Literature DB >> 21203131

2-[(E)-(5-Amino-2,3-diphenyl-quinoxalin-6-yl)imino-meth-yl]-4-chloro-phenol.

Hoong-Kun Fun, Reza Kia, Paul R Raithby.   

Abstract

The title Schiff base compound, C(27)H(19)ClN(4)O, features two intra-molecular O-H⋯N and N-H⋯N hydrogen bonds involving the hydr-oxy and amino groups to generate S(6) and S(5) ring motifs, respectively. In the crystal structure, weak inter-molecular N-H⋯O and C-H⋯N inter-actions, together with π-π contacts [centroid-centroid distances = 3.6294 (11)-3.6881 (11) Å], link neighboring mol-ecules.

Entities:  

Year:  2008        PMID： 21203131      PMCID： PMC2962046          DOI： 10.1107/S1600536808020023

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


Related literature

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Corden et al. (1996 ▶); Fun et al. (2008 ▶); Govindasamy et al. (1999 ▶). For applications and bioactivities, see: Anderson et al. (1997 ▶); Cohen & Schmidt (1964 ▶); Granovski et al. (1993 ▶); Li & Chang (1991 ▶); Shahrokhian et al. (2000 ▶); Unaleroglu & Hökelek (2002 ▶).

Experimental

Crystal data

C27H19ClN4O M = 450.91 Monoclinic, a = 22.8728 (11) Å b = 7.3068 (4) Å c = 12.5632 (6) Å β = 92.037 (2)° V = 2098.32 (18) Å3 Z = 4 Mo Kα radiation μ = 0.21 mm−1 T = 100.0 (1) K 0.55 × 0.09 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.843, T max = 0.985 25593 measured reflections 6180 independent reflections 4118 reflections with I > 2σ(I) R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.052 wR(F 2) = 0.159 S = 1.01 6180 reflections 310 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.40 e Å−3 Δρmin = −0.41 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, 2003 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020023/tk2279sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020023/tk2279Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C27H19ClN4OF000 = 936
Mr = 450.91Dx = 1.427 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2969 reflections
a = 22.8728 (11) Åθ = 2.9–28.1º
b = 7.3068 (4) ŵ = 0.21 mm−1
c = 12.5632 (6) ÅT = 100.0 (1) K
β = 92.037 (2)ºBlock, yellow
V = 2098.32 (18) Å30.55 × 0.09 × 0.07 mm
Z = 4
Bruker SMART APEXII CCD area-detector diffractometer6180 independent reflections
Radiation source: fine-focus sealed tube4118 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.062
T = 100.0(1) Kθmax = 30.1º
φ and ω scansθmin = 0.9º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −32→31
Tmin = 0.843, Tmax = 0.985k = −10→10
25593 measured reflectionsl = −17→17
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.159  w = 1/[σ2(Fo2) + (0.0879P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
6180 reflectionsΔρmax = 0.40 e Å−3
310 parametersΔρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
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
Cl10.26328 (2)0.46708 (7)0.59559 (4)0.02813 (14)
O10.44768 (6)0.2687 (2)0.91204 (10)0.0252 (3)
N10.52358 (6)0.3641 (2)0.77495 (12)0.0200 (3)
N20.72297 (7)0.4713 (2)0.88154 (11)0.0174 (3)
N30.75971 (6)0.3333 (2)0.68619 (11)0.0185 (3)
N40.60625 (8)0.4640 (2)0.92698 (13)0.0263 (4)
C10.40599 (8)0.3116 (3)0.83649 (14)0.0203 (4)
C20.34744 (8)0.2879 (3)0.85952 (15)0.0236 (4)
H2A0.33750.24020.92510.028*
C30.30418 (8)0.3350 (3)0.78542 (15)0.0233 (4)
H3A0.26510.31990.80130.028*
C40.31874 (8)0.4049 (3)0.68704 (15)0.0214 (4)
C50.37624 (8)0.4249 (3)0.66116 (14)0.0211 (4)
H5A0.38550.47000.59460.025*
C60.42106 (8)0.3773 (2)0.73536 (14)0.0197 (4)
C70.48149 (8)0.3948 (3)0.70633 (14)0.0206 (4)
H7A0.49010.42870.63730.025*
C80.58278 (7)0.3677 (2)0.74723 (14)0.0183 (3)
C90.60160 (8)0.3128 (3)0.64598 (14)0.0206 (4)
H9A0.57390.28130.59320.025*
C100.65962 (8)0.3050 (3)0.62430 (14)0.0205 (4)
H10A0.67130.26840.55740.025*
C110.70168 (7)0.3530 (2)0.70445 (13)0.0179 (3)
C120.79775 (7)0.3790 (2)0.76358 (13)0.0175 (3)
C130.77919 (7)0.4620 (2)0.86047 (13)0.0169 (3)
C140.68362 (7)0.4111 (2)0.80547 (13)0.0169 (3)
C150.62300 (8)0.4161 (2)0.82744 (13)0.0173 (3)
C160.85933 (7)0.3244 (2)0.74618 (13)0.0186 (4)
C170.88232 (8)0.3426 (3)0.64549 (14)0.0211 (4)
H17A0.86030.39930.59130.025*
C180.93766 (8)0.2771 (3)0.62536 (14)0.0232 (4)
H18A0.95290.29250.55830.028*
C190.97043 (8)0.1884 (3)0.70519 (15)0.0241 (4)
H19A1.00720.14190.69120.029*
C200.94797 (8)0.1695 (3)0.80613 (14)0.0221 (4)
H20A0.96980.11120.86000.027*
C210.89277 (8)0.2380 (3)0.82614 (13)0.0217 (4)
H21A0.87800.22600.89380.026*
C220.82037 (8)0.5458 (2)0.93956 (13)0.0181 (4)
C230.86747 (8)0.6521 (3)0.90850 (14)0.0218 (4)
H23A0.87430.66750.83650.026*
C240.90422 (8)0.7350 (3)0.98433 (15)0.0250 (4)
H24A0.93500.80810.96300.030*
C250.89514 (8)0.7091 (3)1.09180 (15)0.0244 (4)
H25A0.92050.76171.14260.029*
C260.84845 (8)0.6051 (3)1.12332 (14)0.0227 (4)
H26A0.84220.58871.19540.027*
C270.81078 (8)0.5246 (2)1.04769 (13)0.0194 (4)
H27A0.77900.45631.06940.023*
H1O10.4828 (12)0.299 (4)0.881 (2)0.062 (9)*
H1N40.5681 (12)0.531 (4)0.9337 (19)0.052 (8)*
H2N40.6396 (13)0.516 (4)0.976 (2)0.060 (8)*
U11U22U33U12U13U23
Cl10.0190 (2)0.0284 (3)0.0367 (3)0.0003 (2)−0.00334 (18)−0.0011 (2)
O10.0226 (7)0.0291 (8)0.0241 (6)0.0010 (6)0.0023 (5)0.0007 (6)
N10.0176 (7)0.0168 (7)0.0256 (8)−0.0017 (6)0.0014 (6)−0.0025 (6)
N20.0188 (7)0.0151 (7)0.0184 (7)0.0010 (6)0.0009 (5)0.0010 (6)
N30.0183 (7)0.0180 (7)0.0194 (7)0.0015 (6)0.0001 (5)0.0003 (6)
N40.0242 (8)0.0304 (9)0.0242 (8)0.0028 (8)0.0009 (6)−0.0002 (7)
C10.0223 (9)0.0162 (8)0.0223 (8)−0.0010 (7)0.0013 (7)−0.0036 (7)
C20.0245 (9)0.0206 (9)0.0262 (9)−0.0020 (8)0.0060 (7)−0.0033 (7)
C30.0182 (8)0.0210 (9)0.0308 (9)−0.0009 (8)0.0039 (7)−0.0060 (8)
C40.0178 (8)0.0161 (8)0.0302 (9)0.0003 (7)−0.0017 (7)−0.0042 (7)
C50.0212 (9)0.0173 (9)0.0251 (9)−0.0020 (8)0.0022 (7)−0.0012 (7)
C60.0191 (8)0.0158 (8)0.0244 (9)−0.0004 (7)0.0017 (7)−0.0026 (7)
C70.0212 (9)0.0174 (9)0.0234 (8)−0.0006 (8)0.0027 (7)−0.0012 (7)
C80.0170 (8)0.0142 (8)0.0237 (8)−0.0002 (7)0.0021 (6)0.0005 (7)
C90.0196 (8)0.0191 (9)0.0230 (8)−0.0005 (7)−0.0012 (7)−0.0031 (7)
C100.0225 (9)0.0197 (9)0.0193 (8)0.0021 (8)0.0002 (7)−0.0018 (7)
C110.0178 (8)0.0164 (8)0.0194 (8)0.0004 (7)0.0007 (6)−0.0009 (7)
C120.0181 (8)0.0164 (8)0.0179 (8)0.0002 (7)0.0022 (6)0.0024 (6)
C130.0168 (8)0.0161 (8)0.0179 (8)0.0007 (7)0.0011 (6)0.0019 (6)
C140.0176 (8)0.0142 (8)0.0190 (8)0.0011 (7)0.0014 (6)0.0012 (6)
C150.0185 (8)0.0135 (8)0.0199 (8)0.0017 (7)0.0024 (6)0.0016 (7)
C160.0164 (8)0.0178 (8)0.0218 (8)−0.0005 (7)0.0009 (6)−0.0016 (7)
C170.0198 (8)0.0230 (9)0.0206 (8)−0.0022 (8)0.0006 (7)0.0013 (7)
C180.0200 (9)0.0296 (10)0.0202 (8)−0.0031 (8)0.0032 (7)−0.0018 (7)
C190.0154 (8)0.0278 (10)0.0292 (9)0.0005 (8)0.0034 (7)−0.0014 (8)
C200.0178 (8)0.0251 (10)0.0234 (9)0.0030 (8)−0.0014 (7)0.0012 (8)
C210.0212 (9)0.0260 (10)0.0182 (8)0.0013 (8)0.0030 (7)−0.0001 (7)
C220.0171 (8)0.0165 (8)0.0204 (8)0.0032 (7)−0.0008 (6)−0.0015 (7)
C230.0205 (8)0.0220 (9)0.0231 (8)0.0011 (8)0.0032 (7)−0.0005 (7)
C240.0200 (9)0.0237 (10)0.0314 (10)−0.0031 (8)0.0035 (7)−0.0025 (8)
C250.0198 (9)0.0250 (10)0.0280 (9)0.0008 (8)−0.0040 (7)−0.0052 (8)
C260.0254 (9)0.0224 (9)0.0202 (8)0.0025 (8)−0.0003 (7)−0.0006 (7)
C270.0170 (8)0.0202 (9)0.0210 (8)−0.0001 (7)0.0023 (6)−0.0011 (7)
Cl1—C41.7414 (19)C10—H10A0.9300
O1—C11.358 (2)C11—C141.414 (2)
O1—H1O10.93 (3)C12—C131.437 (2)
N1—C71.289 (2)C12—C161.488 (2)
N1—C81.410 (2)C13—C221.478 (2)
N2—C131.324 (2)C14—C151.424 (2)
N2—C141.362 (2)C16—C211.392 (2)
N3—C121.324 (2)C16—C171.393 (2)
N3—C111.363 (2)C17—C181.385 (2)
N4—C151.366 (2)C17—H17A0.9300
N4—H1N41.01 (3)C18—C191.391 (3)
N4—H2N41.03 (3)C18—H18A0.9300
C1—C21.391 (3)C19—C201.392 (3)
C1—C61.412 (2)C19—H19A0.9300
C2—C31.378 (3)C20—C211.389 (2)
C2—H2A0.9300C20—H20A0.9300
C3—C41.389 (3)C21—H21A0.9300
C3—H3A0.9300C22—C271.392 (2)
C4—C51.374 (2)C22—C231.395 (2)
C5—C61.405 (2)C23—C241.387 (3)
C5—H5A0.9300C23—H23A0.9300
C6—C71.448 (2)C24—C251.386 (3)
C7—H7A0.9300C24—H24A0.9300
C8—C151.386 (2)C25—C261.380 (3)
C8—C91.415 (2)C25—H25A0.9300
C9—C101.365 (2)C26—C271.390 (2)
C9—H9A0.9300C26—H26A0.9300
C10—C111.412 (2)C27—H27A0.9300
C1—O1—H1O1104.0 (16)N2—C13—C22116.42 (15)
C7—N1—C8122.17 (15)C12—C13—C22122.95 (15)
C13—N2—C14117.74 (14)N2—C14—C11121.32 (15)
C12—N3—C11117.91 (15)N2—C14—C15118.65 (15)
C15—N4—H1N4118.3 (14)C11—C14—C15119.96 (16)
C15—N4—H2N4114.3 (16)N4—C15—C8122.02 (16)
H1N4—N4—H2N4113 (2)N4—C15—C14119.38 (16)
O1—C1—C2118.90 (16)C8—C15—C14118.58 (15)
O1—C1—C6121.29 (16)C21—C16—C17118.89 (16)
C2—C1—C6119.81 (17)C21—C16—C12120.97 (15)
C3—C2—C1120.12 (17)C17—C16—C12119.83 (15)
C3—C2—H2A119.9C18—C17—C16120.63 (17)
C1—C2—H2A119.9C18—C17—H17A119.7
C2—C3—C4120.27 (17)C16—C17—H17A119.7
C2—C3—H3A119.9C17—C18—C19120.12 (16)
C4—C3—H3A119.9C17—C18—H18A119.9
C5—C4—C3120.78 (17)C19—C18—H18A119.9
C5—C4—Cl1119.81 (14)C18—C19—C20119.77 (17)
C3—C4—Cl1119.40 (14)C18—C19—H19A120.1
C4—C5—C6119.91 (17)C20—C19—H19A120.1
C4—C5—H5A120.0C21—C20—C19119.75 (17)
C6—C5—H5A120.0C21—C20—H20A120.1
C5—C6—C1119.04 (16)C19—C20—H20A120.1
C5—C6—C7119.45 (16)C20—C21—C16120.81 (16)
C1—C6—C7121.51 (16)C20—C21—H21A119.6
N1—C7—C6120.88 (16)C16—C21—H21A119.6
N1—C7—H7A119.6C27—C22—C23119.01 (16)
C6—C7—H7A119.6C27—C22—C13119.40 (16)
C15—C8—N1116.33 (15)C23—C22—C13121.53 (15)
C15—C8—C9120.70 (16)C24—C23—C22120.41 (16)
N1—C8—C9122.82 (15)C24—C23—H23A119.8
C10—C9—C8121.32 (16)C22—C23—H23A119.8
C10—C9—H9A119.3C25—C24—C23120.07 (18)
C8—C9—H9A119.3C25—C24—H24A120.0
C9—C10—C11119.34 (16)C23—C24—H24A120.0
C9—C10—H10A120.3C26—C25—C24119.92 (17)
C11—C10—H10A120.3C26—C25—H25A120.0
N3—C11—C10119.78 (15)C24—C25—H25A120.0
N3—C11—C14120.02 (15)C25—C26—C27120.26 (16)
C10—C11—C14120.09 (16)C25—C26—H26A119.9
N3—C12—C13121.47 (15)C27—C26—H26A119.9
N3—C12—C16115.16 (15)C26—C27—C22120.28 (17)
C13—C12—C16123.18 (15)C26—C27—H27A119.9
N2—C13—C12120.61 (15)C22—C27—H27A119.9
O1—C1—C2—C3178.24 (16)C10—C11—C14—N2−175.02 (16)
C6—C1—C2—C3−2.5 (3)N3—C11—C14—C15−174.42 (16)
C1—C2—C3—C40.5 (3)C10—C11—C14—C151.8 (3)
