Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229614025546/yp3085sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229614025546/yp3085Isup2.hkl |
CCDC reference: 1035564
Recently, helical coordination polymers (CPs) have received much attention because of their molecular self-assembly and potential applications in asymmetric catalysis, nonlinear optics and biomimetic chemistry (Zhang et al., 2005; Zhao et al., 2008; Piguet et al., 1997). Significant effort has been devoted to producing CPs with helical structures using various approaches. One of the most successful approaches is the rational selection of flexible N-containing bridging ligands and metal cations to construct target CPs with the desired properties (Chen et al., 2009; Liu, Yu et al., 2014).
Flexible N-containing bridging linkers, such as 1,4-bis[(pyridin-4-yl)methoxy]benzene, 1,4-bis[(pyridin-3-yl)methoxy]benzene and 1,3-bis[(pyridin-4-yl)methoxy]benzene, have been employed as linkers to construct versatile functional CPs (Li, Qin et al., 2012; Li, Zhao et al. 2012; Liu et al., 2010; Oh et al., 2005; Steel & Fitchett, 2013). Liu and co-workers have investigated the coordination chemistry of 1,3-bis[(pyridin-4-yl)methoxy]benzene with ZnII, AgI and HgII salts to form several helical complexes and cage-like structures (Liu et al., 2010). Li and co-workers have prepared and structurally characterized some two- or three-dimensional entangled structures through the assembly of 1,4-bis[(pyridin-4-yl)methoxy]benzene with ZnII salts (Li, Qin et al., 2012). However, to the best of our knowledge, the coordination chemistry of 1,3-bis[(pyridin-3-yl)methoxy]benzene (bpmb) has attracted little attention. A mixed-ligand system consisting of two types of ligand provides more variability in the construction of different topologies (Liu, Yu et al., 2014). Thus, we reacted Zn(OAc)2·2H2O (OAc is acetate) with bpmb and benzene-1,4-dicarboxylic acid (H2L) to produce the title compound, [Zn(L)(bpmb)(H2O)]n, (I).
1,3-Bis[(pyridin-3-yl)methoxy]benzene (bpmb) was prepared according to the literature method of Xiao et al. (2011). All other chemicals and reagents were obtained from commercial sources (Sigma–Aldrich) and used as received. A mixture of Zn(OAc)2·2H2O (9 mg, 0.04 mmol), benzene-1,4-dicarboxylic acid (3 mg, 0.02 mmol), bpmb (6 mg, 0.02 mmol) and H2O (4 ml) was sealed in a 10 ml Pyrex glass tube and heated at 423 K for 4 d, then cooled to room temperature at a rate of 5 K h-1. Colourless blocks of (I) were collected and dried in air (yield 4 mg, 37%, based on bpmb). IR (KBr disc, ν, cm-1): 3396 (w), 3030 (w), 2980 (w), 1659 (m), 1602 (s), 1575 (s), 1535 (m), 1458 (m), 1389 (m), 1326 (w), 1244 (w), 1158 (m), 1041 (m), 990 (w), 889 (w), 862 (w), 837 (w), 786 (m), 646 (m).
Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms were placed in geometrically idealized positions, with C—H = 0.93 Å for aromatic H atoms, C—H = 0.97 Å for methylene H atoms and O—H = 0.85 Å for coordinated water H atoms, and refined as riding, with Uiso(H) = 1.2Ueq(C,O).
Compound (I) crystallizes in the monoclinic space group P21/c and its asymmetric unit contains one [Zn(L)(bpmb)(H2O)] unit. Each ZnII centre is tetrahedrally coordinated by two carboxylate O atoms [O3 and O6i; symmetry code: (i) -x + 1, y + 1/2, -z + 1/2] from two L2- ligands, one O atom from a water ligand (O1W) and one N atom from one bpmb ligand (Table 2). A weak interaction [2.5190 (15) Å] exists between atoms Zn1 and O4 (Fig. 1).
