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The title compound, C15H13NO3, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The A mol­ecules are linked by two C—H...O hydrogen bonds into a sheet of R44(33) rings, and the B mol­ecules are linked into a C(13) chain by C—H...O hydrogen bonds. The mol­ecules are also connected by three C—H...π inter­actions, resulting in a three-dimensional structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045503/at2399sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045503/at2399Isup2.hkl
Contains datablock I

CCDC reference: 654272

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.015 Å
  • R factor = 0.103
  • wR factor = 0.303
  • Data-to-parameter ratio = 6.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95 PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 15
Alert level C RFACG01_ALERT_3_C The value of the R factor is > 0.10 R factor given 0.103 RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.303 STRVA01_ALERT_4_C Flack parameter is too small From the CIF: _refine_ls_abs_structure_Flack -10.000 From the CIF: _refine_ls_abs_structure_Flack_su 10.000 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 10.00 PLAT033_ALERT_2_C Flack Parameter Value Deviates 2 * su from zero. -10.00 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT084_ALERT_2_C High R2 Value .................................. 0.30 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.85 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.59 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8A PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8B
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 2363 Count of symmetry unique reflns 2475 Completeness (_total/calc) 95.47% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

We have reported recently the crystal structures of some Schiff bases compounds (Yang et al., 2007a,b). As part of our study of Schiff bases compounds, we report here the crystal structure of the title compound (I).

The compound (I) crystallizes in monoclinic space group P21/c, with two independent molecules in the asymmetric unit. In the asymmetric unit, the molecules A and B are likned by one C—H···π intercation [C13A···Cg2B = 3.69 (4) Å, H13A···Cg2B = 3.05 Å, C13A—H13A···Cg2B = 127°; where Cg2B is the centroid of the ring C9B–C17B] (Table 1 and Fig. 1). The molecules A and B have an E configuration, the dihedral angle between the two benzene rings are 46.3 (3)° for molecule A and 43.5 (2)° for molecule B, respectively. The geometric parameters in (I) are normal (Allen et al., 1987).

In the crystal structure of (I), atom C8A in the molecule A at (x, y, z) acts as hydrogen-bond donor, via H8A, to atom O3A in the molecule A at (x, y, -1 + z), forming a simple C(13) chain (Bernstein et al., 1995). Similarly, atom C15A at (x, y, z) acts as hydrogen-bond donor, via H15B, to O2A at (x, -1 + y, 1 + z), producing a C(14) chain. The combination of the two chains generates a R44(33) ring (Table 1 and Fig. 2).

In (I), atom C8B in the molecule B at (x, y, z) acts as hydrogen-bond donor, via H8C, to atom O3B in the molecule B at (x, y, -1 + z), forming a simple C(13) chain running parallel to the [001] direction (Table 1 and Fig.3).

The molecules are also connected by three C—H···π interactions, resulting in a three-dimensional structure (see Table 1).

Related literature top

For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Yang et al. (2007a,b).

Experimental top

The mixture containing piperonaldehyde (1.5 g, 10 mmol) and 4-methoxyaniline (1.23 g, 10 mmol) was refluxed for about 4 h in ethanol (30 ml), then the reaction mixture was cooled and the products were filtered off, washed with ethanol and dried. Colourless crystals of (I) suitatble for X-ray structure analysis were obtained by recrystallizing the crude product from ethanol [m.p.383–385 K].

Refinement top

H atoms were placed in calculated positions with C—H = 0.93–0.97 Å, and refined in riding mode with Uiso(H) = 1.2 or 1.5Ueq(C).

Structure description top

We have reported recently the crystal structures of some Schiff bases compounds (Yang et al., 2007a,b). As part of our study of Schiff bases compounds, we report here the crystal structure of the title compound (I).

The compound (I) crystallizes in monoclinic space group P21/c, with two independent molecules in the asymmetric unit. In the asymmetric unit, the molecules A and B are likned by one C—H···π intercation [C13A···Cg2B = 3.69 (4) Å, H13A···Cg2B = 3.05 Å, C13A—H13A···Cg2B = 127°; where Cg2B is the centroid of the ring C9B–C17B] (Table 1 and Fig. 1). The molecules A and B have an E configuration, the dihedral angle between the two benzene rings are 46.3 (3)° for molecule A and 43.5 (2)° for molecule B, respectively. The geometric parameters in (I) are normal (Allen et al., 1987).

