Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045503/at2399sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045503/at2399Isup2.hkl |
CCDC reference: 654272
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Yang et al. (2007a,b).
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].
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).
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).
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).
C15H13NO3 | F(000) = 536 |
Mr = 255.26 | Dx = 1.331 Mg m−3 |
Monoclinic, P21 | Melting point: 383 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 14.497 (2) Å | Cell parameters from 741 reflections |
b = 6.1192 (14) Å | θ = 2.3–21.0° |
c = 14.732 (2) Å | µ = 0.09 mm−1 |
β = 102.819 (2)° | T = 298 K |
V = 1274.3 (4) Å3 | Needle, colourless |
Z = 4 | 0.57 × 0.18 × 0.11 mm |
Bruker SMART CCD area-detector diffractometer | 2363 independent reflections |
Radiation source: fine-focus sealed tube | 1115 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.099 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→17 |
Tmin = 0.949, Tmax = 0.990 | k = −7→7 |
6121 measured reflections | l = −17→12 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.103 | H-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 reflections | Δρmax = 0.33 e Å−3 |
345 parameters | Δρmin = −0.29 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with 1668 Freidel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −10 (10) |
C15H13NO3 | V = 1274.3 (4) Å3 |
Mr = 255.26 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 14.497 (2) Å | µ = 0.09 mm−1 |
b = 6.1192 (14) Å | T = 298 K |
c = 14.732 (2) Å | 0.57 × 0.18 × 0.11 mm |
β = 102.819 (2)° |
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 = 0.990 | Rint = 0.099 |
6121 measured reflections |
R[F2 > 2σ(F2)] = 0.103 | H-atom parameters constrained |
wR(F2) = 0.303 | Δρmax = 0.33 e Å−3 |
S = 0.95 | Δρmin = −0.29 e Å−3 |
2363 reflections | Absolute structure: Flack (1983), with 1668 Freidel pairs |
345 parameters | Absolute structure parameter: −10 (10) |
1 restraint |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.6221 (5) | 0.9203 (17) | 0.3790 (6) | 0.056 (2) | |
O1A | 0.5892 (6) | 0.9143 (17) | 0.0183 (5) | 0.089 (3) | |
O2A | 0.6377 (6) | 1.2521 (18) | −0.0237 (6) | 0.089 (3) | |
O3A | 0.6112 (5) | 0.7729 (15) | 0.7511 (5) | 0.074 (2) | |
C1A | 0.6309 (7) | 1.118 (2) | 0.3467 (7) | 0.061 (3) | |
