Abstract
In the crystal structure of the title compound, [Co(C2H4NO2)(C9H6NO)2]·CH3OH, the CoIII atom is chelated by two quinolin-8-olate and one glycinate anions in a distorted octahedral coordination geometry. The five-membered chelating glycinate ring assumes an envelope conformation. The complex molecules are assembled by intermolecular N—H⋯O hydrogen bonding.
Related literature
For a related structure, see: Li et al. (2003 ▶).
Experimental
Crystal data
[Co(C2H4NO2)(C9H6NO)2]·CH4O
M r = 453.33
Triclinic,
a = 9.8377 (4) Å
b = 10.6526 (4) Å
c = 10.7369 (4) Å
α = 82.047 (1)°
β = 76.289 (1)°
γ = 64.941 (1)°
V = 989.32 (7) Å3
Z = 2
Mo Kα radiation
μ = 0.91 mm−1
T = 273 (2) K
0.20 × 0.15 × 0.12 mm
Data collection
Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.840, T max = 0.899
11346 measured reflections
3486 independent reflections
3261 reflections with I > 2σ(I)
R int = 0.017
Refinement
R[F 2 > 2σ(F 2)] = 0.028
wR(F 2) = 0.093
S = 1.00
3486 reflections
281 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρmax = 0.28 e Å−3
Δρmin = −0.36 e Å−3
Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supplementary Material
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808013135/xu2418sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013135/xu2418Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Enhanced figure: interactive version of Fig. 3
Table 1. Selected geometric parameters (Å, °).
| Co1—O1 | 1.9045 (12) |
| Co1—O3 | 1.8926 (13) |
| Co1—O4 | 1.9002 (13) |
| Co1—N1 | 1.9373 (14) |
| Co1—N2 | 1.9179 (15) |
| Co1—N3 | 1.9309 (15) |
| O3—Co1—O4 | 90.60 (6) |
| O3—Co1—O1 | 89.93 (6) |
| O4—Co1—O1 | 176.81 (5) |
| O3—Co1—N2 | 176.47 (5) |
| O4—Co1—N2 | 85.88 (6) |
| O1—Co1—N2 | 93.56 (6) |
| O3—Co1—N3 | 87.07 (7) |
| O4—Co1—N3 | 91.14 (6) |
| O1—Co1—N3 | 85.75 (6) |
| N2—Co1—N3 | 92.71 (7) |
| O3—Co1—N1 | 85.82 (6) |
| O4—Co1—N1 | 92.39 (6) |
| O1—Co1—N1 | 90.79 (6) |
| N2—Co1—N1 | 94.60 (6) |
| N3—Co1—N1 | 172.09 (7) |
Table 2. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O5—H5⋯O2i | 0.82 | 1.92 | 2.743 (3) | 175 |
| N3—H21⋯O5 | 0.85 (2) | 2.17 (3) | 2.950 (3) | 153 (2) |
| N3—H22⋯O3ii | 0.86 (3) | 2.10 (3) | 2.952 (2) | 169 (2) |
Symmetry codes: (i)
; (ii)
.
Acknowledgments
This work was supported by the Youth Science Foundation of Shanxi Datong University, China (No. 2007Q08).
supplementary crystallographic information
Comment
The 8–hydroxyquinoline (HQ) is a very good ligand, forms complex compounds with various metal ions in solution. The strong chelating action of HQ in solution has been extensively studied and widely used in analytical chemistry. In this work, we use glycin and 8–hydroxyquinoline as bidedtate ligand to synthesize the title complex, (I).
The molecular structure of the title compound is shown in Fig. 1. The CoIII atom is chelated by two 8-hydroxyquinoline and one glycin anions in a distorted octahedral coordination geometry. The Co—N bond distances are longer than Co—O bond distances (Table 1), which agrees with that found in a related structure, tris(8-quinolinolato)-cobalt(III) methanol solvate (Li et al. 2003). The two 8-hydroxyquinolate rings are almost perpendicular to each other with a dihedral angle of 81.0°. The five-membered chelating ring of the glycin assumes an envelope conformation, with N3 atom at the flap position. The complex molecules are assembled by intermolecular N–H···O hydrogen bonding (Table 2). Lattice methanol molecule is linked with complex via O—H···O and N—H···O hydrogen bonding (Fig. 2).
