Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033752/hb2477sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033752/hb2477Isup2.hkl |
CCDC reference: 657585
Cobalt diacetate tetrahydrate (1 mmol), 1,3-adamantanedicarboxylic acid (1 mmol) and 1,10-phenanthroline (2 mmol) were dissolved in ethanol (50 ml). The solution was set aside for the growth of the yellow plates of (I), which were isolated after a week.
The carbon-bound H atoms were positioned geometrically (C–H = 0.93–0.97 Å), and refined as riding with Uiso(H) = 1.2Ueq(C). The H atoms of water were placed (O—H = 0.85 Å) to generate a chemically plausible hydrogen bonding scheme and refined as riding with Uiso(H) = 1.2Ueq(O). In the resulting scheme, which should be regarded as tentative, the O4w water molecule forms only one hydrogen bond.
The crystal structures of an enormous number of metal(II) dicarboxylates have been reported (CSD Version 5.28, May 2007; Allen, 2002). However, there is no example of a metal 1,3-adamantanedicarboxylate; the crystal structure of the dicarboxylic acid itself has been known for some time (Glidewell & Ferguson, 1996).
The cobalt(II) atom in the title compound, (I), (Fig. 1), is chelated by two N-heterocycles; it is also linked datively to a water molecule and covalently to a single O atom of the dicarboxylate dianion in an all-cis octahedral geometry (Table 1). The mononuclear complex exists as as a zwitterion (i.e. formal Co+ and free –CO2- carboxyate anion in the same molecule). The component species of (I) are linked into a chain by ay of O—H···O interactions (Table 2).
There are no examples of metal derivatives of this dicarboxylic acid according to the Cambridge Structural Database (Version 5.28; May 2007; Allen, 2002). For the structure of the free acid, see: Glidewell & Ferguson (1996).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).
Fig. 1. View of the molecular structure of (I); displacement ellipsoids are drawn at the 50% probabilty level and hydrogen atoms as spheres of arbitrary radius. |
[Co(C12H14O4)(C12H8N2)2(H2O)]·4H2O | Z = 2 |
Mr = 731.65 | F(000) = 766 |
Triclinic, P1 | Dx = 1.429 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9902 (2) Å | Cell parameters from 7731 reflections |
b = 13.2497 (2) Å | θ = 2.5–27.4° |
c = 15.6671 (2) Å | µ = 0.57 mm−1 |
α = 69.277 (1)° | T = 295 K |
β = 77.067 (1)° | Plate, yellow |
γ = 87.328 (1)° | 0.39 × 0.31 × 0.09 mm |
V = 1700.12 (5) Å3 |
Bruker APEX II CCD diffractometer | 7692 independent reflections |
Radiation source: fine-focus sealed tube | 6662 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 27.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.813, Tmax = 0.951 | k = −17→17 |
29003 measured reflections | l = −20→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0966P)2 + 1.4193P] where P = (Fo2 + 2Fc2)/3 |
7692 reflections | (Δ/σ)max = 0.001 |
451 parameters | Δρmax = 0.70 e Å−3 |
24 restraints | Δρmin = −0.77 e Å−3 |
[Co(C12H14O4)(C12H8N2)2(H2O)]·4H2O | γ = 87.328 (1)° |
Mr = 731.65 | V = 1700.12 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.9902 (2) Å | Mo Kα radiation |
b = 13.2497 (2) Å | µ = 0.57 mm−1 |
c = 15.6671 (2) Å | T = 295 K |
α = 69.277 (1)° | 0.39 × 0.31 × 0.09 mm |
β = 77.067 (1)° |
Bruker APEX II CCD diffractometer | 7692 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 6662 reflections with I > 2σ(I) |
