Acta Cryst. (2008). E64, o1089 [ doi:10.1107/S1600536808013846 ]
In the title compound, C37H27Cl2NO2, the 3,4-dichlorophenyl ring makes a dihedral angle of 46.66 (6)° with the phenyl ring. The molecular structure is stabilized by weak intramolecular C-H
O interactions and the crystal structure is stabilized by weak intermolecular C-HO interactions. The C-C-C-C-C five-membered ring is planar, while the C-C-C-C-N five-membered ring adopts a half-chair conformation.
1.0 mol of (E) -2-benzylidene-4-(3,4-dichlorophenyl)-3,4-dihydronaphthale-1 (2H)-one (1.0 g), 1.0 mol of acenaphthaquinoline (0.65 g) and 1.0 mol of sarcosine was refluxed in 10 ml of methanol for about 5.0 hrs. The solvent was removedand the crude solid was recrystallized from ethanol.
H atoms were positioned geometrically and refined using riding model with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.98Å and Uiso(H) = 1.2Ueq(C) for CH, C—H = 0.97Å and Uiso(H) = 1.2Ueq(C) for CH2, C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for CH3.
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./bt2710fig1thm.gif)
| Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. |
![[Figure 2]](./bt2710fig2thm.gif)
| Fig. 2. The packing of (I), viewed down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted. |
| C37H27Cl2NO2 | F000 = 2448 |
| Mr = 588.50 | Dx = 1.332 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation λ = 0.71073 Å |
| a = 39.6142 (12) Å | θ = 2.0–25.5º |
| b = 8.3031 (2) Å | µ = 0.26 mm−1 |
| c = 18.1810 (5) Å | T = 293 (2) K |
| β = 101.135 (3)º | Block, pale yellow |
| V = 5867.5 (3) Å3 | 0.3 × 0.2 × 0.2 mm |
| Z = 8 |
| Bruker APEXII CCD diffractometer | 8160 independent reflections |
| Radiation source: fine-focus sealed tube | 5776 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.033 |
| T = 293(2) K | θmax = 29.6º |
| ω scans | θmin = 1.1º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −54→54 |
| Tmin = 0.976, Tmax = 0.979 | k = −11→11 |
| 67467 measured reflections | l = −25→25 |
| 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)] = 0.049 | H-atom parameters constrained |
| wR(F2) = 0.152 | w = 1/[σ2(Fo2) + (0.0658P)2 + 5.0424P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.06 | (Δ/σ)max < 0.001 |
| 8160 reflections | Δρmax = 0.47 e Å−3 |
| 380 parameters | Δρmin = −0.32 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C37H27Cl2NO2 | V = 5867.5 (3) Å3 |
| Mr = 588.50 | Z = 8 |
| Monoclinic, C2/c | Mo Kα |
| a = 39.6142 (12) Å | µ = 0.26 mm−1 |
