organic compounds
A new polymorph of 1-({[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminio}methyl)naphthalen-2-olate
aSchool of Chinese Materia Medica, Shanxi University of Traditional Chinese Medicine, Taiyuan 030024, People's Republic of China, and bDepartment of Chemistry, Taiyuan Normal University, Taiyuan 030031, People's Republic of China
*Correspondence e-mail: ruitaozhu@126.com
The title compound, C15H17NO4, containing two molecules in the is a polymorph of the published by Martínez et al. [(2011). Eur. J. Org. Chem. pp. 3137-3145] which at 120 K is monoclinic with one molecule in the Both molecules in the title compound are in the trans form. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds connect molecules, forming a two-dimensional network parallel to (001).
Keywords: Schiff base; 2-hydroxy-1-naphthaldehyde; O—H⋯O hydrogen bonding; N—H⋯O hydrogen bonding; crystal structure.
CCDC reference: 1419383
1. Related literature
For applications of et al. (2007); Chen et al. (2008); May et al.(2004). For background to the potential use of the title compound, see: Dong et al. (2014); Liu et al. (2014). For the structures of related derived from 2-hydroxynapthaldehyde, see: Wang et al. (2011); Kennedy et al. (2013); Abu-Dief et al. (2015). For the first polymorph, see: Martínez et al. (2011).
see: Weber2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: SMART (Bruker, 2002); cell SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 1419383
https://doi.org/10.1107/S205698901501539X/lh5776sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901501539X/lh5776Isup2.hkl
Schiff bases have been receiving considerable attention for many years, mainly due to their importance as ligands in metal complexes with special magnetic (Weber et al., 2007) and selective fluorescence sensor (Dong et al., 2014; Liu et al. , 2014), catalytic (Chen et al., 2008) and biological properties (May et al., 2004).
As a part of our studies on the synthesis and structural properties of
with naphthaldehyde and methylamine, we have determined the structure of the title compound (Fig. 1). Some examples of related structures already appear in the literature (Wang et al., 2011; Kennedy et al., 2013; Abu-Dief et al., 2015). The structure of the title compound contains two molecules in the (Fig. 1) in contrast to the polymorph in which there is a single molecule (Martínez et al., 2011). Both molecules in the title compound are in the trans form. In the crystal, N—H···O and O—H···O hydrogen bonds connect molecules forming a two-dimensional network parallel to (001) (Fig. 2).An ethanol solution (10 mL) of tris(hydroxymethyl)aminomethane (tris, 0.1 mol, 0.1211g) was added to another ethanol (10mL) containing 2-hydroxy-1-naphthaldehyde (0.1 mol, 0.1728 g), Then the solution was refluxed for 2 h and cooled to room temperature. The mixture was filtered and dried under vacuum. The title compound was crystallized as block crystals from a solution of ethanol by slow evaporation.
All H atoms were visible in differnce Fourier maps and the presence of those bonded bonded to N1 and N2 confirm the enolate form. Utimately, all H atoms were placed in calculated positions with C—H = 0.93–0.97Å, N—H = 0.86Å and O—H = 0.82Å and were included in the refinment in a riding-motion approximation with Uiso(H)=1.2Ueq(C,N) and Uiso(H)=1.5Ueq(O).
Schiff bases have been receiving considerable attention for many years, mainly due to their importance as ligands in metal complexes with special magnetic (Weber et al., 2007) and selective fluorescence sensor (Dong et al., 2014; Liu et al. , 2014), catalytic (Chen et al., 2008) and biological properties (May et al., 2004).
As a part of our studies on the synthesis and structural properties of
with naphthaldehyde and methylamine, we have determined the structure of the title compound (Fig. 1). Some examples of related structures already appear in the literature (Wang et al., 2011; Kennedy et al., 2013; Abu-Dief et al., 2015). The structure of the title compound contains two molecules in the (Fig. 1) in contrast to the polymorph in which there is a single molecule (Martínez et al., 2011). Both molecules in the title compound are in the trans form. In the crystal, N—H···O and O—H···O hydrogen bonds connect molecules forming a two-dimensional network parallel to (001) (Fig. 2).For applications of
see: Weber et al. (2007); Chen et al. (2008); May et al.(2004). For background to the potential use of the title compound, see: Dong et al. (2014); Liu et al. (2014). For the structures of related derived from 2-hydroxynapthaldehyde, see: Wang et al. (2011); Kennedy et al. (2013); Abu-Dief et al. (2015). For the first polymorph, see: Martínez et al. (2011).An ethanol solution (10 mL) of tris(hydroxymethyl)aminomethane (tris, 0.1 mol, 0.1211g) was added to another ethanol (10mL) containing 2-hydroxy-1-naphthaldehyde (0.1 mol, 0.1728 g), Then the solution was refluxed for 2 h and cooled to room temperature. The mixture was filtered and dried under vacuum. The title compound was crystallized as block crystals from a solution of ethanol by slow evaporation.
detailsAll H atoms were visible in differnce Fourier maps and the presence of those bonded bonded to N1 and N2 confirm the enolate form. Utimately, all H atoms were placed in calculated positions with C—H = 0.93–0.97Å, N—H = 0.86Å and O—H = 0.82Å and were included in the refinment in a riding-motion approximation with Uiso(H)=1.2Ueq(C,N) and Uiso(H)=1.5Ueq(O).
