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Bright-blue crystals of the centrosymmetric title compound, [Cu(C
2N
3)
2(C
11H
6N
2O)
2], were obtained by reacting copper(II) chloride with 4,5-diazafluoren-9-one (dafo) and sodium dicyanamide. X-ray diffraction analysis reveals that the dicyanamide and dafo ligands are bonded to the Cu atom to give a distorted octahedral geometry. The dicyanamide anions are terminally bonded in
trans postitions. Weak C—H
O and C—H
N interactions help to define the crystal packing.
Supporting information
CCDC reference: 239068
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.043
- wR factor = 0.102
- Data-to-parameter ratio = 11.7
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
Alert level B
PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C13
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - C12 .. 5.69 su
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... N3
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C12
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A .. N5 .. 2.69 Ang.
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Sheldrick, 1995); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Bis(4,5-diazafluorene-9-one)dicyanamidocopper(II)
top
Crystal data top
[Cu(C2N3)2(C11H6N2O)2] | F(000) = 566 |
Mr = 560.00 | Dx = 1.565 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 8.2935 (12) Å | θ = 5.9–11.4° |
b = 14.9729 (10) Å | µ = 0.97 mm−1 |
c = 9.7568 (11) Å | T = 293 K |
β = 101.192 (11)° | Platelet, blue |
V = 1188.5 (2) Å3 | 0.25 × 0.15 × 0.10 mm |
Z = 2 | |
Data collection top
Bruker P4 diffractometer | 1524 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 25.0°, θmin = 2.5° |
ω scans | h = −1→9 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→17 |
Tmin = 0.855, Tmax = 0.908 | l = −11→11 |
2758 measured reflections | 3 standard reflections every 100 reflections |
2090 independent reflections | intensity decay: none |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.001P)2 + 1.2P] where P = (Fo2 + 2Fc2)/3 |
2090 reflections | (Δ/σ)max = 0.006 |
178 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.39 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 1.0000 | 0.0000 | 0.0000 | 0.05003 (19) | |
O1 | 0.7164 (4) | −0.0688 (2) | 0.5431 (3) | 0.0918 (10) | |
N1 | 0.8154 (3) | 0.02041 (19) | 0.1013 (3) | 0.0516 (7) | |
N2 | 1.0964 (4) | −0.0945 (2) | 0.2355 (3) | 0.0599 (8) | |
N3 | 1.1946 (5) | 0.2309 (3) | 0.2451 (4) | 0.0965 (13) | |
N4 | 1.1091 (4) | 0.1055 (2) | 0.0927 (3) | 0.0626 (8) | |
N5 | 1.4638 (6) | 0.2838 (3) | 0.3530 (5) | 0.1172 (16) | |
C1 | 0.6802 (4) | 0.0715 (3) | 0.0611 (4) | 0.0628 (10) | |
H1A | 0.6659 | 0.1000 | −0.0251 | 0.075* | |
C2 | 0.5635 (5) | 0.0831 (3) | 0.1410 (4) | 0.0719 (11) | |
H2A | 0.4733 | 0.1195 | 0.1088 | 0.086* | |
C3 | 0.5786 (5) | 0.0412 (3) | 0.2695 (4) | 0.0697 (11) | |
H3A | 0.4994 | 0.0476 | 0.3245 | 0.084* | |
C4 | 0.7158 (4) | −0.0101 (3) | 0.3115 (4) | 0.0572 (9) | |
C5 | 0.7804 (5) | −0.0625 (3) | 0.4420 (4) | 0.0660 (10) | |
C6 | 0.9408 (5) | −0.1007 (3) | 0.4228 (4) | 0.0616 (10) | |
C7 | 1.0551 (6) | −0.1542 (3) | 0.5031 (4) | 0.0739 (12) | |
H7A | 1.0420 | −0.1742 | 0.5905 | 0.089* | |
C8 | 1.1909 (6) | −0.1773 (3) | 0.4484 (4) | 0.0773 (12) | |
H8A | 1.2716 | −0.2137 | 0.4997 | 0.093* | |
C9 | 1.2084 (5) | −0.1469 (3) | 0.3176 (4) | 0.0722 (11) | |
H9A | 1.3021 | −0.1634 | 0.2847 | 0.087* | |
C10 | 0.8296 (4) | −0.0185 (2) | 0.2249 (4) | 0.0513 (9) | |
C11 | 0.9684 (4) | −0.0740 (2) | 0.2920 (4) | 0.0524 (8) | |
C12 | 1.1588 (5) | 0.1622 (3) | 0.1629 (4) | 0.0634 (10) | |
C13 | 1.3445 (6) | 0.2558 (3) | 0.2990 (4) | 0.0705 (11) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0425 (3) | 0.0600 (4) | 0.0488 (3) | −0.0034 (3) | 0.0120 (2) | −0.0063 (3) |
O1 | 0.107 (2) | 0.107 (3) | 0.0740 (19) | 0.009 (2) | 0.0494 (18) | 0.0108 (18) |
N1 | 0.0435 (15) | 0.0612 (19) | 0.0502 (16) | −0.0002 (13) | 0.0092 (12) | −0.0038 (14) |
N2 | 0.0575 (19) | 0.0617 (19) | 0.0609 (18) | 0.0052 (15) | 0.0124 (15) | −0.0033 (15) |
N3 | 0.087 (3) | 0.071 (2) | 0.115 (3) | 0.010 (2) | −0.023 (2) | −0.029 (2) |
N4 | 0.0501 (18) | 0.068 (2) | 0.069 (2) | −0.0039 (16) | 0.0100 (15) | −0.0160 (18) |
N5 | 0.093 (3) | 0.101 (3) | 0.144 (4) | −0.022 (3) | −0.009 (3) | −0.035 (3) |
C1 | 0.053 (2) | 0.077 (3) | 0.058 (2) | 0.005 (2) | 0.0102 (18) | −0.002 (2) |
C2 | 0.052 (2) | 0.091 (3) | 0.074 (3) | 0.013 (2) | 0.015 (2) | −0.004 (2) |
C3 | 0.055 (2) | 0.087 (3) | 0.072 (3) | 0.000 (2) | 0.025 (2) | −0.014 (2) |
C4 | 0.055 (2) | 0.063 (2) | 0.058 (2) | −0.0050 (19) | 0.0210 (17) | −0.0074 (18) |
C5 | 0.076 (3) | 0.068 (3) | 0.060 (2) | −0.005 (2) | 0.027 (2) | −0.008 (2) |
C6 | 0.076 (3) | 0.056 (2) | 0.053 (2) | −0.004 (2) | 0.0128 (19) | −0.0040 (18) |
C7 | 0.098 (3) | 0.067 (3) | 0.057 (2) | 0.000 (2) | 0.015 (2) | 0.000 (2) |
C8 | 0.083 (3) | 0.072 (3) | 0.071 (3) | 0.014 (2) | 0.001 (2) | 0.002 (2) |
C9 | 0.064 (2) | 0.075 (3) | 0.076 (3) | 0.014 (2) | 0.010 (2) | −0.007 (2) |
C10 | 0.0479 (19) | 0.055 (2) | 0.053 (2) | −0.0078 (16) | 0.0154 (15) | −0.0098 (16) |
C11 | 0.054 (2) | 0.053 (2) | 0.0510 (19) | −0.0032 (17) | 0.0124 (16) | −0.0063 (16) |
C12 | 0.056 (2) | 0.064 (3) | 0.065 (2) | 0.009 (2) | 0.0016 (19) | 0.005 (2) |
C13 | 0.074 (3) | 0.055 (2) | 0.078 (3) | −0.003 (2) | 0.001 (2) | −0.008 (2) |
Geometric parameters (Å, º) top
Cu1—N4i | 1.954 (3) | C2—C3 | 1.386 (6) |
Cu1—N4 | 1.954 (3) | C2—H2A | 0.9300 |
Cu1—N1i | 2.001 (3) | C3—C4 | 1.368 (5) |
Cu1—N1 | 2.001 (3) | C3—H3A | 0.9300 |
Cu1—N2 | 2.684 (3) | C4—C10 | 1.390 (5) |
O1—C5 | 1.211 (4) | C4—C5 | 1.503 (5) |
N1—C10 | 1.324 (4) | C5—C6 | 1.493 (6) |
N1—C1 | 1.350 (4) | C6—C7 | 1.366 (6) |
N2—C11 | 1.324 (4) | C6—C11 | 1.398 (5) |
N2—C9 | 1.354 (5) | C7—C8 | 1.381 (6) |
N3—C12 | 1.301 (5) | C7—H7A | 0.9300 |
N3—C13 | 1.307 (6) | C8—C9 | 1.388 (6) |
N4—C12 | 1.118 (5) | C8—H8A | 0.9300 |
N5—C13 | 1.109 (5) | C9—H9A | 0.9300 |
C1—C2 | 1.366 (5) | C10—C11 | 1.467 (5) |
C1—H1A | 0.9300 | | |
| | | |
N2—Cu1—N1 | 77.7 (3) | C10—C4—C5 | 107.2 (3) |
N4—Cu1—N2 | 89.8 (4) | O1—C5—C6 | 127.9 (4) |
N4i—Cu1—N4 | 180.0 (2) | O1—C5—C4 | 126.1 (4) |
N4i—Cu1—N1i | 88.74 (12) | C6—C5—C4 | 105.9 (3) |
N4—Cu1—N1i | 91.26 (12) | C7—C6—C11 | 118.2 (4) |
N4i—Cu1—N1 | 91.26 (12) | C7—C6—C5 | 133.6 (4) |
N4—Cu1—N1 | 88.74 (12) | C11—C6—C5 | 108.2 (3) |
N1i—Cu1—N1 | 180.0 (2) | C6—C7—C8 | 116.9 (4) |
C10—N1—C1 | 115.8 (3) | C6—C7—H7A | 121.5 |
C10—N1—Cu1 | 116.2 (2) | C8—C7—H7A | 121.5 |
C1—N1—Cu1 | 127.9 (2) | C7—C8—C9 | 120.8 (4) |
C11—N2—C9 | 113.7 (3) | C7—C8—H8A | 119.6 |
C12—N3—C13 | 124.0 (4) | C9—C8—H8A | 119.6 |
C12—N4—Cu1 | 168.6 (3) | N2—C9—C8 | 123.5 (4) |
N1—C1—C2 | 123.1 (4) | N2—C9—H9A | 118.2 |
N1—C1—H1A | 118.4 | C8—C9—H9A | 118.2 |
C2—C1—H1A | 118.4 | N1—C10—C4 | 124.3 (3) |
C1—C2—C3 | 120.6 (4) | N1—C10—C11 | 125.4 (3) |
C1—C2—H2A | 119.7 | C4—C10—C11 | 110.3 (3) |
C3—C2—H2A | 119.7 | N2—C11—C6 | 126.9 (4) |
C4—C3—C2 | 116.7 (4) | N2—C11—C10 | 124.7 (3) |
C4—C3—H3A | 121.7 | C6—C11—C10 | 108.4 (3) |
C2—C3—H3A | 121.7 | N4—C12—N3 | 171.7 (5) |
C3—C4—C10 | 119.5 (4) | N5—C13—N3 | 172.2 (5) |
C3—C4—C5 | 133.3 (3) | | |
Symmetry code: (i) −x+2, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···N5ii | 0.93 | 2.54 | 3.260 (3) | 134 |
C9—H9A···N5iii | 0.93 | 2.69 | 3.605 (3) | 170 |
C3—H3A···O1iv | 0.93 | 2.42 | 3.352 (3) | 177 |
Symmetry codes: (ii) x−1, −y+1/2, z−1/2; (iii) −x+3, y−1/2, −z+1/2; (iv) −x+1, −y, −z+1. |
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