H1A | 0.6380 | 1.2347 | 0.3881 | 0.073* | |
C2A | 0.6299 (7) | 1.162 (2) | 0.2514 (8) | 0.061 (3) | |
C3A | 0.6029 (7) | 0.995 (2) | 0.1830 (6) | 0.055 (3) | |
H3A | 0.5837 | 0.8580 | 0.1989 | 0.066* | |
C4A | 0.6063 (7) | 1.044 (2) | 0.0925 (7) | 0.060 (3) | |
C5A | 0.6351 (8) | 1.250 (2) | 0.0672 (8) | 0.063 (3) | |
C6A | 0.6617 (8) | 1.416 (2) | 0.1340 (8) | 0.074 (3) | |
H6A | 0.6821 | 1.5520 | 0.1180 | 0.089* | |
C7A | 0.6564 (7) | 1.369 (2) | 0.2239 (8) | 0.065 (3) | |
H7A | 0.6709 | 1.4784 | 0.2685 | 0.078* | |
C8A | 0.6020 (12) | 1.046 (3) | −0.0599 (8) | 0.106 (5) | |
H8A | 0.6462 | 0.9762 | −0.0913 | 0.127* | |
H8B | 0.5421 | 1.0648 | −0.1042 | 0.127* | |
C9A | 0.6204 (6) | 0.8953 (18) | 0.4729 (6) | 0.048 (2) | |
C14A | 0.6592 (7) | 0.6977 (18) | 0.5177 (7) | 0.055 (3) | |
H14A | 0.6855 | 0.5962 | 0.4838 | 0.066* | |
C13A | 0.6591 (6) | 0.6538 (19) | 0.6074 (7) | 0.054 (3) | |
H13A | 0.6873 | 0.5264 | 0.6349 | 0.065* | |
C12A | 0.6169 (7) | 0.798 (2) | 0.6591 (6) | 0.056 (3) | |
C11A | 0.5796 (7) | 0.9931 (18) | 0.6168 (7) | 0.053 (3) | |
H11A | 0.5537 | 1.0945 | 0.6511 | 0.064* | |
C10A | 0.5803 (6) | 1.037 (2) | 0.5270 (7) | 0.058 (3) | |
H10A | 0.5531 | 1.1664 | 0.5006 | 0.070* | |
C15A | 0.6397 (11) | 0.565 (2) | 0.7928 (8) | 0.107 (5) | |
H15A | 0.5998 | 0.4524 | 0.7595 | 0.161* | |
H15B | 0.6341 | 0.5659 | 0.8565 | 0.161* | |
H15C | 0.7042 | 0.5366 | 0.7903 | 0.161* | |
N1B | 0.8902 (5) | 0.4200 (18) | 0.4322 (5) | 0.058 (2) | |
O1B | 0.9310 (6) | 0.4245 (16) | 0.0858 (5) | 0.087 (3) | |
O2B | 0.8841 (6) | 0.7662 (16) | 0.0242 (5) | 0.083 (3) | |
O3B | 0.8685 (5) | 0.2769 (16) | 0.8033 (5) | 0.073 (2) | |
C1B | 0.8780 (6) | 0.617 (2) | 0.3959 (7) | 0.059 (3) | |
H1B | 0.8673 | 0.7332 | 0.4329 | 0.070* | |
C2B | 0.8809 (7) | 0.658 (2) | 0.2997 (8) | 0.058 (3) | |
C3B | 0.9081 (7) | 0.501 (2) | 0.2429 (6) | 0.054 (3) | |
H3B | 0.9264 | 0.3628 | 0.2669 | 0.065* | |
C4B | 0.9082 (7) | 0.545 (2) | 0.1546 (7) | 0.060 (3) | |
C5B | 0.8787 (7) | 0.760 (2) | 0.1160 (7) | 0.061 (3) | |
C6B | 0.8521 (7) | 0.914 (2) | 0.1707 (8) | 0.068 (3) | |
H6B | 0.8331 | 1.0519 | 0.1467 | 0.082* | |
C7B | 0.8534 (7) | 0.866 (2) | 0.2635 (8) | 0.062 (3) | |
H7B | 0.8359 | 0.9717 | 0.3016 | 0.074* | |
C8B | 0.9174 (12) | 0.556 (3) | 0.0050 (10) | 0.114 (5) | |
H8C | 0.8717 | 0.4874 | −0.0450 | 0.137* | |
H8D | 0.9766 | 0.5708 | −0.0148 | 0.137* | |
