Longipilin acetate

Ospina, O.L.; Rojas, C.A.; Vega, D.

doi:10.1107/S1600536806007215

Longipilin acetate

Longipilin acetate, C₂₃H₂₈O₉, is a compound isolated from Espeletia killipii, a Colombian native plant. The molecule contains two non-planar rings, a ten-membered ring and a five-membered lactone. Various substituents around the ten-membered ring provide very weak intramolecular hydrogen-bonding interactions that determine the molecular folding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007215/sj2008sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007215/sj2008Isup2.hkl Contains datablock I

CCDC reference: 605176

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.010 Å
R factor = 0.043
wR factor = 0.138
Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         35 Perc.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C20    -   C21     ..      10.96 su

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.105
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ...    2297.00 Ang-3
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.66 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.34 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C9     ..  O17     ..      97.90 Deg.
PLAT756_ALERT_4_C H...A   Calc     2.57000, Rep    2.570(6) ......  Senseless su
              H23B -O12     1.555   1.455
PLAT756_ALERT_4_C H...A   Calc     2.52000, Rep    2.520(7) ......  Senseless su
              H18B -O4      1.555   2.675
PLAT756_ALERT_4_C H...A   Calc     2.49000, Rep   2.490(10) ......  Senseless su
              H18C -O15     1.555   3.467
PLAT756_ALERT_4_C H...A   Calc     2.58000, Rep    2.584(5) ......  Senseless su
              H14A -O19     1.555   2.674
PLAT756_ALERT_4_C H...A   Calc     2.25000, Rep    2.252(9) ......  Senseless su
              H8   -O19     1.555   1.555
PLAT756_ALERT_4_C H...A   Calc     2.51000, Rep    2.506(3) ......  Senseless su
              H6   -O8      1.555   1.555
PLAT756_ALERT_4_C H...A   Calc     2.39000, Rep    2.392(4) ......  Senseless su
              H9   -O17     1.555   1.555
PLAT756_ALERT_4_C H...A   Calc     2.38000, Rep    2.382(5) ......  Senseless su
              H1   -O15     1.555   1.555
PLAT756_ALERT_4_C H...A   Calc     2.46000, Rep    2.458(9) ......  Senseless su
              H8   -O16     1.555   1.555
PLAT758_ALERT_4_C D-H..A  Calc      107.00, Rep    106.6(3) ......  Senseless su
              C8   -H8   -O19     1.555   1.555   1.555
PLAT758_ALERT_4_C D-H..A  Calc      105.00, Rep    105.0(3) ......  Senseless su
              C6   -H6   -O8      1.555   1.555   1.555
PLAT758_ALERT_4_C D-H..A  Calc       98.00, Rep     97.9(3) ......  Senseless su
              C9   -H9   -O17     1.555   1.555   1.555
PLAT758_ALERT_4_C D-H..A  Calc      105.00, Rep    104.6(3) ......  Senseless su
              C1   -H1   -O15     1.555   1.555   1.555
PLAT758_ALERT_4_C D-H..A  Calc      108.00, Rep    108.3(3) ......  Senseless su
              C8   -H8   -O16     1.555   1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.51
           From the CIF: _reflns_number_total               2990
           Count of symmetry unique reflns         2993
           Completeness (_total/calc)             99.90%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  25 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
  16 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC6S Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC6S Diffractometer Control Software; data reduction: MSC/AFC6S Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Longipilin acetate top

Crystal data top

C₂₃H₂₈O₉	F(000) = 952
M_r = 448.45	D_x = 1.297 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 20 reflections
a = 8.354 (9) Å	θ = 20–25°
b = 16.39 (7) Å	µ = 0.1 mm⁻¹
c = 16.78 (1) Å	T = 293 K
V = 2297 (9) Å³	Prism, colourless
Z = 4	0.6 × 0.4 × 0.3 mm

Data collection top

Rigaku AFC6 diffractometer	R_int = 0.105
ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: ψ scan (MSC/AFC6S Diffractometer Control Software; Molecular Structure Corporation, 1993)	h = −10→10
T_min = 0.95, T_max = 0.97	k = −21→0
5981 measured reflections	l = −21→1
2990 independent reflections	3 standard reflections every 147 reflections
1032 reflections with I > 2σ(I)	intensity decay: none

