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In the structure of the title complex, [Cu(C14H9N3O4)(C4H9NO)], the Cu atom is coordinated by two O atoms and one N atom from the N-salicylaldehyde p-nitro­benzoyl­hydrazone ligand and one N atom from a morpholine mol­ecule, forming a square-planar Cu(ONO)(N) coordination. The g factors derived by an electron paramagnetic resonance study are typical for square-planar complexes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805017642/rz6081sup1.cif
Contains datablocks d, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805017642/rz6081Isup2.hkl
Contains datablock I

CCDC reference: 277762

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.054
  • wR factor = 0.120
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT093_ALERT_1_A No su's on H-atoms, but refinement reported as . mixed
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3A PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4N ... ?
1 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 4 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 1 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 (Siemens, 1996); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1994); software used to prepare material for publication: SHELXTL.

(N-Salicylaldehyde-p-nitrobenzoylhydrazonato-κ3O,N,O') (morpholine-κN)copper(II) top
Crystal data top
[Cu(C14H9N3O4)(C4H9NO)]F(000) = 1784
Mr = 433.90Dx = 1.625 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3892 reflections
a = 15.054 (7) Åθ = 2.3–27.2°
b = 6.538 (3) ŵ = 1.27 mm1
c = 36.230 (15) ÅT = 293 K
β = 95.800 (6)°Needle, blue
V = 3548 (3) Å30.10 × 0.08 × 0.05 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
3892 independent reflections
Radiation source: fine-focus sealed tube2581 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
φ and ω scansθmax = 27.2°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1819
Tmin = 0.885, Tmax = 0.938k = 88
8552 measured reflectionsl = 4634
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0497P)2 + 1.9541P]
where P = (Fo2 + 2Fc2)/3
3892 reflections(Δ/σ)max = 0.001
272 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.38 e Å3
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*/UeqOcc. (<1)
Cu10.22389 (3)0.07069 (7)0.365297 (12)0.03771 (16)
O10.22101 (16)0.0999 (4)0.32320 (7)0.0426 (6)
O20.21382 (17)0.2334 (4)0.40890 (7)0.0470 (7)
O3A0.1385 (13)0.738 (3)0.5661 (6)0.078 (5)0.50
O4A0.047 (2)0.523 (4)0.5802 (8)0.068 (7)0.50
O3B0.067 (2)0.499 (4)0.5859 (8)0.074 (8)0.50
