Phenyl 3,4-O-isopropyl­idene-6-O-pivalyl-β-d-galactopyran­oside

Jia, J.; Zhang, Y.; Wang, X.-Z.; Shao, T.-F.; Wang, J.

doi:10.1107/S1600536806035264

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Phenyl 3,4-O-isopropylidene-6-O-pivalyl-β-D-galactopyranoside

J. Jia, Y. Zhang, X.-Z. Wang, T.-F. Shao and J. Wang

In the title compound, C₂₀H₂₈O₇, the six-membered sugar ring adopts a distorted chair conformation. Intermolecular O—H

O hydrogen bonds link the molecules into zigzag chains extending along the a axis. The crystal packing is further stabilized by weak intermolecular C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035264/cv2108sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035264/cv2108Isup2.hkl Contains datablock I

CCDC reference: 624186

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.058
wR factor = 0.171
Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
REFLT03_ALERT_1_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           28.29
           From the CIF: _diffrn_reflns_theta_full          28.29
           From the CIF: _reflns_number_total               2897
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3054
           Completeness (_total/calc)             94.86%
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.77 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.68 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.47 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C17'
PLAT301_ALERT_3_C Main Residue  Disorder .........................      13.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10A   ..  O4      ..       2.61 Ang.

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           28.29
           From the CIF: _reflns_number_total               2897
           Count of symmetry unique reflns         3054
           Completeness (_total/calc)             94.86%
           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
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          S

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

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

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL.

Phenyl 3,4-O-isopropylidene-6-O-pivalyl-β-D-galactopyranoside top

Crystal data top

C₂₀H₂₈O₇	F(000) = 816
M_r = 380.42	D_x = 1.178 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1528 reflections
a = 5.8611 (11) Å	θ = 2.4–22.4°
b = 18.529 (3) Å	µ = 0.09 mm⁻¹
c = 19.756 (4) Å	T = 298 K
V = 2145.5 (7) Å³	Block, colourless
Z = 4	0.5 × 0.34 × 0.2 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2897 independent reflections
Radiation source: fine-focus sealed tube	1993 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
φ and ω scans	θ_max = 28.3°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.970, T_max = 0.981	k = −23→20
12805 measured reflections	l = −25→22

Refinement top

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.1046P)² + 0.091P] where P = (F_o² + 2F_c²)/3
2897 reflections	(Δ/σ)_max < 0.001
260 parameters	Δρ_max = 0.32 e Å⁻³
44 restraints	Δρ_min = −0.21 e Å⁻³

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	Occ. (<1)
C17	0.8991 (17)	1.1729 (5)	−0.1111 (4)	0.093 (2)	0.630 (7)
C18	0.742 (2)	1.1635 (6)	−0.1732 (5)	0.104 (3)	0.630 (7)
H18D	0.7684	1.1170	−0.1932	0.156*	0.630 (7)
H18E	0.7745	1.2005	−0.2057	0.156*	0.630 (7)
H18F	0.5856	1.1670	−0.1592	0.156*	0.630 (7)
C19	1.019 (3)	1.2421 (5)	−0.0853 (5)	0.132 (3)	0.630 (7)
H19D	1.1388	1.2291	−0.0545	0.198*	0.630 (7)
H19E	0.9100	1.2721	−0.0624	0.198*	0.630 (7)
H19F	1.0823	1.2679	−0.1230	0.198*	0.630 (7)
C20	1.0904 (19)	1.1310 (6)	−0.1459 (5)	0.124 (3)	0.630 (7)
H20D	1.2157	1.1251	−0.1151	0.185*	0.630 (7)
H20E	1.1409	1.1571	−0.1851	0.185*	0.630 (7)
H20F	1.0349	1.0844	−0.1594	0.185*	0.630 (7)
C17'	0.888 (3)	1.1820 (8)	−0.1038 (8)	0.093 (2)	0.370 (7)
C18'	0.701 (3)	1.1919 (10)	−0.1556 (9)	0.104 (3)	0.370 (7)
H18A	0.5668	1.2100	−0.1337	0.156*	0.370 (7)
H18B	0.6679	1.1463	−0.1765	0.156*	0.370 (7)
H18C	0.7507	1.2256	−0.1895	0.156*	0.370 (7)
C19'	0.776 (4)	1.2535 (8)	−0.0859 (10)	0.132 (3)	0.370 (7)
H19A	0.8455	1.2730	−0.0459	0.198*	0.370 (7)
H19B	0.6161	1.2460	−0.0779	0.198*	0.370 (7)
H19C	0.7949	1.2868	−0.1228	0.198*	0.370 (7)
C20'	1.142 (3)	1.1941 (12)	−0.1108 (9)	0.124 (3)	0.370 (7)
H20A	1.2111	1.1950	−0.0667	0.185*	0.370 (7)
H20B	1.1690	1.2394	−0.1331	0.185*	0.370 (7)
H20C	1.2078	1.1558	−0.1370	0.185*	0.370 (7)
O1	0.6387 (4)	0.95281 (11)	−0.05225 (11)	0.0527 (6)
O2	0.3875 (4)	0.94308 (11)	0.08182 (11)	0.0558 (6)
O3	0.1960 (4)	0.83956 (11)	0.05772 (11)	0.0582 (6)
O4	0.3897 (4)	0.77271 (11)	−0.06708 (12)	0.0578 (6)
H4A	0.4878	0.7415	−0.0626	0.087*
O5	0.6176 (5)	1.10829 (13)	−0.05010 (14)	0.0730 (8)
O6	0.9602 (7)	1.1087 (3)	−0.0074 (3)	0.1405 (17)
O7	0.7670 (4)	0.85682 (12)	−0.11170 (10)	0.0550 (6)
C1	0.4452 (6)	0.99333 (15)	−0.03063 (17)	0.0532 (8)
H1A	0.3572	1.0069	−0.0708	0.064*
C2	0.2913 (6)	0.95101 (15)	0.01567 (16)	0.0498 (8)
H2A	0.1430	0.9752	0.0190	0.060*
C3	0.2560 (6)	0.87252 (15)	−0.00501 (16)	0.0486 (7)
H3A	0.1277	0.8691	−0.0366	0.058*
C4	0.4640 (6)	0.83739 (15)	−0.03557 (16)	0.0477 (7)
H4B	0.5739	0.8260	0.0002	0.057*
C5	0.5717 (6)	0.88877 (16)	−0.08581 (16)	0.0482 (7)
H5A	0.4643	0.8999	−0.1224	0.058*
C6	0.2728 (7)	0.88452 (17)	0.11277 (17)	0.0563 (8)
C7	0.0638 (9)	0.9096 (2)	0.1514 (3)	0.0910 (14)
H7A	−0.0350	0.9360	0.1216	0.136*
H7B	0.1101	0.9403	0.1881	0.136*
H7C	−0.0161	0.8685	0.1691	0.136*
C8	0.4402 (9)	0.8437 (2)	0.1558 (2)	0.0804 (12)
H8A	0.5683	0.8294	0.1287	0.121*
H8B	0.3676	0.8016	0.1742	0.121*
H8C	0.4917	0.8741	0.1921	0.121*
C9	0.8623 (6)	0.88369 (16)	−0.17077 (15)	0.0512 (8)
C10	1.0601 (7)	0.84970 (18)	−0.19154 (17)	0.0575 (8)
H10A	1.1210	0.8123	−0.1658	0.069*
C11	1.1677 (8)	0.8711 (2)	−0.25043 (18)	0.0702 (10)
H11A	1.3022	0.8488	−0.2640	0.084*
C12	1.0757 (10)	0.9254 (2)	−0.2889 (2)	0.0855 (14)
H12A	1.1445	0.9391	−0.3293	0.103*
C13	0.8841 (10)	0.9590 (3)	−0.2675 (2)	0.0924 (15)
H13A	0.8242	0.9964	−0.2933	0.111*
C14	0.7740 (9)	0.9394 (2)	−0.2082 (2)	0.0780 (12)
H14A	0.6432	0.9635	−0.1941	0.094*
C15	0.5319 (7)	1.06115 (17)	0.00195 (19)	0.0640 (10)
H15A	0.4096	1.0848	0.0265	0.077*
H15B	0.6527	1.0497	0.0338	0.077*
C16	0.8331 (8)	1.1290 (2)	−0.0492 (2)	0.0790 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C17'	0.070 (3)	0.080 (4)	0.129 (4)	−0.016 (3)	−0.001 (3)	0.042 (3)
C18'	0.110 (5)	0.108 (6)	0.094 (5)	0.005 (5)	0.016 (4)	0.010 (4)
C19'	0.182 (7)	0.083 (4)	0.132 (4)	−0.019 (5)	0.032 (6)	0.015 (3)
C20'	0.118 (5)	0.143 (6)	0.110 (5)	0.000 (5)	0.019 (5)	0.028 (4)
C17	0.070 (3)	0.080 (4)	0.129 (4)	−0.016 (3)	−0.001 (3)	0.042 (3)
C18	0.110 (5)	0.108 (6)	0.094 (5)	0.005 (5)	0.016 (4)	0.010 (4)
C19	0.182 (7)	0.083 (4)	0.132 (4)	−0.019 (5)	0.032 (6)	0.015 (3)
C20	0.118 (5)	0.143 (6)	0.110 (5)	0.000 (5)	0.019 (5)	0.028 (4)
O1	0.0489 (12)	0.0439 (11)	0.0652 (13)	−0.0038 (10)	−0.0010 (12)	0.0011 (9)
O2	0.0609 (14)	0.0442 (11)	0.0622 (13)	−0.0133 (11)	0.0037 (12)	−0.0031 (10)
O3	0.0656 (14)	0.0444 (11)	0.0647 (13)	−0.0177 (11)	0.0037 (12)	0.0026 (10)
O4	0.0560 (14)	0.0358 (10)	0.0816 (15)	0.0055 (10)	−0.0117 (13)	−0.0015 (9)
O5	0.0781 (18)	0.0500 (13)	0.0908 (18)	−0.0117 (14)	−0.0006 (16)	0.0177 (13)
O6	0.081 (2)	0.176 (4)	0.165 (4)	−0.030 (3)	−0.024 (3)	0.093 (3)
O7	0.0577 (14)	0.0522 (11)	0.0550 (12)	0.0089 (11)	0.0008 (11)	0.0108 (10)
C1	0.0553 (19)	0.0365 (14)	0.0679 (19)	0.0016 (14)	0.0005 (17)	0.0073 (14)
C2	0.0470 (17)	0.0377 (14)	0.0646 (19)	0.0025 (13)	−0.0005 (16)	0.0033 (13)
C3	0.0434 (16)	0.0422 (15)	0.0602 (17)	−0.0043 (14)	−0.0051 (15)	0.0015 (14)
C4	0.0468 (17)	0.0376 (14)	0.0587 (17)	0.0025 (13)	−0.0083 (15)	0.0033 (13)
C5	0.0463 (17)	0.0440 (15)	0.0544 (17)	0.0037 (14)	−0.0076 (15)	0.0034 (13)
C6	0.062 (2)	0.0456 (15)	0.0610 (19)	−0.0105 (17)	0.0088 (17)	−0.0035 (15)
C7	0.088 (3)	0.078 (3)	0.107 (3)	−0.013 (3)	0.041 (3)	−0.020 (2)
C8	0.091 (3)	0.077 (3)	0.073 (2)	−0.013 (2)	−0.011 (2)	0.014 (2)
C9	0.0583 (19)	0.0440 (15)	0.0513 (17)	−0.0038 (16)	−0.0014 (16)	0.0013 (13)
C10	0.063 (2)	0.0524 (17)	0.0577 (18)	−0.0035 (17)	−0.0042 (18)	−0.0004 (15)
C11	0.071 (3)	0.072 (2)	0.067 (2)	−0.010 (2)	0.009 (2)	−0.0072 (19)
C12	0.104 (4)	0.085 (3)	0.068 (2)	−0.026 (3)	0.010 (3)	0.009 (2)
C13	0.105 (4)	0.084 (3)	0.088 (3)	0.007 (3)	0.002 (3)	0.038 (2)
C14	0.081 (3)	0.071 (2)	0.082 (3)	0.008 (2)	−0.001 (2)	0.024 (2)
C15	0.075 (2)	0.0415 (16)	0.075 (2)	−0.0092 (17)	0.008 (2)	0.0094 (16)
C16	0.059 (2)	0.070 (2)	0.108 (3)	0.000 (2)	0.001 (2)	0.026 (2)

Geometric parameters (Å, º) top

C17'—C16	1.493 (10)	O5—C15	1.440 (4)
C17'—C18'	1.511 (10)	O6—C16	1.174 (5)
C17'—C20'	1.512 (10)	O7—C9	1.386 (4)
C17'—C19'	1.522 (10)	O7—C5	1.387 (4)
C18'—H18A	0.9600	C1—C15	1.501 (5)
C18'—H18B	0.9600	C1—C2	1.505 (4)
C18'—H18C	0.9600	C1—H1A	0.9800
C19'—H19A	0.9600	C2—C3	1.525 (4)
C19'—H19B	0.9600	C2—H2A	0.9800
C19'—H19C	0.9600	C3—C4	1.508 (5)
C20'—H20A	0.9600	C3—H3A	0.9800
C20'—H20B	0.9600	C4—C5	1.513 (4)
C20'—H20C	0.9600	C4—H4B	0.9800
C17—C16	1.520 (8)	C5—H5A	0.9800
C17—C20	1.528 (9)	C6—C8	1.502 (6)
C17—C18	1.543 (8)	C6—C7	1.517 (6)
C17—C19	1.547 (9)	C7—H7A	0.9600
C18—H18D	0.9600	C7—H7B	0.9600
C18—H18E	0.9600	C7—H7C	0.9600
C18—H18F	0.9600	C8—H8A	0.9600
C19—H19D	0.9600	C8—H8B	0.9600
C19—H19E	0.9600	C8—H8C	0.9600
C19—H19F	0.9600	C9—C14	1.371 (5)
C20—H20D	0.9600	C9—C10	1.382 (5)
C20—H20E	0.9600	C10—C11	1.382 (5)
C20—H20F	0.9600	C10—H10A	0.9300
O1—C5	1.415 (4)	C11—C12	1.371 (6)
O1—C1	1.426 (4)	C11—H11A	0.9300
O2—C6	1.415 (4)	C12—C13	1.352 (7)
O2—C2	1.431 (4)	C12—H12A	0.9300
O3—C3	1.426 (4)	C13—C14	1.386 (6)
O3—C6	1.442 (4)	C13—H13A	0.9300
O4—C4	1.419 (4)	C14—H14A	0.9300
O4—H4A	0.8200	C15—H15A	0.9700
O5—C16	1.320 (5)	C15—H15B	0.9700

