2-(2-Hydr­oxy-1-naphthyl­diazen­yl)­pyridinium [1-(2-pyridyldiazen­yl)-2-naphtholato-κ3N,N′,O]tris­(thio­cyanato-κN)chromium(III) methanol solvate

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

doi:10.1107/S1600536807040688

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2-(2-Hydroxy-1-naphthyldiazenyl)pyridinium [1-(2-pyridyldiazenyl)-2-naphtholato-κ³N,N′,O]tris(thiocyanato-κN)chromium(III) methanol solvate

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

In the title compound, (C₁₅H₁₂N₃O)[Cr(C₁₅H₁₀N₃O)(NCS)₃]·CH₄O, the Cr^III 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 π–π interactions [centroid–centroid separation 3.594 (4) Å] and O—H

N and O—H

S hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040688/cs2044sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040688/cs2044Isup2.hkl Contains datablock I

CCDC reference: 660156

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.012 Å
R factor = 0.067
wR factor = 0.209
Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         39 Perc.
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C22
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C25
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C16

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT213_ALERT_2_C Atom C21     has ADP max/min Ratio .............       3.50 prola
PLAT213_ALERT_2_C Atom C22     has ADP max/min Ratio .............       3.60 prola
PLAT213_ALERT_2_C Atom C24     has ADP max/min Ratio .............       3.60 prola
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.87 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C22    -   C23     ..       5.61 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C24
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C23
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C26
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C28
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       3.63
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C19    -C28           1.44 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range .......  C19    -C28           0.22 Ang.
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         12

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cr1         (3)       3.47

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  19 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  18 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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 Cr^III 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 C₂_V. 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%).

Structure description top

For related literature, see: Spek (2003).

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

	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.
	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]·CH₄O	Z = 2
M_r = 756.82	F(000) = 778
Triclinic, P1	D_x = 1.435 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.5045 (11) Å	Cell parameters from 943 reflections
b = 12.3189 (11) Å	θ = 2.4–18.5°
c = 12.5197 (12) Å	µ = 0.56 mm⁻¹
α = 95.568 (2)°	T = 273 K
β = 91.851 (2)°	Block, dark green
γ = 96.973 (2)°	0.25 × 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 tube	2997 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
φ and ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→10
T_min = 0.874, T_max = 0.912	k = −16→16
11793 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.209	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0826P)²] where P = (F_o² + 2F_c²)/3
7770 reflections	(Δ/σ)_max < 0.001
454 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

(C₁₅H₁₂N₃O)[Cr(C₁₅H₁₀N₃O)(NCS)₃]·CH₄O	γ = 96.973 (2)°
M_r = 756.82	V = 1751.1 (3) Å³
Triclinic, P1	Z = 2
a = 11.5045 (11) Å	Mo Kα radiation
b = 12.3189 (11) Å	µ = 0.56 mm⁻¹
c = 12.5197 (12) Å	T = 273 K
α = 95.568 (2)°	0.25 × 0.22 × 0.17 mm
β = 91.851 (2)°

