[Tetra­kis(3-chloro­phen­yl)porphyrinato]zinc(II)

The title compound, [Zn(C₄₄H₂₈Cl₄N₄)], is a four-coordinate zinc–porphyrin complex, with 3-chloro­phenyl substituents at the meso positions of the planar metallo­porphyrin core. The mol­ecules are located on crystallographic inversion centres, exhibiting partial orientational disorder of the aryl residues. The crystal packing is stabilized by van der Waals forces and inter­molecular Cl...Cl inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 110 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.061
• wR factor = 0.171
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.04
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.

   0 ALERT level A = In general: serious problem
   0 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

[Tetrakis(3-chlorophenyl)porphyrinato]zinc(II)

Crystal data

[Zn(C44H24Cl4N4)]	F(000) = 828
Mr = 815.84	Dx = 1.539 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.7205 (4) Å	Cell parameters from 3801 reflections
b = 9.4071 (3) Å	θ = 2.6–27.9°
c = 13.5925 (5) Å	µ = 1.04 mm^−1
β = 110.7208 (17)°	T = 110 K
V = 1760.50 (10) Å^3	Prism, violet
Z = 2	0.40 × 0.35 × 0.25 mm

Data collection

Nonius KappaCCD area-detector diffractometer	4179 independent reflections
Radiation source: fine-focus sealed tube	2961 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 56 microns pixels mm^-1	θmax = 27.9°, θmin = 2.6°
1° φ scans	h = −19→18
Absorption correction: multi-scan (Blessing, 1995)	k = −12→12
Tmin = 0.681, Tmax = 0.781	l = −17→17
12967 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.171	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0873P)^2 + 1.8321P] where P = (Fo^2 + 2Fc^2)/3
4179 reflections	(Δ/σ)max < 0.001
251 parameters	Δρmax = 1.49 e Å^−3
0 restraints	Δρmin = −0.73 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	Occ. (<1)
Zn	0.0000	0.5000	0.0000	0.03056 (19)
C1	0.0188 (2)	0.6401 (4)	−0.1948 (3)	0.0337 (7)
C2	−0.0369 (3)	0.7207 (4)	−0.2871 (3)	0.0392 (8)
H2	−0.0135	0.7588	−0.3385	0.047*
C3	−0.1280 (3)	0.7316 (4)	−0.2867 (3)	0.0399 (8)
H3	−0.1806	0.7796	−0.3376	0.048*
C4	−0.1312 (2)	0.6577 (4)	−0.1958 (3)	0.0346 (7)
C5	−0.2129 (2)	0.6501 (4)	−0.1658 (3)	0.0336 (7)
C6	−0.2158 (2)	0.5855 (3)	−0.0737 (3)	0.0323 (7)
C7	−0.2996 (2)	0.5771 (4)	−0.0437 (3)	0.0348 (8)
H7	−0.3619	0.6156	−0.0814	0.042*
C8	−0.2741 (2)	0.5040 (3)	0.0485 (3)	0.0325 (7)
H8	−0.3147	0.4818	0.0872	0.039*
C9	−0.1727 (2)	0.4668 (4)	0.0758 (3)	0.0323 (7)
C10	−0.1172 (3)	0.3938 (4)	0.1669 (3)	0.0334 (7)
N21	−0.0404 (2)	0.6032 (3)	−0.1398 (2)	0.0324 (6)
N22	−0.1384 (2)	0.5172 (3)	0.0003 (2)	0.0316 (6)
C25	−0.3050 (3)	0.7174 (4)	−0.2380 (3)	0.0374 (8)
C26	−0.3518 (3)	0.6655 (4)	−0.3396 (3)	0.0452 (9)
H26	−0.3261	0.5860	−0.3641	0.054*
C27	−0.4364 (3)	0.7309 (5)	−0.4044 (3)	0.0560 (12)
H27	−0.4682	0.6956	−0.4736	0.067*	0.347 (3)
C28	−0.4749 (3)	0.8450 (5)	−0.3713 (4)	0.0598 (12)
H28	−0.5328	0.8884	−0.4166	0.072*
C29	−0.4284 (3)	0.8972 (5)	−0.2708 (4)	0.0592 (12)
H29	−0.4548	0.9766	−0.2470	0.071*	0.653 (3)
C30	−0.3440 (3)	0.8341 (4)	−0.2042 (3)	0.0461 (9)
H30	−0.3126	0.8709	−0.1354	0.055*
C31	−0.1660 (2)	0.3539 (4)	0.2429 (3)	0.0353 (8)
C32	−0.2414 (3)	0.2550 (4)	0.2165 (3)	0.0411 (8)
H32	−0.2606	0.2087	0.1502	0.049*
C33	−0.2891 (3)	0.2235 (4)	0.2861 (3)	0.0445 (9)
H33	−0.3412	0.1573	0.2666	0.053*
C34	−0.2593 (3)	0.2885 (4)	0.3843 (3)	0.0442 (9)
H34	−0.2909	0.2673	0.4326	0.053*
C35	−0.1843 (3)	0.3845 (4)	0.4099 (3)	0.0429 (9)
C36	−0.1370 (3)	0.4189 (4)	0.3417 (3)	0.0390 (8)
H36	−0.0854	0.4859	0.3615	0.047*
Cl1	−0.49746 (12)	0.6797 (2)	−0.52779 (13)	0.0613 (6)	0.653 (3)
Cl1'	−0.4805 (2)	1.0225 (3)	−0.2402 (3)	0.0602 (11)	0.347 (3)
Cl2	−0.15001 (9)	0.47244 (14)	0.53082 (8)	0.0612 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn	0.0307 (3)	0.0312 (3)	0.0268 (3)	0.0016 (2)	0.0065 (2)	0.0027 (2)
C1	0.0360 (18)	0.0319 (16)	0.0308 (17)	−0.0004 (14)	0.0088 (14)	0.0034 (13)
C2	0.040 (2)	0.0390 (18)	0.0357 (18)	0.0002 (16)	0.0093 (16)	0.0093 (15)
C3	0.043 (2)	0.0380 (19)	0.0347 (18)	0.0046 (16)	0.0090 (16)	0.0107 (15)
C4	0.0339 (17)	0.0319 (16)	0.0321 (17)	0.0015 (14)	0.0044 (14)	0.0061 (14)
C5	0.0308 (17)	0.0317 (16)	0.0326 (17)	0.0001 (14)	0.0044 (14)	0.0022 (13)
C6	0.0327 (17)	0.0307 (16)	0.0288 (16)	−0.0001 (13)	0.0051 (14)	−0.0001 (13)
C7	0.0311 (17)	0.0320 (17)	0.0356 (18)	0.0016 (14)	0.0047 (14)	−0.0012 (14)
C8	0.0323 (17)	0.0321 (16)	0.0305 (16)	−0.0008 (14)	0.0079 (14)	−0.0004 (14)
C9	0.0322 (17)	0.0326 (16)	0.0308 (17)	−0.0007 (14)	0.0095 (14)	−0.0019 (13)
C10	0.0373 (18)	0.0306 (16)	0.0302 (17)	−0.0006 (14)	0.0095 (14)	−0.0003 (13)
N21	0.0315 (14)	0.0311 (14)	0.0306 (14)	0.0027 (11)	0.0060 (12)	0.0043 (11)
N22	0.0324 (14)	0.0317 (14)	0.0277 (14)	0.0000 (11)	0.0069 (12)	0.0000 (11)
C25	0.0311 (17)	0.0392 (18)	0.0382 (19)	−0.0019 (15)	0.0077 (15)	0.0108 (15)
C26	0.040 (2)	0.051 (2)	0.039 (2)	−0.0033 (17)	0.0060 (16)	0.0116 (17)
C27	0.038 (2)	0.075 (3)	0.043 (2)	−0.010 (2)	−0.0011 (18)	0.020 (2)
C28	0.035 (2)	0.073 (3)	0.064 (3)	0.010 (2)	0.008 (2)	0.029 (2)
C29	0.042 (2)	0.059 (3)	0.073 (3)	0.012 (2)	0.015 (2)	0.021 (2)
C30	0.0364 (19)	0.044 (2)	0.054 (2)	0.0033 (17)	0.0114 (18)	0.0118 (18)
C31	0.0338 (17)	0.0363 (18)	0.0341 (18)	0.0049 (15)	0.0098 (14)	0.0063 (14)
C32	0.044 (2)	0.0393 (19)	0.0372 (19)	−0.0015 (16)	0.0107 (17)	0.0025 (15)
C33	0.046 (2)	0.044 (2)	0.044 (2)	−0.0041 (17)	0.0171 (18)	0.0033 (17)
C34	0.047 (2)	0.047 (2)	0.041 (2)	0.0029 (18)	0.0175 (17)	0.0114 (17)
C35	0.052 (2)	0.046 (2)	0.0298 (18)	0.0087 (17)	0.0133 (17)	0.0052 (15)
C36	0.041 (2)	0.0392 (19)	0.0350 (18)	0.0008 (16)	0.0110 (16)	0.0047 (15)
Cl1	0.0462 (9)	0.0831 (13)	0.0392 (9)	−0.0075 (8)	−0.0040 (7)	0.0040 (8)
Cl1'	0.0446 (17)	0.0510 (18)	0.074 (2)	0.0177 (13)	0.0076 (15)	−0.0102 (15)
Cl2	0.0670 (7)	0.0800 (8)	0.0349 (5)	−0.0102 (6)	0.0161 (5)	−0.0058 (5)

Geometric parameters (Å, º)

Zn—N21^i	2.027 (3)	C25—C30	1.389 (6)
Zn—N21	2.027 (3)	C25—C26	1.395 (5)
Zn—N22^i	2.045 (3)	C26—C27	1.389 (5)
Zn—N22	2.045 (3)	C26—H26	0.9500
C1—N21	1.378 (4)	C27—C28	1.362 (7)
C1—C10^i	1.399 (5)	C27—Cl1	1.669 (5)
C1—C2	1.447 (5)	C27—H27	0.9500
C2—C3	1.347 (5)	C28—C29	1.384 (7)
C2—H2	0.9500	C28—H28	0.9500
C3—C4	1.434 (5)	C29—C30	1.386 (5)
C3—H3	0.9500	C29—Cl1'	1.541 (6)
C4—N21	1.382 (4)	C29—H29	0.9500
C4—C5	1.401 (5)	C30—H30	0.9500
C5—C6	1.405 (5)	C31—C32	1.395 (5)
C5—C25	1.504 (5)	C31—C36	1.398 (5)
C6—N22	1.383 (4)	C32—C33	1.395 (5)
C6—C7	1.432 (5)	C32—H32	0.9500
C7—C8	1.360 (5)	C33—C34	1.391 (6)
C7—H7	0.9500	C33—H33	0.9500
C8—C9	1.447 (5)	C34—C35	1.372 (6)
C8—H8	0.9500	C34—H34	0.9500
C9—N22	1.379 (4)	C35—C36	1.381 (5)
C9—C10	1.399 (5)	C35—Cl2	1.747 (4)
C10—C1^i	1.399 (5)	C36—H36	0.9500
C10—C31	1.499 (5)
N21^i—Zn—N21	180.0	C6—N22—Zn	126.9 (2)
N21^i—Zn—N22^i	90.12 (11)	C30—C25—C26	119.1 (3)
N21—Zn—N22^i	89.88 (11)	C30—C25—C5	120.0 (3)
N21^i—Zn—N22	89.88 (11)	C26—C25—C5	120.9 (3)
N21—Zn—N22	90.12 (11)	C27—C26—C25	119.4 (4)
N22^i—Zn—N22	180.0	C27—C26—H26	120.3
N21—C1—C10^i	126.1 (3)	C25—C26—H26	120.3
N21—C1—C2	109.3 (3)	C28—C27—C26	121.6 (4)
C10^i—C1—C2	124.7 (3)	C28—C27—Cl1	114.8 (3)
C3—C2—C1	107.2 (3)	C26—C27—Cl1	123.6 (4)
C3—C2—H2	126.4	C28—C27—H27	119.1
C1—C2—H2	126.4	C26—C27—H27	119.4
C2—C3—C4	107.7 (3)	C27—C28—C29	119.2 (4)
C2—C3—H3	126.2	C27—C28—H28	120.5
C4—C3—H3	126.2	C29—C28—H28	120.3
N21—C4—C5	125.7 (3)	C28—C29—C30	120.5 (5)
N21—C4—C3	109.5 (3)	C28—C29—Cl1'	114.8 (4)
C5—C4—C3	124.7 (3)	C30—C29—Cl1'	124.6 (4)
C4—C5—C6	125.5 (3)	C28—C29—H29	119.7
C4—C5—C25	117.2 (3)	C30—C29—H29	119.7
C6—C5—C25	117.3 (3)	C25—C30—C29	120.2 (4)
N22—C6—C5	124.9 (3)	C25—C30—H30	120.0
N22—C6—C7	109.8 (3)	C29—C30—H30	119.9
C5—C6—C7	125.3 (3)	C32—C31—C36	118.9 (3)
C8—C7—C6	107.7 (3)	C32—C31—C10	121.4 (3)
C8—C7—H7	126.1	C36—C31—C10	119.6 (3)
C6—C7—H7	126.1	C31—C32—C33	120.9 (3)
C7—C8—C9	106.4 (3)	C31—C32—H32	119.5
C7—C8—H8	126.8	C33—C32—H32	119.6
C9—C8—H8	126.8	C34—C33—C32	119.6 (4)
N22—C9—C10	125.1 (3)	C34—C33—H33	120.3
N22—C9—C8	110.0 (3)	C32—C33—H33	120.1
C10—C9—C8	124.9 (3)	C35—C34—C33	119.0 (3)
C1^i—C10—C9	125.2 (3)	C35—C34—H34	120.6
C1^i—C10—C31	117.3 (3)	C33—C34—H34	120.4
C9—C10—C31	117.4 (3)	C34—C35—C36	122.4 (4)
C1—N21—C4	106.4 (3)	C34—C35—Cl2	119.3 (3)
C1—N21—Zn	126.7 (2)	C36—C35—Cl2	118.3 (3)
C4—N21—Zn	126.8 (2)	C35—C36—C31	119.2 (4)
C9—N22—C6	106.0 (3)	C35—C36—H36	120.5
C9—N22—Zn	127.1 (2)	C31—C36—H36	120.3

Symmetry code: (i) −x, −y+1, −z.