Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048574/dn2091sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048574/dn2091Isup2.hkl |
CCDC reference: 629650
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.010 Å
- Disorder in main residue
- R factor = 0.054
- wR factor = 0.193
- Data-to-parameter ratio = 10.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C19
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT301_ALERT_3_C Main Residue Disorder ......................... 18.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 4 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: MSC/AFC Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Sheldrick, 2000); software used to prepare material for publication: SHELXTL-NT (Sheldrick, 2000) and PLATON (Spek, 2003).
[Cu(C5HF6O2)2(C12H10N2)2] | Z = 1 |
Mr = 842.10 | F(000) = 423 |
Triclinic, P1 | Dx = 1.530 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1513 (18) Å | Cell parameters from 25 reflections |
b = 10.009 (2) Å | θ = 7.5–17.5° |
c = 10.424 (2) Å | µ = 0.70 mm−1 |
α = 74.23 (3)° | T = 295 K |
β = 84.12 (3)° | Plate, green |
γ = 87.98 (3)° | 0.35 × 0.25 × 0.12 mm |
V = 913.9 (3) Å3 |
Rigaku AFC-6 diffractometer | 1907 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.039 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
ω/2θ scans | h = −10→10 |
Absorption correction: ψ scan (North et al., 1968) | k = −11→11 |
Tmin = 0.80, Tmax = 0.91 | l = −2→12 |
4174 measured reflections | 3 standard reflections every 150 reflections |
3219 independent reflections | intensity decay: 2% |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.193 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0916P)2 + 1.5666P] where P = (Fo2 + 2Fc2)/3 |
3219 reflections | (Δ/σ)max < 0.001 |
306 parameters | Δρmax = 0.41 e Å−3 |
224 restraints | Δρmin = −0.48 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cu1 | 0.5000 | 0.5000 | 0.5000 | 0.0491 (4) | |
C1 | 0.4159 (7) | 0.1611 (7) | 0.8436 (7) | 0.0622 (16) | |
H1 | 0.4645 | 0.1230 | 0.9195 | 0.075* | |
C2 | 0.4714 (7) | 0.2770 (7) | 0.7507 (7) | 0.0624 (17) | |
H2 | 0.5572 | 0.3153 | 0.7654 | 0.075* | |
N3 | 0.4069 (5) | 0.3377 (5) | 0.6388 (5) | 0.0489 (11) | |
C4 | 0.2822 (6) | 0.2815 (6) | 0.6220 (6) | 0.0557 (15) | |
H4 | 0.2349 | 0.3231 | 0.5461 | 0.067* | |
C5 | 0.2209 (6) | 0.1658 (7) | 0.7110 (6) | 0.0581 (15) | |
H5 | 0.1339 | 0.1310 | 0.6945 | 0.070* | |
C6 | 0.2882 (6) | 0.0993 (6) | 0.8268 (6) | 0.0546 (15) | |
C7 | 0.2331 (7) | −0.0268 (7) | 0.9256 (7) | 0.0623 (16) | |
H7 | 0.2848 | −0.0587 | 1.0005 | 0.075* | |
C8 | 0.1180 (7) | −0.1006 (7) | 0.9202 (7) | 0.0625 (16) | |
H8 | 0.0637 | −0.0688 | 0.8470 | 0.075* | |
