.3829 pixels mm-1	θmax = 70.0°, θmin = 4.4°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −11→11
Tmin = 0.824, Tmax = 1.000	l = −4→21

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.058	w = 1/[σ2(Fo2) + (0.0289P)2 + 2.9758P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.150	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.36 e Å−3
6054 reflections	Δρmin = −0.30 e Å−3
389 parameters	Absolute structure: Flack x determined using 2632 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.05 (8)

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. Refined as a 2-component twin.

	x	y	z	Uiso*/Ueq
C1	1.1431 (5)	0.8972 (6)	0.9253 (3)	0.0153 (10)
N2	1.1842 (4)	0.7850 (5)	0.8817 (2)	0.0163 (9)
C3	1.1862 (5)	0.8314 (6)	0.8053 (3)	0.0149 (10)
C4	1.1266 (5)	0.9782 (6)	0.8025 (3)	0.0143 (10)
C5	1.0975 (5)	1.0166 (5)	0.8717 (3)	0.0135 (9)
C6	1.0311 (5)	1.1589 (6)	0.8845 (3)	0.0159 (10)
H6	1.0984	1.2269	0.9115	0.019*
C7	0.9703 (5)	1.2250 (6)	0.8039 (3)	0.0167 (10)
C8	1.0752 (5)	1.2122 (5)	0.7508 (3)	0.0144 (10)
H8	1.1580	1.2596	0.7765	0.017*
C9	1.0343 (5)	1.2809 (6)	0.6718 (3)	0.0194 (11)
H9A	1.0006	1.3791	0.6779	0.023*
H9B	0.9620	1.2237	0.6426	0.023*
C10	1.1482 (5)	1.2899 (7)	0.6264 (3)	0.0231 (11)
H10A	1.1855	1.1924	0.6231	0.028*
H10B	1.2183	1.3519	0.6543	0.028*
C11	1.1059 (7)	1.3504 (8)	0.5454 (4)	0.0349 (15)
H11A	1.0380	1.2864	0.5171	0.042*
H11B	1.0657	1.4463	0.5487	0.042*
C12	1.2195 (8)	1.3646 (9)	0.5007 (4)	0.0433 (19)
H12A	1.2627	1.2697	0.4998	0.052*
H12B	1.2852	1.4326	0.5278	0.052*
C13	1.1771 (12)	1.4175 (13)	0.4187 (5)	0.080 (4)
H13A	1.1119	1.3511	0.3913	0.120*
H13B	1.2538	1.4211	0.3936	0.120*
H13C	1.1387	1.5138	0.4189	0.120*
C14	1.2311 (5)	0.7567 (6)	0.7508 (3)	0.0213 (11)
H14A	1.2660	0.6629	0.7611	0.026*
H14B	1.2277	0.7979	0.7021	0.026*
C15	0.8381 (5)	1.1508 (6)	0.7705 (3)	0.0193 (10)
H15A	0.8540	1.0495	0.7600	0.029*
H15B	0.7986	1.1992	0.7235	0.029*
H15C	0.7782	1.1570	0.8070	0.029*
C16	1.2068 (6)	0.5407 (6)	0.9208 (3)	0.0203 (11)
H16A	1.1648	0.5103	0.8701	0.031*
H16B	1.1400	0.5521	0.9528	0.031*
H16C	1.2706	0.4678	0.9429	0.031*
