Literature DB >> 22904959

(1S,3R)-3-Isobutyl-2,3-dihydro-spiro[benzo[f]isoindole-1,3'-indoline]-2',4,9-trione methanol monosolvate.

Garima Sharma, S Vasanth Kumar, Habibah A Wahab, Mohd Mustaqim Rosli, Hoong-Kun Fun.   

Abstract

In the title compound, C(23)H(20)N(2)O(3)·CH(3)OH, the hexa-hydro-1H-benzo[f]isoindole and indoline rings are planar, with maximum deviations of 0.092 (1) and -0.095 (1) Å, respectively. The dihedral angle between these two rings is 88.03 (4)°. An O-H⋯N inter-action links the main mol-ecule and the methanol solvent mol-ecule. An intra-molecular C-H⋯O inter-action forms an S(6) ring motif. In the crystal, the mol-ecules form two-dimensional layers parallel to the bc plane through N-H⋯O and C-H⋯O inter-actions.

Entities:  

Year:  2012        PMID: 22904959      PMCID: PMC3414972          DOI: 10.1107/S1600536812032643

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


Related literature

For biological activities of naphtho­quinones, see: Babula et al. (2007 ▶). For detailed literature on naphtho­quinone chemistry, see: Chen et al. (2011 ▶); Silva et al. (2002 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C23H20N2O3·CH4O M = 404.45 Monoclinic, a = 10.8485 (2) Å b = 11.9605 (2) Å c = 16.5705 (3) Å β = 111.246 (1)° V = 2003.95 (6) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 100 K 0.32 × 0.20 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.971, T max = 0.990 23197 measured reflections 5871 independent reflections 4460 reflections with I > 2σ(I) R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.135 S = 1.03 5871 reflections 286 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.63 e Å−3 Δρmin = −0.46 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536812032643/xu5595sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032643/xu5595Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812032643/xu5595Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C23H20N2O3·CH4OF(000) = 856
Mr = 404.45Dx = 1.341 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7290 reflections
a = 10.8485 (2) Åθ = 2.6–30.1°
b = 11.9605 (2) ŵ = 0.09 mm1
c = 16.5705 (3) ÅT = 100 K
β = 111.246 (1)°Block, brown
V = 2003.95 (6) Å30.32 × 0.20 × 0.11 mm
Z = 4
Bruker SMART APEXII CCD area-detector diffractometer5871 independent reflections
Radiation source: fine-focus sealed tube4460 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −15→14
Tmin = 0.971, Tmax = 0.990k = −14→16
23197 measured reflectionsl = −23→23
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0597P)2 + 0.9585P] where P = (Fo2 + 2Fc2)/3