| b = 8.3031 (2) Å | T = 293 (2) K |
| c = 18.1810 (5) Å | 0.3 × 0.2 × 0.2 mm |
| β = 101.135 (3)º |
| Bruker APEXII CCD diffractometer | 8160 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5776 reflections with I > 2σ(I) |
| Tmin = 0.976, Tmax = 0.979 | Rint = 0.033 |
| 67467 measured reflections |
| R[F2 > 2σ(F2)] = 0.049 | 380 parameters |
| wR(F2) = 0.152 | H-atom parameters constrained |
| S = 1.06 | Δρmax = 0.47 e Å−3 |
| 8160 reflections | Δρmin = −0.32 e Å−3 |
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 | ||
| Cl1 | −0.002080 (13) | 0.34019 (9) | 0.38789 (4) | 0.06938 (19) | |
| Cl2 | −0.014144 (16) | 0.71550 (10) | 0.36697 (4) | 0.0841 (2) | |
| O1 | −0.19815 (3) | 0.41995 (17) | 0.58966 (8) | 0.0475 (3) | |
| O2 | −0.12583 (4) | −0.06851 (17) | 0.48514 (7) | 0.0512 (3) | |
| C9 | −0.16950 (4) | 0.23492 (18) | 0.52002 (8) | 0.0299 (3) | |
| C10 | −0.17115 (4) | 0.36502 (19) | 0.57873 (9) | 0.0333 (3) | |
| C25 | −0.16332 (4) | 0.06301 (19) | 0.56048 (9) | 0.0333 (3) | |
| C17 | −0.20508 (4) | 0.2125 (2) | 0.46665 (9) | 0.0346 (3) | |
| H17 | −0.2226 | 0.2408 | 0.4959 | 0.042* | |
| C1 | −0.08342 (4) | 0.4158 (2) | 0.48236 (9) | 0.0357 (3) | |
| C7 | −0.10569 (4) | 0.3176 (2) | 0.52492 (9) | 0.0355 (3) | |
| H7 | −0.0949 | 0.2116 | 0.5348 | 0.043* | |
| N1 | −0.19450 (4) | −0.02695 (18) | 0.52975 (9) | 0.0425 (3) | |
| C6 | −0.08905 (5) | 0.5788 (2) | 0.47013 (11) | 0.0469 (4) | |
| H6 | −0.1074 | 0.6281 | 0.4862 | 0.056* | |
| C8 | −0.14162 (4) | 0.2907 (2) | 0.47710 (9) | 0.0336 (3) | |
| H8A | −0.1398 | 0.2109 | 0.4391 | 0.040* | |
| H8B | −0.1492 | 0.3905 | 0.4514 | 0.040* | |
| C18 | −0.21192 (4) | 0.3169 (2) | 0.39763 (9) | 0.0381 (4) | |
| C26 | −0.12974 (4) | −0.0201 (2) | 0.54571 (10) | 0.0383 (4) | |
| C2 | −0.05649 (4) | 0.3440 (2) | 0.45610 (9) | 0.0388 (4) | |
| H2 | −0.0526 | 0.2341 | 0.4630 | 0.047* | |
| C3 | −0.03528 (4) | 0.4344 (3) | 0.41954 (10) | 0.0434 (4) | |
| C11 | −0.13780 (4) | 0.4193 (2) | 0.62382 (9) | 0.0365 (3) | |
| C16 | −0.10692 (4) | 0.3935 (2) | 0.59997 (9) | 0.0385 (4) | |
| C35 | −0.15689 (5) | 0.0661 (2) | 0.64538 (9) | 0.0398 (4) | |
| C36 | −0.12327 (5) | 0.0156 (2) | 0.67380 (10) | 0.0442 (4) | |
| C24 | −0.20754 (5) | 0.0320 (2) | 0.45465 (11) | 0.0432 (4) | |
| H24A | −0.2311 | −0.0019 | 0.4366 | 0.052* | |
| H24B | −0.1934 | −0.0037 | 0.4198 | 0.052* | |
| C27 | −0.10569 (5) | −0.0354 (2) | 0.61808 (11) | 0.0454 (4) | |
| C4 | −0.04084 (5) | 0.5976 (3) | 0.40924 (11) | 0.0494 (5) | |
| C23 | −0.20506 (5) | 0.2687 (3) | 0.32921 (11) | 0.0517 (5) | |
