Literature DB >> 21580817

Tris{N-[(anthracen-9-yl)methyl-ene-amino]thio-ureato}cobalt(III) tetra-hydrate.

Jianying Zhao1, Yu Zhang.   

Abstract

In the title complex, [Co(C(16)H(12)N(3)S)(3)]·4H(2)O, the central Co(III) atom is in a distorted octa-hedral coordination environment. There are three N-[(anthracen-9-yl)-methyl-ene-amino]-thio-ureate ligands coordinated to the Co(III) atom via three imine N and three thio-amide S atoms. The Co-S and Co-N bond distances are in expected ranges [2.2194 (8)-2.2545 (8) and 1.926 (2)-1.985 (2)Å, respectively]. The endocyclic S-Co-N bond angles in the five-membered chelate rings range from 82.91 (7) to 85.33 (7)°. The structure contains four water mol-ecules which are disordered over 12 sites and link the complex mol-ecules into a three-dimensional network through N-H⋯O, O-H⋯O, O-H⋯N, and O-H⋯S hydrogen bonds.

Entities:  

Year:  2008        PMID： 21580817      PMCID： PMC2959531          DOI： 10.1107/S1600536808031425

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related structures, see: Chandra et al. (2003 ▶); Funston et al. (2003 ▶); Casas et al. (2000 ▶); Rodriguez-Arguelles et al. (2004 ▶); Saha et al. (2003 ▶). For biological activities, see: He et al. (2003 ▶); Horton et al. (2003 ▶); Kabanos et al. (1992 ▶); Navarrete-Vazquez et al. (2001 ▶); Ozden et al., 2005 ▶; Pawar et al. (2004 ▶).