Tmin = 0.813, Tmax = 0.951 | Rint = 0.022 |
29003 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 24 restraints |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.70 e Å−3 |
7692 reflections | Δρmin = −0.77 e Å−3 |
451 parameters |
x | y | z | Uiso*/Ueq | ||
Co1 | 0.77668 (4) | 0.73276 (3) | 0.75869 (2) | 0.03448 (13) | |
O1 | 0.6078 (2) | 0.83204 (14) | 0.80147 (12) | 0.0363 (4) | |
O2 | 0.4719 (3) | 0.8737 (2) | 0.69354 (19) | 0.0733 (9) | |
O3 | 0.1345 (3) | 1.27607 (18) | 0.67492 (17) | 0.0592 (6) | |
O4 | 0.3830 (2) | 1.29932 (16) | 0.61730 (14) | 0.0505 (5) | |
O1w | 0.6634 (3) | 0.73629 (19) | 0.65170 (16) | 0.0555 (6) | |
H1w1 | 0.5867 | 0.7761 | 0.6530 | 0.083* | |
H1w2 | 0.6335 | 0.6725 | 0.6609 | 0.083* | |
O2w | 0.6797 (4) | 0.6062 (2) | 0.55445 (16) | 0.0676 (7) | |
H2w1 | 0.6602 | 0.6391 | 0.5006 | 0.101* | |
H2w2 | 0.7708 | 0.5826 | 0.5469 | 0.101* | |
O3w | 0.6600 (3) | 0.3795 (2) | 0.6404 (2) | 0.0763 (8) | |
H3w1 | 0.5898 | 0.3520 | 0.6253 | 0.114* | |
H3w2 | 0.7455 | 0.3718 | 0.6058 | 0.114* | |
O4w | 0.9756 (4) | 0.3754 (3) | 0.5430 (2) | 0.1015 (11) | |
H4w1 | 1.0274 | 0.3433 | 0.5838 | 0.152* | |
H4w2 | 0.9818 | 0.3394 | 0.5057 | 0.152* | |
O5w | 0.8633 (4) | 0.3016 (4) | 0.7950 (3) | 0.1137 (13) | |
H5w1 | 0.9500 | 0.2925 | 0.7622 | 0.171* | |
H5w2 | 0.8028 | 0.3231 | 0.7571 | 0.171* | |
N1 | 0.9384 (2) | 0.87944 (17) | 0.67661 (14) | 0.0344 (4) | |
N2 | 0.9945 (2) | 0.67309 (17) | 0.68646 (14) | 0.0340 (4) | |
N3 | 0.6912 (2) | 0.55917 (16) | 0.84887 (14) | 0.0309 (4) | |
N4 | 0.8511 (2) | 0.68960 (15) | 0.89783 (13) | 0.0273 (4) | |
C1 | 0.9074 (4) | 0.9812 (2) | 0.6682 (2) | 0.0433 (6) | |
H1 | 0.8163 | 0.9948 | 0.7036 | 0.052* | |
C2 | 1.0050 (4) | 1.0683 (2) | 0.6089 (2) | 0.0517 (7) | |
H2 | 0.9787 | 1.1384 | 0.6045 | 0.062* | |
C3 | 1.1392 (4) | 1.0497 (3) | 0.5574 (2) | 0.0532 (8) | |
H3 | 1.2055 | 1.1072 | 0.5175 | 0.064* | |
C4 | 1.1780 (3) | 0.9432 (2) | 0.56434 (18) | 0.0434 (6) | |
C5 | 1.3174 (3) | 0.9163 (3) | 0.5126 (2) | 0.0559 (9) | |
H5 | 1.3870 | 0.9712 | 0.4717 | 0.067* | |
C6 | 1.3490 (3) | 0.8135 (3) | 0.5221 (2) | 0.0554 (8) | |
H6 | 1.4412 | 0.7983 | 0.4887 | 0.066* | |
C7 | 1.2439 (3) | 0.7268 (3) | 0.58235 (18) | 0.0450 (6) | |
C8 | 1.2697 (4) | 0.6184 (3) | 0.5932 (2) | 0.0544 (8) | |
H8 | 1.3625 | 0.5992 | 0.5637 | 0.065* | |
C9 | 1.1598 (4) | 0.5413 (3) | 0.6466 (2) | 0.0520 (7) | |
H9 | 1.1757 | 0.4693 | 0.6534 | 0.062* | |
C10 | 1.0223 (3) | 0.5719 (2) | 0.69122 (19) | 0.0413 (6) | |
H10 | 0.9463 | 0.5189 | 0.7261 | 0.050* | |
C11 | 1.1034 (3) | 0.7501 (2) | 0.63264 (16) | 0.0341 (5) | |
C12 | 1.0721 (3) | 0.8606 (2) | 0.62498 (16) | 0.0342 (5) | |
C13 | 0.6101 (3) | 0.4955 (2) | 0.8254 (2) | 0.0394 (5) | |
H13 | 0.5920 | 0.5200 | 0.7654 | 0.047* | |
C14 | 0.5510 (3) | 0.3934 (2) | 0.8872 (2) | 0.0452 (6) | |
H14 | 0.4945 | 0.3517 | 0.8682 | 0.054* | |
C15 | 0.5765 (3) | 0.3556 (2) | 0.9748 (2) | 0.0412 (6) | |
H15 | 0.5365 | 0.2883 | 1.0165 | 0.049* | |
C16 | 0.6643 (3) | 0.41909 (18) | 1.00232 (18) | 0.0333 (5) | |
C17 | 0.6976 (3) | 0.3850 (2) | 1.09303 (19) | 0.0409 (6) | |
H17 | 0.6602 | 0.3181 | 1.1368 | 0.049* | |
C18 | 0.7823 (3) | 0.4483 (2) | 1.11631 (18) | 0.0400 (6) | |
H18 | 0.8045 | 0.4237 | 1.1753 | 0.048* | |
C19 | 0.8386 (3) | 0.55296 (19) | 1.05137 (16) | 0.0310 (5) | |
