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Acta Cryst. (2007). E63, o3094-o3095
https://doi.org/10.1107/S1600536807026141
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5,5′-Dimeth­oxy-2,2′-[1,2-phenyl­ene­bis(nitrilo­methyl­idyne)]diphenol

N. E. Eltayeb, S. G. Teoh, S. Chantrapromma, H.-K. Fun and K. Ibrahim
The title compound, C22H20N2O4, is a Schiff base ligand. The dihedral angles between the central and two outer benzene rings are 2.20 (12) and 58.29 (12)°. Two O—H...N intra­molecular hydrogen bonds involving the two hydr­oxy groups generate S(6) ring motifs. In the crystal structure, mol­ecules are stacked approximately along the a axis and are linked by weak inter­molecular C—H...O inter­actions. The crystal structure is stabilized by intra­molecular O—H...N hydrogen bonds, weak C—H...O inter­molecular inter­actions and C—H...π inter­actions.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026141/om2130sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026141/om2130Isup2.hkl
Contains datablock I

CCDC reference: 654870

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.053
  • wR factor = 0.173
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O3     -   H1O3   ...       1.03 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2


Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

Schiff base compounds have received much attention because of their potential applications. Some of these compounds exhibit various pharmacological activities, such as anticancer (Dao et al., 2000), anti-HIV (Sriram et al., 2006), antibacterial and antifungal (Karthikeyan et al., 2006) properties. In addition, some of them may be used as analytical reagents for the determination of trace elements (Eltayeb & Ahmed, 2005a,b). Recently we have reported the crystal structures of 2,2'-[1,2-phenylenebis(nitrilomethylidyne)]bis(5-methylphenol) (Eltayeb, Teoh, Chantrapromma et al., 2007a) and 6,6'-Dimethyl-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol (Eltayeb, Teoh, Chantrapromma et al., 2007b). As an extension of our investigations of Schiff base ligands and their complexes, the title compound was synthesized by the reaction of o-phenylenediamine and 4-methoxysalicylaldehyde, and its crystal structure is reported here.

In the structure of the title compound, the C15–C20 benzene ring is almost planar with the o-phenylaniline as indicated by the dihedral angle between the C8–C13 and C15–C20 benzene rings being 2.20 (12)° and the torsion angle C13/N2/C14/C15 = 178.2 (2)°. The C1–C6 benzene ring makes the dihedral angles of 58.29 (12)° and 57.60 (12)° with C8–C13 and C15–C20 benzene rings, respectively and the torsion angle C8/N1/C7/C6 is -178.8 (2)°. The two methoxy groups are slightly deviated from the mean planes of C1–C6 and C15–C20 benzene rings with the torsion angles C21/O2/C3/C2 = 5.5 (4)° and C22/O4/C18/C19 = -5.8 (4)°. The two intramolecular hydrogen bonds, O1—H1O1···N1 and O3—H1O3···N2 generate S(6) ring motifs (Bernstein et al., 1995). Bond lengths and angles are in normal ranges (Allen et al., 1987) and comparable to those in related structures (Eltayeb, Teoh, Chantrapromma et al., 2007a; 2007b; Eltayeb, Teoh, Teh et al., 2007a; 2007b).

In the crystal, the molecules are stacked approximately along the a axis and are linked by weak C—H···O intermolecular interactions (Table 1). The crystal is stabilized by O—H···N intramolecular hydrogen bonds, weak C—H···O intermolecular interactions and C—H···π interactions (Table 1); Cg1 and Cg2 are the centroids of C1–C6 and C8–C13 benzene rings, respectively.

Related literature top

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Eltayeb, Teoh, Chantrapromma et al. (2007a,b); Eltayeb, Teoh, Teh et al. (2007a,b). For related literature on pharmacological activities and applications, see: Dao et al. (2000); Karthikeyan et al. (2006); Sriram et al. (2006); Eltayeb & Ahmed (2005a,b).

For related literature, see: Allen et al. (1987).

