Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044558/at2396sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044558/at2396Isup2.hkl |
CCDC reference: 649515
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.050
- wR factor = 0.067
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.72 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C37 - C38 .. 5.28 su PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Bernstein et al. (1995); Liu et al. (2007); Xia et al. (2007).
A solution of 3-methoxysalicylaldehyde (1.52 g, 10 mmol) and 4-hydroxy aniline (1.09 g, 10 mmol) in ethanol -chloroform (v/v = 1/1) (30 ml) was stirred for 8 h and NaBH4 (0.756 g, 20 mmol) were added, the mixture solution was stirred under room temperature for 48 h and then mixtures was filtered. The filtrate was allowed to evaporate slowly, giving single crystals of (I) suitable for X-ray structure analysis..
All H atoms were located in difference Fourier maps and then repositioned geometrically. They were refined as riding, with C—H distances of 0.93 (aryl), 0.96 (methyl) or 0.97 Å (methylene) and O—H = 0.82 Å. Uiso(H) values were set at xUeq(carrier atom), where x = 1.5 for methyl and hydroxy, x = 1.2 for the other H atoms.
We have recently reported the supramolecular structures of amine derivatives containing hydroxy and methoxy groups, for example, N-(2-hydroxy-3-methoxybenzyl)-4-chloroaniline (Liu et al., 2007), and 6,6'-dimethoxy-2,2'-(2,2,4-trimethylimidazolidine-1,3-diyldimethylene)diphenol (Xia et al., 2007). We have now continued our studies in this area with the title compound, (I), an aniline derivative containing hydroxy and methoxy groups.
Compound (I) crystallizes with the two independent molecules in the asymmetric unit and Z = 4 in the triclinic space group P1 (Fig. 1). In the molecules, the dihedral angles between the phenyl ring (C1–C5) and other two phenyl rings (C8–C13) and (C16–C21) are 86.37 (10)° and 39.09 (10)°, respectively, and the dihedral angles between the phenyl ring (C23–C28) and other two phenyl rings (C30–C35) and (C38–C43) are 48.28 (9)° and 87.37 (9)°, respectively. The C—N bonds involving atom N1 are longer than those involving atom N2 (excluding C15—N1 and C29—N2 bond). The bond angles around the N1 atom are almost in agreement with those around the N2 atom.
The molecules of (I) are linked by O—H···O and C—H···O hydrogen bonds (Table 2) into centrosymmetric tetramers, and these tetramers are further linked by O—H···O, C—H···O hydrogen bonds to form two chains. Atom O6 in the molecule at (1 - x, 2 - y, 1 - z) act as a hydrogen-bond donors, respectively, to atoms O2 and O3 in the molecule at (x, y, z). At the same time, atom O4 in the molecule at (x, y, z) acts as hydrogen-bond donor to atom O6 in the molecule at (x, -1 + y, z), so generating R44(26) and R44(24) (Bernstein et al., 1995) tetramers centred at (1/2, 1/2, 1/2) (Fig. 2). The tetramers are linked into a [011] chain by O—H···O and C—H···O hydrogen bonds. Atom O1 in the molecules at (x, y, z) act as donors, respectively, to atoms O9 and O10 in the molecules at (- x, 1 - y, - z), atoms C5 and O7 in the molecule at (x, y, z) and (x, -1 + y, z) act as hydrogen-bond donors, respectively, to atoms O7 and O1 in the molecule at (x, -1 + y, z) and (x, y, z). Propagation by inversion and translation of these four interactions then generates a chain running parallel to the [011] direction containing R44(24) rings and R44(30) rings centred at (n, n, n) (n = zero or integer), R44(26) and R44(24) rings centred at (1/2 + n, 1/2 + n, 1/2 + n) (n = zero or integer) (Fig. 3). In a similar way, the tetramers are linked into a chain by O—H···O and C—H···O hydrogen bonds parallel to the a axis direction. Atom O6 in the molecule at (-1 + x, -1 + y, z) and (1 - x, 2 - y, 1 - z) accept hydrogen bond from atom C14 in the molecule at (x, y, z), and at the same time, acts as donor to atom O3 in the molecule at (x, y, z), respectively, propagation by inversion and translation of these two interactions then generates a chain running parallel to the a axis direction containing R44(10) rings centred at (n, 1/2, 1/2) (n = zero or integer), R44(26) and R44(24) rings centred at (1/2 + n, 1/2, 1/2) (n = zero or integer) (Fig. 4).
