2,3,4,6-Tetra-O-acetyl-N-(2-hydroxy­benzyl­idene)-β-d-galactopyran­osylamine

Akkurt, M.; Yıldırım, S.Ö.; Jarrahpour, A.A.; Alvand, P.; Büyükgüngör, O.

doi:10.1107/S1600536806011329

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2,3,4,6-Tetra-O-acetyl-N-(2-hydroxybenzylidene)-β-D-galactopyranosylamine

M. Akkurt, S. Ö. Yıldırım, A. A. Jarrahpour, P. Alvand and O. Büyükgüngör

In the title compound, C₂₁H₂₅NO₁₀, the six-membered pyranosyl ring adopts a chair conformation. The crystal structure contains intra- and intermolecular hydrogen-bonding interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011329/sg2019sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011329/sg2019Isup2.hkl Contains datablock I

CCDC reference: 608483

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R factor = 0.041
wR factor = 0.102
Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
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        C20
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

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               2894
           Count of symmetry unique reflns         2970
           Completeness (_total/calc)             97.44%
           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
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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).

2,3,4,6-Tetra-O-acetyl-N-(2-hydroxybenzylidene)-β-D-galactopyranosylamine top

Crystal data top

C₂₁H₂₅NO₁₀	F(000) = 952
M_r = 451.42	D_x = 1.319 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 16444 reflections
a = 7.8014 (4) Å	θ = 1.7–27.4°
b = 15.2381 (11) Å	µ = 0.11 mm⁻¹
c = 19.1271 (10) Å	T = 296 K
V = 2273.8 (2) Å³	Prism, colorless
Z = 4	0.57 × 0.50 × 0.45 mm

Data collection top

Stoe IPDS-2 diffractometer	2894 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2002 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.091
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.5°, θ_min = 2.1°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −19→19
T_min = 0.942, T_max = 0.954	l = −24→24
16920 measured reflections

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0555P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
2894 reflections	Δρ_max = 0.14 e Å⁻³
298 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0146 (18)

