Literature DB >> 21201608

Tetra-aqua-(1,10-phenanthroline)zinc(II) 3,6-dicarboxy-bicyclo-[2.2.2]oct-7-ene-2,5-dicarboxyl-ate.

Chun-Hui Yu1.   

Abstract

In the title compound, [Zn(C(12)n class="Species">H(8)N(2))(H(2)O)(4)](C(12)H(10)O(8)), each Zn(II) atom is six-coordinated by two N atoms from one phenanthroline mol-ecule and by four O atoms from four water mol-ecules in a distorted octa-hedral environment. In the crystal structure, ions are linked by O-H⋯O hydrogen bonds.

Entities:  

Year:  2008        PMID： 21201608      PMCID： PMC2960719          DOI： 10.1107/S1600536808025622

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related literature, see: Ma et al. (2003 ▶); Hu (2008 ▶).

Experimental

Crystal data

[Zn(n class="CellLine">C12H8N2)(H2O)4](C12H10O8) M = 599.84 Monoclinic, a = 7.4550 (2) Å b = 13.5991 (4) Å c = 22.9833 (7) Å β = 91.555 (1)° V = 2329.22 (12) Å3 Z = 4 Mo Kα radiation μ = 1.13 mm−1 T = 293 (2) K 0.33 × 0.22 × 0.19 mm

Data collection

Bruker APEX CCD area-detector diffractometer Absorption correction: multi-scan (SAINT; Bruker, 1998 ▶) T min = 0.687, T max = 0.805 14301 measured reflections 5626 independent reflections 3854 reflections with I > 2σ(I) R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.122 S = 0.96 5626 reflections 382 parameters 12 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.50 e Å−3 Δρmin = −0.59 e Å−3 Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025622/bt2766sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025622/bt2766Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Zn(C12H8N2)(H2O)4](C12H10O8)F000 = 1240
Mr = 599.84Dx = 1.711 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5626 reflections
a = 7.4550 (2) Åθ = 1.1–28.3º
b = 13.5991 (4) ŵ = 1.13 mm−1
c = 22.9833 (7) ÅT = 293 (2) K
β = 91.5550 (10)ºBlock, colorless
V = 2329.22 (12) Å30.33 × 0.22 × 0.19 mm
Z = 4
Bruker APEX CCD area-detector diffractometer5626 independent reflections
Radiation source: fine-focus sealed tube3854 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.048
T = 293(2) Kθmax = 28.3º
φ and ω scansθmin = 1.7º
Absorption correction: multi-scan(SAINT; Bruker, 1998)h = −9→8
Tmin = 0.687, Tmax = 0.805k = −14→18
14301 measured reflectionsl = −29→30
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122  w = 1/[σ2(Fo2) + (0.0613P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
5626 reflectionsΔρmax = 0.50 e Å−3
382 parametersΔρmin = −0.59 e Å−3
12 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
C1−0.2556 (4)0.2855 (2)0.61401 (12)0.0348 (7)
H1−0.25290.22640.63440.042*
C2−0.2659 (4)0.3745 (3)0.64532 (13)0.0414 (8)
H2−0.27080.37340.68570.050*
C4−0.2686 (5)0.4609 (3)0.61680 (15)0.0459 (9)
H4−0.27560.51940.63760.055*
C5−0.2610 (5)0.4632 (2)0.55588 (14)0.0399 (8)
C6−0.2629 (6)0.5510 (2)0.52184 (18)0.0570 (10)
H6−0.26280.61170.54050.068*
C7−0.2648 (6)0.5479 (2)0.46388 (18)0.0554 (10)
H7−0.26920.60640.44300.067*
C8−0.2603 (5)0.4564 (2)0.43289 (15)0.0385 (8)
C9−0.2666 (4)0.4472 (2)0.37212 (14)0.0409 (8)
H9−0.27270.50320.34890.049*
C10−0.2639 (4)0.3579 (2)0.34720 (13)0.0377 (8)
H10−0.26940.35230.30690.045*
C11−0.2527 (4)0.2731 (2)0.38191 (12)0.0307 (7)
H11−0.25020.21180.36410.037*
C12−0.2538 (4)0.3703 (2)0.52783 (12)0.0272 (6)
C13−0.2518 (4)0.3674 (2)0.46512 (12)0.0271 (6)
C140.1068 (4)0.06219 (19)0.70078 (12)0.0268 (6)
C150.2475 (4)0.12469 (19)0.73318 (11)0.0220 (6)
H150.32950.08080.75480.026*
C160.3605 (4)0.19231 (18)0.69329 (10)0.0206 (5)
H160.48690.17840.70270.025*
C170.3320 (4)0.1720 (2)0.62817 (11)0.0252 (6)
C180.3279 (3)0.30060 (18)0.70964 (10)0.0187 (5)
H180.38940.34450.68290.022*
C190.1500 (4)0.19201 (18)0.77770 (11)0.0209 (5)
H190.07440.15240.80290.025*
C200.0380 (4)0.26442 (19)0.74361 (11)0.0243 (6)
H20−0.08570.26920.74690.029*
C0210.2081 (4)0.3018 (2)0.86562 (11)0.0234 (6)
C210.1303 (4)0.32112 (19)0.70833 (11)0.0245 (6)
H210.07730.36930.68490.029*
C220.4016 (4)0.31473 (18)0.77246 (11)0.0211 (5)
H220.52460.28920.77320.025*
C230.4151 (4)0.4227 (2)0.79029 (11)0.0262 (6)
C250.2936 (4)0.24790 (18)0.81443 (10)0.0216 (6)
H250.37710.19900.83090.026*
N1−0.2458 (3)0.27831 (16)0.43985 (9)0.0246 (5)
N2−0.2495 (3)0.28378 (17)0.55612 (9)0.0255 (5)
O10.2699 (3)0.23710 (15)0.59560 (8)0.0417 (6)
O20.3860 (3)0.08866 (14)0.60983 (8)0.0348 (5)
O1W−0.4920 (3)0.13197 (19)0.49279 (10)0.0375 (5)
O30.1019 (3)−0.02720 (15)0.72076 (9)0.0469 (6)
H30.0255−0.05870.70240.070*
O2W−0.1668 (4)0.06205 (18)0.43708 (11)0.0422 (6)
O40.0122 (3)0.09170 (16)0.66157 (10)0.0473 (6)
O3W−0.2116 (4)0.0585 (2)0.56396 (12)0.0490 (6)
O50.3699 (3)0.49114 (14)0.76039 (9)0.0399 (5)
O4W0.0517 (3)0.17941 (19)0.50606 (9)0.0401 (6)
O60.4927 (3)0.42964 (15)0.84189 (8)0.0374 (5)
H6A0.49950.48770.85140.056*
O70.2531 (3)0.27139 (14)0.91541 (8)0.0336 (5)
O80.0968 (3)0.36877 (15)0.85579 (8)0.0371 (5)
Zn1−0.22063 (5)0.16487 (2)0.499735 (13)0.02916 (12)
HW22−0.223 (4)0.013 (2)0.4325 (16)0.063 (13)*
HW410.113 (5)0.198 (3)0.5355 (10)0.095*
HW21−0.092 (4)0.069 (3)0.4124 (14)0.074 (15)*
HW420.109 (4)0.195 (2)0.4781 (9)0.037 (10)*
HW12−0.551 (4)0.168 (2)0.4714 (11)0.043 (11)*
HW11−0.551 (5)0.118 (3)0.5214 (12)0.079 (15)*
HW31−0.282 (6)0.057 (3)0.5893 (17)0.119*
HW32−0.195 (6)0.009 (2)0.5475 (17)0.083 (18)*
U11U22U33U12U13U23
C10.0317 (17)0.049 (2)0.0242 (14)0.0001 (14)0.0003 (12)−0.0013 (14)
C20.0318 (18)0.067 (2)0.0255 (15)0.0106 (16)−0.0019 (13)−0.0162 (16)
C40.043 (2)0.049 (2)0.0447 (19)0.0084 (16)−0.0065 (16)−0.0268 (17)
C50.045 (2)0.0296 (17)0.0447 (19)0.0040 (14)−0.0066 (15)−0.0126 (15)
C60.079 (3)0.0198 (17)0.072 (3)0.0021 (16)−0.007 (2)−0.0094 (18)
C70.074 (3)0.0221 (18)0.070 (3)0.0012 (17)−0.004 (2)0.0069 (17)
C80.044 (2)0.0230 (16)0.0478 (19)−0.0010 (13)−0.0031 (15)0.0094 (14)
C90.041 (2)0.0408 (19)0.0404 (18)−0.0060 (15)−0.0033 (15)0.0234 (15)
C100.0336 (18)0.054 (2)0.0251 (15)0.0009 (14)0.0010 (13)0.0107 (15)
C110.0318 (16)0.0369 (17)0.0235 (14)0.0024 (13)−0.0001 (12)0.0001 (13)
C120.0309 (16)0.0223 (14)0.0283 (15)−0.0003 (11)−0.0022 (12)−0.0038 (12)
C130.0319 (16)0.0208 (14)0.0283 (14)−0.0005 (11)−0.0027 (12)0.0022 (12)
C140.0353 (17)0.0180 (14)0.0273 (14)−0.0034 (11)0.0054 (13)−0.0008 (11)
C150.0283 (15)0.0176 (13)0.0201 (13)−0.0006 (10)0.0004 (11)0.0004 (10)
C160.0236 (14)0.0201 (13)0.0180 (12)0.0012 (10)0.0012 (11)0.0023 (10)
C170.0331 (16)0.0264 (15)0.0161 (12)−0.0042 (12)−0.0006 (11)−0.0004 (11)
C180.0241 (14)0.0152 (12)0.0167 (12)−0.0037 (10)0.0017 (10)0.0019 (10)
C190.0234 (14)0.0178 (13)0.0218 (13)−0.0028 (10)0.0054 (11)0.0012 (10)
C200.0220 (14)0.0252 (14)0.0255 (14)0.0014 (11)−0.0029 (11)−0.0002 (11)
C0210.0296 (15)0.0219 (14)0.0188 (13)−0.0019 (11)0.0028 (11)−0.0009 (11)
C210.0279 (15)0.0220 (14)0.0233 (13)0.0030 (11)−0.0051 (11)0.0010 (11)
C220.0233 (14)0.0196 (13)0.0203 (13)0.0002 (10)−0.0001 (11)0.0007 (10)
C230.0341 (16)0.0241 (15)0.0204 (13)−0.0099 (12)0.0031 (12)−0.0014 (11)
