Literature DB >> 21201490

4-[3-(Trifluoro-meth-yl)phen-yl]-5,6,7,8-tetra-hydro-cinnolin-3(2H)-one.

Xin Wang1, Xiao-Mao Zou, You-Quan Zhu, Xu-Hong Hu, Hua-Zheng Yang.   

Abstract

The title compound, C(15)H(13)F(3)N(2)O, contains one benzene ring, one cyclo-hexane ring and a pyridazine ring. The dihedral angle formed by the pyridazine ring with the benzene ring is 61.5 (2)°. The crystal structure is stabilized by two inter-molecular hydrogen bonds (N-H⋯O and C-H⋯F). The cyclohexane ring adopts a screw-boat conformation. The CF(3) group is disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.

Entities:  

Year:  2008        PMID： 21201490      PMCID： PMC2960356          DOI： 10.1107/S1600536808000871

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related literature, see: Heinisch & Kopelent (1992 ▶); Kolar & Tisler (1999 ▶).

Experimental

Crystal data

C15H13F3N2O M = 294.27 Monoclinic, a = 8.929 (3) Å b = 11.443 (4) Å c = 27.448 (8) Å β = 94.232 (6)° V = 2796.6 (15) Å3 Z = 8 Mo Kα radiation μ = 0.12 mm−1 T = 294 (2) K 0.22 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.975, T max = 0.982 7053 measured reflections 2485 independent reflections 1098 reflections with I > 2σ(I) R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.068 wR(F 2) = 0.211 S = 1.02 2485 reflections 223 parameters 85 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.32 e Å−3 Δρmin = −0.27 e Å−3 Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000871/at2529sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000871/at2529Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H13F3N2OF000 = 1216
Mr = 294.27Dx = 1.398 Mg m−3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1012 reflections
a = 8.929 (3) Åθ = 2.9–20.2º
b = 11.443 (4) ŵ = 0.12 mm−1
c = 27.448 (8) ÅT = 294 (2) K
β = 94.232 (6)ºPrism, colourless
V = 2796.6 (15) Å30.22 × 0.20 × 0.16 mm
Z = 8
Bruker SMART CCD area-detector diffractometer2485 independent reflections
Radiation source: fine-focus sealed tube1098 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.061
T = 294(2) Kθmax = 25.0º
φ and ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.975, Tmax = 0.982k = −13→8
7053 measured reflectionsl = −32→32
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.212  w = 1/[σ2(Fo2) + (0.0738P)2 + 4.8514P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
2485 reflectionsΔρmax = 0.32 e Å−3
223 parametersΔρmin = −0.27 e Å−3
85 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0029 (8)
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.
xyzUiso*/UeqOcc. (<1)
F11.1701 (18)0.1095 (16)0.2649 (5)0.144 (5)0.429 (9)
F21.3627 (15)0.1988 (12)0.2422 (6)0.167 (5)0.429 (9)
F31.274 (2)0.0347 (12)0.2066 (5)0.139 (5)0.429 (9)
F1'1.2515 (15)0.1731 (11)0.2699 (3)0.152 (4)0.571 (9)
F2'1.3577 (10)0.0982 (12)0.2113 (4)0.130 (4)0.571 (9)
F3'1.1498 (13)0.0330 (10)0.2327 (5)0.170 (4)0.571 (9)
O11.0587 (4)0.0810 (3)0.05160 (12)0.0661 (10)
N10.6764 (5)0.0930 (3)0.00974 (15)0.0601 (11)
N20.8244 (5)0.0709 (4)0.01511 (15)0.0579 (11)
C10.6214 (5)0.1615 (4)0.04183 (19)0.0547 (13)
C20.4543 (5)0.1771 (5)0.0370 (2)0.0755 (16)
H2A0.42360.19600.00330.091*
H2B0.40740.10350.04460.091*
C30.3977 (7)0.2691 (7)0.0689 (3)0.120 (3)
H3A0.40010.34310.05180.144*
H3B0.29350.25220.07390.144*
C40.4780 (7)0.2826 (7)0.1160 (3)0.103 (2)
H4A0.45990.21410.13560.124*
H4B0.43730.34960.13220.124*
C50.6424 (6)0.2986 (5)0.11490 (19)0.0708 (16)
H5A0.68910.28720.14760.085*
H5B0.66220.37840.10530.085*
C60.7142 (5)0.2159 (4)0.08030 (17)0.0533 (13)
C70.8642 (5)0.1920 (4)0.08449 (15)0.0480 (12)
C80.9248 (6)0.1122 (4)0.05062 (16)0.0497 (12)
C90.9705 (5)0.2428 (4)0.12244 (17)0.0539 (13)
C100.9951 (6)0.3607 (5)0.1261 (2)0.0813 (18)
H100.94500.41070.10360.098*
C111.0930 (7)0.4069 (6)0.1624 (3)0.111 (3)
H111.10750.48720.16470.133*
C121.1682 (7)0.3337 (8)0.1950 (3)0.110 (3)
H121.23390.36430.21960.133*
C131.1474 (6)0.2162 (7)0.1915 (2)0.083 (2)
C141.0497 (5)0.1703 (5)0.15529 (17)0.0650 (15)
H141.03690.08980.15300.078*
C151.2323 (9)0.1368 (8)0.2247 (2)0.114 (3)
H20.862 (5)0.023 (4)−0.0072 (14)0.081 (18)*
U11U22U33U12U13U23
F10.165 (9)0.167 (9)0.102 (7)0.031 (7)0.032 (7)0.026 (7)
F20.139 (8)0.198 (9)0.157 (8)0.018 (7)−0.044 (7)0.025 (7)
F30.150 (9)0.146 (8)0.118 (7)0.075 (7)−0.004 (7)0.012 (6)
F1'0.179 (8)0.207 (8)0.064 (4)−0.003 (7)−0.021 (5)0.006 (5)
F2'0.102 (5)0.166 (8)0.123 (6)0.071 (5)0.011 (5)0.020 (6)
F3'0.158 (7)0.185 (7)0.157 (7)0.032 (6)−0.052 (6)0.061 (6)
O10.057 (2)0.068 (2)0.071 (2)0.0144 (17)−0.0021 (17)−0.0177 (19)
N10.059 (3)0.052 (3)0.068 (3)0.002 (2)−0.004 (2)−0.001 (2)
N20.058 (3)0.053 (3)0.061 (3)0.007 (2)−0.005 (2)−0.010 (2)
C10.053 (3)0.045 (3)0.065 (3)0.000 (2)−0.004 (3)0.004 (3)
C20.054 (3)0.071 (4)0.099 (4)0.002 (3)−0.004 (3)0.003 (4)