C16—C17'—C18'	114.3 (12)	O3—C3—C4	111.3 (3)
C16—C17'—C20'	112.2 (11)	O3—C3—C2	102.1 (2)
C18'—C17'—C20'	129.3 (14)	C4—C3—C2	114.2 (3)
C16—C17'—C19'	108.2 (11)	O3—C3—H3A	109.7
C18'—C17'—C19'	74.7 (12)	C4—C3—H3A	109.7
C20'—C17'—C19'	108.5 (18)	C2—C3—H3A	109.7
C17'—C18'—H18A	109.5	O4—C4—C3	107.0 (3)
C17'—C18'—H18B	109.5	O4—C4—C5	111.8 (3)
H18A—C18'—H18B	109.5	C3—C4—C5	109.2 (2)
C17'—C18'—H18C	109.5	O4—C4—H4B	109.6
H18A—C18'—H18C	109.5	C3—C4—H4B	109.6
H18B—C18'—H18C	109.5	C5—C4—H4B	109.6
C17'—C19'—H19A	109.5	O7—C5—O1	107.6 (3)
C17'—C19'—H19B	109.5	O7—C5—C4	108.5 (2)
H19A—C19'—H19B	109.5	O1—C5—C4	109.6 (2)
C17'—C19'—H19C	109.5	O7—C5—H5A	110.4
H19A—C19'—H19C	109.5	O1—C5—H5A	110.4
H19B—C19'—H19C	109.5	C4—C5—H5A	110.4
C17'—C20'—H20A	109.5	O2—C6—O3	105.4 (2)
C17'—C20'—H20B	109.5	O2—C6—C8	108.7 (3)
H20A—C20'—H20B	109.5	O3—C6—C8	109.9 (3)
C17'—C20'—H20C	109.5	O2—C6—C7	111.5 (3)
H20A—C20'—H20C	109.5	O3—C6—C7	107.7 (3)
H20B—C20'—H20C	109.5	C8—C6—C7	113.4 (4)
C16—C17—C20	106.1 (7)	C6—C7—H7A	109.5
C16—C17—C18	115.3 (7)	C6—C7—H7B	109.5
C20—C17—C18	91.3 (8)	H7A—C7—H7B	109.5
C16—C17—C19	107.1 (7)	C6—C7—H7C	109.5
C20—C17—C19	103.7 (9)	H7A—C7—H7C	109.5
C18—C17—C19	128.8 (8)	H7B—C7—H7C	109.5
C17—C18—H18D	109.5	C6—C8—H8A	109.5
C17—C18—H18E	109.5	C6—C8—H8B	109.5
H18D—C18—H18E	109.5	H8A—C8—H8B	109.5
C17—C18—H18F	109.5	C6—C8—H8C	109.5
H18D—C18—H18F	109.5	H8A—C8—H8C	109.5
H18E—C18—H18F	109.5	H8B—C8—H8C	109.5
C17—C19—H19D	109.5	C14—C9—C10	120.0 (3)
C17—C19—H19E	109.5	C14—C9—O7	124.9 (4)
H19D—C19—H19E	109.5	C10—C9—O7	115.1 (3)
C17—C19—H19F	109.5	C11—C10—C9	120.1 (3)
H19D—C19—H19F	109.5	C11—C10—H10A	119.9
H19E—C19—H19F	109.5	C9—C10—H10A	119.9
C17—C20—H20D	109.5	C12—C11—C10	119.9 (4)
C17—C20—H20E	109.5	C12—C11—H11A	120.1
H20D—C20—H20E	109.5	C10—C11—H11A	120.1
C17—C20—H20F	109.5	C13—C12—C11	119.4 (4)
H20D—C20—H20F	109.5	C13—C12—H12A	120.3
H20E—C20—H20F	109.5	C11—C12—H12A	120.3
C5—O1—C1	111.2 (2)	C12—C13—C14	122.1 (4)
C6—O2—C2	106.6 (2)	C12—C13—H13A	119.0
C3—O3—C6	109.3 (2)	C14—C13—H13A	119.0
C4—O4—H4A	109.5	C9—C14—C13	118.5 (4)
C16—O5—C15	120.0 (3)	C9—C14—H14A	120.7
C9—O7—C5	119.3 (3)	C13—C14—H14A	120.7
O1—C1—C15	107.4 (3)	O5—C15—C1	108.7 (3)
O1—C1—C2	112.6 (2)	O5—C15—H15A	110.0
C15—C1—C2	112.3 (3)	C1—C15—H15A	110.0
O1—C1—H1A	108.1	O5—C15—H15B	110.0
C15—C1—H1A	108.1	C1—C15—H15B	110.0
C2—C1—H1A	108.1	H15A—C15—H15B	108.3
O2—C2—C1	111.9 (3)	O6—C16—O5	121.6 (4)
O2—C2—C3	101.5 (2)	O6—C16—C17'	125.5 (7)
C1—C2—C3	114.5 (3)	O5—C16—C17'	112.9 (7)
O2—C2—H2A	109.5	O6—C16—C17	125.2 (5)
C1—C2—H2A	109.5	O5—C16—C17	112.8 (5)
C3—C2—H2A	109.5

