Tetra­aqua(2,2′-bi­pyridine)­zinc(II) terephthalate

Xu, H.; Liang, Y.; Su, Z.; Zhao, Y.; Shao, K.; Zhang, H.; Yue, S.

doi:10.1107/S1600536803029210

Tetraaqua(2,2′-bipyridine)zinc(II) terephthalate

H. Xu, Y. Liang, Z. Su, Y. Zhao, K. Shao, H. Zhang and S. Yue

A discrete zinc(II) coordination complex, [Zn(bpy)(H₂O)₄](tp) [bpy = 2,2′-bipyridine (C₁₀H₈N₂) and tp = terephthalate (C₈H₄O₄)], has been prepared from the hydrothermal reaction of Zn(CH₃COO)₂·2H₂O, bpy and terephthalic acid in water. The zinc ion has a distorted octahedral coordination environment, with two N atoms from bpy and four water molecules. The terephthalate anion does not coordinate to the Zn^II metal center. Hydrogen bonds and π–π stacking interactions play important roles in the production of a three-dimensional supramolecular structure.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803029210/ww6148sup1.cif Contains datablocks I, Zn1
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803029210/ww6148Isup2.hkl Contains datablock I

CCDC reference: 234786

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.060
wR factor = 0.201
Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.90
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.08
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT731_ALERT_1_C Bond    Calc     0.85(7), Rep     0.85(2) ......       3.50 su-Rat
              O8W  -H2      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.84(6), Rep     0.84(2) ......       3.00 su-Rat
              O7W  -H7      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(7), Rep     0.85(2) ......       3.50 su-Rat
              O7W  -H3      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(6), Rep     0.85(2) ......       3.00 su-Rat
              O6W  -H6      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.84(6), Rep     0.84(2) ......       3.00 su-Rat
              O6W  -H1      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(6), Rep     0.85(2) ......       3.00 su-Rat
              O5W  -H5      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(5), Rep     0.84(2) ......       2.50 su-Rat
              O5W  -H11     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(6), Rep     0.84(2) ......       3.00 su-Rat
              O7W  -H7      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(6), Rep     0.85(2) ......       3.00 su-Rat
              O6W  -H6      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(6), Rep     0.85(2) ......       3.00 su-Rat
              O5W  -H5      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(7), Rep     0.85(2) ......       3.50 su-Rat
              O7W  -H3      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(7), Rep     0.85(2) ......       3.50 su-Rat
              O8W  -H2      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(6), Rep     0.84(2) ......       3.00 su-Rat
              O6W  -H1      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(5), Rep     0.84(2) ......       2.50 su-Rat
              O5W  -H11     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.79(6), Rep     1.78(2) ......       3.00 su-Rat
              H6   -O1      1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.91(7), Rep     1.90(3) ......       2.33 su-Rat
              H3   -O3      1.555   1.654
PLAT736_ALERT_1_C H...A   Calc     1.91(6), Rep     1.90(2) ......       3.00 su-Rat
              H2   -O2      1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.87(5), Rep     1.87(2) ......       2.50 su-Rat
              H11  -O1      1.555   4.575
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C8 H4 O4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  23 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

  19 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: RAPID-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 1997).

