In the title mononuclear complex, [Fe(C6H5N3O)6](ClO4)3·2C2H3N, the FeIII ion shows a close-to-ideal octahedral geometry coordinated by six O atoms from six 1-hydroxybenzotriazole ligands. The ligand benzotriazole exists as a zwitterion.
Supporting information
CCDC reference: 283767
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.114
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 1
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT390_ALERT_3_C Deviating Methyl C8 X-C-H Bond Angle ...... 117.00 Deg.
PLAT390_ALERT_3_C Deviating Methyl C8 X-C-H Bond Angle ...... 117.00 Deg.
PLAT390_ALERT_3_C Deviating Methyl C8 X-C-H Bond Angle ...... 117.00 Deg.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 36.00 A 3
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1
O1 -FE1 -O1 -N1 -140.19 0.17 7.555 1.555 1.555 1.555
Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 29.00
From the CIF: _reflns_number_total 2319
From the CIF: _diffrn_reflns_limit_ max hkl 0. 13. 38.
From the CIF: _diffrn_reflns_limit_ min hkl -11. 0. 0.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 13. 13. 38.
Calculated minimum hkl -13. -13. -38.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
4 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
3 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Hexakis(1-oxido-1
H-benzotriazol-3-ium-
κO)iron(III)
tris(perchlorate) acetonitrile disolvate
top
Crystal data top
[Fe(C6H5N3O)6](ClO4)3·2C2H3N | Dx = 1.617 Mg m−3 |
Mr = 1247.09 | Mo Kα radiation, λ = 0.71073 Å |
Hexagonal, P63/m | Cell parameters from 164 reflections |
a = 10.2197 (4) Å | θ = 2.5–26° |
c = 28.3118 (14) Å | µ = 0.55 mm−1 |
V = 2560.79 (19) Å3 | T = 293 K |
Z = 2 | Hexagonal block, colorless |
F(000) = 1274 | 0.32 × 0.30 × 0.18 mm |
Data collection top
Bruker APEX area-dector diffractometer | 2319 independent reflections |
Radiation source: fine-focus sealed tube | 1935 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.000 |
φ and ω scans | θmax = 29.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→9 |
Tmin = 0.845, Tmax = 0.908 | k = −12→13 |
2319 measured reflections | l = −34→38 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0334P)2 + 5.4288P] where P = (Fo2 + 2Fc2)/3 |
2319 reflections | (Δ/σ)max < 0.001 |
137 parameters | Δρmax = 1.18 e Å−3 |
0 restraints | Δρmin = −0.75 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Fe1 | 0.0000 | 0.0000 | 0.0000 | 0.00954 (16) | |
Cl1 | 0.30616 (8) | 0.27232 (9) | 0.2500 | 0.01748 (17) | |
O1 | 0.14007 (16) | 0.18082 (16) | 0.03900 (5) | 0.0128 (3) | |
O2 | 0.1535 (3) | 0.2543 (4) | 0.2500 | 0.0312 (6) | |
O3 | 0.4140 (3) | 0.4313 (3) | 0.2500 | 0.0313 (6) | |
O4 | 0.3204 (2) | 0.2028 (2) | 0.20818 (6) | 0.0275 (4) | |