C5—O1—C1—C15	−178.0 (2)	C5—O7—C9—C10	178.2 (3)
C5—O1—C1—C2	57.9 (3)	C14—C9—C10—C11	−0.8 (5)
C6—O2—C2—C1	−160.9 (3)	O7—C9—C10—C11	178.8 (3)
C6—O2—C2—C3	−38.3 (3)	C9—C10—C11—C12	−1.1 (5)
O1—C1—C2—O2	73.9 (3)	C10—C11—C12—C13	2.1 (6)
C15—C1—C2—O2	−47.5 (4)	C11—C12—C13—C14	−1.2 (8)
O1—C1—C2—C3	−40.9 (4)	C10—C9—C14—C13	1.7 (6)
C15—C1—C2—C3	−162.4 (3)	O7—C9—C14—C13	−177.9 (4)
C6—O3—C3—C4	101.7 (3)	C12—C13—C14—C9	−0.7 (7)
C6—O3—C3—C2	−20.4 (3)	C16—O5—C15—C1	−120.3 (4)
O2—C2—C3—O3	35.3 (3)	O1—C1—C15—O5	72.8 (3)
C1—C2—C3—O3	156.0 (3)	C2—C1—C15—O5	−162.9 (3)
O2—C2—C3—C4	−84.9 (3)	C15—O5—C16—O6	1.7 (8)
C1—C2—C3—C4	35.8 (4)	C15—O5—C16—C17'	−175.7 (9)
O3—C3—C4—O4	79.5 (3)	C15—O5—C16—C17	174.8 (5)
C2—C3—C4—O4	−165.6 (2)	C18'—C17'—C16—O6	173.1 (11)
O3—C3—C4—C5	−159.3 (2)	C20'—C17'—C16—O6	14 (2)
C2—C3—C4—C5	−44.4 (4)	C19'—C17'—C16—O6	−105.9 (13)
C9—O7—C5—O1	−78.5 (3)	C18'—C17'—C16—O5	−9.6 (17)
C9—O7—C5—C4	163.0 (2)	C20'—C17'—C16—O5	−168.9 (13)
C1—O1—C5—O7	173.4 (2)	C19'—C17'—C16—O5	71.4 (16)
C1—O1—C5—C4	−68.8 (3)	C18'—C17'—C16—C17	82 (6)
O4—C4—C5—O7	−63.9 (3)	C20'—C17'—C16—C17	−77 (6)
C3—C4—C5—O7	177.9 (2)	C19'—C17'—C16—C17	163 (7)
O4—C4—C5—O1	178.9 (2)	C20—C17—C16—O6	53.0 (11)
C3—C4—C5—O1	60.7 (3)	C18—C17—C16—O6	152.3 (8)
C2—O2—C6—O3	26.3 (3)	C19—C17—C16—O6	−57.2 (12)
C2—O2—C6—C8	144.0 (3)	C20—C17—C16—O5	−119.8 (7)
C2—O2—C6—C7	−90.4 (4)	C18—C17—C16—O5	−20.5 (10)
C3—O3—C6—O2	−2.3 (4)	C19—C17—C16—O5	130.0 (8)
C3—O3—C6—C8	−119.3 (3)	C20—C17—C16—C17'	148 (7)
C3—O3—C6—C7	116.8 (3)	C18—C17—C16—C17'	−112 (6)
C5—O7—C9—C14	−2.2 (5)	C19—C17—C16—C17'	38 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3ⁱ	0.82	1.94	2.754 (3)	173
C3—H3A···O7ⁱⁱ	0.98	2.59	3.570 (4)	175
C10—H10A···O4ⁱⁱⁱ	0.93	2.61	3.437 (4)	148

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

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