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Acta Cryst. (2009). E65, o741    [ doi:10.1107/S1600536809008046 ]

4-(2,3,4-Trimethoxy-6-methylbenzylideneamino)phenol

C.-Y. Wang

Abstract top

The asymmetric unit of the title compound, C17H19NO4, contains two independent molecules in which the dihedral angles between the two benzene rings are 83.1 (2) and 88.5 (2)°. Each molecule adopts a trans configuration with respect to the C=N bond. In the crystal structure, molecules are linked by intermolecular O-H...N hydrogen bonds, forming two independent one-dimensional chains running along the b-axis direction.

Comment top

The preparation, properties and applications of Schiff bases are important in the development of coordination chemistry (see e.g. Yu et al., 2007). In this paper, the structure of the title compound, (I), is reported. The asymmetric unit of (I) is shown in Fig. 1. The bond lengths and angles of the title compound agree with those in the related compound (E)—N-(2,3,4-Trimethoxy-6-methylbenzylidene)naphthalen-1-amine (Wang, 2008), as representative example. The asymmetric unit of the title compound consists of two independent molecules, in which the dihedral angles between the two benzene rings in each are 83.1 (2)° [for rings C2-C7 and C12-C17] and 88.5 (2)° [for rings C19-C24 and C29-C34]. The molecules adopt a trans configuration about the central C=N bond. In the crystal structure, molecules are linked by intermolecular O—H···N hydrogen bonds to form two independent one-dimensional chains running along the b axis direction (Fig. 2 and Table 1).

Related literature top

For the preparation, properties and applications of Schiff bases, see: Yu et al. (2007).For a related structure, see: Wang (2009).

Experimental top

A mixture of 4-aminophenol (0.545 g, 5 mmol) and 2,3,4-trimethoxy-6-methylbenzaldehyde (1.04 g, 5 mmol) in ethyl alcohol (30 ml) was refluxed for 2 h. After cooling the precipitate was filtered and dried. The crude product of 20 mg was dissolved in 20 ml of ethyl alcohol by heating on a magnetic stirrer. The solution was filtered to remove impurities, and then left at room temperature. After a week single crystals of (I) suitable for structure determination were obtained.

