Bis[2-(1-naphthyl­imino­meth­yl)phenolato-κ²N,O]copper(II)

In the title complex, [Cu(C₁₇H₁₂NO)₂], the Cu^II ion is coordinated by two bidentate ligands in a trans arrangement, forming a CuN₂O₂ slightly distorted square-planar configuration.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.015 Å
• R factor = 0.067
• wR factor = 0.176
• Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.530
           From the CIF: _refine_ls_abs_structure_Flack_su    0.030
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.53
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.63 mm
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.68 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.10
PLAT335_ALERT_2_C Large Benzene C-C Range .......  C8     -C13           0.21 Ang.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         15

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.01
           From the CIF: _reflns_number_total               3714
           Count of symmetry unique reflns         2305
           Completeness (_total/calc)            161.13%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1409
           Fraction of Friedel pairs measured     0.611
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis[2-(1-naphthyliminomethyl)phenolato-κ²N,O]copper(II)

Crystal data

[Cu(C17H12NO)2]	F(000) = 574
Mr = 556.09	Dx = 1.419 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 1831 reflections
a = 8.6600 (15) Å	θ = 2.4–25.2°
b = 12.190 (2) Å	µ = 0.87 mm^−1
c = 12.496 (2) Å	T = 298 K
β = 99.317 (2)°	Needle, blue
V = 1301.7 (4) Å^3	0.63 × 0.21 × 0.14 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	3714 independent reflections
Radiation source: fine-focus sealed tube	2599 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.609, Tmax = 0.887	k = −13→14
6484 measured reflections	l = −14→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.176	w = 1/[σ^2(Fo^2) + (0.0956P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
3714 reflections	Δρmax = 0.89 e Å^−3
352 parameters	Δρmin = −0.45 e Å^−3
257 restraints	Absolute structure: Flack (1983), with 1411 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.53 (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.

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.62940 (14)	0.38367 (7)	0.71098 (12)	0.0449 (3)
N1	0.7949 (10)	0.3992 (6)	0.8407 (8)	0.042 (2)
N2	0.4660 (10)	0.3695 (6)	0.5771 (8)	0.044 (2)
O1	0.6662 (8)	0.2334 (4)	0.7037 (7)	0.060 (2)
O2	0.5956 (9)	0.5345 (4)	0.7160 (8)	0.062 (2)
C1	0.8428 (10)	0.3182 (7)	0.9022 (9)	0.045 (2)
H1	0.9076	0.3348	0.9670	0.054*
C2	0.8074 (11)	0.2051 (7)	0.8822 (9)	0.052 (2)
C3	0.7240 (11)	0.1672 (7)	0.7807 (9)	0.052 (2)
C4	0.7099 (13)	0.0541 (7)	0.7655 (11)	0.068 (3)
H4	0.6604	0.0267	0.6992	0.082*
C5	0.7681 (13)	−0.0175 (8)	0.8469 (11)	0.076 (3)
H5	0.7570	−0.0925	0.8346	0.091*
C6	0.8428 (15)	0.0193 (9)	0.9471 (12)	0.081 (3)
H6	0.8774	−0.0299	1.0027	0.097*
C7	0.8641 (15)	0.1290 (9)	0.9619 (11)	0.074 (3)
H7	0.9185	0.1540	1.0276	0.089*
C8	0.8561 (9)	0.5059 (7)	0.8726 (8)	0.0378 (18)
C9	0.8137 (11)	0.5560 (7)	0.9541 (9)	0.052 (2)
H9	0.7484	0.5214	0.9958	0.063*
C10	0.8696 (12)	0.6686 (8)	0.9804 (9)	0.059 (3)
H10	0.8368	0.7050	1.0382	0.070*
C11	0.9609 (11)	0.7171 (7)	0.9267 (9)	0.055 (2)
H11	0.9955	0.7876	0.9462	0.067*
C12	1.0099 (9)	0.6655 (7)	0.8386 (8)	0.050 (2)
C13	0.9550 (9)	0.5574 (6)	0.8096 (7)	0.0410 (18)
C14	1.0075 (10)	0.5062 (7)	0.7220 (8)	0.051 (2)
H14	0.9748	0.4350	0.7038	0.062*
C15	1.1049 (12)	0.5572 (8)	0.6627 (10)	0.068 (3)
H15	1.1384	0.5209	0.6051	0.082*
C16	1.1547 (13)	0.6652 (9)	0.6890 (11)	0.073 (3)
H16	1.2202	0.7007	0.6481	0.088*
C17	1.1090 (11)	0.7162 (8)	0.7711 (11)	0.063 (3)
H17	1.1421	0.7880	0.7862	0.076*
C18	0.4198 (11)	0.4511 (7)	0.5145 (8)	0.048 (2)
H18	0.3551	0.4356	0.4493	0.057*
C19	0.4594 (11)	0.5625 (7)	0.5369 (9)	0.049 (2)
C20	0.5446 (10)	0.5980 (6)	0.6332 (8)	0.047 (2)
C21	0.5777 (11)	0.7106 (7)	0.6473 (10)	0.058 (2)
H21	0.6327	0.7355	0.7129	0.070*
C22	0.5297 (12)	0.7841 (8)	0.5654 (10)	0.067 (3)
H22	0.5542	0.8581	0.5749	0.080*
C23	0.4441 (13)	0.7472 (8)	0.4681 (10)	0.071 (3)
H23	0.4093	0.7979	0.4139	0.085*
C24	0.4097 (12)	0.6382 (8)	0.4499 (10)	0.054 (2)
H24	0.3560	0.6141	0.3835	0.065*
C25	0.4153 (11)	0.2617 (8)	0.5389 (9)	0.051 (2)
C26	0.4628 (13)	0.2187 (9)	0.4494 (10)	0.069 (3)
H26	0.5232	0.2597	0.4090	0.083*
C27	0.4180 (15)	0.1102 (10)	0.4192 (13)	0.085 (3)
H27	0.4495	0.0794	0.3581	0.102*
C28	0.3321 (15)	0.0519 (10)	0.4765 (13)	0.087 (3)
H28	0.3043	−0.0191	0.4536	0.104*
C29	0.2820 (13)	0.0905 (8)	0.5674 (11)	0.078 (3)
C30	0.3183 (11)	0.2027 (7)	0.5973 (9)	0.054 (2)
C31	0.2556 (11)	0.2457 (8)	0.6848 (9)	0.065 (2)
H31	0.2806	0.3174	0.7064	0.078*
C32	0.1605 (14)	0.1876 (10)	0.7392 (11)	0.085 (3)
H32	0.1141	0.2206	0.7932	0.102*
C33	0.133 (2)	0.0783 (10)	0.7133 (19)	0.102 (3)
H33	0.0761	0.0362	0.7553	0.122*
C34	0.1860 (14)	0.0317 (10)	0.6300 (12)	0.088 (3)
H34	0.1598	−0.0408	0.6123	0.106*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0458 (5)	0.0335 (5)	0.0494 (6)	−0.0061 (5)	−0.0099 (4)	0.0025 (6)
N1	0.038 (4)	0.038 (4)	0.046 (5)	−0.006 (3)	−0.003 (4)	0.001 (3)
N2	0.046 (4)	0.044 (4)	0.039 (5)	−0.009 (3)	−0.003 (4)	−0.005 (3)
O1	0.070 (5)	0.039 (3)	0.060 (4)	−0.004 (3)	−0.026 (4)	0.001 (3)
O2	0.078 (5)	0.034 (3)	0.061 (4)	0.003 (3)	−0.025 (4)	0.001 (3)
C1	0.037 (4)	0.042 (4)	0.051 (5)	−0.001 (4)	−0.008 (4)	0.003 (4)
C2	0.046 (4)	0.038 (4)	0.065 (5)	0.007 (4)	−0.010 (4)	0.011 (4)
C3	0.047 (4)	0.036 (4)	0.067 (5)	−0.001 (4)	−0.007 (4)	0.002 (4)
C4	0.065 (5)	0.038 (4)	0.091 (6)	−0.004 (4)	−0.018 (5)	0.000 (4)
C5	0.074 (6)	0.036 (4)	0.107 (7)	0.000 (4)	−0.020 (5)	0.011 (5)
C6	0.083 (6)	0.048 (5)	0.101 (7)	0.009 (5)	−0.018 (6)	0.027 (5)
C7	0.076 (6)	0.056 (5)	0.083 (7)	0.008 (5)	−0.014 (6)	0.018 (5)
C8	0.032 (4)	0.033 (4)	0.043 (4)	0.001 (3)	−0.010 (4)	−0.002 (3)
C9	0.046 (5)	0.049 (5)	0.059 (6)	−0.006 (4)	−0.002 (4)	−0.003 (4)
C10	0.060 (5)	0.048 (5)	0.061 (6)	0.005 (4)	−0.010 (5)	−0.019 (5)
C11	0.051 (5)	0.038 (4)	0.068 (6)	−0.004 (4)	−0.017 (5)	−0.001 (4)
C12	0.035 (4)	0.037 (4)	0.069 (5)	−0.005 (3)	−0.014 (4)	0.008 (4)
C13	0.032 (4)	0.035 (4)	0.051 (5)	0.001 (3)	−0.009 (4)	0.004 (3)
C14	0.044 (4)	0.046 (4)	0.063 (5)	−0.002 (4)	0.005 (4)	−0.002 (4)
C15	0.046 (5)	0.074 (5)	0.086 (7)	−0.001 (4)	0.015 (5)	0.002 (5)
C16	0.051 (5)	0.075 (6)	0.094 (8)	−0.013 (5)	0.011 (6)	0.013 (5)
C17	0.043 (5)	0.045 (5)	0.094 (7)	−0.015 (4)	−0.010 (5)	0.011 (4)
C18	0.048 (4)	0.046 (4)	0.043 (5)	−0.003 (4)	−0.008 (4)	0.003 (4)
C19	0.048 (4)	0.040 (4)	0.052 (5)	0.002 (3)	−0.007 (4)	0.002 (4)
C20	0.045 (4)	0.034 (4)	0.059 (5)	0.001 (3)	−0.005 (4)	0.006 (4)
C21	0.054 (5)	0.040 (4)	0.073 (6)	−0.003 (4)	−0.009 (5)	−0.002 (4)
C22	0.073 (5)	0.037 (4)	0.084 (6)	0.000 (4)	−0.010 (5)	0.013 (4)
C23	0.087 (6)	0.043 (5)	0.077 (6)	0.008 (4)	−0.003 (5)	0.018 (5)
C24	0.066 (5)	0.040 (5)	0.055 (6)	0.008 (4)	0.003 (5)	0.001 (4)
C25	0.046 (4)	0.046 (4)	0.054 (5)	0.000 (4)	−0.014 (4)	−0.009 (4)
C26	0.057 (5)	0.072 (5)	0.072 (6)	0.006 (5)	−0.006 (5)	−0.021 (5)
C27	0.068 (6)	0.079 (6)	0.097 (8)	0.019 (5)	−0.017 (6)	−0.037 (6)
C28	0.072 (6)	0.062 (6)	0.113 (8)	0.008 (5)	−0.029 (6)	−0.030 (5)
C29	0.060 (5)	0.056 (5)	0.101 (6)	−0.007 (4)	−0.037 (5)	−0.002 (5)
C30	0.046 (4)	0.039 (4)	0.065 (5)	−0.007 (4)	−0.022 (4)	0.000 (4)
C31	0.060 (5)	0.068 (5)	0.061 (6)	−0.017 (4)	−0.008 (5)	0.009 (5)
C32	0.070 (6)	0.101 (6)	0.077 (8)	−0.022 (5)	−0.009 (6)	0.022 (6)
C33	0.078 (6)	0.106 (7)	0.108 (8)	−0.030 (7)	−0.025 (6)	0.025 (8)
C34	0.068 (6)	0.065 (6)	0.116 (8)	−0.027 (5)	−0.035 (6)	0.015 (6)

Geometric parameters (Å, º)

Cu1—O1	1.864 (6)	C15—C16	1.408 (14)
Cu1—O2	1.864 (5)	C15—H15	0.9300
Cu1—N1	1.991 (9)	C16—C17	1.315 (16)
Cu1—N2	2.016 (9)	C16—H16	0.9300
N1—C1	1.279 (11)	C17—H17	0.9300
N1—C8	1.436 (11)	C18—C19	1.418 (12)
N2—C18	1.288 (12)	C18—H18	0.9300
N2—C25	1.442 (12)	C19—C20	1.376 (13)
O1—C3	1.293 (11)	C19—C24	1.438 (15)
O2—C20	1.310 (12)	C20—C21	1.407 (11)
C1—C2	1.426 (12)	C21—C22	1.373 (14)
C1—H1	0.9300	C21—H21	0.9300
C2—C7	1.391 (14)	C22—C23	1.392 (15)
C2—C3	1.431 (14)	C22—H22	0.9300
C3—C4	1.395 (12)	C23—C24	1.373 (13)
C4—C5	1.372 (15)	C23—H23	0.9300
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.387 (17)	C25—C26	1.358 (16)
C5—H5	0.9300	C25—C30	1.398 (14)
C6—C7	1.358 (14)	C26—C27	1.413 (14)
C6—H6	0.9300	C26—H26	0.9300
C7—H7	0.9300	C27—C28	1.320 (19)
C8—C9	1.292 (12)	C27—H27	0.9300
C8—C13	1.402 (13)	C28—C29	1.365 (18)
C9—C10	1.475 (13)	C28—H28	0.9300
C9—H9	0.9300	C29—C34	1.424 (18)
C10—C11	1.263 (14)	C29—C30	1.439 (12)
C10—H10	0.9300	C30—C31	1.399 (14)
C11—C12	1.392 (14)	C31—C32	1.351 (15)
C11—H11	0.9300	C31—H31	0.9300
C12—C13	1.428 (11)	C32—C33	1.383 (15)
C12—C17	1.437 (14)	C32—H32	0.9300
C13—C14	1.398 (13)	C33—C34	1.33 (2)
C14—C15	1.360 (14)	C33—H33	0.9300
C14—H14	0.9300	C34—H34	0.9300
O1—Cu1—O2	178.7 (5)	C16—C15—H15	120.2
O1—Cu1—N1	91.5 (3)	C17—C16—C15	120.4 (10)
O2—Cu1—N1	88.6 (3)	C17—C16—H16	119.8
O1—Cu1—N2	88.7 (3)	C15—C16—H16	119.8
O2—Cu1—N2	91.1 (3)	C16—C17—C12	122.6 (9)
N1—Cu1—N2	178.4 (5)	C16—C17—H17	118.7
C1—N1—C8	117.6 (9)	C12—C17—H17	118.7
C1—N1—Cu1	122.5 (7)	N2—C18—C19	125.3 (10)
C8—N1—Cu1	119.7 (6)	N2—C18—H18	117.4
C18—N2—C25	117.0 (9)	C19—C18—H18	117.4
C18—N2—Cu1	123.1 (7)	C20—C19—C18	123.6 (9)
C25—N2—Cu1	119.2 (6)	C20—C19—C24	120.8 (9)
C3—O1—Cu1	128.7 (7)	C18—C19—C24	115.6 (10)
C20—O2—Cu1	126.3 (7)	O2—C20—C19	124.7 (8)
N1—C1—C2	127.0 (10)	O2—C20—C21	116.2 (9)
N1—C1—H1	116.5	C19—C20—C21	119.1 (9)
C2—C1—H1	116.5	C22—C21—C20	120.8 (10)
C7—C2—C1	118.6 (10)	C22—C21—H21	119.6
C7—C2—C3	119.3 (9)	C20—C21—H21	119.6
C1—C2—C3	122.0 (9)	C21—C22—C23	119.6 (9)
O1—C3—C4	120.0 (10)	C21—C22—H22	120.2
O1—C3—C2	122.6 (8)	C23—C22—H22	120.2
C4—C3—C2	117.4 (9)	C24—C23—C22	121.9 (10)
C5—C4—C3	120.9 (12)	C24—C23—H23	119.1
C5—C4—H4	119.6	C22—C23—H23	119.1
C3—C4—H4	119.6	C23—C24—C19	117.7 (11)
C4—C5—C6	121.7 (10)	C23—C24—H24	121.1
C4—C5—H5	119.1	C19—C24—H24	121.1
C6—C5—H5	119.1	C26—C25—C30	121.2 (10)
C7—C6—C5	118.3 (11)	C26—C25—N2	120.5 (10)
C7—C6—H6	120.8	C30—C25—N2	118.2 (9)
C5—C6—H6	120.8	C25—C26—C27	118.4 (13)
C6—C7—C2	122.3 (12)	C25—C26—H26	120.8
C6—C7—H7	118.8	C27—C26—H26	120.8
C2—C7—H7	118.8	C28—C27—C26	120.9 (14)
C9—C8—C13	120.5 (8)	C28—C27—H27	119.6
C9—C8—N1	120.5 (9)	C26—C27—H27	119.6
C13—C8—N1	118.8 (8)	C27—C28—C29	123.3 (12)
C8—C9—C10	119.4 (9)	C27—C28—H28	118.4
C8—C9—H9	120.3	C29—C28—H28	118.4
C10—C9—H9	120.3	C28—C29—C34	125.2 (12)
C11—C10—C9	121.9 (10)	C28—C29—C30	117.3 (12)
C11—C10—H10	119.1	C34—C29—C30	117.3 (13)
C9—C10—H10	119.1	C25—C30—C31	123.8 (8)
C10—C11—C12	120.4 (9)	C25—C30—C29	118.6 (11)
C10—C11—H11	119.8	C31—C30—C29	117.6 (10)
C12—C11—H11	119.8	C32—C31—C30	122.8 (11)
C11—C12—C13	119.1 (8)	C32—C31—H31	118.6
C11—C12—C17	123.9 (9)	C30—C31—H31	118.6
C13—C12—C17	117.0 (9)	C31—C32—C33	118.9 (15)
C14—C13—C8	123.0 (8)	C31—C32—H32	120.5
C14—C13—C12	118.3 (8)	C33—C32—H32	120.5
C8—C13—C12	118.6 (8)	C34—C33—C32	121.8 (16)
C15—C14—C13	122.1 (9)	C34—C33—H33	119.1
C15—C14—H14	118.9	C32—C33—H33	119.1
C13—C14—H14	118.9	C33—C34—C29	121.3 (13)
C14—C15—C16	119.6 (11)	C33—C34—H34	119.3
C14—C15—H15	120.2	C29—C34—H34	119.3