Literature DB >> 22412548

{2-[(3-Bromo-benzyl-idene)amino]-5-chloro-phen-yl}(phen-yl)methanone.

M Aslam, I Anis, N Afza, M Safder, S Yousuf.   

Abstract

In the title compound, C(20)H(13)BrClNO, the azomethine double bond [C=N = 1.246 (4) Å] adopts an E conformation. The bromo- and chlorophenyl rings are inclined to one another by 13.70 (11)°, and form dihedral angles of 76.68 (10) and 74.24 (7)°, respectively, with the phenyl ring. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds to form double stranded chains propagating along the b-axis direction.

Entities:  

Year:  2012        PMID： 22412548      PMCID： PMC3295437          DOI： 10.1107/S1600536812004667

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


Related literature

For background information and preparation of Schiff bases, see: Khan et al. (2009 ▶); Aslam et al. (2011a ▶,b ▶); Zeb & Yousuf (2011 ▶). For the crystal structures of related Schiff bases, see: Aslam et al. (2011a ▶,b ▶); Cox et al. (2008 ▶).

Experimental

Crystal data

C20H13BrClNO M = 398.67 Orthorhombic, a = 16.2068 (12) Å b = 7.8839 (6) Å c = 27.262 (2) Å V = 3483.4 (5) Å3 Z = 8 Mo Kα radiation μ = 2.52 mm−1 T = 273 K 0.52 × 0.21 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.354, T max = 0.704 19261 measured reflections 3243 independent reflections 1931 reflections with I > 2σ(I) R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.045 wR(F 2) = 0.115 S = 1.01 3243 reflections 217 parameters H-atom parameters constrained Δρmax = 0.40 e Å−3 Δρmin = −0.64 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812004667/pv2506sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004667/pv2506Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812004667/pv2506Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H13BrClNOF(000) = 1600
Mr = 398.67Dx = 1.520 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2145 reflections
a = 16.2068 (12) Åθ = 2.5–20.5°
b = 7.8839 (6) ŵ = 2.52 mm−1
c = 27.262 (2) ÅT = 273 K
V = 3483.4 (5) Å3Block, yellow
Z = 80.52 × 0.21 × 0.15 mm
Bruker SMART APEX CCD area-detector diffractometer1931 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.056
ω scanθmax = 25.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −19→19
Tmin = 0.354, Tmax = 0.704k = −9→9
19261 measured reflectionsl = −33→33
3243 independent 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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0377P)2 + 3.0254P] where P = (Fo2 + 2Fc2)/3
3243 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 0.40 e Å−3
0 restraintsΔρmin = −0.64 e Å−3
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
Br10.08907 (4)0.01989 (9)0.238025 (19)0.1197 (3)
Cl10.20842 (7)−0.43108 (16)0.61666 (4)0.0784 (4)
O10.04701 (14)−0.5034 (3)0.44146 (10)0.0608 (7)
N10.21723 (16)−0.2133 (4)0.40923 (10)0.0480 (7)
C10.1977 (2)−0.0784 (5)0.31387 (12)0.0564 (10)
H1B0.1496−0.10920.33020.068*