C20 | 0.9240 (3) | 0.6234 (2) | 1.07304 (18) | 0.0371 (5) | |
H20 | 0.9488 | 0.6020 | 1.1313 | 0.045* | |
C21 | 0.9700 (3) | 0.7228 (2) | 1.00833 (19) | 0.0380 (5) | |
H21 | 1.0273 | 0.7698 | 1.0216 | 0.046* | |
C22 | 0.9300 (3) | 0.75346 (19) | 0.92164 (18) | 0.0342 (5) | |
H22 | 0.9604 | 0.8221 | 0.8785 | 0.041* | |
C23 | 0.8062 (2) | 0.58983 (17) | 0.96187 (15) | 0.0260 (4) | |
C24 | 0.7189 (2) | 0.52079 (17) | 0.93618 (16) | 0.0278 (4) | |
C25 | 0.5087 (3) | 0.88646 (18) | 0.76021 (16) | 0.0290 (4) | |
C26 | 0.4244 (2) | 0.96943 (17) | 0.79885 (15) | 0.0249 (4) | |
C27 | 0.2706 (3) | 0.91488 (18) | 0.86213 (18) | 0.0342 (5) | |
H27A | 0.2136 | 0.8921 | 0.8260 | 0.041* | |
H27B | 0.2895 | 0.8513 | 0.9127 | 0.041* | |
C28 | 0.1772 (3) | 0.99344 (19) | 0.90258 (17) | 0.0347 (5) | |
H28A | 0.0802 | 0.9578 | 0.9426 | 0.042* | |
C29 | 0.1454 (3) | 1.09256 (19) | 0.82272 (17) | 0.0321 (5) | |
H29A | 0.0854 | 1.1423 | 0.8482 | 0.039* | |
H29B | 0.0871 | 1.0707 | 0.7866 | 0.039* | |
C30 | 0.2957 (2) | 1.14894 (17) | 0.75907 (15) | 0.0262 (4) | |
C31 | 0.3852 (3) | 1.18280 (18) | 0.81816 (16) | 0.0303 (5) | |
H31A | 0.4809 | 1.2190 | 0.7789 | 0.036* | |
H31B | 0.3265 | 1.2329 | 0.8437 | 0.036* | |
C32 | 0.4172 (3) | 1.0835 (2) | 0.89789 (16) | 0.0320 (5) | |
H32A | 0.4746 | 1.1062 | 0.9348 | 0.038* | |
C33 | 0.5125 (3) | 1.00539 (19) | 0.85689 (16) | 0.0300 (5) | |
H33A | 0.6087 | 1.0408 | 0.8177 | 0.036* | |
H33B | 0.5347 | 0.9428 | 0.9072 | 0.036* | |
C34 | 0.2674 (3) | 1.0273 (2) | 0.96088 (17) | 0.0397 (6) | |
H34A | 0.2082 | 1.0759 | 0.9882 | 0.048* | |
H34B | 0.2880 | 0.9642 | 1.0113 | 0.048* | |
C35 | 0.3915 (2) | 1.06957 (17) | 0.71942 (15) | 0.0259 (4) | |
H35A | 0.3368 | 1.0477 | 0.6817 | 0.031* | |
H35B | 0.4872 | 1.1052 | 0.6795 | 0.031* | |
C36 | 0.2686 (3) | 1.24950 (19) | 0.67744 (17) | 0.0344 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0349 (2) | 0.0314 (2) | 0.0364 (2) | 0.00510 (14) | −0.00779 (14) | −0.01162 (14) |
O1 | 0.0384 (9) | 0.0373 (9) | 0.0373 (9) | 0.0179 (7) | −0.0151 (7) | −0.0164 (7) |
O2 | 0.1009 (19) | 0.0826 (17) | 0.0847 (17) | 0.0644 (16) | −0.0679 (16) | −0.0664 (15) |
O3 | 0.0485 (12) | 0.0522 (12) | 0.0643 (14) | 0.0218 (10) | −0.0229 (11) | −0.0017 (10) |
O4 | 0.0548 (12) | 0.0409 (10) | 0.0415 (11) | 0.0051 (9) | −0.0130 (9) | 0.0037 (8) |
O1w | 0.0627 (13) | 0.0641 (14) | 0.0657 (14) | 0.0315 (11) | −0.0372 (11) | −0.0439 (12) |
O2w | 0.114 (2) | 0.0533 (13) | 0.0486 (12) | 0.0234 (13) | −0.0352 (13) | −0.0253 (11) |
O3w | 0.0752 (17) | 0.0716 (17) | 0.0724 (17) | −0.0151 (14) | −0.0187 (14) | −0.0103 (13) |
O4w | 0.085 (2) | 0.138 (3) | 0.086 (2) | 0.031 (2) | −0.0518 (18) | −0.029 (2) |
O5w | 0.092 (2) | 0.147 (3) | 0.102 (3) | 0.049 (2) | −0.014 (2) | −0.054 (2) |
N1 | 0.0387 (11) | 0.0315 (10) | 0.0309 (10) | 0.0000 (8) | −0.0064 (8) | −0.0091 (8) |
N2 | 0.0368 (10) | 0.0351 (10) | 0.0297 (10) | 0.0074 (8) | −0.0076 (8) | −0.0117 (8) |
N3 | 0.0287 (9) | 0.0299 (9) | 0.0362 (10) | 0.0006 (7) | −0.0074 (8) | −0.0142 (8) |
N4 | 0.0239 (8) | 0.0238 (8) | 0.0323 (9) | 0.0004 (7) | −0.0041 (7) | −0.0086 (7) |
C1 | 0.0518 (15) | 0.0335 (13) | 0.0440 (14) | 0.0004 (11) | −0.0118 (12) | −0.0122 (11) |
C2 | 0.072 (2) | 0.0324 (13) | 0.0526 (17) | −0.0076 (13) | −0.0249 (16) | −0.0089 (12) |
