The reactions of (R)- and (S)-4-(1-carboxyethoxy)benzoic acid (H2CBA) with 1,3-bis(2-methyl-1H-imidazol-1-yl)benzene (1,3-BMIB) ligands afforded a pair of homochiral coordination polymers (CPs), namely, poly[[[μ-1,3-bis(2-methyl-1H-imidazol-1-yl)benzene][μ-(S)-4-(1-carboxylatoethoxy)benzoato]zinc(II)] monohydrate], {[Zn(C10H8O5)(C14H14N4)]·H2O}n or {[Zn{(S)-CBA}(1,3-BMIB)]·H2O}n (1-L), and poly[[[μ-1,3-bis(2-methyl-1H-imidazol-1-yl)benzene][μ-(R)-4-(1-carboxylatoethoxy)benzoato]zinc(II)] monohydrate] (1-D). Three kinds of helical chains exist in compounds 1-D and 1-L, which are constructed from ZnII atoms, 1,3-BMIB ligands and/or CBA2− ligands. When the as-synthesized crystals of 1-L and 1-D were further heated in the mother liquor or air, poly[[μ-1,3-bis(2-methyl-1H-imidazol-1-yl)benzene][μ-(S)-4-(1-carboxylatoethoxy)benzoato]zinc(II)], [Zn(C10H8O5)(C14H14N4)]n or [Zn{(S)-CBA}(1,3-BMIB)]n (2-L), and poly[[μ-1,3-bis(2-methyl-1H-imidazol-1-yl)benzene][μ-(R)-4-(1-carboxylatoethoxy)benzoato]zinc(II)] (2-D) were obtained, respectively. The single-crystal structure analysis revealed that 2-L and 2-D only contained one type of helical chain formed by ZnII atoms and 1,3-BMIB and CBA2− ligands, which indicated that the helical chains were reconstructed though solid-to-solid transformation. This result not only means the realization of helical transformation, but also gives a feasible strategy to build homochiral CPs.
Supporting information
CCDC references: 1958857; 1958858; 1958856; 1946491
For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015). Program(s) used to solve structure: olex2.solve (Bourhis et al., 2015) for 1-L; SHELXT (Sheldrick, 2015) for 1-D, 2-L, 2-D. Program(s) used to refine structure: olex2.refine (Bourhis et al., 2015) for 1-L, 2-D; SHELXL (Sheldrick, 2015) for 1-D, 2-L. For all structures, molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
Poly[[[µ-1,3-bis(2-methyl-1
H-imidazol-1-yl)benzene][µ-(
S)-4-(1-carboxylatoethoxy)benzoato]zinc(II)] monohydrate] (1-L)
top
Crystal data top
[Zn(C10H8O5)(C14H14N4)]·H2O | F(000) = 548 |
Mr = 529.84 | Dx = 1.491 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2880 (4) Å | Cell parameters from 8441 reflections |
b = 14.3767 (7) Å | θ = 3.9–29.8° |
c = 10.2288 (6) Å | µ = 1.09 mm−1 |
β = 104.514 (5)° | T = 293 K |
V = 1179.91 (11) Å3 | Needle, clear light colourless |
Z = 2 | 0.3 × 0.1 × 0.1 mm |
Data collection top
Rigaku XtaLAB Pro (Kappa single) diffractometer | 6194 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 5693 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
ω scans | θmax = 30.2°, θmin = 3.8° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −11→11 |
Tmin = 0.478, Tmax = 1.000 | k = −19→20 |
19699 measured reflections | l = −13→14 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.030 | w = 1/[σ2(Fo2) + (0.0459P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.075 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.28 e Å−3 |
6194 reflections | Δρmin = −0.21 e Å−3 |
322 parameters | Absolute structure: Flack x determined using 2428 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
1 restraint | Absolute structure parameter: −0.001 (6) |
Primary atom site location: iterative | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.51793 (3) | 0.74584 (2) | 0.59921 (3) | 0.02583 (9) | |
O4 | 0.3271 (3) | 0.67670 (18) | 0.4913 (2) | 0.0396 (5) | |
N4 | 1.3900 (3) | 0.27523 (16) | 0.5652 (2) | 0.0286 (5) | |
O3 | −0.3244 (3) | 0.47615 (16) | 0.1553 (2) | 0.0358 (5) | |
O5 | 0.2201 (3) | 0.6331 (2) | 0.6615 (2) | 0.0479 (6) | |
N2 | 0.8508 (3) | 0.54199 (15) | 0.7928 (2) | 0.0261 (4) | |
N3 | 1.2466 (3) | 0.30978 (17) | 0.7128 (2) | 0.0289 (5) | |
N1 | 0.6837 (3) | 0.66032 (16) | 0.7219 (2) | 0.0268 (4) | |
C13 | 0.6972 (3) | 0.56792 (19) | 0.7187 (3) | 0.0260 (5) | |
O1 | −0.4270 (3) | 0.34784 (17) | 0.3121 (3) | 0.0467 (6) | |
C23 | 1.2460 (3) | 0.30886 (18) | 0.5804 (3) | 0.0267 (5) | |
C24 | 1.1000 (4) | 0.3374 (2) | 0.4698 (3) | 0.0338 (6) | |
H24A | 1.069737 | 0.400239 | 0.484539 | 0.051* | |
H24B | 1.007604 | 0.296878 | 0.468987 | 0.051* | |
H24C | 1.128620 | 0.333303 | 0.384671 | 0.051* | |
C11 | 0.8337 (4) | 0.69346 (19) | 0.8015 (3) | 0.0314 (6) | |
H11 | 0.858932 | 0.755668 | 0.821801 | 0.038* | |
C18 | 1.0489 (4) | 0.2708 (2) | 0.8434 (3) | 0.0343 (6) | |
H18 | 1.094039 | 0.211256 | 0.855355 | 0.041* | |
C10 | 0.2150 (3) | 0.63880 (19) | 0.5398 (3) | 0.0290 (5) | |
C14 | 0.5687 (4) | 0.5007 (2) | 0.6464 (3) | 0.0377 (6) | |
H14A | 0.622145 | 0.449918 | 0.613023 | 0.057* | |
H14B | 0.493857 | 0.531482 | 0.572132 | 0.057* | |
H14C | 0.507225 | 0.477357 | 0.707481 | 0.057* | |
C19 | 1.1116 (3) | 0.33627 (19) | 0.7707 (3) | 0.0270 (5) | |
C7 | 0.0706 (3) | 0.59693 (18) | 0.4381 (3) | 0.0253 (5) | |
C2 | −0.4930 (3) | 0.4819 (2) | 0.1681 (3) | 0.0340 (6) | |
H2 | −0.507837 | 0.541491 | 0.210263 | 0.041* | |
C12 | 0.9374 (4) | 0.6209 (2) | 0.8448 (3) | 0.0322 (6) | |
H12 | 1.045714 | 0.623745 | 0.899022 | 0.039* | |
C9 | −0.0443 (4) | 0.5212 (2) | 0.2242 (3) | 0.0308 (6) | |
H9 | −0.030080 | 0.496758 | 0.143611 | 0.037* | |
C4 | −0.1995 (3) | 0.51568 (19) | 0.2538 (3) | 0.0276 (5) | |
C22 | 1.4847 (3) | 0.2532 (3) | 0.6940 (3) | 0.0331 (6) | |
H22 | 1.592010 | 0.228731 | 0.713874 | 0.040* | |
C6 | −0.0835 (3) | 0.5887 (2) | 0.4678 (3) | 0.0296 (5) | |
H6 | −0.096250 | 0.610150 | 0.550386 | 0.035* | |
O1W | 0.3209 (5) | 0.7408 (4) | 0.9013 (3) | 0.0882 (12) | |
H1WA | 0.306104 | 0.696865 | 0.843916 | 0.132* | |
H1WB | 0.359603 | 0.785233 | 0.863601 | 0.132* | |
C5 | −0.2188 (3) | 0.5491 (2) | 0.3768 (3) | 0.0316 (6) | |
H5 | −0.321433 | 0.544877 | 0.397667 | 0.038* | |
C16 | 0.8513 (4) | 0.3838 (2) | 0.8826 (3) | 0.0327 (6) | |
H16 | 0.764199 | 0.400080 | 0.920399 | 0.039* | |
O2 | −0.6857 (4) | 0.3961 (3) | 0.2546 (5) | 0.0851 (13) | |
C15 | 0.9167 (3) | 0.44873 (18) | 0.8095 (3) | 0.0254 (5) | |
C8 | 0.0881 (3) | 0.5629 (2) | 0.3142 (3) | 0.0301 (5) | |
H8 | 0.190045 | 0.568381 | 0.292278 | 0.036* | |
