Diaqua­bis[4-(dimethyl­amino)benzoato-κO](nicotinamide-κN¹)cobalt(II) dihydrate

The title complex, [Co(C₉H₁₀NO₂)₂(C₆H₆N₂O)₂(H₂O)₂]·2H₂O, is monomeric with the Co atom situated on a crystallographic center of inversion. It contains two 4-(dimethyl­amino)benzoate (DMAB) and two nicotinamide (NA) ligands, and two coordinated and two uncoordinated water mol­ecules, all ligands being monodentate. The four O atoms coordinating the Co atom form a slightly distorted square-planar arrangement, while the distorted octa­hedral coordination is completed by the two NA N atoms in the axial positions. The crystal structure is determined by intra- and inter­molecular O—H...O and N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.075
• wR factor = 0.196
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      2.180
            Test value =      2.025
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.19
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       2.18 e/A   
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H32    ...          ?

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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).

Diaquabis[4-(dimethylamino)benzoato-κO](nicotinamide-κN¹)cobalt(II) dihydrate

Crystal data

[Co(C9H10NO2)2(C6H6N2O)2(H2O)2]·2H2O	Z = 1
Mr = 703.61	F(000) = 369
Triclinic, P1	Dx = 1.474 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 8.198 (2) Å	Cell parameters from 25 reflections
b = 9.968 (1) Å	θ = 5.6–21.6°
c = 10.2003 (9) Å	µ = 4.82 mm^−1
α = 76.252 (9)°	T = 294 K
β = 89.10 (1)°	Block, pink
γ = 78.29 (1)°	0.35 × 0.25 × 0.20 mm
V = 792.4 (2) Å^3

Data collection

Enraf–Nonius TurboCAD4 diffractometer	2645 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 74.3°, θmin = 4.5°
nonprofiled ω scans	h = −10→0
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.268, Tmax = 0.378	l = −12→12
3467 measured reflections	3 standard reflections every 120 min
3231 independent reflections	intensity decay: 1%

