Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037063/ci2427sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037063/ci2427Isup2.hkl |
CCDC reference: 660191
Key indicators
- Single-crystal X-ray study
- T = 203 K
- Mean (C-C) = 0.005 Å
- R factor = 0.055
- wR factor = 0.162
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
Alert level C REFLT03_ALERT_1_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 32.49 From the CIF: _diffrn_reflns_theta_full 32.49 From the CIF: _reflns_number_total 4496 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4753 Completeness (_total/calc) 94.59% PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 1 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.973 Tmax scaled 0.973 Tmin scaled 0.929 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 32.49 From the CIF: _reflns_number_total 4496 Count of symmetry unique reflns 4753 Completeness (_total/calc) 94.59% 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 ....... 2
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 3 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 4 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 structures, see: Yathirajan et al. (2007); Harrison et al. (2006); Patil et al. (2006). For related literature, see: Dhar et al. (1981); Opletalova & Sedivy et al. (1999); Sarojini et al. (2006).
4-Nitrobenzaldehyde (1.81 g, 0.01 mol) in ethanol (50 ml) was mixed with 1-(4-methyl phenyl) ethanone (1.34 ml, 0.01 mol) and the mixture was treated with 10 ml of 10% KOH. The reaction mixture was then kept for constant stirring. The solid precipitate obtained was filtered, washed with ethanol and dried. The crystal growth was carried out in acetone solvent by the slow evaporation technique (m.p. 435 K). Analysis found: C 71.78, H 4.83, N 5.18%; C16H13NO3 requires: C 71.90, H 4.90, N 5.24%.
All H atoms were refined using a riding model with C—H = 0.94–0.97 Å, and Uiso(H) = 1.18–1.50Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs were averaged.
Chalcone is an aromatic ketone that forms a central core for a variety of important biological compounds, which are known collectively as chalcones. Chalcones and the corresponding heterocyclic analogs are valuable intermediates in organic synthesis and show numerous biological effects. The non-linear optical (NLO) effects in organic molecules originates from a strong donor–acceptor intermolecular interaction, a delocalized π electron system and also the ability to crystallize in non-centro symmetric space groups. Chalcones are finding applications as organic non-linear optical materials due to their good SHG conversion efficiencies. Herein we report the synthesis and crystal structure of a new chalcone, the title compound.
The asymmetric unit of the title compound contains two independent molecules A and B both of which are shown in Fig. 1. The C9—C8—C1—C6 and C9—C10—C11—C12 torsion angles [(A) -0.8 (5), 6.4 (5)°; (B) 5.2 (4), -8.2 (5)°] indicate that the 4-methylphenyl and 4-nitrophenyl groups are slightly twisted with respect to the central O1/C8—C11 plane.
In the crystal structure, the independent molecues exist as a pseudo inversion-related pair with the centroids of the 4-methylphenyl and 4-nitrophenyl rings separated by a distance of 3.7550 (17) Å, indicating π-π stacking interaction. Crystal packing shows each of these independent molecules form sheets approximately parallel to the ab plane (Fig. 2). The sheets formed by these molecules are alternatively stacked along the c axis and are cross-linked by C—H···O intermolecular hydrogen-bonding interactions (Table 1).
For related structures, see: Yathirajan et al. (2007); Harrison et al. (2006); Patil et al. (2006). For related literature, see: Dhar et al. (1981); Opletalova & Sedivy et al. (1999); Sarojini et al. (2006).
Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C16H13NO3 | F(000) = 560 |
Mr = 267.27 | Dx = 1.350 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yc | Cell parameters from 10389 reflections |
a = 5.97300 (1) Å | θ = 4.6–32.4° |
b = 15.0731 (5) Å | µ = 0.09 mm−1 |
c = 14.6768 (4) Å | T = 203 K |
β = 95.785 (2)° | Block, colourless |
V = 1314.65 (6) Å3 | 0.47 × 0.41 × 0.29 mm |
Z = 4 |
Oxford Diffraction Gemini R diffractometer | 4496 independent reflections |
Radiation source: fine-focus sealed tube | 2661 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.5°, θmin = 4.6° |
φ and ω scans | h = −8→9 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −22→21 |
Tmin = 0.955, Tmax = 1.000 | l = −21→22 |
37695 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | H-atom parameters constrained |
S = 1.25 | w = 1/[σ2(Fo2) + (0.0728P)2] where P = (Fo2 + 2Fc2)/3 |
4496 reflections | (Δ/σ)max = 0.001 |
363 parameters | Δρmax = 0.23 e Å−3 |
2 restraints | Δρmin = −0.23 e Å−3 |
C16H13NO3 | V = 1314.65 (6) Å3 |
Mr = 267.27 | Z = 4 |
Monoclinic, Pc | Mo Kα radiation |
a = 5.97300 (1) Å | µ = 0.09 mm−1 |
b = 15.0731 (5) Å | T = 203 K |
c = 14.6768 (4) Å | 0.47 × 0.41 × 0.29 mm |
β = 95.785 (2)° |
Oxford Diffraction Gemini R diffractometer | 4496 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 2661 reflections with I > 2σ(I) |
Tmin = 0.955, Tmax = 1.000 | Rint = 0.051 |
37695 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 2 restraints |
wR(F2) = 0.162 | H-atom parameters constrained |
S = 1.25 | Δρmax = 0.23 e Å−3 |
4496 reflections | Δρmin = −0.23 e Å−3 |
363 parameters |
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 | ||
O1A | 0.5810 (4) | 0.15276 (19) | 0.3609 (2) | 0.0598 (7) | |
O2A | −0.5435 (4) | 0.5503 (2) | 0.1891 (2) | 0.0638 (7) | |
O3A | −0.2876 (5) | 0.6415 (2) | 0.2422 (2) | 0.0717 (9) | |
N1A | −0.3572 (5) | 0.5665 (2) | 0.22697 (19) | 0.0434 (7) | |
C1A | 0.3401 (6) | 0.0319 (3) | 0.3272 (2) | 0.0377 (7) | |
C2A | 0.5097 (5) | −0.0293 (3) | 0.3529 (2) | 0.0434 (8) | |
H2A | 0.6549 | −0.0089 | 0.3732 | 0.052* | |
C3A | 0.4681 (6) | −0.1196 (3) | 0.3492 (3) | 0.0501 (9) | |
H3A | 0.5850 | −0.1594 | 0.3676 | 0.060* | |
C4A | 0.2560 (5) | −0.1524 (2) | 0.3185 (2) | 0.0406 (8) | |
C5A | 0.0874 (6) | −0.0926 (3) | 0.2929 (2) | 0.0452 (9) | |
H5A | −0.0568 | −0.1136 | 0.2718 | 0.054* | |
C6A | 0.1261 (5) | −0.0018 (2) | 0.2977 (2) | 0.0431 (8) | |
H6A | 0.0072 | 0.0376 | 0.2809 | 0.052* | |
C7A | 0.2110 (7) | −0.2512 (3) | 0.3134 (3) | 0.0546 (9) | |
H7A | 0.0911 | −0.2631 | 0.2654 | 0.082* | |
H7B | 0.1665 | −0.2717 | 0.3716 | 0.082* | |
