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In the title compound, [Cu(C15H11ClN2O3)(C5H5N)], the hydrazide ligand chelates to the central Cu atom in an O,N,O'-tridentate manner and the pyridine mol­ecule coordin­ates through the N atom, forming a distorted square-planar geometry. The compound has a trans configuration with cis angles about the Cu atom between 81.1 (2) and 95.7 (2)°. The mol­ecule is discrete, with no significant intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804014357/na6340sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804014357/na6340Isup2.hkl
Contains datablock I

CCDC reference: 245148

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.026
  • wR factor = 0.076
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O1 .. 5.41 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - N2 .. 5.71 su PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 11 N3 -CU1 -N2 -C8 118.30 0.40 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 14 N3 -CU1 -N2 -N1 -56.90 0.40 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 16 N2 -CU1 -N3 -C16 65.10 0.50 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 19 N2 -CU1 -N3 -C20 -116.10 0.40 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON ( Spek, 2003).

{4-Chloro-2'-[(3-methoxy-2- oxidophenyl)methylidene]benzohydrazido}(pyridine)copper(II) top
Crystal data top
[Cu(C15H11ClN2O3)(C5H5N)]Z = 2
Mr = 445.35F(000) = 454
Triclinic, P1Dx = 1.607 Mg m3
a = 7.6672 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.3085 (7) ÅCell parameters from 7701 reflections
c = 14.6960 (12) Åθ = 2.4–27.0°
α = 97.960 (2)°µ = 1.36 mm1
β = 93.595 (2)°T = 273 K
γ = 95.405 (1)°Block, dark blue
V = 920.31 (13) Å30.41 × 0.36 × 0.24 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3984 independent reflections
Radiation source: fine-focus sealed tube3772 reflections with I > 2/s(I)
Graphite monochromatorRint = 0.017
Detector resolution: 83.66 pixels mm-1θmax = 27.0°, θmin = 2.4°
ω scansh = 99
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1010
Tmin = 0.592, Tmax = 0.721l = 1818
10319 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)] = 0.026H-atom parameters constrained
wR(F2) = 0.076 w = 1/[σ2(Fo2) + (0.0446P)2 + 0.1871P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3984 reflectionsΔρmax = 0.25 e Å3
255 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0119 (18)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.75487 (2)0.52913 (2)0.090779 (11)0.03938 (9)
