organic compounds
1-[5-(2-Chlorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one
aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 Pulau, Pinang, Malaysia, and bDepartment of P.G. Studies in Chemistry, Alvas 5, 6 College, Moodbidri, Karnataka 574 227, India
*Correspondence e-mail: farook@usm.my
The title compound, C18H17ClN2O, crystallized with two independent molecules (the S and R enantiomers) in the The molecules are V-shaped with the two aromatic rings inclined to one another by 78.78 (11) and 81.23 (11)°. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming chains along the c-axis direction. The chains are linked via C—H⋯π interactions, forming a three-dimensional framework. The was refined as a two-component twin.
CCDC reference: 1443745
Structure description
Pyrazoline derivatives are well known for their versatile pharmacological activities (Sarojini et al., 2010; Samshuddin et al., 2012). Many 1,3,5-triaryl-2-pyrazolines have a variety of industrial applications; used as scintillation solutes (Wiley et al., 1958) and as fluorescent agents (Zhi-Yun et al., 1999). In view of the importance of pyrazolines the title compound, a new N-acetyl substituted pyrazoline derivative, was prepared by the condensation of (2E)-3-(2-chlorophenyl)-1-(4-methylphenyl)prop-2-en-1-one and hydrazine hydrate in the presence of acetic acid.
The title compound, Fig. 1, crystallized with two independent molecules (A and B: the S and R enantiomers, respectively) in the The pyrazole ring in molecule A has an with the chiral C atom, C7A, as the flap. In molecule B the pyrazole ring has a twist conformation on the CH—CH2 (C7B—C8B) bond. Their mean planes are inclined to the 4-methylbenzene ring by 5.65 (12)° in A and by 8.99 (12)° in B. The two aromatic rings are inclined to one another by 78.78 (11)° in molecule A and by 81.23 (11)° in molecule B.
In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming chains along [001]; see Table 1 and Fig. 2. The chains are linked via C—H⋯π interactions forming a three-dimensional framework (Table 1).
Synthesis and crystallization
A mixture of (2E)-3-(2-chlorophenyl)-1-(4-methylphenyl)prop-2-en-1-one (2.56 g, 0.01 mol) and hydrazine hydrate (1 ml) in 30 ml acetic acid was refluxed for 8 h. The reaction mixture was cooled and poured into 100 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from ethanol by slow evaporation (yield 70%; m.p. 409–412 K).
Refinement
Crystal data, data collection and structure . The was refined as a 2-component twin [180° rotation about the b* axis; BASF = 0.431 (1)].
details are summarized in Table 2
|
Structural data
CCDC reference: 1443745
10.1107/S2414314615024608/su4006sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314615024608/su4006Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314615024608/su4006Isup3.cml
A mixture of (2E)-3-(2-chlorophenyl)-1-(4-methylphenyl)prop-2-en-1-one (2.56 g, 0.01 mol) and hydrazine hydrate (1 ml) in 30 ml acetic acid was refluxed for 8 h. The reaction mixture was cooled and poured into 100 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from ethanol by slow evaporation (yield 70%; m.p. 409–412 K).
Crystal data, data collection and structure
details are summarized in Table 2. The was refined as a 2-component twin [180° rotation about the b* axis; BASF = 0.431 (1)].Pyrazoline derivatives are well known for their versatile pharmacological activities (Sarojini et al., 2010; Samshuddin et al., 2012). Many 1,3,5-triaryl-2-pyrazolines have a variety of industrial application; used as scintillation solutes (Wiley et al., 1958) and as fluorescent agents (Zhi-Yun et al., 1999). In view of the importance of pyrazolines the title compound, new N-acetyl substituted pyrazoline derivative, was prepared by the condensation of (2E)-3-(2-chlorophenyl)-1-(4-methylphenyl)prop-2-en-1-one and hydrazine hydrate in the presence of acetic acid.
The title compound, Fig. 1, crystallized with two independent molecules (A and B: the S and R enantiomers, respectively) in the
The pyrazole ring in molecule A has an with the chiral C atom, C7A, as the flap. In molecule B the pyrazole ring has a twist conformation on the CH—CH2 (C7B—C8B) bond. Their mean planes are inclined to the 4-methylbenzene ring by 5.65 (12)° in A and by 8.99 (12)° in B. The two aromatic rings are inclined to one another by 78.78 (11)° in molecule A and by 81.23 (11)° in molecule B.In the crystal, molecules are linked via C—H···O hydrogen bonds, forming chains along [001]; see Table 1 and Fig. 2. The chains are linked via C—H···π interactions forming a three-dimensional framework (Table 1).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).Fig. 1. The molecular structure of the title compound, showin the atom labelling and 50% probability displacement ellipsoids. | |
Fig. 2. The crystal packing of the title compound viewed along the b axis. Hydrogen bonds are shown as dashed lines (see Table 1). |
C18H17ClN2O | Z = 4 |
Mr = 312.79 | F(000) = 656 |
Triclinic, P1 | Dx = 1.316 Mg m−3 |
a = 11.0767 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.0670 (13) Å | Cell parameters from 9954 reflections |
c = 12.1600 (13) Å | θ = 2.3–25.1° |
α = 90.825 (2)° | µ = 0.25 mm−1 |
β = 102.5614 (19)° | T = 100 K |
γ = 95.142 (2)° | Block, colourless |
V = 1579.1 (3) Å3 | 0.49 × 0.31 × 0.29 mm |
Bruker APEX DUO CCD area-detector diffractometer | 5665 independent reflections |
Radiation source: fine-focus sealed tube | 5334 reflections with I > 2σ(I) |
Graphite monochromator | θmax = 25.1°, θmin = 1.7° |
φ and ω scans | h = −13→12 |
Absorption correction: multi-scan (TWINABS; Bruker, 2009) | k = −14→14 |
Tmin = 0.711, Tmax = 0.857 | l = 0→14 |
5665 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0832P)2 + 0.2751P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
5665 reflections | Δρmax = 0.34 e Å−3 |
402 parameters | Δρmin = −0.35 e Å−3 |
C18H17ClN2O | γ = 95.142 (2)° |
Mr = 312.79 | V = 1579.1 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.0767 (12) Å | Mo Kα radiation |
b = 12.0670 (13) Å | µ = 0.25 mm−1 |
c = 12.1600 (13) Å | T = 100 K |
α = 90.825 (2)° | 0.49 × 0.31 × 0.29 mm |
β = 102.5614 (19)° |
Bruker APEX DUO CCD area-detector diffractometer | 5665 measured reflections |
Absorption correction: multi-scan (TWINABS; Bruker, 2009) | 5665 independent reflections |
Tmin = 0.711, Tmax = 0.857 | 5334 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.34 e Å−3 |
5665 reflections | Δρmin = −0.35 e Å−3 |
402 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. Refined as a 2-component twin |
x | y | z | Uiso*/Ueq | ||
Cl1A | 0.21908 (7) | 0.08540 (5) | 0.04400 (6) | 0.03442 (17) | |
O1A | 0.03134 (16) | 0.25816 (14) | 0.32387 (14) | 0.0274 (4) | |
N1A | 0.09059 (18) | 0.37602 (16) | 0.20123 (16) | 0.0204 (4) | |
N2A | 0.10951 (17) | 0.48329 (16) | 0.16358 (16) | 0.0187 (4) | |
C1A | 0.3041 (2) | 0.1604 (2) | 0.1639 (2) | 0.0240 (5) | |
C2A | 0.4170 (3) | 0.1255 (2) | 0.2180 (2) | 0.0345 (6) | |
H2AA | 0.4466 | 0.0610 | 0.1912 | 0.041* | |
C3A | 0.4860 (2) | 0.1861 (3) | 0.3118 (2) | 0.0350 (6) | |
H3AA | 0.5632 | 0.1628 | 0.3503 | 0.042* | |
C4A | 0.4431 (2) | 0.2799 (2) | 0.3495 (2) | 0.0305 (6) | |
H4AA | 0.4911 | 0.3217 | 0.4134 | 0.037* | |
C5A | 0.3302 (2) | 0.3133 (2) | 0.2942 (2) | 0.0240 (5) | |
H5AA | 0.3016 | 0.3782 | 0.3210 | 0.029* | |
C6A | 0.2577 (2) | 0.25441 (18) | 0.20064 (19) | 0.0195 (5) | |
C7A | 0.1359 (2) | 0.29186 (19) | 0.13625 (19) | 0.0194 (5) | |
H7AA | 0.0720 | 0.2269 | 0.1139 | 0.023* | |
C8A | 0.1540 (2) | 0.35784 (18) | 0.03170 (19) | 0.0202 (5) | |
H8AA | 0.2357 | 0.3484 | 0.0140 | 0.024* | |
H8AB | 0.0873 | 0.3351 | −0.0353 | 0.024* | |
C9A | 0.14683 (19) | 0.47560 (19) | 0.07111 (18) | 0.0178 (4) | |
C10A | 0.17624 (19) | 0.57493 (18) | 0.01095 (18) | 0.0176 (4) | |
C11A | 0.1686 (2) | 0.68142 (19) | 0.05564 (19) | 0.0208 (5) | |
H11A | 0.1440 | 0.6891 | 0.1253 | 0.025* | |
C12A | 0.1967 (2) | 0.7746 (2) | −0.0014 (2) | 0.0238 (5) | |
H12A | 0.1900 | 0.8461 | 0.0292 | 0.029* | |
C13A | 0.2347 (2) | 0.7666 (2) | −0.1027 (2) | 0.0220 (5) | |
C14A | 0.2435 (2) | 0.6615 (2) | −0.1464 (2) | 0.0229 (5) | |
H14A | 0.2698 | 0.6544 | −0.2153 | 0.027* | |
C15A | 0.2146 (2) | 0.56628 (19) | −0.09058 (19) | 0.0211 (5) | |
H15A | 0.2209 | 0.4949 | −0.1218 | 0.025* | |
C16A | 0.0419 (2) | 0.3539 (2) | 0.2927 (2) | 0.0222 (5) | |
C17A | 0.0064 (2) | 0.4513 (2) | 0.3527 (2) | 0.0274 (5) | |
H17A | −0.0123 | 0.5112 | 0.2999 | 0.041* | |
H17B | 0.0754 | 0.4780 | 0.4151 | 0.041* | |
H17C | −0.0671 | 0.4283 | 0.3824 | 0.041* | |
C18A | 0.2599 (3) | 0.8699 (2) | −0.1655 (2) | 0.0310 (6) | |
H18A | 0.3182 | 0.9237 | −0.1146 | 0.047* | |
H18B | 0.1818 | 0.9030 | −0.1936 | 0.047* | |
H18C | 0.2959 | 0.8503 | −0.2291 | 0.047* | |
Cl1B | 0.31200 (6) | 0.46911 (5) | 0.58780 (6) | 0.03452 (17) | |
O1B | 0.02652 (17) | 0.27178 (15) | 0.76408 (14) | 0.0297 (4) | |
N1B | 0.11108 (19) | 0.15285 (16) | 0.66688 (16) | 0.0213 (4) | |
N2B | 0.12585 (17) | 0.04611 (15) | 0.63221 (16) | 0.0194 (4) | |
C1B | 0.3553 (2) | 0.3952 (2) | 0.7108 (2) | 0.0249 (5) | |
C2B | 0.4501 (2) | 0.4432 (2) | 0.7954 (2) | 0.0318 (6) | |
H2BA | 0.4881 | 0.5156 | 0.7877 | 0.038* | |
C3B | 0.4892 (2) | 0.3849 (3) | 0.8915 (2) | 0.0380 (7) | |
H3BA | 0.5547 | 0.4169 | 0.9502 | 0.046* | |
C4B | 0.4327 (2) | 0.2796 (3) | 0.9023 (2) | 0.0365 (6) | |
H4BA | 0.4602 | 0.2390 | 0.9679 | 0.044* | |
C5B | 0.3363 (2) | 0.2337 (2) | 0.8175 (2) | 0.0292 (5) | |
H5BA | 0.2976 | 0.1618 | 0.8259 | 0.035* | |
C6B | 0.2944 (2) | 0.2914 (2) | 0.71936 (19) | 0.0221 (5) | |
C7B | 0.1899 (2) | 0.23941 (19) | 0.62557 (19) | 0.0206 (5) | |
H7BA | 0.1388 | 0.2980 | 0.5879 | 0.025* | |
C8B | 0.2386 (2) | 0.17185 (19) | 0.53747 (19) | 0.0222 (5) | |
H8BA | 0.1997 | 0.1905 | 0.4595 | 0.027* | |
H8BB | 0.3300 | 0.1848 | 0.5488 | 0.027* | |
C9B | 0.1987 (2) | 0.05402 (18) | 0.56220 (18) | 0.0183 (5) | |
C10B | 0.2338 (2) | −0.04471 (19) | 0.51034 (19) | 0.0194 (5) | |
C11B | 0.1761 (2) | −0.15102 (19) | 0.52063 (19) | 0.0202 (5) | |
H11B | 0.1133 | −0.1601 | 0.5629 | 0.024* | |
C12B | 0.2099 (2) | −0.2424 (2) | 0.4697 (2) | 0.0243 (5) | |
H12B | 0.1704 | −0.3140 | 0.4779 | 0.029* | |
C13B | 0.3016 (2) | −0.2322 (2) | 0.4060 (2) | 0.0239 (5) | |
C14B | 0.3578 (2) | −0.1270 (2) | 0.3965 (2) | 0.0245 (5) | |
H14B | 0.4204 | −0.1181 | 0.3540 | 0.029* | |
C15B | 0.3254 (2) | −0.0342 (2) | 0.44718 (19) | 0.0219 (5) | |
H15B | 0.3655 | 0.0371 | 0.4390 | 0.026* | |
C16B | 0.0340 (2) | 0.1753 (2) | 0.73584 (19) | 0.0235 (5) | |
C17B | −0.0383 (2) | 0.0777 (2) | 0.7745 (2) | 0.0286 (5) | |
H17D | −0.0357 | 0.0114 | 0.7278 | 0.043* | |
H17E | −0.1248 | 0.0938 | 0.7674 | 0.043* | |
H17F | −0.0017 | 0.0643 | 0.8535 | 0.043* | |
C18B | 0.3362 (3) | −0.3328 (2) | 0.3498 (2) | 0.0321 (6) | |
H18D | 0.2606 | −0.3786 | 0.3121 | 0.048* | |
H18E | 0.3865 | −0.3764 | 0.4066 | 0.048* | |
H18F | 0.3841 | −0.3088 | 0.2939 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1A | 0.0516 (4) | 0.0218 (3) | 0.0306 (3) | 0.0038 (3) | 0.0108 (3) | −0.0039 (2) |
O1A | 0.0261 (9) | 0.0289 (9) | 0.0274 (9) | 0.0012 (7) | 0.0065 (7) | 0.0094 (7) |
N1A | 0.0215 (10) | 0.0197 (9) | 0.0215 (10) | 0.0038 (8) | 0.0071 (8) | 0.0035 (8) |
N2A | 0.0166 (9) | 0.0203 (9) | 0.0193 (9) | 0.0019 (7) | 0.0039 (7) | 0.0031 (7) |
C1A | 0.0285 (12) | 0.0234 (12) | 0.0217 (12) | 0.0027 (10) | 0.0089 (10) | 0.0059 (9) |
C2A | 0.0416 (16) | 0.0355 (14) | 0.0361 (15) | 0.0198 (12) | 0.0221 (13) | 0.0154 (12) |
C3A | 0.0187 (12) | 0.0581 (18) | 0.0316 (14) | 0.0114 (12) | 0.0082 (10) | 0.0222 (13) |
C4A | 0.0204 (12) | 0.0435 (15) | 0.0239 (12) | −0.0046 (11) | −0.0002 (10) | 0.0084 (11) |
C5A | 0.0199 (12) | 0.0261 (12) | 0.0249 (12) | −0.0029 (9) | 0.0045 (9) | 0.0044 (9) |
C6A | 0.0199 (11) | 0.0190 (11) | 0.0209 (11) | −0.0014 (9) | 0.0081 (9) | 0.0062 (9) |
C7A | 0.0208 (11) | 0.0182 (11) | 0.0191 (11) | 0.0017 (9) | 0.0039 (9) | 0.0010 (8) |
C8A | 0.0224 (12) | 0.0206 (11) | 0.0180 (11) | 0.0035 (9) | 0.0044 (9) | 0.0009 (9) |
C9A | 0.0120 (10) | 0.0233 (11) | 0.0164 (10) | 0.0030 (9) | −0.0006 (8) | −0.0002 (9) |
C10A | 0.0116 (10) | 0.0227 (11) | 0.0179 (11) | 0.0022 (8) | 0.0013 (8) | 0.0011 (9) |
C11A | 0.0182 (11) | 0.0264 (12) | 0.0184 (11) | 0.0029 (9) | 0.0049 (9) | 0.0016 (9) |
C12A | 0.0250 (12) | 0.0198 (11) | 0.0272 (12) | 0.0037 (9) | 0.0062 (10) | 0.0004 (9) |
C13A | 0.0168 (11) | 0.0251 (11) | 0.0237 (11) | 0.0019 (9) | 0.0034 (9) | 0.0051 (9) |
C14A | 0.0187 (11) | 0.0332 (13) | 0.0179 (11) | 0.0040 (9) | 0.0060 (9) | 0.0011 (9) |
C15A | 0.0182 (11) | 0.0242 (11) | 0.0197 (11) | 0.0038 (9) | 0.0013 (9) | −0.0009 (9) |
C16A | 0.0146 (11) | 0.0321 (13) | 0.0197 (11) | 0.0024 (9) | 0.0028 (9) | 0.0044 (10) |
C17A | 0.0258 (12) | 0.0362 (14) | 0.0217 (12) | 0.0028 (10) | 0.0087 (10) | 0.0014 (10) |
C18A | 0.0360 (15) | 0.0280 (13) | 0.0325 (14) | 0.0045 (11) | 0.0139 (12) | 0.0080 (11) |
Cl1B | 0.0337 (3) | 0.0277 (3) | 0.0408 (4) | −0.0019 (3) | 0.0069 (3) | 0.0074 (3) |
O1B | 0.0291 (9) | 0.0328 (10) | 0.0269 (9) | 0.0100 (8) | 0.0032 (7) | −0.0061 (7) |
N1B | 0.0205 (10) | 0.0215 (10) | 0.0223 (10) | 0.0029 (8) | 0.0053 (8) | 0.0004 (8) |
N2B | 0.0187 (9) | 0.0198 (9) | 0.0196 (9) | 0.0019 (7) | 0.0038 (8) | −0.0006 (7) |
C1B | 0.0217 (12) | 0.0279 (12) | 0.0272 (13) | 0.0030 (10) | 0.0097 (10) | −0.0031 (10) |
C2B | 0.0185 (12) | 0.0384 (15) | 0.0388 (15) | −0.0025 (11) | 0.0099 (11) | −0.0140 (12) |
C3B | 0.0151 (12) | 0.066 (2) | 0.0313 (15) | −0.0015 (12) | 0.0050 (11) | −0.0158 (13) |
C4B | 0.0229 (13) | 0.0617 (19) | 0.0241 (13) | 0.0077 (13) | 0.0014 (10) | 0.0039 (12) |
C5B | 0.0245 (12) | 0.0385 (14) | 0.0238 (12) | 0.0054 (11) | 0.0030 (10) | 0.0025 (11) |
C6B | 0.0200 (12) | 0.0265 (12) | 0.0200 (11) | 0.0039 (10) | 0.0046 (9) | −0.0025 (9) |
C7B | 0.0211 (11) | 0.0206 (11) | 0.0195 (11) | 0.0023 (9) | 0.0027 (9) | 0.0012 (9) |
C8B | 0.0274 (12) | 0.0214 (11) | 0.0181 (11) | 0.0010 (9) | 0.0061 (9) | 0.0014 (9) |
C9B | 0.0161 (11) | 0.0216 (11) | 0.0159 (10) | 0.0014 (9) | 0.0009 (8) | 0.0023 (8) |
C10B | 0.0183 (11) | 0.0242 (11) | 0.0152 (10) | 0.0022 (9) | 0.0028 (8) | 0.0025 (9) |
C11B | 0.0170 (11) | 0.0239 (11) | 0.0187 (11) | 0.0005 (9) | 0.0025 (9) | 0.0016 (9) |
C12B | 0.0266 (12) | 0.0204 (11) | 0.0238 (12) | 0.0009 (9) | 0.0013 (10) | 0.0014 (9) |
C13B | 0.0244 (12) | 0.0286 (12) | 0.0173 (11) | 0.0072 (10) | −0.0001 (9) | −0.0030 (9) |
C14B | 0.0215 (12) | 0.0328 (13) | 0.0200 (11) | 0.0032 (10) | 0.0062 (9) | −0.0008 (10) |
C15B | 0.0199 (11) | 0.0255 (11) | 0.0204 (11) | 0.0005 (9) | 0.0052 (9) | 0.0023 (9) |
C16B | 0.0170 (11) | 0.0342 (13) | 0.0182 (10) | 0.0049 (10) | 0.0005 (9) | −0.0008 (10) |
C17B | 0.0218 (12) | 0.0425 (14) | 0.0229 (12) | 0.0027 (11) | 0.0080 (10) | −0.0001 (11) |
C18B | 0.0371 (15) | 0.0338 (14) | 0.0245 (13) | 0.0074 (12) | 0.0036 (11) | −0.0043 (11) |
Cl1A—C1A | 1.744 (3) | Cl1B—C1B | 1.751 (3) |
O1A—C16A | 1.225 (3) | O1B—C16B | 1.225 (3) |
N1A—C16A | 1.357 (3) | N1B—C16B | 1.361 (3) |
N1A—N2A | 1.393 (3) | N1B—N2B | 1.384 (3) |
N1A—C7A | 1.466 (3) | N1B—C7B | 1.466 (3) |
N2A—C9A | 1.285 (3) | N2B—C9B | 1.293 (3) |
C1A—C2A | 1.385 (4) | C1B—C2B | 1.379 (4) |
C1A—C6A | 1.394 (3) | C1B—C6B | 1.385 (4) |
C2A—C3A | 1.385 (4) | C2B—C3B | 1.380 (4) |
C2A—H2AA | 0.9500 | C2B—H2BA | 0.9500 |
C3A—C4A | 1.376 (4) | C3B—C4B | 1.386 (4) |
C3A—H3AA | 0.9500 | C3B—H3BA | 0.9500 |
C4A—C5A | 1.383 (4) | C4B—C5B | 1.381 (4) |
C4A—H4AA | 0.9500 | C4B—H4BA | 0.9500 |
C5A—C6A | 1.386 (3) | C5B—C6B | 1.401 (3) |
C5A—H5AA | 0.9500 | C5B—H5BA | 0.9500 |
C6A—C7A | 1.515 (3) | C6B—C7B | 1.519 (3) |
C7A—C8A | 1.550 (3) | C7B—C8B | 1.551 (3) |
C7A—H7AA | 1.0000 | C7B—H7BA | 1.0000 |
C8A—C9A | 1.508 (3) | C8B—C9B | 1.505 (3) |
C8A—H8AA | 0.9900 | C8B—H8BA | 0.9900 |
C8A—H8AB | 0.9900 | C8B—H8BB | 0.9900 |
C9A—C10A | 1.462 (3) | C9B—C10B | 1.462 (3) |
C10A—C15A | 1.396 (3) | C10B—C15B | 1.397 (3) |
C10A—C11A | 1.405 (3) | C10B—C11B | 1.401 (3) |
C11A—C12A | 1.377 (3) | C11B—C12B | 1.377 (3) |
C11A—H11A | 0.9500 | C11B—H11B | 0.9500 |
C12A—C13A | 1.390 (3) | C12B—C13B | 1.403 (4) |
C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
C13A—C14A | 1.388 (3) | C13B—C14B | 1.381 (4) |
C13A—C18A | 1.508 (3) | C13B—C18B | 1.504 (3) |
C14A—C15A | 1.391 (3) | C14B—C15B | 1.383 (3) |
C14A—H14A | 0.9500 | C14B—H14B | 0.9500 |
C15A—H15A | 0.9500 | C15B—H15B | 0.9500 |
C16A—C17A | 1.501 (3) | C16B—C17B | 1.503 (4) |
C17A—H17A | 0.9800 | C17B—H17D | 0.9800 |
C17A—H17B | 0.9800 | C17B—H17E | 0.9800 |
C17A—H17C | 0.9800 | C17B—H17F | 0.9800 |
C18A—H18A | 0.9800 | C18B—H18D | 0.9800 |
C18A—H18B | 0.9800 | C18B—H18E | 0.9800 |
C18A—H18C | 0.9800 | C18B—H18F | 0.9800 |
C16A—N1A—N2A | 122.91 (19) | C16B—N1B—N2B | 123.3 (2) |
C16A—N1A—C7A | 124.13 (19) | C16B—N1B—C7B | 123.1 (2) |
N2A—N1A—C7A | 112.85 (17) | N2B—N1B—C7B | 113.53 (18) |
C9A—N2A—N1A | 107.83 (18) | C9B—N2B—N1B | 107.86 (18) |
C2A—C1A—C6A | 122.2 (2) | C2B—C1B—C6B | 122.6 (2) |
C2A—C1A—Cl1A | 118.7 (2) | C2B—C1B—Cl1B | 118.1 (2) |
C6A—C1A—Cl1A | 119.08 (19) | C6B—C1B—Cl1B | 119.29 (19) |
C3A—C2A—C1A | 118.9 (2) | C1B—C2B—C3B | 119.2 (3) |
C3A—C2A—H2AA | 120.6 | C1B—C2B—H2BA | 120.4 |
C1A—C2A—H2AA | 120.6 | C3B—C2B—H2BA | 120.4 |
C4A—C3A—C2A | 120.2 (2) | C2B—C3B—C4B | 120.0 (2) |
C4A—C3A—H3AA | 119.9 | C2B—C3B—H3BA | 120.0 |
C2A—C3A—H3AA | 119.9 | C4B—C3B—H3BA | 120.0 |
C3A—C4A—C5A | 120.0 (2) | C5B—C4B—C3B | 119.9 (3) |
C3A—C4A—H4AA | 120.0 | C5B—C4B—H4BA | 120.0 |
C5A—C4A—H4AA | 120.0 | C3B—C4B—H4BA | 120.0 |
C4A—C5A—C6A | 121.7 (2) | C4B—C5B—C6B | 121.3 (3) |
C4A—C5A—H5AA | 119.2 | C4B—C5B—H5BA | 119.4 |
C6A—C5A—H5AA | 119.2 | C6B—C5B—H5BA | 119.4 |
C5A—C6A—C1A | 117.0 (2) | C1B—C6B—C5B | 116.9 (2) |
C5A—C6A—C7A | 122.5 (2) | C1B—C6B—C7B | 122.1 (2) |
C1A—C6A—C7A | 120.4 (2) | C5B—C6B—C7B | 120.9 (2) |
N1A—C7A—C6A | 111.47 (19) | N1B—C7B—C6B | 111.94 (18) |
N1A—C7A—C8A | 101.24 (17) | N1B—C7B—C8B | 101.23 (18) |
C6A—C7A—C8A | 111.26 (19) | C6B—C7B—C8B | 112.36 (19) |
N1A—C7A—H7AA | 110.8 | N1B—C7B—H7BA | 110.3 |
C6A—C7A—H7AA | 110.8 | C6B—C7B—H7BA | 110.3 |
C8A—C7A—H7AA | 110.8 | C8B—C7B—H7BA | 110.3 |
C9A—C8A—C7A | 101.45 (17) | C9B—C8B—C7B | 101.85 (18) |
C9A—C8A—H8AA | 111.5 | C9B—C8B—H8BA | 111.4 |
C7A—C8A—H8AA | 111.5 | C7B—C8B—H8BA | 111.4 |
C9A—C8A—H8AB | 111.5 | C9B—C8B—H8BB | 111.4 |
C7A—C8A—H8AB | 111.5 | C7B—C8B—H8BB | 111.4 |
H8AA—C8A—H8AB | 109.3 | H8BA—C8B—H8BB | 109.3 |
N2A—C9A—C10A | 121.0 (2) | N2B—C9B—C10B | 121.5 (2) |
N2A—C9A—C8A | 114.3 (2) | N2B—C9B—C8B | 114.06 (19) |
C10A—C9A—C8A | 124.68 (19) | C10B—C9B—C8B | 124.4 (2) |
C15A—C10A—C11A | 118.7 (2) | C15B—C10B—C11B | 118.4 (2) |
C15A—C10A—C9A | 120.9 (2) | C15B—C10B—C9B | 120.1 (2) |
C11A—C10A—C9A | 120.4 (2) | C11B—C10B—C9B | 121.5 (2) |
C12A—C11A—C10A | 120.1 (2) | C12B—C11B—C10B | 120.2 (2) |
C12A—C11A—H11A | 120.0 | C12B—C11B—H11B | 119.9 |
C10A—C11A—H11A | 120.0 | C10B—C11B—H11B | 119.9 |
C11A—C12A—C13A | 121.6 (2) | C11B—C12B—C13B | 121.5 (2) |
C11A—C12A—H12A | 119.2 | C11B—C12B—H12B | 119.3 |
C13A—C12A—H12A | 119.2 | C13B—C12B—H12B | 119.3 |
C14A—C13A—C12A | 118.5 (2) | C14B—C13B—C12B | 117.7 (2) |
C14A—C13A—C18A | 121.2 (2) | C14B—C13B—C18B | 121.5 (2) |
C12A—C13A—C18A | 120.3 (2) | C12B—C13B—C18B | 120.7 (2) |
C13A—C14A—C15A | 120.9 (2) | C13B—C14B—C15B | 121.7 (2) |
C13A—C14A—H14A | 119.6 | C13B—C14B—H14B | 119.2 |
C15A—C14A—H14A | 119.6 | C15B—C14B—H14B | 119.2 |
C14A—C15A—C10A | 120.4 (2) | C14B—C15B—C10B | 120.5 (2) |
C14A—C15A—H15A | 119.8 | C14B—C15B—H15B | 119.8 |
C10A—C15A—H15A | 119.8 | C10B—C15B—H15B | 119.8 |
O1A—C16A—N1A | 119.9 (2) | O1B—C16B—N1B | 119.8 (2) |
O1A—C16A—C17A | 123.2 (2) | O1B—C16B—C17B | 123.0 (2) |
N1A—C16A—C17A | 116.9 (2) | N1B—C16B—C17B | 117.2 (2) |
C16A—C17A—H17A | 109.5 | C16B—C17B—H17D | 109.5 |
C16A—C17A—H17B | 109.5 | C16B—C17B—H17E | 109.5 |
H17A—C17A—H17B | 109.5 | H17D—C17B—H17E | 109.5 |
C16A—C17A—H17C | 109.5 | C16B—C17B—H17F | 109.5 |
H17A—C17A—H17C | 109.5 | H17D—C17B—H17F | 109.5 |
H17B—C17A—H17C | 109.5 | H17E—C17B—H17F | 109.5 |
C13A—C18A—H18A | 109.5 | C13B—C18B—H18D | 109.5 |
C13A—C18A—H18B | 109.5 | C13B—C18B—H18E | 109.5 |
H18A—C18A—H18B | 109.5 | H18D—C18B—H18E | 109.5 |
C13A—C18A—H18C | 109.5 | C13B—C18B—H18F | 109.5 |
H18A—C18A—H18C | 109.5 | H18D—C18B—H18F | 109.5 |
H18B—C18A—H18C | 109.5 | H18E—C18B—H18F | 109.5 |
C16A—N1A—N2A—C9A | −174.9 (2) | C16B—N1B—N2B—C9B | 176.0 (2) |
C7A—N1A—N2A—C9A | 8.8 (2) | C7B—N1B—N2B—C9B | −6.2 (2) |
C6A—C1A—C2A—C3A | 0.0 (4) | C6B—C1B—C2B—C3B | 1.9 (4) |
Cl1A—C1A—C2A—C3A | 178.68 (19) | Cl1B—C1B—C2B—C3B | −177.57 (19) |
C1A—C2A—C3A—C4A | −0.6 (4) | C1B—C2B—C3B—C4B | −0.3 (4) |
C2A—C3A—C4A—C5A | 0.6 (4) | C2B—C3B—C4B—C5B | −0.8 (4) |
C3A—C4A—C5A—C6A | 0.0 (4) | C3B—C4B—C5B—C6B | 0.5 (4) |
C4A—C5A—C6A—C1A | −0.6 (3) | C2B—C1B—C6B—C5B | −2.2 (3) |
C4A—C5A—C6A—C7A | −177.7 (2) | Cl1B—C1B—C6B—C5B | 177.29 (18) |
C2A—C1A—C6A—C5A | 0.6 (3) | C2B—C1B—C6B—C7B | 180.0 (2) |
Cl1A—C1A—C6A—C5A | −178.08 (17) | Cl1B—C1B—C6B—C7B | −0.5 (3) |
C2A—C1A—C6A—C7A | 177.8 (2) | C4B—C5B—C6B—C1B | 1.0 (4) |
Cl1A—C1A—C6A—C7A | −0.9 (3) | C4B—C5B—C6B—C7B | 178.8 (2) |
C16A—N1A—C7A—C6A | −72.6 (3) | C16B—N1B—C7B—C6B | 69.3 (3) |
N2A—N1A—C7A—C6A | 103.7 (2) | N2B—N1B—C7B—C6B | −108.6 (2) |
C16A—N1A—C7A—C8A | 169.0 (2) | C16B—N1B—C7B—C8B | −170.9 (2) |
N2A—N1A—C7A—C8A | −14.7 (2) | N2B—N1B—C7B—C8B | 11.3 (2) |
C5A—C6A—C7A—N1A | −15.5 (3) | C1B—C6B—C7B—N1B | −159.0 (2) |
C1A—C6A—C7A—N1A | 167.55 (19) | C5B—C6B—C7B—N1B | 23.2 (3) |
C5A—C6A—C7A—C8A | 96.8 (3) | C1B—C6B—C7B—C8B | 87.8 (3) |
C1A—C6A—C7A—C8A | −80.2 (3) | C5B—C6B—C7B—C8B | −89.9 (3) |
N1A—C7A—C8A—C9A | 14.0 (2) | N1B—C7B—C8B—C9B | −11.2 (2) |
C6A—C7A—C8A—C9A | −104.6 (2) | C6B—C7B—C8B—C9B | 108.4 (2) |
N1A—N2A—C9A—C10A | −179.30 (19) | N1B—N2B—C9B—C10B | 179.58 (19) |
N1A—N2A—C9A—C8A | 1.9 (2) | N1B—N2B—C9B—C8B | −2.4 (3) |
C7A—C8A—C9A—N2A | −10.7 (2) | C7B—C8B—C9B—N2B | 9.1 (3) |
C7A—C8A—C9A—C10A | 170.6 (2) | C7B—C8B—C9B—C10B | −173.0 (2) |
N2A—C9A—C10A—C15A | −178.8 (2) | N2B—C9B—C10B—C15B | −171.4 (2) |
C8A—C9A—C10A—C15A | −0.1 (3) | C8B—C9B—C10B—C15B | 10.8 (3) |
N2A—C9A—C10A—C11A | 2.4 (3) | N2B—C9B—C10B—C11B | 9.7 (3) |
C8A—C9A—C10A—C11A | −179.0 (2) | C8B—C9B—C10B—C11B | −168.1 (2) |
C15A—C10A—C11A—C12A | 1.0 (3) | C15B—C10B—C11B—C12B | 0.3 (3) |
C9A—C10A—C11A—C12A | 179.9 (2) | C9B—C10B—C11B—C12B | 179.2 (2) |
C10A—C11A—C12A—C13A | −0.9 (4) | C10B—C11B—C12B—C13B | −0.5 (3) |
C11A—C12A—C13A—C14A | 0.2 (4) | C11B—C12B—C13B—C14B | 0.5 (3) |
C11A—C12A—C13A—C18A | 177.5 (2) | C11B—C12B—C13B—C18B | −179.2 (2) |
C12A—C13A—C14A—C15A | 0.3 (3) | C12B—C13B—C14B—C15B | −0.3 (4) |
C18A—C13A—C14A—C15A | −177.0 (2) | C18B—C13B—C14B—C15B | 179.3 (2) |
C13A—C14A—C15A—C10A | −0.2 (3) | C13B—C14B—C15B—C10B | 0.1 (4) |
C11A—C10A—C15A—C14A | −0.5 (3) | C11B—C10B—C15B—C14B | −0.1 (3) |
C9A—C10A—C15A—C14A | −179.3 (2) | C9B—C10B—C15B—C14B | −179.1 (2) |
N2A—N1A—C16A—O1A | −177.6 (2) | N2B—N1B—C16B—O1B | 179.2 (2) |
C7A—N1A—C16A—O1A | −1.6 (3) | C7B—N1B—C16B—O1B | 1.6 (3) |
N2A—N1A—C16A—C17A | 0.9 (3) | N2B—N1B—C16B—C17B | −0.4 (3) |
C7A—N1A—C16A—C17A | 176.8 (2) | C7B—N1B—C16B—C17B | −178.1 (2) |
Cg3 and Cg6 are the centroids of rings C10A–C15A and C10B–C15B, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8A—H8AB···O1Bi | 0.99 | 2.48 | 3.362 (3) | 149 |
C11B—H11B···O1Aii | 0.95 | 2.56 | 3.458 (3) | 159 |
C8B—H8BA···O1A | 0.99 | 2.42 | 3.319 (3) | 151 |
C3A—H3AA···Cg6iii | 0.95 | 2.69 | 3.550 (3) | 151 |
C3B—H3BA···Cg3iv | 0.95 | 2.95 | 3.616 (3) | 128 |
Symmetry codes: (i) x, y, z−1; (ii) −x, −y, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+1. |
Cg3 and Cg6 are the centroids of rings C10A–C15A and C10B–C15B, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8A—H8AB···O1Bi | 0.99 | 2.48 | 3.362 (3) | 149 |
C11B—H11B···O1Aii | 0.95 | 2.56 | 3.458 (3) | 159 |
C8B—H8BA···O1A | 0.99 | 2.42 | 3.319 (3) | 151 |
C3A—H3AA···Cg6iii | 0.95 | 2.69 | 3.550 (3) | 151 |
C3B—H3BA···Cg3iv | 0.95 | 2.95 | 3.616 (3) | 128 |
Symmetry codes: (i) x, y, z−1; (ii) −x, −y, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C18H17ClN2O |
Mr | 312.79 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 11.0767 (12), 12.0670 (13), 12.1600 (13) |
α, β, γ (°) | 90.825 (2), 102.5614 (19), 95.142 (2) |
V (Å3) | 1579.1 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.25 |
Crystal size (mm) | 0.49 × 0.31 × 0.29 |
Data collection | |
Diffractometer | Bruker APEX DUO CCD area-detector |
Absorption correction | Multi-scan (TWINABS; Bruker, 2009) |
Tmin, Tmax | 0.711, 0.857 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5665, 5665, 5334 |
Rint | ? |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.119, 1.10 |
No. of reflections | 5665 |
No. of parameters | 402 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.35 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS2013 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Acknowledgements
SS thanks the Alva's Education Foundation, Moodbidri, for the research facilities. The authors would like to thank the Universiti Malaysia Kelantan, SLAI from Malaysian Ministry of Higher Education and Universiti Sains Malaysia for the RU research Grant (Nos. PKIMIA/846017 and 1001/PKIMIA/811269) which partly supported this work.
References
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