5871 reflections(Δ/σ)max < 0.001
286 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = −0.46 e Å3
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
O10.09694 (11)0.90322 (10)0.51378 (7)0.0300 (3)
O20.56629 (10)1.07980 (8)0.70838 (7)0.0186 (2)
O30.35764 (11)1.07705 (9)0.83896 (7)0.0235 (2)
N10.33921 (12)0.82889 (10)0.78597 (8)0.0160 (2)
N20.56151 (12)1.00095 (10)0.91874 (8)0.0187 (3)
C10.40186 (14)1.06328 (11)0.56677 (9)0.0159 (3)
C20.46388 (15)1.13840 (12)0.52980 (9)0.0187 (3)
H2A0.54691.16980.56400.022*
C30.40491 (16)1.16770 (12)0.44316 (10)0.0219 (3)
H3A0.44691.21980.41830.026*
C40.28436 (16)1.12071 (13)0.39287 (10)0.0234 (3)
H4A0.24501.13990.33340.028*
C50.22110 (16)1.04605 (13)0.42882 (9)0.0218 (3)
H5A0.13851.01460.39400.026*
C60.27860 (14)1.01691 (11)0.51630 (9)0.0179 (3)
C70.20717 (15)0.93985 (12)0.55492 (9)0.0198 (3)
C80.27704 (14)0.90981 (12)0.64722 (9)0.0172 (3)
C90.22425 (14)0.83749 (12)0.70212 (9)0.0170 (3)
H9A0.15030.87770.71220.020*
C100.44298 (13)0.91165 (11)0.78621 (9)0.0146 (3)
C110.39672 (14)0.95085 (11)0.69362 (9)0.0155 (3)
C120.46506 (14)1.03460 (11)0.66010 (9)0.0148 (3)
C130.17636 (14)0.72159 (12)0.66517 (9)0.0177 (3)
H13A0.25080.68150.65700.021*
H13B0.10610.73070.60740.021*
C140.12248 (14)0.64910 (12)0.72118 (10)0.0184 (3)
H14A0.18870.64840.78170.022*
C15−0.00825 (16)0.69353 (14)0.72296 (12)0.0297 (4)
H15A−0.03980.64430.75870.044*
H15B−0.07380.69570.66390.044*
H15C0.00480.76910.74750.044*
C160.10456 (16)0.52942 (13)0.68612 (11)0.0238 (3)
H16A0.06290.48390.71830.036*
H16B0.19110.49770.69290.036*
H16C0.04820.53000.62460.036*
C170.44567 (14)1.00939 (12)0.84967 (9)0.0170 (3)
C180.58027 (13)0.86393 (11)0.82701 (9)0.0151 (3)
C190.64232 (14)0.77902 (12)0.79995 (9)0.0182 (3)
H19A0.60090.74480.74500.022*
C200.76752 (15)0.74465 (13)0.85537 (10)0.0223 (3)
H20A0.81260.68720.83760.027*
C210.82649 (15)0.79390 (14)0.93626 (11)0.0252 (3)
H21A0.91060.76800.97370.030*
C220.76496 (15)0.88039 (13)0.96365 (10)0.0232 (3)
H22A0.80560.91401.01890.028*
C230.64231 (14)0.91542 (12)0.90724 (9)0.0172 (3)
O40.31230 (12)0.84323 (11)0.94796 (8)0.0309 (3)
C240.1798 (2)0.8342 (2)0.93687 (13)0.0425 (5)
H24A0.15070.75670.92260.064*
H24B0.12740.88350.88960.064*
H24C0.16760.85610.99050.064*
H1N10.3759 (17)0.7609 (16)0.7870 (11)0.021 (4)*
H1N20.587 (2)1.0493 (17)0.9621 (13)0.031 (5)*
H1O40.317 (2)0.842 (2)0.8928 (17)0.056 (7)*
U11U22U33U12U13U23
O10.0248 (6)0.0283 (6)0.0245 (6)−0.0059 (5)−0.0059 (5)0.0056 (5)
O20.0176 (5)0.0176 (5)0.0178 (5)−0.0019 (4)0.0029 (4)−0.0001 (4)
O30.0241 (6)0.0198 (5)0.0255 (6)0.0038 (4)0.0076 (5)−0.0032 (4)
N10.0158 (6)0.0149 (6)0.0149 (5)−0.0019 (4)0.0027 (5)−0.0005 (4)
N20.0202 (6)0.0187 (6)0.0149 (6)−0.0024 (5)0.0036 (5)−0.0056 (5)
C10.0193 (7)0.0131 (6)0.0137 (6)0.0038 (5)0.0042 (5)−0.0008 (5)
C20.0237 (7)0.0154 (7)0.0175 (7)0.0014 (5)0.0078 (6)−0.0017 (5)
C30.0307 (8)0.0182 (7)0.0188 (7)0.0041 (6)0.0114 (6)0.0035 (5)
C40.0309 (8)0.0223 (7)0.0152 (7)0.0071 (6)0.0060 (6)0.0032 (5)
C50.0246 (7)0.0191 (7)0.0163 (7)0.0037 (6)0.0009 (6)−0.0003 (5)
C60.0212 (7)0.0138 (6)0.0155 (6)0.0036 (5)0.0028 (5)−0.0003 (5)
C70.0207 (7)0.0150 (6)0.0176 (7)0.0002 (5)−0.0004 (6)0.0002 (5)
C80.0180 (7)0.0141 (6)0.0157 (6)0.0005 (5)0.0018 (5)0.0005 (5)
C90.0148 (6)0.0164 (6)0.0165 (6)−0.0011 (5)0.0017 (5)−0.0002 (5)
C100.0151 (6)0.0139 (6)0.0126 (6)−0.0014 (5)0.0024 (5)−0.0011 (5)
C110.0176 (6)0.0136 (6)0.0130 (6)0.0012 (5)0.0026 (5)0.0000 (5)
C120.0166 (6)0.0118 (6)0.0145 (6)0.0020 (5)0.0040 (5)−0.0006 (5)
C130.0155 (6)0.0171 (7)0.0168 (6)−0.0019 (5)0.0013 (5)−0.0012 (5)
C140.0161 (6)0.0182 (7)0.0189 (7)−0.0016 (5)0.0039 (5)−0.0015 (5)
C150.0235 (8)0.0269 (8)0.0410 (10)−0.0014 (6)0.0146 (7)−0.0059 (7)
C160.0257 (8)0.0176 (7)0.0269 (8)−0.0032 (6)0.0080 (6)−0.0015 (6)
C170.0194 (7)0.0145 (6)0.0172 (6)−0.0024 (5)0.0066 (6)−0.0010 (5)
C180.0156 (6)0.0142 (6)0.0144 (6)−0.0005 (5)0.0043 (5)0.0025 (5)
C190.0203 (7)0.0163 (7)0.0190 (7)−0.0016 (5)0.0085 (6)0.0020 (5)
C200.0215 (7)0.0187 (7)0.0298 (8)0.0030 (6)0.0130 (6)0.0069 (6)
C210.0166 (7)0.0272 (8)0.0285 (8)0.0015 (6)0.0043 (6)0.0110 (6)
C220.0198 (7)0.0275 (8)0.0172 (7)−0.0036 (6)0.0004 (6)0.0033 (6)
C230.0180 (7)0.0174 (7)0.0152 (6)−0.0026 (5)0.0048 (5)0.0019 (5)
O40.0261 (6)0.0436 (7)0.0229 (6)−0.0067 (5)0.0087 (5)−0.0121 (5)
C240.0354 (10)0.0640 (14)0.0313 (10)−0.0139 (9)0.0161 (8)−0.0126 (9)
O1—C71.2231 (18)C11—C121.470 (2)
O2—C121.2254 (17)C13—C141.532 (2)
O3—C171.2147 (18)C13—H13A0.9900
N1—C91.4969 (18)C13—H13B0.9900
N1—C101.4979 (18)C14—C151.525 (2)
N1—H1N10.902 (19)C14—C161.531 (2)
N2—C171.3627 (19)C14—H14A1.0000
N2—C231.4043 (19)C15—H15A0.9800
N2—H1N20.88 (2)C15—H15B0.9800
C1—C21.391 (2)C15—H15C0.9800
C1—C61.409 (2)C16—H16A0.9800
C1—C121.4870 (19)C16—H16B0.9800
C2—C31.388 (2)C16—H16C0.9800
C2—H2A0.9500C18—C191.380 (2)
C3—C41.390 (2)C18—C231.3969 (19)
C3—H3A0.9500C19—C201.398 (2)
C4—C51.386 (2)C19—H19A0.9500
C4—H4A0.9500C20—C211.390 (2)
C5—C61.3989 (19)C20—H20A0.9500
C5—H5A0.9500C21—C221.393 (2)
C6—C71.490 (2)C21—H21A0.9500
C7—C81.484 (2)C22—C231.385 (2)
C8—C111.3395 (19)C22—H22A0.9500
C8—C91.510 (2)O4—C241.386 (2)
C9—C131.528 (2)O4—H1O40.93 (3)
C9—H9A1.0000C24—H24A0.9800
C10—C111.5059 (19)C24—H24B0.9800
C10—C181.5072 (19)C24—H24C0.9800
C10—C171.5656 (19)
C9—N1—C10109.25 (11)C14—C13—H13A108.6
C9—N1—H1N1107.0 (11)C9—C13—H13B108.6
C10—N1—H1N1105.6 (12)C14—C13—H13B108.6
C17—N2—C23111.78 (12)H13A—C13—H13B107.5
C17—N2—H1N2123.9 (13)C15—C14—C16110.01 (13)
C23—N2—H1N2123.9 (13)C15—C14—C13112.09 (13)
C2—C1—C6119.98 (13)C16—C14—C13108.85 (12)
C2—C1—C12119.52 (13)C15—C14—H14A108.6
C6—C1—C12120.48 (13)C16—C14—H14A108.6
C3—C2—C1120.22 (14)C13—C14—H14A108.6
C3—C2—H2A119.9C14—C15—H15A109.5
C1—C2—H2A119.9C14—C15—H15B109.5
C2—C3—C4119.93 (15)H15A—C15—H15B109.5
C2—C3—H3A120.0C14—C15—H15C109.5
C4—C3—H3A120.0H15A—C15—H15C109.5
C5—C4—C3120.53 (14)H15B—C15—H15C109.5
C5—C4—H4A119.7C14—C16—H16A109.5
C3—C4—H4A119.7C14—C16—H16B109.5
C4—C5—C6120.12 (14)H16A—C16—H16B109.5
C4—C5—H5A119.9C14—C16—H16C109.5
C6—C5—H5A119.9H16A—C16—H16C109.5
C5—C6—C1119.20 (14)H16B—C16—H16C109.5
C5—C6—C7119.56 (13)O3—C17—N2127.52 (13)
C1—C6—C7121.22 (12)O3—C17—C10125.24 (13)
O1—C7—C8121.25 (14)N2—C17—C10107.21 (12)
O1—C7—C6122.55 (13)C19—C18—C23120.68 (13)
C8—C7—C6116.20 (12)C19—C18—C10130.70 (13)
C11—C8—C7121.98 (14)C23—C18—C10108.48 (12)
C11—C8—C9111.37 (12)C18—C19—C20118.38 (14)
C7—C8—C9126.57 (12)C18—C19—H19A120.8
N1—C9—C8103.19 (11)C20—C19—H19A120.8
N1—C9—C13110.95 (11)C21—C20—C19120.48 (15)
C8—C9—C13115.22 (12)C21—C20—H20A119.8
N1—C9—H9A109.1C19—C20—H20A119.8
C8—C9—H9A109.1C20—C21—C22121.43 (14)
C13—C9—H9A109.1C20—C21—H21A119.3
N1—C10—C11103.32 (10)C22—C21—H21A119.3
N1—C10—C18111.75 (11)C23—C22—C21117.46 (14)
C11—C10—C18119.03 (12)C23—C22—H22A121.3
N1—C10—C17109.04 (11)C21—C22—H22A121.3
C11—C10—C17111.72 (11)C22—C23—C18121.51 (14)
C18—C10—C17101.93 (11)C22—C23—N2128.54 (14)
C8—C11—C12123.34 (12)C18—C23—N2109.95 (12)
C8—C11—C10111.50 (13)C24—O4—H1O4106.8 (15)
C12—C11—C10124.73 (12)O4—C24—H24A109.5
O2—C12—C11120.62 (12)O4—C24—H24B109.5
O2—C12—C1122.93 (13)H24A—C24—H24B109.5
C11—C12—C1116.40 (12)O4—C24—H24C109.5
C9—C13—C14114.79 (12)H24A—C24—H24C109.5
C9—C13—H13A108.6H24B—C24—H24C109.5
C6—C1—C2—C3−0.2 (2)C10—C11—C12—O2−1.2 (2)
C12—C1—C2—C3−178.75 (13)C8—C11—C12—C1−7.1 (2)
C1—C2—C3—C4−0.9 (2)C10—C11—C12—C1−178.98 (12)
C2—C3—C4—C51.1 (2)C2—C1—C12—O25.0 (2)
C3—C4—C5—C6−0.3 (2)C6—C1—C12—O2−173.59 (13)
C4—C5—C6—C1−0.8 (2)C2—C1—C12—C11−177.33 (13)
C4—C5—C6—C7177.73 (14)C6—C1—C12—C114.10 (19)
C2—C1—C6—C51.0 (2)N1—C9—C13—C1463.48 (16)
C12—C1—C6—C5179.55 (13)C8—C9—C13—C14−179.76 (12)
C2—C1—C6—C7−177.48 (13)C9—C13—C14—C1569.24 (16)
C12—C1—C6—C71.1 (2)C9—C13—C14—C16−168.83 (12)
C5—C6—C7—O1−2.5 (2)C23—N2—C17—O3−177.45 (15)
C1—C6—C7—O1175.95 (15)C23—N2—C17—C104.59 (16)
C5—C6—C7—C8177.82 (13)N1—C10—C17—O3−67.24 (18)
C1—C6—C7—C8−3.7 (2)C11—C10—C17—O346.32 (19)
O1—C7—C8—C11−178.74 (15)C18—C10—C17—O3174.49 (14)
C6—C7—C8—C110.9 (2)N1—C10—C17—N2110.78 (13)
O1—C7—C8—C9−2.3 (2)C11—C10—C17—N2−135.65 (13)
C6—C7—C8—C9177.34 (13)C18—C10—C17—N2−7.49 (14)
C10—N1—C9—C811.53 (14)N1—C10—C18—C1967.08 (19)
C10—N1—C9—C13135.47 (12)C11—C10—C18—C19−53.3 (2)
C11—C8—C9—N1−7.48 (16)C17—C10—C18—C19−176.60 (14)
C7—C8—C9—N1175.79 (13)N1—C10—C18—C23−108.46 (13)
C11—C8—C9—C13−128.56 (13)C11—C10—C18—C23131.21 (13)
C7—C8—C9—C1354.71 (19)C17—C10—C18—C237.86 (14)
C9—N1—C10—C11−11.27 (14)C23—C18—C19—C201.1 (2)
C9—N1—C10—C18−140.42 (12)C10—C18—C19—C20−173.99 (14)
C9—N1—C10—C17107.68 (12)C18—C19—C20—C211.1 (2)
C7—C8—C11—C124.6 (2)C19—C20—C21—C22−1.7 (2)
C9—C8—C11—C12−172.30 (13)C20—C21—C22—C230.2 (2)
C7—C8—C11—C10177.44 (13)C21—C22—C23—C182.0 (2)
C9—C8—C11—C100.53 (17)C21—C22—C23—N2−179.06 (14)
N1—C10—C11—C86.65 (15)C19—C18—C23—C22−2.7 (2)
C18—C10—C11—C8131.18 (13)C10—C18—C23—C22173.37 (13)
C17—C10—C11—C8−110.43 (14)C19—C18—C23—N2178.20 (13)
N1—C10—C11—C12179.36 (12)C10—C18—C23—N2−5.73 (16)
C18—C10—C11—C12−56.11 (18)C17—N2—C23—C22−178.43 (15)
C17—C10—C11—C1262.28 (18)C17—N2—C23—C180.59 (17)
C8—C11—C12—O2170.65 (14)
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O2i0.903 (19)2.249 (19)3.1410 (16)169.7 (17)
N2—H1N2···O4ii0.89 (2)1.97 (2)2.8346 (18)165 (2)
O4—H1O4···N10.93 (3)1.88 (3)2.8085 (18)174 (2)
C13—H13B···O10.992.563.1919 (18)121
C19—H19A···O3i0.952.573.3368 (18)138
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A DA D—H⋯A
N1—H1N1⋯O2i 0.903 (19)2.249 (19)3.1410 (16)169.7 (17)
N2—H1N2⋯O4ii 0.89 (2)1.97 (2)2.8346 (18)165 (2)
O4—H1O4⋯N10.93 (3)1.88 (3)2.8085 (18)174 (2)
C13—H13B⋯O10.992.563.1919 (18)121
C19—H19A⋯O3i 0.952.573.3368 (18)138

Symmetry codes: (i) ; (ii) .

  4 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Synthesis of new beta-substituted meso-tetraphenylporphyrins via 1,3-dipolar cycloaddition reactions. 1.

Authors:  Ana M G Silva; Augusto C Tomé; Maria G P M S Neves; Artur M S Silva; José A S Cavaleiro
Journal:  J Org Chem       Date:  2002-02-08       Impact factor: 4.354

Review 3.  [Naphthoquinones and their pharmacological properties].

Authors:  P Babula; V Adam; L Havel; R Kizek
Journal:  Ceska Slov Farm       Date:  2007-06

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total
  1 in total

1.  (3'R)-3'-Benzyl-2',3'-dihydro-1H-spiro-[indole-3,1'-naphtho-[2,3-c]pyrrole]-2,4',9'-trione.

Authors:  Garima Sharma; S Vasanth Kumar; Habibah A Wahab; Mohd Mustaqim Rosli; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-08-25
  1 in total

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