In (I), the L2- ligands adopt a µ2-η1:η1 coordination mode to link two ZnII cations. The L2- anions bridge these metal centres in a head-to-tail fashion via the monodentate aromatic carboxylate atoms O3 and O6, to form a one-dimensional [Zn(L)]n chain extending along the b axis (Fig. 2; purple represents the L2- ligands), with a Zn···Zn separation of 10.955 (5) Å. Notably, only one N atom (N1) of the bpmb ligand is bound to a ZnII centre. The other N atom (N2) is employed as an acceptor and interacts with the H atom of the water ligand (O1W), forming an intramolecular hydrogen bond (O1W—H1WB···N2i). These hydrogen-bonding interactions induce the formation of a one-dimensional helical [Zn(L)(bpmb)(H2O)]n chain (Fig. 2). Adjacent one-dimensional arrays are interconnected via O1W—H1WA···O4ii hydrogen bonds [symmetry code: (ii) x - 1, y, z] between the aqua ligands O1W and the uncoordinated carboxylate O4 atoms of L2-, resulting in two-dimensional corrugated sheets extending in the ab plane.
A previously reported ZnII coordination polymer, viz. [Zn(L)(3-bpmb)(H2O)]n, (II), assembled from 1,4-bis[(pyridin-3-yl)methoxy]benzene (3-bpmb) and H2L, shows a three-dimensional coordination framework (Li, Zhao et al., 2012). In (II), each ZnII cation is five-coordinated and displays a distorted square-pyramidal coordination geometry. The 3-bpmb ligands in (II) adopt a bridging mode to connect two adjacent ZnII cations, resulting in a meso-helical [Zn(3-bpmb)]n chain, while in (I) only one N atom of the bpmb ligand coordinates to the ZnII centre, resulting in helical chains, which are rare in the literature.
In conclusion, a new zinc coordination polymer, (I), containing infinite helical chains has been prepared under solvothermal conditions using flexible bpmb and L2- ligands. The structural differences between (I) and (II) suggest that the substituted positions of the N atoms in bpmb and 3-bpmb ligands significantly affect the helicity of the resulting CPs.
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
[Zn(C8H4O4)(C18H16N2O2)(H2O)] | F(000) = 1112 |
Mr = 539.82 | Dx = 1.519 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.0706 (12) Å | Cell parameters from 5574 reflections |
b = 17.914 (4) Å | θ = 2.2–27.1° |
c = 21.750 (4) Å | µ = 1.09 mm−1 |
β = 93.54 (3)° | T = 296 K |
V = 2360.9 (8) Å3 | Block, colourless |
Z = 4 | 0.25 × 0.25 × 0.25 mm |
Bruker APEXII CCD area-detector diffractometer | 3617 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