O4B0.1075 (14)0.786 (3)0.5582 (6)0.065 (4)0.50
O50.46962 (17)0.4718 (4)0.33022 (8)0.0531 (8)
N10.1515 (2)0.1121 (5)0.39117 (8)0.0375 (7)
N20.1283 (2)0.0373 (5)0.42531 (8)0.0445 (8)
N30.0962 (3)0.5897 (6)0.55969 (10)0.0550 (9)
N40.30535 (18)0.2736 (5)0.34362 (8)0.0354 (7)
H4N0.26900.35250.32780.071 (15)*
C10.1774 (2)0.2728 (6)0.31768 (10)0.0355 (8)
C20.1291 (2)0.3717 (5)0.34440 (10)0.0356 (8)
C30.0872 (2)0.5576 (6)0.33542 (11)0.0429 (9)
H3A0.05620.62170.35310.052*
C40.0897 (2)0.6498 (6)0.30170 (11)0.0454 (10)
H4A0.06140.77450.29650.054*
C50.1355 (3)0.5524 (6)0.27543 (11)0.0473 (10)
H5A0.13680.61090.25210.057*
C60.1788 (3)0.3709 (6)0.28340 (10)0.0452 (10)
H6A0.21010.31090.26540.054*
C70.1180 (2)0.2832 (6)0.37965 (10)0.0420 (9)
H7A0.08400.35500.39540.050*
C80.1644 (2)0.1410 (6)0.43099 (10)0.0394 (9)
C90.1456 (2)0.2563 (6)0.46473 (10)0.0376 (9)
C100.0987 (3)0.1672 (6)0.49192 (10)0.0455 (10)
H10A0.07840.03330.48890.055*
C110.0821 (3)0.2743 (6)0.52303 (10)0.0461 (10)
H11A0.05100.21450.54110.055*
C120.1126 (2)0.4731 (6)0.52681 (10)0.0390 (9)
C130.1574 (3)0.5654 (7)0.50024 (11)0.0480 (10)
H13A0.17560.70100.50290.058*
C140.1749 (3)0.4557 (6)0.46975 (11)0.0474 (10)
H14A0.20710.51620.45200.057*
C150.3525 (3)0.4172 (7)0.37000 (11)0.0514 (11)
H15A0.39080.34060.38820.062*
H15B0.30910.49030.38310.062*
C160.4079 (3)0.5684 (7)0.35146 (12)0.0569 (12)
H16A0.36890.65600.33540.068*
H16B0.44000.65400.37020.068*
C170.4242 (3)0.3434 (7)0.30314 (11)0.0527 (11)
H17A0.46730.27800.28880.063*
H17B0.38470.42560.28630.063*
C180.3703 (3)0.1813 (6)0.32060 (11)0.0461 (10)
H18A0.33870.09880.30120.055*
H18B0.41030.09220.33590.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0403 (3)0.0365 (3)0.0380 (3)0.0084 (2)0.01202 (18)0.0020 (2)
O10.0536 (16)0.0358 (16)0.0413 (15)0.0165 (12)0.0183 (12)0.0059 (12)
O20.0580 (17)0.0460 (17)0.0404 (15)0.0186 (13)0.0215 (13)0.0060 (13)
O3A0.098 (13)0.070 (13)0.070 (11)0.035 (8)0.032 (8)0.038 (8)
O4A0.082 (9)0.066 (10)0.063 (11)0.017 (9)0.047 (10)0.002 (7)
O3B0.13 (2)0.056 (7)0.039 (6)0.010 (7)0.036 (9)0.009 (6)
O4B0.103 (13)0.036 (6)0.060 (7)0.007 (6)0.021 (7)0.006 (4)
O50.0428 (15)0.0512 (19)0.0678 (19)0.0171 (13)0.0181 (13)0.0080 (15)
N10.0445 (18)0.0353 (19)0.0341 (17)0.0055 (14)0.0111 (13)0.0012 (14)
N20.054 (2)0.043 (2)0.0395 (18)0.0119 (16)0.0202 (15)0.0057 (16)
N30.061 (2)0.060 (3)0.046 (2)0.013 (2)0.0140 (18)0.014 (2)
N40.0330 (16)0.0357 (18)0.0388 (17)0.0032 (14)0.0106 (14)0.0023 (14)
C10.0325 (19)0.033 (2)0.042 (2)0.0027 (16)0.0077 (15)0.0021 (17)
C20.0318 (19)0.037 (2)0.039 (2)0.0009 (15)0.0076 (15)0.0003 (16)
C30.036 (2)0.042 (2)0.052 (2)0.0085 (18)0.0128 (17)0.003 (2)
C40.043 (2)0.037 (2)0.056 (3)0.0079 (17)0.0035 (19)0.0061 (19)
C50.053 (2)0.050 (3)0.040 (2)0.006 (2)0.0078 (18)0.006 (2)
C60.051 (2)0.047 (3)0.039 (2)0.0079 (19)0.0086 (18)0.0015 (18)
C70.040 (2)0.043 (2)0.045 (2)0.0061 (18)0.0155 (17)0.0052 (19)
C80.039 (2)0.043 (2)0.037 (2)0.0021 (17)0.0078 (16)0.0011 (17)
C90.037 (2)0.042 (2)0.034 (2)0.0031 (17)0.0048 (15)0.0015 (17)
C100.057 (3)0.036 (2)0.045 (2)0.0115 (19)0.0161 (19)0.0032 (18)
C110.054 (2)0.047 (3)0.040 (2)0.008 (2)0.0143 (18)0.0018 (19)
C120.041 (2)0.041 (2)0.035 (2)0.0018 (17)0.0058 (16)0.0049 (17)
C130.050 (2)0.043 (2)0.052 (2)0.016 (2)0.0132 (19)0.007 (2)
C140.051 (2)0.051 (3)0.043 (2)0.011 (2)0.0158 (18)0.001 (2)
C150.057 (2)0.054 (3)0.046 (2)0.024 (2)0.0192 (19)0.019 (2)
C160.054 (3)0.048 (3)0.073 (3)0.019 (2)0.025 (2)0.014 (2)
C170.050 (2)0.062 (3)0.050 (3)0.015 (2)0.023 (2)0.003 (2)
C180.047 (2)0.047 (3)0.048 (2)0.0116 (19)0.0197 (19)0.0073 (19)
Geometric parameters (Å, º) top
Cu1—O11.886 (2)C4—H4A0.9300
Cu1—O21.923 (3)C5—C61.370 (5)
Cu1—N11.924 (3)C5—H5A0.9300
Cu1—N42.019 (3)C6—H6A0.9300
O1—C11.312 (4)C7—H7A0.9300
O2—C81.296 (4)C8—C91.487 (5)
O3A—N31.17 (2)C9—C141.382 (5)
O4A—N31.19 (2)C9—C101.396 (5)
O3B—N31.24 (3)C10—C111.371 (5)
O4B—N31.30 (2)C10—H10A0.9300
O5—C171.414 (5)C11—C121.380 (5)
O5—C161.414 (5)C11—H11A0.9300
N1—C71.279 (5)C12—C131.370 (5)
N1—N21.406 (4)C13—C141.365 (5)
N2—C81.294 (5)C13—H13A0.9300
N3—C121.456 (5)C14—H14A0.9300
N4—C151.470 (5)C15—C161.496 (5)
N4—C181.477 (4)C15—H15A0.9700
N4—H4N0.9100C15—H15B0.9700
C1—C61.400 (5)C16—H16A0.9700
C1—C21.424 (5)C16—H16B0.9700
C2—C31.393 (5)C17—C181.512 (5)
C2—C71.427 (5)C17—H17A0.9700
C3—C41.366 (5)C17—H17B0.9700
C3—H3A0.9300C18—H18A0.9700
C4—C51.385 (5)C18—H18B0.9700
O1—Cu1—O2173.66 (10)C2—C7—H7A117.7
O1—Cu1—N193.38 (12)N2—C8—O2125.4 (4)
O2—Cu1—N181.24 (12)N2—C8—C9118.4 (3)
O1—Cu1—N492.24 (11)O2—C8—C9116.1 (3)
O2—Cu1—N493.30 (11)C14—C9—C10118.5 (4)
N1—Cu1—N4173.77 (12)C14—C9—C8120.1 (3)
C1—O1—Cu1127.1 (2)C10—C9—C8121.4 (4)
C8—O2—Cu1110.3 (2)C11—C10—C9120.9 (4)
O4B—O3A—N388 (5)C11—C10—H10A119.5
O3A—O4B—N364 (4)C9—C10—H10A119.5
C17—O5—C16110.1 (3)C10—C11—C12118.4 (4)
C7—N1—N2117.8 (3)C10—C11—H11A120.8
C7—N1—Cu1127.4 (3)C12—C11—H11A120.8
N2—N1—Cu1114.6 (2)C13—C12—C11121.8 (4)
C8—N2—N1108.4 (3)C13—C12—N3118.7 (4)
O3A—N3—O4A122.9 (17)C11—C12—N3119.5 (3)
O3B—N3—O4B124.3 (16)C14—C13—C12119.1 (4)
O3A—N3—C12117.6 (11)C14—C13—H13A120.5