C20.1939 (3)−0.0077 (5)0.26789 (13)0.0657 (11)
C30.2627 (3)0.0425 (5)0.24302 (14)0.0756 (13)
H3A0.25850.09120.21210.091*
C40.3383 (3)0.0196 (6)0.26466 (15)0.0806 (14)
H4A0.38590.05350.24840.097*
C50.3439 (2)−0.0533 (6)0.31041 (14)0.0720 (12)
H5A0.3955−0.06910.32460.086*
C60.2739 (2)−0.1034 (5)0.33568 (12)0.0508 (9)
C70.2795 (2)−0.1732 (5)0.38504 (12)0.0517 (9)
H7A0.3314−0.18830.39900.062*
C80.22119 (19)−0.2687 (4)0.45845 (11)0.0421 (8)
C90.2910 (2)−0.2620 (5)0.48817 (12)0.0501 (9)
H9A0.3406−0.22250.47530.060*
C100.2873 (2)−0.3135 (5)0.53632 (12)0.0534 (9)
H10A0.3342−0.30890.55590.064*
C110.2143 (2)−0.3715 (5)0.55527 (12)0.0508 (9)
C120.1447 (2)−0.3843 (4)0.52657 (12)0.0485 (9)
H12A0.0960−0.42770.53960.058*
C130.14765 (18)−0.3321 (4)0.47808 (11)0.0400 (8)
C140.07325 (18)−0.3588 (5)0.44606 (11)0.0431 (8)
C150.03203 (19)−0.2139 (4)0.42183 (11)0.0427 (8)
C160.0429 (2)−0.0504 (5)0.43778 (14)0.0581 (10)
H16A0.0776−0.02860.46420.070*
C18−0.0479 (3)0.0481 (6)0.37522 (18)0.0799 (13)
H18A−0.07460.13690.35930.096*
C19−0.0588 (2)−0.1138 (6)0.35928 (15)0.0706 (12)
H19A−0.0930−0.13520.33260.085*
C170.0027 (2)0.0814 (6)0.41493 (17)0.0750 (12)
H17A0.00960.19200.42610.090*
C20−0.0199 (2)−0.2447 (5)0.38228 (13)0.0553 (9)
H20A−0.0281−0.35530.37140.066*
U11U22U33U12U13U23
Br10.1021 (4)0.1846 (7)0.0725 (4)0.0117 (4)−0.0213 (3)0.0344 (4)
Cl10.0843 (7)0.0996 (9)0.0513 (5)−0.0078 (6)−0.0055 (5)0.0208 (6)
O10.0485 (14)0.0481 (16)0.0857 (19)−0.0091 (13)−0.0129 (13)−0.0014 (13)
N10.0384 (15)0.059 (2)0.0470 (16)−0.0057 (14)0.0019 (13)0.0018 (14)
C10.060 (2)0.066 (3)0.043 (2)−0.005 (2)0.0067 (17)−0.0031 (18)
C20.081 (3)0.072 (3)0.044 (2)−0.002 (2)−0.0013 (19)−0.003 (2)
C30.109 (4)0.077 (3)0.041 (2)−0.012 (3)0.012 (2)−0.001 (2)
C40.087 (4)0.100 (4)0.055 (2)−0.028 (3)0.024 (2)−0.005 (2)
C50.060 (2)0.099 (3)0.056 (2)−0.016 (2)0.0112 (19)−0.006 (2)
C60.054 (2)0.056 (2)0.0417 (18)−0.0070 (18)0.0043 (16)−0.0089 (17)
C70.042 (2)0.065 (3)0.048 (2)−0.0048 (18)−0.0032 (17)−0.0059 (18)
C80.0406 (18)0.041 (2)0.0442 (18)−0.0010 (16)−0.0002 (15)−0.0022 (15)
C90.0437 (19)0.056 (2)0.051 (2)−0.0079 (18)−0.0024 (17)0.0021 (17)
C100.046 (2)0.063 (3)0.051 (2)−0.0029 (18)−0.0121 (17)0.0017 (18)
C110.055 (2)0.051 (2)0.0462 (19)−0.0017 (19)−0.0016 (17)0.0047 (17)
C120.0436 (19)0.049 (2)0.053 (2)−0.0058 (17)0.0027 (16)0.0057 (17)
C130.0356 (18)0.0359 (19)0.0483 (19)−0.0002 (15)−0.0017 (14)0.0002 (15)
C140.0329 (17)0.048 (2)0.0480 (19)−0.0035 (17)0.0048 (14)−0.0056 (17)
C150.0356 (17)0.042 (2)0.0503 (19)0.0025 (16)0.0022 (15)−0.0020 (16)
C160.046 (2)0.052 (3)0.077 (3)0.0043 (19)−0.0056 (19)−0.007 (2)
C180.066 (3)0.076 (3)0.098 (3)0.016 (3)−0.003 (3)0.026 (3)
C190.059 (3)0.084 (3)0.069 (3)0.007 (2)−0.015 (2)0.011 (2)
C170.065 (3)0.052 (3)0.109 (3)0.006 (2)0.002 (3)−0.001 (2)
C200.050 (2)0.061 (2)0.055 (2)0.0024 (19)−0.0054 (18)−0.0049 (19)
Br1—C21.896 (4)C9—H9A0.9300
Cl1—C111.741 (3)C10—C111.369 (5)
