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In the title complex, [Cu(C4O4)(C12H8N2)(H2O)2]·2H2O, the CuII centre exhibits a slightly distorted square-pyramidal coordination geometry, defined by two N atoms from a 1,10-phenanthroline (phen) mol­ecule, one O atom from an acetyl­enedicarboxyl­ate dianion (ace2-), and two O atoms from two coordinated water mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051087/at2169sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051087/at2169Isup2.hkl
Contains datablock I

CCDC reference: 633585

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.029
  • wR factor = 0.077
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.36 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C13 - C14 ... 1.47 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C15 - C16 ... 1.48 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
0 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 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(Acetylenedicarboxylato)diaqua(1,10-phenanthroline)copper(II) dihydrate top
Crystal data top
[Cu(C4O4)(C12H8N2)(H2O)2]·2H2OF(000) = 876
Mr = 427.85Dx = 1.645 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 13970 reflections
a = 9.1304 (18) Åθ = 3.0–27.4°
b = 17.414 (4) ŵ = 1.31 mm1
c = 10.964 (2) ÅT = 295 K
β = 97.74 (3)°Block, blue
V = 1727.3 (6) Å30.35 × 0.25 × 0.15 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3939 independent reflections
Radiation source: fine-focus sealed tube3470 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 10.000 pixels mm-1θmax = 27.4°, θmin = 3.0°
ω scansh = 1110
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 2122
Tmin = 0.656, Tmax = 0.827l = 1414
16607 measured reflections
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0367P)2 + 0.8958P]
where P = (Fo2 + 2Fc2)/3
3939 reflections(Δ/σ)max = 0.001
244 parametersΔρmax = 0.78 e Å3
0 restraintsΔρmin = 0.33 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*/Ueq
Cu10.70087 (2)0.658304 (12)0.684575 (19)0.02818 (8)
O10.60525 (19)0.59639 (9)0.90489 (15)0.0522 (4)
O1W0.55665 (17)0.74143 (9)0.67262 (15)0.0501 (4)
H1W20.56120.78020.62610.075*
H1W10.49390.75060.72140.075*
O2W0.86975 (16)0.72894 (10)0.61217 (14)0.0497 (4)
H2W10.93980.75720.64570.075*
H2W20.86710.73290.53460.075*
O3W0.8328 (3)0.94291 (15)0.5015 (3)0.1013 (8)
H3W10.90990.92920.47150.152*
H3W20.84630.98820.52960.152*
O4W0.5922 (2)0.85237 (9)0.51590 (14)0.0524 (4)
H4W10.66540.88290.52100.079*
H4W20.59020.82670.44970.079*
O20.76097 (16)0.68587 (9)0.85641 (12)0.0406 (3)
O30.61832 (15)0.78044 (9)1.29637 (13)0.0424 (3)
O40.85608 (16)0.74546 (9)1.34458 (13)0.0426 (3)
N10.82128 (17)0.56146 (9)0.69047 (15)0.0346 (3)
N20.61435 (17)0.61510 (9)0.51965 (14)0.0324 (3)
C10.9218 (2)0.53565 (13)0.7795 (2)0.0469 (5)
H10.94150.56370.85200.056*
C20.9991 (3)0.46729 (15)0.7673 (3)0.0611 (7)
H21.06860.45030.83140.073*
C30.9725 (3)0.42566 (13)0.6616 (3)0.0607 (7)
H31.02420.38040.65320.073*
C40.8671 (3)0.45115 (12)0.5657 (2)0.0496 (6)
C50.8280 (3)0.41203 (14)0.4511 (3)0.0650 (8)
H50.87620.36660.43650.078*
C60.7233 (4)0.43947 (15)0.3641 (3)0.0669 (8)
H60.70060.41250.29070.080*
C70.6459 (3)0.50928 (13)0.3815 (2)0.0487 (5)
C80.5339 (3)0.54086 (16)0.2965 (2)0.0611 (7)
H80.50640.51670.22120.073*
C90.4655 (3)0.60650 (16)0.3236 (2)0.0554 (6)
H90.39080.62730.26720.067*
C100.5077 (2)0.64306 (13)0.43720 (19)0.0420 (5)
H100.45980.68800.45510.050*
C110.6825 (2)0.54921 (11)0.49268 (18)0.0352 (4)
C120.7935 (2)0.52020 (11)0.58520 (19)0.0357 (4)
C130.6902 (2)0.65081 (11)0.93060 (17)0.0328 (4)
C140.7123 (2)0.68090 (11)1.05673 (17)0.0344 (4)
C150.7244 (2)0.70830 (11)1.15667 (17)0.0334 (4)
C160.7342 (2)0.74772 (10)1.27675 (16)0.0303 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03150 (13)0.03003 (12)0.02346 (12)0.00232 (9)0.00542 (8)0.00351 (8)
O10.0635 (10)0.0505 (9)0.0440 (9)0.0185 (8)0.0123 (7)0.0149 (7)
O1W0.0527 (9)0.0525 (9)0.0495 (9)0.0229 (7)0.0228 (7)0.0058 (7)
O2W0.0377 (8)0.0709 (11)0.0402 (8)0.0165 (7)0.0037 (6)0.0083 (7)
O3W0.0853 (16)0.0933 (17)0.130 (2)0.0077 (14)0.0298 (15)0.0329 (16)
O4W0.0693 (11)0.0522 (9)0.0356 (8)0.0049 (8)0.0066 (7)0.0066 (7)
O20.0506 (8)0.0460 (8)0.0259 (7)0.0067 (7)0.0082 (6)0.0067 (6)
O30.0390 (7)0.0532 (9)0.0357 (7)0.0061 (7)0.0075 (6)0.0123 (6)
O40.0382 (7)0.0595 (9)0.0291 (7)0.0018 (7)0.0008 (5)0.0080 (6)
N10.0367 (8)0.0333 (8)0.0352 (8)0.0028 (7)0.0101 (6)0.0016 (7)
N20.0344 (8)0.0352 (8)0.0280 (8)0.0060 (7)0.0055 (6)0.0016 (6)
C10.0464 (12)0.0491 (12)0.0453 (12)0.0078 (10)0.0065 (9)0.0112 (10)
C20.0515 (14)0.0560 (15)0.0778 (19)0.0175 (12)0.0161 (12)0.0307 (14)
C30.0601 (15)0.0354 (11)0.094 (2)0.0128 (11)0.0372 (15)0.0155 (13)
C40.0544 (13)0.0286 (9)0.0733 (16)0.0028 (9)0.0365 (12)0.0028 (10)
C50.0798 (19)0.0345 (11)0.091 (2)0.0086 (12)0.0493 (17)0.0236 (13)
C60.091 (2)0.0498 (14)0.0684 (18)0.0270 (15)0.0410 (16)0.0341 (13)
C70.0620 (14)0.0471 (12)0.0409 (12)0.0244 (11)0.0215 (10)0.0161 (10)
C80.0807 (18)0.0697 (17)0.0329 (11)0.0395 (15)0.0074 (11)0.0131 (11)
C90.0594 (14)0.0690 (16)0.0342 (11)0.0274 (13)0.0071 (10)0.0069 (11)
C100.0423 (11)0.0474 (11)0.0348 (10)0.0120 (9)0.0006 (8)0.0067 (9)
C110.0421 (10)0.0332 (9)0.0332 (10)0.0123 (8)0.0156 (8)0.0075 (7)
C120.0405 (10)0.0281 (9)0.0424 (11)0.0033 (8)0.0201 (8)0.0026 (8)
C130.0368 (9)0.0346 (9)0.0267 (9)0.0037 (8)0.0031 (7)0.0053 (7)
C140.0368 (10)0.0377 (9)0.0293 (9)0.0009 (8)0.0065 (7)0.0023 (8)
C150.0318 (9)0.0396 (10)0.0291 (9)0.0029 (8)0.0045 (7)0.0033 (8)
C160.0360 (9)0.0325 (9)0.0234 (8)0.0029 (8)0.0074 (7)0.0009 (7)
Geometric parameters (Å, º) top
Cu1—O1W1.9494 (15)C1—H10.9300
Cu1—O21.9499 (14)C2—C31.360 (4)
Cu1—N12.0094 (16)C2—H20.9300
Cu1—N22.0186 (16)C3—C41.399 (4)
Cu1—O2W2.2024 (15)C3—H30.9300
O1—C131.233 (2)C4—C121.408 (3)
O1W—H1W20.8500C4—C51.432 (4)
O1W—H1W10.8500C5—C61.344 (4)
O2W—H2W10.8500C5—H50.9300
O2W—H2W20.8499C6—C71.432 (4)
O3W—H3W10.8499C6—H60.9300
O3W—H3W20.8499C7—C81.401 (4)
O4W—H4W10.8500C7—C111.404 (3)
O4W—H4W20.8500C8—C91.355 (4)
O2—C131.262 (2)C8—H80.9300
O3—C161.246 (2)C9—C101.406 (3)
O4—C161.253 (2)C9—H90.9300
N1—C11.325 (3)C10—H100.9300
N1—C121.354 (3)C11—C121.427 (3)
N2—C101.329 (3)C13—C141.467 (3)
N2—C111.357 (2)C14—C151.187 (3)
C1—C21.400 (3)C15—C161.477 (2)
O1W—Cu1—O288.96 (7)C3—C4—C5125.0 (2)
O1W—Cu1—N1170.78 (7)C12—C4—C5118.2 (3)
O2—Cu1—N195.39 (7)C6—C5—C4121.6 (2)
O1W—Cu1—N292.13 (7)C6—C5—H5119.2
O2—Cu1—N2169.25 (6)C4—C5—H5119.2
N1—Cu1—N282.09 (7)C5—C6—C7121.5 (2)
O1W—Cu1—O2W93.46 (7)C5—C6—H6119.2
O2—Cu1—O2W95.23 (6)C7—C6—H6119.2
N1—Cu1—O2W94.23 (7)C8—C7—C11116.8 (2)
N2—Cu1—O2W95.38 (6)C8—C7—C6125.0 (2)
Cu1—O1W—H1W2122.9C11—C7—C6118.2 (2)
Cu1—O1W—H1W1127.2C9—C8—C7120.1 (2)
H1W2—O1W—H1W1108.6C9—C8—H8119.9
Cu1—O2W—H2W1133.6C7—C8—H8119.9
Cu1—O2W—H2W2118.6C8—C9—C10119.8 (2)
H2W1—O2W—H2W2107.7C8—C9—H9120.1
H3W1—O3W—H3W2108.3C10—C9—H9120.1
H4W1—O4W—H4W2108.1N2—C10—C9121.7 (2)
C13—O2—Cu1113.68 (12)N2—C10—H10119.2
C1—N1—C12118.65 (18)C9—C10—H10119.2
C1—N1—Cu1129.05 (15)N2—C11—C7123.1 (2)
C12—N1—Cu1112.28 (13)N2—C11—C12116.58 (16)
C10—N2—C11118.50 (17)C7—C11—C12120.32 (19)
C10—N2—Cu1129.45 (15)N1—C12—C4123.0 (2)
C11—N2—Cu1112.02 (13)N1—C12—C11116.85 (17)
N1—C1—C2121.7 (2)C4—C12—C11120.2 (2)
N1—C1—H1119.1O1—C13—O2125.82 (18)
C2—C1—H1119.1O1—C13—C14119.48 (18)
C3—C2—C1120.0 (2)O2—C13—C14114.68 (16)
C3—C2—H2120.0C15—C14—C13176.3 (2)
C1—C2—H2120.0C14—C15—C16175.7 (2)
C2—C3—C4119.8 (2)O3—C16—O4128.24 (17)
C2—C3—H3120.1O3—C16—C15114.56 (16)
C4—C3—H3120.1O4—C16—C15117.19 (17)
C3—C4—C12116.8 (2)
O1W—Cu1—O2—C1390.63 (14)C11—C7—C8—C90.6 (3)
N1—Cu1—O2—C1381.23 (14)C6—C7—C8—C9178.5 (2)
N2—Cu1—O2—C135.3 (4)C7—C8—C9—C100.3 (3)
O2W—Cu1—O2—C13175.99 (14)C11—N2—C10—C90.5 (3)
O2—Cu1—N1—C18.66 (19)Cu1—N2—C10—C9177.17 (15)
N2—Cu1—N1—C1178.14 (19)C8—C9—C10—N20.3 (3)
O2W—Cu1—N1—C187.01 (18)C10—N2—C11—C70.2 (3)
O2—Cu1—N1—C12173.03 (13)Cu1—N2—C11—C7177.87 (15)
N2—Cu1—N1—C123.55 (12)C10—N2—C11—C12178.36 (17)
O2W—Cu1—N1—C1291.30 (13)Cu1—N2—C11—C123.6 (2)
O1W—Cu1—N2—C105.54 (17)C8—C7—C11—N20.3 (3)
O2—Cu1—N2—C10101.2 (4)C6—C7—C11—N2178.80 (19)
N1—Cu1—N2—C10178.32 (18)C8—C7—C11—C12178.86 (19)
O2W—Cu1—N2—C1088.14 (17)C6—C7—C11—C120.3 (3)
O1W—Cu1—N2—C11176.64 (13)C1—N1—C12—C40.3 (3)
O2—Cu1—N2—C1181.0 (4)Cu1—N1—C12—C4178.23 (15)
N1—Cu1—N2—C113.86 (12)C1—N1—C12—C11178.79 (18)
O2W—Cu1—N2—C1189.68 (13)Cu1—N1—C12—C112.7 (2)
C12—N1—C1—C20.0 (3)C3—C4—C12—N10.3 (3)
Cu1—N1—C1—C2178.26 (16)C5—C4—C12—N1179.55 (19)
N1—C1—C2—C30.4 (4)C3—C4—C12—C11178.79 (18)
C1—C2—C3—C40.4 (4)C5—C4—C12—C110.5 (3)
C2—C3—C4—C120.1 (3)N2—C11—C12—N10.6 (2)
C2—C3—C4—C5179.2 (2)C7—C11—C12—N1179.21 (17)
C3—C4—C5—C6178.7 (2)N2—C11—C12—C4178.50 (17)
C12—C4—C5—C60.5 (3)C7—C11—C12—C40.1 (3)
C4—C5—C6—C70.1 (4)Cu1—O2—C13—O19.8 (3)
C5—C6—C7—C8178.8 (2)Cu1—O2—C13—C14168.67 (13)
C5—C6—C7—C110.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W2···O4W0.851.792.634 (2)170
O1W—H1W1···O4i0.851.972.809 (2)171
O2W—H2W1···O3ii0.852.262.832 (2)125
O2W—H2W2···O4iii0.852.082.934 (2)178
O3W—H3W1···O1ii0.852.072.914 (3)176
O3W—H3W2···O1iv0.852.042.891 (3)176
O4W—H4W1···O3W0.851.892.726 (3)169
O4W—H4W2···O3iii0.851.912.752 (2)169
Symmetry codes: (i) x1/2, y+3/2, z1/2; (ii) x+1/2, y+3/2, z1/2; (iii) x, y, z1; (iv) x+3/2, y+1/2, z+3/2.
 

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