Experimental

Crystal data

[Co(C16H12N3S)3]·4H2O M = 966.03 Triclinic, a = 9.8907 (19) Å b = 17.073 (3) Å c = 17.511 (4) Å α = 91.315 (7)° β = 99.920 (6)° γ = 93.972 (6)° V = 2903.9 (10) Å3 Z = 2 Mo Kα radiation μ = 0.45 mm−1 T = 291 (2) K 0.28 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.886, T max = 0.916 36568 measured reflections 11268 independent reflections 8244 reflections with I > 2σ(I) R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.057 wR(F 2) = 0.132 S = 1.04 11268 reflections 723 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.90 e Å−3 Δρmin = −0.92 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031425/pv2097sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031425/pv2097Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Co(C16H12N3S)3]·4H2OZ = 2
Mr = 966.03F(000) = 1004
Triclinic, P1Dx = 1.105 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8907 (19) ÅCell parameters from 5672 reflections
b = 17.073 (3) Åθ = 2.1–25.1°
c = 17.511 (4) ŵ = 0.45 mm−1
α = 91.315 (7)°T = 291 K
β = 99.920 (6)°Block, dark brown
γ = 93.972 (6)°0.28 × 0.22 × 0.20 mm
V = 2903.9 (10) Å3
Bruker SMART APEX CCD diffractometer11268 independent reflections
Radiation source: fine-focus sealed tube8244 reflections with I > 2σ(I)
graphiteRint = 0.054
φ and ω scansθmax = 26.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −11→12
Tmin = 0.886, Tmax = 0.916k = −21→21
36568 measured reflectionsl = −21→19
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0616P)2 + 1.0884P] where P = (Fo2 + 2Fc2)/3
11268 reflections(Δ/σ)max < 0.001
723 parametersΔρmax = 0.90 e Å−3
0 restraintsΔρmin = −0.92 e Å−3
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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)2.9231 (0.0039) x + 5.2249 (0.0137) y + 14.3798 (0.0073) z = 8.0721 (0.0041)* -0.0965 (0.0029) C1 * -0.0957 (0.0029) C2 * -0.0036 (0.0029) C3 * 0.0943 (0.0029) C4 * 0.1068 (0.0032) C5 * 0.0348 (0.0029) C6 * -0.0687 (0.0029) C7 * -0.0824 (0.0030) C8 * -0.0553 (0.0032) C9 * -0.0172 (0.0030) C10 * 0.0763 (0.0032) C11 * 0.0979 (0.0031) C12 * 0.0622 (0.0029) C13 * -0.0529 (0.0030) C14Rms deviation of fitted atoms = 0.0741- 4.9814 (0.0075) x + 4.3447 (0.0118) y + 15.7855 (0.0071) z = 7.5113 (0.0076)Angle to previous plane (with approximate e.s.d.) = 47.70 (0.05)* -0.0696 (0.0009) Co1 * 0.0932 (0.0014) N1 * -0.0516 (0.0018) N2 * -0.0286 (0.0017) C16 * 0.0566 (0.0011) S1Rms deviation of fitted atoms = 0.06362.8734 (0.0035) x + 5.6841 (0.0129) y + 14.2322 (0.0068) z = 7.3855 (0.0124)Angle to previous plane (with approximate e.s.d.) = 47.60 (0.05)* 0.0309 (0.0024) C17 * 0.0141 (0.0027) C18 * -0.0339 (0.0027) C19 * -0.0535 (0.0030) C20 * -0.0297 (0.0030) C21 * 0.0358 (0.0030) C22 * 0.0565 (0.0029) C23 * 0.0204 (0.0029) C24 * 0.0095 (0.0030) C25 * -0.0415 (0.0030) C26 * -0.0419 (0.0028) C27 * -0.0195 (0.0027) C28 * 0.0296 (0.0027) C29 * 0.0231 (0.0027) C30Rms deviation of fitted atoms = 0.0341- 9.1789 (0.0035) x + 2.1487 (0.0123) y - 3.5707 (0.0144) z = 0.8355 (0.0111)Angle to previous plane (with approximate e.s.d.) = 54.95 (0.06)* -0.0837 (0.0009) Co1 * 0.1056 (0.0013) N4 * -0.0460 (0.0017) N5 * -0.0487 (0.0018) C32 * 0.0728 (0.0012) S2Rms deviation of fitted atoms = 0.07486.3204 (0.0049) x + 12.0610 (0.0065) y + 0.3576 (0.0128) z = 7.7520 (0.0036)Angle to previous plane (with approximate e.s.d.) = 52.76 (0.06)* 0.0549 (0.0024) C33 * 0.0124 (0.0026) C34 * 0.0290 (0.0026) C35 * -0.0236 (0.0026) C36 * -0.0270 (0.0027) C37 * -0.0047 (0.0027) C38 * -0.0022 (0.0027) C39 * -0.0012 (0.0030) C40 * 0.0058 (0.0030) C41 * 0.0210 (0.0032) C42 * 0.0245 (0.0031) C43 * -0.0395 (0.0030) C44 * -0.0445 (0.0030) C45 * -0.0047 (0.0028) C46Rms deviation of fitted atoms = 0.0267- 0.9842 (0.0075) x + 16.5335 (0.0046) y - 4.5518 (0.0118) z = 10.6006 (0.0060)Angle to previous plane (with approximate e.s.d.) = 51.51 (0.05)* 0.1181 (0.0009) Co1 * -0.1461 (0.0013) N7 * 0.0569 (0.0016) N8 * 0.0834 (0.0015) C48 * -0.1122 (0.0010) S3Rms deviation of fitted atoms = 0.1078
