Crystal structure of trans-di­aqua­bis­(4-cyano­benzoato-κO)bis­(N,N-di­ethyl­nicotinamide-κN)zinc(II)

In the crystal, the title centrosymmetric Zn^II complex mol­ecules are linked by O—H...O hydrogen bonds into supra­molecular chains propagating along the [110] direction.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.084
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.978 Note
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.43 Report
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         39 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         61 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density          10 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

trans-Diaquabis(4-cyanobenzoato-κO)bis(N,N-diethylnicotinamide-κN)zinc(II)

Crystal data

[Zn(C8H4NO2)2(C10H14N2O)2(H2O)2]	Z = 1
Mr = 750.13	F(000) = 392
Triclinic, P1	Dx = 1.378 Mg m^−3
a = 7.4916 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5915 (3) Å	Cell parameters from 9994 reflections
c = 15.0343 (6) Å	θ = 2.8–28.2°
α = 86.363 (3)°	µ = 0.74 mm^−1
β = 75.894 (2)°	T = 296 K
γ = 74.390 (2)°	Prism, translucent intense colourless
V = 903.87 (6) Å^3	0.45 × 0.30 × 0.24 mm

Data collection

Bruker SMART BREEZE CCD diffractometer	4366 independent reflections
Radiation source: fine-focus sealed tube	4029 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −9→9
Tmin = 0.74, Tmax = 0.84	k = −11→11
19149 measured reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0458P)^2 + 0.2769P] where P = (Fo^2 + 2Fc^2)/3
4366 reflections	(Δ/σ)max < 0.001
242 parameters	Δρmax = 0.56 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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.

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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.0000	0.0000	0.0000	0.02730 (8)
O1	0.10666 (18)	0.0679 (2)	−0.22778 (9)	0.0585 (4)
O2	0.23197 (15)	0.01976 (13)	−0.10544 (7)	0.0340 (2)
O3	0.51295 (19)	−0.62718 (18)	−0.11834 (9)	0.0571 (4)
O4	0.19075 (17)	−0.10842 (16)	0.08623 (9)	0.0414 (3)
H41	0.115 (3)	−0.110 (3)	0.1366 (17)	0.056 (7)*
H42	0.277 (3)	−0.191 (3)	0.0848 (16)	0.059 (7)*
N1	1.1465 (3)	−0.2028 (3)	−0.46622 (14)	0.0755 (6)
N2	0.02013 (16)	−0.22996 (14)	−0.05596 (8)	0.0288 (2)
N3	0.4843 (2)	−0.58488 (17)	−0.26504 (9)	0.0402 (3)
C1	0.2428 (2)	0.02304 (18)	−0.19037 (10)	0.0324 (3)
C2	0.4408 (2)	−0.03327 (17)	−0.25173 (10)	0.0304 (3)
C3	0.4653 (2)	−0.0552 (2)	−0.34513 (11)	0.0423 (4)
H3	0.3593	−0.0388	−0.3698	0.051*
C4	0.6461 (3)	−0.1012 (2)	−0.40159 (11)	0.0466 (4)
H4	0.6621	−0.1157	−0.4641	0.056*
C5	0.8044 (2)	−0.12572 (19)	−0.36423 (11)	0.0383 (3)
C6	0.7815 (2)	−0.1071 (2)	−0.27117 (12)	0.0415 (4)
H6	0.8876	−0.1252	−0.2463	0.050*
C7	0.5995 (2)	−0.0614 (2)	−0.21525 (11)	0.0368 (3)
H7	0.5836	−0.0493	−0.1525	0.044*
C8	0.9951 (3)	−0.1689 (2)	−0.42235 (13)	0.0507 (4)
C9	−0.1333 (2)	−0.28196 (18)	−0.05414 (10)	0.0323 (3)
H9	−0.2528	−0.2183	−0.0253	0.039*
C10	−0.1218 (2)	−0.4269 (2)	−0.09346 (12)	0.0379 (3)
H10	−0.2314	−0.4600	−0.0909	0.045*
C11	0.0555 (2)	−0.52178 (18)	−0.13656 (11)	0.0386 (3)
H11	0.0669	−0.6187	−0.1644	0.046*
C12	0.2158 (2)	−0.47000 (17)	−0.13758 (10)	0.0317 (3)
C13	0.1916 (2)	−0.32445 (17)	−0.09573 (10)	0.0302 (3)
H13	0.2994	−0.2907	−0.0952	0.036*
C14	0.4178 (2)	−0.56899 (17)	−0.17441 (11)	0.0354 (3)
C15	0.3800 (3)	−0.5002 (2)	−0.33283 (12)	0.0488 (4)
H15A	0.4514	−0.4299	−0.3693	0.059*
H15B	0.2577	−0.4329	−0.3008	0.059*
C16	0.3474 (3)	−0.6144 (3)	−0.39581 (16)	0.0663 (6)
H16A	0.2720	−0.5537	−0.4359	0.099*
H16B	0.2815	−0.6874	−0.3600	0.099*
H16C	0.4680	−0.6748	−0.4317	0.099*
C17	0.6830 (3)	−0.6752 (2)	−0.30132 (13)	0.0481 (4)
H17A	0.6893	−0.7410	−0.3527	0.058*
H17B	0.7267	−0.7473	−0.2542	0.058*
C18	0.8137 (4)	−0.5660 (4)	−0.3324 (2)	0.0831 (8)
H18A	0.9426	−0.6304	−0.3527	0.125*
H18B	0.8053	−0.4984	−0.2823	0.125*
H18C	0.7766	−0.4997	−0.3821	0.125*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02409 (12)	0.02632 (12)	0.02797 (13)	−0.00158 (8)	−0.00370 (8)	−0.00585 (8)
O1	0.0317 (6)	0.0954 (11)	0.0390 (7)	−0.0015 (6)	−0.0080 (5)	0.0024 (7)
O2	0.0289 (5)	0.0415 (6)	0.0297 (5)	−0.0098 (4)	−0.0014 (4)	−0.0061 (4)
O3	0.0501 (7)	0.0621 (8)	0.0419 (7)	0.0212 (6)	−0.0165 (6)	−0.0093 (6)
O4	0.0310 (6)	0.0488 (7)	0.0375 (6)	0.0048 (5)	−0.0113 (5)	−0.0020 (5)
N1	0.0492 (10)	0.0958 (16)	0.0549 (11)	0.0045 (10)	0.0111 (9)	−0.0003 (10)
N2	0.0268 (6)	0.0263 (5)	0.0297 (6)	−0.0019 (4)	−0.0049 (5)	−0.0032 (4)
N3	0.0392 (7)	0.0349 (7)	0.0353 (7)	0.0061 (5)	−0.0050 (6)	−0.0021 (5)
C1	0.0295 (7)	0.0314 (7)	0.0343 (7)	−0.0074 (5)	−0.0040 (6)	−0.0017 (6)
C2	0.0314 (7)	0.0303 (7)	0.0284 (7)	−0.0094 (5)	−0.0033 (6)	−0.0001 (5)
C3	0.0372 (8)	0.0564 (10)	0.0321 (8)	−0.0091 (7)	−0.0094 (6)	−0.0015 (7)
C4	0.0471 (10)	0.0597 (11)	0.0266 (7)	−0.0070 (8)	−0.0034 (7)	−0.0035 (7)
C5	0.0343 (8)	0.0374 (8)	0.0349 (8)	−0.0048 (6)	0.0025 (6)	−0.0014 (6)
C6	0.0318 (8)	0.0527 (10)	0.0379 (8)	−0.0086 (7)	−0.0059 (6)	−0.0035 (7)
C7	0.0334 (8)	0.0469 (9)	0.0287 (7)	−0.0099 (6)	−0.0040 (6)	−0.0046 (6)
C8	0.0421 (10)	0.0553 (11)	0.0406 (9)	−0.0013 (8)	0.0036 (8)	0.0016 (8)
C9	0.0281 (7)	0.0340 (7)	0.0323 (7)	−0.0042 (5)	−0.0067 (6)	−0.0002 (6)
C10	0.0364 (8)	0.0381 (8)	0.0436 (9)	−0.0124 (6)	−0.0148 (7)	0.0002 (7)
C11	0.0466 (9)	0.0285 (7)	0.0422 (8)	−0.0065 (6)	−0.0158 (7)	−0.0061 (6)
C12	0.0349 (7)	0.0258 (6)	0.0296 (7)	0.0007 (5)	−0.0077 (6)	−0.0015 (5)
C13	0.0276 (7)	0.0275 (6)	0.0323 (7)	−0.0032 (5)	−0.0052 (5)	−0.0024 (5)
C14	0.0373 (8)	0.0257 (6)	0.0367 (8)	0.0032 (6)	−0.0080 (6)	−0.0054 (6)
C15	0.0511 (10)	0.0477 (10)	0.0367 (9)	0.0030 (8)	−0.0089 (8)	0.0050 (7)
C16	0.0596 (13)	0.0810 (16)	0.0555 (12)	−0.0073 (11)	−0.0190 (10)	−0.0058 (11)
C17	0.0395 (9)	0.0476 (9)	0.0434 (9)	0.0054 (7)	−0.0015 (7)	−0.0057 (8)
C18	0.0576 (14)	0.099 (2)	0.093 (2)	−0.0287 (14)	−0.0102 (13)	0.0008 (16)

Geometric parameters (Å, º)

Zn1—O2	2.0842 (10)	C6—H6	0.9300
Zn1—O2^i	2.0842 (10)	C7—C6	1.384 (2)
Zn1—O4	2.1503 (11)	C7—H7	0.9300
Zn1—O4^i	2.1503 (11)	C8—N1	1.135 (3)
Zn1—N2	2.1501 (11)	C9—C10	1.385 (2)
Zn1—N2^i	2.1501 (11)	C9—H9	0.9300
O1—C1	1.2436 (19)	C10—H10	0.9300
O2—C1	1.2584 (18)	C11—C10	1.383 (2)
O3—C14	1.231 (2)	C11—H11	0.9300
O4—H41	0.83 (2)	C12—C11	1.385 (2)
O4—H42	0.82 (2)	C12—C14	1.509 (2)
N2—C9	1.3348 (19)	C13—C12	1.384 (2)
N2—C13	1.3389 (17)	C13—H13	0.9300
N3—C14	1.334 (2)	C15—C16	1.510 (3)
N3—C15	1.472 (2)	C15—H15A	0.9700
N3—C17	1.467 (2)	C15—H15B	0.9700
C1—C2	1.513 (2)	C16—H16A	0.9600
C2—C3	1.389 (2)	C16—H16B	0.9600
C2—C7	1.386 (2)	C16—H16C	0.9600
C3—C4	1.380 (2)	C17—C18	1.508 (3)
C3—H3	0.9300	C17—H17A	0.9700
C4—H4	0.9300	C17—H17B	0.9700
C5—C4	1.393 (2)	C18—H18A	0.9600
C5—C6	1.382 (2)	C18—H18B	0.9600
C5—C8	1.446 (2)	C18—H18C	0.9600
O2—Zn1—O2^i	180.00 (7)	C6—C7—H7	119.7
O2—Zn1—O4	89.94 (5)	N1—C8—C5	178.4 (2)
O2^i—Zn1—O4	90.06 (5)	N2—C9—C10	122.61 (14)
O2—Zn1—O4^i	90.06 (5)	N2—C9—H9	118.7
O2^i—Zn1—O4^i	89.94 (5)	C10—C9—H9	118.7
O2—Zn1—N2	88.48 (4)	C9—C10—H10	120.6
O2^i—Zn1—N2	91.52 (4)	C11—C10—C9	118.88 (14)
O2—Zn1—N2^i	91.52 (4)	C11—C10—H10	120.6
O2^i—Zn1—N2^i	88.48 (4)	C10—C11—C12	118.92 (14)
O4^i—Zn1—O4	180.00 (10)	C10—C11—H11	120.5
N2—Zn1—O4	92.36 (5)	C12—C11—H11	120.5
N2^i—Zn1—O4	87.64 (5)	C11—C12—C14	124.06 (13)
N2—Zn1—O4^i	87.64 (5)	C13—C12—C11	118.44 (13)
N2^i—Zn1—O4^i	92.36 (5)	C13—C12—C14	117.28 (13)
N2^i—Zn1—N2	180.00 (6)	N2—C13—C12	122.99 (13)
C1—O2—Zn1	127.55 (9)	N2—C13—H13	118.5
Zn1—O4—H41	101.6 (16)	C12—C13—H13	118.5
Zn1—O4—H42	135.9 (16)	O3—C14—N3	123.94 (14)
H41—O4—H42	106 (2)	O3—C14—C12	117.46 (14)
C9—N2—Zn1	122.37 (9)	N3—C14—C12	118.58 (13)
C9—N2—C13	118.12 (12)	N3—C15—C16	112.80 (17)
C13—N2—Zn1	119.50 (9)	N3—C15—H15A	109.0
C14—N3—C15	124.36 (14)	N3—C15—H15B	109.0
C14—N3—C17	118.81 (14)	C16—C15—H15A	109.0
C17—N3—C15	116.34 (14)	C16—C15—H15B	109.0
O1—C1—O2	126.05 (14)	H15A—C15—H15B	107.8
O1—C1—C2	117.65 (14)	C15—C16—H16A	109.5
O2—C1—C2	116.30 (13)	C15—C16—H16B	109.5
C3—C2—C1	120.47 (14)	C15—C16—H16C	109.5
C7—C2—C3	119.42 (14)	H16A—C16—H16B	109.5
C7—C2—C1	120.10 (13)	H16A—C16—H16C	109.5
C2—C3—H3	119.8	H16B—C16—H16C	109.5
C4—C3—C2	120.43 (15)	N3—C17—C18	112.50 (18)
C4—C3—H3	119.8	N3—C17—H17A	109.1
C3—C4—C5	119.49 (15)	N3—C17—H17B	109.1
C3—C4—H4	120.3	C18—C17—H17A	109.1
C5—C4—H4	120.3	C18—C17—H17B	109.1
C4—C5—C8	120.56 (16)	H17A—C17—H17B	107.8
C6—C5—C4	120.54 (15)	C17—C18—H18A	109.5
C6—C5—C8	118.90 (16)	C17—C18—H18B	109.5
C5—C6—C7	119.41 (15)	C17—C18—H18C	109.5
C5—C6—H6	120.3	H18A—C18—H18B	109.5
C7—C6—H6	120.3	H18A—C18—H18C	109.5
C2—C7—H7	119.7	H18B—C18—H18C	109.5
C6—C7—C2	120.68 (15)
O4—Zn1—O2—C1	153.35 (13)	C15—N3—C17—C18	73.3 (2)
O4^i—Zn1—O2—C1	−26.65 (13)	O1—C1—C2—C3	−8.8 (2)
N2—Zn1—O2—C1	60.99 (12)	O1—C1—C2—C7	170.29 (16)
N2^i—Zn1—O2—C1	−119.01 (12)	O2—C1—C2—C3	171.11 (15)
O2—Zn1—N2—C9	−144.71 (12)	O2—C1—C2—C7	−9.8 (2)
O2^i—Zn1—N2—C9	35.29 (12)	C1—C2—C3—C4	177.77 (16)
O2—Zn1—N2—C13	34.08 (11)	C7—C2—C3—C4	−1.4 (3)
O2^i—Zn1—N2—C13	−145.92 (11)	C1—C2—C7—C6	−177.60 (15)
O4—Zn1—N2—C9	125.41 (12)	C3—C2—C7—C6	1.5 (2)
O4^i—Zn1—N2—C9	−54.59 (12)	C2—C3—C4—C5	0.0 (3)
O4—Zn1—N2—C13	−55.80 (11)	C6—C5—C4—C3	1.2 (3)
O4^i—Zn1—N2—C13	124.20 (11)	C8—C5—C4—C3	−178.01 (18)
Zn1—O2—C1—O1	25.4 (2)	C4—C5—C6—C7	−1.0 (3)
Zn1—O2—C1—C2	−154.52 (10)	C8—C5—C6—C7	178.20 (17)
Zn1—N2—C9—C10	177.24 (12)	C2—C7—C6—C5	−0.4 (3)
C13—N2—C9—C10	−1.6 (2)	N2—C9—C10—C11	−0.1 (2)
Zn1—N2—C13—C12	−176.49 (11)	C12—C11—C10—C9	1.1 (2)
C9—N2—C13—C12	2.3 (2)	C13—C12—C11—C10	−0.4 (2)
C15—N3—C14—O3	−172.38 (18)	C14—C12—C11—C10	174.11 (15)
C15—N3—C14—C12	5.8 (2)	C11—C12—C14—O3	−107.28 (19)
C17—N3—C14—O3	−0.7 (3)	C11—C12—C14—N3	74.5 (2)
C17—N3—C14—C12	177.46 (14)	C13—C12—C14—O3	67.3 (2)
C14—N3—C15—C16	−121.41 (19)	C13—C12—C14—N3	−111.00 (17)
C17—N3—C15—C16	66.7 (2)	N2—C13—C12—C11	−1.4 (2)
C14—N3—C17—C18	−99.1 (2)	N2—C13—C12—C14	−176.26 (13)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O1^i	0.83 (2)	1.84 (2)	2.6419 (19)	161 (2)
O4—H42···O3^ii	0.82 (2)	2.03 (2)	2.827 (2)	163 (2)

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y−1, −z.