In the crystal structure of (I), atom C8A in the molecule A at (x, y, z) acts as hydrogen-bond donor, via H8A, to atom O3A in the molecule A at (x, y, -1 + z), forming a simple C(13) chain (Bernstein et al., 1995). Similarly, atom C15A at (x, y, z) acts as hydrogen-bond donor, via H15B, to O2A at (x, -1 + y, 1 + z), producing a C(14) chain. The combination of the two chains generates a R44(33) ring (Table 1 and Fig. 2).

In (I), atom C8B in the molecule B at (x, y, z) acts as hydrogen-bond donor, via H8C, to atom O3B in the molecule B at (x, y, -1 + z), forming a simple C(13) chain running parallel to the [001] direction (Table 1 and Fig.3).

The molecules are also connected by three C—H···π interactions, resulting in a three-dimensional structure (see Table 1).

For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Yang et al. (2007a,b).

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. A view of the two independent molecules of (I) in the asymmetric unit, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of part of the crystal structure of molecule A, showing R44(33) rings. For clarity, H atoms bonded to C atoms have been omitted. Dashed lines indicate hydrogen bonds [Symmetry codes: (*) x, y,-1 + z; (#) x, -1 + y, 1 + z].
[Figure 3] Fig. 3. A view of part of the crystal structure of molecule B, showing the formation of a C(13) chain along [001]. For clarity, H atoms bonded to C atoms have been omitted. Dashed lines indicate hydrogen bonds [Symmetry codes: (*) x, y, -1 + z; (#) x, y, 1 + z].
(E)-4-Methoxy-N-(3,4-methylenedioxybenzylidene)aniline top
Crystal data top
C15H13NO3F(000) = 536
Mr = 255.26Dx = 1.331 Mg m3
Monoclinic, P21Melting point: 383 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 14.497 (2) ÅCell parameters from 741 reflections
b = 6.1192 (14) Åθ = 2.3–21.0°
c = 14.732 (2) ŵ = 0.09 mm1
β = 102.819 (2)°T = 298 K
V = 1274.3 (4) Å3Needle, colourless
Z = 40.57 × 0.18 × 0.11 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2363 independent reflections
Radiation source: fine-focus sealed tube1115 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.099
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1717
Tmin = 0.949, Tmax = 0.990k = 77
6121 measured reflectionsl = 1712
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.103H-atom parameters constrained
wR(F2) = 0.303 w = 1/[σ2(Fo2) + (0.1804P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max = 0.026