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.
xyzUiso*/UeqOcc. (<1)
C1−0.0004 (4)0.49552 (19)0.37467 (18)0.0451 (8)
C20.1076 (3)0.44401 (18)0.37149 (18)0.0414 (7)
C30.2263 (4)0.4681 (2)0.3450 (2)0.0495 (8)
H30.23510.51780.32490.059*
C40.3333 (4)0.4189 (2)0.3479 (2)0.0504 (8)
H40.41310.43550.32960.060*
C50.3203 (4)0.3449 (2)0.3783 (2)0.0605 (10)
H50.39140.31180.37990.073*
C60.2032 (4)0.3201 (2)0.4062 (2)0.0525 (9)
H60.19580.27070.42700.063*
C70.0951 (4)0.3695 (2)0.40299 (18)0.0464 (8)
C8−0.0213 (4)0.34682 (19)0.4339 (2)0.0501 (9)
H8−0.02990.29630.45210.060*
C9−0.1257 (4)0.39649 (19)0.4390 (2)0.0507 (9)
C10−0.2356 (4)0.3693 (2)0.4739 (2)0.0557 (10)
H10−0.24340.31850.49140.067*
C11−0.3298 (4)0.4211 (2)0.4807 (2)0.0638 (11)
H11−0.40330.40550.50500.077*
C12−0.3229 (4)0.4970 (2)0.4532 (2)0.0530 (9)
H12−0.39240.52980.45810.064*
C13−0.2153 (4)0.5235 (2)0.4192 (2)0.0504 (8)
H13−0.20870.57480.40280.060*
C14−0.1148 (4)0.47218 (18)0.40945 (18)0.0424 (7)
C150.0225 (3)0.57617 (17)0.34798 (17)0.0354 (6)
H150.10310.60450.37160.043*
C16−0.2661 (3)0.61425 (16)0.22101 (18)0.0339 (6)
C17−0.0070 (3)0.93633 (15)0.14856 (15)0.0295 (6)
C18−0.1222 (3)0.98154 (16)0.15258 (17)0.0344 (6)
C19−0.2345 (3)0.95054 (17)0.18427 (19)0.0401 (7)
H19−0.23480.90010.20320.048*
C20−0.3452 (4)0.9954 (2)0.1873 (2)0.0496 (8)
H20−0.41960.97500.20840.060*
C21−0.3457 (4)1.07082 (19)0.1590 (2)0.0496 (8)
H21−0.42081.10040.16030.060*
C22−0.2347 (4)1.1015 (2)0.1289 (2)0.0521 (9)
H22−0.23431.15220.11070.062*
C23−0.1224 (3)1.05713 (18)0.12542 (19)0.0419 (7)
C24−0.0095 (4)1.08603 (19)0.08854 (19)0.0464 (8)
H24−0.01091.13570.06780.056*
C250.0994 (4)1.0419 (2)0.08340 (19)0.0481 (8)
C260.2076 (4)1.0709 (2)0.0464 (2)0.0522 (9)
H260.20441.12020.02500.063*
C270.3174 (4)1.0272 (2)0.0417 (2)0.0516 (9)
H270.38831.04800.01790.062*
C280.3252 (3)0.95342 (19)0.07113 (19)0.0458 (8)
H280.39940.92410.06670.055*
C290.2176 (4)0.92301 (19)0.1084 (2)0.0462 (8)
H290.22240.87370.12980.055*
C300.1043 (3)0.96635 (17)0.11354 (17)0.0377 (7)
C31−0.0046 (3)0.85530 (15)0.17471 (16)0.0285 (6)
H31−0.00420.81680.13630.034*
C32−0.0260 (3)0.86221 (17)0.36530 (18)0.0384 (7)
C330.0539 (3)0.61759 (16)0.04899 (16)0.0329 (6)
C34−0.0004 (3)0.64474 (17)−0.02610 (18)0.0388 (7)
C35−0.1012 (3)0.69926 (18)−0.0367 (2)0.0460 (8)
H35−0.13460.71940.00560.055*
C36−0.1496 (4)0.7224 (2)−0.1095 (2)0.0504 (9)
H36−0.21970.7565−0.11630.060*
C37−0.0970 (4)0.6965 (2)−0.1755 (2)0.0519 (9)
H37−0.13120.7145−0.22430.062*
C380.0059 (4)0.6442 (2)−0.1668 (2)0.0516 (9)
H380.04200.6276−0.20960.062*
C390.0548 (3)0.61660 (19)−0.09285 (19)0.0450 (8)
C400.1544 (4)0.56412 (17)−0.0809 (2)0.0524 (9)
H400.18960.5466−0.12360.063*
C410.2052 (3)0.53602 (18)−0.0105 (2)0.0451 (8)
C420.3102 (4)0.4819 (2)0.0004 (2)0.0568 (9)
H420.34590.4651−0.04240.068*
C430.3600 (4)0.4540 (2)0.0715 (2)0.0538 (9)
H430.43080.42040.07740.065*
C440.3018 (4)0.4773 (2)0.1356 (2)0.0519 (9)
H440.33180.45680.18380.062*
C450.2022 (4)0.5293 (2)0.1283 (2)0.0524 (9)
H450.16700.54390.17200.063*
C460.1509 (3)0.56158 (18)0.05700 (19)0.0427 (7)
C47−0.0038 (3)0.64530 (16)0.11451 (16)0.0336 (6)
H47−0.09780.63420.11220.040*
