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The title compound, [Cu(C7H4O5S)(C12H8N2)(H2O)2]·H2O, contains a monomeric zwitterion in which the CuII atom displays a square-pyramidal geometry defined by two N atoms of one 1,10-phenanthroline, one O atom from the carboxylate group of the 3-sulfonatobenzoate, and two O atoms from two water mol­ecules. Extensive O—H...O inter­molecular hydrogen bonds generate a two-dimensional network, enhancing the stability of the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030989/ng6211sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030989/ng6211Isup2.hkl
Contains datablock I

CCDC reference: 289821

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.033
  • wR factor = 0.090
  • Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc. PLAT417_ALERT_2_C Short Inter D-H..H-D H6B .. H8A .. 2.13 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O6 .. C13 .. 2.97 Ang.
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 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 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 (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Diaqua(1,10-phenanthroline)(3-sulfonatobenzoato)copper(II) monohydrate top
Crystal data top
[Cu(C7H4O5S)(C12H8N2)(H2O)2]·H2OZ = 2
Mr = 497.95F(000) = 510
Triclinic, P1Dx = 1.717 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.6047 (9) ÅCell parameters from 3706 reflections
b = 10.5469 (11) Åθ = 2.5–28.1°
c = 11.7021 (13) ŵ = 1.30 mm1
α = 79.123 (1)°T = 295 K
β = 84.585 (1)°Plate, blue
γ = 67.500 (1)°0.30 × 0.13 × 0.11 mm
V = 963.25 (18) Å3
Data collection top
Bruker APEX area-detector
diffractometer
3735 independent reflections
Radiation source: fine-focus sealed tube3288 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1010
Tmin = 0.697, Tmax = 0.871k = 1212
7553 measured reflectionsl = 1414
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.0579P)2 + 0.5382P]
where P = (Fo2 + 2Fc2)/3
3735 reflections(Δ/σ)max < 0.001
326 parametersΔρmax = 0.41 e Å3
45 restraintsΔρmin = 0.32 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)
Cu10.56217 (3)0.28147 (3)0.64880 (2)0.02723 (11)
S10.36747 (9)0.23057 (7)0.09785 (6)0.04046 (18)
N10.7017 (2)0.10039 (19)0.59524 (17)0.0271 (4)
N20.7536 (2)0.2204 (2)0.75881 (17)0.0287 (4)
O10.4165 (2)0.32828 (17)0.51763 (14)0.0327 (4)
