Download citation
Download citation
link to html
The title compound, [Cu(C7H4ClO2)2(C12H8N2)(H2O)], is a monomer in which the p-chlorobenzoate ligand is synthesized in situ from 4-carboxy­benzene­boronic acid. The coordination around the CuII atom is square pyramidal. Two monodentate benzoate ligands are cis-arranged. Hydrogen bonds occur between coordinated water mol­ecules and benzoate ligands, while π–π stacking inter­actions consolidate the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029965/kp2042sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029965/kp2042Isup2.hkl
Contains datablock I

CCDC reference: 621396

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.040
  • wR factor = 0.105
  • Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H5A .. O1 .. 2.61 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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).

Aquabis(p-chlorobenzoato)(1,10-phenanthroline)copper(II) top
Crystal data top
[Cu(C7H4ClO2)2(C12H8N2)(H2O)]Z = 2
Mr = 572.86F(000) = 582
Triclinic, P1Dx = 1.637 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9427 (7) ÅCell parameters from 3247 reflections
b = 10.7301 (9) Åθ = 2.2–27.8°
c = 14.8175 (12) ŵ = 1.21 mm1
α = 100.404 (1)°T = 295 K
β = 95.328 (1)°Block, dark-blue
γ = 108.582 (1)°0.25 × 0.21 × 0.16 mm
V = 1161.90 (17) Å3
Data collection top
Bruker APEX area-detector
diffractometer
4081 independent reflections
Radiation source: fine-focus sealed tube3751 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
φ and ω scansθmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 99
Tmin = 0.751, Tmax = 0.830k = 1211
6190 measured reflectionsl = 1717
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0608P)2 + 0.8244P]
where P = (Fo2 + 2Fc2)/3
4081 reflections(Δ/σ)max < 0.001
331 parametersΔρmax = 0.37 e Å3
3 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
Cu10.14902 (4)0.48764 (3)0.39711 (2)0.03437 (13)
Cl10.87847 (14)0.67660 (11)0.02563 (7)0.0705 (3)
Cl20.79441 (15)1.00566 (12)0.90913 (7)0.0783 (3)
N10.1942 (3)0.3329 (2)0.44169 (15)0.0318 (5)
N20.0079 (3)0.3359 (2)0.29113 (16)0.0365 (5)
O10.3659 (3)0.5456 (2)0.30509 (14)0.0418 (5)
O20.2169 (3)0.6451 (2)0.22413 (16)0.0544 (6)
O30.2754 (3)0.60659 (19)0.51625 (14)0.0442 (5)
O40.2331 (3)0.7991 (2)0.50550 (16)0.0556 (6)
