Download citation
Download citation
link to html
In the title compound, C17H13ClN4O2, the dihedral angle between the benzene and quinoline ring systems is 20.95 (4)°. C—H...O and C—H...N hydrogen bonds, as well as π–π stacking inter­actions, are observed in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023020/ci6616sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023020/ci6616Isup2.hkl
Contains datablock I

CCDC reference: 282296

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.044
  • wR factor = 0.067
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.149 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.15 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - C5 .. 5.16 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C13 - C14 .. 6.08 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLUTON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

N-(4-Chloro-2-nitrophenyl)-N-methyl-N'-(quinolin-4-ylmethylene)hydrazine top
Crystal data top
C17H13ClN4O2F(000) = 704
Mr = 340.76Dx = 1.456 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6356 reflections
a = 12.5083 (15) Åθ = 1.6–25.7°
b = 6.9995 (5) ŵ = 0.26 mm1
c = 17.885 (2) ÅT = 296 K
β = 96.988 (10)°Prism, yellow
V = 1554.2 (3) Å30.50 × 0.42 × 0.32 mm
Z = 4
Data collection top
Stoe IPDS-II
diffractometer
3049 independent reflections
Radiation source: fine-focus sealed tube1276 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.149
ω scansθmax = 26.0°, θmin = 1.6°
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
h = 1515
Tmin = 0.918, Tmax = 0.975k = 88
21401 measured reflectionsl = 2222
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)] = 0.044H-atom parameters constrained
wR(F2) = 0.067 w = 1/[σ2(Fo2) + (0.0033P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max = 0.001
3049 reflectionsΔρmax = 0.16 e Å3
219 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00128 (8)
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
Cl10.85026 (6)0.35779 (14)0.01746 (5)0.0830 (3)
O10.46862 (15)0.0322 (3)0.08221 (11)0.0712 (7)
O20.43639 (14)0.3242 (3)0.04797 (12)0.0846 (8)
N10.08395 (17)0.2698 (4)0.21312 (15)0.0698 (8)
N20.48635 (15)0.2338 (3)0.22032 (11)0.0450 (6)
N30.59546 (16)0.2127 (3)0.23563 (12)0.0455 (6)
N40.49464 (17)0.1976 (4)0.07562 (13)0.0529 (7)
C10.7755 (2)0.3177 (4)0.05596 (16)0.0543 (8)
C20.8244 (2)0.3121 (4)0.12910 (17)0.0558 (8)
H20.89830.33110.13910.067*
C30.76519 (19)0.2788 (4)0.18752 (15)0.0502 (8)
H30.80000.27830.23650.060*
C40.65390 (19)0.2453 (4)0.17580 (15)0.0417 (7)
C50.60854 (18)0.2502 (4)0.10084 (15)0.0420 (7)
C60.6666 (2)0.2877 (4)0.04191 (15)0.0499 (8)
H60.63210.29260.00720.060*
C70.64514 (18)0.1868 (4)0.31306 (14)0.0573 (9)
H7A0.63920.30300.34070.086*
H7B0.71980.15480.31320.086*
H7C0.60920.08550.33620.086*
C80.42592 (19)0.2187 (4)0.27261 (16)0.0492 (8)
H80.45570.19740.32210.059*
C90.3077 (2)0.2357 (4)0.25343 (15)0.0458 (7)
C100.24085 (19)0.2709 (4)0.31029 (15)0.0455 (8)
C110.2765 (2)0.2925 (4)0.38690 (17)0.0504 (8)
H110.34980.28440.40330.061*
C120.2064 (2)0.3250 (4)0.43836 (16)0.0610 (9)
H120.23200.33830.48910.073*
C130.0956 (2)0.3385 (5)0.4145 (2)0.0748 (10)
H130.04780.36020.44950.090*
C140.0582 (2)0.3200 (5)0.34087 (19)0.0681 (10)
H140.01550.32960.32580.082*
C150.1276 (2)0.2868 (4)0.28710 (17)0.0541 (8)
C160.1495 (2)0.2362 (5)0.16368 (18)0.0712 (10)
H160.11970.22420.11370.085*
C170.2620 (2)0.2164 (4)0.17968 (16)0.0594 (9)
H170.30430.19100.14160.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0589 (5)0.1141 (8)0.0806 (6)0.0083 (5)0.0265 (4)0.0025 (6)
O10.0594 (13)0.0751 (17)0.0781 (17)0.0244 (13)0.0046 (11)0.0176 (14)
O20.0449 (12)0.118 (2)0.0860 (17)0.0063 (13)0.0130 (11)0.0468 (15)
N10.0396 (14)0.094 (2)0.072 (2)0.0038 (14)0.0095 (14)0.0061 (17)
N20.0353 (13)0.0507 (16)0.0471 (15)0.0011 (11)0.0024 (11)0.0011 (12)
N30.0345 (12)0.0600 (18)0.0396 (14)0.0039 (11)0.0054 (10)0.0005 (12)
N40.0419 (15)0.070 (2)0.0461 (16)0.0028 (14)0.0019 (11)0.0021 (15)
C10.0426 (17)0.059 (2)0.062 (2)0.0014 (15)0.0102 (15)0.0005 (17)
C20.0314 (14)0.057 (2)0.077 (2)0.0024 (14)0.0002 (15)0.0101 (18)
C30.0352 (16)0.056 (2)0.056 (2)0.0023 (14)0.0071 (14)0.0072 (16)
C40.0397 (16)0.0387 (18)0.0457 (17)0.0033 (13)0.0007 (13)0.0026 (14)
C50.0302 (14)0.0451 (18)0.0485 (18)0.0009 (13)0.0034 (13)0.0031 (15)
C60.0452 (17)0.053 (2)0.0497 (19)0.0024 (14)0.0003 (14)0.0018 (15)
C70.0519 (18)0.069 (2)0.0470 (18)0.0060 (16)0.0114 (14)0.0068 (17)
C80.0411 (16)0.052 (2)0.0528 (19)0.0022 (14)0.0026 (15)0.0025 (16)
C90.0403 (16)0.0435 (19)0.052 (2)0.0063 (13)0.0029 (14)0.0028 (15)
C100.0399 (16)0.042 (2)0.054 (2)0.0063 (14)0.0026 (15)0.0043 (16)
C110.0386 (15)0.057 (2)0.0553 (19)0.0045 (14)0.0049 (14)0.0065 (16)
C120.0549 (18)0.074 (2)0.0539 (19)0.0039 (17)0.0073 (16)0.0023 (17)
C130.051 (2)0.084 (3)0.093 (3)0.0051 (19)0.0243 (17)0.002 (2)
C140.0428 (18)0.084 (3)0.078 (2)0.0041 (17)0.0071 (17)0.003 (2)
C150.0387 (16)0.058 (2)0.065 (2)0.0082 (15)0.0038 (15)0.0022 (17)
C160.048 (2)0.098 (3)0.062 (2)0.0063 (18)0.0137 (16)0.004 (2)
C170.0489 (18)0.073 (2)0.055 (2)0.0087 (16)0.0011 (15)0.0040 (17)
Geometric parameters (Å, º) top
Cl1—C11.725 (3)C7—H7B0.96
O1—N41.212 (3)C7—H7C0.96
O2—N41.213 (3)C8—C91.482 (3)
N1—C161.298 (3)C8—H80.93
N1—C151.374 (3)C9—C171.379 (3)
N2—C81.276 (3)C9—C101.414 (3)
N2—N31.367 (2)C10—C111.397 (3)
N3—C41.386 (3)C10—C151.431 (3)
N3—C71.459 (3)C11—C121.365 (3)
N4—C51.487 (3)C11—H110.93
C1—C61.372 (3)C12—C131.403 (3)
C1—C21.375 (3)C12—H120.93
C2—C31.372 (4)C13—C141.349 (4)
C2—H20.93C13—H130.93
C3—C41.402 (3)C14—C151.392 (4)
C3—H30.93C14—H140.93
C4—C51.391 (3)C16—C171.409 (3)
C5—C61.376 (3)C16—H160.93
C6—H60.93C17—H170.93
C7—H7A0.96
C16—N1—C15117.5 (2)H7B—C7—H7C109.5
C8—N2—N3120.7 (2)N2—C8—C9119.1 (2)
N2—N3—C4115.8 (2)N2—C8—H8120.4
N2—N3—C7120.2 (2)C9—C8—H8120.4
C4—N3—C7123.3 (2)C17—C9—C10119.5 (2)
O1—N4—O2125.6 (2)C17—C9—C8120.0 (3)
O1—N4—C5117.7 (2)C10—C9—C8120.5 (3)
O2—N4—C5116.7 (3)C11—C10—C9125.3 (2)
C6—C1—C2119.1 (3)C11—C10—C15117.6 (3)
C6—C1—Cl1120.3 (2)C9—C10—C15117.1 (3)
C2—C1—Cl1120.6 (2)C12—C11—C10121.7 (3)
C3—C2—C1120.7 (3)C12—C11—H11119.2
C3—C2—H2119.7C10—C11—H11119.2
C1—C2—H2119.7C11—C12—C13119.8 (3)
C2—C3—C4122.2 (3)C11—C12—H12120.1
C2—C3—H3118.9C13—C12—H12120.1
C4—C3—H3118.9C14—C13—C12120.3 (3)
N3—C4—C5123.8 (2)C14—C13—H13119.9
N3—C4—C3121.3 (2)C12—C13—H13119.9
C5—C4—C3114.9 (3)C13—C14—C15121.2 (3)
C6—C5—C4123.5 (2)C13—C14—H14119.4
C6—C5—N4113.0 (2)C15—C14—H14119.4
C4—C5—N4123.3 (3)N1—C15—C14118.1 (3)
C1—C6—C5119.6 (3)N1—C15—C10122.4 (3)
C1—C6—H6120.2C14—C15—C10119.5 (3)
C5—C6—H6120.2N1—C16—C17125.3 (3)
N3—C7—H7A109.5N1—C16—H16117.4
N3—C7—H7B109.5C17—C16—H16117.4
H7A—C7—H7B109.5C9—C17—C16118.2 (3)
N3—C7—H7C109.5C9—C17—H17120.9
H7A—C7—H7C109.5C16—C17—H17120.9
C8—N2—N3—C4175.6 (2)N2—C8—C9—C1717.2 (4)
C8—N2—N3—C74.6 (4)N2—C8—C9—C10163.0 (3)
C6—C1—C2—C30.6 (4)C17—C9—C10—C11179.7 (3)
Cl1—C1—C2—C3179.5 (2)C8—C9—C10—C110.1 (4)
C1—C2—C3—C41.3 (4)C17—C9—C10—C150.7 (4)
N2—N3—C4—C516.3 (4)C8—C9—C10—C15179.6 (2)
C7—N3—C4—C5172.9 (2)C9—C10—C11—C12179.6 (3)
N2—N3—C4—C3162.8 (2)C15—C10—C11—C120.8 (4)
C7—N3—C4—C37.9 (4)C10—C11—C12—C130.3 (5)
C2—C3—C4—N3179.7 (3)C11—C12—C13—C140.2 (5)
C2—C3—C4—C50.5 (4)C12—C13—C14—C150.2 (5)
N3—C4—C5—C6178.2 (3)C16—N1—C15—C14179.1 (3)
C3—C4—C5—C61.0 (4)C16—N1—C15—C100.8 (4)
N3—C4—C5—N47.7 (4)C13—C14—C15—N1179.9 (3)
C3—C4—C5—N4173.1 (3)C13—C14—C15—C100.3 (5)
O1—N4—C5—C6107.7 (3)C11—C10—C15—N1179.4 (3)
O2—N4—C5—C670.1 (3)C9—C10—C15—N10.3 (4)
O1—N4—C5—C466.9 (4)C11—C10—C15—C140.8 (4)
O2—N4—C5—C4115.2 (3)C9—C10—C15—C14179.5 (3)
C2—C1—C6—C50.8 (4)C15—N1—C16—C170.3 (5)
Cl1—C1—C6—C5178.1 (2)C10—C9—C17—C161.1 (4)
C4—C5—C6—C11.7 (4)C8—C9—C17—C16179.1 (3)
N4—C5—C6—C1172.9 (2)N1—C16—C17—C90.7 (5)
N3—N2—C8—C9177.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N1i0.932.573.420 (3)153
C7—H7A···O1ii0.962.603.468 (3)151
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1/2, z+1/2.
 

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