Literature DB >> 21200583

Diacetonitrile-tetra-kis{μ(2)-3-anilinocarbonyl-1-[(5-chloro-2-oxidophen-yl)diazen-yl]-2-naphtholato}tetra-aqua-diiron(III)disodium(I) dihydrate.

Sato Yohei1, Uta Kazuya, Jin Mizuguchi.   

Abstract

The title compound, [Fe(2)Na(2)(C(23)H(14)ClN(3)O(3))(4)(C(2)H(3)N)(2)(H(2)O)(4)]·2H(2)O, is a hydrated Fe-azo complex dimer that is used as a charge-control agent in electrophotography. The mol-ecule is a centrosymmetric dimer with two octa-hedral Fe(III) units linked by two bridging five-coordinate Na(I) cations. Each Fe(III) atom is chelated by the N and two O atoms from two 3-anilinocarbonyl-1-[(5-chloro-2-oxidophen-yl)diazen-yl]-2-naph-tholate ligands. The Na(+) cation is coordinated by a carbonyl O atom from the two ligands of each octa-hedral Fe(III) unit, two water mol-ecules and the N atom of an acetonitrile mol-ecule. Two solvent water mol-ecules complete the structure. In the crystal structure, the dimeric mol-ecules are bridged by a pair of discrete inter-molecular O-H⋯O hydrogen bonds, one of which involves a sodium-bound water mol-ecule and a hydrate water, and the other a 5-chloro-phenolate O atom and a water molecule to form an extended chain along b.

Entities:  

Year:  2007        PMID： 21200583      PMCID： PMC2915160          DOI： 10.1107/S1600536807066895

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


Related literature

For general background to charge-control agents, see Tanaka (1995 ▶); and for the preparation of the title compound, see Yasumatsu et al. (2006 ▶). For related structures, see: Mizuguchi, Sato, Uta & Sato (2007 ▶); Mizuguchi et al. (2007a ▶,b ▶); Mizuguchi, Uta & Sato (2007 ▶).

Experimental

Crystal data

[Fe2Na2(C23H14ClN3O3)4(C2H3N)2(H2O)4]·2H2O M = 2011.21 Triclinic, a = 11.4416 (5) Å b = 14.1161 (7) Å c = 15.0105 (7) Å α = 72.396 (1)° β = 76.2850 (9)° γ = 83.015 (1)° V = 2241.67 (18) Å3 Z = 1 Mo Kα radiation μ = 0.53 mm−1 T = 93.1 K 0.30 × 0.09 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.793, T max = 0.976 40907 measured reflections 8133 independent reflections 4163 reflections with I > 2σ(I) R int = 0.125