H7C | 0.3464 | −0.2820 | 0.3001 | 0.082* | |
C8A | 0.3919 (5) | 0.1278 (2) | 0.3334 (2) | 0.0394 (7) | |
C9A | 0.2096 (5) | 0.1932 (3) | 0.3060 (2) | 0.0403 (8) | |
H9A | 0.0735 | 0.1738 | 0.2746 | 0.048* | |
C10A | 0.2392 (5) | 0.2787 (2) | 0.3258 (2) | 0.0382 (7) | |
H10A | 0.3773 | 0.2948 | 0.3579 | 0.046* | |
C11A | 0.0756 (5) | 0.3511 (2) | 0.30221 (19) | 0.0349 (7) | |
C12A | −0.1442 (5) | 0.3358 (2) | 0.2625 (2) | 0.0400 (7) | |
H12A | −0.1949 | 0.2772 | 0.2523 | 0.048* | |
C13A | −0.2877 (5) | 0.4058 (3) | 0.2381 (2) | 0.0408 (8) | |
H13A | −0.4348 | 0.3957 | 0.2110 | 0.049* | |
C14A | −0.2081 (5) | 0.4915 (2) | 0.2549 (2) | 0.0371 (7) | |
C15A | 0.0033 (5) | 0.5092 (2) | 0.2955 (2) | 0.0407 (7) | |
H15A | 0.0516 | 0.5679 | 0.3069 | 0.049* | |
C16A | 0.1458 (5) | 0.4373 (2) | 0.3197 (2) | 0.0404 (7) | |
H16A | 0.2914 | 0.4479 | 0.3482 | 0.048* | |
O1B | −0.3940 (4) | 0.40110 (19) | 0.4712 (2) | 0.0581 (7) | |
O2B | 0.7162 (4) | −0.0017 (2) | 0.6455 (2) | 0.0614 (8) | |
O3B | 0.4447 (5) | −0.0907 (2) | 0.6053 (2) | 0.0647 (8) | |
N1B | 0.5230 (5) | −0.0162 (2) | 0.61432 (18) | 0.0430 (7) | |
C1B | −0.1587 (5) | 0.5225 (2) | 0.51618 (18) | 0.0326 (6) | |
C2B | −0.3283 (6) | 0.5826 (3) | 0.4924 (2) | 0.0404 (8) | |
H2B | −0.4714 | 0.5618 | 0.4695 | 0.048* | |
C3B | −0.2924 (5) | 0.6731 (2) | 0.5014 (2) | 0.0444 (8) | |
H3B | −0.4124 | 0.7125 | 0.4862 | 0.053* | |
C4B | −0.0826 (5) | 0.7064 (3) | 0.5323 (2) | 0.0399 (8) | |
C5B | 0.0894 (5) | 0.6454 (2) | 0.5563 (2) | 0.0416 (7) | |
H5B | 0.2329 | 0.6662 | 0.5786 | 0.050* | |
C6B | 0.0532 (5) | 0.5552 (3) | 0.5479 (2) | 0.0391 (8) | |
H6B | 0.1723 | 0.5155 | 0.5638 | 0.047* | |
C7B | −0.0428 (6) | 0.8042 (3) | 0.5426 (3) | 0.0533 (9) | |
H7D | 0.1068 | 0.8146 | 0.5730 | 0.080* | |
H7E | −0.1538 | 0.8296 | 0.5789 | 0.080* | |
H7F | −0.0557 | 0.8319 | 0.4826 | 0.080* | |
C8B | −0.2056 (5) | 0.4258 (3) | 0.5051 (2) | 0.0378 (8) | |
C9B | −0.0307 (5) | 0.3598 (3) | 0.5351 (2) | 0.0411 (8) | |
H9B | 0.1033 | 0.3785 | 0.5688 | 0.049* | |
C10B | −0.0609 (5) | 0.2744 (2) | 0.5152 (2) | 0.0375 (7) | |
H10B | −0.1970 | 0.2588 | 0.4812 | 0.045* | |
C11B | 0.0964 (5) | 0.2023 (2) | 0.54079 (19) | 0.0353 (7) | |
C12B | 0.3171 (5) | 0.2161 (2) | 0.5814 (2) | 0.0416 (8) | |
H12B | 0.3699 | 0.2743 | 0.5926 | 0.050* | |
C13B | 0.4571 (5) | 0.1451 (2) | 0.6050 (2) | 0.0407 (7) | |
H13B | 0.6043 | 0.1546 | 0.6324 | 0.049* | |
C14B | 0.3778 (5) | 0.0600 (2) | 0.5879 (2) | 0.0358 (7) | |
C15B | 0.1615 (5) | 0.0439 (3) | 0.5465 (2) | 0.0422 (8) | |
H15B | 0.1097 | −0.0143 | 0.5351 | 0.051* | |
