Literature DB >> 22606118

6,6'-Dimeth-oxy-2,2'-[(E,E')-(2,4,6-trimethyl-1,3-phenyl-ene)bis-(nitrilo-methanylyl-idene)]diphenol chloro-form monosolvate.

Hadariah Bahron, Najihah Abu Bakar, Bohari M Yamin, M Sukeri M Yusof.   

Abstract

In the title compound, C(25)H(26)N(2)O(4)·CHCl(3), the aromatic rings of the imino-methyl-6-meth-oxy-phenol fragments make dihedral angles of 58.33 (6) and 87.74 (6)° with the central benzene ring. The mol-ecular conformation is stabilized by intra-molecular O-H⋯N hydrogen bonds. In the crystal, an inter-molecular C-H⋯O hydrogen bond involving the chloro-form solvent mol-ecule is observed. The crystal packing is further stabilized by π-π stacking inter-actions [centroid-centroid distances = 3.739 (3)-3.776 (3) Å] between the benzene rings of centrosymmetrically related mol-ecules.

Entities:  

Year:  2012        PMID: 22606118      PMCID: PMC3344115          DOI: 10.1107/S1600536812011531

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


Related literature

For a related structure, see: Yamin et al. (2009 ▶). For the synthetic procedure, see: Hernández-Molina et al. (1997 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C25H26N2O4·CHCl3 M = 537.85 Triclinic, a = 10.162 (2) Å b = 10.486 (2) Å c = 12.640 (3) Å α = 99.315 (4)° β = 93.140 (4)° γ = 90.196 (4)° V = 1327.0 (5) Å3 Z = 2 Mo Kα radiation μ = 0.38 mm−1 T = 298 K 0.50 × 0.47 × 0.44 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.833, T max = 0.851 14608 measured reflections 4947 independent reflections 3799 reflections with I > 2σ(I) R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.150 S = 1.04 4947 reflections 329 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.42 e Å−3 Δρmin = −0.43 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011531/rz2720sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011531/rz2720Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C25H26N2O4·CHCl3Z = 2
Mr = 537.85F(000) = 560
Triclinic, P1Dx = 1.346 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.162 (2) ÅCell parameters from 5967 reflections
b = 10.486 (2) Åθ = 2.0–25.5°
c = 12.640 (3) ŵ = 0.38 mm1
α = 99.315 (4)°T = 298 K
β = 93.140 (4)°Block, colourless
γ = 90.196 (4)°0.50 × 0.47 × 0.44 mm
V = 1327.0 (5) Å3
Bruker SMART APEX CCD area-detector diffractometer4947 independent reflections
Radiation source: fine-focus sealed tube3799 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Detector resolution: 83.66 pixels mm-1θmax = 25.5°, θmin = 2.0°