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. | |
Fig. 2. Part of the crystal structure with the hydrogen bonds drawn as dashed lines. |
C15H17NO4 | F(000) = 1168 |
Mr = 275.30 | Dx = 1.343 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3152 reflections |
a = 9.3540 (8) Å | θ = 2.5–25.6° |
b = 10.0280 (9) Å | µ = 0.10 mm−1 |
c = 29.036 (3) Å | T = 293 K |
β = 91.559 (1)° | Block, colorless |
V = 2722.6 (4) Å3 | 0.49 × 0.45 × 0.44 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 4775 independent reflections |
Radiation source: fine-focus sealed tube | 2778 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
φ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −11→11 |
Tmin = 0.954, Tmax = 0.958 | k = −10→11 |
13224 measured reflections | l = −34→24 |
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)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0453P)2 + 1.3323P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
4775 reflections | Δρmax = 0.37 e Å−3 |
368 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0078 (7) |
C15H17NO4 | V = 2722.6 (4) Å3 |
Mr = 275.30 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.3540 (8) Å | µ = 0.10 mm−1 |
b = 10.0280 (9) Å | T = 293 K |
c = 29.036 (3) Å | 0.49 × 0.45 × 0.44 mm |
β = 91.559 (1)° |
Bruker SMART CCD area-detector diffractometer | 4775 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 2778 reflections with I > 2σ(I) |
Tmin = 0.954, Tmax = 0.958 | Rint = 0.043 |
13224 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.37 e Å−3 |
4775 reflections | Δρmin = −0.20 e Å−3 |
368 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4266 (2) | 0.5340 (2) | 0.65750 (7) | 0.0368 (5) | |
H1 | 0.3778 | 0.4957 | 0.6784 | 0.044* | |
N2 | 0.9319 (2) | 0.9508 (2) | 0.67169 (7) | 0.0368 (5) | |
H2 | 0.8792 | 0.9830 | 0.6928 | 0.044* | |
O1 | 0.80392 (19) | 0.5859 (2) | 0.68816 (8) | 0.0621 (6) | |
H1C | 0.8582 | 0.5347 | 0.7020 | 0.093* | |
O2 | 0.49270 (19) | 0.54635 (19) | 0.74996 (6) | 0.0468 (5) | |
H2C | 0.4247 | 0.5638 | 0.7662 | 0.070* | |
O3 | 0.4541 (2) | 0.8049 (2) | 0.63099 (6) | 0.0501 (5) | |
H3 | 0.4281 | 0.8446 | 0.6540 | 0.075* | |
O4 | 0.20984 (19) | 0.3874 (2) | 0.67796 (6) | 0.0510 (5) | |
O5 | 0.9988 (2) | 0.93735 (19) | 0.76456 (6) | 0.0470 (5) | |
H5 | 0.9340 | 0.9140 | 0.7812 | 0.071* | |
O6 | 1.31332 (18) | 0.91941 (18) | 0.70090 (7) | 0.0493 (5) | |
H6 | 1.3611 | 0.9706 | 0.7171 | 0.074* | |
O7 | 1.1405 (2) | 0.7931 (2) | 0.61213 (6) | 0.0560 (6) | |
H7 | 1.2275 | 0.7836 | 0.6111 | 0.084* | |
O8 | 0.71162 (19) | 1.0887 (2) | 0.69349 (7) | 0.0553 (6) | |
C1 | 0.6809 (3) | 0.5160 (3) | 0.67280 (9) | 0.0414 (7) | |
