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The title compound, C22H23NO5, crystallizes with two independent mol­ecules in the asymmetric unit. In one molecule, the dihedral angle between one outer ring and the central ring is 86.37 (10)°, while that between the two outer rings is 88.99 (10)°; in the other molecule, these angles are 87.37 (9) and 88.14 (9)°, respectively. The mol­ecules are linked into two chains by a combination of O—H...O and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044558/at2396sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044558/at2396Isup2.hkl
Contains datablock I

CCDC reference: 649515

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Comment top

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).

Related literature top

For related literature, see: Bernstein et al. (1995); Liu et al. (2007); Xia et al. (2007).

Experimental top

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..

Refinement top

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.

Structure description top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are at the 30% probability level.
[Figure 2] Fig. 2. A larger portion of the crystal structure of (I), showing the formation of a hydrogen-bonded tetramers built from C—H···O and O—H···O. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds. [Symmetry codes: (A) x, 1 - y, z, (B) 1 - x, 2 - y, 1 - z].
[Figure 3] Fig. 3. A larger portion of the crystal structure of (I), showing the formation of a hydrogen-bonded chains built from C—H···O and O—H···O. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds.
[Figure 4] Fig. 4. A larger portion of the crystal structure of (I), showing the formation of a hydrogen-bonded chains built from C—H···O and O—H···O. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds.
4-Hydroxy-N,N-bis(2-hydroxy-3-methoxybenzyl)aniline top
Crystal data top
C22H23NO5Z = 4
Mr = 381.41F(000) = 808
Triclinic, P1Dx = 1.324 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.4059 (19) ÅCell parameters from 1304 reflections
b = 13.699 (2) Åθ = 2.3–27.8°
c = 15.196 (2) ŵ = 0.09 mm1
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
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
6656 independent reflections
Radiation source: fine-focus sealed tube2772 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.978, Tmax = 0.986k = 167