O1	1.1050 (4)	1.0568 (4)	0.73717 (19)	0.0172 (7)
O2	0.9541 (4)	1.3789 (4)	0.8112 (2)	0.0183 (8)
H2	0.8942	1.3951	0.8359	0.027*
O3	0.9324 (4)	1.1327 (4)	0.9312 (2)	0.0213 (8)
H3	0.9060	1.2114	0.9456	0.032*
O4	1.1447 (4)	0.8881 (4)	0.99543 (19)	0.0183 (8)
O5	1.2747 (4)	0.6794 (4)	0.9159 (2)	0.0194 (8)
C1A	0.4815 (5)	1.9716 (6)	0.8996 (3)	0.0156 (10)
N2A	0.4361 (4)	2.0638 (5)	0.8379 (2)	0.0174 (9)
C3A	0.4890 (5)	2.0271 (6)	0.7717 (3)	0.0159 (10)
C4A	0.5564 (5)	1.8865 (6)	0.7938 (3)	0.0136 (9)
C5A	0.5529 (5)	1.8520 (5)	0.8678 (3)	0.0147 (10)
C6A	0.6116 (5)	1.7116 (5)	0.9032 (3)	0.0140 (10)
H6A	0.5393	1.6398	0.9020	0.017*
C7A	0.7097 (5)	1.6545 (5)	0.8525 (3)	0.0126 (9)
C8A	0.6355 (5)	1.6563 (5)	0.7676 (3)	0.0140 (10)
H8A	0.5498	1.6055	0.7656	0.017*
C9A	0.7086 (5)	1.5840 (6)	0.7096 (3)	0.0191 (11)
H9AA	0.7419	1.4891	0.7296	0.023*
H9AB	0.7853	1.6439	0.7038	0.023*
C10A	0.6212 (6)	1.5621 (7)	0.6302 (3)	0.0223 (11)
H10C	0.5384	1.5139	0.6364	0.027*
H10D	0.5986	1.6572	0.6066	0.027*
C11A	0.6921 (6)	1.4697 (7)	0.5771 (3)	0.0270 (13)
H11C	0.7732	1.5202	0.5699	0.032*
H11D	0.7183	1.3768	0.6023	0.032*
C12A	0.6074 (6)	1.4392 (8)	0.4983 (3)	0.0295 (14)
H12C	0.5805	1.5318	0.4730	0.035*
H12D	0.5269	1.3871	0.5051	0.035*
C13A	0.6823 (7)	1.3483 (8)	0.4466 (3)	0.0344 (15)
H13D	0.6244	1.3297	0.3982	0.052*
H13E	0.7096	1.2566	0.4715	0.052*
H13F	0.7599	1.4013	0.4377	0.052*
C14A	0.4806 (5)	2.1038 (6)	0.7075 (3)	0.0210 (11)
H14C	0.4356	2.1932	0.7026	0.025*
H14D	0.5198	2.0685	0.6671	0.025*
C15A	0.8399 (5)	1.7422 (6)	0.8646 (3)	0.0160 (10)
H15D	0.8201	1.8444	0.8550	0.024*
H15E	0.8958	1.7077	0.8296	0.024*
H15F	0.8858	1.7298	0.9168	0.024*
C16A	0.5035 (6)	2.3002 (6)	0.8752 (4)	0.0273 (12)
H16D	0.5616	2.2998	0.8376	0.041*
H16E	0.5520	2.2663	0.9238	0.041*
H16F	0.4719	2.3983	0.8809	0.041*
O1A	0.6069 (4)	1.8064 (4)	0.74144 (18)	0.0166 (7)
O2A	0.7369 (3)	1.5024 (4)	0.86892 (19)	0.0145 (7)
H2A	0.7410	1.4877	0.9152	0.022*
O3A	0.6775 (3)	1.7297 (4)	0.98091 (18)	0.0145 (7)
H3A	0.6363	1.6850	1.0097	0.022*
O4A	0.4586 (4)	1.9909 (4)	0.9650 (2)	0.0179 (7)
O5A	0.3911 (4)	2.2045 (4)	0.8499 (2)	0.0186 (8)