H1A | 0.6645 | 0.4406 | 0.6929 | 0.050* | |
H1B | 0.6943 | 0.4826 | 0.6419 | 0.050* | |
C2 | 0.5234 (3) | 0.6581 (3) | 0.72181 (8) | 0.0409 (7) | |
H2A | 0.6065 | 0.7050 | 0.7343 | 0.049* | |
H2B | 0.4430 | 0.7193 | 0.7212 | 0.049* | |
C3 | 0.5793 (3) | 0.7303 (3) | 0.64202 (9) | 0.0401 (7) | |
H3A | 0.6485 | 0.7884 | 0.6573 | 0.048* | |
H3B | 0.6206 | 0.6993 | 0.6137 | 0.048* | |
C4 | 0.5521 (2) | 0.6100 (3) | 0.67308 (8) | 0.0327 (6) | |
C5 | 0.3813 (3) | 0.5185 (3) | 0.61482 (9) | 0.0352 (6) | |
H5A | 0.4329 | 0.5604 | 0.5920 | 0.042* | |
C6 | 0.2609 (2) | 0.4436 (2) | 0.60076 (9) | 0.0341 (6) | |
C7 | 0.1775 (3) | 0.3805 (3) | 0.63474 (10) | 0.0403 (7) | |
C8 | 0.0531 (3) | 0.3070 (3) | 0.61916 (11) | 0.0558 (8) | |
H8A | −0.0056 | 0.2676 | 0.6406 | 0.067* | |
C9 | 0.0206 (3) | 0.2948 (3) | 0.57391 (12) | 0.0593 (9) | |
H9 | −0.0601 | 0.2458 | 0.5652 | 0.071* | |
C10 | 0.1033 (3) | 0.3528 (3) | 0.53867 (10) | 0.0465 (7) | |
C11 | 0.2235 (3) | 0.4311 (3) | 0.55185 (9) | 0.0386 (6) | |
C12 | 0.2988 (3) | 0.4917 (3) | 0.51637 (9) | 0.0521 (8) | |
H12 | 0.3777 | 0.5446 | 0.5239 | 0.063* | |
C13 | 0.2595 (3) | 0.4752 (4) | 0.47095 (11) | 0.0626 (9) | |
H13 | 0.3120 | 0.5169 | 0.4483 | 0.075* | |
C14 | 0.1425 (4) | 0.3972 (3) | 0.45827 (12) | 0.0653 (9) | |
H14 | 0.1170 | 0.3856 | 0.4274 | 0.078* | |
C15 | 0.0658 (3) | 0.3381 (3) | 0.49156 (12) | 0.0584 (9) | |
H15 | −0.0134 | 0.2867 | 0.4831 | 0.070* | |
C16 | 1.0373 (3) | 0.8292 (3) | 0.73559 (9) | 0.0427 (7) | |
H16A | 0.9611 | 0.7635 | 0.7346 | 0.051* | |
H16B | 1.1231 | 0.7866 | 0.7480 | 0.051* | |
C17 | 1.1832 (2) | 0.9830 (3) | 0.68673 (9) | 0.0389 (7) | |
H17A | 1.1919 | 1.0195 | 0.6560 | 0.047* | |
H17B | 1.1621 | 1.0556 | 0.7076 | 0.047* | |
C18 | 1.0944 (3) | 0.7591 (3) | 0.65660 (9) | 0.0421 (7) | |
H18A | 1.1673 | 0.7048 | 0.6718 | 0.051* | |
H18B | 1.0083 | 0.7056 | 0.6535 | 0.051* | |
C19 | 1.0635 (2) | 0.8799 (3) | 0.68711 (8) | 0.0340 (6) | |
C20 | 0.8883 (3) | 0.9693 (3) | 0.62907 (8) | 0.0343 (6) | |
H20 | 0.9424 | 0.9323 | 0.6059 | 0.041* | |
C21 | 0.7644 (2) | 1.0416 (2) | 0.61581 (8) | 0.0332 (6) | |
C22 | 0.6788 (3) | 1.0992 (3) | 0.65039 (10) | 0.0399 (7) | |
C23 | 0.5528 (3) | 1.1703 (3) | 0.63563 (11) | 0.0544 (8) | |
H23 | 0.4930 | 1.2061 | 0.6575 | 0.065* | |
C24 | 0.5195 (3) | 1.1862 (3) | 0.59069 (12) | 0.0601 (9) | |
H24 | 0.4369 | 1.2330 | 0.5825 | 0.072* | |
C25 | 0.6046 (3) | 1.1347 (3) | 0.55519 (10) | 0.0468 (7) | |
C26 | 0.7267 (3) | 1.0578 (3) | 0.56717 (9) | 0.0379 (6) | |
C27 | 0.8045 (3) | 1.0038 (3) | 0.53105 (9) | 0.0499 (8) | |
H27 | 0.8845 | 0.9517 | 0.5379 | 0.060* | |
C28 | 0.7657 (4) | 1.0257 (4) | 0.48594 (10) | 0.0666 (10) | |