N1 | 0.09896 (19) | 0.22205 (19) | 0.07812 (6) | 0.0116 (3) | |
N2 | 0.1374 (2) | 0.1934 (2) | 0.11941 (6) | 0.0136 (3) | |
N3 | 0.0886 (2) | 0.2563 (2) | 0.15069 (6) | 0.0145 (3) | |
N4 | 0.3333 | 0.6667 | 0.08686 (19) | 0.0400 (10) | |
C1 | 0.0190 (2) | 0.3257 (2) | 0.12983 (7) | 0.0131 (4) | |
C2 | −0.0438 (2) | 0.4106 (2) | 0.14744 (8) | 0.0170 (4) | |
H2A | −0.0483 | 0.4262 | 0.1796 | 0.020* | |
C3 | −0.0982 (2) | 0.4692 (2) | 0.11410 (8) | 0.0188 (4) | |
H3A | −0.1386 | 0.5284 | 0.1240 | 0.023* | |
C4 | −0.0948 (2) | 0.4423 (3) | 0.06480 (8) | 0.0186 (4) | |
H4A | −0.1352 | 0.4826 | 0.0438 | 0.022* | |
C5 | −0.0339 (2) | 0.3592 (2) | 0.04734 (8) | 0.0154 (4) | |
H5A | −0.0322 | 0.3410 | 0.0152 | 0.019* | |
C6 | 0.0256 (2) | 0.3035 (2) | 0.08134 (7) | 0.0121 (4) | |
C7 | 0.3333 | 0.6667 | 0.1271 (2) | 0.0298 (10) | |
C8 | 0.3333 | 0.6667 | 0.1786 (2) | 0.0327 (11) | |
H8A | 0.417 (4) | 0.751 (4) | 0.1938 (12) | 0.051 (11)* | |
H3B | 0.104 (3) | 0.245 (3) | 0.1823 (11) | 0.023 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.0108 (2) | 0.0108 (2) | 0.0069 (3) | 0.00542 (10) | 0.000 | 0.000 |
Cl1 | 0.0205 (4) | 0.0215 (4) | 0.0100 (3) | 0.0102 (3) | 0.000 | 0.000 |
O1 | 0.0136 (7) | 0.0156 (7) | 0.0094 (6) | 0.0074 (6) | 0.0010 (5) | −0.0032 (5) |
O2 | 0.0241 (13) | 0.0592 (19) | 0.0157 (11) | 0.0250 (13) | 0.000 | 0.000 |
O3 | 0.0364 (15) | 0.0242 (13) | 0.0221 (12) | 0.0069 (11) | 0.000 | 0.000 |
O4 | 0.0378 (10) | 0.0348 (10) | 0.0155 (8) | 0.0222 (9) | 0.0003 (7) | −0.0068 (7) |
N1 | 0.0119 (7) | 0.0119 (7) | 0.0101 (7) | 0.0053 (6) | −0.0011 (6) | −0.0012 (6) |
N2 | 0.0145 (8) | 0.0149 (8) | 0.0100 (8) | 0.0064 (7) | −0.0019 (6) | −0.0014 (6) |
N3 | 0.0164 (8) | 0.0152 (8) | 0.0108 (8) | 0.0070 (7) | −0.0005 (6) | −0.0015 (6) |
N4 | 0.0330 (14) | 0.0330 (14) | 0.054 (3) | 0.0165 (7) | 0.000 | 0.000 |
C1 | 0.0126 (9) | 0.0119 (9) | 0.0125 (9) | 0.0045 (7) | −0.0001 (7) | −0.0005 (7) |
C2 | 0.0166 (10) | 0.0145 (9) | 0.0164 (10) | 0.0052 (8) | 0.0029 (8) | −0.0037 (8) |
C3 | 0.0170 (10) | 0.0145 (9) | 0.0262 (11) | 0.0088 (8) | 0.0055 (8) | −0.0010 (8) |
C4 | 0.0172 (10) | 0.0176 (10) | 0.0227 (11) | 0.0100 (8) | 0.0023 (8) | 0.0052 (8) |
C5 | 0.0149 (9) | 0.0157 (9) | 0.0147 (9) | 0.0069 (8) | 0.0007 (7) | 0.0019 (8) |
C6 | 0.0116 (9) | 0.0098 (8) | 0.0137 (9) | 0.0044 (7) | 0.0015 (7) | −0.0013 (7) |
C7 | 0.0184 (12) | 0.0184 (12) | 0.053 (3) | 0.0092 (6) | 0.000 | 0.000 |
C8 | 0.0237 (13) | 0.0237 (13) | 0.051 (3) | 0.0119 (7) | 0.000 | 0.000 |
Geometric parameters (Å, º) top
Fe1—O1 | 2.0095 (14) | N3—H3B | 0.92 (3) |
Fe1—O1i | 2.0095 (14) | N4—C7 | 1.139 (7) |
Fe1—O1ii | 2.0095 (14) | C1—C6 | 1.398 (3) |