For related literature, see: Bernstein et al. (1995); Liu et al. (2007); Xia et al. (2007).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
C22H23NO5 | Z = 4 |
Mr = 381.41 | F(000) = 808 |
Triclinic, P1 | Dx = 1.324 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4059 (19) Å | Cell parameters from 1304 reflections |
b = 13.699 (2) Å | θ = 2.3–27.8° |
c = 15.196 (2) Å | µ = 0.09 mm−1 |
α = 113.549 (3)° | T = 298 K |
β = 96.908 (2)° | Block, colourless |
γ = 99.792 (2)° | 0.24 × 0.17 × 0.15 mm |
V = 1914.0 (5) Å3 |
Siemens SMART 1000 CCD area-detector diffractometer | 6656 independent reflections |
Radiation source: fine-focus sealed tube | 2772 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.978, Tmax = 0.986 | k = −16→7 |
10128 measured reflections | l = −18→18 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.067 | H-atom parameters constrained |
S = 0.89 | w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3 |
6656 reflections | (Δ/σ)max = 0.012 |
505 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C22H23NO5 | γ = 99.792 (2)° |
Mr = 381.41 | V = 1914.0 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.4059 (19) Å | Mo Kα radiation |
b = 13.699 (2) Å | µ = 0.09 mm−1 |
c = 15.196 (2) Å | T = 298 K |
α = 113.549 (3)° | 0.24 × 0.17 × 0.15 mm |
β = 96.908 (2)° |
Siemens SMART 1000 CCD area-detector diffractometer | 6656 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2772 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.986 | Rint = 0.041 |
10128 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.067 | H-atom parameters constrained |
S = 0.89 | Δρmax = 0.15 e Å−3 |
6656 reflections | Δρmin = −0.18 e Å−3 |
505 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 | 0.3458 (2) | 0.5001 (2) | 0.18136 (16) | 0.0403 (7) | |
N2 | 0.4358 (2) | 0.9610 (2) | 0.19252 (16) | 0.0401 (7) | |
O1 | 0.1094 (2) | 0.05510 (17) | −0.04810 (14) | 0.0731 (8) | |
H1 | 0.0418 | 0.0440 | −0.0879 | 0.110* | |
O2 | 0.24705 (18) | 0.55357 (17) | 0.34615 (12) | 0.0549 (7) | |
H2 | 0.3008 | 0.5341 | 0.3113 | 0.082* | |
O3 | 0.0467 (2) | 0.5905 (2) | 0.42750 (15) | 0.0678 (8) | |
O4 | 0.5303 (2) | 0.49388 (16) | 0.35279 (14) | 0.0595 (7) | |
H4 | 0.5355 | 0.4929 | 0.4067 | 0.089* | |
O5 | 0.6420 (2) | 0.64758 (17) | 0.53099 (15) | 0.0599 (7) | |
O6 | 0.6991 (2) | 1.39497 (17) | 0.44554 (14) | 0.0664 (7) | |
H6 | 0.7205 | 1.4046 | 0.5027 | 0.100* | |
O7 | 0.30272 (19) | 0.95072 (16) | −0.00158 (13) | 0.0532 (6) | |
H7 | 0.2383 | 0.9564 | −0.0344 | 0.080* | |
O8 | 0.1087 (2) | 0.80271 (18) | −0.14366 (15) | 0.0647 (7) | |
O9 | 0.17730 (18) | 0.98333 (16) | 0.17445 (13) | 0.0548 (6) | |
H9 | 0.2501 | 0.9817 | 0.1591 | 0.082* | |
O10 | −0.0183 (2) | 1.0235 (2) | 0.25875 (15) | 0.0716 (8) | |
C1 | 0.2808 (3) | 0.3875 (3) | 0.1176 (2) | 0.0420 (9) | |
C2 | 0.1742 (3) | 0.3542 (3) | 0.0402 (2) | 0.0552 (10) | |
H2A | 0.1425 | 0.4065 | 0.0252 | 0.066* | |
C3 | 0.1133 (3) | 0.2432 (3) | −0.0159 (2) | 0.0610 (11) | |
H3 | 0.0402 | 0.2219 | −0.0669 | 0.073* | |
C4 | 0.1614 (3) | 0.1659 (3) | 0.0042 (2) | 0.0514 (10) | |
C5 | 0.2668 (3) | 0.1982 (3) | 0.0823 (2) | 0.0586 (10) | |
H5 | 0.2980 | 0.1459 | 0.0974 | 0.070* | |
C6 | 0.3257 (3) | 0.3077 (3) | 0.1376 (2) | 0.0512 (9) | |
H6A | 0.3972 | 0.3286 | 0.1895 | 0.061* | |
C7 | 0.2828 (3) | 0.5848 (2) | 0.1707 (2) | 0.0451 (9) | |
H7A | 0.2599 | 0.5679 | 0.1016 | 0.054* | |
H7B | 0.3468 | 0.6552 | 0.2033 | 0.054* | |
C8 | 0.1581 (3) | 0.5936 (2) | 0.2131 (2) | 0.0393 (8) | |
C9 | 0.1497 (3) | 0.5826 (2) | 0.2980 (2) | 0.0425 (9) | |
C10 | 0.0415 (3) | 0.6043 (3) | 0.3434 (2) | 0.0489 (9) | |
C11 | −0.0580 (3) | 0.6366 (3) | 0.3011 (2) | 0.0575 (10) | |
H11 | −0.1302 | 0.6515 | 0.3304 | 0.069* | |