10128 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H-atom parameters constrained
S = 0.89 w = 1/[σ2(Fo2)]
where P = (Fo2 + 2Fc2)/3
6656 reflections(Δ/σ)max = 0.012
505 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C22H23NO5γ = 99.792 (2)°
Mr = 381.41V = 1914.0 (5) Å3
Triclinic, P1Z = 4
a = 10.4059 (19) ÅMo Kα radiation
b = 13.699 (2) ŵ = 0.09 mm1
c = 15.196 (2) ÅT = 298 K
α = 113.549 (3)°0.24 × 0.17 × 0.15 mm
β = 96.908 (2)°
Data collection top
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 = 0.986Rint = 0.041
10128 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.067H-atom parameters constrained
S = 0.89Δρmax = 0.15 e Å3
6656 reflectionsΔρmin = 0.18 e Å3
505 parameters
Special details top

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) top
xyzUiso*/Ueq
N10.3458 (2)0.5001 (2)0.18136 (16)0.0403 (7)
N20.4358 (2)0.9610 (2)0.19252 (16)0.0401 (7)
O10.1094 (2)0.05510 (17)0.04810 (14)0.0731 (8)
H10.04180.04400.08790.110*
O20.24705 (18)0.55357 (17)0.34615 (12)0.0549 (7)
H20.30080.53410.31130.082*
O30.0467 (2)0.5905 (2)0.42750 (15)0.0678 (8)
O40.5303 (2)0.49388 (16)0.35279 (14)0.0595 (7)
H40.53550.49290.40670.089*
O50.6420 (2)0.64758 (17)0.53099 (15)0.0599 (7)
O60.6991 (2)1.39497 (17)0.44554 (14)0.0664 (7)
H60.72051.40460.50270.100*
O70.30272 (19)0.95072 (16)0.00158 (13)0.0532 (6)
H70.23830.95640.03440.080*
O80.1087 (2)0.80271 (18)0.14366 (15)0.0647 (7)
O90.17730 (18)0.98333 (16)0.17445 (13)0.0548 (6)
H90.25010.98170.15910.082*
O100.0183 (2)1.0235 (2)0.25875 (15)0.0716 (8)
C10.2808 (3)0.3875 (3)0.1176 (2)0.0420 (9)
C20.1742 (3)0.3542 (3)0.0402 (2)0.0552 (10)
H2A0.14250.40650.02520.066*
C30.1133 (3)0.2432 (3)0.0159 (2)0.0610 (11)
H30.04020.22190.06690.073*
C40.1614 (3)0.1659 (3)0.0042 (2)0.0514 (10)
C50.2668 (3)0.1982 (3)0.0823 (2)0.0586 (10)
H50.29800.14590.09740.070*
C60.3257 (3)0.3077 (3)0.1376 (2)0.0512 (9)
H6A0.39720.32860.18950.061*
C70.2828 (3)0.5848 (2)0.1707 (2)0.0451 (9)
H7A0.25990.56790.10160.054*
H7B0.34680.65520.20330.054*
C80.1581 (3)0.5936 (2)0.2131 (2)0.0393 (8)
C90.1497 (3)0.5826 (2)0.2980 (2)0.0425 (9)
C100.0415 (3)0.6043 (3)0.3434 (2)0.0489 (9)
C110.0580 (3)0.6366 (3)0.3011 (2)0.0575 (10)
H110.13020.65150.33040.069*
C120.0498 (3)0.6467 (3)0.2150 (2)0.0593 (11)
H120.11760.66760.18620.071*
C130.0569 (3)0.6264 (3)0.1709 (2)0.0544 (10)
H130.06160.63440.11330.065*
C140.0543 (3)0.6161 (3)0.4813 (2)0.0928 (15)
H14A0.05680.69120.49870.139*
H14B0.03580.60540.53980.139*