ϕ and ω scans | θmax = 25.3°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −7→7 |
Tmin = 0.759, Tmax = 0.761 | k = −21→21 |
16703 measured reflections | l = −26→26 |
4279 independent reflections |
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)] = 0.027 | Hydrogen site location: mixed |
wR(F2) = 0.069 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0325P)2 + 0.7485P] where P = (Fo2 + 2Fc2)/3 |
4279 reflections | (Δ/σ)max = 0.003 |
325 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
[Zn(C8H4O4)(C18H16N2O2)(H2O)] | V = 2360.9 (8) Å3 |
Mr = 539.82 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.0706 (12) Å | µ = 1.09 mm−1 |
b = 17.914 (4) Å | T = 296 K |
c = 21.750 (4) Å | 0.25 × 0.25 × 0.25 mm |
β = 93.54 (3)° |
Bruker APEXII CCD area-detector diffractometer | 4279 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | 3617 reflections with I > 2σ(I) |
Tmin = 0.759, Tmax = 0.761 | Rint = 0.029 |
16703 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
wR(F2) = 0.069 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.22 e Å−3 |
4279 reflections | Δρmin = −0.26 e Å−3 |
325 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.05847 (4) | 0.92079 (2) | 0.31918 (2) | 0.03109 (8) | |
C1 | −0.1698 (3) | 0.93378 (11) | 0.43514 (10) | 0.0383 (5) | |
H1 | −0.2775 | 0.9577 | 0.4101 | 0.046* | |
C2 | −0.2010 (4) | 0.92626 (12) | 0.49689 (10) | 0.0426 (5) | |
H2 | −0.3260 | 0.9459 | 0.5135 | 0.051* | |
C3 | −0.0443 (4) | 0.88922 (12) | 0.53366 (10) | 0.0416 (5) | |
H3 | −0.0637 | 0.8830 | 0.5754 | 0.050* | |
C4 | 0.1426 (3) | 0.86114 (11) | 0.50832 (9) | 0.0359 (4) | |
C5 | 0.1642 (3) | 0.87254 (11) | 0.44631 (9) | 0.0354 (4) | |
H5 | 0.2905 | 0.8551 | 0.4289 | 0.042* | |
C6 | 0.3145 (4) | 0.82046 (12) | 0.54820 (9) | 0.0430 (5) | |
H6A | 0.4008 | 0.8559 | 0.5734 | 0.052* | |
H6B | 0.2437 | 0.7862 | 0.5753 | 0.052* | |
C7 | 0.6189 (4) | 0.73840 (11) | 0.53915 (9) | 0.0409 (5) | |
C8 | 0.6466 (4) | 0.72967 (12) | 0.60222 (10) | 0.0475 (5) | |
H8 | 0.5529 | 0.7535 | 0.6282 | 0.057* | |
C9 | 0.8166 (4) | 0.68480 (13) | 0.62595 (11) | 0.0548 (6) | |
H9 | 0.8374 | 0.6788 | 0.6684 | 0.066* | |
C10 | 0.9550 (4) | 0.64899 (14) | 0.58831 (11) | 0.0576 (6) | |
H10 | 1.0678 | 0.6187 | 0.6050 | 0.069* | |
C11 | 0.9252 (4) | 0.65839 (13) | 0.52491 (10) | 0.0506 (6) | |
C12 | 0.7594 (4) | 0.70389 (12) | 0.50010 (10) | 0.0451 (5) | |
H12 | 0.7420 | 0.7113 | 0.4578 | 0.054* | |
C13 | 1.0801 (4) | 0.63360 (14) | 0.42775 (11) | 0.0582 (6) | |
H13A | 1.1290 | 0.6845 | 0.4220 | 0.070* | |
