Download citation
Download citation
link to html
The title compound, C17H18N2O2, was synthesized by the reaction of 2-hydroxy­benzoyl­hydrazine with 4-isopropyl­benzaldehyde in ethanol. The mol­ecule is non-planar and the dihedral angle between the two aromatic rings is 21.9 (2)°. The crystal structure involves inter­molecular O—H...O and intra­molecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007385/hg6148sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007385/hg6148Isup2.hkl
Contains datablock I

CCDC reference: 270444

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.076
  • wR factor = 0.228
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C15
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.107 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.18 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT731_ALERT_1_C Bond Calc 0.86(4), Rep 0.862(19) ...... 2.11 su-Rat O2 -H2 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(4), Rep 0.862(19) ...... 2.11 su-Rat O2 -H2 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-Hydroxy-2'-(4-isopropylbenzylidene)benzohydrazide top
Crystal data top
C17H18N2O2F(000) = 600
Mr = 282.33Dx = 1.237 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1484 reflections
a = 4.9264 (19) Åθ = 4.7–45.4°
b = 28.000 (11) ŵ = 0.08 mm1
c = 11.098 (4) ÅT = 293 K
β = 97.957 (7)°Block, colorless
V = 1516.1 (10) Å30.35 × 0.33 × 0.08 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer
3116 independent reflections
Radiation source: fine-focus sealed tube1720 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.107
φ and ω scansθmax = 26.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 66
Tmin = 0.972, Tmax = 0.994k = 3435
8199 measured reflectionsl = 137
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)] = 0.076H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.228 w = 1/[σ2(Fo2) + (0.1071P)2
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.004
3116 reflectionsΔρmax = 0.25 e Å3
205 parametersΔρmin = 0.22 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.7881 (5)0.27046 (8)0.86197 (18)0.0655 (7)
O20.9434 (5)0.26408 (8)0.5039 (2)0.0640 (7)
N10.6670 (5)0.23717 (9)0.6786 (2)0.0448 (7)
N20.4978 (5)0.20445 (8)0.7234 (2)0.0458 (7)
C10.8110 (7)0.26850 (10)0.7534 (3)0.0437 (8)
C20.9947 (6)0.30130 (9)0.6980 (2)0.0420 (7)
C31.1170 (8)0.33746 (12)0.7725 (3)0.0642 (10)
H31.07380.34060.85110.077*
C41.3014 (9)0.36891 (13)0.7321 (3)0.0797 (13)
H41.38060.39290.78340.096*
C51.3678 (8)0.36471 (12)0.6161 (3)0.0667 (10)
H51.49270.38570.58920.080*