2363 reflectionsΔρmax = 0.33 e Å3
345 parametersΔρmin = 0.29 e Å3
1 restraintAbsolute structure: Flack (1983), with 1668 Freidel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 10 (10)
Crystal data top
C15H13NO3V = 1274.3 (4) Å3
Mr = 255.26Z = 4
Monoclinic, P21Mo Kα radiation
a = 14.497 (2) ŵ = 0.09 mm1
b = 6.1192 (14) ÅT = 298 K
c = 14.732 (2) Å0.57 × 0.18 × 0.11 mm
β = 102.819 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2363 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1115 reflections with I > 2σ(I)
Tmin = 0.949, Tmax = 0.990Rint = 0.099
6121 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.103H-atom parameters constrained
wR(F2) = 0.303Δρmax = 0.33 e Å3
S = 0.95Δρmin = 0.29 e Å3
2363 reflectionsAbsolute structure: Flack (1983), with 1668 Freidel pairs
345 parametersAbsolute structure parameter: 10 (10)
1 restraint
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
N1A0.6221 (5)0.9203 (17)0.3790 (6)0.056 (2)
O1A0.5892 (6)0.9143 (17)0.0183 (5)0.089 (3)
O2A0.6377 (6)1.2521 (18)0.0237 (6)0.089 (3)
O3A0.6112 (5)0.7729 (15)0.7511 (5)0.074 (2)
C1A0.6309 (7)1.118 (2)0.3467 (7)0.061 (3)
H1A0.63801.23470.38810.073*
C2A0.6299 (7)1.162 (2)0.2514 (8)0.061 (3)
C3A0.6029 (7)0.995 (2)0.1830 (6)0.055 (3)
H3A0.58370.85800.19890.066*
C4A0.6063 (7)1.044 (2)0.0925 (7)0.060 (3)
C5A0.6351 (8)1.250 (2)0.0672 (8)0.063 (3)
C6A0.6617 (8)1.416 (2)0.1340 (8)0.074 (3)
H6A0.68211.55200.11800.089*
C7A0.6564 (7)1.369 (2)0.2239 (8)0.065 (3)
H7A0.67091.47840.26850.078*
C8A0.6020 (12)1.046 (3)0.0599 (8)0.106 (5)
H8A0.64620.97620.09130.127*
H8B0.54211.06480.10420.127*
C9A0.6204 (6)0.8953 (18)0.4729 (6)0.048 (2)
C14A0.6592 (7)0.6977 (18)0.5177 (7)0.055 (3)
H14A0.68550.59620.48380.066*
C13A0.6591 (6)0.6538 (19)0.6074 (7)0.054 (3)
H13A0.68730.52640.63490.065*
C12A0.6169 (7)0.798 (2)0.6591 (6)0.056 (3)
C11A0.5796 (7)0.9931 (18)0.6168 (7)0.053 (3)
H11A0.55371.09450.65110.064*
C10A0.5803 (6)1.037 (2)0.5270 (7)0.058 (3)
H10A0.55311.16640.50060.070*
C15A0.6397 (11)0.565 (2)0.7928 (8)0.107 (5)
H15A0.59980.45240.75950.161*
H15B0.63410.56590.85650.161*
H15C0.70420.53660.79030.161*
N1B0.8902 (5)0.4200 (18)0.4322 (5)0.058 (2)
O1B0.9310 (6)0.4245 (16)0.0858 (5)0.087 (3)
O2B0.8841 (6)0.7662 (16)0.0242 (5)0.083 (3)
O3B0.8685 (5)0.2769 (16)0.8033 (5)0.073 (2)
C1B0.8780 (6)0.617 (2)0.3959 (7)0.059 (3)
H1B0.86730.73320.43290.070*
C2B0.8809 (7)0.658 (2)0.2997 (8)0.058 (3)
C3B0.9081 (7)0.501 (2)0.2429 (6)0.054 (3)