Fe1—O1iii | 2.0095 (14) | C1—C2 | 1.403 (3) |
Fe1—O1iv | 2.0095 (14) | C2—C3 | 1.375 (3) |
Fe1—O1v | 2.0095 (14) | C2—H2A | 0.9300 |
Cl1—O4 | 1.4251 (17) | C3—C4 | 1.427 (3) |
Cl1—O4vi | 1.4251 (17) | C3—H3A | 0.9300 |
Cl1—O3 | 1.436 (3) | C4—C5 | 1.372 (3) |
Cl1—O2 | 1.477 (3) | C4—H4A | 0.9300 |
O1—N1 | 1.326 (2) | C5—C6 | 1.402 (3) |
N1—N2 | 1.312 (2) | C5—H5A | 0.9300 |
N1—C6 | 1.374 (3) | C7—C8 | 1.459 (8) |
N2—N3 | 1.329 (2) | C8—H8A | 0.96 (3) |
N3—C1 | 1.365 (3) | | |
| | | |
O1i—Fe1—O1 | 180.00 (10) | N1—N2—N3 | 105.01 (16) |
O1i—Fe1—O1ii | 92.70 (6) | N2—N3—C1 | 112.47 (17) |
O1—Fe1—O1ii | 87.30 (6) | N2—N3—H3B | 117.3 (19) |
O1i—Fe1—O1iii | 87.30 (6) | C1—N3—H3B | 130.2 (19) |
O1—Fe1—O1iii | 92.70 (6) | N3—C1—C6 | 105.09 (18) |
O1ii—Fe1—O1iii | 180.00 (9) | N3—C1—C2 | 133.30 (19) |
O1i—Fe1—O1iv | 92.70 (6) | C6—C1—C2 | 121.54 (19) |
O1—Fe1—O1iv | 87.30 (6) | C3—C2—C1 | 115.77 (19) |
O1ii—Fe1—O1iv | 92.70 (6) | C3—C2—H2A | 122.1 |
O1iii—Fe1—O1iv | 87.30 (6) | C1—C2—H2A | 122.1 |
O1i—Fe1—O1v | 87.30 (6) | C2—C3—C4 | 122.2 (2) |
O1—Fe1—O1v | 92.70 (6) | C2—C3—H3A | 118.9 |
O1ii—Fe1—O1v | 87.30 (6) | C4—C3—H3A | 118.9 |
O1iii—Fe1—O1v | 92.70 (6) | C5—C4—C3 | 122.3 (2) |
O1iv—Fe1—O1v | 180.00 (11) | C5—C4—H4A | 118.9 |
O4—Cl1—O4vi | 112.35 (16) | C3—C4—H4A | 118.9 |
O4—Cl1—O3 | 110.60 (11) | C4—C5—C6 | 115.3 (2) |
O4vi—Cl1—O3 | 110.60 (11) | C4—C5—H5A | 122.4 |
O4—Cl1—O2 | 107.62 (11) | C6—C5—H5A | 122.4 |
O4vi—Cl1—O2 | 107.62 (11) | N1—C6—C1 | 104.40 (18) |
O3—Cl1—O2 | 107.84 (18) | N1—C6—C5 | 132.76 (19) |
N1—O1—Fe1 | 123.92 (12) | C1—C6—C5 | 122.85 (19) |
N2—N1—O1 | 119.70 (16) | N4—C7—C8 | 180.000 (1) |
N2—N1—C6 | 113.02 (17) | C7—C8—H8A | 117 (2) |
O1—N1—C6 | 127.14 (17) | | |
| | | |
O1i—Fe1—O1—N1 | −140.19 (17) | C1—C2—C3—C4 | 1.6 (3) |
O1ii—Fe1—O1—N1 | 93.28 (11) | C2—C3—C4—C5 | −1.5 (3) |
O1iii—Fe1—O1—N1 | −86.72 (11) | C3—C4—C5—C6 | −0.4 (3) |
O1iv—Fe1—O1—N1 | −173.89 (14) | N2—N1—C6—C1 | −0.1 (2) |
O1v—Fe1—O1—N1 | 6.11 (14) | O1—N1—C6—C1 | −175.78 (18) |
Fe1—O1—N1—N2 | 103.06 (18) | N2—N1—C6—C5 | 179.6 (2) |
Fe1—O1—N1—C6 | −81.6 (2) | O1—N1—C6—C5 | 3.9 (4) |
O1—N1—N2—N3 | 176.14 (16) | N3—C1—C6—N1 | 0.1 (2) |
C6—N1—N2—N3 | 0.2 (2) | C2—C1—C6—N1 | 177.53 (18) |
N1—N2—N3—C1 | −0.1 (2) | N3—C1—C6—C5 | −179.67 (19) |
N2—N3—C1—C6 | 0.0 (2) | C2—C1—C6—C5 | −2.2 (3) |
N2—N3—C1—C2 | −177.0 (2) | C4—C5—C6—N1 | −177.4 (2) |
N3—C1—C2—C3 | 176.8 (2) | C4—C5—C6—C1 | 2.3 (3) |
C6—C1—C2—C3 | 0.2 (3) | | |
Symmetry codes: (i) −x, −y, −z; (ii) x−y, x, −z; (iii) −x+y, −x, z; (iv) y, −x+y, −z; (v) −y, x−y, z; (vi) x, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O2 | 0.92 (3) | 1.97 (3) | 2.8912 (19) | 171 (3) |
N3—H3B···O4 | 0.92 (3) | 2.57 (3) | 3.139 (3) | 121 (2) |