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
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.050
- wR factor = 0.167
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O4W - H4W2 ... ?
Alert level C PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 20 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Co1 - O1 .. 7.15 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C28 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C32 = ... R PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1 (2) 1.33 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 24
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 4 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 1 ALERT type 5 Informative message, check
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).
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. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
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).