O20.2621 (2)0.55564 (18)0.50948 (15)0.0365 (4)
O30.4868 (6)0.2973 (5)0.0460 (4)0.0495 (10)0.830 (13)
O40.2656 (7)0.2245 (8)0.0137 (5)0.0786 (17)0.830 (13)
O50.4636 (8)0.0988 (3)0.1716 (3)0.0679 (15)0.830 (13)
O5'0.361 (3)0.0988 (14)0.1411 (18)0.062 (6)0.170 (13)
O3'0.511 (2)0.251 (2)0.080 (2)0.040 (5)0.170 (13)
O4'0.257 (3)0.290 (2)0.0109 (17)0.046 (5)0.170 (13)
O60.4540 (2)0.46817 (17)0.68786 (15)0.0325 (4)
O70.4053 (3)0.1820 (2)0.77963 (17)0.0461 (5)
O80.3438 (3)0.5443 (2)0.89276 (18)0.0533 (5)
C10.6715 (3)0.0430 (2)0.5126 (2)0.0320 (5)
H10.57490.09110.46940.038*
C20.7795 (3)0.0872 (3)0.4882 (2)0.0381 (6)
H20.75380.12480.43010.046*
C30.9226 (3)0.1589 (3)0.5499 (2)0.0384 (6)
H30.99520.24560.53420.046*
C40.9594 (3)0.1007 (2)0.6372 (2)0.0335 (5)
C51.1070 (3)0.1645 (3)0.7065 (3)0.0430 (7)
H51.18390.25190.69580.052*
C61.1370 (3)0.1010 (3)0.7866 (3)0.0439 (7)
H61.23540.14420.82860.053*
C71.0204 (3)0.0317 (3)0.8083 (2)0.0353 (6)
C81.0425 (3)0.1031 (3)0.8913 (2)0.0407 (6)
H81.13960.06620.93480.049*
C90.9198 (4)0.2276 (3)0.9077 (2)0.0397 (6)
H90.93190.27470.96380.048*
C100.7771 (3)0.2836 (3)0.8403 (2)0.0346 (5)
H100.69500.36840.85250.042*
C110.8441 (3)0.0296 (2)0.6565 (2)0.0277 (5)
C120.8729 (3)0.0961 (2)0.7440 (2)0.0283 (5)
C130.3056 (3)0.4427 (2)0.47330 (19)0.0254 (5)
C140.2233 (3)0.4366 (2)0.3683 (2)0.0267 (5)
C150.3140 (3)0.3455 (2)0.2937 (2)0.0278 (5)
H150.42500.28740.30960.033*
C160.2398 (3)0.3405 (3)0.1951 (2)0.0303 (5)
C170.0731 (3)0.4229 (3)0.1728 (2)0.0360 (6)
H170.02280.41780.10770.043*
C180.0179 (3)0.5129 (3)0.2483 (2)0.0368 (6)
H180.13070.56740.23470.044*
C190.0572 (3)0.5224 (3)0.3437 (2)0.0316 (5)
H190.00360.58660.39180.038*
H6A0.383 (3)0.509 (3)0.6354 (16)0.050*
H6B0.411 (3)0.487 (3)0.7535 (12)0.050*
H7A0.458 (3)0.0949 (11)0.791 (2)0.050*
H7B0.369 (4)0.209 (2)0.8436 (15)0.050*
H8A0.376 (4)0.4665 (17)0.938 (2)0.050*
H8B0.401 (3)0.590 (2)0.905 (3)0.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02651 (17)0.02456 (17)0.02792 (17)0.00366 (12)0.00646 (11)0.00776 (11)
S10.0476 (4)0.0400 (4)0.0364 (4)0.0148 (3)0.0019 (3)0.0157 (3)
N10.0268 (10)0.0242 (10)0.0301 (10)0.0081 (8)0.0021 (8)0.0060 (8)
N20.0303 (10)0.0300 (10)0.0257 (10)0.0112 (8)0.0026 (8)0.0037 (8)
O10.0375 (9)0.0271 (9)0.0316 (9)0.0057 (7)0.0138 (7)0.0073 (7)
O20.0372 (9)0.0309 (9)0.0345 (9)0.0007 (7)0.0083 (7)0.0114 (7)
O30.051 (2)0.052 (2)0.041 (2)0.0152 (18)0.0049 (16)0.0075 (17)
O40.061 (2)0.117 (4)0.078 (3)0.032 (3)0.004 (2)0.066 (3)
O50.090 (3)0.0330 (15)0.067 (2)0.0090 (16)0.0044 (19)0.0103 (13)
O5'0.080 (11)0.036 (6)0.066 (9)0.019 (6)0.032 (7)0.015 (5)
O3'0.026 (6)0.054 (9)0.041 (8)0.013 (6)0.001 (6)0.015 (6)
O4'0.039 (7)0.059 (9)0.031 (6)0.003 (6)0.006 (5)0.026 (6)
O60.0356 (9)0.0293 (9)0.0298 (9)0.0059 (7)0.0049 (7)0.0101 (7)
O70.0509 (12)0.0377 (10)0.0420 (11)0.0122 (9)0.0091 (9)0.0024 (9)
O80.0675 (15)0.0456 (12)0.0404 (12)0.0116 (11)0.0103 (10)0.0082 (9)
C10.0320 (12)0.0284 (12)0.0362 (13)0.0107 (10)0.0024 (10)0.0075 (10)
C20.0429 (15)0.0325 (13)0.0442 (15)0.0168 (12)0.0045 (12)0.0160 (11)
C30.0382 (14)0.0241 (12)0.0508 (16)0.0093 (11)0.0081 (12)0.0106 (11)
C40.0308 (12)0.0264 (12)0.0395 (14)0.0088 (10)0.0039 (10)0.0031 (10)
C50.0310 (13)0.0295 (13)0.0553 (17)0.0002 (11)0.0025 (12)0.0010 (12)
C60.0293 (13)0.0392 (15)0.0517 (17)0.0048 (11)0.0105 (12)0.0070 (13)
C70.0304 (12)0.0381 (14)0.0348 (13)0.0138 (11)0.0064 (10)0.0054 (11)
C80.0376 (14)0.0478 (16)0.0373 (14)0.0198 (12)0.0152 (11)0.0067 (12)
C90.0512 (16)0.0452 (15)0.0289 (13)0.0250 (13)0.0105 (11)0.0013 (11)
C100.0406 (14)0.0360 (13)0.0300 (13)0.0165 (11)0.0037 (10)0.0060 (10)
C110.0258 (11)0.0251 (11)0.0293 (12)0.0082 (9)0.0001 (9)0.0011 (9)
C120.0264 (11)0.0296 (12)0.0266 (12)0.0099 (10)0.0026 (9)0.0009 (9)
C130.0226 (11)0.0284 (12)0.0244 (11)0.0086 (9)0.0007 (9)0.0051 (9)
C140.0282 (11)0.0266 (11)0.0259 (11)0.0117 (9)0.0014 (9)0.0022 (9)
C150.0286 (11)0.0272 (12)0.0272 (12)0.0103 (9)0.0047 (9)0.0020 (9)
C160.0355 (13)0.0320 (12)0.0263 (12)0.0157 (10)0.0017 (10)0.0051 (9)
C170.0383 (14)0.0442 (15)0.0300 (13)0.0201 (12)0.0102 (10)0.0020 (11)
C180.0249 (12)0.0405 (14)0.0399 (14)0.0083 (11)0.0091 (10)0.0010 (11)
C190.0263 (12)0.0314 (13)0.0331 (13)0.0072 (10)0.0014 (10)0.0035 (10)
Geometric parameters (Å, º) top
Cu1—O11.9427 (16)C3—C41.402 (4)
Cu1—O61.9518 (17)C3—H30.9300
Cu1—O72.3141 (19)C4—C111.399 (3)
Cu1—N12.0090 (19)C4—C51.435 (4)
Cu1—N22.0150 (19)C5—C61.344 (4)
S1—O3'1.33 (2)C5—H50.9300
S1—O41.404 (5)C6—C71.429 (4)
S1—O5'1.407 (15)C6—H60.9300
S1—O51.471 (4)C7—C121.401 (3)
S1—O31.481 (5)C7—C81.404 (4)
S1—O4'1.544 (19)C8—C91.368 (4)
S1—C161.771 (2)C8—H80.9300
N1—C11.326 (3)C9—C101.389 (4)
N1—C111.355 (3)C9—H90.9300
N2—C101.332 (3)C10—H100.9300
