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Di-2-pyridyl ketone reacts with copper(II) nitrate and sodium adamantane-1-carboxyl­ate in aceto­nitrile–water to form bis­[bis(2-pyridyl)­methanediol]copper(II) bis­(adamantane-1-carboxyl­ate), [Cu(C11H10N2O2)2](C11H15O2)2. The Cu atom in this dicationic complex occupies a special position at an inversion centre and has a tetragonally distorted octahedral coordination, formed by four `normal' Cu—N [2.0114 (16) and 2.0155 (16) Å] and two `long' Cu—O bonds [2.3690 (14) Å]. The methanediol hydroxyl groups are hydrogen-bonded to the adamantane-1-carboxyl­ate anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009237/ya6199sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009237/ya6199Isup2.hkl
Contains datablock I

CCDC reference: 239082

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.112
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 27.00 From the CIF: _reflns_number_total 4078 From the CIF: _diffrn_reflns_limit_ max hkl 29. 11. 19. From the CIF: _diffrn_reflns_limit_ min hkl -26. -14. -19. TEST1: Expected hkl limits for theta max Calculated maximum hkl 31. 14. 19. Calculated minimum hkl -31. -14. -19.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Bis[bis(2-pyridyl)methanediol-κ3N,N',O]copper(II) bis(adamantane-1-carboxylate) top
Crystal data top
[Cu(C11H10N2O2)2](C11H15O2)2F(000) = 1740
Mr = 826.42Dx = 1.413 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 24.947 (5) ÅCell parameters from 9994 reflections
b = 11.5988 (17) Åθ = 3.0–27.0°
c = 15.284 (3) ŵ = 0.62 mm1
β = 118.576 (3)°T = 293 K
V = 3883.8 (11) Å3Block, blue
Z = 40.38 × 0.32 × 0.30 mm
Data collection top
Rigaku Mercury CCD area-detector
diffractometer
4078 independent reflections
Radiation source: rotating-anode generator3389 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
ω scansθmax = 27.0°, θmin = 3.0°
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2002)
h = 2629
Tmin = 0.789, Tmax = 0.829k = 1411
9994 measured reflectionsl = 1919
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.053P)2]
where P = (Fo2 + 2Fc2)/3
4078 reflections(Δ/σ)max < 0.001
267 parametersΔρmax = 0.45 e Å3
2 restraintsΔρmin = 0.39 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
Cu10.00000.50000.00000.01953 (13)
O10.05699 (6)0.35312 (12)0.02569 (11)0.0221 (3)
H10.0803 (10)0.320 (2)0.0286 (12)0.057 (9)*
O20.02137 (7)0.17372 (12)0.10132 (11)0.0250 (3)
H20.0517 (9)0.143 (2)0.0521 (15)0.060 (9)*