Cl10.75367 (8)0.34476 (8)0.49596 (3)0.07209 (16)
O10.78306 (15)0.44294 (14)0.03628 (8)0.0432 (2)
O20.75302 (16)0.65257 (15)0.20830 (8)0.0468 (3)
O30.76142 (18)0.75695 (17)0.38279 (8)0.0561 (3)
N10.61711 (18)0.65172 (16)0.06421 (9)0.0420 (3)
N20.63615 (17)0.68417 (16)0.03158 (9)0.0389 (3)
N30.85531 (17)0.34606 (16)0.14420 (9)0.0395 (3)
C10.6130 (2)0.55112 (19)0.25473 (11)0.0424 (3)
H10.54000.62920.23370.051*
C20.6247 (2)0.5098 (2)0.34804 (11)0.0470 (4)
H20.55920.55820.39010.056*
C30.7359 (2)0.3949 (2)0.37793 (11)0.0455 (4)
C40.8321 (2)0.3196 (2)0.31736 (12)0.0483 (4)
H40.90610.24260.33880.058*
C50.8168 (2)0.3600 (2)0.22447 (11)0.0437 (3)
H50.87950.30810.18290.052*
C60.70917 (19)0.47720 (18)0.19159 (10)0.0369 (3)
C70.70261 (19)0.52495 (18)0.09123 (10)0.0374 (3)
C80.5635 (2)0.80707 (19)0.07073 (11)0.0421 (3)
H80.50170.86660.03290.051*
C90.5712 (2)0.85798 (18)0.16786 (11)0.0403 (3)
C100.6657 (2)0.77813 (18)0.23097 (11)0.0392 (3)
C110.6641 (2)0.83791 (19)0.32630 (11)0.0427 (3)
C120.5708 (2)0.9662 (2)0.35613 (12)0.0494 (4)
H120.56981.00230.41890.059*
C130.4776 (3)1.0427 (2)0.29249 (13)0.0556 (4)
H130.41401.12880.31300.067*
C140.4796 (2)0.9914 (2)0.20069 (13)0.0493 (4)
H140.41981.04490.15880.059*
C150.7647 (3)0.8069 (3)0.47861 (13)0.0702 (6)
H15A0.80930.92020.49280.105*
H15B0.83930.74250.51020.105*
H15C0.64780.79210.49810.105*
C160.9210 (3)0.2269 (2)0.09047 (12)0.0523 (4)
H160.91810.22990.02740.063*
C170.9926 (3)0.1005 (3)0.12474 (14)0.0663 (6)
H171.03800.02010.08540.080*
C180.9966 (3)0.0935 (2)0.21774 (14)0.0580 (5)
H181.04280.00790.24230.070*
C190.9308 (3)0.2154 (2)0.27300 (12)0.0529 (4)
H190.93250.21450.33630.064*
C200.8621 (2)0.3397 (2)0.23469 (11)0.0462 (4)
H200.81860.42260.27320.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.04743 (13)0.03901 (12)0.03373 (12)0.01612 (8)0.00137 (8)0.00537 (8)
Cl10.0962 (4)0.0831 (4)0.0374 (2)0.0299 (3)0.0042 (2)0.0034 (2)
O10.0505 (6)0.0463 (6)0.0358 (5)0.0189 (5)0.0018 (4)0.0082 (4)
O20.0540 (7)0.0494 (7)0.0387 (6)0.0254 (5)0.0003 (5)0.0005 (5)
O30.0653 (8)0.0671 (8)0.0389 (6)0.0290 (6)0.0027 (5)0.0032 (5)
N10.0511 (7)0.0416 (7)0.0362 (6)0.0136 (6)0.0043 (5)0.0094 (5)
N20.0446 (7)0.0373 (6)0.0363 (6)0.0092 (5)0.0031 (5)0.0078 (5)
N30.0438 (7)0.0385 (6)0.0375 (6)0.0113 (5)0.0011 (5)0.0059 (5)
C10.0498 (8)0.0390 (8)0.0412 (8)0.0134 (6)0.0040 (6)0.0089 (6)
C20.0578 (10)0.0455 (9)0.0397 (8)0.0137 (7)0.0008 (7)0.0097 (7)
