The structure of the title compound, C17H23N3O10, (2), has been determined as part of our investigation into the synthetic utility of the glucosyl triazole unit in carbohydrate chemistry. Compound (2) was synthesized by the 1,3-dipolar cycloaddition reaction of propargyl alcohol with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl azide under conditions which afforded (2) exclusively with complete retention of anomeric stereochemistry. The six-membered carbohydrate ring adopts a chair conformation. The non-H substituents are located in equatorial positions.
Supporting information
CCDC reference: 628385
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- R factor = 0.038
- wR factor = 0.110
- Data-to-parameter ratio = 7.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.09
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.78 Ratio
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.51 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C31
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C41
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C61
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C42
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 25.00
From the CIF: _reflns_number_total 1922
Count of symmetry unique reflns 1924
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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
6 ALERT level G = General alerts; check
5 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
0 ALERT type 5 Informative message, check
Data collection: MSC/AFC7 Diffractometer Control (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 2003).
4-hydroxymethyl-1-(2',3',4',6'-tetra-
O-acetyl-
β-
D-glucopyranosyl)
-1,2,3-triazole
top
Crystal data top
C17H23N3O10 | F(000) = 452 |
Mr = 429.38 | Dx = 1.390 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2yb | Cell parameters from 22 reflections |
a = 14.8103 (19) Å | θ = 12.9–17.5° |
b = 9.3896 (16) Å | µ = 0.12 mm−1 |
c = 7.6195 (11) Å | T = 295 K |
β = 104.504 (10)° | Prism, colorless |
V = 1025.8 (3) Å3 | 0.35 × 0.20 × 0.20 mm |
Z = 2 | |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.018 |
Radiation source: Rigaku rotating anode | θmax = 25.0°, θmin = 2.6° |
Graphite monochromator | h = 0→17 |
ω–2θ scans | k = −11→11 |
2399 measured reflections | l = −9→8 |
1922 independent reflections | 3 standard reflections every 150 reflections |
