Bis(N-benzoyl­glycinato)diimidazole­cobalt(II)

In the title compound, [Co(C₉H₈NO₃)₂(C₃H₄N₂)₂], the Co^II atom, located on a twofold rotation axis, is coordinated by two N atoms and two O atoms in a distorted tetra­hedral geometry. The imine groups from the hippurate anion as well as the imidazole ligand act as donors in N—H...O hydrogen bonds; the two inter­molecular N—H...O hydrogen bonds create a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.039
• wR factor = 0.060
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           28.50
           From the CIF: _reflns_number_total               2899
           From the CIF: _diffrn_reflns_limit_ max hkl   37.   14.   19.
           From the CIF: _diffrn_reflns_limit_ min hkl  -37.  -14.  -19.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   39.   15.   20.
           Calculated minimum hkl  -39.  -15.  -20.
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.50
           From the CIF: _reflns_number_total               2899
           Count of symmetry unique reflns         1657
           Completeness (_total/calc)            174.95%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1242
           Fraction of Friedel pairs measured     0.750
           Are heavy atom types Z>Si present        yes

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and Mercury (Version 1.2.1; Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

Bis(N-benzoylglycinato)diimidazolecobalt(II)

Crystal data

[Co(C9H8NO3)2(C3H4N2)2]	F(000) = 2280
Mr = 551.42	Dx = 1.452 Mg m^−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 6391 reflections
a = 29.245 (11) Å	θ = 2–27°
b = 11.540 (5) Å	µ = 0.73 mm^−1
c = 14.945 (6) Å	T = 100 K
V = 5044 (4) Å^3	Tetrahedron, violet–blue
Z = 8	0.15 × 0.15 × 0.14 mm

Data collection

Kuma KM-4-CCD κ-geometry diffractometer	2899 independent reflections
Radiation source: fine-focus sealed tube	2212 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
ω scans	θmax = 28.5°, θmin = 3.1°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003)	h = −37→37
Tmin = 0.890, Tmax = 0.927	k = −14→14
8319 measured reflections	l = −19→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.061	w = 1/[σ^2(Fo^2) + (0.014P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
2899 reflections	Δρmax = 0.47 e Å^−3
174 parameters	Δρmin = −0.45 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1325 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.004 (14)

Special details

Experimental. Safety note: the perchlorates are potentially explosive. Although we have experienced no accidents so far, all compounds containing perchlorate should be handled with care and in small amounts. Spectroscopic analysis: IR (KBr pellets, cm^-1): 3301, 3137, 3064, 2944, 2868, 1634, 1605, 1540, 1490, 1419, 1401, 1297, 1257, 1072, 1002, 948, 931, 839, 728,699, 58, 618; UV-VIS (reflectance mode, cm^-1): 7780, 8660, 18330, 19450.

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	0.7500	0.7500	0.50000 (3)	0.01862 (14)
O1	0.69301 (5)	0.76707 (16)	0.56648 (12)	0.0227 (5)
O2	0.70744 (7)	0.61589 (17)	0.65493 (14)	0.0275 (5)
N1	0.63176 (7)	0.67005 (19)	0.76317 (16)	0.0188 (6)
H1	0.6362 (9)	0.691 (3)	0.8177 (19)	0.023*
O3	0.59616 (6)	0.54229 (17)	0.67278 (13)	0.0245 (5)
C1	0.68509 (9)	0.7030 (3)	0.63441 (18)	0.0200 (6)
C2	0.64463 (9)	0.7451 (2)	0.69005 (17)	0.0194 (6)
H2A	0.6521	0.8224	0.7147	0.023*
H2B	0.6179	0.7544	0.6500	0.023*
C3	0.60810 (8)	0.5726 (2)	0.7496 (2)	0.0188 (6)
C4	0.59662 (9)	0.4999 (2)	0.82952 (18)	0.0163 (7)
C5	0.62064 (9)	0.5075 (2)	0.91002 (17)	0.0204 (6)
H5	0.6442	0.5635	0.9165	0.024*
C6	0.61044 (9)	0.4342 (2)	0.98039 (18)	0.0247 (7)
H6	0.6271	0.4397	1.0348	0.030*
C7	0.57588 (9)	0.3526 (2)	0.97158 (19)	0.0257 (7)
H7	0.5690	0.3019	1.0198	0.031*
C8	0.55147 (9)	0.3454 (3)	0.8923 (2)	0.0277 (7)
H8	0.5275	0.2903	0.8864	0.033*
C9	0.56187 (9)	0.4180 (2)	0.82180 (19)	0.0248 (7)
H9	0.5452	0.4120	0.7675	0.030*
N3	0.75153 (7)	0.61080 (18)	0.41903 (14)	0.0177 (5)
C10	0.77519 (9)	0.5968 (3)	0.34294 (19)	0.0190 (7)
H10	0.7929	0.6555	0.3150	0.023*
N2	0.77046 (7)	0.4888 (2)	0.31161 (16)	0.0206 (5)
H2	0.7846 (8)	0.462 (2)	0.255 (2)	0.025*
C11	0.74274 (9)	0.4300 (2)	0.36998 (18)	0.0235 (7)
H11	0.7333	0.3514	0.3652	0.028*
C12	0.73127 (9)	0.5055 (2)	0.43604 (17)	0.0193 (6)
H12	0.7123	0.4884	0.4859	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co	0.0206 (3)	0.0199 (3)	0.0153 (3)	0.0013 (3)	0.000	0.000
O1	0.0234 (10)	0.0292 (12)	0.0156 (11)	0.0056 (9)	0.0044 (9)	0.0062 (9)
O2	0.0319 (12)	0.0268 (13)	0.0238 (12)	0.0114 (10)	0.0072 (10)	0.0110 (10)
N1	0.0249 (12)	0.0188 (13)	0.0128 (15)	−0.0040 (10)	0.0035 (12)	0.0002 (11)
O3	0.0321 (13)	0.0263 (13)	0.0152 (12)	0.0025 (9)	−0.0010 (10)	−0.0044 (10)
C1	0.0210 (15)	0.0252 (16)	0.0137 (15)	−0.0023 (13)	−0.0006 (13)	−0.0003 (13)
C2	0.0287 (15)	0.0167 (15)	0.0129 (14)	−0.0005 (13)	0.0056 (12)	0.0044 (13)
C3	0.0171 (13)	0.0250 (16)	0.0143 (15)	0.0049 (12)	0.0008 (14)	−0.0024 (15)
C4	0.0170 (14)	0.0191 (16)	0.0127 (16)	0.0034 (13)	0.0013 (11)	−0.0035 (13)
C5	0.0186 (14)	0.0248 (17)	0.0179 (16)	0.0005 (13)	0.0012 (12)	0.0011 (14)
C6	0.0232 (15)	0.0288 (18)	0.0220 (19)	0.0007 (13)	0.0006 (13)	0.0026 (14)
C7	0.0255 (16)	0.0287 (18)	0.0228 (19)	−0.0001 (13)	0.0036 (13)	0.0092 (13)
C8	0.0212 (17)	0.0358 (19)	0.0262 (18)	−0.0089 (14)	0.0025 (14)	0.0028 (15)
C9	0.0194 (16)	0.039 (2)	0.0157 (17)	−0.0062 (14)	−0.0011 (12)	−0.0033 (15)
N3	0.0190 (12)	0.0173 (13)	0.0169 (13)	−0.0022 (11)	−0.0020 (11)	−0.0030 (10)
C10	0.0195 (15)	0.0195 (17)	0.0182 (17)	0.0001 (13)	0.0019 (13)	−0.0025 (13)
N2	0.0165 (12)	0.0258 (15)	0.0193 (13)	0.0030 (11)	−0.0005 (10)	−0.0017 (13)
C11	0.0257 (17)	0.0167 (16)	0.0281 (18)	0.0008 (13)	−0.0067 (14)	−0.0012 (13)
C12	0.0226 (14)	0.0192 (16)	0.0159 (15)	−0.0020 (13)	−0.0038 (11)	0.0032 (14)

Geometric parameters (Å, º)