H14C0.13890.56910.44180.139*
C150.4914 (3)0.5294 (2)0.18503 (19)0.0474 (9)
H15A0.50580.55200.13340.057*
H15B0.52720.46550.17360.057*
C160.5636 (3)0.6209 (3)0.2829 (2)0.0416 (8)
C170.5774 (3)0.5989 (3)0.3648 (2)0.0426 (9)
C180.6368 (3)0.6832 (3)0.4588 (2)0.0460 (9)
C190.6838 (3)0.7870 (3)0.4686 (2)0.0573 (10)
H190.72310.84300.53060.069*
C200.6738 (3)0.8101 (3)0.3875 (3)0.0610 (10)
H200.70710.88100.39490.073*
C210.6141 (3)0.7272 (3)0.2955 (2)0.0532 (10)
H210.60760.74290.24120.064*
C220.7085 (3)0.7266 (3)0.62790 (19)0.0703 (12)
H22A0.79830.75730.62720.105*
H22B0.71010.69150.67140.105*
H22C0.66200.78390.65010.105*
C230.5141 (3)1.0693 (3)0.2602 (2)0.0379 (8)
C240.5500 (3)1.1011 (2)0.3610 (2)0.0441 (9)
H240.53041.04990.38620.053*
C250.6153 (3)1.2095 (3)0.4240 (2)0.0488 (9)
H250.63941.23040.49100.059*
C260.6440 (3)1.2852 (3)0.3870 (2)0.0470 (9)
C270.6139 (3)1.2538 (3)0.2871 (2)0.0444 (9)
H270.63781.30420.26180.053*
C280.5477 (3)1.1467 (3)0.2252 (2)0.0446 (9)
H280.52531.12630.15810.054*
C290.4974 (3)0.9035 (2)0.10890 (18)0.0453 (9)
H29A0.56420.87150.13010.054*
H29B0.54130.95570.08730.054*
C300.3925 (3)0.8142 (3)0.0244 (2)0.0408 (9)
C310.2957 (3)0.8415 (3)0.0254 (2)0.0421 (8)
C320.1927 (3)0.7609 (3)0.1006 (2)0.0476 (9)
C330.1868 (3)0.6525 (3)0.1228 (2)0.0561 (10)
H330.11750.59850.17110.067*
C340.2835 (3)0.6227 (3)0.0739 (2)0.0563 (10)
H340.27980.54920.08970.068*
C350.3846 (3)0.7035 (3)0.0020 (2)0.0499 (9)
H350.44980.68340.03010.060*
C360.0044 (3)0.7281 (3)0.2222 (2)0.0889 (14)
H36A0.04110.68200.27400.133*
H36B0.04680.76780.24610.133*
H36C0.05210.68360.19990.133*
C370.3824 (3)0.8887 (2)0.2352 (2)0.0482 (9)
H37A0.45500.88610.28000.058*
H37B0.34820.81530.18290.058*
C380.2732 (3)0.9204 (2)0.2897 (2)0.0412 (8)
C390.1764 (3)0.9610 (3)0.2540 (2)0.0416 (9)
C400.0678 (3)0.9796 (3)0.2994 (2)0.0495 (9)
C410.0546 (3)0.9549 (3)0.3772 (2)0.0598 (10)
H410.01820.96630.40670.072*
C420.1512 (4)0.9124 (3)0.4117 (2)0.0624 (11)
H420.14220.89450.46400.075*
C430.2600 (3)0.8967 (3)0.3690 (2)0.0542 (10)
H430.32510.87000.39370.065*
C440.1383 (3)1.0354 (3)0.2931 (2)0.1023 (16)
H44A0.18780.96540.28490.154*
H44B0.19071.06320.25640.154*
H44C0.11751.08570.36140.154*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0402 (17)0.0338 (17)0.0422 (16)0.0135 (14)0.0027 (13)0.0116 (14)
N20.0455 (17)0.0407 (18)0.0356 (15)0.0143 (15)0.0119 (13)0.0154 (15)
O10.0832 (19)0.0469 (17)0.0662 (16)0.0112 (15)0.0242 (14)0.0142 (14)