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)
T_min = 0.874, T_max = 0.912	R_int = 0.039
11793 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.209	H-atom parameters constrained
S = 0.96	Δρ_max = 0.30 e Å⁻³
7770 reflections	Δρ_min = −0.40 e Å⁻³
454 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cr1	0.67707 (7)	0.78088 (6)	0.54026 (6)	0.0578 (3)
C1	0.4376 (4)	0.7422 (4)	0.4627 (4)	0.0548 (12)
C2	0.4604 (4)	0.6584 (4)	0.5301 (4)	0.0559 (13)
C3	0.3659 (5)	0.5775 (4)	0.5483 (4)	0.0677 (15)
H3	0.3784	0.5222	0.5913	0.081*
C4	0.2590 (5)	0.5803 (4)	0.5038 (5)	0.0727 (16)
H4	0.1985	0.5276	0.5190	0.087*
C5	0.2331 (4)	0.6610 (4)	0.4336 (5)	0.0665 (15)
C6	0.1223 (5)	0.6589 (5)	0.3868 (6)	0.0886 (19)
H6	0.0619	0.6078	0.4051	0.106*
C7	0.0996 (5)	0.7317 (5)	0.3128 (6)	0.102 (2)
H7	0.0250	0.7287	0.2807	0.122*
C8	0.1902 (5)	0.8092 (5)	0.2875 (6)	0.100 (2)
H8	0.1760	0.8576	0.2374	0.120*
C9	0.2999 (4)	0.8154 (4)	0.3350 (5)	0.0741 (16)
H9A	0.3587	0.8689	0.3180	0.089*
C10	0.3250 (4)	0.7413 (4)	0.4100 (4)	0.0620 (14)
C11	0.6506 (4)	0.9631 (4)	0.4199 (4)	0.0536 (12)
C12	0.6706 (5)	1.0577 (4)	0.3700 (4)	0.0674 (15)
H12	0.6115	1.0803	0.3281	0.081*
C13	0.7799 (5)	1.1187 (4)	0.3829 (5)	0.0785 (17)
H13	0.7958	1.1828	0.3495	0.094*
C14	0.8649 (5)	1.0833 (5)	0.4458 (5)	0.0891 (19)
H14	0.9392	1.1229	0.4549	0.107*
C15	0.8397 (4)	0.9896 (5)	0.4951 (5)	0.0799 (17)
H15	0.8968	0.9684	0.5402	0.096*
C16	0.7459 (4)	0.6619 (4)	0.3243 (5)	0.0631 (14)
C17	0.8993 (4)	0.7003 (4)	0.6412 (4)	0.0530 (12)
C18	0.6145 (4)	0.9187 (5)	0.7523 (5)	0.0639 (14)
C19	0.9169 (7)	0.2356 (8)	1.0362 (5)	0.106 (3)
C20	1.0369 (13)	0.2950 (12)	1.0400 (8)	0.156 (6)
C21	1.1309 (12)	0.2374 (15)	1.0798 (11)	0.221 (10)
H21	1.2080	0.2703	1.0786	0.265*
C22	1.1116 (19)	0.1451 (17)	1.1155 (14)	0.244 (14)
H22	1.1756	0.1118	1.1369	0.293*
C23	0.9927 (12)	0.0864 (11)	1.1256 (7)	0.171 (5)
C24	0.9728 (15)	−0.0160 (12)	1.1704 (12)	0.214 (10)
H24	1.0357	−0.0445	1.2011	0.256*
C25	0.8660 (16)	−0.0715 (12)	1.1694 (12)	0.223 (10)
H25	0.8551	−0.1393	1.1969	0.268*
C26	0.7713 (10)	−0.0280 (7)	1.1273 (6)	0.157 (4)
H26	0.6962	−0.0657	1.1276	0.188*
C27	0.7892 (10)	0.0735 (7)	1.0842 (6)	0.130 (4)
H27	0.7253	0.1026	1.0561	0.156*
C28	0.8979 (9)	0.1299 (9)	1.0829 (6)	0.120 (4)
C29	0.7445 (5)	0.3957 (6)	0.8938 (4)	0.0848 (18)