Tetraaqua(2,2'-bipyridine)zinc(II) terephthalate top

Crystal data top

[Zn(C₁₀H₈N₂)(H₂O)₄](C₈H₄O₄)	F(000) = 944
M_r = 457.73	D_x = 1.556 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13997 reflections
a = 7.641 (2) Å	θ = 1.7–27.5°
b = 23.508 (5) Å	µ = 1.31 mm⁻¹
c = 11.134 (2) Å	T = 293 K
β = 102.40 (3)°	Block, colorless
V = 1953.5 (7) Å³	0.41 × 0.38 × 0.23 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4476 independent reflections
Radiation source: fine-focus sealed tube	3222 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.5°, θ_min = 1.7°
ω scans	h = 0→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = 0→30
T_min = 0.540, T_max = 0.737	l = −14→14
4476 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.202	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²)(0.1219P)².4398P] where P = (F_o² + 2F_c²)/3
4476 reflections	(Δ/σ)_max < 0.001
286 parameters	Δρ_max = 2.25 e Å⁻³
8 restraints	Δρ_min = −0.58 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.71111 (6)	0.63942 (2)	0.77627 (4)	0.02283 (19)
O8W	0.4267 (5)	0.63496 (17)	0.7618 (3)	0.0398 (8)
O4	−0.1296 (4)	0.69475 (15)	1.4610 (3)	0.0348 (8)
O7W	0.9920 (5)	0.64433 (19)	0.7876 (3)	0.0433 (9)
O6W	0.7243 (5)	0.70105 (15)	0.9069 (3)	0.0387 (8)
O2	0.2964 (5)	0.66631 (18)	0.9635 (3)	0.0408 (9)
N1	0.7397 (5)	0.57087 (15)	0.9059 (4)	0.0301 (8)
O5W	0.6744 (5)	0.69313 (14)	0.6297 (3)	0.0326 (7)
O3	0.1231 (5)	0.66285 (18)	1.5811 (3)	0.0432 (9)
C10	0.7093 (9)	0.5640 (2)	0.5447 (5)	0.0451 (13)
H20A	0.6891	0.5982	0.5022	0.080*
N2	0.7144 (5)	0.56418 (16)	0.6649 (3)	0.0312 (8)
O1	0.5448 (4)	0.69988 (14)	1.0846 (3)	0.0349 (7)
C17	0.3118 (6)	0.6841 (2)	1.3916 (4)	0.0306 (10)
H36A	0.3810	0.6833	1.4713	0.080*
C20	0.0341 (6)	0.68061 (17)	1.4817 (4)	0.0254 (9)
C19	0.3831 (6)	0.68417 (18)	1.0655 (4)	0.0264 (9)
C15	0.0218 (6)	0.6857 (2)	1.2528 (4)	0.0320 (10)
H32A	−0.1025	0.6872	1.2393	0.080*
C16	0.1238 (6)	0.68378 (17)	1.3723 (4)	0.0233 (8)
C11	0.7480 (6)	0.51835 (19)	0.8605 (4)	0.0308 (9)
C12	0.7442 (6)	0.51529 (19)	0.7271 (4)	0.0303 (9)
C1	0.7436 (8)	0.5767 (2)	1.0266 (5)	0.0415 (12)
H11A	0.7367	0.6132	1.0578	0.080*
C13	0.2912 (6)	0.68542 (17)	1.1718 (4)	0.0239 (8)
C18	0.3945 (6)	0.6857 (2)	1.2920 (4)	0.0305 (10)
H35A	0.5189	0.6869	1.3052	0.080*
C14	0.1054 (6)	0.6855 (2)	1.1535 (4)	0.0325 (10)
H33A	0.0362	0.6854	1.0739	0.080*
C4	0.7599 (9)	0.4708 (2)	0.9366 (5)	0.0475 (14)
H14A	0.7657	0.4345	0.9042	0.080*
C7	0.7695 (9)	0.4650 (2)	0.6667 (6)	0.0489 (14)
H17A	0.7906	0.4311	0.7107	0.080*
C9	0.7327 (10)	0.5151 (3)	0.4792 (6)	0.0587 (17)
H19A	0.7276	0.5164	0.3951	0.080*
C2	0.7575 (10)	0.5310 (3)	1.1070 (6)	0.0578 (16)
H12A	0.7627	0.5364	1.1904	0.080*
C8	0.7634 (10)	0.4653 (3)	0.5431 (6)	0.0594 (17)
H18A	0.7801	0.4317	0.5027	0.080*
C3	0.7632 (10)	0.4774 (3)	1.0586 (6)	0.0606 (18)
H13A	0.7693	0.4457	1.1091	0.080*
H7	1.066 (9)	0.654 (3)	0.852 (4)	0.080*
H6	0.668 (9)	0.700 (4)	0.965 (5)	0.080*
H5	0.749 (8)	0.696 (3)	0.583 (6)	0.080*
H4	0.375 (11)	0.644 (3)	0.690 (3)	0.080*
H3	1.050 (10)	0.650 (3)	0.732 (6)	0.080*
H2	0.377 (10)	0.647 (3)	0.818 (5)	0.080*
H1	0.783 (9)	0.7315 (19)	0.911 (7)	0.080*
H11	0.626 (10)	0.7256 (16)	0.620 (7)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0272 (3)	0.0227 (3)	0.0203 (3)	0.00129 (19)	0.00877 (18)	0.00109 (18)
O8W	0.0292 (17)	0.061 (2)	0.0305 (17)	0.0017 (16)	0.0096 (14)	−0.0010 (17)
O4	0.0336 (17)	0.0439 (19)	0.0315 (17)	0.0144 (15)	0.0171 (14)	0.0109 (14)
O7W	0.0254 (17)	0.078 (3)	0.0287 (18)	−0.0013 (17)	0.0097 (14)	0.0018 (18)
O6W	0.051 (2)	0.0325 (17)	0.0410 (19)	−0.0118 (16)	0.0294 (17)	−0.0148 (15)
O2	0.0386 (18)	0.067 (2)	0.0198 (16)	−0.0089 (18)	0.0138 (13)	−0.0075 (15)
N1	0.034 (2)	0.0264 (18)	0.033 (2)	0.0020 (16)	0.0123 (16)	0.0050 (15)
O5W	0.0381 (18)	0.0323 (17)	0.0327 (17)	0.0093 (14)	0.0196 (14)	0.0103 (14)
O3	0.0387 (19)	0.068 (2)	0.0251 (17)	0.0103 (18)	0.0117 (14)	0.0077 (16)
C10	0.072 (4)	0.037 (3)	0.029 (2)	−0.001 (3)	0.017 (2)	−0.002 (2)
N2	0.040 (2)	0.0257 (18)	0.0298 (19)	0.0007 (16)	0.0127 (16)	−0.0012 (15)
O1	0.0339 (17)	0.0378 (17)	0.0377 (18)	−0.0122 (15)	0.0184 (14)	−0.0107 (15)
C17	0.030 (2)	0.039 (2)	0.024 (2)	−0.0044 (19)	0.0088 (17)	−0.0036 (18)
C20	0.034 (2)	0.026 (2)	0.0220 (19)	0.0027 (17)	0.0184 (17)	0.0006 (16)
C19	0.032 (2)	0.024 (2)	0.026 (2)	−0.0020 (17)	0.0120 (17)	−0.0002 (16)
C15	0.027 (2)	0.045 (3)	0.025 (2)	0.0048 (19)	0.0067 (17)	0.0020 (19)
C16	0.026 (2)	0.027 (2)	0.0202 (18)	0.0029 (16)	0.0119 (15)	0.0014 (15)
C11	0.033 (2)	0.026 (2)	0.034 (2)	0.0010 (18)	0.0070 (18)	0.0047 (18)
C12	0.031 (2)	0.024 (2)	0.035 (2)	0.0008 (17)	0.0072 (18)	−0.0034 (18)
C1	0.054 (3)	0.042 (3)	0.031 (2)	0.005 (2)	0.016 (2)	0.007 (2)
C13	0.029 (2)	0.026 (2)	0.0186 (18)	−0.0033 (16)	0.0105 (15)	−0.0002 (16)
C18	0.025 (2)	0.041 (3)	0.028 (2)	−0.0049 (19)	0.0113 (17)	−0.0036 (18)
C14	0.032 (2)	0.044 (3)	0.022 (2)	0.003 (2)	0.0067 (17)	0.0002 (18)
C4	0.066 (4)	0.027 (2)	0.050 (3)	0.004 (2)	0.014 (3)	0.008 (2)
C7	0.067 (4)	0.027 (2)	0.054 (3)	0.005 (2)	0.016 (3)	−0.008 (2)
C9	0.091 (5)	0.050 (4)	0.040 (3)	−0.003 (3)	0.026 (3)	−0.012 (3)
C2	0.079 (5)	0.058 (4)	0.038 (3)	0.007 (3)	0.018 (3)	0.016 (3)
C8	0.090 (5)	0.041 (3)	0.052 (3)	0.008 (3)	0.024 (3)	−0.018 (3)
C3	0.094 (5)	0.045 (3)	0.043 (3)	0.001 (3)	0.014 (3)	0.022 (3)