C17 | 0.9166 (4) | 0.2949 (2) | 0.8989 (3) | 0.0374 (6) | |
H17 | 0.872383 | 0.250961 | 0.946893 | 0.045* | |
C20 | 1.0485 (3) | 0.42678 (19) | 0.7534 (3) | 0.0262 (5) | |
H20 | 1.093109 | 0.470911 | 0.705967 | 0.031* | |
C1 | −0.5380 (4) | 0.4033 (2) | 0.2527 (4) | 0.0397 (7) | |
C21 | 1.3978 (4) | 0.2727 (2) | 0.7856 (3) | 0.0363 (7) | |
H21 | 1.431668 | 0.263246 | 0.878372 | 0.044* | |
C3 | −0.6027 (5) | 0.4809 (4) | 0.0251 (5) | 0.0694 (13) | |
H3A | −0.583284 | 0.536225 | −0.021244 | 0.104* | |
H3B | −0.717673 | 0.478495 | 0.027578 | 0.104* | |
H3C | −0.576677 | 0.427252 | −0.021700 | 0.104* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.02048 (12) | 0.02274 (13) | 0.03408 (15) | −0.00142 (13) | 0.00648 (9) | 0.00106 (13) |
O4 | 0.0296 (10) | 0.0456 (12) | 0.0419 (12) | −0.0166 (9) | 0.0057 (8) | 0.0012 (9) |
N4 | 0.0250 (10) | 0.0260 (10) | 0.0341 (12) | 0.0045 (8) | 0.0065 (9) | −0.0022 (8) |
O3 | 0.0293 (10) | 0.0432 (12) | 0.0341 (11) | −0.0126 (9) | 0.0063 (8) | −0.0062 (9) |
O5 | 0.0398 (12) | 0.0693 (17) | 0.0334 (12) | −0.0167 (12) | 0.0066 (9) | −0.0073 (11) |
N2 | 0.0245 (10) | 0.0226 (11) | 0.0308 (11) | 0.0037 (8) | 0.0060 (8) | −0.0016 (8) |
N3 | 0.0291 (11) | 0.0258 (11) | 0.0312 (12) | 0.0082 (9) | 0.0063 (9) | −0.0005 (8) |
N1 | 0.0257 (10) | 0.0234 (11) | 0.0310 (12) | 0.0014 (8) | 0.0064 (9) | −0.0018 (8) |
C13 | 0.0248 (12) | 0.0242 (13) | 0.0301 (13) | 0.0030 (10) | 0.0094 (10) | 0.0015 (10) |
O1 | 0.0459 (13) | 0.0347 (12) | 0.0606 (15) | −0.0056 (10) | 0.0152 (11) | 0.0093 (10) |
C23 | 0.0271 (12) | 0.0217 (11) | 0.0312 (13) | 0.0035 (10) | 0.0074 (10) | 0.0008 (9) |
C24 | 0.0309 (14) | 0.0366 (15) | 0.0339 (15) | 0.0115 (11) | 0.0082 (11) | 0.0036 (11) |
C11 | 0.0311 (13) | 0.0243 (14) | 0.0349 (14) | 0.0000 (11) | 0.0014 (11) | −0.0059 (10) |
C18 | 0.0383 (14) | 0.0252 (14) | 0.0391 (15) | 0.0057 (10) | 0.0093 (11) | 0.0043 (10) |
C10 | 0.0194 (11) | 0.0275 (13) | 0.0388 (15) | −0.0018 (10) | 0.0047 (10) | −0.0007 (10) |
C14 | 0.0299 (13) | 0.0283 (14) | 0.0503 (17) | −0.0039 (11) | 0.0014 (12) | −0.0005 (12) |
C19 | 0.0261 (12) | 0.0274 (13) | 0.0262 (12) | 0.0048 (10) | 0.0044 (9) | −0.0023 (9) |
C7 | 0.0211 (11) | 0.0219 (11) | 0.0326 (13) | −0.0026 (9) | 0.0062 (9) | 0.0010 (9) |
C2 | 0.0239 (12) | 0.0286 (14) | 0.0444 (16) | −0.0044 (10) | −0.0011 (11) | −0.0025 (11) |
C12 | 0.0302 (13) | 0.0279 (13) | 0.0339 (14) | 0.0014 (11) | −0.0005 (11) | −0.0034 (11) |
C9 | 0.0315 (13) | 0.0321 (15) | 0.0298 (14) | −0.0065 (12) | 0.0097 (11) | −0.0046 (11) |
C4 | 0.0259 (12) | 0.0244 (12) | 0.0317 (13) | −0.0056 (10) | 0.0059 (10) | 0.0014 (9) |
C22 | 0.0273 (10) | 0.0314 (14) | 0.0379 (13) | 0.0081 (13) | 0.0028 (9) | −0.0019 (13) |
C6 | 0.0276 (13) | 0.0317 (14) | 0.0302 (13) | −0.0034 (10) | 0.0088 (10) | −0.0037 (10) |
O1W | 0.112 (3) | 0.110 (3) | 0.0523 (16) | −0.046 (3) | 0.0401 (17) | −0.028 (2) |
C5 | 0.0222 (12) | 0.0392 (16) | 0.0352 (14) | −0.0060 (11) | 0.0105 (10) | −0.0008 (11) |
C16 | 0.0309 (13) | 0.0357 (15) | 0.0338 (14) | 0.0044 (11) | 0.0123 (10) | 0.0055 (11) |
O2 | 0.0463 (17) | 0.062 (2) | 0.162 (4) | −0.0002 (15) | 0.053 (2) | 0.013 (2) |
C15 | 0.0271 (12) | 0.0225 (12) | 0.0250 (12) | 0.0040 (9) | 0.0034 (9) | −0.0001 (9) |
C8 | 0.0239 (12) | 0.0325 (14) | 0.0359 (14) | −0.0047 (10) | 0.0115 (10) | −0.0014 (11) |
C17 | 0.0395 (15) | 0.0335 (16) | 0.0415 (16) | 0.0007 (13) | 0.0147 (12) | 0.0102 (12) |
C20 | 0.0293 (12) | 0.0229 (13) | 0.0271 (13) | 0.0012 (10) | 0.0085 (10) | 0.0015 (10) |
C1 | 0.0360 (15) | 0.0286 (15) | 0.0574 (19) | −0.0063 (12) | 0.0174 (13) | −0.0078 (13) |
C21 | 0.0335 (13) | 0.0374 (16) | 0.0340 (14) | 0.0128 (11) | 0.0009 (11) | −0.0001 (10) |
C3 | 0.047 (2) | 0.091 (4) | 0.055 (2) | −0.004 (2) | −0.0151 (18) | 0.002 (2) |
Geometric parameters (Å, º) top
Zn1—O4 | 1.958 (2) | C14—H14C | 0.9600 |
Zn1—N4i | 2.057 (2) | C19—C20 | 1.397 (4) |
Zn1—N1 | 2.027 (2) | C7—C6 | 1.390 (4) |
Zn1—O1ii | 1.971 (2) | C7—C8 | 1.400 (4) |
O4—C10 | 1.280 (4) | C2—H2 | 0.9800 |
N4—C23 | 1.333 (3) | C2—C1 | 1.526 (4) |
N4—C22 | 1.390 (4) | C2—C3 | 1.517 (5) |
O3—C2 | 1.439 (4) | C12—H12 | 0.9300 |
O3—C4 | 1.374 (3) | C9—H9 | 0.9300 |
O5—C10 | 1.237 (4) | C9—C4 | 1.396 (4) |
N2—C13 | 1.360 (4) | C9—C8 | 1.380 (4) |
N2—C12 | 1.376 (4) | C4—C5 | 1.392 (4) |
N2—C15 | 1.442 (3) | C22—H22 | 0.9300 |
N3—C23 | 1.353 (4) | C22—C21 | 1.347 (4) |
N3—C19 | 1.442 (3) | C6—H6 | 0.9300 |
N3—C21 | 1.393 (4) | C6—C5 | 1.387 (4) |
N1—C13 | 1.334 (4) | O1W—H1WA | 0.8501 |
N1—C11 | 1.388 (4) | O1W—H1WB | 0.8498 |
C13—C14 | 1.490 (4) | C5—H5 | 0.9300 |
O1—C1 | 1.254 (4) | C16—H16 | 0.9300 |
C23—C24 | 1.492 (4) | C16—C15 | 1.389 (4) |
C24—H24A | 0.9600 | C16—C17 | 1.382 (4) |
C24—H24B | 0.9600 | O2—C1 | 1.233 (4) |
C24—H24C | 0.9600 | C15—C20 | 1.391 (4) |
C11—H11 | 0.9300 | C8—H8 | 0.9300 |
C11—C12 | 1.354 (4) | C17—H17 | 0.9300 |
C18—H18 | 0.9300 | C20—H20 | 0.9300 |
C18—C19 | 1.379 (4) | C21—H21 | 0.9300 |
C18—C17 | 1.399 (5) | C3—H3A | 0.9600 |
C10—C7 | 1.501 (4) | C3—H3B | 0.9600 |
C14—H14A | 0.9600 | C3—H3C | 0.9600 |
C14—H14B | 0.9600 | | |
| | | |
O4—Zn1—N4i | 93.20 (9) | C8—C7—C10 | 121.5 (2) |
O4—Zn1—N1 | 111.57 (10) | O3—C2—H2 | 108.8 |
O4—Zn1—O1ii | 106.81 (10) | O3—C2—C1 | 113.0 (2) |
N1—Zn1—N4i | 107.32 (9) | O3—C2—C3 | 105.8 (3) |
O1ii—Zn1—N4i | 119.11 (11) | C1—C2—H2 | 108.8 |
O1ii—Zn1—N1 | 116.40 (10) | C3—C2—H2 | 108.8 |
C10—O4—Zn1 | 124.0 (2) | C3—C2—C1 | 111.5 (3) |
C23—N4—Zn1iii | 134.16 (19) | N2—C12—H12 | 126.8 |
C23—N4—C22 | 106.3 (2) | C11—C12—N2 | 106.4 (2) |
C22—N4—Zn1iii | 119.40 (18) | C11—C12—H12 | 126.8 |
C4—O3—C2 | 118.7 (2) | C4—C9—H9 | 119.9 |
C13—N2—C12 | 108.3 (2) | C8—C9—H9 | 119.9 |
C13—N2—C15 | 126.5 (2) | C8—C9—C4 | 120.1 (3) |
C12—N2—C15 | 125.1 (2) | O3—C4—C9 | 115.5 (2) |
C23—N3—C19 | 127.2 (2) | O3—C4—C5 | 124.7 (2) |
C23—N3—C21 | 107.9 (2) | C5—C4—C9 | 119.8 (3) |
C21—N3—C19 | 124.6 (2) | N4—C22—H22 | 125.1 |
C13—N1—Zn1 | 129.56 (18) | C21—C22—N4 | 109.8 (2) |
C13—N1—C11 | 106.7 (2) | C21—C22—H22 | 125.1 |
C11—N1—Zn1 | 121.55 (18) | C7—C6—H6 | 119.3 |