C12 | −0.0498 (3) | 0.6467 (3) | 0.2150 (2) | 0.0593 (11) | |
H12 | −0.1176 | 0.6676 | 0.1862 | 0.071* | |
C13 | 0.0569 (3) | 0.6264 (3) | 0.1709 (2) | 0.0544 (10) | |
H13 | 0.0616 | 0.6344 | 0.1133 | 0.065* | |
C14 | −0.0543 (3) | 0.6161 (3) | 0.4813 (2) | 0.0928 (15) | |
H14A | −0.0568 | 0.6912 | 0.4987 | 0.139* | |
H14B | −0.0358 | 0.6054 | 0.5398 | 0.139* | |
H14C | −0.1389 | 0.5691 | 0.4418 | 0.139* | |
C15 | 0.4914 (3) | 0.5294 (2) | 0.18503 (19) | 0.0474 (9) | |
H15A | 0.5058 | 0.5520 | 0.1334 | 0.057* | |
H15B | 0.5272 | 0.4655 | 0.1736 | 0.057* | |
C16 | 0.5636 (3) | 0.6209 (3) | 0.2829 (2) | 0.0416 (8) | |
C17 | 0.5774 (3) | 0.5989 (3) | 0.3648 (2) | 0.0426 (9) | |
C18 | 0.6368 (3) | 0.6832 (3) | 0.4588 (2) | 0.0460 (9) | |
C19 | 0.6838 (3) | 0.7870 (3) | 0.4686 (2) | 0.0573 (10) | |
H19 | 0.7231 | 0.8430 | 0.5306 | 0.069* | |
C20 | 0.6738 (3) | 0.8101 (3) | 0.3875 (3) | 0.0610 (10) | |
H20 | 0.7071 | 0.8810 | 0.3949 | 0.073* | |
C21 | 0.6141 (3) | 0.7272 (3) | 0.2955 (2) | 0.0532 (10) | |
H21 | 0.6076 | 0.7429 | 0.2412 | 0.064* | |
C22 | 0.7085 (3) | 0.7266 (3) | 0.62790 (19) | 0.0703 (12) | |
H22A | 0.7983 | 0.7573 | 0.6272 | 0.105* | |
H22B | 0.7101 | 0.6915 | 0.6714 | 0.105* | |
H22C | 0.6620 | 0.7839 | 0.6501 | 0.105* | |
C23 | 0.5141 (3) | 1.0693 (3) | 0.2602 (2) | 0.0379 (8) | |
C24 | 0.5500 (3) | 1.1011 (2) | 0.3610 (2) | 0.0441 (9) | |
H24 | 0.5304 | 1.0499 | 0.3862 | 0.053* | |
C25 | 0.6153 (3) | 1.2095 (3) | 0.4240 (2) | 0.0488 (9) | |
H25 | 0.6394 | 1.2304 | 0.4910 | 0.059* | |
C26 | 0.6440 (3) | 1.2852 (3) | 0.3870 (2) | 0.0470 (9) | |
C27 | 0.6139 (3) | 1.2538 (3) | 0.2871 (2) | 0.0444 (9) | |
H27 | 0.6378 | 1.3042 | 0.2618 | 0.053* | |
C28 | 0.5477 (3) | 1.1467 (3) | 0.2252 (2) | 0.0446 (9) | |
H28 | 0.5253 | 1.1263 | 0.1581 | 0.054* | |
C29 | 0.4974 (3) | 0.9035 (2) | 0.10890 (18) | 0.0453 (9) | |
H29A | 0.5642 | 0.8715 | 0.1301 | 0.054* | |
H29B | 0.5413 | 0.9557 | 0.0873 | 0.054* | |
C30 | 0.3925 (3) | 0.8142 (3) | 0.0244 (2) | 0.0408 (9) | |
C31 | 0.2957 (3) | 0.8415 (3) | −0.0254 (2) | 0.0421 (8) | |
C32 | 0.1927 (3) | 0.7609 (3) | −0.1006 (2) | 0.0476 (9) | |
C33 | 0.1868 (3) | 0.6525 (3) | −0.1228 (2) | 0.0561 (10) | |
H33 | 0.1175 | 0.5985 | −0.1711 | 0.067* | |
C34 | 0.2835 (3) | 0.6227 (3) | −0.0739 (2) | 0.0563 (10) | |
H34 | 0.2798 | 0.5492 | −0.0897 | 0.068* | |
C35 | 0.3846 (3) | 0.7035 (3) | −0.0020 (2) | 0.0499 (9) | |
H35 | 0.4498 | 0.6834 | 0.0301 | 0.060* | |
C36 | 0.0044 (3) | 0.7281 (3) | −0.2222 (2) | 0.0889 (14) | |
H36A | 0.0411 | 0.6820 | −0.2740 | 0.133* | |
H36B | −0.0468 | 0.7678 | −0.2461 | 0.133* | |
H36C | −0.0521 | 0.6836 | −0.1999 | 0.133* | |
C37 | 0.3824 (3) | 0.8887 (2) | 0.2352 (2) | 0.0482 (9) | |
H37A | 0.4550 | 0.8861 | 0.2800 | 0.058* | |
H37B | 0.3482 | 0.8153 | 0.1829 | 0.058* | |
C38 | 0.2732 (3) | 0.9204 (2) | 0.2897 (2) | 0.0412 (8) | |
C39 | 0.1764 (3) | 0.9610 (3) | 0.2540 (2) | 0.0416 (9) | |
C40 | 0.0678 (3) | 0.9796 (3) | 0.2994 (2) | 0.0495 (9) | |
C41 | 0.0546 (3) | 0.9549 (3) | 0.3772 (2) | 0.0598 (10) | |
H41 | −0.0182 | 0.9663 | 0.4067 | 0.072* | |
C42 | 0.1512 (4) | 0.9124 (3) | 0.4117 (2) | 0.0624 (11) | |
H42 | 0.1422 | 0.8945 | 0.4640 | 0.075* | |
C43 | 0.2600 (3) | 0.8967 (3) | 0.3690 (2) | 0.0542 (10) | |
H43 | 0.3251 | 0.8700 | 0.3937 | 0.065* | |
C44 | −0.1383 (3) | 1.0354 (3) | 0.2931 (2) | 0.1023 (16) | |
H44A | −0.1878 | 0.9654 | 0.2849 | 0.154* | |
H44B | −0.1907 | 1.0632 | 0.2564 | 0.154* | |
H44C | −0.1175 | 1.0857 | 0.3614 | 0.154* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0402 (17) | 0.0338 (17) | 0.0422 (16) | 0.0135 (14) | 0.0027 (13) | 0.0116 (14) |
N2 | 0.0455 (17) | 0.0407 (18) | 0.0356 (15) | 0.0143 (15) | 0.0119 (13) | 0.0154 (15) |
O1 | 0.0832 (19) | 0.0469 (17) | 0.0662 (16) | 0.0112 (15) | −0.0242 (14) | 0.0142 (14) |