1460 reflections with I > 2σ(I) | intensity decay: 0.5% |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.058P)2 + 0.1059P] where P = (Fo2 + 2Fc2)/3 |
1922 reflections | (Δ/σ)max = 0.023 |
271 parameters | Δρmax = 0.21 e Å−3 |
1 restraint | Δρmin = −0.23 e Å−3 |
Special details top
Experimental. The scan width was (1.68 + 0.30tanθ)° with an ω scan speed of 16° per minute
(up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were
recorded at each end of the scan, and the scan time:background time ratio was
2:1. |
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 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 | Uiso*/Ueq | |
O1 | 0.39243 (16) | −0.0693 (3) | 0.1477 (3) | 0.0390 (8) | |
O11 | 0.7255 (2) | −0.1489 (3) | −0.0833 (4) | 0.0541 (10) | |
O21 | 0.36392 (17) | 0.1695 (3) | −0.2369 (3) | 0.0418 (8) | |
O22 | 0.4226 (4) | 0.0410 (5) | −0.4281 (6) | 0.0980 (19) | |
O31 | 0.19370 (18) | 0.0092 (3) | −0.3193 (3) | 0.0442 (9) | |
O32 | 0.1149 (2) | 0.2147 (4) | −0.3309 (5) | 0.0774 (14) | |
O41 | 0.13727 (16) | −0.0637 (3) | 0.0042 (3) | 0.0413 (9) | |
O42 | 0.0961 (2) | −0.2866 (4) | −0.0801 (6) | 0.0738 (13) | |
O61 | 0.22242 (19) | −0.2329 (3) | 0.3409 (4) | 0.0474 (9) | |
O62 | 0.2446 (3) | −0.4675 (4) | 0.3614 (5) | 0.0701 (14) | |
N11 | 0.5063 (2) | 0.0624 (3) | 0.0685 (4) | 0.0370 (9) | |
N12 | 0.5590 (2) | 0.1617 (4) | 0.1749 (4) | 0.0462 (11) | |
N13 | 0.6456 (2) | 0.1338 (4) | 0.1775 (5) | 0.0479 (11) | |
C1 | 0.4073 (2) | 0.0555 (4) | 0.0538 (5) | 0.0361 (11) | |
C2 | 0.3496 (3) | 0.0436 (4) | −0.1413 (5) | 0.0356 (11) | |
C3 | 0.2475 (2) | 0.0362 (4) | −0.1368 (4) | 0.0353 (11) | |
C4 | 0.2305 (2) | −0.0844 (4) | −0.0176 (5) | 0.0375 (11) | |
C5 | 0.3000 (3) | −0.0810 (4) | 0.1710 (5) | 0.0384 (11) | |
C6 | 0.3057 (3) | −0.2173 (5) | 0.2782 (6) | 0.0491 (16) | |
C11 | 0.5602 (2) | −0.0307 (4) | 0.0065 (5) | 0.0401 (12) | |
C12 | 0.6487 (2) | 0.0147 (4) | 0.0766 (5) | 0.0377 (11) | |
C13 | 0.7390 (3) | −0.0516 (5) | 0.0625 (6) | 0.0476 (14) | |
C21 | 0.4022 (3) | 0.1542 (5) | −0.3796 (5) | 0.0482 (14) | |
C22 | 0.4140 (3) | 0.2939 (6) | −0.4613 (6) | 0.0595 (16) | |
C31 | 0.1332 (3) | 0.1095 (5) | −0.4034 (6) | 0.0507 (14) | |
C32 | 0.0916 (4) | 0.0671 (8) | −0.5950 (7) | 0.098 (3) | |
C41 | 0.0758 (3) | −0.1718 (5) | −0.0344 (5) | 0.0432 (12) | |
C42 | −0.0177 (3) | −0.1290 (6) | −0.0147 (8) | 0.0643 (19) | |
C61 | 0.2030 (3) | −0.3651 (5) | 0.3861 (5) | 0.0471 (14) | |