H28 | 0.8193 | 0.9881 | 0.4627 | 0.080* | |
C29 | 0.6471 (4) | 1.1036 (4) | 0.47439 (12) | 0.0718 (11) | |
H29 | 0.6221 | 1.1195 | 0.4437 | 0.086* | |
C30 | 0.5683 (4) | 1.1560 (3) | 0.50842 (12) | 0.0660 (10) | |
H30 | 0.4883 | 1.2072 | 0.5007 | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0296 (11) | 0.0475 (14) | 0.0333 (13) | −0.0042 (10) | 0.0018 (9) | 0.0056 (10) |
N2 | 0.0278 (11) | 0.0511 (14) | 0.0316 (12) | 0.0033 (10) | 0.0016 (9) | −0.0024 (10) |
O1 | 0.0331 (11) | 0.0564 (14) | 0.0959 (18) | −0.0041 (10) | −0.0162 (11) | 0.0145 (12) |
O2 | 0.0380 (11) | 0.0629 (13) | 0.0397 (11) | 0.0065 (9) | 0.0037 (8) | 0.0169 (10) |
O3 | 0.0546 (12) | 0.0534 (13) | 0.0419 (11) | 0.0079 (10) | −0.0087 (9) | 0.0062 (10) |
O4 | 0.0441 (11) | 0.0665 (14) | 0.0426 (12) | −0.0097 (10) | 0.0063 (9) | 0.0055 (10) |
O5 | 0.0437 (11) | 0.0620 (13) | 0.0356 (11) | −0.0067 (10) | 0.0048 (8) | −0.0086 (10) |
O6 | 0.0334 (10) | 0.0512 (13) | 0.0626 (14) | 0.0027 (9) | −0.0113 (9) | −0.0158 (10) |
O7 | 0.0493 (12) | 0.0768 (15) | 0.0420 (12) | 0.0052 (12) | 0.0060 (9) | −0.0067 (11) |
O8 | 0.0439 (12) | 0.0816 (16) | 0.0407 (12) | 0.0112 (11) | 0.0049 (9) | −0.0078 (11) |
C1 | 0.0322 (15) | 0.0486 (18) | 0.0434 (16) | −0.0010 (13) | 0.0009 (12) | 0.0029 (13) |
C2 | 0.0423 (15) | 0.0474 (17) | 0.0329 (15) | 0.0007 (13) | −0.0015 (12) | 0.0015 (13) |
C3 | 0.0341 (14) | 0.0450 (17) | 0.0411 (16) | −0.0004 (13) | −0.0006 (12) | 0.0030 (13) |
C4 | 0.0270 (13) | 0.0352 (15) | 0.0357 (15) | −0.0040 (11) | −0.0013 (11) | 0.0055 (12) |
C5 | 0.0322 (14) | 0.0388 (16) | 0.0346 (15) | 0.0034 (12) | 0.0036 (11) | 0.0015 (12) |
C6 | 0.0280 (13) | 0.0326 (15) | 0.0415 (16) | 0.0011 (11) | −0.0002 (11) | −0.0022 (12) |
C7 | 0.0343 (15) | 0.0380 (16) | 0.0486 (18) | 0.0026 (12) | 0.0038 (13) | 0.0031 (13) |
C8 | 0.0478 (18) | 0.055 (2) | 0.064 (2) | −0.0175 (15) | 0.0032 (16) | 0.0070 (17) |
C9 | 0.0485 (18) | 0.051 (2) | 0.078 (3) | −0.0189 (15) | −0.0109 (17) | −0.0016 (18) |
C10 | 0.0438 (17) | 0.0383 (17) | 0.057 (2) | 0.0016 (14) | −0.0068 (14) | −0.0080 (14) |
C11 | 0.0339 (14) | 0.0388 (16) | 0.0429 (16) | 0.0079 (13) | −0.0013 (12) | −0.0037 (13) |
C12 | 0.0437 (17) | 0.070 (2) | 0.0425 (18) | −0.0051 (15) | −0.0020 (14) | −0.0053 (16) |
C13 | 0.061 (2) | 0.083 (3) | 0.0440 (19) | 0.0016 (19) | −0.0021 (16) | −0.0041 (18) |
C14 | 0.073 (2) | 0.074 (2) | 0.047 (2) | 0.013 (2) | −0.0115 (18) | −0.0167 (18) |
C15 | 0.059 (2) | 0.050 (2) | 0.065 (2) | 0.0017 (16) | −0.0177 (17) | −0.0164 (17) |
C16 | 0.0406 (15) | 0.0502 (18) | 0.0372 (16) | −0.0016 (14) | 0.0004 (12) | 0.0007 (14) |