Refinement top

The H atoms were positioned geometrically (C—H = 0.93–0.96 Å; O-H = 0.82Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5 Ueq(methyl C or O).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), drawn with 30% probability ellipsoids.
[Figure 2] Fig. 2. Part of the crystal structure of (I) with hydrogen bonds drawn as dashed lines.
4-(2,3,4-Trimethoxy-6-methylbenzylideneamino)phenol top
Crystal data top
C17H19NO4F(000) = 2560
Mr = 301.33Dx = 1.247 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3411 reflections
a = 20.045 (2) Åθ = 2.5–20.5°
b = 13.2042 (19) ŵ = 0.09 mm−1
c = 24.253 (3) ÅT = 298 K
V = 6419.2 (14) Å3Block, light yellow
Z = 160.49 × 0.48 × 0.42 mm
Data collection top
Bruker SMART CCD
diffractometer		5654 independent reflections
Radiation source: fine-focus sealed tube2589 reflections with I > 2σ(I)
graphiteRint = 0.092
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −19→23
Tmin = 0.958, Tmax = 0.964k = −15→15
25460 measured reflectionsl = −28→22
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + 11.5471P]
where P = (Fo2 + 2Fc2)/3
5654 reflections(Δ/σ)max = 0.001
405 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
C17H19NO4V = 6419.2 (14) Å3
Mr = 301.33Z = 16
Orthorhombic, PbcaMo Kα radiation
a = 20.045 (2) ŵ = 0.09 mm−1
b = 13.2042 (19) ÅT = 298 K
c = 24.253 (3) Å0.49 × 0.48 × 0.42 mm
Data collection top
Bruker SMART CCD
diffractometer		5654 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2589 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.964Rint = 0.092
25460 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.063 w = 1/[σ2(Fo2) + 11.5471P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.206Δρmax = 0.21 e Å−3
S = 1.12Δρmin = −0.22 e Å−3
5654 reflectionsAbsolute structure: ?
405 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
H-atom parameters constrained
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
N10.09178 (18)0.5134 (3)0.75088 (16)0.0456 (10)
N20.16453 (19)1.0602 (3)0.98602 (16)0.0473 (10)
O10.18197 (15)0.3410 (2)0.65385 (12)0.0514 (9)
O20.21163 (16)0.1364 (2)0.67521 (14)0.0556 (9)
O30.20521 (18)0.0660 (3)0.77778 (15)0.0695 (11)
O40.03160 (18)0.9210 (3)0.71702 (15)0.0705 (11)
H4−0.00890.92950.71510.106*
O50.05416 (18)0.9042 (3)0.89798 (14)0.0650 (10)
O60.01757 (18)0.6985 (3)0.91633 (14)0.0644 (10)
O70.03635 (17)0.6176 (2)1.01429 (15)0.0601 (10)
O80.20925 (18)1.4749 (3)0.99430 (17)0.0764 (12)
H80.24821.48850.98710.115*
C10.1457 (2)0.4734 (4)0.73373 (18)0.0447 (12)
H10.17410.51090.71140.054*
C20.1638 (2)0.3693 (4)0.74853 (18)0.0397 (11)
C30.1825 (2)0.3028 (4)0.70673 (18)0.0394 (11)
C40.1949 (2)0.2018 (4)0.71691 (19)0.0456 (12)
C50.1922 (2)0.1671 (4)0.7710 (2)0.0484 (13)
C60.1770 (2)0.2326 (4)0.8130 (2)0.0564 (14)
