Literature DB >> 21202682

Cytenamide acetic acid solvate.

Andrea Johnston, Alastair J Florence, Francesca J A Fabianni, Kenneth Shankland, Colin T Bedford.   

Abstract

IN THE CRYSTAL STRUCTURE OF THE TITLE COMPOUND (SYSTEMATIC NAME: 5H-dibenzo[a,d]cyclo-hepta-triene-5-carboxamide ethanoic acid solvate), C(16)H(13)NO·C(2)H(4)O(2), the cytenamide and solvent mol-ecules form a hydrogen-bonded R(2) (2)(8) dimer motif, which is further connected to form a centrosymmetric double ring motif arrangement. The cycloheptene ring adopts a boat conformation and the dihedral angle between the least-squares planes through the two aromatic rings is 54.7 (2)°.

Entities:  

Year:  2008        PMID： 21202682      PMCID： PMC2961612          DOI： 10.1107/S160053680801550X

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


Related literature

For details on experimental methods used to obtain this form, see: Davis et al. (1964 ▶); Florence et al. (2003 ▶); Florence, Johnston, Fernandes et al. (2006 ▶). For related literature on related mol­ecules, see: Cyr et al. (1987 ▶); Fleischman et al. (2003 ▶); Florence, Johnston, Price et al. (2006 ▶); Florence, Leech et al. (2006 ▶); Bandoli et al. (1992 ▶); Harrison et al. (2006 ▶); Leech et al. (2007 ▶); Florence et al. (2008 ▶) and Johnston et al. (2006 ▶). For other related literature, see: Etter (1990 ▶).

Experimental

Crystal data

C16H13NO·C2H4O2 M = 295.34 Monoclinic, a = 5.8726 (17) Å b = 14.418 (3) Å c = 18.182 (4) Å β = 95.13 (2)° V = 1533.3 (6) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 160 K 0.44 × 0.09 × 0.06 mm