Geometric parameters (Å, º) top

Zn1—O5W	2.034 (3)	C17—H36A	0.9300
Zn1—O6W	2.040 (3)	C20—C16	1.523 (5)
Zn1—O7W	2.126 (4)	C19—C13	1.501 (6)
Zn1—N1	2.143 (4)	C15—C14	1.391 (6)
Zn1—O8W	2.147 (4)	C15—C16	1.391 (6)
Zn1—N2	2.164 (4)	C15—H32A	0.9300
O8W—H4	0.84 (2)	C11—C4	1.395 (7)
O8W—H2	0.85 (2)	C11—C12	1.481 (7)
O4—C20	1.266 (5)	C12—C7	1.394 (7)
O7W—H7	0.84 (2)	C1—C2	1.387 (7)
O7W—H3	0.85 (2)	C1—H11A	0.9300
O6W—H6	0.85 (2)	C13—C14	1.390 (6)
O6W—H1	0.84 (2)	C13—C18	1.400 (6)
O2—C19	1.257 (5)	C18—H35A	0.9300
N1—C11	1.341 (6)	C14—H33A	0.9300
N1—C1	1.345 (6)	C4—C3	1.361 (9)
O5W—H5	0.85 (2)	C4—H14A	0.9300
O5W—H11	0.84 (2)	C7—C8	1.368 (9)
O3—C20	1.240 (5)	C7—H17A	0.9300
C10—N2	1.330 (6)	C9—C8	1.364 (9)
C10—C9	1.392 (8)	C9—H19A	0.9300
C10—H20A	0.9300	C2—C3	1.375 (9)
N2—C12	1.336 (6)	C2—H12A	0.9300
O1—C19	1.263 (6)	C8—H18A	0.9300
C17—C18	1.390 (6)	C3—H13A	0.9300
C17—C16	1.406 (6)

O5W—Zn1—O6W	96.22 (15)	O1—C19—C13	117.9 (4)
O5W—Zn1—O7W	88.71 (14)	C14—C15—C16	120.1 (4)
O6W—Zn1—O7W	91.41 (15)	C14—C15—H32A	119.9
O5W—Zn1—N1	169.56 (15)	C16—C15—H32A	119.9
O6W—Zn1—N1	94.11 (15)	C15—C16—C17	119.3 (4)
O7W—Zn1—N1	92.60 (15)	C15—C16—C20	120.7 (4)
O5W—Zn1—O8W	90.41 (14)	C17—C16—C20	119.9 (4)
O6W—Zn1—O8W	88.98 (15)	N1—C11—C4	120.7 (5)
O7W—Zn1—O8W	179.07 (14)	N1—C11—C12	115.5 (4)
N1—Zn1—O8W	88.21 (15)	C4—C11—C12	123.7 (4)
O5W—Zn1—N2	93.67 (14)	N2—C12—C7	120.4 (5)
O6W—Zn1—N2	169.89 (15)	N2—C12—C11	116.3 (4)
O7W—Zn1—N2	86.70 (16)	C7—C12—C11	123.3 (4)
N1—Zn1—N2	76.08 (15)	N1—C1—C2	123.2 (5)
O8W—Zn1—N2	93.06 (15)	N1—C1—H11A	118.4
Zn1—O8W—H4	109 (6)	C2—C1—H11A	118.4
Zn1—O8W—H2	123 (6)	C14—C13—C18	119.2 (4)
H4—O8W—H2	116 (8)	C14—C13—C19	121.4 (4)
Zn1—O7W—H7	123 (6)	C18—C13—C19	119.4 (4)
Zn1—O7W—H3	130 (6)	C17—C18—C13	120.2 (4)
H7—O7W—H3	103 (8)	C17—C18—H35A	119.9
Zn1—O6W—H6	124 (6)	C13—C18—H35A	119.9
Zn1—O6W—H1	126 (6)	C13—C14—C15	120.8 (4)
H6—O6W—H1	110 (8)	C13—C14—H33A	119.6
C11—N1—C1	118.6 (4)	C15—C14—H33A	119.6
C11—N1—Zn1	116.4 (3)	C3—C4—C11	119.9 (5)
C1—N1—Zn1	125.0 (3)	C3—C4—H14A	120.0
Zn1—O5W—H5	123 (5)	C11—C4—H14A	120.0
Zn1—O5W—H11	130 (5)	C8—C7—C12	120.1 (5)
H5—O5W—H11	100 (7)	C8—C7—H17A	119.9
N2—C10—C9	123.4 (5)	C12—C7—H17A	119.9
N2—C10—H20A	118.3	C8—C9—C10	117.5 (5)
C9—C10—H20A	118.3	C8—C9—H19A	121.2
C10—N2—C12	118.9 (4)	C10—C9—H19A	121.2
C10—N2—Zn1	125.3 (3)	C3—C2—C1	117.5 (6)
C12—N2—Zn1	115.3 (3)	C3—C2—H12A	121.3
C18—C17—C16	120.2 (4)	C1—C2—H12A	121.3
C18—C17—H36A	119.9	C9—C8—C7	119.7 (5)
C16—C17—H36A	119.9	C9—C8—H18A	120.2
O3—C20—O4	125.6 (4)	C7—C8—H18A	120.2
O3—C20—C16	118.4 (4)	C4—C3—C2	120.1 (5)
O4—C20—C16	116.0 (4)	C4—C3—H13A	120.0
O2—C19—O1	123.8 (4)	C2—C3—H13A	120.0
O2—C19—C13	118.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7W—H7···O2ⁱ	0.84 (2)	1.95 (4)	2.749 (5)	159 (8)
O6W—H6···O1	0.85 (2)	1.78 (2)	2.638 (5)	178 (9)
O5W—H5···O4ⁱⁱ	0.85 (2)	1.80 (3)	2.643 (4)	167 (8)
O8W—H4···O3ⁱⁱⁱ	0.84 (2)	2.09 (6)	2.803 (5)	142 (8)
O7W—H3···O3ⁱⁱ	0.85 (2)	1.90 (3)	2.732 (5)	166 (8)
O8W—H2···O2	0.85 (2)	1.90 (2)	2.745 (5)	170 (8)
O6W—H1···O4^iv	0.84 (2)	1.90 (3)	2.706 (5)	160 (8)
O5W—H11···O1^v	0.84 (2)	1.87 (2)	2.710 (5)	171 (8)

Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z−1; (iii) x, y, z−1; (iv) x+1, −y+3/2, z−1/2; (v) x, −y+3/2, z−1/2.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

Tetra­aqua(2,2′-bi­pyridine)­zinc(II) terephthalate

Supporting information

Key indicators

checkCIF/PLATON results

Tetraaqua(2,2′-bipyridine)zinc(II) terephthalate