Aqua­(1,10-phenanthroline)bis­(trichloro­acetato)copper(II)

In the title compound, [Cu(C₂Cl₃O₂)₂(C₁₂H₈N₂)(H₂O)], the copper(II) ion is five-coordinated by four basal atoms (two N atoms from a 1,10-phenanthroline mol­ecule and two O atoms from two trichloro­acetate anions) and one axial aqua mol­ecule, in a distorted square-pyramidal coordination geometry. Moreover, two adjacent mononuclear units are associated by intra- and inter­molecular O—H...O hydrogen bonds to form a grid dimer. The hydrogen-bonding pattern could be described in graph-set terminology as R₁¹(6)R₁²(8).

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.083
• wR factor = 0.167
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O4
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C2

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         13
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3    ..  O4      ..       3.10 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  Cl6    ..  C12     ..       3.23 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.83(5), Rep   0.824(19) ......       2.63 su-Rat
              O5   -H5A     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.82(5), Rep     0.82(2) ......       2.50 su-Rat
              O5   -H5B     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.83(5), Rep   0.824(19) ......       2.63 su-Rat
              O5   -H5A     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.82(5), Rep     0.82(2) ......       2.50 su-Rat
              O5   -H5B     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.82(5), Rep     0.82(2) ......       2.50 su-Rat
              O5   -H5B     1.555   1.555

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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

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Computing details

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: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Aqua(1,10-phenanthroline)bis(trichloroacetato)copper(II)

Crystal data

[Cu(C2Cl3O2)2(C12H8N2)(H2O)]	F(000) = 1164
Mr = 586.51	Dx = 1.763 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3444 reflections
a = 11.8410 (7) Å	θ = 2.3–24.2°
b = 12.5940 (8) Å	µ = 1.75 mm^−1
c = 17.8365 (8) Å	T = 298 K
β = 123.817 (3)°	Prism, blue
V = 2209.9 (2) Å^3	0.22 × 0.15 × 0.12 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	3892 independent reflections
Radiation source: fine-focus sealed tube	3535 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −14→14
Tmin = 0.700, Tmax = 0.818	k = −14→14
20876 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H-atom parameters constrained
S = 1.31	w = 1/[σ^2(Fo^2) + (0.0476P)^2 + 6.2996P] where P = (Fo^2 + 2Fc^2)/3
3892 reflections	(Δ/σ)max < 0.001
277 parameters	Δρmax = 0.66 e Å^−3
3 restraints	Δρmin = −0.42 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.71560 (7)	0.99526 (5)	0.38037 (5)	0.0369 (2)
Cl1	0.8873 (3)	1.3749 (2)	0.52031 (15)	0.0975 (9)
Cl2	0.8834 (3)	1.3856 (2)	0.3597 (2)	0.1105 (10)
Cl3	0.63702 (19)	1.36123 (15)	0.34962 (16)	0.0760 (7)
Cl4	0.9491 (2)	1.04204 (18)	0.23170 (13)	0.0689 (6)
Cl5	0.9596 (2)	0.81923 (18)	0.27282 (17)	0.0804 (7)
Cl6	0.7519 (3)	0.8991 (2)	0.09909 (14)	0.0905 (8)
O1	0.7292 (4)	1.1486 (3)	0.3757 (3)	0.0481 (11)
O2	0.9516 (6)	1.1762 (4)	0.4615 (5)	0.110 (3)
O3	0.8326 (4)	0.9638 (3)	0.3369 (3)	0.0412 (10)
O4	0.6415 (5)	0.9514 (5)	0.2020 (4)	0.0748 (16)
O5	0.8779 (4)	0.9816 (4)	0.5281 (3)	0.0485 (11)
H5A	0.923 (5)	0.927 (2)	0.538 (5)	0.058*
H5B	0.922 (5)	1.037 (2)	0.545 (5)	0.058*
N1	0.5447 (5)	1.0151 (4)	0.3791 (3)	0.0411 (12)
N2	0.6713 (5)	0.8418 (4)	0.3803 (3)	0.0392 (12)
C1	0.8338 (7)	1.2034 (5)	0.4171 (5)	0.0482 (16)
C2	0.8096 (6)	1.3252 (5)	0.4103 (4)	0.0428 (15)
C3	0.7627 (6)	0.9495 (5)	0.2529 (4)	0.0389 (14)
C4	0.8504 (7)	0.9279 (6)	0.2149 (5)	0.0514 (17)
C5	0.4820 (7)	1.1034 (6)	0.3757 (5)	0.0526 (17)
H5	0.5153	1.1682	0.3710	0.063*
C6	0.3665 (8)	1.1017 (7)	0.3788 (5)	0.067 (2)
H6	0.3228	1.1648	0.3751	0.080*
C7	0.3185 (7)	1.0075 (8)	0.3873 (5)	0.070 (2)
H7	0.2441	1.0065	0.3921	0.084*
C8	0.3804 (7)	0.9121 (7)	0.3888 (5)	0.0579 (19)
C9	0.3376 (8)	0.8071 (9)	0.3948 (6)	0.077 (3)
H9	0.2632	0.8001	0.3992	0.092*
C10	0.4000 (9)	0.7202 (8)	0.3944 (6)	0.078 (3)
H10	0.3691	0.6541	0.3989	0.093*
C11	0.5152 (7)	0.7261 (6)	0.3871 (4)	0.0549 (19)
C12	0.5848 (8)	0.6393 (6)	0.3836 (5)	0.065 (2)
H12	0.5554	0.5709	0.3837	0.078*
C13	0.6956 (8)	0.6538 (6)	0.3799 (5)	0.062 (2)
H13	0.7425	0.5960	0.3777	0.074*
C14	0.7372 (7)	0.7574 (5)	0.3795 (5)	0.0521 (17)
H14	0.8142	0.7675	0.3786	0.063*
C15	0.5628 (6)	0.8267 (5)	0.3847 (4)	0.0416 (15)
C16	0.4944 (6)	0.9208 (6)	0.3847 (4)	0.0429 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0348 (4)	0.0297 (4)	0.0521 (5)	−0.0001 (3)	0.0278 (4)	−0.0022 (3)
Cl1	0.1070 (19)	0.0893 (17)	0.0594 (13)	0.0143 (14)	0.0235 (13)	−0.0266 (12)
Cl2	0.142 (2)	0.0966 (19)	0.154 (3)	0.0097 (17)	0.120 (2)	0.0365 (18)
Cl3	0.0508 (11)	0.0416 (10)	0.0973 (16)	0.0102 (8)	0.0174 (11)	0.0023 (10)
Cl4	0.0629 (12)	0.0868 (14)	0.0636 (12)	−0.0231 (10)	0.0393 (10)	0.0035 (10)
Cl5	0.0834 (15)	0.0781 (14)	0.0992 (16)	0.0366 (12)	0.0630 (14)	0.0127 (12)
Cl6	0.0972 (17)	0.123 (2)	0.0445 (11)	−0.0267 (15)	0.0355 (12)	−0.0218 (12)
O1	0.041 (2)	0.030 (2)	0.075 (3)	−0.002 (2)	0.034 (2)	−0.002 (2)
O2	0.045 (3)	0.044 (3)	0.174 (7)	0.007 (3)	0.020 (4)	−0.014 (4)
O3	0.036 (2)	0.047 (2)	0.046 (3)	−0.0058 (19)	0.027 (2)	−0.008 (2)
O4	0.033 (3)	0.112 (5)	0.064 (3)	0.012 (3)	0.018 (3)	0.017 (3)
O5	0.040 (2)	0.056 (3)	0.049 (3)	0.001 (2)	0.025 (2)	−0.001 (2)
N1	0.034 (3)	0.045 (3)	0.047 (3)	0.003 (2)	0.024 (2)	−0.001 (2)
N2	0.034 (3)	0.035 (3)	0.048 (3)	−0.004 (2)	0.023 (2)	0.000 (2)
C1	0.045 (4)	0.030 (3)	0.065 (5)	0.000 (3)	0.028 (4)	−0.001 (3)
C2	0.047 (4)	0.029 (3)	0.050 (4)	0.002 (3)	0.026 (3)	−0.002 (3)
C3	0.031 (3)	0.034 (3)	0.050 (4)	0.005 (3)	0.022 (3)	0.011 (3)
C4	0.053 (4)	0.055 (4)	0.045 (4)	−0.004 (3)	0.027 (3)	0.002 (3)
C5	0.048 (4)	0.057 (4)	0.053 (4)	0.012 (3)	0.029 (4)	0.003 (3)
C6	0.047 (4)	0.086 (6)	0.071 (5)	0.024 (4)	0.034 (4)	0.001 (4)
C7	0.039 (4)	0.122 (8)	0.053 (4)	0.006 (5)	0.027 (4)	−0.005 (5)
C8	0.036 (4)	0.088 (6)	0.044 (4)	−0.003 (4)	0.019 (3)	0.001 (4)
C9	0.043 (4)	0.115 (8)	0.074 (6)	−0.027 (5)	0.033 (4)	0.005 (5)
C10	0.058 (5)	0.085 (7)	0.077 (6)	−0.030 (5)	0.028 (5)	0.005 (5)
C11	0.044 (4)	0.062 (5)	0.043 (4)	−0.019 (4)	0.015 (3)	0.004 (3)
C12	0.072 (5)	0.040 (4)	0.058 (5)	−0.021 (4)	0.020 (4)	0.000 (3)
C13	0.060 (5)	0.039 (4)	0.071 (5)	−0.006 (3)	0.027 (4)	−0.006 (4)
C14	0.050 (4)	0.040 (4)	0.060 (4)	0.002 (3)	0.027 (4)	0.000 (3)
C15	0.038 (3)	0.046 (4)	0.038 (3)	−0.014 (3)	0.019 (3)	−0.003 (3)
C16	0.028 (3)	0.065 (4)	0.031 (3)	−0.006 (3)	0.014 (3)	−0.003 (3)

Geometric parameters (Å, º)

