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The title compound, [Cu(C5H9NO7P)(C4H14N3)]·1.5H2O, was isolated from the hydro­thermal reaction (under mild conditions) between N-(phosphono­meth­yl)imino­diacetic acid (H4pmida), diethyl­enetriamine (det) and copper(II) acetate. The structure contains discrete neutral [Cu(Hpmida)(Hdet)] complexes which are involved in a strong and extensive hydrogen-bonding network including the water mol­ecules of crystallization. Inter­actions between adjacent complexes involve hydrogen bonds of two graph-set motifs, R21(6) and R22(8), which are also responsible for the highly asymmetrical Jahn–Teller distortion of the copper(II) environment.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806001139/cv2001sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806001139/cv2001Isup2.hkl
Contains datablock I

CCDC reference: 298400

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.039
  • wR factor = 0.095
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

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Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: SHELXTL.

[N-(2-Ammonioethyl)ethylenediamine-κ2N,N'][hydrogen N-(phosphonatomethyl)iminodiacetato]copper(II) sesquihydrate top
Crystal data top
[Cu(C5H9NO7P)(C4H14N3)]·1.5H2OF(000) = 1744
Mr = 418.84Dx = 1.781 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 846 reflections
a = 15.554 (3) Åθ = 3.0–26.8°
b = 9.5377 (19) ŵ = 1.55 mm1
c = 21.441 (4) ÅT = 100 K
β = 100.86 (3)°Prism, blue
V = 3123.8 (11) Å30.13 × 0.09 × 0.09 mm
Z = 8
Data collection top
Bruker SMART CCD-1000
diffractometer
3450 independent reflections
Radiation source: fine-focus sealed tube2507 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
Thin–slice ω and φ scansθmax = 27.2°, θmin = 3.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 1919
Tmin = 0.824, Tmax = 0.873k = 1212
13186 measured reflectionsl = 2727
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)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0421P)2 + 9.0176P]
where P = (Fo2 + 2Fc2)/3
3450 reflections(Δ/σ)max < 0.001
241 parametersΔρmax = 0.69 e Å3
14 restraintsΔρmin = 0.52 e Å3
Special details top

Experimental. (See detailed section in the paper)