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O1	0.2683 (3)	0.69455 (16)	0.85467 (14)	0.0977 (9)
O2	0.78910 (19)	0.86100 (11)	0.79170 (9)	0.0626 (5)
O3	0.5878 (2)	0.67966 (10)	0.69770 (10)	0.0658 (6)
O4	0.3390 (2)	0.74805 (14)	0.67811 (13)	0.0892 (8)
O5	0.8122 (2)	0.74932 (12)	0.59644 (9)	0.0672 (6)
O6	0.9913 (4)	0.6366 (2)	0.58817 (15)	0.1320 (12)
O7	0.85338 (18)	0.91263 (11)	0.64846 (9)	0.0601 (5)
O8	1.0448 (3)	0.91674 (19)	0.56098 (14)	0.1038 (9)
O9	1.1984 (2)	0.95461 (13)	0.74765 (11)	0.0765 (7)
O10	1.1346 (3)	1.07594 (17)	0.69024 (18)	0.1147 (12)
N1	0.5476 (2)	0.77608 (14)	0.82324 (11)	0.0629 (6)
C1	0.2302 (3)	0.7639 (2)	0.89524 (15)	0.0726 (9)
C2	0.0753 (4)	0.7631 (3)	0.9314 (2)	0.0992 (13)
C3	0.0312 (6)	0.8324 (4)	0.9713 (3)	0.1263 (19)
C4	0.1383 (6)	0.9048 (4)	0.9777 (3)	0.1333 (19)
C5	0.2921 (5)	0.9053 (3)	0.94259 (19)	0.1027 (14)
C6	0.3397 (3)	0.83622 (18)	0.90047 (14)	0.0690 (9)
C7	0.5013 (3)	0.83824 (17)	0.86228 (14)	0.0639 (8)
C8	0.7073 (3)	0.77898 (16)	0.78504 (13)	0.0599 (7)
C9	0.6734 (3)	0.76214 (14)	0.70773 (13)	0.0574 (7)
C10	0.8438 (3)	0.75784 (15)	0.67004 (12)	0.0570 (7)
C11	0.9438 (3)	0.84211 (15)	0.68264 (14)	0.0579 (7)
C12	0.9561 (3)	0.86178 (18)	0.75977 (14)	0.0627 (8)
C13	0.4191 (3)	0.68175 (19)	0.68112 (16)	0.0717 (9)
C14	0.3534 (5)	0.5926 (3)	0.6687 (3)	0.129 (2)
C15	0.9013 (3)	0.6890 (2)	0.56006 (17)	0.0751 (10)
C16	0.8781 (4)	0.6991 (3)	0.48453 (18)	0.0980 (13)
C17	0.9135 (3)	0.94171 (17)	0.58662 (16)	0.0688 (9)
C18	0.7963 (4)	1.0058 (2)	0.55449 (19)	0.0918 (11)
C19	1.0281 (3)	0.9502 (2)	0.77726 (17)	0.0741 (9)
C20	1.2325 (4)	1.0185 (2)	0.70322 (17)	0.0764 (10)
C21	1.4055 (4)	1.0074 (3)	0.6720 (2)	0.1074 (15)
HO1	0.370 (5)	0.711 (2)	0.830 (2)	0.102 (11)*
H2	0.00260	0.71490	0.92800	0.1190*
H3	−0.07290	0.83180	0.99500	0.1510*
H4	0.10640	0.95220	1.00530	0.1600*
H5	0.36530	0.95310	0.94740	0.1230*
H7	0.57230	0.88690	0.86690	0.0770*
H8	0.78370	0.73310	0.80300	0.0720*
H9	0.60370	0.80980	0.68830	0.0690*
H10	0.91000	0.70740	0.68680	0.0680*
H11	1.05910	0.83660	0.66280	0.0700*
H12	1.02710	0.81670	0.78200	0.0750*
H14A	0.28120	0.57540	0.70700	0.1930*
H14B	0.44780	0.55240	0.66500	0.1930*
H14C	0.28830	0.59170	0.62620	0.1930*
H16A	0.98770	0.70730	0.46270	0.1470*
H16B	0.80680	0.74920	0.47550	0.1470*
H16C	0.82450	0.64740	0.46590	0.1470*
H18A	0.86170	1.05080	0.53160	0.1370*
H18B	0.72580	1.03180	0.59010	0.1370*
H18C	0.72490	0.97670	0.52080	0.1370*
H19A	0.95640	0.99610	0.75780	0.0890*
H19B	1.03320	0.95790	0.82760	0.0890*
H21A	1.39440	0.99340	0.62330	0.1610*
H21B	1.46470	0.96080	0.69550	0.1610*
H21C	1.46920	1.06100	0.67710	0.1610*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0866 (13)	0.0907 (15)	0.1159 (18)	−0.0226 (11)	0.0256 (13)	−0.0028 (14)
O2	0.0543 (8)	0.0642 (9)	0.0694 (10)	−0.0047 (7)	0.0100 (7)	−0.0065 (8)
O3	0.0580 (8)	0.0557 (9)	0.0838 (12)	−0.0023 (7)	−0.0048 (8)	0.0003 (8)
O4	0.0636 (10)	0.0901 (14)	0.1139 (16)	0.0087 (11)	−0.0110 (10)	0.0012 (13)
O5	0.0657 (9)	0.0730 (11)	0.0629 (9)	0.0074 (8)	−0.0004 (8)	−0.0072 (9)
O6	0.135 (2)	0.151 (2)	0.110 (2)	0.077 (2)	−0.0270 (17)	−0.0502 (19)
O7	0.0498 (7)	0.0607 (9)	0.0699 (10)	0.0052 (7)	0.0088 (7)	0.0039 (8)
O8	0.0814 (13)	0.1268 (18)	0.1031 (16)	0.0311 (13)	0.0400 (12)	0.0292 (14)
O9	0.0532 (9)	0.0781 (12)	0.0982 (14)	−0.0047 (8)	0.0104 (9)	−0.0063 (11)
O10	0.0914 (14)	0.0868 (14)	0.166 (3)	−0.0134 (13)	−0.0034 (16)	0.0195 (17)
N1	0.0595 (10)	0.0632 (11)	0.0659 (12)	0.0014 (8)	0.0102 (9)	0.0054 (10)
C1	0.0661 (14)	0.0819 (18)	0.0697 (15)	0.0050 (13)	0.0128 (12)	0.0175 (15)
C2	0.0767 (18)	0.119 (3)	0.102 (2)	0.0001 (18)	0.0246 (17)	0.033 (2)
C3	0.105 (3)	0.151 (4)	0.123 (3)	0.024 (3)	0.062 (2)	0.028 (3)
C4	0.134 (3)	0.146 (4)	0.120 (3)	0.015 (3)	0.066 (3)	−0.024 (3)
C5	0.111 (2)	0.112 (3)	0.085 (2)	−0.001 (2)	0.032 (2)	−0.020 (2)
C6	0.0698 (14)	0.0808 (17)	0.0565 (13)	0.0078 (13)	0.0121 (12)	0.0118 (13)
C7	0.0646 (12)	0.0642 (14)	0.0628 (14)	−0.0028 (11)	0.0041 (12)	0.0003 (12)
C8	0.0566 (12)	0.0556 (12)	0.0674 (14)	0.0015 (9)	0.0052 (10)	0.0022 (11)
C9	0.0530 (10)	0.0495 (11)	0.0697 (14)	0.0022 (9)	0.0032 (10)	0.0010 (11)
C10	0.0560 (11)	0.0547 (12)	0.0603 (13)	0.0085 (10)	0.0008 (9)	−0.0016 (11)
C11	0.0462 (10)	0.0583 (12)	0.0693 (14)	0.0059 (9)	0.0050 (10)	0.0017 (11)
C12	0.0497 (11)	0.0684 (14)	0.0700 (15)	0.0008 (10)	0.0039 (10)	−0.0054 (12)
C13	0.0627 (13)	0.0739 (17)	0.0786 (17)	−0.0057 (13)	−0.0071 (12)	0.0041 (14)
C14	0.105 (3)	0.091 (2)	0.190 (5)	−0.033 (2)	−0.058 (3)	0.017 (3)
C15	0.0511 (12)	0.0918 (19)	0.0823 (18)	−0.0007 (13)	−0.0029 (12)	−0.0265 (16)
C16	0.0828 (18)	0.136 (3)	0.0751 (19)	−0.0123 (19)	0.0024 (15)	−0.037 (2)
C17	0.0580 (13)	0.0671 (14)	0.0813 (18)	0.0030 (11)	0.0125 (12)	0.0060 (13)
C18	0.0864 (18)	0.093 (2)	0.096 (2)	0.0201 (16)	0.0157 (17)	0.0276 (18)
C19	0.0533 (12)	0.0834 (17)	0.0855 (18)	−0.0089 (12)	0.0101 (12)	−0.0149 (15)
C20	0.0683 (15)	0.0708 (17)	0.090 (2)	−0.0170 (14)	−0.0001 (14)	−0.0079 (16)
C21	0.0793 (19)	0.124 (3)	0.119 (3)	−0.0302 (19)	0.0304 (18)	−0.024 (2)