C2—C3—C4—C51.3 (3)N1—C8—C15—N4−2.2 (3)
C2—C3—C4—Cl1−178.91 (14)C9—C8—C15—N4−177.84 (17)
C3—C4—C5—C6−1.1 (3)N1—C8—C15—C14176.25 (16)
Cl1—C4—C5—C6179.12 (14)C9—C8—C15—C140.6 (3)
C4—C5—C6—C1−0.9 (3)N2—C14—C15—N4−6.2 (3)
C4—C5—C6—C7178.53 (17)C11—C14—C15—N4176.85 (17)
O1—C1—C6—C5−178.08 (16)N2—C14—C15—C8175.28 (16)
C2—C1—C6—C52.7 (3)C11—C14—C15—C8−1.6 (3)
O1—C1—C6—C72.5 (3)N3—C12—C16—C21−132.71 (18)
C2—C1—C6—C7−176.75 (17)C13—C12—C16—C2142.4 (3)
C8—N1—C7—C6175.52 (16)N3—C12—C16—C1740.8 (2)
C5—C6—C7—N1175.24 (17)C13—C12—C16—C17−144.14 (18)
C1—C6—C7—N1−5.3 (3)C21—C16—C17—C18−0.4 (3)
C7—N1—C8—C15151.46 (17)C12—C16—C17—C18−174.06 (17)
C7—N1—C8—C9−33.0 (3)C16—C17—C18—C191.4 (3)
C15—C8—C9—C100.3 (3)C17—C18—C19—C20−1.5 (3)
N1—C8—C9—C10−175.08 (17)C18—C19—C20—C210.5 (3)
C8—C9—C10—C11−0.1 (3)C19—C20—C21—C160.5 (3)
C12—N3—C11—C10−179.68 (16)C17—C16—C21—C20−0.6 (3)
C12—N3—C11—C14−3.4 (3)C12—C16—C21—C20173.01 (17)
C9—C10—C11—N3175.32 (17)N2—C13—C22—C2740.2 (2)
C9—C10—C11—C14−0.9 (3)C12—C13—C22—C27−141.69 (18)
C11—N3—C12—C13−5.4 (3)N2—C13—C22—C23−137.21 (17)
C11—N3—C12—C16169.78 (15)C12—C13—C22—C2340.9 (3)
C14—N2—C13—C12−4.3 (2)C27—C22—C23—C240.1 (3)
C14—N2—C13—C22173.81 (15)C13—C22—C23—C24177.55 (17)
N3—C12—C13—N29.7 (3)C22—C23—C24—C251.5 (3)
C16—C12—C13—N2−165.05 (17)C23—C24—C25—C26−1.9 (3)
N3—C12—C13—C22−168.31 (16)C24—C25—C26—C270.7 (3)
C16—C12—C13—C2216.9 (3)C25—C26—C27—C221.0 (3)
C13—N2—C14—C11−4.5 (3)C23—C22—C27—C26−1.4 (3)
C13—N2—C14—C15178.63 (16)C13—C22—C27—C26−178.89 (17)
N3—C11—C14—N28.7 (3)
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N10.93 (3)1.72 (3)2.584 (2)153 (2)
N4—H1N4···O1i1.01 (3)2.47 (3)3.099 (2)120.4 (18)
N4—H2N4···N21.04 (3)2.31 (3)2.750 (2)104.3 (17)
C27—H27A···N3ii0.932.623.373 (2)138
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1O1⋯N10.93 (3)1.72 (3)2.584 (2)153 (2)
N4—H1N4⋯O1i1.01 (3)2.47 (3)3.099 (2)120.4 (18)
N4—H2N4⋯N21.04 (3)2.31 (3)2.750 (2)104.3 (17)
C27—H27A⋯N3ii0.932.623.373 (2)138

Symmetry codes: (i) ; (ii) .

  3 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.  Salicylate-selective electrodes based on AI(III) and Sn(IV) salophens

Authors: 
Journal:  Anal Chem       Date:  2000-03-01       Impact factor: 6.986

3.  2-[(E)-(5-Amino-2,3-diphenyl-quinoxalin-6-yl)imino-meth-yl]-4-bromo-phenol.

Authors:  Hoong-Kun Fun; Reza Kia; Paul R Raithby
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-06-13
  3 in total

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