C30	0.7542 (5)	0.4775 (6)	0.8238 (4)	0.097 (2)
H30	0.8272	0.5149	0.8122	0.116*
C31	0.6560 (7)	0.5021 (6)	0.7725 (5)	0.105 (2)
H31	0.6620	0.5569	0.7261	0.126*
C32	0.5476 (6)	0.4462 (6)	0.7889 (6)	0.102 (2)
H32	0.4804	0.4622	0.7534	0.123*
C33	0.5414 (6)	0.3685 (6)	0.8571 (5)	0.103 (2)
H33	0.4689	0.3305	0.8695	0.124*
C34	0.4037 (9)	0.7067 (6)	0.8293 (7)	0.171 (4)
H34A	0.3448	0.7471	0.8023	0.256*
H34B	0.3691	0.6336	0.8392	0.256*
H34C	0.4647	0.7031	0.7790	0.256*
N1	0.5352 (3)	0.8163 (3)	0.4601 (3)	0.0515 (10)
N2	0.5393 (3)	0.9016 (3)	0.4073 (3)	0.0543 (10)
N3	0.7350 (3)	0.9268 (3)	0.4807 (3)	0.0617 (11)
N4	0.7172 (4)	0.7007 (4)	0.4042 (4)	0.0668 (12)
N5	0.8219 (4)	0.7427 (4)	0.6115 (3)	0.0690 (12)
N6	0.6368 (4)	0.8688 (4)	0.6740 (4)	0.0663 (12)
N7	0.8267 (4)	0.2708 (5)	0.9922 (4)	0.0939 (17)
N8	0.8414 (4)	0.3668 (6)	0.9466 (4)	0.0974 (18)
N9	0.6382 (4)	0.3447 (4)	0.9076 (4)	0.0877 (15)
H9	0.6312	0.2944	0.9509	0.105*
O1	0.5634 (3)	0.6576 (3)	0.5728 (3)	0.0601 (9)
O2	1.0568 (5)	0.3861 (8)	1.0048 (5)	0.158 (4)
H2	0.9979	0.3994	0.9724	0.236*
O3	0.4523 (5)	0.7608 (5)	0.9300 (4)	0.1310 (18)
H3A	0.5003	0.8131	0.9193	0.196*
S1	0.78500 (16)	0.60433 (18)	0.21174 (16)	0.1208 (7)
S2	1.00656 (11)	0.64120 (11)	0.68460 (12)	0.0674 (4)
S3	0.58372 (16)	0.98911 (14)	0.86114 (13)	0.0944 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cr1	0.0502 (5)	0.0543 (5)	0.0720 (6)	0.0090 (4)	−0.0011 (4)	0.0206 (4)
C1	0.047 (3)	0.048 (3)	0.071 (3)	0.000 (2)	0.001 (3)	0.021 (3)
C2	0.053 (3)	0.048 (3)	0.068 (3)	0.006 (2)	0.001 (3)	0.013 (3)
C3	0.072 (4)	0.049 (3)	0.085 (4)	0.002 (3)	0.018 (3)	0.025 (3)
C4	0.068 (4)	0.047 (3)	0.102 (4)	−0.008 (3)	0.016 (3)	0.014 (3)
C5	0.049 (3)	0.046 (3)	0.101 (4)	−0.006 (2)	−0.002 (3)	0.007 (3)
C6	0.055 (4)	0.064 (4)	0.141 (6)	−0.010 (3)	−0.013 (4)	0.008 (4)
C7	0.057 (4)	0.084 (5)	0.160 (7)	−0.001 (4)	−0.028 (4)	0.014 (5)
C8	0.059 (4)	0.086 (4)	0.151 (6)	−0.011 (3)	−0.043 (4)	0.032 (4)
C9	0.054 (3)	0.058 (3)	0.109 (4)	−0.005 (3)	−0.022 (3)	0.025 (3)
C10	0.051 (3)	0.044 (3)	0.090 (4)	−0.001 (2)	−0.001 (3)	0.012 (3)
C11	0.044 (3)	0.044 (3)	0.073 (3)	0.000 (2)	−0.002 (3)	0.017 (3)
C12	0.059 (3)	0.054 (3)	0.090 (4)	−0.002 (3)	−0.007 (3)	0.024 (3)
C13	0.065 (4)	0.056 (3)	0.115 (5)	−0.003 (3)	0.008 (4)	0.022 (3)
C14	0.047 (3)	0.070 (4)	0.149 (6)	−0.014 (3)	0.001 (4)	0.034 (4)