C62 | 0.1235 (4) | −0.3668 (6) | 0.4732 (8) | 0.0705 (19) | |
H1 | 0.38820 | 0.13730 | 0.10930 | 0.0440* | |
H2 | 0.36710 | −0.03840 | −0.19760 | 0.0430* | |
H3 | 0.22890 | 0.12440 | −0.09480 | 0.0430* | |
H4 | 0.23450 | −0.17300 | −0.07470 | 0.0450* | |
H5 | 0.28670 | −0.00240 | 0.23960 | 0.0460* | |
H6A | 0.31160 | −0.29530 | 0.20340 | 0.0590* | |
H6B | 0.35840 | −0.21330 | 0.37940 | 0.0590* | |
H11 | 0.54050 | −0.11040 | −0.06930 | 0.0470* | |
H11A | 0.73710 | −0.10740 | −0.17510 | 0.0640* | |
H13A | 0.78000 | 0.02210 | 0.04440 | 0.0580* | |
H13B | 0.76600 | −0.10010 | 0.17200 | 0.0580* | |
H22A | 0.46830 | 0.34020 | −0.39040 | 0.0720* | |
H22B | 0.42060 | 0.28090 | −0.58110 | 0.0720* | |
H22C | 0.36100 | 0.35250 | −0.46480 | 0.0720* | |
H32A | 0.11510 | −0.02230 | −0.61720 | 0.1170* | |
H32B | 0.10800 | 0.13680 | −0.67370 | 0.1170* | |
H32C | 0.02590 | 0.06380 | −0.61640 | 0.1170* | |
H41A | −0.06220 | −0.13930 | −0.12780 | 0.0780* | |
H42B | −0.01610 | −0.03220 | 0.02300 | 0.0780* | |
H42C | −0.03460 | −0.18770 | 0.07320 | 0.0780* | |
H62A | 0.06860 | −0.33440 | 0.38910 | 0.0860* | |
H62B | 0.11440 | −0.46010 | 0.51150 | 0.0860* | |
H62C | 0.13700 | −0.30440 | 0.57570 | 0.0860* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0298 (12) | 0.0440 (16) | 0.0422 (14) | −0.0004 (12) | 0.0069 (10) | 0.0060 (13) |
O11 | 0.0546 (17) | 0.0474 (17) | 0.0656 (19) | 0.0019 (15) | 0.0250 (15) | 0.0041 (16) |
O21 | 0.0430 (14) | 0.0415 (16) | 0.0430 (14) | 0.0051 (13) | 0.0145 (11) | 0.0043 (13) |
O22 | 0.169 (4) | 0.068 (3) | 0.087 (3) | 0.005 (3) | 0.088 (3) | −0.005 (2) |
O31 | 0.0409 (15) | 0.0495 (17) | 0.0371 (14) | 0.0074 (13) | 0.0004 (11) | −0.0095 (13) |
O32 | 0.064 (2) | 0.073 (3) | 0.080 (2) | 0.0263 (19) | −0.0102 (17) | −0.017 (2) |
O41 | 0.0281 (12) | 0.0417 (16) | 0.0546 (16) | −0.0033 (12) | 0.0112 (11) | −0.0108 (14) |
O42 | 0.0462 (18) | 0.051 (2) | 0.124 (3) | −0.0090 (16) | 0.0211 (18) | −0.029 (2) |
O61 | 0.0464 (15) | 0.0444 (17) | 0.0581 (17) | 0.0033 (14) | 0.0256 (13) | 0.0066 (14) |
O62 | 0.092 (3) | 0.047 (2) | 0.080 (2) | 0.0118 (19) | 0.0377 (19) | 0.0085 (18) |
N11 | 0.0329 (15) | 0.0341 (17) | 0.0423 (16) | −0.0022 (14) | 0.0061 (13) | −0.0018 (15) |
N12 | 0.0365 (17) | 0.0426 (19) | 0.0561 (19) | −0.0075 (16) | 0.0050 (15) | −0.0104 (18) |
N13 | 0.0333 (18) | 0.043 (2) | 0.063 (2) | −0.0035 (16) | 0.0041 (15) | −0.0005 (18) |
