Literature DB >> 23284473

(1E,2E)-1,2-Bis[(1-benzyloxymethyl-1H-indol-3-yl)methylidene]hydrazine.

Jacob A Myers1, Frank R Fronczek, Steven F Watkins.   

Abstract

The title compound, C(34)H(30)N(4)O(2), lies on an inversion center and consists of two 3-substituted-1H-indole units linked by a 1,2-dimethyl-enehydrazine bridge. It is one of numerous examples in which two aromatic ring systems are joined by this 4-atom bridge. The geometry of the centrosymmetric bridge is: C(arom)-C = 1.444 (3), C=N = 1.284 (3), N-N = 1.414 (4) Å, C(arom)-C=N = 122.6 (2) and C=N-N = 111.9 (2)°. The nine non-H atoms of the indole unit lie in a plane (δ(r.m.s.) = 0.0089 Å) which is twisted 6.0 (2)° with respect to the hydrazine bridge plane. The benzyl-oxymethyl substituents do not lie in the plane of the rest of the mol-ecule and are in a folded rather than an extended conformation. This is described by the three torsion angles in the middle of the C=N-C-O-C(Bz) group, viz. 98.5 (3), -62.1 (3), and -66.3 (2)°.

Entities:  

Year:  2012        PMID： 23284473      PMCID： PMC3515253          DOI： 10.1107/S1600536812042493

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


Related literature

For the synthesis, see: Shui (1994 ▶). For related structures, see: Burke-Laing & Laing (1976 ▶); Mom & de With (1978 ▶); Biswas et al. (1999 ▶); Rizal et al. (2008 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C34H30N4O2 M = 526.62 Monoclinic, a = 12.8518 (10) Å b = 7.9663 (9) Å c = 13.6810 (12) Å β = 103.672 (5)° V = 1361.0 (2) Å3 Z = 2 Mo Kα radiation μ = 0.08 mm−1 T = 90 K 0.18 × 0.10 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor 1997 ▶) T min = 0.986, T max = 0.996 4340 measured reflections 2678 independent reflections 1481 reflections with I > 2σ(I) R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.056 wR(F 2) = 0.126 S = 0.99 2678 reflections 182 parameters H-atom parameters constrained Δρmax = 0.25 e Å−3 Δρmin = −0.25 e Å−3 Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997 ▶); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997 ▶); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042493/pk2449sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042493/pk2449Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812042493/pk2449Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C34H30N4O2F(000) = 556
Mr = 526.62Dx = 1.285 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2472 reflections
a = 12.8518 (10) Åθ = 2.6–26.0°
b = 7.9663 (9) ŵ = 0.08 mm−1
c = 13.6810 (12) ÅT = 90 K
β = 103.672 (5)°Fragment, colorless
V = 1361.0 (2) Å30.18 × 0.10 × 0.05 mm
Z = 2
Nonius KappaCCD diffractometer2678 independent reflections
Radiation source: sealed tube1481 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromatorRint = 0.067
Detector resolution: 9 pixels mm-1θmax = 26.0°, θmin = 3.0°
CCD rotation images, thick slices scansh = −15→15
Absorption correction: multi-scan (HKLSCALEPACK; Otwinowski & Minor 1997)k = −8→9
Tmin = 0.986, Tmax = 0.996l = −16→16
4340 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.126w = 1/[σ2(Fo2) + (0.0483P)2 + 0.249P] where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
2678 reflectionsΔρmax = 0.25 e Å−3
182 parametersΔρmin = −0.25 e Å−3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.0062 (13)
Primary atom site location: structure-invariant direct methods
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.
xyzUiso*/Ueq
N10.02086 (15)0.0030 (3)0.55263 (14)0.0211 (5)
C10.11765 (18)−0.0511 (3)0.57786 (17)0.0206 (6)
H10.15−0.09170.52680.025*
C20.17927 (18)−0.0526 (3)0.68083 (16)0.0191 (6)
C30.14858 (18)−0.0067 (3)0.77188 (17)0.0180 (6)
C40.05355 (19)0.0445 (3)0.79619 (18)0.0207 (6)
H4−0.01080.05380.74520.025*
C50.05426 (19)0.0813 (3)0.89494 (18)0.0236 (6)
H5−0.00980.11780.91150.028*
C60.14857 (19)0.0654 (3)0.97152 (19)0.0258 (7)
H60.1470.09151.03890.031*
C70.24299 (19)0.0127 (3)0.95068 (17)0.0226 (6)
H70.30660.00111.00230.027*
C80.24147 (18)−0.0229 (3)0.85072 (17)0.0182 (6)
N20.32454 (15)−0.0785 (3)0.81007 (14)0.0190 (5)
C90.28592 (19)−0.0961 (3)0.70805 (17)0.0205 (6)
H90.3269−0.1330.66280.025*
C100.43362 (18)−0.1094 (3)0.86494 (18)0.0218 (6)
H10A0.4327−0.16570.92930.026*
H10B0.468−0.18660.82540.026*
O10.49589 (12)0.0398 (2)0.88566 (11)0.0225 (4)
C110.50844 (19)0.1279 (3)0.79804 (18)0.0241 (6)
H11A0.54350.2370.81940.029*
H11B0.43650.1520.75520.029*
C120.57299 (18)0.0365 (3)0.73523 (18)0.0219 (6)
C130.5658 (2)0.0890 (3)0.63721 (18)0.0276 (7)
H130.51680.17540.60920.033*
C140.6293 (2)0.0168 (4)0.57959 (19)0.0329 (7)
H140.62480.05620.51320.039*
C150.6992 (2)−0.1122 (4)0.6180 (2)0.0352 (7)
H150.7423−0.16190.57820.042*
C160.7056 (2)−0.1679 (4)0.71520 (19)0.0328 (7)
H160.7525−0.25760.74190.039*
C170.64369 (19)−0.0929 (3)0.77379 (19)0.0263 (7)
H170.6497−0.13040.84080.032*
U11U22U33U12U13U23
N10.0247 (12)0.0193 (12)0.0164 (10)0.0004 (11)−0.0011 (9)−0.0027 (10)
C10.0221 (14)0.0174 (15)0.0212 (13)−0.0012 (12)0.0030 (11)−0.0005 (11)
C20.0203 (12)0.0162 (14)0.0186 (13)0.0005 (11)0.0004 (10)−0.0009 (11)
C30.0209 (12)0.0141 (14)0.0185 (13)−0.0019 (12)0.0038 (10)0.0015 (11)
C40.0190 (12)0.0189 (14)0.0225 (14)−0.0022 (12)0.0017 (10)0.0011 (12)
C50.0235 (13)0.0229 (16)0.0272 (14)−0.0017 (12)0.0116 (11)0.0002 (12)
C60.0292 (15)0.0261 (17)0.0228 (14)−0.0024 (13)0.0074 (12)−0.0007 (12)
C70.0253 (13)0.0217 (15)0.0189 (13)0.0000 (13)0.0016 (11)−0.0007 (12)
C80.0196 (12)0.0136 (14)0.0218 (13)−0.0007 (12)0.0059 (10)0.0000 (11)
N20.0198 (11)0.0198 (13)0.0161 (11)0.0003 (9)0.0013 (8)−0.0012 (9)
C90.0237 (13)0.0197 (15)0.0172 (13)0.0002 (12)0.0031 (10)−0.0017 (11)
C100.0214 (13)0.0179 (15)0.0242 (14)0.0003 (12)0.0016 (11)0.0000 (12)
O10.0240 (9)0.0201 (10)0.0220 (9)−0.0030 (8)0.0025 (7)−0.0021 (8)
C110.0241 (13)0.0227 (15)0.0252 (14)−0.0006 (12)0.0052 (11)0.0048 (12)