N2—C13—C14 | 123.5 (2) | C5—C6—C7 | 121.4 (3) |
N1—C13—N2 | 109.4 (2) | C5—C6—H6 | 119.3 |
N1—C13—C14 | 127.1 (2) | H1WA—O1W—H1WB | 104.5 |
C1—O1—Zn1iv | 112.2 (2) | C4—C5—H5 | 120.3 |
N4—C23—N3 | 110.0 (2) | C6—C5—C4 | 119.4 (2) |
N4—C23—C24 | 126.2 (3) | C6—C5—H5 | 120.3 |
N3—C23—C24 | 123.7 (2) | C15—C16—H16 | 120.2 |
C23—C24—H24A | 109.5 | C17—C16—H16 | 120.2 |
C23—C24—H24B | 109.5 | C17—C16—C15 | 119.5 (3) |
C23—C24—H24C | 109.5 | C16—C15—N2 | 120.1 (2) |
H24A—C24—H24B | 109.5 | C16—C15—C20 | 121.5 (2) |
H24A—C24—H24C | 109.5 | C20—C15—N2 | 118.4 (2) |
H24B—C24—H24C | 109.5 | C7—C8—H8 | 119.7 |
N1—C11—H11 | 125.4 | C9—C8—C7 | 120.7 (2) |
C12—C11—N1 | 109.2 (2) | C9—C8—H8 | 119.7 |
C12—C11—H11 | 125.4 | C18—C17—H17 | 119.9 |
C19—C18—H18 | 120.4 | C16—C17—C18 | 120.2 (3) |
C19—C18—C17 | 119.3 (3) | C16—C17—H17 | 119.9 |
C17—C18—H18 | 120.4 | C19—C20—H20 | 121.1 |
O4—C10—C7 | 115.6 (3) | C15—C20—C19 | 117.8 (2) |
O5—C10—O4 | 125.0 (3) | C15—C20—H20 | 121.1 |
O5—C10—C7 | 119.4 (3) | O1—C1—C2 | 119.5 (3) |
C13—C14—H14A | 109.5 | O2—C1—O1 | 123.4 (4) |
C13—C14—H14B | 109.5 | O2—C1—C2 | 117.1 (3) |
C13—C14—H14C | 109.5 | N3—C21—H21 | 127.0 |
H14A—C14—H14B | 109.5 | C22—C21—N3 | 105.9 (3) |
H14A—C14—H14C | 109.5 | C22—C21—H21 | 127.0 |
H14B—C14—H14C | 109.5 | C2—C3—H3A | 109.5 |
C18—C19—N3 | 118.5 (2) | C2—C3—H3B | 109.5 |
C18—C19—C20 | 121.6 (3) | C2—C3—H3C | 109.5 |
C20—C19—N3 | 119.9 (2) | H3A—C3—H3B | 109.5 |
C6—C7—C10 | 120.0 (2) | H3A—C3—H3C | 109.5 |
C6—C7—C8 | 118.5 (2) | H3B—C3—H3C | 109.5 |
Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) −x, y+1/2, −z+1; (iii) −x+2, y−1/2, −z+1; (iv) −x, y−1/2, −z+1. |
Poly[[[µ-1,3-bis(2-methyl-1
H-imidazol-1-yl)benzene][µ-(
R)-4-(1-carboxylatoethoxy)benzoato]zinc(II)] monohydrate] (1-D)
top
Crystal data top
[Zn(C10H8O5)(C14H14N4)]·H2O | F(000) = 548 |
Mr = 529.84 | Dx = 1.494 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2888 (5) Å | Cell parameters from 7886 reflections |
b = 14.3618 (7) Å | θ = 3.9–30.2° |
c = 10.2195 (7) Å | µ = 1.09 mm−1 |
β = 104.509 (7)° | T = 293 K |
V = 1177.75 (13) Å3 | Block, clear light colourless |
Z = 2 | 0.3 × 0.1 × 0.1 mm |
Data collection top
Rigaku XtaLAB Pro (Kappa single) diffractometer | 6215 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 5710 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ω scans | θmax = 30.4°, θmin = 3.7° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −10→11 |
Tmin = 0.565, Tmax = 1.000 | k = −19→20 |
20401 measured reflections | l = −14→14 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.030 | w = 1/[σ2(Fo2) + (0.0425P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.075 | (Δ/σ)max = 0.001 |
S = 1.02 | Δρmax = 0.31 e Å−3 |
6215 reflections | Δρmin = −0.26 e Å−3 |
322 parameters | Absolute structure: Flack x determined using 2451 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
7 restraints | Absolute structure parameter: −0.008 (6) |
Primary atom site location: dual | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.48210 (3) | 0.25388 (2) | 0.40070 (3) | 0.02549 (9) | |
O4 | 0.6728 (3) | 0.32335 (18) | 0.5087 (2) | 0.0395 (5) | |
O3 | 1.3248 (3) | 0.52356 (16) | 0.8448 (2) | 0.0360 (5) | |
N3 | −0.2466 (3) | 0.69014 (17) | 0.2870 (2) | 0.0282 (5) | |
N4 | −0.3904 (3) | 0.72439 (16) | 0.4348 (2) | 0.0280 (5) | |
N2 | 0.1492 (3) | 0.45794 (15) | 0.2070 (2) | 0.0251 (4) | |
O5 | 0.7799 (3) | 0.3663 (2) | 0.3387 (2) | 0.0471 (6) | |
C13 | 0.3027 (4) | 0.43201 (19) | 0.2812 (3) | 0.0257 (5) | |
N1 | 0.3161 (3) | 0.33939 (16) | 0.2778 (2) | 0.0270 (4) | |
O1 | 1.4270 (3) | 0.65166 (17) | 0.6879 (3) | 0.0466 (6) | |
C23 | −0.2456 (3) | 0.69088 (18) | 0.4200 (3) | 0.0264 (5) | |
C24 | −0.1004 (4) | 0.6625 (2) | 0.5301 (3) | 0.0336 (6) | |
H24A | −0.105936 | 0.596754 | 0.545773 | 0.050* | |
H24B | −0.102197 | 0.695690 | 0.611273 | 0.050* | |
H24C | 0.000713 | 0.676533 | 0.504603 | 0.050* | |
C11 | 0.1666 (4) | 0.3063 (2) | 0.1986 (3) | 0.0315 (6) | |
H11 | 0.141426 | 0.243993 | 0.178181 | 0.038* | |
C18 | −0.0484 (4) | 0.7288 (2) | 0.1570 (3) | 0.0339 (6) | |
H18 | −0.093177 | 0.788473 | 0.145326 | 0.041* | |
C17 | −0.1115 (3) | 0.66354 (19) | 0.2299 (3) | 0.0267 (5) | |
C2 | 1.4930 (3) | 0.5178 (2) | 0.8321 (3) | 0.0337 (6) | |
H2 | 1.507562 | 0.458284 | 0.789534 | 0.040* | |
C7 | 0.9292 (3) | 0.40301 (18) | 0.5622 (3) | 0.0253 (5) | |
C12 | 0.0626 (4) | 0.3791 (2) | 0.1555 (3) | 0.0316 (6) | |
H12 | −0.045915 | 0.376219 | 0.101631 | 0.038* | |
C14 | 0.4316 (4) | 0.4990 (2) | 0.3534 (3) | 0.0380 (6) | |
H14A | 0.498175 | 0.518811 | 0.294083 | 0.057* | |
H14B | 0.501453 | 0.469229 | 0.431387 | 0.057* | |
H14C | 0.378152 | 0.552014 | 0.381374 | 0.057* | |
C10 | 0.7850 (3) | 0.36077 (19) | 0.4601 (3) | 0.0282 (5) | |
C20 | 0.1485 (4) | 0.6159 (2) | 0.1176 (3) | 0.0323 (6) | |
H20 | 0.236191 | 0.599851 | 0.080312 | 0.039* | |
O2 | 1.6854 (4) | 0.6042 (2) | 0.7453 (5) | 0.0829 (13) | |
C9 | 1.0445 (4) | 0.4788 (2) | 0.7759 (3) | 0.0307 (6) | |
H9 | 1.030131 | 0.503423 | 0.856422 | 0.037* | |
C19 | 0.0830 (4) | 0.7047 (2) | 0.1008 (3) | 0.0365 (6) | |
H19 | 0.126461 | 0.748535 | 0.052066 | 0.044* | |
O1W | 0.6795 (5) | 0.2592 (4) | 0.0988 (3) | 0.0862 (11) | |
H1WA | 0.653189 | 0.212249 | 0.139562 | 0.129* | |
H1WB | 0.692369 | 0.303019 | 0.156429 | 0.129* | |
C6 | 1.0826 (3) | 0.4112 (2) | 0.5316 (3) | 0.0285 (5) | |
H6 | 1.094798 | 0.390170 | 0.448530 | 0.034* | |
C4 | 1.1997 (3) | 0.48401 (19) | 0.7463 (3) | 0.0278 (5) | |
C15 | 0.0830 (3) | 0.55071 (19) | 0.1904 (3) | 0.0256 (5) | |
C1 | 1.5380 (4) | 0.5968 (2) | 0.7475 (4) | 0.0384 (7) | |
C16 | −0.0486 (3) | 0.57310 (19) | 0.2467 (3) | 0.0265 (5) | |
H16 | −0.093230 | 0.528956 | 0.294219 | 0.032* | |
C5 | 1.2188 (3) | 0.4505 (2) | 0.6238 (3) | 0.0314 (6) | |
H5 | 1.321703 | 0.454171 | 0.603164 | 0.038* | |
C22 | −0.4852 (3) | 0.7468 (3) | 0.3061 (3) | 0.0329 (6) | |
H22 | −0.592149 | 0.771699 | 0.286040 | 0.039* | |
C8 | 0.9124 (3) | 0.4371 (2) | 0.6857 (3) | 0.0298 (5) | |
H8 | 0.810467 | 0.431657 | 0.707636 | 0.036* | |