H13B | 0.9366 | 0.6274 | 0.4062 | 0.070* | |
C14 | 1.2434 (4) | 0.57941 (12) | 0.40348 (10) | 0.0459 (5) | |
C15 | 1.2035 (4) | 0.54481 (13) | 0.34751 (10) | 0.0479 (5) | |
H15 | 1.0704 | 0.5548 | 0.3255 | 0.057* | |
C16 | 1.5836 (4) | 0.51371 (16) | 0.41171 (12) | 0.0632 (7) | |
H16 | 1.7157 | 0.5014 | 0.4333 | 0.076* | |
C17 | 1.5304 (4) | 0.48343 (14) | 0.35481 (11) | 0.0548 (6) | |
H17 | 1.6307 | 0.4512 | 0.3380 | 0.066* | |
C18 | 1.4388 (4) | 0.56246 (14) | 0.43619 (12) | 0.0561 (6) | |
H18 | 1.4720 | 0.5840 | 0.4746 | 0.067* | |
C19 | 0.2979 (4) | 0.80707 (11) | 0.29104 (9) | 0.0388 (5) | |
C20 | 0.3903 (3) | 0.73703 (10) | 0.26583 (9) | 0.0336 (4) | |
C21 | 0.6058 (3) | 0.71618 (11) | 0.28222 (10) | 0.0406 (5) | |
H21 | 0.6920 | 0.7454 | 0.3096 | 0.049* | |
C22 | 0.6929 (3) | 0.65231 (11) | 0.25806 (10) | 0.0393 (5) | |
H22 | 0.8365 | 0.6381 | 0.2701 | 0.047* | |
C23 | 0.5687 (3) | 0.60890 (10) | 0.21598 (9) | 0.0319 (4) | |
C24 | 0.3524 (3) | 0.62906 (10) | 0.20045 (9) | 0.0338 (4) | |
H24 | 0.2662 | 0.5996 | 0.1732 | 0.041* | |
C25 | 0.2634 (3) | 0.69257 (10) | 0.22507 (9) | 0.0350 (4) | |
H25 | 0.1178 | 0.7056 | 0.2143 | 0.042* | |
C26 | 0.6699 (3) | 0.54289 (10) | 0.18561 (10) | 0.0345 (4) | |
N1 | 0.0108 (3) | 0.90773 (8) | 0.40990 (7) | 0.0330 (4) | |
N2 | 1.3434 (3) | 0.49782 (10) | 0.32272 (8) | 0.0485 (5) | |
O1 | 0.4546 (3) | 0.78031 (9) | 0.50984 (6) | 0.0497 (4) | |
O2 | 1.0674 (3) | 0.61795 (11) | 0.49119 (8) | 0.0708 (5) | |
O3 | 0.0969 (3) | 0.82184 (8) | 0.27830 (8) | 0.0543 (4) | |
O4 | 0.4168 (3) | 0.84955 (8) | 0.32416 (7) | 0.0488 (4) | |
O5 | 0.6113 (3) | 0.52729 (8) | 0.13198 (7) | 0.0472 (4) | |
O6 | 0.8176 (2) | 0.50765 (8) | 0.21884 (7) | 0.0447 (4) | |
O1W | −0.2544 (2) | 0.93862 (8) | 0.28920 (7) | 0.0443 (4) | |
H1WA | −0.3516 | 0.9066 | 0.2976 | 0.053* | |
H1WB | −0.2929 | 0.9557 | 0.2537 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.03370 (14) | 0.02834 (12) | 0.03153 (13) | 0.00066 (9) | 0.00432 (9) | 0.00196 (9) |
C1 | 0.0347 (11) | 0.0388 (11) | 0.0415 (12) | 0.0031 (9) | 0.0043 (9) | 0.0015 (9) |
C2 | 0.0379 (12) | 0.0488 (12) | 0.0424 (12) | 0.0044 (10) | 0.0125 (10) | −0.0015 (10) |
C3 | 0.0485 (13) | 0.0462 (12) | 0.0310 (11) | −0.0024 (10) | 0.0087 (10) | 0.0016 (9) |
C4 | 0.0405 (11) | 0.0342 (10) | 0.0331 (11) | −0.0025 (9) | 0.0032 (9) | 0.0008 (8) |
C5 | 0.0346 (11) | 0.0375 (11) | 0.0345 (11) | 0.0023 (9) | 0.0061 (9) | 0.0011 (8) |
C6 | 0.0491 (13) | 0.0482 (12) | 0.0321 (11) | 0.0078 (10) | 0.0055 (10) | 0.0025 (9) |
C7 | 0.0502 (13) | 0.0362 (11) | 0.0355 (11) | 0.0050 (10) | −0.0034 (10) | −0.0003 (9) |
C8 | 0.0593 (14) | 0.0482 (13) | 0.0351 (12) | 0.0115 (11) | 0.0033 (11) | −0.0007 (10) |
C9 | 0.0709 (16) | 0.0570 (14) | 0.0358 (12) | 0.0134 (13) | −0.0039 (12) | 0.0038 (11) |
C10 | 0.0656 (16) | 0.0613 (15) | 0.0450 (14) | 0.0234 (13) | −0.0037 (12) | 0.0033 (11) |
C11 | 0.0590 (15) | 0.0493 (13) | 0.0433 (13) | 0.0135 (11) | 0.0006 (11) | −0.0047 (10) |
C12 | 0.0585 (14) | 0.0450 (12) | 0.0312 (11) | 0.0058 (11) | −0.0011 (10) | −0.0019 (9) |
C13 | 0.0712 (17) | 0.0566 (14) | 0.0470 (14) | 0.0173 (13) | 0.0067 (12) | −0.0033 (11) |
C14 | 0.0522 (14) | 0.0456 (12) | 0.0399 (12) | 0.0041 (10) | 0.0045 (10) | −0.0012 (10) |
C15 | 0.0482 (13) | 0.0549 (13) | 0.0396 (12) | 0.0072 (11) | −0.0054 (10) | 0.0016 (11) |
C16 | 0.0463 (14) | 0.090 (2) | 0.0519 (15) | 0.0137 (14) | −0.0070 (12) | −0.0079 (14) |
C17 | 0.0520 (14) | 0.0661 (16) | 0.0464 (14) | 0.0136 (12) | 0.0046 (11) | −0.0022 (12) |
C18 | 0.0521 (14) | 0.0688 (16) | 0.0466 (14) | −0.0002 (12) | −0.0038 (12) | −0.0126 (12) |
C19 | 0.0486 (13) | 0.0312 (10) | 0.0381 (11) | −0.0005 (9) | 0.0156 (10) | 0.0013 (9) |
C20 | 0.0373 (11) | 0.0297 (10) | 0.0345 (11) | −0.0005 (8) | 0.0077 (9) | 0.0001 (8) |
C21 | 0.0399 (12) | 0.0377 (11) | 0.0437 (12) | −0.0032 (9) | −0.0012 (10) | −0.0090 (9) |
C22 | 0.0313 (11) | 0.0378 (11) | 0.0484 (12) | 0.0031 (9) | 0.0001 (9) | −0.0035 (9) |
C23 | 0.0354 (11) | 0.0279 (9) | 0.0331 (10) | −0.0012 (8) | 0.0073 (8) | 0.0021 (8) |
C24 | 0.0372 (11) | 0.0316 (10) | 0.0326 (10) | −0.0043 (8) | 0.0019 (9) | −0.0013 (8) |
C25 | 0.0295 (10) | 0.0356 (10) | 0.0401 (11) | 0.0012 (8) | 0.0028 (9) | 0.0016 (9) |
C26 | 0.0330 (11) | 0.0293 (10) | 0.0427 (12) | −0.0041 (8) | 0.0127 (9) | −0.0006 (9) |
N1 | 0.0340 (9) | 0.0323 (8) | 0.0329 (9) | 0.0000 (7) | 0.0034 (7) | 0.0021 (7) |
N2 | 0.0539 (12) | 0.0545 (11) | 0.0370 (10) | 0.0086 (9) | 0.0011 (9) | −0.0030 (8) |
O1 | 0.0603 (10) | 0.0575 (9) | 0.0309 (8) | 0.0209 (8) | −0.0008 (7) | 0.0001 (7) |
O2 | 0.0859 (13) | 0.0836 (13) | 0.0438 (10) | 0.0432 (11) | 0.0097 (9) | 0.0014 (9) |
O3 | 0.0472 (9) | 0.0453 (9) | 0.0703 (11) | 0.0126 (7) | 0.0030 (8) | −0.0155 (8) |
O4 | 0.0565 (10) | 0.0384 (8) | 0.0531 (9) | −0.0094 (7) | 0.0165 (8) | −0.0120 (7) |
O5 | 0.0594 (10) | 0.0456 (8) | 0.0374 (8) | 0.0049 (7) | 0.0094 (7) | −0.0056 (7) |
O6 | 0.0418 (8) | 0.0389 (8) | 0.0527 (9) | 0.0107 (7) | −0.0014 (7) | −0.0099 (7) |
O1W | 0.0334 (8) | 0.0524 (9) | 0.0469 (9) | −0.0017 (6) | 0.0007 (7) | 0.0162 (7) |
Zn1—O6i | 1.9360 (14) | C13—C14 | 1.506 (3) |
Zn1—O1W | 1.9954 (14) | C13—H13A | 0.9700 |
Zn1—O3 | 2.0032 (15) | C13—H13B | 0.9700 |
Zn1—N1 | 2.0256 (17) | C14—C15 | 1.374 (3) |
Zn1—C19 | 2.598 (2) | C14—C18 | 1.379 (3) |
C1—N1 | 1.340 (3) | C15—N2 | 1.333 (3) |
C1—C2 | 1.375 (3) | C15—H15 | 0.9300 |
C1—H1 | 0.9300 | C16—C18 | 1.370 (3) |
C2—C3 | 1.375 (3) | C16—C17 | 1.372 (3) |
C2—H2 | 0.9300 | C16—H16 | 0.9300 |
C3—C4 | 1.386 (3) | C17—N2 | 1.321 (3) |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C4—C5 | 1.378 (3) | C18—H18 | 0.9300 |
C4—C6 | 1.504 (3) | C19—O4 | 1.247 (2) |
C5—N1 | 1.342 (2) | C19—O3 | 1.263 (3) |
C5—H5 | 0.9300 | C19—C20 | 1.492 (3) |
C6—O1 | 1.423 (2) | C20—C21 | 1.386 (3) |
C6—H6A | 0.9700 | C20—C25 | 1.389 (3) |
C6—H6B | 0.9700 | C21—C22 | 1.378 (3) |
C7—O1 | 1.373 (2) | C21—H21 | 0.9300 |
C7—C8 | 1.381 (3) | C22—C23 | 1.388 (3) |
C7—C12 | 1.386 (3) | C22—H22 | 0.9300 |
C8—C9 | 1.383 (3) | C23—C24 | 1.383 (3) |
C8—H8 | 0.9300 | C23—C26 | 1.504 (3) |
C9—C10 | 1.368 (3) | C24—C25 | 1.382 (3) |
C9—H9 | 0.9300 | C24—H24 | 0.9300 |
C10—C11 | 1.390 (3) | C25—H25 | 0.9300 |
C10—H10 | 0.9300 | C26—O5 | 1.230 (2) |
C11—O2 | 1.374 (3) | C26—O6 | 1.282 (2) |
C11—C12 | 1.379 (3) | O6—Zn1ii | 1.9359 (14) |
C12—H12 | 0.9300 | O1W—H1WA | 0.8500 |
C13—O2 | 1.415 (3) | O1W—H1WB | 0.8501 |
O6i—Zn1—O1W | 96.83 (6) | H13A—C13—H13B | 108.6 |
O6i—Zn1—O3 | 117.57 (7) | C15—C14—C18 | 117.2 (2) |
O1W—Zn1—O3 | 97.54 (7) | C15—C14—C13 | 121.1 (2) |
O6i—Zn1—N1 | 126.27 (6) | C18—C14—C13 | 121.7 (2) |
O1W—Zn1—N1 | 98.42 (7) | N2—C15—C14 | 124.1 (2) |
O3—Zn1—N1 | 110.96 (7) | N2—C15—H15 | 117.9 |
O6i—Zn1—C19 | 106.97 (7) | C14—C15—H15 | 117.9 |
O1W—Zn1—C19 | 125.71 (7) | C18—C16—C17 | 118.8 (2) |
O3—Zn1—C19 | 28.27 (6) | C18—C16—H16 | 120.6 |
N1—Zn1—C19 | 104.76 (6) | C17—C16—H16 | 120.6 |
N1—C1—C2 | 122.12 (19) | N2—C17—C16 | 123.2 (2) |
N1—C1—H1 | 118.9 | N2—C17—H17 | 118.4 |
C2—C1—H1 | 118.9 | C16—C17—H17 | 118.4 |
C1—C2—C3 | 118.9 (2) | C16—C18—C14 | 119.5 (2) |
C1—C2—H2 | 120.5 | C16—C18—H18 | 120.3 |
C3—C2—H2 | 120.5 | C14—C18—H18 | 120.3 |
C2—C3—C4 | 119.85 (19) | O4—C19—O3 | 121.07 (19) |
C2—C3—H3 | 120.1 | O4—C19—C20 | 120.53 (19) |
C4—C3—H3 | 120.1 | O3—C19—C20 | 118.39 (18) |
C5—C4—C3 | 117.69 (19) | O4—C19—Zn1 | 72.40 (11) |
C5—C4—C6 | 122.14 (18) | O3—C19—Zn1 | 48.70 (10) |
C3—C4—C6 | 120.16 (18) | C20—C19—Zn1 | 166.99 (15) |
N1—C5—C4 | 122.87 (18) | C21—C20—C25 | 119.15 (18) |
N1—C5—H5 | 118.6 | C21—C20—C19 | 120.15 (18) |
C4—C5—H5 | 118.6 | C25—C20—C19 | 120.69 (18) |
O1—C6—C4 | 108.98 (16) | C22—C21—C20 | 120.27 (18) |
O1—C6—H6A | 109.9 | C22—C21—H21 | 119.9 |
C4—C6—H6A | 109.9 | C20—C21—H21 | 119.9 |
O1—C6—H6B | 109.9 | C21—C22—C23 | 120.73 (19) |
C4—C6—H6B | 109.9 | C21—C22—H22 | 119.6 |
H6A—C6—H6B | 108.3 | C23—C22—H22 | 119.6 |
O1—C7—C8 | 124.31 (19) | C24—C23—C22 | 118.92 (18) |
O1—C7—C12 | 114.58 (18) | C24—C23—C26 | 120.35 (17) |
C8—C7—C12 | 121.1 (2) | C22—C23—C26 | 120.67 (17) |
C7—C8—C9 | 118.6 (2) | C25—C24—C23 | 120.56 (18) |
C7—C8—H8 | 120.7 | C25—C24—H24 | 119.7 |
C9—C8—H8 | 120.7 | C23—C24—H24 | 119.7 |
C10—C9—C8 | 121.4 (2) | C24—C25—C20 | 120.32 (18) |
C10—C9—H9 | 119.3 | C24—C25—H25 | 119.8 |
C8—C9—H9 | 119.3 | C20—C25—H25 | 119.8 |
C9—C10—C11 | 119.3 (2) | O5—C26—O6 | 125.01 (18) |
C9—C10—H10 | 120.3 | O5—C26—C23 | 119.53 (18) |
C11—C10—H10 | 120.3 | O6—C26—C23 | 115.45 (17) |
O2—C11—C12 | 124.8 (2) | C1—N1—C5 | 118.51 (17) |
O2—C11—C10 | 114.7 (2) | C1—N1—Zn1 | 121.92 (13) |
C12—C11—C10 | 120.5 (2) | C5—N1—Zn1 | 119.57 (13) |
C11—C12—C7 | 119.1 (2) | C17—N2—C15 | 117.25 (19) |
C11—C12—H12 | 120.5 | C7—O1—C6 | 116.57 (15) |
C7—C12—H12 | 120.5 | C11—O2—C13 | 119.34 (18) |
O2—C13—C14 | 106.90 (19) | C19—O3—Zn1 | 103.03 (13) |
O2—C13—H13A | 110.3 | C26—O6—Zn1ii | 115.57 (13) |
C14—C13—H13A | 110.3 | Zn1—O1W—H1WA | 118.8 |
O2—C13—H13B | 110.3 | Zn1—O1W—H1WB | 123.9 |
C14—C13—H13B | 110.3 | H1WA—O1W—H1WB | 106.3 |
N1—C1—C2—C3 | −1.6 (3) | Zn1—C19—C20—C25 | −1.4 (7) |
C1—C2—C3—C4 | 0.9 (3) | C25—C20—C21—C22 | 0.3 (3) |
C2—C3—C4—C5 | 0.6 (3) | C19—C20—C21—C22 | −178.71 (18) |
C2—C3—C4—C6 | −179.89 (19) | C20—C21—C22—C23 | 1.5 (3) |
C3—C4—C5—N1 | −1.6 (3) | C21—C22—C23—C24 | −2.6 (3) |
C6—C4—C5—N1 | 178.97 (18) | C21—C22—C23—C26 | 174.80 (19) |
C5—C4—C6—O1 | −16.3 (3) | C22—C23—C24—C25 | 1.8 (3) |
C3—C4—C6—O1 | 164.21 (18) | C26—C23—C24—C25 | −175.56 (17) |
O1—C7—C8—C9 | 178.8 (2) | C23—C24—C25—C20 | 0.0 (3) |
C12—C7—C8—C9 | −0.8 (3) | C21—C20—C25—C24 | −1.0 (3) |
C7—C8—C9—C10 | −0.4 (4) | C19—C20—C25—C24 | 177.96 (17) |
C8—C9—C10—C11 | 0.5 (4) | C24—C23—C26—O5 | 32.1 (3) |
C9—C10—C11—O2 | −177.7 (2) | C22—C23—C26—O5 | −145.2 (2) |
C9—C10—C11—C12 | 0.6 (4) | C24—C23—C26—O6 | −149.15 (18) |
O2—C11—C12—C7 | 176.3 (2) | C22—C23—C26—O6 | 33.5 (3) |
C10—C11—C12—C7 | −1.8 (4) | C2—C1—N1—C5 | 0.7 (3) |
O1—C7—C12—C11 | −177.8 (2) | C2—C1—N1—Zn1 | −178.78 (15) |
C8—C7—C12—C11 | 1.9 (3) | C4—C5—N1—C1 | 0.9 (3) |
O2—C13—C14—C15 | 137.8 (2) | C4—C5—N1—Zn1 | −179.58 (15) |
O2—C13—C14—C18 | −42.3 (3) | C16—C17—N2—C15 | 0.7 (4) |
C18—C14—C15—N2 | −1.7 (4) | C14—C15—N2—C17 | 0.9 (4) |
C13—C14—C15—N2 | 178.2 (2) | C8—C7—O1—C6 | 4.0 (3) |
C18—C16—C17—N2 | −1.4 (4) | C12—C7—O1—C6 | −176.30 (19) |
C17—C16—C18—C14 | 0.5 (4) | C4—C6—O1—C7 | −178.57 (17) |
C15—C14—C18—C16 | 0.9 (4) | C12—C11—O2—C13 | 13.5 (4) |
C13—C14—C18—C16 | −179.0 (2) | C10—C11—O2—C13 | −168.2 (2) |
O4—C19—C20—C21 | 4.1 (3) | C14—C13—O2—C11 | −178.5 (2) |
O3—C19—C20—C21 | −175.50 (19) | O4—C19—O3—Zn1 | 2.5 (2) |
Zn1—C19—C20—C21 | 177.6 (5) | C20—C19—O3—Zn1 | −177.93 (14) |
O4—C19—C20—C25 | −174.92 (18) | O5—C26—O6—Zn1ii | −3.2 (3) |
O3—C19—C20—C25 | 5.5 (3) | C23—C26—O6—Zn1ii | 178.12 (12) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1 | 0.93 | 2.38 | 2.729 (2) | 102 |
C5—H5···O4 | 0.93 | 2.45 | 3.176 (3) | 135 |
O1W—H1WA···O4iii | 0.85 | 1.86 | 2.701 (2) | 170 |
O1W—H1WB···N2i | 0.85 | 1.83 | 2.679 (2) | 173 |
C1—H1···O5iv | 0.93 | 2.50 | 3.412 (3) | 165 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (iii) x−1, y, z; (iv) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C8H4O4)(C18H16N2O2)(H2O)] |
Mr | 539.82 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 6.0706 (12), 17.914 (4), 21.750 (4) |
β (°) | 93.54 (3) |
V (Å3) | 2360.9 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.09 |
Crystal size (mm) | 0.25 × 0.25 × 0.25 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2003) |
Tmin, Tmax | 0.759, 0.761 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16703, 4279, 3617 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.069, 1.03 |
No. of reflections | 4279 |
No. of parameters | 325 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.26 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2003), SHELXS2013 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Zn1—O6i | 1.9360 (14) | Zn1—O3 | 2.0032 (15) |
Zn1—O1W | 1.9954 (14) | Zn1—N1 | 2.0256 (17) |
O6i—Zn1—O1W | 96.83 (6) | O6i—Zn1—N1 | 126.27 (6) |
O6i—Zn1—O3 | 117.57 (7) | O1W—Zn1—N1 | 98.42 (7) |
O1W—Zn1—O3 | 97.54 (7) | O3—Zn1—N1 | 110.96 (7) |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1 | 0.93 | 2.38 | 2.729 (2) | 102.0 |
C5—H5···O4 | 0.93 | 2.45 | 3.176 (3) | 134.8 |
O1W—H1WA···O4ii | 0.85 | 1.86 | 2.701 (2) | 170.2 |
O1W—H1WB···N2i | 0.85 | 1.83 | 2.679 (2) | 173.2 |
C1—H1···O5iii | 0.93 | 2.50 | 3.412 (3) | 165.4 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) −x, y+1/2, −z+1/2. |