Diethanol(2-hydr­oxy-2,2-diphenyl­acetato)pyridine­copper(II)

In the title mononuclear complex, [Cu(C₁₄H₁₁O₃)₂(C₅H₅N)₂(C₂H₆O)₂], the Cu atom has a distorted octa­hedral environment, formed by the N atoms of two pyridine mol­ecules, carboxylate O atoms belonging to two 2-hydr­oxy-2,2-diphenyl­acetate ligands and O atoms of two ethanol mol­ecules. The mol­ecule of the complex occupies a special position on a twofold axis, which passes through the Cu atom as well as the N and para-C atoms of each of the two pyridine ligands. One crystallographically independent inter­molecular hydrogen bond, involving the OH group of the hydroxy­diphenyl­acetate ligand and a carbonyl O atom of another acetate ligand of a neighbouring complex, is responsible for the formation of infinite chains running along the a axis of the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.115
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.29 Ratio
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Cu1    -   O4      ..      15.09 su

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O4     -   C21     ..       5.97 su

   0 ALERT level A = In general: serious problem
   2 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
   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); 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.

Diethanol(2-hydroxy-2,2-diphenylacetato)pyridinecopper(II)

Crystal data

[Cu(C14H11O3)2(C5H5N)2(C2H6O)2]	F(000) = 1612
Mr = 768.34	Dx = 1.311 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 17527 reflections
a = 9.7231 (19) Å	θ = 3.0–27.5°
b = 15.992 (2) Å	µ = 0.61 mm^−1
c = 25.143 (3) Å	T = 295 K
β = 95.23 (3)°	Prism, blue
V = 3893.3 (10) Å^3	0.37 × 0.25 × 0.19 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	4450 independent reflections
Radiation source: fine-focus sealed tube	3728 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −12→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −20→19
Tmin = 0.804, Tmax = 0.892	l = −32→32
18339 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0732P)^2 + 1.3059P] where P = (Fo^2 + 2Fc^2)/3
4450 reflections	(Δ/σ)max = 0.002
245 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.5000	0.516221 (17)	0.7500	0.03607 (11)
O1	0.34374 (12)	0.51509 (8)	0.69366 (5)	0.0385 (3)
O2	0.16131 (14)	0.51573 (9)	0.74154 (5)	0.0489 (3)
O3	−0.02049 (12)	0.52096 (9)	0.66105 (5)	0.0450 (3)
O4	0.64179 (17)	0.52433 (12)	0.67319 (7)	0.0692 (5)
N1	0.5000	0.64216 (13)	0.7500	0.0395 (4)
N2	0.5000	0.39003 (13)	0.7500	0.0387 (4)
C1	0.21630 (16)	0.51587 (9)	0.69898 (6)	0.0323 (3)
C2	0.11756 (16)	0.51878 (10)	0.64665 (6)	0.0337 (3)
C3	0.14966 (17)	0.59924 (11)	0.61721 (6)	0.0384 (3)
C4	0.2660 (2)	0.60460 (14)	0.58941 (8)	0.0521 (5)
C5	0.3005 (3)	0.68005 (17)	0.56648 (9)	0.0679 (6)
C6	0.2196 (3)	0.74924 (15)	0.57046 (9)	0.0707 (7)
C7	0.1019 (3)	0.74358 (15)	0.59621 (10)	0.0702 (7)
C8	0.0666 (2)	0.66875 (13)	0.61954 (8)	0.0518 (4)
C9	0.12951 (17)	0.44212 (11)	0.61060 (6)	0.0373 (3)
C10	0.0385 (2)	0.43764 (15)	0.56502 (8)	0.0591 (5)
C11	0.0371 (3)	0.36954 (17)	0.53122 (9)	0.0700 (6)
C12	0.1270 (3)	0.30442 (16)	0.54253 (10)	0.0675 (6)
C13	0.2158 (3)	0.30740 (16)	0.58772 (12)	0.0761 (7)
C14	0.2183 (2)	0.37671 (14)	0.62167 (9)	0.0596 (5)
C15	0.4830 (2)	0.68522 (13)	0.70417 (8)	0.0507 (4)
C16	0.4820 (2)	0.77176 (14)	0.70297 (11)	0.0650 (6)
C17	0.5000	0.81496 (19)	0.7500	0.0693 (10)
C18	0.61338 (19)	0.34676 (12)	0.74107 (8)	0.0466 (4)
C19	0.6167 (2)	0.26032 (13)	0.74116 (9)	0.0557 (5)
C20	0.5000	0.21722 (17)	0.7500	0.0555 (7)
C21	0.6396 (3)	0.4853 (2)	0.62297 (14)	0.0893 (9)
C22	0.6649 (5)	0.5412 (4)	0.57974 (16)	0.1377 (18)
H4	0.3211	0.5577	0.5861	0.063*
H5	0.3793	0.6834	0.5483	0.082*
H6	0.2444	0.7998	0.5558	0.085*
H7	0.0451	0.7901	0.5981	0.084*
H8	−0.0137	0.6655	0.6369	0.062*
H10	−0.0229	0.4814	0.5570	0.071*
H11	−0.0248	0.3678	0.5008	0.084*
H12	0.1274	0.2588	0.5196	0.081*
H13	0.2754	0.2628	0.5960	0.091*
H14	0.2808	0.3784	0.6520	0.071*
H15	0.4715	0.6560	0.6721	0.061*
H16	0.4693	0.8001	0.6706	0.078*
H17	0.5000	0.8731	0.7500	0.083*
H18	0.6929	0.3759	0.7346	0.056*
H19	0.6975	0.2320	0.7353	0.067*
H20	0.5000	0.1591	0.7500	0.067*
H21A	0.5502	0.4591	0.6149	0.107*
H21B	0.7088	0.4415	0.6250	0.107*
H22A	0.5982	0.5856	0.5779	0.107*
H22B	0.6571	0.5108	0.5467	0.107*
H22C	0.7561	0.5642	0.5859	0.107*
H23	−0.0201	0.5169	0.6936	0.068*
H24	0.7212	0.5253	0.6873	0.104*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.03116 (16)	0.03302 (17)	0.04138 (18)	0.000	−0.01106 (11)	0.000
O1	0.0291 (5)	0.0474 (7)	0.0372 (6)	−0.0022 (5)	−0.0068 (5)	0.0037 (5)
O2	0.0437 (7)	0.0720 (9)	0.0305 (6)	0.0047 (6)	0.0002 (5)	0.0027 (6)
O3	0.0280 (6)	0.0681 (9)	0.0383 (6)	0.0013 (5)	−0.0006 (5)	0.0003 (6)
O4	0.0464 (8)	0.0944 (13)	0.0651 (10)	0.0024 (8)	−0.0032 (7)	−0.0054 (9)
N1	0.0348 (9)	0.0372 (10)	0.0452 (11)	0.000	−0.0026 (8)	0.000
N2	0.0390 (10)	0.0361 (10)	0.0387 (10)	0.000	−0.0096 (8)	0.000
C1	0.0331 (7)	0.0312 (7)	0.0310 (7)	0.0003 (6)	−0.0047 (6)	0.0022 (6)
C2	0.0268 (7)	0.0427 (9)	0.0307 (7)	−0.0008 (6)	−0.0030 (6)	0.0017 (6)
C3	0.0403 (8)	0.0441 (9)	0.0288 (7)	−0.0008 (7)	−0.0077 (6)	0.0030 (6)
C4	0.0457 (10)	0.0609 (12)	0.0491 (10)	−0.0004 (9)	0.0009 (8)	0.0165 (9)
C5	0.0662 (14)	0.0823 (17)	0.0545 (12)	−0.0184 (13)	0.0014 (10)	0.0250 (11)
C6	0.1025 (19)	0.0526 (13)	0.0536 (12)	−0.0180 (13)	−0.0100 (12)	0.0158 (10)
C7	0.106 (2)	0.0424 (11)	0.0600 (13)	0.0075 (12)	−0.0062 (13)	0.0024 (10)
C8	0.0644 (12)	0.0476 (10)	0.0423 (9)	0.0079 (9)	−0.0014 (8)	−0.0002 (8)
C9	0.0348 (8)	0.0437 (9)	0.0331 (7)	−0.0063 (7)	0.0007 (6)	−0.0002 (7)
C10	0.0650 (13)	0.0595 (13)	0.0486 (11)	0.0022 (10)	−0.0171 (9)	−0.0069 (9)
C11	0.0801 (16)	0.0754 (16)	0.0506 (12)	−0.0105 (13)	−0.0144 (11)	−0.0178 (11)
C12	0.0689 (14)	0.0662 (14)	0.0682 (14)	−0.0135 (12)	0.0108 (11)	−0.0306 (12)
C13	0.0705 (15)	0.0602 (14)	0.0947 (19)	0.0150 (12)	−0.0078 (13)	−0.0250 (13)
C14	0.0555 (11)	0.0567 (12)	0.0628 (12)	0.0097 (10)	−0.0146 (9)	−0.0150 (10)
C15	0.0492 (10)	0.0475 (10)	0.0547 (11)	−0.0018 (8)	0.0003 (8)	0.0074 (8)
C16	0.0578 (12)	0.0478 (12)	0.0891 (17)	−0.0002 (10)	0.0053 (12)	0.0230 (11)
C17	0.0499 (16)	0.0365 (14)	0.121 (3)	0.000	0.0078 (18)	0.000
C18	0.0428 (9)	0.0427 (10)	0.0533 (10)	−0.0012 (7)	−0.0010 (8)	−0.0056 (8)
C19	0.0600 (12)	0.0438 (10)	0.0634 (12)	0.0086 (9)	0.0063 (10)	−0.0099 (9)
C20	0.0749 (19)	0.0341 (13)	0.0576 (16)	0.000	0.0064 (14)	0.000
C21	0.0719 (18)	0.100 (2)	0.095 (2)	0.0032 (16)	0.0023 (16)	−0.0199 (18)
C22	0.096 (3)	0.232 (6)	0.086 (2)	0.037 (3)	0.012 (2)	0.025 (3)