C9B | 0.8867 (6) | 0.3895 (17) | 0.5252 (6) | 0.044 (2) | |
C10B | 0.9184 (6) | 0.539 (2) | 0.5986 (6) | 0.056 (3) | |
H10B | 0.9446 | 0.6712 | 0.5860 | 0.068* | |
C11B | 0.9114 (7) | 0.493 (2) | 0.6877 (6) | 0.055 (3) | |
H11B | 0.9336 | 0.5949 | 0.7343 | 0.066* | |
C12B | 0.8717 (6) | 0.298 (2) | 0.7113 (7) | 0.052 (3) | |
C13B | 0.8436 (7) | 0.150 (2) | 0.6423 (7) | 0.064 (3) | |
H13B | 0.8205 | 0.0154 | 0.6561 | 0.077* | |
C14B | 0.8489 (7) | 0.1971 (19) | 0.5499 (7) | 0.058 (3) | |
H14B | 0.8260 | 0.0946 | 0.5038 | 0.069* | |
C15B | 0.8285 (10) | 0.076 (2) | 0.8290 (8) | 0.094 (4) | |
H15D | 0.7652 | 0.0589 | 0.7926 | 0.141* | |
H15E | 0.8273 | 0.0800 | 0.8939 | 0.141* | |
H15F | 0.8665 | −0.0456 | 0.8176 | 0.141* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.065 (5) | 0.049 (6) | 0.058 (6) | 0.006 (5) | 0.021 (4) | −0.002 (5) |
O1A | 0.142 (7) | 0.066 (6) | 0.057 (5) | 0.008 (6) | 0.021 (5) | 0.001 (5) |
O2A | 0.129 (7) | 0.076 (7) | 0.068 (6) | 0.000 (6) | 0.038 (5) | 0.021 (6) |
O3A | 0.098 (5) | 0.062 (6) | 0.056 (5) | 0.003 (5) | 0.005 (4) | 0.011 (5) |
C1A | 0.062 (6) | 0.064 (9) | 0.052 (7) | −0.005 (6) | −0.001 (5) | 0.014 (6) |
C2A | 0.069 (6) | 0.052 (7) | 0.065 (7) | 0.006 (6) | 0.019 (5) | 0.011 (7) |
C3A | 0.084 (7) | 0.030 (6) | 0.047 (6) | −0.003 (5) | 0.004 (5) | 0.003 (5) |
C4A | 0.066 (7) | 0.065 (9) | 0.052 (7) | 0.013 (7) | 0.017 (5) | −0.008 (7) |
C5A | 0.083 (7) | 0.047 (8) | 0.062 (7) | 0.008 (6) | 0.021 (6) | 0.019 (7) |
C6A | 0.077 (7) | 0.054 (8) | 0.091 (9) | −0.009 (6) | 0.016 (7) | 0.017 (8) |
C7A | 0.077 (7) | 0.051 (8) | 0.063 (7) | −0.002 (6) | 0.010 (6) | 0.005 (6) |
C8A | 0.148 (12) | 0.114 (15) | 0.060 (8) | −0.017 (12) | 0.033 (8) | 0.008 (10) |
C9A | 0.064 (6) | 0.038 (7) | 0.038 (6) | −0.015 (5) | 0.006 (5) | 0.003 (5) |
C14A | 0.080 (7) | 0.040 (7) | 0.053 (7) | 0.000 (6) | 0.030 (5) | 0.005 (5) |
C13A | 0.039 (5) | 0.046 (7) | 0.068 (7) | −0.007 (5) | −0.009 (5) | 0.008 (6) |
C12A | 0.067 (6) | 0.058 (8) | 0.044 (6) | −0.004 (6) | 0.015 (5) | −0.002 (6) |
C11A | 0.082 (7) | 0.024 (6) | 0.049 (6) | −0.003 (5) | 0.003 (5) | 0.003 (5) |
C10A | 0.057 (6) | 0.040 (7) | 0.068 (7) | −0.001 (5) | −0.004 (5) | −0.002 (6) |
C15A | 0.165 (13) | 0.065 (11) | 0.090 (9) | 0.006 (10) | 0.024 (9) | 0.034 (9) |
N1B | 0.070 (5) | 0.056 (7) | 0.043 (5) | −0.004 (5) | 0.003 (4) | −0.007 (5) |
O1B | 0.153 (8) | 0.065 (6) | 0.048 (4) | 0.011 (6) | 0.031 (5) | 0.009 (5) |
O2B | 0.120 (6) | 0.066 (7) | 0.064 (5) | 0.007 (6) | 0.021 (4) | 0.011 (5) |
O3B | 0.092 (5) | 0.081 (7) | 0.044 (4) | −0.014 (5) | 0.010 (3) | 0.005 (5) |
C1B | 0.055 (6) | 0.068 (9) | 0.048 (6) | −0.007 (6) | 0.003 (5) | −0.008 (6) |
C2B | 0.063 (6) | 0.041 (7) | 0.069 (7) | −0.003 (5) | 0.009 (5) | −0.002 (6) |
C3B | 0.083 (7) | 0.044 (7) | 0.033 (5) | −0.003 (6) | 0.011 (5) | 0.007 (5) |
C4B | 0.079 (7) | 0.057 (9) | 0.050 (7) | −0.015 (6) | 0.025 (5) | −0.002 (7) |
C5B | 0.072 (7) | 0.064 (9) | 0.041 (6) | −0.021 (7) | 0.002 (5) | 0.002 (7) |
C6B | 0.081 (7) | 0.052 (8) | 0.071 (8) | 0.005 (6) | 0.012 (6) | 0.007 (7) |
C7B | 0.062 (6) | 0.054 (8) | 0.069 (8) | −0.008 (6) | 0.011 (5) | −0.007 (6) |
C8B | 0.171 (14) | 0.084 (13) | 0.097 (10) | 0.024 (12) | 0.049 (10) | −0.014 (10) |
C9B | 0.049 (5) | 0.034 (6) | 0.041 (5) | −0.002 (5) | −0.006 (4) | −0.005 (5) |
C10B | 0.044 (5) | 0.051 (7) | 0.072 (7) | −0.009 (5) | 0.010 (5) | −0.015 (6) |
C11B | 0.072 (6) | 0.052 (8) | 0.036 (5) | −0.012 (6) | 0.000 (5) | 0.001 (5) |
C12B | 0.045 (5) | 0.055 (7) | 0.051 (6) | 0.001 (5) | 0.005 (4) | −0.006 (6) |
C13B | 0.089 (7) | 0.047 (7) | 0.056 (7) | 0.000 (6) | 0.012 (6) | −0.003 (6) |
C14B | 0.078 (7) | 0.043 (7) | 0.048 (6) | −0.005 (6) | 0.006 (5) | −0.014 (5) |
C15B | 0.137 (11) | 0.067 (10) | 0.082 (8) | −0.010 (9) | 0.035 (8) | 0.009 (8) |
N1A—C1A | 1.315 (15) | N1B—C1B | 1.315 (15) |
N1A—C9A | 1.397 (11) | N1B—C9B | 1.396 (11) |
O1A—C4A | 1.330 (13) | O1B—C4B | 1.352 (13) |
O1A—C8A | 1.452 (15) | O1B—C8B | 1.414 (16) |
O2A—C5A | 1.348 (13) | O2B—C5B | 1.373 (12) |
O2A—C8A | 1.42 (2) | O2B—C8B | 1.423 (18) |
O3A—C12A | 1.385 (11) | O3B—C12B | 1.373 (11) |
O3A—C15A | 1.434 (15) | O3B—C15B | 1.447 (16) |
C1A—C2A | 1.426 (13) | C1B—C2B | 1.448 (14) |
C1A—H1A | 0.9300 | C1B—H1B | 0.9300 |
C2A—C7A | 1.411 (17) | C2B—C3B | 1.388 (15) |
C2A—C3A | 1.426 (16) | C2B—C7B | 1.402 (17) |
C3A—C4A | 1.379 (13) | C3B—C4B | 1.329 (12) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.403 (17) | C4B—C5B | 1.462 (18) |
C5A—C6A | 1.406 (17) | C5B—C6B | 1.351 (17) |
C6A—C7A | 1.375 (14) | C6B—C7B | 1.396 (14) |
C6A—H6A | 0.9300 | C6B—H6B | 0.9300 |
C7A—H7A | 0.9300 | C7B—H7B | 0.9300 |
C8A—H8A | 0.9700 | C8B—H8C | 0.9700 |
C8A—H8B | 0.9700 | C8B—H8D | 0.9700 |
C9A—C10A | 1.390 (14) | C9B—C14B | 1.381 (15) |
C9A—C14A | 1.431 (14) | C9B—C10B | 1.412 (13) |