C16B | 0.0267 (5) | 0.1153 (2) | 0.5227 (2) | 0.0399 (7) | |
H16B | −0.1182 | 0.1053 | 0.4932 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0407 (13) | 0.0393 (16) | 0.0947 (19) | −0.0026 (11) | −0.0155 (12) | −0.0039 (13) |
O2A | 0.0416 (15) | 0.062 (2) | 0.0841 (18) | 0.0046 (12) | −0.0106 (12) | 0.0084 (15) |
O3A | 0.0562 (16) | 0.0420 (18) | 0.112 (2) | 0.0054 (14) | −0.0137 (15) | 0.0037 (17) |
N1A | 0.0383 (15) | 0.0412 (19) | 0.0508 (15) | 0.0056 (13) | 0.0050 (12) | 0.0063 (13) |
C1A | 0.0336 (16) | 0.039 (2) | 0.0403 (15) | −0.0015 (14) | 0.0033 (12) | −0.0021 (14) |
C2A | 0.0300 (16) | 0.039 (2) | 0.0592 (19) | 0.0030 (14) | −0.0058 (13) | −0.0014 (16) |
C3A | 0.0412 (19) | 0.043 (2) | 0.064 (2) | 0.0060 (17) | −0.0044 (15) | 0.0048 (18) |
C4A | 0.0415 (18) | 0.035 (2) | 0.0452 (16) | 0.0005 (14) | 0.0045 (13) | 0.0006 (13) |
C5A | 0.0380 (18) | 0.041 (2) | 0.0547 (18) | −0.0036 (16) | −0.0031 (14) | −0.0006 (17) |
C6A | 0.0342 (17) | 0.035 (2) | 0.0581 (19) | 0.0046 (14) | −0.0037 (13) | −0.0031 (15) |
C7A | 0.063 (2) | 0.037 (2) | 0.064 (2) | −0.0034 (19) | 0.0048 (17) | 0.0001 (17) |
C8A | 0.0384 (16) | 0.0322 (19) | 0.0460 (16) | 0.0023 (14) | −0.0042 (12) | 0.0004 (13) |
C9A | 0.0396 (18) | 0.033 (2) | 0.0454 (17) | −0.0021 (15) | −0.0077 (13) | −0.0009 (14) |
C10A | 0.0397 (16) | 0.0355 (19) | 0.0385 (14) | 0.0016 (14) | −0.0003 (11) | −0.0018 (13) |
C11A | 0.0342 (16) | 0.0344 (19) | 0.0361 (14) | 0.0011 (13) | 0.0035 (11) | 0.0015 (13) |
C12A | 0.0357 (16) | 0.036 (2) | 0.0477 (16) | −0.0062 (14) | 0.0012 (12) | −0.0008 (14) |
C13A | 0.0304 (16) | 0.043 (2) | 0.0489 (17) | −0.0010 (15) | 0.0036 (13) | −0.0004 (15) |
C14A | 0.0365 (17) | 0.036 (2) | 0.0387 (15) | 0.0028 (14) | 0.0059 (12) | 0.0025 (12) |
C15A | 0.0383 (17) | 0.0344 (19) | 0.0497 (17) | −0.0026 (14) | 0.0053 (13) | 0.0016 (14) |
C16A | 0.0380 (16) | 0.039 (2) | 0.0434 (15) | −0.0029 (14) | −0.0007 (12) | −0.0038 (14) |
O1B | 0.0446 (14) | 0.0446 (16) | 0.0805 (17) | −0.0035 (11) | −0.0155 (11) | −0.0055 (13) |
O2B | 0.0337 (14) | 0.059 (2) | 0.0889 (18) | 0.0037 (11) | −0.0074 (12) | 0.0012 (15) |
O3B | 0.0501 (15) | 0.0375 (17) | 0.103 (2) | 0.0023 (13) | −0.0084 (14) | 0.0014 (15) |
N1B | 0.0379 (16) | 0.0441 (19) | 0.0466 (14) | 0.0029 (13) | 0.0023 (11) | 0.0020 (13) |
C1B | 0.0334 (15) | 0.0319 (18) | 0.0324 (13) | 0.0010 (12) | 0.0033 (11) | 0.0017 (11) |
C2B | 0.0330 (16) | 0.040 (2) | 0.0464 (16) | −0.0027 (14) | −0.0040 (12) | 0.0011 (15) |
C3B | 0.0374 (17) | 0.039 (2) | 0.0555 (18) | 0.0049 (14) | −0.0016 (13) | 0.0005 (15) |
C4B | 0.0392 (17) | 0.038 (2) | 0.0431 (16) | −0.0012 (14) | 0.0075 (13) | 0.0024 (14) |
