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The title compound, [Ni(C17H17N2O2)(NCS)(CH4O)], is a mononuclear nickel(II) complex. The NiII atom has a slightly distorted octahedral geometry, coordinated by two N and two O atoms of the Schiff base ligand, and one terminal N atom from a thio­cyanate anion, together with a methanol mol­ecule. In the crystal structure, the complex forms centrosymmetric O—H...O hydrogen-bonded dimers. The symmetry-related dimers are linked by weak O—H...S hydrogen bonds to form layers parallel to the bc plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011791/ci6382sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011791/ci6382Isup2.hkl
Contains datablock I

CCDC reference: 233773

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.036
  • wR factor = 0.107
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

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Alert level B PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C18
Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

[N,N'-Bis(salicylidene)-1,3-propanediaminato](thiocyanato)(methanol)nickel(II) top
Crystal data top
[Ni(C17H17N2O2)(NCS)(CH4O)]F(000) = 896
Mr = 430.16Dx = 1.413 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3659 reflections
a = 10.508 (3) Åθ = 3.8–24.1°
b = 12.998 (4) ŵ = 1.09 mm1
c = 15.266 (5) ÅT = 298 K
β = 104.201 (4)°Block, green
V = 2021.4 (11) Å30.41 × 0.37 × 0.33 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
3574 independent reflections
Radiation source: fine-focus sealed tube2699 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.651, Tmax = 0.701k = 1215
10472 measured reflectionsl = 1818
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0626P)2]
where P = (Fo2 + 2Fc2)/3
3574 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.40 e Å3
6 restraintsΔρmin = 0.32 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*/UeqOcc. (<1)
Ni10.35315 (4)0.16036 (3)0.02634 (2)0.03663 (15)
N10.1571 (2)0.17513 (18)0.03468 (17)0.0400 (6)
N20.3750 (3)0.30248 (19)0.07830 (17)0.0437 (6)
N30.3190 (3)0.0965 (2)0.15318 (19)0.0557 (7)
O10.34389 (19)0.01910 (14)0.03209 (13)0.0416 (5)
H1A0.38910.02960.01810.080*
O20.54888 (19)0.13999 (14)0.00020 (14)0.0425 (5)
O30.3903 (2)0.22614 (17)0.10772 (14)0.0544 (6)
H30.34410.28570.11350.065*
S10.2029 (2)0.0918 (2)0.33839 (19)0.0767 (7)0.67
S1'0.2583 (9)0.0580 (7)0.3329 (5)0.155 (3)0.33
C10.2710 (3)0.0015 (2)0.0911 (2)0.0376 (7)
