Aqua­(4'-hydr­oxy-2,2';6',6''-terpyrid­yl)copper(II) bis­(perchlorate)

In the title compound, [Cu(C₁₅H₁₁N₃)(H₂O)](ClO₄)₂, the 4'-hydroxy­terpyridine and water mol­ecule are coordinated in the Cu equatorial plane and the two perchlorate ions are semicoordinate in the axial positions. The crystal structure is stabilized by hydrogen bonds between the 4'-hydr­oxy group, the coordinated water mol­ecule and the perchlorate ions, forming two-dimensional sheets.

Key indicators

• Single-crystal X-ray study
• T = 158 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.058
• wR factor = 0.137
• Data-to-parameter ratio = 9.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      24.00 Deg.

Author Response: see _publ_section_exptl_refinement

Alert level B
THETM01_ALERT_3_B  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5723
PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6].....      24.00 Deg.
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Cu     -   O1      ..      10.22 su
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        Cl1

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.5723
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   9.6471
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.65
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.83 Ratio
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C15 H13 Cl2 Cu N3 O10

   1 ALERT level A = In general: serious problem
   5 ALERT level B = Potentially serious problem
   7 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   8 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1992); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1985); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Aqua(4'-hydroxy-2,2',6',6''-terpyridyl)copper(II) perchlorate

Crystal data

[Cu(C15H11N3)(H2O)](ClO4)2	F(000) = 1068
Mr = 529.72	Dx = 1.908 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 17 reflections
a = 8.487 (4) Å	θ = 4.9–12.2°
b = 11.230 (3) Å	µ = 1.54 mm^−1
c = 19.662 (8) Å	T = 158 K
β = 100.19 (3)°	Plate, blue
V = 1844.4 (13) Å^3	0.65 × 0.22 × 0.05 mm
Z = 4

Data collection

Siemens P4 diffractometer	1455 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.058
Graphite monochromator	θmax = 24.0°, θmin = 2.1°
ω scans	h = −9→1
Absorption correction: ψ scan (SHELXTL; Sheldrick, 1985)	k = 0→12
Tmin = 0.634, Tmax = 0.926	l = −20→22
2982 measured reflections	3 standard reflections every 397 reflections
2788 independent reflections	intensity decay: 5.8%

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ^2(Fo^2) + (0.0591P)^2] where P = (Fo^2 + 2Fc^2)/3
2788 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.97 e Å^−3
12 restraints	Δρmin = −0.76 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
Cu	0.16187 (12)	−0.19260 (10)	0.35796 (5)	0.0207 (3)
N1	−0.0418 (8)	−0.2663 (6)	0.3777 (4)	0.0186 (17)
C2	−0.1791 (9)	−0.2830 (7)	0.3328 (4)	0.022 (2)
H2	−0.1860	−0.2554	0.2867	0.026*
C3	−0.3100 (10)	−0.3386 (7)	0.3511 (5)	0.027 (2)
H3	−0.4060	−0.3480	0.3185	0.032*
C4	−0.2991 (10)	−0.3806 (8)	0.4182 (5)	0.025 (2)
H4	−0.3878	−0.4193	0.4320	0.030*
C5	−0.1555 (9)	−0.3654 (7)	0.4653 (5)	0.023 (2)
H5	−0.1448	−0.3933	0.5115	0.028*
C6	−0.0310 (9)	−0.3088 (7)	0.4426 (4)	0.0195 (19)
N7	0.2302 (8)	−0.2323 (5)	0.4533 (3)	0.0161 (16)
C7	0.1279 (9)	−0.2902 (7)	0.4866 (4)	0.0176 (19)
C8	0.1777 (9)	−0.3273 (7)	0.5529 (5)	0.024 (2)
H8	0.1051	−0.3669	0.5769	0.029*
C9	0.3346 (10)	−0.3073 (8)	0.5855 (4)	0.024 (2)
O9	0.3801 (7)	−0.3484 (6)	0.6493 (3)	0.0328 (18)
H9	0.472 (10)	−0.350 (9)	0.665 (5)	0.039*
C10	0.4396 (10)	−0.2496 (8)	0.5486 (4)	0.024 (2)
H10	0.5485	−0.2369	0.5687	0.029*
C11	0.3812 (9)	−0.2122 (7)	0.4833 (4)	0.0174 (19)
C12	0.4695 (9)	−0.1434 (7)	0.4366 (4)	0.018 (2)
C13	0.6207 (9)	−0.0939 (8)	0.4572 (5)	0.025 (2)
H13	0.6758	−0.1036	0.5033	0.030*
C14	0.6899 (10)	−0.0308 (8)	0.4101 (5)	0.026 (2)
H14	0.7939	0.0023	0.4232	0.031*
C15	0.6079 (10)	−0.0163 (8)	0.3445 (5)	0.027 (2)
H15	0.6525	0.0286	0.3116	0.033*
C16	0.4569 (10)	−0.0688 (8)	0.3265 (5)	0.027 (2)
H16	0.4022	−0.0616	0.2802	0.032*
N17	0.3856 (8)	−0.1289 (6)	0.3719 (4)	0.0221 (17)
O10	0.1055 (8)	−0.1677 (6)	0.2590 (3)	0.0287 (17)
H10A	0.113 (11)	−0.222 (8)	0.234 (5)	0.034*
H10B	0.091 (11)	−0.102 (8)	0.242 (5)	0.034*
Cl1	0.0752 (3)	0.1095 (2)	0.35891 (12)	0.0271 (6)
O1	0.0744 (8)	0.0038 (6)	0.3973 (4)	0.059 (2)
O3	0.1609 (8)	0.1992 (7)	0.3996 (4)	0.067 (2)
O5	−0.0827 (7)	0.1521 (6)	0.3350 (3)	0.0465 (19)
O7	0.1533 (10)	0.0880 (7)	0.3005 (4)	0.076 (3)
Cl2	0.2448 (2)	−0.50559 (19)	0.34697 (11)	0.0205 (5)
O2	0.0769 (7)	−0.5214 (5)	0.3457 (3)	0.0265 (15)
O4	0.3287 (7)	−0.5140 (5)	0.4162 (3)	0.0276 (15)
O6	0.3020 (6)	−0.5957 (5)	0.3054 (3)	0.0268 (15)
O8	0.2728 (7)	−0.3911 (5)	0.3186 (3)	0.0280 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0198 (5)	0.0225 (6)	0.0206 (6)	−0.0011 (5)	0.0054 (4)	0.0024 (6)
N1	0.018 (4)	0.009 (4)	0.029 (4)	0.006 (3)	0.005 (3)	0.008 (3)
C2	0.023 (5)	0.019 (5)	0.021 (5)	0.003 (4)	0.000 (4)	0.007 (4)
C3	0.017 (5)	0.015 (5)	0.048 (6)	0.001 (4)	0.004 (4)	−0.007 (5)
C4	0.021 (5)	0.024 (6)	0.032 (6)	−0.009 (4)	0.010 (4)	0.005 (5)
C5	0.024 (5)	0.018 (5)	0.032 (5)	0.002 (4)	0.019 (4)	0.002 (4)
C6	0.027 (4)	0.009 (4)	0.026 (5)	0.005 (4)	0.015 (4)	0.008 (4)
N7	0.021 (4)	0.008 (4)	0.021 (4)	0.001 (3)	0.010 (3)	−0.003 (3)
C7	0.023 (4)	0.009 (5)	0.023 (5)	0.001 (4)	0.011 (4)	0.000 (4)
C8	0.024 (5)	0.015 (5)	0.036 (6)	0.000 (4)	0.009 (4)	−0.002 (4)
C9	0.035 (4)	0.014 (4)	0.022 (4)	0.010 (4)	0.005 (4)	0.005 (4)
O9	0.021 (3)	0.051 (5)	0.026 (4)	0.005 (3)	0.004 (3)	0.006 (3)
C10	0.022 (5)	0.021 (5)	0.029 (6)	0.002 (4)	0.005 (4)	−0.006 (4)
C11	0.013 (4)	0.014 (4)	0.024 (4)	0.009 (3)	0.003 (3)	−0.003 (4)
C12	0.016 (4)	0.018 (5)	0.022 (5)	0.003 (4)	0.009 (4)	0.005 (4)
C13	0.021 (5)	0.024 (5)	0.028 (5)	0.002 (4)	0.000 (4)	−0.002 (5)
C14	0.022 (5)	0.028 (6)	0.029 (6)	−0.007 (4)	0.006 (4)	−0.006 (5)
C15	0.026 (5)	0.021 (5)	0.038 (6)	−0.005 (4)	0.013 (5)	−0.008 (5)
C16	0.032 (5)	0.027 (6)	0.022 (5)	0.002 (5)	0.005 (4)	−0.007 (4)
N17	0.017 (4)	0.020 (4)	0.032 (5)	0.003 (3)	0.011 (4)	0.000 (4)
O10	0.039 (4)	0.020 (4)	0.028 (4)	0.000 (3)	0.008 (3)	0.005 (3)
Cl1	0.0295 (12)	0.0191 (13)	0.0321 (13)	0.0024 (11)	0.0037 (10)	−0.0012 (11)
O1	0.047 (4)	0.047 (5)	0.088 (6)	−0.009 (4)	0.027 (4)	0.033 (5)
O3	0.059 (5)	0.045 (5)	0.084 (6)	−0.017 (4)	−0.023 (4)	0.005 (5)
O5	0.026 (4)	0.058 (5)	0.054 (5)	0.000 (3)	0.002 (3)	0.022 (4)
O7	0.113 (7)	0.055 (5)	0.078 (6)	0.042 (5)	0.063 (6)	0.021 (5)
Cl2	0.0228 (11)	0.0189 (12)	0.0205 (12)	−0.0003 (10)	0.0054 (9)	0.0005 (10)
O2	0.027 (3)	0.017 (4)	0.039 (4)	−0.002 (3)	0.013 (3)	−0.009 (3)
O4	0.031 (3)	0.034 (4)	0.016 (3)	−0.001 (3)	−0.002 (3)	−0.002 (3)
O6	0.029 (3)	0.021 (3)	0.031 (4)	0.004 (3)	0.006 (3)	−0.010 (3)
O8	0.032 (3)	0.025 (4)	0.029 (4)	0.001 (3)	0.010 (3)	0.007 (3)

Geometric parameters (Å, º)

Cu—N7	1.914 (7)	C10—C11	1.359 (11)
Cu—O10	1.940 (7)	C10—H10	0.9500
Cu—N17	2.002 (7)	C11—C12	1.497 (10)
Cu—N1	2.015 (6)	C12—N17	1.354 (10)
N1—C2	1.345 (10)	C12—C13	1.391 (11)
N1—C6	1.349 (10)	C13—C14	1.377 (11)
C2—C3	1.376 (10)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.362 (12)
C3—C4	1.388 (12)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.398 (11)
C4—C5	1.406 (12)	C15—H15	0.9500
C4—H4	0.9500	C16—N17	1.345 (10)
C5—C6	1.373 (10)	C16—H16	0.9500
C5—H5	0.9500	O10—H10A	0.79 (9)
C6—C7	1.483 (11)	O10—H10B	0.80 (9)
N7—C11	1.332 (10)	Cl1—O3	1.406 (7)
N7—C7	1.344 (9)	Cl1—O1	1.407 (7)
C7—C8	1.362 (11)	Cl1—O5	1.423 (6)
C8—C9	1.390 (11)	Cl1—O7	1.444 (7)
C8—H8	0.9500	Cl2—O4	1.423 (6)
C9—O9	1.328 (10)	Cl2—O2	1.432 (6)
C9—C10	1.403 (11)	Cl2—O8	1.438 (6)
O9—H9	0.79 (9)	Cl2—O6	1.438 (6)
N7—Cu—O10	173.7 (3)	C11—C10—H10	120.9
N7—Cu—N17	80.4 (3)	C9—C10—H10	120.9
O10—Cu—N17	98.4 (3)	N7—C11—C10	121.8 (7)
N7—Cu—N1	80.6 (3)	N7—C11—C12	111.3 (7)
O10—Cu—N1	100.7 (3)	C10—C11—C12	126.8 (7)
N17—Cu—N1	161.0 (3)	N17—C12—C13	122.0 (7)
C2—N1—C6	118.5 (7)	N17—C12—C11	113.6 (7)
C2—N1—Cu	127.1 (6)	C13—C12—C11	124.4 (8)
C6—N1—Cu	114.2 (5)	C14—C13—C12	119.5 (8)
N1—C2—C3	122.5 (8)	C14—C13—H13	120.3
N1—C2—H2	118.7	C12—C13—H13	120.3
C3—C2—H2	118.7	C15—C14—C13	119.4 (8)
C2—C3—C4	118.8 (8)	C15—C14—H14	120.3
C2—C3—H3	120.6	C13—C14—H14	120.3
C4—C3—H3	120.6	C14—C15—C16	118.8 (9)
C3—C4—C5	119.3 (7)	C14—C15—H15	120.6
C3—C4—H4	120.4	C16—C15—H15	120.6
C5—C4—H4	120.4	N17—C16—C15	122.9 (8)
C6—C5—C4	118.0 (8)	N17—C16—H16	118.6
C6—C5—H5	121.0	C15—C16—H16	118.6
C4—C5—H5	121.0	C16—N17—C12	117.4 (7)
N1—C6—C5	122.9 (8)	C16—N17—Cu	128.0 (6)
N1—C6—C7	113.9 (7)	C12—N17—Cu	114.5 (5)
C5—C6—C7	123.2 (7)	Cu—O10—H10A	118 (7)
C11—N7—C7	121.3 (7)	Cu—O10—H10B	122 (7)
C11—N7—Cu	119.7 (5)	H10A—O10—H10B	119 (9)
C7—N7—Cu	118.7 (5)	O3—Cl1—O1	110.5 (5)
N7—C7—C8	119.8 (8)	O3—Cl1—O5	108.0 (4)
N7—C7—C6	112.5 (7)	O1—Cl1—O5	111.5 (4)
C8—C7—C6	127.7 (7)	O3—Cl1—O7	107.9 (5)
C7—C8—C9	120.1 (8)	O1—Cl1—O7	109.4 (5)
C7—C8—H8	120.0	O5—Cl1—O7	109.4 (5)
C9—C8—H8	120.0	O4—Cl2—O2	109.7 (4)
O9—C9—C8	118.3 (8)	O4—Cl2—O8	110.0 (4)
O9—C9—C10	122.9 (8)	O2—Cl2—O8	109.7 (4)
C8—C9—C10	118.7 (8)	O4—Cl2—O6	109.6 (4)
C9—O9—H9	118 (7)	O2—Cl2—O6	109.7 (3)
C11—C10—C9	118.2 (8)	O8—Cl2—O6	108.2 (3)
N7—Cu—N1—C2	−178.0 (7)	C7—C8—C9—O9	−177.7 (8)
O10—Cu—N1—C2	−4.3 (7)	C7—C8—C9—C10	−0.6 (13)
N17—Cu—N1—C2	177.4 (7)	O9—C9—C10—C11	179.2 (8)
N7—Cu—N1—C6	−2.2 (6)	C8—C9—C10—C11	2.2 (12)
O10—Cu—N1—C6	171.6 (6)	C7—N7—C11—C10	0.4 (11)
N17—Cu—N1—C6	−6.7 (12)	Cu—N7—C11—C10	−173.3 (6)
C6—N1—C2—C3	1.8 (12)	C7—N7—C11—C12	−178.3 (7)
Cu—N1—C2—C3	177.5 (6)	Cu—N7—C11—C12	7.9 (8)
N1—C2—C3—C4	−1.0 (13)	C9—C10—C11—N7	−2.2 (12)
C2—C3—C4—C5	0.0 (13)	C9—C10—C11—C12	176.4 (8)
C3—C4—C5—C6	0.0 (12)	N7—C11—C12—N17	−7.6 (10)
C2—N1—C6—C5	−1.8 (12)	C10—C11—C12—N17	173.7 (8)
Cu—N1—C6—C5	−178.0 (6)	N7—C11—C12—C13	169.9 (8)
C2—N1—C6—C7	177.4 (7)	C10—C11—C12—C13	−8.8 (13)
Cu—N1—C6—C7	1.2 (9)	N17—C12—C13—C14	−1.7 (13)
C4—C5—C6—N1	0.9 (13)	C11—C12—C13—C14	−179.1 (8)
C4—C5—C6—C7	−178.2 (8)	C12—C13—C14—C15	1.1 (13)
N17—Cu—N7—C11	−4.7 (6)	C13—C14—C15—C16	−1.6 (13)
N1—Cu—N7—C11	176.9 (6)	C14—C15—C16—N17	2.9 (13)
N17—Cu—N7—C7	−178.6 (6)	C15—C16—N17—C12	−3.5 (12)
N1—Cu—N7—C7	2.9 (6)	C15—C16—N17—Cu	172.2 (6)
C11—N7—C7—C8	1.3 (11)	C13—C12—N17—C16	2.9 (12)
Cu—N7—C7—C8	175.1 (6)	C11—C12—N17—C16	−179.5 (7)
C11—N7—C7—C6	−176.9 (7)	C13—C12—N17—Cu	−173.4 (6)
Cu—N7—C7—C6	−3.0 (9)	C11—C12—N17—Cu	4.2 (8)
N1—C6—C7—N7	1.1 (10)	N7—Cu—N17—C16	−176.0 (7)
C5—C6—C7—N7	−179.8 (7)	O10—Cu—N17—C16	10.3 (7)
N1—C6—C7—C8	−176.9 (8)	N1—Cu—N17—C16	−171.4 (7)
C5—C6—C7—C8	2.3 (13)	N7—Cu—N17—C12	−0.2 (6)
N7—C7—C8—C9	−1.1 (12)	O10—Cu—N17—C12	−173.9 (6)
C6—C7—C8—C9	176.7 (8)	N1—Cu—N17—C12	4.4 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9···O6^i	0.79 (9)	2.00 (9)	2.760 (8)	163 (10)
O10—H10A···O5^ii	0.79 (9)	1.95 (9)	2.725 (9)	167 (10)
O10—H10B···O7	0.80 (9)	2.44 (9)	2.993 (10)	127 (8)
O10—H10B···O2^iii	0.80 (9)	2.23 (9)	2.864 (9)	136 (9)

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