O20.0497 (14)0.0766 (17)0.0425 (13)0.0311 (14)0.0086 (11)0.0236 (13)
O30.0593 (16)0.103 (2)0.0558 (16)0.0393 (16)0.0228 (13)0.0376 (16)
O40.0846 (18)0.0442 (16)0.0443 (13)0.0112 (14)0.0006 (12)0.0191 (13)
O50.0720 (17)0.0575 (16)0.0401 (14)0.0163 (14)0.0021 (12)0.0145 (13)
O60.0815 (18)0.0495 (16)0.0497 (15)0.0011 (15)0.0116 (13)0.0156 (13)
O70.0578 (15)0.0422 (15)0.0531 (14)0.0132 (13)0.0004 (11)0.0169 (12)
O80.0612 (16)0.0607 (17)0.0576 (15)0.0106 (14)0.0133 (13)0.0194 (14)
O90.0481 (14)0.0782 (18)0.0484 (14)0.0202 (13)0.0150 (11)0.0341 (14)
O100.0479 (16)0.112 (2)0.0629 (16)0.0313 (16)0.0180 (13)0.0387 (16)
C10.046 (2)0.039 (2)0.038 (2)0.0150 (19)0.0042 (16)0.0126 (18)
C20.060 (2)0.049 (3)0.051 (2)0.020 (2)0.0070 (19)0.018 (2)
C30.063 (3)0.048 (3)0.055 (2)0.009 (2)0.0164 (19)0.015 (2)
C40.065 (3)0.037 (2)0.044 (2)0.011 (2)0.0002 (19)0.0128 (19)
C50.065 (3)0.048 (3)0.059 (2)0.016 (2)0.009 (2)0.024 (2)
C60.052 (2)0.047 (2)0.045 (2)0.012 (2)0.0086 (17)0.016 (2)
C70.051 (2)0.038 (2)0.047 (2)0.0131 (18)0.0041 (17)0.0186 (18)
C80.041 (2)0.035 (2)0.038 (2)0.0122 (17)0.0005 (17)0.0118 (17)
C90.042 (2)0.046 (2)0.039 (2)0.0194 (18)0.0025 (17)0.0162 (18)
C100.045 (2)0.052 (2)0.046 (2)0.017 (2)0.0045 (19)0.016 (2)
C110.049 (2)0.058 (3)0.058 (2)0.022 (2)0.005 (2)0.016 (2)
C120.048 (2)0.055 (3)0.070 (3)0.022 (2)0.004 (2)0.023 (2)
C130.061 (2)0.053 (2)0.048 (2)0.022 (2)0.0008 (19)0.021 (2)
C140.085 (3)0.135 (4)0.086 (3)0.054 (3)0.050 (3)0.055 (3)
C150.048 (2)0.045 (2)0.046 (2)0.0168 (19)0.0068 (17)0.0145 (18)
C160.033 (2)0.044 (2)0.046 (2)0.0137 (18)0.0050 (16)0.016 (2)
C170.036 (2)0.036 (2)0.054 (2)0.0103 (18)0.0055 (18)0.018 (2)
C180.042 (2)0.041 (2)0.044 (2)0.0126 (19)0.0013 (17)0.009 (2)
C190.051 (2)0.050 (3)0.056 (2)0.014 (2)0.0011 (19)0.009 (2)
C200.057 (2)0.047 (2)0.069 (3)0.003 (2)0.001 (2)0.022 (2)
C210.044 (2)0.058 (3)0.062 (2)0.012 (2)0.0053 (19)0.032 (2)
C220.067 (3)0.086 (3)0.040 (2)0.023 (2)0.0016 (19)0.010 (2)
C230.038 (2)0.040 (2)0.036 (2)0.0139 (18)0.0068 (16)0.0162 (18)
C240.050 (2)0.044 (2)0.040 (2)0.0126 (19)0.0059 (17)0.0203 (19)
C250.056 (2)0.048 (2)0.035 (2)0.014 (2)0.0028 (17)0.013 (2)
C260.041 (2)0.041 (2)0.048 (2)0.0066 (19)0.0029 (18)0.013 (2)
C270.049 (2)0.044 (2)0.045 (2)0.0121 (19)0.0071 (17)0.0237 (19)
C280.050 (2)0.045 (2)0.0343 (19)0.011 (2)0.0024 (17)0.0140 (19)
C290.045 (2)0.047 (2)0.039 (2)0.0167 (19)0.0099 (17)0.0123 (18)