Refinement

R[F 2 > 2σ(F 2)] = 0.086 wR(F 2) = 0.264 S = 0.97 8133 reflections 607 parameters H-atom parameters constrained Δρmax = 1.17 e Å−3 Δρmin = −1.00 e Å−3 Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2006 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: CrystalStructure. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807066895/sj2453sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066895/sj2453Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Fe2Na2(C23H14ClN3O3)4(C2H3N)2(H2O)4]·2H2OZ = 1
Mr = 2011.21F000 = 1022.0
Triclinic, P1Dx = 1.481 Mg m−3
Hall symbol: -P 1Mo Kα radiation λ = 0.71075 Å
a = 11.4416 (5) ÅCell parameters from 18467 reflections
b = 14.1161 (7) Åθ = 3.0–25.3º
c = 15.0105 (7) ŵ = 0.53 mm−1
α = 72.396 (1)ºT = 93.1 K
β = 76.2850 (9)ºBlock, black
γ = 83.015 (1)º0.30 × 0.09 × 0.05 mm
V = 2241.67 (18) Å3
Rigaku R-AXIS RAPID diffractometer4163 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.125
ω scansθmax = 25.4º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)h = −13→13
Tmin = 0.793, Tmax = 0.976k = −16→16
40907 measured reflectionsl = −18→18
8133 independent reflections
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.086  w = 1/[σ2(Fo2) + (0.1531P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.264(Δ/σ)max < 0.001
S = 0.97Δρmax = 1.17 e Å−3
8133 reflectionsΔρmin = −1.00 e Å−3
607 parametersExtinction correction: none
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.
xyzUiso*/Ueq
Fe10.35889 (7)0.15898 (6)0.81868 (6)0.0419 (3)
Cl10.89755 (14)0.08974 (12)0.97345 (11)0.0493 (4)
Cl2−0.13236 (15)0.46998 (12)0.94460 (12)0.0570 (4)
Na10.1669 (2)−0.2788 (2)0.66698 (19)0.0631 (7)
O10.3035 (3)0.0314 (2)0.8208 (2)0.0431 (9)
O20.2505 (3)0.1532 (2)0.9412 (2)0.0455 (10)
O30.4037 (3)0.1844 (2)0.6776 (2)0.0441 (10)
O40.4653 (3)0.2573 (2)0.8224 (2)0.0435 (10)
O50.6633 (4)0.2145 (3)0.4266 (3)0.0565 (11)
O60.1263 (3)−0.1752 (3)0.7588 (2)0.0506 (11)
O70.0555 (5)−0.1671 (4)0.5459 (4)0.1103 (15)
O80.2170 (5)−0.4270 (4)0.7749 (4)0.1103 (15)
O90.3764 (4)−0.5671 (3)0.8564 (3)0.0660 (13)
N10.5057 (4)0.0648 (3)0.8650 (3)0.0397 (11)
N20.5346 (4)−0.0289 (3)0.8773 (3)0.0398 (11)
N30.1124 (4)−0.0205 (3)0.7800 (3)0.0454 (12)
N40.2318 (4)0.2816 (3)0.7769 (3)0.0413 (11)
N50.2329 (4)0.3526 (3)0.6989 (3)0.0430 (12)
N60.5554 (4)0.1015 (3)0.5544 (3)0.0449 (12)
N7−0.0136 (6)−0.3582 (5)0.6870 (6)0.101 (2)
C10.5628 (5)0.2210 (4)0.8598 (4)0.0422 (14)
C20.6393 (5)0.2825 (4)0.8750 (4)0.0448 (15)
C30.7400 (5)0.2409 (4)0.9114 (4)0.0473 (15)
C40.7679 (5)0.1382 (4)0.9319 (4)0.0451 (14)
C50.6932 (5)0.0759 (4)0.9196 (4)0.0428 (14)
C60.5913 (5)0.1184 (4)0.8821 (4)0.0436 (14)
C70.3479 (5)−0.0602 (4)0.8343 (4)0.0392 (13)
C80.4605 (5)−0.0899 (4)0.8615 (4)0.0386 (13)
C90.5082 (5)−0.1914 (4)0.8752 (4)0.0402 (14)
C100.6220 (5)−0.2231 (4)0.8991 (4)0.0486 (15)
C110.6632 (6)−0.3209 (4)0.9089 (5)0.0593 (18)
C120.5984 (6)−0.3902 (4)0.8959 (5)0.0592 (18)
C130.4881 (6)−0.3611 (4)0.8720 (5)0.0544 (17)