C5B | 0.0294 (15) | 0.044 (2) | 0.0506 (17) | 0.0007 (14) | −0.0016 (12) | −0.0020 (15) |
C6B | 0.0310 (16) | 0.039 (2) | 0.0463 (17) | −0.0012 (14) | 0.0000 (12) | −0.0025 (15) |
C7B | 0.051 (2) | 0.034 (2) | 0.074 (2) | −0.0020 (17) | 0.0044 (16) | −0.0014 (17) |
C8B | 0.0429 (18) | 0.036 (2) | 0.0335 (14) | −0.0028 (14) | −0.0014 (12) | −0.0014 (13) |
C9B | 0.0372 (17) | 0.040 (2) | 0.0441 (16) | 0.0010 (14) | −0.0043 (12) | −0.0034 (14) |
C10B | 0.0359 (16) | 0.036 (2) | 0.0399 (15) | −0.0008 (14) | 0.0022 (12) | 0.0054 (14) |
C11B | 0.0387 (16) | 0.0319 (18) | 0.0354 (14) | 0.0000 (13) | 0.0040 (11) | 0.0009 (12) |
C12B | 0.0387 (17) | 0.0340 (18) | 0.0518 (18) | −0.0049 (14) | 0.0035 (13) | −0.0021 (14) |
C13B | 0.0352 (16) | 0.041 (2) | 0.0452 (16) | −0.0061 (14) | −0.0004 (12) | −0.0043 (14) |
C14B | 0.0323 (16) | 0.0385 (19) | 0.0364 (14) | 0.0010 (14) | 0.0022 (12) | 0.0000 (13) |
C15B | 0.0373 (18) | 0.037 (2) | 0.0509 (18) | −0.0033 (14) | −0.0028 (13) | −0.0052 (15) |
C16B | 0.0334 (16) | 0.037 (2) | 0.0480 (16) | −0.0073 (14) | −0.0030 (12) | −0.0027 (14) |
O1A—C8A | 1.220 (4) | O1B—C8B | 1.240 (4) |
O2A—N1A | 1.218 (4) | O2B—N1B | 1.217 (4) |
O3A—N1A | 1.217 (4) | O3B—N1B | 1.219 (4) |
N1A—C14A | 1.472 (4) | N1B—C14B | 1.468 (5) |
C1A—C2A | 1.394 (5) | C1B—C2B | 1.378 (5) |
C1A—C6A | 1.403 (5) | C1B—C6B | 1.394 (5) |
C1A—C8A | 1.479 (5) | C1B—C8B | 1.490 (5) |
C2A—C3A | 1.383 (5) | C2B—C3B | 1.385 (5) |
C2A—H2A | 0.94 | C2B—H2B | 0.94 |
C3A—C4A | 1.392 (5) | C3B—C4B | 1.384 (5) |
C3A—H3A | 0.94 | C3B—H3B | 0.94 |
C4A—C5A | 1.376 (5) | C4B—C5B | 1.397 (5) |
C4A—C7A | 1.513 (5) | C4B—C7B | 1.499 (5) |
C5A—C6A | 1.388 (5) | C5B—C6B | 1.380 (5) |
C5A—H5A | 0.94 | C5B—H5B | 0.94 |
C6A—H6A | 0.94 | C6B—H6B | 0.94 |
C7A—H7A | 0.97 | C7B—H7D | 0.97 |
C7A—H7B | 0.97 | C7B—H7E | 0.97 |
C7A—H7C | 0.97 | C7B—H7F | 0.97 |
C8A—C9A | 1.494 (5) | C8B—C9B | 1.476 (5) |
C9A—C10A | 1.328 (5) | C9B—C10B | 1.329 (5) |
C9A—H9A | 0.94 | C9B—H9B | 0.94 |
C10A—C11A | 1.482 (5) | C10B—C11B | 1.461 (5) |
C10A—H10A | 0.94 | C10B—H10B | 0.94 |
C11A—C16A | 1.382 (5) | C11B—C16B | 1.394 (5) |
C11A—C12A | 1.401 (4) | C11B—C12B | 1.407 (5) |
C12A—C13A | 1.384 (5) | C12B—C13B | 1.380 (5) |
C12A—H12A | 0.94 | C12B—H12B | 0.94 |
C13A—C14A | 1.390 (5) | C13B—C14B | 1.381 (5) |
C13A—H13A | 0.94 | C13B—H13B | 0.94 |
C14A—C15A | 1.367 (5) | C14B—C15B | 1.393 (5) |
C15A—C16A | 1.401 (5) | C15B—C16B | 1.367 (5) |
C15A—H15A | 0.94 | C15B—H15B | 0.94 |
C16A—H16A | 0.94 | C16B—H16B | 0.94 |
O2A—N1A—O3A | 123.4 (3) | O2B—N1B—O3B | 123.0 (3) |