Cu1—O1	1.943 (4)	C1—C2	1.552 (8)
Cu1—O3	1.968 (4)	C3—C4	1.548 (9)
Cu1—N2	2.002 (5)	C5—C6	1.400 (10)
Cu1—N1	2.027 (5)	C5—H5	0.9300
Cu1—O5	2.243 (5)	C6—C7	1.360 (12)
Cu1—O4	2.844 (4)	C6—H6	0.9300
Cl1—C2	1.755 (7)	C7—C8	1.400 (11)
Cl2—C2	1.741 (7)	C7—H7	0.9300
Cl3—C2	1.759 (7)	C8—C16	1.397 (9)
Cl4—C4	1.770 (7)	C8—C9	1.442 (12)
Cl5—C4	1.767 (7)	C9—C10	1.323 (13)
Cl6—C4	1.754 (7)	C9—H9	0.9300
O1—C1	1.239 (7)	C10—C11	1.443 (11)
O2—C1	1.208 (8)	C10—H10	0.9300
O3—C3	1.257 (7)	C11—C12	1.391 (11)
O4—C3	1.198 (7)	C11—C15	1.397 (9)
O5—H5A	0.824 (19)	C12—C13	1.362 (11)
O5—H5B	0.82 (2)	C12—H12	0.9300
N1—C5	1.318 (8)	C13—C14	1.396 (9)
N1—C16	1.357 (8)	C13—H13	0.9300
N2—C14	1.324 (8)	C14—H14	0.9300
N2—C15	1.344 (8)	C15—C16	1.435 (9)
O1—Cu1—O3	95.13 (18)	Cl5—C4—Cl4	109.3 (4)
O1—Cu1—N2	170.75 (19)	N1—C5—C6	121.5 (7)
O3—Cu1—N2	92.70 (19)	N1—C5—H5	119.3
O1—Cu1—N1	89.04 (19)	C6—C5—H5	119.3
O3—Cu1—N1	159.72 (19)	C7—C6—C5	119.7 (7)
N2—Cu1—N1	81.9 (2)	C7—C6—H6	120.1
O1—Cu1—O5	95.14 (19)	C5—C6—H6	120.1
O3—Cu1—O5	96.70 (17)	C6—C7—C8	120.3 (7)
N2—Cu1—O5	88.83 (19)	C6—C7—H7	119.9
N1—Cu1—O5	102.69 (19)	C8—C7—H7	119.9
C1—O1—Cu1	127.4 (4)	C16—C8—C7	116.3 (7)
C3—O3—Cu1	110.9 (4)	C16—C8—C9	117.8 (8)
Cu1—O5—H5A	110 (5)	C7—C8—C9	125.9 (7)
Cu1—O5—H5B	109 (5)	C10—C9—C8	122.5 (7)
H5A—O5—H5B	115 (3)	C10—C9—H9	118.7
C5—N1—C16	118.9 (6)	C8—C9—H9	118.7
C5—N1—Cu1	129.5 (5)	C9—C10—C11	121.1 (8)
C16—N1—Cu1	111.5 (4)	C9—C10—H10	119.4
C14—N2—C15	118.4 (6)	C11—C10—H10	119.4
C14—N2—Cu1	128.3 (4)	C12—C11—C15	116.9 (7)
C15—N2—Cu1	113.3 (4)	C12—C11—C10	125.2 (7)
O2—C1—O1	129.7 (6)	C15—C11—C10	117.9 (8)
O2—C1—C2	115.2 (6)	C13—C12—C11	120.5 (7)
O1—C1—C2	115.1 (6)	C13—C12—H12	119.8
C1—C2—Cl2	110.4 (5)	C11—C12—H12	119.8
C1—C2—Cl1	107.8 (5)	C12—C13—C14	118.6 (7)
Cl2—C2—Cl1	108.8 (4)	C12—C13—H13	120.7
C1—C2—Cl3	113.8 (4)	C14—C13—H13	120.7
Cl2—C2—Cl3	108.3 (4)	N2—C14—C13	122.6 (7)
Cl1—C2—Cl3	107.6 (3)	N2—C14—H14	118.7
O4—C3—O3	128.1 (6)	C13—C14—H14	118.7
O4—C3—C4	119.0 (6)	N2—C15—C11	123.0 (6)
O3—C3—C4	112.9 (5)	N2—C15—C16	116.2 (5)
C3—C4—Cl6	112.6 (5)	C11—C15—C16	120.8 (6)
C3—C4—Cl5	109.3 (4)	N1—C16—C8	123.3 (7)
Cl6—C4—Cl5	108.6 (4)	N1—C16—C15	116.9 (5)
C3—C4—Cl4	108.9 (5)	C8—C16—C15	119.8 (6)
Cl6—C4—Cl4	108.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2^i	0.82 (2)	1.97 (3)	2.765 (7)	161 (7)
O5—H5B···O3^i	0.82 (2)	2.46 (5)	2.972 (6)	121 (5)
O5—H5B···O2	0.82 (2)	2.45 (6)	3.056 (9)	131 (6)

Symmetry code: (i) −x+2, −y+2, −z+1.