C30.059 (4)0.150 (7)0.147 (7)0.020 (4)−0.005 (4)−0.044 (6)
C40.068 (4)0.135 (6)0.109 (5)0.009 (4)0.021 (4)−0.014 (5)
C50.065 (3)0.078 (4)0.070 (3)0.018 (3)0.002 (3)−0.009 (3)
C60.059 (3)0.046 (3)0.055 (3)0.006 (2)0.004 (2)0.007 (2)
C70.056 (3)0.041 (3)0.047 (3)0.006 (2)0.001 (2)0.002 (2)
C80.055 (3)0.042 (3)0.051 (3)0.005 (2)0.000 (3)−0.002 (2)
C90.056 (3)0.056 (3)0.049 (3)0.013 (2)0.000 (2)−0.009 (3)
C100.076 (4)0.062 (4)0.102 (5)0.008 (3)−0.020 (3)−0.019 (3)
C110.091 (5)0.085 (5)0.152 (7)0.013 (4)−0.026 (5)−0.055 (5)
C120.074 (4)0.150 (7)0.104 (5)0.032 (5)−0.020 (4)−0.063 (6)
C130.064 (4)0.131 (6)0.051 (3)0.039 (4)−0.009 (3)−0.017 (4)
C140.069 (3)0.076 (4)0.049 (3)0.021 (3)0.002 (3)−0.002 (3)
C150.102 (6)0.155 (7)0.080 (5)0.016 (5)−0.025 (4)−0.003 (5)
F1—C151.310 (9)C4—H4A0.9700
F2—C151.416 (9)C4—H4B0.9700
F3—C151.333 (9)C5—C61.516 (7)
F1'—C151.308 (8)C5—H5A0.9700
F2'—C151.282 (8)C5—H5B0.9700
F3'—C151.423 (9)C6—C71.363 (6)
O1—C81.246 (5)C7—C81.437 (6)
N1—C11.302 (6)C7—C91.476 (6)
N1—N21.343 (5)C9—C101.370 (7)
N2—C81.360 (6)C9—C141.381 (6)
N2—H20.91 (4)C10—C111.382 (8)
C1—C61.435 (6)C10—H100.9300
C1—C21.499 (6)C11—C121.364 (9)
C2—C31.481 (8)C11—H110.9300
C2—H2A0.9700C12—C131.360 (9)
C2—H2B0.9700C12—H120.9300
C3—C41.441 (8)C13—C141.377 (7)
C3—H3A0.9700C13—C151.459 (9)
C3—H3B0.9700C14—H140.9300
C4—C51.482 (7)
C1—N1—N2117.2 (4)C10—C9—C14118.2 (5)
N1—N2—C8127.2 (4)C10—C9—C7122.0 (5)
N1—N2—H2117 (3)C14—C9—C7119.7 (5)
C8—N2—H2116 (3)C9—C10—C11121.2 (6)
N1—C1—C6122.2 (4)C9—C10—H10119.4
N1—C1—C2115.8 (5)C11—C10—H10119.4
C6—C1—C2122.0 (5)C12—C11—C10119.5 (7)
C3—C2—C1114.4 (5)C12—C11—H11120.2
C3—C2—H2A108.7C10—C11—H11120.2
C1—C2—H2A108.7C13—C12—C11120.2 (6)
C3—C2—H2B108.7C13—C12—H12119.9
C1—C2—H2B108.7C11—C12—H12119.9
H2A—C2—H2B107.6C12—C13—C14120.2 (6)
C4—C3—C2115.9 (6)C12—C13—C15120.6 (7)
C4—C3—H3A108.3C14—C13—C15119.1 (7)
C2—C3—H3A108.3C13—C14—C9120.6 (6)
C4—C3—H3B108.3C13—C14—H14119.7
C2—C3—H3B108.3C9—C14—H14119.7
H3A—C3—H3B107.4F2'—C15—F1'109.0 (9)
C3—C4—C5115.0 (6)F2'—C15—F1126.4 (9)
C3—C4—H4A108.5F1'—C15—F146.3 (8)
C5—C4—H4A108.5F2'—C15—F347.0 (8)
C3—C4—H4B108.5F1'—C15—F3127.7 (10)
C5—C4—H4B108.5F1—C15—F3104.7 (12)
H4A—C4—H4B107.5F2'—C15—F263.7 (8)
C4—C5—C6113.7 (5)F1'—C15—F258.2 (8)
C4—C5—H5A108.8F1—C15—F2102.9 (11)
C6—C5—H5A108.8F3—C15—F2108.7 (12)
C4—C5—H5B108.8F2'—C15—F3'103.3 (10)
C6—C5—H5B108.8F1'—C15—F3'98.7 (10)
H5A—C5—H5B107.7F1—C15—F3'54.2 (8)
C7—C6—C1119.0 (4)F3—C15—F3'59.2 (9)
C7—C6—C5122.0 (4)F2—C15—F3'142.0 (8)
C1—C6—C5118.9 (4)F2'—C15—C13117.3 (7)
C6—C7—C8119.2 (4)F1'—C15—C13114.9 (8)
C6—C7—C9123.9 (4)F1—C15—C13116.2 (9)
C8—C7—C9116.9 (4)F3—C15—C13117.3 (8)
O1—C8—N2119.7 (4)F2—C15—C13106.0 (8)
O1—C8—C7125.1 (4)F3'—C15—C13111.4 (7)
N2—C8—C7115.2 (4)
C1—N1—N2—C80.0 (7)C8—C7—C9—C10119.0 (5)
N2—N1—C1—C62.7 (6)C6—C7—C9—C14119.2 (5)
N2—N1—C1—C2−175.5 (4)C8—C7—C9—C14−60.3 (6)
N1—C1—C2—C3−170.9 (5)C14—C9—C10—C11−1.9 (9)
C6—C1—C2—C310.9 (8)C7—C9—C10—C11178.7 (5)
C1—C2—C3—C4−34.6 (9)C9—C10—C11—C120.9 (10)
C2—C3—C4—C552.9 (10)C10—C11—C12—C130.3 (11)
C3—C4—C5—C6−44.3 (8)C11—C12—C13—C14−0.4 (10)
N1—C1—C6—C7−2.3 (7)C11—C12—C13—C15177.2 (7)
C2—C1—C6—C7175.7 (4)C12—C13—C14—C9−0.6 (8)
N1—C1—C6—C5177.4 (4)C15—C13—C14—C9−178.3 (5)
C2—C1—C6—C5−4.5 (7)C10—C9—C14—C131.8 (8)
C4—C5—C6—C7−159.9 (5)C7—C9—C14—C13−178.9 (5)
C4—C5—C6—C120.4 (7)C12—C13—C15—F2'−90.7 (11)
C1—C6—C7—C8−0.6 (6)C14—C13—C15—F2'86.9 (12)
C5—C6—C7—C8179.6 (4)C12—C13—C15—F1'39.4 (13)
C1—C6—C7—C9179.9 (4)C14—C13—C15—F1'−142.9 (10)
C5—C6—C7—C90.2 (7)C12—C13—C15—F191.1 (14)
N1—N2—C8—O1177.9 (4)C14—C13—C15—F1−91.3 (14)
N1—N2—C8—C7−2.7 (7)C12—C13—C15—F3−144.0 (13)
C6—C7—C8—O1−177.8 (4)C14—C13—C15—F333.7 (15)
C9—C7—C8—O11.7 (7)C12—C13—C15—F2−22.5 (12)
C6—C7—C8—N22.9 (6)C14—C13—C15—F2155.2 (10)
C9—C7—C8—N2−177.6 (4)C12—C13—C15—F3'150.6 (10)
C6—C7—C9—C10−61.5 (7)C14—C13—C15—F3'−31.8 (12)
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.91 (4)1.88 (4)2.783 (5)178 (5)
C12—H12···F3'ii0.932.513.362152
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H2⋯O1i0.91 (4)1.88 (4)2.783 (5)178 (5)
C12—H12⋯F3′ii0.932.513.362152

Symmetry codes: (i) ; (ii) .

  2 in total

Review 1.  Pharmacologically active pyridazine derivatives. Part 2.

Authors:  G Heinisch; H Kopelent-Frank
Journal:  Prog Med Chem       Date:  1992

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
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1.  Crystal structure of (E)-3-({6-[2-(4-chloro-phen-yl)ethen-yl]-3-oxo-2,3-di-hydro-pyridazin-4-yl}meth-yl)pyridin-1-ium chloride dihydrate.

Authors:  Said Daoui; Emine Berrin Çınar; Necmi Dege; Noureddine Benchat; Eiad Saif; Khalid Karrouchi
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2022-03-31
  1 in total

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