organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Metacridamide B methanol-d4 monosolvate

aDepartment of Chemistry, Syracuse University, 1-014 Center for Science & Technology, Syracuse, NY 13244-4100, USA, and bUSDA–ARS, Biological IPM Research Unit, Robt. W. Holley Ctr. for Ag. and Health, Tower Rd, Ithaca, NY 14853, USA
*Correspondence e-mail: uenglich@syr.edu

(Received 15 March 2013; accepted 8 April 2013; online 17 April 2013)

The title compound, C35H53NO5·CH3OH {systematic name: (3S,6E,8S,9R,10E,12S,13S,14E,16S,17R)-3-benzyl-9,13-dihy­droxy-6,8,10,12,14,16-hexa­methyl-17-[(2S,4S)-4-methyl­hexan-2-yl]-1-oxa-4-aza­cyclo­hepta­deca-6,10,14-triene-2,5-dione methanol-d4 monosolvate}, was extracted from conidia of the fungus Metarhizium acridum. Crystals were obtained as a methanol-d4 solvate. The tail part of the 4-methyl­hexan-2-yl group exhibits disorder over two positions, with an occupancy ratio of 0.682 (9):0.318 (9). The crystal structure confirms the absolute configuration of nine stereocenters determined previously for the acetyl­ated compound metacridamide A. In the crystal, the methanol-d4 mol­ecule is positioned close to the O atom in the carbonyl group of the peptide bond, forming an O—H⋯O hydrogen bond. It also forms an O—H⋯O hydrogen bond with an adjacent mol­ecule. N—H⋯O and O—H⋯O hydrogen bonds are observed between neighboring mol­ecules.

Related literature

For details of the isolation and purification of the title compound, see: Krasnoff et al. (2012[Krasnoff, S. B., Englich, U., Miller, P. G., Shuler, M. L., Glahn, R. P., Donzelli, B. G. G. & Gibson, D. M. (2012). J. Nat. Prod. 75(2), 175-180.]).

[Scheme 1]

Experimental

Crystal data
  • C35H53NO5·CH4O

  • Mr = 599.83

  • Orthorhombic, P 21 21 21

  • a = 8.5444 (3) Å

  • b = 10.9406 (4) Å

  • c = 37.8017 (15) Å

  • V = 3533.7 (2) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.60 mm−1

  • T = 90 K

  • 0.30 × 0.30 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.841, Tmax = 0.943

  • 15638 measured reflections

  • 6147 independent reflections

  • 6037 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.115

  • S = 1.11

  • 6147 reflections

  • 397 parameters

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.33 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2547 Friedel pairs

  • Flack parameter: 0.12 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N4—H4A⋯O5i 0.88 2.16 2.915 (2) 144
O4—H4B⋯O1Sii 0.84 2.00 2.795 (2) 157
O5—H5A⋯O2iii 0.84 2.06 2.839 (2) 154
O1S—H1S⋯O3 0.84 1.93 2.754 (2) 168
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Related literature top

For details of the isolation and purification of the title compound, see: Krasnoff et al. (2012).

