organic compounds
3-Methoxy-2-[5-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-3-yl]phenol
aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea, bDivision of Bioscience and Biotechnology, BMIC, Konkuk University, Seoul 143-701, Republic of Korea, and cDepartment of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada
*Correspondence e-mail: dskoh@dongduk.ac.kr
The 20H18N2O2, contains two independent molecules in which the dihedral angles between the naphthalene ring system [r.m.s. deviations = 0.012 (1) and 0.015 (1) Å] and the benzene ring are 71.65 (6) and 74.51 (6)°. In the crystal, pairs of N—H⋯O hydrogen bonds form two independent inversion dimers with graph-set notation R22(14). In addition, each molecule contains an intramolecular O—H⋯N hydrogen bond with an S(6) motif.
of the title compound, CCCDC reference: 992239
Related literature
For the synthesis and biological properties of pyrazoline derivatives, see: Hwang et al. (2013); Sharifzadeh et al. (2013); Congiu et al. (2010); Khode et al. (2009); Karthikeyan et al. (2007). For related structures, see: Fun et al. (2012); Jasinski et al. (2010). For hydrogen-bond graph-set notation, see: Bernstein et al. (1995).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2012); cell SAINT (Bruker, 2012); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
CCDC reference: 992239
10.1107/S1600536814005972/is5346sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814005972/is5346Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814005972/is5346Isup3.cml
To a solution of 6-methoxy-2-hydroxyacetophenone (10 mmol, 1.66 g) in 50 ml of ethanol was added 2-naphthaldehyde (10 mmol, 1.56 g) and the temperature was adjusted to around 276–277 K in an ice-bath. To the reaction mixture was added 10 ml of 50% (w/v) aqueous KOH solution and reaction mixture was stirred at room temperature for 60 h. At the end of the reaction, ice water was added to the mixture and acidified with 6 N HCl (pH = 3–4). The resulting precipitate was filtered and washed with water and ethanol. The crude solid was purified by recrystallization from ethanol to give pure chalcone (m.p.; 403–403 K, yield; 63%). Excess hydrazine monohydrate (1 ml of 64–65% solution, 13 mmol) was added to chalcone compound (5 mmol, 1.52 g) in 30 ml anhydrous ethanol, and the solution was refluxed at 363 K for 3 h. The reaction mixture was cooled to room temperature to yield a solid that was then filtered. The crude solids were purified by recrystallization from ethanol to afford pure pyrazolines (m.p.; 403–403 K, yield; 93%). How were the X-ray quality crystals grown. Repeated recrystallization in ethanol gave colourless needle shape crystals suitable for X-ray diffraction.