H3B0.92640.36280.26690.065*
C4B0.9082 (7)0.545 (2)0.1546 (7)0.060 (3)
C5B0.8787 (7)0.760 (2)0.1160 (7)0.061 (3)
C6B0.8521 (7)0.914 (2)0.1707 (8)0.068 (3)
H6B0.83311.05190.14670.082*
C7B0.8534 (7)0.866 (2)0.2635 (8)0.062 (3)
H7B0.83590.97170.30160.074*
C8B0.9174 (12)0.556 (3)0.0050 (10)0.114 (5)
H8C0.87170.48740.04500.137*
H8D0.97660.57080.01480.137*
C9B0.8867 (6)0.3895 (17)0.5252 (6)0.044 (2)
C10B0.9184 (6)0.539 (2)0.5986 (6)0.056 (3)
H10B0.94460.67120.58600.068*
C11B0.9114 (7)0.493 (2)0.6877 (6)0.055 (3)
H11B0.93360.59490.73430.066*
C12B0.8717 (6)0.298 (2)0.7113 (7)0.052 (3)
C13B0.8436 (7)0.150 (2)0.6423 (7)0.064 (3)
H13B0.82050.01540.65610.077*
C14B0.8489 (7)0.1971 (19)0.5499 (7)0.058 (3)
H14B0.82600.09460.50380.069*
C15B0.8285 (10)0.076 (2)0.8290 (8)0.094 (4)
H15D0.76520.05890.79260.141*
H15E0.82730.08000.89390.141*
H15F0.86650.04560.81760.141*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.065 (5)0.049 (6)0.058 (6)0.006 (5)0.021 (4)0.002 (5)
O1A0.142 (7)0.066 (6)0.057 (5)0.008 (6)0.021 (5)0.001 (5)
O2A0.129 (7)0.076 (7)0.068 (6)0.000 (6)0.038 (5)0.021 (6)
O3A0.098 (5)0.062 (6)0.056 (5)0.003 (5)0.005 (4)0.011 (5)
C1A0.062 (6)0.064 (9)0.052 (7)0.005 (6)0.001 (5)0.014 (6)
C2A0.069 (6)0.052 (7)0.065 (7)0.006 (6)0.019 (5)0.011 (7)
C3A0.084 (7)0.030 (6)0.047 (6)0.003 (5)0.004 (5)0.003 (5)
C4A0.066 (7)0.065 (9)0.052 (7)0.013 (7)0.017 (5)0.008 (7)
C5A0.083 (7)0.047 (8)0.062 (7)0.008 (6)0.021 (6)0.019 (7)
C6A0.077 (7)0.054 (8)0.091 (9)0.009 (6)0.016 (7)0.017 (8)
C7A0.077 (7)0.051 (8)0.063 (7)0.002 (6)0.010 (6)0.005 (6)
C8A0.148 (12)0.114 (15)0.060 (8)0.017 (12)0.033 (8)0.008 (10)
C9A0.064 (6)0.038 (7)0.038 (6)0.015 (5)0.006 (5)0.003 (5)
C14A0.080 (7)0.040 (7)0.053 (7)0.000 (6)0.030 (5)0.005 (5)
C13A0.039 (5)0.046 (7)0.068 (7)0.007 (5)0.009 (5)0.008 (6)
C12A0.067 (6)0.058 (8)0.044 (6)0.004 (6)0.015 (5)0.002 (6)
C11A0.082 (7)0.024 (6)0.049 (6)0.003 (5)0.003 (5)0.003 (5)
C10A0.057 (6)0.040 (7)0.068 (7)0.001 (5)0.004 (5)0.002 (6)
C15A0.165 (13)0.065 (11)0.090 (9)0.006 (10)0.024 (9)0.034 (9)
N1B0.070 (5)0.056 (7)0.043 (5)0.004 (5)0.003 (4)0.007 (5)
O1B0.153 (8)0.065 (6)0.048 (4)0.011 (6)0.031 (5)0.009 (5)
O2B0.120 (6)0.066 (7)0.064 (5)0.007 (6)0.021 (4)0.011 (5)
O3B0.092 (5)0.081 (7)0.044 (4)0.014 (5)0.010 (3)0.005 (5)
C1B0.055 (6)0.068 (9)0.048 (6)0.007 (6)0.003 (5)0.008 (6)
C2B0.063 (6)0.041 (7)0.069 (7)0.003 (5)0.009 (5)0.002 (6)
C3B0.083 (7)0.044 (7)0.033 (5)0.003 (6)0.011 (5)0.007 (5)
