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In the title benzoyl­hydrazide derivative, C17H18N2O, the dihedral angle between the benzene rings is 88.45 (8)° and the azomethine double bond adopts an E conformation. In the crystal, mol­ecules are linked by N—H...O and C—H...O hydrogen bonds, forming a chain along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813004388/is5246sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536813004388/is5246Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536813004388/is5246Isup3.cml
Supplementary material

CCDC reference: 935499

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.030
  • wR factor = 0.080
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C3 -- C4 .. 7.4 su
Alert level C STRVA01_ALERT_4_C Flack parameter is too small From the CIF: _refine_ls_abs_structure_Flack -0.800 From the CIF: _refine_ls_abs_structure_Flack_su 1.500 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 1 PLAT915_ALERT_3_C Low Friedel Pair Coverage ...................... 89 Perc.
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF ? PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High . 1.500 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 273 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 273 K PLAT916_ALERT_2_G Hooft y and Flack x Parameter values differ by . 0.50
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

Benzohydrazides represents an important class of organic compounds with a wide range of biological applications (Musharraf et al., 2012; Khan et al., 2012). The title compound was obtained in continuation of our work to synthesize and study the biological activities of benzohydrazide derivatives. Previously, we have published crystal structures of many benzohydrazides derivatives with different substitution pattern on two phenyl rings (Taha et al., 2012a,b; Naz et al., 2012). In the title compound two methyl substituted phenyl rings (C1–C6 and C9–C14) are each planner with dihedral angle of 88.45 (8)° between them. The bond lengths and angles were found to be similar as in structurally related benzohydrazide derivatives (Taha et al., 2012a,b; Naz et al., 2012). The crystal structure stabilize by intermolecular N1—H1A···O1i and C8—H8A···O1i interactions to form a chain along the b axis (symmetry code as in Table 1).

Related literature top

For the applications and biological activity of Schiff bases, see: Musharraf et al. (2012); Khan et al. (2012). For the crystal structures of related compounds, see: Taha et al. (2012a,b); Naz et al. (2012).

Experimental top

The title compound was synthesized by using (0.328 g) 2 mmol of 2,4-dimethylbenzohydrazide and (0.240 g) 2 mmol 2-methylbenzaldehyde as starting material under same conditions and solvents as described in our previous publications (Taha et al., 2012a,b; Naz et al., 2012). The compound was recrystallized by dissolving in methanol to obtain colorless needles (0.474 g, 89% yield). All chemicals were purchased by sigma Aldrich Germany.