C140.4414 (5)−0.2609 (4)0.8604 (4)0.0454 (15)
C150.3295 (5)−0.2294 (4)0.8330 (4)0.0450 (14)
C160.2828 (5)−0.1335 (4)0.8186 (4)0.0398 (13)
C170.1688 (5)−0.1119 (4)0.7845 (4)0.0424 (14)
C180.0062 (5)0.0210 (4)0.7457 (4)0.0452 (15)
C19−0.0736 (6)−0.0332 (5)0.7267 (4)0.0573 (17)
C20−0.1751 (6)0.0128 (5)0.6939 (4)0.0605 (18)
C21−0.1973 (6)0.1163 (5)0.6778 (4)0.0573 (18)
C22−0.1186 (5)0.1703 (5)0.6963 (4)0.0530 (17)
C23−0.0168 (5)0.1234 (5)0.7317 (4)0.0502 (16)
C240.1631 (5)0.2232 (4)0.9440 (4)0.0415 (14)
C250.0855 (5)0.2317 (4)1.0296 (4)0.0434 (14)
C26−0.0026 (5)0.3072 (4)1.0291 (4)0.0471 (15)
C27−0.0182 (5)0.3765 (4)0.9418 (4)0.0444 (14)
C280.0548 (5)0.3704 (4)0.8564 (4)0.0468 (15)
C290.1455 (5)0.2944 (4)0.8573 (4)0.0421 (14)
C300.4013 (5)0.2678 (4)0.6089 (4)0.0452 (15)
C310.3192 (5)0.3486 (4)0.6182 (4)0.0456 (15)
C320.3197 (5)0.4395 (4)0.5399 (4)0.0437 (14)
C330.2371 (5)0.5215 (4)0.5450 (4)0.0484 (15)
C340.2456 (6)0.6069 (4)0.4700 (4)0.0541 (17)
C350.3359 (6)0.6164 (4)0.3864 (4)0.0548 (17)
C360.4139 (6)0.5365 (4)0.3802 (4)0.0510 (16)
C370.4090 (5)0.4471 (4)0.4548 (4)0.0442 (14)
C380.4904 (5)0.3653 (4)0.4471 (4)0.0476 (15)
C390.4874 (5)0.2775 (4)0.5180 (4)0.0452 (15)
C400.5767 (6)0.1949 (5)0.4971 (4)0.0505 (16)
C410.6173 (5)0.0108 (4)0.5470 (4)0.0435 (14)
C420.7141 (5)0.0022 (5)0.4734 (4)0.0564 (17)
C430.7690 (6)−0.0910 (5)0.4735 (5)0.068 (2)
C440.7300 (6)−0.1763 (5)0.5459 (4)0.0577 (17)
C450.6337 (5)−0.1664 (5)0.6187 (4)0.0523 (16)
C460.5787 (5)−0.0738 (4)0.6184 (4)0.0462 (15)
C47−0.0920 (8)−0.4004 (6)0.6882 (6)0.081 (2)
C48−0.1940 (8)−0.4558 (7)0.6902 (6)0.103 (3)
H20.62240.35090.86050.054*
H30.78990.28160.92240.057*
H3N0.14560.01760.80080.054*
H50.70970.00740.93560.051*
H6N0.49580.09700.60240.054*
H100.6683−0.17840.90820.058*
H110.7379−0.34100.92480.071*
H120.6288−0.45570.90330.071*
H130.4439−0.40720.86340.066*
H150.2858−0.27580.82420.053*
H19−0.0590−0.10180.73630.068*
H20−0.2287−0.02450.68250.073*
H21−0.26490.14780.65480.069*
H22−0.13290.23880.68520.064*
H230.03500.16020.74570.060*
H250.09400.18571.08720.052*
H26−0.05210.31281.08630.057*
H280.04410.41590.79910.056*
H330.17650.51770.59950.058*
H340.19010.66000.47470.065*
H350.34210.67540.33690.066*
H360.47260.54120.32460.061*
H380.54890.37130.39110.057*
H420.74180.05830.42460.068*
H430.8335−0.09670.42390.082*
H440.7678−0.23840.54530.069*
H450.6060−0.22220.66790.063*
H460.5138−0.06840.66770.055*
H48A−0.1883−0.46350.62790.123*
H48B−0.2682−0.41980.70810.123*
H48C−0.1919−0.52020.73580.123*
U11U22U33U12U13U23
Fe10.0437 (5)0.0388 (5)0.0420 (5)0.0055 (3)−0.0130 (4)−0.0097 (3)
Cl10.0459 (8)0.0517 (9)0.0505 (9)0.0036 (7)−0.0165 (7)−0.0122 (7)
Cl20.0557 (10)0.0513 (10)0.0614 (11)0.0143 (7)−0.0124 (8)−0.0188 (8)
Na10.0676 (17)0.0632 (18)0.0588 (17)−0.0126 (14)0.0001 (13)−0.0248 (13)
O10.044 (2)0.040 (2)0.046 (2)0.0014 (18)−0.0145 (19)−0.0111 (18)
O20.049 (2)0.041 (2)0.047 (2)0.0134 (19)−0.0170 (19)−0.0129 (19)