C14A—C13A | 1.349 (12) | C10B—C11B | 1.369 (12) |
C14A—H14A | 0.9300 | C10B—H10B | 0.9300 |
C13A—C12A | 1.394 (14) | C11B—C12B | 1.404 (15) |
C13A—H13A | 0.9300 | C11B—H11B | 0.9300 |
C12A—C11A | 1.397 (16) | C12B—C13B | 1.352 (13) |
C11A—C10A | 1.353 (13) | C13B—C14B | 1.410 (13) |
C11A—H11A | 0.9300 | C13B—H13B | 0.9300 |
C10A—H10A | 0.9300 | C14B—H14B | 0.9300 |
C15A—H15A | 0.9600 | C15B—H15D | 0.9600 |
C15A—H15B | 0.9600 | C15B—H15E | 0.9600 |
C15A—H15C | 0.9600 | C15B—H15F | 0.9600 |
C1A—N1A—C9A | 118.9 (10) | C1B—N1B—C9B | 119.4 (10) |
C4A—O1A—C8A | 106.6 (11) | C4B—O1B—C8B | 108.0 (10) |
C5A—O2A—C8A | 106.1 (10) | C5B—O2B—C8B | 105.5 (10) |
C12A—O3A—C15A | 116.4 (10) | C12B—O3B—C15B | 116.1 (9) |
N1A—C1A—C2A | 123.2 (12) | N1B—C1B—C2B | 121.7 (11) |
N1A—C1A—H1A | 118.4 | N1B—C1B—H1B | 119.2 |
C2A—C1A—H1A | 118.4 | C2B—C1B—H1B | 119.2 |
C7A—C2A—C3A | 119.3 (10) | C3B—C2B—C7B | 119.6 (10) |
C7A—C2A—C1A | 120.6 (12) | C3B—C2B—C1B | 123.0 (11) |
C3A—C2A—C1A | 120.2 (12) | C7B—C2B—C1B | 117.4 (11) |
C4A—C3A—C2A | 117.6 (11) | C4B—C3B—C2B | 120.7 (12) |
C4A—C3A—H3A | 121.2 | C4B—C3B—H3B | 119.6 |
C2A—C3A—H3A | 121.2 | C2B—C3B—H3B | 119.6 |
O1A—C4A—C3A | 128.6 (12) | C3B—C4B—O1B | 132.5 (12) |
O1A—C4A—C5A | 109.4 (10) | C3B—C4B—C5B | 120.1 (11) |
C3A—C4A—C5A | 122.0 (11) | O1B—C4B—C5B | 107.4 (9) |
O2A—C5A—C6A | 128.6 (12) | C6B—C5B—O2B | 131.0 (12) |
O2A—C5A—C4A | 110.3 (11) | C6B—C5B—C4B | 119.7 (9) |
C6A—C5A—C4A | 121.0 (10) | O2B—C5B—C4B | 109.4 (11) |
C7A—C6A—C5A | 117.1 (12) | C5B—C6B—C7B | 119.4 (12) |
C7A—C6A—H6A | 121.4 | C5B—C6B—H6B | 120.3 |
C5A—C6A—H6A | 121.4 | C7B—C6B—H6B | 120.3 |
C6A—C7A—C2A | 122.9 (12) | C6B—C7B—C2B | 120.5 (11) |
C6A—C7A—H7A | 118.5 | C6B—C7B—H7B | 119.7 |
C2A—C7A—H7A | 118.5 | C2B—C7B—H7B | 119.7 |
O2A—C8A—O1A | 107.2 (10) | O1B—C8B—O2B | 109.7 (10) |
O2A—C8A—H8A | 110.3 | O1B—C8B—H8C | 109.7 |
O1A—C8A—H8A | 110.3 | O2B—C8B—H8C | 109.7 |
O2A—C8A—H8B | 110.3 | O1B—C8B—H8D | 109.7 |
O1A—C8A—H8B | 110.3 | O2B—C8B—H8D | 109.7 |
H8A—C8A—H8B | 108.5 | H8C—C8B—H8D | 108.2 |
C10A—C9A—N1A | 126.9 (10) | C14B—C9B—N1B | 118.4 (9) |
C10A—C9A—C14A | 115.8 (8) | C14B—C9B—C10B | 115.6 (9) |
N1A—C9A—C14A | 117.2 (10) | N1B—C9B—C10B | 126.0 (10) |
C13A—C14A—C9A | 122.3 (10) | C11B—C10B—C9B | 121.4 (10) |
C13A—C14A—H14A | 118.8 | C11B—C10B—H10B | 119.3 |
C9A—C14A—H14A | 118.9 | C9B—C10B—H10B | 119.3 |
C14A—C13A—C12A | 120.3 (10) | C10B—C11B—C12B | 122.2 (10) |