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.196	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.1423P)^2] where P = (Fo^2 + 2Fc^2)/3
3231 reflections	(Δ/σ)max < 0.001
234 parameters	Δρmax = 2.18 e Å^−3
8 restraints	Δρmin = −0.68 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	0.0000	0.0000	0.0273 (3)
O1	0.1443 (3)	−0.1377 (3)	0.1549 (3)	0.0352 (6)
O2	0.0132 (4)	−0.1222 (3)	0.3444 (3)	0.0474 (8)
O3	0.2284 (4)	0.6299 (3)	−0.1181 (4)	0.0492 (8)
O4	0.1005 (6)	0.1357 (4)	0.3865 (4)	0.0620 (10)
H4A	0.086 (7)	0.053 (3)	0.375 (5)	0.060*
H4B	0.078 (7)	0.135 (6)	0.474 (3)	0.060*
O5	0.1640 (3)	−0.0817 (3)	−0.1404 (3)	0.0354 (6)
H5A	0.115 (6)	−0.021 (4)	−0.219 (3)	0.060*
H5B	0.160 (7)	−0.166 (3)	−0.149 (5)	0.060*
N1	0.4596 (5)	−0.7492 (4)	0.5078 (4)	0.0477 (9)
N2	0.1558 (4)	0.1554 (3)	−0.0076 (3)	0.0311 (6)
N3	0.0065 (5)	0.5849 (4)	−0.2139 (4)	0.0417 (8)
H31	−0.021 (6)	0.670 (5)	−0.264 (5)	0.035 (11)*
H32	−0.042 (8)	0.517 (8)	−0.236 (7)	0.08 (2)*
C1	0.1135 (5)	−0.1888 (4)	0.2758 (4)	0.0320 (8)
C2	0.1994 (5)	−0.3368 (4)	0.3367 (4)	0.0311 (8)
C3	0.3133 (5)	−0.4103 (4)	0.2630 (4)	0.0369 (8)
H3	0.3324	−0.3667	0.1745	0.044*
C4	0.3990 (5)	−0.5465 (4)	0.3177 (4)	0.0402 (9)
H4	0.4751	−0.5924	0.2659	0.048*
C5	0.3723 (5)	−0.6164 (4)	0.4508 (4)	0.0366 (8)
C6	0.2539 (6)	−0.5435 (4)	0.5226 (4)	0.0440 (10)
H6	0.2306	−0.5877	0.6098	0.053*
C7	0.1702 (6)	−0.4063 (4)	0.4662 (4)	0.0407 (9)
H7	0.0927	−0.3603	0.5169	0.049*
C8	0.5807 (7)	−0.8231 (5)	0.4313 (6)	0.0609 (14)
H8A	0.6303	−0.9141	0.4866	0.091*
H8B	0.6657	−0.7697	0.4035	0.091*
H8C	0.5266	−0.8344	0.3531	0.091*
C9	0.4293 (7)	−0.8200 (5)	0.6441 (5)	0.0569 (13)
H9A	0.5015	−0.9116	0.6676	0.085*
H9B	0.3153	−0.8302	0.6500	0.085*
H9C	0.4511	−0.7654	0.7052	0.085*
C10	0.3109 (5)	0.1120 (4)	0.0446 (4)	0.0381 (9)
H10	0.3478	0.0166	0.0846	0.046*
C11	0.4201 (5)	0.2023 (5)	0.0421 (5)	0.0433 (10)
H11	0.5276	0.1683	0.0795	0.052*
C12	0.3646 (5)	0.3444 (4)	−0.0176 (4)	0.0398 (9)
H12	0.4340	0.4079	−0.0195	0.048*
C13	0.2051 (5)	0.3909 (4)	−0.0744 (4)	0.0296 (7)
C14	0.1044 (4)	0.2928 (4)	−0.0666 (4)	0.0293 (7)
H14	−0.0033	0.3239	−0.1039	0.035*
C15	0.1458 (5)	0.5460 (4)	−0.1382 (4)	0.0334 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co	0.0331 (4)	0.0168 (4)	0.0284 (4)	−0.0045 (3)	−0.0049 (3)	0.0017 (3)
O1	0.0382 (14)	0.0272 (13)	0.0319 (13)	−0.0041 (11)	−0.0064 (11)	0.0074 (10)
O2	0.071 (2)	0.0287 (14)	0.0322 (14)	0.0073 (14)	−0.0006 (13)	−0.0014 (11)
O3	0.0554 (19)	0.0254 (14)	0.069 (2)	−0.0131 (13)	0.0003 (15)	−0.0113 (14)
O4	0.098 (3)	0.0346 (17)	0.0475 (19)	−0.0084 (18)	−0.0041 (18)	−0.0017 (15)
O5	0.0419 (15)	0.0245 (13)	0.0369 (14)	−0.0029 (11)	−0.0023 (11)	−0.0051 (11)
N1	0.057 (2)	0.0287 (17)	0.047 (2)	0.0064 (16)	−0.0072 (17)	−0.0010 (15)
N2	0.0366 (16)	0.0205 (13)	0.0345 (15)	−0.0074 (12)	−0.0018 (12)	−0.0016 (11)
N3	0.056 (2)	0.0229 (16)	0.0403 (18)	−0.0051 (15)	−0.0027 (16)	0.0010 (14)
C1	0.041 (2)	0.0205 (16)	0.0315 (18)	−0.0063 (14)	−0.0108 (15)	0.0013 (13)
C2	0.0355 (18)	0.0216 (16)	0.0326 (18)	−0.0032 (14)	−0.0086 (14)	−0.0012 (13)
C3	0.043 (2)	0.0327 (19)	0.0297 (18)	−0.0042 (16)	0.0008 (15)	0.0008 (15)
C4	0.042 (2)	0.034 (2)	0.038 (2)	0.0033 (17)	−0.0009 (16)	−0.0048 (16)
C5	0.041 (2)	0.0254 (17)	0.039 (2)	−0.0031 (15)	−0.0116 (16)	−0.0015 (15)
C6	0.061 (3)	0.031 (2)	0.0294 (19)	0.0008 (18)	0.0024 (18)	0.0052 (15)
C7	0.048 (2)	0.032 (2)	0.034 (2)	0.0031 (17)	0.0034 (17)	−0.0016 (16)
C8	0.070 (3)	0.038 (2)	0.064 (3)	0.013 (2)	−0.006 (3)	−0.011 (2)
C9	0.077 (3)	0.029 (2)	0.053 (3)	−0.004 (2)	−0.019 (2)	0.0080 (19)
C10	0.038 (2)	0.0268 (18)	0.045 (2)	−0.0049 (15)	−0.0112 (16)	0.0000 (16)
C11	0.037 (2)	0.036 (2)	0.054 (2)	−0.0083 (17)	−0.0096 (18)	−0.0048 (18)
C12	0.040 (2)	0.035 (2)	0.048 (2)	−0.0151 (16)	0.0030 (17)	−0.0107 (17)
C13	0.0370 (18)	0.0231 (16)	0.0287 (17)	−0.0073 (14)	0.0038 (14)	−0.0051 (13)
C14	0.0319 (17)	0.0216 (16)	0.0330 (18)	−0.0050 (14)	−0.0032 (14)	−0.0037 (14)
C15	0.044 (2)	0.0232 (17)	0.0329 (18)	−0.0086 (15)	0.0093 (15)	−0.0053 (14)

