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In the title compound, [CuCl2(C4H9NO)(C6H18N3OP)], the Cu atom is situated in a slightly distorted tetra­hedral coordination geometry. The H—N bond of morpholine is in the axial position.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016819/at2258sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016819/at2258Isup2.hkl
Contains datablock I

CCDC reference: 646708

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.024
  • wR factor = 0.063
  • Data-to-parameter ratio = 21.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu - Cl1 .. 13.22 su PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu - Cl2 .. 12.03 su
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95 PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 30 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu - O2 .. 6.85 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu - N1 .. 9.60 su PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A .. CL2 .. 2.91 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A .. O1 .. 2.61 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H5A .. CL1 .. 2.90 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A .. CL1 .. 2.88 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9C .. O1 .. 2.94 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C9 .. O1 .. 3.91 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.947 Tmax scaled 0.577 Tmin scaled 0.501
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1998); software used to prepare material for publication: SHELXTL.

Dichlorido(hexamethylphosphamide)(morpholine-κN)copper(II) top
Crystal data top
[CuCl2(C4H9NO)(C6H18N3OP)]Z = 2
Mr = 400.78F(000) = 418
Triclinic, P1Dx = 1.492 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2649 (3) ÅCell parameters from 8350 reflections
b = 9.7300 (3) Åθ = 3.1–27.5°
c = 12.0927 (3) ŵ = 1.62 mm1
α = 86.150 (1)°T = 153 K
β = 81.821 (1)°Block, green
γ = 67.910 (1)°0.45 × 0.42 × 0.34 mm
V = 891.82 (5) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4029 independent reflections
Radiation source: Rotating Anode3872 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: empirical (using intensity measurements)
(SHELXTL; Siemens, 1998)
h = 1010
Tmin = 0.529, Tmax = 0.609k = 1212
8605 measured reflectionsl = 1315
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)] = 0.024H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.063 w = 1/[σ2(Fo2) + (0.036P)2 + 0.286P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
4029 reflectionsΔρmax = 0.42 e Å3
192 parametersΔρmin = 0.48 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0284 (16)
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
Cu0.655592 (19)0.428567 (16)0.298339 (12)0.01574 (7)
Cl10.82959 (5)0.28743 (4)0.15753 (3)0.03022 (10)
Cl20.38765 (5)0.41614 (4)0.33886 (3)0.02818 (10)
P0.62646 (4)0.75885 (4)0.19969 (3)0.01723 (9)
O11.05800 (15)0.14092 (12)0.54930 (10)0.0311 (2)
O20.64169 (13)0.63533 (11)0.28408 (8)0.0222 (2)
N10.78831 (15)0.36065 (12)0.43573 (10)0.0196 (2)