C9 | 0.0692 (7) | −0.2280 (6) | 1.0202 (6) | 0.0566 (15) | |
N10 | 0.1496 (7) | −0.2752 (6) | 1.1242 (6) | 0.0770 (16) | |
C11 | 0.1039 (9) | −0.3920 (9) | 1.2154 (8) | 0.087 (2) | |
H11 | 0.1593 | −0.4277 | 1.2872 | 0.105* | |
C12 | −0.0197 (9) | −0.4618 (8) | 1.2086 (9) | 0.083 (2) | |
H12 | −0.0481 | −0.5419 | 1.2749 | 0.100* | |
C13 | −0.1010 (9) | −0.4111 (8) | 1.1018 (9) | 0.085 (2) | |
H13 | −0.1850 | −0.4568 | 1.0940 | 0.102* | |
C14 | −0.0565 (8) | −0.2929 (7) | 1.0079 (8) | 0.0715 (18) | |
H14 | −0.1109 | −0.2561 | 0.9355 | 0.086* | |
C15 | 0.5876 (7) | 0.7295 (6) | 0.7783 (6) | 0.093 (3) | |
C16 | 0.5004 (6) | 0.6852 (6) | 0.6789 (6) | 0.0584 (15) | |
C17 | 0.3788 (7) | 0.7634 (7) | 0.6331 (7) | 0.075 (2) | |
H17 | 0.3573 | 0.8433 | 0.6609 | 0.090* | |
C18 | 0.2870 (6) | 0.7301 (7) | 0.5482 (6) | 0.0588 (16) | |
C19 | 0.1604 (7) | 0.8327 (6) | 0.5042 (6) | 0.082 (2) | |
O20 | 0.5549 (4) | 0.5799 (4) | 0.6491 (4) | 0.0602 (11) | |
O21 | 0.2937 (4) | 0.6303 (4) | 0.5009 (4) | 0.0583 (11) | |
F22 | 0.535 (4) | 0.663 (3) | 0.8997 (12) | 0.210 (12) | 0.46 (4) |
F23 | 0.7287 (10) | 0.705 (3) | 0.768 (4) | 0.160 (10) | 0.46 (4) |
F24 | 0.571 (3) | 0.8625 (11) | 0.768 (3) | 0.123 (8) | 0.46 (4) |
F22' | 0.535 (2) | 0.8339 (18) | 0.822 (2) | 0.151 (8) | 0.54 (4) |
F23' | 0.607 (3) | 0.6265 (15) | 0.8846 (14) | 0.136 (7) | 0.54 (4) |
F24' | 0.7200 (11) | 0.765 (2) | 0.7190 (16) | 0.112 (6) | 0.54 (4) |
F25 | 0.1515 (14) | 0.9427 (10) | 0.5496 (12) | 0.133 (5) | 0.610 (16) |
F26 | 0.0329 (8) | 0.7707 (11) | 0.5360 (13) | 0.141 (6) | 0.610 (16) |
F27 | 0.1730 (11) | 0.8803 (10) | 0.3721 (6) | 0.112 (4) | 0.610 (16) |
F25' | 0.1983 (18) | 0.9551 (11) | 0.427 (2) | 0.203 (12) | 0.390 (16) |
F26' | 0.0879 (15) | 0.854 (2) | 0.6136 (9) | 0.107 (6) | 0.390 (16) |
F27' | 0.0649 (14) | 0.7824 (19) | 0.445 (2) | 0.127 (7) | 0.390 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0491 (6) | 0.0501 (7) | 0.0520 (7) | 0.0060 (4) | −0.0138 (5) | −0.0182 (5) |
C1 | 0.058 (4) | 0.064 (4) | 0.062 (4) | 0.003 (3) | −0.020 (3) | −0.008 (3) |
C2 | 0.050 (3) | 0.069 (4) | 0.072 (4) | 0.002 (3) | −0.023 (3) | −0.019 (4) |
N3 | 0.047 (3) | 0.049 (3) | 0.051 (3) | 0.004 (2) | −0.013 (2) | −0.012 (2) |
C4 | 0.051 (3) | 0.061 (4) | 0.054 (4) | 0.002 (3) | −0.013 (3) | −0.010 (3) |
C5 | 0.048 (3) | 0.068 (4) | 0.060 (4) | −0.004 (3) | −0.015 (3) | −0.017 (3) |
C6 | 0.051 (3) | 0.055 (4) | 0.058 (4) | 0.007 (3) | −0.010 (3) | −0.015 (3) |
C7 | 0.055 (4) | 0.067 (4) | 0.064 (4) | 0.006 (3) | −0.014 (3) | −0.014 (3) |
C8 | 0.060 (4) | 0.067 (4) | 0.061 (4) | 0.000 (3) | −0.011 (3) | −0.017 (3) |
C9 | 0.059 (4) | 0.052 (4) | 0.058 (4) | −0.004 (3) | 0.000 (3) | −0.015 (3) |
N10 | 0.075 (4) | 0.077 (4) | 0.074 (4) | −0.007 (3) | −0.017 (3) | −0.008 (3) |
C11 | 0.086 (5) | 0.088 (6) | 0.078 (5) | −0.004 (5) | −0.017 (4) | −0.001 (5) |
C12 | 0.089 (6) | 0.058 (4) | 0.089 (6) | −0.010 (4) | 0.009 (5) | −0.004 (4) |
C13 | 0.071 (5) | 0.076 (5) | 0.118 (7) | −0.017 (4) | 0.002 (5) | −0.043 (5) |
C14 | 0.067 (4) | 0.070 (5) | 0.081 (5) | −0.008 (4) | −0.010 (4) | −0.024 (4) |
C15 | 0.088 (6) | 0.101 (7) | 0.109 (7) | 0.019 (5) | −0.035 (6) | −0.055 (6) |
C16 | 0.062 (4) | 0.059 (4) | 0.060 (4) | 0.005 (3) | −0.014 (3) | −0.023 (3) |
C17 | 0.076 (4) | 0.076 (5) | 0.090 (5) | 0.026 (4) | −0.026 (4) | −0.048 (4) |
C18 | 0.056 (4) | 0.064 (4) | 0.058 (4) | 0.013 (3) | −0.010 (3) | −0.021 (3) |
C19 | 0.080 (5) | 0.083 (5) | 0.089 (6) | 0.024 (4) | −0.015 (5) | −0.031 (5) |
O20 | 0.058 (2) | 0.060 (3) | 0.070 (3) | 0.010 (2) | −0.019 (2) | −0.027 (2) |
O21 | 0.061 (3) | 0.053 (2) | 0.063 (3) | 0.0014 (19) | −0.012 (2) | −0.017 (2) |
F22 | 0.32 (2) | 0.22 (2) | 0.112 (13) | −0.051 (18) | −0.081 (14) | −0.049 (13) |
F23 | 0.132 (13) | 0.188 (18) | 0.22 (2) | 0.089 (12) | −0.136 (13) | −0.127 (15) |
F24 | 0.140 (13) | 0.118 (11) | 0.155 (16) | −0.006 (9) | −0.046 (11) | −0.097 (10) |
F22' | 0.158 (13) | 0.204 (16) | 0.155 (14) | 0.077 (12) | −0.074 (10) | −0.143 (12) |
F23' | 0.178 (15) | 0.163 (12) | 0.065 (8) | −0.012 (10) | −0.059 (8) | −0.009 (7) |
F24' | 0.084 (8) | 0.133 (12) | 0.135 (10) | −0.004 (6) | −0.051 (7) | −0.046 (9) |
F25 | 0.165 (10) | 0.101 (7) | 0.164 (10) | 0.078 (7) | −0.088 (8) | −0.069 (7) |
F26 | 0.063 (5) | 0.172 (9) | 0.152 (10) | 0.023 (5) | −0.015 (6) | 0.016 (8) |
F27 | 0.140 (8) | 0.086 (7) | 0.106 (6) | 0.040 (6) | −0.043 (6) | −0.015 (5) |
F25' | 0.153 (15) | 0.138 (16) | 0.23 (2) | 0.063 (12) | 0.031 (16) | 0.065 (16) |
F26' | 0.088 (9) | 0.130 (13) | 0.124 (11) | 0.068 (9) | −0.039 (8) | −0.068 (10) |
F27' | 0.111 (11) | 0.159 (12) | 0.142 (12) | 0.047 (9) | −0.082 (9) | −0.072 (10) |
Cu1—N3 | 2.006 (5) | C11—H11 | 0.9300 |
Cu1—N3i | 2.006 (5) | C12—C13 | 1.373 (11) |
Cu1—O20i | 2.042 (4) | C12—H12 | 0.9300 |
Cu1—O20 | 2.042 (4) | C13—C14 | 1.359 (10) |
Cu1—O21i | 2.257 (4) | C13—H13 | 0.9300 |
Cu1—O21 | 2.257 (4) | C14—H14 | 0.9300 |
C1—C2 | 1.368 (9) | C15—F23 | 1.306 (5) |
C1—C6 | 1.390 (8) | C15—F22' | 1.308 (5) |
C1—H1 | 0.9300 | C15—F22 | 1.309 (5) |
C2—N3 | 1.345 (7) | C15—F24 | 1.312 (5) |
C2—H2 | 0.9300 | C15—F23' | 1.315 (5) |
N3—C4 | 1.338 (7) | C15—F24' | 1.317 (5) |
C4—C5 | 1.368 (8) | C15—C16 | 1.534 (8) |
C4—H4 | 0.9300 | C16—O20 | 1.251 (7) |
C5—C6 | 1.402 (8) | C16—C17 | 1.387 (7) |
C5—H5 | 0.9300 | C17—C18 | 1.390 (7) |
C6—C7 | 1.463 (9) | C17—H17 | 0.9300 |
C7—C8 | 1.322 (9) | C18—O21 | 1.226 (7) |
C7—H7 | 0.9300 | C18—C19 | 1.541 (8) |
C8—C9 | 1.461 (9) | C19—F25' | 1.305 (5) |
C8—H8 | 0.9300 | C19—F27' | 1.306 (5) |
C9—N10 | 1.341 (8) | C19—F25 | 1.308 (5) |
C9—C14 | 1.376 (9) | C19—F26 | 1.310 (5) |
N10—C11 | 1.339 (9) | C19—F26' | 1.322 (5) |
C11—C12 | 1.368 (11) | C19—F27 | 1.323 (5) |
N3—Cu1—N3i | 180.0 (2) | C12—C11—H11 | 118.2 |
N3—Cu1—O20i | 90.50 (18) | C11—C12—C13 | 118.6 (7) |
N3i—Cu1—O20i | 89.50 (18) | C11—C12—H12 | 120.7 |
N3—Cu1—O20 | 89.50 (18) | C13—C12—H12 | 120.7 |
N3i—Cu1—O20 | 90.50 (18) | C14—C13—C12 | 118.8 (7) |
O20i—Cu1—O20 | 180.000 (1) | C14—C13—H13 | 120.6 |
N3—Cu1—O21i | 87.49 (16) | C12—C13—H13 | 120.6 |
N3i—Cu1—O21i | 92.51 (16) | C13—C14—C9 | 119.7 (7) |
O20i—Cu1—O21i | 85.89 (15) | C13—C14—H14 | 120.1 |
O20—Cu1—O21i | 94.11 (15) | C9—C14—H14 | 120.1 |
N3—Cu1—O21 | 92.51 (16) | F23—C15—F22 | 107.4 (5) |
N3i—Cu1—O21 | 87.49 (16) | F23—C15—F24 | 106.9 (5) |
O20i—Cu1—O21 | 94.11 (15) | F22—C15—F24 | 106.8 (5) |
O20—Cu1—O21 | 85.89 (15) | F22'—C15—F23' | 106.6 (5) |
O21i—Cu1—O21 | 180.000 (1) | F22'—C15—F24' | 106.7 (5) |
C2—C1—C6 | 121.3 (6) | F23'—C15—F24' | 105.8 (5) |
C2—C1—H1 | 119.4 | F23—C15—C16 | 115.6 (11) |
C6—C1—H1 | 119.4 | F22'—C15—C16 | 117.1 (9) |
N3—C2—C1 | 122.6 (6) | F22—C15—C16 | 108.2 (12) |
N3—C2—H2 | 118.7 | F24—C15—C16 | 111.5 (10) |
C1—C2—H2 | 118.7 | F23'—C15—C16 | 112.1 (8) |
C4—N3—C2 | 117.1 (5) | F24'—C15—C16 | 107.8 (8) |
C4—N3—Cu1 | 121.9 (4) | O20—C16—C17 | 129.1 (5) |
C2—N3—Cu1 | 121.0 (4) | O20—C16—C15 | 112.0 (5) |
N3—C4—C5 | 123.2 (5) | C17—C16—C15 | 118.8 (5) |
N3—C4—H4 | 118.4 | C16—C17—C18 | 124.2 (6) |
C5—C4—H4 | 118.4 | C16—C17—H17 | 117.9 |
C4—C5—C6 | 120.6 (6) | C18—C17—H17 | 117.9 |
C4—C5—H5 | 119.7 | O21—C18—C17 | 128.9 (5) |
C6—C5—H5 | 119.7 | O21—C18—C19 | 114.6 (5) |
C1—C6—C5 | 115.2 (6) | C17—C18—C19 | 116.6 (5) |
C1—C6—C7 | 120.3 (6) | F25'—C19—F27' | 107.6 (5) |
C5—C6—C7 | 124.4 (6) | F25—C19—F26 | 107.5 (5) |
C8—C7—C6 | 127.2 (6) | F25'—C19—F26' | 106.3 (5) |
C8—C7—H7 | 116.4 | F27'—C19—F26' | 105.8 (5) |
C6—C7—H7 | 116.4 | F25—C19—F27 | 105.7 (4) |
C7—C8—C9 | 125.2 (6) | F26—C19—F27 | 105.5 (4) |
C7—C8—H8 | 117.4 | F25'—C19—C18 | 116.3 (9) |
C9—C8—H8 | 117.4 | F27'—C19—C18 | 112.5 (8) |
N10—C9—C14 | 122.4 (6) | F25—C19—C18 | 116.6 (6) |
N10—C9—C8 | 117.3 (6) | F26—C19—C18 | 111.2 (6) |
C14—C9—C8 | 120.3 (6) | F26'—C19—C18 | 107.6 (7) |
C9—N10—C11 | 116.8 (6) | F27—C19—C18 | 109.6 (6) |
N10—C11—C12 | 123.6 (7) | C16—O20—Cu1 | 126.7 (4) |
N10—C11—H11 | 118.2 | C18—O21—Cu1 | 121.2 (4) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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