C21 | −0.3973 (4) | 0.7267 (2) | 0.2145 (3) | 0.0351 (6) | |
H21 | −0.431254 | 0.735679 | 0.121465 | 0.042* | |
C3 | 1.6031 (6) | 0.5184 (4) | 0.9750 (4) | 0.0698 (13) | |
H3A | 1.576314 | 0.571478 | 1.022691 | 0.105* | |
H3B | 1.717888 | 0.521691 | 0.972223 | 0.105* | |
H3C | 1.584916 | 0.462461 | 1.020711 | 0.105* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.02078 (13) | 0.02224 (13) | 0.03327 (14) | −0.00144 (13) | 0.00644 (9) | 0.00090 (14) |
O4 | 0.0294 (10) | 0.0448 (12) | 0.0421 (11) | −0.0168 (9) | 0.0050 (8) | 0.0003 (10) |
O3 | 0.0297 (10) | 0.0430 (12) | 0.0340 (10) | −0.0133 (9) | 0.0055 (8) | −0.0076 (9) |
N3 | 0.0301 (11) | 0.0247 (11) | 0.0299 (11) | 0.0076 (9) | 0.0075 (9) | 0.0000 (9) |
N4 | 0.0256 (10) | 0.0261 (10) | 0.0321 (11) | 0.0045 (8) | 0.0068 (8) | −0.0020 (8) |
N2 | 0.0229 (10) | 0.0233 (11) | 0.0295 (10) | 0.0038 (8) | 0.0071 (8) | −0.0007 (8) |
O5 | 0.0390 (12) | 0.0668 (17) | 0.0342 (11) | −0.0156 (12) | 0.0070 (9) | −0.0086 (11) |
C13 | 0.0266 (13) | 0.0222 (12) | 0.0296 (12) | 0.0028 (10) | 0.0095 (10) | 0.0015 (10) |
N1 | 0.0278 (11) | 0.0216 (11) | 0.0315 (11) | 0.0019 (8) | 0.0075 (9) | −0.0007 (8) |
O1 | 0.0463 (13) | 0.0352 (12) | 0.0594 (14) | −0.0052 (10) | 0.0154 (11) | 0.0106 (10) |
C23 | 0.0268 (12) | 0.0201 (11) | 0.0324 (12) | 0.0023 (10) | 0.0078 (10) | −0.0014 (10) |
C24 | 0.0326 (14) | 0.0352 (15) | 0.0328 (13) | 0.0116 (12) | 0.0078 (11) | 0.0044 (11) |
C11 | 0.0324 (14) | 0.0248 (13) | 0.0339 (13) | 0.0003 (11) | 0.0021 (11) | −0.0056 (10) |
C18 | 0.0390 (14) | 0.0246 (14) | 0.0378 (14) | 0.0055 (10) | 0.0087 (11) | 0.0038 (10) |
C17 | 0.0277 (12) | 0.0248 (12) | 0.0265 (12) | 0.0052 (10) | 0.0049 (10) | −0.0019 (9) |
C2 | 0.0249 (13) | 0.0271 (13) | 0.0448 (15) | −0.0048 (11) | 0.0005 (11) | −0.0041 (12) |
C7 | 0.0239 (12) | 0.0206 (11) | 0.0310 (12) | −0.0032 (9) | 0.0061 (10) | 0.0011 (9) |
C12 | 0.0297 (14) | 0.0273 (13) | 0.0336 (14) | 0.0011 (11) | 0.0004 (11) | −0.0040 (11) |
C14 | 0.0308 (14) | 0.0286 (14) | 0.0496 (16) | −0.0036 (12) | 0.0010 (13) | 0.0005 (13) |
C10 | 0.0206 (11) | 0.0256 (13) | 0.0370 (14) | −0.0044 (10) | 0.0048 (10) | −0.0015 (10) |
C20 | 0.0318 (13) | 0.0352 (15) | 0.0322 (13) | 0.0044 (11) | 0.0123 (10) | 0.0046 (11) |
O2 | 0.0458 (17) | 0.058 (2) | 0.160 (4) | −0.0007 (15) | 0.053 (2) | 0.008 (2) |
C9 | 0.0307 (13) | 0.0320 (15) | 0.0304 (13) | −0.0049 (12) | 0.0096 (11) | −0.0022 (11) |
C19 | 0.0373 (15) | 0.0343 (16) | 0.0395 (15) | 0.0017 (13) | 0.0127 (12) | 0.0126 (12) |
O1W | 0.111 (3) | 0.106 (3) | 0.0530 (15) | −0.040 (3) | 0.0407 (17) | −0.025 (2) |
C6 | 0.0290 (13) | 0.0297 (13) | 0.0283 (12) | −0.0026 (11) | 0.0100 (10) | −0.0037 (10) |
C4 | 0.0279 (13) | 0.0235 (12) | 0.0311 (12) | −0.0054 (10) | 0.0056 (10) | 0.0004 (10) |
C15 | 0.0255 (12) | 0.0230 (12) | 0.0266 (11) | 0.0029 (10) | 0.0032 (9) | −0.0006 (9) |
C1 | 0.0366 (15) | 0.0267 (14) | 0.0553 (18) | −0.0062 (12) | 0.0177 (13) | −0.0064 (13) |
C16 | 0.0305 (13) | 0.0213 (12) | 0.0281 (12) | 0.0025 (11) | 0.0081 (10) | 0.0020 (10) |
C5 | 0.0233 (12) | 0.0370 (15) | 0.0352 (13) | −0.0066 (11) | 0.0096 (10) | −0.0023 (11) |
C22 | 0.0275 (11) | 0.0315 (14) | 0.0364 (12) | 0.0083 (13) | 0.0021 (9) | −0.0041 (14) |
C8 | 0.0245 (12) | 0.0313 (13) | 0.0360 (13) | −0.0036 (11) | 0.0121 (10) | −0.0016 (11) |
C21 | 0.0340 (13) | 0.0368 (16) | 0.0317 (13) | 0.0119 (11) | 0.0030 (10) | 0.0013 (10) |
C3 | 0.053 (2) | 0.089 (4) | 0.051 (2) | −0.001 (2) | −0.0168 (18) | −0.001 (2) |
Geometric parameters (Å, º) top
Zn1—O4 | 1.959 (2) | C2—C3 | 1.516 (5) |
Zn1—N4i | 2.055 (2) | C7—C10 | 1.503 (4) |
Zn1—N1 | 2.028 (2) | C7—C6 | 1.388 (4) |
Zn1—O1ii | 1.971 (2) | C7—C8 | 1.393 (4) |
O4—C10 | 1.278 (4) | C12—H12 | 0.9300 |
O3—C2 | 1.435 (4) | C14—H14A | 0.9600 |
O3—C4 | 1.374 (3) | C14—H14B | 0.9600 |
N3—C23 | 1.358 (4) | C14—H14C | 0.9600 |
N3—C17 | 1.438 (3) | C20—H20 | 0.9300 |
N3—C21 | 1.386 (4) | C20—C19 | 1.379 (4) |
N4—C23 | 1.336 (4) | C20—C15 | 1.389 (4) |
N4—C22 | 1.391 (3) | O2—C1 | 1.232 (4) |
N2—C13 | 1.360 (4) | C9—H9 | 0.9300 |
N2—C12 | 1.373 (4) | C9—C4 | 1.396 (4) |
N2—C15 | 1.435 (3) | C9—C8 | 1.379 (4) |
O5—C10 | 1.234 (4) | C19—H19 | 0.9300 |
C13—N1 | 1.336 (4) | O1W—H1WA | 0.8501 |
C13—C14 | 1.488 (4) | O1W—H1WB | 0.8499 |
N1—C11 | 1.384 (4) | C6—H6 | 0.9300 |
O1—C1 | 1.249 (4) | C6—C5 | 1.395 (4) |
C23—C24 | 1.484 (4) | C4—C5 | 1.387 (4) |
C24—H24A | 0.9600 | C15—C16 | 1.392 (4) |
C24—H24B | 0.9600 | C16—H16 | 0.9300 |
C24—H24C | 0.9600 | C5—H5 | 0.9300 |
C11—H11 | 0.9300 | C22—H22 | 0.9300 |
C11—C12 | 1.357 (4) | C22—C21 | 1.353 (4) |
C18—H18 | 0.9300 | C8—H8 | 0.9300 |
C18—C17 | 1.378 (4) | C21—H21 | 0.9300 |
C18—C19 | 1.396 (4) | C3—H3A | 0.9600 |
C17—C16 | 1.394 (4) | C3—H3B | 0.9600 |
C2—H2 | 0.9800 | C3—H3C | 0.9600 |
C2—C1 | 1.528 (4) | | |
| | | |
O4—Zn1—N4i | 93.20 (9) | C11—C12—H12 | 126.8 |
O4—Zn1—N1 | 111.52 (10) | C13—C14—H14A | 109.5 |
O4—Zn1—O1ii | 106.91 (10) | C13—C14—H14B | 109.5 |
N1—Zn1—N4i | 107.39 (9) | C13—C14—H14C | 109.5 |
O1ii—Zn1—N4i | 119.00 (10) | H14A—C14—H14B | 109.5 |
O1ii—Zn1—N1 | 116.39 (10) | H14A—C14—H14C | 109.5 |
C10—O4—Zn1 | 124.0 (2) | H14B—C14—H14C | 109.5 |
C4—O3—C2 | 118.8 (2) | O4—C10—C7 | 115.5 (2) |
C23—N3—C17 | 126.8 (2) | O5—C10—O4 | 125.0 (3) |
C23—N3—C21 | 108.1 (2) | O5—C10—C7 | 119.5 (2) |
C21—N3—C17 | 125.0 (2) | C19—C20—H20 | 120.2 |
C23—N4—Zn1iii | 133.93 (19) | C19—C20—C15 | 119.7 (2) |
C23—N4—C22 | 106.7 (2) | C15—C20—H20 | 120.2 |
C22—N4—Zn1iii | 119.27 (18) | C4—C9—H9 | 120.0 |
C13—N2—C12 | 108.3 (2) | C8—C9—H9 | 120.0 |
C13—N2—C15 | 126.7 (2) | C8—C9—C4 | 119.9 (3) |
C12—N2—C15 | 124.9 (2) | C18—C19—H19 | 119.9 |
N2—C13—C14 | 123.7 (3) | C20—C19—C18 | 120.1 (3) |
N1—C13—N2 | 109.3 (2) | C20—C19—H19 | 119.9 |
N1—C13—C14 | 127.0 (3) | H1WA—O1W—H1WB | 104.5 |
C13—N1—Zn1 | 129.42 (19) | C7—C6—H6 | 119.5 |
C13—N1—C11 | 106.8 (2) | C7—C6—C5 | 120.9 (2) |
C11—N1—Zn1 | 121.54 (18) | C5—C6—H6 | 119.5 |
C1—O1—Zn1iv | 112.0 (2) | O3—C4—C9 | 115.5 (2) |
N3—C23—C24 | 123.9 (2) | O3—C4—C5 | 124.7 (2) |
N4—C23—N3 | 109.6 (2) | C5—C4—C9 | 119.8 (3) |
N4—C23—C24 | 126.4 (2) | C20—C15—N2 | 120.1 (2) |
C23—C24—H24A | 109.5 | C20—C15—C16 | 121.2 (3) |
C23—C24—H24B | 109.5 | C16—C15—N2 | 118.8 (2) |
C23—C24—H24C | 109.5 | O1—C1—C2 | 119.3 (3) |
H24A—C24—H24B | 109.5 | O2—C1—O1 | 123.4 (3) |
H24A—C24—H24C | 109.5 | O2—C1—C2 | 117.3 (3) |
H24B—C24—H24C | 109.5 | C17—C16—H16 | 120.9 |
N1—C11—H11 | 125.4 | C15—C16—C17 | 118.1 (2) |
C12—C11—N1 | 109.1 (2) | C15—C16—H16 | 120.9 |
C12—C11—H11 | 125.4 | C6—C5—H5 | 120.2 |
C17—C18—H18 | 120.2 | C4—C5—C6 | 119.6 (2) |
C17—C18—C19 | 119.6 (3) | C4—C5—H5 | 120.2 |
C19—C18—H18 | 120.2 | N4—C22—H22 | 125.3 |
C18—C17—N3 | 118.5 (2) | C21—C22—N4 | 109.3 (2) |
C18—C17—C16 | 121.3 (2) | C21—C22—H22 | 125.3 |
C16—C17—N3 | 120.2 (2) | C7—C8—H8 | 119.5 |
O3—C2—H2 | 108.7 | C9—C8—C7 | 121.0 (2) |
O3—C2—C1 | 112.9 (2) | C9—C8—H8 | 119.5 |
O3—C2—C3 | 106.1 (3) | N3—C21—H21 | 126.9 |
C1—C2—H2 | 108.7 | C22—C21—N3 | 106.3 (2) |
C3—C2—H2 | 108.7 | C22—C21—H21 | 126.9 |
C3—C2—C1 | 111.5 (3) | C2—C3—H3A | 109.5 |
C6—C7—C10 | 119.4 (2) | C2—C3—H3B | 109.5 |
C6—C7—C8 | 118.7 (2) | C2—C3—H3C | 109.5 |
C8—C7—C10 | 121.9 (2) | H3A—C3—H3B | 109.5 |
N2—C12—H12 | 126.8 | H3A—C3—H3C | 109.5 |
C11—C12—N2 | 106.4 (2) | H3B—C3—H3C | 109.5 |
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) −x+2, y−1/2, −z+1; (iii) −x, y+1/2, −z+1; (iv) −x+2, y+1/2, −z+1. |
Poly[[µ-1,3-bis(2-methyl-1
H-imidazol-1-yl)benzene][µ-(
S)-4-(1-carboxylatoethoxy)benzoato]zinc(II)] (2-L)
top
Crystal data top
[Zn(C10H8O5)(C14H14N4)] | F(000) = 528 |
Mr = 511.82 | Dx = 1.473 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0631 (8) Å | Cell parameters from 5842 reflections |
b = 11.8412 (7) Å | θ = 3.9–29.8° |
c = 11.6382 (10) Å | µ = 1.11 mm−1 |
β = 112.456 (10)° | T = 293 K |
V = 1154.28 (18) Å3 | Block, clear light yellow |
Z = 2 | 0.15 × 0.1 × 0.1 mm |
Data collection top
Rigaku XtaLAB Pro (Kappa single) diffractometer | 5673 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 5031 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
ω scans | θmax = 30.3°, θmin = 3.8° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −11→12 |
Tmin = 0.467, Tmax = 1.000 | k = −16→16 |
12526 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.036P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.075 | (Δ/σ)max = 0.002 |
S = 0.97 | Δρmax = 0.32 e Å−3 |
5673 reflections | Δρmin = −0.29 e Å−3 |
310 parameters | Absolute structure: Flack x determined using 2014 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
13 restraints | Absolute structure parameter: 0.003 (7) |
Primary atom site location: dual | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.85708 (3) | 0.88907 (3) | 1.09586 (3) | 0.03087 (9) | |
N1 | 0.7886 (3) | 0.90974 (19) | 0.9114 (2) | 0.0354 (6) | |
O3 | 0.8012 (3) | 0.24398 (17) | 1.3363 (2) | 0.0478 (6) | |
O1 | 0.7395 (3) | −0.0119 (2) | 1.1625 (3) | 0.0504 (6) | |
O4 | 0.8516 (3) | 0.73831 (19) | 1.1595 (2) | 0.0479 (6) | |
O5 | 0.5935 (3) | 0.7135 (2) | 1.0510 (3) | 0.0547 (6) | |
N2 | 0.7128 (3) | 0.8826 (3) | 0.71044 (19) | 0.0341 (4) | |
N4 | 0.0995 (3) | 0.8927 (3) | 0.1581 (2) | 0.0378 (5) | |
N3 | 0.3470 (3) | 0.8496 (2) | 0.2766 (2) | 0.0372 (6) | |
C8 | 0.8802 (4) | 0.5311 (2) | 1.2763 (3) | 0.0354 (6) | |
H8 | 0.962002 | 0.583432 | 1.310142 | 0.042* | |
C7 | 0.7426 (3) | 0.5620 (2) | 1.1749 (3) | 0.0313 (6) | |
C10 | 0.7238 (4) | 0.6798 (3) | 1.1236 (3) | 0.0367 (6) | |
C6 | 0.6248 (4) | 0.4821 (3) | 1.1233 (3) | 0.0377 (6) | |
H6 | 0.532931 | 0.501915 | 1.055807 | 0.045* | |
C20 | 0.5285 (3) | 0.8639 (2) | 0.4957 (3) | 0.0332 (7) | |
H20 | 0.465825 | 0.920858 | 0.508407 | 0.040* | |
C13 | 0.7597 (3) | 0.8319 (2) | 0.8240 (3) | 0.0322 (6) | |
C11 | 0.7122 (4) | 0.9980 (3) | 0.7288 (3) | 0.0448 (7) | |
H11 | 0.684595 | 1.053725 | 0.667827 | 0.054* | |
C4 | 0.7758 (4) | 0.3446 (2) | 1.2742 (3) | 0.0341 (6) | |
C19 | 0.4858 (4) | 0.8127 (3) | 0.3796 (3) | 0.0355 (6) | |
C12 | 0.7595 (5) | 1.0138 (3) | 0.8521 (3) | 0.0442 (8) | |
H12 | 0.770887 | 1.083428 | 0.891509 | 0.053* | |
C15 | 0.6672 (4) | 0.8280 (2) | 0.5923 (3) | 0.0331 (6) | |
C14 | 0.7726 (5) | 0.7081 (3) | 0.8456 (4) | 0.0468 (8) | |
H14A | 0.876294 | 0.682787 | 0.852411 | 0.070* | |
H14B | 0.692121 | 0.670328 | 0.777256 | 0.070* | |
H14C | 0.757874 | 0.691004 | 0.921163 | 0.070* | |
C9 | 0.8964 (4) | 0.4243 (2) | 1.3269 (3) | 0.0373 (7) | |
H9 | 0.987084 | 0.405480 | 1.395813 | 0.045* | |
C24 | 0.1477 (4) | 0.8563 (4) | 0.3807 (3) | 0.0548 (12) | |
H24A | 0.172802 | 0.924569 | 0.428911 | 0.082* | |
H24B | 0.203266 | 0.794085 | 0.431798 | 0.082* | |
H24C | 0.034740 | 0.842977 | 0.350696 | 0.082* | |
C1 | 0.8001 (4) | 0.0828 (3) | 1.2059 (3) | 0.0396 (7) | |
C23 | 0.1977 (3) | 0.8678 (3) | 0.2732 (3) | 0.0355 (7) | |
C21 | 0.3419 (4) | 0.8653 (4) | 0.1567 (3) | 0.0524 (11) | |
H21 | 0.426570 | 0.858421 | 0.130609 | 0.063* | |
C22 | 0.1898 (3) | 0.8925 (5) | 0.0859 (3) | 0.0474 (7) | |
H22 | 0.151636 | 0.908670 | 0.001344 | 0.057* | |
C2 | 0.7127 (4) | 0.1447 (2) | 1.2755 (4) | 0.0433 (8) | |
H2 | 0.605732 | 0.166403 | 1.217639 | 0.052* | |
C18 | 0.5785 (4) | 0.7275 (3) | 0.3603 (3) | 0.0447 (7) | |
H18 | 0.548406 | 0.693124 | 0.282865 | 0.054* | |
C16 | 0.7633 (4) | 0.7439 (3) | 0.5739 (3) | 0.0410 (7) | |
H16 | 0.856807 | 0.721652 | 0.638363 | 0.049* | |
C5 | 0.6404 (4) | 0.3721 (3) | 1.1700 (3) | 0.0410 (7) | |
H5 | 0.561952 | 0.318316 | 1.132368 | 0.049* | |
C17 | 0.7166 (4) | 0.6938 (3) | 0.4574 (4) | 0.0470 (8) | |
H17 | 0.779074 | 0.636791 | 0.444391 | 0.056* | |
O2 | 0.9116 (5) | 0.1261 (3) | 1.1897 (5) | 0.1081 (17) | |
C3 | 0.7006 (10) | 0.0728 (4) | 1.3796 (6) | 0.100 (2) | |
H3A | 0.805896 | 0.055284 | 1.438225 | 0.150* | |
H3B | 0.644849 | 0.004096 | 1.345619 | 0.150* | |
H3C | 0.643493 | 0.113673 | 1.420804 | 0.150* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.03162 (14) | 0.03157 (14) | 0.02546 (14) | 0.00130 (16) | 0.00646 (10) | 0.00020 (16) |
N1 | 0.0354 (11) | 0.0372 (17) | 0.0274 (11) | 0.0047 (10) | 0.0050 (9) | 0.0011 (9) |
O3 | 0.0685 (16) | 0.0252 (9) | 0.0402 (13) | −0.0071 (10) | 0.0102 (12) | −0.0024 (9) |
O1 | 0.0443 (13) | 0.0434 (12) | 0.0621 (17) | −0.0041 (10) | 0.0188 (12) | −0.0228 (11) |
O4 | 0.0532 (14) | 0.0354 (11) | 0.0477 (15) | −0.0033 (10) | 0.0110 (12) | 0.0088 (10) |
O5 | 0.0475 (14) | 0.0558 (14) | 0.0552 (16) | 0.0158 (12) | 0.0134 (12) | 0.0189 (12) |
N2 | 0.0346 (10) | 0.0395 (11) | 0.0243 (10) | 0.0042 (14) | 0.0069 (8) | 0.0041 (14) |
N4 | 0.0324 (10) | 0.0519 (12) | 0.0265 (10) | −0.0003 (16) | 0.0086 (8) | 0.0008 (16) |
N3 | 0.0298 (12) | 0.0560 (14) | 0.0236 (12) | 0.0013 (10) | 0.0078 (9) | 0.0017 (10) |
C8 | 0.0307 (14) | 0.0304 (13) | 0.0385 (16) | −0.0025 (11) | 0.0059 (12) | −0.0030 (12) |
C7 | 0.0328 (14) | 0.0347 (13) | 0.0269 (14) | 0.0045 (11) | 0.0118 (11) | −0.0015 (11) |
C10 | 0.0436 (17) | 0.0363 (14) | 0.0336 (16) | 0.0075 (12) | 0.0186 (14) | 0.0023 (12) |
C6 | 0.0332 (15) | 0.0436 (16) | 0.0306 (15) | −0.0009 (13) | 0.0057 (12) | 0.0018 (12) |
C20 | 0.0284 (12) | 0.0431 (19) | 0.0256 (12) | 0.0037 (10) | 0.0076 (10) | 0.0006 (11) |
C13 | 0.0307 (14) | 0.0370 (15) | 0.0276 (15) | 0.0030 (11) | 0.0096 (12) | 0.0006 (12) |
C11 | 0.058 (2) | 0.0378 (15) | 0.0338 (17) | 0.0048 (14) | 0.0118 (15) | 0.0062 (13) |
C4 | 0.0438 (17) | 0.0267 (11) | 0.0319 (15) | −0.0012 (11) | 0.0145 (13) | −0.0050 (11) |
C19 | 0.0297 (14) | 0.0483 (16) | 0.0268 (14) | 0.0001 (12) | 0.0091 (12) | 0.0034 (12) |
C12 | 0.058 (2) | 0.0348 (15) | 0.0346 (18) | −0.0009 (15) | 0.0115 (15) | 0.0005 (14) |
C15 | 0.0312 (14) | 0.0409 (15) | 0.0252 (14) | 0.0014 (12) | 0.0086 (11) | 0.0008 (11) |
C14 | 0.067 (2) | 0.0390 (16) | 0.0380 (19) | 0.0087 (16) | 0.0240 (17) | 0.0037 (14) |
C9 | 0.0341 (15) | 0.0304 (13) | 0.0390 (17) | 0.0030 (10) | 0.0045 (13) | −0.0005 (11) |
C24 | 0.0352 (16) | 0.102 (4) | 0.0277 (15) | −0.0012 (16) | 0.0124 (13) | 0.0015 (17) |
C1 | 0.0401 (17) | 0.0376 (15) | 0.0426 (19) | −0.0037 (13) | 0.0174 (15) | −0.0049 (14) |
C23 | 0.0320 (13) | 0.047 (2) | 0.0254 (13) | −0.0004 (12) | 0.0082 (10) | 0.0003 (12) |
C21 | 0.0376 (15) | 0.091 (3) | 0.0305 (15) | 0.0053 (17) | 0.0153 (12) | 0.0085 (17) |
C22 | 0.0395 (14) | 0.077 (2) | 0.0249 (12) | 0.002 (2) | 0.0109 (11) | 0.010 (2) |
C2 | 0.054 (2) | 0.0285 (13) | 0.054 (2) | −0.0101 (13) | 0.0278 (17) | −0.0099 (13) |
C18 | 0.0428 (17) | 0.058 (2) | 0.0297 (16) | 0.0048 (15) | 0.0104 (14) | −0.0078 (14) |
C16 | 0.0335 (15) | 0.0540 (17) | 0.0331 (16) | 0.0101 (13) | 0.0098 (13) | 0.0018 (14) |
C5 | 0.0388 (14) | 0.042 (2) | 0.0353 (14) | −0.0102 (14) | 0.0061 (11) | −0.0035 (14) |
C17 | 0.0452 (19) | 0.058 (2) | 0.0368 (19) | 0.0155 (15) | 0.0153 (15) | −0.0019 (15) |
O2 | 0.098 (3) | 0.084 (2) | 0.188 (5) | −0.037 (2) | 0.106 (3) | −0.054 (3) |
C3 | 0.197 (7) | 0.051 (2) | 0.094 (4) | −0.043 (3) | 0.103 (5) | −0.021 (3) |
Geometric parameters (Å, º) top
Zn1—N1 | 2.010 (2) | C11—C12 | 1.345 (5) |
Zn1—O1i | 1.935 (2) | C4—C9 | 1.396 (4) |
Zn1—O4 | 1.941 (2) | C4—C5 | 1.395 (4) |
Zn1—N4ii | 2.034 (2) | C19—C18 | 1.385 (5) |
N1—C13 | 1.322 (4) | C12—H12 | 0.9300 |
N1—C12 | 1.387 (4) | C15—C16 | 1.392 (4) |
O3—C4 | 1.366 (4) | C14—H14A | 0.9600 |
O3—C2 | 1.446 (4) | C14—H14B | 0.9600 |
O1—C1 | 1.265 (4) | C14—H14C | 0.9600 |
O4—C10 | 1.275 (4) | C9—H9 | 0.9300 |
O5—C10 | 1.227 (4) | C24—H24A | 0.9600 |
N2—C13 | 1.363 (4) | C24—H24B | 0.9600 |
N2—C11 | 1.383 (5) | C24—H24C | 0.9600 |
N2—C15 | 1.430 (4) | C24—C23 | 1.491 (4) |
N4—C23 | 1.328 (4) | C1—C2 | 1.519 (4) |
N4—C22 | 1.378 (3) | C1—O2 | 1.210 (4) |
N3—C19 | 1.435 (4) | C21—H21 | 0.9300 |
N3—C23 | 1.356 (4) | C21—C22 | 1.347 (4) |
N3—C21 | 1.391 (4) | C22—H22 | 0.9300 |
C8—H8 | 0.9300 | C2—H2 | 0.9800 |
C8—C7 | 1.399 (4) | C2—C3 | 1.519 (6) |
C8—C9 | 1.379 (4) | C18—H18 | 0.9300 |
C7—C10 | 1.501 (4) | C18—C17 | 1.386 (5) |
C7—C6 | 1.381 (4) | C16—H16 | 0.9300 |
C6—H6 | 0.9300 | C16—C17 | 1.389 (5) |
C6—C5 | 1.397 (5) | C5—H5 | 0.9300 |
C20—H20 | 0.9300 | C17—H17 | 0.9300 |
C20—C19 | 1.393 (4) | C3—H3A | 0.9600 |
C20—C15 | 1.394 (4) | C3—H3B | 0.9600 |
C13—C14 | 1.485 (4) | C3—H3C | 0.9600 |
C11—H11 | 0.9300 | | |
| | | |
N1—Zn1—N4ii | 103.21 (9) | C16—C15—C20 | 121.2 (3) |
O1i—Zn1—N1 | 111.21 (11) | C13—C14—H14A | 109.5 |
O1i—Zn1—O4 | 107.84 (12) | C13—C14—H14B | 109.5 |
O1i—Zn1—N4ii | 122.00 (12) | C13—C14—H14C | 109.5 |
O4—Zn1—N1 | 118.51 (10) | H14A—C14—H14B | 109.5 |
O4—Zn1—N4ii | 93.74 (13) | H14A—C14—H14C | 109.5 |
C13—N1—Zn1 | 128.8 (2) | H14B—C14—H14C | 109.5 |
C13—N1—C12 | 107.0 (3) | C8—C9—C4 | 119.7 (3) |
C12—N1—Zn1 | 124.2 (2) | C8—C9—H9 | 120.2 |
C4—O3—C2 | 120.0 (3) | C4—C9—H9 | 120.2 |
C1—O1—Zn1iii | 118.4 (2) | H24A—C24—H24B | 109.5 |
C10—O4—Zn1 | 121.8 (2) | H24A—C24—H24C | 109.5 |
C13—N2—C11 | 107.7 (3) | H24B—C24—H24C | 109.5 |
C13—N2—C15 | 127.0 (3) | C23—C24—H24A | 109.5 |
C11—N2—C15 | 125.3 (3) | C23—C24—H24B | 109.5 |
C23—N4—Zn1iv | 124.79 (19) | C23—C24—H24C | 109.5 |
C23—N4—C22 | 106.8 (2) | O1—C1—C2 | 113.9 (3) |
C22—N4—Zn1iv | 126.53 (18) | O2—C1—O1 | 125.0 (3) |
C23—N3—C19 | 128.2 (2) | O2—C1—C2 | 121.0 (3) |
C23—N3—C21 | 107.4 (2) | N4—C23—N3 | 109.9 (2) |
C21—N3—C19 | 124.2 (3) | N4—C23—C24 | 124.4 (3) |
C7—C8—H8 | 119.5 | N3—C23—C24 | 125.6 (3) |
C9—C8—H8 | 119.5 | N3—C21—H21 | 126.9 |
C9—C8—C7 | 121.0 (3) | C22—C21—N3 | 106.2 (3) |
C8—C7—C10 | 120.5 (3) | C22—C21—H21 | 126.9 |
C6—C7—C8 | 118.7 (3) | N4—C22—H22 | 125.2 |
C6—C7—C10 | 120.8 (3) | C21—C22—N4 | 109.6 (3) |
O4—C10—C7 | 115.1 (3) | C21—C22—H22 | 125.2 |
O5—C10—O4 | 124.3 (3) | O3—C2—C1 | 110.4 (3) |
O5—C10—C7 | 120.6 (3) | O3—C2—H2 | 109.9 |
C7—C6—H6 | 119.2 | O3—C2—C3 | 105.1 (3) |
C7—C6—C5 | 121.5 (3) | C1—C2—H2 | 109.9 |
C5—C6—H6 | 119.2 | C3—C2—C1 | 111.5 (3) |
C19—C20—H20 | 120.6 | C3—C2—H2 | 109.9 |
C19—C20—C15 | 118.7 (3) | C19—C18—H18 | 120.3 |
C15—C20—H20 | 120.6 | C19—C18—C17 | 119.5 (3) |
N1—C13—N2 | 109.6 (3) | C17—C18—H18 | 120.3 |
N1—C13—C14 | 125.3 (3) | C15—C16—H16 | 120.7 |
N2—C13—C14 | 125.1 (3) | C17—C16—C15 | 118.7 (3) |
N2—C11—H11 | 126.8 | C17—C16—H16 | 120.7 |