Refinement top

The title compound crystallizes with one methanol solvent molecule in the asymmetric unit. The aliphatic sidechain C20 - C22 has been found to be disordered and therefore modeled with 2 parts A and B, keeping the C20A and C20B restrained in positional and displacement parameters, while C21A, C21B,and C22A, C22B resp. were restrained in their anisotropic displacement parameters. Occupancy has been refined to be 0.682 (9)/0.318 (9). All hydrogen atoms have been placed in idealized positions (riding model) with displacement parameters Uiso 1.2 times the values of the resp. carrier atom for CH and CH2 and 1.5 times the value of the carrier atom for CH3 and OH groups.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. : The molecular structure of the title compound with displacement ellipsoids drawn at 50% probability level. The atoms of the minor disordered component C20B–C22B have been omitted for clarity.
(3S,6E,8S,9R,10E,12S,13S,14E,16S,17R)-3-Benzyl-9,13-dihydroxy-6,8,10,12,14,16- hexamethyl-17-[(2S,4S)-4-methylhexan-2-yl]-1-oxa-4-azacycloheptadeca-6,10,14-triene-2,5-dione methanol-d4 monosolvate top
Crystal data top
C35H53NO5·CH4OF(000) = 1312
Mr = 599.83Dx = 1.127 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54178 Å
a = 8.5444 (3) Åθ = 4.2–67.8°
b = 10.9406 (4) ŵ = 0.60 mm1
c = 37.8017 (15) ÅT = 90 K
V = 3533.7 (2) Å3Block, colourless
Z = 40.30 × 0.30 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
6147 independent reflections
Radiation source: microfocus sourse, Incoatec ImuS micro-focus sealed tube6037 reflections with I > 2σ(I)
Incoatech ImuS multilayer optics monochromatorRint = 0.021
ϕ and ω scansθmax = 68.2°, θmin = 4.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 510
Tmin = 0.841, Tmax = 0.943k = 1312
15638 measured reflectionsl = 4145
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0564P)2 + 1.4912P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
6147 reflectionsΔρmax = 0.28 e Å3
397 parametersΔρmin = 0.33 e Å3
0 restraintsAbsolute structure: Flack (1983), 2547 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.12 (18)
Crystal data top
C35H53NO5·CH4OV = 3533.7 (2) Å3
Mr = 599.83Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 8.5444 (3) ŵ = 0.60 mm1
b = 10.9406 (4) ÅT = 90 K
c = 37.8017 (15) Å0.30 × 0.30 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
6147 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
6037 reflections with I > 2σ(I)
Tmin = 0.841, Tmax = 0.943Rint = 0.021
15638 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.115Δρmax = 0.28 e Å3
S = 1.11Δρmin = 0.33 e Å3
6147 reflectionsAbsolute structure: Flack (1983), 2547 Friedel pairs
