Literature DB >> 21582199

2-[(4-tert-Butyl-anilino)(phen-yl)meth-yl]cyclo-hexa-none.

Hoong-Kun Fun, Suchada Chantrapromma, Sankappa Rai, Prakash Shetty, Arun M Isloor.   

Abstract

In the mol-ecule of the title compound, C(23)H(29)NO, the cyclo-hexa-none ring has been distorted from the standard chair conformation by the ketone group such that part of the ring is almost flat. The remaining [(4-tert-butyl-anilino)(phen-yl)meth-yl] portion of the mol-ecule is in an equatorial position on the cyclo-hexa-none ring. The dihedral angle between the two benzene rings is 81.52 (8)°. In the crystal packing, mol-ecules are linked by N-H⋯O hydrogen bonds into infinite one-dimensional chains along the a axis and these chains are stacked down the c axis. The crystal structure is further stabilized by weak C-H⋯O and C-H⋯π inter-actions.

Entities:  

Year:  2009        PMID： 21582199      PMCID： PMC2968565          DOI： 10.1107/S1600536809004954

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


Related literature

For values of bond lengths, see: Allen et al. (1987 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For information on the Mannich reaction, see: Kobayashi & Ishitani (1999 ▶); Bohme & Haake (1976 ▶). For background to the bioactivity and applications of beta-amino carbonyl compounds, see, for example: Arend et al. (1988 ▶); Isloor, Sunil et al. (2009 ▶); Isloor, Kalluraya et al. (2009 ▶); Jadhav et al. (2008 ▶); Kalluraya et al. (2001 ▶). For puckering parameters, see: Cremer & Pople, (1975 ▶). For the stability of the temperature controller, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C23H29NO M = 335.47 Triclinic, a = 6.5315 (2) Å b = 12.3946 (3) Å c = 12.8853 (3) Å α = 62.973 (1)° β = 86.347 (2)° γ = 85.103 (2)° V = 925.46 (4) Å3 Z = 2 Mo Kα radiation μ = 0.07 mm−1 T = 100 K 0.52 × 0.41 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.953, T max = 0.992 17722 measured reflections 4449 independent reflections 3584 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.124 S = 1.07 4449 reflections 233 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.39 e Å−3 Δρmin = −0.23 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004954/sj2573sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004954/sj2573Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C23H29NOZ = 2
Mr = 335.47F(000) = 364
Triclinic, P1Dx = 1.204 Mg m−3
Hall symbol: -P 1Melting point = 439–441 K
a = 6.5315 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.3946 (3) ÅCell parameters from 4449 reflections
c = 12.8853 (3) Åθ = 1.8–28.0°
α = 62.973 (1)°µ = 0.07 mm−1
β = 86.347 (2)°T = 100 K
γ = 85.103 (2)°Plate, colorless
V = 925.46 (4) Å30.52 × 0.41 × 0.11 mm
Bruker SMART APEXII CCD area-detector diffractometer4449 independent reflections
Radiation source: fine-focus sealed tube3584 reflections with I > 2σ(I)
graphiteRint = 0.027
Detector resolution: 8.33 pixels mm-1θmax = 28.0°, θmin = 1.8°
ω scansh = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −16→16
Tmin = 0.953, Tmax = 0.992l = −16→16
17722 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0465P)2 + 0.607P] where P = (Fo2 + 2Fc2)/3
4449 reflections(Δ/σ)max < 0.001
233 parametersΔρmax = 0.39 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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*/Ueq
O11.32798 (15)0.71893 (10)0.43723 (9)0.0200 (2)
N10.75282 (19)0.58289 (11)0.55557 (10)0.0157 (3)
C11.1976 (2)0.75037 (12)0.36390 (12)0.0147 (3)
C21.2523 (2)0.82454 (13)0.23594 (12)0.0183 (3)
H2A1.29740.76910.20370.022*
H2B1.36800.87140.22990.022*
C31.0809 (2)0.91152 (13)0.16072 (12)0.0176 (3)
H3A1.06220.98160.17590.021*
H3B1.11920.93960.07900.021*
C40.8804 (2)0.84862 (14)0.18722 (12)0.0189 (3)
H4A0.89680.78090.16840.023*
H4B0.77270.90510.13960.023*
C50.8193 (2)0.80271 (14)0.31607 (12)0.0194 (3)
H5A0.68750.76700.33080.023*
H5B0.80420.87070.33460.023*
C60.9799 (2)0.70785 (12)0.39536 (12)0.0146 (3)
H6A0.97810.63840.37850.018*
C70.9298 (2)0.65755 (12)0.52741 (12)0.0144 (3)
H7A1.04740.60320.56820.017*
C80.9016 (2)0.75555 (12)0.56920 (12)0.0153 (3)
C91.0660 (2)0.78409 (13)0.61390 (12)0.0183 (3)
H9A1.19300.74190.62000.022*
C101.0424 (3)0.87519 (14)0.64956 (13)0.0220 (3)
H10A1.15350.89410.67850.026*
C110.8531 (3)0.93747 (14)0.64179 (13)0.0233 (3)
H11A0.83770.99940.66410.028*
C120.6871 (2)0.90756 (14)0.60086 (13)0.0216 (3)
H12A0.55920.94800.59770.026*
C130.7104 (2)0.81741 (13)0.56449 (12)0.0184 (3)
H13A0.59800.79810.53680.022*
C140.6904 (2)0.51586 (12)0.67217 (12)0.0147 (3)
C150.4914 (2)0.47478 (13)0.69928 (12)0.0159 (3)
H15A0.40040.49530.63960.019*
C160.4279 (2)0.40402 (12)0.81375 (12)0.0165 (3)
H16A0.29450.37880.82880.020*
C170.5577 (2)0.36937 (12)0.90732 (12)0.0159 (3)
C180.7558 (2)0.41071 (13)0.87917 (12)0.0173 (3)
H18A0.84720.38920.93890.021*
C190.8215 (2)0.48285 (13)0.76503 (12)0.0172 (3)
H19A0.95410.50940.75030.021*
C200.4898 (2)0.28876 (13)1.03410 (12)0.0178 (3)
C210.5531 (3)0.15560 (14)1.06508 (14)0.0280 (4)
H21A0.48730.13271.01420.042*
H21B0.51210.10481.14440.042*
H21C0.69960.14611.05600.042*
C220.2558 (2)0.30252 (16)1.05089 (14)0.0277 (4)
H22A0.18890.27031.00780.042*
H22B0.21330.38691.02330.042*
H22C0.21910.25901.13210.042*
C230.5907 (3)0.32236 (15)1.11896 (13)0.0235 (3)
H23A0.73670.30551.11690.035*
H23B0.53700.27541.19650.035*
H23C0.56160.40721.09660.035*
H1N10.646 (3)0.6162 (18)0.5096 (17)0.030 (5)*
U11U22U33U12U13U23
O10.0126 (5)0.0257 (6)0.0188 (5)−0.0004 (4)−0.0006 (4)−0.0076 (4)
N10.0128 (6)0.0171 (6)0.0142 (6)−0.0028 (5)−0.0003 (5)−0.0043 (5)
C10.0119 (6)0.0148 (6)0.0168 (7)0.0009 (5)0.0008 (5)−0.0072 (5)
C20.0135 (7)0.0216 (7)0.0163 (7)−0.0015 (5)0.0028 (5)−0.0059 (6)
C30.0182 (7)0.0177 (7)0.0140 (7)−0.0012 (5)0.0004 (5)−0.0048 (6)
C40.0169 (7)0.0221 (7)0.0150 (7)−0.0011 (6)−0.0028 (5)−0.0058 (6)
C50.0121 (7)0.0243 (8)0.0161 (7)−0.0004 (5)0.0000 (5)−0.0044 (6)
C60.0121 (6)0.0158 (6)0.0147 (7)−0.0012 (5)−0.0003 (5)−0.0057 (5)
C70.0110 (6)0.0150 (6)0.0140 (6)−0.0008 (5)−0.0001 (5)−0.0039 (5)
C80.0159 (7)0.0151 (6)0.0117 (6)−0.0024 (5)0.0017 (5)−0.0032 (5)
C90.0155 (7)0.0205 (7)0.0153 (7)−0.0028 (5)0.0007 (5)−0.0048 (6)
C100.0262 (8)0.0234 (8)0.0158 (7)−0.0079 (6)−0.0007 (6)−0.0074 (6)
C110.0362 (9)0.0175 (7)0.0152 (7)−0.0017 (6)0.0016 (6)−0.0067 (6)
C120.0236 (8)0.0206 (7)0.0161 (7)0.0040 (6)0.0006 (6)−0.0054 (6)
C130.0162 (7)0.0207 (7)0.0151 (7)−0.0008 (5)0.0001 (5)−0.0056 (6)
C140.0142 (7)0.0125 (6)0.0156 (7)0.0002 (5)0.0012 (5)−0.0051 (5)
C150.0137 (7)0.0160 (7)0.0163 (7)−0.0005 (5)−0.0025 (5)−0.0058 (5)
C160.0126 (6)0.0156 (7)0.0199 (7)−0.0018 (5)0.0014 (5)−0.0068 (6)
C170.0160 (7)0.0138 (6)0.0157 (7)0.0006 (5)0.0021 (5)−0.0054 (5)
C180.0148 (7)0.0189 (7)0.0162 (7)0.0010 (5)−0.0027 (5)−0.0063 (6)
C190.0116 (6)0.0193 (7)0.0187 (7)−0.0016 (5)0.0006 (5)−0.0070 (6)
C200.0168 (7)0.0176 (7)0.0150 (7)−0.0005 (5)0.0018 (5)−0.0042 (6)
C210.0387 (10)0.0179 (7)0.0216 (8)−0.0027 (7)0.0058 (7)−0.0046 (6)
C220.0184 (8)0.0376 (9)0.0187 (8)−0.0029 (7)0.0047 (6)−0.0059 (7)
C230.0262 (8)0.0249 (8)0.0168 (7)−0.0020 (6)0.0009 (6)−0.0072 (6)
O1—C11.2172 (17)C11—C121.382 (2)
N1—C141.3996 (18)C11—H11A0.9300
N1—C71.4657 (17)C12—C131.389 (2)
N1—H1N10.89 (2)C12—H12A0.9300
C1—C21.5149 (19)C13—H13A0.9300
C1—C61.5244 (19)C14—C191.399 (2)
C2—C31.529 (2)C14—C151.4019 (19)
C2—H2A0.9700C15—C161.388 (2)
C2—H2B0.9700C15—H15A0.9300
C3—C41.521 (2)C16—C171.398 (2)
C3—H3A0.9700C16—H16A0.9300
C3—H3B0.9700C17—C181.397 (2)
C4—C51.5281 (19)C17—C201.5376 (19)
C4—H4A0.9700C18—C191.392 (2)
C4—H4B0.9700C18—H18A0.9300
C5—C61.537 (2)C19—H19A0.9300
C5—H5A0.9700C20—C231.535 (2)
C5—H5B0.9700C20—C221.535 (2)
C6—C71.5462 (18)C20—C211.536 (2)
C6—H6A0.9800C21—H21A0.9600
C7—C81.5307 (19)C21—H21B0.9600
C7—H7A0.9800C21—H21C0.9600
C8—C91.392 (2)C22—H22A0.9600
C8—C131.398 (2)C22—H22B0.9600
C9—C101.394 (2)C22—H22C0.9600
C9—H9A0.9300C23—H23A0.9600
C10—C111.384 (2)C23—H23B0.9600
C10—H10A0.9300C23—H23C0.9600
C14—N1—C7119.50 (12)C12—C11—C10119.94 (14)
C14—N1—H1N1111.8 (13)C12—C11—H11A120.0
C7—N1—H1N1115.8 (13)C10—C11—H11A120.0
O1—C1—C2120.57 (12)C11—C12—C13120.31 (14)
O1—C1—C6121.72 (12)C11—C12—H12A119.8
C2—C1—C6117.49 (12)C13—C12—H12A119.8
C1—C2—C3116.04 (12)C12—C13—C8120.49 (14)
C1—C2—H2A108.3C12—C13—H13A119.8
C3—C2—H2A108.3C8—C13—H13A119.8
C1—C2—H2B108.3C19—C14—N1122.84 (13)
C3—C2—H2B108.3C19—C14—C15117.33 (12)
H2A—C2—H2B107.4N1—C14—C15119.78 (13)
C4—C3—C2110.53 (12)C16—C15—C14121.08 (13)
C4—C3—H3A109.5C16—C15—H15A119.5
C2—C3—H3A109.5C14—C15—H15A119.5
C4—C3—H3B109.5C15—C16—C17122.24 (13)
C2—C3—H3B109.5C15—C16—H16A118.9
H3A—C3—H3B108.1C17—C16—H16A118.9
C3—C4—C5110.11 (12)C18—C17—C16116.14 (13)
C3—C4—H4A109.6C18—C17—C20121.38 (13)
C5—C4—H4A109.6C16—C17—C20122.47 (13)
C3—C4—H4B109.6C19—C18—C17122.45 (13)
C5—C4—H4B109.6C19—C18—H18A118.8
H4A—C4—H4B108.2C17—C18—H18A118.8
C4—C5—C6111.74 (12)C18—C19—C14120.75 (13)
C4—C5—H5A109.3C18—C19—H19A119.6
C6—C5—H5A109.3C14—C19—H19A119.6
C4—C5—H5B109.3C23—C20—C22107.70 (13)
C6—C5—H5B109.3C23—C20—C21108.66 (13)
H5A—C5—H5B107.9C22—C20—C21109.07 (13)
C1—C6—C5112.30 (11)C23—C20—C17111.26 (12)
C1—C6—C7112.15 (11)C22—C20—C17111.07 (12)
C5—C6—C7114.88 (11)C21—C20—C17109.02 (12)
C1—C6—H6A105.5C20—C21—H21A109.5
C5—C6—H6A105.5C20—C21—H21B109.5
C7—C6—H6A105.5H21A—C21—H21B109.5
N1—C7—C8113.40 (11)C20—C21—H21C109.5
N1—C7—C6108.22 (11)H21A—C21—H21C109.5
C8—C7—C6113.68 (11)H21B—C21—H21C109.5
N1—C7—H7A107.1C20—C22—H22A109.5
C8—C7—H7A107.1C20—C22—H22B109.5
C6—C7—H7A107.1H22A—C22—H22B109.5
C9—C8—C13118.57 (13)C20—C22—H22C109.5
C9—C8—C7120.52 (13)H22A—C22—H22C109.5
C13—C8—C7120.91 (13)H22B—C22—H22C109.5
C8—C9—C10120.75 (14)C20—C23—H23A109.5
C8—C9—H9A119.6C20—C23—H23B109.5
C10—C9—H9A119.6H23A—C23—H23B109.5
C11—C10—C9119.90 (14)C20—C23—H23C109.5
C11—C10—H10A120.1H23A—C23—H23C109.5
C9—C10—H10A120.1H23B—C23—H23C109.5
O1—C1—C2—C3−149.78 (14)C9—C10—C11—C121.3 (2)
C6—C1—C2—C335.51 (18)C10—C11—C12—C13−1.7 (2)
C1—C2—C3—C4−45.58 (17)C11—C12—C13—C80.2 (2)
C2—C3—C4—C558.62 (16)C9—C8—C13—C121.7 (2)
C3—C4—C5—C6−62.20 (16)C7—C8—C13—C12−178.96 (13)
O1—C1—C6—C5148.61 (14)C7—N1—C14—C19−22.0 (2)
C2—C1—C6—C5−36.74 (17)C7—N1—C14—C15160.68 (12)
O1—C1—C6—C717.48 (18)C19—C14—C15—C16−0.1 (2)
C2—C1—C6—C7−167.88 (12)N1—C14—C15—C16177.38 (13)
C4—C5—C6—C149.83 (16)C14—C15—C16—C17−0.5 (2)
C4—C5—C6—C7179.57 (12)C15—C16—C17—C180.3 (2)
C14—N1—C7—C8−59.87 (16)C15—C16—C17—C20−178.69 (13)
C14—N1—C7—C6173.04 (12)C16—C17—C18—C190.4 (2)
C1—C6—C7—N1−161.06 (11)C20—C17—C18—C19179.42 (13)
C5—C6—C7—N169.13 (15)C17—C18—C19—C14−1.0 (2)
C1—C6—C7—C872.02 (15)N1—C14—C19—C18−176.59 (13)
C5—C6—C7—C8−57.80 (16)C15—C14—C19—C180.8 (2)
N1—C7—C8—C9141.87 (13)C18—C17—C20—C2334.25 (18)
C6—C7—C8—C9−93.95 (15)C16—C17—C20—C23−146.77 (14)
N1—C7—C8—C13−37.48 (17)C18—C17—C20—C22154.21 (14)
C6—C7—C8—C1386.69 (15)C16—C17—C20—C22−26.80 (19)
C13—C8—C9—C10−2.1 (2)C18—C17—C20—C21−85.57 (17)
C7—C8—C9—C10178.51 (12)C16—C17—C20—C2193.41 (17)
C8—C9—C10—C110.7 (2)
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O1i0.89 (2)2.35 (2)3.2050 (16)161.6 (19)
C9—H9A···O10.932.593.1146 (19)116
C2—H2A···Cg1ii0.972.603.4992 (19)155
C23—H23C···Cg1iii0.962.993.747 (2)137
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1N1⋯O1i0.89 (2)2.35 (2)3.2050 (16)161.6 (19)
C9—H9A⋯O10.932.593.1146 (19)116
C2—H2A⋯Cg1ii0.972.603.4992 (19)155
C23—H23C⋯Cg1iii0.962.993.747 (2)137

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C14–C19 ring.

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  4 in total
  4 in total

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Authors:  Klaus Harms; M Saeed Abaee; Mohammad M Mojtahedi; A Wahid Mesbah
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-02-17

2.  rac-3-[(3-Chloro-anilino)(4-chloro-phenyl)meth-yl]thian-4-one.

Authors:  Klaus Harms; M Saeed Abaee; Mohammad M Mojtahedi; A Wahid Mesbah
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3.  2-[Anilino(phen-yl)meth-yl]cyclo-heptan-one.

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-12-19

4.  2-[(Anilino)(2-nitro-phen-yl)meth-yl]cyclo-hexa-none.

Authors:  Bagher Eftekhari-Sis; Sahar Mohajer; Orhan Büyükgüngör
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-09-01
  4 in total

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