ω scanh = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2000)k = −12→12
Tmin = 0.833, Tmax = 0.851l = −15→15
14608 measured 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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0709P)2 + 0.542P] where P = (Fo2 + 2Fc2)/3
4947 reflections(Δ/σ)max < 0.001
329 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = −0.43 e Å3
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
Cl10.03110 (10)0.62554 (11)0.86722 (8)0.1141 (4)
Cl20.27407 (11)0.52065 (10)0.93526 (9)0.1134 (3)
Cl30.12916 (12)0.69304 (10)1.08602 (7)0.1112 (4)
O10.66016 (19)0.17533 (16)0.16568 (15)0.0666 (5)
O20.78095 (19)0.01822 (19)0.02179 (15)0.0774 (5)
O30.24675 (16)0.87363 (16)0.38440 (18)0.0742 (6)
O40.12149 (18)1.08231 (16)0.3545 (2)0.0897 (7)
N10.47101 (18)0.21937 (16)0.29251 (15)0.0518 (4)
N20.24295 (18)0.62506 (16)0.38954 (16)0.0527 (4)
C10.4031 (2)0.28405 (19)0.47697 (18)0.0500 (5)
C20.3505 (2)0.3788 (2)0.55115 (18)0.0536 (5)
H20.35150.36650.62240.064*
C30.2966 (2)0.4910 (2)0.52441 (18)0.0512 (5)
C40.2981 (2)0.50847 (18)0.41760 (18)0.0473 (5)
C50.3573 (2)0.42049 (19)0.34071 (17)0.0492 (5)
C60.4070 (2)0.30635 (19)0.37139 (18)0.0474 (5)
C70.4551 (3)0.1628 (2)0.5135 (2)0.0662 (6)
H7A0.38970.09520.49670.099*
H7B0.47500.17940.58960.099*
H7C0.53360.13670.47740.099*
C80.2394 (3)0.5905 (2)0.6084 (2)0.0705 (7)
H8A0.14490.58730.59930.106*
H8B0.27070.67490.60100.106*
H8C0.26600.57260.67850.106*
C90.3669 (3)0.4462 (2)0.2278 (2)0.0721 (7)
H9A0.28970.41230.18510.108*
H9B0.44370.40500.19770.108*
H9C0.37350.53760.22830.108*
C100.4370 (2)0.1001 (2)0.26946 (18)0.0520 (5)
H100.36650.06980.30270.062*
C110.5068 (2)0.0109 (2)0.19195 (18)0.0515 (5)
C120.6140 (2)0.0524 (2)0.14253 (18)0.0529 (5)
C130.6780 (2)−0.0339 (2)0.06563 (19)0.0599 (6)
C140.6338 (3)−0.1596 (2)0.0417 (2)0.0716 (7)
H140.6758−0.2175−0.00890.086*
C150.5280 (3)−0.2015 (2)0.0915 (2)0.0767 (8)
H150.4998−0.28720.07450.092*
C160.4642 (3)−0.1179 (2)0.1656 (2)0.0655 (6)
H160.3927−0.14670.19850.079*
C170.8454 (3)−0.0624 (4)−0.0602 (3)0.1006 (11)
H17A0.8850−0.1334−0.03150.151*
H17B0.9125−0.0134−0.08700.151*
H17C0.7824−0.0949−0.11770.151*
C180.1223 (2)0.6255 (2)0.36095 (18)0.0513 (5)
H180.07490.54830.35330.062*
C190.0532 (2)0.7410 (2)0.33923 (17)0.0498 (5)
C20−0.0803 (2)0.7342 (3)0.3063 (2)0.0689 (7)
H20−0.12440.65490.29570.083*
C21−0.1466 (3)0.8424 (3)0.2894 (3)0.0801 (8)
H21−0.23530.83640.26660.096*
C22−0.0827 (3)0.9608 (3)0.3060 (2)0.0720 (7)
H22−0.12901.03460.29560.086*
C230.0486 (2)0.9705 (2)0.3378 (2)0.0595 (6)
C240.1182 (2)0.8603 (2)0.35432 (18)0.0499 (5)