397 parametersAbsolute structure parameter: 0.12 (18)
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.24840 (16)0.71863 (13)0.14560 (3)0.0243 (3)
C20.4004 (2)0.70726 (18)0.13849 (5)0.0218 (4)
O20.50540 (16)0.75006 (13)0.15593 (4)0.0277 (3)
C30.4207 (2)0.63685 (18)0.10401 (5)0.0224 (4)
H3A0.33730.57290.10270.027*
C250.5796 (2)0.57359 (19)0.10150 (5)0.0268 (4)
H25A0.58750.53090.07850.032*
H25B0.66350.63590.10250.032*
C260.6035 (2)0.48209 (19)0.13115 (5)0.0263 (4)
C270.7262 (3)0.4954 (2)0.15475 (8)0.0491 (7)
H27A0.79640.56220.15220.059*
C280.7478 (4)0.4124 (3)0.18209 (9)0.0583 (8)
H28A0.83270.42250.19800.070*
C290.6469 (3)0.3158 (2)0.18613 (6)0.0413 (6)
H29A0.66210.25870.20480.050*
C28'0.5243 (3)0.3021 (2)0.16313 (6)0.0355 (5)
H28B0.45380.23570.16590.043*
C27'0.5026 (3)0.3848 (2)0.13574 (6)0.0306 (5)
H27B0.41720.37440.11990.037*
N40.39658 (19)0.72275 (15)0.07506 (4)0.0224 (3)
H4A0.46160.78460.07280.027*
C50.2785 (2)0.71150 (17)0.05146 (5)0.0225 (4)
O30.18573 (18)0.62545 (13)0.05191 (4)0.0315 (3)
C60.2685 (2)0.80822 (18)0.02370 (5)0.0242 (4)
C300.2266 (4)0.7595 (2)0.01239 (6)0.0461 (7)
H30A0.22230.82720.02930.069*
H30B0.12420.71920.01130.069*
H30C0.30600.70040.02000.069*
C70.2905 (2)0.92489 (18)0.03213 (5)0.0227 (4)
H7A0.31440.94190.05620.027*
C80.2815 (2)1.03320 (18)0.00752 (5)0.0230 (4)
H8A0.23021.00630.01490.028*
C310.4462 (3)1.0795 (2)0.00130 (6)0.0289 (5)
H31A0.50721.01320.01190.043*
H31B0.49781.10720.02040.043*
H31C0.43881.14780.01800.043*
C90.1814 (2)1.13529 (18)0.02408 (5)0.0231 (4)
H9A0.18191.20660.00750.028*
O40.25721 (16)1.17147 (13)0.05594 (4)0.0254 (3)
H4B0.20521.22720.06570.038*
C100.0131 (2)1.09516 (17)0.02921 (5)0.0220 (4)
C320.0729 (2)1.0701 (2)0.00471 (5)0.0266 (4)
H32A0.18031.04460.00060.040*
H32B0.01941.00490.01770.040*
H32C0.07511.14450.01910.040*
C110.0488 (2)1.08391 (18)0.06150 (5)0.0240 (4)
H11A0.01821.10260.08080.029*
C120.2128 (2)1.04501 (19)0.07077 (5)0.0249 (4)
H12A0.26481.01950.04830.030*
C330.3060 (3)1.1537 (2)0.08555 (6)0.0319 (5)
H33A0.30381.22120.06850.048*
H33B0.25911.18060.10790.048*
H33C0.41461.12880.08970.048*
C130.2092 (2)0.93239 (19)0.09515 (5)0.0251 (4)
H13A0.15630.86530.08180.030*
O50.36908 (17)0.89529 (14)0.10053 (4)0.0311 (3)
H5A0.37530.85280.11900.047*
C140.1219 (2)0.94720 (18)0.12989 (5)0.0249 (4)
C340.1984 (3)1.0210 (3)0.15900 (6)0.0426 (6)
H34A0.12981.02250.17980.064*
H34B0.29870.98350.16540.064*
H34C0.21621.10470.15070.064*
C150.0193 (2)0.89721 (18)0.13276 (5)0.0247 (4)
H15A0.05010.84510.11390.030*
C160.1368 (2)0.91269 (19)0.16215 (5)0.0248 (4)
H16A0.08490.95740.18200.030*
C350.2724 (3)0.99202 (19)0.14830 (6)0.0291 (4)
H35A0.35021.00300.16710.044*
H35B0.23191.07200.14100.044*
H35C0.32130.95160.12800.044*
C170.1972 (2)0.79026 (18)0.17640 (5)0.0237 (4)
H17A0.28870.80530.19230.028*
C180.0781 (2)0.7101 (2)0.19556 (5)0.0269 (4)
H18A0.01650.70110.18020.032*
C230.1484 (3)0.5832 (2)0.20208 (7)0.0404 (6)
H23A0.18010.54710.17950.061*
H23B0.07010.53080.21340.061*
H23C0.23990.59070.21760.061*
C190.0280 (3)0.7675 (2)0.23088 (5)0.0291 (5)
H19A0.11860.76640.24720.035*
H19B0.00000.85410.22670.035*
C20A0.1103 (3)0.7044 (2)0.24910 (6)0.0365 (5)0.682 (9)
H20A0.10310.61380.24590.044*0.682 (9)
C21A0.2660 (7)0.7548 (8)0.23126 (16)0.0597 (19)0.682 (9)
H21A0.28450.83970.23930.072*0.682 (9)
H21B0.25240.75640.20530.072*0.682 (9)
C22A0.4090 (6)0.6764 (9)0.24045 (15)0.081 (3)0.682 (9)
H22A0.50250.71150.22940.121*0.682 (9)
H22B0.42290.67450.26620.121*0.682 (9)
H22C0.39300.59300.23170.121*0.682 (9)
C20B0.1103 (3)0.7044 (2)0.24910 (6)0.0365 (5)0.318 (9)
H20B0.07160.61820.25020.044*0.318 (9)
C21B0.2570 (18)0.6875 (16)0.2317 (4)0.0597 (19)0.318 (9)
H21C0.23530.65950.20730.072*0.318 (9)
H21D0.30820.76840.22990.072*0.318 (9)
C22B0.3761 (15)0.598 (2)0.2483 (3)0.081 (3)0.318 (9)
H22D0.47350.59960.23460.121*0.318 (9)
H22E0.39780.62230.27270.121*0.318 (9)
H22F0.33270.51500.24800.121*0.318 (9)
C240.1175 (3)0.7359 (2)0.28804 (6)0.0387 (6)
H24A0.20820.69560.29880.058*
H24B0.12740.82470.29080.058*
H24C0.02160.70790.29970.058*
O1S0.1574 (2)0.39740 (14)0.08205 (4)0.0401 (4)
H1S0.17140.46140.07020.060*
C1S0.0341 (5)0.4107 (3)0.10224 (10)0.0731 (10)
H1S10.03900.35220.12180.110*
H1S20.06070.39580.08830.110*
H1S30.03160.49410.11170.110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0167 (7)0.0315 (7)0.0248 (6)0.0010 (6)0.0008 (5)0.0037 (6)
C20.0168 (9)0.0244 (9)0.0241 (9)0.0012 (8)0.0000 (8)0.0032 (8)
O20.0186 (7)0.0381 (8)0.0264 (7)0.0016 (6)0.0009 (6)0.0002 (6)
C30.0204 (10)0.0239 (9)0.0228 (9)0.0016 (8)0.0002 (8)0.0035 (8)
C250.0226 (10)0.0300 (10)0.0278 (10)0.0017 (9)0.0041 (8)0.0030 (8)
C260.0217 (10)0.0288 (10)0.0284 (10)0.0048 (8)0.0028 (8)0.0016 (8)
C270.0400 (15)0.0413 (13)0.0661 (17)0.0103 (12)0.0229 (13)0.0200 (12)
C280.0549 (18)0.0533 (16)0.0666 (18)0.0072 (14)0.0357 (16)0.0187 (14)
C290.0524 (16)0.0339 (12)0.0378 (12)0.0042 (11)0.0116 (11)0.0112 (10)
C28'0.0372 (13)0.0321 (11)0.0374 (11)0.0027 (10)0.0026 (10)0.0042 (9)
C27'0.0264 (11)0.0323 (11)0.0330 (10)0.0047 (9)0.0037 (9)0.0005 (9)
N40.0200 (8)0.0241 (8)0.0231 (8)0.0014 (7)0.0009 (6)0.0037 (7)
C50.0205 (9)0.0211 (9)0.0260 (9)0.0024 (8)0.0002 (8)0.0049 (7)
O30.0353 (8)0.0255 (7)0.0337 (8)0.0039 (7)0.0108 (7)0.0016 (6)
C60.0233 (10)0.0275 (10)0.0217 (9)0.0024 (8)0.0027 (8)0.0016 (7)
