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The title complex, [Co(C28H20N4O2)(CH3OH)], can be described as a single-stranded helix with the CoII atom having a distorted trigonal–bipyramidal configuration. Edge-to-face π–π stacking inter­actions, C—H...π inter­actions between the aromatic rings and O—H...O hydrogen bonds lead to a three-dimensional network in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806036348/ac2040sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806036348/ac2040Isup2.hkl
Contains datablock I

CCDC reference: 623957

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.055
  • wR factor = 0.149
  • Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.02 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... H2A C2 H2A PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... H5A C5 H5A PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... H5A C5 H5A PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... H2A H2A CG1 PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... H5A H5A CG1 PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... H5A H5A CG2 PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... H2A C2 H2A CG1 PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... H5A C5 H5A CG1 PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... H5A C5 H5A CG2
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 12 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 0 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

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

{1,2-Bis[(2-oxidobenzylidene)hydrazozo]1,2-diphenylethane}(methanol)cobalt(II) top
Crystal data top
[Co(C28H20N4O2)(CH4O)]Z = 2
Mr = 535.45F(000) = 554
Triclinic, P1Dx = 1.437 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.298 (2) ÅCell parameters from 867 reflections
b = 10.455 (2) Åθ = 2.5–26.9°
c = 14.523 (3) ŵ = 0.73 mm1
α = 95.668 (4)°T = 293 K
β = 103.721 (4)°Block, red
γ = 112.567 (4)°0.22 × 0.20 × 0.18 mm
V = 1237.8 (5) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3617 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.083
Graphite monochromatorθmax = 25.1°, θmin = 2.2°
φ/ω scansh = 1011
6207 measured reflectionsk = 1112
4310 independent reflectionsl = 1714
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0888P)2 + 0.024P]
where P = (Fo2 + 2Fc2)/3
4310 reflections(Δ/σ)max < 0.001