Geometric parameters (Å, º)

Co—O1	2.037 (2)	C3—C4	1.383 (5)
Co—O1^i	2.037 (2)	C3—H3	0.9300
Co—O5^i	2.138 (3)	C4—H4	0.9300
Co—N2^i	2.187 (3)	C5—C6	1.397 (6)
Co—N2	2.187 (3)	C5—C4	1.407 (6)
O1—C1	1.260 (4)	C6—H6	0.9300
O2—C1	1.260 (5)	C7—C6	1.389 (5)
O3—C15	1.232 (5)	C7—H7	0.9300
O4—H4B	0.91 (2)	C8—H8A	0.9600
O4—H4A	0.885 (18)	C8—H8B	0.9600
O5—Co	2.138 (3)	C8—H8C	0.9600
O5—H5A	0.928 (18)	C9—H9A	0.9600
O5—H5B	0.88 (2)	C9—H9B	0.9600
N1—C5	1.365 (5)	C9—H9C	0.9600
N1—C9	1.445 (6)	C10—C11	1.388 (6)
N1—C8	1.445 (6)	C10—H10	0.9300
N2—C10	1.333 (5)	C11—H11	0.9300
N2—C14	1.341 (4)	C12—C11	1.387 (6)
N3—C15	1.325 (6)	C12—H12	0.9300
N3—H31	0.86 (5)	C13—C12	1.382 (6)
N3—H32	0.92 (7)	C13—C14	1.390 (5)
C2—C7	1.380 (5)	C14—H14	0.9300
C2—C3	1.391 (5)	C15—C13	1.509 (5)
C2—C1	1.488 (5)
O1—Co—O1^i	180.00 (19)	C5—C4—H4	119.7
O1—Co—O5	89.4 (1)	N1—C5—C6	121.4 (4)
O1^i—Co—O5	90.6 (1)	N1—C5—C4	121.4 (4)
O1—Co—O5^i	90.59 (10)	C6—C5—C4	117.1 (3)
O1^i—Co—O5^i	89.41 (10)	C7—C6—C5	121.3 (4)
O5—Co—O5^i	180.0 (2)	C7—C6—H6	119.3
O1—Co—N2^i	88.92 (11)	C5—C6—H6	119.3
O1^i—Co—N2^i	91.08 (11)	C2—C7—C6	121.5 (4)
O5—Co—N2^i	92.88 (11)	C2—C7—H7	119.3
O5^i—Co—N2^i	87.12 (11)	C6—C7—H7	119.3
O1—Co—N2	91.1 (1)	N1—C8—H8A	109.5
O1^i—Co—N2	88.9 (1)	N1—C8—H8B	109.5
O5—Co—N2	87.1 (1)	H8A—C8—H8B	109.5
O5^i—Co—N2	92.9 (1)	N1—C8—H8C	109.5
N2^i—Co—N2	180.00 (13)	H8A—C8—H8C	109.5
C1—O1—Co	132.0 (2)	H8B—C8—H8C	109.5
H4B—O4—H4A	105 (4)	N1—C9—H9A	109.5
Co—O5—H5A	98 (3)	N1—C9—H9B	109.5
Co—O5—H5B	117 (4)	H9A—C9—H9B	109.5
H5A—O5—H5B	105 (4)	N1—C9—H9C	109.5
C5—N1—C9	120.7 (4)	H9A—C9—H9C	109.5
C5—N1—C8	120.5 (4)	H9B—C9—H9C	109.5
C9—N1—C8	118.7 (4)	N2—C10—C11	123.2 (4)
C10—N2—C14	118.0 (3)	N2—C10—H10	118.4
C10—N2—Co	119.0 (2)	C11—C10—H10	118.4
C14—N2—Co	123.0 (2)	C12—C11—C10	118.2 (4)
C15—N3—H31	120 (3)	C12—C11—H11	120.9
C15—N3—H32	120 (4)	C10—C11—H11	120.9
H31—N3—H32	117 (5)	C13—C12—C11	119.4 (4)
O2—C1—O1	123.5 (3)	C13—C12—H12	120.3
O2—C1—C2	119.7 (3)	C11—C12—H12	120.3
O1—C1—C2	116.8 (3)	C12—C13—C14	118.3 (3)
C7—C2—C3	117.6 (3)	C12—C13—C15	118.9 (3)
C7—C2—C1	122.2 (3)	C14—C13—C15	122.8 (3)
C3—C2—C1	120.3 (3)	N2—C14—C13	122.9 (3)
C4—C3—C2	121.9 (4)	N2—C14—H14	118.5
C4—C3—H3	119.1	C13—C14—H14	118.5
C2—C3—H3	119.1	O3—C15—N3	123.2 (4)
C3—C4—C5	120.7 (4)	O3—C15—C13	118.9 (4)
C3—C4—H4	119.7	N3—C15—C13	117.9 (3)
O5—Co—O1—C1	−156.9 (3)	C3—C2—C1—O2	−178.5 (4)
O5^i—Co—O1—C1	23.1 (3)	C7—C2—C1—O1	−177.1 (4)
N2^i—Co—O1—C1	−64.0 (3)	C3—C2—C1—O1	2.7 (5)
N2—Co—O1—C1	116.0 (3)	C7—C2—C3—C4	−2.1 (6)
O1—Co—N2—C10	21.3 (3)	C1—C2—C3—C4	178.1 (4)
O1^i—Co—N2—C10	−158.7 (3)	C3—C2—C7—C6	1.5 (6)
O5—Co—N2—C10	−68.1 (3)	C1—C2—C7—C6	−178.7 (4)
O5^i—Co—N2—C10	111.9 (3)	C2—C3—C4—C5	0.6 (6)
O1—Co—N2—C14	−161.0 (3)	N1—C5—C4—C3	−177.9 (4)
O1^i—Co—N2—C14	19.0 (3)	C6—C5—C4—C3	1.4 (6)
O5—Co—N2—C14	109.7 (3)	N1—C5—C6—C7	177.3 (4)
O5^i—Co—N2—C14	−70.3 (3)	C4—C5—C6—C7	−2.0 (7)
Co—O1—C1—O2	−33.7 (6)	C2—C7—C6—C5	0.6 (7)
Co—O1—C1—C2	145.0 (3)	N2—C10—C11—C12	0.0 (7)
C9—N1—C5—C6	1.4 (7)	C13—C12—C11—C10	−1.1 (6)
C8—N1—C5—C6	179.6 (4)	C12—C13—C14—N2	−0.6 (6)
C9—N1—C5—C4	−179.3 (4)	C15—C13—C14—N2	−178.7 (3)
C8—N1—C5—C4	−1.1 (7)	C14—C13—C12—C11	1.4 (6)
C14—N2—C10—C11	0.8 (6)	C15—C13—C12—C11	179.6 (4)
Co—N2—C10—C11	178.7 (3)	O3—C15—C13—C12	−12.4 (5)
C10—N2—C14—C13	−0.5 (5)	N3—C15—C13—C12	167.5 (4)
Co—N2—C14—C13	−178.3 (3)	O3—C15—C13—C14	165.7 (4)
C7—C2—C1—O2	1.7 (6)	N3—C15—C13—C14	−14.4 (5)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O2	0.88 (3)	2.06 (4)	2.930 (5)	171 (5)
O4—H4B···O2^ii	0.91 (3)	1.97 (4)	2.866 (5)	168 (6)
O5—H5A···O2^i	0.92 (3)	1.83 (4)	2.731 (4)	165 (4)
O5—H5B···O3^iii	0.87 (3)	1.95 (3)	2.770 (4)	157 (5)
N3—H31···O4^iv	0.86 (5)	2.02 (5)	2.890 (5)	176 (6)

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