O2 | 0.0497 (14) | 0.0766 (17) | 0.0425 (13) | 0.0311 (14) | 0.0086 (11) | 0.0236 (13) |
O3 | 0.0593 (16) | 0.103 (2) | 0.0558 (16) | 0.0393 (16) | 0.0228 (13) | 0.0376 (16) |
O4 | 0.0846 (18) | 0.0442 (16) | 0.0443 (13) | 0.0112 (14) | −0.0006 (12) | 0.0191 (13) |
O5 | 0.0720 (17) | 0.0575 (16) | 0.0401 (14) | 0.0163 (14) | −0.0021 (12) | 0.0145 (13) |
O6 | 0.0815 (18) | 0.0495 (16) | 0.0497 (15) | 0.0011 (15) | −0.0116 (13) | 0.0156 (13) |
O7 | 0.0578 (15) | 0.0422 (15) | 0.0531 (14) | 0.0132 (13) | −0.0004 (11) | 0.0169 (12) |
O8 | 0.0612 (16) | 0.0607 (17) | 0.0576 (15) | 0.0106 (14) | −0.0133 (13) | 0.0194 (14) |
O9 | 0.0481 (14) | 0.0782 (18) | 0.0484 (14) | 0.0202 (13) | 0.0150 (11) | 0.0341 (14) |
O10 | 0.0479 (16) | 0.112 (2) | 0.0629 (16) | 0.0313 (16) | 0.0180 (13) | 0.0387 (16) |
C1 | 0.046 (2) | 0.039 (2) | 0.038 (2) | 0.0150 (19) | 0.0042 (16) | 0.0126 (18) |
C2 | 0.060 (2) | 0.049 (3) | 0.051 (2) | 0.020 (2) | −0.0070 (19) | 0.018 (2) |
C3 | 0.063 (3) | 0.048 (3) | 0.055 (2) | 0.009 (2) | −0.0164 (19) | 0.015 (2) |
C4 | 0.065 (3) | 0.037 (2) | 0.044 (2) | 0.011 (2) | −0.0002 (19) | 0.0128 (19) |
C5 | 0.065 (3) | 0.048 (3) | 0.059 (2) | 0.016 (2) | −0.009 (2) | 0.024 (2) |
C6 | 0.052 (2) | 0.047 (2) | 0.045 (2) | 0.012 (2) | −0.0086 (17) | 0.016 (2) |
C7 | 0.051 (2) | 0.038 (2) | 0.047 (2) | 0.0131 (18) | 0.0041 (17) | 0.0186 (18) |
C8 | 0.041 (2) | 0.035 (2) | 0.038 (2) | 0.0122 (17) | 0.0005 (17) | 0.0118 (17) |
C9 | 0.042 (2) | 0.046 (2) | 0.039 (2) | 0.0194 (18) | 0.0025 (17) | 0.0162 (18) |
C10 | 0.045 (2) | 0.052 (2) | 0.046 (2) | 0.017 (2) | 0.0045 (19) | 0.016 (2) |
C11 | 0.049 (2) | 0.058 (3) | 0.058 (2) | 0.022 (2) | 0.005 (2) | 0.016 (2) |
C12 | 0.048 (2) | 0.055 (3) | 0.070 (3) | 0.022 (2) | −0.004 (2) | 0.023 (2) |
C13 | 0.061 (2) | 0.053 (2) | 0.048 (2) | 0.022 (2) | 0.0008 (19) | 0.021 (2) |
C14 | 0.085 (3) | 0.135 (4) | 0.086 (3) | 0.054 (3) | 0.050 (3) | 0.055 (3) |
C15 | 0.048 (2) | 0.045 (2) | 0.046 (2) | 0.0168 (19) | 0.0068 (17) | 0.0145 (18) |
C16 | 0.033 (2) | 0.044 (2) | 0.046 (2) | 0.0137 (18) | 0.0050 (16) | 0.016 (2) |
C17 | 0.036 (2) | 0.036 (2) | 0.054 (2) | 0.0103 (18) | 0.0055 (18) | 0.018 (2) |
C18 | 0.042 (2) | 0.041 (2) | 0.044 (2) | 0.0126 (19) | −0.0013 (17) | 0.009 (2) |
C19 | 0.051 (2) | 0.050 (3) | 0.056 (2) | 0.014 (2) | 0.0011 (19) | 0.009 (2) |
C20 | 0.057 (2) | 0.047 (2) | 0.069 (3) | 0.003 (2) | −0.001 (2) | 0.022 (2) |
C21 | 0.044 (2) | 0.058 (3) | 0.062 (2) | 0.012 (2) | 0.0053 (19) | 0.032 (2) |
C22 | 0.067 (3) | 0.086 (3) | 0.040 (2) | 0.023 (2) | −0.0016 (19) | 0.010 (2) |
C23 | 0.038 (2) | 0.040 (2) | 0.036 (2) | 0.0139 (18) | 0.0068 (16) | 0.0162 (18) |
C24 | 0.050 (2) | 0.044 (2) | 0.040 (2) | 0.0126 (19) | 0.0059 (17) | 0.0203 (19) |
C25 | 0.056 (2) | 0.048 (2) | 0.035 (2) | 0.014 (2) | −0.0028 (17) | 0.013 (2) |
C26 | 0.041 (2) | 0.041 (2) | 0.048 (2) | 0.0066 (19) | −0.0029 (18) | 0.013 (2) |
C27 | 0.049 (2) | 0.044 (2) | 0.045 (2) | 0.0121 (19) | 0.0071 (17) | 0.0237 (19) |
C28 | 0.050 (2) | 0.045 (2) | 0.0343 (19) | 0.011 (2) | 0.0024 (17) | 0.0140 (19) |
C29 | 0.045 (2) | 0.047 (2) | 0.039 (2) | 0.0167 (19) | 0.0099 (17) | 0.0123 (18) |
C30 | 0.046 (2) | 0.042 (2) | 0.0344 (19) | 0.0163 (19) | 0.0110 (16) | 0.0131 (18) |
C31 | 0.055 (2) | 0.033 (2) | 0.039 (2) | 0.0121 (19) | 0.0170 (17) | 0.0134 (18) |
C32 | 0.050 (2) | 0.042 (2) | 0.036 (2) | 0.009 (2) | 0.0028 (18) | 0.0050 (19) |
C33 | 0.056 (2) | 0.046 (3) | 0.047 (2) | 0.004 (2) | 0.0112 (19) | 0.005 (2) |
C34 | 0.061 (3) | 0.045 (2) | 0.059 (2) | 0.019 (2) | 0.018 (2) | 0.015 (2) |
C35 | 0.050 (2) | 0.048 (2) | 0.052 (2) | 0.022 (2) | 0.0125 (18) | 0.018 (2) |
C36 | 0.074 (3) | 0.090 (3) | 0.076 (3) | −0.005 (3) | −0.028 (2) | 0.031 (3) |