O1—C141.223 (4)C10—H10A0.9300
N1—C71.246 (4)C11—C121.377 (4)
N1—C81.412 (4)C12—C131.385 (4)
C1—C21.373 (5)C12—H12A0.9300
C1—C61.384 (5)C13—C141.503 (4)
C1—H1B0.9300C14—C151.479 (5)
C2—C31.365 (6)C15—C161.372 (5)
C3—C41.371 (6)C15—C201.389 (4)
C3—H3A0.9300C16—C171.376 (5)
C4—C51.376 (6)C16—H16A0.9300
C4—H4A0.9300C18—C191.360 (6)
C5—C61.385 (5)C18—C171.383 (6)
C5—H5A0.9300C18—H18A0.9300
C6—C71.457 (5)C19—C201.363 (5)
C7—H7A0.9300C19—H19A0.9300
C8—C91.393 (4)C17—H17A0.9300
C8—C131.399 (4)C20—H20A0.9300
C9—C101.375 (4)
C7—N1—C8123.0 (3)C10—C11—C12121.2 (3)
C2—C1—C6119.4 (4)C10—C11—Cl1120.0 (3)
C2—C1—H1B120.3C12—C11—Cl1118.8 (3)
C6—C1—H1B120.3C11—C12—C13119.4 (3)
C3—C2—C1122.3 (4)C11—C12—H12A120.3
C3—C2—Br1119.1 (3)C13—C12—H12A120.3
C1—C2—Br1118.6 (3)C12—C13—C8120.1 (3)
C2—C3—C4118.6 (4)C12—C13—C14119.0 (3)
C2—C3—H3A120.7C8—C13—C14120.7 (3)
C4—C3—H3A120.7O1—C14—C15121.1 (3)
C3—C4—C5120.2 (4)O1—C14—C13118.0 (3)
C3—C4—H4A119.9C15—C14—C13120.9 (3)
C5—C4—H4A119.9C16—C15—C20119.3 (3)
C4—C5—C6121.1 (4)C16—C15—C14121.7 (3)
C4—C5—H5A119.5C20—C15—C14119.0 (3)
C6—C5—H5A119.5C15—C16—C17120.4 (4)
C1—C6—C5118.4 (3)C15—C16—H16A119.8
C1—C6—C7120.4 (3)C17—C16—H16A119.8
C5—C6—C7121.1 (3)C19—C18—C17120.4 (4)
N1—C7—C6122.3 (3)C19—C18—H18A119.8
N1—C7—H7A118.9C17—C18—H18A119.8
C6—C7—H7A118.9C18—C19—C20120.2 (4)
C9—C8—C13118.9 (3)C18—C19—H19A119.9
C9—C8—N1125.3 (3)C20—C19—H19A119.9
C13—C8—N1115.8 (3)C16—C17—C18119.4 (4)
C10—C9—C8120.6 (3)C16—C17—H17A120.3
C10—C9—H9A119.7C18—C17—H17A120.3
C8—C9—H9A119.7C19—C20—C15120.3 (4)
C11—C10—C9119.8 (3)C19—C20—H20A119.8
C11—C10—H10A120.1C15—C20—H20A119.8
C9—C10—H10A120.1
C6—C1—C2—C3−1.4 (6)C11—C12—C13—C80.7 (5)
C6—C1—C2—Br1178.4 (3)C11—C12—C13—C14175.4 (3)
C1—C2—C3—C40.7 (6)C9—C8—C13—C121.1 (5)
Br1—C2—C3—C4−179.0 (3)N1—C8—C13—C12−177.9 (3)
C2—C3—C4—C50.3 (7)C9—C8—C13—C14−173.5 (3)
C3—C4—C5—C6−0.6 (7)N1—C8—C13—C147.5 (4)
C2—C1—C6—C51.0 (6)C12—C13—C14—O1−57.2 (4)
C2—C1—C6—C7178.1 (3)C8—C13—C14—O1117.5 (4)
C4—C5—C6—C10.0 (6)C12—C13—C14—C15121.4 (3)
C4—C5—C6—C7−177.1 (4)C8—C13—C14—C15−63.9 (4)
C8—N1—C7—C6−174.9 (3)O1—C14—C15—C16159.3 (3)
C1—C6—C7—N10.3 (6)C13—C14—C15—C16−19.3 (5)
C5—C6—C7—N1177.3 (4)O1—C14—C15—C20−19.9 (5)
C7—N1—C8—C910.0 (5)C13—C14—C15—C20161.6 (3)
C7—N1—C8—C13−171.1 (3)C20—C15—C16—C170.1 (5)
C13—C8—C9—C10−1.4 (5)C14—C15—C16—C17−179.0 (3)
N1—C8—C9—C10177.5 (3)C17—C18—C19—C20−0.1 (6)
C8—C9—C10—C11−0.1 (5)C15—C16—C17—C18−0.9 (6)
C9—C10—C11—C122.0 (6)C19—C18—C17—C160.9 (6)
C9—C10—C11—Cl1−178.2 (3)C18—C19—C20—C15−0.8 (6)
C10—C11—C12—C13−2.3 (5)C16—C15—C20—C190.7 (5)
Cl1—C11—C12—C13177.9 (3)C14—C15—C20—C19179.9 (3)
D—H···AD—HH···AD···AD—H···A
C12—H12A···O1i0.932.443.346 (4)166
C17—H17A···O1ii0.932.513.428 (5)168
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C12—H12A⋯O1i0.932.443.346 (4)166
C17—H17A⋯O1ii0.932.513.428 (5)168

Symmetry codes: (i) ; (ii) .

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