In the title compound, C21H25NO10, the six-membered pyranosyl ring adopts a chair conformation. The crystal structure contains intra- and intermolecular hydrogen-bonding interactions.
Supporting information
CCDC reference: 608483
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
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 |
Mr = 451.42 | Dx = 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 | Rint = 0.091 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.5°, θmin = 2.1° |
ω scans | h = −10→10 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −19→19 |
Tmin = 0.942, Tmax = 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(Fo2) + (0.0555P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
2894 reflections | Δρmax = 0.14 e Å−3 |
298 parameters | Δρmin = −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 | Uiso*/Ueq | |
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···O3vii | 3.404 (4) |
O2···O7 | 2.894 (2) | C1···H3ix | 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···C16iv | 3.228 (4) | C8···HO1 | 2.96 (4) |
O5···O3 | 2.818 (2) | C13···HO1 | 2.91 (4) |
O5···O7 | 2.699 (2) | C19···H14Aviii | 3.0900 |
O5···C17 | 3.042 (3) | C21···H18Bv | 2.9700 |
O5···O8 | 3.203 (3) | HO1···N1 | 1.71 (4) |
O6···C14v | 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···C16vi | 3.261 (4) | H3···C1x | 2.9800 |
O8···O5 | 3.203 (3) | H4···H21Axi | 2.4000 |
O10···C17 | 3.330 (4) | H5···H7 | 2.4500 |
O10···C8vii | 3.364 (4) | H7···O2 | 2.2600 |
O1···H18Bi | 2.7000 | H7···H5 | 2.4500 |
O2···H7 | 2.2600 | H7···H14Bviii | 2.6000 |
O4···H11iii | 2.5800 | H8···H10 | 2.4600 |
O4···H9 | 2.2800 | H8···H12 | 2.3200 |
O5···H16Aiv | 2.8500 | H8···O10ii | 2.4800 |
O6···H14Cv | 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···H16Cvi | 2.4500 | H10···H8 | 2.4600 |
O8···H11 | 2.3000 | H11···O4v | 2.5800 |
O9···H11 | 2.6500 | H11···O8 | 2.3000 |
O10···H19A | 2.2500 | H11···O9 | 2.6500 |
O10···H8vii | 2.4800 | H12···C1v | 2.8000 |
N1···O1 | 2.579 (3) | H12···C2v | 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···O4v | 3.401 (3) | H16A···O5vi | 2.8500 |
C11···C20 | 3.529 (4) | H16C···O8iv | 2.4500 |
C13···N1 | 3.234 (4) | H18B···C21iii | 2.9700 |
C14···O6iii | 3.287 (5) | H18B···O1viii | 2.7000 |
C16···O8iv | 3.261 (4) | H19A···O7 | 2.5800 |
C16···O4vi | 3.228 (4) | H19A···O10 | 2.2500 |
C17···O10 | 3.330 (4) | H19A···H14Aviii | 2.3100 |
C17···C20 | 3.541 (4) | H19B···C4v | 3.0900 |
C17···O5 | 3.042 (3) | H19B···C5v | 3.0900 |
C18···O1viii | 3.398 (4) | H21A···H4xii | 2.4000 |
C20···C17 | 3.541 (4) | H21B···H9v | 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···O4v | 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···O8iv | 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. |