C4B0.079 (7)0.057 (9)0.050 (7)0.015 (6)0.025 (5)0.002 (7)
C5B0.072 (7)0.064 (9)0.041 (6)0.021 (7)0.002 (5)0.002 (7)
C6B0.081 (7)0.052 (8)0.071 (8)0.005 (6)0.012 (6)0.007 (7)
C7B0.062 (6)0.054 (8)0.069 (8)0.008 (6)0.011 (5)0.007 (6)
C8B0.171 (14)0.084 (13)0.097 (10)0.024 (12)0.049 (10)0.014 (10)
C9B0.049 (5)0.034 (6)0.041 (5)0.002 (5)0.006 (4)0.005 (5)
C10B0.044 (5)0.051 (7)0.072 (7)0.009 (5)0.010 (5)0.015 (6)
C11B0.072 (6)0.052 (8)0.036 (5)0.012 (6)0.000 (5)0.001 (5)
C12B0.045 (5)0.055 (7)0.051 (6)0.001 (5)0.005 (4)0.006 (6)
C13B0.089 (7)0.047 (7)0.056 (7)0.000 (6)0.012 (6)0.003 (6)
C14B0.078 (7)0.043 (7)0.048 (6)0.005 (6)0.006 (5)0.014 (5)
C15B0.137 (11)0.067 (10)0.082 (8)0.010 (9)0.035 (8)0.009 (8)
Geometric parameters (Å, º) top
N1A—C1A1.315 (15)N1B—C1B1.315 (15)
N1A—C9A1.397 (11)N1B—C9B1.396 (11)
O1A—C4A1.330 (13)O1B—C4B1.352 (13)
O1A—C8A1.452 (15)O1B—C8B1.414 (16)
O2A—C5A1.348 (13)O2B—C5B1.373 (12)
O2A—C8A1.42 (2)O2B—C8B1.423 (18)
O3A—C12A1.385 (11)O3B—C12B1.373 (11)
O3A—C15A1.434 (15)O3B—C15B1.447 (16)
C1A—C2A1.426 (13)C1B—C2B1.448 (14)
C1A—H1A0.9300C1B—H1B0.9300
C2A—C7A1.411 (17)C2B—C3B1.388 (15)
C2A—C3A1.426 (16)C2B—C7B1.402 (17)
C3A—C4A1.379 (13)C3B—C4B1.329 (12)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.403 (17)C4B—C5B1.462 (18)
C5A—C6A1.406 (17)C5B—C6B1.351 (17)
C6A—C7A1.375 (14)C6B—C7B1.396 (14)
C6A—H6A0.9300C6B—H6B0.9300
C7A—H7A0.9300C7B—H7B0.9300
C8A—H8A0.9700C8B—H8C0.9700
C8A—H8B0.9700C8B—H8D0.9700
C9A—C10A1.390 (14)C9B—C14B1.381 (15)
C9A—C14A1.431 (14)C9B—C10B1.412 (13)
C14A—C13A1.349 (12)C10B—C11B1.369 (12)
C14A—H14A0.9300C10B—H10B0.9300
C13A—C12A1.394 (14)C11B—C12B1.404 (15)
C13A—H13A0.9300C11B—H11B0.9300
C12A—C11A1.397 (16)C12B—C13B1.352 (13)
C11A—C10A1.353 (13)C13B—C14B1.410 (13)
C11A—H11A0.9300C13B—H13B0.9300
C10A—H10A0.9300C14B—H14B0.9300
C15A—H15A0.9600C15B—H15D0.9600
C15A—H15B0.9600C15B—H15E0.9600
C15A—H15C0.9600C15B—H15F0.9600
C1A—N1A—C9A118.9 (10)C1B—N1B—C9B119.4 (10)
C4A—O1A—C8A106.6 (11)C4B—O1B—C8B108.0 (10)
C5A—O2A—C8A106.1 (10)C5B—O2B—C8B105.5 (10)
C12A—O3A—C15A116.4 (10)C12B—O3B—C15B116.1 (9)
N1A—C1A—C2A123.2 (12)N1B—C1B—C2B121.7 (11)
N1A—C1A—H1A118.4N1B—C1B—H1B119.2
C2A—C1A—H1A118.4C2B—C1B—H1B119.2
C7A—C2A—C3A119.3 (10)C3B—C2B—C7B119.6 (10)
C7A—C2A—C1A120.6 (12)C3B—C2B—C1B123.0 (11)
C3A—C2A—C1A120.2 (12)C7B—C2B—C1B117.4 (11)
C4A—C3A—C2A117.6 (11)C4B—C3B—C2B120.7 (12)
C4A—C3A—H3A121.2C4B—C3B—H3B119.6
C2A—C3A—H3A121.2C2B—C3B—H3B119.6
O1A—C4A—C3A128.6 (12)C3B—C4B—O1B132.5 (12)