C1 | 0.0293 (18) | 0.037 (2) | 0.041 (2) | −0.0006 (16) | 0.0067 (15) | −0.0030 (18) |
C2 | 0.0334 (19) | 0.033 (2) | 0.040 (2) | 0.0016 (16) | 0.0084 (15) | −0.0011 (17) |
C3 | 0.0312 (18) | 0.042 (2) | 0.0296 (18) | 0.0020 (16) | 0.0019 (14) | −0.0067 (16) |
C4 | 0.0314 (18) | 0.037 (2) | 0.045 (2) | 0.0015 (16) | 0.0111 (15) | −0.0084 (18) |
C5 | 0.0350 (18) | 0.039 (2) | 0.043 (2) | −0.0029 (17) | 0.0129 (16) | 0.0027 (18) |
C6 | 0.040 (2) | 0.051 (3) | 0.061 (3) | 0.007 (2) | 0.0213 (19) | 0.008 (2) |
C11 | 0.036 (2) | 0.036 (2) | 0.048 (2) | 0.0003 (17) | 0.0101 (17) | −0.0015 (17) |
C12 | 0.0353 (19) | 0.033 (2) | 0.042 (2) | −0.0020 (16) | 0.0047 (16) | 0.0086 (17) |
C13 | 0.033 (2) | 0.042 (2) | 0.065 (3) | 0.0006 (19) | 0.0069 (18) | 0.008 (2) |
C21 | 0.050 (2) | 0.057 (3) | 0.038 (2) | −0.003 (2) | 0.0116 (17) | −0.007 (2) |
C22 | 0.063 (3) | 0.067 (3) | 0.047 (2) | −0.005 (3) | 0.011 (2) | 0.012 (2) |
C31 | 0.035 (2) | 0.064 (3) | 0.049 (2) | 0.012 (2) | 0.0029 (18) | −0.008 (2) |
C32 | 0.086 (4) | 0.149 (7) | 0.045 (3) | 0.062 (4) | −0.011 (3) | −0.018 (4) |
C41 | 0.029 (2) | 0.046 (2) | 0.052 (2) | −0.0034 (18) | 0.0051 (17) | −0.005 (2) |
C42 | 0.041 (3) | 0.073 (4) | 0.080 (3) | −0.013 (2) | 0.017 (2) | −0.014 (3) |
C61 | 0.050 (2) | 0.049 (3) | 0.042 (2) | −0.001 (2) | 0.0109 (18) | 0.006 (2) |
C62 | 0.066 (3) | 0.068 (3) | 0.089 (4) | 0.000 (3) | 0.041 (3) | 0.017 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.419 (5) | C12—C13 | 1.503 (6) |
O1—C5 | 1.428 (5) | C21—C22 | 1.481 (7) |
O11—C13 | 1.413 (5) | C31—C32 | 1.490 (7) |
O21—C2 | 1.432 (5) | C41—C42 | 1.485 (7) |
O21—C21 | 1.354 (5) | C61—C62 | 1.489 (8) |
O22—C21 | 1.189 (7) | C1—H1 | 0.9500 |
O31—C3 | 1.442 (4) | C2—H2 | 0.9500 |
O31—C31 | 1.346 (5) | C3—H3 | 0.9500 |
O32—C31 | 1.196 (6) | C4—H4 | 0.9500 |
O41—C4 | 1.445 (4) | C5—H5 | 0.9500 |
O41—C41 | 1.346 (5) | C6—H6A | 0.9500 |
O42—C41 | 1.194 (6) | C6—H6B | 0.9500 |
O61—C6 | 1.437 (5) | C11—H11 | 0.9500 |
O61—C61 | 1.339 (5) | C13—H13A | 0.9500 |
O62—C61 | 1.182 (6) | C13—H13B | 0.9500 |
O11—H11A | 0.8500 | C22—H22A | 0.9500 |
N11—N12 | 1.349 (4) | C22—H22B | 0.9500 |
N11—C11 | 1.347 (5) | C22—H22C | 0.9500 |
N11—C1 | 1.444 (4) | C32—H32A | 0.9400 |
N12—N13 | 1.304 (4) | C32—H32B | 0.9600 |
N13—C12 | 1.364 (5) | C32—H32C | 0.9500 |
C1—C2 | 1.522 (5) | C42—H41A | 0.9500 |
C2—C3 | 1.523 (5) | C42—H42B | 0.9500 |
C3—C4 | 1.512 (5) | C42—H42C | 0.9500 |
C4—C5 | 1.544 (5) | C62—H62A | 0.9500 |