Geometric parameters (Å, º) top

O1—C1	1.344 (4)	C12—C19	1.498 (4)
O2—C8	1.409 (3)	C13—C14	1.471 (5)
O2—C12	1.439 (3)	C15—C16	1.464 (5)
O3—C9	1.436 (3)	C17—C18	1.472 (4)
O3—C13	1.354 (3)	C20—C21	1.486 (5)
O4—C13	1.189 (3)	C2—H2	0.9300
O5—C10	1.435 (3)	C3—H3	0.9300
O5—C15	1.346 (3)	C4—H4	0.9300
O6—C15	1.192 (4)	C5—H5	0.9300
O7—C11	1.442 (3)	C7—H7	0.9300
O7—C17	1.347 (3)	C8—H8	0.9800
O8—C17	1.198 (4)	C9—H9	0.9800
O9—C19	1.446 (3)	C10—H10	0.9800
O9—C20	1.319 (4)	C11—H11	0.9800
O10—C20	1.188 (4)	C12—H12	0.9800
O1—HO1	0.96 (4)	C14—H14A	0.9600
N1—C8	1.445 (3)	C14—H14B	0.9600
N1—C7	1.259 (3)	C14—H14C	0.9600
C1—C2	1.392 (4)	C16—H16A	0.9600
C1—C6	1.398 (4)	C16—H16B	0.9600
C2—C3	1.348 (7)	C16—H16C	0.9600
C3—C4	1.389 (8)	C18—H18A	0.9600
C4—C5	1.375 (6)	C18—H18B	0.9600
C5—C6	1.377 (5)	C18—H18C	0.9600
C6—C7	1.457 (3)	C19—H19A	0.9700
C8—C9	1.524 (4)	C19—H19B	0.9700
C9—C10	1.514 (3)	C21—H21A	0.9600
C10—C11	1.522 (3)	C21—H21B	0.9600
C11—C12	1.509 (4)	C21—H21C	0.9600