C250.0571 (3)1.1989 (3)0.3692 (3)0.0928 (10)
H25A0.00831.20920.30400.139*
H25B0.12051.26810.38800.139*
H25C−0.00231.20050.42590.139*
C260.1719 (3)0.6559 (3)0.9533 (2)0.0741 (7)
H260.21960.72990.93490.089*
H30.275 (3)0.797 (4)0.392 (3)0.109 (11)*
H10.605 (3)0.218 (3)0.210 (3)0.101 (11)*
U11U22U33U12U13U23
Cl10.1134 (7)0.1233 (8)0.0967 (6)0.0259 (6)−0.0080 (5)−0.0049 (5)
Cl20.1231 (8)0.1002 (7)0.1177 (7)0.0351 (6)0.0131 (6)0.0177 (5)
Cl30.1584 (9)0.1091 (7)0.0672 (5)−0.0003 (6)0.0309 (5)0.0097 (4)
O10.0770 (12)0.0468 (9)0.0746 (11)0.0004 (8)0.0250 (9)−0.0016 (8)
O20.0793 (12)0.0798 (12)0.0697 (11)0.0162 (10)0.0216 (9)−0.0039 (9)
O30.0490 (9)0.0427 (9)0.1321 (17)0.0056 (7)−0.0044 (9)0.0210 (10)
O40.0635 (11)0.0417 (9)0.167 (2)0.0105 (8)0.0093 (12)0.0248 (11)
N10.0546 (10)0.0388 (9)0.0620 (11)0.0110 (8)0.0091 (8)0.0065 (8)
N20.0534 (11)0.0344 (9)0.0710 (12)0.0073 (7)0.0058 (9)0.0095 (8)
C10.0467 (11)0.0418 (11)0.0622 (13)0.0061 (9)0.0012 (10)0.0108 (9)
C20.0590 (13)0.0491 (12)0.0537 (12)0.0043 (10)0.0039 (10)0.0112 (10)
C30.0528 (12)0.0405 (11)0.0595 (13)0.0037 (9)0.0080 (10)0.0035 (9)
C40.0465 (11)0.0322 (10)0.0632 (13)0.0035 (8)0.0039 (9)0.0075 (9)
C50.0522 (12)0.0391 (10)0.0570 (12)0.0042 (9)0.0063 (9)0.0086 (9)
C60.0442 (11)0.0361 (10)0.0611 (13)0.0061 (8)0.0058 (9)0.0048 (9)
C70.0717 (16)0.0554 (14)0.0740 (16)0.0197 (12)−0.0027 (12)0.0193 (12)
C80.0881 (18)0.0522 (14)0.0700 (16)0.0146 (12)0.0194 (14)0.0012 (12)
C90.099 (2)0.0565 (14)0.0644 (15)0.0228 (13)0.0172 (14)0.0164 (12)
C100.0503 (12)0.0442 (12)0.0611 (13)0.0078 (9)0.0026 (10)0.0078 (10)
C110.0571 (13)0.0389 (11)0.0565 (12)0.0099 (9)−0.0030 (10)0.0041 (9)
C120.0609 (13)0.0429 (11)0.0531 (12)0.0129 (10)−0.0018 (10)0.0043 (9)
C130.0659 (15)0.0569 (14)0.0540 (13)0.0201 (11)−0.0001 (11)0.0014 (10)
C140.0876 (19)0.0573 (15)0.0625 (15)0.0236 (13)−0.0011 (14)−0.0115 (12)
C150.095 (2)0.0425 (13)0.0849 (19)0.0075 (13)−0.0076 (16)−0.0082 (12)
C160.0721 (16)0.0461 (13)0.0753 (16)0.0021 (11)−0.0032 (13)0.0034 (11)
C170.082 (2)0.125 (3)0.082 (2)0.0240 (19)0.0192 (16)−0.0254 (19)
C180.0572 (13)0.0373 (10)0.0595 (13)0.0008 (9)0.0072 (10)0.0066 (9)
C190.0520 (12)0.0442 (11)0.0544 (12)0.0071 (9)0.0059 (9)0.0102 (9)
C200.0565 (14)0.0592 (14)0.0923 (19)−0.0024 (11)−0.0047 (13)0.0196 (13)
C210.0532 (14)0.0771 (18)0.113 (2)0.0059 (13)−0.0115 (14)0.0308 (16)
C220.0593 (15)0.0619 (15)0.101 (2)0.0180 (12)0.0056 (14)0.0310 (14)
C230.0548 (13)0.0452 (12)0.0817 (16)0.0100 (10)0.0116 (11)0.0177 (11)
C240.0452 (11)0.0457 (11)0.0603 (13)0.0090 (9)0.0083 (9)0.0109 (9)