| H23 | −0.1958 | 0.1672 | 0.3246 | 0.062* | |
| C5 | −0.06793 (5) | 0.6693 (3) | 0.43455 (12) | 0.0529 (5) | |
| H5 | −0.0719 | 0.7792 | 0.4275 | 0.063* | |
| C15 | −0.07627 (5) | 0.4379 (3) | 0.64733 (11) | 0.0572 (5) | |
| H15 | −0.0554 | 0.4209 | 0.6322 | 0.069* | |
| C19 | −0.22596 (5) | 0.4685 (3) | 0.40187 (13) | 0.0539 (5) | |
| H19 | −0.2313 | 0.5030 | 0.4469 | 0.065* | |
| C12 | −0.13751 (6) | 0.4898 (3) | 0.69397 (11) | 0.0521 (5) | |
| H12 | −0.1581 | 0.5081 | 0.7098 | 0.062* | |
| C31 | −0.10852 (7) | 0.0127 (3) | 0.75047 (12) | 0.0620 (6) | |
| C34 | −0.17765 (6) | 0.1082 (2) | 0.69419 (11) | 0.0532 (5) | |
| H34 | −0.2005 | 0.1372 | 0.6770 | 0.064* | |
| C22 | −0.21188 (6) | 0.3698 (3) | 0.26740 (12) | 0.0648 (6) | |
| H22 | −0.2073 | 0.3351 | 0.2217 | 0.078* | |
| C14 | −0.07653 (7) | 0.5065 (4) | 0.71610 (12) | 0.0726 (7) | |
| H14 | −0.0559 | 0.5357 | 0.7470 | 0.087* | |
| C37 | −0.19281 (6) | −0.2006 (2) | 0.53935 (14) | 0.0607 (6) | |
| H37A | −0.2155 | −0.2451 | 0.5263 | 0.091* | |
| H37B | −0.1832 | −0.2258 | 0.5907 | 0.091* | |
| H37C | −0.1786 | −0.2457 | 0.5074 | 0.091* | |
| C13 | −0.10704 (7) | 0.5319 (3) | 0.73924 (12) | 0.0696 (7) | |
| H13 | −0.1070 | 0.5779 | 0.7859 | 0.083* | |
| C28 | −0.07225 (6) | −0.0877 (3) | 0.63682 (15) | 0.0686 (6) | |
| H28 | −0.0603 | −0.1229 | 0.6006 | 0.082* | |
| C32 | −0.13034 (9) | 0.0616 (3) | 0.79920 (12) | 0.0757 (8) | |
| H32 | −0.1220 | 0.0632 | 0.8507 | 0.091* | |
| C21 | −0.22524 (6) | 0.5203 (4) | 0.27320 (15) | 0.0713 (7) | |
| H21 | −0.2296 | 0.5883 | 0.2318 | 0.086* | |
| C20 | −0.23216 (7) | 0.5694 (3) | 0.34039 (16) | 0.0728 (7) | |
| H20 | −0.2411 | 0.6717 | 0.3448 | 0.087* | |
| C33 | −0.16333 (8) | 0.1062 (3) | 0.77166 (13) | 0.0709 (7) | |
| H33 | −0.1771 | 0.1369 | 0.8053 | 0.085* | |
| C30 | −0.07403 (8) | −0.0392 (4) | 0.76769 (16) | 0.0849 (9) | |
| H30 | −0.0627 | −0.0418 | 0.8175 | 0.102* | |
| C29 | −0.05687 (8) | −0.0856 (4) | 0.71354 (19) | 0.0918 (10) | |
| H29 | −0.0340 | −0.1173 | 0.7276 | 0.110* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0432 (3) | 0.0965 (5) | 0.0761 (4) | 0.0129 (3) | 0.0307 (2) | −0.0009 (3) |
| Cl2 | 0.0595 (3) | 0.0979 (5) | 0.1025 (5) | −0.0085 (3) | 0.0344 (3) | 0.0410 (4) |
| O1 | 0.0376 (6) | 0.0514 (8) | 0.0557 (8) | 0.0082 (6) | 0.0145 (5) | −0.0118 (6) |
| O2 | 0.0620 (8) | 0.0522 (8) | 0.0423 (7) | 0.0176 (6) | 0.0172 (6) | −0.0053 (6) |
| C9 | 0.0268 (6) | 0.0317 (7) | 0.0319 (7) | 0.0013 (6) | 0.0077 (5) | −0.0011 (6) |