C120.0209 (13)0.0204 (14)0.0224 (13)−0.0035 (12)0.0016 (11)−0.0009 (12)
C130.0292 (14)0.0246 (16)0.0274 (15)−0.0002 (13)0.0031 (12)0.0045 (13)
C140.0357 (15)0.0386 (19)0.0251 (15)−0.0055 (15)0.0088 (12)−0.0007 (14)
C150.0326 (16)0.0410 (19)0.0348 (17)0.0004 (15)0.0136 (13)−0.0079 (15)
C160.0295 (15)0.0346 (18)0.0324 (16)0.0066 (14)0.0036 (12)−0.0025 (14)
C170.0229 (14)0.0330 (17)0.0218 (14)0.0017 (13)0.0030 (11)−0.0008 (13)
N1—C11.284 (3)C9—H90.95
N1—N1i1.414 (4)C10—O11.424 (3)
C1—C21.444 (3)C10—H10A0.99
C1—H10.95C10—H10B0.99
C2—C91.377 (3)O1—C111.431 (3)
C2—C31.440 (3)C11—C121.514 (3)
C3—C41.400 (3)C11—H11A0.99
C3—C81.413 (3)C11—H11B0.99
C4—C51.380 (3)C12—C131.387 (3)
C4—H40.95C12—C171.393 (4)
C5—C61.408 (3)C13—C141.386 (3)
C5—H50.95C13—H130.95
C6—C71.376 (3)C14—C151.384 (4)
C6—H60.95C14—H140.95
C7—C81.392 (3)C15—C161.385 (4)
C7—H70.95C15—H150.95
C8—N21.388 (3)C16—C171.391 (3)
N2—C91.373 (3)C16—H160.95
N2—C101.446 (3)C17—H170.95
C1—N1—N1i111.9 (2)O1—C10—N2113.05 (19)
N1—C1—C2122.6 (2)O1—C10—H10A109
N1—C1—H1118.7N2—C10—H10A109
C2—C1—H1118.7O1—C10—H10B109
C9—C2—C3106.77 (19)N2—C10—H10B109
C9—C2—C1123.2 (2)H10A—C10—H10B107.8
C3—C2—C1130.0 (2)C10—O1—C11114.34 (17)
C4—C3—C8118.2 (2)O1—C11—C12115.2 (2)
C4—C3—C2135.4 (2)O1—C11—H11A108.5
C8—C3—C2106.41 (19)C12—C11—H11A108.5
C5—C4—C3119.3 (2)O1—C11—H11B108.5
C5—C4—H4120.3C12—C11—H11B108.5
C3—C4—H4120.3H11A—C11—H11B107.5
C4—C5—C6121.0 (2)C13—C12—C17118.5 (2)
C4—C5—H5119.5C13—C12—C11118.9 (2)
C6—C5—H5119.5C17—C12—C11122.5 (2)
C7—C6—C5121.3 (2)C12—C13—C14120.8 (2)
C7—C6—H6119.4C12—C13—H13119.6
C5—C6—H6119.4C14—C13—H13119.6
C6—C7—C8117.2 (2)C15—C14—C13120.5 (2)
C6—C7—H7121.4C15—C14—H14119.7
C8—C7—H7121.4C13—C14—H14119.7
N2—C8—C7128.7 (2)C16—C15—C14119.3 (3)
N2—C8—C3108.3 (2)C16—C15—H15120.4
C7—C8—C3123.0 (2)C14—C15—H15120.4
C9—N2—C8108.20 (19)C15—C16—C17120.2 (3)
C9—N2—C10125.7 (2)C15—C16—H16119.9
C8—N2—C10126.11 (19)C17—C16—H16119.9
N2—C9—C2110.3 (2)C16—C17—C12120.7 (2)
N2—C9—H9124.9C16—C17—H17119.6
C2—C9—H9124.9C12—C17—H17119.6
C1i—N1i—N1—C1180C7—C8—N2—C10−1.0 (4)
N1i—N1—C1—C2177.9 (2)C3—C8—N2—C10179.2 (2)
N1—C1—C2—C9−174.1 (2)C8—N2—C9—C20.2 (3)
N1—C1—C2—C33.4 (4)C10—N2—C9—C2−178.6 (2)
C9—C2—C3—C4−178.3 (3)C3—C2—C9—N2−0.8 (3)
C1—C2—C3—C44.0 (5)C1—C2—C9—N2177.2 (2)
C9—C2—C3—C81.0 (3)C9—N2—C10—O198.5 (3)
C1—C2—C3—C8−176.8 (2)C8—N2—C10—O1−80.1 (3)
C8—C3—C4—C51.6 (4)N2—C10—O1—C11−62.1 (3)
C2—C3—C4—C5−179.2 (3)C10—O1—C11—C12−66.3 (2)
C3—C4—C5—C6−1.0 (4)O1—C11—C12—C13163.0 (2)
C4—C5—C6—C70.0 (4)O1—C11—C12—C17−20.4 (3)
C5—C6—C7—C80.5 (4)C17—C12—C13—C14−1.4 (4)
C6—C7—C8—N2−179.5 (2)C11—C12—C13—C14175.3 (2)
C6—C7—C8—C30.2 (4)C12—C13—C14—C151.7 (4)
C4—C3—C8—N2178.5 (2)C13—C14—C15—C16−0.4 (4)
C2—C3—C8—N2−0.9 (3)C14—C15—C16—C17−1.0 (4)
C4—C3—C8—C7−1.2 (4)C15—C16—C17—C121.3 (4)
C2—C3—C8—C7179.4 (2)C13—C12—C17—C160.0 (4)
C7—C8—N2—C9−179.8 (3)C11—C12—C17—C16−176.7 (2)
C3—C8—N2—C90.4 (3)
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