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The title compound crystallizes in the ortho­rhom­bic space group Pbca. The phenol ring is inclined to the benzo­nitrile ring by 25.65 (3)°. The configuration about the C=N bond is E, stabilized by a strong intra­molecular O—H...N hydrogen bond that forms an S(6) ring motif.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020008907/zl2787sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989020008907/zl2787Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020008907/zl2787Isup3.cml
Supplementary material

CCDC reference: 2013269

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.103
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 ..N1 . 2.77 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H15A ..O1 . 2.74 Ang. PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 19.941 Check PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.069 Check PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G PLAT063_ALERT_4_G Crystal Size Possibly too Large for Beam Size .. 0.73 mm PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still 35% Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 5 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 5 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2018/3 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009), Mercury (Macrae et al., 2020); software used to prepare material for publication: WinGX (Farrugia, 2012), PLATON (Spek, 2020), SHELXL2018/3 (Sheldrick, 2015b) and publCIF (Westrip, 2010).

2-[(2-Hydroxy-5-methylbenzylidene)amino]benzonitrile top
Crystal data top
C15H12N2ODx = 1.262 Mg m3
Mr = 236.27Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 13160 reflections
a = 7.8139 (3) Åθ = 1.5–25.8°
b = 27.047 (1) ŵ = 0.08 mm1
c = 11.7683 (5) ÅT = 296 K
V = 2487.14 (17) Å3Prism, colorless
Z = 80.73 × 0.42 × 0.24 mm
F(000) = 992
Data collection top
STOE IPDS 2
diffractometer
2270 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1552 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.040
Detector resolution: 6.67 pixels mm-1θmax = 25.3°, θmin = 1.5°
rotation method scansh = 99
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 3232
Tmin = 0.951, Tmax = 0.989l = 1414
15314 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0529P)2 + 0.0539P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2270 reflectionsΔρmax = 0.10 e Å3
167 parametersΔρmin = 0.09 e Å3
0 restraintsExtinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: dualExtinction coefficient: 0.0048 (9)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4510 (2)0.43624 (6)0.56936 (18)0.0817 (5)
C20.4377 (2)0.43849 (6)0.69096 (14)0.0740 (4)
C30.3751 (3)0.48102 (6)0.7420 (2)0.0926 (5)
H30.3432030.5079740.6977130.111*
C40.3606 (3)0.48315 (8)0.8578 (2)0.1034 (6)
H40.3167460.5113340.8924600.124*
C50.4108 (3)0.44357 (8)0.92255 (18)0.0991 (6)
H50.4013740.4453151.0012200.119*
C60.4752 (2)0.40119 (6)0.87308 (15)0.0836 (5)
H60.5105440.3749220.9183420.100*
C70.48704 (18)0.39788 (5)0.75604 (13)0.0686 (4)
C80.54747 (18)0.31307 (5)0.73859 (12)0.0641 (4)
H80.4994190.3085290.8101270.077*
C90.61539 (17)0.27095 (5)0.67918 (11)0.0598 (4)
C100.69055 (18)0.27512 (6)0.57110 (12)0.0654 (4)
C110.7545 (2)0.23368 (6)0.51800 (14)0.0759 (4)
H110.8055390.2364380.4469000.091*
C120.7430 (2)0.18837 (7)0.56968 (15)0.0800 (5)
H120.7874890.1608290.5327330.096*
C130.6667 (2)0.18226 (6)0.67585 (15)0.0780 (5)
C140.6052 (2)0.22403 (5)0.72774 (13)0.0696 (4)
H140.5541520.2209060.7987750.084*
C150.6544 (3)0.13194 (6)0.7305 (2)0.1221 (8)
H15A0.6730660.1349710.8108470.183*
H15B0.7395870.1105010.6984570.183*
H15C0.5427810.1183290.7170440.183*
O10.70348 (16)0.31893 (4)0.51676 (10)0.0877 (4)
H10.654 (3)0.3432 (6)0.5601 (13)0.132*
N10.4603 (3)0.43494 (6)0.47293 (15)0.1085 (6)
N20.55113 (16)0.35659 (5)0.69604 (10)0.0681 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0981 (12)0.0574 (9)0.0896 (13)0.0001 (8)0.0131 (11)0.0016 (9)
C20.0722 (9)0.0636 (9)0.0861 (11)0.0043 (7)0.0017 (8)0.0097 (9)
C30.0903 (12)0.0715 (11)0.1160 (15)0.0009 (9)0.0017 (11)0.0165 (11)
C40.1000 (14)0.0856 (13)0.1245 (18)0.0013 (11)0.0128 (13)0.0354 (13)
C50.1078 (14)0.0977 (14)0.0919 (13)0.0108 (12)0.0155 (11)0.0295 (12)
C60.0909 (12)0.0832 (11)0.0766 (11)0.0075 (9)0.0047 (9)0.0145 (9)
C70.0653 (9)0.0666 (9)0.0738 (10)0.0066 (7)0.0033 (7)0.0123 (8)
C80.0613 (8)0.0729 (9)0.0582 (8)0.0055 (7)0.0024 (7)0.0020 (7)
C90.0557 (7)0.0681 (9)0.0558 (8)0.0041 (6)0.0009 (6)0.0045 (7)
C100.0618 (8)0.0749 (10)0.0597 (8)0.0040 (7)0.0004 (7)0.0017 (8)
C110.0704 (9)0.0948 (12)0.0624 (9)0.0027 (9)0.0066 (7)0.0124 (9)
C120.0785 (10)0.0809 (11)0.0804 (11)0.0103 (8)0.0002 (9)0.0180 (9)
C130.0823 (11)0.0691 (10)0.0827 (11)0.0009 (8)0.0020 (9)0.0063 (8)
C140.0729 (9)0.0715 (9)0.0645 (9)0.0027 (7)0.0048 (7)0.0020 (8)
C150.156 (2)0.0725 (12)0.1380 (18)0.0078 (13)0.0243 (15)0.0080 (12)
O10.1075 (9)0.0844 (8)0.0713 (7)0.0015 (7)0.0194 (6)0.0055 (6)
N10.1567 (16)0.0760 (10)0.0927 (12)0.0039 (9)0.0181 (11)0.0018 (9)
N20.0721 (8)0.0658 (8)0.0663 (7)0.0029 (6)0.0019 (6)0.0029 (6)
Geometric parameters (Å, º) top
C1—N11.138 (2)C9—C141.3940 (19)
C1—C21.436 (3)C9—C101.406 (2)
C2—C31.387 (2)C10—O11.3503 (17)
C2—C71.393 (2)C10—C111.377 (2)
C3—C41.369 (3)C11—C121.371 (2)
C3—H30.9300C11—H110.9300
C4—C51.371 (3)C12—C131.394 (2)
C4—H40.9300C12—H120.9300
C5—C61.381 (2)C13—C141.371 (2)
C5—H50.9300C13—C151.509 (2)
C6—C71.383 (2)C14—H140.9300
C6—H60.9300C15—H15A0.9600
C7—N21.4130 (18)C15—H15B0.9600
C8—N21.2795 (17)C15—H15C0.9600
C8—C91.4380 (19)O1—H10.92 (2)
C8—H80.9300
N1—C1—C2179.2 (2)C10—C9—C8122.05 (13)
C3—C2—C7120.90 (16)O1—C10—C11118.18 (14)
C3—C2—C1119.48 (16)O1—C10—C9122.02 (14)
C7—C2—C1119.62 (14)C11—C10—C9119.80 (15)
C4—C3—C2119.7 (2)C12—C11—C10120.16 (15)
C4—C3—H3120.2C12—C11—H11119.9
C2—C3—H3120.2C10—C11—H11119.9
C3—C4—C5119.78 (19)C11—C12—C13122.10 (15)
C3—C4—H4120.1C11—C12—H12119.0
C5—C4—H4120.1C13—C12—H12119.0
C4—C5—C6121.21 (19)C14—C13—C12116.84 (15)
C4—C5—H5119.4C14—C13—C15122.08 (17)
C6—C5—H5119.4C12—C13—C15121.08 (16)
C5—C6—C7119.87 (18)C13—C14—C9123.19 (15)
C5—C6—H6120.1C13—C14—H14118.4
C7—C6—H6120.1C9—C14—H14118.4
C6—C7—C2118.54 (14)C13—C15—H15A109.5
C6—C7—N2124.92 (15)C13—C15—H15B109.5
C2—C7—N2116.51 (14)H15A—C15—H15B109.5
N2—C8—C9122.03 (13)C13—C15—H15C109.5
N2—C8—H8119.0H15A—C15—H15C109.5
C9—C8—H8119.0H15B—C15—H15C109.5
C14—C9—C10117.90 (14)C10—O1—H1109.5
C14—C9—C8120.05 (13)C8—N2—C7121.58 (13)
C7—C2—C3—C40.4 (3)C14—C9—C10—C111.4 (2)
C1—C2—C3—C4179.34 (17)C8—C9—C10—C11179.69 (14)
C2—C3—C4—C51.2 (3)O1—C10—C11—C12179.53 (15)
C3—C4—C5—C60.4 (3)C9—C10—C11—C120.8 (2)
C4—C5—C6—C71.1 (3)C10—C11—C12—C130.4 (3)
C5—C6—C7—C21.9 (2)C11—C12—C13—C140.9 (3)
C5—C6—C7—N2179.77 (15)C11—C12—C13—C15179.52 (18)
C3—C2—C7—C61.1 (2)C12—C13—C14—C90.3 (2)
C1—C2—C7—C6179.13 (15)C15—C13—C14—C9179.81 (17)
C3—C2—C7—N2179.21 (14)C10—C9—C14—C130.9 (2)
C1—C2—C7—N21.1 (2)C8—C9—C14—C13179.80 (14)
N2—C8—C9—C14178.55 (13)C9—C8—N2—C7178.75 (13)
N2—C8—C9—C100.3 (2)C6—C7—N2—C825.3 (2)
C14—C9—C10—O1178.93 (14)C2—C7—N2—C8156.72 (13)
C8—C9—C10—O10.0 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C9–C14 ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.921.832.6280 (16)145
C4—H4···N1i0.932.773.610 (3)150
C15—H15A···O1ii0.962.743.641 (3)158
C11—H11···Cg1iii0.932.853.654 (16)146
Symmetry codes: (i) x+1/2, y+1, z+1/2; (ii) x, y+1/2, z+1/2; (iii) x+1/2, y+1/2, z+1.
Comparison of selected observed (X-ray data) and calculated (DFT) geometric parameters (Å, °) top
ParameterX-rayB3LYP/6–311G(d,p)
O1—C101.3503 (17)1.3366
N2—C81.2795 (17)1.2909
N2—C71.4130 (18)1.3979
C1—N11.138 (2)1.155
C1—C21.436 (3)1.429
C8—C91.4380 (19)1.4432
N1—C1—C2179.2 (2)178.3
C8—N2—C7121.58 (13)121.07
N2—C8—C9122.03 (13)122.79
C7—N2—C8—C9-178.75 (13)-176.57
 

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