N20.54578 (17)0.74479 (14)0.08587 (10)0.0253 (3)
N30.82077 (16)0.76671 (14)0.16544 (11)0.0267 (3)
N40.48884 (16)0.91640 (13)0.25292 (10)0.0222 (2)
C10.97856 (19)0.33145 (16)0.40627 (13)0.0240 (3)
H1A0.99360.42440.37810.029*
H1B1.02770.25810.34560.029*
C21.0793 (2)0.27328 (17)0.50529 (14)0.0303 (3)
H2A1.20580.25300.48190.036*
H2B1.03630.34940.56400.036*
C30.8763 (2)0.17025 (18)0.58591 (14)0.0311 (3)
H3A0.83340.24520.64550.037*
H3B0.86280.07820.61780.037*
C40.7659 (2)0.22637 (16)0.49076 (13)0.0269 (3)
H4A0.80030.14730.43490.032*
H4B0.64030.25040.51980.032*
C50.6654 (3)0.65370 (18)0.00528 (13)0.0336 (4)
H5A0.69950.54860.01620.040*
H5B0.77060.67890.02060.040*
H5C0.60600.67250.07250.040*
C60.3729 (2)0.7305 (2)0.10148 (15)0.0397 (4)
H6A0.32000.75770.03170.048*
H6B0.29600.79660.16100.048*
H6C0.38770.62770.12210.048*
C70.9815 (2)0.6342 (2)0.15735 (15)0.0345 (4)
H7A1.04300.62650.08120.041*
H7B0.95150.54620.17540.041*
H7C1.05800.64070.21010.041*
C80.8451 (3)0.9012 (2)0.12091 (19)0.0467 (5)
H8A0.92510.92280.16330.056*
H8B0.73120.98410.12720.056*
H8C0.89550.88720.04220.056*
C90.5095 (2)0.95434 (18)0.36369 (13)0.0295 (3)
H9A0.57101.02380.35590.035*
H9B0.57800.86410.40260.035*
H9C0.39321.00060.40670.035*
C100.3864 (3)1.04420 (18)0.18870 (15)0.0423 (4)
H10A0.26171.07590.21890.051*
H10B0.40161.01680.11030.051*
H10C0.42731.12570.19380.051*
H1N0.747 (3)0.432 (2)0.4906 (16)0.033 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.01737 (10)0.01202 (9)0.01717 (10)0.00475 (7)0.00180 (6)0.00086 (6)
Cl10.0376 (2)0.02628 (18)0.02246 (17)0.00716 (16)0.00039 (14)0.00843 (14)
Cl20.02323 (18)0.02811 (18)0.0355 (2)0.01267 (15)0.00037 (14)0.00593 (15)
P0.01936 (17)0.01403 (16)0.01816 (17)0.00625 (13)0.00074 (12)0.00235 (12)
O10.0317 (6)0.0212 (5)0.0403 (6)0.0072 (5)0.0141 (5)0.0053 (5)
O20.0261 (5)0.0161 (4)0.0241 (5)0.0078 (4)0.0032 (4)0.0006 (4)
N10.0222 (6)0.0139 (5)0.0205 (5)0.0046 (4)0.0012 (4)0.0015 (4)
N20.0302 (7)0.0268 (6)0.0199 (6)0.0111 (5)0.0032 (5)0.0052 (5)
N30.0233 (6)0.0219 (6)0.0350 (7)0.0106 (5)0.0022 (5)0.0013 (5)
N40.0261 (6)0.0159 (5)0.0208 (6)0.0028 (5)0.0038 (4)0.0033 (4)
C10.0219 (7)0.0217 (7)0.0285 (7)0.0083 (6)0.0031 (5)0.0001 (6)
C20.0317 (8)0.0236 (7)0.0391 (9)0.0115 (6)0.0134 (7)0.0020 (6)
C30.0363 (9)0.0275 (7)0.0293 (8)0.0117 (7)0.0076 (6)0.0082 (6)
C40.0274 (7)0.0223 (7)0.0318 (8)0.0106 (6)0.0059 (6)0.0076 (6)
C50.0531 (10)0.0238 (7)0.0188 (7)0.0092 (7)0.0002 (7)0.0047 (6)
C60.0395 (9)0.0582 (11)0.0311 (8)0.0262 (9)0.0114 (7)0.0038 (8)
C70.0207 (7)0.0375 (9)0.0398 (9)0.0070 (7)0.0027 (6)0.0010 (7)
C80.0425 (10)0.0328 (9)0.0672 (13)0.0229 (8)0.0095 (9)0.0025 (9)
C90.0356 (8)0.0263 (7)0.0267 (7)0.0100 (6)0.0040 (6)0.0101 (6)
C100.0558 (11)0.0212 (7)0.0330 (9)0.0054 (8)0.0079 (8)0.0012 (7)
Geometric parameters (Å, º) top
Cu—O21.9687 (10)C3—C41.514 (2)
Cu—N12.0557 (12)C3—H3A0.9900
Cu—Cl12.2328 (4)C3—H3B0.9900
Cu—Cl22.2458 (4)C4—H4A0.9900
P—O21.5032 (10)C4—H4B0.9900
P—N31.6295 (12)C5—H5A0.9800
P—N41.6342 (12)C5—H5B0.9800
P—N21.6472 (13)C5—H5C0.9800
O1—C21.4230 (18)C6—H6A0.9800
O1—C31.428 (2)C6—H6B0.9800
N1—C11.4827 (18)C6—H6C0.9800
N1—C41.4882 (17)C7—H7A0.9800
N1—H1N0.93 (2)C7—H7B0.9800
N2—C51.463 (2)C7—H7C0.9800
N2—C61.471 (2)C8—H8A0.9800
N3—C81.454 (2)C8—H8B0.9800
N3—C71.459 (2)C8—H8C0.9800
N4—C101.4600 (19)C9—H9A0.9800
N4—C91.4624 (19)C9—H9B0.9800
C1—C21.512 (2)C9—H9C0.9800
C1—H1A0.9900C10—H10A0.9800
C1—H1B0.9900C10—H10B0.9800
C2—H2A0.9900C10—H10C0.9800
C2—H2B0.9900
O2—Cu—N1100.04 (4)C4—C3—H3B109.3
O2—Cu—Cl1112.87 (3)H3A—C3—H3B108.0
N1—Cu—Cl1106.08 (3)N1—C4—C3111.63 (12)
O2—Cu—Cl2111.63 (3)N1—C4—H4A109.3
N1—Cu—Cl2109.18 (3)C3—C4—H4A109.3
Cl1—Cu—Cl2115.633 (15)N1—C4—H4B109.3
O2—P—N3108.33 (6)C3—C4—H4B109.3
O2—P—N4110.06 (6)H4A—C4—H4B108.0
N3—P—N4109.94 (6)N2—C5—H5A109.5
O2—P—N2115.07 (6)N2—C5—H5B109.5
N3—P—N2109.40 (7)H5A—C5—H5B109.5
N4—P—N2103.95 (6)N2—C5—H5C109.5
C2—O1—C3109.80 (12)H5A—C5—H5C109.5
P—O2—Cu141.91 (7)H5B—C5—H5C109.5
C1—N1—C4109.40 (11)N2—C6—H6A109.5
C1—N1—Cu111.42 (9)N2—C6—H6B109.5
C4—N1—Cu112.24 (9)H6A—C6—H6B109.5
C1—N1—H1N106.1 (12)N2—C6—H6C109.5
C4—N1—H1N105.4 (12)H6A—C6—H6C109.5
Cu—N1—H1N111.9 (12)H6B—C6—H6C109.5
C5—N2—C6112.47 (13)N3—C7—H7A109.5
C5—N2—P118.61 (11)N3—C7—H7B109.5
C6—N2—P116.81 (10)H7A—C7—H7B109.5
C8—N3—C7114.42 (13)N3—C7—H7C109.5
C8—N3—P122.36 (12)H7A—C7—H7C109.5
C7—N3—P122.28 (10)H7B—C7—H7C109.5
C10—N4—C9113.49 (12)N3—C8—H8A109.5
C10—N4—P125.08 (11)N3—C8—H8B109.5
C9—N4—P118.14 (10)H8A—C8—H8B109.5
N1—C1—C2111.90 (12)N3—C8—H8C109.5
N1—C1—H1A109.2H8A—C8—H8C109.5
C2—C1—H1A109.2H8B—C8—H8C109.5
N1—C1—H1B109.2N4—C9—H9A109.5
C2—C1—H1B109.2N4—C9—H9B109.5
H1A—C1—H1B107.9H9A—C9—H9B109.5
O1—C2—C1110.78 (12)N4—C9—H9C109.5
O1—C2—H2A109.5H9A—C9—H9C109.5
C1—C2—H2A109.5H9B—C9—H9C109.5
O1—C2—H2B109.5N4—C10—H10A109.5
C1—C2—H2B109.5N4—C10—H10B109.5
H2A—C2—H2B108.1H10A—C10—H10B109.5
O1—C3—C4111.51 (13)N4—C10—H10C109.5
O1—C3—H3A109.3H10A—C10—H10C109.5
C4—C3—H3A109.3H10B—C10—H10C109.5
O1—C3—H3B109.3
N3—P—O2—Cu101.33 (11)N4—P—N3—C835.99 (16)
N4—P—O2—Cu138.44 (10)N2—P—N3—C877.56 (15)
N2—P—O2—Cu21.44 (13)O2—P—N3—C735.41 (15)
N1—Cu—O2—P153.94 (10)N4—P—N3—C7155.72 (13)
Cl1—Cu—O2—P41.60 (11)N2—P—N3—C790.73 (14)
Cl2—Cu—O2—P90.65 (10)O2—P—N4—C10153.39 (14)
O2—Cu—N1—C176.62 (9)N3—P—N4—C1087.36 (15)
Cl1—Cu—N1—C140.89 (9)N2—P—N4—C1029.65 (16)
Cl2—Cu—N1—C1166.13 (8)O2—P—N4—C948.50 (13)
O2—Cu—N1—C4160.29 (9)N3—P—N4—C970.75 (12)
Cl1—Cu—N1—C482.20 (9)N2—P—N4—C9172.23 (11)
Cl2—Cu—N1—C443.04 (10)C4—N1—C1—C252.14 (16)
O2—P—N2—C584.28 (12)Cu—N1—C1—C2176.84 (9)
N3—P—N2—C537.92 (13)C3—O1—C2—C160.69 (17)
N4—P—N2—C5155.30 (11)N1—C1—C2—O157.86 (17)
O2—P—N2—C655.50 (14)C2—O1—C3—C460.17 (17)
N3—P—N2—C6177.69 (12)C1—N1—C4—C351.09 (16)
N4—P—N2—C664.92 (13)Cu—N1—C4—C3175.31 (10)
O2—P—N3—C8156.29 (14)O1—C3—C4—N156.08 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···Cl2i0.93 (2)2.49 (2)3.399 (2)168 (2)
C2—H2A···Cl2ii0.992.913.648 (2)132
C4—H4A···O1iii0.992.613.353 (2)132
C5—H5A···Cl10.982.903.821 (2)157
C6—H6A···Cl1iv0.982.883.798 (2)156
C9—H9C···O1v0.982.943.915 (2)176
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z; (iii) x+2, y, z+1; (iv) x+1, y+1, z; (v) x1, y+1, z.
 

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