Hydrogen atoms bonded to C atoms were placed in calculated positions with C—H distances ranging from 0.95–1.00 Å and included in the
in a riding-model approximation with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl). H atoms bonded to N and O atoms were refined independently with isotropic displacement parameters.Data collection: APEX2 (Bruker, 2012); cell
SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The asymmetric unit of title compound showing 30% probability ellipsoids. | |
Fig. 2. Part of the crystal structure showing hydrogen bonds as dashed lines. |
C20H18N2O2 | F(000) = 1344 |
Mr = 318.36 | Dx = 1.320 Mg m−3 |
Monoclinic, P2/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2yc | Cell parameters from 857 reflections |
a = 21.0215 (15) Å | θ = 3.3–56.5° |
b = 5.6564 (5) Å | µ = 0.69 mm−1 |
c = 28.785 (2) Å | T = 147 K |
β = 110.543 (3)° | Needle, colourless |
V = 3205.1 (4) Å3 | 0.17 × 0.10 × 0.07 mm |
Z = 8 |
Bruker Kappa APEX DUO CCD diffractometer | 5506 independent reflections |
Radiation source: Bruker ImuS | 4776 reflections with I > 2σ(I) |
Multi-layer optics monochromator | Rint = 0.045 |
ϕ and ω scans | θmax = 66.8°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −24→23 |
Tmin = 0.695, Tmax = 0.753 | k = −6→6 |
43387 measured reflections | l = −33→33 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0508P)2 + 0.6182P] where P = (Fo2 + 2Fc2)/3 |
5506 reflections | (Δ/σ)max = 0.001 |
451 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C20H18N2O2 | V = 3205.1 (4) Å3 |
Mr = 318.36 | Z = 8 |
Monoclinic, P2/c | Cu Kα radiation |
a = 21.0215 (15) Å | µ = 0.69 mm−1 |
b = 5.6564 (5) Å | T = 147 K |
c = 28.785 (2) Å | 0.17 × 0.10 × 0.07 mm |
β = 110.543 (3)° |
Bruker Kappa APEX DUO CCD diffractometer | 5506 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | 4776 reflections with I > 2σ(I) |
Tmin = 0.695, Tmax = 0.753 | Rint = 0.045 |
43387 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.17 e Å−3 |
5506 reflections | Δρmin = −0.20 e Å−3 |
451 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 | 0.49628 (5) | 0.5886 (2) | 0.56791 (4) | 0.0409 (3) | |
O2A | 0.34244 (6) | 1.2274 (2) | 0.54722 (4) | 0.0440 (3) | |
N1A | 0.41312 (6) | 0.7105 (2) | 0.48182 (4) | 0.0315 (3) | |
N2A | 0.38431 (6) | 0.7224 (2) | 0.42980 (4) | 0.0326 (3) | |
C1A | 0.39789 (6) | 0.8982 (2) | 0.50121 (5) | 0.0246 (3) | |
C2A | 0.35765 (6) | 1.0709 (2) | 0.46192 (5) | 0.0254 (3) | |
H2AA | 0.3748 | 1.2344 | 0.4698 | 0.030* | |
H2AB | 0.3087 | 1.0666 | 0.4572 | 0.030* | |
C3A | 0.37111 (6) | 0.9740 (2) | 0.41647 (5) | 0.0277 (3) | |
H3AA | 0.4136 | 1.0476 | 0.4149 | 0.033* | |
C4A | 0.31402 (6) | 1.0150 (2) | 0.36773 (5) | 0.0252 (3) | |