Co—O1^i	1.950 (2)	C5—H5	0.9500
Co—O1	1.950 (2)	C6—C7	1.387 (4)
Co—N3	2.012 (2)	C6—H6	0.9500
Co—N3^i	2.012 (2)	C7—C8	1.386 (4)
O1—C1	1.277 (3)	C7—H7	0.9500
O2—C1	1.238 (3)	C8—C9	1.380 (4)
N1—C3	1.336 (3)	C8—H8	0.9500
N1—C2	1.444 (3)	C9—H9	0.9500
N1—H1	0.86 (3)	N3—C10	1.341 (3)
O3—C3	1.250 (3)	N3—C12	1.375 (3)
C1—C2	1.526 (4)	C10—N2	1.339 (4)
C2—H2A	0.9900	C10—H10	0.9500
C2—H2B	0.9900	N2—C11	1.371 (3)
C3—C4	1.497 (4)	N2—H2	0.98 (3)
C4—C9	1.393 (4)	C11—C12	1.359 (3)
C4—C5	1.396 (3)	C11—H11	0.9500
C5—C6	1.382 (4)	C12—H12	0.9500
O1^i—Co—O1	118.74 (11)	C5—C6—C7	120.0 (3)
O1^i—Co—N3	101.93 (8)	C5—C6—H6	120.0
O1—Co—N3	113.96 (8)	C7—C6—H6	120.0
O1^i—Co—N3^i	113.96 (8)	C8—C7—C6	119.8 (3)
O1—Co—N3^i	101.93 (8)	C8—C7—H7	120.1
N3—Co—N3^i	106.04 (12)	C6—C7—H7	120.1
C1—O1—Co	120.11 (17)	C9—C8—C7	120.2 (3)
C3—N1—C2	121.7 (2)	C9—C8—H8	119.9
C3—N1—H1	117 (2)	C7—C8—H8	119.9
C2—N1—H1	121 (2)	C8—C9—C4	120.7 (3)
O2—C1—O1	124.8 (3)	C8—C9—H9	119.7
O2—C1—C2	122.2 (3)	C4—C9—H9	119.7
O1—C1—C2	113.0 (2)	C10—N3—C12	105.8 (2)
N1—C2—C1	115.1 (2)	C10—N3—Co	128.17 (19)
N1—C2—H2A	108.5	C12—N3—Co	125.77 (18)
C1—C2—H2A	108.5	N2—C10—N3	110.8 (2)
N1—C2—H2B	108.5	N2—C10—H10	124.6
C1—C2—H2B	108.5	N3—C10—H10	124.6
H2A—C2—H2B	107.5	C10—N2—C11	107.4 (2)
O3—C3—N1	121.2 (3)	C10—N2—H2	122.8 (13)
O3—C3—C4	120.9 (2)	C11—N2—H2	129.7 (14)
N1—C3—C4	117.8 (3)	C12—C11—N2	106.9 (3)
C9—C4—C5	118.8 (3)	C12—C11—H11	126.6
C9—C4—C3	118.5 (3)	N2—C11—H11	126.6
C5—C4—C3	122.7 (2)	C11—C12—N3	109.0 (2)
C6—C5—C4	120.6 (3)	C11—C12—H12	125.5
C6—C5—H5	119.7	N3—C12—H12	125.5
C4—C5—H5	119.7
O1^i—Co—O1—C1	−43.55 (18)	C3—C4—C5—C6	−176.4 (2)
N3—Co—O1—C1	76.6 (2)	C4—C5—C6—C7	−0.4 (4)
N3^i—Co—O1—C1	−169.7 (2)	C5—C6—C7—C8	−0.4 (4)
Co—O1—C1—O2	−12.4 (4)	C6—C7—C8—C9	0.9 (4)
Co—O1—C1—C2	167.29 (16)	C7—C8—C9—C4	−0.6 (4)
C3—N1—C2—C1	−77.2 (3)	C5—C4—C9—C8	−0.2 (4)
O2—C1—C2—N1	−5.5 (4)	C3—C4—C9—C8	177.0 (2)
O1—C1—C2—N1	174.8 (2)	C12—N3—C10—N2	0.4 (3)
C2—N1—C3—O3	0.1 (4)	Co—N3—C10—N2	174.87 (16)
C2—N1—C3—C4	179.6 (2)	N3—C10—N2—C11	−0.3 (3)
O3—C3—C4—C9	−18.5 (3)	C10—N2—C11—C12	0.1 (3)
N1—C3—C4—C9	162.0 (2)	N2—C11—C12—N3	0.1 (3)
O3—C3—C4—C5	158.6 (3)	C10—N3—C12—C11	−0.3 (3)
N1—C3—C4—C5	−20.9 (4)	Co—N3—C12—C11	−174.98 (17)
C9—C4—C5—C6	0.7 (4)

Symmetry code: (i) −x+3/2, −y+3/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^ii	0.86 (3)	2.03 (3)	2.846 (3)	159 (3)
N2—H2···O2^iii	0.98 (3)	1.77 (3)	2.713 (3)	160 (2)

Symmetry codes: (ii) −x+5/4, y+1/4, z+1/4; (iii) −x+3/2, −y+1, z−1/2.