H60.17680.20890.84920.068*
C70.1621 (2)0.3331 (4)0.80274 (19)0.0498 (13)
C80.2416 (3)0.3325 (5)0.6226 (2)0.0737 (17)
H8A0.27940.34020.64660.111*
H8B0.24250.38430.59490.111*
H8C0.24330.26720.60530.111*
C90.1551 (3)0.0923 (5)0.6491 (3)0.0854 (19)
H9A0.13230.04920.67480.128*
H9B0.16930.05310.61790.128*
H9C0.12550.14500.63700.128*
C100.1876 (4)0.0206 (5)0.8287 (3)0.103 (2)
H10A0.21470.04850.85760.155*
H10B0.1947−0.05120.82660.155*
H10C0.14140.03390.83640.155*
C110.1440 (3)0.4002 (5)0.8507 (2)0.0784 (19)
H11A0.09650.40020.85560.118*
H11B0.15900.46800.84360.118*
H11C0.16500.37530.88360.118*
C120.0783 (2)0.6174 (4)0.73988 (19)0.0427 (12)
C130.1269 (2)0.6905 (4)0.7358 (2)0.0564 (14)
H130.17160.67200.73820.068*
C140.1104 (3)0.7909 (4)0.7282 (2)0.0598 (15)
H140.14410.83920.72590.072*
C150.0449 (3)0.8208 (4)0.7239 (2)0.0525 (13)
C16−0.0032 (2)0.7480 (4)0.7281 (2)0.0600 (15)
H16−0.04790.76630.72530.072*
C170.0131 (2)0.6478 (4)0.7362 (2)0.0565 (14)
H17−0.02070.60000.73930.068*
C180.1073 (2)1.0219 (4)0.97645 (19)0.0497 (13)
H180.07441.06260.96110.060*
C190.0916 (2)0.9151 (3)0.98894 (19)0.0431 (12)
C200.0615 (2)0.8572 (4)0.94810 (19)0.0437 (12)
C210.0456 (2)0.7570 (4)0.9569 (2)0.0441 (12)
C220.0562 (2)0.7160 (4)1.0086 (2)0.0455 (12)
C230.0853 (2)0.7717 (4)1.0497 (2)0.0499 (13)
H230.09210.74261.08420.060*
C240.1049 (2)0.8722 (4)1.0404 (2)0.0472 (12)
C25−0.0055 (3)0.8951 (6)0.8685 (3)0.103 (2)
H25A−0.00300.83760.84440.154*
H25B−0.01260.95530.84710.154*
H25C−0.04190.88640.89380.154*
C260.0659 (3)0.6435 (5)0.8855 (3)0.100 (2)
H26A0.09440.69000.86630.150*
H26B0.04370.60050.85930.150*
H26C0.09210.60270.91000.150*
C270.0461 (3)0.5706 (4)1.0661 (2)0.0809 (19)
H27A0.09290.56951.07470.121*
H27B0.02940.50251.06480.121*
H27C0.02260.60791.09400.121*
C280.1402 (3)0.9258 (4)1.0866 (2)0.0735 (17)
H28A0.18760.91871.08200.110*
H28B0.12700.89661.12120.110*
H28C0.12860.99631.08610.110*
C290.1736 (2)1.1670 (3)0.98294 (18)0.0427 (12)
C300.2359 (2)1.2045 (4)0.9702 (2)0.0481 (13)
H300.26981.16020.96010.058*
C310.2483 (2)1.3071 (4)0.9724 (2)0.0507 (13)
H310.29011.33170.96250.061*
C320.1995 (2)1.3735 (4)0.9891 (2)0.0481 (12)
C330.1365 (2)1.3370 (4)1.0002 (2)0.0570 (14)
H330.10251.38151.00960.068*
C340.1242 (2)1.2354 (4)0.9973 (2)0.0526 (13)
H340.08161.21161.00520.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.043 (2)0.043 (3)0.051 (2)0.0044 (19)−0.0004 (19)−0.006 (2)
N20.047 (2)0.040 (3)0.055 (3)−0.0077 (19)0.004 (2)−0.001 (2)
O10.054 (2)0.058 (2)0.042 (2)0.0144 (17)0.0005 (16)0.0045 (17)
O20.061 (2)0.049 (2)0.057 (2)0.0103 (18)0.0036 (18)−0.0065 (18)
O30.077 (3)0.059 (3)0.072 (3)0.017 (2)0.014 (2)0.020 (2)
O40.068 (2)0.040 (2)0.103 (3)0.0017 (18)0.023 (2)0.006 (2)
O50.073 (3)0.070 (3)0.052 (2)−0.020 (2)−0.0142 (19)0.0144 (19)
O60.071 (3)0.064 (3)0.058 (2)−0.011 (2)−0.0055 (19)−0.015 (2)
O70.073 (2)0.038 (2)0.069 (2)−0.0106 (18)−0.0024 (19)0.0068 (19)
O80.069 (3)0.038 (2)0.122 (4)−0.0053 (19)0.000 (2)−0.004 (2)
C10.045 (3)0.047 (3)0.042 (3)0.005 (2)−0.003 (2)−0.002 (2)
C20.035 (2)0.049 (3)0.036 (3)0.007 (2)−0.002 (2)0.000 (2)
C30.036 (3)0.045 (3)0.038 (3)0.005 (2)−0.003 (2)0.002 (2)
C40.042 (3)0.049 (3)0.046 (3)0.007 (2)0.004 (2)−0.001 (3)
C50.046 (3)0.045 (3)0.054 (3)0.015 (2)0.002 (2)0.010 (3)
C60.057 (3)0.069 (4)0.043 (3)0.014 (3)0.003 (2)0.016 (3)
C70.050 (3)0.061 (4)0.038 (3)0.013 (3)−0.001 (2)−0.003 (3)
C80.067 (4)0.097 (5)0.057 (3)0.013 (3)0.016 (3)0.017 (3)
C90.095 (5)0.078 (5)0.084 (5)−0.012 (4)−0.007 (4)−0.029 (4)
C100.140 (6)0.072 (5)0.098 (5)0.018 (4)0.027 (5)0.042 (4)
C110.096 (5)0.096 (5)0.043 (3)0.034 (4)−0.002 (3)−0.006 (3)
C120.040 (3)0.040 (3)0.048 (3)0.003 (2)0.003 (2)−0.005 (2)
C130.041 (3)0.050 (4)0.078 (4)0.002 (3)0.014 (3)−0.007 (3)
C140.051 (3)0.046 (3)0.082 (4)−0.008 (3)0.017 (3)−0.003 (3)
C150.053 (3)0.039 (3)0.066 (3)0.003 (3)0.013 (3)0.001 (3)
C160.043 (3)0.047 (3)0.091 (4)0.005 (3)−0.001 (3)0.002 (3)
C170.039 (3)0.041 (3)0.090 (4)−0.001 (2)−0.003 (3)0.000 (3)
C180.051 (3)0.045 (3)0.054 (3)−0.004 (2)−0.002 (2)0.002 (3)
C190.042 (3)0.036 (3)0.051 (3)−0.003 (2)0.000 (2)−0.004 (2)
C200.044 (3)0.046 (3)0.041 (3)−0.004 (2)0.001 (2)0.003 (2)
C210.042 (3)0.042 (3)0.048 (3)−0.009 (2)−0.004 (2)−0.007 (3)
C220.043 (3)0.039 (3)0.054 (3)−0.005 (2)0.004 (2)−0.003 (3)
C230.055 (3)0.048 (3)0.046 (3)−0.004 (3)−0.006 (2)0.003 (3)
C240.052 (3)0.043 (3)0.046 (3)−0.007 (2)−0.005 (2)−0.001 (3)
C250.099 (5)0.119 (6)0.090 (5)−0.004 (4)−0.043 (4)0.030 (5)
C260.126 (6)0.093 (5)0.082 (5)−0.013 (4)0.028 (4)−0.038 (4)
C270.113 (5)0.049 (4)0.081 (4)−0.013 (3)−0.001 (4)0.019 (3)
C280.108 (5)0.059 (4)0.054 (3)−0.024 (3)−0.015 (3)−0.002 (3)
C290.046 (3)0.038 (3)0.044 (3)−0.005 (2)0.002 (2)−0.002 (2)
C300.043 (3)0.040 (3)0.061 (3)−0.001 (2)0.003 (2)−0.002 (2)
C310.043 (3)0.045 (3)0.063 (3)−0.010 (2)0.000 (3)0.003 (3)
C320.051 (3)0.033 (3)0.060 (3)−0.004 (2)−0.007 (3)0.003 (2)
C330.050 (3)0.043 (3)0.078 (4)0.003 (3)0.005 (3)−0.004 (3)
C340.041 (3)0.048 (3)0.068 (4)−0.005 (2)0.006 (2)−0.001 (3)
Geometric parameters (Å, °) top
N1—C11.272 (5)C12—C171.370 (6)
N1—C121.426 (6)C12—C131.375 (6)
N2—C181.274 (5)C13—C141.379 (7)
N2—C291.424 (6)C13—H130.9300
O1—C31.378 (5)C14—C151.375 (7)
O1—C81.420 (5)C14—H140.9300
O2—C41.371 (5)C15—C161.366 (6)
O2—C91.423 (6)C16—C171.376 (7)
O3—C51.371 (6)C16—H160.9300
O3—C101.417 (6)C17—H170.9300
O4—C151.360 (5)C18—C191.477 (6)
O4—H40.8200C18—H180.9300
O5—C201.373 (5)C19—C201.390 (6)
O5—C251.398 (6)C19—C241.396 (6)
O6—C211.371 (5)C20—C211.378 (6)
O6—C261.424 (6)C21—C221.382 (6)
O7—C221.367 (5)C22—C231.368 (6)
O7—C271.415 (6)C23—C241.403 (6)
