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In the title compound, [CuCl(C12H8N2)2]2(C10H4O8)·2H2O, the CuII cation has a five-coordinate environment made up of one chloride anion and four N atoms of two 1,10-phenanthroline ligands. Hydro­gen bonds between the benzene-1,2,4,5-tetra­carboxyl­ate(2-) anion and water mol­ecules produce a linear hydrogen-bonded chain. The anion lies on a special position of \overline 1 site symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803028101/ng6004sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803028101/ng6004Isup2.hkl
Contains datablock I

CCDC reference: 231823

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.032
  • wR factor = 0.091
  • Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



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 ............ 2.00 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.16 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C25 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C29 PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.37 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C28 - C29 = 1.53 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O3 .. C3 = 2.95 Ang. PLAT731_ALERT_1_C Bond Calc 0.86(4), Rep 0.855(10) ...... 4.00 su-Rat O5 -H31 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.849(10) ...... 3.00 su-Rat O5 -H30 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(4), Rep 0.855(10) ...... 4.00 su-Rat O5 -H31 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(3), Rep 0.849(10) ...... 3.00 su-Rat O5 -H30 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 2.02(4), Rep 2.025(14) ...... 2.86 su-Rat H31 -O1 1.555 2.666
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis[bis(1,10-phenanthroline)chlorocopper(II)] benzene-1,2,4,5-tetracarboxylate(2-) dihydrate top
Crystal data top
[CuCl(C12H8N2)2]2(C10H4O8)·2H2OZ = 1
Mr = 1206.96F(000) = 616
Triclinic, P1Dx = 1.607 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.1324 (7) ÅCell parameters from 426 reflections
b = 11.3356 (8) Åθ = 2.3–21.4°
c = 12.2000 (9) ŵ = 1.03 mm1
α = 104.041 (1)°T = 273 K
β = 95.208 (1)°Prism, blue
γ = 110.685 (1)°0.34 × 0.28 × 0.13 mm
V = 1247.48 (15) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4388 independent reflections
Radiation source: fine-focus sealed tube3992 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
φ and ω scansθmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1112
Tmin = 0.714, Tmax = 0.874k = 138
6633 measured reflectionsl = 1214
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)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091 w = 1/[σ2(Fo2) + (0.0509P)2 + 0.4259P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.005
4388 reflectionsΔρmax = 0.46 e Å3
374 parametersΔρmin = 0.30 e Å3
5 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0094 (12)