O2A—N1A—C14A | 118.2 (3) | O2B—N1B—C14B | 118.1 (3) |
O3A—N1A—C14A | 118.4 (3) | O3B—N1B—C14B | 118.9 (3) |
C2A—C1A—C6A | 117.3 (3) | C2B—C1B—C6B | 118.1 (3) |
C2A—C1A—C8A | 119.2 (3) | C2B—C1B—C8B | 119.4 (3) |
C6A—C1A—C8A | 123.5 (3) | C6B—C1B—C8B | 122.5 (3) |
C3A—C2A—C1A | 121.2 (3) | C1B—C2B—C3B | 121.4 (3) |
C3A—C2A—H2A | 119.4 | C1B—C2B—H2B | 119.3 |
C1A—C2A—H2A | 119.4 | C3B—C2B—H2B | 119.3 |
C2A—C3A—C4A | 121.1 (3) | C2B—C3B—C4B | 121.0 (3) |
C2A—C3A—H3A | 119.5 | C2B—C3B—H3B | 119.5 |
C4A—C3A—H3A | 119.5 | C4B—C3B—H3B | 119.5 |
C5A—C4A—C3A | 118.2 (3) | C3B—C4B—C5B | 117.6 (3) |
C5A—C4A—C7A | 120.6 (3) | C3B—C4B—C7B | 121.3 (3) |
C3A—C4A—C7A | 121.1 (3) | C5B—C4B—C7B | 121.1 (3) |
C4A—C5A—C6A | 121.2 (3) | C6B—C5B—C4B | 121.4 (3) |
C4A—C5A—H5A | 119.4 | C6B—C5B—H5B | 119.3 |
C6A—C5A—H5A | 119.4 | C4B—C5B—H5B | 119.3 |
C5A—C6A—C1A | 121.0 (3) | C5B—C6B—C1B | 120.5 (3) |
C5A—C6A—H6A | 119.5 | C5B—C6B—H6B | 119.8 |
C1A—C6A—H6A | 119.5 | C1B—C6B—H6B | 119.8 |
C4A—C7A—H7A | 109.5 | C4B—C7B—H7D | 109.5 |
C4A—C7A—H7B | 109.5 | C4B—C7B—H7E | 109.5 |
H7A—C7A—H7B | 109.5 | H7D—C7B—H7E | 109.5 |
C4A—C7A—H7C | 109.5 | C4B—C7B—H7F | 109.5 |
H7A—C7A—H7C | 109.5 | H7D—C7B—H7F | 109.5 |
H7B—C7A—H7C | 109.5 | H7E—C7B—H7F | 109.5 |
O1A—C8A—C1A | 120.2 (3) | O1B—C8B—C9B | 120.3 (3) |
O1A—C8A—C9A | 120.7 (3) | O1B—C8B—C1B | 119.3 (3) |
C1A—C8A—C9A | 119.1 (3) | C9B—C8B—C1B | 120.4 (3) |
C10A—C9A—C8A | 120.3 (3) | C10B—C9B—C8B | 120.7 (3) |
C10A—C9A—H9A | 119.9 | C10B—C9B—H9B | 119.7 |
C8A—C9A—H9A | 119.9 | C8B—C9B—H9B | 119.7 |
C9A—C10A—C11A | 126.4 (3) | C9B—C10B—C11B | 126.5 (3) |
C9A—C10A—H10A | 116.8 | C9B—C10B—H10B | 116.7 |
C11A—C10A—H10A | 116.8 | C11B—C10B—H10B | 116.7 |
C16A—C11A—C12A | 119.1 (3) | C16B—C11B—C12B | 118.0 (3) |
C16A—C11A—C10A | 117.9 (3) | C16B—C11B—C10B | 118.6 (3) |
C12A—C11A—C10A | 123.0 (3) | C12B—C11B—C10B | 123.4 (3) |
C13A—C12A—C11A | 120.8 (3) | C13B—C12B—C11B | 120.6 (3) |
C13A—C12A—H12A | 119.6 | C13B—C12B—H12B | 119.7 |
C11A—C12A—H12A | 119.6 | C11B—C12B—H12B | 119.7 |
C12A—C13A—C14A | 118.1 (3) | C14B—C13B—C12B | 119.1 (3) |
C12A—C13A—H13A | 120.9 | C14B—C13B—H13B | 120.4 |
C14A—C13A—H13A | 120.9 | C12B—C13B—H13B | 120.4 |
C15A—C14A—C13A | 122.9 (3) | C13B—C14B—C15B | 121.8 (3) |
C15A—C14A—N1A | 118.6 (3) | C13B—C14B—N1B | 119.7 (3) |
C13A—C14A—N1A | 118.5 (3) | C15B—C14B—N1B | 118.4 (3) |
C14A—C15A—C16A | 118.1 (3) | C16B—C15B—C14B | 118.1 (3) |
C14A—C15A—H15A | 121.0 | C16B—C15B—H15B | 121.0 |
C16A—C15A—H15A | 121.0 | C14B—C15B—H15B | 121.0 |
C11A—C16A—C15A | 121.0 (3) | C15B—C16B—C11B | 122.3 (3) |
C11A—C16A—H16A | 119.5 | C15B—C16B—H16B | 118.8 |