C3 | 0.0631 (19) | 0.0504 (16) | 0.0394 (15) | −0.0260 (14) | −0.0178 (14) | −0.0004 (12) |
C4 | 0.0434 (14) | 0.0561 (16) | 0.0275 (12) | −0.0148 (12) | −0.0114 (10) | −0.0067 (11) |
C5 | 0.0390 (14) | 0.088 (3) | 0.0316 (13) | −0.0221 (15) | −0.0024 (11) | −0.0101 (14) |
C6 | 0.0347 (14) | 0.093 (3) | 0.0340 (14) | −0.0021 (15) | −0.0008 (11) | −0.0203 (15) |
C7 | 0.0339 (12) | 0.0724 (19) | 0.0304 (12) | 0.0074 (12) | −0.0069 (10) | −0.0211 (13) |
C8 | 0.0452 (15) | 0.081 (2) | 0.0447 (16) | 0.0286 (16) | −0.0123 (13) | −0.0339 (16) |
C9 | 0.0604 (18) | 0.0557 (17) | 0.0480 (16) | 0.0275 (15) | −0.0182 (14) | −0.0277 (14) |
C10 | 0.0466 (14) | 0.0398 (13) | 0.0396 (13) | 0.0137 (11) | −0.0126 (11) | −0.0162 (11) |
C11 | 0.0299 (11) | 0.0466 (14) | 0.0252 (11) | 0.0034 (10) | −0.0062 (9) | −0.0121 (10) |
C12 | 0.0351 (12) | 0.0418 (13) | 0.0251 (11) | −0.0037 (10) | −0.0089 (9) | −0.0090 (9) |
C13 | 0.0387 (13) | 0.0388 (13) | 0.0463 (14) | −0.0006 (10) | −0.0115 (11) | −0.0205 (11) |
C14 | 0.0378 (13) | 0.0367 (13) | 0.0696 (19) | −0.0038 (11) | −0.0100 (13) | −0.0296 (13) |
C15 | 0.0349 (12) | 0.0249 (11) | 0.0602 (17) | −0.0037 (9) | −0.0029 (11) | −0.0148 (11) |
C16 | 0.0278 (10) | 0.0234 (10) | 0.0452 (13) | 0.0015 (8) | −0.0018 (9) | −0.0118 (10) |
C17 | 0.0442 (14) | 0.0246 (11) | 0.0418 (14) | 0.0008 (10) | −0.0031 (11) | −0.0010 (10) |
C18 | 0.0450 (14) | 0.0337 (12) | 0.0331 (12) | 0.0033 (10) | −0.0082 (11) | −0.0025 (10) |
C19 | 0.0293 (11) | 0.0294 (11) | 0.0311 (11) | 0.0048 (9) | −0.0058 (9) | −0.0081 (9) |
C20 | 0.0374 (12) | 0.0439 (14) | 0.0326 (12) | 0.0049 (10) | −0.0112 (10) | −0.0149 (10) |
C21 | 0.0364 (12) | 0.0386 (13) | 0.0441 (14) | −0.0029 (10) | −0.0101 (11) | −0.0197 (11) |
C22 | 0.0331 (11) | 0.0288 (11) | 0.0388 (13) | −0.0038 (9) | −0.0066 (10) | −0.0099 (9) |
C23 | 0.0215 (9) | 0.0242 (10) | 0.0309 (11) | 0.0036 (7) | −0.0037 (8) | −0.0096 (8) |
C24 | 0.0233 (9) | 0.0233 (10) | 0.0354 (11) | 0.0039 (8) | −0.0038 (8) | −0.0108 (9) |
C25 | 0.0316 (11) | 0.0251 (10) | 0.0310 (11) | 0.0062 (8) | −0.0079 (9) | −0.0104 (8) |
C26 | 0.0254 (10) | 0.0238 (9) | 0.0257 (10) | 0.0056 (8) | −0.0077 (8) | −0.0083 (8) |
C27 | 0.0320 (11) | 0.0254 (10) | 0.0397 (13) | 0.0017 (9) | −0.0029 (10) | −0.0079 (9) |
C28 | 0.0276 (11) | 0.0313 (11) | 0.0369 (12) | 0.0013 (9) | 0.0025 (9) | −0.0079 (10) |
C29 | 0.0254 (10) | 0.0322 (11) | 0.0416 (13) | 0.0072 (9) | −0.0094 (9) | −0.0159 (10) |
C30 | 0.0281 (10) | 0.0238 (10) | 0.0286 (10) | 0.0064 (8) | −0.0102 (8) | −0.0099 (8) |
C31 | 0.0341 (11) | 0.0284 (10) | 0.0335 (11) | 0.0026 (9) | −0.0101 (9) | −0.0158 (9) |
C32 | 0.0352 (11) | 0.0392 (12) | 0.0291 (11) | 0.0088 (10) | −0.0135 (9) | −0.0182 (10) |
C33 | 0.0308 (11) | 0.0361 (11) | 0.0270 (10) | 0.0092 (9) | −0.0126 (9) | −0.0130 (9) |
C34 | 0.0444 (14) | 0.0444 (14) | 0.0261 (11) | 0.0128 (11) | −0.0031 (10) | −0.0116 (10) |
C35 | 0.0303 (10) | 0.0249 (10) | 0.0244 (10) | 0.0063 (8) | −0.0099 (8) | −0.0093 (8) |
C36 | 0.0454 (13) | 0.0266 (11) | 0.0344 (12) | 0.0107 (10) | −0.0166 (10) | −0.0111 (9) |
Co1—O1 | 2.114 (2) | C13—C14 | 1.400 (4) |
Co1—O1w | 2.134 (2) | C13—H13 | 0.9300 |
Co1—N1 | 2.281 (2) | C14—C15 | 1.352 (4) |
Co1—N2 | 2.288 (2) | C14—H14 | 0.9300 |
Co1—N3 | 2.293 (2) | C15—C16 | 1.410 (3) |
Co1—N4 | 2.294 (2) | C15—H15 | 0.9300 |
C25—O1 | 1.264 (3) | C16—C24 | 1.406 (3) |