C15	0.040 (3)	0.078 (4)	0.124 (5)	0.002 (3)	−0.008 (3)	0.031 (4)
C16	0.049 (3)	0.064 (4)	0.077 (4)	−0.002 (3)	0.001 (3)	0.021 (3)
C17	0.051 (3)	0.052 (3)	0.058 (3)	0.003 (2)	0.005 (3)	0.018 (2)
C18	0.052 (3)	0.064 (4)	0.077 (4)	0.005 (3)	−0.012 (3)	0.021 (3)
C19	0.092 (5)	0.167 (8)	0.062 (4)	0.069 (6)	−0.024 (4)	−0.034 (5)
C20	0.132 (10)	0.257 (16)	0.081 (7)	0.087 (12)	−0.018 (7)	−0.046 (8)
C21	0.125 (9)	0.38 (2)	0.150 (11)	0.169 (15)	−0.083 (8)	−0.158 (14)
C22	0.234 (16)	0.34 (3)	0.167 (13)	0.24 (2)	−0.118 (12)	−0.149 (16)
C23	0.204 (11)	0.199 (12)	0.117 (7)	0.153 (10)	−0.081 (8)	−0.079 (7)
C24	0.34 (2)	0.171 (15)	0.145 (9)	0.201 (17)	−0.130 (14)	−0.068 (10)
C25	0.41 (3)	0.142 (12)	0.126 (8)	0.147 (16)	−0.101 (16)	−0.042 (8)
C26	0.263 (12)	0.109 (7)	0.111 (6)	0.100 (8)	−0.041 (7)	−0.006 (5)
C27	0.209 (10)	0.114 (7)	0.078 (5)	0.100 (7)	−0.050 (6)	−0.018 (5)
C28	0.134 (7)	0.156 (9)	0.079 (5)	0.108 (7)	−0.045 (5)	−0.036 (5)
C29	0.067 (4)	0.127 (5)	0.059 (4)	−0.009 (4)	−0.006 (3)	0.033 (4)
C30	0.071 (4)	0.150 (6)	0.064 (4)	−0.029 (4)	−0.012 (3)	0.042 (4)
C31	0.116 (6)	0.119 (6)	0.077 (4)	−0.017 (5)	−0.032 (4)	0.050 (4)
C32	0.076 (5)	0.121 (6)	0.115 (5)	0.003 (4)	−0.021 (4)	0.058 (5)
C33	0.074 (4)	0.118 (6)	0.121 (5)	0.005 (4)	−0.019 (4)	0.054 (5)
C34	0.278 (13)	0.092 (6)	0.141 (8)	0.003 (7)	0.079 (9)	0.009 (6)
N1	0.048 (2)	0.046 (2)	0.064 (2)	0.0084 (19)	0.002 (2)	0.016 (2)
N2	0.048 (2)	0.043 (2)	0.072 (3)	−0.0033 (18)	−0.009 (2)	0.023 (2)
N3	0.043 (2)	0.059 (3)	0.084 (3)	0.002 (2)	−0.005 (2)	0.021 (2)
N4	0.064 (3)	0.063 (3)	0.076 (3)	0.010 (2)	0.013 (3)	0.018 (3)
N5	0.057 (3)	0.073 (3)	0.082 (3)	0.019 (2)	−0.003 (2)	0.025 (2)
N6	0.062 (3)	0.064 (3)	0.075 (3)	0.013 (2)	−0.004 (3)	0.013 (3)
N7	0.082 (4)	0.149 (5)	0.058 (3)	0.045 (4)	−0.012 (3)	0.011 (3)
N8	0.065 (3)	0.169 (6)	0.062 (3)	0.021 (4)	−0.012 (3)	0.032 (4)
N9	0.072 (3)	0.113 (4)	0.083 (3)	0.001 (3)	−0.006 (3)	0.053 (3)
O1	0.057 (2)	0.052 (2)	0.075 (2)	0.0083 (17)	0.0027 (18)	0.0236 (17)
O2	0.050 (3)	0.331 (12)	0.083 (4)	0.039 (6)	−0.017 (3)	−0.034 (5)
O3	0.162 (5)	0.117 (4)	0.122 (4)	0.006 (4)	0.041 (4)	0.059 (4)
S1	0.0898 (13)	0.1460 (18)	0.1114 (14)	−0.0141 (12)	0.0249 (12)	−0.0339 (13)
S2	0.0527 (8)	0.0620 (9)	0.0906 (10)	0.0118 (7)	−0.0018 (7)	0.0200 (8)
S3	0.1116 (14)	0.0906 (12)	0.0783 (11)	0.0090 (10)	0.0017 (10)	0.0002 (9)

