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In the title compound, [Co(C9H8NO3)2(C3H4N2)2], the CoII 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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011901/is2017sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011901/is2017Isup2.hkl
Contains datablock I

CCDC reference: 608421

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

Computing details top

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) top
Crystal data top
[Co(C9H8NO3)2(C3H4N2)2]F(000) = 2280
Mr = 551.42Dx = 1.452 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 6391 reflections
a = 29.245 (11) Åθ = 2–27°
b = 11.540 (5) ŵ = 0.73 mm1
c = 14.945 (6) ÅT = 100 K
V = 5044 (4) Å3Tetrahedron, violet–blue
Z = 80.15 × 0.15 × 0.14 mm
Data collection top
Kuma KM-4-CCD κ-geometry
diffractometer
2899 independent reflections
Radiation source: fine-focus sealed tube2212 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
ω scansθmax = 28.5°, θmin = 3.1°
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2003)
h = 3737
Tmin = 0.890, Tmax = 0.927k = 1414
8319 measured reflectionsl = 1919
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.061 w = 1/[σ2(Fo2) + (0.014P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
2899 reflectionsΔρmax = 0.47 e Å3
174 parametersΔρmin = 0.45 e Å3
1 restraintAbsolute structure: Flack (1983), 1325 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.004 (14)
Special details top