O4A—N3—C12119.2 (13)C12—C13—H13A120.5
O3B—N3—C12118.7 (12)C13—C14—C9121.1 (4)
O4B—N3—C12116.8 (11)C13—C14—H14A119.4
C15—N4—C18108.9 (3)C9—C14—H14A119.4
C15—N4—Cu1116.0 (2)N4—C15—C16112.6 (3)
C18—N4—Cu1114.5 (2)N4—C15—H15A109.1
C15—N4—H4N105.5C16—C15—H15A109.1
C18—N4—H4N105.5N4—C15—H15B109.1
Cu1—N4—H4N105.5C16—C15—H15B109.1
O1—C1—C6118.6 (3)H15A—C15—H15B107.8
O1—C1—C2124.7 (3)O5—C16—C15112.1 (4)
C6—C1—C2116.7 (3)O5—C16—H16A109.2
C3—C2—C1119.2 (3)C15—C16—H16A109.2
C3—C2—C7118.2 (3)O5—C16—H16B109.2
C1—C2—C7122.6 (3)C15—C16—H16B109.2
C4—C3—C2122.8 (3)H16A—C16—H16B107.9
C4—C3—H3A118.6O5—C17—C18111.6 (3)
C2—C3—H3A118.6O5—C17—H17A109.3
C3—C4—C5118.2 (4)C18—C17—H17A109.3
C3—C4—H4A120.9O5—C17—H17B109.3
C5—C4—H4A120.9C18—C17—H17B109.3
C6—C5—C4120.8 (4)H17A—C17—H17B108.0
C6—C5—H5A119.6N4—C18—C17111.3 (3)
C4—C5—H5A119.6N4—C18—H18A109.4
C5—C6—C1122.3 (4)C17—C18—H18A109.4
C5—C6—H6A118.8N4—C18—H18B109.4
C1—C6—H6A118.8C17—C18—H18B109.4
N1—C7—C2124.7 (3)H18A—C18—H18B108.0
N1—C7—H7A117.7
N1—Cu1—O1—C12.9 (3)C1—C2—C7—N11.9 (6)
N4—Cu1—O1—C1179.8 (3)N1—N2—C8—O20.2 (5)
N1—Cu1—O2—C81.5 (3)N1—N2—C8—C9177.0 (3)
N4—Cu1—O2—C8178.5 (3)Cu1—O2—C8—N21.5 (5)
O1—Cu1—N1—C70.4 (3)Cu1—O2—C8—C9175.9 (2)
O2—Cu1—N1—C7176.2 (3)N2—C8—C9—C14173.0 (4)
O1—Cu1—N1—N2175.1 (2)O2—C8—C9—C144.6 (5)
O2—Cu1—N1—N21.5 (2)N2—C8—C9—C107.2 (6)
C7—N1—N2—C8176.4 (3)O2—C8—C9—C10175.3 (3)
Cu1—N1—N2—C81.1 (4)C14—C9—C10—C110.2 (6)
O4B—O3A—N3—O4A91 (5)C8—C9—C10—C11179.7 (4)
O4B—O3A—N3—O3B111 (5)C9—C10—C11—C120.2 (6)
O4B—O3A—N3—C1296 (4)C10—C11—C12—C131.0 (6)
O3A—O4B—N3—O4A106 (5)C10—C11—C12—N3179.7 (4)
O3A—O4B—N3—O3B86 (5)O3A—N3—C12—C1316.9 (10)
O3A—O4B—N3—C1299 (4)O4A—N3—C12—C13169 (2)
O1—Cu1—N4—C15162.5 (3)O3B—N3—C12—C13170 (2)
O2—Cu1—N4—C1520.6 (3)O4B—N3—C12—C1314.6 (10)
O1—Cu1—N4—C1834.2 (3)O3A—N3—C12—C11163.8 (9)
O2—Cu1—N4—C18148.9 (3)O4A—N3—C12—C1110 (2)
Cu1—O1—C1—C6175.7 (3)O3B—N3—C12—C1110 (2)
Cu1—O1—C1—C25.2 (5)O4B—N3—C12—C11164.7 (9)
O1—C1—C2—C3178.5 (3)C11—C12—C13—C142.2 (6)
C6—C1—C2—C30.5 (5)N3—C12—C13—C14178.5 (4)
O1—C1—C2—C74.6 (6)C12—C13—C14—C92.2 (6)
C6—C1—C2—C7176.4 (3)C10—C9—C14—C131.0 (6)
C1—C2—C3—C40.6 (6)C8—C9—C14—C13179.1 (4)
C7—C2—C3—C4176.5 (4)C18—N4—C15—C1651.9 (5)
C2—C3—C4—C50.4 (6)Cu1—N4—C15—C16177.2 (3)
C3—C4—C5—C61.5 (6)C17—O5—C16—C1557.9 (5)
C4—C5—C6—C11.6 (6)N4—C15—C16—O555.7 (5)
O1—C1—C6—C5179.6 (4)C16—O5—C17—C1858.9 (5)
C2—C1—C6—C50.5 (6)C15—N4—C18—C1752.4 (4)
N2—N1—C7—C2174.7 (3)Cu1—N4—C18—C17175.9 (3)
Cu1—N1—C7—C20.2 (6)O5—C17—C18—N457.4 (5)
C3—C2—C7—N1178.9 (4)
 

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