Geometric parameters (Å, º) top

Cr1—O1	1.964 (3)	C18—S3	1.616 (6)
Cr1—N4	1.981 (5)	C19—N7	1.299 (7)
Cr1—N5	1.992 (4)	C19—C28	1.473 (12)
Cr1—N1	2.003 (4)	C19—C20	1.479 (15)
Cr1—N6	2.003 (5)	C20—O2	1.244 (13)
Cr1—N3	2.058 (4)	C20—C21	1.463 (15)
C1—N1	1.362 (5)	C21—C22	1.26 (3)
C1—C10	1.433 (6)	C21—H21	0.9300
C1—C2	1.438 (6)	C22—C23	1.48 (2)
C2—O1	1.286 (5)	C22—H22	0.9300
C2—C3	1.422 (6)	C23—C28	1.387 (10)
C3—C4	1.339 (7)	C23—C24	1.43 (2)
C3—H3	0.9300	C24—C25	1.33 (2)
C4—C5	1.440 (7)	C24—H24	0.9300
C4—H4	0.9300	C25—C26	1.382 (14)
C5—C6	1.381 (7)	C25—H25	0.9300
C5—C10	1.416 (6)	C26—C27	1.404 (11)
C6—C7	1.391 (8)	C26—H26	0.9300
C6—H6	0.9300	C27—C28	1.356 (12)
C7—C8	1.392 (8)	C27—H27	0.9300
C7—H7	0.9300	C29—N9	1.330 (7)
C8—C9	1.368 (7)	C29—N8	1.379 (7)
C8—H8	0.9300	C29—C30	1.395 (8)
C9—C10	1.419 (7)	C30—C31	1.362 (8)
C9—H9A	0.9300	C30—H30	0.9300
C11—N3	1.358 (5)	C31—C32	1.381 (8)
C11—C12	1.374 (6)	C31—H31	0.9300
C11—N2	1.403 (5)	C32—C33	1.341 (8)
C12—C13	1.380 (7)	C32—H32	0.9300
C12—H12	0.9300	C33—N9	1.340 (7)
C13—C14	1.374 (7)	C33—H33	0.9300
C13—H13	0.9300	C34—O3	1.430 (9)
C14—C15	1.366 (7)	C34—H34A	0.9600
C14—H14	0.9300	C34—H34B	0.9600
C15—N3	1.346 (6)	C34—H34C	0.9600
C15—H15	0.9300	N1—N2	1.292 (4)
C16—N4	1.143 (6)	N7—N8	1.356 (7)
C16—S1	1.617 (6)	N9—H9	0.8600
C17—N5	1.155 (5)	O2—H2	0.8200
C17—S2	1.612 (5)	O3—H3A	0.8200
C18—N6	1.159 (6)

O1—Cr1—N4	92.38 (16)	O2—C20—C21	122.2 (16)
O1—Cr1—N5	100.34 (15)	O2—C20—C19	121.2 (12)
N4—Cr1—N5	89.61 (17)	C21—C20—C19	116.5 (13)
O1—Cr1—N1	80.57 (14)	C22—C21—C20	123 (2)
N4—Cr1—N1	87.03 (16)	C22—C21—H21	118.7
N5—Cr1—N1	176.56 (16)	C20—C21—H21	118.7
O1—Cr1—N6	89.83 (16)	C21—C22—C23	123.9 (15)
N4—Cr1—N6	177.12 (17)	C21—C22—H22	118.0
N5—Cr1—N6	91.81 (17)	C23—C22—H22	118.0
N1—Cr1—N6	91.51 (16)	C28—C23—C24	118.9 (15)
O1—Cr1—N3	157.01 (15)	C28—C23—C22	118.1 (14)
N4—Cr1—N3	89.21 (17)	C24—C23—C22	122.9 (12)
N5—Cr1—N3	102.61 (16)	C25—C24—C23	121.4 (15)
N1—Cr1—N3	76.61 (15)	C25—C24—H24	119.3
N6—Cr1—N3	88.04 (17)	C23—C24—H24	119.3
N1—C1—C10	128.6 (4)	C24—C25—C26	119.7 (17)
N1—C1—C2	110.1 (4)	C24—C25—H25	120.1
C10—C1—C2	121.3 (4)	C26—C25—H25	120.1
O1—C2—C3	121.4 (4)	C25—C26—C27	119.6 (13)
O1—C2—C1	120.5 (4)	C25—C26—H26	120.2
C3—C2—C1	118.1 (5)	C27—C26—H26	120.2
C4—C3—C2	120.5 (5)	C28—C27—C26	121.3 (10)
C4—C3—H3	119.8	C28—C27—H27	119.4
C2—C3—H3	119.8	C26—C27—H27	119.4
C3—C4—C5	123.2 (5)	C27—C28—C23	119.1 (12)
C3—C4—H4	118.4	C27—C28—C19	121.3 (7)
C5—C4—H4	118.4	C23—C28—C19	119.6 (11)
C6—C5—C10	120.1 (5)	N9—C29—N8	120.4 (5)
C6—C5—C4	121.3 (5)	N9—C29—C30	117.9 (6)
C10—C5—C4	118.6 (5)	N8—C29—C30	121.7 (6)
C5—C6—C7	121.3 (6)	C31—C30—C29	119.5 (6)
C5—C6—H6	119.4	C31—C30—H30	120.2
C7—C6—H6	119.4	C29—C30—H30	120.2
C6—C7—C8	118.9 (6)	C30—C31—C32	120.4 (6)
C6—C7—H7	120.6	C30—C31—H31	119.8
C8—C7—H7	120.6	C32—C31—H31	119.8
C9—C8—C7	121.1 (6)	C33—C32—C31	118.5 (6)
C9—C8—H8	119.4	C33—C32—H32	120.8
C7—C8—H8	119.4	C31—C32—H32	120.8
C8—C9—C10	120.8 (5)	N9—C33—C32	120.9 (6)
C8—C9—H9A	119.6	N9—C33—H33	119.6
C10—C9—H9A	119.6	C32—C33—H33	119.6
C5—C10—C9	117.8 (5)	O3—C34—H34A	109.5
C5—C10—C1	118.1 (4)	O3—C34—H34B	109.5
C9—C10—C1	124.0 (4)	H34A—C34—H34B	109.5
N3—C11—C12	122.3 (4)	O3—C34—H34C	109.5
N3—C11—N2	118.9 (4)	H34A—C34—H34C	109.5
C12—C11—N2	118.8 (4)	H34B—C34—H34C	109.5
C11—C12—C13	118.8 (5)	N2—N1—C1	123.5 (4)
C11—C12—H12	120.6	N2—N1—Cr1	121.4 (3)
C13—C12—H12	120.6	C1—N1—Cr1	115.1 (3)
C14—C13—C12	119.0 (5)	N1—N2—C11	110.8 (4)
C14—C13—H13	120.5	C15—N3—C11	117.7 (4)
C12—C13—H13	120.5	C15—N3—Cr1	130.0 (4)
C15—C14—C13	119.7 (5)	C11—N3—Cr1	112.2 (3)
C15—C14—H14	120.1	C16—N4—Cr1	174.6 (5)
C13—C14—H14	120.1	C17—N5—Cr1	166.2 (4)
N3—C15—C14	122.3 (5)	C18—N6—Cr1	179.0 (4)
N3—C15—H15	118.9	C19—N7—N8	119.3 (7)
C14—C15—H15	118.9	N7—N8—C29	116.7 (5)
N4—C16—S1	178.7 (5)	C29—N9—C33	122.8 (5)
N5—C17—S2	179.1 (5)	C29—N9—H9	118.6
N6—C18—S3	179.6 (6)	C33—N9—H9	118.6
N7—C19—C28	117.8 (8)	C2—O1—Cr1	113.7 (3)
N7—C19—C20	123.4 (10)	C20—O2—H2	109.5
C28—C19—C20	118.8 (8)	C34—O3—H3A	109.5