C17 | 0.0316 (14) | 0.0442 (17) | 0.0409 (16) | 0.0006 (12) | −0.0007 (12) | −0.0027 (13) |
C18 | 0.0390 (15) | 0.0477 (18) | 0.0397 (17) | 0.0002 (13) | 0.0001 (12) | −0.0054 (13) |
C19 | 0.0274 (13) | 0.0444 (16) | 0.0299 (14) | 0.0012 (12) | −0.0031 (11) | −0.0012 (12) |
C20 | 0.0313 (14) | 0.0426 (16) | 0.0291 (14) | −0.0034 (12) | 0.0022 (11) | −0.0030 (12) |
C21 | 0.0271 (13) | 0.0342 (15) | 0.0381 (15) | −0.0039 (11) | −0.0024 (11) | 0.0023 (12) |
C22 | 0.0313 (14) | 0.0414 (17) | 0.0470 (18) | −0.0006 (12) | 0.0020 (12) | −0.0042 (13) |
C23 | 0.0475 (18) | 0.0482 (19) | 0.067 (2) | 0.0123 (15) | 0.0002 (16) | −0.0088 (16) |
C24 | 0.0533 (19) | 0.0450 (19) | 0.081 (3) | 0.0147 (15) | −0.0151 (18) | 0.0043 (17) |
C25 | 0.0475 (17) | 0.0376 (17) | 0.0546 (19) | −0.0048 (14) | −0.0116 (14) | 0.0112 (14) |
C26 | 0.0382 (15) | 0.0371 (16) | 0.0380 (16) | −0.0084 (13) | −0.0059 (12) | 0.0049 (13) |
C27 | 0.0432 (17) | 0.066 (2) | 0.0402 (17) | −0.0057 (15) | −0.0022 (14) | 0.0035 (15) |
C28 | 0.068 (2) | 0.094 (3) | 0.0384 (18) | −0.017 (2) | −0.0031 (16) | 0.0068 (18) |
C29 | 0.080 (3) | 0.089 (3) | 0.046 (2) | −0.026 (2) | −0.0203 (19) | 0.028 (2) |
C30 | 0.065 (2) | 0.061 (2) | 0.070 (2) | −0.0049 (18) | −0.0240 (19) | 0.0281 (19) |
N1—C5 | 1.308 (3) | C10—C15 | 1.411 (4) |
N1—C4 | 1.461 (3) | C10—C11 | 1.415 (4) |
N1—H1 | 0.8600 | C11—C12 | 1.402 (4) |
N2—C20 | 1.306 (3) | C12—C13 | 1.369 (4) |
N2—C19 | 1.480 (3) | C12—H12 | 0.9300 |
N2—H2 | 0.8600 | C13—C14 | 1.387 (4) |
O1—C1 | 1.409 (3) | C13—H13 | 0.9300 |
O1—H1C | 0.8200 | C14—C15 | 1.356 (4) |
O2—C2 | 1.421 (3) | C14—H14 | 0.9300 |
O2—H2C | 0.8200 | C15—H15 | 0.9300 |
O3—C3 | 1.419 (3) | C16—C19 | 1.523 (3) |
O3—H3 | 0.8200 | C16—H16A | 0.9700 |
O4—C7 | 1.285 (3) | C16—H16B | 0.9700 |
O5—C16 | 1.425 (3) | C17—C19 | 1.525 (3) |
O5—H5 | 0.8200 | C17—H17A | 0.9700 |
O6—C17 | 1.425 (3) | C17—H17B | 0.9700 |
O6—H6 | 0.8200 | C18—C19 | 1.532 (3) |
O7—C18 | 1.414 (3) | C18—H18A | 0.9700 |
O7—H7 | 0.8200 | C18—H18B | 0.9700 |
O8—C22 | 1.285 (3) | C20—C21 | 1.412 (3) |
C1—C4 | 1.530 (3) | C20—H20 | 0.9300 |
C1—H1A | 0.9700 | C21—C22 | 1.423 (3) |
C1—H1B | 0.9700 | C21—C26 | 1.455 (3) |
C2—C4 | 1.526 (3) | C22—C23 | 1.433 (4) |
C2—H2A | 0.9700 | C23—C24 | 1.343 (4) |
C2—H2B | 0.9700 | C23—H23 | 0.9300 |
C3—C4 | 1.532 (3) | C24—C25 | 1.417 (4) |
C3—H3A | 0.9700 | C24—H24 | 0.9300 |
C3—H3B | 0.9700 | C25—C30 | 1.407 (4) |
C5—C6 | 1.405 (3) | C25—C26 | 1.414 (4) |
C5—H5A | 0.9300 | C26—C27 | 1.401 (4) |
C6—C7 | 1.423 (3) | C27—C28 | 1.367 (4) |
C6—C11 | 1.459 (3) | C27—H27 | 0.9300 |
C7—C8 | 1.440 (4) | C28—C29 | 1.391 (5) |
C8—C9 | 1.346 (4) | C28—H28 | 0.9300 |
C8—H8A | 0.9300 | C29—C30 | 1.355 (5) |