C5A | 0.31489 (7) | 1.2249 (2) | 0.34150 (5) | 0.0297 (3) | |
H5AA | 0.3516 | 1.3323 | 0.3544 | 0.036* | |
C6A | 0.26385 (7) | 1.2767 (2) | 0.29782 (5) | 0.0304 (3) | |
H6AA | 0.2657 | 1.4192 | 0.2809 | 0.036* | |
C7A | 0.20822 (7) | 1.1210 (2) | 0.27751 (5) | 0.0267 (3) | |
C8A | 0.15504 (7) | 1.1653 (3) | 0.23166 (5) | 0.0335 (3) | |
H8AA | 0.1560 | 1.3055 | 0.2137 | 0.040* | |
C9A | 0.10281 (7) | 1.0100 (3) | 0.21309 (5) | 0.0379 (4) | |
H9AA | 0.0679 | 1.0421 | 0.1823 | 0.045* | |
C10A | 0.10019 (7) | 0.8025 (3) | 0.23919 (5) | 0.0361 (3) | |
H10A | 0.0632 | 0.6961 | 0.2261 | 0.043* | |
C11A | 0.15082 (7) | 0.7530 (3) | 0.28344 (5) | 0.0305 (3) | |
H11A | 0.1485 | 0.6122 | 0.3008 | 0.037* | |
C12A | 0.20652 (6) | 0.9091 (2) | 0.30362 (5) | 0.0250 (3) | |
C13A | 0.26073 (6) | 0.8605 (2) | 0.34863 (5) | 0.0249 (3) | |
H13A | 0.2602 | 0.7180 | 0.3659 | 0.030* | |
C14A | 0.42050 (6) | 0.9222 (2) | 0.55531 (5) | 0.0267 (3) | |
C15A | 0.39484 (7) | 1.0994 (3) | 0.57825 (5) | 0.0312 (3) | |
C16A | 0.42105 (7) | 1.1334 (3) | 0.62929 (5) | 0.0381 (4) | |
H16A | 0.4040 | 1.2561 | 0.6442 | 0.046* | |
C17A | 0.47218 (7) | 0.9862 (3) | 0.65800 (5) | 0.0440 (4) | |
H17A | 0.4907 | 1.0107 | 0.6928 | 0.053* | |
C18A | 0.49680 (7) | 0.8056 (3) | 0.63740 (6) | 0.0437 (4) | |
H18A | 0.5315 | 0.7049 | 0.6579 | 0.052* | |
C19A | 0.47060 (6) | 0.7707 (3) | 0.58629 (5) | 0.0320 (3) | |
C20A | 0.31232 (10) | 1.4005 (3) | 0.56934 (6) | 0.0507 (5) | |
H20A | 0.2743 | 1.4766 | 0.5435 | 0.076* | |
H20B | 0.3463 | 1.5199 | 0.5863 | 0.076* | |
H20C | 0.2957 | 1.3235 | 0.5934 | 0.076* | |
O1B | −0.09997 (5) | −0.95204 (18) | 0.51393 (4) | 0.0354 (2) | |
O2B | −0.06378 (5) | −0.28470 (19) | 0.62119 (4) | 0.0374 (3) | |
N1B | 0.01760 (6) | −0.7754 (2) | 0.55421 (5) | 0.0369 (3) | |
N2B | 0.08805 (6) | −0.7481 (2) | 0.56768 (5) | 0.0386 (3) | |
C1B | −0.00720 (6) | −0.6051 (2) | 0.57246 (5) | 0.0272 (3) | |
C2B | 0.04742 (6) | −0.4300 (2) | 0.59985 (5) | 0.0273 (3) | |
H2BA | 0.0617 | −0.4504 | 0.6362 | 0.033* | |
H2BB | 0.0323 | −0.2649 | 0.5911 | 0.033* | |
C3B | 0.10441 (6) | −0.4987 (3) | 0.58063 (5) | 0.0302 (3) | |
H3BA | 0.0992 | −0.4067 | 0.5498 | 0.036* | |
C4B | 0.17604 (6) | −0.4685 (2) | 0.61734 (5) | 0.0254 (3) | |
C5B | 0.21368 (7) | −0.2659 (2) | 0.61442 (5) | 0.0299 (3) | |
H5BA | 0.1936 | −0.1499 | 0.5897 | 0.036* | |
C6B | 0.27874 (7) | −0.2345 (2) | 0.64672 (5) | 0.0305 (3) | |
H6BA | 0.3032 | −0.0968 | 0.6441 | 0.037* | |
C7B | 0.31015 (6) | −0.4033 (2) | 0.68385 (5) | 0.0257 (3) | |
C8B | 0.37838 (7) | −0.3815 (3) | 0.71720 (5) | 0.0336 (3) | |
H8BA | 0.4044 | −0.2473 | 0.7151 | 0.040* | |
C9B | 0.40695 (7) | −0.5509 (3) | 0.75216 (5) | 0.0365 (4) | |