N1—C1—C2—O1	−3.8 (6)	C29—C30—C31—C32	−0.4 (11)
C10—C1—C2—O1	176.8 (4)	C30—C31—C32—C33	0.7 (11)
N1—C1—C2—C3	175.9 (4)	C31—C32—C33—N9	−0.5 (11)
C10—C1—C2—C3	−3.4 (7)	C10—C1—N1—N2	0.6 (8)
O1—C2—C3—C4	179.4 (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—C5	2.0 (8)	C2—C1—N1—Cr1	3.7 (5)
C3—C4—C5—C6	178.0 (5)	O1—Cr1—N1—N2	−180.0 (4)
C3—C4—C5—C10	0.1 (8)	N4—Cr1—N1—N2	−87.1 (3)
C10—C5—C6—C7	2.7 (9)	N6—Cr1—N1—N2	90.4 (4)
C4—C5—C6—C7	−175.1 (6)	N3—Cr1—N1—N2	2.8 (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—C1	90.6 (3)
C7—C8—C9—C10	1.3 (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—C9	175.8 (5)	C1—N1—N2—C11	179.7 (4)
C6—C5—C10—C1	178.4 (5)	Cr1—N1—N2—C11	−2.9 (5)
C4—C5—C10—C1	−3.8 (7)	N3—C11—N2—N1	0.9 (6)
C8—C9—C10—C5	0.1 (8)	C12—C11—N2—N1	−179.4 (4)
C8—C9—C10—C1	179.6 (5)	C14—C15—N3—C11	−4.1 (8)
N1—C1—C10—C5	−173.8 (5)	C14—C15—N3—Cr1	177.6 (4)
C2—C1—C10—C5	5.4 (7)	C12—C11—N3—C15	2.9 (7)
N1—C1—C10—C9	6.7 (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—Cr1	1.2 (5)
N2—C11—C12—C13	179.6 (5)	O1—Cr1—N3—C15	169.4 (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—N3	3.0 (10)	N1—Cr1—N3—C15	176.4 (5)
N7—C19—C20—O2	3.4 (16)	N6—Cr1—N3—C15	84.4 (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—C11	85.2 (3)
C28—C19—C20—C21	6.6 (12)	N5—Cr1—N3—C11	174.6 (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—C17	50.8 (17)
C21—C22—C23—C28	7 (2)	N4—Cr1—N5—C17	−41.6 (16)
C21—C22—C23—C24	−177.3 (15)	N6—Cr1—N5—C17	140.9 (16)
C28—C23—C24—C25	2 (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—N8	0.2 (10)
C24—C25—C26—C27	1 (2)	C19—N7—N8—C29	175.0 (5)
C25—C26—C27—C28	0.1 (13)	N9—C29—N8—N7	14.2 (9)
C26—C27—C28—C23	−0.4 (12)	C30—C29—N8—N7	−165.0 (6)
C26—C27—C28—C19	179.1 (6)	N8—C29—N9—C33	−179.0 (6)
C24—C23—C28—C27	−0.5 (13)	C30—C29—N9—C33	0.3 (10)
C22—C23—C28—C27	175.3 (10)	C32—C33—N9—C29	0.0 (11)
C24—C23—C28—C19	180.0 (9)	C3—C2—O1—Cr1	−177.8 (4)
C22—C23—C28—C19	−4.2 (13)	C1—C2—O1—Cr1	2.0 (6)
N7—C19—C28—C27	−2.9 (11)	N4—Cr1—O1—C2	−86.4 (3)
C20—C19—C28—C27	178.1 (8)	N5—Cr1—O1—C2	−176.4 (3)
N7—C19—C28—C23	176.6 (6)	N1—Cr1—O1—C2	0.2 (3)
C20—C19—C28—C23	−2.3 (11)	N6—Cr1—O1—C2	91.7 (3)
N9—C29—C30—C31	−0.1 (10)	N3—Cr1—O1—C2	7.2 (6)
N8—C29—C30—C31	179.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···S3	0.82	2.45	3.234 (5)	161
O2—H2···N7	0.82	2.41	2.840 (9)	114
O2—H2···N8	0.82	1.81	2.536 (8)	147