O50.0398 (3)0.6158 (2)0.35876 (15)0.0445 (5)
C10.2960 (4)0.3347 (3)0.51826 (19)0.0367 (6)
H10.35960.41720.55870.044*
C20.3114 (4)0.2175 (3)0.5404 (2)0.0417 (7)
H20.38430.22260.59470.050*
C30.2190 (4)0.0953 (3)0.4820 (2)0.0418 (7)
H30.22840.01670.49650.050*
C40.1099 (4)0.0891 (3)0.4002 (2)0.0361 (6)
C50.0070 (4)0.0327 (3)0.3335 (2)0.0482 (8)
H50.01030.11490.34390.058*
C60.0946 (4)0.0306 (3)0.2560 (2)0.0478 (8)
H60.15990.11140.21420.057*
C70.1040 (4)0.0933 (3)0.2369 (2)0.0412 (7)
C80.2043 (4)0.1038 (3)0.1574 (2)0.0490 (8)
H80.27010.02690.11200.059*
C90.2049 (4)0.2268 (4)0.1470 (2)0.0508 (8)
H90.27070.23480.09440.061*
C100.1063 (4)0.3412 (3)0.2158 (2)0.0464 (7)
H100.10980.42460.20840.056*
C110.1017 (3)0.2117 (2)0.38324 (18)0.0312 (6)
C120.0063 (4)0.2132 (3)0.30169 (19)0.0331 (6)
C130.3449 (4)0.6024 (3)0.2400 (2)0.0387 (6)
C140.4823 (4)0.6235 (3)0.17522 (19)0.0374 (6)
C150.6419 (4)0.5993 (3)0.1931 (2)0.0444 (7)
H150.66600.56970.24650.053*
C160.7660 (4)0.6182 (3)0.1330 (2)0.0482 (8)
H160.87420.60380.14630.058*
C170.7268 (4)0.6589 (3)0.0529 (2)0.0462 (7)
C180.5708 (5)0.6850 (4)0.0337 (2)0.0538 (8)
H180.54740.71410.02010.065*
C190.4491 (4)0.6678 (3)0.0947 (2)0.0481 (7)
H190.34350.68600.08220.058*
C200.3027 (4)0.7314 (3)0.5455 (2)0.0379 (6)
C210.4278 (4)0.7985 (3)0.6361 (2)0.0368 (6)
C220.4937 (4)0.7252 (3)0.6892 (2)0.0405 (7)
H220.46000.63230.66830.049*
C230.6086 (4)0.7878 (3)0.7728 (2)0.0455 (7)
H230.65280.73800.80790.055*
C240.6561 (4)0.9258 (3)0.8028 (2)0.0485 (8)
C250.5959 (4)1.0025 (3)0.7510 (2)0.0508 (8)
H250.63131.09550.77180.061*
C260.4819 (4)0.9381 (3)0.6678 (2)0.0452 (7)
H260.44050.98860.63220.054*
H5A0.095 (5)0.634 (4)0.3133 (17)0.080*
H5B0.085 (5)0.684 (3)0.4040 (16)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0402 (2)0.02628 (19)0.0357 (2)0.01193 (14)0.00110 (14)0.00598 (14)
Cl10.0662 (6)0.0775 (7)0.0582 (5)0.0087 (5)0.0233 (5)0.0139 (5)
Cl20.0806 (7)0.0814 (7)0.0473 (5)0.0111 (6)0.0045 (5)0.0114 (5)
N10.0366 (12)0.0243 (11)0.0341 (12)0.0101 (9)0.0062 (10)0.0059 (9)
N20.0342 (12)0.0368 (13)0.0376 (13)0.0109 (10)0.0046 (10)0.0090 (10)
O10.0422 (11)0.0432 (11)0.0426 (11)0.0144 (9)0.0059 (9)0.0165 (9)
O20.0596 (14)0.0633 (15)0.0563 (14)0.0330 (12)0.0146 (12)0.0287 (12)
O30.0598 (13)0.0271 (10)0.0406 (11)0.0138 (9)0.0037 (10)0.0025 (8)