O1···N1	2.579 (3)	C20···C11	3.529 (4)
O1···C18ⁱ	3.398 (4)	C20···O3^vii	3.404 (4)
O2···O7	2.894 (2)	C1···H3^ix	2.9800
O3···O5	2.818 (2)	C1···H12ⁱⁱⁱ	2.8000
O3···C20ⁱⁱ	3.404 (4)	C2···H12ⁱⁱⁱ	3.0000
O3···N1	2.833 (3)	C4···H19Bⁱⁱⁱ	3.0900
O4···C11ⁱⁱⁱ	3.401 (3)	C5···H19Bⁱⁱⁱ	3.0900
O4···N1	3.246 (3)	C7···HO1	2.28 (3)
O4···C16^iv	3.228 (4)	C8···HO1	2.96 (4)
O5···O3	2.818 (2)	C13···HO1	2.91 (4)
O5···O7	2.699 (2)	C19···H14A^viii	3.0900
O5···C17	3.042 (3)	C21···H18B^v	2.9700
O5···O8	3.203 (3)	HO1···N1	1.71 (4)
O6···C14^v	3.287 (5)	HO1···C7	2.28 (3)
O7···O5	2.699 (2)	HO1···C8	2.96 (4)
O7···O2	2.894 (2)	HO1···C13	2.91 (4)
O8···C16^vi	3.261 (4)	H3···C1^x	2.9800
O8···O5	3.203 (3)	H4···H21A^xi	2.4000
O10···C17	3.330 (4)	H5···H7	2.4500
O10···C8^vii	3.364 (4)	H7···O2	2.2600
O1···H18Bⁱ	2.7000	H7···H5	2.4500
O2···H7	2.2600	H7···H14B^viii	2.6000
O4···H11ⁱⁱⁱ	2.5800	H8···H10	2.4600
O4···H9	2.2800	H8···H12	2.3200
O5···H16A^iv	2.8500	H8···O10ⁱⁱ	2.4800
O6···H14C^v	2.5200	H9···O4	2.2800
O6···H10	2.2600	H9···O7	2.6100
O7···H19A	2.5800	H9···H21Bⁱⁱⁱ	2.5500
O7···H9	2.6100	H10···O6	2.2600
O8···H16C^vi	2.4500	H10···H8	2.4600
O8···H11	2.3000	H11···O4^v	2.5800
O9···H11	2.6500	H11···O8	2.3000
O10···H19A	2.2500	H11···O9	2.6500
O10···H8^vii	2.4800	H12···C1^v	2.8000
N1···O1	2.579 (3)	H12···C2^v	3.0000
N1···O3	2.833 (3)	H12···H8	2.3200
N1···O4	3.246 (3)	H14A···C19ⁱ	3.0900
N1···C13	3.234 (4)	H14A···H19Aⁱ	2.3100
N1···HO1	1.71 (4)	H14B···H7ⁱ	2.6000
C8···O10ⁱⁱ	3.364 (4)	H14C···O6ⁱⁱⁱ	2.5200
C11···O4^v	3.401 (3)	H16A···O5^vi	2.8500
C11···C20	3.529 (4)	H16C···O8^iv	2.4500
C13···N1	3.234 (4)	H18B···C21ⁱⁱⁱ	2.9700
C14···O6ⁱⁱⁱ	3.287 (5)	H18B···O1^viii	2.7000
C16···O8^iv	3.261 (4)	H19A···O7	2.5800
C16···O4^vi	3.228 (4)	H19A···O10	2.2500
C17···O10	3.330 (4)	H19A···H14A^viii	2.3100
C17···C20	3.541 (4)	H19B···C4^v	3.0900
C17···O5	3.042 (3)	H19B···C5^v	3.0900
C18···O1^viii	3.398 (4)	H21A···H4^xii	2.4000
C20···C17	3.541 (4)	H21B···H9^v	2.5500