O30.049 (2)0.040 (2)0.041 (2)0.0019 (18)−0.0088 (19)−0.0106 (18)
O40.044 (2)0.040 (2)0.049 (2)0.0070 (18)−0.0202 (19)−0.0115 (18)
O50.057 (2)0.054 (2)0.052 (2)0.006 (2)−0.002 (2)−0.016 (2)
O60.049 (2)0.053 (2)0.051 (2)−0.001 (2)−0.013 (2)−0.014 (2)
O70.114 (3)0.112 (3)0.107 (3)−0.011 (2)−0.047 (3)−0.014 (2)
O80.114 (3)0.112 (3)0.107 (3)−0.011 (2)−0.047 (3)−0.014 (2)
O90.067 (3)0.050 (2)0.084 (3)−0.001 (2)−0.019 (2)−0.022 (2)
N10.038 (2)0.040 (2)0.039 (2)0.001 (2)−0.007 (2)−0.011 (2)
N20.050 (3)0.033 (2)0.034 (2)0.005 (2)−0.011 (2)−0.009 (2)
N30.046 (2)0.046 (3)0.047 (3)0.003 (2)−0.015 (2)−0.016 (2)
N40.042 (2)0.040 (2)0.041 (2)0.001 (2)−0.009 (2)−0.012 (2)
N50.049 (3)0.040 (2)0.033 (2)0.003 (2)−0.010 (2)−0.002 (2)
N60.050 (3)0.039 (3)0.041 (2)0.003 (2)−0.008 (2)−0.009 (2)
N70.073 (4)0.088 (5)0.164 (8)0.003 (4)−0.057 (5)−0.047 (5)
C10.042 (3)0.047 (3)0.037 (3)0.003 (2)−0.010 (2)−0.012 (2)
C20.048 (3)0.037 (3)0.051 (3)0.010 (2)−0.022 (3)−0.010 (2)
C30.046 (3)0.044 (3)0.052 (4)−0.002 (2)−0.005 (3)−0.017 (2)
C40.045 (3)0.046 (3)0.047 (3)−0.001 (2)−0.014 (2)−0.014 (2)
C50.048 (3)0.041 (3)0.042 (3)0.007 (2)−0.018 (2)−0.013 (2)
C60.050 (3)0.038 (3)0.042 (3)0.001 (2)−0.016 (2)−0.008 (2)
C70.046 (3)0.034 (3)0.041 (3)0.005 (2)−0.011 (2)−0.018 (2)
C80.038 (3)0.038 (3)0.039 (3)0.010 (2)−0.016 (2)−0.009 (2)
C90.044 (3)0.038 (3)0.039 (3)0.007 (2)−0.010 (2)−0.013 (2)
C100.057 (3)0.040 (3)0.052 (3)0.003 (3)−0.020 (3)−0.012 (2)
C110.052 (4)0.050 (4)0.080 (5)0.016 (3)−0.029 (3)−0.021 (3)
C120.060 (4)0.038 (3)0.089 (5)0.017 (3)−0.034 (3)−0.024 (3)
C130.059 (4)0.039 (3)0.072 (4)−0.001 (3)−0.019 (3)−0.022 (3)
C140.050 (3)0.038 (3)0.048 (3)0.003 (2)−0.010 (2)−0.015 (2)
C150.043 (3)0.044 (3)0.049 (3)−0.001 (2)−0.010 (2)−0.015 (2)
C160.040 (3)0.043 (3)0.039 (3)0.003 (2)−0.017 (2)−0.010 (2)
C170.047 (3)0.037 (3)0.041 (3)0.005 (2)−0.011 (2)−0.010 (2)
C180.042 (3)0.054 (4)0.040 (3)0.005 (3)−0.013 (2)−0.014 (2)
C190.055 (4)0.060 (4)0.059 (4)0.014 (3)−0.024 (3)−0.018 (3)
C200.058 (4)0.070 (5)0.055 (4)0.003 (3)−0.019 (3)−0.017 (3)
C210.055 (4)0.061 (4)0.060 (4)0.015 (3)−0.026 (3)−0.019 (3)
C220.049 (3)0.059 (4)0.048 (4)0.019 (3)−0.019 (3)−0.013 (3)
C230.049 (3)0.057 (4)0.043 (3)0.005 (3)−0.007 (2)−0.016 (3)
C240.047 (3)0.037 (3)0.040 (3)−0.001 (2)−0.011 (2)−0.009 (2)
C250.048 (3)0.039 (3)0.042 (3)0.002 (2)−0.015 (2)−0.006 (2)
C260.046 (3)0.049 (3)0.048 (3)0.003 (3)−0.012 (2)−0.017 (3)
C270.046 (3)0.038 (3)0.051 (3)0.015 (2)−0.016 (2)−0.016 (2)
C280.053 (3)0.039 (3)0.047 (3)0.005 (2)−0.013 (3)−0.012 (2)
C290.037 (3)0.041 (3)0.048 (3)0.004 (2)−0.014 (2)−0.011 (2)
C300.053 (3)0.041 (3)0.037 (3)−0.003 (2)−0.012 (2)−0.003 (2)
C310.058 (4)0.034 (3)0.046 (3)0.008 (2)−0.018 (3)−0.013 (2)
C320.050 (3)0.042 (3)0.037 (3)0.002 (2)−0.012 (2)−0.007 (2)
C330.055 (3)0.045 (3)0.046 (3)0.006 (3)−0.013 (3)−0.014 (2)
C340.061 (4)0.040 (3)0.058 (4)0.011 (3)−0.019 (3)−0.009 (3)
C350.073 (4)0.045 (4)0.041 (3)−0.003 (3)−0.009 (3)−0.006 (2)
C360.062 (4)0.047 (4)0.043 (3)−0.003 (3)−0.011 (3)−0.011 (2)
C370.051 (3)0.043 (3)0.037 (3)0.006 (2)−0.013 (2)−0.010 (2)
C380.057 (4)0.045 (3)0.039 (3)−0.004 (3)−0.008 (3)−0.010 (2)
C390.043 (3)0.047 (3)0.047 (3)0.006 (2)−0.014 (2)−0.015 (2)
C400.056 (4)0.054 (4)0.044 (3)0.004 (3)−0.015 (3)−0.015 (3)
C410.050 (3)0.041 (3)0.043 (3)0.002 (2)−0.015 (2)−0.014 (2)
C420.060 (4)0.046 (4)0.051 (4)0.000 (3)0.000 (3)−0.006 (3)
C430.070 (4)0.052 (4)0.064 (4)−0.001 (3)0.010 (3)−0.008 (3)
C440.064 (4)0.050 (4)0.052 (4)0.013 (3)−0.006 (3)−0.015 (3)
C450.054 (4)0.048 (4)0.051 (4)−0.004 (3)−0.011 (3)−0.010 (3)
C460.047 (3)0.047 (3)0.041 (3)0.003 (2)−0.010 (2)−0.009 (2)
C470.069 (5)0.086 (6)0.089 (6)0.012 (4)−0.027 (4)−0.024 (4)
C480.097 (7)0.106 (7)0.105 (7)−0.010 (5)−0.039 (6)−0.015 (5)
Fe1—O11.970 (4)C15—C161.366 (8)
Fe1—O21.944 (3)C15—H150.930
Fe1—O31.986 (3)C16—C171.477 (8)
Fe1—O41.976 (4)C18—C191.387 (11)
Fe1—N12.127 (4)C18—C231.397 (9)
Fe1—N42.161 (4)C19—C201.381 (10)
Cl1—C41.729 (6)C19—H190.930
Cl2—C271.743 (6)C20—C211.408 (10)
Na1—O5i2.222 (4)C20—H200.930
Na1—O62.238 (5)C21—C221.373 (11)
Na1—O72.508 (7)C21—H210.930
Na1—O82.329 (6)C22—C231.404 (9)
Na1—N72.381 (9)C22—H220.930
O1—C71.304 (6)C23—H230.930
O2—C241.320 (6)C24—C251.407 (8)
O3—C301.312 (6)C24—C291.424 (7)
O4—C11.344 (7)C25—C261.375 (8)
O5—C401.253 (7)C25—H250.930
O6—C171.258 (8)C26—C271.413 (8)
N1—N21.290 (6)C26—H260.930
N1—C61.420 (9)C27—C281.375 (8)
N2—C81.384 (8)C28—C291.398 (8)
N3—C171.361 (7)C28—H280.930
N3—C181.424 (8)C30—C311.406 (8)
N3—H3N0.860C30—C391.460 (8)
N4—N51.289 (5)C31—C321.455 (7)
N4—C291.409 (7)C32—C331.412 (8)
N5—C311.380 (7)C32—C371.418 (7)
N6—C401.353 (7)C33—C341.373 (7)
N6—C411.407 (7)C33—H330.930
N6—H6N0.860C34—C351.406 (8)
N7—C471.130 (13)C34—H340.930
C1—C21.404 (10)C35—C361.363 (9)
C1—C61.400 (8)C35—H350.930
C2—C31.382 (8)C36—C371.408 (7)
C2—H20.930C36—H360.930
C3—C41.401 (8)C37—C381.408 (8)
C3—H30.930C38—C391.366 (7)
C4—C51.376 (10)C38—H380.930
C5—C61.404 (8)C39—C401.511 (9)
C5—H50.930C41—C421.390 (8)
C7—C81.420 (8)C41—C461.379 (7)
C7—C161.449 (9)C42—C431.387 (9)
C8—C91.441 (7)C42—H420.930
C9—C101.417 (8)C43—C441.393 (8)
C9—C141.410 (10)C43—H430.930
C10—C111.379 (9)C44—C451.382 (8)
C10—H100.930C44—H440.930
C11—C121.380 (11)C45—C461.379 (9)
C11—H110.930C45—H450.930
C12—C131.374 (10)C46—H460.930
C12—H120.930C47—C481.472 (14)
C13—C141.424 (8)C48—H48A0.960
C13—H130.930C48—H48B0.960
C14—C151.417 (9)C48—H48C0.960
O4···O9ii2.710 (6)O9···O4iii2.710 (6)
O8···O92.730 (7)O9···O82.730 (7)
O1—Fe1—O290.26 (17)N3—C17—C16117.7 (6)
O1—Fe1—O385.60 (17)N3—C18—C19124.4 (5)
O1—Fe1—O4160.14 (15)N3—C18—C23116.0 (6)
O1—Fe1—N181.72 (18)C19—C18—C23119.5 (5)
O1—Fe1—N4111.90 (19)C18—C19—C20120.8 (6)
O2—Fe1—O3155.71 (17)C18—C19—H19119.9
O2—Fe1—O496.86 (18)C20—C19—H19119.3
O2—Fe1—N1100.35 (16)C19—C20—C21119.9 (7)
O2—Fe1—N479.14 (16)C19—C20—H20120.1
O3—Fe1—O495.02 (17)C21—C20—H20120.1
O3—Fe1—N1102.70 (16)C20—C21—C22119.5 (6)
O3—Fe1—N480.26 (17)C20—C21—H21120.2
O4—Fe1—N178.78 (18)C22—C21—H21120.2
O4—Fe1—N487.69 (18)C21—C22—C23120.7 (6)
N1—Fe1—N4166.3 (2)C21—C22—H22119.6
O5i—Na1—O697.7 (2)C23—C22—H22119.6
O5i—Na1—O788.35 (19)C18—C23—C22119.5 (7)
O5i—Na1—O8108.0 (2)C18—C23—H23120.3
O5i—Na1—N7149.5 (3)C22—C23—H23120.3
O6—Na1—O792.9 (2)O2—C24—C25123.0 (4)
O6—Na1—O8101.3 (2)O2—C24—C29119.4 (4)
O6—Na1—N7107.6 (2)C25—C24—C29117.6 (5)
O7—Na1—O8156.4 (2)C24—C25—C26120.8 (5)
O7—Na1—N773.9 (2)C24—C25—H25119.6
O8—Na1—N783.8 (2)C26—C25—H25119.6
Fe1—O1—C7136.1 (4)C25—C26—C27120.2 (5)
Fe1—O2—C24117.8 (3)C25—C26—H26119.9
Fe1—O3—C30130.3 (4)C27—C26—H26119.9
Fe1—O4—C1116.7 (3)Cl2—C27—C26118.6 (4)
Na1i—O5—C40159.8 (5)Cl2—C27—C28120.6 (4)
Na1—O6—C17145.0 (3)C26—C27—C28120.8 (5)
Fe1—N1—N2133.6 (4)C27—C28—C29118.8 (5)
Fe1—N1—C6112.0 (3)C27—C28—H28120.6
N2—N1—C6114.3 (4)C29—C28—H28120.6
N1—N2—C8120.5 (4)N4—C29—C24112.6 (4)
C17—N3—C18129.2 (6)N4—C29—C28125.6 (5)
C17—N3—H3N115.4C24—C29—C28121.7 (5)
C18—N3—H3N115.4O3—C30—C31123.1 (5)
Fe1—N4—N5132.3 (3)O3—C30—C39118.8 (5)
Fe1—N4—C29110.8 (3)C31—C30—C39118.1 (4)
N5—N4—C29115.6 (4)N5—C31—C30125.8 (4)
N4—N5—C31119.2 (4)N5—C31—C32113.0 (5)
C40—N6—C41129.3 (4)C30—C31—C32121.1 (5)
C40—N6—H6N115.3C31—C32—C33123.2 (5)
C41—N6—H6N115.4C31—C32—C37118.6 (5)
Na1—N7—C47171.9 (8)C33—C32—C37118.2 (4)
O4—C1—C2122.4 (5)C32—C33—C34120.4 (5)
O4—C1—C6119.0 (6)C32—C33—H33119.8
C2—C1—C6118.5 (5)C34—C33—H33119.8
C1—C2—C3119.7 (5)C33—C34—C35121.9 (5)
C1—C2—H2120.1C33—C34—H34119.0
C3—C2—H2120.1C35—C34—H34119.0
C2—C3—C4120.8 (6)C34—C35—C36117.9 (5)
C2—C3—H3119.6C34—C35—H35121.1
C4—C3—H3119.6C36—C35—H35121.1
Cl1—C4—C3119.3 (5)C35—C36—C37122.6 (5)
Cl1—C4—C5120.0 (4)C35—C36—H36118.7
C3—C4—C5120.7 (5)C37—C36—H36118.7
C4—C5—C6118.3 (5)C32—C37—C36119.0 (5)
C4—C5—H5120.8C32—C37—C38119.2 (4)
C6—C5—H5120.8C36—C37—C38121.8 (5)
N1—C6—C1112.8 (5)C37—C38—C39123.0 (5)
N1—C6—C5125.3 (5)C37—C38—H38118.5
C1—C6—C5121.9 (6)C39—C38—H38118.5
O1—C7—C8121.8 (6)C30—C39—C38119.8 (5)
O1—C7—C16119.5 (5)C30—C39—C40123.5 (4)
C8—C7—C16118.7 (5)C38—C39—C40116.7 (5)
N2—C8—C7125.9 (5)O5—C40—N6123.1 (5)
N2—C8—C9113.4 (5)O5—C40—C39119.5 (5)
C7—C8—C9120.8 (6)N6—C40—C39117.3 (4)
C8—C9—C10122.4 (6)N6—C41—C42124.1 (4)
C8—C9—C14118.9 (5)N6—C41—C46117.0 (4)
C10—C9—C14118.7 (5)C42—C41—C46118.9 (5)
C9—C10—C11119.3 (6)C41—C42—C43119.3 (5)
C9—C10—H10120.4C41—C42—H42120.3
C11—C10—H10120.4C43—C42—H42120.3
C10—C11—C12122.8 (6)C42—C43—C44121.6 (6)
C10—C11—H11118.6C42—C43—H43119.2
C12—C11—H11118.6C44—C43—H43119.2
C11—C12—C13119.0 (6)C43—C44—C45118.3 (6)
C11—C12—H12120.5C43—C44—H44120.8
C13—C12—H12120.5C45—C44—H44120.8
C12—C13—C14120.7 (7)C44—C45—C46120.1 (5)
C12—C13—H13119.5C44—C45—H45119.9
C14—C13—H13119.8C46—C45—H45120.0
C9—C14—C13119.6 (5)C41—C46—C45121.8 (5)
C9—C14—C15119.3 (5)C41—C46—H46119.1
C13—C14—C15121.1 (6)C45—C46—H46119.1
C14—C15—C16123.0 (6)N7—C47—C48179.8 (9)
C14—C15—H15118.7C47—C48—H48A109.5
C16—C15—H15118.3C47—C48—H48B109.5
C7—C16—C15119.3 (5)C47—C48—H48C109.5
C7—C16—C17124.6 (5)H48A—C48—H48B109.5
C15—C16—C17116.1 (6)H48A—C48—H48C109.5
