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The title compound, C11H14ClN2O, was prepared by the reaction between p-chloro­hypnone and acetohydrazide. The asymmetric unit consists of two crystallographically independent mol­ecules. Symmetry-related mol­ecules form two N—H...O and weak C—H...O hydrogen-bonded chains. Weak inter­actions between the dimers stabilize the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026736/at2316sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026736/at2316Isup2.hkl
Contains datablock I

CCDC reference: 654890

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.055
  • wR factor = 0.191
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT414_ALERT_2_C Short Intra D-H..H-X H2A .. H9C .. 1.94 Ang.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL023_ALERT_1_A There is a mismatched ^ on line 120 form the first two dimer by N2---H2A...O2^i^ and weak C9---H9C...O2^i If you require a ^ then it should be escaped with a \, i.e. \^ Otherwise there must be a matching closing ~, e.g. ^12^C PUBL023_ALERT_1_A There is a mismatched ^ on line 121 ^hydrogen bonds , and the second two dimer N4---H4A...O1^ii ^and If you require a ^ then it should be escaped with a \, i.e. \^ Otherwise there must be a matching closing ~, e.g. ^12^C
2 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

Comment top

As part of our search for new schiff base compounds we synthesized the title compound (I), and describe its structure here.

The independent molecules in the asymmetric unit (Fig.1) are linked together to form the first two dimer by N2—H2A···O2i and weak C9—H9C···O2i hydrogen bonds, and the second two dimer N4—H4A···O1ii and C20—H20C···O1ii hydrogen bonds [symmetry codes: (i) x, y - 1, z - 1; (ii) x, y + 1, z + 1] (Table 2, Fig. 2). The structure is stabilized by weak-interactions between the dimers.

Related literature top

For related literature, see: Cimerman et al. (1997); Sutherland & Hoy (1968); Tucker et al. (1975).

Experimental top

A mixture of the p-chlorohypnone (0.1 mol), and acetohydrazide (0.1 mol) was stirred in refluxing ethanol (30 ml) for 5 h to afford the title compound (0.087 mol, yield 87%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Refinement top

The H atoms bound to the N atoms were found from a difference Fourier map and refined freely. The remained H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H = 0.93–0.96 Å, and with Uiso = 1.2Ueq(Caromatic) or 1.5Ueq(Cmethyl).

Structure description top

As part of our search for new schiff base compounds we synthesized the title compound (I), and describe its structure here.

The independent molecules in the asymmetric unit (Fig.1) are linked together to form the first two dimer by N2—H2A···O2i and weak C9—H9C···O2i hydrogen bonds, and the second two dimer N4—H4A···O1ii and C20—H20C···O1ii hydrogen bonds [symmetry codes: (i) x, y - 1, z - 1; (ii) x, y + 1, z + 1] (Table 2, Fig. 2). The structure is stabilized by weak-interactions between the dimers.

For related literature, see: Cimerman et al. (1997); Sutherland & Hoy (1968); Tucker et al. (1975).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of two independent molecules of the title compound in the asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the N—H.·O and weak C—H.·O hydrogen-bonded dimers. [Symmetry codes: (a) x, y - 1, z - 1; (b) x, y + 1, z + 1]. For clarity, the hydrogen atoms not involving hydrogen bonding are omitted.
N'-[1-(4-Chlorophenyl)ethylidene]acetohydrazine top
Crystal data top
C11H14ClN2OZ = 8
Mr = 190.24F(000) = 816
Monoclinic, P21/nDx = 1.210 Mg m3
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 7.2462 (14) Åθ = 1.6–25.0°
b = 25.710 (5) ŵ = 0.08 mm1
c = 11.616 (2) ÅT = 294 K
β = 105.159 (4)°Block, colourless
V = 2088.8 (7) Å30.22 × 0.20 × 0.14 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1849 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
Graphite monochromatorθmax = 25.0°, θmin = 1.6°
φ and ω scansh = 58
10760 measured reflectionsk = 3029
3691 independent reflectionsl = 139
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)] = 0.055H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.191 w = 1/[σ2(Fo2) + (0.0932P)2 + 0.0086P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.002
3691 reflectionsΔρmax = 0.25 e Å3
268 parametersΔρmin = 0.15 e Å3
2 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.034 (4)
Crystal data top
C11H14ClN2OV = 2088.8 (7) Å3
Mr = 190.24Z = 8
Monoclinic, P21/nMo Kα radiation
a = 7.2462 (14) ŵ = 0.08 mm1
b = 25.710 (5) ÅT = 294 K
c = 11.616 (2) Å0.22 × 0.20 × 0.14 mm
β = 105.159 (4)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
1849 reflections with I > 2σ(I)
10760 measured reflectionsRint = 0.054
3691 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0552 restraints
wR(F2) = 0.191H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.25 e Å3
3691 reflectionsΔρmin = 0.15 e Å3
268 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
O10.2533 (3)0.12503 (8)0.0950 (2)0.0807 (7)
O20.2528 (3)1.01951 (8)1.0905 (2)0.0770 (7)
N10.2490 (3)0.16788 (8)0.1870 (2)0.0514 (6)
N20.2523 (3)0.13483 (9)0.0946 (2)0.0552 (6)
N30.2353 (3)0.97667 (8)0.8058 (2)0.0555 (7)
N40.2507 (4)1.00931 (9)0.9010 (2)0.0596 (7)
C10.2288 (4)0.29725 (12)0.6570 (3)0.0724 (10)
H1A0.35000.29800.71560.109*
H1B0.13060.28730.69430.109*
H1C0.20080.33110.62210.109*
C20.2367 (4)0.25878 (11)0.5618 (3)0.0526 (7)
C30.1961 (4)0.27272 (11)0.4439 (3)0.0597 (8)
H30.16330.30700.42270.072*
C40.2024 (4)0.23771 (10)0.3567 (3)0.0547 (8)
H40.17360.24880.27780.066*
C50.2503 (3)0.18636 (10)0.3828 (2)0.0448 (7)
C60.2918 (4)0.17274 (12)0.5007 (3)0.0648 (9)
H60.32540.13850.52240.078*
C70.2851 (4)0.20834 (12)0.5880 (3)0.0663 (9)
H70.31450.19750.66720.080*
C80.2555 (3)0.14834 (10)0.2888 (3)0.0470 (7)
C90.2613 (5)0.09175 (10)0.3161 (3)0.0760 (10)
H9A0.13330.07890.30400.114*
H9B0.33100.08620.39760.114*
H9C0.32330.07360.26440.114*
C100.2411 (4)0.15422 (11)0.0140 (3)0.0545 (8)
C110.2128 (4)0.21087 (11)0.0330 (3)0.0631 (9)
H11A0.31420.22920.02170.095*
H11B0.09240.22080.01960.095*
H11C0.21350.21940.11330.095*
C120.1844 (5)0.84704 (13)0.3241 (3)0.0907 (12)
H12A0.07840.85650.25880.136*
H12B0.16310.81300.35220.136*
H12C0.29960.84690.29800.136*
C130.2035 (4)0.88583 (12)0.4237 (3)0.0633 (8)
C140.2189 (4)0.93726 (13)0.4059 (3)0.0706 (9)
H140.21790.94920.33020.085*
C150.2361 (4)0.97266 (12)0.4971 (3)0.0661 (9)
H150.24581.00790.48110.079*
C160.2394 (4)0.95761 (10)0.6107 (2)0.0481 (7)
C170.2238 (5)0.90498 (11)0.6279 (3)0.0704 (9)
H170.22490.89280.70350.085*
C180.2067 (5)0.87037 (12)0.5374 (3)0.0764 (10)
H180.19700.83510.55280.092*
C190.2579 (4)0.99517 (10)0.7081 (3)0.0517 (8)
C200.3030 (5)1.05082 (11)0.6893 (3)0.0796 (10)
H20A0.18621.07020.66380.119*
H20B0.37221.05280.62930.119*
H20C0.37951.06510.76260.119*
C210.2446 (4)0.99006 (12)1.0067 (3)0.0593 (8)
C220.2293 (5)0.93300 (11)1.0181 (3)0.0763 (10)
H22A0.34290.91671.00730.114*
H22B0.12020.92050.95840.114*
H22C0.21500.92471.09590.114*
H2A0.262 (4)0.1001 (4)0.102 (3)0.077 (10)*
H4A0.232 (4)1.0439 (5)0.894 (3)0.100 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.132 (2)0.0583 (13)0.0566 (16)0.0028 (12)0.0340 (13)0.0090 (12)
O20.1214 (19)0.0576 (13)0.0579 (15)0.0037 (11)0.0338 (12)0.0112 (12)
N10.0608 (15)0.0450 (13)0.0508 (17)0.0039 (10)0.0190 (11)0.0075 (12)
N20.0782 (17)0.0394 (15)0.0508 (17)0.0038 (11)0.0220 (12)0.0043 (13)
N30.0723 (16)0.0459 (14)0.0515 (18)0.0001 (11)0.0218 (12)0.0059 (13)
N40.0869 (18)0.0422 (15)0.0548 (19)0.0023 (12)0.0278 (13)0.0080 (14)
C10.078 (2)0.073 (2)0.066 (2)0.0039 (16)0.0180 (16)0.0181 (18)
C20.0531 (17)0.0536 (18)0.050 (2)0.0021 (13)0.0117 (13)0.0085 (15)
C30.075 (2)0.0426 (17)0.063 (2)0.0058 (13)0.0220 (16)0.0006 (16)
C40.0693 (19)0.0496 (17)0.0450 (19)0.0027 (13)0.0148 (14)0.0067 (15)
C50.0486 (16)0.0420 (16)0.0453 (19)0.0004 (11)0.0150 (13)0.0022 (14)
C60.095 (2)0.0449 (18)0.053 (2)0.0042 (15)0.0160 (16)0.0040 (16)
C70.090 (2)0.064 (2)0.043 (2)0.0047 (16)0.0125 (16)0.0036 (16)
C80.0528 (17)0.0423 (16)0.046 (2)0.0044 (11)0.0136 (13)0.0034 (14)
C90.124 (3)0.0448 (18)0.060 (2)0.0002 (16)0.0245 (19)0.0017 (16)