	U11	U22	U33	U12	U13	U23
C1	0.015 (2)	0.013 (2)	0.017 (2)	−0.004 (2)	−0.0009 (19)	−0.0023 (19)
N2	0.016 (2)	0.013 (2)	0.018 (2)	0.0036 (17)	−0.0009 (16)	0.0025 (17)
C3	0.011 (2)	0.018 (2)	0.016 (2)	−0.0028 (19)	0.0039 (18)	0.0019 (19)
C4	0.014 (2)	0.016 (2)	0.015 (2)	−0.0008 (19)	0.0064 (18)	−0.0002 (19)
C5	0.010 (2)	0.014 (2)	0.017 (2)	−0.0018 (19)	0.0024 (17)	−0.0027 (19)
C6	0.017 (2)	0.017 (2)	0.014 (2)	0.001 (2)	0.0063 (19)	−0.0035 (19)
C7	0.017 (2)	0.012 (2)	0.022 (3)	0.001 (2)	0.006 (2)	−0.0002 (19)
C8	0.013 (2)	0.012 (2)	0.017 (2)	0.0003 (18)	−0.0002 (18)	0.0007 (19)
C9	0.018 (2)	0.021 (3)	0.018 (2)	0.005 (2)	0.0005 (19)	0.006 (2)
C10	0.022 (3)	0.027 (3)	0.020 (3)	0.009 (2)	0.003 (2)	0.008 (2)
C11	0.037 (4)	0.041 (4)	0.027 (3)	0.016 (3)	0.009 (3)	0.017 (3)
C12	0.055 (5)	0.047 (4)	0.035 (3)	0.015 (4)	0.027 (3)	0.021 (3)
C13	0.113 (9)	0.095 (8)	0.046 (5)	0.054 (7)	0.049 (5)	0.046 (5)
C14	0.021 (3)	0.022 (3)	0.022 (3)	0.005 (2)	0.009 (2)	−0.002 (2)
C15	0.016 (2)	0.020 (3)	0.021 (2)	0.000 (2)	0.003 (2)	0.000 (2)
C16	0.024 (3)	0.012 (2)	0.026 (3)	0.000 (2)	0.007 (2)	0.000 (2)
O1	0.0200 (18)	0.0170 (18)	0.0144 (16)	0.0042 (15)	0.0022 (13)	−0.0008 (14)
O2	0.0174 (18)	0.0135 (17)	0.0253 (19)	0.0032 (14)	0.0075 (15)	0.0004 (14)
O3	0.030 (2)	0.0158 (18)	0.0222 (18)	0.0035 (16)	0.0158 (16)	−0.0017 (15)
O4	0.0252 (19)	0.0170 (17)	0.0123 (16)	−0.0038 (15)	0.0022 (14)	0.0014 (14)
O5	0.0177 (18)	0.0127 (18)	0.0263 (19)	0.0023 (14)	−0.0006 (15)	0.0034 (14)
C1A	0.013 (2)	0.013 (2)	0.021 (2)	−0.0010 (19)	0.0022 (19)	−0.0025 (19)
N2A	0.021 (2)	0.011 (2)	0.020 (2)	0.0053 (18)	0.0049 (17)	−0.0022 (17)
C3A	0.010 (2)	0.016 (2)	0.023 (2)	−0.0024 (19)	0.0038 (18)	−0.005 (2)
C4A	0.010 (2)	0.014 (2)	0.017 (2)	−0.0044 (19)	0.0032 (18)	−0.0027 (19)
C5A	0.013 (2)	0.014 (2)	0.019 (2)	−0.0059 (19)	0.0059 (19)	−0.0034 (19)
C6A	0.016 (2)	0.014 (2)	0.012 (2)	−0.0061 (19)	0.0038 (18)	−0.0016 (18)
C7A	0.012 (2)	0.011 (2)	0.015 (2)	0.0008 (19)	0.0008 (18)	0.0019 (18)
C8A	0.014 (2)	0.014 (2)	0.013 (2)	0.0007 (19)	−0.0007 (18)	0.0015 (18)
C9A	0.018 (3)	0.024 (3)	0.015 (2)	0.006 (2)	0.002 (2)	0.000 (2)
C10A	0.023 (3)	0.028 (3)	0.016 (2)	0.006 (2)	0.004 (2)	−0.005 (2)
C11A	0.031 (3)	0.032 (3)	0.018 (3)	0.010 (3)	0.003 (2)	−0.004 (2)
C12A	0.029 (3)	0.041 (4)	0.019 (3)	0.006 (3)	0.003 (2)	−0.008 (2)
C13A	0.040 (4)	0.043 (4)	0.020 (3)	0.003 (3)	0.005 (3)	−0.010 (3)
C14A	0.021 (3)	0.021 (3)	0.021 (3)	0.005 (2)	0.005 (2)	0.003 (2)
C15A	0.017 (2)	0.018 (2)	0.014 (2)	−0.002 (2)	0.0056 (18)	0.0015 (19)
C16A	0.029 (3)	0.017 (3)	0.036 (3)	−0.011 (2)	0.006 (2)	−0.008 (2)
O1A	0.0188 (17)	0.0195 (18)	0.0120 (15)	0.0060 (15)	0.0039 (13)	0.0011 (14)
O2A	0.0181 (17)	0.0128 (17)	0.0122 (15)	0.0024 (14)	0.0016 (13)	0.0016 (13)
O3A	0.0175 (17)	0.0154 (17)	0.0104 (15)	−0.0013 (14)	0.0022 (13)	0.0008 (13)
O4A	0.0234 (19)	0.0152 (18)	0.0175 (17)	0.0020 (15)	0.0105 (14)	−0.0016 (14)
O5A	0.0157 (18)	0.0102 (17)	0.0301 (19)	0.0022 (14)	0.0044 (15)	−0.0040 (15)

C1—N2	1.385 (7)	C1A—N2A	1.386 (7)
C1—C5	1.460 (7)	C1A—C5A	1.472 (7)
C1—O4	1.234 (6)	C1A—O4A	1.226 (6)
N2—C3	1.412 (6)	N2A—C3A	1.406 (7)
N2—O5	1.391 (5)	N2A—O5A	1.389 (5)
C3—C4	1.463 (7)	C3A—C4A	1.471 (7)
C3—C14	1.320 (7)	C3A—C14A	1.318 (7)
C4—C5	1.349 (7)	C4A—C5A	1.347 (7)
C4—O1	1.339 (6)	C4A—O1A	1.345 (6)
C5—C6	1.495 (7)	C5A—C6A	1.498 (7)
C6—H6	0.9800	C6A—H6A	0.9800
C6—C7	1.563 (7)	C6A—C7A	1.540 (7)
C6—O3	1.423 (6)	C6A—O3A	1.422 (6)
C7—C8	1.540 (7)	C7A—C8A	1.549 (6)
C7—C15	1.523 (7)	C7A—C15A	1.526 (7)
C7—O2	1.419 (6)	C7A—O2A	1.431 (6)
C8—H8	0.9800	C8A—H8A	0.9800
C8—C9	1.514 (7)	C8A—C9A	1.515 (7)
C8—O1	1.475 (6)	C8A—O1A	1.455 (6)
C9—H9A	0.9700	C9A—H9AA	0.9700
C9—H9B	0.9700	C9A—H9AB	0.9700
C9—C10	1.518 (7)	C9A—C10A	1.529 (7)
C10—H10A	0.9700	C10A—H10C	0.9700
C10—H10B	0.9700	C10A—H10D	0.9700
C10—C11	1.519 (7)	C10A—C11A	1.528 (7)
C11—H11A	0.9700	C11A—H11C	0.9700
C11—H11B	0.9700	C11A—H11D	0.9700
C11—C12	1.510 (9)	C11A—C12A	1.523 (8)
C12—H12A	0.9700	C12A—H12C	0.9700
C12—H12B	0.9700	C12A—H12D	0.9700
C12—C13	1.511 (10)	C12A—C13A	1.527 (8)
C13—H13A	0.9600	C13A—H13D	0.9600
C13—H13B	0.9600	C13A—H13E	0.9600
C13—H13C	0.9600	C13A—H13F	0.9600
C14—H14A	0.9300	C14A—H14C	0.9300
C14—H14B	0.9300	C14A—H14D	0.9300
C15—H15A	0.9600	C15A—H15D	0.9600
C15—H15B	0.9600	C15A—H15E	0.9600
C15—H15C	0.9600	C15A—H15F	0.9600
C16—H16A	0.9600	C16A—H16D	0.9600
C16—H16B	0.9600	C16A—H16E	0.9600
C16—H16C	0.9600	C16A—H16F	0.9600
C16—O5	1.448 (6)	C16A—O5A	1.442 (6)
O2—H2	0.8200	O2A—H2A	0.8200
O3—H3	0.8200	O3A—H3A	0.8200
N2—C1—C5	106.4 (4)	N2A—C1A—C5A	105.5 (4)
O4—C1—N2	123.6 (5)	O4A—C1A—N2A	123.9 (5)
O4—C1—C5	129.9 (5)	O4A—C1A—C5A	130.6 (5)
C1—N2—C3	111.3 (4)	C1A—N2A—C3A	112.5 (4)
C1—N2—O5	120.6 (4)	C1A—N2A—O5A	120.8 (4)
O5—N2—C3	120.0 (4)	O5A—N2A—C3A	122.0 (4)
N2—C3—C4	103.3 (4)	N2A—C3A—C4A	102.4 (4)
C14—C3—N2	127.0 (5)	C14A—C3A—N2A	127.4 (5)
C14—C3—C4	129.7 (5)	C14A—C3A—C4A	130.1 (5)
C5—C4—C3	111.2 (4)	C5A—C4A—C3A	111.6 (4)
O1—C4—C3	121.4 (4)	O1A—C4A—C3A	120.4 (4)
O1—C4—C5	127.4 (5)	O1A—C4A—C5A	127.9 (5)
C1—C5—C6	130.4 (4)	C1A—C5A—C6A	131.2 (4)
C4—C5—C1	107.1 (4)	C4A—C5A—C1A	107.1 (4)
C4—C5—C6	122.5 (5)	C4A—C5A—C6A	121.6 (4)
C5—C6—H6	109.0	C5A—C6A—H6A	108.7
C5—C6—C7	108.3 (4)	C5A—C6A—C7A	107.3 (4)
C7—C6—H6	109.0	C7A—C6A—H6A	108.7
O3—C6—C5	108.9 (4)	O3A—C6A—C5A	112.7 (4)
O3—C6—H6	109.0	O3A—C6A—H6A	108.7
O3—C6—C7	112.6 (4)	O3A—C6A—C7A	110.8 (4)
C8—C7—C6	108.5 (4)	C6A—C7A—C8A	107.6 (4)
C15—C7—C6	111.0 (4)	C15A—C7A—C6A	112.0 (4)
C15—C7—C8	112.8 (4)	C15A—C7A—C8A	113.0 (4)
O2—C7—C6	109.4 (4)	O2A—C7A—C6A	109.3 (4)
O2—C7—C8	103.5 (4)	O2A—C7A—C8A	104.4 (4)
O2—C7—C15	111.4 (4)	O2A—C7A—C15A	110.3 (4)
C7—C8—H8	108.3	C7A—C8A—H8A	107.8
C9—C8—C7	114.8 (4)	C9A—C8A—C7A	115.7 (4)
C9—C8—H8	108.3	C9A—C8A—H8A	107.8
O1—C8—C7	110.8 (4)	O1A—C8A—C7A	110.5 (4)
O1—C8—H8	108.3	O1A—C8A—H8A	107.8
O1—C8—C9	106.1 (4)	O1A—C8A—C9A	106.8 (4)
C8—C9—H9A	108.9	C8A—C9A—H9AA	108.9
C8—C9—H9B	108.9	C8A—C9A—H9AB	108.9
C8—C9—C10	113.3 (4)	C8A—C9A—C10A	113.5 (4)
H9A—C9—H9B	107.7	H9AA—C9A—H9AB	107.7
C10—C9—H9A	108.9	C10A—C9A—H9AA	108.9
C10—C9—H9B	108.9	C10A—C9A—H9AB	108.9
C9—C10—H10A	108.9	C9A—C10A—H10C	109.3
C9—C10—H10B	108.9	C9A—C10A—H10D	109.3
C9—C10—C11	113.5 (4)	H10C—C10A—H10D	107.9
H10A—C10—H10B	107.7	C11A—C10A—C9A	111.7 (5)
C11—C10—H10A	108.9	C11A—C10A—H10C	109.3
C11—C10—H10B	108.9	C11A—C10A—H10D	109.3
C10—C11—H11A	108.8	C10A—C11A—H11C	108.7
C10—C11—H11B	108.8	C10A—C11A—H11D	108.7
H11A—C11—H11B	107.7	H11C—C11A—H11D	107.6
C12—C11—C10	113.9 (5)	C12A—C11A—C10A	114.0 (5)
C12—C11—H11A	108.8	C12A—C11A—H11C	108.7
C12—C11—H11B	108.8	C12A—C11A—H11D	108.7
C11—C12—H12A	108.7	C11A—C12A—H12C	109.1
C11—C12—H12B	108.7	C11A—C12A—H12D	109.1
C11—C12—C13	114.2 (7)	C11A—C12A—C13A	112.4 (5)
H12A—C12—H12B	107.6	H12C—C12A—H12D	107.8
C13—C12—H12A	108.7	C13A—C12A—H12C	109.1
C13—C12—H12B	108.7	C13A—C12A—H12D	109.1
C12—C13—H13A	109.5	C12A—C13A—H13D	109.5
C12—C13—H13B	109.5	C12A—C13A—H13E	109.5
C12—C13—H13C	109.5	C12A—C13A—H13F	109.5
H13A—C13—H13B	109.5	H13D—C13A—H13E	109.5
H13A—C13—H13C	109.5	H13D—C13A—H13F	109.5
H13B—C13—H13C	109.5	H13E—C13A—H13F	109.5
C3—C14—H14A	120.0	C3A—C14A—H14C	120.0
C3—C14—H14B	120.0	C3A—C14A—H14D	120.0
H14A—C14—H14B	120.0	H14C—C14A—H14D	120.0
C7—C15—H15A	109.5	C7A—C15A—H15D	109.5
C7—C15—H15B	109.5	C7A—C15A—H15E	109.5
C7—C15—H15C	109.5	C7A—C15A—H15F	109.5
H15A—C15—H15B	109.5	H15D—C15A—H15E	109.5
H15A—C15—H15C	109.5	H15D—C15A—H15F	109.5
H15B—C15—H15C	109.5	H15E—C15A—H15F	109.5
H16A—C16—H16B	109.5	H16D—C16A—H16E	109.5
H16A—C16—H16C	109.5	H16D—C16A—H16F	109.5
H16B—C16—H16C	109.5	H16E—C16A—H16F	109.5
O5—C16—H16A	109.5	O5A—C16A—H16D	109.5
O5—C16—H16B	109.5	O5A—C16A—H16E	109.5
O5—C16—H16C	109.5	O5A—C16A—H16F	109.5
C4—O1—C8	112.3 (4)	C4A—O1A—C8A	111.8 (4)
C7—O2—H2	109.5	C7A—O2A—H2A	109.5
C6—O3—H3	109.5	C6A—O3A—H3A	109.5
N2—O5—C16	110.1 (4)	N2A—O5A—C16A	109.9 (4)
C1—N2—C3—C4	−6.7 (5)	C1A—N2A—C3A—C4A	8.7 (5)
C1—N2—C3—C14	173.8 (5)	C1A—N2A—C3A—C14A	−170.0 (5)
C1—N2—O5—C16	107.4 (5)	C1A—N2A—O5A—C16A	76.8 (6)
C1—C5—C6—C7	−165.0 (5)	C1A—C5A—C6A—C7A	−162.9 (5)
C1—C5—C6—O3	−42.4 (7)	C1A—C5A—C6A—O3A	−40.7 (7)
N2—C1—C5—C4	−6.6 (5)	N2A—C1A—C5A—C4A	5.5 (5)
N2—C1—C5—C6	173.7 (5)	N2A—C1A—C5A—C6A	−172.8 (5)
N2—C3—C4—C5	2.4 (5)	N2A—C3A—C4A—C5A	−5.0 (5)
N2—C3—C4—O1	−176.8 (4)	N2A—C3A—C4A—O1A	172.2 (4)
C3—N2—O5—C16	−106.7 (5)	C3A—N2A—O5A—C16A	−77.1 (6)
C3—C4—C5—C1	2.5 (6)	C3A—C4A—C5A—C1A	−0.2 (6)
C3—C4—C5—C6	−177.7 (4)	C3A—C4A—C5A—C6A	178.2 (4)
C3—C4—O1—C8	−166.3 (4)	C3A—C4A—O1A—C8A	−164.3 (4)