N2—C121.352 (3)C11—C121.432 (3)
O1—C131.270 (3)C13—C141.499 (3)
O2—C131.248 (3)C14—C151.381 (3)
O6—H6A0.841 (10)C14—C191.391 (3)
O6—H6B0.845 (10)C15—C161.389 (3)
O7—H7A0.845 (10)C15—H150.9300
O7—H7B0.842 (10)C16—C171.383 (4)
O8—H8A0.848 (10)C17—C181.383 (4)
O8—H8B0.85 (3)C17—H170.9300
C1—C21.397 (3)C18—C191.379 (4)
C1—H10.9300C18—H180.9300
C2—C31.363 (4)C19—H190.9300
C2—H20.9300
O1—Cu1—O691.97 (7)C4—C3—H3120.3
O1—Cu1—N189.23 (7)C11—C4—C3117.2 (2)
O6—Cu1—N1170.77 (8)C11—C4—C5118.1 (2)
O1—Cu1—N2167.56 (8)C3—C4—C5124.7 (2)
O6—Cu1—N295.26 (7)C6—C5—C4121.7 (2)
N1—Cu1—N282.04 (8)C6—C5—H5119.2
O1—Cu1—O795.96 (8)C4—C5—H5119.2
O6—Cu1—O795.93 (7)C5—C6—C7121.1 (2)
N1—Cu1—O793.04 (7)C5—C6—H6119.4
N2—Cu1—O793.35 (8)C7—C6—H6119.4
O3'—S1—O4127.4 (9)C12—C7—C8116.9 (2)
O3'—S1—O5'122.5 (10)C12—C7—C6118.9 (2)
O4—S1—O5'80.6 (11)C8—C7—C6124.2 (2)
O3'—S1—O586.3 (9)C9—C8—C7119.3 (2)
O4—S1—O5117.1 (3)C9—C8—H8120.3
O4—S1—O3112.0 (3)C7—C8—H8120.3
O5'—S1—O3141.3 (9)C8—C9—C10119.9 (2)
O5—S1—O3107.8 (2)C8—C9—H9120.0
O3'—S1—O4'111.8 (11)C10—C9—H9120.0
O5'—S1—O4'106.4 (11)N2—C10—C9122.4 (2)
O5—S1—O4'142.1 (8)N2—C10—H10118.8
O3—S1—O4'92.0 (9)C9—C10—H10118.8
O3'—S1—C16108.1 (9)N1—C11—C4123.2 (2)
O4—S1—C16109.1 (2)N1—C11—C12116.3 (2)
O5'—S1—C16105.4 (6)C4—C11—C12120.5 (2)
O5—S1—C16105.52 (15)N2—C12—C7123.6 (2)
O3—S1—C16104.39 (19)N2—C12—C11116.8 (2)
O4'—S1—C16100.1 (7)C7—C12—C11119.6 (2)
C1—N1—C11118.0 (2)O2—C13—O1125.8 (2)
C1—N1—Cu1129.34 (16)O2—C13—C14119.2 (2)
C11—N1—Cu1112.62 (15)O1—C13—C14115.0 (2)
C10—N2—C12117.8 (2)C15—C14—C19119.3 (2)
C10—N2—Cu1129.90 (17)C15—C14—C13119.6 (2)
C12—N2—Cu1112.28 (15)C19—C14—C13121.1 (2)
C13—O1—Cu1131.38 (15)C14—C15—C16120.1 (2)
Cu1—O6—H6A103 (2)C14—C15—H15119.9
Cu1—O6—H6B125 (2)C16—C15—H15119.9
H6A—O6—H6B110.6 (16)C17—C16—C15120.5 (2)
Cu1—O7—H7A108 (2)C17—C16—S1121.69 (19)
Cu1—O7—H7B122 (2)C15—C16—S1117.80 (19)
H7A—O7—H7B110.1 (16)C16—C17—C18119.2 (2)
H8A—O8—H8B109.1 (16)C16—C17—H17120.4
N1—C1—C2122.4 (2)C18—C17—H17120.4
N1—C1—H1118.8C19—C18—C17120.5 (2)
C2—C1—H1118.8C19—C18—H18119.7
C3—C2—C1119.7 (2)C17—C18—H18119.7
C3—C2—H2120.2C18—C19—C14120.3 (2)
C1—C2—H2120.2C18—C19—H19119.9
C2—C3—C4119.4 (2)C14—C19—H19119.9
C2—C3—H3120.3
O1—Cu1—N1—C19.0 (2)C5—C4—C11—C120.5 (3)
N2—Cu1—N1—C1179.9 (2)C10—N2—C12—C71.0 (3)
O7—Cu1—N1—C186.9 (2)Cu1—N2—C12—C7178.87 (18)
O1—Cu1—N1—C11172.32 (16)C10—N2—C12—C11179.5 (2)
N2—Cu1—N1—C111.21 (15)Cu1—N2—C12—C110.6 (3)
O7—Cu1—N1—C1191.75 (16)C8—C7—C12—N20.5 (4)
O1—Cu1—N2—C10133.7 (3)C6—C7—C12—N2179.1 (2)
O6—Cu1—N2—C108.4 (2)C8—C7—C12—C11179.0 (2)
N1—Cu1—N2—C10179.6 (2)C6—C7—C12—C111.5 (3)
O7—Cu1—N2—C1087.8 (2)N1—C11—C12—N21.7 (3)
O1—Cu1—N2—C1246.1 (4)C4—C11—C12—N2178.6 (2)
O6—Cu1—N2—C12171.42 (16)N1—C11—C12—C7177.8 (2)
N1—Cu1—N2—C120.31 (15)C4—C11—C12—C71.9 (3)
O7—Cu1—N2—C1292.30 (16)Cu1—O1—C13—O21.9 (4)
O6—Cu1—O1—C135.1 (2)Cu1—O1—C13—C14178.00 (15)
N1—Cu1—O1—C13165.7 (2)O2—C13—C14—C15147.9 (2)
N2—Cu1—O1—C13120.4 (3)O1—C13—C14—C1532.0 (3)
O7—Cu1—O1—C13101.3 (2)O2—C13—C14—C1931.4 (3)
C11—N1—C1—C20.8 (4)O1—C13—C14—C19148.7 (2)
Cu1—N1—C1—C2177.76 (18)C19—C14—C15—C160.3 (3)
N1—C1—C2—C30.6 (4)C13—C14—C15—C16179.0 (2)
C1—C2—C3—C40.0 (4)C14—C15—C16—C172.3 (4)
C2—C3—C4—C110.4 (4)C14—C15—C16—S1175.53 (18)
C2—C3—C4—C5178.9 (2)O3'—S1—C16—C17131.7 (11)
C11—C4—C5—C61.2 (4)O4—S1—C16—C1710.6 (4)
C3—C4—C5—C6178.0 (3)O5'—S1—C16—C1795.8 (14)
C4—C5—C6—C71.7 (4)O5—S1—C16—C17137.2 (3)
C5—C6—C7—C120.3 (4)O3—S1—C16—C17109.3 (3)
C5—C6—C7—C8179.2 (3)O4'—S1—C16—C1714.6 (10)
C12—C7—C8—C91.8 (4)O3'—S1—C16—C1546.1 (11)
C6—C7—C8—C9177.8 (2)O4—S1—C16—C15171.7 (4)
C7—C8—C9—C101.6 (4)O5'—S1—C16—C1586.5 (14)
C12—N2—C10—C91.3 (4)O5—S1—C16—C1545.0 (3)
Cu1—N2—C10—C9178.60 (18)O3—S1—C16—C1568.5 (3)
C8—C9—C10—N20.0 (4)O4'—S1—C16—C15163.2 (10)
C1—N1—C11—C40.4 (3)C15—C16—C17—C181.5 (4)
Cu1—N1—C11—C4178.44 (18)S1—C16—C17—C18176.2 (2)
C1—N1—C11—C12179.3 (2)C16—C17—C18—C191.2 (4)
Cu1—N1—C11—C121.9 (3)C17—C18—C19—C143.2 (4)
C3—C4—C11—N10.2 (4)C15—C14—C19—C182.4 (4)
C5—C4—C11—N1179.1 (2)C13—C14—C19—C18178.3 (2)
C3—C4—C11—C12179.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6A···O20.84 (1)1.77 (1)2.587 (2)165 (3)
O6—H6B···O80.85 (1)1.81 (1)2.647 (3)170 (3)
O7—H7A···O5i0.85 (1)1.87 (1)2.701 (3)169 (3)
O7—H7A···O5i0.85 (1)2.10 (3)2.904 (19)158 (3)
O7—H7B···O4ii0.84 (1)2.04 (2)2.877 (19)173 (3)
O7—H7B···O4ii0.84 (1)2.11 (2)2.929 (6)163 (3)
O8—H8A···O3ii0.85 (1)1.94 (1)2.778 (6)169 (3)
O8—H8A···O4ii0.85 (1)2.41 (3)3.04 (3)132 (2)
O8—H8A···O3ii0.85 (1)2.49 (3)3.33 (3)170 (2)
O8—H8B···O3iii0.85 (3)1.98 (1)2.817 (6)171 (3)
O8—H8B···O3iii0.85 (3)2.12 (3)2.95 (2)166 (3)
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1; (iii) x+1, y+1, z+1.
 

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