C5—C6 | 1.509 (6) | C62—H62B | 0.9400 |
C11—C12 | 1.354 (5) | C62—H62C | 0.9600 |
| | | |
O1···N12 | 3.252 (4) | C4···H1 | 3.1000 |
O11···C3i | 3.373 (5) | C11···H2 | 2.8900 |
O11···O62ii | 2.839 (5) | C12···H6Aii | 2.9500 |
O21···C31 | 3.381 (5) | C13···H3i | 3.0800 |
O21···N11 | 2.901 (4) | C31···H62Av | 3.0600 |
O21···O31 | 2.868 (4) | C32···H42Biii | 3.0900 |
O21···C11ii | 3.359 (5) | C61···H11Ai | 3.0400 |
O22···C5iii | 3.341 (6) | C62···H32Cvi | 2.7800 |
O31···O21 | 2.868 (4) | H1···C4 | 3.1000 |
O31···O41 | 2.877 (3) | H1···H3 | 2.4800 |
O32···C13ii | 3.386 (6) | H1···H5 | 2.3900 |
O41···O61 | 3.013 (4) | H1···O11ii | 2.6000 |
O41···O31 | 2.877 (3) | H2···O22 | 2.2400 |
O61···O41 | 3.013 (4) | H2···C11 | 2.8900 |
O61···C41 | 3.180 (5) | H2···H11 | 2.6000 |
O62···O11i | 2.839 (5) | H3···O32 | 2.3000 |
O62···C13i | 3.392 (6) | H3···H1 | 2.4800 |
O62···C22iv | 3.382 (7) | H3···O11ii | 2.5200 |
O1···H22Ai | 2.5500 | H3···C13ii | 3.0800 |
O11···H3i | 2.5200 | H4···O42 | 2.3000 |
O11···H11 | 2.7900 | H4···H6A | 2.4300 |
O11···H1i | 2.6000 | H4···N13i | 2.7800 |
O22···H5iii | 2.8400 | H5···O22viii | 2.8400 |
O22···H6Biii | 2.8400 | H5···H1 | 2.3900 |
O22···H2 | 2.2400 | H6A···O62 | 2.3800 |
O32···H13Bii | 2.5600 | H6A···H4 | 2.4300 |
O32···H42Cv | 2.7000 | H6A···C12i | 2.9500 |
O32···H62Av | 2.6800 | H6B···O22viii | 2.8400 |
O32···H3 | 2.3000 | H6B···O62 | 2.9100 |
O42···H13Ai | 2.5300 | H6B···H22Ai | 2.6000 |
O42···H4 | 2.3000 | H11···O11 | 2.7900 |
O42···H42Bvi | 2.6800 | H11···C2 | 3.1000 |
O42···H62Ciii | 2.8400 | H11···H2 | 2.6000 |
O42···H32Cvii | 2.9100 | H11···N12i | 2.6100 |
O61···H32Aviii | 2.6100 | H11A···O62ii | 2.0000 |
O62···H22Civ | 2.5400 | H11A···C61ii | 3.0400 |
O62···H6A | 2.3800 | H13A···O42ii | 2.5300 |
O62···H6B | 2.9100 | H13B···O32i | 2.5600 |
O62···H11Ai | 2.0000 | H22A···O1ii | 2.5500 |
N11···O21 | 2.901 (4) | H22A···H6Bii | 2.6000 |
N12···O1 | 3.252 (4) | H22C···O62ix | 2.5400 |
N12···H11ii | 2.6100 | H32A···O61iii | 2.6100 |
N13···H4ii | 2.7800 | H32B···H41Ax | 2.5800 |
C3···O11ii | 3.373 (5) | H32C···O42x | 2.9100 |
C5···O22viii | 3.341 (6) | H32C···C62v | 2.7800 |
C11···O21i | 3.359 (5) | H32C···H62Bv | 2.4200 |
C13···O32i | 3.386 (6) | H41A···H32Bvii | 2.5800 |
C13···O62ii | 3.392 (6) | H42B···C32viii | 3.0900 |
C22···O62ix | 3.382 (7) | H42B···O42v | 2.6800 |
C31···O21 | 3.381 (5) | H42C···O32vi | 2.7000 |
C32···C62v | 3.588 (9) | H62A···O32vi | 2.6800 |
C41···O61 | 3.180 (5) | H62A···C31vi | 3.0600 |
C62···C32vi | 3.588 (9) | H62B···H32Cvi | 2.4200 |
C2···H11 | 3.1000 | H62C···O42viii | 2.8400 |
| | | |
C1—O1—C5 | 113.6 (3) | C1—C2—H2 | 111.00 |
C2—O21—C21 | 117.8 (3) | C3—C2—H2 | 111.00 |
C3—O31—C31 | 118.5 (3) | O31—C3—H3 | 110.00 |
C4—O41—C41 | 119.2 (3) | C2—C3—H3 | 110.00 |
C6—O61—C61 | 116.0 (3) | C4—C3—H3 | 110.00 |
C13—O11—H11A | 109.00 | O41—C4—H4 | 110.00 |
N12—N11—C11 | 110.8 (3) | C3—C4—H4 | 110.00 |
C1—N11—C11 | 128.6 (3) | C5—C4—H4 | 110.00 |
N12—N11—C1 | 120.1 (3) | O1—C5—H5 | 110.00 |
N11—N12—N13 | 106.8 (3) | C4—C5—H5 | 110.00 |
N12—N13—C12 | 109.1 (3) | C6—C5—H5 | 111.00 |
O1—C1—N11 | 106.3 (3) | O61—C6—H6A | 110.00 |
O1—C1—C2 | 108.2 (3) | O61—C6—H6B | 109.00 |
N11—C1—C2 | 113.0 (3) | C5—C6—H6A | 109.00 |
O21—C2—C3 | 108.9 (3) | C5—C6—H6B | 109.00 |
C1—C2—C3 | 107.4 (3) | H6A—C6—H6B | 110.00 |
O21—C2—C1 | 108.5 (3) | N11—C11—H11 | 127.00 |
O31—C3—C2 | 107.4 (3) | C12—C11—H11 | 128.00 |
O31—C3—C4 | 108.2 (3) | O11—C13—H13A | 109.00 |
C2—C3—C4 | 111.3 (3) | O11—C13—H13B | 109.00 |
O41—C4—C3 | 106.0 (3) | C12—C13—H13A | 109.00 |
O41—C4—C5 | 108.9 (3) | C12—C13—H13B | 109.00 |
C3—C4—C5 | 111.8 (3) | H13A—C13—H13B | 109.00 |
O1—C5—C6 | 102.0 (3) | C21—C22—H22A | 110.00 |
C4—C5—C6 | 114.8 (3) | C21—C22—H22B | 110.00 |
O1—C5—C4 | 108.8 (3) | C21—C22—H22C | 110.00 |
O61—C6—C5 | 109.3 (4) | H22A—C22—H22B | 109.00 |
N11—C11—C12 | 104.9 (3) | H22A—C22—H22C | 109.00 |
N13—C12—C11 | 108.3 (3) | H22B—C22—H22C | 109.00 |
C11—C12—C13 | 129.2 (4) | C31—C32—H32A | 110.00 |
N13—C12—C13 | 122.4 (3) | C31—C32—H32B | 109.00 |
O11—C13—C12 | 111.8 (3) | C31—C32—H32C | 109.00 |
O21—C21—O22 | 122.3 (4) | H32A—C32—H32B | 109.00 |
O21—C21—C22 | 111.2 (4) | H32A—C32—H32C | 111.00 |
O22—C21—C22 | 126.5 (4) | H32B—C32—H32C | 109.00 |
O31—C31—O32 | 124.0 (4) | C41—C42—H41A | 109.00 |
O31—C31—C32 | 110.0 (4) | C41—C42—H42B | 110.00 |
O32—C31—C32 | 126.0 (5) | C41—C42—H42C | 109.00 |
O41—C41—C42 | 111.8 (4) | H41A—C42—H42B | 109.00 |
O42—C41—C42 | 125.7 (4) | H41A—C42—H42C | 110.00 |
O41—C41—O42 | 122.6 (4) | H42B—C42—H42C | 109.00 |
O61—C61—C62 | 111.7 (4) | C61—C62—H62A | 110.00 |
O62—C61—C62 | 124.3 (5) | C61—C62—H62B | 110.00 |
O61—C61—O62 | 124.0 (4) | C61—C62—H62C | 109.00 |
O1—C1—H1 | 110.00 | H62A—C62—H62B | 110.00 |
N11—C1—H1 | 110.00 | H62A—C62—H62C | 109.00 |
C2—C1—H1 | 110.00 | H62B—C62—H62C | 109.00 |
O21—C2—H2 | 110.00 | | |