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
Cu10.23538 (2)0.10668 (4)0.132226 (18)0.00688 (12)
N10.34312 (17)0.2186 (3)0.17493 (12)0.0073 (5)
P10.30292 (5)0.40584 (9)0.07210 (4)0.00747 (18)
C10.3380 (2)0.3698 (3)0.15638 (15)0.0089 (7)
H1A0.39650.41230.17060.011*
H1B0.29700.41720.17970.011*
C20.3474 (2)0.2055 (3)0.24443 (14)0.0078 (6)
H2A0.30320.26800.25750.009*
H2B0.40590.23580.26710.009*
C30.3307 (2)0.0542 (3)0.26326 (15)0.0089 (7)
C40.4198 (2)0.1490 (3)0.15576 (15)0.0085 (7)
H4A0.44910.08870.19100.010*
H4B0.46210.22150.14810.010*
C50.3945 (2)0.0603 (3)0.09647 (15)0.0095 (7)
O10.20715 (14)0.3415 (2)0.05913 (10)0.0097 (5)
H1E0.19880.29710.02470.015*
O20.35884 (14)0.3314 (2)0.03204 (10)0.0098 (5)
O30.29945 (14)0.5630 (2)0.06753 (10)0.0096 (5)
O40.28878 (14)0.0246 (2)0.22037 (11)0.0110 (5)
O50.35708 (15)0.0218 (2)0.31987 (11)0.0127 (5)
O60.31422 (14)0.0283 (2)0.07996 (10)0.0092 (5)
O70.45402 (15)0.0210 (2)0.06915 (11)0.0131 (5)
N20.14219 (18)0.2108 (3)0.16686 (13)0.0098 (6)
H2C0.152 (2)0.2996 (13)0.1707 (14)0.015*
H2D0.133 (2)0.179 (3)0.2023 (9)0.015*
N30.13586 (17)0.0039 (3)0.08189 (13)0.0079 (6)
H3A0.137 (2)0.028 (4)0.0447 (8)0.012*
N40.11728 (17)0.3898 (3)0.04291 (13)0.0095 (6)
H4C0.1024 (17)0.421 (3)0.0771 (8)0.014*
H4D0.1725 (7)0.403 (3)0.0451 (12)0.014*
H4E0.0893 (16)0.437 (3)0.0110 (9)0.014*
C60.0589 (2)0.1878 (3)0.12097 (16)0.0111 (7)
H6A0.05770.24570.08250.013*
H6B0.00830.21430.14040.013*
C70.0540 (2)0.0340 (3)0.10368 (17)0.0119 (7)
H7A0.04770.02320.14110.014*
H7B0.00290.01620.06950.014*
C80.1552 (2)0.1550 (3)0.08324 (15)0.0077 (6)
H8A0.15330.19160.12620.009*
H8B0.21550.16860.07550.009*
C90.0920 (2)0.2401 (3)0.03429 (16)0.0083 (7)
H9A0.03120.22670.04070.010*
H9B0.09560.20910.00920.010*
O1W0.14486 (16)0.2123 (3)0.31568 (11)0.0168 (6)
H1C0.171 (2)0.172 (3)0.3549 (10)0.025*
H1D0.164 (2)0.3051 (17)0.3128 (15)0.025*
O2W0.00000.0624 (4)0.25000.0183 (8)
H2E0.042 (2)0.121 (3)0.2750 (17)0.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.00715 (19)0.0056 (2)0.0076 (2)0.00084 (16)0.00060 (14)0.00143 (16)
N10.0102 (13)0.0059 (13)0.0058 (13)0.0015 (10)0.0014 (10)0.0010 (11)
P10.0095 (4)0.0064 (4)0.0065 (4)0.0007 (3)0.0013 (3)0.0001 (3)
C10.0127 (16)0.0036 (16)0.0109 (17)0.0013 (12)0.0033 (13)0.0007 (12)
C20.0116 (16)0.0086 (16)0.0027 (15)0.0005 (13)0.0003 (12)0.0029 (12)
C30.0082 (16)0.0107 (17)0.0082 (17)0.0008 (13)0.0030 (13)0.0011 (13)
C40.0067 (15)0.0113 (16)0.0072 (16)0.0006 (12)0.0005 (12)0.0008 (13)
C50.0118 (16)0.0056 (15)0.0101 (17)0.0013 (12)0.0003 (13)0.0032 (13)
O10.0117 (12)0.0115 (12)0.0061 (11)0.0027 (9)0.0020 (9)0.0021 (9)
O20.0109 (11)0.0103 (12)0.0082 (11)0.0012 (9)0.0018 (9)0.0002 (9)
O30.0158 (12)0.0030 (11)0.0098 (12)0.0013 (9)0.0016 (9)0.0013 (9)
O40.0151 (12)0.0066 (12)0.0109 (12)0.0024 (9)0.0016 (9)0.0011 (10)
O50.0207 (13)0.0086 (12)0.0078 (12)0.0015 (10)0.0001 (10)0.0013 (9)
O60.0080 (11)0.0092 (12)0.0104 (12)0.0023 (9)0.0011 (9)0.0040 (9)
O70.0106 (12)0.0141 (13)0.0153 (13)0.0001 (10)0.0044 (10)0.0049 (10)
N20.0140 (15)0.0056 (14)0.0106 (15)0.0017 (11)0.0042 (12)0.0006 (11)
N30.0091 (14)0.0051 (13)0.0100 (14)0.0005 (11)0.0028 (11)0.0037 (11)
N40.0101 (13)0.0077 (14)0.0104 (14)0.0005 (12)0.0015 (11)0.0026 (12)
C60.0095 (16)0.0121 (18)0.0112 (17)0.0024 (13)0.0006 (13)0.0006 (14)
C70.0111 (16)0.0109 (17)0.0141 (18)0.0013 (13)0.0039 (13)0.0018 (14)
C80.0079 (15)0.0058 (15)0.0083 (16)0.0001 (12)0.0008 (12)0.0003 (13)
C90.0102 (16)0.0028 (15)0.0111 (17)0.0026 (12)0.0003 (13)0.0002 (12)
O1W0.0195 (14)0.0141 (13)0.0143 (13)0.0064 (11)0.0032 (10)0.0037 (11)
O2W0.0186 (19)0.0163 (19)0.018 (2)0.0000.0015 (15)0.000
Geometric parameters (Å, º) top
Cu1—O61.959 (2)O1—H1E0.8400
Cu1—N22.011 (3)N2—C61.488 (4)
Cu1—N32.011 (3)N2—H2C0.862 (10)
Cu1—N12.052 (3)N2—H2D0.856 (10)
Cu1—O42.289 (2)N3—C81.471 (4)
Cu1—O12.721 (3)N3—C71.480 (4)
N1—C21.484 (4)N3—H3A0.856 (10)
N1—C41.489 (4)N4—C91.483 (4)
N1—C11.494 (4)N4—H4C0.86 (2)
P1—O31.503 (2)N4—H4D0.86 (2)
P1—O21.510 (2)N4—H4E0.86 (2)
P1—O11.586 (2)C6—C71.511 (4)
P1—C11.819 (3)C6—H6A0.9900
C1—H1A0.9900C6—H6B0.9900
C1—H1B0.9900C7—H7A0.9900
C2—C31.534 (5)C7—H7B0.9900
C2—H2A0.9900C8—C91.529 (4)
C2—H2B0.9900C8—H8A0.9900
C3—O51.245 (4)C8—H8B0.9900
C3—O41.269 (4)C9—H9A0.9900
C4—C51.516 (4)C9—H9B0.9900
C4—H4A0.9900O1W—H1C0.944 (10)
C4—H4B0.9900O1W—H1D0.938 (10)
C5—O71.243 (4)O2W—H2E0.95 (3)
C5—O61.269 (4)
O6—Cu1—N2166.47 (10)O7—C5—C4117.7 (3)
O6—Cu1—N389.68 (10)O6—C5—C4117.0 (3)
N2—Cu1—N385.51 (11)P1—O1—Cu1100.07 (11)
O6—Cu1—N184.68 (10)P1—O1—H1E109.5
N2—Cu1—N199.38 (11)C3—O4—Cu1109.4 (2)
N3—Cu1—N1173.73 (11)C5—O6—Cu1116.0 (2)
O6—Cu1—O495.43 (9)C6—N2—Cu1106.3 (2)
N2—Cu1—O498.05 (10)C6—N2—H2C109 (2)
N3—Cu1—O4106.21 (10)Cu1—N2—H2C113 (2)
N1—Cu1—O477.13 (9)C6—N2—H2D105 (2)
O6—Cu1—O192.02 (8)Cu1—N2—H2D114 (2)
N2—Cu1—O175.92 (10)H2C—N2—H2D109.1 (16)
N3—Cu1—O195.73 (9)C8—N3—C7114.7 (3)
N1—Cu1—O181.86 (9)C8—N3—Cu1111.64 (19)
O4—Cu1—O1156.91 (8)C7—N3—Cu1108.8 (2)
C2—N1—C4110.6 (2)C8—N3—H3A109 (3)
C2—N1—C1109.8 (2)C7—N3—H3A112 (2)
C4—N1—C1111.3 (2)Cu1—N3—H3A100 (2)
C2—N1—Cu1106.44 (19)C9—N4—H4C109 (2)
C4—N1—Cu1105.88 (19)C9—N4—H4D113 (2)
C1—N1—Cu1112.67 (19)H4C—N4—H4D109.2 (15)
O3—P1—O2116.72 (13)C9—N4—H4E109 (2)
O3—P1—O1110.68 (13)H4C—N4—H4E108.7 (15)
O2—P1—O1110.00 (13)H4D—N4—H4E108.6 (15)
O3—P1—C1104.68 (14)N2—C6—C7107.6 (3)
O2—P1—C1112.29 (14)N2—C6—H6A110.2
O1—P1—C1101.29 (14)C7—C6—H6A110.2
N1—C1—P1115.9 (2)N2—C6—H6B110.2
N1—C1—H1A108.3C7—C6—H6B110.2
P1—C1—H1A108.3H6A—C6—H6B108.5
N1—C1—H1B108.3N3—C7—C6108.0 (3)