C300.046 (2)0.042 (2)0.0344 (19)0.0163 (19)0.0110 (16)0.0131 (18)
C310.055 (2)0.033 (2)0.039 (2)0.0121 (19)0.0170 (17)0.0134 (18)
C320.050 (2)0.042 (2)0.036 (2)0.009 (2)0.0028 (18)0.0050 (19)
C330.056 (2)0.046 (3)0.047 (2)0.004 (2)0.0112 (19)0.005 (2)
C340.061 (3)0.045 (2)0.059 (2)0.019 (2)0.018 (2)0.015 (2)
C350.050 (2)0.048 (2)0.052 (2)0.022 (2)0.0125 (18)0.018 (2)
C360.074 (3)0.090 (3)0.076 (3)0.005 (3)0.028 (2)0.031 (3)
C370.053 (2)0.040 (2)0.044 (2)0.0095 (19)0.0027 (17)0.0134 (18)
C380.049 (2)0.036 (2)0.037 (2)0.0080 (18)0.0118 (17)0.0137 (18)
C390.047 (2)0.042 (2)0.0300 (19)0.0022 (18)0.0081 (17)0.0125 (17)
C400.041 (2)0.061 (3)0.041 (2)0.006 (2)0.0055 (18)0.018 (2)
C410.056 (3)0.072 (3)0.044 (2)0.007 (2)0.0194 (19)0.018 (2)
C420.075 (3)0.064 (3)0.048 (2)0.004 (2)0.016 (2)0.028 (2)
C430.066 (3)0.045 (2)0.048 (2)0.012 (2)0.0113 (19)0.018 (2)
C440.069 (3)0.157 (5)0.115 (3)0.055 (3)0.050 (3)0.073 (3)
Geometric parameters (Å, º) top
N1—C11.438 (3)C15—H15B0.9700
N1—C71.478 (3)C16—C211.388 (4)
N1—C151.487 (3)C16—C171.390 (4)
N2—C231.446 (3)C17—C181.408 (4)
N2—C371.457 (3)C18—C191.363 (4)
N2—C291.488 (3)C19—C201.388 (4)
O1—C41.371 (3)C19—H190.9300
O1—H10.8200C20—C211.383 (4)
O2—C91.383 (3)C20—H200.9300
O2—H20.8200C21—H210.9300
O3—C101.362 (3)C22—H22A0.9600
O3—C141.414 (3)C22—H22B0.9600
O4—C171.368 (3)C22—H22C0.9600
O4—H40.8200C23—C281.378 (4)
O5—C181.366 (3)C23—C241.396 (3)
O5—C221.430 (3)C24—C251.395 (4)
O6—C261.377 (3)C24—H240.9300
O6—H60.8200C25—C261.371 (4)
O7—C311.378 (3)C25—H250.9300
O7—H70.8200C26—C271.381 (3)
O8—C321.362 (3)C27—C281.382 (4)
O8—C361.408 (3)C27—H270.9300
O9—C391.361 (3)C28—H280.9300
O9—H90.8200C29—C301.513 (3)
O10—C401.375 (3)C29—H29A0.9700
O10—C441.421 (3)C29—H29B0.9700
C1—C21.381 (3)C30—C311.379 (4)
C1—C61.383 (4)C30—C351.390 (4)
C2—C31.396 (4)C31—C321.403 (4)
C2—H2A0.9300C32—C331.373 (4)
C3—C41.367 (4)C33—C341.390 (4)
C3—H30.9300C33—H330.9300
C4—C51.381 (4)C34—C351.373 (4)
C5—C61.374 (4)C34—H340.9300
C5—H50.9300C35—H350.9300
C6—H6A0.9300C36—H36A0.9600
C7—C81.518 (4)C36—H36B0.9600
C7—H7A0.9700C36—H36C0.9600
C7—H7B0.9700C37—C381.508 (4)
C8—C91.368 (4)C37—H37A0.9700
C8—C131.397 (3)C37—H37B0.9700
C9—C101.403 (4)C38—C431.384 (4)
C10—C111.379 (4)C38—C391.385 (4)
C11—C121.381 (4)C39—C401.400 (4)
C11—H110.9300C40—C411.370 (4)
C12—C131.376 (4)C41—C421.393 (4)
C12—H120.9300C41—H410.9300
C13—H130.9300C42—C431.377 (4)
C14—H14A0.9600C42—H420.9300
C14—H14B0.9600C43—H430.9300