Experimental top

The title compound was synthesized by adding 4-methoxysalicylaldehyde (0.608 g, 4 mmol) into a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol 95% (20 ml). The mixture was refluxed with stirring for half an hour. The resultant yellow solution was filtered. Yellow needle-shaped single crystals suitable for x-ray structure determination were formed after one week of slow evaporation of the solvent at room temperature.

Refinement top

Hydroxyl H atoms were located from the difference map and isotropically refined. The O—H distance was restrainted to be 1.02 Å. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.96 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups.

Structure description top

Schiff base compounds have received much attention because of their potential applications. Some of these compounds exhibit various pharmacological activities, such as anticancer (Dao et al., 2000), anti-HIV (Sriram et al., 2006), antibacterial and antifungal (Karthikeyan et al., 2006) properties. In addition, some of them may be used as analytical reagents for the determination of trace elements (Eltayeb & Ahmed, 2005a,b). Recently we have reported the crystal structures of 2,2'-[1,2-phenylenebis(nitrilomethylidyne)]bis(5-methylphenol) (Eltayeb, Teoh, Chantrapromma et al., 2007a) and 6,6'-Dimethyl-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol (Eltayeb, Teoh, Chantrapromma et al., 2007b). As an extension of our investigations of Schiff base ligands and their complexes, the title compound was synthesized by the reaction of o-phenylenediamine and 4-methoxysalicylaldehyde, and its crystal structure is reported here.

In the structure of the title compound, the C15–C20 benzene ring is almost planar with the o-phenylaniline as indicated by the dihedral angle between the C8–C13 and C15–C20 benzene rings being 2.20 (12)° and the torsion angle C13/N2/C14/C15 = 178.2 (2)°. The C1–C6 benzene ring makes the dihedral angles of 58.29 (12)° and 57.60 (12)° with C8–C13 and C15–C20 benzene rings, respectively and the torsion angle C8/N1/C7/C6 is -178.8 (2)°. The two methoxy groups are slightly deviated from the mean planes of C1–C6 and C15–C20 benzene rings with the torsion angles C21/O2/C3/C2 = 5.5 (4)° and C22/O4/C18/C19 = -5.8 (4)°. The two intramolecular hydrogen bonds, O1—H1O1···N1 and O3—H1O3···N2 generate S(6) ring motifs (Bernstein et al., 1995). Bond lengths and angles are in normal ranges (Allen et al., 1987) and comparable to those in related structures (Eltayeb, Teoh, Chantrapromma et al., 2007a; 2007b; Eltayeb, Teoh, Teh et al., 2007a; 2007b).

In the crystal, the molecules are stacked approximately along the a axis and are linked by weak C—H···O intermolecular interactions (Table 1). The crystal is stabilized by O—H···N intramolecular hydrogen bonds, weak C—H···O intermolecular interactions and C—H···π interactions (Table 1); Cg1 and Cg2 are the centroids of C1–C6 and C8–C13 benzene rings, respectively.

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Eltayeb, Teoh, Chantrapromma et al. (2007a,b); Eltayeb, Teoh, Teh et al. (2007a,b). For related literature on pharmacological activities and applications, see: Dao et al. (2000); Karthikeyan et al. (2006); Sriram et al. (2006); Eltayeb & Ahmed (2005a,b).

For related literature, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The asymmetric unit, showing 50% probability displacement ellipsoids and the atomic numbering. Hydrogen bonds were drawn as dashed lines.
[Figure 2] Fig. 2. The crystal packing, viewed along the a axis. Hydrogen bonds were drawn as dashed lines.
5,5'-Dimethoxy-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol top
Crystal data top
C22H20N2O4F(000) = 792
Mr = 376.40Dx = 1.358 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3248 reflections
a = 6.2038 (3) Åθ = 2.3–25.0°
b = 17.8512 (8) ŵ = 0.09 mm−1
c = 16.6216 (9) ÅT = 100 K
β = 91.072 (3)°Needle, yellow
V = 1840.44 (16) Å30.56 × 0.09 × 0.07 mm
Z = 4
Data collection top
Bruker SMART APEX II CCD area-detector
diffractometer		3243 independent reflections
Radiation source: fine-focus sealed tube2216 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 2.3°
ω scansh = −7→7
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −21→19
Tmin = 0.949, Tmax = 0.994l = −19→17
13290 measured reflections
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0933P)2]
where P = (Fo2 + 2Fc2)/3
3243 reflections(Δ/σ)max < 0.001
262 parametersΔρmax = 0.33 e Å−3
1 restraintΔρmin = −0.40 e Å−3
Crystal data top
C22H20N2O4V = 1840.44 (16) Å3
Mr = 376.40Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.2038 (3) ŵ = 0.09 mm−1
b = 17.8512 (8) ÅT = 100 K
c = 16.6216 (9) Å0.56 × 0.09 × 0.07 mm
β = 91.072 (3)°
Data collection top
Bruker SMART APEX II CCD area-detector
diffractometer		3243 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		2216 reflections with I > 2σ(I)
Tmin = 0.949, Tmax = 0.994Rint = 0.065
13290 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0531 restraint
wR(F2) = 0.173H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.33 e Å−3
3243 reflectionsΔρmin = −0.40 e Å−3
262 parameters
Special details top

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
O10.0703 (3)0.32653 (11)0.80217 (12)0.0248 (5)
O2−0.0700 (3)0.55094 (10)0.65403 (12)0.0286 (5)
O30.2304 (3)0.35378 (10)0.98638 (11)0.0228 (5)
H1O30.105 (3)0.3163 (13)0.9890 (18)0.034*
O40.8395 (3)0.41639 (10)1.15245 (11)0.0263 (5)
N1−0.2356 (4)0.27947 (12)0.89576 (13)0.0220 (5)
N2−0.0249 (3)0.25266 (11)1.03707 (13)0.0195 (5)
C1−0.0650 (4)0.38340 (14)0.78190 (15)0.0202 (6)
C20.0077 (4)0.43688 (14)0.72876 (15)0.0201 (6)
H2A0.14500.43300.70760.024*
C3−0.1249 (4)0.49629 (15)0.70726 (16)0.0232 (6)
C4−0.3302 (5)0.50314 (15)0.73896 (16)0.0252 (6)
H4A−0.41680.54390.72540.030*
C5−0.4034 (4)0.44916 (15)0.79042 (16)0.0243 (6)
H5A−0.54120.45350.81100.029*
C6−0.2752 (4)0.38736 (14)0.81284 (15)0.0203 (6)
C7−0.3570 (4)0.33203 (14)0.86776 (16)0.0214 (6)
H7A−0.50020.33450.88320.026*
C8−0.3254 (4)0.22534 (14)0.94862 (15)0.0198 (6)
C9−0.5118 (4)0.18563 (14)0.92858 (17)0.0240 (6)
H9A−0.58740.19650.88120.029*
C10−0.5849 (4)0.12966 (16)0.97942 (17)0.0258 (7)
H10A−0.70900.10290.96590.031*
C11−0.4735 (5)0.11399 (15)1.04981 (17)0.0261 (7)
H11A−0.52170.07601.08320.031*
C12−0.2898 (4)0.15427 (14)1.07156 (17)0.0243 (6)
H12A−0.21860.14431.12010.029*
C13−0.2122 (4)0.20983 (14)1.02039 (15)0.0203 (6)
C140.0948 (4)0.24777 (14)1.10232 (16)0.0223 (6)
H14A0.05510.21481.14270.027*
C150.2837 (4)0.29153 (14)1.11309 (15)0.0196 (6)
C160.4149 (4)0.28349 (15)1.18253 (15)0.0225 (6)
H16A0.37520.24931.22180.027*
C170.5979 (5)0.32428 (14)1.19388 (17)0.0237 (6)
H17A0.68380.31731.23970.028*
C180.6564 (4)0.37763 (14)1.13482 (16)0.0212 (6)
C190.5320 (4)0.38755 (14)1.06639 (16)0.0208 (6)
H19A0.57210.42321.02870.025*
C200.3453 (4)0.34473 (14)1.05253 (15)0.0199 (6)
C210.1296 (5)0.54218 (18)0.6133 (2)0.0395 (8)
H21A0.14710.58260.57590.059*
H21B0.12900.49540.58470.059*
H21C0.24670.54260.65180.059*
C220.9184 (5)0.46624 (15)1.09219 (17)0.0259 (7)
H22A1.05820.48451.10840.039*
H22B0.82090.50771.08580.039*
H22C0.92890.44001.04200.039*
H1O10.005 (6)0.2990 (19)0.837 (2)0.052 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0248 (11)0.0254 (11)0.0245 (11)0.0065 (9)0.0051 (9)0.0069 (9)
O20.0292 (11)0.0256 (11)0.0309 (11)−0.0004 (8)0.0014 (9)0.0105 (8)
O30.0213 (10)0.0253 (11)0.0219 (10)−0.0029 (8)0.0004 (8)0.0020 (8)
O40.0249 (11)0.0268 (11)0.0272 (11)−0.0061 (9)0.0005 (8)−0.0013 (8)
N10.0262 (13)0.0227 (12)0.0173 (12)−0.0010 (10)0.0029 (10)−0.0014 (9)
N20.0187 (12)0.0174 (12)0.0226 (12)0.0009 (9)0.0024 (9)−0.0019 (9)
C10.0233 (15)0.0204 (15)0.0167 (14)0.0018 (11)−0.0013 (11)−0.0037 (11)
C20.0173 (14)0.0243 (15)0.0188 (14)0.0012 (11)0.0031 (11)−0.0016 (11)
C30.0267 (16)0.0216 (15)0.0213 (14)−0.0036 (12)−0.0015 (12)−0.0003 (11)
C40.0259 (16)0.0215 (15)0.0282 (15)0.0048 (12)−0.0020 (12)0.0005 (12)
C50.0201 (14)0.0286 (16)0.0243 (15)0.0040 (12)0.0018 (12)−0.0031 (12)
C60.0221 (15)0.0216 (15)0.0171 (13)0.0001 (11)0.0003 (11)−0.0017 (11)
C70.0184 (14)0.0250 (15)0.0209 (14)−0.0022 (12)0.0014 (11)−0.0043 (11)
C80.0196 (14)0.0198 (14)0.0200 (14)0.0020 (11)0.0065 (11)−0.0026 (11)
C90.0238 (15)0.0273 (16)0.0209 (14)0.0005 (12)0.0003 (11)−0.0013 (12)
C100.0201 (15)0.0284 (16)0.0289 (16)−0.0034 (12)0.0030 (12)−0.0039 (12)
C110.0292 (17)0.0220 (16)0.0273 (16)−0.0047 (12)0.0056 (13)0.0031 (12)
C120.0270 (16)0.0233 (15)0.0227 (15)−0.0004 (12)0.0027 (12)0.0011 (11)
C130.0203 (14)0.0182 (14)0.0226 (14)0.0009 (11)0.0043 (11)−0.0021 (11)
C140.0265 (15)0.0178 (15)0.0227 (15)0.0003 (12)0.0043 (12)0.0005 (11)
C150.0220 (14)0.0176 (14)0.0194 (14)−0.0005 (11)0.0053 (11)−0.0025 (11)
C160.0255 (15)0.0203 (15)0.0218 (14)−0.0005 (12)0.0024 (12)0.0021 (11)
C170.0261 (15)0.0226 (15)0.0223 (14)0.0021 (12)−0.0004 (12)−0.0024 (11)
C180.0186 (14)0.0208 (15)0.0243 (14)0.0018 (11)0.0011 (11)−0.0065 (11)
C190.0221 (15)0.0168 (14)0.0237 (14)−0.0012 (11)0.0076 (12)−0.0001 (11)
C200.0224 (15)0.0187 (14)0.0187 (14)0.0067 (11)0.0044 (11)−0.0042 (11)
C210.0301 (17)0.043 (2)0.046 (2)−0.0013 (14)0.0111 (15)0.0236 (15)
C220.0232 (15)0.0272 (15)0.0274 (15)−0.0058 (12)0.0046 (12)−0.0019 (12)
Geometric parameters (Å, º) top
O1—C11.356 (3)C9—C101.390 (4)
O1—H1O10.87 (4)C9—H9A0.9300
O2—C31.364 (3)C10—C111.377 (4)
O2—C211.432 (3)C10—H10A0.9300
O3—C201.309 (3)C11—C121.389 (4)
O3—H1O31.028 (10)C11—H11A0.9300
O4—C181.358 (3)C12—C131.398 (4)
O4—C221.433 (3)C12—H12A0.9300
N1—C71.285 (3)C14—C151.417 (4)
N1—C81.426 (3)C14—H14A0.9300
N2—C141.306 (3)C15—C161.407 (4)
N2—C131.414 (3)C15—C201.441 (4)
C1—C21.382 (4)C16—C171.359 (4)
C1—C61.412 (4)C16—H16A0.9300
C2—C31.385 (4)C17—C181.420 (4)
C2—H2A0.9300C17—H17A0.9300
C3—C41.393 (4)C18—C191.374 (4)
C4—C51.371 (4)C19—C201.403 (4)
C4—H4A0.9300C19—H19A0.9300
C5—C61.406 (4)C21—H21A0.9600
C5—H5A0.9300C21—H21B0.9600
C6—C71.444 (4)C21—H21C0.9600
C7—H7A0.9300C22—H22A0.9600
C8—C91.391 (4)C22—H22B0.9600
C8—C131.401 (4)C22—H22C0.9600
C1—O1—H1O1107 (2)C11—C12—C13119.9 (3)
C3—O2—C21117.2 (2)C11—C12—H12A120.0
C20—O3—H1O3106.5 (17)C13—C12—H12A120.0
C18—O4—C22117.4 (2)C12—C13—C8119.0 (2)
C7—N1—C8119.0 (2)C12—C13—N2123.8 (2)
C14—N2—C13125.4 (2)C8—C13—N2117.2 (2)
O1—C1—C2117.9 (2)N2—C14—C15121.6 (2)
O1—C1—C6121.2 (2)N2—C14—H14A119.2
C2—C1—C6120.9 (2)C15—C14—H14A119.2
C1—C2—C3119.6 (2)C16—C15—C14120.8 (2)
C1—C2—H2A120.2C16—C15—C20118.9 (2)
C3—C2—H2A120.2C14—C15—C20120.3 (2)
O2—C3—C2124.1 (2)C17—C16—C15121.9 (2)
O2—C3—C4115.0 (2)C17—C16—H16A119.1
C2—C3—C4120.8 (2)C15—C16—H16A119.1
C5—C4—C3119.3 (2)C16—C17—C18119.1 (3)
C5—C4—H4A120.3C16—C17—H17A120.4
C3—C4—H4A120.3C18—C17—H17A120.4
C4—C5—C6121.6 (3)O4—C18—C19124.6 (2)
C4—C5—H5A119.2O4—C18—C17114.6 (2)
C6—C5—H5A119.2C19—C18—C17120.8 (2)
C5—C6—C1117.7 (2)C18—C19—C20121.0 (2)
C5—C6—C7120.0 (2)C18—C19—H19A119.5
C1—C6—C7122.3 (2)C20—C19—H19A119.5
N1—C7—C6121.2 (2)O3—C20—C19120.4 (2)
N1—C7—H7A119.4O3—C20—C15121.4 (2)
C6—C7—H7A119.4C19—C20—C15118.2 (2)
C9—C8—C13120.3 (2)O2—C21—H21A109.5
C9—C8—N1122.0 (2)O2—C21—H21B109.5
C13—C8—N1117.6 (2)H21A—C21—H21B109.5
C10—C9—C8120.0 (3)O2—C21—H21C109.5
C10—C9—H9A120.0H21A—C21—H21C109.5
C8—C9—H9A120.0H21B—C21—H21C109.5
C11—C10—C9119.9 (3)O4—C22—H22A109.5
C11—C10—H10A120.1O4—C22—H22B109.5
C9—C10—H10A120.1H22A—C22—H22B109.5
C10—C11—C12120.8 (3)O4—C22—H22C109.5
C10—C11—H11A119.6H22A—C22—H22C109.5
C12—C11—H11A119.6H22B—C22—H22C109.5
O1—C1—C2—C3−179.3 (2)C11—C12—C13—N2−179.0 (2)
C6—C1—C2—C31.8 (4)C9—C8—C13—C12−0.3 (4)
C21—O2—C3—C25.5 (4)N1—C8—C13—C12−176.7 (2)
C21—O2—C3—C4−173.5 (3)C9—C8—C13—N2−179.6 (2)
C1—C2—C3—O2−178.5 (2)N1—C8—C13—N24.0 (3)
C1—C2—C3—C40.5 (4)C14—N2—C13—C12−2.1 (4)
O2—C3—C4—C5177.3 (2)C14—N2—C13—C8177.1 (2)
C2—C3—C4—C5−1.8 (4)C13—N2—C14—C15178.2 (2)
C3—C4—C5—C60.8 (4)N2—C14—C15—C16−177.7 (2)
C4—C5—C6—C11.4 (4)N2—C14—C15—C201.9 (4)
C4—C5—C6—C7179.4 (3)C14—C15—C16—C17179.3 (2)