C9—C10 | 1.424 (4) | C29—H29 | 0.9300 |
C9—H9 | 0.9300 | C30—H30 | 0.9300 |
C5—N1—C4 | 126.3 (2) | C15—C14—C13 | 119.1 (3) |
C5—N1—H1 | 116.9 | C15—C14—H14 | 120.4 |
C4—N1—H1 | 116.9 | C13—C14—H14 | 120.4 |
C20—N2—C19 | 126.2 (2) | C14—C15—C10 | 121.5 (3) |
C20—N2—H2 | 116.9 | C14—C15—H15 | 119.2 |
C19—N2—H2 | 116.9 | C10—C15—H15 | 119.2 |
C1—O1—H1C | 109.5 | O5—C16—C19 | 110.0 (2) |
C2—O2—H2C | 109.5 | O5—C16—H16A | 109.7 |
C3—O3—H3 | 109.5 | C19—C16—H16A | 109.7 |
C16—O5—H5 | 109.5 | O5—C16—H16B | 109.7 |
C17—O6—H6 | 109.5 | C19—C16—H16B | 109.7 |
C18—O7—H7 | 109.5 | H16A—C16—H16B | 108.2 |
O1—C1—C4 | 109.2 (2) | O6—C17—C19 | 108.4 (2) |
O1—C1—H1A | 109.8 | O6—C17—H17A | 110.0 |
C4—C1—H1A | 109.8 | C19—C17—H17A | 110.0 |
O1—C1—H1B | 109.8 | O6—C17—H17B | 110.0 |
C4—C1—H1B | 109.8 | C19—C17—H17B | 110.0 |
H1A—C1—H1B | 108.3 | H17A—C17—H17B | 108.4 |
O2—C2—C4 | 109.1 (2) | O7—C18—C19 | 113.9 (2) |
O2—C2—H2A | 109.9 | O7—C18—H18A | 108.8 |
C4—C2—H2A | 109.9 | C19—C18—H18A | 108.8 |
O2—C2—H2B | 109.9 | O7—C18—H18B | 108.8 |
C4—C2—H2B | 109.9 | C19—C18—H18B | 108.8 |
H2A—C2—H2B | 108.3 | H18A—C18—H18B | 107.7 |
O3—C3—C4 | 113.5 (2) | N2—C19—C16 | 106.65 (19) |
O3—C3—H3A | 108.9 | N2—C19—C17 | 106.0 (2) |
C4—C3—H3A | 108.9 | C16—C19—C17 | 111.7 (2) |
O3—C3—H3B | 108.9 | N2—C19—C18 | 111.9 (2) |
C4—C3—H3B | 108.9 | C16—C19—C18 | 107.9 (2) |
H3A—C3—H3B | 107.7 | C17—C19—C18 | 112.5 (2) |
N1—C4—C2 | 106.98 (19) | N2—C20—C21 | 124.3 (2) |
N1—C4—C1 | 107.7 (2) | N2—C20—H20 | 117.8 |
C2—C4—C1 | 111.0 (2) | C21—C20—H20 | 117.8 |
N1—C4—C3 | 111.9 (2) | C20—C21—C22 | 119.3 (2) |
C2—C4—C3 | 109.5 (2) | C20—C21—C26 | 119.8 (2) |
C1—C4—C3 | 109.8 (2) | C22—C21—C26 | 120.9 (2) |
N1—C5—C6 | 125.1 (2) | O8—C22—C21 | 122.0 (2) |
N1—C5—H5A | 117.5 | O8—C22—C23 | 120.3 (2) |
C6—C5—H5A | 117.5 | C21—C22—C23 | 117.7 (3) |
C5—C6—C7 | 119.1 (2) | C24—C23—C22 | 121.1 (3) |
C5—C6—C11 | 119.9 (2) | C24—C23—H23 | 119.5 |
C7—C6—C11 | 121.0 (2) | C22—C23—H23 | 119.5 |
O4—C7—C6 | 122.3 (2) | C23—C24—C25 | 123.0 (3) |
O4—C7—C8 | 120.1 (2) | C23—C24—H24 | 118.5 |
C6—C7—C8 | 117.6 (3) | C25—C24—H24 | 118.5 |
C9—C8—C7 | 120.8 (3) | C30—C25—C26 | 119.5 (3) |
C9—C8—H8A | 119.6 | C30—C25—C24 | 121.4 (3) |
C7—C8—H8A | 119.6 | C26—C25—C24 | 119.1 (3) |
C8—C9—C10 | 123.5 (3) | C27—C26—C25 | 117.3 (3) |
C8—C9—H9 | 118.2 | C27—C26—C21 | 124.5 (2) |
C10—C9—H9 | 118.2 | C25—C26—C21 | 118.2 (2) |
C15—C10—C11 | 119.7 (3) | C28—C27—C26 | 121.7 (3) |
C15—C10—C9 | 121.9 (3) | C28—C27—H27 | 119.2 |
C11—C10—C9 | 118.4 (3) | C26—C27—H27 | 119.2 |
C12—C11—C10 | 116.9 (3) | C27—C28—C29 | 120.7 (3) |
C12—C11—C6 | 124.4 (2) | C27—C28—H28 | 119.7 |