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 (Å2) top
xyzUiso*/Ueq
Co0.75000.75000.50000 (3)0.01862 (14)
O10.69301 (5)0.76707 (16)0.56648 (12)0.0227 (5)
O20.70744 (7)0.61589 (17)0.65493 (14)0.0275 (5)
N10.63176 (7)0.67005 (19)0.76317 (16)0.0188 (6)
H10.6362 (9)0.691 (3)0.8177 (19)0.023*
O30.59616 (6)0.54229 (17)0.67278 (13)0.0245 (5)
C10.68509 (9)0.7030 (3)0.63441 (18)0.0200 (6)
C20.64463 (9)0.7451 (2)0.69005 (17)0.0194 (6)
H2A0.65210.82240.71470.023*
H2B0.61790.75440.65000.023*
C30.60810 (8)0.5726 (2)0.7496 (2)0.0188 (6)
C40.59662 (9)0.4999 (2)0.82952 (18)0.0163 (7)
C50.62064 (9)0.5075 (2)0.91002 (17)0.0204 (6)
H50.64420.56350.91650.024*
C60.61044 (9)0.4342 (2)0.98039 (18)0.0247 (7)
H60.62710.43971.03480.030*
C70.57588 (9)0.3526 (2)0.97158 (19)0.0257 (7)
H70.56900.30191.01980.031*
C80.55147 (9)0.3454 (3)0.8923 (2)0.0277 (7)
H80.52750.29030.88640.033*
C90.56187 (9)0.4180 (2)0.82180 (19)0.0248 (7)
H90.54520.41200.76750.030*
N30.75153 (7)0.61080 (18)0.41903 (14)0.0177 (5)
C100.77519 (9)0.5968 (3)0.34294 (19)0.0190 (7)
H100.79290.65550.31500.023*
N20.77046 (7)0.4888 (2)0.31161 (16)0.0206 (5)
H20.7846 (8)0.462 (2)0.255 (2)0.025*
C110.74274 (9)0.4300 (2)0.36998 (18)0.0235 (7)
H110.73330.35140.36520.028*
C120.73127 (9)0.5055 (2)0.43604 (17)0.0193 (6)
H120.71230.48840.48590.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co0.0206 (3)0.0199 (3)0.0153 (3)0.0013 (3)0.0000.000
O10.0234 (10)0.0292 (12)0.0156 (11)0.0056 (9)0.0044 (9)0.0062 (9)
O20.0319 (12)0.0268 (13)0.0238 (12)0.0114 (10)0.0072 (10)0.0110 (10)
N10.0249 (12)0.0188 (13)0.0128 (15)0.0040 (10)0.0035 (12)0.0002 (11)
O30.0321 (13)0.0263 (13)0.0152 (12)0.0025 (9)0.0010 (10)0.0044 (10)
C10.0210 (15)0.0252 (16)0.0137 (15)0.0023 (13)0.0006 (13)0.0003 (13)
C20.0287 (15)0.0167 (15)0.0129 (14)0.0005 (13)0.0056 (12)0.0044 (13)
C30.0171 (13)0.0250 (16)0.0143 (15)0.0049 (12)0.0008 (14)0.0024 (15)
C40.0170 (14)0.0191 (16)0.0127 (16)0.0034 (13)0.0013 (11)0.0035 (13)
C50.0186 (14)0.0248 (17)0.0179 (16)0.0005 (13)0.0012 (12)0.0011 (14)
C60.0232 (15)0.0288 (18)0.0220 (19)0.0007 (13)0.0006 (13)0.0026 (14)
C70.0255 (16)0.0287 (18)0.0228 (19)0.0001 (13)0.0036 (13)0.0092 (13)
C80.0212 (17)0.0358 (19)0.0262 (18)0.0089 (14)0.0025 (14)0.0028 (15)
C90.0194 (16)0.039 (2)0.0157 (17)0.0062 (14)0.0011 (12)0.0033 (15)
N30.0190 (12)0.0173 (13)0.0169 (13)0.0022 (11)0.0020 (11)0.0030 (10)
C100.0195 (15)0.0195 (17)0.0182 (17)0.0001 (13)0.0019 (13)0.0025 (13)
N20.0165 (12)0.0258 (15)0.0193 (13)0.0030 (11)0.0005 (10)0.0017 (13)
C110.0257 (17)0.0167 (16)0.0281 (18)0.0008 (13)0.0067 (14)0.0012 (13)
C120.0226 (14)0.0192 (16)0.0159 (15)0.0020 (13)0.0038 (11)0.0032 (14)
Geometric parameters (Å, º) top
Co—O1i1.950 (2)C5—H50.9500
Co—O11.950 (2)C6—C71.387 (4)
Co—N32.012 (2)C6—H60.9500
Co—N3i2.012 (2)C7—C81.386 (4)
O1—C11.277 (3)C7—H70.9500
O2—C11.238 (3)C8—C91.380 (4)
N1—C31.336 (3)C8—H80.9500
N1—C21.444 (3)C9—H90.9500
N1—H10.86 (3)N3—C101.341 (3)
O3—C31.250 (3)N3—C121.375 (3)
C1—C21.526 (4)C10—N21.339 (4)
C2—H2A0.9900C10—H100.9500
C2—H2B0.9900N2—C111.371 (3)
C3—C41.497 (4)N2—H20.98 (3)
C4—C91.393 (4)C11—C121.359 (3)
C4—C51.396 (3)C11—H110.9500
C5—C61.382 (4)C12—H120.9500
O1i—Co—O1118.74 (11)C5—C6—C7120.0 (3)
O1i—Co—N3101.93 (8)C5—C6—H6120.0
O1—Co—N3113.96 (8)C7—C6—H6120.0
O1i—Co—N3i113.96 (8)C8—C7—C6119.8 (3)
O1—Co—N3i101.93 (8)C8—C7—H7120.1
N3—Co—N3i106.04 (12)C6—C7—H7120.1
C1—O1—Co120.11 (17)C9—C8—C7120.2 (3)
C3—N1—C2121.7 (2)C9—C8—H8119.9
C3—N1—H1117 (2)C7—C8—H8119.9
C2—N1—H1121 (2)C8—C9—C4120.7 (3)
O2—C1—O1124.8 (3)C8—C9—H9119.7
O2—C1—C2122.2 (3)C4—C9—H9119.7
O1—C1—C2113.0 (2)C10—N3—C12105.8 (2)
N1—C2—C1115.1 (2)C10—N3—Co128.17 (19)
N1—C2—H2A108.5C12—N3—Co125.77 (18)
C1—C2—H2A108.5N2—C10—N3110.8 (2)
N1—C2—H2B108.5N2—C10—H10124.6
C1—C2—H2B108.5N3—C10—H10124.6
H2A—C2—H2B107.5C10—N2—C11107.4 (2)
O3—C3—N1121.2 (3)C10—N2—H2122.8 (13)
O3—C3—C4120.9 (2)C11—N2—H2129.7 (14)
N1—C3—C4117.8 (3)C12—C11—N2106.9 (3)
C9—C4—C5118.8 (3)C12—C11—H11126.6
C9—C4—C3118.5 (3)N2—C11—H11126.6
C5—C4—C3122.7 (2)C11—C12—N3109.0 (2)
C6—C5—C4120.6 (3)C11—C12—H12125.5
C6—C5—H5119.7N3—C12—H12125.5
C4—C5—H5119.7
O1i—Co—O1—C143.55 (18)C3—C4—C5—C6176.4 (2)
N3—Co—O1—C176.6 (2)C4—C5—C6—C70.4 (4)
N3i—Co—O1—C1169.7 (2)C5—C6—C7—C80.4 (4)
Co—O1—C1—O212.4 (4)C6—C7—C8—C90.9 (4)
Co—O1—C1—C2167.29 (16)C7—C8—C9—C40.6 (4)
C3—N1—C2—C177.2 (3)C5—C4—C9—C80.2 (4)
O2—C1—C2—N15.5 (4)C3—C4—C9—C8177.0 (2)
O1—C1—C2—N1174.8 (2)C12—N3—C10—N20.4 (3)
C2—N1—C3—O30.1 (4)Co—N3—C10—N2174.87 (16)
C2—N1—C3—C4179.6 (2)N3—C10—N2—C110.3 (3)
O3—C3—C4—C918.5 (3)C10—N2—C11—C120.1 (3)
N1—C3—C4—C9162.0 (2)N2—C11—C12—N30.1 (3)
O3—C3—C4—C5158.6 (3)C10—N3—C12—C110.3 (3)
N1—C3—C4—C520.9 (4)Co—N3—C12—C11174.98 (17)
C9—C4—C5—C60.7 (4)
Symmetry code: (i) x+3/2, y+3/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3ii0.86 (3)2.03 (3)2.846 (3)159 (3)
N2—H2···O2iii0.98 (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, z1/2.
 

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