C100.071 (2)0.0454 (18)0.050 (2)0.0032 (13)0.0206 (15)0.0030 (16)
C110.083 (2)0.0534 (19)0.054 (2)0.0039 (15)0.0191 (16)0.0022 (15)
C120.124 (3)0.080 (2)0.066 (3)0.012 (2)0.022 (2)0.021 (2)
C130.077 (2)0.058 (2)0.056 (2)0.0105 (15)0.0178 (16)0.0055 (17)
C140.098 (2)0.071 (2)0.046 (2)0.0070 (17)0.0255 (17)0.0062 (18)
C150.097 (2)0.0483 (19)0.059 (2)0.0055 (15)0.0306 (18)0.0085 (16)
C160.0583 (17)0.0414 (16)0.049 (2)0.0051 (12)0.0223 (14)0.0044 (14)
C170.119 (3)0.0452 (19)0.055 (2)0.0039 (16)0.0372 (19)0.0044 (16)
C180.120 (3)0.0487 (19)0.064 (3)0.0007 (17)0.032 (2)0.0041 (18)
C190.0629 (19)0.0452 (16)0.051 (2)0.0008 (12)0.0220 (15)0.0063 (14)
C200.124 (3)0.0492 (19)0.077 (3)0.0136 (17)0.046 (2)0.0042 (17)
C210.078 (2)0.0488 (19)0.056 (2)0.0018 (14)0.0250 (16)0.0054 (17)
C220.123 (3)0.052 (2)0.060 (2)0.0063 (17)0.033 (2)0.0012 (16)
Geometric parameters (Å, º) top
O1—C101.225 (3)C9—H9C0.9600
O2—C211.223 (3)C10—C111.479 (4)
N1—C81.274 (3)C11—H11A0.9600
N1—N21.374 (3)C11—H11B0.9600
N2—C101.339 (4)C11—H11C0.9600
N2—H2A0.897 (10)C12—C131.505 (4)
N3—C191.280 (3)C12—H12A0.9600
N3—N41.369 (3)C12—H12B0.9600
N4—C211.335 (4)C12—H12C0.9600
N4—H4A0.900 (10)C13—C141.347 (4)
C1—C21.495 (4)C13—C181.374 (4)
C1—H1A0.9600C14—C151.378 (4)
C1—H1B0.9600C14—H140.9300
C1—H1C0.9600C15—C161.369 (4)
C2—C71.357 (4)C15—H150.9300
C2—C31.372 (4)C16—C171.377 (4)
C3—C41.364 (4)C16—C191.467 (4)
C3—H30.9300C17—C181.359 (4)
C4—C51.379 (3)C17—H170.9300
C4—H40.9300C18—H180.9300
C5—C61.368 (4)C19—C201.496 (4)
C5—C81.474 (4)C20—H20A0.9600
C6—C71.377 (4)C20—H20B0.9600
C6—H60.9300C20—H20C0.9600
C7—H70.9300C21—C221.480 (4)
C8—C91.487 (4)C22—H22A0.9600
C9—H9A0.9600C22—H22B0.9600
C9—H9B0.9600C22—H22C0.9600
C8—N1—N2118.5 (2)H11A—C11—H11B109.5
C10—N2—N1119.8 (2)C10—C11—H11C109.5
C10—N2—H2A116 (2)H11A—C11—H11C109.5
N1—N2—H2A124 (2)H11B—C11—H11C109.5
C19—N3—N4119.1 (2)C13—C12—H12A109.5
C21—N4—N3120.0 (3)C13—C12—H12B109.5
C21—N4—H4A114 (2)H12A—C12—H12B109.5
N3—N4—H4A123 (2)C13—C12—H12C109.5
C2—C1—H1A109.5H12A—C12—H12C109.5
C2—C1—H1B109.5H12B—C12—H12C109.5
H1A—C1—H1B109.5C14—C13—C18116.7 (3)
C2—C1—H1C109.5C14—C13—C12121.8 (3)
H1A—C1—H1C109.5C18—C13—C12121.5 (3)
H1B—C1—H1C109.5C13—C14—C15121.7 (3)
C7—C2—C3116.7 (3)C13—C14—H14119.1
C7—C2—C1121.6 (3)C15—C14—H14119.1
C3—C2—C1121.7 (3)C16—C15—C14122.0 (3)
C4—C3—C2121.9 (3)C16—C15—H15119.0
C4—C3—H3119.0C14—C15—H15119.0
C2—C3—H3119.0C15—C16—C17115.9 (3)
C3—C4—C5121.6 (3)C15—C16—C19122.2 (3)
C3—C4—H4119.2C17—C16—C19122.0 (3)
C5—C4—H4119.2C18—C17—C16121.7 (3)
C6—C5—C4116.2 (3)C18—C17—H17119.1
C6—C5—C8122.0 (2)C16—C17—H17119.1
C4—C5—C8121.7 (3)C17—C18—C13122.0 (3)