C480.2714 (3)0.72902 (16)0.24213 (17)0.0329 (6)
Co1−0.01722 (4)0.72094 (2)0.26757 (2)0.02906 (11)
N1−0.0574 (2)0.61179 (13)0.29523 (14)0.0318 (5)
N2−0.1777 (2)0.56985 (13)0.25965 (13)0.0324 (5)
N3−0.3917 (3)0.58207 (18)0.18756 (17)0.0433 (6)
H3B−0.382 (4)0.534 (2)0.179 (2)0.052*
H3A−0.440 (4)0.598 (2)0.147 (2)0.052*
N4−0.0029 (2)0.83041 (12)0.24356 (13)0.0254 (5)
N50.0057 (2)0.88954 (13)0.29963 (14)0.0320 (5)
N6−0.0234 (3)0.91326 (19)0.42362 (19)0.0514 (8)
H6B−0.088 (4)0.901 (2)0.448 (2)0.062*
H6A−0.033 (4)0.959 (2)0.406 (2)0.062*
N70.0635 (2)0.68505 (13)0.17780 (14)0.0327 (5)
N80.1979 (2)0.70442 (13)0.17449 (14)0.0330 (5)
N90.4071 (3)0.7494 (2)0.2452 (2)0.0519 (8)
H9B0.454 (4)0.721 (2)0.278 (2)0.062*
H9A0.425 (4)0.798 (2)0.259 (2)0.062*
O10.1493 (6)0.0369 (3)0.3188 (4)0.048 (3)0.390 (10)
H1X0.23000.03920.31320.058*0.39 (8)
H1Y0.15210.05170.36400.058*0.39 (8)
O20.2155 (9)0.8786 (6)0.6169 (6)0.061 (4)0.301 (12)
H2X0.20500.89590.57320.073*0.301 (9)
H2Y0.23850.83390.61130.073*0.301 (9)
O30.1224 (8)0.7650 (6)0.7284 (5)0.055 (4)0.309 (11)
H3X0.16720.72690.72470.065*0.309 (9)
H3Y0.15480.78510.77120.065*0.309 (8)
O40.4442 (8)0.7059 (5)0.7923 (5)0.076 (4)0.400 (13)
H4X0.44620.69270.83720.091*0.400 (11)
H4Y0.52150.69930.78360.091*0.400 (10)
O50.5254 (7)0.7669 (6)1.0002 (6)0.055 (4)0.304 (11)
H5X0.54280.80961.02360.066*0.304 (9)
H5Y0.52340.77700.95450.066*0.304 (9)
O60.3423 (14)0.1055 (6)0.2972 (7)0.076 (6)0.297 (14)
H6X0.29570.12550.26040.091*0.297 (12)
H6Y0.41690.10140.28370.091*0.297 (10)
O70.4935 (8)0.6024 (4)0.3438 (5)0.065 (3)0.392 (12)
H7X0.42040.60010.36010.078*0.392 (9)
H7Y0.48040.57090.30680.078*0.392 (10)
O80.6008 (10)0.7804 (7)0.3965 (6)0.066 (5)0.300 (12)
H8X0.56130.74850.42100.079*0.300 (10)
H8Y0.67490.76240.39460.079*0.300 (9)
O90.5014 (9)0.1250 (5)0.5405 (6)0.057 (4)0.308 (11)
H9X0.55420.16290.53530.068*0.308 (8)
H9Y0.54610.09870.57300.068*0.308 (9)
O10−0.5834 (6)0.6894 (3)0.0820 (3)0.040 (2)0.396 (9)
H10X−0.57520.71740.12150.048*0.396 (7)
H10Y−0.65620.66300.08080.048*0.396 (7)
O110.3213 (9)0.9052 (5)0.2864 (5)0.051 (3)0.299 (11)
H11X0.26170.87380.29750.061*0.299 (8)
H11Y0.32860.94080.31940.061*0.299 (8)
O120.3964 (8)0.0380 (4)0.6305 (4)0.041 (3)0.304 (9)
H12X0.46810.06590.64280.049*0.304 (7)
H12Y0.37820.04010.58310.049*0.304 (7)
S1−0.23532 (7)0.71424 (4)0.20858 (4)0.03045 (16)
S2−0.06780 (7)0.76419 (4)0.37977 (4)0.03041 (16)
S30.20521 (7)0.73627 (4)0.32576 (4)0.03020 (16)
U11U22U33U12U13U23
C10.055 (2)0.0498 (18)0.0292 (17)0.0107 (15)−0.0014 (14)0.0085 (14)
C20.0452 (18)0.0451 (16)0.0315 (16)−0.0018 (13)0.0016 (14)−0.0007 (13)
C30.054 (2)0.056 (2)0.040 (2)0.0048 (16)0.0127 (16)−0.0105 (15)
C40.050 (2)0.061 (2)0.040 (2)0.0086 (16)0.0090 (16)−0.0141 (16)
C50.061 (2)0.068 (2)0.052 (2)−0.0215 (19)0.0207 (19)0.0004 (18)
C60.055 (2)0.0536 (19)0.043 (2)−0.0176 (16)0.0001 (16)0.0068 (16)
C70.054 (2)0.0527 (18)0.0256 (16)−0.0164 (16)−0.0026 (14)−0.0070 (14)
C80.054 (2)0.0430 (17)0.045 (2)−0.0120 (15)−0.0091 (16)0.0158 (15)
C90.058 (2)0.0423 (17)0.044 (2)−0.0014 (15)−0.0107 (17)0.0074 (14)
C100.045 (2)0.0503 (19)0.060 (2)−0.0008 (15)−0.0211 (18)0.0073 (17)
C110.054 (2)0.075 (3)0.055 (2)0.0200 (19)−0.0152 (19)0.004 (2)
C120.054 (2)0.068 (2)0.0380 (19)0.0226 (17)0.0055 (16)0.0048 (16)
C130.047 (2)0.070 (2)0.0362 (19)0.0193 (16)0.0070 (15)0.0017 (16)
C140.054 (2)0.0458 (17)0.0261 (16)0.0120 (14)0.0000 (14)0.0045 (13)
C150.0332 (15)0.0418 (15)0.0308 (16)0.0037 (12)0.0032 (12)0.0059 (12)
C160.0304 (15)0.0316 (13)0.0392 (17)0.0005 (11)0.0066 (12)−0.0048 (12)
C170.0335 (14)0.0313 (13)0.0199 (13)−0.0092 (11)−0.0005 (11)−0.0029 (10)
C180.0319 (15)0.0376 (14)0.0323 (16)−0.0071 (11)0.0070 (12)−0.0089 (12)
C190.0446 (17)0.0360 (15)0.0425 (19)0.0025 (12)0.0156 (14)0.0011 (13)
C200.0437 (19)0.0543 (19)0.051 (2)0.0133 (15)0.0053 (16)−0.0027 (16)
C210.0474 (19)0.0459 (18)0.058 (2)0.0074 (14)0.0158 (17)−0.0156 (16)
C220.0446 (19)0.0510 (19)0.060 (2)−0.0004 (15)0.0111 (17)−0.0119 (17)
C230.0414 (17)0.0415 (16)0.0420 (18)−0.0150 (13)0.0141 (14)−0.0114 (14)
C240.058 (2)0.0477 (17)0.0354 (18)−0.0217 (15)0.0259 (15)−0.0075 (14)
C250.056 (2)0.0495 (18)0.0337 (18)−0.0192 (16)0.0042 (15)−0.0006 (14)
C260.061 (2)0.056 (2)0.038 (2)−0.0121 (17)0.0085 (17)0.0184 (16)
C270.058 (2)0.0489 (18)0.0406 (19)−0.0233 (16)−0.0036 (16)0.0122 (15)
C280.0393 (17)0.0466 (17)0.0426 (19)−0.0135 (13)−0.0124 (14)0.0100 (14)
C290.053 (2)0.0393 (16)0.0402 (19)−0.0077 (14)−0.0051 (15)0.0033 (13)
C300.0427 (17)0.0417 (15)0.0246 (15)−0.0119 (13)0.0011 (13)−0.0011 (12)
C310.0326 (14)0.0260 (12)0.0261 (15)0.0078 (10)0.0011 (11)−0.0001 (10)
C320.0441 (17)0.0351 (14)0.0339 (17)−0.0042 (12)0.0049 (13)−0.0089 (12)
C330.0406 (16)0.0355 (14)0.0200 (14)−0.0050 (12)0.0016 (12)−0.0038 (11)
C340.0409 (17)0.0396 (15)0.0317 (16)−0.0076 (12)−0.0014 (13)0.0037 (12)
C350.0468 (19)0.0441 (17)0.048 (2)−0.0062 (14)0.0135 (16)0.0017 (15)
C360.0457 (19)0.0495 (18)0.053 (2)−0.0158 (15)0.0091 (16)−0.0041 (16)
C370.054 (2)0.0531 (19)0.044 (2)−0.0133 (16)0.0030 (16)0.0041 (16)
C380.064 (2)0.0493 (18)0.042 (2)−0.0105 (16)0.0150 (17)0.0034 (15)
C390.0414 (18)0.0444 (17)0.0424 (19)−0.0155 (14)−0.0034 (15)−0.0053 (14)
C400.079 (3)0.0286 (14)0.045 (2)−0.0024 (15)0.0009 (18)−0.0004 (13)
C410.0434 (18)0.0377 (15)0.050 (2)0.0052 (13)−0.0036 (15)−0.0020 (14)
C420.064 (2)0.052 (2)0.054 (2)0.0149 (17)0.0047 (19)0.0014 (17)
C430.057 (2)0.0507 (19)0.049 (2)0.0201 (16)−0.0081 (17)−0.0192 (16)
C440.049 (2)0.0514 (19)0.053 (2)0.0117 (15)0.0029 (17)−0.0125 (16)
C450.055 (2)0.055 (2)0.047 (2)0.0086 (16)0.0036 (17)0.0029 (16)
C460.0429 (17)0.0398 (16)0.0400 (18)−0.0031 (13)−0.0047 (14)−0.0065 (13)
C470.0365 (15)0.0388 (14)0.0247 (15)0.0169 (12)−0.0030 (12)0.0035 (11)
C480.0381 (16)0.0325 (13)0.0293 (15)0.0083 (11)0.0076 (12)−0.0040 (11)
Co10.0298 (2)0.02984 (19)0.0273 (2)0.00171 (14)0.00459 (15)−0.00025 (14)
N10.0262 (12)0.0308 (11)0.0387 (14)0.0020 (9)0.0062 (10)0.0010 (10)
N20.0363 (13)0.0337 (12)0.0248 (12)−0.0071 (10)0.0023 (10)0.0033 (9)
N30.0337 (14)0.0530 (16)0.0384 (16)−0.0031 (12)−0.0049 (12)0.0016 (13)
N40.0235 (11)0.0252 (10)0.0251 (12)−0.0057 (8)0.0016 (9)−0.0074 (9)
N50.0302 (12)0.0365 (12)0.0295 (13)0.0019 (9)0.0077 (10)−0.0101 (10)
N60.0503 (17)0.0517 (16)0.0505 (19)−0.0176 (14)0.0152 (14)−0.0189 (14)
N70.0421 (14)0.0288 (11)0.0273 (13)−0.0043 (10)0.0102 (10)−0.0050 (9)
N80.0378 (13)0.0291 (11)0.0289 (13)−0.0081 (9)0.0017 (10)−0.0025 (9)
N90.0481 (18)0.0562 (18)0.055 (2)0.0013 (14)0.0224 (15)−0.0152 (15)
O10.038 (4)0.066 (4)0.037 (4)−0.020 (3)0.005 (3)−0.002 (3)
O20.057 (6)0.063 (6)0.067 (7)0.006 (4)0.022 (5)0.006 (4)
O30.035 (5)0.089 (7)0.038 (5)0.002 (4)0.003 (3)−0.012 (4)
O40.058 (5)0.090 (6)0.074 (7)−0.024 (4)0.011 (4)−0.013 (4)
O50.031 (4)0.081 (7)0.050 (6)−0.013 (4)0.006 (3)0.010 (4)
O60.084 (9)0.083 (8)0.064 (8)−0.025 (6)0.038 (6)−0.030 (6)
O70.054 (5)0.057 (4)0.077 (6)−0.011 (3)−0.001 (4)0.005 (4)
O80.040 (6)0.099 (8)0.054 (6)−0.003 (5)0.005 (4)−0.033 (5)
O90.052 (6)0.049 (5)0.068 (7)0.003 (4)0.009 (4)−0.008 (4)
O100.034 (3)0.049 (3)0.035 (4)0.005 (2)0.004 (2)−0.016 (2)
O110.064 (6)0.046 (5)0.036 (5)−0.006 (4)−0.003 (4)0.008 (4)
O120.051 (5)0.038 (4)0.027 (4)−0.015 (3)−0.003 (3)−0.001 (3)
S10.0306 (4)0.0308 (3)0.0294 (4)0.0021 (3)0.0041 (3)0.0000 (3)
