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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620000182/jx3053sup1.cif
Contains datablocks 1-L, 1-D, 2-L, 2-D, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620000182/jx30531-Lsup2.hkl
Contains datablock 1-L

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620000182/jx30531-Dsup3.hkl
Contains datablock 1-D

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620000182/jx30532-Lsup4.hkl
Contains datablock 2-L

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620000182/jx30532-Dsup5.hkl
Contains datablock 2-D

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229620000182/jx3053sup6.pdf
Additional figures and tables

CCDC references: 1958857; 1958858; 1958856; 1946491

Computing details top

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-1H-imidazol-1-yl)benzene][µ-(S)-4-(1-carboxylatoethoxy)benzoato]zinc(II)] monohydrate] (1-L) top
Crystal data top
[Zn(C10H8O5)(C14H14N4)]·H2OF(000) = 548
Mr = 529.84Dx = 1.491 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 8.2880 (4) ÅCell parameters from 8441 reflections
b = 14.3767 (7) Åθ = 3.9–29.8°
c = 10.2288 (6) ŵ = 1.09 mm1
β = 104.514 (5)°T = 293 K
V = 1179.91 (11) Å3Needle, clear light colourless
Z = 20.3 × 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 Source5693 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ω scansθmax = 30.2°, θmin = 3.8°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
h = 1111
Tmin = 0.478, Tmax = 1.000k = 1920
19699 measured reflectionsl = 1314
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-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 = 1.00Δρmax = 0.28 e Å3
6194 reflectionsΔρmin = 0.21 e Å3
322 parametersAbsolute structure: Flack x determined using 2428 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute 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
xyzUiso*/Ueq
Zn10.51793 (3)0.74584 (2)0.59921 (3)0.02583 (9)
O40.3271 (3)0.67670 (18)0.4913 (2)0.0396 (5)
N41.3900 (3)0.27523 (16)0.5652 (2)0.0286 (5)
O30.3244 (3)0.47615 (16)0.1553 (2)0.0358 (5)
O50.2201 (3)0.6331 (2)0.6615 (2)0.0479 (6)
N20.8508 (3)0.54199 (15)0.7928 (2)0.0261 (4)
N31.2466 (3)0.30978 (17)0.7128 (2)0.0289 (5)
N10.6837 (3)0.66032 (16)0.7219 (2)0.0268 (4)
C130.6972 (3)0.56792 (19)0.7187 (3)0.0260 (5)
O10.4270 (3)0.34784 (17)0.3121 (3)0.0467 (6)
C231.2460 (3)0.30886 (18)0.5804 (3)0.0267 (5)
C241.1000 (4)0.3374 (2)0.4698 (3)0.0338 (6)
H24A1.0697370.4002390.4845390.051*
H24B1.0076040.2968780.4689870.051*
H24C1.1286200.3333030.3846710.051*
C110.8337 (4)0.69346 (19)0.8015 (3)0.0314 (6)
H110.8589320.7556680.8218010.038*
C181.0489 (4)0.2708 (2)0.8434 (3)0.0343 (6)
H181.0940390.2112560.8553550.041*
C100.2150 (3)0.63880 (19)0.5398 (3)0.0290 (5)
C140.5687 (4)0.5007 (2)0.6464 (3)0.0377 (6)
H14A0.6221450.4499180.6130230.057*
H14B0.4938570.5314820.5721320.057*
H14C0.5072250.4773570.7074810.057*
C191.1116 (3)0.33627 (19)0.7707 (3)0.0270 (5)
C70.0706 (3)0.59693 (18)0.4381 (3)0.0253 (5)
C20.4930 (3)0.4819 (2)0.1681 (3)0.0340 (6)
H20.5078370.5414910.2102630.041*
C120.9374 (4)0.6209 (2)0.8448 (3)0.0322 (6)
H121.0457140.6237450.8990220.039*
C90.0443 (4)0.5212 (2)0.2242 (3)0.0308 (6)
H90.0300800.4967580.1436110.037*
C40.1995 (3)0.51568 (19)0.2538 (3)0.0276 (5)
C221.4847 (3)0.2532 (3)0.6940 (3)0.0331 (6)
H221.5920100.2287310.7138740.040*
C60.0835 (3)0.5887 (2)0.4678 (3)0.0296 (5)
H60.0962500.6101500.5503860.035*
O1W0.3209 (5)0.7408 (4)0.9013 (3)0.0882 (12)
H1WA0.3061040.6968650.8439160.132*
H1WB0.3596030.7852330.8636010.132*
C50.2188 (3)0.5491 (2)0.3768 (3)0.0316 (6)
H50.3214330.5448770.3976670.038*
C160.8513 (4)0.3838 (2)0.8826 (3)0.0327 (6)
H160.7641990.4000800.9203990.039*
O20.6857 (4)0.3961 (3)0.2546 (5)0.0851 (13)
C150.9167 (3)0.44873 (18)0.8095 (3)0.0254 (5)
C80.0881 (3)0.5629 (2)0.3142 (3)0.0301 (5)
H80.1900450.5683810.2922780.036*
C170.9166 (4)0.2949 (2)0.8989 (3)0.0374 (6)
H170.8723830.2509610.9468930.045*
C201.0485 (3)0.42678 (19)0.7534 (3)0.0262 (5)
H201.0931090.4709110.7059670.031*
C10.5380 (4)0.4033 (2)0.2527 (4)0.0397 (7)
C211.3978 (4)0.2727 (2)0.7856 (3)0.0363 (7)
H211.4316680.2632460.8783720.044*
C30.6027 (5)0.4809 (4)0.0251 (5)0.0694 (13)
H3A0.5832840.5362250.0212440.104*
H3B0.7176730.4784950.0275780.104*
H3C0.5766770.4272520.0217000.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02048 (12)0.02274 (13)0.03408 (15)0.00142 (13)0.00648 (9)0.00106 (13)
O40.0296 (10)0.0456 (12)0.0419 (12)0.0166 (9)0.0057 (8)0.0012 (9)
N40.0250 (10)0.0260 (10)0.0341 (12)0.0045 (8)0.0065 (9)0.0022 (8)
O30.0293 (10)0.0432 (12)0.0341 (11)0.0126 (9)0.0063 (8)0.0062 (9)
O50.0398 (12)0.0693 (17)0.0334 (12)0.0167 (12)0.0066 (9)0.0073 (11)
N20.0245 (10)0.0226 (11)0.0308 (11)0.0037 (8)0.0060 (8)0.0016 (8)
N30.0291 (11)0.0258 (11)0.0312 (12)0.0082 (9)0.0063 (9)0.0005 (8)
N10.0257 (10)0.0234 (11)0.0310 (12)0.0014 (8)0.0064 (9)0.0018 (8)
C130.0248 (12)0.0242 (13)0.0301 (13)0.0030 (10)0.0094 (10)0.0015 (10)
O10.0459 (13)0.0347 (12)0.0606 (15)0.0056 (10)0.0152 (11)0.0093 (10)
C230.0271 (12)0.0217 (11)0.0312 (13)0.0035 (10)0.0074 (10)0.0008 (9)
C240.0309 (14)0.0366 (15)0.0339 (15)0.0115 (11)0.0082 (11)0.0036 (11)
C110.0311 (13)0.0243 (14)0.0349 (14)0.0000 (11)0.0014 (11)0.0059 (10)
C180.0383 (14)0.0252 (14)0.0391 (15)0.0057 (10)0.0093 (11)0.0043 (10)
C100.0194 (11)0.0275 (13)0.0388 (15)0.0018 (10)0.0047 (10)0.0007 (10)
C140.0299 (13)0.0283 (14)0.0503 (17)0.0039 (11)0.0014 (12)0.0005 (12)
C190.0261 (12)0.0274 (13)0.0262 (12)0.0048 (10)0.0044 (9)0.0023 (9)
C70.0211 (11)0.0219 (11)0.0326 (13)0.0026 (9)0.0062 (9)0.0010 (9)
C20.0239 (12)0.0286 (14)0.0444 (16)0.0044 (10)0.0011 (11)0.0025 (11)
C120.0302 (13)0.0279 (13)0.0339 (14)0.0014 (11)0.0005 (11)0.0034 (11)
C90.0315 (13)0.0321 (15)0.0298 (14)0.0065 (12)0.0097 (11)0.0046 (11)
C40.0259 (12)0.0244 (12)0.0317 (13)0.0056 (10)0.0059 (10)0.0014 (9)
C220.0273 (10)0.0314 (14)0.0379 (13)0.0081 (13)0.0028 (9)0.0019 (13)
C60.0276 (13)0.0317 (14)0.0302 (13)0.0034 (10)0.0088 (10)0.0037 (10)
O1W0.112 (3)0.110 (3)0.0523 (16)0.046 (3)0.0401 (17)0.028 (2)
C50.0222 (12)0.0392 (16)0.0352 (14)0.0060 (11)0.0105 (10)0.0008 (11)
C160.0309 (13)0.0357 (15)0.0338 (14)0.0044 (11)0.0123 (10)0.0055 (11)
O20.0463 (17)0.062 (2)0.162 (4)0.0002 (15)0.053 (2)0.013 (2)
C150.0271 (12)0.0225 (12)0.0250 (12)0.0040 (9)0.0034 (9)0.0001 (9)
C80.0239 (12)0.0325 (14)0.0359 (14)0.0047 (10)0.0115 (10)0.0014 (11)
C170.0395 (15)0.0335 (16)0.0415 (16)0.0007 (13)0.0147 (12)0.0102 (12)
C200.0293 (12)0.0229 (13)0.0271 (13)0.0012 (10)0.0085 (10)0.0015 (10)
C10.0360 (15)0.0286 (15)0.0574 (19)0.0063 (12)0.0174 (13)0.0078 (13)
C210.0335 (13)0.0374 (16)0.0340 (14)0.0128 (11)0.0009 (11)0.0001 (10)
C30.047 (2)0.091 (4)0.055 (2)0.004 (2)0.0151 (18)0.002 (2)
Geometric parameters (Å, º) top
Zn1—O41.958 (2)C14—H14C0.9600
Zn1—N4i2.057 (2)C19—C201.397 (4)
Zn1—N12.027 (2)C7—C61.390 (4)
Zn1—O1ii1.971 (2)C7—C81.400 (4)
O4—C101.280 (4)C2—H20.9800
N4—C231.333 (3)C2—C11.526 (4)
N4—C221.390 (4)C2—C31.517 (5)
O3—C21.439 (4)C12—H120.9300
O3—C41.374 (3)C9—H90.9300
O5—C101.237 (4)C9—C41.396 (4)
N2—C131.360 (4)C9—C81.380 (4)
N2—C121.376 (4)C4—C51.392 (4)
N2—C151.442 (3)C22—H220.9300
N3—C231.353 (4)C22—C211.347 (4)
N3—C191.442 (3)C6—H60.9300
N3—C211.393 (4)C6—C51.387 (4)
N1—C131.334 (4)O1W—H1WA0.8501
N1—C111.388 (4)O1W—H1WB0.8498
C13—C141.490 (4)C5—H50.9300
O1—C11.254 (4)C16—H160.9300
C23—C241.492 (4)C16—C151.389 (4)
C24—H24A0.9600C16—C171.382 (4)
C24—H24B0.9600O2—C11.233 (4)
C24—H24C0.9600C15—C201.391 (4)
C11—H110.9300C8—H80.9300
C11—C121.354 (4)C17—H170.9300
C18—H180.9300C20—H200.9300
C18—C191.379 (4)C21—H210.9300
C18—C171.399 (5)C3—H3A0.9600
C10—C71.501 (4)C3—H3B0.9600
C14—H14A0.9600C3—H3C0.9600
C14—H14B0.9600
O4—Zn1—N4i93.20 (9)C8—C7—C10121.5 (2)
O4—Zn1—N1111.57 (10)O3—C2—H2108.8
O4—Zn1—O1ii106.81 (10)O3—C2—C1113.0 (2)
N1—Zn1—N4i107.32 (9)O3—C2—C3105.8 (3)
O1ii—Zn1—N4i119.11 (11)C1—C2—H2108.8
O1ii—Zn1—N1116.40 (10)C3—C2—H2108.8
C10—O4—Zn1124.0 (2)C3—C2—C1111.5 (3)
C23—N4—Zn1iii134.16 (19)N2—C12—H12126.8
C23—N4—C22106.3 (2)C11—C12—N2106.4 (2)
C22—N4—Zn1iii119.40 (18)C11—C12—H12126.8
C4—O3—C2118.7 (2)C4—C9—H9119.9
C13—N2—C12108.3 (2)C8—C9—H9119.9
C13—N2—C15126.5 (2)C8—C9—C4120.1 (3)
C12—N2—C15125.1 (2)O3—C4—C9115.5 (2)
C23—N3—C19127.2 (2)O3—C4—C5124.7 (2)
C23—N3—C21107.9 (2)C5—C4—C9119.8 (3)
C21—N3—C19124.6 (2)N4—C22—H22125.1
C13—N1—Zn1129.56 (18)C21—C22—N4109.8 (2)
C13—N1—C11106.7 (2)C21—C22—H22125.1
C11—N1—Zn1121.55 (18)C7—C6—H6119.3
N2—C13—C14123.5 (2)C5—C6—C7121.4 (3)
N1—C13—N2109.4 (2)C5—C6—H6119.3
N1—C13—C14127.1 (2)H1WA—O1W—H1WB104.5
C1—O1—Zn1iv112.2 (2)C4—C5—H5120.3
N4—C23—N3110.0 (2)C6—C5—C4119.4 (2)
N4—C23—C24126.2 (3)C6—C5—H5120.3
N3—C23—C24123.7 (2)C15—C16—H16120.2
C23—C24—H24A109.5C17—C16—H16120.2
C23—C24—H24B109.5C17—C16—C15119.5 (3)
C23—C24—H24C109.5C16—C15—N2120.1 (2)
H24A—C24—H24B109.5C16—C15—C20121.5 (2)
H24A—C24—H24C109.5C20—C15—N2118.4 (2)
H24B—C24—H24C109.5C7—C8—H8119.7
N1—C11—H11125.4C9—C8—C7120.7 (2)
C12—C11—N1109.2 (2)C9—C8—H8119.7
C12—C11—H11125.4C18—C17—H17119.9
C19—C18—H18120.4C16—C17—C18120.2 (3)
C19—C18—C17119.3 (3)C16—C17—H17119.9
C17—C18—H18120.4C19—C20—H20121.1
O4—C10—C7115.6 (3)C15—C20—C19117.8 (2)
O5—C10—O4125.0 (3)C15—C20—H20121.1
O5—C10—C7119.4 (3)O1—C1—C2119.5 (3)
C13—C14—H14A109.5O2—C1—O1123.4 (4)
C13—C14—H14B109.5O2—C1—C2117.1 (3)
C13—C14—H14C109.5N3—C21—H21127.0
H14A—C14—H14B109.5C22—C21—N3105.9 (3)
H14A—C14—H14C109.5C22—C21—H21127.0
H14B—C14—H14C109.5C2—C3—H3A109.5
C18—C19—N3118.5 (2)C2—C3—H3B109.5
C18—C19—C20121.6 (3)C2—C3—H3C109.5
C20—C19—N3119.9 (2)H3A—C3—H3B109.5
C6—C7—C10120.0 (2)H3A—C3—H3C109.5
C6—C7—C8118.5 (2)H3B—C3—H3C109.5
Symmetry codes: (i) x+2, y+1/2, z+1; (ii) x, y+1/2, z+1; (iii) x+2, y1/2, z+1; (iv) x, y1/2, z+1.
Poly[[[µ-1,3-bis(2-methyl-1H-imidazol-1-yl)benzene][µ-(R)-4-(1-carboxylatoethoxy)benzoato]zinc(II)] monohydrate] (1-D) top
Crystal data top
[Zn(C10H8O5)(C14H14N4)]·H2OF(000) = 548
Mr = 529.84Dx = 1.494 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 8.2888 (5) ÅCell parameters from 7886 reflections
b = 14.3618 (7) Åθ = 3.9–30.2°
c = 10.2195 (7) ŵ = 1.09 mm1
β = 104.509 (7)°T = 293 K
V = 1177.75 (13) Å3Block, clear light colourless
Z = 20.3 × 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 Source5710 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ω scansθmax = 30.4°, θmin = 3.7°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
h = 1011
Tmin = 0.565, Tmax = 1.000k = 1920
20401 measured reflectionsl = 1414
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-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 = 1.02Δρmax = 0.31 e Å3
6215 reflectionsΔρmin = 0.26 e Å3
322 parametersAbsolute structure: Flack x determined using 2451 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
7 restraintsAbsolute 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
xyzUiso*/Ueq
Zn10.48210 (3)0.25388 (2)0.40070 (3)0.02549 (9)
O40.6728 (3)0.32335 (18)0.5087 (2)0.0395 (5)
O31.3248 (3)0.52356 (16)0.8448 (2)0.0360 (5)
N30.2466 (3)0.69014 (17)0.2870 (2)0.0282 (5)
N40.3904 (3)0.72439 (16)0.4348 (2)0.0280 (5)
N20.1492 (3)0.45794 (15)0.2070 (2)0.0251 (4)
O50.7799 (3)0.3663 (2)0.3387 (2)0.0471 (6)
C130.3027 (4)0.43201 (19)0.2812 (3)0.0257 (5)
N10.3161 (3)0.33939 (16)0.2778 (2)0.0270 (4)
O11.4270 (3)0.65166 (17)0.6879 (3)0.0466 (6)
C230.2456 (3)0.69088 (18)0.4200 (3)0.0264 (5)
C240.1004 (4)0.6625 (2)0.5301 (3)0.0336 (6)
H24A0.1059360.5967540.5457730.050*
H24B0.1021970.6956900.6112730.050*
H24C0.0007130.6765330.5046030.050*
C110.1666 (4)0.3063 (2)0.1986 (3)0.0315 (6)
H110.1414260.2439930.1781810.038*
C180.0484 (4)0.7288 (2)0.1570 (3)0.0339 (6)
H180.0931770.7884730.1453260.041*
C170.1115 (3)0.66354 (19)0.2299 (3)0.0267 (5)
C21.4930 (3)0.5178 (2)0.8321 (3)0.0337 (6)
H21.5075620.4582840.7895340.040*
C70.9292 (3)0.40301 (18)0.5622 (3)0.0253 (5)
C120.0626 (4)0.3791 (2)0.1555 (3)0.0316 (6)
H120.0459150.3762190.1016310.038*
C140.4316 (4)0.4990 (2)0.3534 (3)0.0380 (6)
H14A0.4981750.5188110.2940830.057*
H14B0.5014530.4692290.4313870.057*
H14C0.3781520.5520140.3813740.057*
C100.7850 (3)0.36077 (19)0.4601 (3)0.0282 (5)
C200.1485 (4)0.6159 (2)0.1176 (3)0.0323 (6)
H200.2361910.5998510.0803120.039*
O21.6854 (4)0.6042 (2)0.7453 (5)0.0829 (13)
C91.0445 (4)0.4788 (2)0.7759 (3)0.0307 (6)
H91.0301310.5034230.8564220.037*
C190.0830 (4)0.7047 (2)0.1008 (3)0.0365 (6)
H190.1264610.7485350.0520660.044*
O1W0.6795 (5)0.2592 (4)0.0988 (3)0.0862 (11)
H1WA0.6531890.2122490.1395620.129*
H1WB0.6923690.3030190.1564290.129*
C61.0826 (3)0.4112 (2)0.5316 (3)0.0285 (5)
H61.0947980.3901700.4485300.034*
C41.1997 (3)0.48401 (19)0.7463 (3)0.0278 (5)
C150.0830 (3)0.55071 (19)0.1904 (3)0.0256 (5)
C11.5380 (4)0.5968 (2)0.7475 (4)0.0384 (7)
C160.0486 (3)0.57310 (19)0.2467 (3)0.0265 (5)
H160.0932300.5289560.2942190.032*
C51.2188 (3)0.4505 (2)0.6238 (3)0.0314 (6)
H51.3217030.4541710.6031640.038*
C220.4852 (3)0.7468 (3)0.3061 (3)0.0329 (6)
H220.5921490.7716990.2860400.039*
C80.9124 (3)0.4371 (2)0.6857 (3)0.0298 (5)
H80.8104670.4316570.7076360.036*
C210.3973 (4)0.7267 (2)0.2145 (3)0.0351 (6)
H210.4312540.7356790.1214650.042*
C31.6031 (6)0.5184 (4)0.9750 (4)0.0698 (13)
H3A1.5763140.5714781.0226910.105*
H3B1.7178880.5216910.9722230.105*
H3C1.5849160.4624611.0207110.105*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02078 (13)0.02224 (13)0.03327 (14)0.00144 (13)0.00644 (9)0.00090 (14)
O40.0294 (10)0.0448 (12)0.0421 (11)0.0168 (9)0.0050 (8)0.0003 (10)
O30.0297 (10)0.0430 (12)0.0340 (10)0.0133 (9)0.0055 (8)0.0076 (9)
N30.0301 (11)0.0247 (11)0.0299 (11)0.0076 (9)0.0075 (9)0.0000 (9)
N40.0256 (10)0.0261 (10)0.0321 (11)0.0045 (8)0.0068 (8)0.0020 (8)
N20.0229 (10)0.0233 (11)0.0295 (10)0.0038 (8)0.0071 (8)0.0007 (8)
O50.0390 (12)0.0668 (17)0.0342 (11)0.0156 (12)0.0070 (9)0.0086 (11)
C130.0266 (13)0.0222 (12)0.0296 (12)0.0028 (10)0.0095 (10)0.0015 (10)
N10.0278 (11)0.0216 (11)0.0315 (11)0.0019 (8)0.0075 (9)0.0007 (8)
O10.0463 (13)0.0352 (12)0.0594 (14)0.0052 (10)0.0154 (11)0.0106 (10)
C230.0268 (12)0.0201 (11)0.0324 (12)0.0023 (10)0.0078 (10)0.0014 (10)
C240.0326 (14)0.0352 (15)0.0328 (13)0.0116 (12)0.0078 (11)0.0044 (11)
C110.0324 (14)0.0248 (13)0.0339 (13)0.0003 (11)0.0021 (11)0.0056 (10)
C180.0390 (14)0.0246 (14)0.0378 (14)0.0055 (10)0.0087 (11)0.0038 (10)
C170.0277 (12)0.0248 (12)0.0265 (12)0.0052 (10)0.0049 (10)0.0019 (9)
C20.0249 (13)0.0271 (13)0.0448 (15)0.0048 (11)0.0005 (11)0.0041 (12)
C70.0239 (12)0.0206 (11)0.0310 (12)0.0032 (9)0.0061 (10)0.0011 (9)
C120.0297 (14)0.0273 (13)0.0336 (14)0.0011 (11)0.0004 (11)0.0040 (11)
C140.0308 (14)0.0286 (14)0.0496 (16)0.0036 (12)0.0010 (13)0.0005 (13)
C100.0206 (11)0.0256 (13)0.0370 (14)0.0044 (10)0.0048 (10)0.0015 (10)
C200.0318 (13)0.0352 (15)0.0322 (13)0.0044 (11)0.0123 (10)0.0046 (11)
O20.0458 (17)0.058 (2)0.160 (4)0.0007 (15)0.053 (2)0.008 (2)
C90.0307 (13)0.0320 (15)0.0304 (13)0.0049 (12)0.0096 (11)0.0022 (11)
C190.0373 (15)0.0343 (16)0.0395 (15)0.0017 (13)0.0127 (12)0.0126 (12)
O1W0.111 (3)0.106 (3)0.0530 (15)0.040 (3)0.0407 (17)0.025 (2)
C60.0290 (13)0.0297 (13)0.0283 (12)0.0026 (11)0.0100 (10)0.0037 (10)
C40.0279 (13)0.0235 (12)0.0311 (12)0.0054 (10)0.0056 (10)0.0004 (10)
C150.0255 (12)0.0230 (12)0.0266 (11)0.0029 (10)0.0032 (9)0.0006 (9)
C10.0366 (15)0.0267 (14)0.0553 (18)0.0062 (12)0.0177 (13)0.0064 (13)
C160.0305 (13)0.0213 (12)0.0281 (12)0.0025 (11)0.0081 (10)0.0020 (10)
C50.0233 (12)0.0370 (15)0.0352 (13)0.0066 (11)0.0096 (10)0.0023 (11)
C220.0275 (11)0.0315 (14)0.0364 (12)0.0083 (13)0.0021 (9)0.0041 (14)
C80.0245 (12)0.0313 (13)0.0360 (13)0.0036 (11)0.0121 (10)0.0016 (11)
C210.0340 (13)0.0368 (16)0.0317 (13)0.0119 (11)0.0030 (10)0.0013 (10)
C30.053 (2)0.089 (4)0.051 (2)0.001 (2)0.0168 (18)0.001 (2)
Geometric parameters (Å, º) top
Zn1—O41.959 (2)C2—C31.516 (5)
Zn1—N4i2.055 (2)C7—C101.503 (4)
Zn1—N12.028 (2)C7—C61.388 (4)
Zn1—O1ii1.971 (2)C7—C81.393 (4)
O4—C101.278 (4)C12—H120.9300
O3—C21.435 (4)C14—H14A0.9600
O3—C41.374 (3)C14—H14B0.9600
N3—C231.358 (4)C14—H14C0.9600
N3—C171.438 (3)C20—H200.9300
N3—C211.386 (4)C20—C191.379 (4)
N4—C231.336 (4)C20—C151.389 (4)
N4—C221.391 (3)O2—C11.232 (4)
N2—C131.360 (4)C9—H90.9300
N2—C121.373 (4)C9—C41.396 (4)
N2—C151.435 (3)C9—C81.379 (4)
O5—C101.234 (4)C19—H190.9300
C13—N11.336 (4)O1W—H1WA0.8501
C13—C141.488 (4)O1W—H1WB0.8499
N1—C111.384 (4)C6—H60.9300
O1—C11.249 (4)C6—C51.395 (4)
C23—C241.484 (4)C4—C51.387 (4)
C24—H24A0.9600C15—C161.392 (4)
C24—H24B0.9600C16—H160.9300
C24—H24C0.9600C5—H50.9300
C11—H110.9300C22—H220.9300
C11—C121.357 (4)C22—C211.353 (4)
C18—H180.9300C8—H80.9300
C18—C171.378 (4)C21—H210.9300
C18—C191.396 (4)C3—H3A0.9600
C17—C161.394 (4)C3—H3B0.9600
C2—H20.9800C3—H3C0.9600
C2—C11.528 (4)
O4—Zn1—N4i93.20 (9)C11—C12—H12126.8
O4—Zn1—N1111.52 (10)C13—C14—H14A109.5
O4—Zn1—O1ii106.91 (10)C13—C14—H14B109.5
N1—Zn1—N4i107.39 (9)C13—C14—H14C109.5
O1ii—Zn1—N4i119.00 (10)H14A—C14—H14B109.5
O1ii—Zn1—N1116.39 (10)H14A—C14—H14C109.5
C10—O4—Zn1124.0 (2)H14B—C14—H14C109.5
C4—O3—C2118.8 (2)O4—C10—C7115.5 (2)
C23—N3—C17126.8 (2)O5—C10—O4125.0 (3)
C23—N3—C21108.1 (2)O5—C10—C7119.5 (2)
C21—N3—C17125.0 (2)C19—C20—H20120.2
C23—N4—Zn1iii133.93 (19)C19—C20—C15119.7 (2)
C23—N4—C22106.7 (2)C15—C20—H20120.2
C22—N4—Zn1iii119.27 (18)C4—C9—H9120.0
C13—N2—C12108.3 (2)C8—C9—H9120.0
C13—N2—C15126.7 (2)C8—C9—C4119.9 (3)
C12—N2—C15124.9 (2)C18—C19—H19119.9
N2—C13—C14123.7 (3)C20—C19—C18120.1 (3)
N1—C13—N2109.3 (2)C20—C19—H19119.9
N1—C13—C14127.0 (3)H1WA—O1W—H1WB104.5
C13—N1—Zn1129.42 (19)C7—C6—H6119.5
C13—N1—C11106.8 (2)C7—C6—C5120.9 (2)
C11—N1—Zn1121.54 (18)C5—C6—H6119.5
C1—O1—Zn1iv112.0 (2)O3—C4—C9115.5 (2)
N3—C23—C24123.9 (2)O3—C4—C5124.7 (2)
N4—C23—N3109.6 (2)C5—C4—C9119.8 (3)
N4—C23—C24126.4 (2)C20—C15—N2120.1 (2)
C23—C24—H24A109.5C20—C15—C16121.2 (3)
C23—C24—H24B109.5C16—C15—N2118.8 (2)
C23—C24—H24C109.5O1—C1—C2119.3 (3)
H24A—C24—H24B109.5O2—C1—O1123.4 (3)
H24A—C24—H24C109.5O2—C1—C2117.3 (3)
H24B—C24—H24C109.5C17—C16—H16120.9
N1—C11—H11125.4C15—C16—C17118.1 (2)
C12—C11—N1109.1 (2)C15—C16—H16120.9
C12—C11—H11125.4C6—C5—H5120.2
C17—C18—H18120.2C4—C5—C6119.6 (2)
C17—C18—C19119.6 (3)C4—C5—H5120.2
C19—C18—H18120.2N4—C22—H22125.3
C18—C17—N3118.5 (2)C21—C22—N4109.3 (2)
C18—C17—C16121.3 (2)C21—C22—H22125.3
C16—C17—N3120.2 (2)C7—C8—H8119.5
O3—C2—H2108.7C9—C8—C7121.0 (2)
O3—C2—C1112.9 (2)C9—C8—H8119.5
O3—C2—C3106.1 (3)N3—C21—H21126.9
C1—C2—H2108.7C22—C21—N3106.3 (2)
C3—C2—H2108.7C22—C21—H21126.9
C3—C2—C1111.5 (3)C2—C3—H3A109.5
C6—C7—C10119.4 (2)C2—C3—H3B109.5
C6—C7—C8118.7 (2)C2—C3—H3C109.5
C8—C7—C10121.9 (2)H3A—C3—H3B109.5
N2—C12—H12126.8H3A—C3—H3C109.5
C11—C12—N2106.4 (2)H3B—C3—H3C109.5
Symmetry codes: (i) x, y1/2, z+1; (ii) x+2, y1/2, z+1; (iii) x, y+1/2, z+1; (iv) x+2, y+1/2, z+1.
Poly[[µ-1,3-bis(2-methyl-1H-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 = 511.82Dx = 1.473 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.0631 (8) ÅCell parameters from 5842 reflections
b = 11.8412 (7) Åθ = 3.9–29.8°
c = 11.6382 (10) ŵ = 1.11 mm1
β = 112.456 (10)°T = 293 K
V = 1154.28 (18) Å3Block, clear light yellow
Z = 20.15 × 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 Source5031 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω scansθmax = 30.3°, θmin = 3.8°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
h = 1112
Tmin = 0.467, Tmax = 1.000k = 1616
12526 measured reflectionsl = 1616
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 0.97Δρmax = 0.32 e Å3
5673 reflectionsΔρmin = 0.29 e Å3
310 parametersAbsolute structure: Flack x determined using 2014 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
13 restraintsAbsolute 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
xyzUiso*/Ueq
Zn10.85708 (3)0.88907 (3)1.09586 (3)0.03087 (9)
N10.7886 (3)0.90974 (19)0.9114 (2)0.0354 (6)
O30.8012 (3)0.24398 (17)1.3363 (2)0.0478 (6)
O10.7395 (3)0.0119 (2)1.1625 (3)0.0504 (6)
O40.8516 (3)0.73831 (19)1.1595 (2)0.0479 (6)
O50.5935 (3)0.7135 (2)1.0510 (3)0.0547 (6)
N20.7128 (3)0.8826 (3)0.71044 (19)0.0341 (4)
N40.0995 (3)0.8927 (3)0.1581 (2)0.0378 (5)
N30.3470 (3)0.8496 (2)0.2766 (2)0.0372 (6)
C80.8802 (4)0.5311 (2)1.2763 (3)0.0354 (6)
H80.9620020.5834321.3101420.042*
C70.7426 (3)0.5620 (2)1.1749 (3)0.0313 (6)
C100.7238 (4)0.6798 (3)1.1236 (3)0.0367 (6)
C60.6248 (4)0.4821 (3)1.1233 (3)0.0377 (6)
H60.5329310.5019151.0558070.045*
C200.5285 (3)0.8639 (2)0.4957 (3)0.0332 (7)
H200.4658250.9208580.5084070.040*
C130.7597 (3)0.8319 (2)0.8240 (3)0.0322 (6)
C110.7122 (4)0.9980 (3)0.7288 (3)0.0448 (7)
H110.6845951.0537250.6678270.054*
C40.7758 (4)0.3446 (2)1.2742 (3)0.0341 (6)
C190.4858 (4)0.8127 (3)0.3796 (3)0.0355 (6)
C120.7595 (5)1.0138 (3)0.8521 (3)0.0442 (8)
H120.7708871.0834280.8915090.053*
C150.6672 (4)0.8280 (2)0.5923 (3)0.0331 (6)
C140.7726 (5)0.7081 (3)0.8456 (4)0.0468 (8)
H14A0.8762940.6827870.8524110.070*
H14B0.6921210.6703280.7772560.070*
H14C0.7578740.6910040.9211630.070*
C90.8964 (4)0.4243 (2)1.3269 (3)0.0373 (7)
H90.9870840.4054801.3958130.045*
C240.1477 (4)0.8563 (4)0.3807 (3)0.0548 (12)
H24A0.1728020.9245690.4289110.082*
H24B0.2032660.7940850.4317980.082*
H24C0.0347400.8429770.3506960.082*
C10.8001 (4)0.0828 (3)1.2059 (3)0.0396 (7)
C230.1977 (3)0.8678 (3)0.2732 (3)0.0355 (7)
C210.3419 (4)0.8653 (4)0.1567 (3)0.0524 (11)
H210.4265700.8584210.1306090.063*
C220.1898 (3)0.8925 (5)0.0859 (3)0.0474 (7)
H220.1516360.9086700.0013440.057*
C20.7127 (4)0.1447 (2)1.2755 (4)0.0433 (8)
H20.6057320.1664031.2176390.052*
C180.5785 (4)0.7275 (3)0.3603 (3)0.0447 (7)
H180.5484060.6931240.2828650.054*
C160.7633 (4)0.7439 (3)0.5739 (3)0.0410 (7)
H160.8568070.7216520.6383630.049*
C50.6404 (4)0.3721 (3)1.1700 (3)0.0410 (7)
H50.5619520.3183161.1323680.049*
C170.7166 (4)0.6938 (3)0.4574 (4)0.0470 (8)
H170.7790740.6367910.4443910.056*
O20.9116 (5)0.1261 (3)1.1897 (5)0.1081 (17)
C30.7006 (10)0.0728 (4)1.3796 (6)0.100 (2)
H3A0.8058960.0552841.4382250.150*
H3B0.6448490.0040961.3456190.150*
H3C0.6434930.1136731.4208040.150*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.03162 (14)0.03157 (14)0.02546 (14)0.00130 (16)0.00646 (10)0.00020 (16)
N10.0354 (11)0.0372 (17)0.0274 (11)0.0047 (10)0.0050 (9)0.0011 (9)
O30.0685 (16)0.0252 (9)0.0402 (13)0.0071 (10)0.0102 (12)0.0024 (9)
O10.0443 (13)0.0434 (12)0.0621 (17)0.0041 (10)0.0188 (12)0.0228 (11)
O40.0532 (14)0.0354 (11)0.0477 (15)0.0033 (10)0.0110 (12)0.0088 (10)
O50.0475 (14)0.0558 (14)0.0552 (16)0.0158 (12)0.0134 (12)0.0189 (12)
N20.0346 (10)0.0395 (11)0.0243 (10)0.0042 (14)0.0069 (8)0.0041 (14)
N40.0324 (10)0.0519 (12)0.0265 (10)0.0003 (16)0.0086 (8)0.0008 (16)
N30.0298 (12)0.0560 (14)0.0236 (12)0.0013 (10)0.0078 (9)0.0017 (10)
C80.0307 (14)0.0304 (13)0.0385 (16)0.0025 (11)0.0059 (12)0.0030 (12)
C70.0328 (14)0.0347 (13)0.0269 (14)0.0045 (11)0.0118 (11)0.0015 (11)
C100.0436 (17)0.0363 (14)0.0336 (16)0.0075 (12)0.0186 (14)0.0023 (12)
C60.0332 (15)0.0436 (16)0.0306 (15)0.0009 (13)0.0057 (12)0.0018 (12)
C200.0284 (12)0.0431 (19)0.0256 (12)0.0037 (10)0.0076 (10)0.0006 (11)
C130.0307 (14)0.0370 (15)0.0276 (15)0.0030 (11)0.0096 (12)0.0006 (12)
C110.058 (2)0.0378 (15)0.0338 (17)0.0048 (14)0.0118 (15)0.0062 (13)
C40.0438 (17)0.0267 (11)0.0319 (15)0.0012 (11)0.0145 (13)0.0050 (11)
C190.0297 (14)0.0483 (16)0.0268 (14)0.0001 (12)0.0091 (12)0.0034 (12)
C120.058 (2)0.0348 (15)0.0346 (18)0.0009 (15)0.0115 (15)0.0005 (14)
C150.0312 (14)0.0409 (15)0.0252 (14)0.0014 (12)0.0086 (11)0.0008 (11)
C140.067 (2)0.0390 (16)0.0380 (19)0.0087 (16)0.0240 (17)0.0037 (14)
C90.0341 (15)0.0304 (13)0.0390 (17)0.0030 (10)0.0045 (13)0.0005 (11)
C240.0352 (16)0.102 (4)0.0277 (15)0.0012 (16)0.0124 (13)0.0015 (17)
C10.0401 (17)0.0376 (15)0.0426 (19)0.0037 (13)0.0174 (15)0.0049 (14)
C230.0320 (13)0.047 (2)0.0254 (13)0.0004 (12)0.0082 (10)0.0003 (12)
C210.0376 (15)0.091 (3)0.0305 (15)0.0053 (17)0.0153 (12)0.0085 (17)
C220.0395 (14)0.077 (2)0.0249 (12)0.002 (2)0.0109 (11)0.010 (2)
C20.054 (2)0.0285 (13)0.054 (2)0.0101 (13)0.0278 (17)0.0099 (13)
C180.0428 (17)0.058 (2)0.0297 (16)0.0048 (15)0.0104 (14)0.0078 (14)
C160.0335 (15)0.0540 (17)0.0331 (16)0.0101 (13)0.0098 (13)0.0018 (14)
C50.0388 (14)0.042 (2)0.0353 (14)0.0102 (14)0.0061 (11)0.0035 (14)
C170.0452 (19)0.058 (2)0.0368 (19)0.0155 (15)0.0153 (15)0.0019 (15)
O20.098 (3)0.084 (2)0.188 (5)0.037 (2)0.106 (3)0.054 (3)
C30.197 (7)0.051 (2)0.094 (4)0.043 (3)0.103 (5)0.021 (3)
Geometric parameters (Å, º) top
Zn1—N12.010 (2)C11—C121.345 (5)
Zn1—O1i1.935 (2)C4—C91.396 (4)
Zn1—O41.941 (2)C4—C51.395 (4)
Zn1—N4ii2.034 (2)C19—C181.385 (5)
N1—C131.322 (4)C12—H120.9300
N1—C121.387 (4)C15—C161.392 (4)
O3—C41.366 (4)C14—H14A0.9600
O3—C21.446 (4)C14—H14B0.9600
O1—C11.265 (4)C14—H14C0.9600
O4—C101.275 (4)C9—H90.9300
O5—C101.227 (4)C24—H24A0.9600
N2—C131.363 (4)C24—H24B0.9600
N2—C111.383 (5)C24—H24C0.9600
N2—C151.430 (4)C24—C231.491 (4)
N4—C231.328 (4)C1—C21.519 (4)
N4—C221.378 (3)C1—O21.210 (4)
N3—C191.435 (4)C21—H210.9300
N3—C231.356 (4)C21—C221.347 (4)
N3—C211.391 (4)C22—H220.9300
C8—H80.9300C2—H20.9800
C8—C71.399 (4)C2—C31.519 (6)
C8—C91.379 (4)C18—H180.9300
C7—C101.501 (4)C18—C171.386 (5)
C7—C61.381 (4)C16—H160.9300
C6—H60.9300C16—C171.389 (5)
C6—C51.397 (5)C5—H50.9300
C20—H200.9300C17—H170.9300
C20—C191.393 (4)C3—H3A0.9600
C20—C151.394 (4)C3—H3B0.9600
C13—C141.485 (4)C3—H3C0.9600
C11—H110.9300
N1—Zn1—N4ii103.21 (9)C16—C15—C20121.2 (3)
O1i—Zn1—N1111.21 (11)C13—C14—H14A109.5
O1i—Zn1—O4107.84 (12)C13—C14—H14B109.5
O1i—Zn1—N4ii122.00 (12)C13—C14—H14C109.5
O4—Zn1—N1118.51 (10)H14A—C14—H14B109.5
O4—Zn1—N4ii93.74 (13)H14A—C14—H14C109.5
C13—N1—Zn1128.8 (2)H14B—C14—H14C109.5
C13—N1—C12107.0 (3)C8—C9—C4119.7 (3)
C12—N1—Zn1124.2 (2)C8—C9—H9120.2
C4—O3—C2120.0 (3)C4—C9—H9120.2
C1—O1—Zn1iii118.4 (2)H24A—C24—H24B109.5
C10—O4—Zn1121.8 (2)H24A—C24—H24C109.5
C13—N2—C11107.7 (3)H24B—C24—H24C109.5
C13—N2—C15127.0 (3)C23—C24—H24A109.5
C11—N2—C15125.3 (3)C23—C24—H24B109.5
C23—N4—Zn1iv124.79 (19)C23—C24—H24C109.5
C23—N4—C22106.8 (2)O1—C1—C2113.9 (3)
C22—N4—Zn1iv126.53 (18)O2—C1—O1125.0 (3)
C23—N3—C19128.2 (2)O2—C1—C2121.0 (3)
C23—N3—C21107.4 (2)N4—C23—N3109.9 (2)
C21—N3—C19124.2 (3)N4—C23—C24124.4 (3)
C7—C8—H8119.5N3—C23—C24125.6 (3)
C9—C8—H8119.5N3—C21—H21126.9
C9—C8—C7121.0 (3)C22—C21—N3106.2 (3)
C8—C7—C10120.5 (3)C22—C21—H21126.9
C6—C7—C8118.7 (3)N4—C22—H22125.2
C6—C7—C10120.8 (3)C21—C22—N4109.6 (3)
O4—C10—C7115.1 (3)C21—C22—H22125.2
O5—C10—O4124.3 (3)O3—C2—C1110.4 (3)
O5—C10—C7120.6 (3)O3—C2—H2109.9
C7—C6—H6119.2O3—C2—C3105.1 (3)
C7—C6—C5121.5 (3)C1—C2—H2109.9
C5—C6—H6119.2C3—C2—C1111.5 (3)
C19—C20—H20120.6C3—C2—H2109.9
C19—C20—C15118.7 (3)C19—C18—H18120.3
C15—C20—H20120.6C19—C18—C17119.5 (3)
N1—C13—N2109.6 (3)C17—C18—H18120.3
N1—C13—C14125.3 (3)C15—C16—H16120.7
N2—C13—C14125.1 (3)C17—C16—C15118.7 (3)
N2—C11—H11126.8C17—C16—H16120.7
C12—C11—N2106.4 (3)C6—C5—H5120.6
C12—C11—H11126.8C4—C5—C6118.7 (3)
O3—C4—C9114.3 (3)C4—C5—H5120.6
O3—C4—C5125.3 (3)C18—C17—C16121.1 (3)
C5—C4—C9120.3 (3)C18—C17—H17119.5
C20—C19—N3120.5 (3)C16—C17—H17119.5
C18—C19—N3118.6 (3)C2—C3—H3A109.5
C18—C19—C20120.8 (3)C2—C3—H3B109.5
N1—C12—H12125.4C2—C3—H3C109.5
C11—C12—N1109.3 (3)H3A—C3—H3B109.5
C11—C12—H12125.4H3A—C3—H3C109.5
C20—C15—N2118.6 (3)H3B—C3—H3C109.5
C16—C15—N2120.2 (3)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z+1; (iii) x, y1, z; (iv) x1, y, z1.
Poly[[µ-1,3-bis(2-methyl-1H-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 = 511.82Dx = 1.473 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.0571 (6) ÅCell parameters from 7631 reflections
b = 11.8439 (6) Åθ = 4.0–30.1°
c = 11.6393 (7) ŵ = 1.11 mm1
β = 112.441 (8)°T = 293 K
V = 1154.01 (13) Å3Block, clear light yellow
Z = 20.2 × 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 Source5479 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω scansθmax = 30.2°, θmin = 3.6°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
h = 1212
Tmin = 0.827, Tmax = 1.000k = 1616
13923 measured reflectionsl = 1616
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.05Δρmax = 0.31 e Å3
5843 reflectionsΔρmin = 0.21 e Å3
310 parametersAbsolute structure: Flack x determined using 2321 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
13 restraintsAbsolute 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
xyzUiso*/Ueq
Zn10.14333 (3)0.82617 (2)0.09573 (2)0.02945 (8)
O40.1480 (3)0.02288 (17)0.1597 (2)0.0459 (5)
N10.2120 (2)0.80530 (17)0.08906 (17)0.0339 (5)
O10.2605 (2)0.72742 (17)0.1628 (2)0.0479 (5)
O30.1988 (3)0.47126 (15)0.33648 (19)0.0464 (5)
N40.9002 (2)0.8222 (3)0.84149 (16)0.0355 (4)
O50.4068 (3)0.0020 (2)0.0510 (2)0.0530 (5)
N20.2880 (2)0.8323 (2)0.28963 (15)0.0326 (4)
N30.6531 (2)0.8655 (2)0.72319 (17)0.0360 (5)
C100.2762 (3)0.0355 (2)0.1235 (2)0.0348 (5)
C200.4716 (3)0.8511 (2)0.5045 (2)0.0317 (5)
H200.5341210.7938700.4919510.038*
C110.2407 (4)0.7011 (2)0.1479 (3)0.0421 (6)
H110.2293010.6314690.1084360.050*
C70.2572 (3)0.1535 (2)0.1753 (2)0.0297 (4)
C240.8529 (3)0.8586 (4)0.6197 (2)0.0532 (10)
H24A0.9652340.8744470.6495710.080*
H24B0.7946260.9190810.5669320.080*
H24C0.8310590.7893230.5733120.080*
C150.3330 (3)0.8871 (2)0.4079 (2)0.0315 (5)
C60.3753 (3)0.2336 (2)0.1233 (2)0.0368 (5)
H60.4673120.2139730.0559460.044*
C80.1195 (3)0.1841 (2)0.2768 (2)0.0338 (5)
H80.0377440.1317960.3107170.041*
C190.5145 (3)0.9027 (2)0.6202 (2)0.0338 (5)
C160.2361 (3)0.9708 (3)0.4255 (2)0.0389 (5)
H160.1425130.9927950.3608700.047*
C210.6573 (3)0.8499 (3)0.8432 (2)0.0490 (9)
H210.5725080.8570110.8691650.059*
C130.2411 (3)0.8831 (2)0.1763 (2)0.0310 (5)
C220.8093 (3)0.8224 (4)0.9138 (2)0.0462 (6)
H220.8473780.8059460.9982670.055*
C140.2281 (4)1.0072 (2)0.1545 (3)0.0450 (6)
H14A0.2393741.0239490.0775200.067*
H14B0.3107641.0448800.2214080.067*
H14C0.1256081.0329070.1503240.067*
C120.2879 (4)0.7168 (2)0.2715 (2)0.0431 (6)
H120.3148480.6611310.3324860.052*
C10.2004 (3)0.6323 (2)0.2054 (2)0.0374 (5)
C230.8028 (3)0.8475 (2)0.7271 (2)0.0336 (6)
C90.1036 (3)0.2911 (2)0.3273 (2)0.0344 (5)
H90.0130290.3099180.3963230.041*
C40.2238 (3)0.3706 (2)0.2746 (2)0.0327 (5)
C180.4218 (3)0.9876 (3)0.6399 (3)0.0425 (6)
H180.4520631.0219650.7173470.051*
C170.2825 (4)1.0211 (3)0.5424 (3)0.0457 (7)
H170.2195781.0778240.5554710.055*
C50.3585 (3)0.3433 (2)0.1703 (2)0.0393 (6)
H50.4363360.3974610.1324940.047*
C20.2863 (3)0.5705 (2)0.2763 (3)0.0409 (6)
H20.3936490.5489000.2190260.049*
O20.0887 (4)0.5886 (3)0.1895 (5)0.1041 (14)
C30.2982 (8)0.6431 (3)0.3794 (5)0.0956 (19)
H3A0.3573630.6034480.4198990.143*
H3B0.3519270.7123710.3450900.143*
H3C0.1928850.6594560.4387780.143*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02966 (12)0.03049 (12)0.02352 (11)0.00130 (12)0.00491 (8)0.00027 (12)
O40.0505 (11)0.0337 (9)0.0458 (11)0.0033 (8)0.0100 (9)0.0088 (8)
N10.0350 (9)0.0362 (14)0.0250 (8)0.0037 (8)0.0052 (7)0.0012 (7)
O10.0434 (10)0.0409 (10)0.0577 (12)0.0032 (9)0.0173 (9)0.0211 (10)
O30.0676 (13)0.0238 (8)0.0390 (10)0.0075 (8)0.0107 (9)0.0038 (8)
N40.0289 (8)0.0506 (10)0.0230 (7)0.0010 (13)0.0054 (6)0.0025 (12)
O50.0447 (11)0.0540 (12)0.0542 (12)0.0149 (10)0.0120 (10)0.0211 (11)
N20.0309 (8)0.0388 (9)0.0226 (7)0.0053 (11)0.0042 (6)0.0032 (11)
N30.0286 (9)0.0561 (12)0.0198 (8)0.0008 (8)0.0053 (7)0.0026 (8)
C100.0408 (13)0.0349 (12)0.0323 (12)0.0075 (10)0.0177 (11)0.0033 (10)
C200.0279 (10)0.0401 (15)0.0250 (9)0.0041 (8)0.0076 (8)0.0011 (8)
C110.0538 (16)0.0326 (13)0.0334 (13)0.0004 (12)0.0095 (12)0.0008 (11)
C70.0301 (10)0.0320 (11)0.0267 (10)0.0031 (9)0.0106 (9)0.0011 (9)
C240.0327 (12)0.103 (3)0.0240 (10)0.0003 (14)0.0103 (9)0.0033 (14)
C150.0276 (10)0.0407 (12)0.0231 (10)0.0001 (9)0.0065 (8)0.0001 (9)
C60.0289 (11)0.0453 (14)0.0296 (11)0.0016 (10)0.0038 (9)0.0028 (10)
C80.0307 (11)0.0278 (10)0.0362 (12)0.0026 (9)0.0051 (9)0.0022 (9)
C190.0269 (10)0.0480 (13)0.0234 (10)0.0001 (9)0.0062 (9)0.0022 (9)
C160.0320 (11)0.0513 (14)0.0300 (11)0.0088 (11)0.0082 (9)0.0005 (11)
C210.0362 (11)0.086 (3)0.0263 (10)0.0052 (14)0.0140 (9)0.0076 (13)
C130.0279 (10)0.0370 (12)0.0251 (10)0.0036 (9)0.0068 (8)0.0008 (10)
C220.0377 (11)0.0752 (18)0.0237 (9)0.0034 (18)0.0094 (8)0.0093 (17)
C140.0658 (19)0.0370 (13)0.0366 (14)0.0093 (13)0.0247 (13)0.0039 (12)
C120.0576 (16)0.0354 (12)0.0310 (12)0.0062 (11)0.0112 (12)0.0060 (10)
C10.0375 (13)0.0356 (12)0.0397 (14)0.0028 (10)0.0153 (12)0.0028 (11)
C230.0299 (10)0.0452 (17)0.0231 (9)0.0017 (9)0.0072 (8)0.0001 (9)
C90.0314 (11)0.0285 (10)0.0342 (11)0.0015 (8)0.0023 (9)0.0000 (9)
C40.0424 (13)0.0253 (9)0.0305 (10)0.0013 (9)0.0140 (10)0.0041 (9)
C180.0403 (13)0.0565 (16)0.0279 (11)0.0042 (12)0.0098 (11)0.0066 (11)
C170.0430 (14)0.0585 (17)0.0352 (13)0.0158 (13)0.0147 (12)0.0019 (13)
C50.0380 (11)0.0386 (16)0.0340 (10)0.0119 (11)0.0058 (9)0.0042 (11)
C20.0516 (15)0.0263 (11)0.0498 (15)0.0098 (11)0.0248 (13)0.0096 (11)
O20.095 (2)0.078 (2)0.183 (4)0.0364 (18)0.102 (3)0.051 (2)
C30.188 (6)0.0495 (19)0.091 (3)0.043 (3)0.100 (4)0.023 (2)
Geometric parameters (Å, º) top
Zn1—O4i1.944 (2)C15—C161.390 (4)
Zn1—N12.0131 (19)C6—H60.9300
Zn1—O11.9328 (19)C6—C51.396 (4)
Zn1—N4ii2.0388 (17)C8—H80.9300
O4—C101.277 (3)C8—C91.381 (4)
N1—C111.388 (3)C19—C181.384 (4)
N1—C131.321 (3)C16—H160.9300
O1—C11.266 (3)C16—C171.395 (4)
O3—C41.367 (3)C21—H210.9300
O3—C21.441 (3)C21—C221.346 (4)
N4—C221.384 (3)C13—C141.490 (4)
N4—C231.321 (3)C22—H220.9300
O5—C101.227 (3)C14—H14A0.9600
N2—C151.433 (3)C14—H14B0.9600
N2—C131.361 (3)C14—H14C0.9600
N2—C121.384 (4)C12—H120.9300
N3—C191.435 (3)C1—C21.521 (3)
N3—C211.396 (3)C1—O21.212 (4)
N3—C231.356 (3)C9—H90.9300
C10—C71.506 (3)C9—C41.393 (3)
C20—H200.9300C4—C51.391 (4)
C20—C151.395 (3)C18—H180.9300
C20—C191.392 (3)C18—C171.394 (4)
C11—H110.9300C17—H170.9300
C11—C121.348 (4)C5—H50.9300
C7—C61.384 (4)C2—H20.9800
C7—C81.399 (3)C2—C31.513 (5)
C24—H24A0.9600C3—H3A0.9600
C24—H24B0.9600C3—H3B0.9600
C24—H24C0.9600C3—H3C0.9600
C24—C231.489 (3)
O4i—Zn1—N1118.65 (9)C17—C16—H16120.8
O4i—Zn1—N4ii93.58 (11)N3—C21—H21127.1
N1—Zn1—N4ii103.35 (8)C22—C21—N3105.9 (2)
O1—Zn1—O4i107.83 (10)C22—C21—H21127.1
O1—Zn1—N1111.34 (9)N1—C13—N2109.5 (2)
O1—Zn1—N4ii121.71 (10)N1—C13—C14125.3 (2)
C10—O4—Zn1iii121.45 (17)N2—C13—C14125.2 (2)
C11—N1—Zn1124.06 (17)N4—C22—H22125.2
C13—N1—Zn1128.72 (17)C21—C22—N4109.7 (2)
C13—N1—C11107.2 (2)C21—C22—H22125.2
C1—O1—Zn1118.44 (18)C13—C14—H14A109.5
C4—O3—C2120.4 (2)C13—C14—H14B109.5
C22—N4—Zn1iv126.45 (14)C13—C14—H14C109.5
C23—N4—Zn1iv124.78 (16)H14A—C14—H14B109.5
C23—N4—C22106.81 (19)H14A—C14—H14C109.5
C13—N2—C15126.8 (3)H14B—C14—H14C109.5
C13—N2—C12107.9 (2)N2—C12—H12126.9
C12—N2—C15125.2 (2)C11—C12—N2106.3 (2)
C21—N3—C19123.9 (2)C11—C12—H12126.9
C23—N3—C19128.42 (19)O1—C1—C2114.1 (2)
C23—N3—C21107.53 (19)O2—C1—O1125.4 (3)
O4—C10—C7114.8 (2)O2—C1—C2120.5 (3)
O5—C10—O4124.6 (3)N4—C23—N3110.10 (19)
O5—C10—C7120.6 (2)N4—C23—C24124.5 (2)
C15—C20—H20120.7N3—C23—C24125.4 (2)
C19—C20—H20120.7C8—C9—H9120.1
C19—C20—C15118.6 (2)C8—C9—C4119.7 (2)
N1—C11—H11125.4C4—C9—H9120.1
C12—C11—N1109.1 (2)O3—C4—C9114.4 (2)
C12—C11—H11125.4O3—C4—C5125.2 (2)
C6—C7—C10120.7 (2)C5—C4—C9120.4 (2)
C6—C7—C8118.9 (2)C19—C18—H18120.3
C8—C7—C10120.5 (2)C19—C18—C17119.3 (3)
H24A—C24—H24B109.5C17—C18—H18120.3
H24A—C24—H24C109.5C16—C17—H17119.5
H24B—C24—H24C109.5C18—C17—C16121.0 (3)
C23—C24—H24A109.5C18—C17—H17119.5
C23—C24—H24B109.5C6—C5—H5120.5
C23—C24—H24C109.5C4—C5—C6119.1 (2)
C20—C15—N2118.3 (2)C4—C5—H5120.5
C16—C15—N2120.0 (2)O3—C2—C1110.8 (2)
C16—C15—C20121.6 (2)O3—C2—H2109.6
C7—C6—H6119.4O3—C2—C3105.7 (3)
C7—C6—C5121.1 (2)C1—C2—H2109.6
C5—C6—H6119.4C3—C2—C1111.3 (3)
C7—C8—H8119.6C3—C2—H2109.6
C9—C8—C7120.8 (2)C2—C3—H3A109.5
C9—C8—H8119.6C2—C3—H3B109.5
C20—C19—N3120.3 (2)C2—C3—H3C109.5
C18—C19—N3118.6 (2)H3A—C3—H3B109.5
C18—C19—C20121.1 (2)H3A—C3—H3C109.5
C15—C16—H16120.8H3B—C3—H3C109.5
C15—C16—C17118.4 (2)
Symmetry codes: (i) x, y+1, z; (ii) x1, y, z1; (iii) x, y1, z; (iv) x+1, y, z+1.
 

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