C8—O2—C12	112.27 (18)	C3—C4—H4	120.00
C9—O3—C13	117.56 (19)	C5—C4—H4	120.00
C10—O5—C15	118.7 (2)	C4—C5—H5	119.00
C11—O7—C17	118.21 (18)	C6—C5—H5	119.00
C19—O9—C20	118.2 (2)	N1—C7—H7	119.00
C1—O1—HO1	105 (2)	C6—C7—H7	119.00
C7—N1—C8	121.6 (2)	O2—C8—H8	109.00
O1—C1—C2	118.2 (3)	N1—C8—H8	109.00
C2—C1—C6	120.1 (3)	C9—C8—H8	109.00
O1—C1—C6	121.7 (2)	O3—C9—H9	110.00
C1—C2—C3	119.7 (4)	C8—C9—H9	110.00
C2—C3—C4	121.2 (4)	C10—C9—H9	110.00
C3—C4—C5	119.1 (5)	O5—C10—H10	110.00
C4—C5—C6	121.1 (4)	C9—C10—H10	110.00
C1—C6—C5	118.7 (3)	C11—C10—H10	110.00
C5—C6—C7	120.7 (3)	O7—C11—H11	110.00
C1—C6—C7	120.6 (2)	C10—C11—H11	110.00
N1—C7—C6	122.0 (2)	C12—C11—H11	110.00
O2—C8—C9	108.40 (19)	O2—C12—H12	109.00
N1—C8—C9	109.63 (19)	C11—C12—H12	109.00
O2—C8—N1	111.83 (19)	C19—C12—H12	109.00
O3—C9—C10	107.87 (18)	C13—C14—H14A	109.00
C8—C9—C10	108.48 (19)	C13—C14—H14B	109.00
O3—C9—C8	110.96 (19)	C13—C14—H14C	110.00
O5—C10—C11	108.65 (19)	H14A—C14—H14B	109.00
C9—C10—C11	109.77 (19)	H14A—C14—H14C	109.00
O5—C10—C9	108.68 (19)	H14B—C14—H14C	110.00
O7—C11—C10	107.83 (19)	C15—C16—H16A	109.00
C10—C11—C12	110.8 (2)	C15—C16—H16B	109.00
O7—C11—C12	109.05 (19)	C15—C16—H16C	109.00
O2—C12—C11	110.85 (19)	H16A—C16—H16B	110.00
C11—C12—C19	114.9 (2)	H16A—C16—H16C	109.00
O2—C12—C19	104.6 (2)	H16B—C16—H16C	109.00
O3—C13—C14	110.8 (3)	C17—C18—H18A	110.00
O4—C13—C14	126.4 (3)	C17—C18—H18B	109.00
O3—C13—O4	122.8 (2)	C17—C18—H18C	110.00
O5—C15—C16	112.0 (3)	H18A—C18—H18B	109.00
O6—C15—C16	126.1 (3)	H18A—C18—H18C	109.00
O5—C15—O6	121.9 (3)	H18B—C18—H18C	110.00
O7—C17—C18	111.6 (2)	O9—C19—H19A	110.00
O8—C17—C18	124.8 (3)	O9—C19—H19B	110.00
O7—C17—O8	123.6 (3)	C12—C19—H19A	110.00
O9—C19—C12	107.4 (2)	C12—C19—H19B	110.00
O9—C20—C21	111.0 (3)	H19A—C19—H19B	108.00
O10—C20—C21	125.7 (3)	C20—C21—H21A	109.00
O9—C20—O10	123.3 (3)	C20—C21—H21B	109.00
C1—C2—H2	120.00	C20—C21—H21C	109.00
C3—C2—H2	120.00	H21A—C21—H21B	110.00
C2—C3—H3	119.00	H21A—C21—H21C	110.00
C4—C3—H3	119.00	H21B—C21—H21C	109.00