Data collection

Oxford Diffraction Gemini diffractometer Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2007 ▶) T min = 0.84, T max = 0.99 16235 measured reflections 2759 independent reflections 2025 reflections with I > 2σ(I) R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.089 wR(F 2) = 0.148 S = 1.08 2759 reflections 199 parameters H-atom parameters constrained Δρmax = 0.43 e Å−3 Δρmin = −0.37 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: PLATON (Spek, 2003 ▶) and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON. Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801550X/om2234sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680801550X/om2234Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H13NO·C2H4O2F000 = 624
Mr = 295.34Dx = 1.279 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3006 reflections
a = 5.8726 (17) Åθ = 3–26º
b = 14.418 (3) ŵ = 0.09 mm−1
c = 18.182 (4) ÅT = 160 K
β = 95.13 (2)ºNeedle, colourless
V = 1533.3 (6) Å30.44 × 0.09 × 0.06 mm
Z = 4
Oxford Diffraction Gemini diffractometer2759 independent reflections
Monochromator: graphite2025 reflections with I > 2σ(I)
Detector resolution: 15.9745 pixels mm-1Rint = 0.065
T = 160 Kθmax = 25.2º
ω scansθmin = 2.7º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)h = −7→7
Tmin = 0.84, Tmax = 0.99k = −17→17
16235 measured reflectionsl = −21→21
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.089  Method = Modified Sheldrick w = 1/[σ2(F2) + 3.15P], where P = (max(Fo2,0) + 2Fc2)/3
wR(F2) = 0.148(Δ/σ)max = 0.0002
S = 1.08Δρmax = 0.43 e Å−3
2759 reflectionsΔρmin = −0.37 e Å−3
199 parametersExtinction correction: None
Primary atom site location: structure-invariant direct methods
xyzUiso*/Ueq
C10.8743 (7)0.1556 (2)0.5586 (2)0.0377
C21.0683 (7)0.2065 (3)0.52488 (19)0.0394
H21.20720.17090.53950.0464*
C31.0494 (7)0.2106 (2)0.4415 (2)0.0359
H30.36430.61940.82620.0919*
C41.2134 (7)0.1675 (3)0.4031 (2)0.0434
H41.33620.13550.42910.0517*
C51.2009 (8)0.1694 (3)0.3270 (2)0.0489
H51.31550.14170.30230.0588*
C61.0206 (8)0.2134 (3)0.2876 (2)0.0492
H61.01150.21460.23610.0589*
C70.8543 (8)0.2557 (3)0.3251 (2)0.0479
H70.72870.28340.29800.0554*
C80.8695 (7)0.2579 (2)0.4025 (2)0.0391
C90.7017 (8)0.3120 (3)0.4383 (2)0.0500
H90.55400.31380.41400.0595*
C100.7341 (8)0.3609 (3)0.5012 (2)0.0548
H100.60620.39330.51490.0651*
C110.9405 (9)0.3695 (3)0.5504 (2)0.0537
C120.9797 (11)0.4529 (3)0.5910 (3)0.0745
H120.87010.49890.58670.0940*
C131.1748 (15)0.4673 (4)0.6361 (3)0.1040
H131.19570.52300.66180.1120*
C141.3377 (12)0.3999 (5)0.6437 (3)0.0924
H141.47160.40960.67450.1038*
C151.3053 (9)0.3160 (3)0.6066 (2)0.0620
H151.41960.27000.61210.0709*
C161.1082 (8)0.3006 (3)0.5609 (2)0.0448
C170.6177 (7)0.5488 (3)0.8287 (2)0.0425
C180.8000 (7)0.5266 (3)0.7809 (2)0.0554
H18a0.91630.57300.78540.0834*
H18b0.87130.46980.79650.0835*
H18c0.74320.52180.73030.0833*
O10.8339 (5)0.17284 (18)0.62261 (13)0.0490
O20.6154 (5)0.52248 (18)0.89214 (14)0.0484
O30.4556 (5)0.6020 (2)0.79594 (15)0.0614
N10.7638 (6)0.0891 (2)0.51942 (16)0.0425
H1N0.78700.08130.47270.0503*
H2N0.66690.05460.54190.0502*
U11U22U33U12U13U23
C10.051 (3)0.0295 (19)0.030 (2)−0.0027 (18)−0.0055 (18)0.0048 (16)
C20.046 (2)0.038 (2)0.032 (2)−0.0007 (18)−0.0058 (18)0.0005 (17)
C30.049 (2)0.0252 (18)0.033 (2)−0.0068 (17)0.0016 (18)0.0008 (16)
C40.056 (3)0.038 (2)0.036 (2)−0.0023 (19)−0.001 (2)−0.0003 (18)
C50.061 (3)0.045 (2)0.041 (2)−0.002 (2)0.009 (2)−0.008 (2)
C60.075 (3)0.044 (2)0.028 (2)−0.004 (2)0.002 (2)0.0015 (18)
C70.064 (3)0.040 (2)0.038 (2)−0.002 (2)−0.008 (2)0.0106 (19)
C80.052 (3)0.030 (2)0.035 (2)−0.0051 (18)0.0013 (19)0.0049 (16)
C90.062 (3)0.038 (2)0.050 (3)0.004 (2)0.006 (2)0.013 (2)
C100.079 (3)0.030 (2)0.059 (3)0.008 (2)0.029 (3)0.012 (2)
C110.090 (4)0.038 (2)0.036 (2)−0.014 (2)0.019 (2)0.0013 (19)
C120.141 (5)0.041 (3)0.049 (3)−0.023 (3)0.046 (3)−0.005 (2)