Refinement top

H atoms on methyl and phenyl groups were positioned geometrically with C—H = 0.96 and 0.93 Å, respectively, and constrained to ride on their parent atoms with Uiso(H) = 1.5Ueq(Cmethyl) or 1.2Ueq(Cphenyl). A rotating group model was applied to the methyl groups. The H atoms on the nitrogen was located in a difference Fourier map and refined isotropically [N—H = 0.832 (15) Å]. The Hooft y parameter was -0.3 (5).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at 30% probability level.
[Figure 2] Fig. 2. A crystal packing diagram of the title compound. Only hydrogen atoms involved in the hydrogen bonds (dashed lines) are shown.
(E)-2,4-Dimethyl-N'-(2-methylbenzylidene)benzohydrazide top
Crystal data top
C17H18N2OF(000) = 568
Mr = 266.33Dx = 1.202 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 4590 reflections
a = 26.1151 (10) Åθ = 2.4–27.4°
b = 4.9484 (2) ŵ = 0.08 mm1
c = 11.3933 (4) ÅT = 273 K
V = 1472.33 (10) Å3Block, colorles
Z = 40.56 × 0.55 × 0.23 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2577 independent reflections
Radiation source: fine-focus sealed tube2483 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scanθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 2531
Tmin = 0.959, Tmax = 0.983k = 55
8023 measured reflectionsl = 1313
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)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.080 w = 1/[σ2(Fo2) + (0.0459P)2 + 0.1205P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2577 reflectionsΔρmax = 0.12 e Å3
189 parametersΔρmin = 0.14 e Å3
1 restraintExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.016 (2)
Crystal data top
C17H18N2OV = 1472.33 (10) Å3
Mr = 266.33Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 26.1151 (10) ŵ = 0.08 mm1
b = 4.9484 (2) ÅT = 273 K
c = 11.3933 (4) Å0.56 × 0.55 × 0.23 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2577 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
2483 reflections with I > 2σ(I)
Tmin = 0.959, Tmax = 0.983Rint = 0.021
8023 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0301 restraint
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.12 e Å3
2577 reflectionsΔρmin = 0.14 e Å3
189 parameters
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
O10.40241 (5)0.5493 (2)0.43046 (18)0.0938 (6)
N10.38352 (4)0.1086 (2)0.44326 (11)0.0438 (3)
H1A0.3925 (5)0.050 (3)0.4301 (13)0.039 (4)*
N20.33498 (4)0.1558 (2)0.48752 (10)0.0448 (3)
C10.49419 (6)0.0399 (3)0.44104 (14)0.0500 (3)
H1B0.47970.03460.50820.060*
C20.54235 (6)0.0412 (3)0.40641 (15)0.0600 (4)
H2B0.56010.16790.45100.072*
C30.56461 (6)0.0633 (4)0.30653 (15)0.0605 (4)
C40.53740 (6)0.2556 (4)0.24413 (14)0.0588 (4)
H4A0.55240.32970.17750.071*
C50.48869 (6)0.3437 (3)0.27612 (13)0.0488 (4)
C60.46699 (5)0.2308 (3)0.37737 (12)0.0426 (3)
C70.41514 (5)0.3145 (3)0.41905 (14)0.0480 (3)
C80.30625 (5)0.0517 (3)0.49163 (13)0.0459 (3)
H8A0.31810.21570.46240.055*
C90.25464 (5)0.0345 (3)0.54203 (13)0.0458 (3)
C100.24424 (6)0.1476 (3)0.63203 (14)0.0553 (4)
H10A0.27030.25790.66020.066*
C110.19599 (7)0.1674 (4)0.68005 (15)0.0656 (5)
H11A0.18930.29220.73920.079*
C120.15778 (7)0.0008 (4)0.63967 (17)0.0665 (5)
H12A0.12520.01080.67220.080*
C130.16772 (6)0.1808 (3)0.55115 (18)0.0628 (4)
H13A0.14140.29220.52480.075*
C140.21564 (5)0.2029 (3)0.50006 (14)0.0500 (3)
C150.22448 (7)0.3941 (3)0.39994 (17)0.0652 (4)
H15A0.19400.49790.38620.098*
H15B0.25220.51360.41890.098*
H15C0.23290.29330.33060.098*
C160.61613 (7)0.0348 (6)0.2648 (2)0.0969 (8)
H16A0.63830.06060.33110.145*
H16B0.63080.09690.21290.145*
H16C0.61200.20300.22390.145*
C170.46107 (8)0.5471 (4)0.20175 (18)0.0736 (5)
H17A0.42500.50910.20280.110*
H17B0.47350.53700.12260.110*
H17C0.46700.72510.23230.110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0731 (8)0.0328 (5)0.1753 (17)0.0011 (5)0.0407 (10)0.0067 (8)
N10.0394 (6)0.0335 (5)0.0587 (7)0.0032 (4)0.0055 (5)0.0042 (5)
N20.0388 (6)0.0451 (6)0.0505 (6)0.0038 (5)0.0034 (5)0.0020 (5)
C10.0471 (8)0.0556 (8)0.0472 (8)0.0015 (6)0.0033 (7)0.0003 (7)
C20.0467 (8)0.0745 (10)0.0586 (10)0.0108 (7)0.0058 (8)0.0036 (8)
C30.0421 (8)0.0810 (11)0.0583 (9)0.0034 (7)0.0019 (8)0.0175 (8)
C40.0589 (10)0.0728 (10)0.0448 (8)0.0218 (8)0.0111 (7)0.0100 (7)
C50.0555 (9)0.0431 (7)0.0477 (8)0.0127 (6)0.0011 (7)0.0043 (6)