O1—C1—C6—C5178.4 (2)C20—C15—C16—C17−0.2 (4)
C2—C1—C6—C5−2.7 (4)C15—C16—C17—C181.3 (4)
O1—C1—C6—C70.5 (4)C22—O4—C18—C19−5.8 (4)
C2—C1—C6—C7179.3 (2)C22—O4—C18—C17174.5 (2)
C8—N1—C7—C6−178.8 (2)C16—C17—C18—O4178.8 (2)
C5—C6—C7—N1−172.6 (2)C16—C17—C18—C19−0.9 (4)
C1—C6—C7—N15.3 (4)O4—C18—C19—C20179.6 (2)
C7—N1—C8—C952.6 (3)C17—C18—C19—C20−0.7 (4)
C7—N1—C8—C13−131.1 (3)C18—C19—C20—O3−178.7 (2)
C13—C8—C9—C10−0.8 (4)C18—C19—C20—C151.8 (4)
N1—C8—C9—C10175.4 (2)C16—C15—C20—O3179.2 (2)
C8—C9—C10—C110.4 (4)C14—C15—C20—O3−0.4 (4)
C9—C10—C11—C121.0 (4)C16—C15—C20—C19−1.3 (3)
C10—C11—C12—C13−2.1 (4)C14—C15—C20—C19179.1 (2)
C11—C12—C13—C81.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N10.87 (3)1.83 (4)2.615 (3)149 (3)
O3—H1O3···N21.03 (2)1.61 (2)2.555 (3)150 (2)
C7—H7A···O3i0.932.443.283 (3)150
C10—H10A···O2ii0.932.573.362 (3)143
C12—H12A···Cg1iii0.932.803.614 (3)147
C21—H21A···Cg2iv0.962.563.412 (3)149
C22—H22A···Cg1v0.962.683.396 (3)132
Symmetry codes: (i) x−1, y, z; (ii) −x−1, y−1/2, −z+3/2; (iii) x, −y−1/2, z−1/2; (iv) −x, y+1/2, −z+3/2; (v) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formulaC22H20N2O4
Mr376.40
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)6.2038 (3), 17.8512 (8), 16.6216 (9)
β (°) 91.072 (3)
V (Å3)1840.44 (16)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.56 × 0.09 × 0.07
Data collection
DiffractometerBruker SMART APEX II CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.949, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections		13290, 3243, 2216
Rint0.065
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.173, 1.10
No. of reflections3243
No. of parameters262
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.33, −0.40

Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N10.87 (3)1.83 (4)2.615 (3)149 (3)
O3—H1O3···N21.03 (2)1.61 (2)2.555 (3)150 (2)
C7—H7A···O3i0.932.44143.283 (3)150
C10—H10A···O2ii0.932.57133.362 (3)143
C12—H12A···Cg1iii0.932.79753.614 (3)147
C21—H21A···Cg2iv0.962.55543.412 (3)149
C22—H22A···Cg1v0.962.67553.396 (3)132
Symmetry codes: (i) x−1, y, z; (ii) −x−1, y−1/2, −z+3/2; (iii) x, −y−1/2, z−1/2; (iv) −x, y+1/2, −z+3/2; (v) −x+1, −y+1, −z+2.
 

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