O8—C321.360 (5)C23—H230.9300
O8—H80.8200C24—C281.503 (6)
C1—C21.466 (6)C25—H25A0.9600
C1—H10.9300C25—H25B0.9600
C2—C31.392 (6)C25—H25C0.9600
C2—C71.399 (6)C26—H26A0.9600
C3—C41.380 (6)C26—H26B0.9600
C4—C51.389 (6)C26—H26C0.9600
C5—C61.371 (7)C27—H27A0.9600
C6—C71.383 (7)C27—H27B0.9600
C6—H60.9300C27—H27C0.9600
C7—C111.507 (7)C28—H28A0.9600
C8—H8A0.9600C28—H28B0.9600
C8—H8B0.9600C28—H28C0.9600
C8—H8C0.9600C29—C301.379 (6)
C9—H9A0.9600C29—C341.385 (6)
C9—H9B0.9600C30—C311.379 (6)
C9—H9C0.9600C30—H300.9300
C10—H10A0.9600C31—C321.375 (6)
C10—H10B0.9600C31—H310.9300
C10—H10C0.9600C32—C331.377 (6)
C11—H11A0.9600C33—C341.367 (7)
C11—H11B0.9600C33—H330.9300
C11—H11C0.9600C34—H340.9300
C1—N1—C12120.0 (4)C15—C16—H16119.4
C18—N2—C29119.8 (4)C17—C16—H16119.4
C3—O1—C8117.5 (4)C12—C17—C16121.2 (5)
C4—O2—C9113.0 (4)C12—C17—H17119.4
C5—O3—C10118.0 (4)C16—C17—H17119.4
C15—O4—H4109.5N2—C18—C19122.2 (5)
C20—O5—C25120.4 (4)N2—C18—H18118.9
C21—O6—C26112.7 (4)C19—C18—H18118.9
C22—O7—C27117.8 (4)C20—C19—C24119.8 (4)
C32—O8—H8109.5C20—C19—C18118.2 (4)
N1—C1—C2121.3 (4)C24—C19—C18122.0 (4)
N1—C1—H1119.4O5—C20—C21123.2 (4)
C2—C1—H1119.4O5—C20—C19115.4 (4)
C3—C2—C7118.4 (4)C21—C20—C19121.2 (4)
C3—C2—C1118.6 (4)O6—C21—C20121.6 (4)
C7—C2—C1123.0 (4)O6—C21—C22119.7 (4)
O1—C3—C4121.4 (4)C20—C21—C22118.7 (4)
O1—C3—C2116.4 (4)O7—C22—C23124.2 (5)
C4—C3—C2121.9 (4)O7—C22—C21114.7 (4)
O2—C4—C3121.4 (4)C23—C22—C21121.1 (4)
O2—C4—C5119.9 (4)C22—C23—C24120.7 (5)
C3—C4—C5118.7 (4)C22—C23—H23119.7
O3—C5—C6124.5 (5)C24—C23—H23119.7
O3—C5—C4115.3 (5)C19—C24—C23118.3 (4)
C6—C5—C4120.3 (5)C19—C24—C28124.4 (4)
C5—C6—C7121.2 (5)C23—C24—C28117.2 (4)
C5—C6—H6119.4O5—C25—H25A109.5
C7—C6—H6119.4O5—C25—H25B109.5
C6—C7—C2119.5 (4)H25A—C25—H25B109.5
C6—C7—C11118.5 (5)O5—C25—H25C109.5
C2—C7—C11122.0 (5)H25A—C25—H25C109.5
O1—C8—H8A109.5H25B—C25—H25C109.5
O1—C8—H8B109.5O6—C26—H26A109.5
H8A—C8—H8B109.5O6—C26—H26B109.5
O1—C8—H8C109.5H26A—C26—H26B109.5
H8A—C8—H8C109.5O6—C26—H26C109.5
H8B—C8—H8C109.5H26A—C26—H26C109.5
O2—C9—H9A109.5H26B—C26—H26C109.5
O2—C9—H9B109.5O7—C27—H27A109.5
H9A—C9—H9B109.5O7—C27—H27B109.5
O2—C9—H9C109.5H27A—C27—H27B109.5
H9A—C9—H9C109.5O7—C27—H27C109.5
H9B—C9—H9C109.5H27A—C27—H27C109.5
O3—C10—H10A109.5H27B—C27—H27C109.5
O3—C10—H10B109.5C24—C28—H28A109.5
H10A—C10—H10B109.5C24—C28—H28B109.5
O3—C10—H10C109.5H28A—C28—H28B109.5
H10A—C10—H10C109.5C24—C28—H28C109.5
H10B—C10—H10C109.5H28A—C28—H28C109.5
C7—C11—H11A109.5H28B—C28—H28C109.5
C7—C11—H11B109.5C30—C29—C34118.0 (4)
H11A—C11—H11B109.5C30—C29—N2118.9 (4)
C7—C11—H11C109.5C34—C29—N2122.8 (4)
H11A—C11—H11C109.5C31—C30—C29120.6 (5)
H11B—C11—H11C109.5C31—C30—H30119.7
C17—C12—C13117.7 (5)C29—C30—H30119.7
C17—C12—N1118.4 (4)C32—C31—C30120.5 (5)
C13—C12—N1123.8 (4)C32—C31—H31119.7
C12—C13—C14121.0 (5)C30—C31—H31119.7