O1A—C4A—C5A109.4 (10)C3B—C4B—C5B120.1 (11)
C3A—C4A—C5A122.0 (11)O1B—C4B—C5B107.4 (9)
O2A—C5A—C6A128.6 (12)C6B—C5B—O2B131.0 (12)
O2A—C5A—C4A110.3 (11)C6B—C5B—C4B119.7 (9)
C6A—C5A—C4A121.0 (10)O2B—C5B—C4B109.4 (11)
C7A—C6A—C5A117.1 (12)C5B—C6B—C7B119.4 (12)
C7A—C6A—H6A121.4C5B—C6B—H6B120.3
C5A—C6A—H6A121.4C7B—C6B—H6B120.3
C6A—C7A—C2A122.9 (12)C6B—C7B—C2B120.5 (11)
C6A—C7A—H7A118.5C6B—C7B—H7B119.7
C2A—C7A—H7A118.5C2B—C7B—H7B119.7
O2A—C8A—O1A107.2 (10)O1B—C8B—O2B109.7 (10)
O2A—C8A—H8A110.3O1B—C8B—H8C109.7
O1A—C8A—H8A110.3O2B—C8B—H8C109.7
O2A—C8A—H8B110.3O1B—C8B—H8D109.7
O1A—C8A—H8B110.3O2B—C8B—H8D109.7
H8A—C8A—H8B108.5H8C—C8B—H8D108.2
C10A—C9A—N1A126.9 (10)C14B—C9B—N1B118.4 (9)
C10A—C9A—C14A115.8 (8)C14B—C9B—C10B115.6 (9)
N1A—C9A—C14A117.2 (10)N1B—C9B—C10B126.0 (10)
C13A—C14A—C9A122.3 (10)C11B—C10B—C9B121.4 (10)
C13A—C14A—H14A118.8C11B—C10B—H10B119.3
C9A—C14A—H14A118.9C9B—C10B—H10B119.3
C14A—C13A—C12A120.3 (10)C10B—C11B—C12B122.2 (10)
C14A—C13A—H13A119.9C10B—C11B—H11B118.9
C12A—C13A—H13A119.8C12B—C11B—H11B118.9
O3A—C12A—C13A126.3 (11)C13B—C12B—O3B127.6 (11)
O3A—C12A—C11A115.5 (10)C13B—C12B—C11B117.0 (9)
C13A—C12A—C11A118.2 (9)O3B—C12B—C11B115.3 (9)
C10A—C11A—C12A121.3 (10)C12B—C13B—C14B121.2 (11)
C10A—C11A—H11A119.4C12B—C13B—H13B119.4
C12A—C11A—H11A119.4C14B—C13B—H13B119.4
C11A—C10A—C9A122.1 (10)C9B—C14B—C13B122.5 (10)
C11A—C10A—H10A119.0C9B—C14B—H14B118.8
C9A—C10A—H10A118.9C13B—C14B—H14B118.8
O3A—C15A—H15A109.5O3B—C15B—H15D109.5
O3A—C15A—H15B109.5O3B—C15B—H15E109.5
H15A—C15A—H15B109.5H15D—C15B—H15E109.5
O3A—C15A—H15C109.5O3B—C15B—H15F109.5
H15A—C15A—H15C109.5H15D—C15B—H15F109.5
H15B—C15A—H15C109.5H15E—C15B—H15F109.5
C9A—N1A—C1A—C2A177.6 (8)C9B—N1B—C1B—C2B180.0 (7)
N1A—C1A—C2A—C7A168.5 (10)N1B—C1B—C2B—C3B8.3 (15)
N1A—C1A—C2A—C3A10.9 (15)N1B—C1B—C2B—C7B170.7 (10)
C7A—C2A—C3A—C4A1.5 (15)C7B—C2B—C3B—C4B0.1 (15)
C1A—C2A—C3A—C4A177.9 (9)C1B—C2B—C3B—C4B178.9 (9)
C8A—O1A—C4A—C3A179.6 (11)C2B—C3B—C4B—O1B179.8 (10)
C8A—O1A—C4A—C5A3.6 (13)C2B—C3B—C4B—C5B0.5 (15)
C2A—C3A—C4A—O1A176.4 (10)C8B—O1B—C4B—C3B179.8 (13)
C2A—C3A—C4A—C5A0.0 (15)C8B—O1B—C4B—C5B0.1 (13)
C8A—O2A—C5A—C6A179.2 (13)C8B—O2B—C5B—C6B179.6 (13)
C8A—O2A—C5A—C4A4.8 (14)C8B—O2B—C5B—C4B0.4 (13)
O1A—C4A—C5A—O2A0.8 (13)C3B—C4B—C5B—C6B0.4 (15)
C3A—C4A—C5A—O2A176.3 (9)O1B—C4B—C5B—C6B179.8 (9)
O1A—C4A—C5A—C6A177.1 (10)C3B—C4B—C5B—O2B179.6 (9)
C3A—C4A—C5A—C6A0.1 (17)O1B—C4B—C5B—O2B0.2 (11)
O2A—C5A—C6A—C7A176.9 (10)O2B—C5B—C6B—C7B179.8 (10)
C4A—C5A—C6A—C7A1.3 (17)C4B—C5B—C6B—C7B0.2 (15)