C30.0538 (9)0.0455 (8)0.0361 (8)0.0057 (7)0.0034 (6)0.0017 (6)
C40.0492 (9)0.0484 (9)0.0482 (9)0.0153 (7)0.0051 (7)0.0019 (7)
C50.0435 (8)0.0457 (8)0.0435 (8)0.0133 (6)0.0006 (6)0.0076 (7)
C60.0374 (7)0.0360 (7)0.0383 (7)0.0046 (6)0.0027 (6)0.0084 (6)
C70.0377 (7)0.0385 (7)0.0375 (7)0.0057 (6)0.0030 (5)0.0090 (6)
C80.0478 (8)0.0357 (7)0.0459 (8)0.0115 (6)0.0042 (6)0.0115 (6)
C90.0454 (8)0.0314 (7)0.0456 (8)0.0084 (6)0.0072 (6)0.0068 (6)
C100.0399 (7)0.0352 (7)0.0431 (8)0.0078 (6)0.0055 (6)0.0041 (6)
C110.0464 (8)0.0397 (8)0.0428 (8)0.0078 (6)0.0062 (6)0.0047 (6)
C120.0644 (10)0.0401 (8)0.0455 (9)0.0119 (7)0.0154 (7)0.0028 (7)
C130.0754 (12)0.0368 (8)0.0595 (11)0.0223 (8)0.0189 (9)0.0071 (7)
C140.0623 (10)0.0363 (8)0.0536 (10)0.0188 (7)0.0096 (8)0.0102 (7)
C150.0889 (15)0.0834 (15)0.0406 (10)0.0308 (12)0.0039 (9)0.0027 (9)
C160.0717 (11)0.0489 (9)0.0387 (8)0.0238 (8)0.0014 (7)0.0040 (7)
C170.0964 (16)0.0528 (11)0.0540 (11)0.0376 (11)0.0032 (10)0.0033 (9)
C180.0706 (12)0.0496 (10)0.0587 (11)0.0214 (9)0.0016 (9)0.0180 (8)
C190.0623 (11)0.0604 (10)0.0409 (9)0.0154 (8)0.0031 (7)0.0186 (8)
C200.0522 (9)0.0491 (9)0.0404 (8)0.0158 (7)0.0067 (7)0.0083 (7)
Geometric parameters (Å, º) top
Cu1—O21.8842 (11)C6—C71.479 (2)
Cu1—N21.9174 (13)C8—C91.427 (2)
Cu1—O11.9380 (11)C8—H80.9300
Cu1—N31.9996 (13)C9—C141.412 (2)
Cl1—C31.7439 (17)C9—C101.415 (2)
O1—C71.2907 (18)C10—C111.421 (2)
O2—C101.3080 (18)C11—C121.376 (2)
O3—C111.367 (2)C12—C131.398 (3)
O3—C151.410 (2)C12—H120.9300
N1—C71.320 (2)C13—C141.359 (3)
N1—N21.3920 (18)C13—H130.9300
N2—C81.292 (2)C14—H140.9300
N3—C161.336 (2)C15—H15A0.9600
N3—C201.336 (2)C15—H15B0.9600
C1—C21.377 (2)C15—H15C0.9600
C1—C61.393 (2)C16—C171.370 (3)
C1—H10.9300C16—H160.9300
C2—C31.384 (2)C17—C181.375 (3)
C2—H20.9300C17—H170.9300
C3—C41.374 (2)C18—C191.364 (3)
C4—C51.375 (2)C18—H180.9300
C4—H40.9300C19—C201.374 (2)
C5—C61.391 (2)C19—H190.9300
C5—H50.9300C20—H200.9300
O2—Cu1—N292.63 (5)C14—C9—C10119.86 (15)
O2—Cu1—O1168.10 (5)C14—C9—C8118.17 (15)
N2—Cu1—O181.18 (5)C10—C9—C8121.97 (14)
O2—Cu1—N391.85 (5)O2—C10—C9124.98 (14)
N2—Cu1—N3172.75 (5)O2—C10—C11117.53 (14)
O1—Cu1—N395.38 (5)C9—C10—C11117.49 (14)
C7—O1—Cu1110.25 (9)O3—C11—C12124.73 (15)
C10—O2—Cu1127.40 (10)O3—C11—C10114.06 (14)
C11—O3—C15117.73 (14)C12—C11—C10121.20 (15)
C7—N1—N2108.51 (12)C11—C12—C13120.27 (16)
C8—N2—N1117.40 (13)C11—C12—H12119.9
C8—N2—Cu1127.27 (11)C13—C12—H12119.9
N1—N2—Cu1115.17 (10)C14—C13—C12120.15 (16)
C16—N3—C20117.62 (14)C14—C13—H13119.9