S20.0318 (4)0.0314 (3)0.0277 (4)0.0015 (3)0.0048 (3)−0.0006 (3)
S30.0316 (4)0.0317 (3)0.0270 (4)0.0016 (3)0.0047 (3)−0.0002 (3)
C1—C141.413 (5)C35—H350.9300
C1—C21.437 (5)C36—C371.419 (5)
C1—C151.479 (4)C36—H360.9300
C2—C31.376 (5)C37—C381.392 (5)
C2—C71.404 (4)C37—H370.9300
C3—C41.390 (5)C38—C391.406 (5)
C3—H30.9300C38—H380.9300
C4—C51.389 (5)C39—C401.370 (5)
C4—H40.9300C40—C411.360 (5)
C5—C61.376 (5)C40—H400.9300
C5—H50.9300C41—C421.429 (5)
C6—C71.401 (5)C41—C461.450 (5)
C6—H60.9300C42—C431.366 (5)
C7—C81.390 (5)C42—H420.9300
C8—C91.394 (5)C43—C441.408 (5)
C8—H80.9300C43—H430.9300
C9—C101.393 (5)C44—C451.363 (5)
C9—C141.407 (4)C44—H440.9300
C10—C111.346 (5)C45—C461.404 (5)
C10—H100.9300C45—H450.9300
C11—C121.392 (5)C47—N71.334 (4)
C11—H110.9300C47—H470.9300
C12—C131.362 (5)C48—N81.322 (4)
C12—H120.9300C48—N91.354 (4)
C13—C141.398 (5)C48—S31.710 (3)
C13—H130.9300Co1—N41.926 (2)
C15—N11.300 (4)Co1—N11.967 (2)
C15—H150.9300Co1—N71.985 (2)
C16—N21.307 (4)Co1—S12.2195 (9)
C16—N31.353 (4)Co1—S22.2314 (9)
C16—S11.738 (3)Co1—S32.2544 (9)
C17—C301.421 (4)N1—N21.386 (3)
C17—C181.430 (4)N3—O103.130 (6)
C17—C311.468 (3)N3—H3B0.85 (4)
C18—C231.386 (4)N3—H3A0.85 (4)
C18—C191.403 (4)N4—N51.380 (3)
C19—C201.386 (4)N6—H6B0.85 (4)
C19—H190.9300N6—H6A0.85 (4)
C20—C211.390 (5)N7—N81.359 (3)
C20—H200.9300N9—O83.002 (9)
C21—C221.375 (5)N9—O73.162 (8)
C21—H210.9300N9—H9B0.85 (4)
C22—C231.395 (5)N9—H9A0.85 (4)
C22—H220.9300O1—H1X0.8200
C23—C241.447 (4)O1—H1Y0.8200
C24—C251.370 (5)O2—H2X0.8200
C24—H240.9300O2—H2Y0.8200
C25—C301.406 (4)O3—H3X0.8200
C25—C261.410 (5)O3—H3Y0.8200
C26—C271.372 (5)O4—H4X0.8200
C26—H260.9300O4—H4Y0.8200
C27—C281.374 (4)O5—H5X0.8200
C27—H270.9300O5—H5Y0.8200
C28—C291.416 (5)O6—H6X0.8200
C28—H280.9300O6—H6Y0.8200
C29—C301.399 (5)O7—H7X0.8200
C29—H290.9300O7—H7Y0.8200
C31—N41.285 (3)O8—H8X0.8200
C31—H310.9300O8—H8Y0.8200
C32—N61.323 (4)O9—H9X0.8200
C32—N51.329 (4)O9—H9Y0.8200
C32—S21.731 (3)O10—H10X0.8200
C33—C461.393 (4)O10—H10Y0.8200
C33—C341.432 (4)O11—H11X0.8200
C33—C471.450 (4)O11—H11Y0.8200
C34—C351.403 (5)O12—H12X0.8200
C34—C391.458 (5)O12—H12Y0.8200
C35—C361.360 (5)
C14—C1—C2120.9 (3)C35—C36—C37122.5 (4)
C14—C1—C15122.2 (3)C35—C36—H36118.7
C2—C1—C15116.5 (3)C37—C36—H36118.7
C3—C2—C7119.7 (3)C38—C37—C36119.7 (3)
C3—C2—C1122.0 (3)C38—C37—H37120.2
C7—C2—C1118.1 (3)C36—C37—H37120.2
C2—C3—C4120.7 (3)C37—C38—C39119.4 (3)
C2—C3—H3119.6C37—C38—H38120.3
C4—C3—H3119.6C39—C38—H38120.3
C5—C4—C3119.6 (4)C40—C39—C38122.1 (3)
C5—C4—H4120.2C40—C39—C34118.3 (3)
C3—C4—H4120.2C38—C39—C34119.6 (3)
C6—C5—C4120.6 (4)C41—C40—C39124.2 (4)
C6—C5—H5119.7C41—C40—H40117.9
C4—C5—H5119.7C39—C40—H40117.9
C5—C6—C7119.9 (3)C40—C41—C42123.0 (4)
C5—C6—H6120.1C40—C41—C46119.0 (3)
C7—C6—H6120.1C42—C41—C46118.0 (3)
C8—C7—C6120.6 (3)C43—C42—C41122.3 (4)
C8—C7—C2119.8 (3)C43—C42—H42118.8
C6—C7—C2119.5 (3)C41—C42—H42118.8
C7—C8—C9122.9 (3)C42—C43—C44118.6 (3)
C7—C8—H8118.5C42—C43—H43120.7
C9—C8—H8118.5C44—C43—H43120.7
C10—C9—C8118.6 (3)C45—C44—C43121.3 (4)
C10—C9—C14122.8 (3)C45—C44—H44119.4
C8—C9—C14118.6 (3)C43—C44—H44119.4
C11—C10—C9116.0 (4)C44—C45—C46122.2 (4)
C11—C10—H10122.0C44—C45—H45118.9
C9—C10—H10122.0C46—C45—H45118.9
C10—C11—C12123.4 (4)C33—C46—C45123.1 (3)
C10—C11—H11118.3C33—C46—C41119.3 (3)
C12—C11—H11118.3C45—C46—C41117.5 (3)
C13—C12—C11120.6 (4)N7—C47—C33127.0 (3)
C13—C12—H12119.7N7—C47—H47116.5
C11—C12—H12119.7C33—C47—H47116.5
C12—C13—C14118.9 (3)N8—C48—N9118.0 (3)
C12—C13—H13120.6N8—C48—S3123.8 (2)
C14—C13—H13120.6N9—C48—S3118.3 (2)
C13—C14—C9118.3 (3)N4—Co1—N1172.00 (9)
C13—C14—C1122.0 (3)N4—Co1—N794.66 (9)
C9—C14—C1119.6 (3)N1—Co1—N791.26 (10)
N1—C15—C1127.2 (3)N4—Co1—S188.56 (7)
N1—C15—H15116.4N1—Co1—S185.33 (7)
C1—C15—H15116.4N7—Co1—S197.49 (8)
N2—C16—N3119.4 (3)N4—Co1—S284.94 (7)
N2—C16—S1124.8 (2)N1—Co1—S290.23 (8)
N3—C16—S1115.9 (2)N7—Co1—S2169.43 (7)
C30—C17—C18120.9 (3)S1—Co1—S293.06 (3)
C30—C17—C31117.6 (3)N4—Co1—S387.64 (6)
C18—C17—C31121.3 (2)N1—Co1—S398.44 (7)
C23—C18—C19119.5 (3)N7—Co1—S382.91 (7)
C23—C18—C17119.7 (3)S1—Co1—S3176.20 (3)
C19—C18—C17120.8 (3)S2—Co1—S386.52 (3)
C20—C19—C18119.7 (3)C15—N1—N2116.8 (2)
C20—C19—H19120.1C15—N1—Co1123.06 (19)
C18—C19—H19120.1N2—N1—Co1120.16 (17)
C19—C20—C21120.5 (3)C16—N2—N1112.9 (2)
C19—C20—H20119.8C16—N3—O10117.1 (2)
C21—C20—H20119.8C16—N3—H3B106 (3)
C22—C21—C20119.7 (3)O10—N3—H3B127 (3)
C22—C21—H21120.2C16—N3—H3A126 (3)
C20—C21—H21120.2H3B—N3—H3A106 (4)
C21—C22—C23120.6 (3)C31—N4—N5113.9 (2)
C21—C22—H22119.7C31—N4—Co1123.90 (18)
C23—C22—H22119.7N5—N4—Co1122.16 (17)
C18—C23—C22120.0 (3)C32—N5—N4111.6 (2)
C18—C23—C24118.5 (3)C32—N6—H6B110 (3)
C22—C23—C24121.4 (3)C32—N6—H6A110 (3)
C25—C24—C23121.6 (3)H6B—N6—H6A109 (4)
C25—C24—H24119.2C47—N7—N8113.1 (2)
C23—C24—H24119.2C47—N7—Co1126.3 (2)
C24—C25—C30120.7 (3)N8—N7—Co1120.45 (17)
C24—C25—C26120.6 (3)C48—N8—N7113.3 (2)
C30—C25—C26118.6 (3)C48—N9—O8121.9 (3)
C27—C26—C25120.9 (3)C48—N9—O792.1 (2)
C27—C26—H26119.6O8—N9—O762.7 (3)
C25—C26—H26119.6C48—N9—H9B109 (3)
C26—C27—C28121.7 (3)O8—N9—H9B45 (3)
C26—C27—H27119.2C48—N9—H9A110 (3)
C28—C27—H27119.2O8—N9—H9A65 (3)
C27—C28—C29118.5 (3)O7—N9—H9A127 (3)
C27—C28—H28120.7H9B—N9—H9A109 (4)
C29—C28—H28120.7H1X—O1—H1Y104.5
C30—C29—C28120.7 (3)H2X—O2—H2Y104.5
C30—C29—H29119.6H3X—O3—H3Y104.5
C28—C29—H29119.6H4X—O4—H4Y104.5
C29—C30—C25119.6 (3)H5X—O5—H5Y104.5
C29—C30—C17121.9 (3)H6X—O6—H6Y104.5
C25—C30—C17118.5 (3)N9—O7—H7X90.9
N4—C31—C17128.7 (2)N9—O7—H7Y95.5
N4—C31—H31115.7H7X—O7—H7Y104.5
C17—C31—H31115.7N9—O8—H8X95.9
N6—C32—N5117.7 (3)N9—O8—H8Y110.5
N6—C32—S2118.1 (3)H8X—O8—H8Y104.5
N5—C32—S2124.2 (2)H9X—O9—H9Y104.5
C46—C33—C34120.4 (3)N3—O10—H10X84.2
C46—C33—C47121.6 (3)N3—O10—H10Y98.0
C34—C33—C47117.8 (3)H10X—O10—H10Y104.5
C35—C34—C33122.0 (3)H11X—O11—H11Y104.5
C35—C34—C39119.4 (3)H12X—O12—H12Y104.5
C33—C34—C39118.6 (3)C16—S1—Co195.29 (10)
C36—C35—C34119.3 (3)C32—S2—Co194.97 (11)
C36—C35—H35120.3C48—S3—Co195.59 (10)
C34—C35—H35120.3
D—H···AD—HH···AD···AD—H···A
N3—H3A···O100.85 (4)2.36 (4)3.130 (6)151 (3)
N9—H9B···O70.85 (4)2.38 (4)3.162 (8)153 (4)
N9—H9B···O80.85 (4)2.47 (4)3.002 (9)122 (3)
N9—H9A···O110.85 (4)2.24 (4)2.957 (9)142 (4)
O1—H1X···O60.821.592.263 (11)137
O1—H1X···O11i0.822.583.013 (11)114
O7—H7Y···N3ii0.822.623.158 (10)124
O8—H8Y···S2ii0.822.603.371 (10)157
O9—H9Y···O11iii0.822.593.300 (12)146
O12—H12X···O11iii0.822.253.003 (11)153
O10—H10X···N9iv0.822.263.033 (6)157
O10—H10Y···N8iv0.822.482.939 (6)116
O11—H11X···S30.822.463.165 (8)145
O11—H11X···N50.822.573.163 (9)130
O11—H11Y···O1v0.822.503.013 (11)122
O12—H12Y···O90.822.062.494 (12)113
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N3—H3A⋯O100.85 (4)2.36 (4)3.130 (6)151 (3)
N9—H9B⋯O70.85 (4)2.38 (4)3.162 (8)153 (4)
N9—H9B⋯O80.85 (4)2.47 (4)3.002 (9)122 (3)
N9—H9A⋯O110.85 (4)2.24 (4)2.957 (9)142 (4)
O1—H1X⋯O60.821.592.263 (11)137
O1—H1X⋯O11i0.822.583.013 (11)114
O7—H7Y⋯N3ii0.822.623.158 (10)124
O8—H8Y⋯S2ii0.822.603.371 (10)157
O9—H9Y⋯O11iii0.822.593.300 (12)146
O12—H12X⋯O11iii0.822.253.003 (11)153
O10—H10X⋯N9iv0.822.263.033 (6)157
O10—H10Y⋯N8iv0.822.482.939 (6)116
O11—H11X⋯S30.822.463.165 (8)145
O11—H11X⋯N50.822.573.163 (9)130
O11—H11Y⋯O1v0.822.503.013 (11)122
O12—H12Y⋯O90.822.062.494 (12)113

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

  6 in total

Review 1.  The combinatorial synthesis of bicyclic privileged structures or privileged substructures.

Authors:  Douglas A Horton; Gregory T Bourne; Mark L Smythe
Journal:  Chem Rev       Date:  2003-03       Impact factor: 60.622

2.  2-piperidin-4-yl-benzimidazoles with broad spectrum antibacterial activities.

Authors:  Yun He; Baogen Wu; Jun Yang; Dale Robinson; Lisa Risen; Ray Ranken; Lawrence Blyn; Suzie Sheng; Eric E Swayze
Journal:  Bioorg Med Chem Lett       Date:  2003-10-06       Impact factor: 2.823

3.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

4.  Synthesis and antiparasitic activity of 2-(trifluoromethyl)-benzimidazole derivatives.

Authors:  G Navarrete-Vázquez; R Cedillo; A Hernández-Campos; L Yépez; F Hernädez-Luis; J Valdez; R Morales; R Cortés; M Hernández; R Castillo
Journal:  Bioorg Med Chem Lett       Date:  2001-01-22       Impact factor: 2.823

5.  Synthesis and potent antimicrobial activity of some novel methyl or ethyl 1H-benzimidazole-5-carboxylates derivatives carrying amide or amidine groups.

Authors:  Seçkin Ozden; Dilek Atabey; Sulhiye Yildiz; Hakan Göker
Journal:  Bioorg Med Chem       Date:  2005-03-01       Impact factor: 3.641

6.  Studies of antimicrobial activity of N-alkyl and N-acyl 2-(4-thiazolyl)-1H-benzimidazoles.

Authors:  N S Pawar; D S Dalal; S R Shimpi; P P Mahulikar
Journal:  Eur J Pharm Sci       Date:  2004-02       Impact factor: 4.384
  6 in total

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