Experimental details

Crystal data
Chemical formula	(C₁₅H₁₂N₃O)[Cr(C₁₅H₁₀N₃O)(NCS)₃]·CH₄O
M_r	756.82
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	11.5045 (11), 12.3189 (11), 12.5197 (12)
α, β, γ (°)	95.568 (2), 91.851 (2), 96.973 (2)
V (Å³)	1751.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.56
Crystal size (mm)	0.25 × 0.22 × 0.17

Data collection
Diffractometer	Bruker SMART APEX II CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.874, 0.912
No. of measured, independent and observed [I > 2σ(I)] reflections	11793, 7770, 2997
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.209, 0.96
No. of reflections	7770
No. of parameters	454
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.40

Computer programs: APEX2 (Bruker, DATE?), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

Cr1—O1	1.964 (3)	Cr1—N1	2.003 (4)
Cr1—N4	1.981 (5)	Cr1—N6	2.003 (5)
Cr1—N5	1.992 (4)	Cr1—N3	2.058 (4)

O1—Cr1—N4	92.38 (16)	N5—Cr1—N6	91.81 (17)
O1—Cr1—N5	100.34 (15)	N1—Cr1—N6	91.51 (16)
N4—Cr1—N5	89.61 (17)	O1—Cr1—N3	157.01 (15)
O1—Cr1—N1	80.57 (14)	N4—Cr1—N3	89.21 (17)
N4—Cr1—N1	87.03 (16)	N5—Cr1—N3	102.61 (16)
N5—Cr1—N1	176.56 (16)	N1—Cr1—N3	76.61 (15)
O1—Cr1—N6	89.83 (16)	N6—Cr1—N3	88.04 (17)
N4—Cr1—N6	177.12 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···S3	0.82	2.45	3.234 (5)	161
O2—H2···N7	0.82	2.41	2.840 (9)	114
O2—H2···N8	0.82	1.81	2.536 (8)	147

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