Geometric parameters (Å, º)

Cu1—O1	1.9807 (13)	C9—C14	1.369 (3)
Cu1—O1^i	1.9807 (13)	C9—C10	1.384 (3)
Cu1—O4	2.476 (2)	C10—C11	1.381 (3)
Cu1—O4^i	2.476 (2)	C10—H10	0.9300
Cu1—N1	2.014 (2)	C11—C12	1.373 (4)
Cu1—N2	2.018 (2)	C11—H11	0.9300
O1—C1	1.258 (2)	C12—C13	1.364 (4)
O2—C1	1.239 (2)	C12—H12	0.9300
O3—C2	1.4221 (19)	C13—C14	1.398 (3)
O3—H23	0.8200	C13—H13	0.9300
O4—C21	1.407 (4)	C14—H14	0.9300
O4—H24	0.8200	C15—C16	1.384 (3)
N1—C15^i	1.340 (2)	C15—H15	0.9300
N1—C15	1.340 (2)	C16—C17	1.367 (3)
N2—C18	1.338 (2)	C16—H16	0.9300
N2—C18^i	1.338 (2)	C17—C16^i	1.367 (3)
C1—C2	1.557 (2)	C17—H17	0.9300
C2—C3	1.531 (2)	C18—C19	1.383 (3)
C2—C9	1.535 (2)	C18—H18	0.9300
C3—C8	1.378 (3)	C19—C20	1.363 (3)
C3—C4	1.385 (3)	C19—H19	0.9300
C4—C5	1.392 (3)	C20—C19^i	1.363 (3)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.366 (4)	C21—C22	1.446 (5)
C5—H5	0.9300	C21—H21A	0.9700
C6—C7	1.369 (4)	C21—H21B	0.9700
C6—H6	0.9300	C22—H22A	0.9600
C7—C8	1.389 (3)	C22—H22B	0.9600
C7—H7	0.9300	C22—H22C	0.9600
C8—H8	0.9300
O1—Cu1—O1^i	178.95 (7)	C9—C2—C1	113.64 (13)
O1—Cu1—N1	90.52 (4)	C9—C10—H10	119.3
O1—Cu1—N2	89.48 (4)	C9—C14—C13	120.4 (2)
O4—Cu1—O1	83.57 (6)	C9—C14—H14	119.8
O4—Cu1—N1	87.05 (7)	C10—C9—C2	116.93 (16)
O4—Cu1—N2	93.05 (7)	C10—C11—H11	120.0
O4—Cu1—O1^i	96.55 (7)	C11—C10—C9	121.3 (2)
O4^i—Cu1—O4	174.00 (7)	C11—C10—H10	119.3
N1—Cu1—N2	180.000 (1)	C11—C12—H12	120.4
O1^i—Cu1—N1	90.52 (4)	C12—C13—C14	120.7 (2)
O1^i—Cu1—N2	89.48 (4)	C12—C13—H13	119.6
O4^i—Cu1—O1	96.49 (6)	C12—C11—C10	120.0 (2)
O4^i—Cu1—N1	87.00 (5)	C12—C11—H11	120.0
O4^i—Cu1—N2	93.00 (5)	C13—C12—C11	119.3 (2)
O4^i—Cu1—O1^i	83.57 (6)	C13—C12—H12	120.4
O1—C1—C2	116.60 (13)	C13—C14—H14	119.8
O2—C1—O1	126.74 (15)	C14—C9—C10	118.20 (18)
O2—C1—C2	116.65 (14)	C14—C9—C2	124.78 (16)
O3—C2—C3	109.95 (13)	C14—C13—H13	119.6
O3—C2—C9	107.09 (13)	C15^i—N1—C15	118.1 (2)
O3—C2—C1	108.01 (13)	C15^i—N1—Cu1	120.93 (12)
O4—C21—H21B	108.7	C15—N1—Cu1	120.93 (12)
O4—C21—H21A	108.7	C15—C16—H16	120.5
N1—C15—C16	122.2 (2)	C16—C17—C16^i	119.3 (3)
N1—C15—H15	118.9	C16—C17—H17	120.4
N2—C18—C19	122.44 (19)	C16^i—C17—H17	120.4
N2—C18—H18	118.8	C16—C15—H15	118.9
C1—O1—Cu1	128.50 (11)	C17—C16—C15	119.1 (2)
C2—O3—H23	109.5	C17—C16—H16	120.5
C3—C2—C9	110.85 (13)	C18—N2—C18^i	117.7 (2)
C3—C2—C1	107.25 (12)	C18—N2—Cu1	121.15 (11)
C3—C4—C5	120.1 (2)	C18^i—N2—Cu1	121.15 (11)
C3—C4—H4	120.0	C18—C19—H19	120.5
C3—C8—C7	120.6 (2)	C19^i—C20—C19	119.2 (3)
C3—C8—H8	119.7	C19^i—C20—H20	120.4
C4—C3—C2	120.52 (16)	C19—C20—H20	120.4
C4—C5—H5	119.7	C19—C18—H18	118.8
C5—C4—H4	120.0	C20—C19—C18	119.1 (2)
C5—C6—C7	119.5 (2)	C20—C19—H19	120.5
C5—C6—H6	120.2	C21—O4—H24	109.5
C6—C5—C4	120.7 (2)	C21—C22—H22A	109.5
C6—C5—H5	119.7	C21—C22—H22B	109.5
C6—C7—C8	120.4 (2)	C21—C22—H22C	109.5
C6—C7—H7	119.8	C22—C21—H21A	108.7
C7—C6—H6	120.2	C22—C21—H21B	108.7
C7—C8—H8	119.7	H21A—C21—H21B	107.6
C8—C3—C4	118.69 (18)	H22A—C22—H22B	109.5
C8—C3—C2	120.74 (16)	H22A—C22—H22C	109.5
C8—C7—H7	119.8	H22B—C22—H22C	109.5
Cu1—O1—C1—O2	−1.7 (3)	C1—C2—C3—C4	76.55 (19)
Cu1—O1—C1—C2	177.25 (10)	C1—C2—C9—C14	−0.8 (2)
Cu1—N1—C15—C16	179.74 (15)	C1—C2—C9—C10	175.87 (16)
Cu1—N2—C18—C19	179.59 (15)	C2—C3—C4—C5	−174.71 (18)
O1—Cu1—N1—C15^i	138.41 (10)	C2—C3—C8—C7	175.04 (18)
O1^i—Cu1—N1—C15^i	−41.59 (10)	C2—C9—C10—C11	−177.2 (2)
O1—Cu1—N1—C15	−41.59 (10)	C2—C9—C14—C13	176.3 (2)
O1^i—Cu1—N1—C15	138.41 (10)	C3—C4—C5—C6	−0.8 (3)
O1—Cu1—N2—C18	123.33 (10)	C3—C2—C9—C14	120.1 (2)
O1^i—Cu1—N2—C18	−56.67 (10)	C3—C2—C9—C10	−63.3 (2)
O1—Cu1—N2—C18^i	−56.67 (10)	C4—C5—C6—C7	−1.5 (4)
O1^i—Cu1—N2—C18^i	123.33 (10)	C4—C3—C8—C7	−2.4 (3)
O1—C1—C2—O3	−178.86 (14)	C5—C6—C7—C8	1.9 (4)
O1—C1—C2—C3	−60.39 (18)	C6—C7—C8—C3	0.1 (4)
O1—C1—C2—C9	62.48 (18)	C8—C3—C4—C5	2.8 (3)
O2—C1—C2—O3	0.2 (2)	C9—C2—C3—C4	−48.0 (2)
O2—C1—C2—C3	118.65 (16)	C9—C2—C3—C8	134.54 (17)
O2—C1—C2—C9	−118.48 (16)	C9—C10—C11—C12	0.1 (4)
O3—C2—C3—C8	16.3 (2)	C10—C11—C12—C13	0.9 (4)
O3—C2—C9—C10	56.7 (2)	C10—C9—C14—C13	−0.3 (3)
O3—C2—C3—C4	−166.24 (16)	C11—C12—C13—C14	−1.6 (4)
O3—C2—C9—C14	−119.96 (19)	C12—C13—C14—C9	1.3 (4)
N1—Cu1—O1—C1	−88.85 (13)	C14—C9—C10—C11	−0.4 (3)
N1—C15—C16—C17	0.5 (3)	C15^i—N1—C15—C16	−0.26 (15)
N2—Cu1—O1—C1	91.15 (13)	C15—C16—C17—C16^i	−0.25 (14)
N2—C18—C19—C20	0.8 (3)	C18^i—N2—C18—C19	−0.41 (15)
C1—C2—C3—C8	−100.88 (18)	C18—C19—C20—C19^i	−0.4 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H23···O2	0.82	2.04	2.564 (2)	121
O3—H23···O2^ii	0.82	2.23	2.914 (2)	142
O4—H24···O2^i	0.82	2.04	2.745 (2)	144

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x, y, −z+3/2.