C130.207 (9)0.063 (4)0.049 (3)−0.076 (5)0.053 (5)−0.028 (3)
C140.138 (6)0.100 (5)0.042 (3)−0.083 (5)0.027 (3)−0.023 (3)
C150.082 (4)0.072 (3)0.032 (2)−0.036 (3)0.007 (2)−0.009 (2)
C160.066 (3)0.040 (2)0.029 (2)−0.017 (2)0.006 (2)0.0005 (17)
C170.054 (3)0.034 (2)0.038 (2)0.0012 (19)−0.007 (2)−0.0052 (18)
C180.062 (3)0.055 (3)0.048 (3)0.004 (2)0.000 (2)−0.010 (2)
O10.073 (2)0.0466 (16)0.0272 (15)−0.0191 (15)0.0036 (14)−0.0021 (12)
O20.064 (2)0.0436 (16)0.0359 (16)0.0114 (14)−0.0044 (14)0.0061 (13)
O30.082 (2)0.067 (2)0.0351 (16)0.0330 (18)0.0035 (15)0.0077 (14)
N10.064 (2)0.0351 (18)0.0269 (17)−0.0113 (16)−0.0012 (16)0.0012 (14)
O1—C11.234 (4)C11—C121.419 (6)
O2—C171.216 (5)C12—C131.364 (10)
O3—C171.322 (5)C13—C141.362 (10)
O3—H30.8400C14—C151.390 (8)
N1—C11.329 (5)C15—C161.381 (6)
N1—H1N0.8800C2—H20.9800
N1—H2N0.8800C4—H40.9500
C1—C21.529 (6)C5—H50.9300
C2—C161.516 (6)C6—H60.9300
C2—C31.511 (5)C7—H70.9400
C3—C81.397 (5)C9—H90.9400
C3—C41.386 (6)C10—H100.9400
C4—C51.379 (5)C12—H120.9200
C5—C61.379 (6)C13—H130.9300
C6—C71.382 (6)C14—H140.9300
C7—C81.403 (5)C15—H150.9400
C8—C91.455 (6)C17—C181.473 (6)
C9—C101.343 (5)C18—H18A0.9500
C10—C111.446 (6)C18—H18B0.9500
C11—C161.400 (7)C18—H18C0.9500
C17—O3—H3111.00C1—C2—H2106.00
H1N—N1—H2N122.00C16—C2—H2105.00
C1—N1—H1N120.00C3—C2—H2106.00
C1—N1—H2N118.00C3—C4—H4120.00
N1—C1—C2118.5 (3)C5—C4—H4119.00
O1—C1—N1121.7 (3)C6—C5—H5120.00
O1—C1—C2119.7 (3)C4—C5—H5120.00
C1—C2—C3115.5 (3)C5—C6—H6120.00
C3—C2—C16113.2 (3)C7—C6—H6120.00
C1—C2—C16110.4 (3)C6—C7—H7119.00
C4—C3—C8119.4 (3)C8—C7—H7120.00
C2—C3—C4119.7 (3)C10—C9—H9116.00
C2—C3—C8120.9 (3)C8—C9—H9116.00
C3—C4—C5121.3 (4)C11—C10—H10116.00
C4—C5—C6120.0 (4)C9—C10—H10116.00
C5—C6—C7119.4 (3)C11—C12—H12119.00
C6—C7—C8121.4 (4)C13—C12—H12119.00
C3—C8—C7118.4 (4)C12—C13—H13120.00
C7—C8—C9118.4 (4)C14—C13—H13120.00
C3—C8—C9123.1 (3)C15—C14—H14120.00
C8—C9—C10127.8 (4)C13—C14—H14120.00
C9—C10—C11128.3 (4)C14—C15—H15120.00
C10—C11—C12118.9 (4)C16—C15—H15120.00
C12—C11—C16116.8 (4)O2—C17—C18124.2 (4)
C10—C11—C16124.3 (4)O3—C17—C18113.1 (3)
C11—C12—C13122.0 (5)O2—C17—O3122.7 (4)
C12—C13—C14119.8 (5)C17—C18—H18A110.00
C13—C14—C15120.5 (6)C17—C18—H18B110.00
C14—C15—C16120.2 (5)C17—C18—H18C112.00
C2—C16—C11119.8 (4)H18A—C18—H18B107.00
C11—C16—C15120.6 (4)H18A—C18—H18C109.00
C2—C16—C15119.5 (4)H18B—C18—H18C109.00
O1—C1—C2—C3−157.1 (3)C5—C6—C7—C82.5 (7)
O1—C1—C2—C16−27.1 (5)C6—C7—C8—C3−4.4 (6)
N1—C1—C2—C327.5 (5)C6—C7—C8—C9173.5 (4)
N1—C1—C2—C16157.4 (3)C3—C8—C9—C1033.2 (6)
C1—C2—C3—C4−116.5 (4)C7—C8—C9—C10−144.6 (4)
C1—C2—C3—C864.0 (4)C8—C9—C10—C11−2.4 (7)
C16—C2—C3—C4114.9 (4)C9—C10—C11—C12149.6 (5)
C16—C2—C3—C8−64.6 (5)C9—C10—C11—C16−30.0 (7)
C1—C2—C16—C11−67.0 (5)C10—C11—C12—C13−177.3 (5)
C1—C2—C16—C15110.0 (4)C16—C11—C12—C132.4 (8)
C3—C2—C16—C1164.2 (5)C10—C11—C16—C2−5.9 (6)
C3—C2—C16—C15−118.8 (4)C10—C11—C16—C15177.2 (4)
C2—C3—C4—C5179.6 (4)C12—C11—C16—C2174.4 (4)
C8—C3—C4—C5−0.8 (6)C12—C11—C16—C15−2.5 (6)
C2—C3—C8—C7−177.0 (4)C11—C12—C13—C14−0.8 (9)
C2—C3—C8—C95.2 (5)C12—C13—C14—C15−0.9 (9)
C4—C3—C8—C73.5 (5)C13—C14—C15—C160.8 (8)
C4—C3—C8—C9−174.3 (4)C14—C15—C16—C2−175.9 (4)
C3—C4—C5—C6−1.1 (7)C14—C15—C16—C111.0 (7)
C4—C5—C6—C70.3 (7)
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.882.272.888 (4)128
N1—H2N···O2ii0.882.183.018 (4)158
O3—H3···O1iii0.841.732.565 (4)169
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1N⋯O2i0.882.272.888 (4)128
N1—H2N⋯O2ii0.882.183.018 (4)158
O3—H3⋯O1iii0.841.732.565 (4)169

Symmetry codes: (i) ; (ii) ; (iii) .

  5 in total

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Journal:  J Pharm Sci       Date:  2006-09       Impact factor: 3.534

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5.  Liquid chromatographic methods for assay of carbamazepine, 10,11-dihydrocarbamazepine, and related compounds in carbamazepine drug substance and tablets.

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