| | | |
C5—O1—C1—N11 | 170.7 (3) | N12—N11—C1—O1 | −108.7 (3) |
C5—O1—C1—C2 | −67.7 (4) | N11—N12—N13—C12 | −1.5 (4) |
C1—O1—C5—C4 | 60.3 (4) | N12—N13—C12—C13 | −175.8 (4) |
C1—O1—C5—C6 | −178.0 (3) | N12—N13—C12—C11 | 1.2 (4) |
C21—O21—C2—C1 | 118.4 (3) | O1—C1—C2—O21 | 179.8 (3) |
C21—O21—C2—C3 | −125.0 (3) | N11—C1—C2—C3 | 179.6 (3) |
C2—O21—C21—O22 | 1.1 (6) | O1—C1—C2—C3 | 62.2 (4) |
C2—O21—C21—C22 | −178.9 (3) | N11—C1—C2—O21 | −62.9 (4) |
C31—O31—C3—C2 | −115.5 (4) | C1—C2—C3—O31 | −173.8 (3) |
C31—O31—C3—C4 | 124.2 (3) | O21—C2—C3—C4 | −172.9 (3) |
C3—O31—C31—O32 | −7.0 (6) | O21—C2—C3—O31 | 68.9 (4) |
C3—O31—C31—C32 | 174.7 (4) | C1—C2—C3—C4 | −55.5 (4) |
C41—O41—C4—C3 | 126.9 (3) | O31—C3—C4—C5 | 168.4 (3) |
C41—O41—C4—C5 | −112.6 (3) | O31—C3—C4—O41 | −73.1 (3) |
C4—O41—C41—O42 | 2.8 (6) | C2—C3—C4—O41 | 169.1 (3) |
C4—O41—C41—C42 | −176.7 (3) | C2—C3—C4—C5 | 50.6 (4) |
C61—O61—C6—C5 | 159.4 (3) | O41—C4—C5—C6 | 79.4 (4) |
C6—O61—C61—O62 | −7.3 (6) | O41—C4—C5—O1 | −167.2 (3) |
C6—O61—C61—C62 | 172.0 (4) | C3—C4—C5—O1 | −50.3 (4) |
C1—N11—N12—N13 | 173.5 (3) | C3—C4—C5—C6 | −163.8 (3) |
C11—N11—N12—N13 | 1.3 (4) | O1—C5—C6—O61 | 170.1 (3) |
N12—N11—C1—C2 | 132.8 (3) | C4—C5—C6—O61 | −72.4 (4) |
C11—N11—C1—O1 | 61.9 (4) | N11—C11—C12—C13 | 176.3 (4) |
C11—N11—C1—C2 | −56.6 (5) | N11—C11—C12—N13 | −0.4 (4) |
N12—N11—C11—C12 | −0.6 (4) | C11—C12—C13—O11 | 19.1 (6) |
C1—N11—C11—C12 | −171.9 (3) | N13—C12—C13—O11 | −164.6 (4) |
Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x+1, y+1/2, −z; (iii) x, y, z−1; (iv) x, y−1, z+1; (v) −x, y+1/2, −z; (vi) −x, y−1/2, −z; (vii) −x, y−1/2, −z−1; (viii) x, y, z+1; (ix) x, y+1, z−1; (x) −x, y+1/2, −z−1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11A···O62ii | 0.8500 | 2.0000 | 2.839 (5) | 166.00 |
C1—H1···O11ii | 0.9500 | 2.6000 | 3.442 (5) | 148.00 |
C2—H2···O22 | 0.9500 | 2.2400 | 2.670 (7) | 106.00 |
C3—H3···O32 | 0.9500 | 2.3000 | 2.720 (5) | 106.00 |
C3—H3···O11ii | 0.9500 | 2.5200 | 3.373 (5) | 148.00 |
C4—H4···O42 | 0.9500 | 2.3000 | 2.705 (5) | 105.00 |
C11—H11···N12i | 0.9500 | 2.6100 | 3.485 (5) | 154.00 |
C13—H13A···O42ii | 0.9500 | 2.5300 | 3.466 (6) | 166.00 |
C13—H13B···O32i | 0.9500 | 2.5600 | 3.386 (6) | 146.00 |
C22—H22A···O1ii | 0.9500 | 2.5500 | 3.485 (5) | 168.00 |
C22—H22C···O62ix | 0.9500 | 2.5400 | 3.382 (7) | 148.00 |
Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x+1, y+1/2, −z; (ix) x, y+1, z−1. |