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
Cu10.24732 (2)0.91663 (2)0.20963 (2)0.03775 (12)
Cl10.34267 (6)0.82258 (6)0.06828 (5)0.04827 (16)
O10.88315 (19)0.6249 (2)0.50569 (19)0.0704 (6)
O20.7969 (2)0.6520 (3)0.3499 (2)0.1046 (10)
O30.5737 (2)0.5563 (3)0.21317 (18)0.0872 (8)
O40.3492 (2)0.4471 (2)0.20433 (16)0.0804 (7)
O50.0295 (3)0.4912 (3)0.3320 (2)0.0831 (7)
N10.05525 (19)0.76799 (18)0.15257 (15)0.0400 (4)
N20.11811 (18)1.02440 (18)0.17589 (14)0.0375 (4)
N30.23036 (18)0.94894 (17)0.38435 (15)0.0378 (4)
N40.43377 (19)1.07138 (18)0.28032 (15)0.0388 (4)
C10.0281 (3)0.6415 (2)0.1394 (2)0.0496 (6)
H10.10230.61760.16300.060*
C20.1086 (3)0.5432 (3)0.0912 (2)0.0571 (7)
H20.12430.45520.08250.068*
C30.2185 (3)0.5764 (3)0.0571 (2)0.0557 (7)
H30.30900.51100.02290.067*
C40.1952 (2)0.7099 (3)0.07352 (17)0.0471 (6)
C50.3044 (2)0.7565 (3)0.0456 (2)0.0571 (7)
H50.39840.69610.01530.068*
C60.2738 (3)0.8855 (3)0.0622 (2)0.0569 (7)
H60.34750.91260.04430.068*
C70.1307 (2)0.9824 (3)0.10656 (18)0.0453 (5)
C80.0908 (3)1.1183 (3)0.1232 (2)0.0534 (6)
H80.15981.15080.10520.064*
C90.0491 (3)1.2030 (3)0.1658 (2)0.0527 (6)
H90.07591.29320.17810.063*
C100.1514 (3)1.1520 (2)0.19067 (19)0.0437 (5)
H100.24681.20990.21870.052*
C110.0212 (2)0.9405 (2)0.13558 (16)0.0370 (5)
C120.0544 (2)0.8027 (2)0.12087 (16)0.0381 (5)
C130.1254 (2)0.8900 (2)0.4338 (2)0.0469 (5)
H130.04360.82040.38770.056*
C140.1332 (3)0.9284 (3)0.5524 (2)0.0550 (6)
H140.05630.88670.58420.066*
C150.2544 (3)1.0277 (3)0.6216 (2)0.0547 (6)
H150.26101.05290.70100.066*
C160.3686 (3)1.0915 (2)0.57306 (19)0.0417 (5)
C170.5020 (3)1.1935 (2)0.6385 (2)0.0484 (6)
H170.51661.21960.71850.058*
C180.6071 (3)1.2524 (2)0.5856 (2)0.0478 (6)
H180.69311.31790.62990.057*
C190.5883 (2)1.2159 (2)0.4626 (2)0.0411 (5)
C200.6901 (2)1.2768 (2)0.4022 (2)0.0499 (6)
H200.77721.34420.44210.060*
C210.6612 (3)1.2369 (2)0.2849 (2)0.0534 (6)
H210.72681.27910.24440.064*
C220.5324 (3)1.1324 (2)0.2260 (2)0.0484 (6)
H220.51501.10440.14590.058*
C230.4597 (2)1.1137 (2)0.39706 (18)0.0355 (4)
C240.3500 (2)1.0493 (2)0.45273 (17)0.0351 (4)
C250.4699 (3)0.4986 (2)0.2584 (2)0.0481 (6)
C260.3739 (2)0.4507 (2)0.42571 (18)0.0371 (5)
H260.28670.41660.37420.044*
C270.4987 (2)0.5034 (2)0.38457 (17)0.0361 (4)
C280.6304 (2)0.5549 (2)0.46221 (18)0.0363 (4)
C290.7826 (3)0.6148 (2)0.4387 (2)0.0482 (6)
H310.054 (4)0.446 (3)0.371 (3)0.113 (15)*
H300.016 (3)0.538 (3)0.361 (2)0.080 (11)*
H320.6417 (18)0.600 (4)0.2713 (15)0.139 (19)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03054 (16)0.03856 (17)0.03669 (17)0.00831 (12)0.00643 (11)0.00573 (11)
Cl10.0405 (3)0.0549 (3)0.0436 (3)0.0185 (3)0.0101 (2)0.0037 (3)
O10.0376 (10)0.0858 (14)0.0859 (14)0.0096 (9)0.0137 (9)0.0430 (12)
O20.0521 (12)0.173 (3)0.0727 (14)0.0040 (14)0.0254 (11)0.0625 (17)
O30.0648 (13)0.148 (2)0.0498 (11)0.0264 (14)0.0246 (11)0.0472 (14)
O40.0682 (13)0.1003 (17)0.0411 (10)0.0024 (12)0.0040 (9)0.0237 (10)
O50.0890 (17)0.1016 (19)0.0873 (16)0.0590 (15)0.0328 (13)0.0392 (15)
N10.0365 (10)0.0388 (10)0.0359 (9)0.0078 (8)0.0076 (7)0.0057 (8)
N20.0348 (9)0.0411 (10)0.0326 (9)0.0124 (8)0.0078 (7)0.0071 (7)
N30.0338 (9)0.0398 (10)0.0370 (9)0.0118 (8)0.0078 (7)0.0100 (8)
N40.0340 (9)0.0398 (10)0.0385 (9)0.0104 (8)0.0093 (7)0.0090 (8)
C10.0533 (14)0.0425 (13)0.0465 (13)0.0130 (11)0.0143 (11)0.0081 (10)
C20.0639 (17)0.0403 (13)0.0476 (13)0.0014 (12)0.0189 (12)0.0043 (11)
C30.0446 (14)0.0582 (16)0.0350 (11)0.0072 (12)0.0111 (10)0.0020 (11)
C40.0362 (12)0.0610 (15)0.0265 (10)0.0018 (10)0.0092 (9)0.0068 (10)
C50.0289 (11)0.089 (2)0.0360 (12)0.0066 (12)0.0051 (9)0.0139 (13)
C60.0369 (13)0.099 (2)0.0378 (12)0.0285 (14)0.0098 (10)0.0221 (13)
C70.0400 (12)0.0727 (17)0.0293 (10)0.0265 (11)0.0129 (9)0.0165 (10)
C80.0615 (16)0.0778 (18)0.0401 (12)0.0451 (15)0.0177 (11)0.0212 (12)
C90.0697 (17)0.0550 (15)0.0440 (13)0.0351 (13)0.0161 (12)0.0150 (11)
C100.0482 (13)0.0426 (13)0.0374 (11)0.0168 (10)0.0096 (9)0.0074 (9)
C110.0342 (11)0.0507 (13)0.0245 (9)0.0151 (9)0.0095 (8)0.0091 (9)
C120.0311 (10)0.0485 (12)0.0266 (9)0.0081 (9)0.0079 (8)0.0072 (9)
C130.0388 (12)0.0486 (13)0.0496 (13)0.0107 (10)0.0128 (10)0.0160 (11)
C140.0563 (15)0.0610 (16)0.0518 (14)0.0199 (13)0.0256 (12)0.0228 (12)
C150.0715 (17)0.0586 (15)0.0386 (12)0.0269 (14)0.0191 (12)0.0167 (11)
C160.0528 (13)0.0386 (12)0.0377 (11)0.0225 (10)0.0080 (10)0.0112 (9)
C170.0639 (15)0.0415 (12)0.0357 (11)0.0230 (12)0.0009 (10)0.0043 (10)
C180.0495 (13)0.0351 (12)0.0483 (13)0.0157 (10)0.0078 (11)0.0015 (10)
C190.0390 (12)0.0314 (11)0.0486 (12)0.0140 (9)0.0033 (9)0.0057 (9)
C200.0364 (12)0.0337 (12)0.0677 (16)0.0064 (9)0.0066 (11)0.0063 (11)
C210.0442 (13)0.0430 (13)0.0661 (16)0.0077 (11)0.0224 (12)0.0138 (12)
C220.0451 (13)0.0486 (13)0.0482 (13)0.0126 (11)0.0175 (10)0.0137 (11)
C230.0344 (10)0.0313 (10)0.0405 (11)0.0143 (9)0.0062 (8)0.0080 (9)
C240.0384 (11)0.0336 (10)0.0359 (10)0.0176 (9)0.0073 (8)0.0095 (9)
C250.0575 (15)0.0487 (13)0.0379 (12)0.0183 (12)0.0161 (11)0.0135 (10)
C260.0378 (11)0.0330 (11)0.0366 (10)0.0116 (9)0.0069 (9)0.0070 (9)
C270.0440 (12)0.0316 (10)0.0331 (10)0.0151 (9)0.0128 (9)0.0080 (8)
C280.0374 (11)0.0311 (10)0.0403 (11)0.0117 (9)0.0152 (9)0.0100 (9)
C290.0413 (13)0.0475 (13)0.0546 (14)0.0125 (10)0.0213 (11)0.0157 (11)
Geometric parameters (Å, º) top
Cu1—N11.9949 (18)C8—C91.365 (4)
Cu1—N22.1569 (18)C8—H80.9300
Cu1—N32.1071 (17)C9—C101.397 (3)
Cu1—N42.0047 (18)C9—H90.9300
Cu1—Cl12.2763 (6)C10—H100.9300
O1—C291.200 (3)C11—C121.438 (3)
O2—C291.256 (3)C13—C141.392 (3)
O3—C251.278 (3)C13—H130.9300
O3—H320.851 (10)C14—C151.365 (4)
O4—C251.197 (3)C14—H140.9300
O5—H310.855 (10)C15—C161.398 (3)
O5—H300.849 (10)C15—H150.9300
N1—C11.326 (3)C16—C241.402 (3)
N1—C121.358 (3)C16—C171.433 (3)
N2—C101.325 (3)C17—C181.351 (4)
N2—C111.355 (3)C17—H170.9300
N3—C131.323 (3)C18—C191.432 (3)
N3—C241.357 (3)C18—H180.9300
N4—C221.331 (3)C19—C201.402 (3)
N4—C231.356 (3)C19—C231.405 (3)
C1—C21.397 (4)C20—C211.361 (4)
C1—H10.9300C20—H200.9300
C2—C31.357 (4)C21—C221.395 (3)
C2—H20.9300C21—H210.9300
C3—C41.407 (4)C22—H220.9300
C3—H30.9300C23—C241.426 (3)
C4—C121.404 (3)C25—C271.525 (3)
C4—C51.431 (4)C26—C28i1.388 (3)
C5—C61.342 (4)C26—C271.391 (3)
C5—H50.9300C26—H260.9300
C6—C71.430 (4)C27—C281.404 (3)
C6—H60.9300C28—C26i1.388 (3)
C7—C111.402 (3)C28—C291.535 (3)
C7—C81.405 (4)
N1—Cu1—N280.38 (7)C7—C11—C12119.8 (2)
N1—Cu1—N394.34 (7)N1—C12—C4122.7 (2)
N1—Cu1—N4174.67 (7)N1—C12—C11117.33 (18)
N1—Cu1—Cl192.15 (5)C4—C12—C11120.0 (2)
N2—Cu1—N497.93 (7)N3—C13—C14122.4 (2)
N2—Cu1—N393.90 (7)N3—C13—H13118.8
N2—Cu1—Cl1121.04 (5)C14—C13—H13118.8
N3—Cu1—N480.70 (7)C15—C14—C13119.5 (2)
N3—Cu1—Cl1145.05 (5)C15—C14—H14120.2
N4—Cu1—Cl193.04 (5)C13—C14—H14120.2
C25—O3—H32102.6 (11)C14—C15—C16119.9 (2)
H31—O5—H30118.9 (19)C14—C15—H15120.0
C1—N1—C12118.74 (19)C16—C15—H15120.0
C1—N1—Cu1126.14 (17)C15—C16—C24116.8 (2)
C12—N1—Cu1115.07 (14)C15—C16—C17124.2 (2)
C10—N2—C11118.37 (19)C24—C16—C17119.1 (2)
C10—N2—Cu1131.65 (15)C18—C17—C16121.0 (2)
C11—N2—Cu1109.95 (14)C18—C17—H17119.5
C13—N3—C24118.23 (19)C16—C17—H17119.5
C13—N3—Cu1130.97 (15)C17—C18—C19121.2 (2)
C24—N3—Cu1110.79 (13)C17—C18—H18119.4
C22—N4—C23118.40 (19)C19—C18—H18119.4
C22—N4—Cu1127.43 (16)C20—C19—C23117.2 (2)
C23—N4—Cu1114.15 (14)C20—C19—C18124.1 (2)
N1—C1—C2122.0 (2)C23—C19—C18118.7 (2)
N1—C1—H1119.0C21—C20—C19119.8 (2)
C2—C1—H1119.0C21—C20—H20120.1
C3—C2—C1119.8 (3)C19—C20—H20120.1
C3—C2—H2120.1C20—C21—C22119.6 (2)
C1—C2—H2120.1C20—C21—H21120.2
C2—C3—C4119.9 (2)C22—C21—H21120.2
C2—C3—H3120.1N4—C22—C21122.3 (2)
C4—C3—H3120.1N4—C22—H22118.9
C12—C4—C3116.8 (2)C21—C22—H22118.9
C12—C4—C5118.5 (2)N4—C23—C19122.64 (19)
C3—C4—C5124.6 (2)N4—C23—C24117.11 (18)
C6—C5—C4121.4 (2)C19—C23—C24120.25 (19)
C6—C5—H5119.3N3—C24—C16123.1 (2)
C4—C5—H5119.3N3—C24—C23117.13 (18)
C5—C6—C7121.6 (2)C16—C24—C23119.8 (2)
C5—C6—H6119.2O4—C25—O3120.5 (2)
C7—C6—H6119.2O4—C25—C27119.7 (2)
C11—C7—C8116.8 (2)O3—C25—C27119.6 (2)
C11—C7—C6118.6 (2)C28i—C26—C27124.9 (2)
C8—C7—C6124.6 (2)C28i—C26—H26117.5
C9—C8—C7120.1 (2)C27—C26—H26117.5
C9—C8—H8119.9C26—C27—C28117.60 (19)
C7—C8—H8119.9C26—C27—C25113.23 (19)
C8—C9—C10119.0 (2)C28—C27—C25129.2 (2)
C8—C9—H9120.5C26i—C28—C27117.46 (19)
C10—C9—H9120.5C26i—C28—C29114.4 (2)
N2—C10—C9122.7 (2)C27—C28—C29128.15 (19)
N2—C10—H10118.7O1—C29—O2122.5 (2)
C9—C10—H10118.7O1—C29—C28119.0 (2)
N2—C11—C7122.9 (2)O2—C29—C28118.5 (2)
N2—C11—C12117.23 (18)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H31···O1i0.86 (1)2.03 (1)2.864 (3)167 (3)
O5—H30···O1ii0.85 (1)2.31 (2)3.096 (3)154 (3)
O3—H32···O20.85 (1)1.59 (2)2.404 (3)158 (4)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y, z.
 

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