A second polymorph of (5,10,15,20-tetra­phenyl­porphyrinato)copper(II)

In the title compound, [Cu(C₄₄H₂₈N₄)], the copper ion is located at the center of the centrosymmetric and perfectly planar porphyrin ring.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.104
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C6     -C7_f          1.36 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      36.00 A   3 
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.12 Ratio

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(5,10,15,20-tetraphenylporphyrinato)copper(II)

Crystal data

[Cu(C44H28N4)]	Dx = 1.290 Mg m^−3
Mr = 676.24	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4/m	Cell parameters from 7160 reflections
Hall symbol: -I 4	θ = 2.2–27.9°
a = 13.3747 (19) Å	µ = 0.66 mm^−1
c = 9.7348 (19) Å	T = 293 K
V = 1741.4 (5) Å^3	Prism, purple
Z = 2	0.20 × 0.20 × 0.20 mm
F(000) = 698

Data collection

Bruker SMART 1K CCD diffractometer	971 independent reflections
Radiation source: fine-focus sealed tube	697 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
φ and ω scans	θmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −16→16
Tmin = 0.879, Tmax = 0.879	k = −16→16
17594 measured reflections	l = −12→12

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0477P)^2 + 0.8877P] where P = (Fo^2 + 2Fc^2)/3
971 reflections	(Δ/σ)max < 0.001
69 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.35 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.

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	0.0000	0.0000	0.0000	0.0519 (3)
N1	0.03524 (18)	0.14495 (19)	0.0000	0.0559 (7)
C1	0.1301 (2)	0.1860 (2)	0.0000	0.0570 (8)
C2	0.1225 (3)	0.2935 (2)	0.0000	0.0683 (10)
H2	0.1756	0.3384	0.0000	0.082*
C3	0.0260 (3)	0.3168 (2)	0.0000	0.0687 (10)
H3	−0.0006	0.3810	0.0000	0.082*
C4	−0.0297 (2)	0.2255 (2)	0.0000	0.0574 (8)
C5	−0.1333 (2)	0.2194 (2)	0.0000	0.0567 (8)
C6	−0.1916 (2)	0.3159 (2)	0.0000	0.0581 (8)
C7	−0.2181 (2)	0.3603 (2)	0.1200 (3)	0.0842 (9)
H7	−0.2000	0.3312	0.2031	0.101*
C8	−0.2724 (3)	0.4493 (2)	0.1196 (4)	0.0940 (10)
H8	−0.2899	0.4793	0.2023	0.113*
C9	−0.2994 (3)	0.4918 (3)	0.0000	0.0860 (13)
H9	−0.3367	0.5504	0.0000	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0429 (3)	0.0429 (3)	0.0701 (6)	0.000	0.000	0.000
N1	0.0433 (14)	0.0476 (14)	0.0769 (19)	−0.0014 (11)	0.000	0.000
C1	0.0466 (17)	0.0480 (17)	0.076 (2)	−0.0053 (14)	0.000	0.000
C2	0.058 (2)	0.0455 (18)	0.102 (3)	−0.0078 (16)	0.000	0.000
C3	0.059 (2)	0.0427 (17)	0.104 (3)	−0.0002 (15)	0.000	0.000
C4	0.0531 (19)	0.0437 (17)	0.075 (2)	0.0023 (14)	0.000	0.000
C5	0.0512 (18)	0.0460 (17)	0.073 (2)	0.0051 (14)	0.000	0.000
C6	0.0468 (17)	0.0450 (17)	0.082 (2)	0.0003 (13)	0.000	0.000
C7	0.098 (2)	0.0700 (17)	0.085 (2)	0.0213 (16)	−0.0015 (16)	−0.0056 (15)
C8	0.096 (2)	0.0693 (18)	0.117 (3)	0.0192 (16)	0.0078 (19)	−0.0209 (18)
C9	0.057 (2)	0.045 (2)	0.155 (5)	0.0027 (17)	0.000	0.000

Geometric parameters (Å, º)

Cu1—N1^i	1.995 (2)	C4—C5	1.389 (5)
Cu1—N1	1.995 (2)	C5—C1^i	1.387 (4)
Cu1—N1^ii	1.995 (2)	C5—C6	1.507 (4)
Cu1—N1^iii	1.995 (2)	C6—C7^iv	1.358 (3)
N1—C1	1.382 (4)	C6—C7	1.358 (3)
N1—C4	1.384 (4)	C7—C8	1.393 (4)
C1—C5^iii	1.387 (4)	C7—H7	0.9300
C1—C2	1.440 (4)	C8—C9	1.345 (4)
C2—C3	1.328 (5)	C8—H8	0.9300
C2—H2	0.9300	C9—C8^iv	1.345 (4)
C3—C4	1.430 (5)	C9—H9	0.9300
C3—H3	0.9300
N1^i—Cu1—N1	90.0	N1—C4—C5	125.5 (3)
N1^i—Cu1—N1^ii	90.0	N1—C4—C3	109.7 (3)
N1—Cu1—N1^ii	180.0	C5—C4—C3	124.8 (3)
N1^i—Cu1—N1^iii	180.00 (14)	C1^i—C5—C4	123.9 (3)
N1—Cu1—N1^iii	90.0	C1^i—C5—C6	118.3 (3)
N1^ii—Cu1—N1^iii	90.0	C4—C5—C6	117.8 (3)
C1—N1—C4	105.5 (3)	C7^iv—C6—C7	118.7 (3)
C1—N1—Cu1	127.1 (2)	C7^iv—C6—C5	120.67 (17)
C4—N1—Cu1	127.5 (2)	C7—C6—C5	120.67 (17)
N1—C1—C5^iii	126.0 (3)	C6—C7—C8	120.5 (3)
N1—C1—C2	109.4 (3)	C6—C7—H7	119.7
C5^iii—C1—C2	124.6 (3)	C8—C7—H7	119.7
C3—C2—C1	107.6 (3)	C9—C8—C7	120.2 (3)
C3—C2—H2	126.2	C9—C8—H8	119.9
C1—C2—H2	126.2	C7—C8—H8	119.9
C2—C3—C4	107.8 (3)	C8^iv—C9—C8	119.9 (4)
C2—C3—H3	126.1	C8^iv—C9—H9	120.1
C4—C3—H3	126.1	C8—C9—H9	120.1
N1^i—Cu1—N1—C1	180.0	C2—C3—C4—C5	180.0
N1^i—Cu1—N1—C4	0.0	N1—C4—C5—C1^i	0.0
C4—N1—C1—C5^iii	180.0	C3—C4—C5—C1^i	180.0
Cu1—N1—C1—C5^iii	0.0	N1—C4—C5—C6	180.0
C4—N1—C1—C2	0.0	C3—C4—C5—C6	0.0
Cu1—N1—C1—C2	180.0	C1^i—C5—C6—C7^iv	−90.2 (3)
N1—C1—C2—C3	0.0	C4—C5—C6—C7^iv	89.8 (3)
C5^iii—C1—C2—C3	180.0	C1^i—C5—C6—C7	90.2 (3)
C1—C2—C3—C4	0.0	C4—C5—C6—C7	−89.8 (3)
C1—N1—C4—C5	180.0	C7^iv—C6—C7—C8	0.6 (6)
Cu1—N1—C4—C5	0.0	C5—C6—C7—C8	−179.7 (3)
C1—N1—C4—C3	0.0	C6—C7—C8—C9	0.3 (5)
Cu1—N1—C4—C3	180.0	C7—C8—C9—C8^iv	−1.3 (7)
C2—C3—C4—N1	0.0

Symmetry codes: (i) −y, x, −z; (ii) −x, −y, −z; (iii) y, −x, z; (iv) x, y, −z.