H9BA | 0.4528 | −0.5350 | 0.7737 | 0.044* | |
C10B | 0.36893 (7) | −0.7484 (3) | 0.75651 (5) | 0.0349 (3) | |
H10B | 0.3887 | −0.8631 | 0.7815 | 0.042* | |
C11B | 0.30344 (7) | −0.7755 (3) | 0.72472 (5) | 0.0294 (3) | |
H11B | 0.2783 | −0.9107 | 0.7277 | 0.035* | |
C12B | 0.27239 (6) | −0.6065 (2) | 0.68752 (5) | 0.0234 (3) | |
C13B | 0.20506 (6) | −0.6342 (2) | 0.65330 (5) | 0.0249 (3) | |
H13B | 0.1797 | −0.7702 | 0.6554 | 0.030* | |
C14B | −0.07952 (6) | −0.6070 (2) | 0.56665 (5) | 0.0260 (3) | |
C15B | −0.10804 (6) | −0.4417 (3) | 0.59036 (5) | 0.0289 (3) | |
C16B | −0.17715 (7) | −0.4442 (3) | 0.58272 (5) | 0.0328 (3) | |
H16B | −0.1959 | −0.3304 | 0.5985 | 0.039* | |
C17B | −0.21851 (7) | −0.6140 (3) | 0.55187 (5) | 0.0362 (3) | |
H17B | −0.2658 | −0.6137 | 0.5464 | 0.043* | |
C18B | −0.19260 (7) | −0.7822 (3) | 0.52909 (5) | 0.0344 (3) | |
H18B | −0.2215 | −0.8983 | 0.5084 | 0.041* | |
C19B | −0.12339 (7) | −0.7809 (3) | 0.53664 (5) | 0.0293 (3) | |
C20B | −0.09006 (7) | −0.1221 (3) | 0.64781 (6) | 0.0381 (4) | |
H20D | −0.0534 | −0.0195 | 0.6683 | 0.057* | |
H20E | −0.1093 | −0.2096 | 0.6691 | 0.057* | |
H20F | −0.1256 | −0.0254 | 0.6243 | 0.057* | |
H1OA | 0.4697 (11) | 0.574 (4) | 0.5327 (9) | 0.078 (7)* | |
H1OB | −0.0542 (11) | −0.935 (4) | 0.5237 (8) | 0.069 (6)* | |
H2NA | 0.4147 (8) | 0.653 (3) | 0.4179 (6) | 0.043 (5)* | |
H2NB | 0.1010 (8) | −0.803 (3) | 0.5426 (7) | 0.049 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0324 (5) | 0.0480 (7) | 0.0397 (6) | 0.0140 (5) | 0.0092 (5) | 0.0120 (5) |
O2A | 0.0597 (7) | 0.0477 (7) | 0.0276 (5) | 0.0247 (6) | 0.0192 (5) | 0.0042 (5) |
N1A | 0.0282 (6) | 0.0323 (7) | 0.0286 (6) | 0.0055 (5) | 0.0032 (5) | −0.0009 (5) |
N2A | 0.0313 (6) | 0.0335 (7) | 0.0279 (6) | 0.0108 (5) | 0.0041 (5) | −0.0042 (5) |
C1A | 0.0209 (6) | 0.0250 (7) | 0.0276 (7) | −0.0002 (5) | 0.0083 (5) | 0.0007 (6) |
C2A | 0.0281 (6) | 0.0246 (7) | 0.0240 (7) | 0.0012 (5) | 0.0097 (5) | 0.0007 (5) |
C3A | 0.0254 (6) | 0.0298 (7) | 0.0288 (7) | −0.0006 (6) | 0.0106 (5) | −0.0019 (6) |
C4A | 0.0269 (6) | 0.0286 (7) | 0.0240 (6) | 0.0037 (6) | 0.0137 (5) | −0.0019 (5) |
C5A | 0.0317 (7) | 0.0281 (7) | 0.0327 (7) | −0.0012 (6) | 0.0157 (6) | −0.0026 (6) |
C6A | 0.0374 (7) | 0.0254 (7) | 0.0325 (7) | 0.0032 (6) | 0.0176 (6) | 0.0051 (6) |
C7A | 0.0314 (7) | 0.0277 (7) | 0.0245 (7) | 0.0086 (6) | 0.0142 (6) | 0.0024 (5) |
C8A | 0.0377 (8) | 0.0341 (8) | 0.0301 (7) | 0.0111 (7) | 0.0137 (6) | 0.0091 (6) |
C9A | 0.0339 (7) | 0.0470 (9) | 0.0279 (7) | 0.0123 (7) | 0.0047 (6) | 0.0058 (7) |
C10A | 0.0296 (7) | 0.0398 (9) | 0.0354 (8) | 0.0012 (6) | 0.0067 (6) | −0.0025 (7) |
C11A | 0.0319 (7) | 0.0287 (7) | 0.0308 (7) | 0.0038 (6) | 0.0109 (6) | 0.0022 (6) |