C12—C11—N2 | 106.4 (3) | C6—C5—H5 | 120.6 |
C12—C11—H11 | 126.8 | C4—C5—C6 | 118.7 (3) |
O3—C4—C9 | 114.3 (3) | C4—C5—H5 | 120.6 |
O3—C4—C5 | 125.3 (3) | C18—C17—C16 | 121.1 (3) |
C5—C4—C9 | 120.3 (3) | C18—C17—H17 | 119.5 |
C20—C19—N3 | 120.5 (3) | C16—C17—H17 | 119.5 |
C18—C19—N3 | 118.6 (3) | C2—C3—H3A | 109.5 |
C18—C19—C20 | 120.8 (3) | C2—C3—H3B | 109.5 |
N1—C12—H12 | 125.4 | C2—C3—H3C | 109.5 |
C11—C12—N1 | 109.3 (3) | H3A—C3—H3B | 109.5 |
C11—C12—H12 | 125.4 | H3A—C3—H3C | 109.5 |
C20—C15—N2 | 118.6 (3) | H3B—C3—H3C | 109.5 |
C16—C15—N2 | 120.2 (3) | | |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z+1; (iii) x, y−1, z; (iv) x−1, y, z−1. |
Poly[[µ-1,3-bis(2-methyl-1
H-imidazol-1-yl)benzene][µ-(
R)-4-(1-carboxylatoethoxy)benzoato]zinc(II)] (2-D)
top
Crystal data top
[Zn(C10H8O5)(C14H14N4)] | F(000) = 528 |
Mr = 511.82 | Dx = 1.473 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0571 (6) Å | Cell parameters from 7631 reflections |
b = 11.8439 (6) Å | θ = 4.0–30.1° |
c = 11.6393 (7) Å | µ = 1.11 mm−1 |
β = 112.441 (8)° | T = 293 K |
V = 1154.01 (13) Å3 | Block, clear light yellow |
Z = 2 | 0.2 × 0.2 × 0.2 mm |
Data collection top
Rigaku XtaLAB Pro (Kappa single) diffractometer | 5843 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 5479 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 30.2°, θmin = 3.6° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −12→12 |
Tmin = 0.827, Tmax = 1.000 | k = −16→16 |
13923 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.027 | w = 1/[σ2(Fo2) + (0.0458P)2 + 0.0091P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.070 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.31 e Å−3 |
5843 reflections | Δρmin = −0.21 e Å−3 |
310 parameters | Absolute structure: Flack x determined using 2321 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
13 restraints | Absolute structure parameter: −0.010 (5) |
Primary atom site location: dual | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.14333 (3) | 0.82617 (2) | −0.09573 (2) | 0.02945 (8) | |
O4 | 0.1480 (3) | −0.02288 (17) | −0.1597 (2) | 0.0459 (5) | |
N1 | 0.2120 (2) | 0.80530 (17) | 0.08906 (17) | 0.0339 (5) | |
O1 | 0.2605 (2) | 0.72742 (17) | −0.1628 (2) | 0.0479 (5) | |
O3 | 0.1988 (3) | 0.47126 (15) | −0.33648 (19) | 0.0464 (5) | |
N4 | 0.9002 (2) | 0.8222 (3) | 0.84149 (16) | 0.0355 (4) | |
O5 | 0.4068 (3) | 0.0020 (2) | −0.0510 (2) | 0.0530 (5) | |
N2 | 0.2880 (2) | 0.8323 (2) | 0.28963 (15) | 0.0326 (4) | |
N3 | 0.6531 (2) | 0.8655 (2) | 0.72319 (17) | 0.0360 (5) | |
C10 | 0.2762 (3) | 0.0355 (2) | −0.1235 (2) | 0.0348 (5) | |
C20 | 0.4716 (3) | 0.8511 (2) | 0.5045 (2) | 0.0317 (5) | |
H20 | 0.534121 | 0.793870 | 0.491951 | 0.038* | |
C11 | 0.2407 (4) | 0.7011 (2) | 0.1479 (3) | 0.0421 (6) | |
H11 | 0.229301 | 0.631469 | 0.108436 | 0.050* | |
C7 | 0.2572 (3) | 0.1535 (2) | −0.1753 (2) | 0.0297 (4) | |
C24 | 0.8529 (3) | 0.8586 (4) | 0.6197 (2) | 0.0532 (10) | |
H24A | 0.965234 | 0.874447 | 0.649571 | 0.080* | |
H24B | 0.794626 | 0.919081 | 0.566932 | 0.080* | |
H24C | 0.831059 | 0.789323 | 0.573312 | 0.080* | |
C15 | 0.3330 (3) | 0.8871 (2) | 0.4079 (2) | 0.0315 (5) | |
C6 | 0.3753 (3) | 0.2336 (2) | −0.1233 (2) | 0.0368 (5) | |
H6 | 0.467312 | 0.213973 | −0.055946 | 0.044* | |
C8 | 0.1195 (3) | 0.1841 (2) | −0.2768 (2) | 0.0338 (5) | |
H8 | 0.037744 | 0.131796 | −0.310717 | 0.041* | |
C19 | 0.5145 (3) | 0.9027 (2) | 0.6202 (2) | 0.0338 (5) | |
C16 | 0.2361 (3) | 0.9708 (3) | 0.4255 (2) | 0.0389 (5) | |
H16 | 0.142513 | 0.992795 | 0.360870 | 0.047* | |
C21 | 0.6573 (3) | 0.8499 (3) | 0.8432 (2) | 0.0490 (9) | |
H21 | 0.572508 | 0.857011 | 0.869165 | 0.059* | |
C13 | 0.2411 (3) | 0.8831 (2) | 0.1763 (2) | 0.0310 (5) | |
C22 | 0.8093 (3) | 0.8224 (4) | 0.9138 (2) | 0.0462 (6) | |
H22 | 0.847378 | 0.805946 | 0.998267 | 0.055* | |
C14 | 0.2281 (4) | 1.0072 (2) | 0.1545 (3) | 0.0450 (6) | |
H14A | 0.239374 | 1.023949 | 0.077520 | 0.067* | |
H14B | 0.310764 | 1.044880 | 0.221408 | 0.067* | |
H14C | 0.125608 | 1.032907 | 0.150324 | 0.067* | |
C12 | 0.2879 (4) | 0.7168 (2) | 0.2715 (2) | 0.0431 (6) | |
H12 | 0.314848 | 0.661131 | 0.332486 | 0.052* | |
C1 | 0.2004 (3) | 0.6323 (2) | −0.2054 (2) | 0.0374 (5) | |
C23 | 0.8028 (3) | 0.8475 (2) | 0.7271 (2) | 0.0336 (6) | |
C9 | 0.1036 (3) | 0.2911 (2) | −0.3273 (2) | 0.0344 (5) | |
H9 | 0.013029 | 0.309918 | −0.396323 | 0.041* | |
C4 | 0.2238 (3) | 0.3706 (2) | −0.2746 (2) | 0.0327 (5) | |
C18 | 0.4218 (3) | 0.9876 (3) | 0.6399 (3) | 0.0425 (6) | |
H18 | 0.452063 | 1.021965 | 0.717347 | 0.051* | |
C17 | 0.2825 (4) | 1.0211 (3) | 0.5424 (3) | 0.0457 (7) | |
H17 | 0.219578 | 1.077824 | 0.555471 | 0.055* | |
C5 | 0.3585 (3) | 0.3433 (2) | −0.1703 (2) | 0.0393 (6) | |
H5 | 0.436336 | 0.397461 | −0.132494 | 0.047* | |
C2 | 0.2863 (3) | 0.5705 (2) | −0.2763 (3) | 0.0409 (6) | |
H2 | 0.393649 | 0.548900 | −0.219026 | 0.049* | |
O2 | 0.0887 (4) | 0.5886 (3) | −0.1895 (5) | 0.1041 (14) | |
C3 | 0.2982 (8) | 0.6431 (3) | −0.3794 (5) | 0.0956 (19) | |
H3A | 0.357363 | 0.603448 | −0.419899 | 0.143* | |
H3B | 0.351927 | 0.712371 | −0.345090 | 0.143* | |
H3C | 0.192885 | 0.659456 | −0.438778 | 0.143* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.02966 (12) | 0.03049 (12) | 0.02352 (11) | 0.00130 (12) | 0.00491 (8) | 0.00027 (12) |
O4 | 0.0505 (11) | 0.0337 (9) | 0.0458 (11) | −0.0033 (8) | 0.0100 (9) | 0.0088 (8) |
N1 | 0.0350 (9) | 0.0362 (14) | 0.0250 (8) | 0.0037 (8) | 0.0052 (7) | 0.0012 (7) |
O1 | 0.0434 (10) | 0.0409 (10) | 0.0577 (12) | −0.0032 (9) | 0.0173 (9) | −0.0211 (10) |
O3 | 0.0676 (13) | 0.0238 (8) | 0.0390 (10) | −0.0075 (8) | 0.0107 (9) | −0.0038 (8) |
N4 | 0.0289 (8) | 0.0506 (10) | 0.0230 (7) | −0.0010 (13) | 0.0054 (6) | 0.0025 (12) |
O5 | 0.0447 (11) | 0.0540 (12) | 0.0542 (12) | 0.0149 (10) | 0.0120 (10) | 0.0211 (11) |
N2 | 0.0309 (8) | 0.0388 (9) | 0.0226 (7) | 0.0053 (11) | 0.0042 (6) | 0.0032 (11) |
N3 | 0.0286 (9) | 0.0561 (12) | 0.0198 (8) | 0.0008 (8) | 0.0053 (7) | 0.0026 (8) |
C10 | 0.0408 (13) | 0.0349 (12) | 0.0323 (12) | 0.0075 (10) | 0.0177 (11) | 0.0033 (10) |
C20 | 0.0279 (10) | 0.0401 (15) | 0.0250 (9) | 0.0041 (8) | 0.0076 (8) | 0.0011 (8) |
C11 | 0.0538 (16) | 0.0326 (13) | 0.0334 (13) | 0.0004 (12) | 0.0095 (12) | 0.0008 (11) |
C7 | 0.0301 (10) | 0.0320 (11) | 0.0267 (10) | 0.0031 (9) | 0.0106 (9) | −0.0011 (9) |
C24 | 0.0327 (12) | 0.103 (3) | 0.0240 (10) | −0.0003 (14) | 0.0103 (9) | 0.0033 (14) |
C15 | 0.0276 (10) | 0.0407 (12) | 0.0231 (10) | 0.0001 (9) | 0.0065 (8) | 0.0001 (9) |
C6 | 0.0289 (11) | 0.0453 (14) | 0.0296 (11) | −0.0016 (10) | 0.0038 (9) | 0.0028 (10) |
C8 | 0.0307 (11) | 0.0278 (10) | 0.0362 (12) | −0.0026 (9) | 0.0051 (9) | −0.0022 (9) |
C19 | 0.0269 (10) | 0.0480 (13) | 0.0234 (10) | −0.0001 (9) | 0.0062 (9) | 0.0022 (9) |
C16 | 0.0320 (11) | 0.0513 (14) | 0.0300 (11) | 0.0088 (11) | 0.0082 (9) | 0.0005 (11) |
C21 | 0.0362 (11) | 0.086 (3) | 0.0263 (10) | 0.0052 (14) | 0.0140 (9) | 0.0076 (13) |
C13 | 0.0279 (10) | 0.0370 (12) | 0.0251 (10) | 0.0036 (9) | 0.0068 (8) | 0.0008 (10) |
C22 | 0.0377 (11) | 0.0752 (18) | 0.0237 (9) | 0.0034 (18) | 0.0094 (8) | 0.0093 (17) |
C14 | 0.0658 (19) | 0.0370 (13) | 0.0366 (14) | 0.0093 (13) | 0.0247 (13) | 0.0039 (12) |
C12 | 0.0576 (16) | 0.0354 (12) | 0.0310 (12) | 0.0062 (11) | 0.0112 (12) | 0.0060 (10) |
C1 | 0.0375 (13) | 0.0356 (12) | 0.0397 (14) | −0.0028 (10) | 0.0153 (12) | −0.0028 (11) |
C23 | 0.0299 (10) | 0.0452 (17) | 0.0231 (9) | −0.0017 (9) | 0.0072 (8) | 0.0001 (9) |
C9 | 0.0314 (11) | 0.0285 (10) | 0.0342 (11) | 0.0015 (8) | 0.0023 (9) | 0.0000 (9) |
C4 | 0.0424 (13) | 0.0253 (9) | 0.0305 (10) | −0.0013 (9) | 0.0140 (10) | −0.0041 (9) |
C18 | 0.0403 (13) | 0.0565 (16) | 0.0279 (11) | 0.0042 (12) | 0.0098 (11) | −0.0066 (11) |
C17 | 0.0430 (14) | 0.0585 (17) | 0.0352 (13) | 0.0158 (13) | 0.0147 (12) | −0.0019 (13) |
C5 | 0.0380 (11) | 0.0386 (16) | 0.0340 (10) | −0.0119 (11) | 0.0058 (9) | −0.0042 (11) |
C2 | 0.0516 (15) | 0.0263 (11) | 0.0498 (15) | −0.0098 (11) | 0.0248 (13) | −0.0096 (11) |
O2 | 0.095 (2) | 0.078 (2) | 0.183 (4) | −0.0364 (18) | 0.102 (3) | −0.051 (2) |
C3 | 0.188 (6) | 0.0495 (19) | 0.091 (3) | −0.043 (3) | 0.100 (4) | −0.023 (2) |
Geometric parameters (Å, º) top
Zn1—O4i | 1.944 (2) | C15—C16 | 1.390 (4) |
Zn1—N1 | 2.0131 (19) | C6—H6 | 0.9300 |
Zn1—O1 | 1.9328 (19) | C6—C5 | 1.396 (4) |
Zn1—N4ii | 2.0388 (17) | C8—H8 | 0.9300 |
O4—C10 | 1.277 (3) | C8—C9 | 1.381 (4) |
N1—C11 | 1.388 (3) | C19—C18 | 1.384 (4) |
N1—C13 | 1.321 (3) | C16—H16 | 0.9300 |
O1—C1 | 1.266 (3) | C16—C17 | 1.395 (4) |
O3—C4 | 1.367 (3) | C21—H21 | 0.9300 |
O3—C2 | 1.441 (3) | C21—C22 | 1.346 (4) |
N4—C22 | 1.384 (3) | C13—C14 | 1.490 (4) |
N4—C23 | 1.321 (3) | C22—H22 | 0.9300 |
O5—C10 | 1.227 (3) | C14—H14A | 0.9600 |
N2—C15 | 1.433 (3) | C14—H14B | 0.9600 |
N2—C13 | 1.361 (3) | C14—H14C | 0.9600 |
N2—C12 | 1.384 (4) | C12—H12 | 0.9300 |
N3—C19 | 1.435 (3) | C1—C2 | 1.521 (3) |
N3—C21 | 1.396 (3) | C1—O2 | 1.212 (4) |
N3—C23 | 1.356 (3) | C9—H9 | 0.9300 |
C10—C7 | 1.506 (3) | C9—C4 | 1.393 (3) |
C20—H20 | 0.9300 | C4—C5 | 1.391 (4) |
C20—C15 | 1.395 (3) | C18—H18 | 0.9300 |
C20—C19 | 1.392 (3) | C18—C17 | 1.394 (4) |
C11—H11 | 0.9300 | C17—H17 | 0.9300 |
C11—C12 | 1.348 (4) | C5—H5 | 0.9300 |
C7—C6 | 1.384 (4) | C2—H2 | 0.9800 |
C7—C8 | 1.399 (3) | C2—C3 | 1.513 (5) |
C24—H24A | 0.9600 | C3—H3A | 0.9600 |
C24—H24B | 0.9600 | C3—H3B | 0.9600 |
C24—H24C | 0.9600 | C3—H3C | 0.9600 |
C24—C23 | 1.489 (3) | | |
| | | |
O4i—Zn1—N1 | 118.65 (9) | C17—C16—H16 | 120.8 |
O4i—Zn1—N4ii | 93.58 (11) | N3—C21—H21 | 127.1 |
N1—Zn1—N4ii | 103.35 (8) | C22—C21—N3 | 105.9 (2) |
O1—Zn1—O4i | 107.83 (10) | C22—C21—H21 | 127.1 |
O1—Zn1—N1 | 111.34 (9) | N1—C13—N2 | 109.5 (2) |
O1—Zn1—N4ii | 121.71 (10) | N1—C13—C14 | 125.3 (2) |
C10—O4—Zn1iii | 121.45 (17) | N2—C13—C14 | 125.2 (2) |
C11—N1—Zn1 | 124.06 (17) | N4—C22—H22 | 125.2 |
C13—N1—Zn1 | 128.72 (17) | C21—C22—N4 | 109.7 (2) |
C13—N1—C11 | 107.2 (2) | C21—C22—H22 | 125.2 |
C1—O1—Zn1 | 118.44 (18) | C13—C14—H14A | 109.5 |
C4—O3—C2 | 120.4 (2) | C13—C14—H14B | 109.5 |
C22—N4—Zn1iv | 126.45 (14) | C13—C14—H14C | 109.5 |
C23—N4—Zn1iv | 124.78 (16) | H14A—C14—H14B | 109.5 |
C23—N4—C22 | 106.81 (19) | H14A—C14—H14C | 109.5 |
C13—N2—C15 | 126.8 (3) | H14B—C14—H14C | 109.5 |
C13—N2—C12 | 107.9 (2) | N2—C12—H12 | 126.9 |
C12—N2—C15 | 125.2 (2) | C11—C12—N2 | 106.3 (2) |
C21—N3—C19 | 123.9 (2) | C11—C12—H12 | 126.9 |
C23—N3—C19 | 128.42 (19) | O1—C1—C2 | 114.1 (2) |
C23—N3—C21 | 107.53 (19) | O2—C1—O1 | 125.4 (3) |
O4—C10—C7 | 114.8 (2) | O2—C1—C2 | 120.5 (3) |
O5—C10—O4 | 124.6 (3) | N4—C23—N3 | 110.10 (19) |
O5—C10—C7 | 120.6 (2) | N4—C23—C24 | 124.5 (2) |
C15—C20—H20 | 120.7 | N3—C23—C24 | 125.4 (2) |
C19—C20—H20 | 120.7 | C8—C9—H9 | 120.1 |
C19—C20—C15 | 118.6 (2) | C8—C9—C4 | 119.7 (2) |
N1—C11—H11 | 125.4 | C4—C9—H9 | 120.1 |
C12—C11—N1 | 109.1 (2) | O3—C4—C9 | 114.4 (2) |
C12—C11—H11 | 125.4 | O3—C4—C5 | 125.2 (2) |
C6—C7—C10 | 120.7 (2) | C5—C4—C9 | 120.4 (2) |
C6—C7—C8 | 118.9 (2) | C19—C18—H18 | 120.3 |
C8—C7—C10 | 120.5 (2) | C19—C18—C17 | 119.3 (3) |
H24A—C24—H24B | 109.5 | C17—C18—H18 | 120.3 |
H24A—C24—H24C | 109.5 | C16—C17—H17 | 119.5 |
H24B—C24—H24C | 109.5 | C18—C17—C16 | 121.0 (3) |
C23—C24—H24A | 109.5 | C18—C17—H17 | 119.5 |
C23—C24—H24B | 109.5 | C6—C5—H5 | 120.5 |
C23—C24—H24C | 109.5 | C4—C5—C6 | 119.1 (2) |
C20—C15—N2 | 118.3 (2) | C4—C5—H5 | 120.5 |
C16—C15—N2 | 120.0 (2) | O3—C2—C1 | 110.8 (2) |
C16—C15—C20 | 121.6 (2) | O3—C2—H2 | 109.6 |
C7—C6—H6 | 119.4 | O3—C2—C3 | 105.7 (3) |
C7—C6—C5 | 121.1 (2) | C1—C2—H2 | 109.6 |
C5—C6—H6 | 119.4 | C3—C2—C1 | 111.3 (3) |
C7—C8—H8 | 119.6 | C3—C2—H2 | 109.6 |
C9—C8—C7 | 120.8 (2) | C2—C3—H3A | 109.5 |
C9—C8—H8 | 119.6 | C2—C3—H3B | 109.5 |
C20—C19—N3 | 120.3 (2) | C2—C3—H3C | 109.5 |
C18—C19—N3 | 118.6 (2) | H3A—C3—H3B | 109.5 |
C18—C19—C20 | 121.1 (2) | H3A—C3—H3C | 109.5 |
C15—C16—H16 | 120.8 | H3B—C3—H3C | 109.5 |
C15—C16—C17 | 118.4 (2) | | |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y, z−1; (iii) x, y−1, z; (iv) x+1, y, z+1. |