| C10 | 0.0334 (7) | 0.0320 (8) | 0.0362 (8) | 0.0021 (6) | 0.0108 (6) | −0.0002 (6) |
| C25 | 0.0366 (8) | 0.0317 (8) | 0.0331 (7) | 0.0021 (6) | 0.0102 (6) | −0.0006 (6) |
| C17 | 0.0280 (7) | 0.0380 (8) | 0.0377 (8) | −0.0003 (6) | 0.0058 (6) | −0.0020 (6) |
| C1 | 0.0268 (7) | 0.0431 (9) | 0.0378 (8) | 0.0014 (6) | 0.0071 (6) | 0.0029 (7) |
| C7 | 0.0273 (7) | 0.0400 (9) | 0.0399 (8) | 0.0017 (6) | 0.0082 (6) | 0.0047 (7) |
| N1 | 0.0428 (8) | 0.0347 (7) | 0.0488 (8) | −0.0066 (6) | 0.0065 (6) | 0.0001 (6) |
| C6 | 0.0383 (9) | 0.0485 (10) | 0.0573 (11) | 0.0094 (8) | 0.0178 (8) | 0.0096 (8) |
| C8 | 0.0276 (7) | 0.0396 (8) | 0.0344 (7) | 0.0010 (6) | 0.0083 (6) | 0.0016 (6) |
| C18 | 0.0279 (7) | 0.0455 (9) | 0.0389 (8) | −0.0036 (6) | 0.0013 (6) | 0.0006 (7) |
| C26 | 0.0429 (9) | 0.0324 (8) | 0.0406 (9) | 0.0075 (7) | 0.0103 (7) | 0.0020 (7) |
| C2 | 0.0313 (7) | 0.0447 (9) | 0.0410 (9) | 0.0037 (7) | 0.0082 (6) | 0.0004 (7) |
| C3 | 0.0280 (7) | 0.0638 (12) | 0.0392 (9) | 0.0030 (7) | 0.0089 (6) | 0.0001 (8) |
| C11 | 0.0386 (8) | 0.0358 (8) | 0.0352 (8) | −0.0032 (7) | 0.0080 (6) | −0.0018 (6) |
| C16 | 0.0336 (8) | 0.0457 (9) | 0.0356 (8) | −0.0050 (7) | 0.0055 (6) | 0.0045 (7) |
| C35 | 0.0531 (10) | 0.0342 (8) | 0.0339 (8) | −0.0060 (7) | 0.0132 (7) | 0.0014 (6) |
| C36 | 0.0578 (11) | 0.0364 (9) | 0.0358 (8) | −0.0069 (8) | 0.0029 (7) | 0.0044 (7) |
| C24 | 0.0397 (9) | 0.0416 (9) | 0.0458 (9) | −0.0068 (7) | 0.0020 (7) | −0.0038 (7) |
| C27 | 0.0452 (9) | 0.0426 (10) | 0.0452 (10) | 0.0057 (8) | 0.0012 (7) | 0.0057 (8) |
| C4 | 0.0348 (8) | 0.0651 (13) | 0.0491 (10) | −0.0040 (8) | 0.0103 (7) | 0.0153 (9) |
| C23 | 0.0545 (11) | 0.0560 (12) | 0.0442 (10) | −0.0072 (9) | 0.0084 (8) | −0.0038 (9) |
| C5 | 0.0462 (10) | 0.0489 (11) | 0.0652 (12) | 0.0041 (8) | 0.0146 (9) | 0.0148 (9) |
| C15 | 0.0393 (9) | 0.0862 (16) | 0.0440 (10) | −0.0144 (10) | 0.0026 (8) | 0.0033 (10) |
| C19 | 0.0498 (10) | 0.0540 (12) | 0.0578 (12) | 0.0095 (9) | 0.0098 (9) | 0.0082 (9) |
| C12 | 0.0575 (11) | 0.0569 (12) | 0.0439 (10) | −0.0085 (9) | 0.0152 (9) | −0.0114 (9) |
| C31 | 0.0863 (16) | 0.0539 (12) | 0.0392 (10) | −0.0176 (11) | −0.0046 (10) | 0.0067 (9) |
| C34 | 0.0725 (13) | 0.0464 (11) | 0.0488 (10) | −0.0088 (9) | 0.0317 (10) | 0.0003 (8) |
| C22 | 0.0663 (13) | 0.0867 (18) | 0.0395 (10) | −0.0265 (13) | 0.0055 (9) | 0.0027 (11) |
| C14 | 0.0606 (13) | 0.109 (2) | 0.0426 (11) | −0.0316 (14) | −0.0049 (10) | −0.0049 (12) |