C14A—C13A—H13A | 119.9 | C10B—C11B—H11B | 118.9 |
C12A—C13A—H13A | 119.8 | C12B—C11B—H11B | 118.9 |
O3A—C12A—C13A | 126.3 (11) | C13B—C12B—O3B | 127.6 (11) |
O3A—C12A—C11A | 115.5 (10) | C13B—C12B—C11B | 117.0 (9) |
C13A—C12A—C11A | 118.2 (9) | O3B—C12B—C11B | 115.3 (9) |
C10A—C11A—C12A | 121.3 (10) | C12B—C13B—C14B | 121.2 (11) |
C10A—C11A—H11A | 119.4 | C12B—C13B—H13B | 119.4 |
C12A—C11A—H11A | 119.4 | C14B—C13B—H13B | 119.4 |
C11A—C10A—C9A | 122.1 (10) | C9B—C14B—C13B | 122.5 (10) |
C11A—C10A—H10A | 119.0 | C9B—C14B—H14B | 118.8 |
C9A—C10A—H10A | 118.9 | C13B—C14B—H14B | 118.8 |
O3A—C15A—H15A | 109.5 | O3B—C15B—H15D | 109.5 |
O3A—C15A—H15B | 109.5 | O3B—C15B—H15E | 109.5 |
H15A—C15A—H15B | 109.5 | H15D—C15B—H15E | 109.5 |
O3A—C15A—H15C | 109.5 | O3B—C15B—H15F | 109.5 |
H15A—C15A—H15C | 109.5 | H15D—C15B—H15F | 109.5 |
H15B—C15A—H15C | 109.5 | H15E—C15B—H15F | 109.5 |
C9A—N1A—C1A—C2A | −177.6 (8) | C9B—N1B—C1B—C2B | −180.0 (7) |
N1A—C1A—C2A—C7A | −168.5 (10) | N1B—C1B—C2B—C3B | −8.3 (15) |
N1A—C1A—C2A—C3A | 10.9 (15) | N1B—C1B—C2B—C7B | 170.7 (10) |
C7A—C2A—C3A—C4A | 1.5 (15) | C7B—C2B—C3B—C4B | −0.1 (15) |
C1A—C2A—C3A—C4A | −177.9 (9) | C1B—C2B—C3B—C4B | 178.9 (9) |
C8A—O1A—C4A—C3A | 179.6 (11) | C2B—C3B—C4B—O1B | 179.8 (10) |
C8A—O1A—C4A—C5A | −3.6 (13) | C2B—C3B—C4B—C5B | −0.5 (15) |
C2A—C3A—C4A—O1A | 176.4 (10) | C8B—O1B—C4B—C3B | 179.8 (13) |
C2A—C3A—C4A—C5A | 0.0 (15) | C8B—O1B—C4B—C5B | 0.1 (13) |
C8A—O2A—C5A—C6A | −179.2 (13) | C8B—O2B—C5B—C6B | 179.6 (13) |
C8A—O2A—C5A—C4A | 4.8 (14) | C8B—O2B—C5B—C4B | −0.4 (13) |
O1A—C4A—C5A—O2A | −0.8 (13) | C3B—C4B—C5B—C6B | 0.4 (15) |
C3A—C4A—C5A—O2A | 176.3 (9) | O1B—C4B—C5B—C6B | −179.8 (9) |
O1A—C4A—C5A—C6A | −177.1 (10) | C3B—C4B—C5B—O2B | −179.6 (9) |
C3A—C4A—C5A—C6A | −0.1 (17) | O1B—C4B—C5B—O2B | 0.2 (11) |
O2A—C5A—C6A—C7A | −176.9 (10) | O2B—C5B—C6B—C7B | −179.8 (10) |
C4A—C5A—C6A—C7A | −1.3 (17) | C4B—C5B—C6B—C7B | 0.2 (15) |
C5A—C6A—C7A—C2A | 2.9 (16) | C5B—C6B—C7B—C2B | −0.8 (15) |
C3A—C2A—C7A—C6A | −3.1 (16) | C3B—C2B—C7B—C6B | 0.7 (15) |
C1A—C2A—C7A—C6A | 176.3 (9) | C1B—C2B—C7B—C6B | −178.3 (8) |
C5A—O2A—C8A—O1A | −6.8 (15) | C4B—O1B—C8B—O2B | −0.4 (16) |
C4A—O1A—C8A—O2A | 6.4 (15) | C5B—O2B—C8B—O1B | 0.5 (15) |
C1A—N1A—C9A—C10A | 35.4 (14) | C1B—N1B—C9B—C14B | 145.3 (10) |
C1A—N1A—C9A—C14A | −148.3 (9) | C1B—N1B—C9B—C10B | −34.5 (14) |
C10A—C9A—C14A—C13A | −1.5 (13) | C14B—C9B—C10B—C11B | 0.0 (14) |
N1A—C9A—C14A—C13A | −178.3 (9) | N1B—C9B—C10B—C11B | 179.8 (9) |
C9A—C14A—C13A—C12A | 2.6 (13) | C9B—C10B—C11B—C12B | −0.7 (15) |
C15A—O3A—C12A—C13A | −9.1 (15) | C15B—O3B—C12B—C13B | −1.5 (15) |
C15A—O3A—C12A—C11A | 173.5 (11) | C15B—O3B—C12B—C11B | −179.5 (10) |
C14A—C13A—C12A—O3A | 179.5 (9) | C10B—C11B—C12B—C13B | 2.6 (14) |
C14A—C13A—C12A—C11A | −3.2 (13) | C10B—C11B—C12B—O3B | −179.2 (9) |
O3A—C12A—C11A—C10A | −179.6 (9) | O3B—C12B—C13B—C14B | 178.3 (9) |
C13A—C12A—C11A—C10A | 2.8 (15) | C11B—C12B—C13B—C14B | −3.8 (14) |
C12A—C11A—C10A—C9A | −1.9 (15) | N1B—C9B—C14B—C13B | 179.0 (9) |
N1A—C9A—C10A—C11A | 177.6 (9) | C10B—C9B—C14B—C13B | −1.2 (14) |
C14A—C9A—C10A—C11A | 1.2 (13) | C12B—C13B—C14B—C9B | 3.2 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8A—H8A···O3Ai | 0.97 | 2.58 | 3.28 (2) | 129 |
C8B—H8C···O3Bi | 0.97 | 2.57 | 3.36 (2) | 139 |
C15A—H15B···O2Aii | 0.96 | 2.60 | 3.32 (2) | 132 |
C13A—H13A···Cg2B | 0.93 | 3.05 | 3.69 (4) | 127 |
C10A—H10A···Cg2Aiii | 0.93 | 2.70 | 3.45 (4) | 138 |
C13B—H13B···Cg2Aiv | 0.93 | 3.09 | 3.70 (4) | 124 |
Symmetry codes: (i) x, y, z−1; (ii) x, y−1, z+1; (iii) −x+1, y+1/2, −z+1; (iv) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C15H13NO3 |
Mr | 255.26 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 14.497 (2), 6.1192 (14), 14.732 (2) |
β (°) | 102.819 (2) |
V (Å3) | 1274.3 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.57 × 0.18 × 0.11 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.949, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6121, 2363, 1115 |
Rint | 0.099 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.103, 0.303, 0.95 |
No. of reflections | 2363 |
No. of parameters | 345 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.29 |
Absolute structure | Flack (1983), with 1668 Freidel pairs |
Absolute structure parameter | −10 (10) |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
C8A—H8A···O3Ai | 0.97 | 2.58 | 3.28 (2) | 128.5 |
C8B—H8C···O3Bi | 0.97 | 2.57 | 3.36 (2) | 139.0 |
C15A—H15B···O2Aii | 0.96 | 2.60 | 3.32 (2) | 131.7 |
C13A—H13A···Cg2B | 0.93 | 3.05 | 3.69 (4) | 127.1 |
C10A—H10A···Cg2Aiii | 0.93 | 2.70 | 3.45 (4) | 138.4 |
C13B—H13B···Cg2Aiv | 0.93 | 3.09 | 3.70 (4) | 124.3 |
Symmetry codes: (i) x, y, z−1; (ii) x, y−1, z+1; (iii) −x+1, y+1/2, −z+1; (iv) x, y−1, z. |
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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).