C12—O2—C8—C9	−64.9 (2)	O1—C1—C2—C3	−178.5 (4)
C12—O2—C8—N1	174.17 (19)	C1—C2—C3—C4	−0.6 (7)
C8—O2—C12—C11	60.3 (3)	C2—C3—C4—C5	−0.1 (8)
C8—O2—C12—C19	−175.3 (2)	C3—C4—C5—C6	1.2 (7)
C13—O3—C9—C10	−135.4 (2)	C4—C5—C6—C7	178.7 (4)
C9—O3—C13—C14	176.7 (3)	C4—C5—C6—C1	−1.6 (5)
C9—O3—C13—O4	−3.8 (4)	C1—C6—C7—N1	0.5 (4)
C13—O3—C9—C8	105.9 (2)	C5—C6—C7—N1	−179.8 (3)
C15—O5—C10—C11	106.8 (2)	O2—C8—C9—C10	62.4 (2)
C10—O5—C15—O6	8.2 (4)	N1—C8—C9—O3	−56.9 (2)
C10—O5—C15—C16	−169.6 (2)	N1—C8—C9—C10	−175.23 (19)
C15—O5—C10—C9	−133.8 (2)	O2—C8—C9—O3	−179.23 (17)
C17—O7—C11—C12	137.8 (2)	O3—C9—C10—O5	64.5 (2)
C11—O7—C17—C18	173.0 (2)	C8—C9—C10—C11	−56.6 (2)
C17—O7—C11—C10	−101.8 (2)	C8—C9—C10—O5	−175.25 (18)
C11—O7—C17—O8	−5.7 (4)	O3—C9—C10—C11	−176.82 (19)
C19—O9—C20—O10	5.6 (5)	O5—C10—C11—C12	170.96 (18)
C20—O9—C19—C12	122.7 (3)	O5—C10—C11—O7	51.7 (2)
C19—O9—C20—C21	−173.6 (3)	C9—C10—C11—C12	52.2 (3)
C7—N1—C8—O2	−6.2 (3)	C9—C10—C11—O7	−67.0 (2)
C8—N1—C7—C6	179.4 (2)	C10—C11—C12—C19	−170.9 (2)
C7—N1—C8—C9	−126.4 (2)	C10—C11—C12—O2	−52.6 (3)
O1—C1—C6—C5	179.5 (3)	O7—C11—C12—C19	−52.4 (3)
C2—C1—C6—C7	−179.3 (3)	O7—C11—C12—O2	65.9 (2)
C6—C1—C2—C3	0.2 (5)	C11—C12—C19—O9	−59.4 (3)
C2—C1—C6—C5	0.9 (4)	O2—C12—C19—O9	178.9 (2)
O1—C1—C6—C7	−0.7 (4)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y−1/2, −z+3/2; (iii) x−1, y, z; (iv) x−1/2, −y+3/2, −z+1; (v) x+1, y, z; (vi) x+1/2, −y+3/2, −z+1; (vii) −x+2, y+1/2, −z+3/2; (viii) −x+1, y+1/2, −z+3/2; (ix) x+1/2, −y+3/2, −z+2; (x) x−1/2, −y+3/2, −z+2; (xi) −x+3/2, −y+2, z+1/2; (xii) −x+3/2, −y+2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—HO1···N1	0.96 (4)	1.71 (4)	2.579 (3)	150 (3)
C7—H7···O2	0.93	2.26	2.643 (3)	104
C8—H8···O10ⁱⁱ	0.98	2.48	3.364 (4)	150
C9—H9···O4	0.98	2.28	2.678 (3)	103
C10—H10···O6	0.98	2.26	2.681 (4)	104
C11—H11···O4^v	0.98	2.58	3.401 (3)	141
C11—H11···O8	0.98	2.30	2.707 (4)	104
C14—H14C···O6ⁱⁱⁱ	0.96	2.52	3.287 (5)	137
C16—H16C···O8^iv	0.96	2.45	3.261 (4)	143
C19—H19A···O10	0.97	2.25	2.671 (4)	105

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

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