C10—C11—C6 | 118.6 (2) | C29—C28—H28 | 119.7 |
C13—C12—C11 | 121.9 (3) | C30—C29—C28 | 119.2 (3) |
C13—C12—H12 | 119.1 | C30—C29—H29 | 120.4 |
C11—C12—H12 | 119.1 | C28—C29—H29 | 120.4 |
C12—C13—C14 | 120.8 (3) | C29—C30—C25 | 121.6 (3) |
C12—C13—H13 | 119.6 | C29—C30—H30 | 119.2 |
C14—C13—H13 | 119.6 | C25—C30—H30 | 119.2 |
C5—N1—C4—C2 | 152.3 (2) | C20—N2—C19—C16 | −154.9 (2) |
C5—N1—C4—C1 | −88.3 (3) | C20—N2—C19—C17 | 85.9 (3) |
C5—N1—C4—C3 | 32.4 (3) | C20—N2—C19—C18 | −37.1 (3) |
O2—C2—C4—N1 | 56.2 (3) | O5—C16—C19—N2 | −55.8 (3) |
O2—C2—C4—C1 | −60.9 (3) | O5—C16—C19—C17 | 59.7 (3) |
O2—C2—C4—C3 | 177.73 (19) | O5—C16—C19—C18 | −176.2 (2) |
O1—C1—C4—N1 | −179.4 (2) | O6—C17—C19—N2 | −179.39 (19) |
O1—C1—C4—C2 | −62.6 (3) | O6—C17—C19—C16 | 64.8 (3) |
O1—C1—C4—C3 | 58.5 (3) | O6—C17—C19—C18 | −56.8 (3) |
O3—C3—C4—N1 | 45.6 (3) | O7—C18—C19—N2 | 71.4 (3) |
O3—C3—C4—C2 | −72.8 (3) | O7—C18—C19—C16 | −171.6 (2) |
O3—C3—C4—C1 | 165.1 (2) | O7—C18—C19—C17 | −47.9 (3) |
C4—N1—C5—C6 | 179.3 (2) | C19—N2—C20—C21 | −177.7 (2) |
N1—C5—C6—C7 | 1.3 (4) | N2—C20—C21—C22 | −0.2 (4) |
N1—C5—C6—C11 | −178.4 (2) | N2—C20—C21—C26 | 179.0 (2) |
C5—C6—C7—O4 | −1.3 (4) | C20—C21—C22—O8 | 0.8 (4) |
C11—C6—C7—O4 | 178.4 (2) | C26—C21—C22—O8 | −178.4 (2) |
C5—C6—C7—C8 | 178.6 (2) | C20—C21—C22—C23 | −179.1 (2) |
C11—C6—C7—C8 | −1.6 (4) | C26—C21—C22—C23 | 1.6 (4) |
O4—C7—C8—C9 | −177.6 (3) | O8—C22—C23—C24 | 177.6 (3) |
C6—C7—C8—C9 | 2.5 (4) | C21—C22—C23—C24 | −2.4 (4) |
C7—C8—C9—C10 | −0.7 (5) | C22—C23—C24—C25 | 0.1 (5) |
C8—C9—C10—C15 | −179.8 (3) | C23—C24—C25—C30 | −178.5 (3) |
C8—C9—C10—C11 | −2.0 (5) | C23—C24—C25—C26 | 3.0 (5) |
C15—C10—C11—C12 | 0.6 (4) | C30—C25—C26—C27 | −1.3 (4) |
C9—C10—C11—C12 | −177.2 (3) | C24—C25—C26—C27 | 177.2 (3) |
C15—C10—C11—C6 | −179.4 (2) | C30—C25—C26—C21 | 177.8 (2) |
C9—C10—C11—C6 | 2.8 (4) | C24—C25—C26—C21 | −3.6 (4) |
C5—C6—C11—C12 | −1.2 (4) | C20—C21—C26—C27 | 1.2 (4) |
C7—C6—C11—C12 | 179.0 (3) | C22—C21—C26—C27 | −179.6 (3) |
C5—C6—C11—C10 | 178.7 (2) | C20—C21—C26—C25 | −177.9 (2) |
C7—C6—C11—C10 | −1.0 (4) | C22—C21—C26—C25 | 1.4 (4) |
C10—C11—C12—C13 | −0.7 (4) | C25—C26—C27—C28 | 0.9 (4) |
C6—C11—C12—C13 | 179.3 (3) | C21—C26—C27—C28 | −178.2 (3) |
C11—C12—C13—C14 | 0.0 (5) | C26—C27—C28—C29 | 0.3 (5) |
C12—C13—C14—C15 | 0.7 (5) | C27—C28—C29—C30 | −1.1 (5) |
C13—C14—C15—C10 | −0.8 (5) | C28—C29—C30—C25 | 0.7 (5) |
C11—C10—C15—C14 | 0.1 (4) | C26—C25—C30—C29 | 0.5 (5) |
C9—C10—C15—C14 | 177.9 (3) | C24—C25—C30—C29 | −178.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4 | 0.86 | 1.91 | 2.587 (3) | 135 |
N2—H2···O8 | 0.86 | 1.89 | 2.575 (2) | 135 |
O1—H1C···O5i | 0.82 | 1.90 | 2.715 (3) | 172 |
O2—H2C···O8ii | 0.82 | 1.77 | 2.589 (3) | 173 |
O3—H3···O6iii | 0.82 | 1.91 | 2.706 (3) | 163 |
O5—H5···O4iv | 0.82 | 1.84 | 2.650 (2) | 171 |
O6—H6···O2v | 0.82 | 1.81 | 2.609 (2) | 163 |
O7—H7···O3vi | 0.82 | 2.19 | 2.972 (2) | 159 |
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x−1, y, z; (iv) −x+1, y+1/2, −z+3/2; (v) −x+2, y+1/2, −z+3/2; (vi) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4 | 0.86 | 1.91 | 2.587 (3) | 135 |
N2—H2···O8 | 0.86 | 1.89 | 2.575 (2) | 135 |
O1—H1C···O5i | 0.82 | 1.90 | 2.715 (3) | 172 |
O2—H2C···O8ii | 0.82 | 1.77 | 2.589 (3) | 173 |
O3—H3···O6iii | 0.82 | 1.91 | 2.706 (3) | 163 |
O5—H5···O4iv | 0.82 | 1.84 | 2.650 (2) | 171 |
O6—H6···O2v | 0.82 | 1.81 | 2.609 (2) | 163 |
O7—H7···O3vi | 0.82 | 2.19 | 2.972 (2) | 159 |
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x−1, y, z; (iv) −x+1, y+1/2, −z+3/2; (v) −x+2, y+1/2, −z+3/2; (vi) x+1, y, z. |
Acknowledgements
We gratefully acknowledge the Natural Science Foundation of Shanxi province (grant No. 2015011107), the Research Fund for the Doctoral Program of Shanxi University of Traditional Chinese Medicine (2014) and the College Student's Innovation Traning Project of Shanxi Province (grant No. 2013319).
References
Abu-Dief, A. M., Abdelbaky, M. S. M. & Garcia-Granda, S. (2015). Acta Cryst. E71, o496–o497. CSD CrossRef IUCr Journals Google Scholar
Bruker (2002). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Z. H., Morimoto, H., Matsunaga, S. & Shibasaki, M. (2008). J. Am. Chem. Soc. 130, 2170–2171. Web of Science CSD CrossRef PubMed CAS Google Scholar
Dong, H. K., Ye, S. I., Hyun, K. & Cheal, K. (2014). Inorg. Chem. Commun. 45, 15–19. Google Scholar
Kennedy, A. R., Akkurt, M., Abdelhamid, A. A., Mohamed, S. K. & Miller, G. J. (2013). Acta Cryst. E69, o850–o851. CSD CrossRef IUCr Journals Google Scholar
Liu, Z. C., Li, Y. X., Ding, Y. J., Yang, Z. Y., Wang, B. D., Li, Y., Li, T. R., Luo, W., Zhu, W. P., Xie, J. P. & Wang, C. J. (2014). Sens. Actuators B Chem. 197, 200–205. CrossRef CAS Google Scholar
Martínez, R. F., Ávalos, M., Babiano, R., Cintas, P., Jiménez, J. L., Light, M. E. & Palacios, J. C. (2011). Eur. J. Org. Chem. pp. 3137–3145. Google Scholar
May, J. P., Ting, R., Lermer, L., Thomas, J. M., Roupioz, Y. & Perrin, D. M. (2004). J. Am. Chem. Soc. 126, 4145–4156. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, J., Zhang, J., Yang, P. & Chen, T. (2011). Acta Cryst. E67, o1618. CSD CrossRef IUCr Journals Google Scholar
Weber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem. 633, 1159–1162. Web of Science CSD CrossRef CAS Google Scholar
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