C300.080 (2)0.0273 (11)0.0307 (11)0.0019 (13)0.0210 (12)0.0005 (9)
C70.0170 (9)0.0293 (10)0.0218 (9)0.0022 (8)0.0007 (7)0.0010 (8)
C80.0211 (10)0.0253 (10)0.0226 (9)0.0007 (8)0.0009 (8)0.0015 (7)
C310.0252 (11)0.0290 (11)0.0326 (11)0.0013 (9)0.0032 (9)0.0039 (9)
C90.0204 (10)0.0241 (9)0.0247 (9)0.0019 (8)0.0022 (8)0.0011 (8)
O40.0195 (7)0.0280 (7)0.0287 (7)0.0010 (6)0.0011 (6)0.0040 (5)
C100.0196 (10)0.0192 (9)0.0272 (10)0.0033 (7)0.0006 (8)0.0004 (7)
C320.0216 (10)0.0321 (11)0.0262 (10)0.0015 (9)0.0020 (8)0.0013 (8)
C110.0208 (10)0.0239 (10)0.0275 (10)0.0001 (8)0.0021 (8)0.0009 (8)
C120.0193 (10)0.0286 (10)0.0269 (10)0.0000 (8)0.0005 (8)0.0013 (8)
C330.0227 (11)0.0326 (11)0.0405 (12)0.0020 (9)0.0034 (9)0.0010 (9)
C130.0174 (10)0.0312 (10)0.0267 (10)0.0023 (8)0.0003 (8)0.0008 (8)
O50.0210 (7)0.0412 (8)0.0309 (7)0.0090 (6)0.0016 (6)0.0067 (7)
C140.0221 (10)0.0287 (10)0.0240 (10)0.0033 (8)0.0022 (8)0.0014 (8)
C340.0277 (12)0.0697 (17)0.0305 (11)0.0160 (12)0.0036 (10)0.0143 (11)
C150.0234 (10)0.0279 (10)0.0229 (9)0.0011 (8)0.0018 (8)0.0018 (8)
C160.0215 (10)0.0284 (10)0.0245 (9)0.0004 (8)0.0026 (8)0.0032 (8)
C350.0245 (11)0.0302 (10)0.0325 (11)0.0026 (9)0.0011 (9)0.0006 (8)
C170.0188 (9)0.0292 (10)0.0230 (9)0.0001 (8)0.0001 (8)0.0045 (8)
C180.0194 (9)0.0342 (11)0.0270 (10)0.0010 (9)0.0000 (8)0.0012 (9)
C230.0408 (13)0.0316 (12)0.0488 (14)0.0002 (10)0.0149 (11)0.0047 (11)
C190.0296 (11)0.0323 (11)0.0253 (10)0.0021 (9)0.0019 (9)0.0025 (9)
C20A0.0327 (12)0.0436 (13)0.0332 (11)0.0074 (11)0.0069 (10)0.0054 (10)
C21A0.0262 (16)0.121 (6)0.0316 (14)0.002 (4)0.0036 (12)0.010 (4)
C22A0.033 (3)0.173 (8)0.036 (3)0.026 (4)0.0055 (19)0.001 (3)
C20B0.0327 (12)0.0436 (13)0.0332 (11)0.0074 (11)0.0069 (10)0.0054 (10)
C21B0.0262 (16)0.121 (6)0.0316 (14)0.002 (4)0.0036 (12)0.010 (4)
C22B0.033 (3)0.173 (8)0.036 (3)0.026 (4)0.0055 (19)0.001 (3)
C240.0389 (13)0.0482 (14)0.0291 (11)0.0062 (11)0.0055 (10)0.0061 (10)
O1S0.0545 (11)0.0262 (8)0.0396 (9)0.0006 (8)0.0109 (8)0.0003 (7)
C1S0.088 (3)0.062 (2)0.069 (2)0.0158 (19)0.008 (2)0.0059 (17)
Geometric parameters (Å, º) top
O1—C21.332 (2)C33—H33B0.9800
O1—C171.470 (2)C33—H33C0.9800
C2—O21.208 (2)C13—O51.440 (2)
C2—C31.524 (3)C13—C141.519 (3)
C3—N41.457 (2)C13—H13A1.0000
C3—C251.527 (3)O5—H5A0.8400
C3—H3A1.0000C14—C151.330 (3)
C25—C261.517 (3)C14—C341.513 (3)
C25—H25A0.9900C34—H34A0.9800
C25—H25B0.9900C34—H34B0.9800
C26—C27'1.381 (3)C34—H34C0.9800
C26—C271.384 (3)C15—C161.507 (3)
C27—C281.388 (4)C15—H15A0.9500
C27—H27A0.9500C16—C171.533 (3)
C28—C291.372 (4)C16—C351.539 (3)
C28—H28A0.9500C16—H16A1.0000
C29—C28'1.370 (4)C35—H35A0.9800
C29—H29A0.9500C35—H35B0.9800
C28'—C27'1.387 (3)C35—H35C0.9800
C28'—H28B0.9500C17—C181.526 (3)