C15A—C16A—H16A | 119.5 | C11B—C16B—H16B | 118.8 |
C6A—C1A—C2A—C3A | 0.2 (5) | C6B—C1B—C2B—C3B | −1.4 (5) |
C8A—C1A—C2A—C3A | 179.3 (3) | C8B—C1B—C2B—C3B | −179.9 (3) |
C1A—C2A—C3A—C4A | 0.8 (5) | C1B—C2B—C3B—C4B | 1.8 (5) |
C2A—C3A—C4A—C5A | −0.7 (5) | C2B—C3B—C4B—C5B | −1.6 (5) |
C2A—C3A—C4A—C7A | 179.4 (3) | C2B—C3B—C4B—C7B | −179.7 (3) |
C3A—C4A—C5A—C6A | −0.2 (5) | C3B—C4B—C5B—C6B | 1.2 (5) |
C7A—C4A—C5A—C6A | 179.7 (3) | C7B—C4B—C5B—C6B | 179.2 (3) |
C4A—C5A—C6A—C1A | 1.2 (5) | C4B—C5B—C6B—C1B | −0.9 (5) |
C2A—C1A—C6A—C5A | −1.2 (5) | C2B—C1B—C6B—C5B | 0.9 (5) |
C8A—C1A—C6A—C5A | 179.8 (3) | C8B—C1B—C6B—C5B | 179.4 (3) |
C2A—C1A—C8A—O1A | −0.1 (5) | C2B—C1B—C8B—O1B | 2.9 (4) |
C6A—C1A—C8A—O1A | 179.0 (3) | C6B—C1B—C8B—O1B | −175.6 (3) |
C2A—C1A—C8A—C9A | −179.8 (3) | C2B—C1B—C8B—C9B | −176.4 (3) |
C6A—C1A—C8A—C9A | −0.8 (5) | C6B—C1B—C8B—C9B | 5.2 (4) |
O1A—C8A—C9A—C10A | −11.7 (5) | O1B—C8B—C9B—C10B | 9.2 (5) |
C1A—C8A—C9A—C10A | 168.1 (3) | C1B—C8B—C9B—C10B | −171.5 (3) |
C8A—C9A—C10A—C11A | 179.2 (3) | C8B—C9B—C10B—C11B | −179.7 (3) |
C9A—C10A—C11A—C16A | −173.0 (3) | C9B—C10B—C11B—C16B | 173.0 (3) |
C9A—C10A—C11A—C12A | 6.4 (5) | C9B—C10B—C11B—C12B | −8.2 (5) |
C16A—C11A—C12A—C13A | 2.1 (4) | C16B—C11B—C12B—C13B | −1.9 (4) |
C10A—C11A—C12A—C13A | −177.2 (3) | C10B—C11B—C12B—C13B | 179.3 (3) |
C11A—C12A—C13A—C14A | −0.5 (4) | C11B—C12B—C13B—C14B | 0.2 (4) |
C12A—C13A—C14A—C15A | −1.1 (5) | C12B—C13B—C14B—C15B | 0.8 (5) |
C12A—C13A—C14A—N1A | 178.3 (3) | C12B—C13B—C14B—N1B | −178.7 (3) |
O2A—N1A—C14A—C15A | 178.5 (3) | O2B—N1B—C14B—C13B | −4.7 (4) |
O3A—N1A—C14A—C15A | −1.0 (4) | O3B—N1B—C14B—C13B | 174.3 (3) |
O2A—N1A—C14A—C13A | −1.0 (4) | O2B—N1B—C14B—C15B | 175.7 (3) |
O3A—N1A—C14A—C13A | 179.6 (3) | O3B—N1B—C14B—C15B | −5.3 (4) |
C13A—C14A—C15A—C16A | 1.1 (5) | C13B—C14B—C15B—C16B | −0.1 (5) |
N1A—C14A—C15A—C16A | −178.3 (3) | N1B—C14B—C15B—C16B | 179.5 (3) |
C12A—C11A—C16A—C15A | −2.1 (4) | C14B—C15B—C16B—C11B | −1.7 (5) |
C10A—C11A—C16A—C15A | 177.3 (3) | C12B—C11B—C16B—C15B | 2.7 (5) |
C14A—C15A—C16A—C11A | 0.6 (5) | C10B—C11B—C16B—C15B | −178.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6A—H6A···O2Bi | 0.94 | 2.56 | 3.144 (4) | 120 |
C6B—H6B···O2Aii | 0.94 | 2.57 | 3.409 (4) | 148 |
C7B—H7D···O3Biii | 0.97 | 2.48 | 3.361 (5) | 151 |
C16A—H16A···O1Biv | 0.94 | 2.57 | 3.401 (4) | 148 |
Symmetry codes: (i) x−1, −y, z−1/2; (ii) x+1, −y+1, z+1/2; (iii) x, y+1, z; (iv) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H13NO3 |
Mr | 267.27 |
Crystal system, space group | Monoclinic, Pc |
Temperature (K) | 203 |
a, b, c (Å) | 5.97300 (1), 15.0731 (5), 14.6768 (4) |