C14—H14C0.9600C44—H44A0.9600
C15—C161.507 (4)C44—H44B0.9600
C15—H15A0.9700C44—H44C0.9600
C1—N1—C7117.0 (2)C20—C21—H21119.5
C1—N1—C15114.4 (2)C16—C21—H21119.5
C7—N1—C15110.1 (2)O5—C22—H22A109.5
C23—N2—C37116.8 (2)O5—C22—H22B109.5
C23—N2—C29114.3 (2)H22A—C22—H22B109.5
C37—N2—C29111.6 (2)O5—C22—H22C109.5
C4—O1—H1109.5H22A—C22—H22C109.5
C9—O2—H2109.5H22B—C22—H22C109.5
C10—O3—C14118.7 (3)C28—C23—C24118.3 (3)
C17—O4—H4109.5C28—C23—N2118.9 (3)
C18—O5—C22116.9 (3)C24—C23—N2122.6 (3)
C26—O6—H6109.5C25—C24—C23120.1 (3)
C31—O7—H7109.5C25—C24—H24119.9
C32—O8—C36117.8 (3)C23—C24—H24119.9
C39—O9—H9109.5C26—C25—C24120.1 (3)
C40—O10—C44118.3 (3)C26—C25—H25120.0
C2—C1—C6118.1 (3)C24—C25—H25120.0
C2—C1—N1124.5 (3)C25—C26—O6123.1 (3)
C6—C1—N1117.3 (3)C25—C26—C27120.3 (3)
C1—C2—C3120.9 (3)O6—C26—C27116.6 (3)
C1—C2—H2A119.5C26—C27—C28119.3 (3)
C3—C2—H2A119.5C26—C27—H27120.3
C4—C3—C2119.8 (3)C28—C27—H27120.3
C4—C3—H3120.1C23—C28—C27121.7 (3)
C2—C3—H3120.1C23—C28—H28119.1
C3—C4—O1123.7 (3)C27—C28—H28119.1
C3—C4—C5119.8 (3)N2—C29—C30110.5 (2)
O1—C4—C5116.4 (3)N2—C29—H29A109.5
C6—C5—C4120.0 (3)C30—C29—H29A109.5
C6—C5—H5120.0N2—C29—H29B109.5
C4—C5—H5120.0C30—C29—H29B109.5
C5—C6—C1121.3 (3)H29A—C29—H29B108.1
C5—C6—H6A119.3C31—C30—C35117.7 (3)
C1—C6—H6A119.3C31—C30—C29119.9 (3)
N1—C7—C8113.4 (3)C35—C30—C29122.3 (3)
N1—C7—H7A108.9O7—C31—C30118.7 (3)
C8—C7—H7A108.9O7—C31—C32119.7 (3)
N1—C7—H7B108.9C30—C31—C32121.5 (3)
C8—C7—H7B108.9O8—C32—C33127.7 (3)
H7A—C7—H7B107.7O8—C32—C31113.5 (3)
C9—C8—C13119.4 (3)C33—C32—C31118.9 (3)
C9—C8—C7121.3 (3)C32—C33—C34120.7 (3)
C13—C8—C7118.9 (3)C32—C33—H33119.6
C8—C9—O2123.1 (3)C34—C33—H33119.6
C8—C9—C10121.0 (3)C35—C34—C33119.0 (3)
O2—C9—C10115.8 (3)C35—C34—H34120.5
O3—C10—C11126.2 (3)C33—C34—H34120.5
O3—C10—C9114.6 (3)C34—C35—C30122.1 (3)
C11—C10—C9119.2 (3)C34—C35—H35118.9
C10—C11—C12119.6 (3)C30—C35—H35118.9
C10—C11—H11120.2O8—C36—H36A109.5
C12—C11—H11120.2O8—C36—H36B109.5
C13—C12—C11121.2 (3)H36A—C36—H36B109.5
C13—C12—H12119.4O8—C36—H36C109.5
C11—C12—H12119.4H36A—C36—H36C109.5
C12—C13—C8119.5 (3)H36B—C36—H36C109.5
C12—C13—H13120.2N2—C37—C38115.6 (3)
C8—C13—H13120.2N2—C37—H37A108.4
O3—C14—H14A109.5C38—C37—H37A108.4
O3—C14—H14B109.5N2—C37—H37B108.4
H14A—C14—H14B109.5C38—C37—H37B108.4
O3—C14—H14C109.5H37A—C37—H37B107.4
H14A—C14—H14C109.5C43—C38—C39119.4 (3)
H14B—C14—H14C109.5C43—C38—C37119.8 (3)
N1—C15—C16111.2 (2)C39—C38—C37120.4 (3)
N1—C15—H15A109.4O9—C39—C38124.1 (3)