O40.0699 (15)0.0377 (12)0.0584 (14)0.0273 (11)0.0084 (12)0.0022 (10)
O50.0503 (13)0.0417 (12)0.0463 (12)0.0230 (10)0.0047 (10)0.0107 (10)
C10.0413 (16)0.0323 (14)0.0341 (14)0.0115 (12)0.0023 (12)0.0054 (11)
C20.0470 (17)0.0407 (16)0.0395 (16)0.0173 (14)0.0038 (13)0.0112 (13)
C30.0486 (17)0.0328 (15)0.0486 (17)0.0168 (13)0.0117 (14)0.0132 (13)
C40.0383 (15)0.0278 (14)0.0412 (15)0.0082 (11)0.0126 (12)0.0075 (11)
C50.058 (2)0.0276 (15)0.0536 (19)0.0083 (14)0.0135 (16)0.0050 (13)
C60.0500 (18)0.0302 (15)0.0497 (19)0.0024 (13)0.0078 (15)0.0040 (13)
C70.0374 (16)0.0418 (16)0.0367 (15)0.0060 (13)0.0087 (13)0.0017 (13)
C80.0392 (17)0.054 (2)0.0388 (17)0.0036 (14)0.0036 (13)0.0026 (14)
C90.0422 (17)0.067 (2)0.0368 (17)0.0136 (16)0.0028 (14)0.0097 (15)
C100.0434 (17)0.0491 (18)0.0458 (18)0.0146 (14)0.0014 (14)0.0137 (14)
C110.0314 (14)0.0258 (13)0.0354 (14)0.0079 (11)0.0102 (11)0.0051 (11)
C120.0313 (14)0.0292 (14)0.0352 (14)0.0058 (11)0.0085 (11)0.0052 (11)
C130.0431 (16)0.0303 (14)0.0368 (15)0.0081 (12)0.0000 (12)0.0046 (12)
C140.0456 (16)0.0269 (14)0.0342 (14)0.0072 (12)0.0033 (12)0.0046 (11)
C150.0490 (18)0.0403 (16)0.0454 (17)0.0141 (14)0.0056 (14)0.0167 (13)
C160.0486 (18)0.0433 (18)0.0543 (19)0.0164 (15)0.0084 (15)0.0137 (15)
C170.0501 (18)0.0377 (16)0.0397 (16)0.0032 (14)0.0092 (14)0.0022 (13)
C180.062 (2)0.058 (2)0.0366 (17)0.0120 (17)0.0040 (15)0.0164 (15)
C190.0481 (18)0.0506 (19)0.0438 (17)0.0155 (15)0.0001 (14)0.0128 (14)
C200.0429 (16)0.0290 (14)0.0422 (16)0.0134 (12)0.0100 (13)0.0055 (12)
C210.0392 (15)0.0309 (14)0.0407 (16)0.0122 (12)0.0138 (13)0.0048 (12)
C220.0481 (17)0.0322 (15)0.0393 (16)0.0113 (13)0.0112 (13)0.0054 (12)
C230.0471 (18)0.0496 (18)0.0387 (16)0.0159 (15)0.0083 (14)0.0081 (14)
C240.0442 (18)0.0534 (19)0.0377 (16)0.0097 (15)0.0074 (14)0.0023 (14)
C250.0536 (19)0.0351 (16)0.0523 (19)0.0075 (14)0.0117 (16)0.0060 (14)
C260.0503 (18)0.0319 (15)0.0518 (18)0.0144 (14)0.0097 (15)0.0037 (13)
Geometric parameters (Å, º) top
Cu1—O12.297 (2)C7—C81.402 (4)
Cu1—O31.948 (2)C8—C91.358 (5)
Cu1—O51.980 (2)C8—H80.9300
Cu1—N12.014 (2)C9—C101.395 (5)
Cu1—N22.023 (2)C9—H90.9300
Cl1—C171.742 (3)C10—H100.9300
Cl2—C241.737 (3)C11—C121.421 (4)
N1—C11.324 (4)C13—C141.510 (4)
N1—C111.359 (3)C14—C151.385 (4)
N2—C101.323 (4)C14—C191.394 (4)
N2—C121.357 (3)C15—C161.382 (4)
O1—C131.255 (3)C15—H150.9300
O2—C131.262 (4)C16—C171.378 (4)
O3—C201.271 (3)C16—H160.9300
O4—C201.239 (3)C17—C181.372 (5)
O5—H5A0.86 (3)C18—C191.377 (5)
O5—H5B0.85 (3)C18—H180.9300
C1—C21.393 (4)C19—H190.9300
C1—H10.9300C20—C211.503 (4)
C2—C31.366 (4)C21—C221.385 (4)
C2—H20.9300C21—C261.396 (4)
C3—C41.401 (4)C22—C231.384 (4)
C3—H30.9300C22—H220.9300
C4—C111.403 (4)C23—C241.381 (5)
C4—C51.434 (4)C23—H230.9300
C5—C61.348 (5)C24—C251.380 (5)
C5—H50.9300C25—C261.379 (5)
C6—C71.432 (4)C25—H250.9300
C6—H60.9300C26—H260.9300
C7—C121.400 (4)
O3—Cu1—O594.73 (9)C9—C10—H10118.7
O3—Cu1—N189.28 (8)N1—C11—C4123.0 (3)
O5—Cu1—N1164.96 (9)N1—C11—C12116.8 (2)
O3—Cu1—N2167.24 (9)C4—C11—C12120.2 (2)
O5—Cu1—N291.99 (9)N2—C12—C7123.0 (3)
N1—Cu1—N281.56 (9)N2—C12—C11116.4 (2)
O3—Cu1—O1100.60 (8)C7—C12—C11120.7 (3)
O5—Cu1—O190.81 (8)O1—C13—O2125.0 (3)
N1—Cu1—O1102.72 (8)O1—C13—C14118.7 (3)
N2—Cu1—O190.12 (8)O2—C13—C14116.3 (3)
C1—N1—C11118.2 (2)C15—C14—C19118.5 (3)
C1—N1—Cu1129.15 (19)C15—C14—C13121.7 (3)
C11—N1—Cu1112.63 (17)C19—C14—C13119.8 (3)
C10—N2—C12118.0 (3)C16—C15—C14121.1 (3)
C10—N2—Cu1129.3 (2)C16—C15—H15119.4
C12—N2—Cu1112.67 (18)C14—C15—H15119.4
C13—O1—Cu1121.27 (19)C17—C16—C15118.9 (3)
C20—O3—Cu1129.42 (19)C17—C16—H16120.6
Cu1—O5—H5A100 (3)C15—C16—H16120.6
Cu1—O5—H5B102 (3)C18—C17—C16121.4 (3)
H5A—O5—H5B107.5 (16)C18—C17—Cl1119.4 (3)
N1—C1—C2122.4 (3)C16—C17—Cl1119.2 (3)
N1—C1—H1118.8C17—C18—C19119.3 (3)
C2—C1—H1118.8C17—C18—H18120.3
C3—C2—C1119.8 (3)C19—C18—H18120.3
C3—C2—H2120.1C18—C19—C14120.8 (3)
C1—C2—H2120.1C18—C19—H19119.6
C2—C3—C4119.5 (3)C14—C19—H19119.6
C2—C3—H3120.2O4—C20—O3125.0 (3)
C4—C3—H3120.2O4—C20—C21118.9 (2)
C3—C4—C11117.0 (3)O3—C20—C21116.1 (3)
C3—C4—C5124.8 (3)C22—C21—C26118.7 (3)
C11—C4—C5118.2 (3)C22—C21—C20121.6 (3)
C6—C5—C4121.4 (3)C26—C21—C20119.8 (3)
C6—C5—H5119.3C23—C22—C21121.2 (3)
C4—C5—H5119.3C23—C22—H22119.4
C5—C6—C7121.4 (3)C21—C22—H22119.4
C5—C6—H6119.3C24—C23—C22118.5 (3)
C7—C6—H6119.3C24—C23—H23120.8
C12—C7—C8117.1 (3)C22—C23—H23120.8
C12—C7—C6118.1 (3)C25—C24—C23122.0 (3)
C8—C7—C6124.7 (3)C25—C24—Cl2118.8 (3)
C9—C8—C7119.6 (3)C23—C24—Cl2119.2 (3)
C9—C8—H8120.2C26—C25—C24118.6 (3)
C7—C8—H8120.2C26—C25—H25120.7
C8—C9—C10119.6 (3)C24—C25—H25120.7
C8—C9—H9120.2C25—C26—C21121.1 (3)
C10—C9—H9120.2C25—C26—H26119.5
N2—C10—C9122.7 (3)C21—C26—H26119.5
N2—C10—H10118.7
O3—Cu1—N1—C18.4 (2)C3—C4—C11—C12180.0 (2)
O5—Cu1—N1—C1114.2 (4)C5—C4—C11—C120.0 (4)
N2—Cu1—N1—C1179.5 (3)C10—N2—C12—C70.2 (4)
O1—Cu1—N1—C192.3 (2)Cu1—N2—C12—C7179.7 (2)
O3—Cu1—N1—C11170.37 (18)C10—N2—C12—C11179.7 (3)
O5—Cu1—N1—C1164.6 (4)Cu1—N2—C12—C110.2 (3)
N2—Cu1—N1—C110.72 (17)C8—C7—C12—N21.1 (4)
O1—Cu1—N1—C1188.93 (18)C6—C7—C12—N2178.9 (3)
O3—Cu1—N2—C10136.4 (4)C8—C7—C12—C11178.7 (3)
O5—Cu1—N2—C1014.6 (3)C6—C7—C12—C111.2 (4)
N1—Cu1—N2—C10179.1 (3)N1—C11—C12—N20.9 (4)
O1—Cu1—N2—C1076.2 (3)C4—C11—C12—N2179.4 (2)
O3—Cu1—N2—C1244.3 (5)N1—C11—C12—C7179.0 (2)
O5—Cu1—N2—C12166.08 (18)C4—C11—C12—C70.8 (4)
N1—Cu1—N2—C120.26 (18)Cu1—O1—C13—O27.5 (4)
O1—Cu1—N2—C12103.11 (18)Cu1—O1—C13—C14173.08 (17)
O3—Cu1—O1—C13114.2 (2)O1—C13—C14—C159.0 (4)
O5—Cu1—O1—C1319.2 (2)O2—C13—C14—C15170.4 (3)
N1—Cu1—O1—C13154.1 (2)O1—C13—C14—C19170.6 (3)
N2—Cu1—O1—C1372.8 (2)O2—C13—C14—C199.9 (4)
O5—Cu1—O3—C2012.6 (3)C19—C14—C15—C160.0 (4)
N1—Cu1—O3—C20178.1 (3)C13—C14—C15—C16179.6 (3)
N2—Cu1—O3—C20134.1 (4)C14—C15—C16—C171.6 (5)
O1—Cu1—O3—C2079.1 (3)C15—C16—C17—C182.2 (5)
C11—N1—C1—C20.1 (4)C15—C16—C17—Cl1177.5 (2)
Cu1—N1—C1—C2178.9 (2)C16—C17—C18—C191.3 (5)
N1—C1—C2—C30.1 (5)Cl1—C17—C18—C19178.4 (3)
C1—C2—C3—C40.2 (4)C17—C18—C19—C140.4 (5)
C2—C3—C4—C110.3 (4)C15—C14—C19—C181.0 (5)
C2—C3—C4—C5179.8 (3)C13—C14—C19—C18178.6 (3)
C3—C4—C5—C6179.7 (3)Cu1—O3—C20—O49.0 (5)
C11—C4—C5—C60.4 (4)Cu1—O3—C20—C21171.72 (18)
C4—C5—C6—C70.1 (5)O4—C20—C21—C22172.6 (3)
C5—C6—C7—C120.9 (5)O3—C20—C21—C226.7 (4)
C5—C6—C7—C8179.1 (3)O4—C20—C21—C268.2 (4)
C12—C7—C8—C90.8 (4)O3—C20—C21—C26172.4 (3)
C6—C7—C8—C9179.2 (3)C26—C21—C22—C231.0 (4)
C7—C8—C9—C100.3 (5)C20—C21—C22—C23179.8 (3)
C12—N2—C10—C91.0 (4)C21—C22—C23—C240.3 (5)
Cu1—N2—C10—C9178.3 (2)C22—C23—C24—C251.5 (5)
C8—C9—C10—N21.2 (5)C22—C23—C24—Cl2178.0 (2)
C1—N1—C11—C40.2 (4)C23—C24—C25—C261.3 (5)
Cu1—N1—C11—C4179.2 (2)Cl2—C24—C25—C26178.2 (2)
C1—N1—C11—C12180.0 (2)C24—C25—C26—C210.1 (5)
Cu1—N1—C11—C121.1 (3)C22—C21—C26—C251.2 (4)
C3—C4—C11—N10.3 (4)C20—C21—C26—C25179.6 (3)
C5—C4—C11—N1179.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O10.86 (3)2.61 (4)3.053 (3)113 (3)
O5—H5A···O20.86 (3)1.71 (3)2.554 (3)170 (4)
O5—H5B···O30.85 (3)2.56 (4)2.890 (3)104 (3)
O5—H5B···O40.85 (3)1.80 (2)2.620 (3)161 (4)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds