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Acta Cryst. (2007). E63, m2406    [ doi:10.1107/S1600536807040688 ]

2-(2-Hydroxy-1-naphthyldiazenyl)pyridinium [1-(2-pyridyldiazenyl)-2-naphtholato-[kappa]3N,N',O]tris(thiocyanato-[kappa]N)chromium(III) methanol solvate

T.-F. Liu, H.-Y. Lv, B.-T. Zhao and J.-G. Wang

Abstract top

In the title compound, (C15H12N3O)[Cr(C15H10N3O)(NCS)3]·CH4O, the CrIII atom is coordinated by two N atoms and one O atom from the tridentate 1-(2-pyridyldiazenyl)-2-naphtholate (PAN) ligand and three N atoms from thiocyanate ions in a distorted octahedral arrangement. Another uncoordinated and protonated PAN molecule and a methanol solvent molecule are present in the asymmetric unit. The crystal packing is stabilized by [pi]-[pi] interactions [centroid-centroid separation 3.594 (4) Å] and O-H...N and O-H...S hydrogen bonds.

Comment top

The color reactions of metal ions and PAN (1-(pyridin-2-yldiazenyl)naphthalen-2-ol) were a useful method in spectrophotometric determination. We report herein the crystal structure of a chromium(III) complex where the CrIII ion is coordinated by a PAN− and three thiocyanate ions.

The crystal structure of (I) consists of a [Cr(PAN)(NCS)3]− anion, an uncoordinated protonated PAN cation and a methanol molecule (Fig. 1). The chromium ion has a slightly distorted octahedral coordination geometry, its symmetry being close to C2V. The Cr—N(PAN) bond distances are 2.006 (4) and 2.058 (5) Å, the Cr—O bond distance is 1.970 (4) Å. The ligand is planar, the dihedral angle between two aromatic rings is 6.5 (3)°. The Cr—N(NCS) bond distances vary in the range 1.981 (6)–2.001 (6) Å, and the thiocyanate ligands are almost linear with N–C–S angles 178.6 (6)–179.4 (7)°.

The uncoordinated PAN is protonated at (N9), the dihedral angle between two aromatic rings is 15.4 (2)°. Related aromatic rings A and Bi [ring A: C5, C6, C7, C8, C9 and C10; ring B: N9, C29, C30, C31, C32 and C33; symmetry code: (i) 1 − x, y, 1 − z) show π-π stacking with a ring-ring separation of 3.594 (4) Å. A C—S···Cg (π-ring centre) interaction from the C17—S2 bond to ring Rii [ring R: C19, C20, C21, C22, C23 and C28; symmetry code: (ii) −x, 1 − y, 1 − z) is also obsered [C17···Cg = 3.684 (7), S···Cg = 3.483 (5) Å and C17—S···Cg = 84.1 (2)°] (Fig. 2). The crystal packing is characterized by three conventional hydrogen bonds, c.f. Table (Spek, 2003).

Related literature top

For related literature, see: Spek (2003).

Experimental top

A methanol solution of PAN (0.3 mmol, 3 ml) was mixed with a methanol solution of chromium(III) nitrate (0.3 mmol, 3 ml). The resulting solution was kept under stirring for about 30 min, and then an aqueous solution of KSCN (0.6 mmol, 6 ml) was added to the mixture. Dark green single crystals were obtained after three weeks (yield 32%).

Refinement top

The hydrogen atoms were assigned with isotropic displacement factors and included in the final refinement cycles by use of geometrical restraints (Car–H = 0.93 Å; CMe–H = 0.96 Å; N–H = 0.86 Å; O–H = 0.82 Å).

Computing details top

Data collection: APEX2 (Bruker, DATE?); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a).

Figures top
[Figure 1] Fig. 1. ORTEP plot of [Cr(C10H6NO2)2(NCS)(C2H6O)]; displacement ellipsoids are drawn at the 30% probability, and hydrogen atoms are shown as spheres of arbitrary radii.
[Figure 2] Fig. 2. The π-π stacking interactions between PAN ligands and C—S ring contacts.
2-(2-Hydroxy-1-naphthyldiazenyl)pyridinium [1-(2-pyridyldiazenyl)-2-naphtholato-κ3N,N',O]tris(thiocyanato- κN)chromium(III) methanol solvate top
Crystal data top
(C15H12N3O)[Cr(C15H10N3O)(NCS)3]·CH4OZ = 2
Mr = 756.82F000 = 778
Triclinic, P1Dx = 1.435 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 11.5045 (11) ÅCell parameters from 943 reflections
b = 12.3189 (11) Åθ = 2.4–18.5º
c = 12.5197 (12) ŵ = 0.56 mm−1
α = 95.568 (2)ºT = 273 (2) K
β = 91.851 (2)ºBlock, dark green
γ = 96.973 (2)º0.25 × 0.22 × 0.17 mm
V = 1751.1 (3) Å3
Data collection top
Bruker SMART APEX II CCD
diffractometer		7770 independent reflections
Radiation source: fine-focus sealed tube2997 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.039
T = 291(2) Kθmax = 27.5º
φ and ω scansθmin = 2.3º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −15→10
Tmin = 0.874, Tmax = 0.912k = −16→16
11793 measured reflectionsl = −16→16
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)] = 0.067H-atom parameters constrained
wR(F2) = 0.209  w = 1/[σ2(Fo2) + (0.0826P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
7770 reflectionsΔρmax = 0.30 e Å−3
454 parametersΔρmin = −0.40 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
(C15H12N3O)[Cr(C15H10N3O)(NCS)3]·CH4Oγ = 96.973 (2)º
Mr = 756.82V = 1751.1 (3) Å3
Triclinic, P1Z = 2
a = 11.5045 (11) ÅMo Kα
b = 12.3189 (11) ŵ = 0.56 mm−1
c = 12.5197 (12) ÅT = 273 (2) K
α = 95.568 (2)º0.25 × 0.22 × 0.17 mm
β = 91.851 (2)º
Data collection top
Bruker SMART APEX II CCD
diffractometer		7770 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2997 reflections with I > 2σ(I)
Tmin = 0.874, Tmax = 0.912Rint = 0.039
11793 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.067454 parameters
wR(F2) = 0.209H-atom parameters constrained
S = 0.96Δρmax = 0.30 e Å−3
7770 reflectionsΔρmin = −0.40 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cr10.67707 (7)0.78088 (6)0.54026 (6)0.0578 (3)
C10.4376 (4)0.7422 (4)0.4627 (4)0.0548 (12)
C20.4604 (4)0.6584 (4)0.5301 (4)0.0559 (13)
C30.3659 (5)0.5775 (4)0.5483 (4)0.0677 (15)
H30.37840.52220.59130.081*
C40.2590 (5)0.5803 (4)0.5038 (5)0.0727 (16)
H40.19850.52760.51900.087*
C50.2331 (4)0.6610 (4)0.4336 (5)0.0665 (15)
C60.1223 (5)0.6589 (5)0.3868 (6)0.0886 (19)
H60.06190.60780.40510.106*
C70.0996 (5)0.7317 (5)0.3128 (6)0.102 (2)
H70.02500.72870.28070.122*
C80.1902 (5)0.8092 (5)0.2875 (6)0.100 (2)
H80.17600.85760.23740.120*
C90.2999 (4)0.8154 (4)0.3350 (5)0.0741 (16)
H9A0.35870.86890.31800.089*
C100.3250 (4)0.7413 (4)0.4100 (4)0.0620 (14)
C110.6506 (4)0.9631 (4)0.4199 (4)0.0536 (12)
C120.6706 (5)1.0577 (4)0.3700 (4)0.0674 (15)
H120.61151.08030.32810.081*
C130.7799 (5)1.1187 (4)0.3829 (5)0.0785 (17)
H130.79581.18280.34950.094*
C140.8649 (5)1.0833 (5)0.4458 (5)0.0891 (19)
H140.93921.12290.45490.107*
C150.8397 (4)0.9896 (5)0.4951 (5)0.0799 (17)
H150.89680.96840.54020.096*
C160.7459 (4)0.6619 (4)0.3243 (5)0.0631 (14)
C170.8993 (4)0.7003 (4)0.6412 (4)0.0530 (12)
C180.6145 (4)0.9187 (5)0.7523 (5)0.0639 (14)
C190.9169 (7)0.2356 (8)1.0362 (5)0.106 (3)
C201.0369 (13)0.2950 (12)1.0400 (8)0.156 (6)
C211.1309 (12)0.2374 (15)1.0798 (11)0.221 (10)
H211.20800.27031.07860.265*
C221.1116 (19)0.1451 (17)1.1155 (14)0.244 (14)
H221.17560.11181.13690.293*
C230.9927 (12)0.0864 (11)1.1256 (7)0.171 (5)
C240.9728 (15)−0.0160 (12)1.1704 (12)0.214 (10)
H241.0357−0.04451.20110.256*
C250.8660 (16)−0.0715 (12)1.1694 (12)0.223 (10)
H250.8551−0.13931.19690.268*
C260.7713 (10)−0.0280 (7)1.1273 (6)0.157 (4)
H260.6962−0.06571.12760.188*
C270.7892 (10)0.0735 (7)1.0842 (6)0.130 (4)
H270.72530.10261.05610.156*
C280.8979 (9)0.1299 (9)1.0829 (6)0.120 (4)
C290.7445 (5)0.3957 (6)0.8938 (4)0.0848 (18)
C300.7542 (5)0.4775 (6)0.8238 (4)0.097 (2)
H300.82720.51490.81220.116*
C310.6560 (7)0.5021 (6)0.7725 (5)0.105 (2)
H310.66200.55690.72610.126*
C320.5476 (6)0.4462 (6)0.7889 (6)0.102 (2)
H320.48040.46220.75340.123*
C330.5414 (6)0.3685 (6)0.8571 (5)0.103 (2)
H330.46890.33050.86950.124*
C340.4037 (9)0.7067 (6)0.8293 (7)0.171 (4)
H34A0.34480.74710.80230.256*
H34B0.36910.63360.83920.256*
H34C0.46470.70310.77900.256*
N10.5352 (3)0.8163 (3)0.4601 (3)0.0515 (10)
N20.5393 (3)0.9016 (3)0.4073 (3)0.0543 (10)
N30.7350 (3)0.9268 (3)0.4807 (3)0.0617 (11)
N40.7172 (4)0.7007 (4)0.4042 (4)0.0668 (12)
N50.8219 (4)0.7427 (4)0.6115 (3)0.0690 (12)
N60.6368 (4)0.8688 (4)0.6740 (4)0.0663 (12)
N70.8267 (4)0.2708 (5)0.9922 (4)0.0939 (17)
N80.8414 (4)0.3668 (6)0.9466 (4)0.0974 (18)
N90.6382 (4)0.3447 (4)0.9076 (4)0.0877 (15)
H90.63120.29440.95090.105*
O10.5634 (3)0.6576 (3)0.5728 (3)0.0601 (9)
O21.0568 (5)0.3861 (8)1.0048 (5)0.158 (4)
H20.99790.39940.97240.236*
O30.4523 (5)0.7608 (5)0.9300 (4)0.1310 (18)
H3A0.50030.81310.91930.196*
S10.78500 (16)0.60433 (18)0.21174 (16)0.1208 (7)
S21.00656 (11)0.64120 (11)0.68460 (12)0.0674 (4)
S30.58372 (16)0.98911 (14)0.86114 (13)0.0944 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cr10.0502 (5)0.0543 (5)0.0720 (6)0.0090 (4)−0.0011 (4)0.0206 (4)
C10.047 (3)0.048 (3)0.071 (3)0.000 (2)0.001 (3)0.021 (3)
C20.053 (3)0.048 (3)0.068 (3)0.006 (2)0.001 (3)0.013 (3)
C30.072 (4)0.049 (3)0.085 (4)0.002 (3)0.018 (3)0.025 (3)
C40.068 (4)0.047 (3)0.102 (4)−0.008 (3)0.016 (3)0.014 (3)
C50.049 (3)0.046 (3)0.101 (4)−0.006 (2)−0.002 (3)0.007 (3)
C60.055 (4)0.064 (4)0.141 (6)−0.010 (3)−0.013 (4)0.008 (4)
C70.057 (4)0.084 (5)0.160 (7)−0.001 (4)−0.028 (4)0.014 (5)
C80.059 (4)0.086 (4)0.151 (6)−0.011 (3)−0.043 (4)0.032 (4)
C90.054 (3)0.058 (3)0.109 (4)−0.005 (3)−0.022 (3)0.025 (3)
C100.051 (3)0.044 (3)0.090 (4)−0.001 (2)−0.001 (3)0.012 (3)
C110.044 (3)0.044 (3)0.073 (3)0.000 (2)−0.002 (3)0.017 (3)
C120.059 (3)0.054 (3)0.090 (4)−0.002 (3)−0.007 (3)0.024 (3)
C130.065 (4)0.056 (3)0.115 (5)−0.003 (3)0.008 (4)0.022 (3)
C140.047 (3)0.070 (4)0.149 (6)−0.014 (3)0.001 (4)0.034 (4)
C150.040 (3)0.078 (4)0.124 (5)0.002 (3)−0.008 (3)0.031 (4)
C160.049 (3)0.064 (4)0.077 (4)−0.002 (3)0.001 (3)0.021 (3)
C170.051 (3)0.052 (3)0.058 (3)0.003 (2)0.005 (3)0.018 (2)
C180.052 (3)0.064 (4)0.077 (4)0.005 (3)−0.012 (3)0.021 (3)
C190.092 (5)0.167 (8)0.062 (4)0.069 (6)−0.024 (4)−0.034 (5)
C200.132 (10)0.257 (16)0.081 (7)0.087 (12)−0.018 (7)−0.046 (8)
C210.125 (9)0.38 (2)0.150 (11)0.169 (15)−0.083 (8)−0.158 (14)
C220.234 (16)0.34 (3)0.167 (13)0.24 (2)−0.118 (12)−0.149 (16)
C230.204 (11)0.199 (12)0.117 (7)0.153 (10)−0.081 (8)−0.079 (7)
C240.34 (2)0.171 (15)0.145 (9)0.201 (17)−0.130 (14)−0.068 (10)
C250.41 (3)0.142 (12)0.126 (8)0.147 (16)−0.101 (16)−0.042 (8)
C260.263 (12)0.109 (7)0.111 (6)0.100 (8)−0.041 (7)−0.006 (5)
C270.209 (10)0.114 (7)0.078 (5)0.100 (7)−0.050 (6)−0.018 (5)
C280.134 (7)0.156 (9)0.079 (5)0.108 (7)−0.045 (5)−0.036 (5)
C290.067 (4)0.127 (5)0.059 (4)−0.009 (4)−0.006 (3)0.033 (4)
C300.071 (4)0.150 (6)0.064 (4)−0.029 (4)−0.012 (3)0.042 (4)
C310.116 (6)0.119 (6)0.077 (4)−0.017 (5)−0.032 (4)0.050 (4)
C320.076 (5)0.121 (6)0.115 (5)0.003 (4)−0.021 (4)0.058 (5)
C330.074 (4)0.118 (6)0.121 (5)0.005 (4)−0.019 (4)0.054 (5)
C340.278 (13)0.092 (6)0.141 (8)0.003 (7)0.079 (9)0.009 (6)
N10.048 (2)0.046 (2)0.064 (2)0.0084 (19)0.002 (2)0.016 (2)
N20.048 (2)0.043 (2)0.072 (3)−0.0033 (18)−0.009 (2)0.023 (2)
N30.043 (2)0.059 (3)0.084 (3)0.002 (2)−0.005 (2)0.021 (2)
N40.064 (3)0.063 (3)0.076 (3)0.010 (2)0.013 (3)0.018 (3)
N50.057 (3)0.073 (3)0.082 (3)0.019 (2)−0.003 (2)0.025 (2)
N60.062 (3)0.064 (3)0.075 (3)0.013 (2)−0.004 (3)0.013 (3)
N70.082 (4)0.149 (5)0.058 (3)0.045 (4)−0.012 (3)0.011 (3)
N80.065 (3)0.169 (6)0.062 (3)0.021 (4)−0.012 (3)0.032 (4)
N90.072 (3)0.113 (4)0.083 (3)0.001 (3)−0.006 (3)0.053 (3)
O10.057 (2)0.052 (2)0.075 (2)0.0083 (17)0.0027 (18)0.0236 (17)
O20.050 (3)0.331 (12)0.083 (4)0.039 (6)−0.017 (3)−0.034 (5)
O30.162 (5)0.117 (4)0.122 (4)0.006 (4)0.041 (4)0.059 (4)
S10.0898 (13)0.1460 (18)0.1114 (14)−0.0141 (12)0.0249 (12)−0.0339 (13)
S20.0527 (8)0.0620 (9)0.0906 (10)0.0118 (7)−0.0018 (7)0.0200 (8)
S30.1116 (14)0.0906 (12)0.0783 (11)0.0090 (10)0.0017 (10)0.0002 (9)
Geometric parameters (Å, °) top
Cr1—O11.964 (3)C18—S31.616 (6)
Cr1—N41.981 (5)C19—N71.299 (7)
Cr1—N51.992 (4)C19—C281.473 (12)
Cr1—N12.003 (4)C19—C201.479 (15)
Cr1—N62.003 (5)C20—O21.244 (13)
Cr1—N32.058 (4)C20—C211.463 (15)
C1—N11.362 (5)C21—C221.26 (3)
C1—C101.433 (6)C21—H210.9300
C1—C21.438 (6)C22—C231.48 (2)
C2—O11.286 (5)C22—H220.9300
C2—C31.422 (6)C23—C281.387 (10)
C3—C41.339 (7)C23—C241.43 (2)
C3—H30.9300C24—C251.33 (2)
C4—C51.440 (7)C24—H240.9300
C4—H40.9300C25—C261.382 (14)
C5—C61.381 (7)C25—H250.9300
C5—C101.416 (6)C26—C271.404 (11)
C6—C71.391 (8)C26—H260.9300
C6—H60.9300C27—C281.356 (12)
C7—C81.392 (8)C27—H270.9300
C7—H70.9300C29—N91.330 (7)
C8—C91.368 (7)C29—N81.379 (7)
C8—H80.9300C29—C301.395 (8)
C9—C101.419 (7)C30—C311.362 (8)
C9—H9A0.9300C30—H300.9300
C11—N31.358 (5)C31—C321.381 (8)
C11—C121.374 (6)C31—H310.9300
C11—N21.403 (5)C32—C331.341 (8)
C12—C131.380 (7)C32—H320.9300
C12—H120.9300C33—N91.340 (7)
C13—C141.374 (7)C33—H330.9300
C13—H130.9300C34—O31.430 (9)
C14—C151.366 (7)C34—H34A0.9600
C14—H140.9300C34—H34B0.9600
C15—N31.346 (6)C34—H34C0.9600
C15—H150.9300N1—N21.292 (4)
C16—N41.143 (6)N7—N81.356 (7)
C16—S11.617 (6)N9—H90.8600
C17—N51.155 (5)O2—H20.8200
C17—S21.612 (5)O3—H3A0.8200
C18—N61.159 (6)
O1—Cr1—N492.38 (16)O2—C20—C21122.2 (16)
O1—Cr1—N5100.34 (15)O2—C20—C19121.2 (12)
N4—Cr1—N589.61 (17)C21—C20—C19116.5 (13)
O1—Cr1—N180.57 (14)C22—C21—C20123 (2)
N4—Cr1—N187.03 (16)C22—C21—H21118.7
N5—Cr1—N1176.56 (16)C20—C21—H21118.7
O1—Cr1—N689.83 (16)C21—C22—C23123.9 (15)
N4—Cr1—N6177.12 (17)C21—C22—H22118.0
N5—Cr1—N691.81 (17)C23—C22—H22118.0
N1—Cr1—N691.51 (16)C28—C23—C24118.9 (15)
O1—Cr1—N3157.01 (15)C28—C23—C22118.1 (14)
N4—Cr1—N389.21 (17)C24—C23—C22122.9 (12)
N5—Cr1—N3102.61 (16)C25—C24—C23121.4 (15)
N1—Cr1—N376.61 (15)C25—C24—H24119.3
N6—Cr1—N388.04 (17)C23—C24—H24119.3
N1—C1—C10128.6 (4)C24—C25—C26119.7 (17)
N1—C1—C2110.1 (4)C24—C25—H25120.1
C10—C1—C2121.3 (4)C26—C25—H25120.1
O1—C2—C3121.4 (4)C25—C26—C27119.6 (13)
O1—C2—C1120.5 (4)C25—C26—H26120.2
C3—C2—C1118.1 (5)C27—C26—H26120.2
C4—C3—C2120.5 (5)C28—C27—C26121.3 (10)
C4—C3—H3119.8C28—C27—H27119.4
C2—C3—H3119.8C26—C27—H27119.4
C3—C4—C5123.2 (5)C27—C28—C23119.1 (12)
C3—C4—H4118.4C27—C28—C19121.3 (7)
C5—C4—H4118.4C23—C28—C19119.6 (11)
C6—C5—C10120.1 (5)N9—C29—N8120.4 (5)
C6—C5—C4121.3 (5)N9—C29—C30117.9 (6)
C10—C5—C4118.6 (5)N8—C29—C30121.7 (6)
C5—C6—C7121.3 (6)C31—C30—C29119.5 (6)
C5—C6—H6119.4C31—C30—H30120.2
C7—C6—H6119.4C29—C30—H30120.2
C6—C7—C8118.9 (6)C30—C31—C32120.4 (6)
C6—C7—H7120.6C30—C31—H31119.8
C8—C7—H7120.6C32—C31—H31119.8
C9—C8—C7121.1 (6)C33—C32—C31118.5 (6)
C9—C8—H8119.4C33—C32—H32120.8
C7—C8—H8119.4C31—C32—H32120.8
C8—C9—C10120.8 (5)N9—C33—C32120.9 (6)
C8—C9—H9A119.6N9—C33—H33119.6
C10—C9—H9A119.6C32—C33—H33119.6
C5—C10—C9117.8 (5)O3—C34—H34A109.5
C5—C10—C1118.1 (4)O3—C34—H34B109.5
C9—C10—C1124.0 (4)H34A—C34—H34B109.5
N3—C11—C12122.3 (4)O3—C34—H34C109.5
N3—C11—N2118.9 (4)H34A—C34—H34C109.5
C12—C11—N2118.8 (4)H34B—C34—H34C109.5
C11—C12—C13118.8 (5)N2—N1—C1123.5 (4)
C11—C12—H12120.6N2—N1—Cr1121.4 (3)
C13—C12—H12120.6C1—N1—Cr1115.1 (3)
C14—C13—C12119.0 (5)N1—N2—C11110.8 (4)
C14—C13—H13120.5C15—N3—C11117.7 (4)
C12—C13—H13120.5C15—N3—Cr1130.0 (4)
C15—C14—C13119.7 (5)C11—N3—Cr1112.2 (3)
C15—C14—H14120.1C16—N4—Cr1174.6 (5)
C13—C14—H14120.1C17—N5—Cr1166.2 (4)
N3—C15—C14122.3 (5)C18—N6—Cr1179.0 (4)
N3—C15—H15118.9C19—N7—N8119.3 (7)
C14—C15—H15118.9N7—N8—C29116.7 (5)
N4—C16—S1178.7 (5)C29—N9—C33122.8 (5)
N5—C17—S2179.1 (5)C29—N9—H9118.6
N6—C18—S3179.6 (6)C33—N9—H9118.6
N7—C19—C28117.8 (8)C2—O1—Cr1113.7 (3)
N7—C19—C20123.4 (10)C20—O2—H2109.5
C28—C19—C20118.8 (8)C34—O3—H3A109.5
N1—C1—C2—O1−3.8 (6)C29—C30—C31—C32−0.4 (11)
C10—C1—C2—O1176.8 (4)C30—C31—C32—C330.7 (11)
N1—C1—C2—C3175.9 (4)C31—C32—C33—N9−0.5 (11)
C10—C1—C2—C3−3.4 (7)C10—C1—N1—N20.6 (8)
O1—C2—C3—C4179.4 (5)C2—C1—N1—N2−178.7 (4)
C1—C2—C3—C4−0.3 (8)C10—C1—N1—Cr1−177.0 (4)
C2—C3—C4—C52.0 (8)C2—C1—N1—Cr13.7 (5)
C3—C4—C5—C6178.0 (5)O1—Cr1—N1—N2−180.0 (4)
C3—C4—C5—C100.1 (8)N4—Cr1—N1—N2−87.1 (3)
C10—C5—C6—C72.7 (9)N6—Cr1—N1—N290.4 (4)
C4—C5—C6—C7−175.1 (6)N3—Cr1—N1—N22.8 (3)
C5—C6—C7—C8−1.2 (10)O1—Cr1—N1—C1−2.3 (3)
C6—C7—C8—C9−0.8 (10)N4—Cr1—N1—C190.6 (3)
C7—C8—C9—C101.3 (10)N6—Cr1—N1—C1−91.9 (3)
C6—C5—C10—C9−2.1 (8)N3—Cr1—N1—C1−179.5 (4)
C4—C5—C10—C9175.8 (5)C1—N1—N2—C11179.7 (4)
C6—C5—C10—C1178.4 (5)Cr1—N1—N2—C11−2.9 (5)
C4—C5—C10—C1−3.8 (7)N3—C11—N2—N10.9 (6)
C8—C9—C10—C50.1 (8)C12—C11—N2—N1−179.4 (4)
C8—C9—C10—C1179.6 (5)C14—C15—N3—C11−4.1 (8)
N1—C1—C10—C5−173.8 (5)C14—C15—N3—Cr1177.6 (4)
C2—C1—C10—C55.4 (7)C12—C11—N3—C152.9 (7)
N1—C1—C10—C96.7 (9)N2—C11—N3—C15−177.4 (5)
C2—C1—C10—C9−174.1 (5)C12—C11—N3—Cr1−178.5 (4)
N3—C11—C12—C13−0.7 (8)N2—C11—N3—Cr11.2 (5)
N2—C11—C12—C13179.6 (5)O1—Cr1—N3—C15169.4 (4)
C11—C12—C13—C14−0.4 (9)N4—Cr1—N3—C15−96.4 (5)
C12—C13—C14—C15−0.6 (9)N5—Cr1—N3—C15−7.0 (5)
C13—C14—C15—N33.0 (10)N1—Cr1—N3—C15176.4 (5)
N7—C19—C20—O23.4 (16)N6—Cr1—N3—C1584.4 (5)
C28—C19—C20—O2−177.7 (10)O1—Cr1—N3—C11−9.0 (6)
N7—C19—C20—C21−172.2 (8)N4—Cr1—N3—C1185.2 (3)
C28—C19—C20—C216.6 (12)N5—Cr1—N3—C11174.6 (3)
O2—C20—C21—C22−180.0 (17)N1—Cr1—N3—C11−1.9 (3)
C19—C20—C21—C22−4(2)N6—Cr1—N3—C11−94.0 (3)