| C37 | 0.0711 (14) | 0.0378 (10) | 0.0712 (14) | −0.0094 (9) | 0.0088 (11) | 0.0038 (10) |
| C13 | 0.0773 (16) | 0.0891 (18) | 0.0406 (11) | −0.0263 (14) | 0.0072 (10) | −0.0181 (11) |
| C28 | 0.0535 (12) | 0.0727 (16) | 0.0739 (15) | 0.0180 (11) | −0.0019 (11) | 0.0078 (12) |
| C32 | 0.126 (2) | 0.0698 (16) | 0.0302 (10) | −0.0331 (16) | 0.0127 (12) | 0.0023 (10) |
| C21 | 0.0602 (13) | 0.0862 (19) | 0.0617 (14) | −0.0127 (13) | −0.0026 (11) | 0.0319 (13) |
| C20 | 0.0660 (14) | 0.0633 (15) | 0.0866 (18) | 0.0147 (12) | 0.0085 (13) | 0.0278 (13) |
| C33 | 0.116 (2) | 0.0621 (14) | 0.0454 (11) | −0.0251 (14) | 0.0423 (14) | −0.0041 (10) |
| C30 | 0.093 (2) | 0.087 (2) | 0.0579 (15) | −0.0109 (16) | −0.0288 (15) | 0.0166 (14) |
| C29 | 0.0645 (16) | 0.103 (2) | 0.092 (2) | 0.0113 (16) | −0.0254 (15) | 0.0192 (18) |
| Cl1—C3 | 1.7219 (18) | C36—C27 | 1.401 (3) |
| Cl2—C4 | 1.7266 (19) | C36—C31 | 1.404 (3) |
| O1—C10 | 1.2141 (19) | C24—H24A | 0.9700 |
| O2—C26 | 1.210 (2) | C24—H24B | 0.9700 |
| C9—C10 | 1.529 (2) | C27—C28 | 1.373 (3) |
| C9—C8 | 1.541 (2) | C4—C5 | 1.382 (3) |
| C9—C17 | 1.560 (2) | C23—C22 | 1.387 (3) |
| C9—C25 | 1.603 (2) | C23—H23 | 0.9300 |
| C10—C11 | 1.484 (2) | C5—H5 | 0.9300 |
| C25—N1 | 1.459 (2) | C15—C14 | 1.376 (3) |
| C25—C35 | 1.515 (2) | C15—H15 | 0.9300 |
| C25—C26 | 1.567 (2) | C19—C20 | 1.380 (3) |
| C17—C18 | 1.506 (2) | C19—H19 | 0.9300 |
| C17—C24 | 1.516 (2) | C12—C13 | 1.368 (3) |
| C17—H17 | 0.9800 | C12—H12 | 0.9300 |
| C1—C6 | 1.383 (3) | C31—C30 | 1.409 (4) |
| C1—C2 | 1.385 (2) | C31—C32 | 1.412 (4) |
| C1—C7 | 1.518 (2) | C34—C33 | 1.413 (3) |
| C7—C16 | 1.512 (2) | C34—H34 | 0.9300 |
| C7—C8 | 1.534 (2) | C22—C21 | 1.369 (4) |
| C7—H7 | 0.9800 | C22—H22 | 0.9300 |
| N1—C24 | 1.448 (2) | C14—C13 | 1.371 (4) |
| N1—C37 | 1.452 (2) | C14—H14 | 0.9300 |
| C6—C5 | 1.375 (3) | C37—H37A | 0.9600 |
| C6—H6 | 0.9300 | C37—H37B | 0.9600 |
| C8—H8A | 0.9700 | C37—H37C | 0.9600 |
| C8—H8B | 0.9700 | C13—H13 | 0.9300 |
| C18—C23 | 1.383 (3) | C28—C29 | 1.410 (4) |
| C18—C19 | 1.385 (3) | C28—H28 | 0.9300 |
| C26—C27 | 1.473 (3) | C32—C33 | 1.358 (4) |
| C2—C3 | 1.388 (2) | C32—H32 | 0.9300 |
| C2—H2 | 0.9300 | C21—C20 | 1.365 (4) |
| C3—C4 | 1.380 (3) | C21—H21 | 0.9300 |
| C11—C16 | 1.391 (2) | C20—H20 | 0.9300 |
| C11—C12 | 1.401 (2) | C33—H33 | 0.9300 |
| C16—C15 | 1.396 (2) | C30—C29 | 1.356 (5) |
| C35—C34 | 1.367 (3) | C30—H30 | 0.9300 |
| C35—C36 | 1.397 (3) | C29—H29 | 0.9300 |
| C10—C9—C8 | 105.82 (12) | C17—C24—H24A | 111.5 |
| C10—C9—C17 | 111.28 (12) | N1—C24—H24B | 111.5 |
| C8—C9—C17 | 111.75 (12) | C17—C24—H24B | 111.5 |
| C10—C9—C25 | 109.40 (12) | H24A—C24—H24B | 109.3 |
| C8—C9—C25 | 116.04 (12) | C28—C27—C36 | 120.44 (19) |
| C17—C9—C25 | 102.65 (12) | C28—C27—C26 | 132.5 (2) |
| O1—C10—C11 | 120.92 (15) | C36—C27—C26 | 107.09 (16) |
| O1—C10—C9 | 122.52 (14) | C3—C4—C5 | 119.47 (17) |
| C11—C10—C9 | 116.55 (13) | C3—C4—Cl2 | 121.45 (15) |
| N1—C25—C35 | 111.22 (13) | C5—C4—Cl2 | 119.07 (17) |
| N1—C25—C26 | 113.12 (13) | C18—C23—C22 | 120.8 (2) |
| C35—C25—C26 | 101.58 (13) | C18—C23—H23 | 119.6 |
| N1—C25—C9 | 103.72 (12) | C22—C23—H23 | 119.6 |
| C35—C25—C9 | 115.68 (13) | C6—C5—C4 | 120.22 (19) |
| C26—C25—C9 | 111.90 (12) | C6—C5—H5 | 119.9 |
| C18—C17—C24 | 116.94 (14) | C4—C5—H5 | 119.9 |
| C18—C17—C9 | 116.44 (13) | C14—C15—C16 | 120.8 (2) |
| C24—C17—C9 | 103.44 (13) | C14—C15—H15 | 119.6 |
| C18—C17—H17 | 106.4 | C16—C15—H15 | 119.6 |
| C24—C17—H17 | 106.4 | C20—C19—C18 | 121.2 (2) |
| C9—C17—H17 | 106.4 | C20—C19—H19 | 119.4 |
| C6—C1—C2 | 118.46 (16) | C18—C19—H19 | 119.4 |
| C6—C1—C7 | 121.07 (14) | C13—C12—C11 | 120.4 (2) |
| C2—C1—C7 | 120.46 (16) | C13—C12—H12 | 119.8 |
| C16—C7—C1 | 111.05 (14) | C11—C12—H12 | 119.8 |
| C16—C7—C8 | 112.58 (13) | C36—C31—C30 | 115.2 (2) |
| C1—C7—C8 | 110.86 (13) | C36—C31—C32 | 115.5 (2) |
| C16—C7—H7 | 107.4 | C30—C31—C32 | 129.3 (2) |
| C1—C7—H7 | 107.4 | C35—C34—C33 | 117.9 (2) |
| C8—C7—H7 | 107.4 | C35—C34—H34 | 121.0 |
| C24—N1—C37 | 116.63 (16) | C33—C34—H34 | 121.0 |
| C24—N1—C25 | 108.04 (13) | C21—C22—C23 | 120.5 (2) |
| C37—N1—C25 | 116.51 (16) | C21—C22—H22 | 119.7 |
| C5—C6—C1 | 121.11 (17) | C23—C22—H22 | 119.7 |
| C5—C6—H6 | 119.4 | C13—C14—C15 | 120.3 (2) |
| C1—C6—H6 | 119.4 | C13—C14—H14 | 119.9 |
| C7—C8—C9 | 115.71 (13) | C15—C14—H14 | 119.9 |
| C7—C8—H8A | 108.4 | N1—C37—H37A | 109.5 |
| C9—C8—H8A | 108.4 | N1—C37—H37B | 109.5 |
| C7—C8—H8B | 108.4 | H37A—C37—H37B | 109.5 |
| C9—C8—H8B | 108.4 | N1—C37—H37C | 109.5 |
| H8A—C8—H8B | 107.4 | H37A—C37—H37C | 109.5 |
| C23—C18—C19 | 117.65 (18) | H37B—C37—H37C | 109.5 |
| C23—C18—C17 | 123.25 (17) | C12—C13—C14 | 120.2 (2) |
| C19—C18—C17 | 119.10 (16) | C12—C13—H13 | 119.9 |
| O2—C26—C27 | 127.58 (16) | C14—C13—H13 | 119.9 |
| O2—C26—C25 | 124.35 (16) | C27—C28—C29 | 117.0 (3) |
| C27—C26—C25 | 107.98 (14) | C27—C28—H28 | 121.5 |
| C1—C2—C3 | 120.70 (17) | C29—C28—H28 | 121.5 |
| C1—C2—H2 | 119.6 | C33—C32—C31 | 120.6 (2) |
| C3—C2—H2 | 119.6 | C33—C32—H32 | 119.7 |
| C4—C3—C2 | 120.02 (16) | C31—C32—H32 | 119.7 |
| C4—C3—Cl1 | 120.86 (14) | C20—C21—C22 | 119.3 (2) |
| C2—C3—Cl1 | 119.11 (15) | C20—C21—H21 | 120.4 |
| C16—C11—C12 | 119.67 (16) | C22—C21—H21 | 120.4 |
| C16—C11—C10 | 121.56 (15) | C21—C20—C19 | 120.5 (3) |
| C12—C11—C10 | 118.67 (16) | C21—C20—H20 | 119.7 |
| C11—C16—C15 | 118.65 (17) | C19—C20—H20 | 119.7 |
| C11—C16—C7 | 121.94 (14) | C32—C33—C34 | 122.9 (2) |
| C15—C16—C7 | 119.40 (16) | C32—C33—H33 | 118.5 |
| C34—C35—C36 | 119.14 (18) | C34—C33—H33 | 118.5 |
| C34—C35—C25 | 131.44 (18) | C29—C30—C31 | 121.7 (2) |
| C36—C35—C25 | 109.43 (15) | C29—C30—H30 | 119.1 |
| C35—C36—C27 | 113.24 (16) | C31—C30—H30 | 119.1 |
| C35—C36—C31 | 123.9 (2) | C30—C29—C28 | 122.7 (3) |
| C27—C36—C31 | 122.9 (2) | C30—C29—H29 | 118.6 |
| N1—C24—C17 | 101.37 (14) | C28—C29—H29 | 118.6 |
| N1—C24—H24A | 111.5 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C8—H8A···O2 | 0.97 | 2.49 | 3.045 (2) | 116 |
| C17—H17···O1 | 0.98 | 2.33 | 2.794 (2) | 108 |
| C32—H32···O2i | 0.93 | 2.48 | 3.351 (3) | 156 |
| Symmetry codes: (i) x, −y, z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C8—H8A···O2 | 0.97 | 2.49 | 3.045 (2) | 116 |
| C17—H17···O1 | 0.98 | 2.33 | 2.794 (2) | 108 |
| C32—H32···O2i | 0.93 | 2.48 | 3.351 (3) | 156 |
| Symmetry codes: (i) x, −y, z+1/2. |
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Ramesh, P., Murugavel, S., Pandi, A. S., Murugan, R. & Narayanan, S. S. (2007). Acta Cryst. E63, o4851–o4851.
Sarala, G., Kavitha, C. V., Mantelingu, K., Anandalwar, S. M., Shashidhara Prasad, J. & Rangappa, K. S. (2006). Anal. Sci. 22, x241–x242.
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
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The title compound acts in the central nervous system as a serotonine uptake inhibitor. Another similar compound sertraline hydrochloride is a very effective antidepressant. It selectively blocks serotonine re-uptake and is used for the treatment of depression, as well as dependency and other anxiety-related disorders (Welch et al., 1984).
The geometric parameters in the title compound agree with the reported values of a similar structure (Sarala et al., 2006; Ramesh et al., 2007). The 3,4-dichlorophenyl ring makes a dihedral angle of 46.66 (6) ° with the 4-phenyl ring. The 3,4-dihydro-1(2H)-naphthalenone ring adopts half-chair conformation [torsion angles: C(7)—C(16)—C(11)—C(10) -3.61 (3) °, and C(7)—C(8)—C(9)—C(10) -58.20 (17) °].
The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak intermolecular C—H···O interactions.