C5A—C6A—C7A—C2A2.9 (16)C5B—C6B—C7B—C2B0.8 (15)
C3A—C2A—C7A—C6A3.1 (16)C3B—C2B—C7B—C6B0.7 (15)
C1A—C2A—C7A—C6A176.3 (9)C1B—C2B—C7B—C6B178.3 (8)
C5A—O2A—C8A—O1A6.8 (15)C4B—O1B—C8B—O2B0.4 (16)
C4A—O1A—C8A—O2A6.4 (15)C5B—O2B—C8B—O1B0.5 (15)
C1A—N1A—C9A—C10A35.4 (14)C1B—N1B—C9B—C14B145.3 (10)
C1A—N1A—C9A—C14A148.3 (9)C1B—N1B—C9B—C10B34.5 (14)
C10A—C9A—C14A—C13A1.5 (13)C14B—C9B—C10B—C11B0.0 (14)
N1A—C9A—C14A—C13A178.3 (9)N1B—C9B—C10B—C11B179.8 (9)
C9A—C14A—C13A—C12A2.6 (13)C9B—C10B—C11B—C12B0.7 (15)
C15A—O3A—C12A—C13A9.1 (15)C15B—O3B—C12B—C13B1.5 (15)
C15A—O3A—C12A—C11A173.5 (11)C15B—O3B—C12B—C11B179.5 (10)
C14A—C13A—C12A—O3A179.5 (9)C10B—C11B—C12B—C13B2.6 (14)
C14A—C13A—C12A—C11A3.2 (13)C10B—C11B—C12B—O3B179.2 (9)
O3A—C12A—C11A—C10A179.6 (9)O3B—C12B—C13B—C14B178.3 (9)
C13A—C12A—C11A—C10A2.8 (15)C11B—C12B—C13B—C14B3.8 (14)
C12A—C11A—C10A—C9A1.9 (15)N1B—C9B—C14B—C13B179.0 (9)
N1A—C9A—C10A—C11A177.6 (9)C10B—C9B—C14B—C13B1.2 (14)
C14A—C9A—C10A—C11A1.2 (13)C12B—C13B—C14B—C9B3.2 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8A—H8A···O3Ai0.972.583.28 (2)129
C8B—H8C···O3Bi0.972.573.36 (2)139
C15A—H15B···O2Aii0.962.603.32 (2)132
C13A—H13A···Cg2B0.933.053.69 (4)127
C10A—H10A···Cg2Aiii0.932.703.45 (4)138
C13B—H13B···Cg2Aiv0.933.093.70 (4)124
Symmetry codes: (i) x, y, z1; (ii) x, y1, z+1; (iii) x+1, y+1/2, z+1; (iv) x, y1, z.

Experimental details

Crystal data
Chemical formulaC15H13NO3
Mr255.26
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)14.497 (2), 6.1192 (14), 14.732 (2)
β (°) 102.819 (2)
V3)1274.3 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.57 × 0.18 × 0.11
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.949, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
6121, 2363, 1115
Rint0.099
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.103, 0.303, 0.95
No. of reflections2363
No. of parameters345
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.29
Absolute structureFlack (1983), with 1668 Freidel pairs
Absolute structure parameter10 (10)

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
C8A—H8A···O3Ai0.972.583.28 (2)128.5
C8B—H8C···O3Bi0.972.573.36 (2)139.0
C15A—H15B···O2Aii0.962.603.32 (2)131.7
C13A—H13A···Cg2B0.933.053.69 (4)127.1
C10A—H10A···Cg2Aiii0.932.703.45 (4)138.4
C13B—H13B···Cg2Aiv0.933.093.70 (4)124.3
Symmetry codes: (i) x, y, z1; (ii) x, y1, z+1; (iii) x+1, y+1/2, z+1; (iv) x, y1, z.
 

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