C20—C21—C22—C23−2(3)O1—Cr1—N5—C1750.8 (17)
C21—C22—C23—C287(2)N4—Cr1—N5—C17−41.6 (16)
C21—C22—C23—C24−177.3 (15)N6—Cr1—N5—C17140.9 (16)
C28—C23—C24—C252(2)N3—Cr1—N5—C17−130.7 (16)
C22—C23—C24—C25−173.8 (16)C28—C19—N7—N8−178.7 (5)
C23—C24—C25—C26−2(3)C20—C19—N7—N80.2 (10)
C24—C25—C26—C271(2)C19—N7—N8—C29175.0 (5)
C25—C26—C27—C280.1 (13)N9—C29—N8—N714.2 (9)
C26—C27—C28—C23−0.4 (12)C30—C29—N8—N7−165.0 (6)
C26—C27—C28—C19179.1 (6)N8—C29—N9—C33−179.0 (6)
C24—C23—C28—C27−0.5 (13)C30—C29—N9—C330.3 (10)
C22—C23—C28—C27175.3 (10)C32—C33—N9—C290.0 (11)
C24—C23—C28—C19180.0 (9)C3—C2—O1—Cr1−177.8 (4)
C22—C23—C28—C19−4.2 (13)C1—C2—O1—Cr12.0 (6)
N7—C19—C28—C27−2.9 (11)N4—Cr1—O1—C2−86.4 (3)
C20—C19—C28—C27178.1 (8)N5—Cr1—O1—C2−176.4 (3)
N7—C19—C28—C23176.6 (6)N1—Cr1—O1—C20.2 (3)
C20—C19—C28—C23−2.3 (11)N6—Cr1—O1—C291.7 (3)
N9—C29—C30—C31−0.1 (10)N3—Cr1—O1—C27.2 (6)
N8—C29—C30—C31179.2 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···S30.822.453.234 (5)161
O2—H2···N70.822.412.840 (9)114
O2—H2···N80.821.812.536 (8)147
Table 1
Selected geometric parameters (Å, °) top
Cr1—O11.964 (3)Cr1—N12.003 (4)
Cr1—N41.981 (5)Cr1—N62.003 (5)
Cr1—N51.992 (4)Cr1—N32.058 (4)
O1—Cr1—N492.38 (16)N5—Cr1—N691.81 (17)
O1—Cr1—N5100.34 (15)N1—Cr1—N691.51 (16)
N4—Cr1—N589.61 (17)O1—Cr1—N3157.01 (15)
O1—Cr1—N180.57 (14)N4—Cr1—N389.21 (17)
N4—Cr1—N187.03 (16)N5—Cr1—N3102.61 (16)
N5—Cr1—N1176.56 (16)N1—Cr1—N376.61 (15)
O1—Cr1—N689.83 (16)N6—Cr1—N388.04 (17)
N4—Cr1—N6177.12 (17)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···S30.822.453.234 (5)161
O2—H2···N70.822.412.840 (9)114
O2—H2···N80.821.812.536 (8)147
Acknowledgements top

The authors acknowledge support from the Natural Science Foundation Council of China (NSFC) (grant No. 20401003) and the Excellent Young Scholars Research Fund of the Beijing Institute of Technology (grant No. 000Y07–26).

references
References top

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Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Please check date for APEX2.

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Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Sheldrick, G. M. (1997b). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.