C5—C6—C7121.8 (3)C17—C18—H18119.0
C5—C6—H6119.1C13—C18—H18119.0
C7—C6—H6119.1N3—C19—C16115.6 (2)
C2—C7—C6121.8 (3)N3—C19—C20124.7 (3)
C2—C7—H7119.1C16—C19—C20119.7 (3)
C6—C7—H7119.1C19—C20—H20A109.5
N1—C8—C5115.1 (2)C19—C20—H20B109.5
N1—C8—C9125.2 (3)H20A—C20—H20B109.5
C5—C8—C9119.7 (3)C19—C20—H20C109.5
C8—C9—H9A109.5H20A—C20—H20C109.5
C8—C9—H9B109.5H20B—C20—H20C109.5
H9A—C9—H9B109.5O2—C21—N4119.8 (3)
C8—C9—H9C109.5O2—C21—C22122.1 (3)
H9A—C9—H9C109.5N4—C21—C22118.1 (3)
H9B—C9—H9C109.5C21—C22—H22A109.5
O1—C10—N2119.8 (3)C21—C22—H22B109.5
O1—C10—C11121.6 (3)H22A—C22—H22B109.5
N2—C10—C11118.6 (3)C21—C22—H22C109.5
C10—C11—H11A109.5H22A—C22—H22C109.5
C10—C11—H11B109.5H22B—C22—H22C109.5
C8—N1—N2—C10178.4 (2)N1—N2—C10—C113.9 (4)
C19—N3—N4—C21174.0 (3)C18—C13—C14—C150.3 (5)
C7—C2—C3—C40.5 (4)C12—C13—C14—C15179.9 (3)
C1—C2—C3—C4179.8 (3)C13—C14—C15—C160.3 (5)
C2—C3—C4—C50.1 (4)C14—C15—C16—C170.2 (4)
C3—C4—C5—C60.3 (4)C14—C15—C16—C19179.9 (3)
C3—C4—C5—C8179.4 (2)C15—C16—C17—C180.2 (4)
C4—C5—C6—C70.3 (4)C19—C16—C17—C18180.0 (3)
C8—C5—C6—C7179.4 (3)C16—C17—C18—C130.2 (5)
C3—C2—C7—C60.5 (4)C14—C13—C18—C170.3 (5)
C1—C2—C7—C6179.8 (3)C12—C13—C18—C17179.9 (3)
C5—C6—C7—C20.1 (5)N4—N3—C19—C16179.9 (2)
N2—N1—C8—C5179.7 (2)N4—N3—C19—C200.6 (4)
N2—N1—C8—C91.7 (4)C15—C16—C19—N3171.7 (3)
C6—C5—C8—N1167.5 (2)C17—C16—C19—N38.2 (4)
C4—C5—C8—N112.8 (4)C15—C16—C19—C209.1 (4)
C6—C5—C8—C914.4 (4)C17—C16—C19—C20171.1 (3)
C4—C5—C8—C9165.3 (3)N3—N4—C21—O2177.8 (3)
N1—N2—C10—O1176.5 (2)N3—N4—C21—C222.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.90 (1)2.08 (1)2.965 (3)170 (3)
N4—H4A···O1ii0.90 (1)2.09 (1)2.976 (3)167 (3)
C9—H9C···O2i0.962.393.199 (4)141
C20—H20C···O1ii0.962.603.243 (4)125
Symmetry codes: (i) x, y1, z1; (ii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC11H14ClN2O
Mr190.24
Crystal system, space groupMonoclinic, P21/n
Temperature (K)294
a, b, c (Å)7.2462 (14), 25.710 (5), 11.616 (2)
β (°) 105.159 (4)
V3)2088.8 (7)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.22 × 0.20 × 0.14
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10760, 3691, 1849
Rint0.054
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.191, 1.05
No. of reflections3691
No. of parameters268
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.15

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.898 (11)2.076 (11)2.965 (3)170 (3)
N4—H4A···O1ii0.900 (14)2.093 (13)2.976 (3)167 (3)
C9—H9C···O2i0.962.393.199 (4)141
C20—H20C···O1ii0.962.603.243 (4)125
Symmetry codes: (i) x, y1, z1; (ii) x, y+1, z+1.
 

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