Bis(4,5-di­aza­fluoren-9-one)­dicyan­amido­copper(II)

Bright-blue crystals of the centrosymmetric title compound, [Cu(C₂N₃)₂(C₁₁H₆N₂O)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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

---

Computing details

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)

Crystal data

[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) Å^3	0.25 × 0.15 × 0.10 mm
Z = 2

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.001P)^2 + 1.2P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Cu1—N4^i	1.954 (3)	C2—C3	1.386 (6)
Cu1—N4	1.954 (3)	C2—H2A	0.9300
Cu1—N1^i	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)
N4^i—Cu1—N4	180.0 (2)	O1—C5—C4	126.1 (4)
N4^i—Cu1—N1^i	88.74 (12)	C6—C5—C4	105.9 (3)
N4—Cu1—N1^i	91.26 (12)	C7—C6—C11	118.2 (4)
N4^i—Cu1—N1	91.26 (12)	C7—C6—C5	133.6 (4)
N4—Cu1—N1	88.74 (12)	C11—C6—C5	108.2 (3)
N1^i—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)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N5^ii	0.93	2.54	3.260 (3)	134
C9—H9A···N5^iii	0.93	2.69	3.605 (3)	170
C3—H3A···O1^iv	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.