C4—C5—C6—C7	15.3 (7)	C4A—C5A—C6A—C7A	19.1 (6)
C4—C5—C6—O3	137.9 (5)	C4A—C5A—C6A—O3A	141.3 (4)
C5—C1—N2—C3	8.4 (6)	C5A—C1A—N2A—C3A	−9.1 (6)
C5—C1—N2—O5	157.1 (4)	C5A—C1A—N2A—O5A	−165.3 (4)
C5—C4—O1—C8	14.7 (7)	C5A—C4A—O1A—C8A	12.4 (7)
C5—C6—C7—C8	−45.3 (5)	C5A—C6A—C7A—C8A	−49.7 (5)
C5—C6—C7—C15	79.3 (5)	C5A—C6A—C7A—C15A	75.0 (5)
C5—C6—C7—O2	−157.4 (4)	C5A—C6A—C7A—O2A	−162.5 (4)
C6—C7—C8—C9	−176.2 (4)	C6A—C7A—C8A—C9A	−171.8 (4)
C6—C7—C8—O1	63.7 (5)	C6A—C7A—C8A—O1A	66.7 (5)
C7—C8—C9—C10	170.0 (5)	C7A—C8A—C9A—C10A	168.8 (4)
C7—C8—O1—C4	−47.0 (5)	C7A—C8A—O1A—C4A	−45.8 (5)
C8—C9—C10—C11	176.6 (5)	C8A—C9A—C10A—C11A	−171.9 (5)
C9—C8—O1—C4	−172.2 (4)	C9A—C8A—O1A—C4A	−172.5 (4)
C9—C10—C11—C12	178.0 (6)	C9A—C10A—C11A—C12A	177.7 (5)
C10—C11—C12—C13	177.0 (8)	C10A—C11A—C12A—C13A	179.3 (6)
C14—C3—C4—C5	−178.1 (5)	C14A—C3A—C4A—C5A	173.7 (5)
C14—C3—C4—O1	2.7 (8)	C14A—C3A—C4A—O1A	−9.1 (8)
C15—C7—C8—C9	60.4 (6)	C15A—C7A—C8A—C9A	64.2 (6)
C15—C7—C8—O1	−59.7 (5)	C15A—C7A—C8A—O1A	−57.4 (5)
O1—C4—C5—C1	−178.4 (5)	O1A—C4A—C5A—C1A	−177.1 (5)
O1—C4—C5—C6	1.4 (8)	O1A—C4A—C5A—C6A	1.3 (8)
O1—C8—C9—C10	−67.3 (6)	O1A—C8A—C9A—C10A	−67.7 (6)
O2—C7—C8—C9	−60.1 (5)	O2A—C7A—C8A—C9A	−55.7 (5)
O2—C7—C8—O1	179.8 (4)	O2A—C7A—C8A—O1A	−177.2 (4)
O3—C6—C7—C8	−165.6 (4)	O3A—C6A—C7A—C8A	−173.1 (4)
O3—C6—C7—C15	−41.1 (6)	O3A—C6A—C7A—C15A	−48.4 (5)
O3—C6—C7—O2	82.2 (5)	O3A—C6A—C7A—O2A	74.1 (5)
O4—C1—N2—C3	−173.2 (5)	O4A—C1A—N2A—C3A	173.0 (5)
O4—C1—N2—O5	−24.5 (7)	O4A—C1A—N2A—O5A	16.8 (8)
O4—C1—C5—C4	175.2 (5)	O4A—C1A—C5A—C4A	−176.8 (5)
O4—C1—C5—C6	−4.6 (9)	O4A—C1A—C5A—C6A	5.0 (9)
O5—N2—C3—C4	−155.6 (4)	O5A—N2A—C3A—C4A	164.6 (4)
O5—N2—C3—C14	24.9 (8)	O5A—N2A—C3A—C14A	−14.2 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O2A	0.82	2.04	2.818 (5)	158
O3—H3···O4i	0.82	2.03	2.836 (5)	168
O2A—H2A···O4i	0.82	2.00	2.685 (5)	141
O3A—H3A···O4Aii	0.82	2.10	2.829 (5)	149

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O2H2O2A	0.82	2.04	2.818(5)	158
O3H3O4i	0.82	2.03	2.836(5)	168
O2AH2AO4i	0.82	2.00	2.685(5)	141
O3AH3AO4A ii	0.82	2.10	2.829(5)	149

Symmetry codes: (i) ; (ii) .