C16—C15—H15A109.4O9—C39—C40116.0 (3)
N1—C15—H15B109.4C38—C39—C40120.0 (3)
C16—C15—H15B109.4C41—C40—O10125.7 (3)
H15A—C15—H15B108.0C41—C40—C39120.4 (3)
C21—C16—C17118.4 (3)O10—C40—C39114.0 (3)
C21—C16—C15122.8 (3)C40—C41—C42119.3 (3)
C17—C16—C15118.8 (3)C40—C41—H41120.3
O4—C17—C16118.8 (3)C42—C41—H41120.3
O4—C17—C18120.4 (3)C43—C42—C41120.5 (3)
C16—C17—C18120.8 (3)C43—C42—H42119.8
C19—C18—O5127.5 (3)C41—C42—H42119.8
C19—C18—C17119.2 (3)C42—C43—C38120.5 (3)
O5—C18—C17113.2 (3)C42—C43—H43119.8
C18—C19—C20120.9 (3)C38—C43—H43119.8
C18—C19—H19119.6O10—C44—H44A109.5
C20—C19—H19119.6O10—C44—H44B109.5
C21—C20—C19119.6 (3)H44A—C44—H44B109.5
C21—C20—H20120.2O10—C44—H44C109.5
C19—C20—H20120.2H44A—C44—H44C109.5
C20—C21—C16121.0 (3)H44B—C44—H44C109.5
C7—N1—C1—C28.2 (4)C37—N2—C23—C28169.1 (3)
C15—N1—C1—C2122.7 (3)C29—N2—C23—C2857.9 (3)
C7—N1—C1—C6169.5 (3)C37—N2—C23—C246.7 (4)
C15—N1—C1—C659.6 (4)C29—N2—C23—C24126.3 (3)
C6—C1—C2—C30.2 (5)C28—C23—C24—C251.6 (4)
N1—C1—C2—C3177.5 (3)N2—C23—C24—C25174.3 (3)
C1—C2—C3—C41.5 (5)C23—C24—C25—C260.2 (5)
C2—C3—C4—O1178.8 (3)C24—C25—C26—O6175.0 (3)
C2—C3—C4—C52.4 (6)C24—C25—C26—C272.8 (5)
C3—C4—C5—C62.0 (5)C25—C26—C27—C283.6 (5)
O1—C4—C5—C6179.1 (3)O6—C26—C27—C28174.3 (3)
C4—C5—C6—C10.7 (5)C24—C23—C28—C270.8 (5)
C2—C1—C6—C50.2 (5)N2—C23—C28—C27175.2 (3)
N1—C1—C6—C5178.1 (3)C26—C27—C28—C231.8 (5)
C1—N1—C7—C874.4 (3)C23—N2—C29—C30158.7 (2)
C15—N1—C7—C8152.7 (2)C37—N2—C29—C3066.0 (3)
N1—C7—C8—C938.0 (4)N2—C29—C30—C3166.8 (4)
N1—C7—C8—C13149.7 (3)N2—C29—C30—C35109.3 (3)
C13—C8—C9—O2178.2 (3)C35—C30—C31—O7179.0 (3)
C7—C8—C9—O25.9 (5)C29—C30—C31—O74.7 (4)
C13—C8—C9—C100.3 (5)C35—C30—C31—C320.2 (5)
C7—C8—C9—C10172.0 (3)C29—C30—C31—C32176.5 (3)
C14—O3—C10—C113.4 (5)C36—O8—C32—C331.7 (5)
C14—O3—C10—C9176.7 (3)C36—O8—C32—C31178.0 (3)
C8—C9—C10—O3179.7 (3)O7—C31—C32—O80.7 (4)
O2—C9—C10—O31.7 (4)C30—C31—C32—O8178.0 (3)
C8—C9—C10—C110.4 (5)O7—C31—C32—C33179.6 (3)
O2—C9—C10—C11178.3 (3)C30—C31—C32—C331.7 (5)
O3—C10—C11—C12179.7 (3)O8—C32—C33—C34177.8 (3)
C9—C10—C11—C120.2 (5)C31—C32—C33—C341.9 (5)
C10—C11—C12—C130.8 (5)C32—C33—C34—C350.7 (5)
C11—C12—C13—C80.8 (5)C33—C34—C35—C300.8 (5)
C9—C8—C13—C120.3 (5)C31—C30—C35—C341.1 (5)
C7—C8—C13—C12172.7 (3)C29—C30—C35—C34175.1 (3)
C1—N1—C15—C16151.0 (3)C23—N2—C37—C3869.6 (3)
C7—N1—C15—C1674.8 (3)C29—N2—C37—C38156.3 (2)
N1—C15—C16—C21107.1 (3)N2—C37—C38—C43148.5 (3)
N1—C15—C16—C1771.1 (3)N2—C37—C38—C3939.3 (4)