Refinement
Amino H atoms were located in a difference Fourier map and refined isotropically. Other H atoms were placed in calculated positions and allowed to ride on their attached atoms, with C—H = 0.93–0.97 Å, O–H = 0.82 Å, Uiso(H) = 1.2 or 1.5Ueq(C,O).
Figures
Fig. 1.
The atomic labeling scheme of (I) with displacement ellipsoids at the 30% probability level.
Fig. 2.
A packing diagram of the unit cell showing hydrogen bonds as dashed lines. H atoms, except for those involved in hydrogen bonds, are not included.
Fig. 3.
Interactive view of the complex.
Crystal data
| [Co(C2H4NO2)(C9H6NO)2]·CH4O | Z = 2 |
| Mr = 453.33 | F000 = 468 |
| Triclinic, P1 | Dx = 1.522 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 9.8377 (4) Å | Cell parameters from 7882 reflections |
| b = 10.6526 (4) Å | θ = 2.4–28.2º |
| c = 10.7369 (4) Å | µ = 0.91 mm−1 |
| α = 82.047 (1)º | T = 273 (2) K |
| β = 76.289 (1)º | Block, purple |
| γ = 64.941 (1)º | 0.20 × 0.15 × 0.12 mm |
| V = 989.32 (7) Å3 |
Data collection
| Bruker SMART CCD area-detector diffractometer | 3261 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.017 |
| Monochromator: graphite | θmax = 25.1º |
| φ and ω scans | θmin = 2.0º |
| Absorption correction: multi-scan(SADABS; Sheldrick, 1996) | h = −9→11 |
| Tmin = 0.840, Tmax = 0.899 | k = −12→12 |
| 11346 measured reflections | l = −12→12 |
| 3486 independent reflections |
Refinement
| 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)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.073P)2 + 0.17P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.00 | (Δ/σ)max = 0.001 |
| 3486 reflections | Δρmax = 0.28 e Å−3 |
| 281 parameters | Δρmin = −0.36 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
Special details
| 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)
| x | y | z | Uiso*/Ueq | ||
| Co1 | 0.21615 (2) | 0.26369 (2) | 0.46144 (2) | 0.03237 (12) | |
| O1 | 0.36577 (14) | 0.20861 (13) | 0.56554 (12) | 0.0381 (3) | |
| O2 | 0.46440 (17) | 0.29619 (16) | 0.67761 (14) | 0.0553 (4) | |
| O3 | 0.05933 (15) | 0.33761 (13) | 0.60596 (13) | 0.0418 (3) | |
| O4 | 0.06935 (14) | 0.32742 (13) | 0.35430 (13) | 0.0421 (3) | |
| O5 | 0.4828 (3) | 0.4912 (3) | 0.2562 (2) | 0.1083 (9) | |
| H5 | 0.4933 | 0.5573 | 0.2770 | 0.162* | |
| N1 | 0.18775 (16) | 0.09298 (15) | 0.50938 (14) | 0.0348 (3) | |