C12—C13—H13119.5O8—C32—C31123.5 (5)
C14—C13—H13119.5O8—C32—C33117.3 (5)
C15—C14—C13121.0 (5)C31—C32—C33119.2 (5)
C15—C14—H14119.5C34—C33—C32120.0 (5)
C13—C14—H14119.5C34—C33—H33120.0
O4—C15—C16123.8 (5)C32—C33—H33120.0
O4—C15—C14118.4 (5)C33—C34—C29121.6 (5)
C16—C15—C14117.8 (5)C33—C34—H34119.2
C15—C16—C17121.2 (5)C29—C34—H34119.2
C12—N1—C1—C2174.5 (4)C29—N2—C18—C19−168.3 (4)
N1—C1—C2—C3129.8 (5)N2—C18—C19—C20−130.8 (5)
N1—C1—C2—C7−49.3 (7)N2—C18—C19—C2450.4 (7)
C8—O1—C3—C4−60.4 (6)C25—O5—C20—C2148.7 (7)
C8—O1—C3—C2125.4 (5)C25—O5—C20—C19−136.6 (5)
C7—C2—C3—O1178.6 (4)C24—C19—C20—O5−176.1 (4)
C1—C2—C3—O1−0.5 (6)C18—C19—C20—O55.0 (6)
C7—C2—C3—C44.4 (7)C24—C19—C20—C21−1.4 (7)
C1—C2—C3—C4−174.6 (4)C18—C19—C20—C21179.8 (4)
C9—O2—C4—C3−87.7 (6)C26—O6—C21—C2093.7 (6)
C9—O2—C4—C594.2 (5)C26—O6—C21—C22−88.7 (6)
O1—C3—C4—O24.4 (7)O5—C20—C21—O6−3.8 (7)
C2—C3—C4—O2178.2 (4)C19—C20—C21—O6−178.2 (4)
O1—C3—C4—C5−177.5 (4)O5—C20—C21—C22178.5 (4)
C2—C3—C4—C5−3.6 (7)C19—C20—C21—C224.1 (7)
C10—O3—C5—C615.0 (8)C27—O7—C22—C230.4 (7)
C10—O3—C5—C4−164.8 (5)C27—O7—C22—C21179.6 (4)
O2—C4—C5—O3−1.7 (6)O6—C21—C22—O7−0.5 (6)
C3—C4—C5—O3−179.9 (4)C20—C21—C22—O7177.2 (4)
O2—C4—C5—C6178.5 (4)O6—C21—C22—C23178.7 (4)
C3—C4—C5—C60.3 (7)C20—C21—C22—C23−3.5 (7)
O3—C5—C6—C7−177.7 (5)O7—C22—C23—C24179.3 (4)
C4—C5—C6—C72.1 (8)C21—C22—C23—C240.1 (7)
C5—C6—C7—C2−1.2 (7)C20—C19—C24—C23−2.0 (7)
C5—C6—C7—C11178.3 (5)C18—C19—C24—C23176.8 (4)
C3—C2—C7—C6−2.0 (7)C20—C19—C24—C28176.9 (5)
C1—C2—C7—C6177.0 (4)C18—C19—C24—C28−4.3 (8)
C3—C2—C7—C11178.6 (4)C22—C23—C24—C192.7 (7)
C1—C2—C7—C11−2.4 (7)C22—C23—C24—C28−176.4 (5)
C1—N1—C12—C17152.0 (5)C18—N2—C29—C30−153.0 (5)
C1—N1—C12—C13−31.9 (7)C18—N2—C29—C3433.4 (7)
C17—C12—C13—C14−0.1 (8)C34—C29—C30—C310.6 (7)
N1—C12—C13—C14−176.3 (5)N2—C29—C30—C31−173.3 (4)
C12—C13—C14—C15−0.6 (8)C29—C30—C31—C322.2 (8)
C13—C14—C15—O4179.3 (5)C30—C31—C32—O8177.2 (5)
C13—C14—C15—C160.7 (8)C30—C31—C32—C33−4.2 (8)
O4—C15—C16—C17−178.6 (5)O8—C32—C33—C34−178.0 (5)
C14—C15—C16—C170.0 (8)C31—C32—C33—C343.4 (8)
C13—C12—C17—C160.8 (8)C32—C33—C34—C29−0.5 (8)
N1—C12—C17—C16177.2 (5)C30—C29—C34—C33−1.5 (7)
C15—C16—C17—C12−0.7 (9)N2—C29—C34—C33172.2 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4···N1i0.822.162.866 (5)144
O8—H8···N2ii0.821.992.777 (5)161
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1/2, y+1/2, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4···N1i0.822.162.866 (5)144
O8—H8···N2ii0.821.992.777 (5)161
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1/2, y+1/2, z.
references
References top

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Wang, C.-Y. (2009). Acta Cryst. E65, o56.

Yu, T.-Z., Zhang, K., Yuling Zhao, Y.-L., Yang, C.-H., Zhang, H., Fan, D.-W. & Dong, W.-K. (2007). Inorg. Chem. Commun. 10, 401–403.