C12A | 0.0284 (6) | 0.0259 (7) | 0.0236 (6) | 0.0061 (5) | 0.0129 (5) | 0.0002 (5) |
C13A | 0.0288 (7) | 0.0256 (7) | 0.0226 (6) | 0.0051 (6) | 0.0121 (5) | 0.0039 (5) |
C14A | 0.0227 (6) | 0.0321 (7) | 0.0255 (7) | −0.0040 (6) | 0.0085 (5) | 0.0037 (6) |
C15A | 0.0335 (7) | 0.0348 (8) | 0.0273 (7) | −0.0019 (6) | 0.0134 (6) | 0.0036 (6) |
C16A | 0.0374 (8) | 0.0508 (10) | 0.0294 (8) | −0.0096 (7) | 0.0159 (6) | −0.0042 (7) |
C17A | 0.0285 (7) | 0.0790 (13) | 0.0237 (7) | −0.0118 (8) | 0.0083 (6) | 0.0015 (8) |
C18A | 0.0243 (7) | 0.0737 (12) | 0.0314 (8) | 0.0018 (7) | 0.0076 (6) | 0.0163 (8) |
C19A | 0.0205 (6) | 0.0432 (9) | 0.0327 (7) | −0.0008 (6) | 0.0097 (6) | 0.0087 (6) |
C20A | 0.0778 (12) | 0.0473 (10) | 0.0380 (9) | 0.0246 (9) | 0.0341 (9) | 0.0059 (8) |
O1B | 0.0328 (5) | 0.0364 (6) | 0.0346 (6) | −0.0051 (5) | 0.0088 (4) | −0.0119 (5) |
O2B | 0.0270 (5) | 0.0447 (6) | 0.0431 (6) | −0.0023 (4) | 0.0156 (4) | −0.0194 (5) |
N1B | 0.0234 (6) | 0.0434 (8) | 0.0384 (7) | 0.0017 (5) | 0.0038 (5) | −0.0168 (6) |
N2B | 0.0217 (6) | 0.0481 (8) | 0.0415 (7) | 0.0025 (5) | 0.0054 (5) | −0.0238 (6) |
C1B | 0.0258 (6) | 0.0315 (8) | 0.0229 (7) | 0.0026 (6) | 0.0067 (5) | −0.0045 (6) |
C2B | 0.0232 (6) | 0.0295 (7) | 0.0289 (7) | 0.0012 (5) | 0.0085 (5) | −0.0054 (6) |
C3B | 0.0254 (7) | 0.0395 (8) | 0.0250 (7) | 0.0027 (6) | 0.0079 (6) | −0.0047 (6) |
C4B | 0.0235 (6) | 0.0317 (7) | 0.0228 (6) | 0.0033 (6) | 0.0105 (5) | −0.0058 (6) |
C5B | 0.0353 (7) | 0.0260 (7) | 0.0293 (7) | 0.0046 (6) | 0.0123 (6) | −0.0001 (6) |
C6B | 0.0355 (7) | 0.0238 (7) | 0.0350 (8) | −0.0037 (6) | 0.0160 (6) | −0.0033 (6) |
C7B | 0.0268 (6) | 0.0262 (7) | 0.0272 (7) | −0.0020 (5) | 0.0135 (5) | −0.0076 (5) |
C8B | 0.0286 (7) | 0.0359 (8) | 0.0365 (8) | −0.0088 (6) | 0.0116 (6) | −0.0122 (7) |
C9B | 0.0257 (7) | 0.0480 (9) | 0.0314 (8) | 0.0018 (7) | 0.0044 (6) | −0.0130 (7) |
C10B | 0.0352 (7) | 0.0426 (9) | 0.0252 (7) | 0.0086 (7) | 0.0087 (6) | −0.0014 (6) |
C11B | 0.0324 (7) | 0.0308 (8) | 0.0277 (7) | 0.0012 (6) | 0.0140 (6) | −0.0006 (6) |
C12B | 0.0244 (6) | 0.0264 (7) | 0.0225 (6) | −0.0006 (5) | 0.0121 (5) | −0.0056 (5) |
C13B | 0.0241 (6) | 0.0278 (7) | 0.0264 (7) | −0.0042 (5) | 0.0132 (5) | −0.0055 (6) |
C14B | 0.0242 (6) | 0.0311 (7) | 0.0221 (6) | −0.0002 (6) | 0.0073 (5) | 0.0003 (5) |
C15B | 0.0266 (7) | 0.0350 (8) | 0.0248 (7) | −0.0008 (6) | 0.0088 (5) | −0.0012 (6) |
C16B | 0.0267 (7) | 0.0436 (9) | 0.0306 (7) | 0.0030 (6) | 0.0133 (6) | 0.0022 (6) |
C17B | 0.0251 (7) | 0.0525 (10) | 0.0311 (7) | −0.0027 (7) | 0.0101 (6) | 0.0048 (7) |
C18B | 0.0294 (7) | 0.0445 (9) | 0.0270 (7) | −0.0084 (6) | 0.0069 (6) | −0.0001 (6) |