C21—C16—C17—O4178.7 (3)C43—C38—C39—O9177.6 (3)
C15—C16—C17—O43.0 (4)C37—C38—C39—O95.4 (5)
C21—C16—C17—C182.3 (5)C43—C38—C39—C401.2 (5)
C15—C16—C17—C18176.0 (3)C37—C38—C39—C40173.4 (3)
C22—O5—C18—C192.5 (5)C44—O10—C40—C416.3 (5)
C22—O5—C18—C17176.1 (3)C44—O10—C40—C39173.9 (3)
O4—C17—C18—C19179.5 (3)O9—C39—C40—C41177.0 (3)
C16—C17—C18—C191.5 (5)C38—C39—C40—C411.9 (5)
O4—C17—C18—O50.8 (4)O9—C39—C40—O103.3 (4)
C16—C17—C18—O5179.8 (3)C38—C39—C40—O10177.9 (3)
O5—C18—C19—C20178.5 (3)O10—C40—C41—C42178.9 (3)
C17—C18—C19—C200.0 (5)C39—C40—C41—C420.9 (5)
C18—C19—C20—C210.7 (5)C40—C41—C42—C430.9 (5)
C19—C20—C21—C160.1 (5)C41—C42—C43—C381.6 (5)
C17—C16—C21—C201.6 (5)C39—C38—C43—C420.5 (5)
C15—C16—C21—C20176.6 (3)C37—C38—C43—C42171.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O9i0.822.383.185 (3)168
O1—H1···O10i0.822.352.911 (3)127
O2—H2···N10.821.972.697 (3)147
O4—H4···O50.822.192.640 (3)115
O4—H4···O6ii0.822.492.941 (3)116
O6—H6···O2iii0.822.102.913 (3)171
O6—H6···O3iii0.822.503.008 (3)121
O7—H7···O1iv0.822.112.835 (3)148
O7—H7···O80.822.172.629 (3)115
O9—H9···O70.822.453.023 (3)128
O9—H9···N20.822.042.753 (3)146
C5—H5···O7ii0.932.503.218 (4)134
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x+1, y+2, z+1; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC22H23NO5
Mr381.41
Crystal system, space groupTriclinic, 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)
V3)1914.0 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.24 × 0.17 × 0.15
Data collection
DiffractometerSiemens SMART 1000 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.978, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
10128, 6656, 2772
Rint0.041
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.067, 0.89
No. of reflections6656
No. of parameters505
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.18

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O9i0.822.383.185 (3)167.6
O1—H1···O10i0.822.352.911 (3)126.7
O2—H2···N10.821.972.697 (3)146.5
O4—H4···O50.822.192.640 (3)115.0
O4—H4···O6ii0.822.492.941 (3)115.5
O6—H6···O2iii0.822.102.913 (3)170.5
O6—H6···O3iii0.822.503.008 (3)120.8
O7—H7···O1iv0.822.112.835 (3)147.5
O7—H7···O80.822.172.629 (3)115.4
O9—H9···O70.822.453.023 (3)127.6
O9—H9···N20.822.042.753 (3)145.8
C5—H5···O7ii0.932.503.218 (4)133.8
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x+1, y+2, z+1; (iv) x, y+1, z.
 

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