C61.2504 (7)0.32976 (11)0.5406 (3)0.0540 (8)
H61.29630.32700.46240.065*
C71.0618 (6)0.29816 (10)0.5799 (2)0.0421 (7)
C80.3585 (6)0.17941 (10)0.6420 (3)0.0488 (8)
H80.37650.18540.56110.059*
C90.1715 (6)0.14170 (10)0.6686 (3)0.0465 (8)
C100.1451 (7)0.12720 (11)0.7857 (3)0.0581 (9)
H100.24270.14280.85190.070*
C110.0252 (8)0.08971 (11)0.8044 (3)0.0614 (9)
H110.03800.08030.88370.074*
C120.1772 (7)0.06565 (11)0.7100 (3)0.0532 (8)
C130.1576 (8)0.08177 (15)0.5945 (3)0.0807 (12)
H130.26250.06730.52850.097*
C140.0139 (9)0.11894 (14)0.5744 (3)0.0786 (12)
H140.02290.12880.49510.094*
C150.3609 (8)0.02365 (13)0.7284 (4)0.0687 (10)
C160.3912 (11)0.01337 (18)0.8571 (5)0.1174 (18)
H16A0.22400.00020.89760.136*
H16B0.53870.00880.85980.136*
H16C0.43030.04250.89710.136*
C170.2493 (13)0.02080 (16)0.6705 (6)0.124 (2)
H17A0.07600.02960.71560.131*
H17B0.22570.01390.58790.131*
H17C0.37650.04670.67190.131*
H10.677 (7)0.2384 (11)0.603 (3)0.061 (10)*
H21.051 (8)0.2590 (15)0.450 (3)0.113 (16)*
H150.534 (7)0.0213 (12)0.667 (3)0.075 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1012 (19)0.0708 (15)0.0290 (12)0.0182 (13)0.0251 (12)0.0065 (10)
O20.0870 (18)0.0756 (15)0.0362 (12)0.0240 (13)0.0322 (12)0.0164 (11)
N10.0605 (17)0.0506 (15)0.0270 (13)0.0062 (12)0.0191 (12)0.0032 (11)
N20.0616 (16)0.0470 (14)0.0313 (13)0.0009 (12)0.0155 (12)0.0046 (11)
C10.065 (2)0.0416 (16)0.0277 (15)0.0046 (14)0.0170 (14)0.0019 (12)
C20.0560 (18)0.0417 (16)0.0299 (15)0.0041 (14)0.0110 (13)0.0005 (12)
C30.104 (3)0.0577 (19)0.0329 (17)0.0191 (19)0.0158 (18)0.0045 (14)
C40.121 (3)0.073 (2)0.043 (2)0.040 (2)0.004 (2)0.0018 (17)
C50.080 (3)0.070 (2)0.049 (2)0.0271 (19)0.0033 (18)0.0125 (17)
C60.063 (2)0.063 (2)0.0389 (17)0.0076 (17)0.0179 (15)0.0053 (15)
C70.0571 (19)0.0389 (15)0.0319 (15)0.0028 (14)0.0111 (13)0.0007 (12)
C80.062 (2)0.0543 (18)0.0322 (16)0.0009 (16)0.0132 (14)0.0048 (13)
C90.0573 (19)0.0496 (17)0.0331 (16)0.0025 (14)0.0085 (14)0.0004 (12)
C100.084 (2)0.0543 (19)0.0378 (18)0.0148 (18)0.0158 (17)0.0082 (14)
C110.079 (2)0.062 (2)0.048 (2)0.0120 (19)0.0255 (18)0.0012 (16)
C120.054 (2)0.0543 (18)0.053 (2)0.0024 (15)0.0115 (16)0.0038 (16)
C130.085 (3)0.102 (3)0.051 (2)0.038 (2)0.005 (2)0.006 (2)
C140.099 (3)0.099 (3)0.0342 (19)0.032 (2)0.0027 (19)0.0040 (18)
C150.066 (2)0.063 (2)0.076 (3)0.0115 (19)0.006 (2)0.001 (2)
C160.137 (5)0.106 (4)0.113 (4)0.050 (3)0.026 (3)0.021 (3)
C170.153 (5)0.066 (3)0.188 (6)0.023 (3)0.046 (5)0.023 (3)
Geometric parameters (Å, º) top
O1—C11.227 (3)C9—C141.370 (4)
O2—C71.351 (3)C9—C101.384 (4)
O2—H20.862 (19)C10—C111.378 (4)
N1—C11.341 (4)C10—H100.9300
N1—N21.377 (3)C11—C121.376 (4)
N1—H10.85 (3)C11—H110.9300
N2—C81.268 (4)C12—C131.374 (5)
C1—C21.482 (4)C12—C151.515 (5)
C2—C31.390 (4)C13—C141.378 (5)
C2—C71.398 (4)C13—H130.9300
C3—C41.384 (5)C14—H140.9300
C3—H30.9300C15—C161.484 (6)
C4—C51.376 (5)C15—C171.537 (6)
C4—H40.9300C15—H151.02 (4)
C5—C61.364 (4)C16—H16A0.9600
C5—H50.9300C16—H16B0.9600
C6—C71.396 (4)C16—H16C0.9600
C6—H60.9300C17—H17A0.9600
C8—C91.458 (4)C17—H17B0.9600
C8—H80.9300C17—H17C0.9600
C7—O2—H2107 (3)C11—C10—H10119.9
C1—N1—N2120.5 (2)C9—C10—H10119.9
C1—N1—H1119 (2)C12—C11—C10122.5 (3)
N2—N1—H1120 (2)C12—C11—H11118.8
C8—N2—N1114.0 (2)C10—C11—H11118.8
O1—C1—N1121.6 (3)C13—C12—C11116.6 (3)
O1—C1—C2121.6 (3)C13—C12—C15120.1 (3)
N1—C1—C2116.8 (2)C11—C12—C15123.3 (3)
C3—C2—C7117.6 (3)C12—C13—C14121.5 (3)
C3—C2—C1116.4 (3)C12—C13—H13119.2
C7—C2—C1126.0 (3)C14—C13—H13119.2
C4—C3—C2121.4 (3)C9—C14—C13121.5 (3)
C4—C3—H3119.3C9—C14—H14119.2
C2—C3—H3119.3C13—C14—H14119.2
C5—C4—C3120.0 (3)C16—C15—C12115.0 (4)
C5—C4—H4120.0C16—C15—C17109.5 (4)
C3—C4—H4120.0C12—C15—C17108.5 (3)
C6—C5—C4120.0 (3)C16—C15—H15116.5 (19)
C6—C5—H5120.0C12—C15—H15115 (2)
C4—C5—H5120.0C17—C15—H1589.0 (19)
C5—C6—C7120.5 (3)C15—C16—H16A109.5
C5—C6—H6119.8C15—C16—H16B109.5
C7—C6—H6119.8H16A—C16—H16B109.5
O2—C7—C6120.1 (3)C15—C16—H16C109.5
O2—C7—C2119.5 (3)H16A—C16—H16C109.5
C6—C7—C2120.5 (3)H16B—C16—H16C109.5
N2—C8—C9123.4 (3)C15—C17—H17A109.5
N2—C8—H8118.3C15—C17—H17B109.5
C9—C8—H8118.3H17A—C17—H17B109.5
C14—C9—C10117.6 (3)C15—C17—H17C109.5
C14—C9—C8119.3 (3)H17A—C17—H17C109.5
C10—C9—C8123.1 (3)H17B—C17—H17C109.5
C11—C10—C9120.2 (3)
C1—N1—N2—C8175.0 (3)N1—N2—C8—C9178.3 (2)
N2—N1—C1—O13.2 (4)N2—C8—C9—C14175.1 (3)
N2—N1—C1—C2178.0 (2)N2—C8—C9—C105.3 (5)
O1—C1—C2—C36.5 (4)C14—C9—C10—C112.9 (5)
N1—C1—C2—C3172.3 (3)C8—C9—C10—C11176.7 (3)
O1—C1—C2—C7171.3 (3)C9—C10—C11—C120.8 (6)
N1—C1—C2—C79.9 (4)C10—C11—C12—C131.8 (5)
C7—C2—C3—C40.8 (5)C10—C11—C12—C15178.6 (3)
C1—C2—C3—C4177.2 (3)C11—C12—C13—C142.4 (6)
C2—C3—C4—C50.1 (6)C15—C12—C13—C14178.0 (4)
C3—C4—C5—C60.4 (6)C10—C9—C14—C132.3 (6)
C4—C5—C6—C70.2 (5)C8—C9—C14—C13177.3 (3)
C5—C6—C7—O2179.0 (3)C12—C13—C14—C90.4 (7)
C5—C6—C7—C21.3 (5)C13—C12—C15—C16172.9 (4)
C3—C2—C7—O2178.7 (3)C11—C12—C15—C166.7 (6)
C1—C2—C7—O23.4 (5)C13—C12—C15—C1764.1 (5)
C3—C2—C7—C61.5 (4)C11—C12—C15—C17116.4 (4)
C1—C2—C7—C6176.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.85 (3)1.96 (3)2.630 (3)135 (3)
O2—H2···O1i0.86 (2)1.82 (2)2.653 (3)161 (4)
Symmetry code: (i) x+1/2, y+1/2, z1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds