trans-Bis(3-amino­pyridine)­di­aqua­bis(4-cyano­benzoato)­cobalt(II) dihydrate

The reaction of cobalt(II) acetate with 4-cyano­benzoic acid and 3-amino­pyridine gave the title centrosymmetric complex, [Co(C₈H₄NO₂)₂(C₅H₆N₂)₂(H₂O)₂]·2H₂O. The coordination geometry around the Co^II ion is distorted octahedral, and the 4-cyano­benzoate and 3-amino­pyridine ligands act in a monodentate fashion. The hydrogen bonds among the water mol­ecules and cyano and amino groups ensure a two-dimensional hydrogen-bonding architecture.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.078
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.98

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          8
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C5     -   C8       =       1.44 Ang.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1997); 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: WinGX (Farrugia, 1999).

(I)

Crystal data

[Co(C8H4NO2)2(C5H6N2)2(H2O)2]·2H2O	Z = 1
Mr = 611.47	F(000) = 317
Triclinic, P1	Dx = 1.487 Mg m^−3
a = 7.2359 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.7367 (11) Å	Cell parameters from 1267 reflections
c = 13.2036 (19) Å	θ = 5.5–52.1°
α = 82.309 (3)°	µ = 0.69 mm^−1
β = 76.268 (3)°	T = 293 K
γ = 72.365 (2)°	Plate, purple
V = 682.76 (17) Å^3	0.30 × 0.15 × 0.07 mm

Data collection

CCD area detector diffractometer	2824 independent reflections
Radiation source: fine-focus sealed tube	2360 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 26.8°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −9→9
Tmin = 0.805, Tmax = 0.960	k = −9→9
3999 measured reflections	l = −16→8

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	All H-atom parameters refined
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0241P)^2] where P = (Fo^2 + 2Fc^2)/3
2824 reflections	(Δ/σ)max < 0.001
243 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Co	0.0000	0.5000	1.0000	0.02490 (14)
O1	0.1745 (2)	0.5646 (2)	0.85928 (11)	0.0328 (4)
O2	−0.0370 (2)	0.6649 (2)	0.75114 (13)	0.0419 (4)
O3	0.2375 (2)	0.4694 (2)	1.07516 (14)	0.0321 (4)
O4	0.7688 (4)	0.0495 (4)	0.70500 (19)	0.0665 (7)
N1	0.1228 (3)	0.2187 (2)	0.96200 (15)	0.0293 (4)
N2	0.3739 (3)	−0.2206 (3)	1.0805 (2)	0.0369 (5)
N3	0.9115 (4)	0.7672 (3)	0.39387 (19)	0.0672 (8)
C1	0.1328 (4)	0.6222 (3)	0.77109 (18)	0.0318 (6)
C2	0.3039 (3)	0.6424 (3)	0.68369 (17)	0.0297 (5)
C3	0.4965 (4)	0.5757 (3)	0.69851 (19)	0.0360 (6)
C4	0.6531 (4)	0.6045 (4)	0.6227 (2)	0.0400 (6)
C5	0.6176 (4)	0.7001 (3)	0.52967 (18)	0.0362 (6)
C6	0.4270 (4)	0.7622 (4)	0.5123 (2)	0.0431 (7)
C7	0.2716 (4)	0.7323 (3)	0.58881 (19)	0.0383 (6)
C8	0.7810 (4)	0.7372 (4)	0.4527 (2)	0.0468 (7)
C9	0.1934 (3)	0.0872 (3)	1.03063 (19)	0.0294 (5)
C10	0.3080 (3)	−0.0854 (3)	1.00416 (18)	0.0292 (5)
C11	0.3508 (4)	−0.1229 (3)	0.9006 (2)	0.0378 (6)
C12	0.2763 (4)	0.0102 (3)	0.8296 (2)	0.0395 (6)
C13	0.1632 (4)	0.1772 (3)	0.8620 (2)	0.0351 (6)
H1	0.518 (3)	0.509 (3)	0.7603 (16)	0.027 (6)*
H2	0.783 (3)	0.561 (3)	0.6326 (17)	0.038 (7)*
H3	0.403 (3)	0.822 (3)	0.4502 (19)	0.047 (8)*
H4	0.144 (3)	0.778 (3)	0.5788 (15)	0.025 (6)*
H5	0.162 (3)	0.118 (3)	1.0999 (16)	0.027 (6)*
H6	0.433 (3)	−0.243 (3)	0.8822 (16)	0.037 (6)*
H7	0.300 (3)	−0.012 (3)	0.7578 (17)	0.033 (6)*
H8	0.112 (3)	0.275 (3)	0.8123 (16)	0.030 (6)*
H9	0.360 (4)	−0.188 (3)	1.143 (2)	0.047 (9)*
H10	0.492 (4)	−0.285 (3)	1.0577 (18)	0.041 (8)*
H11	0.188 (4)	0.426 (4)	1.138 (2)	0.074 (11)*
H12	0.263 (4)	0.561 (4)	1.0836 (19)	0.047 (9)*
H13	0.860 (5)	0.090 (4)	0.675 (3)	0.085 (14)*
H14	0.823 (6)	−0.056 (5)	0.708 (3)	0.122 (19)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co	0.0253 (2)	0.0219 (2)	0.0274 (3)	−0.00679 (18)	−0.00673 (19)	0.00115 (18)
O1	0.0371 (9)	0.0371 (9)	0.0261 (9)	−0.0152 (7)	−0.0065 (7)	0.0022 (7)
O2	0.0371 (10)	0.0527 (11)	0.0390 (10)	−0.0188 (8)	−0.0116 (8)	0.0071 (8)
O3	0.0334 (10)	0.0292 (10)	0.0373 (11)	−0.0127 (8)	−0.0123 (8)	0.0033 (8)
O4	0.0606 (16)	0.0679 (18)	0.0645 (16)	−0.0178 (14)	−0.0118 (12)	0.0151 (13)
N1	0.0318 (11)	0.0242 (10)	0.0324 (11)	−0.0075 (8)	−0.0082 (9)	−0.0018 (8)
N2	0.0340 (13)	0.0283 (12)	0.0474 (16)	−0.0074 (10)	−0.0115 (12)	0.0028 (11)
N3	0.0548 (17)	0.0765 (18)	0.0573 (17)	−0.0192 (14)	0.0048 (13)	0.0118 (14)
C1	0.0395 (15)	0.0264 (12)	0.0316 (14)	−0.0126 (11)	−0.0065 (11)	−0.0027 (10)
C2	0.0381 (14)	0.0277 (12)	0.0256 (13)	−0.0121 (10)	−0.0071 (11)	−0.0019 (10)
C3	0.0421 (15)	0.0393 (14)	0.0250 (14)	−0.0091 (12)	−0.0094 (12)	0.0023 (11)
C4	0.0325 (15)	0.0481 (16)	0.0370 (16)	−0.0066 (12)	−0.0079 (12)	−0.0043 (12)
C5	0.0374 (14)	0.0389 (14)	0.0307 (14)	−0.0123 (11)	−0.0008 (11)	−0.0037 (11)
C6	0.0492 (17)	0.0491 (17)	0.0269 (15)	−0.0123 (13)	−0.0083 (13)	0.0090 (12)
C7	0.0348 (15)	0.0455 (16)	0.0342 (15)	−0.0099 (12)	−0.0107 (12)	0.0018 (12)
C8	0.0450 (17)	0.0514 (17)	0.0374 (16)	−0.0109 (14)	−0.0032 (13)	0.0037 (13)
C9	0.0285 (13)	0.0301 (13)	0.0312 (14)	−0.0115 (10)	−0.0057 (11)	−0.0011 (11)
C10	0.0258 (12)	0.0249 (12)	0.0398 (15)	−0.0102 (10)	−0.0107 (11)	0.0017 (10)
C11	0.0369 (15)	0.0269 (13)	0.0488 (17)	−0.0048 (11)	−0.0087 (12)	−0.0098 (12)
C12	0.0514 (17)	0.0354 (14)	0.0318 (16)	−0.0101 (12)	−0.0079 (13)	−0.0087 (12)
C13	0.0413 (15)	0.0289 (13)	0.0373 (15)	−0.0110 (11)	−0.0136 (12)	0.0024 (11)

Geometric parameters (Å, º)

Co—O1	2.0777 (14)	C2—C3	1.383 (3)
Co—O1^i	2.0777 (14)	C2—C7	1.384 (3)
Co—O3	2.1202 (16)	C3—C4	1.374 (3)
Co—O3^i	2.1202 (16)	C3—H1	0.92 (2)
Co—N1	2.1646 (17)	C4—C5	1.384 (3)
Co—N1^i	2.1646 (17)	C4—H2	0.93 (2)
O1—C1	1.262 (2)	C5—C6	1.380 (3)
O2—C1	1.254 (3)	C5—C8	1.439 (3)
O3—H11	0.88 (3)	C6—C7	1.377 (3)
O3—H12	0.81 (3)	C6—H3	0.91 (2)
O4—H13	0.81 (3)	C7—H4	0.92 (2)
O4—H14	0.79 (4)	C9—C10	1.382 (3)
N1—C9	1.333 (3)	C9—H5	0.93 (2)
N1—C13	1.344 (3)	C10—C11	1.378 (3)
N2—C10	1.408 (3)	C11—C12	1.369 (3)
N2—H9	0.86 (3)	C11—H6	0.97 (2)
N2—H10	0.85 (2)	C12—C13	1.365 (3)
N3—C8	1.133 (3)	C12—H7	0.95 (2)
C1—C2	1.510 (3)	C13—H8	0.97 (2)
O1—Co—O1^i	180.0	C4—C3—C2	121.1 (2)
O1—Co—O3	89.44 (7)	C4—C3—H1	120.5 (13)
O1^i—Co—O3	90.56 (7)	C2—C3—H1	118.4 (13)
O1—Co—O3^i	90.56 (7)	C3—C4—C5	119.5 (2)
O1^i—Co—O3^i	89.44 (7)	C3—C4—H2	121.4 (14)
O3—Co—O3^i	180.0	C5—C4—H2	119.1 (14)
O1—Co—N1	87.02 (6)	C6—C5—C4	120.2 (2)
O1^i—Co—N1	92.98 (6)	C6—C5—C8	120.7 (2)
O3—Co—N1	89.01 (7)	C4—C5—C8	119.1 (2)
O3^i—Co—N1	90.99 (7)	C7—C6—C5	119.8 (2)
O1—Co—N1^i	92.98 (6)	C7—C6—H3	119.7 (15)
O1^i—Co—N1^i	87.02 (6)	C5—C6—H3	120.5 (15)
O3—Co—N1^i	90.99 (7)	C6—C7—C2	120.7 (2)
O3^i—Co—N1^i	89.01 (7)	C6—C7—H4	120.1 (13)
N1—Co—N1^i	180.00 (10)	C2—C7—H4	119.1 (13)
C1—O1—Co	131.16 (15)	N3—C8—C5	178.4 (3)
Co—O3—H11	99.5 (19)	N1—C9—C10	123.8 (2)
Co—O3—H12	117.5 (18)	N1—C9—H5	115.9 (13)
H11—O3—H12	107 (2)	C10—C9—H5	120.3 (13)
H13—O4—H14	101 (3)	C11—C10—C9	117.7 (2)
C9—N1—C13	117.1 (2)	C11—C10—N2	120.9 (2)
C9—N1—Co	122.22 (16)	C9—C10—N2	121.3 (2)
C13—N1—Co	119.57 (15)	C12—C11—C10	119.0 (2)
C10—N2—H9	118.0 (17)	C12—C11—H6	123.5 (12)
C10—N2—H10	110.7 (16)	C10—C11—H6	117.5 (12)
H9—N2—H10	112 (2)	C13—C12—C11	119.8 (2)
O2—C1—O1	125.5 (2)	C13—C12—H7	119.2 (13)
O2—C1—C2	118.3 (2)	C11—C12—H7	121.0 (13)
O1—C1—C2	116.2 (2)	N1—C13—C12	122.5 (2)
C3—C2—C7	118.8 (2)	N1—C13—H8	116.5 (12)
C3—C2—C1	120.2 (2)	C12—C13—H8	120.9 (12)
C7—C2—C1	121.0 (2)
O3—Co—O1—C1	−171.73 (18)	C2—C3—C4—C5	−0.7 (4)
O3^i—Co—O1—C1	8.27 (18)	C3—C4—C5—C6	−1.5 (4)
N1—Co—O1—C1	99.23 (18)	C3—C4—C5—C8	177.1 (2)
O1—Co—N1—C9	132.37 (17)	C4—C5—C6—C7	1.4 (4)
O1^i—Co—N1—C9	−47.63 (17)	C8—C5—C6—C7	−177.1 (2)
O3—Co—N1—C9	42.88 (17)	C5—C6—C7—C2	0.8 (4)
O3^i—Co—N1—C9	−137.12 (17)	C3—C2—C7—C6	−3.0 (4)
O1—Co—N1—C13	−35.35 (18)	C1—C2—C7—C6	175.0 (2)
O1^i—Co—N1—C13	144.65 (18)	C13—N1—C9—C10	1.6 (3)
O3—Co—N1—C13	−124.85 (18)	Co—N1—C9—C10	−166.38 (17)
O3^i—Co—N1—C13	55.15 (18)	N1—C9—C10—C11	−0.2 (4)
Co—O1—C1—O2	4.7 (3)	N1—C9—C10—N2	−178.2 (2)
Co—O1—C1—C2	−176.00 (13)	C9—C10—C11—C12	−0.9 (4)
O2—C1—C2—C3	−171.7 (2)	N2—C10—C11—C12	177.1 (2)
O1—C1—C2—C3	8.9 (3)	C10—C11—C12—C13	0.6 (4)
O2—C1—C2—C7	10.3 (3)	C9—N1—C13—C12	−2.0 (3)
O1—C1—C2—C7	−169.1 (2)	Co—N1—C13—C12	166.36 (19)
C7—C2—C3—C4	2.9 (4)	C11—C12—C13—N1	0.9 (4)
C1—C2—C3—C4	−175.1 (2)

Symmetry code: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H11···O2^i	0.88 (3)	1.81 (3)	2.672 (2)	165 (3)
O3—H12···N2^ii	0.81 (3)	2.07 (3)	2.871 (3)	169 (2)
O4—H13···N3^iii	0.81 (3)	2.22 (4)	3.021 (4)	172 (3)
O4—H14···O2^iv	0.79 (4)	2.15 (4)	2.931 (3)	168 (4)

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