C16—N3—Cu1120.92 (11)C12—C13—H13119.9
C20—N3—Cu1121.46 (11)C13—C14—C9120.99 (16)
C2—C1—C6120.74 (15)C13—C14—H14119.5
C2—C1—H1119.6C9—C14—H14119.5
C6—C1—H1119.6O3—C15—H15A109.5
C1—C2—C3118.71 (15)O3—C15—H15B109.5
C1—C2—H2120.6H15A—C15—H15B109.5
C3—C2—H2120.6O3—C15—H15C109.5
C4—C3—C2121.89 (15)H15A—C15—H15C109.5
C4—C3—Cl1119.30 (13)H15B—C15—H15C109.5
C2—C3—Cl1118.81 (13)N3—C16—C17122.54 (17)
C3—C4—C5118.75 (15)N3—C16—H16118.7
C3—C4—H4120.6C17—C16—H16118.7
C5—C4—H4120.6C16—C17—C18119.50 (18)
C4—C5—C6121.11 (15)C16—C17—H17120.3
C4—C5—H5119.4C18—C17—H17120.3
C6—C5—H5119.4C19—C18—C17118.20 (17)
C5—C6—C1118.77 (15)C19—C18—H18120.9
C5—C6—C7120.01 (14)C17—C18—H18120.9
C1—C6—C7121.19 (14)C18—C19—C20119.62 (16)
O1—C7—N1124.57 (13)C18—C19—H19120.2
O1—C7—C6118.26 (13)C20—C19—H19120.2
N1—C7—C6117.15 (13)N3—C20—C19122.51 (16)
N2—C8—C9124.67 (14)N3—C20—H20118.7
N2—C8—H8117.7C19—C20—H20118.7
C9—C8—H8117.7
O2—Cu1—O1—C762.8 (3)C5—C6—C7—O17.5 (2)
N2—Cu1—O1—C73.55 (10)C1—C6—C7—O1174.40 (14)
N3—Cu1—O1—C7170.02 (11)C5—C6—C7—N1171.07 (15)
N2—Cu1—O2—C1011.17 (14)C1—C6—C7—N17.0 (2)
O1—Cu1—O2—C1069.4 (3)N1—N2—C8—C9179.53 (14)
N3—Cu1—O2—C10163.14 (14)Cu1—N2—C8—C95.4 (2)
C7—N1—N2—C8178.74 (14)N2—C8—C9—C14177.74 (16)
C7—N1—N2—Cu15.57 (16)N2—C8—C9—C101.7 (3)
O2—Cu1—N2—C89.85 (15)Cu1—O2—C10—C98.2 (2)
O1—Cu1—N2—C8179.62 (15)Cu1—O2—C10—C11171.13 (11)
N3—Cu1—N2—C8118.3 (4)C14—C9—C10—O2179.12 (15)
O2—Cu1—N2—N1174.96 (10)C8—C9—C10—O20.3 (2)
O1—Cu1—N2—N15.18 (10)C14—C9—C10—C110.2 (2)
N3—Cu1—N2—N156.9 (4)C8—C9—C10—C11179.63 (14)
O2—Cu1—N3—C16166.73 (14)C15—O3—C11—C120.9 (3)
N2—Cu1—N3—C1665.1 (5)C15—O3—C11—C10179.04 (17)
O1—Cu1—N3—C163.80 (14)O2—C10—C11—O32.0 (2)
O2—Cu1—N3—C2012.09 (13)C9—C10—C11—O3178.62 (14)
N2—Cu1—N3—C20116.1 (4)O2—C10—C11—C12177.93 (16)
O1—Cu1—N3—C20177.38 (13)C9—C10—C11—C121.4 (2)
C6—C1—C2—C30.9 (3)O3—C11—C12—C13178.93 (17)
C1—C2—C3—C41.0 (3)C10—C11—C12—C131.1 (3)
C1—C2—C3—Cl1179.00 (13)C11—C12—C13—C140.5 (3)
C2—C3—C4—C50.0 (3)C12—C13—C14—C91.8 (3)
Cl1—C3—C4—C5179.94 (13)C10—C9—C14—C131.4 (3)
C3—C4—C5—C61.3 (3)C8—C9—C14—C13178.06 (17)
C4—C5—C6—C11.5 (2)C20—N3—C16—C170.4 (3)
C4—C5—C6—C7176.64 (14)Cu1—N3—C16—C17179.30 (17)
C2—C1—C6—C50.4 (2)N3—C16—C17—C180.6 (4)
C2—C1—C6—C7177.72 (14)C16—C17—C18—C191.0 (3)
Cu1—O1—C7—N11.48 (19)C17—C18—C19—C200.5 (3)
Cu1—O1—C7—C6179.98 (10)C16—N3—C20—C191.0 (3)
N2—N1—C7—O12.6 (2)Cu1—N3—C20—C19179.84 (14)
N2—N1—C7—C6175.88 (12)C18—C19—C20—N30.5 (3)
 

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