C27'—H27B0.9500C17—H17A1.0000
N4—C51.352 (3)C18—C231.533 (3)
N4—H4A0.8800C18—C191.536 (3)
C5—O31.231 (2)C18—H18A1.0000
C5—C61.493 (3)C23—H23A0.9800
C6—C71.329 (3)C23—H23B0.9800
C6—C301.508 (3)C23—H23C0.9800
C30—H30A0.9800C19—C20A1.532 (3)
C30—H30B0.9800C19—H19A0.9900
C30—H30C0.9800C19—H19B0.9900
C7—C81.509 (3)C20A—C241.513 (3)
C7—H7A0.9500C20A—C21A1.590 (7)
C8—C311.532 (3)C20A—H20A1.0000
C8—C91.540 (3)C21A—C22A1.533 (8)
C8—H8A1.0000C21A—H21A0.9900
C31—H31A0.9800C21A—H21B0.9900
C31—H31B0.9800C22A—H22A0.9800
C31—H31C0.9800C22A—H22B0.9800
C9—O41.424 (2)C22A—H22C0.9800
C9—C101.516 (3)C21B—C22B1.54 (2)
C9—H9A1.0000C21B—H21C0.9900
O4—H4B0.8400C21B—H21D0.9900
C10—C111.336 (3)C22B—H22D0.9800
C10—C321.503 (3)C22B—H22E0.9800
C32—H32A0.9800C22B—H22F0.9800
C32—H32B0.9800C24—H24A0.9800
C32—H32C0.9800C24—H24B0.9800
C11—C121.505 (3)C24—H24C0.9800
C11—H11A0.9500O1S—C1S1.309 (4)
C12—C331.537 (3)O1S—H1S0.8400
C12—C131.539 (3)C1S—H1S10.9800
C12—H12A1.0000C1S—H1S20.9800
C33—H33A0.9800C1S—H1S30.9800
C2—O1—C17119.99 (15)O5—C13—C14111.96 (16)
O2—C2—O1125.29 (18)O5—C13—C12106.95 (16)
O2—C2—C3125.32 (17)C14—C13—C12116.25 (17)
O1—C2—C3109.34 (16)O5—C13—H13A107.1
N4—C3—C2107.46 (15)C14—C13—H13A107.1
N4—C3—C25111.81 (16)C12—C13—H13A107.1
C2—C3—C25112.58 (16)C13—O5—H5A109.5
N4—C3—H3A108.3C15—C14—C34123.51 (19)
C2—C3—H3A108.3C15—C14—C13118.19 (18)
C25—C3—H3A108.3C34—C14—C13118.28 (18)
C26—C25—C3111.91 (16)C14—C34—H34A109.5
C26—C25—H25A109.2C14—C34—H34B109.5
C3—C25—H25A109.2H34A—C34—H34B109.5
C26—C25—H25B109.2C14—C34—H34C109.5
C3—C25—H25B109.2H34A—C34—H34C109.5
H25A—C25—H25B107.9H34B—C34—H34C109.5
C27'—C26—C27118.2 (2)C14—C15—C16128.22 (19)
C27'—C26—C25121.17 (19)C14—C15—H15A115.9
C27—C26—C25120.6 (2)C16—C15—H15A115.9
C26—C27—C28120.7 (2)C15—C16—C17112.65 (17)
C26—C27—H27A119.6C15—C16—C35108.30 (17)
C28—C27—H27A119.6C17—C16—C35111.02 (17)
C29—C28—C27120.2 (2)C15—C16—H16A108.2
C29—C28—H28A119.9C17—C16—H16A108.2
C27—C28—H28A119.9C35—C16—H16A108.2
C28'—C29—C28119.6 (2)C16—C35—H35A109.5
C28'—C29—H29A120.2C16—C35—H35B109.5
C28—C29—H29A120.2H35A—C35—H35B109.5
C29—C28'—C27'120.3 (2)C16—C35—H35C109.5
C29—C28'—H28B119.8H35A—C35—H35C109.5
C27'—C28'—H28B119.8H35B—C35—H35C109.5
C26—C27'—C28'120.9 (2)O1—C17—C18105.55 (16)
C26—C27'—H27B119.6O1—C17—C16106.71 (15)
C28'—C27'—H27B119.6C18—C17—C16116.37 (17)
C5—N4—C3122.85 (17)O1—C17—H17A109.3
C5—N4—H4A118.6C18—C17—H17A109.3
C3—N4—H4A118.6C16—C17—H17A109.3
O3—C5—N4122.75 (18)C17—C18—C23109.59 (17)
O3—C5—C6120.98 (17)C17—C18—C19111.32 (17)
N4—C5—C6116.25 (17)C23—C18—C19109.85 (18)
C7—C6—C5120.27 (17)C17—C18—H18A108.7
C7—C6—C30126.17 (19)C23—C18—H18A108.7
C5—C6—C30113.52 (17)C19—C18—H18A108.7
C6—C30—H30A109.5C18—C23—H23A109.5
C6—C30—H30B109.5C18—C23—H23B109.5
H30A—C30—H30B109.5H23A—C23—H23B109.5
C6—C30—H30C109.5C18—C23—H23C109.5
H30A—C30—H30C109.5H23A—C23—H23C109.5
H30B—C30—H30C109.5H23B—C23—H23C109.5
C6—C7—C8126.82 (18)C20A—C19—C18114.92 (18)
C6—C7—H7A116.6C20A—C19—H19A108.5
C8—C7—H7A116.6C18—C19—H19A108.5
C7—C8—C31110.32 (16)C20A—C19—H19B108.5
C7—C8—C9110.32 (16)C18—C19—H19B108.5
C31—C8—C9111.02 (17)H19A—C19—H19B107.5
C7—C8—H8A108.4C24—C20A—C19111.44 (19)
C31—C8—H8A108.4C24—C20A—C21A107.4 (3)
C9—C8—H8A108.4C19—C20A—C21A107.3 (3)
C8—C31—H31A109.5C24—C20A—H20A110.2
C8—C31—H31B109.5C19—C20A—H20A110.2
H31A—C31—H31B109.5C21A—C20A—H20A110.2
C8—C31—H31C109.5C22A—C21A—C20A112.1 (4)
H31A—C31—H31C109.5C22A—C21A—H21A109.2
H31B—C31—H31C109.5C20A—C21A—H21A109.2
O4—C9—C10113.82 (16)C22A—C21A—H21B109.2
O4—C9—C8107.03 (15)C20A—C21A—H21B109.2
C10—C9—C8111.65 (16)H21A—C21A—H21B107.9
O4—C9—H9A108.1C21A—C22A—H22A109.5
C10—C9—H9A108.1C21A—C22A—H22B109.5
C8—C9—H9A108.1H22A—C22A—H22B109.5
C9—O4—H4B109.5C21A—C22A—H22C109.5
C11—C10—C32124.70 (19)H22A—C22A—H22C109.5
C11—C10—C9121.26 (18)H22B—C22A—H22C109.5
C32—C10—C9114.03 (16)C22B—C21B—H21C107.7
C10—C32—H32A109.5C22B—C21B—H21D107.7
C10—C32—H32B109.5H21C—C21B—H21D107.1
H32A—C32—H32B109.5C21B—C22B—H22D109.5
C10—C32—H32C109.5C21B—C22B—H22E109.5
H32A—C32—H32C109.5H22D—C22B—H22E109.5
H32B—C32—H32C109.5C21B—C22B—H22F109.5
C10—C11—C12127.37 (19)H22D—C22B—H22F109.5
C10—C11—H11A116.3H22E—C22B—H22F109.5
C12—C11—H11A116.3C20A—C24—H24A109.5
C11—C12—C33110.38 (17)C20A—C24—H24B109.5
C11—C12—C13110.32 (16)H24A—C24—H24B109.5
C33—C12—C13114.33 (17)C20A—C24—H24C109.5
C11—C12—H12A107.2H24A—C24—H24C109.5
C33—C12—H12A107.2H24B—C24—H24C109.5
C13—C12—H12A107.2C1S—O1S—H1S109.5
C12—C33—H33A109.5O1S—C1S—H1S1109.5
C12—C33—H33B109.5O1S—C1S—H1S2109.5
H33A—C33—H33B109.5H1S1—C1S—H1S2109.5
C12—C33—H33C109.5O1S—C1S—H1S3109.5
H33A—C33—H33C109.5H1S1—C1S—H1S3109.5
H33B—C33—H33C109.5H1S2—C1S—H1S3109.5
C17—O1—C2—O21.4 (3)C8—C9—C10—C11114.8 (2)
C17—O1—C2—C3176.01 (15)O4—C9—C10—C32173.62 (16)
O2—C2—C3—N496.8 (2)C8—C9—C10—C3265.1 (2)
O1—C2—C3—N480.66 (19)C32—C10—C11—C120.0 (3)
O2—C2—C3—C2526.8 (3)C9—C10—C11—C12179.84 (18)
O1—C2—C3—C25155.80 (16)C10—C11—C12—C33110.0 (2)
N4—C3—C25—C26178.74 (17)C10—C11—C12—C13122.7 (2)
C2—C3—C25—C2660.2 (2)C11—C12—C13—O5175.62 (16)
C3—C25—C26—C27'59.2 (3)C33—C12—C13—O559.3 (2)
C3—C25—C26—C27119.7 (2)C11—C12—C13—C1458.5 (2)
C27'—C26—C27—C280.6 (4)C33—C12—C13—C1466.6 (2)
C25—C26—C27—C28179.5 (3)O5—C13—C14—C15132.99 (19)
C26—C27—C28—C290.2 (5)C12—C13—C14—C15103.7 (2)
C27—C28—C29—C28'0.3 (5)O5—C13—C14—C3448.7 (3)
C28—C29—C28'—C27'0.4 (4)C12—C13—C14—C3474.6 (3)
C27—C26—C27'—C28'0.5 (3)C34—C14—C15—C167.0 (4)
C25—C26—C27'—C28'179.38 (19)C13—C14—C15—C16171.19 (19)
C29—C28'—C27'—C260.0 (4)C14—C15—C16—C17128.9 (2)
C2—C3—N4—C5116.88 (19)C14—C15—C16—C35107.9 (2)
C25—C3—N4—C5119.1 (2)C2—O1—C17—C18131.99 (18)
C3—N4—C5—O32.6 (3)C2—O1—C17—C16103.61 (19)
C3—N4—C5—C6179.08 (17)C15—C16—C17—O151.0 (2)
O3—C5—C6—C7139.5 (2)C35—C16—C17—O170.67 (19)
N4—C5—C6—C742.2 (3)C15—C16—C17—C1866.5 (2)
O3—C5—C6—C3038.4 (3)C35—C16—C17—C18171.86 (17)
N4—C5—C6—C30140.0 (2)O1—C17—C18—C2351.7 (2)
C5—C6—C7—C8178.82 (18)C16—C17—C18—C23169.85 (18)
C30—C6—C7—C81.3 (4)O1—C17—C18—C19173.47 (16)
C6—C7—C8—C31104.4 (2)C16—C17—C18—C1968.4 (2)
C6—C7—C8—C9132.5 (2)C17—C18—C19—C20A170.56 (19)
C7—C8—C9—O461.5 (2)C23—C18—C19—C20A67.9 (2)
C31—C8—C9—O461.1 (2)C18—C19—C20A—C24160.6 (2)
C7—C8—C9—C1063.7 (2)C18—C19—C20A—C21A82.1 (4)
C31—C8—C9—C10173.69 (16)C24—C20A—C21A—C22A74.4 (5)
O4—C9—C10—C116.5 (3)C19—C20A—C21A—C22A165.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O5i0.882.162.915 (2)144
O4—H4B···O1Sii0.842.002.795 (2)157
O5—H5A···O2iii0.842.062.839 (2)154
O1S—H1S···O30.841.932.754 (2)168
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC35H53NO5·CH4O
Mr599.83
Crystal system, space groupOrthorhombic, P212121
Temperature (K)90
a, b, c (Å)8.5444 (3), 10.9406 (4), 37.8017 (15)
V3)3533.7 (2)
Z4
Radiation typeCu Kα
µ (mm1)0.60
Crystal size (mm)0.30 × 0.30 × 0.10
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.841, 0.943
No. of measured, independent and
observed [I > 2σ(I)] reflections
15638, 6147, 6037
Rint0.021
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.115, 1.11
No. of reflections6147
No. of parameters397
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.33
Absolute structureFlack (1983), 2547 Friedel pairs
Absolute structure parameter0.12 (18)

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O5i0.882.162.915 (2)144.0
O4—H4B···O1Sii0.842.002.795 (2)156.6
O5—H5A···O2iii0.842.062.839 (2)153.5
O1S—H1S···O30.841.932.754 (2)167.5
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x1, y, z.
 

Acknowledgements

We gratefully acknowledge J. Zuk (Cornell) and R. Garcia (Cornell University) for technical assistance. The authors gratefully acknowledge support from the National Science Foundation (grant CHE 1048703) and Syracuse University for the purchase of the X-ray instrument.

References

First citationBruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationKrasnoff, S. B., Englich, U., Miller, P. G., Shuler, M. L., Glahn, R. P., Donzelli, B. G. G. & Gibson, D. M. (2012). J. Nat. Prod. 75(2), 175–180.  Web of Science CSD CrossRef
First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds