supplementary materials


hg2790 scheme

Acta Cryst. (2011). E67, m209    [ doi:10.1107/S1600536811001280 ]

catena-Poly[[aquabis[2-(3-benzoylphenyl)propanoato-[kappa]2O1,O1']cadmium(II)]-[mu]-4,4'-bipyridine-[kappa]2N:N']

T. Jiang and S. W. Ng

Abstract top

The 4,4'-bipyridine heterocycle in the polymeric title compound, [Cd(C16H13O3)2(C10H8N2)(H2O)]n, links adjacent Cd(II) ions into a chain running along the c axis. The Cd atom, which lies on a twofold rotation axis, is chelated by the carboxylate unit and exists in a seven-coordinate pentagonal-bipyramidal geometry. The apical sites are occupied by N atoms. The water molecule also lies on the twofold rotation axis. The methyl substituent of the propanoate group is disordered over two positions in a 1:1 ratio. O-H...O hydrogen bonding between water molecules and adjacent carboxylate O atoms is observed.

Comment top

The drug, 2-(3-benzoylphenyl)propanoic acid (Kétoprofène) (Briard & Rossi, 1990), forms a small number of metal derivatives; in the cobalt(II) and nickel(II) derivatives, the carboxyl unit binds in a unidentate manner to the water-coordinated metal atoms (Zhang et al., 2007a, 2007b). In the title cadmium–4,4'-bipyridine adduct (Scheme I), the N-heterocycle links adjacent formula units into a chain running along the c-axis of the monoclinic unit cell. The cadmium atom, which lies on a twofold rotation axis, is chelated by the carboxyl unit and it exists in seven-coordinate pentagonal bipyramidal geometry. The apical sites are occupied by N atoms. The water molecule also lies on the twofold rotation axis (Fig. 1). The methyl subsituent of the carboxylate is disordered over two positions in a 1:1 ratio.

Related literature top

For the crystal structure of the parent carboxylic acid, see: Briard & Rossi (1990). For related metal carboxylates, see: Zhang et al. (2007a, 2007b).

Experimental top

Cadmium nitrate (1 mmol) and 4,4'-bipyridine (1 mmol) were dissolved in ethanol (50 ml); the solution was added to an aqueous solution (50 ml) of 2-(3-benzoylphenyl)propanoic acid (2 mmol). The pH was adjusted to 7 by the addition of aqueous sodium hydroxide. The solution was filtered and then set aside for the growth of crystal.

Refinement top

The methyl substitutent in the carboxylate is disordered over two positions; as the occupancy refined to nearly 50%, the occupancy was then fixed as 50:50. The pair of Cmethine–Cmethyl distances were restained to within 0.01 Å of each other.

All hydrogen atoms were generated geometrically (C–H 0.93 to 0.98, O–H 0.84; U 1.2 to 1.5 Ueq of the arrier atom).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of fragment of the polymeric Cd(H2O)(C10H8N2)(C16H13O3)2 chain at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.
catena-Poly[[aquabis[2-(3-benzoylphenyl)propanoato- κ2O1,O1']cadmium(II)]-µ-4,4'-bipyridine- κ2N:N'] top
Crystal data top
[Cd(C16H13O3)2(C10H8N2)(H2O)]F(000) = 1624
Mr = 793.13Dx = 1.447 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 24003 reflections
a = 28.3242 (5) Åθ = 3.2–27.4°
b = 6.2561 (2) ŵ = 0.65 mm1
c = 23.6171 (4) ÅT = 293 K
β = 119.539 (1)°Prism, colorless
V = 3640.97 (15) Å30.21 × 0.17 × 0.15 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4128 independent reflections
Radiation source: fine-focus sealed tube3904 reflections with I > 2σ(I)
graphiteRint = 0.023
Detector resolution: 10.000 pixels mm-1θmax = 27.4°, θmin = 3.2°
ω scansh = 3633
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 88
Tmin = 0.875, Tmax = 0.908l = 2930
25489 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0418P)2 + 4.0713P]
where P = (Fo2 + 2Fc2)/3
4128 reflections(Δ/σ)max = 0.001
246 parametersΔρmax = 0.86 e Å3
1 restraintΔρmin = 0.32 e Å3
Crystal data top
[Cd(C16H13O3)2(C10H8N2)(H2O)]V = 3640.97 (15) Å3
Mr = 793.13Z = 4
Monoclinic, C2/cMo Kα radiation
a = 28.3242 (5) ŵ = 0.65 mm1
b = 6.2561 (2) ÅT = 293 K
c = 23.6171 (4) Å0.21 × 0.17 × 0.15 mm
β = 119.539 (1)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4128 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
3904 reflections with I > 2σ(I)
Tmin = 0.875, Tmax = 0.908Rint = 0.023
25489 measured reflectionsθmax = 27.4°
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.083Δρmax = 0.86 e Å3
S = 1.10Δρmin = 0.32 e Å3
4128 reflectionsAbsolute structure: ?
246 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cd10.50000.57510 (3)0.75000.03727 (8)
O10.40639 (7)0.6179 (3)0.67563 (9)0.0607 (5)
O20.43201 (9)0.2876 (3)0.70014 (11)0.0704 (5)
O30.40988 (11)0.0777 (4)0.45591 (12)0.0850 (7)
O1W0.50000.9428 (4)0.75000.0785 (10)
H10.46790.98760.73030.118*
N10.50515 (8)0.5506 (3)0.65299 (9)0.0442 (4)
C10.39770 (10)0.4249 (5)0.66638 (11)0.0532 (6)
C20.34256 (14)0.3558 (9)0.60990 (15)0.1154 (18)
H20.35000.20340.60860.138*0.50
H2'0.31860.46120.61360.138*0.50
C30.3003 (2)0.3399 (14)0.6217 (3)0.0763 (17)0.50
H3A0.31350.29570.66590.114*0.50
H3B0.27470.23660.59270.114*0.50
H3C0.28280.47640.61470.114*0.50
C3'0.3174 (3)0.1758 (11)0.6087 (3)0.0765 (18)0.50
H3'10.32170.14940.65110.115*0.50
H3'20.33280.05950.59670.115*0.50
H3'30.27950.18830.57750.115*0.50
C40.33928 (11)0.4258 (6)0.54630 (13)0.0717 (10)
C50.35646 (10)0.2915 (5)0.51355 (11)0.0600 (7)
H50.36990.15680.53040.072*
C60.35392 (10)0.3555 (4)0.45536 (11)0.0512 (5)
C70.33546 (11)0.5580 (4)0.43111 (13)0.0561 (6)
H70.33400.60250.39270.067*
C80.31913 (12)0.6943 (6)0.46458 (15)0.0712 (8)
H80.30700.83120.44880.085*
C90.32088 (12)0.6274 (7)0.52109 (16)0.0799 (10)
H90.30940.71980.54280.096*
C100.37381 (11)0.2037 (4)0.42323 (12)0.0561 (6)
C110.34975 (11)0.2039 (4)0.35106 (12)0.0523 (5)
C120.29677 (12)0.2666 (5)0.30938 (14)0.0625 (7)
H120.27510.31450.32620.075*
C130.27593 (15)0.2578 (6)0.24244 (15)0.0805 (9)
H130.24040.30000.21440.097*
C140.30791 (18)0.1868 (6)0.21779 (16)0.0863 (11)
H140.29380.18030.17300.104*
C150.36051 (17)0.1253 (6)0.25842 (18)0.0837 (10)
H150.38210.07960.24120.100*
C160.38120 (13)0.1315 (5)0.32456 (15)0.0671 (7)
H160.41660.08680.35200.080*
C170.47859 (10)0.6901 (4)0.60522 (10)0.0496 (5)
H170.46080.80290.61250.060*
C180.47596 (10)0.6764 (4)0.54526 (10)0.0492 (5)
H180.45710.77940.51360.059*
C190.50120 (9)0.5111 (4)0.53218 (9)0.0419 (4)
C200.52919 (13)0.3651 (5)0.58225 (12)0.0653 (8)
H200.54710.25030.57620.078*
C210.53023 (13)0.3917 (5)0.64114 (12)0.0634 (8)
H210.54950.29320.67410.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.04538 (13)0.04118 (13)0.02536 (11)0.0000.01752 (9)0.000
O10.0547 (10)0.0751 (14)0.0467 (10)0.0085 (9)0.0207 (8)0.0110 (9)
O20.0836 (14)0.0608 (13)0.0684 (12)0.0055 (11)0.0386 (11)0.0031 (10)
O30.1018 (17)0.0817 (16)0.0668 (14)0.0390 (13)0.0380 (13)0.0248 (11)
O1W0.0694 (18)0.0446 (16)0.093 (2)0.0000.0182 (18)0.000
N10.0528 (10)0.0534 (12)0.0303 (8)0.0050 (8)0.0236 (8)0.0042 (7)
C10.0472 (12)0.082 (2)0.0352 (11)0.0121 (12)0.0238 (10)0.0136 (11)
C20.077 (2)0.227 (5)0.0424 (15)0.081 (3)0.0299 (15)0.035 (2)
C30.046 (3)0.108 (5)0.070 (4)0.010 (3)0.025 (3)0.004 (4)
C3'0.087 (4)0.084 (5)0.058 (3)0.036 (4)0.035 (3)0.007 (3)
C40.0467 (13)0.121 (3)0.0383 (13)0.0263 (16)0.0142 (11)0.0198 (15)
C50.0533 (13)0.0784 (19)0.0374 (11)0.0092 (12)0.0139 (10)0.0032 (12)
C60.0487 (12)0.0573 (14)0.0383 (11)0.0031 (11)0.0144 (9)0.0004 (10)
C70.0565 (14)0.0568 (16)0.0402 (12)0.0005 (11)0.0124 (10)0.0020 (10)
C80.0612 (15)0.069 (2)0.0603 (17)0.0041 (14)0.0122 (13)0.0176 (14)
C90.0555 (16)0.114 (3)0.0595 (18)0.0091 (17)0.0202 (13)0.0391 (19)
C100.0635 (14)0.0530 (15)0.0495 (13)0.0027 (12)0.0260 (11)0.0097 (11)
C110.0624 (14)0.0463 (14)0.0490 (13)0.0069 (11)0.0282 (11)0.0004 (10)
C120.0649 (15)0.0590 (17)0.0550 (14)0.0027 (12)0.0228 (12)0.0084 (12)
C130.089 (2)0.069 (2)0.0538 (16)0.0030 (17)0.0120 (15)0.0080 (14)
C140.124 (3)0.082 (2)0.0515 (16)0.014 (2)0.0419 (19)0.0025 (16)
C150.107 (3)0.093 (3)0.076 (2)0.019 (2)0.064 (2)0.0076 (19)
C160.0711 (17)0.0711 (19)0.0688 (18)0.0083 (14)0.0420 (15)0.0003 (14)
C170.0615 (13)0.0566 (15)0.0361 (11)0.0146 (11)0.0282 (10)0.0063 (10)
C180.0603 (13)0.0560 (14)0.0334 (10)0.0153 (11)0.0247 (10)0.0113 (9)
C190.0490 (11)0.0509 (12)0.0291 (10)0.0035 (9)0.0217 (8)0.0042 (9)
C200.101 (2)0.0636 (17)0.0439 (13)0.0355 (16)0.0457 (14)0.0172 (12)
C210.096 (2)0.0645 (17)0.0384 (12)0.0317 (15)0.0397 (13)0.0189 (11)
Geometric parameters (Å, °) top
Cd1—O1W2.301 (3)C6—C71.382 (4)
Cd1—O1i2.3653 (18)C6—C101.489 (4)
Cd1—O12.3653 (18)C7—C81.388 (4)
Cd1—N12.3713 (17)C7—H70.9300
Cd1—N1i2.3713 (17)C8—C91.376 (5)
Cd1—O22.469 (2)C8—H80.9300
Cd1—O2i2.469 (2)C9—H90.9300
O1—C11.230 (3)C10—C111.491 (3)
O2—C11.247 (4)C11—C121.385 (4)
O3—C101.218 (3)C11—C161.393 (4)
O1W—H10.8400C12—C131.390 (4)
N1—C171.328 (3)C12—H120.9300
N1—C211.329 (3)C13—C141.370 (5)
C1—C21.534 (4)C13—H130.9300
C2—C3'1.325 (6)C14—C151.371 (6)
C2—C31.360 (6)C14—H140.9300
C2—C41.523 (4)C15—C161.372 (4)
C2—H20.9800C15—H150.9300
C2—H2'0.9800C16—H160.9300
C3—H3A0.9600C17—C181.384 (3)
C3—H3B0.9600C17—H170.9300
C3—H3C0.9600C18—C191.376 (3)
C3'—H3'10.9600C18—H180.9300
C3'—H3'20.9600C19—C201.392 (3)
C3'—H3'30.9600C19—C19ii1.494 (4)
C4—C91.382 (5)C20—C211.387 (3)
C4—C51.383 (4)C20—H200.9300
C5—C61.399 (3)C21—H210.9300
C5—H50.9300
O1W—Cd1—O1i83.50 (5)C2—C3'—H3'3109.5
O1W—Cd1—O183.50 (5)H3'1—C3'—H3'3109.5
O1i—Cd1—O1167.01 (11)H3'2—C3'—H3'3109.5
O1W—Cd1—N193.71 (5)C9—C4—C5118.4 (3)
O1i—Cd1—N198.30 (7)C9—C4—C2120.9 (4)
O1—Cd1—N182.55 (7)C5—C4—C2120.7 (4)
O1W—Cd1—N1i93.71 (5)C4—C5—C6120.9 (3)
O1i—Cd1—N1i82.55 (7)C4—C5—H5119.5
O1—Cd1—N1i98.30 (7)C6—C5—H5119.5
N1—Cd1—N1i172.58 (10)C7—C6—C5119.7 (3)
O1W—Cd1—O2136.77 (6)C7—C6—C10122.3 (2)
O1i—Cd1—O2139.63 (8)C5—C6—C10118.0 (3)
O1—Cd1—O253.34 (8)C6—C7—C8119.4 (3)
N1—Cd1—O284.10 (7)C6—C7—H7120.3
N1i—Cd1—O290.49 (7)C8—C7—H7120.3
O1W—Cd1—O2i136.77 (6)C9—C8—C7120.2 (3)
O1i—Cd1—O2i53.34 (8)C9—C8—H8119.9
O1—Cd1—O2i139.63 (8)C7—C8—H8119.9
N1—Cd1—O2i90.49 (7)C8—C9—C4121.4 (3)
N1i—Cd1—O2i84.10 (7)C8—C9—H9119.3
O2—Cd1—O2i86.47 (11)C4—C9—H9119.3
C1—O1—Cd194.23 (16)O3—C10—C6120.0 (2)
C1—O2—Cd188.96 (17)O3—C10—C11119.5 (3)
Cd1—O1W—H1109.5C6—C10—C11120.5 (2)
C17—N1—C21116.76 (19)C12—C11—C16118.8 (3)
C17—N1—Cd1119.96 (15)C12—C11—C10122.5 (2)
C21—N1—Cd1123.07 (15)C16—C11—C10118.7 (3)
O1—C1—O2122.6 (2)C11—C12—C13120.1 (3)
O1—C1—C2117.4 (3)C11—C12—H12120.0
O2—C1—C2120.0 (3)C13—C12—H12120.0
O1—C1—Cd159.23 (13)C14—C13—C12119.8 (3)
O2—C1—Cd164.04 (14)C14—C13—H13120.1
C2—C1—Cd1169.56 (19)C12—C13—H13120.1
C3'—C2—C354.9 (5)C13—C14—C15120.8 (3)
C3'—C2—C4116.9 (4)C13—C14—H14119.6
C3—C2—C4126.2 (4)C15—C14—H14119.6
C3'—C2—C1124.3 (5)C14—C15—C16119.7 (3)
C3—C2—C1117.7 (4)C14—C15—H15120.1
C4—C2—C1108.5 (2)C16—C15—H15120.1
C3'—C2—H245.1C15—C16—C11120.8 (3)
C3—C2—H299.2C15—C16—H16119.6
C4—C2—H299.2C11—C16—H16119.6
C1—C2—H299.2N1—C17—C18123.4 (2)
C3'—C2—H2'100.7N1—C17—H17118.3
C3—C2—H2'46.6C18—C17—H17118.3
C4—C2—H2'100.7C19—C18—C17120.3 (2)
C1—C2—H2'100.7C19—C18—H18119.9
H2—C2—H2'145.7C17—C18—H18119.9
C2—C3—H3A109.5C18—C19—C20116.36 (19)
C2—C3—H3B109.5C18—C19—C19ii122.0 (3)
H3A—C3—H3B109.5C20—C19—C19ii121.6 (3)
C2—C3—H3C109.5C21—C20—C19119.7 (2)
H3A—C3—H3C109.5C21—C20—H20120.2
H3B—C3—H3C109.5C19—C20—H20120.2
C2—C3'—H3'1109.5N1—C21—C20123.5 (2)
C2—C3'—H3'2109.5N1—C21—H21118.3
H3'1—C3'—H3'2109.5C20—C21—H21118.3
O1W—Cd1—O1—C1177.46 (15)Cd1—C1—C2—C42.5 (18)
O1i—Cd1—O1—C1177.46 (15)C3'—C2—C4—C9126.0 (6)
N1—Cd1—O1—C182.84 (15)C3—C2—C4—C961.3 (7)
N1i—Cd1—O1—C189.72 (15)C1—C2—C4—C987.2 (4)
O2—Cd1—O1—C15.33 (14)C3'—C2—C4—C556.3 (6)
O2i—Cd1—O1—C10.9 (2)C3—C2—C4—C5120.9 (7)
C1i—Cd1—O1—C17.4 (4)C1—C2—C4—C590.5 (4)
O1W—Cd1—O2—C19.29 (18)C9—C4—C5—C61.7 (4)
O1i—Cd1—O2—C1175.73 (14)C2—C4—C5—C6179.5 (2)
O1—Cd1—O2—C15.24 (14)C4—C5—C6—C71.9 (4)
N1—Cd1—O2—C179.84 (15)C4—C5—C6—C10179.2 (2)
N1i—Cd1—O2—C1105.24 (15)C5—C6—C7—C80.7 (4)
O2i—Cd1—O2—C1170.71 (18)C10—C6—C7—C8177.9 (3)
C1i—Cd1—O2—C1175.28 (10)C6—C7—C8—C90.6 (4)
O1W—Cd1—N1—C1737.10 (19)C7—C8—C9—C40.7 (5)
O1i—Cd1—N1—C17121.1 (2)C5—C4—C9—C80.4 (4)
O1—Cd1—N1—C1745.85 (19)C2—C4—C9—C8178.2 (3)
O2—Cd1—N1—C1799.6 (2)C7—C6—C10—O3147.3 (3)
O2i—Cd1—N1—C17174.0 (2)C5—C6—C10—O329.9 (4)
O1W—Cd1—N1—C21148.4 (2)C7—C6—C10—C1132.9 (4)
O1i—Cd1—N1—C2164.5 (2)C5—C6—C10—C11149.9 (2)
O1—Cd1—N1—C21128.6 (2)O3—C10—C11—C12151.6 (3)
O2—Cd1—N1—C2174.9 (2)C6—C10—C11—C1228.2 (4)
O2i—Cd1—N1—C2111.5 (2)O3—C10—C11—C1626.2 (4)
C1—Cd1—N1—C21101.9 (2)C6—C10—C11—C16154.0 (3)
C1i—Cd1—N1—C2137.7 (2)C16—C11—C12—C130.4 (4)
Cd1—O1—C1—O210.1 (3)C10—C11—C12—C13178.1 (3)
Cd1—O1—C1—C2168.7 (2)C11—C12—C13—C140.1 (5)
Cd1—O2—C1—O19.6 (3)C12—C13—C14—C150.4 (6)
Cd1—O2—C1—C2169.1 (2)C13—C14—C15—C161.1 (6)
O1W—Cd1—C1—O12.68 (16)C14—C15—C16—C111.4 (5)
O1i—Cd1—C1—O1177.57 (14)C12—C11—C16—C151.0 (5)
N1—Cd1—C1—O193.06 (15)C10—C11—C16—C15178.9 (3)
N1i—Cd1—C1—O193.98 (15)C21—N1—C17—C180.2 (4)
O2—Cd1—C1—O1170.6 (2)Cd1—N1—C17—C18174.6 (2)
O2i—Cd1—C1—O1179.35 (14)N1—C17—C18—C190.6 (4)
O1—C1—C2—C3'150.3 (5)C17—C18—C19—C200.8 (4)
O2—C1—C2—C3'30.9 (6)C17—C18—C19—C19ii179.3 (3)
Cd1—C1—C2—C3'141.2 (14)C18—C19—C20—C210.2 (5)
O1—C1—C2—C385.7 (6)C19ii—C19—C20—C21179.9 (3)
O2—C1—C2—C395.5 (6)C17—N1—C21—C200.9 (5)
Cd1—C1—C2—C3154.1 (13)Cd1—N1—C21—C20173.8 (3)
O1—C1—C2—C465.9 (4)C19—C20—C21—N10.7 (5)
O2—C1—C2—C4112.9 (4)
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H1···O2iii0.842.092.741 (3)135
Symmetry codes: (iii) x, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °)
top
D—H···AD—HH···AD···AD—H···A
O1w—H1···O2i0.842.092.741 (3)135
Symmetry codes: (i) x, y+1, z.
Acknowledgements top

We thank Heilongjiang East University and the University of Malaya for supporting this study.

references
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