337 parametersΔρmax = 0.71 e Å3
0 restraintsΔρmin = 0.35 e Å3
Special details top

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
Co10.10905 (5)0.47892 (5)0.65263 (3)0.03192 (18)
O10.2562 (3)0.6409 (3)0.61474 (17)0.0411 (6)
O20.0835 (3)0.5191 (2)0.63166 (16)0.0344 (5)
N10.2816 (3)0.5387 (3)0.78912 (19)0.0316 (6)
N20.2379 (3)0.5011 (3)0.87312 (19)0.0348 (6)
N30.0648 (3)0.2116 (3)0.71726 (18)0.0301 (6)
N40.0210 (3)0.2953 (3)0.69406 (18)0.0304 (6)
C10.4123 (4)0.7131 (3)0.6515 (2)0.0325 (7)
C20.5027 (5)0.7975 (4)0.5976 (3)0.0439 (9)
H20.44790.80200.53630.053*
C30.6677 (5)0.8729 (4)0.6321 (3)0.0514 (10)
H30.72350.92470.59320.062*
C40.7534 (5)0.8734 (4)0.7243 (3)0.0530 (10)
H40.86610.92430.74720.064*
C50.6709 (4)0.7990 (4)0.7804 (3)0.0453 (9)
H50.72760.80330.84350.054*
C60.5006 (4)0.7146 (3)0.7459 (2)0.0325 (7)
C70.4264 (4)0.6371 (3)0.8098 (2)0.0346 (8)
H70.49010.66050.87420.042*
C80.1784 (4)0.3697 (3)0.8762 (2)0.0292 (7)
C90.1140 (4)0.3313 (4)0.9587 (2)0.0332 (7)
C100.1537 (5)0.4344 (4)1.0389 (3)0.0490 (10)
H100.22720.52701.04360.059*
C110.0838 (6)0.3998 (5)1.1126 (3)0.0597 (12)
H110.10950.46981.16630.072*
C120.0217 (6)0.2649 (5)1.1071 (3)0.0558 (11)
H120.06760.24281.15700.067*
C130.0608 (5)0.1615 (5)1.0285 (3)0.0525 (10)
H130.13350.06911.02460.063*
C140.0084 (5)0.1947 (4)0.9542 (3)0.0423 (9)
H140.01700.12390.90120.051*
C150.1654 (4)0.2520 (3)0.8022 (2)0.0280 (7)
C160.2700 (4)0.1778 (3)0.8293 (2)0.0293 (7)
C170.4109 (5)0.2396 (4)0.9076 (2)0.0421 (9)
H170.43670.32720.94520.051*
C180.5125 (5)0.1736 (5)0.9304 (3)0.0521 (10)
H180.60680.21680.98280.063*
C190.4757 (5)0.0437 (4)0.8760 (3)0.0508 (10)
H190.54430.00130.89180.061*
C200.3362 (5)0.0194 (4)0.7978 (3)0.0437 (9)
H200.31110.10690.76030.052*
C210.2345 (4)0.0473 (4)0.7753 (2)0.0359 (8)
H210.14020.00380.72270.043*
C220.1699 (4)0.2453 (3)0.6925 (2)0.0314 (7)
H220.21180.15890.71070.038*
C230.2777 (4)0.3110 (4)0.6649 (2)0.0321 (7)
C240.4392 (4)0.2384 (4)0.6669 (3)0.0432 (9)
H240.46860.15260.68690.052*
C250.5534 (4)0.2895 (4)0.6406 (3)0.0466 (9)
H250.66000.23870.64110.056*
C260.5078 (4)0.4188 (4)0.6129 (3)0.0425 (9)
H260.58470.45530.59500.051*
C270.3512 (4)0.4938 (4)0.6115 (2)0.0372 (8)
H270.32360.58110.59370.045*
C280.2321 (4)0.4430 (3)0.6358 (2)0.0290 (7)
C290.0110 (6)0.2135 (4)0.4792 (3)0.0589 (11)
H29A0.00000.15630.52590.088*
H29B0.02410.18790.42600.088*
H29C0.12320.19810.45580.088*