C25—O2 | 1.231 (3) | C16—C17 | 1.427 (4) |
C36—O3 | 1.246 (3) | C17—C18 | 1.348 (4) |
C36—O4 | 1.253 (3) | C17—H17 | 0.9300 |
O1w—H1w1 | 0.85 | C18—C19 | 1.432 (3) |
O1w—H1w2 | 0.85 | C18—H18 | 0.9300 |
O2w—H2w1 | 0.86 | C19—C23 | 1.405 (3) |
O2w—H2w2 | 0.86 | C19—C20 | 1.408 (3) |
O3w—H3w1 | 0.86 | C20—C21 | 1.362 (4) |
O3w—H3w2 | 0.86 | C20—H20 | 0.9300 |
O4w—H4w1 | 0.85 | C21—C22 | 1.398 (4) |
O4w—H4w2 | 0.87 | C21—H21 | 0.9300 |
O5w—H5w1 | 0.86 | C22—H22 | 0.9300 |
O5w—H5w2 | 0.86 | C23—C24 | 1.443 (3) |
N1—C1 | 1.330 (3) | C25—C26 | 1.529 (3) |
N1—C12 | 1.357 (3) | C26—C33 | 1.531 (3) |
N2—C10 | 1.331 (3) | C26—C35 | 1.535 (3) |
N2—C11 | 1.352 (3) | C26—C27 | 1.546 (3) |
N3—C13 | 1.331 (3) | C27—C28 | 1.529 (3) |
N3—C24 | 1.357 (3) | C27—H27A | 0.9700 |
N4—C22 | 1.325 (3) | C27—H27B | 0.9700 |
N4—C23 | 1.359 (3) | C28—C29 | 1.528 (3) |
C1—C2 | 1.392 (4) | C28—C34 | 1.533 (4) |
C1—H1 | 0.9300 | C28—H28A | 0.9800 |
C2—C3 | 1.358 (5) | C29—C30 | 1.530 (3) |
C2—H2 | 0.9300 | C29—H29A | 0.9700 |
C3—C4 | 1.409 (5) | C29—H29B | 0.9700 |
C3—H3 | 0.9300 | C30—C31 | 1.538 (3) |
C4—C12 | 1.401 (4) | C30—C35 | 1.540 (3) |
C4—C5 | 1.436 (5) | C30—C36 | 1.540 (3) |
C5—C6 | 1.341 (5) | C31—C32 | 1.528 (3) |
C5—H5 | 0.9300 | C31—H31A | 0.9700 |
C6—C7 | 1.427 (5) | C31—H31B | 0.9700 |
C6—H6 | 0.9300 | C32—C34 | 1.524 (4) |
C7—C8 | 1.401 (5) | C32—C33 | 1.536 (3) |
C7—C11 | 1.414 (3) | C32—H32A | 0.9800 |
C8—C9 | 1.356 (5) | C33—H33A | 0.9700 |
C8—H8 | 0.9300 | C33—H33B | 0.9700 |
C9—C10 | 1.395 (4) | C34—H34A | 0.9700 |
C9—H9 | 0.9300 | C34—H34B | 0.9700 |
C10—H10 | 0.9300 | C35—H35A | 0.9700 |
C11—C12 | 1.445 (4) | C35—H35B | 0.9700 |
O1—Co1—O1w | 89.16 (7) | C17—C18—H18 | 119.6 |
O1—Co1—N1 | 90.53 (8) | C19—C18—H18 | 119.6 |
O1w—Co1—N1 | 98.86 (9) | C23—C19—C20 | 117.3 (2) |
O1—Co1—N2 | 163.25 (8) | C23—C19—C18 | 119.6 (2) |
O1w—Co1—N2 | 91.39 (8) | C20—C19—C18 | 123.1 (2) |
N1—Co1—N2 | 72.85 (8) | C21—C20—C19 | 119.7 (2) |
O1—Co1—N3 | 105.30 (7) | C21—C20—H20 | 120.2 |
O1w—Co1—N3 | 92.71 (9) | C19—C20—H20 | 120.2 |
N1—Co1—N3 | 160.55 (8) | C20—C21—C22 | 119.1 (2) |
N2—Co1—N3 | 91.39 (7) | C20—C21—H21 | 120.5 |
O1—Co1—N4 | 89.86 (7) | C22—C21—H21 | 120.5 |
O1w—Co1—N4 | 164.05 (9) | N4—C22—C21 | 123.3 (2) |
N1—Co1—N4 | 97.07 (7) | N4—C22—H22 | 118.3 |
N2—Co1—N4 | 94.11 (7) | C21—C22—H22 | 118.3 |
N3—Co1—N4 | 72.22 (7) | N4—C23—C19 | 122.8 (2) |
C25—O1—Co1 | 130.01 (15) | N4—C23—C24 | 117.70 (19) |
Co1—O1w—H1w1 | 109.6 | C19—C23—C24 | 119.5 (2) |
Co1—O1w—H1w2 | 109.5 | N3—C24—C16 | 123.2 (2) |
H1w1—O1w—H1w2 | 109.4 | N3—C24—C23 | 117.56 (19) |
H2w1—O2w—H2w2 | 108.6 | C16—C24—C23 | 119.2 (2) |
H3w1—O3w—H3w2 | 107.0 | O2—C25—O1 | 124.1 (2) |
H4w1—O4w—H4w2 | 108.0 | O2—C25—C26 | 118.2 (2) |
H5w1—O5w—H5w2 | 106.2 | O1—C25—C26 | 117.65 (19) |
C1—N1—C12 | 118.0 (2) | C25—C26—C33 | 112.78 (17) |
C1—N1—Co1 | 126.02 (19) | C25—C26—C35 | 110.93 (17) |
C12—N1—Co1 | 115.71 (16) | C33—C26—C35 | 108.73 (17) |
C10—N2—C11 | 117.8 (2) | C25—C26—C27 | 106.81 (18) |
C10—N2—Co1 | 126.68 (18) | C33—C26—C27 | 108.89 (19) |
C11—N2—Co1 | 115.51 (16) | C35—C26—C27 | 108.59 (18) |
C13—N3—C24 | 117.5 (2) | C28—C27—C26 | 110.27 (19) |
C13—N3—Co1 | 126.11 (17) | C28—C27—H27A | 109.6 |
C24—N3—Co1 | 116.30 (14) | C26—C27—H27A | 109.6 |
C22—N4—C23 | 117.8 (2) | C28—C27—H27B | 109.6 |
C22—N4—Co1 | 126.09 (16) | C26—C27—H27B | 109.6 |
C23—N4—Co1 | 116.12 (14) | H27A—C27—H27B | 108.1 |
N1—C1—C2 | 123.0 (3) | C29—C28—C27 | 109.4 (2) |
N1—C1—H1 | 118.5 | C29—C28—C34 | 110.0 (2) |
C2—C1—H1 | 118.5 | C27—C28—C34 | 109.1 (2) |
C3—C2—C1 | 119.2 (3) | C29—C28—H28A | 109.4 |
C3—C2—H2 | 120.4 | C27—C28—H28A | 109.4 |
C1—C2—H2 | 120.4 | C34—C28—H28A | 109.4 |
C2—C3—C4 | 120.0 (3) | C28—C29—C30 | 110.18 (18) |
C2—C3—H3 | 120.0 | C28—C29—H29A | 109.6 |
C4—C3—H3 | 120.0 | C30—C29—H29A | 109.6 |
C12—C4—C3 | 117.0 (3) | C28—C29—H29B | 109.6 |
C12—C4—C5 | 119.4 (3) | C30—C29—H29B | 109.6 |
C3—C4—C5 | 123.7 (3) | H29A—C29—H29B | 108.1 |
C6—C5—C4 | 121.3 (3) | C29—C30—C31 | 108.37 (19) |
C6—C5—H5 | 119.4 | C29—C30—C35 | 109.55 (18) |
C4—C5—H5 | 119.4 | C31—C30—C35 | 108.49 (17) |
C5—C6—C7 | 121.3 (3) | C29—C30—C36 | 111.84 (19) |
C5—C6—H6 | 119.4 | C31—C30—C36 | 109.32 (18) |
C7—C6—H6 | 119.4 | C35—C30—C36 | 109.21 (18) |
C8—C7—C11 | 117.1 (3) | C32—C31—C30 | 110.08 (18) |
C8—C7—C6 | 123.6 (3) | C32—C31—H31A | 109.6 |
C11—C7—C6 | 119.3 (3) | C30—C31—H31A | 109.6 |
C9—C8—C7 | 120.2 (3) | C32—C31—H31B | 109.6 |
C9—C8—H8 | 119.9 | C30—C31—H31B | 109.6 |
C7—C8—H8 | 119.9 | H31A—C31—H31B | 108.2 |
C8—C9—C10 | 118.9 (3) | C34—C32—C31 | 110.0 (2) |
C8—C9—H9 | 120.6 | C34—C32—C33 | 109.7 (2) |
C10—C9—H9 | 120.6 | C31—C32—C33 | 109.38 (18) |
N2—C10—C9 | 123.3 (3) | C34—C32—H32A | 109.2 |
N2—C10—H10 | 118.3 | C31—C32—H32A | 109.2 |
C9—C10—H10 | 118.3 | C33—C32—H32A | 109.2 |
N2—C11—C7 | 122.6 (3) | C26—C33—C32 | 109.86 (17) |
N2—C11—C12 | 118.1 (2) | C26—C33—H33A | 109.7 |
C7—C11—C12 | 119.3 (2) | C32—C33—H33A | 109.7 |
N1—C12—C4 | 122.9 (3) | C26—C33—H33B | 109.7 |
N1—C12—C11 | 117.7 (2) | C32—C33—H33B | 109.7 |
C4—C12—C11 | 119.4 (2) | H33A—C33—H33B | 108.2 |
N3—C13—C14 | 122.9 (3) | C32—C34—C28 | 109.04 (19) |
N3—C13—H13 | 118.6 | C32—C34—H34A | 109.9 |
C14—C13—H13 | 118.6 | C28—C34—H34A | 109.9 |
C15—C14—C13 | 119.8 (2) | C32—C34—H34B | 109.9 |
C15—C14—H14 | 120.1 | C28—C34—H34B | 109.9 |
C13—C14—H14 | 120.1 | H34A—C34—H34B | 108.3 |
C14—C15—C16 | 119.5 (2) | C26—C35—C30 | 110.72 (17) |
C14—C15—H15 | 120.2 | C26—C35—H35A | 109.5 |
C16—C15—H15 | 120.2 | C30—C35—H35A | 109.5 |
C24—C16—C15 | 117.1 (2) | C26—C35—H35B | 109.5 |
C24—C16—C17 | 119.7 (2) | C30—C35—H35B | 109.5 |
C15—C16—C17 | 123.1 (2) | H35A—C35—H35B | 108.1 |
C18—C17—C16 | 121.1 (2) | O3—C36—O4 | 124.0 (2) |
C18—C17—H17 | 119.4 | O3—C36—C30 | 118.1 (2) |
C16—C17—H17 | 119.4 | O4—C36—C30 | 118.0 (2) |
C17—C18—C19 | 120.9 (2) | ||
O1w—Co1—O1—C25 | −14.0 (2) | C24—N3—C13—C14 | 1.4 (4) |
N1—Co1—O1—C25 | 84.9 (2) | Co1—N3—C13—C14 | −174.56 (19) |
N2—Co1—O1—C25 | 78.1 (3) | N3—C13—C14—C15 | −0.4 (4) |
N3—Co1—O1—C25 | −106.5 (2) | C13—C14—C15—C16 | −0.9 (4) |
N4—Co1—O1—C25 | −178.0 (2) | C14—C15—C16—C24 | 1.1 (4) |
O1—Co1—N1—C1 | −1.6 (2) | C14—C15—C16—C17 | −179.5 (2) |
O1w—Co1—N1—C1 | 87.7 (2) | C24—C16—C17—C18 | −0.8 (4) |
N2—Co1—N1—C1 | 176.4 (2) | C15—C16—C17—C18 | 179.9 (3) |
N3—Co1—N1—C1 | −146.5 (2) | C16—C17—C18—C19 | 1.5 (4) |
N4—Co1—N1—C1 | −91.5 (2) | C17—C18—C19—C23 | −0.6 (4) |
O1—Co1—N1—C12 | −174.87 (16) | C17—C18—C19—C20 | 178.2 (3) |
O1w—Co1—N1—C12 | −85.65 (17) | C23—C19—C20—C21 | 0.6 (4) |
N2—Co1—N1—C12 | 3.07 (16) | C18—C19—C20—C21 | −178.2 (2) |
N3—Co1—N1—C12 | 40.2 (3) | C19—C20—C21—C22 | 0.6 (4) |
N4—Co1—N1—C12 | 95.21 (16) | C23—N4—C22—C21 | 0.7 (3) |
O1—Co1—N2—C10 | −172.9 (2) | Co1—N4—C22—C21 | 179.00 (18) |
O1w—Co1—N2—C10 | −81.2 (2) | C20—C21—C22—N4 | −1.3 (4) |
N1—Co1—N2—C10 | 179.9 (2) | C22—N4—C23—C19 | 0.6 (3) |
N3—Co1—N2—C10 | 11.5 (2) | Co1—N4—C23—C19 | −177.88 (16) |
N4—Co1—N2—C10 | 83.8 (2) | C22—N4—C23—C24 | 179.4 (2) |
O1—Co1—N2—C11 | 6.0 (3) | Co1—N4—C23—C24 | 0.9 (2) |
O1w—Co1—N2—C11 | 97.68 (17) | C20—C19—C23—N4 | −1.2 (3) |
N1—Co1—N2—C11 | −1.17 (16) | C18—C19—C23—N4 | 177.6 (2) |
N3—Co1—N2—C11 | −169.58 (17) | C20—C19—C23—C24 | −180.0 (2) |
N4—Co1—N2—C11 | −97.31 (16) | C18—C19—C23—C24 | −1.1 (3) |
O1—Co1—N3—C13 | 94.0 (2) | C13—N3—C24—C16 | −1.1 (3) |
O1w—Co1—N3—C13 | 4.1 (2) | Co1—N3—C24—C16 | 175.24 (17) |
N1—Co1—N3—C13 | −122.6 (3) | C13—N3—C24—C23 | −179.7 (2) |
N2—Co1—N3—C13 | −87.4 (2) | Co1—N3—C24—C23 | −3.4 (2) |
N4—Co1—N3—C13 | 178.8 (2) | C15—C16—C24—N3 | −0.1 (3) |
O1—Co1—N3—C24 | −82.01 (16) | C17—C16—C24—N3 | −179.5 (2) |
O1w—Co1—N3—C24 | −171.88 (16) | C15—C16—C24—C23 | 178.5 (2) |
N1—Co1—N3—C24 | 61.5 (3) | C17—C16—C24—C23 | −0.9 (3) |
N2—Co1—N3—C24 | 96.67 (16) | N4—C23—C24—N3 | 1.7 (3) |
N4—Co1—N3—C24 | 2.80 (15) | C19—C23—C24—N3 | −179.50 (19) |
O1—Co1—N4—C22 | −74.12 (19) | N4—C23—C24—C16 | −176.99 (19) |
O1w—Co1—N4—C22 | −160.5 (2) | C19—C23—C24—C16 | 1.8 (3) |
N1—Co1—N4—C22 | 16.4 (2) | Co1—O1—C25—O2 | 15.9 (4) |
N2—Co1—N4—C22 | 89.59 (19) | Co1—O1—C25—C26 | −167.12 (15) |
N3—Co1—N4—C22 | 179.7 (2) | O2—C25—C26—C33 | −160.6 (3) |
O1—Co1—N4—C23 | 104.25 (15) | O1—C25—C26—C33 | 22.3 (3) |
O1w—Co1—N4—C23 | 17.8 (3) | O2—C25—C26—C35 | −38.4 (3) |
N1—Co1—N4—C23 | −165.24 (15) | O1—C25—C26—C35 | 144.5 (2) |
N2—Co1—N4—C23 | −92.03 (15) | O2—C25—C26—C27 | 79.8 (3) |
N3—Co1—N4—C23 | −1.89 (14) | O1—C25—C26—C27 | −97.3 (2) |
C12—N1—C1—C2 | 0.4 (4) | C25—C26—C27—C28 | −179.01 (19) |
Co1—N1—C1—C2 | −172.8 (2) | C33—C26—C27—C28 | 58.9 (2) |
N1—C1—C2—C3 | −0.6 (4) | C35—C26—C27—C28 | −59.3 (2) |
C1—C2—C3—C4 | 0.0 (4) | C26—C27—C28—C29 | 60.2 (3) |
C2—C3—C4—C12 | 0.7 (4) | C26—C27—C28—C34 | −60.2 (3) |
C2—C3—C4—C5 | −179.9 (3) | C27—C28—C29—C30 | −59.8 (3) |
C12—C4—C5—C6 | −0.9 (4) | C34—C28—C29—C30 | 60.1 (2) |
C3—C4—C5—C6 | 179.8 (3) | C28—C29—C30—C31 | −59.4 (2) |
C4—C5—C6—C7 | 1.5 (4) | C28—C29—C30—C35 | 58.7 (2) |
C5—C6—C7—C8 | 178.5 (3) | C28—C29—C30—C36 | 179.98 (19) |
C5—C6—C7—C11 | 0.3 (4) | C29—C30—C31—C32 | 59.5 (2) |
C11—C7—C8—C9 | 3.0 (4) | C35—C30—C31—C32 | −59.3 (2) |
C6—C7—C8—C9 | −175.3 (3) | C36—C30—C31—C32 | −178.34 (19) |
C7—C8—C9—C10 | −0.9 (4) | C30—C31—C32—C34 | −60.3 (2) |
C11—N2—C10—C9 | 2.6 (4) | C30—C31—C32—C33 | 60.2 (2) |
Co1—N2—C10—C9 | −178.6 (2) | C25—C26—C33—C32 | −176.82 (19) |
C8—C9—C10—N2 | −2.1 (4) | C35—C26—C33—C32 | 59.7 (2) |
C10—N2—C11—C7 | −0.2 (3) | C27—C26—C33—C32 | −58.4 (2) |
Co1—N2—C11—C7 | −179.19 (18) | C34—C32—C33—C26 | 60.4 (2) |
C10—N2—C11—C12 | 178.2 (2) | C31—C32—C33—C26 | −60.4 (2) |
Co1—N2—C11—C12 | −0.8 (3) | C31—C32—C34—C28 | 59.3 (2) |
C8—C7—C11—N2 | −2.5 (4) | C33—C32—C34—C28 | −61.0 (2) |
C6—C7—C11—N2 | 175.8 (2) | C29—C28—C34—C32 | −59.2 (2) |
C8—C7—C11—C12 | 179.1 (2) | C27—C28—C34—C32 | 60.9 (3) |
C6—C7—C11—C12 | −2.6 (4) | C25—C26—C35—C30 | 175.56 (18) |
C1—N1—C12—C4 | 0.4 (3) | C33—C26—C35—C30 | −59.9 (2) |
Co1—N1—C12—C4 | 174.31 (18) | C27—C26—C35—C30 | 58.5 (2) |
C1—N1—C12—C11 | −178.5 (2) | C29—C30—C35—C26 | −58.7 (2) |
Co1—N1—C12—C11 | −4.6 (3) | C31—C30—C35—C26 | 59.5 (2) |
C3—C4—C12—N1 | −1.0 (4) | C36—C30—C35—C26 | 178.53 (18) |
C5—C4—C12—N1 | 179.6 (2) | C29—C30—C36—O3 | 3.6 (3) |
C3—C4—C12—C11 | 177.9 (2) | C31—C30—C36—O3 | −116.4 (3) |
C5—C4—C12—C11 | −1.5 (3) | C35—C30—C36—O3 | 125.0 (2) |
N2—C11—C12—N1 | 3.6 (3) | C29—C30—C36—O4 | −176.1 (2) |
C7—C11—C12—N1 | −177.9 (2) | C31—C30—C36—O4 | 63.9 (3) |
N2—C11—C12—C4 | −175.3 (2) | C35—C30—C36—O4 | −54.6 (3) |
C7—C11—C12—C4 | 3.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O2 | 0.85 | 1.82 | 2.599 (3) | 152 |
O1w—H1w2···O2w | 0.85 | 2.10 | 2.656 (3) | 122 |
O2w—H2w1···O4i | 0.86 | 1.86 | 2.712 (3) | 176 |
O2w—H2w2···O4wii | 0.86 | 2.37 | 3.113 (5) | 145 |
O3w—H3w1···O4iii | 0.86 | 2.06 | 2.895 (4) | 164 |
O3w—H3w2···O4w | 0.86 | 2.08 | 2.913 (5) | 164 |
O4w—H4w1···O3iv | 0.85 | 1.84 | 2.695 (3) | 178 |
O5w—H5w1···O3iv | 0.86 | 1.96 | 2.814 (4) | 173 |
O5w—H5w2···O3w | 0.86 | 2.36 | 3.211 (5) | 174 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x, y−1, z; (iv) x+1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Co(C12H14O4)(C12H8N2)2(H2O)]·4H2O |
Mr | 731.65 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 8.9902 (2), 13.2497 (2), 15.6671 (2) |
α, β, γ (°) | 69.277 (1), 77.067 (1), 87.328 (1) |
V (Å3) | 1700.12 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.57 |
Crystal size (mm) | 0.39 × 0.31 × 0.09 |
Data collection | |
Diffractometer | Bruker APEX II CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.813, 0.951 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29003, 7692, 6662 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.167, 1.06 |
No. of reflections | 7692 |
No. of parameters | 451 |
No. of restraints | 24 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.70, −0.77 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).
Co1—O1 | 2.114 (2) | Co1—N2 | 2.288 (2) |
Co1—O1w | 2.134 (2) | Co1—N3 | 2.293 (2) |
Co1—N1 | 2.281 (2) | Co1—N4 | 2.294 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O2 | 0.85 | 1.82 | 2.599 (3) | 152 |
O1w—H1w2···O2w | 0.85 | 2.10 | 2.656 (3) | 122 |
O2w—H2w1···O4i | 0.86 | 1.86 | 2.712 (3) | 176 |
O2w—H2w2···O4wii | 0.86 | 2.37 | 3.113 (5) | 145 |
O3w—H3w1···O4iii | 0.86 | 2.06 | 2.895 (4) | 164 |
O3w—H3w2···O4w | 0.86 | 2.08 | 2.913 (5) | 164 |
O4w—H4w1···O3iv | 0.85 | 1.84 | 2.695 (3) | 178 |
O5w—H5w1···O3iv | 0.86 | 1.96 | 2.814 (4) | 173 |
O5w—H5w2···O3w | 0.86 | 2.36 | 3.211 (5) | 174 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x, y−1, z; (iv) x+1, y−1, z. |
The crystal structures of an enormous number of metal(II) dicarboxylates have been reported (CSD Version 5.28, May 2007; Allen, 2002). However, there is no example of a metal 1,3-adamantanedicarboxylate; the crystal structure of the dicarboxylic acid itself has been known for some time (Glidewell & Ferguson, 1996).
The cobalt(II) atom in the title compound, (I), (Fig. 1), is chelated by two N-heterocycles; it is also linked datively to a water molecule and covalently to a single O atom of the dicarboxylate dianion in an all-cis octahedral geometry (Table 1). The mononuclear complex exists as as a zwitterion (i.e. formal Co+ and free –CO2- carboxyate anion in the same molecule). The component species of (I) are linked into a chain by ay of O—H···O interactions (Table 2).