Refinement top

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)] = 0.043	H-atom parameters constrained
wR(F²) = 0.138	w = 1/[σ²(F_o²) + (0.0571P)²]
S = 0.92	(Δ/σ)_max < 0.001
2990 reflections	Δρ_max = 0.22 e Å⁻³
294 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Absolute structure: Friedel pairs were merged
Primary atom site location: structure-invariant direct methods

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

	x	y	z	U_iso*/U_eq
C22	0.6685 (10)	1.2812 (5)	0.9424 (5)	0.118 (3)
H22A	0.7724	1.2909	0.9649	0.177*
H22B	0.6201	1.2352	0.9682	0.177*
H22C	0.6025	1.3285	0.9499	0.177*
C21	0.6841 (7)	1.2648 (4)	0.8589 (5)	0.092 (2)
H21	0.6470	1.3063	0.8260	0.110*
C20	0.7417 (6)	1.2015 (3)	0.8210 (4)	0.0608 (15)
C23	0.7463 (7)	1.1969 (4)	0.7301 (4)	0.0845 (19)
H23A	0.7027	1.2462	0.7081	0.127*
H23B	0.6841	1.1511	0.7124	0.127*
H23C	0.8550	1.1905	0.7127	0.127*
C19	0.8083 (6)	1.1322 (3)	0.8686 (4)	0.0558 (14)
C8	0.9079 (5)	0.9948 (3)	0.8515 (3)	0.0442 (12)
H8	0.9331	1.0043	0.9078	0.053*
C9	0.7806 (6)	0.9268 (3)	0.8458 (3)	0.0518 (13)
H9	0.7215	0.9333	0.7958	0.062*
C17	0.5181 (7)	0.9208 (3)	0.9042 (4)	0.0605 (15)
C18	0.4301 (7)	0.9350 (4)	0.9802 (3)	0.0747 (17)
H18A	0.3186	0.9232	0.9726	0.112*
H18B	0.4424	0.9909	0.9961	0.112*
H18C	0.4726	0.9000	1.0209	0.112*
C10	0.8401 (6)	0.8391 (3)	0.8515 (3)	0.0534 (14)
C15	0.9360 (7)	0.8121 (4)	0.9215 (4)	0.0645 (15)
C16	1.0399 (9)	0.8452 (4)	1.0474 (4)	0.104 (2)
H16A	1.1410	0.8198	1.0361	0.156*
H16B	0.9715	0.8068	1.0741	0.156*
H16C	1.0566	0.8918	1.0810	0.156*
C1	0.8011 (7)	0.7827 (3)	0.7982 (4)	0.0669 (16)
H1	0.8460	0.7315	0.8068	0.080*
C2	0.6967 (7)	0.7890 (4)	0.7268 (4)	0.0814 (19)
H2A	0.6235	0.8343	0.7345	0.098*
H2B	0.6329	0.7397	0.7232	0.098*
C3	0.7850 (8)	0.8013 (4)	0.6469 (4)	0.0826 (18)
H3A	0.8729	0.7629	0.6430	0.099*
H3B	0.7121	0.7909	0.6031	0.099*
C4	0.8490 (8)	0.8877 (3)	0.6410 (3)	0.0723 (17)
C14	0.7290 (8)	0.9535 (4)	0.6247 (3)	0.087 (2)
H14A	0.6823	0.9450	0.5730	0.131*
H14B	0.7811	1.0056	0.6259	0.131*
H14C	0.6466	0.9519	0.6645	0.131*
C5	1.0064 (7)	0.9014 (3)	0.6783 (3)	0.0616 (15)
H5	1.0529	0.8534	0.7044	0.074*
C6	1.0541 (7)	0.9806 (3)	0.7130 (3)	0.0579 (14)
H6	0.9804	1.0235	0.6953	0.070*
C12	1.2933 (9)	1.0403 (4)	0.7472 (4)	0.0778 (18)
C11	1.1953 (6)	1.0399 (3)	0.8218 (3)	0.0554 (13)
C13	1.2286 (7)	1.0851 (3)	0.8839 (4)	0.0721 (17)
H13A	1.3169	1.1196	0.8830	0.086*
H13B	1.1639	1.0827	0.9290	0.086*
C7	1.0633 (6)	0.9794 (3)	0.8064 (3)	0.0474 (13)
H7	1.1028	0.9255	0.8223	0.057*
O19	0.8420 (6)	1.1299 (2)	0.9380 (2)	0.0833 (13)