O30.0865 (3)0.3584 (3)0.52345 (16)0.0408 (6)
H3A0.07610.40720.48380.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0255 (3)0.0356 (3)0.0351 (3)0.0107 (2)0.01141 (19)0.01246 (19)
O10.0327 (13)0.0420 (14)0.0408 (13)0.0064 (11)0.0102 (11)0.0161 (11)
O20.0269 (12)0.0349 (13)0.0447 (13)0.0125 (10)0.0141 (10)0.0166 (10)
N10.0341 (15)0.0311 (15)0.0315 (14)0.0122 (13)0.0139 (12)0.0103 (11)
N20.0402 (16)0.0373 (16)0.0294 (14)0.0136 (13)0.0178 (12)0.0118 (12)
N30.0309 (14)0.0305 (14)0.0321 (14)0.0138 (12)0.0123 (12)0.0103 (11)
N40.0298 (15)0.0315 (14)0.0303 (14)0.0135 (12)0.0071 (11)0.0104 (11)
C10.0321 (18)0.0234 (16)0.0388 (18)0.0062 (14)0.0155 (15)0.0039 (13)
C20.046 (2)0.041 (2)0.0391 (19)0.0082 (17)0.0196 (17)0.0102 (16)
C30.053 (2)0.036 (2)0.060 (3)0.0034 (18)0.034 (2)0.0087 (18)
C40.0287 (19)0.040 (2)0.073 (3)0.0041 (17)0.0204 (19)0.004 (2)
C50.0328 (19)0.042 (2)0.048 (2)0.0066 (17)0.0080 (17)0.0043 (17)
C60.0297 (17)0.0280 (17)0.0391 (18)0.0087 (14)0.0155 (15)0.0056 (14)
C70.0330 (18)0.0350 (19)0.0330 (17)0.0116 (16)0.0096 (14)0.0072 (14)
C80.0288 (17)0.0377 (19)0.0271 (16)0.0168 (15)0.0125 (13)0.0110 (13)
C90.0353 (18)0.042 (2)0.0313 (17)0.0215 (16)0.0143 (14)0.0149 (15)
C100.063 (3)0.043 (2)0.039 (2)0.016 (2)0.0222 (19)0.0100 (17)
C110.087 (3)0.064 (3)0.035 (2)0.033 (3)0.028 (2)0.0084 (19)
C120.067 (3)0.078 (3)0.045 (2)0.037 (3)0.038 (2)0.031 (2)
C130.048 (2)0.057 (3)0.059 (3)0.017 (2)0.030 (2)0.029 (2)
C140.045 (2)0.045 (2)0.0376 (19)0.0149 (18)0.0191 (16)0.0116 (16)
C150.0297 (17)0.0310 (17)0.0300 (16)0.0131 (14)0.0173 (14)0.0136 (13)
C160.0336 (17)0.0330 (17)0.0274 (16)0.0146 (14)0.0164 (14)0.0129 (13)
C170.047 (2)0.045 (2)0.0348 (18)0.0223 (18)0.0090 (16)0.0076 (16)
C180.046 (2)0.067 (3)0.047 (2)0.031 (2)0.0049 (18)0.019 (2)
C190.055 (3)0.060 (3)0.061 (3)0.040 (2)0.026 (2)0.029 (2)
C200.051 (2)0.039 (2)0.056 (2)0.0249 (18)0.0295 (19)0.0174 (17)
C210.0333 (18)0.0375 (19)0.0387 (18)0.0134 (16)0.0154 (15)0.0103 (15)
C220.0308 (18)0.0284 (17)0.0332 (17)0.0085 (14)0.0118 (14)0.0108 (13)
C230.0301 (17)0.0396 (19)0.0287 (16)0.0131 (15)0.0138 (14)0.0111 (14)
C240.037 (2)0.054 (2)0.045 (2)0.0169 (18)0.0217 (17)0.0258 (18)
C250.0307 (19)0.068 (3)0.047 (2)0.0194 (19)0.0230 (17)0.0185 (19)
C260.037 (2)0.061 (2)0.042 (2)0.0298 (19)0.0174 (16)0.0095 (17)
C270.040 (2)0.0396 (19)0.0358 (18)0.0203 (16)0.0128 (15)0.0085 (15)
C280.0291 (17)0.0343 (17)0.0253 (16)0.0129 (14)0.0126 (13)0.0053 (13)