C20.3123 (3)0.0750 (2)0.1581 (2)0.0479 (8)
H20.39190.10870.16330.057*
C30.2355 (3)0.0985 (3)0.2173 (2)0.0530 (9)
H3A0.26360.14810.26180.064*
C40.1172 (3)0.0487 (2)0.2110 (2)0.0505 (8)
H40.06590.06420.25100.061*
C50.0771 (3)0.0232 (2)0.1453 (2)0.0469 (8)
H50.00340.05540.14040.056*
C60.1523 (3)0.0504 (2)0.0848 (2)0.0389 (7)
C70.0968 (3)0.1262 (2)0.0155 (2)0.0425 (7)
H70.00780.14040.00680.051*
C80.0778 (3)0.2462 (2)0.1015 (2)0.0513 (8)
H8A0.00800.25400.08920.062*
H8B0.06530.21680.16140.062*
C90.1405 (3)0.3507 (2)0.0999 (2)0.0540 (9)
H9A0.16540.37500.03800.065*
H9B0.07590.39820.13410.065*
C100.2603 (3)0.3523 (2)0.1384 (2)0.0553 (9)
H10A0.24000.31760.19640.066*
H10B0.28210.42320.14830.066*
C110.4843 (4)0.3504 (2)0.0647 (2)0.0516 (9)
H110.48250.41430.09230.062*
C120.6104 (3)0.3160 (2)0.0111 (2)0.0442 (8)
C130.7135 (4)0.3885 (3)0.0068 (3)0.0607 (10)
H130.69750.45450.01700.073*
C140.8357 (4)0.3653 (3)0.0581 (3)0.0618 (10)
H140.90240.41410.06780.074*
C150.8590 (3)0.2686 (3)0.0948 (2)0.0564 (9)
H150.94090.25300.13210.068*
C160.7616 (3)0.1942 (3)0.0771 (2)0.0488 (8)
H160.77930.12900.10220.059*
C170.6377 (3)0.2155 (2)0.0223 (2)0.0418 (7)
C180.2770 (4)0.0888 (3)0.2301 (3)0.0553 (9)
C190.4770 (4)0.1894 (4)0.1875 (3)0.0809 (12)
H19A0.47320.23370.23720.121*
H19B0.56490.18840.17980.121*
H19C0.45160.12100.19990.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0433 (3)0.0305 (2)0.0369 (2)0.00144 (16)0.01150 (18)0.00029 (15)
N10.0407 (15)0.0360 (14)0.0407 (15)0.0035 (11)0.0052 (12)0.0006 (11)
N20.0518 (17)0.0359 (14)0.0426 (16)0.0009 (12)0.0099 (13)0.0035 (11)
N30.071 (2)0.0525 (18)0.0431 (18)0.0005 (14)0.0137 (15)0.0030 (13)
O10.0476 (12)0.0303 (10)0.0526 (13)0.0056 (9)0.0236 (10)0.0051 (9)
O20.0404 (12)0.0306 (11)0.0600 (14)0.0019 (9)0.0192 (11)0.0029 (9)
O30.0659 (15)0.0532 (15)0.0414 (14)0.0101 (11)0.0079 (12)0.0063 (10)
S10.0739 (12)0.111 (2)0.0403 (10)0.0208 (12)0.0036 (9)0.0022 (11)
S1'0.254 (8)0.138 (5)0.061 (3)0.008 (5)0.013 (5)0.022 (3)
C10.0416 (17)0.0317 (16)0.0415 (18)0.0050 (13)0.0141 (14)0.0049 (13)
C20.053 (2)0.0422 (19)0.051 (2)0.0043 (15)0.0187 (17)0.0066 (15)
C30.068 (2)0.045 (2)0.049 (2)0.0031 (17)0.0194 (18)0.0078 (15)
C40.058 (2)0.050 (2)0.049 (2)0.0106 (17)0.0226 (17)0.0030 (16)
C50.0407 (18)0.050 (2)0.051 (2)0.0036 (15)0.0150 (16)0.0070 (16)
C60.0402 (17)0.0346 (16)0.0421 (18)0.0041 (13)0.0104 (14)0.0055 (13)
C70.0367 (17)0.0436 (17)0.0457 (19)0.0041 (14)0.0071 (15)0.0078 (14)
C80.049 (2)0.050 (2)0.048 (2)0.0083 (16)0.0006 (16)0.0076 (15)