O8	0.8357 (4)	1.06756 (19)	0.81889 (19)	0.0515 (9)
O9	0.6729 (4)	0.94351 (19)	0.91180 (19)	0.0563 (9)
O17	0.4638 (5)	0.8924 (2)	0.8433 (3)	0.0837 (13)
O15	0.9815 (8)	0.7437 (3)	0.9312 (3)	0.1133 (18)
O16	0.9650 (4)	0.8709 (2)	0.9732 (2)	0.0714 (11)
O6	1.2170 (5)	1.0003 (3)	0.6882 (2)	0.0762 (11)
O12	1.4252 (5)	1.0704 (3)	0.7377 (3)	0.1073 (16)
O4	0.9941 (6)	0.8958 (2)	0.5927 (2)	0.0857 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C22	0.121 (7)	0.122 (6)	0.111 (6)	0.031 (5)	−0.004 (6)	−0.030 (5)
C21	0.063 (4)	0.083 (5)	0.129 (6)	−0.005 (4)	−0.018 (5)	0.007 (5)
C20	0.046 (3)	0.035 (3)	0.102 (5)	0.004 (3)	0.010 (3)	−0.011 (3)
C23	0.072 (4)	0.085 (4)	0.096 (5)	−0.011 (4)	−0.015 (4)	0.032 (4)
C19	0.053 (3)	0.049 (3)	0.066 (4)	−0.004 (3)	0.009 (3)	−0.005 (3)
C8	0.045 (3)	0.042 (3)	0.046 (3)	0.002 (2)	−0.001 (3)	0.000 (3)
C9	0.054 (3)	0.051 (3)	0.051 (3)	−0.007 (3)	0.010 (3)	−0.008 (3)
C17	0.052 (4)	0.049 (3)	0.080 (4)	0.004 (3)	0.015 (4)	0.003 (3)
C18	0.061 (4)	0.077 (4)	0.086 (4)	0.004 (3)	0.020 (4)	0.021 (4)
C10	0.050 (3)	0.044 (3)	0.066 (4)	−0.001 (3)	0.010 (3)	0.003 (3)
C15	0.071 (4)	0.058 (4)	0.064 (4)	0.005 (4)	0.014 (3)	0.011 (3)
C16	0.098 (5)	0.132 (6)	0.083 (5)	−0.005 (5)	−0.010 (4)	0.035 (4)
C1	0.068 (4)	0.047 (3)	0.086 (4)	−0.001 (3)	0.014 (4)	−0.012 (3)
C2	0.070 (4)	0.070 (4)	0.104 (5)	−0.004 (3)	−0.007 (5)	−0.037 (4)
C3	0.080 (4)	0.086 (4)	0.082 (4)	0.004 (4)	−0.010 (4)	−0.029 (4)
C4	0.076 (4)	0.083 (4)	0.058 (4)	0.016 (4)	0.001 (4)	−0.013 (3)
C14	0.095 (5)	0.102 (4)	0.065 (4)	0.023 (4)	−0.026 (4)	−0.021 (4)
C5	0.070 (4)	0.067 (4)	0.049 (3)	0.010 (3)	0.004 (3)	−0.006 (3)
C6	0.062 (4)	0.060 (3)	0.052 (3)	0.000 (3)	0.007 (3)	0.000 (3)
C12	0.073 (4)	0.066 (4)	0.094 (5)	−0.008 (4)	0.024 (4)	0.015 (4)
C11	0.048 (3)	0.050 (3)	0.068 (4)	−0.004 (3)	0.000 (3)	0.012 (3)
C13	0.065 (4)	0.057 (3)	0.095 (5)	−0.013 (3)	−0.003 (4)	0.000 (4)
C7	0.050 (3)	0.046 (3)	0.046 (3)	−0.001 (3)	0.003 (3)	0.007 (2)
O19	0.126 (4)	0.070 (3)	0.054 (3)	0.013 (3)	0.000 (3)	−0.012 (2)
O8	0.053 (2)	0.0482 (19)	0.0539 (19)	0.0060 (17)	−0.0012 (18)	−0.0004 (19)
O9	0.047 (2)	0.060 (2)	0.061 (2)	−0.0027 (19)	0.012 (2)	−0.0045 (19)
O17	0.061 (3)	0.088 (3)	0.102 (3)	−0.001 (2)	0.002 (3)	−0.028 (3)
O15	0.167 (5)	0.062 (2)	0.111 (4)	0.028 (3)	−0.007 (4)	0.022 (3)
O16	0.076 (3)	0.071 (3)	0.067 (3)	0.004 (2)	−0.005 (2)	0.014 (2)
O6	0.075 (3)	0.083 (2)	0.071 (3)	−0.010 (2)	0.022 (2)	−0.002 (2)
O12	0.077 (3)	0.113 (4)	0.132 (4)	−0.030 (3)	0.038 (3)	0.007 (3)
O4	0.103 (3)	0.097 (3)	0.057 (2)	0.015 (3)	0.009 (3)	−0.009 (2)

Geometric parameters (Å, º) top

C22—C21	1.431 (8)	C16—H16A	0.9600
C22—H22A	0.9600	C16—H16B	0.9600
C22—H22B	0.9600	C16—H16C	0.9600
C22—H22C	0.9600	C1—C2	1.485 (8)
C21—C20	1.309 (9)	C1—H1	0.9300
C21—H21	0.9300	C2—C3	1.544 (8)
C20—C19	1.495 (8)	C2—H2A	0.9700
C20—C23	1.528 (7)	C2—H2B	0.9700
C23—H23A	0.9600	C3—C4	1.517 (10)
C23—H23B	0.9600	C3—H3A	0.9700
C23—H23C	0.9600	C3—H3B	0.9700
C19—O19	1.198 (6)	C4—O4	1.464 (7)
C19—O8	1.368 (7)	C4—C5	1.473 (8)
C8—O8	1.444 (7)	C4—C14	1.497 (8)
C8—C7	1.524 (6)	C14—H14A	0.9600
C8—C9	1.543 (7)	C14—H14B	0.9600
C8—H8	0.9800	C14—H14C	0.9600
C9—O9	1.452 (5)	C5—O4	1.442 (6)
C9—C10	1.524 (9)	C5—C6	1.478 (8)
C9—H9	0.9800	C5—H5	0.9800
C17—O17	1.212 (6)	C6—O6	1.459 (6)
C17—O9	1.352 (7)	C6—C7	1.569 (7)
C17—C18	1.490 (7)	C6—H6	0.9800
C18—H18A	0.9600	C12—O12	1.217 (7)
C18—H18B	0.9600	C12—O6	1.348 (7)
C18—H18C	0.9600	C12—C11	1.496 (8)
C10—C1	1.327 (7)	C11—C13	1.308 (7)
C10—C15	1.488 (7)	C11—C7	1.505 (7)
C15—O15	1.195 (7)	C13—H13A	0.9300
C15—O16	1.321 (7)	C13—H13B	0.9300
C16—O16	1.456 (7)	C7—H7	0.9800