P1—C1—H1B108.3N3—C7—H7A110.1
H1A—C1—H1B107.4C6—C7—H7A110.1
N1—C2—C3111.5 (3)N3—C7—H7B110.1
N1—C2—H2A109.3C6—C7—H7B110.1
C3—C2—H2A109.3H7A—C7—H7B108.4
N1—C2—H2B109.3N3—C8—C9113.8 (3)
C3—C2—H2B109.3N3—C8—H8A108.8
H2A—C2—H2B108.0C9—C8—H8A108.8
O5—C3—O4126.1 (3)N3—C8—H8B108.8
O5—C3—C2116.7 (3)C9—C8—H8B108.8
O4—C3—C2117.1 (3)H8A—C8—H8B107.7
N1—C4—C5112.7 (3)N4—C9—C8107.7 (2)
N1—C4—H4A109.1N4—C9—H9A110.2
C5—C4—H4A109.1C8—C9—H9A110.2
N1—C4—H4B109.1N4—C9—H9B110.2
C5—C4—H4B109.1C8—C9—H9B110.2
H4A—C4—H4B107.8H9A—C9—H9B108.5
O7—C5—O6125.3 (3)H1C—O1W—H1D110.6 (15)
O6—Cu1—N1—C2133.2 (2)O4—Cu1—O1—P144.6 (3)
N2—Cu1—N1—C259.8 (2)O5—C3—O4—Cu1168.6 (3)
O4—Cu1—N1—C236.36 (18)C2—C3—O4—Cu18.6 (3)
O1—Cu1—N1—C2133.99 (19)O6—Cu1—O4—C3109.7 (2)
O6—Cu1—N1—C415.45 (19)N2—Cu1—O4—C371.4 (2)
N2—Cu1—N1—C4177.57 (19)N3—Cu1—O4—C3159.0 (2)
O4—Cu1—N1—C481.38 (19)N1—Cu1—O4—C326.5 (2)
O1—Cu1—N1—C4108.27 (19)O1—Cu1—O4—C31.6 (3)
O6—Cu1—N1—C1106.4 (2)O7—C5—O6—Cu1179.9 (3)
N2—Cu1—N1—C160.6 (2)C4—C5—O6—Cu12.7 (4)
O4—Cu1—N1—C1156.8 (2)N2—Cu1—O6—C5116.0 (4)
O1—Cu1—N1—C113.59 (19)N3—Cu1—O6—C5175.0 (2)
C2—N1—C1—P1164.0 (2)N1—Cu1—O6—C57.8 (2)
C4—N1—C1—P173.2 (3)O4—Cu1—O6—C568.7 (2)
Cu1—N1—C1—P145.6 (3)O1—Cu1—O6—C589.3 (2)
O3—P1—C1—N1177.3 (2)O6—Cu1—N2—C649.1 (5)
O2—P1—C1—N155.1 (3)N3—Cu1—N2—C620.4 (2)
O1—P1—C1—N162.2 (3)N1—Cu1—N2—C6155.6 (2)
C4—N1—C2—C370.4 (3)O4—Cu1—N2—C6126.2 (2)
C1—N1—C2—C3166.4 (2)O1—Cu1—N2—C676.6 (2)
Cu1—N1—C2—C344.2 (3)O6—Cu1—N3—C856.8 (2)
N1—C2—C3—O5159.8 (3)N2—Cu1—N3—C8135.8 (2)
N1—C2—C3—O422.7 (4)O4—Cu1—N3—C838.7 (2)
C2—N1—C4—C5135.4 (3)O1—Cu1—N3—C8148.8 (2)
C1—N1—C4—C5102.2 (3)O6—Cu1—N3—C7175.5 (2)
Cu1—N1—C4—C520.5 (3)N2—Cu1—N3—C78.2 (2)
N1—C4—C5—O7165.7 (3)O4—Cu1—N3—C788.9 (2)
N1—C4—C5—O616.6 (4)O1—Cu1—N3—C783.5 (2)
O3—P1—O1—Cu1149.97 (11)Cu1—N2—C6—C744.8 (3)
O2—P1—O1—Cu179.58 (13)C8—N3—C7—C6160.8 (3)
C1—P1—O1—Cu139.38 (13)Cu1—N3—C7—C634.9 (3)
O6—Cu1—O1—P164.23 (12)N2—C6—C7—N353.3 (3)
N2—Cu1—O1—P1122.00 (13)C7—N3—C8—C968.7 (4)
N3—Cu1—O1—P1154.11 (12)Cu1—N3—C8—C9166.9 (2)
N1—Cu1—O1—P120.10 (12)N3—C8—C9—N4177.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1E···O2i0.841.842.615 (3)153
N2—H2D···O1W0.86 (2)2.42 (2)3.183 (4)148 (3)
N2—H2C···O5ii0.86 (2)2.14 (1)2.980 (4)165 (3)
N3—H3A···O2i0.86 (2)2.13 (2)2.959 (3)162 (3)
N4—H4C···O5iii0.86 (2)2.25 (2)3.014 (4)148 (2)
N4—H4C···O7iv0.86 (2)2.35 (2)2.833 (4)116 (2)
N4—H4D···O3v0.86 (2)1.97 (1)2.819 (4)169 (2)
N4—H4E···O7vi0.86 (2)1.90 (1)2.750 (4)167 (3)
O1W—H1C···O3iii0.94 (1)1.94 (1)2.869 (3)166 (3)
O1W—H1D···O4ii0.94 (1)1.97 (2)2.874 (3)161 (3)
O2W—H2E···O1W0.95 (2)1.89 (3)2.812 (3)166 (4)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1/2, y1/2, z+1/2; (iv) x1/2, y1/2, z; (v) x, y1, z; (vi) x+1/2, y1/2, z.
 

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