C90.059 (2)0.042 (2)0.055 (2)0.0100 (16)0.0033 (17)0.0063 (15)
C100.071 (2)0.041 (2)0.050 (2)0.0033 (16)0.0064 (18)0.0138 (15)
C110.075 (3)0.0342 (18)0.050 (2)0.0019 (16)0.0223 (19)0.0041 (14)
C120.053 (2)0.0366 (17)0.0462 (19)0.0063 (14)0.0193 (16)0.0032 (14)
C130.077 (3)0.038 (2)0.071 (3)0.0152 (18)0.025 (2)0.0047 (17)
C140.062 (3)0.054 (2)0.074 (3)0.0189 (19)0.025 (2)0.0184 (19)
C150.048 (2)0.056 (2)0.066 (2)0.0016 (17)0.0180 (18)0.0210 (18)
C160.045 (2)0.0443 (18)0.061 (2)0.0017 (15)0.0186 (17)0.0051 (15)
C170.0458 (19)0.0385 (18)0.0468 (19)0.0047 (14)0.0219 (15)0.0077 (14)
C180.061 (2)0.052 (2)0.056 (2)0.0060 (17)0.0200 (19)0.0006 (17)
C190.078 (3)0.108 (3)0.054 (3)0.023 (3)0.013 (2)0.005 (2)
Geometric parameters (Å, º) top
Ni1—O22.014 (2)C5—H50.93
Ni1—N12.041 (3)C6—C71.458 (4)
Ni1—N22.045 (3)C7—H70.93
Ni1—O12.054 (2)C8—C91.507 (4)
Ni1—N32.056 (3)C8—H8A0.97
Ni1—O32.163 (2)C8—H8B0.97
N1—C71.277 (4)C9—C101.514 (5)
N1—C81.474 (4)C9—H9A0.97
N2—C111.278 (4)C9—H9B0.97
N2—C101.473 (4)C10—H10A0.97
N3—C181.154 (4)C10—H10B0.97
O1—C11.345 (3)C11—C121.447 (5)
O1—H1A0.85C11—H110.93
O2—C171.340 (3)C12—C171.406 (4)
O3—C191.413 (5)C12—C131.410 (5)
O3—H30.93C13—C141.364 (5)
S1—C181.645 (5)C13—H130.93
S1'—C181.584 (9)C14—C151.373 (5)
C1—C21.389 (4)C14—H140.93
C1—C61.401 (4)C15—C161.385 (4)
C2—C31.386 (4)C15—H150.93
C2—H20.93C16—C171.392 (4)
C3—C41.383 (5)C16—H160.93
C3—H3A0.93C19—H19A0.96
C4—C51.359 (5)C19—H19B0.96
C4—H40.93C19—H19C0.96
C5—C61.401 (4)
O2—Ni1—N1171.89 (9)C6—C7—H7116.5
O2—Ni1—N289.46 (9)N1—C8—C9112.5 (3)
N1—Ni1—N295.64 (10)N1—C8—H8A109.0
O2—Ni1—O187.14 (8)C9—C8—H8A109.1
N1—Ni1—O187.51 (9)N1—C8—H8B109.1
N2—Ni1—O1175.97 (9)C9—C8—H8B109.1
O2—Ni1—N394.02 (10)H8A—C8—H8B107.8
N1—Ni1—N392.23 (11)C8—C9—C10114.1 (3)
N2—Ni1—N390.55 (11)C8—C9—H9A108.8
O1—Ni1—N391.85 (10)C10—C9—H9A108.8
O2—Ni1—O385.59 (8)C8—C9—H9B108.6
N1—Ni1—O388.12 (9)C10—C9—H9B108.8
N2—Ni1—O389.92 (10)H9A—C9—H9B107.6
O1—Ni1—O387.66 (8)N2—C10—C9112.5 (3)
N3—Ni1—O3179.39 (10)N2—C10—H10A109.1
C7—N1—C8116.6 (3)C9—C10—H10A109.3
C7—N1—Ni1123.9 (2)N2—C10—H10B109.1
C8—N1—Ni1119.5 (2)C9—C10—H10B108.9
C11—N2—C10116.9 (3)H10A—C10—H10B107.8
C11—N2—Ni1124.0 (2)N2—C11—C12127.1 (3)
C10—N2—Ni1119.1 (2)N2—C11—H11116.4
C18—N3—Ni1158.3 (3)C12—C11—H11116.4
C1—O1—Ni1124.35 (17)C17—C12—C13118.1 (3)
C1—O1—H1A117.8C17—C12—C11124.7 (3)
Ni1—O1—H1A117.9C13—C12—C11117.2 (3)
C17—O2—Ni1124.65 (18)C14—C13—C12122.2 (3)
C19—O3—Ni1127.6 (2)C14—C13—H13118.8
C19—O3—H3116.1C12—C13—H13119.0
Ni1—O3—H3116.2C13—C14—C15119.0 (3)
O1—C1—C2120.2 (3)C13—C14—H14120.5
O1—C1—C6120.1 (3)C15—C14—H14120.5
C2—C1—C6119.7 (3)C14—C15—C16120.6 (4)
C3—C2—C1120.3 (3)C14—C15—H15119.7
C3—C2—H2119.8C16—C15—H15119.7
C1—C2—H2119.9C15—C16—C17121.1 (3)
C4—C3—C2120.6 (3)C15—C16—H16119.5
C4—C3—H3A119.7C17—C16—H16119.5
C2—C3—H3A119.7O2—C17—C16119.8 (3)
C5—C4—C3118.9 (3)O2—C17—C12121.5 (3)
C5—C4—H4120.5C16—C17—C12118.7 (3)
C3—C4—H4120.6N3—C18—S1'162.6 (5)
C4—C5—C6122.5 (3)N3—C18—S1171.7 (4)
C4—C5—H5118.8O3—C19—H19A109.6
C6—C5—H5118.7O3—C19—H19B109.5
C1—C6—C5118.0 (3)H19A—C19—H19B109.5
C1—C6—C7124.5 (3)O3—C19—H19C109.3
C5—C6—C7117.4 (3)H19A—C19—H19C109.5
N1—C7—C6127.0 (3)H19B—C19—H19C109.5
N1—C7—H7116.5
N2—Ni1—N1—C7154.7 (2)C1—C2—C3—C40.4 (5)
O1—Ni1—N1—C722.8 (2)C2—C3—C4—C50.4 (5)
N3—Ni1—N1—C7114.5 (2)C3—C4—C5—C61.3 (5)
O3—Ni1—N1—C765.0 (2)O1—C1—C6—C5177.3 (3)
N2—Ni1—N1—C825.0 (2)C2—C1—C6—C52.0 (4)
O1—Ni1—N1—C8157.6 (2)O1—C1—C6—C71.7 (4)
N3—Ni1—N1—C865.8 (2)C2—C1—C6—C7177.7 (3)
O3—Ni1—N1—C8114.7 (2)C4—C5—C6—C12.1 (5)
O2—Ni1—N2—C1116.2 (3)C4—C5—C6—C7178.1 (3)
N1—Ni1—N2—C11157.5 (3)C8—N1—C7—C6178.6 (3)
N3—Ni1—N2—C11110.2 (3)Ni1—N1—C7—C61.7 (4)
O3—Ni1—N2—C1169.4 (3)C1—C6—C7—N118.3 (5)
O2—Ni1—N2—C10161.0 (2)C5—C6—C7—N1166.0 (3)
N1—Ni1—N2—C1025.3 (2)C7—N1—C8—C9131.5 (3)
N3—Ni1—N2—C1067.0 (2)Ni1—N1—C8—C948.2 (3)
O3—Ni1—N2—C10113.4 (2)N1—C8—C9—C1071.9 (4)
O2—Ni1—N3—C18131.6 (8)C11—N2—C10—C9133.8 (3)
N1—Ni1—N3—C1853.6 (8)Ni1—N2—C10—C948.8 (3)
N2—Ni1—N3—C1842.1 (8)C8—C9—C10—N272.4 (4)
O1—Ni1—N3—C18141.1 (8)C10—N2—C11—C12177.9 (3)
O2—Ni1—O1—C1135.5 (2)Ni1—N2—C11—C120.6 (5)
N1—Ni1—O1—C138.4 (2)N2—C11—C12—C1711.7 (5)
N3—Ni1—O1—C1130.5 (2)N2—C11—C12—C13169.8 (3)
O3—Ni1—O1—C149.8 (2)C17—C12—C13—C142.8 (5)
N2—Ni1—O2—C1732.2 (2)C11—C12—C13—C14178.7 (3)
O1—Ni1—O2—C17145.7 (2)C12—C13—C14—C151.1 (5)
N3—Ni1—O2—C17122.7 (2)C13—C14—C15—C162.7 (5)
O3—Ni1—O2—C1757.8 (2)C14—C15—C16—C170.5 (5)
O2—Ni1—O3—C1942.6 (3)Ni1—O2—C17—C16150.8 (2)
N1—Ni1—O3—C19132.3 (3)Ni1—O2—C17—C1231.3 (4)
N2—Ni1—O3—C19132.1 (3)C15—C16—C17—O2174.5 (3)
O1—Ni1—O3—C1944.7 (3)C15—C16—C17—C123.4 (4)
Ni1—O1—C1—C2148.9 (2)C13—C12—C17—O2173.0 (3)
Ni1—O1—C1—C631.7 (4)C11—C12—C17—O25.5 (5)
O1—C1—C2—C3178.1 (3)C13—C12—C17—C164.9 (4)
C6—C1—C2—C31.2 (5)C11—C12—C17—C16176.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···S1i0.932.443.352 (10)166
O3—H3···S1i0.932.413.309 (3)163
O1—H1A···O2ii0.851.632.462 (3)166
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y, z.
 

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