C37 | 0.053 (2) | 0.040 (2) | 0.044 (2) | 0.0095 (19) | 0.0027 (17) | 0.0134 (18) |
C38 | 0.049 (2) | 0.036 (2) | 0.037 (2) | 0.0080 (18) | 0.0118 (17) | 0.0137 (18) |
C39 | 0.047 (2) | 0.042 (2) | 0.0300 (19) | 0.0022 (18) | 0.0081 (17) | 0.0125 (17) |
C40 | 0.041 (2) | 0.061 (3) | 0.041 (2) | 0.006 (2) | 0.0055 (18) | 0.018 (2) |
C41 | 0.056 (3) | 0.072 (3) | 0.044 (2) | 0.007 (2) | 0.0194 (19) | 0.018 (2) |
C42 | 0.075 (3) | 0.064 (3) | 0.048 (2) | 0.004 (2) | 0.016 (2) | 0.028 (2) |
C43 | 0.066 (3) | 0.045 (2) | 0.048 (2) | 0.012 (2) | 0.0113 (19) | 0.018 (2) |
C44 | 0.069 (3) | 0.157 (5) | 0.115 (3) | 0.055 (3) | 0.050 (3) | 0.073 (3) |
N1—C1 | 1.438 (3) | C15—H15B | 0.9700 |
N1—C7 | 1.478 (3) | C16—C21 | 1.388 (4) |
N1—C15 | 1.487 (3) | C16—C17 | 1.390 (4) |
N2—C23 | 1.446 (3) | C17—C18 | 1.408 (4) |
N2—C37 | 1.457 (3) | C18—C19 | 1.363 (4) |
N2—C29 | 1.488 (3) | C19—C20 | 1.388 (4) |
O1—C4 | 1.371 (3) | C19—H19 | 0.9300 |
O1—H1 | 0.8200 | C20—C21 | 1.383 (4) |
O2—C9 | 1.383 (3) | C20—H20 | 0.9300 |
O2—H2 | 0.8200 | C21—H21 | 0.9300 |
O3—C10 | 1.362 (3) | C22—H22A | 0.9600 |
O3—C14 | 1.414 (3) | C22—H22B | 0.9600 |
O4—C17 | 1.368 (3) | C22—H22C | 0.9600 |
O4—H4 | 0.8200 | C23—C28 | 1.378 (4) |
O5—C18 | 1.366 (3) | C23—C24 | 1.396 (3) |
O5—C22 | 1.430 (3) | C24—C25 | 1.395 (4) |
O6—C26 | 1.377 (3) | C24—H24 | 0.9300 |
O6—H6 | 0.8200 | C25—C26 | 1.371 (4) |
O7—C31 | 1.378 (3) | C25—H25 | 0.9300 |
O7—H7 | 0.8200 | C26—C27 | 1.381 (3) |
O8—C32 | 1.362 (3) | C27—C28 | 1.382 (4) |
O8—C36 | 1.408 (3) | C27—H27 | 0.9300 |
O9—C39 | 1.361 (3) | C28—H28 | 0.9300 |
O9—H9 | 0.8200 | C29—C30 | 1.513 (3) |
O10—C40 | 1.375 (3) | C29—H29A | 0.9700 |
O10—C44 | 1.421 (3) | C29—H29B | 0.9700 |
C1—C2 | 1.381 (3) | C30—C31 | 1.379 (4) |
C1—C6 | 1.383 (4) | C30—C35 | 1.390 (4) |
C2—C3 | 1.396 (4) | C31—C32 | 1.403 (4) |
C2—H2A | 0.9300 | C32—C33 | 1.373 (4) |
C3—C4 | 1.367 (4) | C33—C34 | 1.390 (4) |
C3—H3 | 0.9300 | C33—H33 | 0.9300 |
C4—C5 | 1.381 (4) | C34—C35 | 1.373 (4) |
C5—C6 | 1.374 (4) | C34—H34 | 0.9300 |
C5—H5 | 0.9300 | C35—H35 | 0.9300 |
C6—H6A | 0.9300 | C36—H36A | 0.9600 |
C7—C8 | 1.518 (4) | C36—H36B | 0.9600 |
C7—H7A | 0.9700 | C36—H36C | 0.9600 |
C7—H7B | 0.9700 | C37—C38 | 1.508 (4) |
C8—C9 | 1.368 (4) | C37—H37A | 0.9700 |
C8—C13 | 1.397 (3) | C37—H37B | 0.9700 |
C9—C10 | 1.403 (4) | C38—C43 | 1.384 (4) |
C10—C11 | 1.379 (4) | C38—C39 | 1.385 (4) |
C11—C12 | 1.381 (4) | C39—C40 | 1.400 (4) |
C11—H11 | 0.9300 | C40—C41 | 1.370 (4) |
C12—C13 | 1.376 (4) | C41—C42 | 1.393 (4) |
C12—H12 | 0.9300 | C41—H41 | 0.9300 |
C13—H13 | 0.9300 | C42—C43 | 1.377 (4) |
C14—H14A | 0.9600 | C42—H42 | 0.9300 |
C14—H14B | 0.9600 | C43—H43 | 0.9300 |
C14—H14C | 0.9600 | C44—H44A | 0.9600 |
C15—C16 | 1.507 (4) | C44—H44B | 0.9600 |
C15—H15A | 0.9700 | C44—H44C | 0.9600 |
C1—N1—C7 | 117.0 (2) | C20—C21—H21 | 119.5 |
C1—N1—C15 | 114.4 (2) | C16—C21—H21 | 119.5 |
C7—N1—C15 | 110.1 (2) | O5—C22—H22A | 109.5 |
C23—N2—C37 | 116.8 (2) | O5—C22—H22B | 109.5 |
C23—N2—C29 | 114.3 (2) | H22A—C22—H22B | 109.5 |
C37—N2—C29 | 111.6 (2) | O5—C22—H22C | 109.5 |
C4—O1—H1 | 109.5 | H22A—C22—H22C | 109.5 |
C9—O2—H2 | 109.5 | H22B—C22—H22C | 109.5 |
C10—O3—C14 | 118.7 (3) | C28—C23—C24 | 118.3 (3) |
C17—O4—H4 | 109.5 | C28—C23—N2 | 118.9 (3) |
C18—O5—C22 | 116.9 (3) | C24—C23—N2 | 122.6 (3) |
C26—O6—H6 | 109.5 | C25—C24—C23 | 120.1 (3) |
C31—O7—H7 | 109.5 | C25—C24—H24 | 119.9 |
C32—O8—C36 | 117.8 (3) | C23—C24—H24 | 119.9 |
C39—O9—H9 | 109.5 | C26—C25—C24 | 120.1 (3) |
C40—O10—C44 | 118.3 (3) | C26—C25—H25 | 120.0 |
C2—C1—C6 | 118.1 (3) | C24—C25—H25 | 120.0 |
C2—C1—N1 | 124.5 (3) | C25—C26—O6 | 123.1 (3) |
C6—C1—N1 | 117.3 (3) | C25—C26—C27 | 120.3 (3) |
C1—C2—C3 | 120.9 (3) | O6—C26—C27 | 116.6 (3) |
C1—C2—H2A | 119.5 | C26—C27—C28 | 119.3 (3) |
C3—C2—H2A | 119.5 | C26—C27—H27 | 120.3 |
C4—C3—C2 | 119.8 (3) | C28—C27—H27 | 120.3 |
C4—C3—H3 | 120.1 | C23—C28—C27 | 121.7 (3) |
C2—C3—H3 | 120.1 | C23—C28—H28 | 119.1 |
C3—C4—O1 | 123.7 (3) | C27—C28—H28 | 119.1 |
C3—C4—C5 | 119.8 (3) | N2—C29—C30 | 110.5 (2) |
O1—C4—C5 | 116.4 (3) | N2—C29—H29A | 109.5 |
C6—C5—C4 | 120.0 (3) | C30—C29—H29A | 109.5 |
C6—C5—H5 | 120.0 | N2—C29—H29B | 109.5 |
C4—C5—H5 | 120.0 | C30—C29—H29B | 109.5 |
C5—C6—C1 | 121.3 (3) | H29A—C29—H29B | 108.1 |
C5—C6—H6A | 119.3 | C31—C30—C35 | 117.7 (3) |
C1—C6—H6A | 119.3 | C31—C30—C29 | 119.9 (3) |
N1—C7—C8 | 113.4 (3) | C35—C30—C29 | 122.3 (3) |
N1—C7—H7A | 108.9 | O7—C31—C30 | 118.7 (3) |
C8—C7—H7A | 108.9 | O7—C31—C32 | 119.7 (3) |
N1—C7—H7B | 108.9 | C30—C31—C32 | 121.5 (3) |
C8—C7—H7B | 108.9 | O8—C32—C33 | 127.7 (3) |
H7A—C7—H7B | 107.7 | O8—C32—C31 | 113.5 (3) |
C9—C8—C13 | 119.4 (3) | C33—C32—C31 | 118.9 (3) |
C9—C8—C7 | 121.3 (3) | C32—C33—C34 | 120.7 (3) |
C13—C8—C7 | 118.9 (3) | C32—C33—H33 | 119.6 |
C8—C9—O2 | 123.1 (3) | C34—C33—H33 | 119.6 |
C8—C9—C10 | 121.0 (3) | C35—C34—C33 | 119.0 (3) |
O2—C9—C10 | 115.8 (3) | C35—C34—H34 | 120.5 |
O3—C10—C11 | 126.2 (3) | C33—C34—H34 | 120.5 |
O3—C10—C9 | 114.6 (3) | C34—C35—C30 | 122.1 (3) |
C11—C10—C9 | 119.2 (3) | C34—C35—H35 | 118.9 |
C10—C11—C12 | 119.6 (3) | C30—C35—H35 | 118.9 |
C10—C11—H11 | 120.2 | O8—C36—H36A | 109.5 |
C12—C11—H11 | 120.2 | O8—C36—H36B | 109.5 |
C13—C12—C11 | 121.2 (3) | H36A—C36—H36B | 109.5 |
C13—C12—H12 | 119.4 | O8—C36—H36C | 109.5 |
C11—C12—H12 | 119.4 | H36A—C36—H36C | 109.5 |
C12—C13—C8 | 119.5 (3) | H36B—C36—H36C | 109.5 |
C12—C13—H13 | 120.2 | N2—C37—C38 | 115.6 (3) |
C8—C13—H13 | 120.2 | N2—C37—H37A | 108.4 |
O3—C14—H14A | 109.5 | C38—C37—H37A | 108.4 |
O3—C14—H14B | 109.5 | N2—C37—H37B | 108.4 |
H14A—C14—H14B | 109.5 | C38—C37—H37B | 108.4 |
O3—C14—H14C | 109.5 | H37A—C37—H37B | 107.4 |
H14A—C14—H14C | 109.5 | C43—C38—C39 | 119.4 (3) |
H14B—C14—H14C | 109.5 | C43—C38—C37 | 119.8 (3) |
N1—C15—C16 | 111.2 (2) | C39—C38—C37 | 120.4 (3) |
N1—C15—H15A | 109.4 | O9—C39—C38 | 124.1 (3) |
C16—C15—H15A | 109.4 | O9—C39—C40 | 116.0 (3) |
N1—C15—H15B | 109.4 | C38—C39—C40 | 120.0 (3) |
C16—C15—H15B | 109.4 | C41—C40—O10 | 125.7 (3) |
H15A—C15—H15B | 108.0 | C41—C40—C39 | 120.4 (3) |
C21—C16—C17 | 118.4 (3) | O10—C40—C39 | 114.0 (3) |
C21—C16—C15 | 122.8 (3) | C40—C41—C42 | 119.3 (3) |
C17—C16—C15 | 118.8 (3) | C40—C41—H41 | 120.3 |
O4—C17—C16 | 118.8 (3) | C42—C41—H41 | 120.3 |
O4—C17—C18 | 120.4 (3) | C43—C42—C41 | 120.5 (3) |
C16—C17—C18 | 120.8 (3) | C43—C42—H42 | 119.8 |
C19—C18—O5 | 127.5 (3) | C41—C42—H42 | 119.8 |
C19—C18—C17 | 119.2 (3) | C42—C43—C38 | 120.5 (3) |
O5—C18—C17 | 113.2 (3) | C42—C43—H43 | 119.8 |
C18—C19—C20 | 120.9 (3) | C38—C43—H43 | 119.8 |
C18—C19—H19 | 119.6 | O10—C44—H44A | 109.5 |
C20—C19—H19 | 119.6 | O10—C44—H44B | 109.5 |
C21—C20—C19 | 119.6 (3) | H44A—C44—H44B | 109.5 |
C21—C20—H20 | 120.2 | O10—C44—H44C | 109.5 |
C19—C20—H20 | 120.2 | H44A—C44—H44C | 109.5 |
C20—C21—C16 | 121.0 (3) | H44B—C44—H44C | 109.5 |
C7—N1—C1—C2 | 8.2 (4) | C37—N2—C23—C28 | −169.1 (3) |
C15—N1—C1—C2 | −122.7 (3) | C29—N2—C23—C28 | 57.9 (3) |
C7—N1—C1—C6 | −169.5 (3) | C37—N2—C23—C24 | 6.7 (4) |
C15—N1—C1—C6 | 59.6 (4) | C29—N2—C23—C24 | −126.3 (3) |
C6—C1—C2—C3 | 0.2 (5) | C28—C23—C24—C25 | 1.6 (4) |
N1—C1—C2—C3 | −177.5 (3) | N2—C23—C24—C25 | −174.3 (3) |
C1—C2—C3—C4 | −1.5 (5) | C23—C24—C25—C26 | 0.2 (5) |
C2—C3—C4—O1 | −178.8 (3) | C24—C25—C26—O6 | 175.0 (3) |
C2—C3—C4—C5 | 2.4 (6) | C24—C25—C26—C27 | −2.8 (5) |
C3—C4—C5—C6 | −2.0 (5) | C25—C26—C27—C28 | 3.6 (5) |
O1—C4—C5—C6 | 179.1 (3) | O6—C26—C27—C28 | −174.3 (3) |
C4—C5—C6—C1 | 0.7 (5) | C24—C23—C28—C27 | −0.8 (5) |
C2—C1—C6—C5 | 0.2 (5) | N2—C23—C28—C27 | 175.2 (3) |
N1—C1—C6—C5 | 178.1 (3) | C26—C27—C28—C23 | −1.8 (5) |
C1—N1—C7—C8 | 74.4 (3) | C23—N2—C29—C30 | −158.7 (2) |
C15—N1—C7—C8 | −152.7 (2) | C37—N2—C29—C30 | 66.0 (3) |
N1—C7—C8—C9 | 38.0 (4) | N2—C29—C30—C31 | 66.8 (4) |
N1—C7—C8—C13 | −149.7 (3) | N2—C29—C30—C35 | −109.3 (3) |
C13—C8—C9—O2 | −178.2 (3) | C35—C30—C31—O7 | −179.0 (3) |
C7—C8—C9—O2 | −5.9 (5) | C29—C30—C31—O7 | 4.7 (4) |
C13—C8—C9—C10 | −0.3 (5) | C35—C30—C31—C32 | −0.2 (5) |
C7—C8—C9—C10 | 172.0 (3) | C29—C30—C31—C32 | −176.5 (3) |
C14—O3—C10—C11 | −3.4 (5) | C36—O8—C32—C33 | −1.7 (5) |
C14—O3—C10—C9 | 176.7 (3) | C36—O8—C32—C31 | 178.0 (3) |
C8—C9—C10—O3 | −179.7 (3) | O7—C31—C32—O8 | 0.7 (4) |
O2—C9—C10—O3 | −1.7 (4) | C30—C31—C32—O8 | −178.0 (3) |
C8—C9—C10—C11 | 0.4 (5) | O7—C31—C32—C33 | −179.6 (3) |
O2—C9—C10—C11 | 178.3 (3) | C30—C31—C32—C33 | 1.7 (5) |
O3—C10—C11—C12 | −179.7 (3) | O8—C32—C33—C34 | 177.8 (3) |
C9—C10—C11—C12 | 0.2 (5) | C31—C32—C33—C34 | −1.9 (5) |
C10—C11—C12—C13 | −0.8 (5) | C32—C33—C34—C35 | 0.7 (5) |
C11—C12—C13—C8 | 0.8 (5) | C33—C34—C35—C30 | 0.8 (5) |
C9—C8—C13—C12 | −0.3 (5) | C31—C30—C35—C34 | −1.1 (5) |
C7—C8—C13—C12 | −172.7 (3) | C29—C30—C35—C34 | 175.1 (3) |
C1—N1—C15—C16 | −151.0 (3) | C23—N2—C37—C38 | 69.6 (3) |
C7—N1—C15—C16 | 74.8 (3) | C29—N2—C37—C38 | −156.3 (2) |
N1—C15—C16—C21 | −107.1 (3) | N2—C37—C38—C43 | −148.5 (3) |
N1—C15—C16—C17 | 71.1 (3) | N2—C37—C38—C39 | 39.3 (4) |
C21—C16—C17—O4 | −178.7 (3) | C43—C38—C39—O9 | −177.6 (3) |
C15—C16—C17—O4 | 3.0 (4) | C37—C38—C39—O9 | −5.4 (5) |
C21—C16—C17—C18 | 2.3 (5) | C43—C38—C39—C40 | 1.2 (5) |
C15—C16—C17—C18 | −176.0 (3) | C37—C38—C39—C40 | 173.4 (3) |
C22—O5—C18—C19 | −2.5 (5) | C44—O10—C40—C41 | −6.3 (5) |
C22—O5—C18—C17 | 176.1 (3) | C44—O10—C40—C39 | 173.9 (3) |
O4—C17—C18—C19 | 179.5 (3) | O9—C39—C40—C41 | 177.0 (3) |
C16—C17—C18—C19 | −1.5 (5) | C38—C39—C40—C41 | −1.9 (5) |
O4—C17—C18—O5 | 0.8 (4) | O9—C39—C40—O10 | −3.3 (4) |
C16—C17—C18—O5 | 179.8 (3) | C38—C39—C40—O10 | 177.9 (3) |
O5—C18—C19—C20 | 178.5 (3) | O10—C40—C41—C42 | −178.9 (3) |
C17—C18—C19—C20 | 0.0 (5) | C39—C40—C41—C42 | 0.9 (5) |
C18—C19—C20—C21 | 0.7 (5) | C40—C41—C42—C43 | 0.9 (5) |
C19—C20—C21—C16 | 0.1 (5) | C41—C42—C43—C38 | −1.6 (5) |
C17—C16—C21—C20 | −1.6 (5) | C39—C38—C43—C42 | 0.5 (5) |
C15—C16—C21—C20 | 176.6 (3) | C37—C38—C43—C42 | −171.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O9i | 0.82 | 2.38 | 3.185 (3) | 168 |
O1—H1···O10i | 0.82 | 2.35 | 2.911 (3) | 127 |
O2—H2···N1 | 0.82 | 1.97 | 2.697 (3) | 147 |
O4—H4···O5 | 0.82 | 2.19 | 2.640 (3) | 115 |
O4—H4···O6ii | 0.82 | 2.49 | 2.941 (3) | 116 |
O6—H6···O2iii | 0.82 | 2.10 | 2.913 (3) | 171 |
O6—H6···O3iii | 0.82 | 2.50 | 3.008 (3) | 121 |
O7—H7···O1iv | 0.82 | 2.11 | 2.835 (3) | 148 |
O7—H7···O8 | 0.82 | 2.17 | 2.629 (3) | 115 |
O9—H9···O7 | 0.82 | 2.45 | 3.023 (3) | 128 |
O9—H9···N2 | 0.82 | 2.04 | 2.753 (3) | 146 |
C5—H5···O7ii | 0.93 | 2.50 | 3.218 (4) | 134 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y−1, z; (iii) −x+1, −y+2, −z+1; (iv) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C22H23NO5 |
Mr | 381.41 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 10.4059 (19), 13.699 (2), 15.196 (2) |
α, β, γ (°) | 113.549 (3), 96.908 (2), 99.792 (2) |
V (Å3) | 1914.0 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.24 × 0.17 × 0.15 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.978, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10128, 6656, 2772 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.067, 0.89 |
No. of reflections | 6656 |
No. of parameters | 505 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.18 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O9i | 0.82 | 2.38 | 3.185 (3) | 167.6 |
O1—H1···O10i | 0.82 | 2.35 | 2.911 (3) | 126.7 |
O2—H2···N1 | 0.82 | 1.97 | 2.697 (3) | 146.5 |
O4—H4···O5 | 0.82 | 2.19 | 2.640 (3) | 115.0 |
O4—H4···O6ii | 0.82 | 2.49 | 2.941 (3) | 115.5 |
O6—H6···O2iii | 0.82 | 2.10 | 2.913 (3) | 170.5 |
O6—H6···O3iii | 0.82 | 2.50 | 3.008 (3) | 120.8 |
O7—H7···O1iv | 0.82 | 2.11 | 2.835 (3) | 147.5 |
O7—H7···O8 | 0.82 | 2.17 | 2.629 (3) | 115.4 |
O9—H9···O7 | 0.82 | 2.45 | 3.023 (3) | 127.6 |
O9—H9···N2 | 0.82 | 2.04 | 2.753 (3) | 145.8 |
C5—H5···O7ii | 0.93 | 2.50 | 3.218 (4) | 133.8 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y−1, z; (iii) −x+1, −y+2, −z+1; (iv) x, y+1, z. |
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We have recently reported the supramolecular structures of amine derivatives containing hydroxy and methoxy groups, for example, N-(2-hydroxy-3-methoxybenzyl)-4-chloroaniline (Liu et al., 2007), and 6,6'-dimethoxy-2,2'-(2,2,4-trimethylimidazolidine-1,3-diyldimethylene)diphenol (Xia et al., 2007). We have now continued our studies in this area with the title compound, (I), an aniline derivative containing hydroxy and methoxy groups.
Compound (I) crystallizes with the two independent molecules in the asymmetric unit and Z = 4 in the triclinic space group P1 (Fig. 1). In the molecules, the dihedral angles between the phenyl ring (C1–C5) and other two phenyl rings (C8–C13) and (C16–C21) are 86.37 (10)° and 39.09 (10)°, respectively, and the dihedral angles between the phenyl ring (C23–C28) and other two phenyl rings (C30–C35) and (C38–C43) are 48.28 (9)° and 87.37 (9)°, respectively. The C—N bonds involving atom N1 are longer than those involving atom N2 (excluding C15—N1 and C29—N2 bond). The bond angles around the N1 atom are almost in agreement with those around the N2 atom.
The molecules of (I) are linked by O—H···O and C—H···O hydrogen bonds (Table 2) into centrosymmetric tetramers, and these tetramers are further linked by O—H···O, C—H···O hydrogen bonds to form two chains. Atom O6 in the molecule at (1 - x, 2 - y, 1 - z) act as a hydrogen-bond donors, respectively, to atoms O2 and O3 in the molecule at (x, y, z). At the same time, atom O4 in the molecule at (x, y, z) acts as hydrogen-bond donor to atom O6 in the molecule at (x, -1 + y, z), so generating R44(26) and R44(24) (Bernstein et al., 1995) tetramers centred at (1/2, 1/2, 1/2) (Fig. 2). The tetramers are linked into a [011] chain by O—H···O and C—H···O hydrogen bonds. Atom O1 in the molecules at (x, y, z) act as donors, respectively, to atoms O9 and O10 in the molecules at (- x, 1 - y, - z), atoms C5 and O7 in the molecule at (x, y, z) and (x, -1 + y, z) act as hydrogen-bond donors, respectively, to atoms O7 and O1 in the molecule at (x, -1 + y, z) and (x, y, z). Propagation by inversion and translation of these four interactions then generates a chain running parallel to the [011] direction containing R44(24) rings and R44(30) rings centred at (n, n, n) (n = zero or integer), R44(26) and R44(24) rings centred at (1/2 + n, 1/2 + n, 1/2 + n) (n = zero or integer) (Fig. 3). In a similar way, the tetramers are linked into a chain by O—H···O and C—H···O hydrogen bonds parallel to the a axis direction. Atom O6 in the molecule at (-1 + x, -1 + y, z) and (1 - x, 2 - y, 1 - z) accept hydrogen bond from atom C14 in the molecule at (x, y, z), and at the same time, acts as donor to atom O3 in the molecule at (x, y, z), respectively, propagation by inversion and translation of these two interactions then generates a chain running parallel to the a axis direction containing R44(10) rings centred at (n, 1/2, 1/2) (n = zero or integer), R44(26) and R44(24) rings centred at (1/2 + n, 1/2, 1/2) (n = zero or integer) (Fig. 4).