C19B | 0.0317 (7) | 0.0327 (8) | 0.0233 (7) | −0.0017 (6) | 0.0093 (6) | 0.0013 (6) |
C20B | 0.0360 (8) | 0.0412 (9) | 0.0420 (9) | 0.0031 (7) | 0.0198 (7) | −0.0120 (7) |
O1A—C19A | 1.3539 (19) | O1B—C19B | 1.3536 (17) |
O1A—H1OA | 0.97 (2) | O1B—H1OB | 0.91 (2) |
O2A—C15A | 1.3582 (17) | O2B—C15B | 1.3648 (17) |
O2A—C20A | 1.4313 (18) | O2B—C20B | 1.4269 (17) |
N1A—C1A | 1.2910 (18) | N1B—C1B | 1.2915 (18) |
N1A—N2A | 1.4059 (16) | N1B—N2B | 1.4016 (16) |
N2A—C3A | 1.4745 (18) | N2B—C3B | 1.469 (2) |
N2A—H2NA | 0.914 (18) | N2B—H2NB | 0.911 (19) |
C1A—C14A | 1.4664 (18) | C1B—C14B | 1.4699 (18) |
C1A—C2A | 1.5091 (18) | C1B—C2B | 1.5121 (18) |
C2A—C3A | 1.5338 (18) | C2B—C3B | 1.5354 (18) |
C2A—H2AA | 0.9900 | C2B—H2BA | 0.9900 |
C2A—H2AB | 0.9900 | C2B—H2BB | 0.9900 |
C3A—C4A | 1.5104 (18) | C3B—C4B | 1.5155 (18) |
C3A—H3AA | 1.0000 | C3B—H3BA | 1.0000 |
C4A—C13A | 1.3742 (19) | C4B—C13B | 1.3706 (19) |
C4A—C5A | 1.4104 (19) | C4B—C5B | 1.412 (2) |
C5A—C6A | 1.368 (2) | C5B—C6B | 1.369 (2) |
C5A—H5AA | 0.9500 | C5B—H5BA | 0.9500 |
C6A—C7A | 1.416 (2) | C6B—C7B | 1.413 (2) |
C6A—H6AA | 0.9500 | C6B—H6BA | 0.9500 |
C7A—C8A | 1.4210 (19) | C7B—C12B | 1.4216 (19) |
C7A—C12A | 1.4218 (19) | C7B—C8B | 1.4239 (19) |
C8A—C9A | 1.361 (2) | C8B—C9B | 1.366 (2) |
C8A—H8AA | 0.9500 | C8B—H8BA | 0.9500 |
C9A—C10A | 1.405 (2) | C9B—C10B | 1.404 (2) |
C9A—H9AA | 0.9500 | C9B—H9BA | 0.9500 |
C10A—C11A | 1.372 (2) | C10B—C11B | 1.368 (2) |
C10A—H10A | 0.9500 | C10B—H10B | 0.9500 |
C11A—C12A | 1.4181 (19) | C11B—C12B | 1.4128 (19) |
C11A—H11A | 0.9500 | C11B—H11B | 0.9500 |
C12A—C13A | 1.4200 (18) | C12B—C13B | 1.4211 (18) |
C13A—H13A | 0.9500 | C13B—H13B | 0.9500 |
C14A—C19A | 1.4070 (19) | C14B—C15B | 1.4096 (19) |
C14A—C15A | 1.408 (2) | C14B—C19B | 1.4159 (19) |
C15A—C16A | 1.390 (2) | C15B—C16B | 1.3909 (18) |
C16A—C17A | 1.381 (2) | C16B—C17B | 1.387 (2) |
C16A—H16A | 0.9500 | C16B—H16B | 0.9500 |
C17A—C18A | 1.371 (3) | C17B—C18B | 1.372 (2) |
C17A—H17A | 0.9500 | C17B—H17B | 0.9500 |
C18A—C19A | 1.392 (2) | C18B—C19B | 1.3936 (19) |
C18A—H18A | 0.9500 | C18B—H18B | 0.9500 |
C20A—H20A | 0.9800 | C20B—H20D | 0.9800 |
C20A—H20B | 0.9800 | C20B—H20E | 0.9800 |
C20A—H20C | 0.9800 | C20B—H20F | 0.9800 |
C19A—O1A—H1OA | 108.1 (13) | C19B—O1B—H1OB | 107.5 (14) |
C15A—O2A—C20A | 117.08 (12) | C15B—O2B—C20B | 117.68 (10) |
C1A—N1A—N2A | 109.97 (11) | C1B—N1B—N2B | 110.08 (11) |
N1A—N2A—C3A | 107.15 (11) | N1B—N2B—C3B | 107.86 (11) |
N1A—N2A—H2NA | 106.4 (11) | N1B—N2B—H2NB | 108.9 (11) |
C3A—N2A—H2NA | 114.3 (11) | C3B—N2B—H2NB | 114.9 (12) |
N1A—C1A—C14A | 119.87 (12) | N1B—C1B—C14B | 119.81 (12) |
N1A—C1A—C2A | 111.55 (11) | N1B—C1B—C2B | 111.08 (11) |
C14A—C1A—C2A | 128.58 (12) | C14B—C1B—C2B | 129.05 (11) |