C250.086 (2)0.0506 (15)0.141 (3)0.0160 (14)0.0102 (19)0.0142 (17)
C260.0911 (19)0.0671 (16)0.0665 (16)−0.0008 (14)0.0179 (14)0.0136 (13)
Cl1—C261.745 (3)C9—H9B0.9600
Cl2—C261.753 (3)C9—H9C0.9600
Cl3—C261.738 (3)C10—C111.457 (3)
O1—C121.351 (3)C10—H100.9300
O1—H10.89 (4)C11—C121.388 (3)
O2—C131.363 (3)C11—C161.399 (3)
O2—C171.419 (3)C12—C131.406 (3)
O3—C241.340 (3)C13—C141.372 (4)
O3—H30.88 (4)C14—C151.380 (4)
O4—C231.366 (3)C14—H140.9300
O4—C251.379 (3)C15—C161.368 (4)
N1—C101.280 (3)C15—H150.9300
N1—C61.425 (3)C16—H160.9300
N2—C181.259 (3)C17—H17A0.9600
N2—C41.435 (3)C17—H17B0.9600
C1—C21.381 (3)C17—H17C0.9600
C1—C61.394 (3)C18—C191.458 (3)
C1—C71.509 (3)C18—H180.9300
C2—C31.383 (3)C19—C241.394 (3)
C2—H20.9300C19—C201.395 (3)
C3—C41.392 (3)C20—C211.362 (4)
C3—C81.505 (3)C20—H200.9300
C4—C51.391 (3)C21—C221.380 (4)
C5—C61.404 (3)C21—H210.9300
C5—C91.503 (3)C22—C231.370 (3)
C7—H7A0.9600C22—H220.9300
C7—H7B0.9600C23—C241.396 (3)
C7—H7C0.9600C25—H25A0.9600
C8—H8A0.9600C25—H25B0.9600
C8—H8B0.9600C25—H25C0.9600
C8—H8C0.9600C26—H260.9800
C9—H9A0.9600
C12—O1—H1106 (2)O2—C13—C14126.2 (2)
C13—O2—C17117.6 (2)O2—C13—C12114.9 (2)
C24—O3—H3107 (2)C14—C13—C12118.9 (2)
C23—O4—C25118.9 (2)C13—C14—C15121.0 (2)
C10—N1—C6121.59 (19)C13—C14—H14119.5
C18—N2—C4118.54 (18)C15—C14—H14119.5
C2—C1—C6117.92 (19)C16—C15—C14120.5 (2)
C2—C1—C7119.0 (2)C16—C15—H15119.7
C6—C1—C7123.0 (2)C14—C15—H15119.7
C1—C2—C3123.1 (2)C15—C16—C11119.9 (3)
C1—C2—H2118.5C15—C16—H16120.0
C3—C2—H2118.5C11—C16—H16120.0
C2—C3—C4117.53 (19)O2—C17—H17A109.5
C2—C3—C8120.8 (2)O2—C17—H17B109.5
C4—C3—C8121.6 (2)H17A—C17—H17B109.5
C5—C4—C3121.95 (18)O2—C17—H17C109.5
C5—C4—N2120.19 (19)H17A—C17—H17C109.5
C3—C4—N2117.76 (18)H17B—C17—H17C109.5
C4—C5—C6118.1 (2)N2—C18—C19123.36 (19)
C4—C5—C9121.06 (19)N2—C18—H18118.3
C6—C5—C9120.87 (19)C19—C18—H18118.3
C1—C6—C5121.22 (19)C24—C19—C20119.0 (2)
C1—C6—N1121.34 (18)C24—C19—C18120.59 (19)
C5—C6—N1117.24 (19)C20—C19—C18120.4 (2)
C1—C7—H7A109.5C21—C20—C19120.7 (2)
C1—C7—H7B109.5C21—C20—H20119.7
H7A—C7—H7B109.5C19—C20—H20119.7
C1—C7—H7C109.5C20—C21—C22120.3 (2)
H7A—C7—H7C109.5C20—C21—H21119.9
H7B—C7—H7C109.5C22—C21—H21119.9
C3—C8—H8A109.5C23—C22—C21120.4 (2)
C3—C8—H8B109.5C23—C22—H22119.8
H8A—C8—H8B109.5C21—C22—H22119.8
C3—C8—H8C109.5O4—C23—C22125.1 (2)
H8A—C8—H8C109.5O4—C23—C24114.9 (2)
H8B—C8—H8C109.5C22—C23—C24120.0 (2)
C5—C9—H9A109.5O3—C24—C19122.20 (18)
C5—C9—H9B109.5O3—C24—C23118.2 (2)
H9A—C9—H9B109.5C19—C24—C23119.6 (2)
C5—C9—H9C109.5O4—C25—H25A109.5
H9A—C9—H9C109.5O4—C25—H25B109.5
H9B—C9—H9C109.5H25A—C25—H25B109.5
N1—C10—C11121.1 (2)O4—C25—H25C109.5
N1—C10—H10119.5H25A—C25—H25C109.5
C11—C10—H10119.5H25B—C25—H25C109.5
C12—C11—C16119.4 (2)Cl3—C26—Cl1110.58 (17)
C12—C11—C10120.85 (19)Cl3—C26—Cl2110.98 (16)
C16—C11—C10119.7 (2)Cl1—C26—Cl2109.26 (16)
O1—C12—C11121.96 (19)Cl3—C26—H26108.7
O1—C12—C13117.9 (2)Cl1—C26—H26108.7
C11—C12—C13120.2 (2)Cl2—C26—H26108.7
C6—C1—C2—C33.1 (3)C17—O2—C13—C143.3 (4)
C7—C1—C2—C3−177.8 (2)C17—O2—C13—C12−176.9 (2)
C1—C2—C3—C4−1.0 (3)O1—C12—C13—O2−0.5 (3)
C1—C2—C3—C8179.3 (2)C11—C12—C13—O2179.3 (2)
C2—C3—C4—C5−3.3 (3)O1—C12—C13—C14179.3 (2)
C8—C3—C4—C5176.4 (2)C11—C12—C13—C14−0.9 (3)
C2—C3—C4—N2−179.66 (19)O2—C13—C14—C15−180.0 (2)
C8—C3—C4—N20.0 (3)C12—C13—C14—C150.3 (4)
C18—N2—C4—C593.5 (3)C13—C14—C15—C160.4 (4)
C18—N2—C4—C3−90.1 (3)C14—C15—C16—C11−0.4 (4)
C3—C4—C5—C65.2 (3)C12—C11—C16—C15−0.2 (3)
N2—C4—C5—C6−178.49 (19)C10—C11—C16—C15178.8 (2)
C3—C4—C5—C9−175.3 (2)C4—N2—C18—C19174.8 (2)
N2—C4—C5—C91.0 (3)N2—C18—C19—C24−3.0 (3)
C2—C1—C6—C5−1.0 (3)N2—C18—C19—C20179.1 (2)
C7—C1—C6—C5179.9 (2)C24—C19—C20—C21−0.2 (4)
C2—C1—C6—N1173.84 (19)C18—C19—C20—C21177.7 (3)
C7—C1—C6—N1−5.2 (3)C19—C20—C21—C22−0.8 (5)
C4—C5—C6—C1−3.0 (3)C20—C21—C22—C231.2 (5)
C9—C5—C6—C1177.5 (2)C25—O4—C23—C2218.3 (4)
C4—C5—C6—N1−178.06 (18)C25—O4—C23—C24−162.4 (3)
C9—C5—C6—N12.4 (3)C21—C22—C23—O4178.7 (3)
C10—N1—C6—C158.0 (3)C21—C22—C23—C24−0.5 (4)
C10—N1—C6—C5−126.9 (2)C20—C19—C24—O3−179.0 (2)
C6—N1—C10—C11−177.39 (19)C18—C19—C24—O33.0 (3)
N1—C10—C11—C121.3 (3)C20—C19—C24—C230.9 (3)
N1—C10—C11—C16−177.7 (2)C18—C19—C24—C23−177.1 (2)
C16—C11—C12—O1−179.3 (2)O4—C23—C24—O30.1 (3)
C10—C11—C12—O11.7 (3)C22—C23—C24—O3179.4 (2)
C16—C11—C12—C130.8 (3)O4—C23—C24—C19−179.9 (2)
C10—C11—C12—C13−178.2 (2)C22—C23—C24—C19−0.6 (4)
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.89 (3)1.76 (4)2.566 (3)150 (3)
O3—H3···N20.87 (4)1.83 (4)2.618 (2)150 (4)
C26—H26···O1i0.982.163.071 (4)154
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
O1—H1⋯N10.89 (3)1.76 (4)2.566 (3)150 (3)
O3—H3⋯N20.87 (4)1.83 (4)2.618 (2)150 (4)
C26—H26⋯O1i0.982.163.071 (4)154

Symmetry code: (i) .

  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.  6,6'-Dimeth-oxy-2,2'-[(E,E')-(4-chloro-m-phenyl-ene)bis-(nitrilo-methyl-idyne)]diphenol.

Authors:  Bohari M Yamin; Siti Najihah A Bakar; Karimah Kassim; Hadariah Bahron
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-09-30

3.  Structure validation in chemical crystallography.

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

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