C21—C22—H22A	109.5	C1—C2—C3	115.4 (5)
C21—C22—H22B	109.5	C1—C2—H2A	108.4
H22A—C22—H22B	109.5	C3—C2—H2A	108.4
C21—C22—H22C	109.5	C1—C2—H2B	108.4
H22A—C22—H22C	109.5	C3—C2—H2B	108.4
H22B—C22—H22C	109.5	H2A—C2—H2B	107.5
C20—C21—C22	131.1 (7)	C4—C3—C2	110.3 (5)
C20—C21—H21	114.4	C4—C3—H3A	109.6
C22—C21—H21	114.4	C2—C3—H3A	109.6
C21—C20—C19	118.6 (6)	C4—C3—H3B	109.6
C21—C20—C23	122.2 (6)	C2—C3—H3B	109.6
C19—C20—C23	119.1 (5)	H3A—C3—H3B	108.1
C20—C23—H23A	109.5	O4—C4—C5	58.8 (4)
C20—C23—H23B	109.5	O4—C4—C14	112.9 (5)
H23A—C23—H23B	109.5	C5—C4—C14	124.5 (5)
C20—C23—H23C	109.5	O4—C4—C3	114.3 (5)
H23A—C23—H23C	109.5	C5—C4—C3	115.4 (5)
H23B—C23—H23C	109.5	C14—C4—C3	116.6 (6)
O19—C19—O8	121.9 (5)	C4—C14—H14A	109.5
O19—C19—C20	129.1 (5)	C4—C14—H14B	109.5
O8—C19—C20	108.9 (5)	H14A—C14—H14B	109.5
O8—C8—C7	107.7 (4)	C4—C14—H14C	109.5
O8—C8—C9	106.6 (4)	H14A—C14—H14C	109.5
C7—C8—C9	115.9 (4)	H14B—C14—H14C	109.5
O8—C8—H8	108.8	O4—C5—C4	60.3 (4)
C7—C8—H8	108.8	O4—C5—C6	117.8 (5)
C9—C8—H8	108.8	C4—C5—C6	122.8 (5)
O9—C9—C10	109.4 (4)	O4—C5—H5	114.9
O9—C9—C8	104.1 (4)	C4—C5—H5	114.9
C10—C9—C8	116.9 (5)	C6—C5—H5	114.9
O9—C9—H9	108.7	O6—C6—C5	109.5 (4)
C10—C9—H9	108.7	O6—C6—C7	104.0 (4)
C8—C9—H9	108.7	C5—C6—C7	113.3 (4)
O17—C17—O9	122.9 (5)	O6—C6—H6	110.0
O17—C17—C18	126.7 (5)	C5—C6—H6	110.0
O9—C17—C18	110.4 (5)	C7—C6—H6	110.0
C17—C18—H18A	109.5	O12—C12—O6	121.9 (6)
C17—C18—H18B	109.5	O12—C12—C11	127.4 (7)
H18A—C18—H18B	109.5	O6—C12—C11	110.7 (5)
C17—C18—H18C	109.5	C13—C11—C12	123.2 (5)
H18A—C18—H18C	109.5	C13—C11—C7	131.7 (5)
H18B—C18—H18C	109.5	C12—C11—C7	105.1 (5)
C1—C10—C15	117.2 (5)	C11—C13—H13A	120.0
C1—C10—C9	122.3 (5)	C11—C13—H13B	120.0
C15—C10—C9	120.4 (5)	H13A—C13—H13B	120.0
O15—C15—O16	122.5 (6)	C11—C7—C8	115.4 (4)
O15—C15—C10	123.9 (6)	C11—C7—C6	101.5 (4)
O16—C15—C10	113.6 (5)	C8—C7—C6	116.9 (4)
O16—C16—H16A	109.5	C11—C7—H7	107.5
O16—C16—H16B	109.5	C8—C7—H7	107.5
H16A—C16—H16B	109.5	C6—C7—H7	107.5
O16—C16—H16C	109.5	C19—O8—C8	118.6 (4)
H16A—C16—H16C	109.5	C17—O9—C9	118.0 (4)
H16B—C16—H16C	109.5	C15—O16—C16	115.4 (5)
C10—C1—C2	129.8 (5)	C12—O6—C6	109.8 (4)
C10—C1—H1	115.1	C5—O4—C4	60.9 (3)
C2—C1—H1	115.1

