(2,2′-Bipyrid­yl)methano­lbis(trichloro­acetato)copper(II)

In the title compound, [Cu(C₂Cl₃O₂)₂(C₁₀H₈N₂)(CH₄O)], the Cu^II cation is coordinated by bipyridyl N atoms, two trichloro­acetato O atoms and one methanol O atom in a distorted tetra­gonal pyramidal geometry. In the crystal structure, inter­molecular O—H...O, C—H...O and π–π inter­actions are found.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.049
• wR factor = 0.123
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C13

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.948
            Tmax scaled      0.583 Tmin scaled      0.505
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

(2,2'-Bipyridyl)methanolbis(trichloroacetato)copper(II)

Crystal data

[Cu(C2Cl3O2)2(C10H8N2)(CH4O)]	Z = 2
Mr = 576.51	F(000) = 574
Triclinic, P1	Dx = 1.787 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.278 (3) Å	Cell parameters from 2841 reflections
b = 9.863 (3) Å	θ = 2.5–27.1°
c = 12.356 (3) Å	µ = 1.80 mm^−1
α = 76.540 (3)°	T = 293 K
β = 76.941 (3)°	Block, blue
γ = 87.618 (4)°	0.40 × 0.40 × 0.30 mm
V = 1071.1 (5) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3695 independent reflections
Radiation source: fine-focus sealed tube	3233 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −10→11
Tmin = 0.533, Tmax = 0.615	k = −11→5
4439 measured reflections	l = −14→13

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0584P)^2 + 1.0108P] where P = (Fo^2 + 2Fc^2)/3
3695 reflections	(Δ/σ)max = 0.003
263 parameters	Δρmax = 0.66 e Å^−3
0 restraints	Δρmin = −0.56 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	0.58166 (5)	0.75028 (5)	0.68362 (4)	0.04209 (17)
N1	0.5505 (3)	0.7244 (3)	0.5346 (2)	0.0377 (7)
N2	0.4115 (3)	0.8773 (3)	0.6691 (3)	0.0412 (7)
O1	0.7632 (3)	0.6427 (3)	0.6710 (2)	0.0520 (7)
O2	0.7005 (3)	0.4648 (4)	0.8222 (3)	0.0674 (9)
O3	0.6191 (3)	0.8061 (4)	0.8158 (3)	0.0592 (8)
O4	0.7894 (4)	0.9637 (4)	0.7132 (3)	0.0714 (9)
O5	0.4325 (3)	0.5722 (3)	0.8034 (2)	0.0539 (7)
H11	0.4981	0.5211	0.8239	0.065*
Cl1	0.96254 (16)	0.37020 (14)	0.63365 (13)	0.0776 (4)
Cl2	0.99905 (16)	0.40411 (17)	0.85058 (12)	0.0841 (4)
Cl3	1.07541 (13)	0.62839 (13)	0.65420 (11)	0.0673 (3)
Cl4	0.6296 (2)	0.8344 (2)	1.03595 (11)	0.1021 (6)
Cl5	0.9271 (2)	0.8037 (2)	0.91668 (15)	0.1181 (7)
Cl6	0.8017 (3)	1.0762 (2)	0.90936 (16)	0.1226 (8)
C1	0.6312 (4)	0.6440 (4)	0.4706 (3)	0.0446 (9)
H1	0.7127	0.5983	0.4935	0.053*
C2	0.5968 (5)	0.6271 (4)	0.3716 (3)	0.0512 (10)
H2	0.6551	0.5716	0.3279	0.061*
C3	0.4760 (5)	0.6929 (5)	0.3387 (3)	0.0532 (11)
H3	0.4497	0.6812	0.2731	0.064*
C4	0.3934 (5)	0.7769 (4)	0.4039 (3)	0.0473 (9)
H4	0.3115	0.8232	0.3822	0.057*
C5	0.4334 (4)	0.7918 (4)	0.5014 (3)	0.0365 (8)
C6	0.3542 (4)	0.8786 (4)	0.5779 (3)	0.0380 (8)
C7	0.2310 (5)	0.9560 (4)	0.5604 (4)	0.0508 (10)
H7	0.1940	0.9586	0.4960	0.061*
C8	0.1636 (5)	1.0291 (5)	0.6398 (4)	0.0609 (12)
H8	0.0781	1.0788	0.6309	0.073*
C9	0.2223 (5)	1.0287 (5)	0.7317 (4)	0.0592 (12)
H9	0.1785	1.0796	0.7849	0.071*
C10	0.3470 (5)	0.9520 (5)	0.7445 (4)	0.0533 (11)
H10	0.3877	0.9519	0.8068	0.064*
C11	0.9500 (5)	0.4899 (4)	0.7231 (4)	0.0483 (10)
C12	0.7869 (4)	0.5377 (5)	0.7436 (3)	0.0461 (10)
C13	0.7652 (5)	0.9033 (5)	0.9129 (4)	0.0581 (12)
C14	0.7201 (5)	0.8933 (4)	0.8010 (3)	0.0462 (10)
C15	0.3273 (6)	0.5939 (6)	0.9011 (4)	0.0739 (15)
H15A	0.3687	0.6560	0.9357	0.111*
H15B	0.3028	0.5063	0.9549	0.111*
H15C	0.2396	0.6340	0.8784	0.111*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0384 (3)	0.0529 (3)	0.0392 (3)	0.0035 (2)	−0.0119 (2)	−0.0162 (2)
N1	0.0370 (16)	0.0418 (17)	0.0348 (16)	−0.0015 (13)	−0.0067 (13)	−0.0107 (13)
N2	0.0385 (17)	0.0455 (19)	0.0408 (17)	−0.0011 (14)	−0.0056 (14)	−0.0153 (15)
O1	0.0447 (16)	0.0652 (19)	0.0426 (15)	0.0133 (14)	−0.0119 (12)	−0.0057 (14)
O2	0.0523 (19)	0.079 (2)	0.0581 (19)	−0.0005 (17)	−0.0029 (16)	0.0013 (17)
O3	0.0551 (18)	0.080 (2)	0.0541 (17)	−0.0060 (16)	−0.0170 (14)	−0.0333 (16)
O4	0.093 (3)	0.070 (2)	0.0463 (18)	−0.0101 (19)	−0.0238 (18)	0.0055 (17)
O5	0.0488 (16)	0.0657 (19)	0.0459 (16)	−0.0071 (14)	−0.0029 (13)	−0.0162 (14)
Cl1	0.0747 (9)	0.0691 (8)	0.0913 (10)	0.0081 (6)	−0.0051 (7)	−0.0371 (7)
Cl2	0.0708 (8)	0.1004 (11)	0.0734 (8)	−0.0004 (7)	−0.0377 (7)	0.0169 (8)
Cl3	0.0499 (6)	0.0627 (7)	0.0813 (8)	−0.0085 (5)	−0.0136 (6)	−0.0001 (6)
Cl4	0.1290 (14)	0.1255 (14)	0.0470 (7)	−0.0558 (11)	0.0051 (8)	−0.0243 (8)
Cl5	0.0886 (11)	0.1609 (18)	0.0959 (12)	0.0091 (11)	−0.0564 (10)	0.0214 (11)
Cl6	0.183 (2)	0.0966 (12)	0.0959 (12)	−0.0677 (13)	−0.0146 (12)	−0.0406 (10)
C1	0.043 (2)	0.048 (2)	0.043 (2)	0.0020 (17)	−0.0038 (17)	−0.0148 (18)
C2	0.059 (3)	0.052 (3)	0.044 (2)	0.000 (2)	−0.006 (2)	−0.0192 (19)
C3	0.067 (3)	0.058 (3)	0.035 (2)	−0.011 (2)	−0.010 (2)	−0.0121 (19)
C4	0.053 (2)	0.047 (2)	0.044 (2)	0.0000 (19)	−0.0169 (19)	−0.0085 (18)
C5	0.0385 (19)	0.0350 (19)	0.0347 (18)	−0.0049 (15)	−0.0069 (15)	−0.0057 (15)
C6	0.037 (2)	0.0343 (19)	0.041 (2)	−0.0060 (15)	−0.0068 (16)	−0.0048 (16)
C7	0.051 (2)	0.047 (2)	0.054 (2)	0.0025 (19)	−0.015 (2)	−0.007 (2)
C8	0.051 (3)	0.049 (3)	0.081 (3)	0.011 (2)	−0.012 (2)	−0.014 (2)
C9	0.053 (3)	0.057 (3)	0.068 (3)	0.004 (2)	0.001 (2)	−0.027 (2)
C10	0.053 (3)	0.059 (3)	0.053 (2)	0.000 (2)	−0.007 (2)	−0.026 (2)
C11	0.048 (2)	0.048 (2)	0.047 (2)	0.0008 (18)	−0.0132 (18)	−0.0046 (19)
C12	0.046 (2)	0.060 (3)	0.037 (2)	0.004 (2)	−0.0128 (18)	−0.018 (2)
C13	0.068 (3)	0.065 (3)	0.044 (2)	−0.020 (2)	−0.019 (2)	−0.008 (2)
C14	0.054 (2)	0.048 (2)	0.043 (2)	0.007 (2)	−0.0228 (19)	−0.012 (2)
C15	0.068 (3)	0.088 (4)	0.057 (3)	−0.011 (3)	0.011 (2)	−0.022 (3)

Geometric parameters (Å, º)

Cu1—O3	1.945 (3)	C1—H1	0.9300
Cu1—O1	1.949 (3)	C2—C3	1.366 (6)
Cu1—N2	1.988 (3)	C2—H2	0.9300
Cu1—N1	2.000 (3)	C3—C4	1.379 (6)
Cu1—O5	2.293 (3)	C3—H3	0.9300
N1—C1	1.338 (5)	C4—C5	1.378 (5)
N1—C5	1.344 (5)	C4—H4	0.9300
N2—C10	1.342 (5)	C5—C6	1.475 (5)
N2—C6	1.347 (5)	C6—C7	1.378 (6)
O1—C12	1.251 (5)	C7—C8	1.373 (6)
O2—C12	1.214 (5)	C7—H7	0.9300
O3—C14	1.252 (5)	C8—C9	1.366 (7)
O4—C14	1.201 (5)	C8—H8	0.9300
O5—C15	1.423 (5)	C9—C10	1.375 (6)
O5—H11	0.8200	C9—H9	0.9300
Cl1—C11	1.779 (4)	C10—H10	0.9300
Cl2—C11	1.754 (4)	C11—C12	1.549 (6)
Cl3—C11	1.757 (4)	C13—C14	1.558 (5)
Cl4—C13	1.755 (5)	C15—H15A	0.9600
Cl5—C13	1.764 (5)	C15—H15B	0.9600
Cl6—C13	1.742 (5)	C15—H15C	0.9600
C1—C2	1.379 (6)
O3—Cu1—O1	90.68 (13)	C7—C6—C5	124.2 (3)
O3—Cu1—N2	94.66 (13)	C8—C7—C6	118.9 (4)
O1—Cu1—N2	170.13 (12)	C8—C7—H7	120.6
O3—Cu1—N1	170.90 (13)	C6—C7—H7	120.6
O1—Cu1—N1	92.35 (12)	C9—C8—C7	120.0 (4)
N2—Cu1—N1	81.16 (12)	C9—C8—H8	120.0
O3—Cu1—O5	89.46 (12)	C7—C8—H8	120.0
O1—Cu1—O5	95.77 (12)	C8—C9—C10	119.0 (4)
N2—Cu1—O5	92.58 (12)	C8—C9—H9	120.5
N1—Cu1—O5	98.76 (11)	C10—C9—H9	120.5
C1—N1—C5	119.3 (3)	N2—C10—C9	121.4 (4)
C1—N1—Cu1	125.9 (3)	N2—C10—H10	119.3
C5—N1—Cu1	114.7 (2)	C9—C10—H10	119.3
C10—N2—C6	119.5 (4)	C12—C11—Cl2	111.9 (3)
C10—N2—Cu1	125.6 (3)	C12—C11—Cl3	112.7 (3)
C6—N2—Cu1	114.8 (2)	Cl2—C11—Cl3	108.7 (2)
C12—O1—Cu1	125.0 (3)	C12—C11—Cl1	105.6 (3)
C14—O3—Cu1	118.6 (3)	Cl2—C11—Cl1	108.7 (2)
C15—O5—Cu1	121.3 (3)	Cl3—C11—Cl1	109.0 (2)
C15—O5—H11	109.5	O2—C12—O1	129.7 (4)
Cu1—O5—H11	97.7	O2—C12—C11	116.4 (4)
N1—C1—C2	121.9 (4)	O1—C12—C11	113.8 (4)
N1—C1—H1	119.1	C14—C13—Cl6	110.1 (3)
C2—C1—H1	119.1	C14—C13—Cl4	112.8 (3)
C3—C2—C1	119.1 (4)	Cl6—C13—Cl4	109.3 (3)
C3—C2—H2	120.5	C14—C13—Cl5	105.7 (3)
C1—C2—H2	120.5	Cl6—C13—Cl5	110.2 (3)
C2—C3—C4	119.2 (4)	Cl4—C13—Cl5	108.7 (3)
C2—C3—H3	120.4	O4—C14—O3	129.0 (4)
C4—C3—H3	120.4	O4—C14—C13	117.0 (4)
C5—C4—C3	119.5 (4)	O3—C14—C13	113.9 (4)
C5—C4—H4	120.3	O5—C15—H15A	109.5
C3—C4—H4	120.3	O5—C15—H15B	109.5
N1—C5—C4	121.0 (3)	H15A—C15—H15B	109.5
N1—C5—C6	114.5 (3)	O5—C15—H15C	109.5
C4—C5—C6	124.5 (4)	H15A—C15—H15C	109.5
N2—C6—C7	121.1 (4)	H15B—C15—H15C	109.5
N2—C6—C5	114.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H11···O2	0.82	1.93	2.699 (5)	155
C4—H4···O4^i	0.93	2.42	3.247 (6)	148
C7—H7···O4^i	0.93	2.49	3.336 (7)	151

Symmetry code: (i) −x+1, −y+2, −z+1.