O30.12284 (7)0.25115 (12)0.13899 (11)0.0348 (4)
O40.11084 (8)0.08570 (13)0.05863 (12)0.0398 (4)
N10.05219 (7)0.44792 (14)0.14190 (12)0.0200 (4)
N20.02517 (7)0.35479 (14)0.04258 (12)0.0201 (4)
C10.09584 (10)0.51072 (17)0.21536 (16)0.0229 (5)
H1A0.10340.58530.20160.027*
C20.12955 (10)0.4680 (2)0.30983 (16)0.0272 (5)
H2A0.16000.51260.35910.033*
C30.11786 (10)0.35782 (19)0.33132 (16)0.0277 (5)
H3A0.13970.32820.39540.033*
C40.07314 (9)0.29246 (18)0.25574 (15)0.0239 (5)
H4A0.06470.21790.26800.029*
C50.04150 (9)0.33997 (17)0.16237 (15)0.0204 (4)
C60.00710 (9)0.27666 (17)0.07176 (15)0.0201 (4)
C70.01956 (9)0.25758 (17)0.00043 (14)0.0194 (4)
C80.03840 (9)0.15242 (18)0.01637 (16)0.0263 (5)
H8A0.03550.08640.01570.032*
C90.06184 (11)0.1473 (2)0.08244 (18)0.0346 (6)
H9A0.07450.07710.09580.041*
C100.06630 (11)0.2465 (2)0.12818 (18)0.0336 (6)
H10A0.08150.24420.17310.040*
C110.04776 (10)0.34887 (19)0.10597 (16)0.0268 (5)
H11A0.05110.41620.13610.032*
C120.13414 (9)0.14572 (18)0.13606 (16)0.0237 (5)
C130.17830 (9)0.08766 (17)0.23438 (15)0.0221 (4)
C140.14054 (10)0.00991 (17)0.26649 (17)0.0257 (5)
H14A0.11100.05640.27500.031*
H14B0.11840.04680.21510.031*
C150.18263 (10)0.0513 (2)0.36438 (17)0.0329 (5)
H15A0.15820.09980.38430.040*
C160.21781 (11)0.0369 (2)0.44579 (17)0.0351 (5)
H16A0.24400.00250.50770.042*
H16B0.18950.08460.45630.042*
C170.25661 (10)0.1128 (2)0.41527 (17)0.0303 (5)
H17A0.27920.16970.46750.036*
C180.21442 (10)0.17452 (18)0.31777 (16)0.0283 (5)
H18A0.23850.22330.29830.034*
H18B0.18620.22340.32780.034*
C190.22395 (10)0.01053 (17)0.21990 (17)0.0270 (5)
H19A0.20180.04580.16800.032*
H19B0.24810.05750.19930.032*
C200.26603 (10)0.0515 (2)0.31735 (18)0.0319 (5)
H20A0.29470.10030.30730.038*
C210.22771 (11)0.1267 (2)0.34903 (19)0.0383 (6)
H21A0.20560.18390.29810.046*
H21B0.25430.16670.41050.046*
C220.30169 (10)0.0368 (2)0.39906 (18)0.0342 (5)
H22A0.32630.08440.37980.041*
H22B0.32880.00270.46050.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0236 (2)0.0161 (2)0.0155 (2)0.00254 (13)0.00667 (16)0.00004 (13)
O10.0213 (7)0.0212 (8)0.0204 (8)0.0013 (6)0.0072 (6)0.0020 (6)
O20.0303 (8)0.0210 (8)0.0216 (8)0.0043 (6)0.0108 (7)0.0017 (6)
O30.0372 (9)0.0190 (8)0.0284 (9)0.0044 (7)0.0003 (7)0.0010 (7)
O40.0505 (10)0.0255 (9)0.0238 (9)0.0092 (8)0.0019 (8)0.0025 (7)
N10.0218 (9)0.0188 (9)0.0167 (9)0.0015 (7)0.0072 (7)0.0015 (7)
N20.0227 (9)0.0204 (9)0.0151 (8)0.0014 (7)0.0073 (7)0.0011 (7)
C10.0227 (11)0.0229 (11)0.0215 (11)0.0012 (8)0.0093 (9)0.0036 (8)