C22—C21—C20—C19	−1.5 (11)	O12—C12—C11—C13	12.4 (9)
C22—C21—C20—C23	179.8 (7)	O6—C12—C11—C13	−168.7 (5)
C21—C20—C19—O19	−13.4 (10)	O12—C12—C11—C7	−167.5 (6)
C23—C20—C19—O19	165.2 (6)	O6—C12—C11—C7	11.4 (6)
C21—C20—C19—O8	169.6 (5)	C13—C11—C7—C8	28.2 (8)
C23—C20—C19—O8	−11.7 (7)	C12—C11—C7—C8	−152.0 (4)
O8—C8—C9—O9	−77.9 (4)	C13—C11—C7—C6	155.6 (5)
C7—C8—C9—O9	162.3 (4)	C12—C11—C7—C6	−24.5 (5)
O8—C8—C9—C10	161.4 (4)	O8—C8—C7—C11	69.3 (5)
C7—C8—C9—C10	41.5 (6)	C9—C8—C7—C11	−171.5 (4)
O9—C9—C10—C1	113.4 (5)	O8—C8—C7—C6	−49.9 (5)
C8—C9—C10—C1	−128.7 (5)	C9—C8—C7—C6	69.3 (6)
O9—C9—C10—C15	−62.2 (6)	O6—C6—C7—C11	29.5 (5)
C8—C9—C10—C15	55.7 (6)	C5—C6—C7—C11	148.3 (5)
C1—C10—C15—O15	1.4 (8)	O6—C6—C7—C8	156.0 (4)
C9—C10—C15—O15	177.2 (6)	C5—C6—C7—C8	−85.2 (6)
C1—C10—C15—O16	−177.7 (5)	O19—C19—O8—C8	−0.2 (8)
C9—C10—C15—O16	−1.9 (7)	C20—C19—O8—C8	177.0 (4)
C15—C10—C1—C2	174.3 (6)	C7—C8—O8—C19	−120.8 (4)
C9—C10—C1—C2	−1.4 (9)	C9—C8—O8—C19	114.2 (4)
C10—C1—C2—C3	98.6 (7)	O17—C17—O9—C9	−5.0 (7)
C1—C2—C3—C4	−73.7 (7)	C18—C17—O9—C9	174.3 (4)
C2—C3—C4—O4	150.7 (5)	C10—C9—O9—C17	−83.3 (6)
C2—C3—C4—C5	85.2 (6)	C8—C9—O9—C17	151.1 (4)
C2—C3—C4—C14	−74.6 (7)	O15—C15—O16—C16	−6.9 (8)
C14—C4—C5—O4	−97.7 (6)	C10—C15—O16—C16	172.2 (4)
C3—C4—C5—O4	104.2 (5)	O12—C12—O6—C6	−172.4 (5)
O4—C4—C5—C6	105.8 (6)	C11—C12—O6—C6	8.6 (6)
C14—C4—C5—C6	8.0 (9)	C5—C6—O6—C12	−145.6 (5)
C3—C4—C5—C6	−150.0 (5)	C7—C6—O6—C12	−24.2 (5)
O4—C5—C6—O6	−64.5 (6)	C6—C5—O4—C4	−113.8 (6)
C4—C5—C6—O6	−135.4 (5)	C14—C4—O4—C5	117.6 (6)
O4—C5—C6—C7	180.0 (5)	C3—C4—O4—C5	−106.0 (6)
C4—C5—C6—C7	109.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23B···O12ⁱ	0.96	2.57 (1)	3.39 (1)	144 (1)
C18—H18B···O4ⁱⁱ	0.96	2.52 (1)	3.41 (1)	155 (1)
C18—H18C···O15ⁱⁱⁱ	0.96	2.49 (1)	3.31 (1)	144 (1)
C14—H14A···O19^iv	0.96	2.58 (1)	3.47 (1)	153 (1)
C8—H8···O19	0.98	2.25 (1)	2.704 (9)	107 (1)
C6—H6···O8	0.98	2.51 (1)	2.919 (7)	105 (1)
C9—H9···O17	0.98	2.39 (1)	2.706 (7)	98 (1)
C1—H1···O15	0.93	2.38 (1)	2.767 (8)	105 (1)
C8—H8···O16	0.98	2.46 (1)	2.919 (8)	108 (1)

Symmetry codes: (i) x−1, y, z; (ii) −x+3/2, −y+2, z+1/2; (iii) x−1/2, −y+3/2, −z+2; (iv) −x+3/2, −y+2, z−1/2.

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