β (°) | 95.785 (2) |
V (Å3) | 1314.65 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.47 × 0.41 × 0.29 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini R |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.955, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 37695, 4496, 2661 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.756 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.162, 1.25 |
No. of reflections | 4496 |
No. of parameters | 363 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.23 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis PRO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C6A—H6A···O2Bi | 0.94 | 2.56 | 3.144 (4) | 120 |
C6B—H6B···O2Aii | 0.94 | 2.57 | 3.409 (4) | 148 |
C7B—H7D···O3Biii | 0.97 | 2.48 | 3.361 (5) | 151 |
C16A—H16A···O1Biv | 0.94 | 2.57 | 3.401 (4) | 148 |
Symmetry codes: (i) x−1, −y, z−1/2; (ii) x+1, −y+1, z+1/2; (iii) x, y+1, z; (iv) x+1, y, z. |
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Chalcone is an aromatic ketone that forms a central core for a variety of important biological compounds, which are known collectively as chalcones. Chalcones and the corresponding heterocyclic analogs are valuable intermediates in organic synthesis and show numerous biological effects. The non-linear optical (NLO) effects in organic molecules originates from a strong donor–acceptor intermolecular interaction, a delocalized π electron system and also the ability to crystallize in non-centro symmetric space groups. Chalcones are finding applications as organic non-linear optical materials due to their good SHG conversion efficiencies. Herein we report the synthesis and crystal structure of a new chalcone, the title compound.
The asymmetric unit of the title compound contains two independent molecules A and B both of which are shown in Fig. 1. The C9—C8—C1—C6 and C9—C10—C11—C12 torsion angles [(A) -0.8 (5), 6.4 (5)°; (B) 5.2 (4), -8.2 (5)°] indicate that the 4-methylphenyl and 4-nitrophenyl groups are slightly twisted with respect to the central O1/C8—C11 plane.
In the crystal structure, the independent molecues exist as a pseudo inversion-related pair with the centroids of the 4-methylphenyl and 4-nitrophenyl rings separated by a distance of 3.7550 (17) Å, indicating π-π stacking interaction. Crystal packing shows each of these independent molecules form sheets approximately parallel to the ab plane (Fig. 2). The sheets formed by these molecules are alternatively stacked along the c axis and are cross-linked by C—H···O intermolecular hydrogen-bonding interactions (Table 1).