C20.0223 (11)0.0341 (12)0.0196 (11)0.0007 (9)0.0054 (9)0.0068 (10)
C30.0283 (11)0.0332 (13)0.0175 (11)0.0059 (10)0.0078 (9)0.0020 (9)
C40.0281 (11)0.0234 (11)0.0213 (11)0.0013 (9)0.0125 (9)0.0021 (9)
C50.0235 (10)0.0192 (10)0.0195 (11)0.0020 (8)0.0110 (9)0.0017 (8)
C60.0236 (10)0.0174 (10)0.0185 (11)0.0005 (8)0.0094 (9)0.0002 (8)
C70.0175 (10)0.0194 (10)0.0168 (10)0.0018 (8)0.0046 (8)0.0003 (8)
C80.0298 (12)0.0208 (11)0.0296 (12)0.0031 (9)0.0153 (10)0.0012 (9)
C90.0427 (14)0.0261 (12)0.0420 (15)0.0086 (11)0.0259 (12)0.0027 (11)
C100.0402 (14)0.0351 (14)0.0377 (14)0.0070 (11)0.0285 (12)0.0018 (11)
C110.0294 (11)0.0284 (12)0.0268 (12)0.0018 (10)0.0167 (10)0.0023 (9)
C120.0215 (10)0.0225 (11)0.0252 (12)0.0010 (9)0.0096 (9)0.0021 (9)
C130.0216 (10)0.0191 (10)0.0225 (11)0.0013 (8)0.0081 (9)0.0005 (8)
C140.0221 (11)0.0270 (12)0.0257 (12)0.0011 (8)0.0095 (10)0.0007 (9)
C150.0327 (13)0.0346 (14)0.0276 (13)0.0050 (10)0.0113 (10)0.0060 (10)
C160.0306 (12)0.0492 (15)0.0193 (12)0.0041 (11)0.0069 (10)0.0004 (11)
C170.0267 (12)0.0330 (13)0.0229 (12)0.0011 (10)0.0051 (9)0.0058 (10)
C180.0262 (11)0.0242 (12)0.0286 (12)0.0000 (9)0.0083 (10)0.0044 (9)
C190.0260 (12)0.0271 (12)0.0275 (13)0.0057 (9)0.0124 (10)0.0002 (9)
C200.0266 (11)0.0294 (13)0.0355 (14)0.0123 (10)0.0116 (10)0.0015 (10)
C210.0383 (14)0.0293 (13)0.0343 (14)0.0050 (11)0.0069 (11)0.0074 (11)
C220.0221 (11)0.0411 (14)0.0314 (13)0.0034 (11)0.0063 (10)0.0041 (11)
Geometric parameters (Å, º) top
Cu1—N2i2.0114 (16)C10—C111.375 (3)
Cu1—N22.0114 (16)C10—H10A0.9300
Cu1—N12.0155 (16)C11—H11A0.9300
Cu1—N1i2.0155 (17)C12—C131.530 (3)
Cu1—O1i2.3690 (14)C13—C181.534 (3)
Cu1—O12.3690 (14)C13—C141.544 (3)
O1—C61.412 (2)C13—C191.545 (3)
O1—H10.845 (10)C14—C151.530 (3)
O2—C61.382 (2)C14—H14A0.9700
O2—H20.848 (10)C14—H14B0.9700
O3—C121.261 (2)C15—C161.523 (3)
O4—C121.251 (3)C15—C211.529 (3)
N1—C11.344 (3)C15—H15A0.9800
N1—C51.348 (3)C16—C171.537 (3)
N2—C111.335 (3)C16—H16A0.9700
N2—C71.346 (3)C16—H16B0.9700
C1—C21.370 (3)C17—C181.530 (3)
C1—H1A0.9300C17—C221.540 (3)
C2—C31.385 (3)C17—H17A0.9800
C2—H2A0.9300C18—H18A0.9700
C3—C41.386 (3)C18—H18B0.9700
C3—H3A0.9300C19—C201.530 (3)
C4—C51.373 (3)C19—H19A0.9700
C4—H4A0.9300C19—H19B0.9700
C5—C61.523 (3)C20—C221.528 (3)
C6—C71.541 (3)C20—C211.534 (3)
C7—C81.375 (3)C20—H20A0.9800
C8—C91.389 (3)C21—H21A0.9700
C8—H8A0.9300C21—H21B0.9700
C9—C101.378 (3)C22—H22A0.9700
C9—H9A0.9300C22—H22B0.9700
N2i—Cu1—N2180.00 (9)O4—C12—C13118.33 (18)
N2i—Cu1—N192.51 (7)O3—C12—C13117.40 (18)
N2—Cu1—N187.49 (7)C12—C13—C18112.82 (17)
N2i—Cu1—N1i87.49 (7)C12—C13—C14107.88 (16)
N2—Cu1—N1i92.51 (7)C18—C13—C14108.95 (17)
N1—Cu1—N1i180.00 (7)C12—C13—C19110.36 (17)
N2i—Cu1—O1i75.91 (6)C18—C13—C19108.61 (17)
N2—Cu1—O1i104.09 (6)C14—C13—C19108.11 (17)
N1—Cu1—O1i105.30 (6)C15—C14—C13110.13 (17)
N1i—Cu1—O1i74.70 (6)C15—C14—H14A109.6
N2i—Cu1—O1104.09 (6)C13—C14—H14A109.6
N2—Cu1—O175.91 (6)C15—C14—H14B109.6
N1—Cu1—O174.70 (6)C13—C14—H14B109.6
N1i—Cu1—O1105.30 (6)H14A—C14—H14B108.1
O1i—Cu1—O1180.00 (6)C16—C15—C21109.31 (19)
C6—O1—Cu194.51 (10)C16—C15—C14110.2 (2)
C6—O1—H1103.4 (19)C21—C15—C14109.05 (19)
Cu1—O1—H1110.6 (19)C16—C15—H15A109.4
C6—O2—H2109 (2)C21—C15—H15A109.4
C1—N1—C5118.72 (17)C14—C15—H15A109.4
C1—N1—Cu1125.78 (14)C15—C16—C17109.72 (19)
C5—N1—Cu1115.50 (13)C15—C16—H16A109.7
C11—N2—C7119.33 (17)C17—C16—H16A109.7
C11—N2—Cu1125.68 (14)C15—C16—H16B109.7
C7—N2—Cu1114.96 (13)C17—C16—H16B109.7
N1—C1—C2121.9 (2)H16A—C16—H16B108.2
N1—C1—H1A119.1C18—C17—C16108.91 (17)
C2—C1—H1A119.1C18—C17—C22109.05 (18)
C1—C2—C3119.4 (2)C16—C17—C22109.6 (2)
C1—C2—H2A120.3C18—C17—H17A109.8
C3—C2—H2A120.3C16—C17—H17A109.8
C2—C3—C4118.9 (2)C22—C17—H17A109.8
C2—C3—H3A120.5C17—C18—C13111.05 (17)
C4—C3—H3A120.5C17—C18—H18A109.4
C5—C4—C3118.7 (2)C13—C18—H18A109.4
C5—C4—H4A120.7C17—C18—H18B109.4
C3—C4—H4A120.7C13—C18—H18B109.4
N1—C5—C4122.34 (18)H18A—C18—H18B108.0
N1—C5—C6113.36 (17)C20—C19—C13110.00 (18)
C4—C5—C6124.27 (18)C20—C19—H19A109.7
O2—C6—O1113.72 (16)C13—C19—H19A109.7
O2—C6—C5109.67 (16)C20—C19—H19B109.7
O1—C6—C5106.20 (15)C13—C19—H19B109.7
O2—C6—C7111.91 (16)H19A—C19—H19B108.2
O1—C6—C7108.26 (15)C22—C20—C19109.95 (19)
C5—C6—C7106.70 (15)C22—C20—C21109.3 (2)
N2—C7—C8121.83 (19)C19—C20—C21109.48 (18)
N2—C7—C6113.97 (16)C22—C20—H20A109.4
C8—C7—C6124.16 (18)C19—C20—H20A109.4
C7—C8—C9118.3 (2)C21—C20—H20A109.4
C7—C8—H8A120.8C15—C21—C20109.8 (2)
C9—C8—H8A120.8C15—C21—H21A109.7
C10—C9—C8119.8 (2)C20—C21—H21A109.7
C10—C9—H9A120.1C15—C21—H21B109.7
C8—C9—H9A120.1C20—C21—H21B109.7
C11—C10—C9118.5 (2)H21A—C21—H21B108.2
C11—C10—H10A120.7C20—C22—C17109.31 (18)
C9—C10—H10A120.7C20—C22—H22A109.8
N2—C11—C10122.1 (2)C17—C22—H22A109.8
N2—C11—H11A118.9C20—C22—H22B109.8
C10—C11—H11A118.9C17—C22—H22B109.8
O4—C12—O3124.26 (19)H22A—C22—H22B108.3
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.85 (1)1.70 (1)2.545 (2)176 (3)
O2—H2···O40.85 (1)1.76 (1)2.604 (2)173 (3)
 

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