C290.077 (3)0.045 (2)0.046 (2)0.020 (2)0.014 (2)0.0052 (18)
O30.0473 (15)0.0435 (14)0.0356 (13)0.0199 (12)0.0161 (11)0.0130 (11)
Geometric parameters (Å, º) top
Co1—O11.951 (2)C12—H120.9300
Co1—O21.954 (2)C13—C141.388 (5)
Co1—O32.073 (2)C13—H130.9300
Co1—N42.074 (3)C14—H140.9300
Co1—N12.091 (3)C15—C161.470 (4)
O1—C11.293 (4)C16—C211.381 (5)
O2—C281.323 (4)C16—C171.387 (5)
N1—C71.283 (4)C17—C181.370 (5)
N1—N21.420 (4)C17—H170.9300
N2—C81.279 (4)C18—C191.374 (6)
N3—C151.273 (4)C18—H180.9300
N3—N41.408 (4)C19—C201.380 (6)
N4—C221.272 (4)C19—H190.9300
C1—C21.406 (5)C20—C211.375 (5)
C1—C61.417 (5)C20—H200.9300
C2—C31.362 (5)C21—H210.9300
C2—H20.9300C22—C231.424 (5)
C3—C41.385 (6)C22—H220.9300
C3—H30.9300C23—C241.408 (5)
C4—C51.349 (5)C23—C281.419 (5)
C4—H40.9300C24—C251.357 (5)
C5—C61.415 (5)C24—H240.9300
C5—H50.9300C25—C261.385 (5)
C6—C71.420 (5)C25—H250.9300
C7—H70.9300C26—C271.370 (5)
C8—C91.485 (4)C26—H260.9300
C8—C151.499 (4)C27—C281.391 (5)
C9—C141.372 (5)C27—H270.9300
C9—C101.378 (5)C29—O31.416 (5)
C10—C111.388 (5)C29—H29A0.9600
C10—H100.9300C29—H29B0.9600
C11—C121.355 (6)C29—H29C0.9600
C11—H110.9300O3—H3A0.8200
C12—C131.365 (6)
O1—Co1—O2100.42 (10)C12—C13—H13120.1
O1—Co1—O386.66 (10)C14—C13—H13120.1
O2—Co1—O3107.04 (10)C9—C14—C13120.4 (4)
O1—Co1—N4171.45 (10)C9—C14—H14119.8
O2—Co1—N488.05 (10)C13—C14—H14119.8
O3—Co1—N489.79 (10)N3—C15—C16118.6 (3)
O1—Co1—N189.15 (10)N3—C15—C8122.6 (3)
O2—Co1—N1121.73 (10)C16—C15—C8118.8 (3)
O3—Co1—N1130.97 (10)C21—C16—C17118.1 (3)
N4—Co1—N187.31 (10)C21—C16—C15120.9 (3)
C1—O1—Co1129.3 (2)C17—C16—C15120.9 (3)
C28—O2—Co1131.0 (2)C18—C17—C16121.0 (4)
C7—N1—N2112.4 (3)C18—C17—H17119.5
C7—N1—Co1123.4 (2)C16—C17—H17119.5
N2—N1—Co1122.3 (2)C17—C18—C19120.3 (4)
C8—N2—N1118.0 (3)C17—C18—H18119.9
C15—N3—N4115.2 (3)C19—C18—H18119.9
C22—N4—N3117.6 (3)C18—C19—C20119.6 (3)
C22—N4—Co1127.9 (2)C18—C19—H19120.2
N3—N4—Co1114.22 (19)C20—C19—H19120.2
O1—C1—C2120.0 (3)C21—C20—C19119.9 (4)
O1—C1—C6123.4 (3)C21—C20—H20120.0
C2—C1—C6116.6 (3)C19—C20—H20120.0
C3—C2—C1122.3 (3)C20—C21—C16121.1 (3)
C3—C2—H2118.9C20—C21—H21119.5
C1—C2—H2118.9C16—C21—H21119.5
C2—C3—C4120.8 (4)N4—C22—C23125.2 (3)
C2—C3—H3119.6N4—C22—H22117.4
C4—C3—H3119.6C23—C22—H22117.4
C5—C4—C3119.1 (4)C24—C23—C28118.9 (3)
C5—C4—H4120.5C24—C23—C22116.9 (3)
C3—C4—H4120.5C28—C23—C22124.1 (3)
C4—C5—C6121.9 (4)C25—C24—C23122.2 (3)
C4—C5—H5119.0C25—C24—H24118.9
C6—C5—H5119.0C23—C24—H24118.9
C5—C6—C1119.2 (3)C24—C25—C26118.6 (3)
C5—C6—C7117.4 (3)C24—C25—H25120.7
C1—C6—C7123.3 (3)C26—C25—H25120.7
N1—C7—C6127.5 (3)C27—C26—C25120.9 (3)
N1—C7—H7116.2C27—C26—H26119.5
C6—C7—H7116.2C25—C26—H26119.5
N2—C8—C9117.0 (3)C26—C27—C28121.9 (3)
N2—C8—C15125.2 (3)C26—C27—H27119.0
C9—C8—C15117.8 (3)C28—C27—H27119.0
C14—C9—C10119.2 (3)O2—C28—C27119.2 (3)
C14—C9—C8120.7 (3)O2—C28—C23123.4 (3)
C10—C9—C8120.0 (3)C27—C28—C23117.4 (3)
C9—C10—C11119.8 (4)O3—C29—H29A109.5
C9—C10—H10120.1O3—C29—H29B109.5
C11—C10—H10120.1H29A—C29—H29B109.5
C12—C11—C10120.6 (4)O3—C29—H29C109.5
C12—C11—H11119.7H29A—C29—H29C109.5
C10—C11—H11119.7H29B—C29—H29C109.5
C11—C12—C13120.1 (4)C29—O3—Co1131.6 (2)
C11—C12—H12119.9C29—O3—H3A109.5
C13—C12—H12119.9Co1—O3—H3A103.7
C12—C13—C14119.9 (4)
O2—Co1—O1—C1143.1 (3)C5—C6—C7—N1168.2 (3)
O3—Co1—O1—C1110.2 (3)C1—C6—C7—N113.1 (6)
N1—Co1—O1—C120.9 (3)N1—N2—C8—C9172.4 (3)
O1—Co1—O2—C28173.2 (3)N1—N2—C8—C156.1 (5)
O3—Co1—O2—C2883.5 (3)N2—C8—C9—C14161.3 (3)
N4—Co1—O2—C285.6 (3)C15—C8—C9—C1417.3 (4)
N1—Co1—O2—C2891.3 (3)N2—C8—C9—C1015.6 (5)
O1—Co1—N1—C78.3 (3)C15—C8—C9—C10165.8 (3)
O2—Co1—N1—C7110.1 (3)N4—N3—C15—C16174.9 (3)
O3—Co1—N1—C776.5 (3)N4—N3—C15—C86.7 (4)
N4—Co1—N1—C7163.9 (3)N2—C8—C15—N371.1 (4)
O1—Co1—N1—N2154.9 (2)C9—C8—C15—N3107.4 (3)
O2—Co1—N1—N253.2 (3)N2—C8—C15—C16110.5 (4)
O3—Co1—N1—N2120.3 (2)C9—C8—C15—C1671.0 (4)
N4—Co1—N1—N232.9 (2)N3—C15—C16—C2116.0 (4)
C7—N1—N2—C8130.0 (3)C8—C15—C16—C21162.5 (3)
Co1—N1—N2—C865.1 (3)N3—C15—C16—C17161.3 (3)
C15—N3—N4—C22105.1 (3)C8—C15—C16—C1720.2 (4)
C15—N3—N4—Co180.9 (3)N3—N4—C22—C23176.0 (3)
O2—Co1—N4—C224.8 (3)Co1—N4—C22—C232.9 (5)
O3—Co1—N4—C22102.2 (3)N4—C22—C23—C24179.4 (3)
N1—Co1—N4—C22126.7 (3)N4—C22—C23—C280.4 (5)
O2—Co1—N4—N3178.1 (2)Co1—O2—C28—C27176.0 (2)
O3—Co1—N4—N371.0 (2)Co1—O2—C28—C234.5 (5)
N1—Co1—N4—N360.0 (2)O1—Co1—O3—C29176.2 (3)
Co1—O1—C1—C2161.2 (2)O2—Co1—O3—C2976.3 (3)
Co1—O1—C1—C619.8 (5)N4—Co1—O3—C2911.6 (3)
N2—N1—C7—C6169.9 (3)N1—Co1—O3—C2997.9 (3)
Co1—N1—C7—C65.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O2i0.821.922.699 (3)159
C29—H29C···O1i0.962.603.313 (6)131
C2—H2A···Cg1i0.932.74 (1)3.404 (8)127 (1)
C5—H5A···Cg1ii0.933.13 (1)3.90 (2)139 (1)
C5—H5A···Cg2iii0.932.98 (1)3.804 (8)145 (1)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1, z+2; (iii) x+1, y+1, z+2.
 

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