O6—C17—N3121.1 (5)H48B—C48—H48C109.5
O6—C17—C16121.2 (5)
O1—Fe1—O2—C24−116.4 (4)C3—C4—C5—C62.7 (8)
O2—Fe1—O1—C7−107.1 (5)C4—C5—C6—N1179.9 (4)
O1—Fe1—O3—C30145.6 (5)C4—C5—C6—C1−1.8 (8)
O3—Fe1—O1—C796.8 (5)O1—C7—C8—N20.3 (6)
O1—Fe1—O4—C1−18.3 (7)O1—C7—C8—C9−179.5 (4)
O4—Fe1—O1—C74.2 (8)O1—C7—C16—C15−179.8 (3)
O1—Fe1—N1—N24.6 (4)O1—C7—C16—C172.3 (8)
O1—Fe1—N1—C6−178.2 (3)C8—C7—C16—C151.8 (7)
N1—Fe1—O1—C7−6.7 (5)C8—C7—C16—C17−176.1 (5)
O1—Fe1—N4—N5−105.7 (6)C16—C7—C8—N2178.7 (4)
O1—Fe1—N4—C2988.5 (4)C16—C7—C8—C9−1.2 (7)
N4—Fe1—O1—C7174.5 (4)N2—C8—C9—C10−2.1 (7)
O2—Fe1—O3—C3064.8 (7)N2—C8—C9—C14−179.5 (4)
O3—Fe1—O2—C24−36.6 (7)C7—C8—C9—C10177.8 (5)
O2—Fe1—O4—C191.9 (3)C7—C8—C9—C140.4 (6)
O4—Fe1—O2—C2482.2 (4)C8—C9—C10—C11−178.4 (5)
O2—Fe1—N1—N293.4 (4)C8—C9—C14—C13178.9 (5)
O2—Fe1—N1—C6−89.4 (3)C8—C9—C14—C15−0.2 (6)
N1—Fe1—O2—C24162.0 (4)C10—C9—C14—C131.4 (8)
O2—Fe1—N4—N5168.5 (6)C10—C9—C14—C15−177.7 (5)
O2—Fe1—N4—C292.6 (4)C14—C9—C10—C11−1.0 (8)
N4—Fe1—O2—C24−4.1 (4)C9—C10—C11—C120.2 (7)
O3—Fe1—O4—C1−109.3 (3)C10—C11—C12—C130.2 (7)
O4—Fe1—O3—C30−54.3 (5)C11—C12—C13—C140.2 (7)
O3—Fe1—N1—N2−78.9 (4)C12—C13—C14—C9−1.0 (9)
O3—Fe1—N1—C698.3 (3)C12—C13—C14—C15178.1 (6)
N1—Fe1—O3—C30−133.9 (5)C9—C14—C15—C160.9 (8)
O3—Fe1—N4—N5−24.5 (6)C13—C14—C15—C16−178.2 (5)
O3—Fe1—N4—C29169.7 (4)C14—C15—C16—C7−1.7 (8)
N4—Fe1—O3—C3032.5 (5)C14—C15—C16—C17176.4 (5)
O4—Fe1—N1—N2−171.6 (4)C7—C16—C17—O6169.3 (5)
O4—Fe1—N1—C65.6 (3)C7—C16—C17—N3−9.5 (7)
N1—Fe1—O4—C1−7.3 (3)C15—C16—C17—O6−8.7 (7)
O4—Fe1—N4—N571.0 (6)C15—C16—C17—N3172.5 (4)
O4—Fe1—N4—C29−94.8 (4)N3—C18—C19—C20179.7 (5)
N4—Fe1—O4—C1170.7 (3)N3—C18—C23—C22178.8 (5)
N1—Fe1—N4—N579.3 (10)C19—C18—C23—C22−1.7 (8)
N1—Fe1—N4—C29−86.5 (7)C23—C18—C19—C200.2 (7)
N4—Fe1—N1—N2179.9 (5)C18—C19—C20—C211.1 (9)
N4—Fe1—N1—C6−2.9 (9)C19—C20—C21—C22−1.0 (9)
O5i—Na1—O6—C17−15.9 (6)C20—C21—C22—C23−0.4 (8)
O6—Na1—O5i—C40i−161.4 (11)C21—C22—C23—C181.8 (8)
O7—Na1—O5i—C40i−68.7 (12)O2—C24—C25—C26178.6 (6)
O8—Na1—O5i—C40i94.0 (12)O2—C24—C29—N4−2.4 (9)
N7—Na1—O5i—C40i−15.1 (14)O2—C24—C29—C28−179.6 (6)
O7—Na1—O6—C17−104.7 (6)C25—C24—C29—N4177.1 (6)
O8—Na1—O6—C1794.3 (6)C25—C24—C29—C28−0.0 (9)
N7—Na1—O6—C17−178.7 (6)C29—C24—C25—C26−1.0 (10)
Fe1—O1—C7—C85.8 (8)C24—C25—C26—C271.3 (10)
Fe1—O1—C7—C16−172.5 (3)C25—C26—C27—Cl2179.2 (5)
Fe1—O2—C24—C25−174.4 (5)C25—C26—C27—C28−0.7 (10)
Fe1—O2—C24—C295.1 (8)Cl2—C27—C28—C29179.9 (4)
Fe1—O3—C30—C31−29.3 (10)C26—C27—C28—C29−0.3 (8)
Fe1—O3—C30—C39151.0 (5)C27—C28—C29—N4−176.1 (6)
Fe1—O4—C1—C2−173.9 (4)C27—C28—C29—C240.6 (10)
Fe1—O4—C1—C68.1 (6)O3—C30—C31—N50.9 (12)
Na1i—O5—C40—N6−117.5 (11)O3—C30—C31—C32−179.8 (6)
Na1i—O5—C40—C3965.3 (14)O3—C30—C39—C38−176.9 (6)
Na1—O6—C17—N3128.1 (5)O3—C30—C39—C402.4 (10)
Na1—O6—C17—C16−50.6 (8)C31—C30—C39—C383.4 (10)
Fe1—N1—N2—C8−1.7 (7)C31—C30—C39—C40−177.3 (7)
Fe1—N1—C6—C1−3.2 (5)C39—C30—C31—N5−179.4 (6)
Fe1—N1—C6—C5175.3 (4)C39—C30—C31—C32−0.0 (9)
N2—N1—C6—C1174.6 (4)N5—C31—C32—C33−2.4 (10)
N2—N1—C6—C5−7.0 (7)N5—C31—C32—C37176.3 (6)
C6—N1—N2—C8−178.9 (4)C30—C31—C32—C33178.2 (7)
N1—N2—C8—C7−2.0 (7)C30—C31—C32—C37−3.1 (10)
N1—N2—C8—C9177.9 (4)C31—C32—C33—C34177.1 (7)
C17—N3—C18—C1913.2 (8)C31—C32—C37—C36−177.0 (6)
C17—N3—C18—C23−167.3 (5)C31—C32—C37—C382.9 (10)
C18—N3—C17—O6−2.3 (8)C33—C32—C37—C361.7 (10)
C18—N3—C17—C16176.5 (4)C33—C32—C37—C38−178.3 (7)
Fe1—N4—N5—C3110.9 (9)C37—C32—C33—C34−1.6 (11)
Fe1—N4—C29—C24−0.9 (7)C32—C33—C34—C35−0.3 (9)
Fe1—N4—C29—C28176.0 (5)C33—C34—C35—C361.9 (12)
N5—N4—C29—C24−169.4 (5)C34—C35—C36—C37−1.7 (12)
N5—N4—C29—C287.6 (10)C35—C36—C37—C32−0.0 (10)
C29—N4—N5—C31176.2 (6)C35—C36—C37—C38180.0 (7)
N4—N5—C31—C307.2 (11)C32—C37—C38—C390.4 (11)
N4—N5—C31—C32−172.2 (6)C36—C37—C38—C39−179.6 (7)
C40—N6—C41—C42−2.0 (12)C37—C38—C39—C30−3.7 (11)
C40—N6—C41—C46177.4 (7)C37—C38—C39—C40177.0 (7)
C41—N6—C40—O5−2.7 (12)C30—C39—C40—O5−165.1 (7)
C41—N6—C40—C39174.5 (6)C30—C39—C40—N617.5 (11)
O4—C1—C2—C3−178.3 (5)C38—C39—C40—O514.1 (11)
O4—C1—C6—N1−2.8 (7)C38—C39—C40—N6−163.2 (7)
O4—C1—C6—C5178.7 (5)N6—C41—C42—C43179.6 (7)
C2—C1—C6—N1179.0 (4)N6—C41—C46—C45−179.3 (6)
C2—C1—C6—C50.5 (8)C42—C41—C46—C450.1 (8)
C6—C1—C2—C3−0.2 (6)C46—C41—C42—C430.2 (8)
C1—C2—C3—C41.1 (8)C41—C42—C43—C44−0.4 (10)
C2—C3—C4—Cl1177.8 (4)C42—C43—C44—C450.3 (9)
C2—C3—C4—C5−2.4 (8)C43—C44—C45—C460.1 (10)
Cl1—C4—C5—C6−177.5 (4)C44—C45—C46—C41−0.3 (9)
D—H···AD—HH···AD···AD—H···A
N3—H3N···O10.861.942.644 (7)138
N6—H6N···O30.861.972.664 (6)138
O8—H···O9..2.730 (7).
O9—H···O4iii..2.710 (6).
Fe1—O11.970 (4)
Fe1—O21.944 (3)
Fe1—O31.986 (3)
Fe1—O41.976 (4)
Fe1—N12.127 (4)
Fe1—N42.161 (4)
Na1—O5i2.222 (4)
Na1—O62.238 (5)
Na1—O72.508 (7)
Na1—O82.329 (6)
Na1—N72.381 (9)
O1—Fe1—O290.26 (17)
O1—Fe1—O385.60 (17)
O1—Fe1—O4160.14 (15)
O1—Fe1—N181.72 (18)
O1—Fe1—N4111.90 (19)
O2—Fe1—O3155.71 (17)
O2—Fe1—O496.86 (18)
O2—Fe1—N1100.35 (16)
O2—Fe1—N479.14 (16)
O3—Fe1—O495.02 (17)
O3—Fe1—N1102.70 (16)
O3—Fe1—N480.26 (17)
O4—Fe1—N178.78 (18)
O4—Fe1—N487.69 (18)
N1—Fe1—N4166.3 (2)
O5i—Na1—O697.7 (2)
O5i—Na1—O788.35 (19)
O5i—Na1—O8108.0 (2)
O5i—Na1—N7149.5 (3)
O6—Na1—O792.9 (2)
O6—Na1—O8101.3 (2)
O6—Na1—N7107.6 (2)
O7—Na1—O8156.4 (2)
O7—Na1—N773.9 (2)
O8—Na1—N783.8 (2)

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

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N3—H3N⋯O10.861.942.644 (7)138
N6—H6N⋯O30.861.972.664 (6)138
O8—H⋯O9––2.730 (7)–
O9—H⋯O4iii––2.710 (6)–

Symmetry code: (iii) .

  1 in total

1.  SHELXL: high-resolution refinement.

Authors:  G M Sheldrick; T R Schneider
Journal:  Methods Enzymol       Date:  1997       Impact factor: 1.600
  1 in total
  1 in total

1.  (2,6-Bis{5-amino-3-tert-butyl-4-[(3-methyl-1,2,4-thia-diazol-5-yl)diazen-yl]-1H-pyrazol-1-yl}-4-oxo-1,4-dihydro-1,3,5-triazin-1-ido)methanol(phenol)sodium phenol tetra-solvate.

Authors:  Hiroki Shibata; Jin Mizuguchi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-27
  1 in total

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