C1A—C2A—C3A | 100.66 (10) | C1B—C2B—C3B | 101.06 (10) |
C1A—C2A—H2AA | 111.6 | C1B—C2B—H2BA | 111.6 |
C3A—C2A—H2AA | 111.6 | C3B—C2B—H2BA | 111.6 |
C1A—C2A—H2AB | 111.6 | C1B—C2B—H2BB | 111.6 |
C3A—C2A—H2AB | 111.6 | C3B—C2B—H2BB | 111.6 |
H2AA—C2A—H2AB | 109.4 | H2BA—C2B—H2BB | 109.4 |
N2A—C3A—C4A | 113.94 (11) | N2B—C3B—C4B | 111.84 (11) |
N2A—C3A—C2A | 101.37 (11) | N2B—C3B—C2B | 101.06 (11) |
C4A—C3A—C2A | 114.39 (11) | C4B—C3B—C2B | 115.47 (11) |
N2A—C3A—H3AA | 108.9 | N2B—C3B—H3BA | 109.4 |
C4A—C3A—H3AA | 108.9 | C4B—C3B—H3BA | 109.4 |
C2A—C3A—H3AA | 108.9 | C2B—C3B—H3BA | 109.4 |
C13A—C4A—C5A | 118.88 (12) | C13B—C4B—C5B | 119.33 (12) |
C13A—C4A—C3A | 122.98 (12) | C13B—C4B—C3B | 121.31 (12) |
C5A—C4A—C3A | 118.12 (12) | C5B—C4B—C3B | 119.36 (12) |
C6A—C5A—C4A | 121.26 (13) | C6B—C5B—C4B | 120.80 (13) |
C6A—C5A—H5AA | 119.4 | C6B—C5B—H5BA | 119.6 |
C4A—C5A—H5AA | 119.4 | C4B—C5B—H5BA | 119.6 |
C5A—C6A—C7A | 120.92 (13) | C5B—C6B—C7B | 121.10 (13) |
C5A—C6A—H6AA | 119.5 | C5B—C6B—H6BA | 119.5 |
C7A—C6A—H6AA | 119.5 | C7B—C6B—H6BA | 119.5 |
C6A—C7A—C8A | 122.70 (13) | C6B—C7B—C12B | 118.54 (12) |
C6A—C7A—C12A | 118.45 (12) | C6B—C7B—C8B | 122.99 (13) |
C8A—C7A—C12A | 118.83 (13) | C12B—C7B—C8B | 118.46 (13) |
C9A—C8A—C7A | 120.96 (13) | C9B—C8B—C7B | 120.95 (14) |
C9A—C8A—H8AA | 119.5 | C9B—C8B—H8BA | 119.5 |
C7A—C8A—H8AA | 119.5 | C7B—C8B—H8BA | 119.5 |
C8A—C9A—C10A | 120.46 (13) | C8B—C9B—C10B | 120.43 (13) |
C8A—C9A—H9AA | 119.8 | C8B—C9B—H9BA | 119.8 |
C10A—C9A—H9AA | 119.8 | C10B—C9B—H9BA | 119.8 |
C11A—C10A—C9A | 120.27 (14) | C11B—C10B—C9B | 120.01 (14) |
C11A—C10A—H10A | 119.9 | C11B—C10B—H10B | 120.0 |
C9A—C10A—H10A | 119.9 | C9B—C10B—H10B | 120.0 |
C10A—C11A—C12A | 120.87 (13) | C10B—C11B—C12B | 121.32 (13) |
C10A—C11A—H11A | 119.6 | C10B—C11B—H11B | 119.3 |
C12A—C11A—H11A | 119.6 | C12B—C11B—H11B | 119.3 |
C11A—C12A—C13A | 122.43 (12) | C11B—C12B—C13B | 122.25 (12) |
C11A—C12A—C7A | 118.60 (12) | C11B—C12B—C7B | 118.81 (12) |
C13A—C12A—C7A | 118.97 (12) | C13B—C12B—C7B | 118.94 (12) |
C4A—C13A—C12A | 121.50 (12) | C4B—C13B—C12B | 121.28 (12) |
C4A—C13A—H13A | 119.2 | C4B—C13B—H13B | 119.4 |
C12A—C13A—H13A | 119.2 | C12B—C13B—H13B | 119.4 |
C19A—C14A—C15A | 117.46 (13) | C15B—C14B—C19B | 117.35 (12) |
C19A—C14A—C1A | 120.57 (12) | C15B—C14B—C1B | 122.59 (12) |
C15A—C14A—C1A | 121.95 (12) | C19B—C14B—C1B | 120.05 (12) |
O2A—C15A—C16A | 123.43 (13) | O2B—C15B—C16B | 123.04 (12) |
O2A—C15A—C14A | 115.27 (12) | O2B—C15B—C14B | 115.96 (11) |
C16A—C15A—C14A | 121.28 (14) | C16B—C15B—C14B | 120.99 (13) |
C17A—C16A—C15A | 119.08 (15) | C17B—C16B—C15B | 119.57 (13) |
C17A—C16A—H16A | 120.5 | C17B—C16B—H16B | 120.2 |
C15A—C16A—H16A | 120.5 | C15B—C16B—H16B | 120.2 |
C18A—C17A—C16A | 121.53 (14) | C18B—C17B—C16B | 121.40 (13) |
C18A—C17A—H17A | 119.2 | C18B—C17B—H17B | 119.3 |
C16A—C17A—H17A | 119.2 | C16B—C17B—H17B | 119.3 |
C17A—C18A—C19A | 119.57 (14) | C17B—C18B—C19B | 119.32 (14) |
C17A—C18A—H18A | 120.2 | C17B—C18B—H18B | 120.3 |
C19A—C18A—H18A | 120.2 | C19B—C18B—H18B | 120.3 |
O1A—C19A—C18A | 117.18 (13) | O1B—C19B—C18B | 117.24 (12) |
O1A—C19A—C14A | 121.87 (13) | O1B—C19B—C14B | 121.46 (12) |
C18A—C19A—C14A | 120.94 (14) | C18B—C19B—C14B | 121.30 (13) |
O2A—C20A—H20A | 109.5 | O2B—C20B—H20D | 109.5 |
O2A—C20A—H20B | 109.5 | O2B—C20B—H20E | 109.5 |
H20A—C20A—H20B | 109.5 | H20D—C20B—H20E | 109.5 |
O2A—C20A—H20C | 109.5 | O2B—C20B—H20F | 109.5 |
H20A—C20A—H20C | 109.5 | H20D—C20B—H20F | 109.5 |
H20B—C20A—H20C | 109.5 | H20E—C20B—H20F | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···N1A | 0.97 (2) | 1.71 (2) | 2.5754 (15) | 145 (2) |
O1B—H1OB···N1B | 0.91 (2) | 1.71 (2) | 2.5377 (15) | 149 (2) |
N2A—H2NA···O1Ai | 0.914 (18) | 2.234 (18) | 3.0470 (16) | 147.7 (15) |
N2B—H2NB···O1Bii | 0.911 (19) | 2.131 (19) | 2.9787 (16) | 154.4 (15) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y−2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···N1A | 0.97 (2) | 1.71 (2) | 2.5754 (15) | 145 (2) |
O1B—H1OB···N1B | 0.91 (2) | 1.71 (2) | 2.5377 (15) | 149 (2) |
N2A—H2NA···O1Ai | 0.914 (18) | 2.234 (18) | 3.0470 (16) | 147.7 (15) |
N2B—H2NB···O1Bii | 0.911 (19) | 2.131 (19) | 2.9787 (16) | 154.4 (15) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y−2, −z+1. |
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Pyrazolines have been reported to show a broad spectrum of biological activities including antibacterial (Sharifzadeh et al., 2013), anticonvulsant (Karthikeyan et al., 2007), analgesic (Khode et al., 2009) and antitumor properties (Congiu et al., 2010). In continuation of our research interest to develop novel pyrazoline derivatives which show broad range of biological activities (Hwang et al., 2013), the title compound (I) was synthesized and its crystal structure was determined.
The asymmetric unit of (I) contains two indepencent molecules (A and B in Fig. 1). The dihedral angles between the naphthalene ring system [r.m.s. deviations 0.012 (1) Å for A and 0.015 (1) Å for B] and the benzene ring are 71.65 (6) and 74.51 (6)° for molecules A and B, respectively. In the crystal, pairs of N—H···O hydrogen bonds form two independent inversion dimers (Fig. 2) with graph-set notations R22(14) (Bernstein et al., 1995). In addition, each molecule contains an intramolecular O—H···N hydrogen bond with an S(6) notation. Some examples of pyrazoline structures have been published (Fun et al., 2012; Jasinski et al., 2010).