C250.0248 (14)0.0187 (13)0.0213 (13)0.0027 (10)0.0006 (11)0.0001 (11)
N10.0286 (13)0.0241 (12)0.0212 (11)0.0011 (10)−0.0006 (9)0.0011 (10)
N20.0282 (13)0.0278 (13)0.0203 (11)0.0000 (10)−0.0019 (9)−0.0015 (10)
O10.0729 (17)0.0249 (11)0.0264 (10)−0.0026 (10)−0.0152 (11)0.0063 (9)
O20.0529 (14)0.0266 (11)0.0248 (10)0.0048 (9)−0.0025 (10)−0.0068 (9)
O1W0.0282 (12)0.0574 (16)0.0270 (12)−0.0047 (11)0.0014 (10)0.0052 (11)
O30.0640 (17)0.0305 (12)0.0454 (13)−0.0204 (11)−0.0111 (12)0.0083 (10)
O2W0.0487 (16)0.0325 (14)0.0457 (14)−0.0005 (11)0.0034 (12)−0.0171 (11)
O40.0527 (15)0.0370 (13)0.0507 (14)−0.0078 (11)−0.0267 (12)0.0000 (11)
O3W0.0611 (18)0.0372 (15)0.0482 (15)−0.0090 (12)−0.0082 (13)0.0157 (13)
O50.0610 (16)0.0250 (11)0.0330 (11)−0.0052 (10)−0.0117 (10)0.0037 (9)
O4W0.0259 (12)0.0736 (18)0.0208 (10)−0.0078 (11)0.0007 (9)0.0006 (11)
O60.0551 (15)0.0235 (11)0.0328 (11)−0.0068 (9)−0.0142 (10)−0.0010 (9)
O70.0495 (14)0.0329 (12)0.0184 (9)0.0085 (10)0.0031 (9)0.0025 (8)
O80.0507 (14)0.0341 (12)0.0267 (11)0.0174 (10)0.0063 (10)0.0014 (9)
Zn10.0328 (2)0.0265 (2)0.0280 (2)0.00085 (14)−0.00117 (14)0.00085 (14)
C1—N21.333 (3)C18—C211.499 (4)
C1—C21.410 (4)C18—C221.543 (3)
C1—H10.9300C18—H180.9800
C2—C41.346 (5)C19—C201.498 (4)
C2—H20.9300C19—C251.545 (4)
C4—C51.403 (5)C19—H190.9800
C4—H40.9300C20—C211.325 (4)
C5—C121.420 (4)C20—H200.9300
C5—C61.428 (5)C021—O81.248 (3)
C6—C71.333 (6)C021—O71.254 (3)
C6—H60.9300C021—C251.539 (3)
C7—C81.434 (5)C21—H210.9300
C7—H70.9300C22—C231.526 (3)
C8—C91.402 (4)C22—C251.564 (3)
C8—C131.419 (4)C22—H220.9800
C9—C101.343 (4)C23—O51.200 (3)
C9—H90.9300C23—O61.309 (3)
C10—C111.403 (4)C25—H250.9800
C10—H100.9300N1—Zn12.073 (2)
C11—N11.333 (3)N2—Zn12.087 (2)
C11—H110.9300O1W—Zn12.074 (2)
C12—N21.344 (3)O1W—HW120.816 (17)
C12—C131.442 (4)O1W—HW110.826 (18)
C13—N11.345 (3)O3—H30.8200
C14—O41.198 (3)O2W—Zn12.055 (2)
C14—O31.300 (3)O2W—HW220.799 (17)
C14—C151.528 (4)O2W—HW210.809 (17)
C15—C161.561 (3)O3W—Zn12.067 (2)
C15—C191.567 (3)O3W—HW310.80 (4)
C15—H150.9800O3W—HW320.784 (18)
C16—C171.531 (3)O4W—Zn12.041 (2)
C16—C181.541 (3)O4W—HW410.845 (18)
C16—H160.9800O4W—HW420.811 (17)
C17—O11.240 (3)O6—H6A0.8200
C17—O21.279 (3)
N2—C1—C2121.9 (3)C20—C19—H19110.4
N2—C1—H1119.1C25—C19—H19110.4
C2—C1—H1119.1C15—C19—H19110.4
C4—C2—C1120.0 (3)C21—C20—C19114.3 (2)
C4—C2—H2120.0C21—C20—H20122.9
C1—C2—H2120.0C19—C20—H20122.9
C2—C4—C5120.3 (3)O8—C021—O7124.5 (2)
C2—C4—H4119.8O8—C021—C25119.8 (2)
C5—C4—H4119.8O7—C021—C25115.7 (2)
C4—C5—C12115.9 (3)C20—C21—C18113.9 (2)
C4—C5—C6124.4 (3)C20—C21—H21123.0
C12—C5—C6119.7 (3)C18—C21—H21123.0
C7—C6—C5121.4 (3)C23—C22—C18113.0 (2)
C7—C6—H6119.3C23—C22—C25115.1 (2)
C5—C6—H6119.3C18—C22—C25109.2 (2)
C6—C7—C8121.7 (3)C23—C22—H22106.3
C6—C7—H7119.2C18—C22—H22106.3
C8—C7—H7119.2C25—C22—H22106.3
C9—C8—C13116.4 (3)O5—C23—O6124.9 (3)
C9—C8—C7124.9 (3)O5—C23—C22125.2 (2)
C13—C8—C7118.8 (3)O6—C23—C22109.7 (2)
C10—C9—C8120.3 (3)C021—C25—C19110.9 (2)
C10—C9—H9119.8C021—C25—C22115.2 (2)
C8—C9—H9119.8C19—C25—C22108.0 (2)
C9—C10—C11120.1 (3)C021—C25—H25107.5
C9—C10—H10119.9C19—C25—H25107.5
C11—C10—H10119.9C22—C25—H25107.5
N1—C11—C10121.6 (3)C11—N1—C13118.6 (2)
N1—C11—H11119.2C11—N1—Zn1128.64 (19)
C10—C11—H11119.2C13—N1—Zn1112.79 (17)
N2—C12—C5124.0 (3)C1—N2—C12117.8 (3)
N2—C12—C13117.4 (2)C1—N2—Zn1129.8 (2)
C5—C12—C13118.6 (3)C12—N2—Zn1112.28 (17)
N1—C13—C8123.0 (3)Zn1—O1W—HW12115 (2)
N1—C13—C12117.2 (2)Zn1—O1W—HW11122 (3)
C8—C13—C12119.8 (3)HW12—O1W—HW11109 (3)
O4—C14—O3123.8 (3)C14—O3—H3109.5
O4—C14—C15124.2 (2)Zn1—O2W—HW22124 (3)
O3—C14—C15111.9 (2)Zn1—O2W—HW21124 (3)
C14—C15—C16114.5 (2)HW22—O2W—HW21112 (3)
C14—C15—C19108.6 (2)Zn1—O3W—HW31122 (4)
C16—C15—C19107.85 (19)Zn1—O3W—HW32105 (3)
C14—C15—H15108.6HW31—O3W—HW32117 (3)
C16—C15—H15108.6Zn1—O4W—HW41127 (3)
C19—C15—H15108.6Zn1—O4W—HW42121 (2)
C17—C16—C18113.1 (2)HW41—O4W—HW42106 (3)
C17—C16—C15113.9 (2)C23—O6—H6A109.5
C18—C16—C15109.2 (2)O4W—Zn1—O2W84.42 (10)
C17—C16—H16106.7O4W—Zn1—O3W90.23 (10)
C18—C16—H16106.7O2W—Zn1—O3W91.20 (12)
C15—C16—H16106.7O4W—Zn1—N192.69 (9)
O1—C17—O2123.3 (2)O2W—Zn1—N193.26 (10)
O1—C17—C16120.1 (2)O3W—Zn1—N1174.89 (11)
O2—C17—C16116.4 (2)O4W—Zn1—O1W173.09 (10)
C21—C18—C16109.5 (2)O2W—Zn1—O1W90.46 (10)
C21—C18—C22108.7 (2)O3W—Zn1—O1W85.22 (10)
C16—C18—C22107.0 (2)N1—Zn1—O1W92.24 (9)
C21—C18—H18110.5O4W—Zn1—N290.00 (9)
C16—C18—H18110.5O2W—Zn1—N2171.08 (10)
C22—C18—H18110.5O3W—Zn1—N295.79 (11)
C20—C19—C25109.3 (2)N1—Zn1—N280.02 (9)
C20—C19—C15107.7 (2)O1W—Zn1—N295.62 (9)
C25—C19—C15108.5 (2)
D—H···AD—HH···AD···AD—H···A
O3—H3···O8i0.821.882.674 (3)163
O6—H6A···O2ii0.821.842.583 (3)151
O2W—HW22···O2iii0.799 (17)2.06 (2)2.818 (3)158 (4)
O4W—HW41···O10.845 (18)1.86 (2)2.705 (3)174 (4)
O2W—HW21···O8iv0.809 (17)2.121 (18)2.904 (3)163 (4)
O4W—HW42···O7iv0.811 (17)1.876 (17)2.686 (3)177 (3)
O1W—HW12···O7v0.816 (17)2.09 (2)2.884 (3)165 (3)
O1W—HW11···O2vi0.826 (18)2.13 (2)2.923 (3)160 (4)
O3W—HW31···O2vi0.80 (4)2.57 (4)3.233 (4)142 (5)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O3—H3⋯O8i0.821.882.674 (3)163
O6—H6A⋯O2ii0.821.842.583 (3)151
O2W—HW22⋯O2iii0.799 (17)2.06 (2)2.818 (3)158 (4)
O4W—HW41⋯O10.845 (18)1.86 (2)2.705 (3)174 (4)
O2W—HW21⋯O8iv0.809 (17)2.121 (18)2.904 (3)163 (4)
O4W—HW42⋯O7iv0.811 (17)1.876 (17)2.686 (3)177 (3)
O1W—HW12⋯O7v0.816 (17)2.09 (2)2.884 (3)165 (3)
O1W—HW11⋯O2vi0.826 (18)2.13 (2)2.923 (3)160 (4)
O3W—HW31⋯O2vi0.80 (4)2.57 (4)3.233 (4)142 (5)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Bicyclo-[2.2.2]oct-7-ene-2,3,5,6-tetra-carboxylic dianhydride.

Authors:  Tuoping Hu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-05-10

3.  A porous supramolecular architecture from a copper(II) coordination polymer with a 3D four-connected 8(6) net.

Authors:  Jian-Fang Ma; Jin Yang; Guo-Li Zheng; Li Li; Jing-Fu Liu
Journal:  Inorg Chem       Date:  2003-11-17       Impact factor: 5.165
  3 in total

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