C60.0429 (7)0.0367 (6)0.0482 (8)0.0057 (5)0.0015 (6)0.0066 (5)
C70.0460 (8)0.0349 (6)0.0630 (9)0.0006 (5)0.0038 (7)0.0038 (6)
C80.0415 (7)0.0427 (6)0.0534 (8)0.0024 (6)0.0011 (6)0.0018 (6)
C90.0414 (7)0.0469 (7)0.0492 (7)0.0032 (6)0.0032 (6)0.0059 (6)
C100.0508 (9)0.0632 (9)0.0520 (8)0.0002 (7)0.0027 (7)0.0012 (7)
C110.0663 (11)0.0764 (11)0.0541 (9)0.0055 (9)0.0177 (8)0.0022 (8)
C120.0499 (9)0.0789 (11)0.0707 (11)0.0030 (8)0.0207 (9)0.0056 (9)
C130.0458 (8)0.0650 (9)0.0774 (11)0.0079 (7)0.0060 (9)0.0036 (9)
C140.0454 (8)0.0459 (7)0.0586 (8)0.0005 (6)0.0026 (7)0.0066 (6)
C150.0578 (9)0.0578 (9)0.0800 (12)0.0053 (7)0.0007 (9)0.0111 (9)
C160.0501 (11)0.150 (2)0.0910 (16)0.0072 (12)0.0129 (10)0.0378 (15)
C170.0953 (15)0.0592 (10)0.0664 (11)0.0078 (9)0.0073 (11)0.0132 (8)
Geometric parameters (Å, º) top
O1—C71.2156 (17)C9—C141.400 (2)
N1—C71.3401 (17)C10—C111.377 (2)
N1—N21.3842 (16)C10—H10A0.9300
N1—H1A0.832 (15)C11—C121.374 (3)
N2—C81.2723 (18)C11—H11A0.9300
C1—C21.378 (2)C12—C131.376 (3)
C1—C61.387 (2)C12—H12A0.9300
C1—H1B0.9300C13—C141.384 (2)
C2—C31.378 (3)C13—H13A0.9300
C2—H2B0.9300C14—C151.500 (2)
C3—C41.384 (3)C15—H15A0.9600
C3—C161.507 (2)C15—H15B0.9600
C4—C51.393 (2)C15—H15C0.9600
C4—H4A0.9300C16—H16A0.9600
C5—C61.401 (2)C16—H16B0.9600
C5—C171.500 (2)C16—H16C0.9600
C6—C71.4933 (19)C17—H17A0.9600
C8—C91.4675 (19)C17—H17B0.9600
C8—H8A0.9300C17—H17C0.9600
C9—C101.392 (2)
C7—N1—N2120.73 (11)C11—C10—H10A119.4
C7—N1—H1A120.4 (10)C9—C10—H10A119.4
N2—N1—H1A118.9 (10)C12—C11—C10119.26 (16)
C8—N2—N1114.66 (11)C12—C11—H11A120.4
C2—C1—C6121.07 (15)C10—C11—H11A120.4
C2—C1—H1B119.5C11—C12—C13120.04 (15)
C6—C1—H1B119.5C11—C12—H12A120.0
C1—C2—C3120.80 (16)C13—C12—H12A120.0
C1—C2—H2B119.6C12—C13—C14122.03 (16)
C3—C2—H2B119.6C12—C13—H13A119.0
C2—C3—C4117.73 (14)C14—C13—H13A119.0
C2—C3—C16121.07 (18)C13—C14—C9117.84 (15)
C4—C3—C16121.17 (18)C13—C14—C15120.58 (15)
C3—C4—C5123.35 (14)C9—C14—C15121.54 (14)
C3—C4—H4A118.3C14—C15—H15A109.5
C5—C4—H4A118.3C14—C15—H15B109.5
C4—C5—C6117.36 (14)H15A—C15—H15B109.5
C4—C5—C17120.09 (15)C14—C15—H15C109.5
C6—C5—C17122.54 (15)H15A—C15—H15C109.5
C1—C6—C5119.67 (13)H15B—C15—H15C109.5
C1—C6—C7119.13 (13)C3—C16—H16A109.5
C5—C6—C7121.19 (13)C3—C16—H16B109.5
O1—C7—N1122.42 (14)H16A—C16—H16B109.5
O1—C7—C6123.16 (13)C3—C16—H16C109.5
N1—C7—C6114.42 (11)H16A—C16—H16C109.5
N2—C8—C9120.62 (12)H16B—C16—H16C109.5
N2—C8—H8A119.7C5—C17—H17A109.5
C9—C8—H8A119.7C5—C17—H17B109.5
C10—C9—C14119.67 (14)H17A—C17—H17B109.5
C10—C9—C8120.32 (13)C5—C17—H17C109.5
C14—C9—C8120.01 (13)H17A—C17—H17C109.5
C11—C10—C9121.14 (15)H17B—C17—H17C109.5
C7—N1—N2—C8170.77 (14)C5—C6—C7—O149.4 (2)
C6—C1—C2—C30.8 (2)C1—C6—C7—N149.99 (18)
C1—C2—C3—C41.3 (2)C5—C6—C7—N1130.66 (14)
C1—C2—C3—C16176.88 (17)N1—N2—C8—C9176.93 (12)
C2—C3—C4—C51.2 (2)N2—C8—C9—C1030.9 (2)
C16—C3—C4—C5177.01 (16)N2—C8—C9—C14149.45 (15)
C3—C4—C5—C60.5 (2)C14—C9—C10—C110.6 (2)
C3—C4—C5—C17178.19 (16)C8—C9—C10—C11179.71 (15)
C2—C1—C6—C50.0 (2)C9—C10—C11—C121.2 (3)
C2—C1—C6—C7179.36 (14)C10—C11—C12—C130.9 (3)
C4—C5—C6—C10.16 (19)C11—C12—C13—C140.0 (3)
C17—C5—C6—C1178.77 (14)C12—C13—C14—C90.6 (2)
C4—C5—C6—C7179.50 (12)C12—C13—C14—C15177.14 (17)
C17—C5—C6—C71.9 (2)C10—C9—C14—C130.2 (2)
N2—N1—C7—O12.7 (3)C8—C9—C14—C13179.43 (14)
N2—N1—C7—C6177.21 (12)C10—C9—C14—C15177.45 (15)
C1—C6—C7—O1129.9 (2)C8—C9—C14—C152.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.833 (15)2.000 (15)2.8150 (14)166.1 (14)
C8—H8A···O1i0.932.523.2696 (19)138
Symmetry code: (i) x, y1, z.

Experimental details

Crystal data
Chemical formulaC17H18N2O
Mr266.33
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)273
a, b, c (Å)26.1151 (10), 4.9484 (2), 11.3933 (4)
V3)1472.33 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.56 × 0.55 × 0.23
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.959, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
8023, 2577, 2483
Rint0.021
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.080, 1.04
No. of reflections2577
No. of parameters189
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.12, 0.14

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.833 (15)2.000 (15)2.8150 (14)166.1 (14)
C8—H8A···O1i0.932.523.2696 (19)138
Symmetry code: (i) x, y1, z.
 

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