| N2 | 0.36569 (17) | 0.19377 (15) | 0.30857 (14) | 0.0349 (3) | |
| N3 | 0.23374 (19) | 0.43960 (16) | 0.43835 (17) | 0.0397 (4) | |
| C1 | 0.0225 (2) | 0.23999 (19) | 0.67578 (17) | 0.0391 (4) | |
| C2 | −0.0769 (2) | 0.2598 (2) | 0.7924 (2) | 0.0539 (5) | |
| H2 | −0.1231 | 0.3465 | 0.8279 | 0.065* | |
| C3 | −0.1088 (3) | 0.1483 (3) | 0.8583 (2) | 0.0683 (7) | |
| H3 | −0.1735 | 0.1626 | 0.9386 | 0.082* | |
| C4 | −0.0487 (3) | 0.0206 (3) | 0.8091 (2) | 0.0656 (6) | |
| H4 | −0.0744 | −0.0498 | 0.8543 | 0.079* | |
| C5 | 0.0530 (2) | −0.0043 (2) | 0.6888 (2) | 0.0460 (5) | |
| C6 | 0.1205 (2) | −0.1297 (2) | 0.6232 (2) | 0.0528 (5) | |
| H6 | 0.0999 | −0.2057 | 0.6600 | 0.063* | |
| C7 | 0.2144 (2) | −0.1391 (2) | 0.5076 (2) | 0.0504 (5) | |
| H7 | 0.2567 | −0.2210 | 0.4642 | 0.060* | |
| C8 | 0.2488 (2) | −0.02614 (18) | 0.45221 (19) | 0.0413 (4) | |
| H8 | 0.3162 | −0.0354 | 0.3735 | 0.050* | |
| C9 | 0.08930 (19) | 0.10617 (18) | 0.62504 (17) | 0.0364 (4) | |
| C10 | 0.1360 (2) | 0.30635 (18) | 0.23300 (19) | 0.0422 (4) | |
| C11 | 0.0622 (3) | 0.3473 (2) | 0.1301 (2) | 0.0590 (6) | |
| H11 | −0.0435 | 0.3965 | 0.1439 | 0.071* | |
| C12 | 0.1463 (4) | 0.3150 (3) | 0.0052 (2) | 0.0690 (7) | |
| H12 | 0.0939 | 0.3445 | −0.0622 | 0.083* | |
| C13 | 0.3015 (4) | 0.2421 (3) | −0.0224 (2) | 0.0657 (7) | |
| H13 | 0.3530 | 0.2230 | −0.1068 | 0.079* | |
| C14 | 0.3826 (3) | 0.1964 (2) | 0.07908 (19) | 0.0500 (5) | |
| C15 | 0.5417 (3) | 0.1158 (2) | 0.0668 (2) | 0.0576 (5) | |
| H15 | 0.6026 | 0.0903 | −0.0139 | 0.069* | |
| C16 | 0.6059 (2) | 0.0755 (2) | 0.1726 (2) | 0.0558 (5) | |
| H16 | 0.7101 | 0.0205 | 0.1645 | 0.067* | |
| C17 | 0.5149 (2) | 0.1171 (2) | 0.29365 (19) | 0.0438 (4) | |
| H17 | 0.5602 | 0.0904 | 0.3653 | 0.053* | |
| C18 | 0.2987 (2) | 0.23139 (18) | 0.20409 (18) | 0.0393 (4) | |
| C19 | 0.3819 (2) | 0.31043 (19) | 0.60261 (16) | 0.0392 (4) | |
| C20 | 0.2899 (2) | 0.45316 (19) | 0.5487 (2) | 0.0452 (4) | |
| H20A | 0.2040 | 0.5039 | 0.6144 | 0.054* | |
| H20B | 0.3538 | 0.5047 | 0.5221 | 0.054* | |
| C21 | 0.5849 (6) | 0.4394 (5) | 0.1517 (4) | 0.1377 (19) | |
| H21A | 0.5343 | 0.4321 | 0.0885 | 0.207* | |
| H21B | 0.6579 | 0.3490 | 0.1722 | 0.207* | |
| H21C | 0.6367 | 0.4993 | 0.1183 | 0.207* | |
| H22 | 0.143 (3) | 0.502 (3) | 0.436 (2) | 0.060 (7)* | |
| H21 | 0.295 (3) | 0.444 (2) | 0.369 (2) | 0.048 (6)* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Co1 | 0.02705 (16) | 0.02604 (16) | 0.04380 (17) | −0.01193 (11) | −0.00651 (10) | 0.00211 (10) |
| O1 | 0.0359 (7) | 0.0324 (7) | 0.0464 (7) | −0.0132 (5) | −0.0107 (5) | −0.0006 (5) |
| O2 | 0.0585 (9) | 0.0602 (9) | 0.0529 (8) | −0.0229 (7) | −0.0185 (7) | −0.0116 (7) |
| O3 | 0.0365 (7) | 0.0317 (6) | 0.0529 (7) | −0.0144 (5) | 0.0006 (5) | −0.0027 (5) |
| O4 | 0.0315 (6) | 0.0366 (7) | 0.0594 (8) | −0.0142 (5) | −0.0147 (6) | 0.0056 (6) |
| O5 | 0.1061 (17) | 0.1167 (19) | 0.1255 (19) | −0.0846 (16) | 0.0328 (15) | −0.0453 (15) |
| N1 | 0.0294 (7) | 0.0310 (7) | 0.0468 (8) | −0.0139 (6) | −0.0126 (6) | 0.0036 (6) |
| N2 | 0.0330 (8) | 0.0318 (7) | 0.0431 (8) | −0.0165 (6) | −0.0089 (6) | 0.0020 (6) |
| N3 | 0.0316 (8) | 0.0305 (8) | 0.0567 (10) | −0.0144 (7) | −0.0078 (7) | 0.0035 (7) |
| C1 | 0.0321 (9) | 0.0415 (10) | 0.0468 (10) | −0.0187 (7) | −0.0087 (7) | 0.0023 (8) |
| C2 | 0.0489 (12) | 0.0610 (13) | 0.0523 (11) | −0.0273 (10) | 0.0013 (9) | −0.0072 (10) |
| C3 | 0.0685 (15) | 0.0868 (18) | 0.0532 (12) | −0.0460 (14) | 0.0061 (11) | 0.0020 (12) |
| C4 | 0.0710 (15) | 0.0741 (16) | 0.0641 (14) | −0.0506 (13) | −0.0070 (12) | 0.0173 (12) |
| C5 | 0.0414 (10) | 0.0463 (11) | 0.0589 (11) | −0.0272 (9) | −0.0163 (9) | 0.0131 (9) |
| C6 | 0.0506 (11) | 0.0379 (10) | 0.0813 (15) | −0.0285 (9) | −0.0242 (11) | 0.0152 (9) |
| C7 | 0.0458 (11) | 0.0330 (9) | 0.0788 (14) | −0.0189 (8) | −0.0193 (10) | −0.0011 (9) |
| C8 | 0.0377 (9) | 0.0336 (9) | 0.0547 (11) | −0.0146 (7) | −0.0135 (8) | −0.0003 (8) |
| C9 | 0.0310 (9) | 0.0374 (9) | 0.0461 (9) | −0.0185 (7) | −0.0135 (7) | 0.0070 (7) |
| C10 | 0.0461 (10) | 0.0310 (9) | 0.0590 (12) | −0.0226 (8) | −0.0218 (9) | 0.0108 (8) |
| C11 | 0.0656 (14) | 0.0484 (12) | 0.0783 (15) | −0.0302 (11) | −0.0415 (12) | 0.0196 (11) |
| C12 | 0.101 (2) | 0.0613 (15) | 0.0661 (15) | −0.0430 (15) | −0.0491 (15) | 0.0208 (12) |
| C13 | 0.104 (2) | 0.0626 (14) | 0.0471 (12) | −0.0481 (15) | −0.0239 (12) | 0.0099 (10) |
| C14 | 0.0691 (14) | 0.0482 (12) | 0.0451 (10) | −0.0369 (11) | −0.0115 (10) | 0.0026 (9) |
| C15 | 0.0618 (14) | 0.0653 (14) | 0.0516 (12) | −0.0374 (11) | 0.0071 (10) | −0.0148 (10) |
| C16 | 0.0408 (11) | 0.0627 (13) | 0.0630 (13) | −0.0224 (10) | 0.0013 (9) | −0.0159 (10) |
| C17 | 0.0340 (9) | 0.0455 (10) | 0.0523 (10) | −0.0160 (8) | −0.0078 (8) | −0.0051 (8) |
| C18 | 0.0472 (10) | 0.0330 (9) | 0.0463 (10) | −0.0241 (8) | −0.0143 (8) | 0.0062 (7) |
| C19 | 0.0337 (9) | 0.0423 (10) | 0.0383 (9) | −0.0145 (8) | 0.0010 (7) | −0.0084 (7) |
| C20 | 0.0412 (10) | 0.0362 (9) | 0.0614 (12) | −0.0182 (8) | −0.0087 (9) | −0.0070 (8) |
| C21 | 0.197 (5) | 0.142 (4) | 0.116 (3) | −0.129 (4) | 0.030 (3) | −0.047 (3) |
Geometric parameters (Å, °)
| Co1—O1 | 1.9045 (12) | C5—C6 | 1.417 (3) |
| Co1—O3 | 1.8926 (13) | C6—C7 | 1.348 (3) |
| Co1—O4 | 1.9002 (13) | C6—H6 | 0.9300 |
| Co1—N1 | 1.9373 (14) | C7—C8 | 1.403 (3) |
| Co1—N2 | 1.9179 (15) | C7—H7 | 0.9300 |
| Co1—N3 | 1.9309 (15) | C8—H8 | 0.9300 |
| O1—C19 | 1.287 (2) | C10—C11 | 1.384 (3) |
| O2—C19 | 1.225 (2) | C10—C18 | 1.431 (3) |
| O3—C1 | 1.323 (2) | C11—C12 | 1.400 (4) |
| O4—C10 | 1.314 (2) | C11—H11 | 0.9300 |
| O5—C21 | 1.319 (4) | C12—C13 | 1.367 (4) |
| O5—H5 | 0.8200 | C12—H12 | 0.9300 |
| N1—C8 | 1.320 (2) | C13—C14 | 1.413 (3) |
| N1—C9 | 1.365 (2) | C13—H13 | 0.9300 |
| N2—C17 | 1.326 (2) | C14—C18 | 1.405 (3) |
| N2—C18 | 1.362 (2) | C14—C15 | 1.413 (3) |
| N3—C20 | 1.468 (3) | C15—C16 | 1.361 (3) |
| N3—H22 | 0.86 (3) | C15—H15 | 0.9300 |
| N3—H21 | 0.85 (2) | C16—C17 | 1.399 (3) |
| C1—C2 | 1.374 (3) | C16—H16 | 0.9300 |
| C1—C9 | 1.419 (3) | C17—H17 | 0.9300 |
| C2—C3 | 1.410 (3) | C19—C20 | 1.518 (3) |
| C2—H2 | 0.9300 | C20—H20A | 0.9700 |
| C3—C4 | 1.359 (4) | C20—H20B | 0.9700 |
| C3—H3 | 0.9300 | C21—H21A | 0.9600 |
| C4—C5 | 1.414 (3) | C21—H21B | 0.9600 |
| C4—H4 | 0.9300 | C21—H21C | 0.9600 |
| C5—C9 | 1.414 (2) | ||
| O3—Co1—O4 | 90.60 (6) | C6—C7—H7 | 119.8 |
| O3—Co1—O1 | 89.93 (6) | C8—C7—H7 | 119.8 |
| O4—Co1—O1 | 176.81 (5) | N1—C8—C7 | 121.45 (18) |
| O3—Co1—N2 | 176.47 (5) | N1—C8—H8 | 119.3 |
| O4—Co1—N2 | 85.88 (6) | C7—C8—H8 | 119.3 |
| O1—Co1—N2 | 93.56 (6) | N1—C9—C5 | 122.64 (17) |
| O3—Co1—N3 | 87.07 (7) | N1—C9—C1 | 115.27 (15) |
| O4—Co1—N3 | 91.14 (6) | C5—C9—C1 | 122.07 (17) |
| O1—Co1—N3 | 85.75 (6) | O4—C10—C11 | 125.8 (2) |
| N2—Co1—N3 | 92.71 (7) | O4—C10—C18 | 117.56 (16) |
| O3—Co1—N1 | 85.82 (6) | C11—C10—C18 | 116.6 (2) |
| O4—Co1—N1 | 92.39 (6) | C10—C11—C12 | 120.2 (2) |
| O1—Co1—N1 | 90.79 (6) | C10—C11—H11 | 119.9 |
| N2—Co1—N1 | 94.60 (6) | C12—C11—H11 | 119.9 |
| N3—Co1—N1 | 172.09 (7) | C13—C12—C11 | 123.2 (2) |
| C19—O1—Co1 | 113.96 (11) | C13—C12—H12 | 118.4 |
| C1—O3—Co1 | 111.40 (11) | C11—C12—H12 | 118.4 |
| C10—O4—Co1 | 111.26 (11) | C12—C13—C14 | 119.0 (2) |
| C21—O5—H5 | 109.5 | C12—C13—H13 | 120.5 |
| C8—N1—C9 | 119.18 (15) | C14—C13—H13 | 120.5 |
| C8—N1—Co1 | 131.33 (13) | C18—C14—C13 | 117.7 (2) |
| C9—N1—Co1 | 109.46 (12) | C18—C14—C15 | 116.45 (19) |
| C17—N2—C18 | 119.37 (17) | C13—C14—C15 | 125.8 (2) |
| C17—N2—Co1 | 129.99 (13) | C16—C15—C14 | 120.2 (2) |
| C18—N2—Co1 | 110.63 (12) | C16—C15—H15 | 119.9 |
| C20—N3—Co1 | 107.24 (11) | C14—C15—H15 | 119.9 |
| C20—N3—H22 | 111.7 (16) | C15—C16—C17 | 119.9 (2) |
| Co1—N3—H22 | 106.0 (17) | C15—C16—H16 | 120.1 |
| C20—N3—H21 | 110.4 (15) | C17—C16—H16 | 120.1 |
| Co1—N3—H21 | 111.4 (15) | N2—C17—C16 | 121.50 (18) |
| H22—N3—H21 | 110 (2) | N2—C17—H17 | 119.3 |
| O3—C1—C2 | 124.64 (18) | C16—C17—H17 | 119.3 |
| O3—C1—C9 | 117.25 (15) | N2—C18—C14 | 122.54 (18) |
| C2—C1—C9 | 118.10 (17) | N2—C18—C10 | 114.32 (17) |
| C1—C2—C3 | 119.9 (2) | C14—C18—C10 | 123.13 (18) |
| C1—C2—H2 | 120.1 | O2—C19—O1 | 123.35 (17) |
| C3—C2—H2 | 120.1 | O2—C19—C20 | 120.82 (17) |
| C4—C3—C2 | 122.5 (2) | O1—C19—C20 | 115.83 (15) |
| C4—C3—H3 | 118.7 | N3—C20—C19 | 109.90 (15) |
| C2—C3—H3 | 118.7 | N3—C20—H20A | 109.7 |
| C3—C4—C5 | 119.62 (19) | C19—C20—H20A | 109.7 |
| C3—C4—H4 | 120.2 | N3—C20—H20B | 109.7 |
| C5—C4—H4 | 120.2 | C19—C20—H20B | 109.7 |
| C4—C5—C9 | 117.7 (2) | H20A—C20—H20B | 108.2 |
| C4—C5—C6 | 126.22 (19) | O5—C21—H21A | 109.5 |
| C9—C5—C6 | 116.04 (18) | O5—C21—H21B | 109.5 |
| C7—C6—C5 | 120.19 (17) | H21A—C21—H21B | 109.5 |
| C7—C6—H6 | 119.9 | O5—C21—H21C | 109.5 |
| C5—C6—H6 | 119.9 | H21A—C21—H21C | 109.5 |
| C6—C7—C8 | 120.45 (19) | H21B—C21—H21C | 109.5 |
Hydrogen-bond geometry (Å, °)
| D—H···A | D—H | H···A | D···A | D—H···A |
| O5—H5···O2i | 0.82 | 1.92 | 2.743 (3) | 175 |
| N3—H21···O5 | 0.85 (2) | 2.17 (3) | 2.950 (3) | 153 (2) |
| N3—H22···O3ii | 0.86 (3) | 2.10 (3) | 2.952 (2) | 169 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2418).
References
- Li, D.-X., Xu, D.-J., Gu, J.-M. & Xu, Y.-Z. (2003). Acta Cryst. E59, m543–m545.
- Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808013135/xu2418sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013135/xu2418Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Enhanced figure: interactive version of Fig. 3



