The molecule of the title comound, [Cu(C36H20N4)], is not entirely planar in the crystal structure (i.e. not D4h), but is slightly deformed, with only Ci symmetry. The molecules are stacked along the b axis in a herring-bone fashion.
Supporting information
CCDC reference: 624951
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.008 Å
- R factor = 0.099
- wR factor = 0.266
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level A
RINTA01_ALERT_3_A The value of Rint is greater than 0.20
Rint given 0.206
| Author Response: The single crystal used for the present analysis was extremely small
(0.1x0.02x0.02 mm^3^). In addition, the crystallinity was found to be rather
poor.
|
PLAT020_ALERT_3_A The value of Rint is greater than 0.10 ......... 0.21
| Author Response: The single crystal used for the present analysis was extremely small
(0.1x0.02x0.02 mm^3^). In addition, the crystallinity was found to be rather
poor.
|
Alert level C
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.266
PLAT084_ALERT_2_C High R2 Value .................................. 0.27
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.60
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
2 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.
[29H,31
H-Tetrabenzo[b,g,l,q]porphinato(2-)-
κ4N21,
N22,
N23,
N24]copper(II)
top
Crystal data top
[Cu(C36H20N4)] | F(000) = 586.00 |
Mr = 572.11 | Dx = 1.599 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54187 Å |
Hall symbol: -P 2yn | Cell parameters from 7284 reflections |
a = 12.339 (2) Å | θ = 3.0–68.2° |
b = 6.5940 (12) Å | µ = 1.58 mm−1 |
c = 14.908 (3) Å | T = 93 K |
β = 101.537 (12)° | Needle, black |
V = 1188.5 (4) Å3 | 0.10 × 0.02 × 0.02 mm |
Z = 2 | |
Data collection top
Rigaku R-AXIS RAPID-F imaging-plate diffractometer | 1347 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.206 |
ω scans | θmax = 68.3° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −14→14 |
Tmin = 0.860, Tmax = 0.969 | k = −7→7 |
11140 measured reflections | l = −17→17 |
2161 independent reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.099 | w = 1/[σ2(Fo2) + (0.1369P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.266 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 1.43 e Å−3 |
2161 reflections | Δρmin = −0.55 e Å−3 |
188 parameters | |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using reflections with F2 > 2 σ(F2). The weighted
R-factor(wR), goodness of fit (S) and R-factor
(gt) are based on F, with F set to zero for negative F.
The threshold expression of F2 > 2 σ(F2) is used only for
calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.5000 | 0.5000 | 0.5000 | 0.0298 (5) | |
N1 | 0.6275 (4) | 0.5827 (8) | 0.4407 (3) | 0.0321 (12) | |
N2 | 0.4170 (4) | 0.7492 (7) | 0.4497 (3) | 0.0290 (12) | |
C1 | 0.7281 (5) | 0.4816 (9) | 0.4474 (4) | 0.0287 (14) | |
C2 | 0.8008 (5) | 0.5987 (10) | 0.4021 (4) | 0.0330 (14) | |
C3 | 0.9096 (5) | 0.5686 (10) | 0.3913 (4) | 0.0355 (15) | |
C4 | 0.9576 (5) | 0.7181 (9) | 0.3470 (4) | 0.0348 (15) | |
C5 | 0.9004 (5) | 0.8934 (10) | 0.3124 (4) | 0.0344 (15) | |
C6 | 0.7908 (5) | 0.9248 (10) | 0.3230 (4) | 0.0332 (14) | |
C7 | 0.7438 (4) | 0.7743 (9) | 0.3686 (3) | 0.0279 (13) | |
C8 | 0.6347 (4) | 0.7599 (9) | 0.3938 (4) | 0.0288 (13) | |
C9 | 0.5556 (4) | 0.9077 (10) | 0.3739 (3) | 0.0285 (13) | |
C10 | 0.4538 (4) | 0.9015 (9) | 0.4005 (4) | 0.0286 (13) | |
C11 | 0.3717 (4) | 1.0609 (9) | 0.3781 (4) | 0.0279 (13) | |
C12 | 0.3714 (4) | 1.2484 (9) | 0.3331 (4) | 0.0303 (14) | |
C13 | 0.2757 (5) | 1.3617 (9) | 0.3200 (4) | 0.0311 (14) | |
C14 | 0.1827 (5) | 1.2935 (9) | 0.3520 (4) | 0.0322 (14) | |
C15 | 0.1836 (4) | 1.1166 (10) | 0.3990 (4) | 0.0338 (14) | |
C16 | 0.2808 (5) | 0.9988 (8) | 0.4134 (4) | 0.0276 (13) | |
C17 | 0.3111 (4) | 0.8060 (9) | 0.4587 (4) | 0.0277 (13) | |
C18 | 0.2448 (5) | 0.6994 (9) | 0.5068 (4) | 0.0299 (13) | |
H3 | 0.9492 | 0.4494 | 0.4136 | 0.043* | |
H4 | 1.0319 | 0.7010 | 0.3398 | 0.042* | |
H5 | 0.9356 | 0.9919 | 0.2815 | 0.041* | |
H6 | 0.7507 | 1.0432 | 0.3001 | 0.040* | |
H9 | 0.5713 | 1.0218 | 0.3397 | 0.034* | |
H12 | 0.4350 | 1.2954 | 0.3125 | 0.036* | |
H13 | 0.2726 | 1.4878 | 0.2888 | 0.037* | |
H14 | 0.1172 | 1.3731 | 0.3406 | 0.039* | |
H15 | 0.1206 | 1.0736 | 0.4215 | 0.041* | |
H18 | 0.1744 | 0.7556 | 0.5085 | 0.036* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0183 (7) | 0.0338 (8) | 0.0383 (8) | −0.0001 (5) | 0.0079 (5) | 0.0005 (5) |
N1 | 0.020 (2) | 0.038 (3) | 0.039 (2) | 0.005 (2) | 0.006 (2) | −0.000 (2) |
N2 | 0.018 (2) | 0.034 (3) | 0.036 (2) | −0.003 (2) | 0.007 (2) | −0.003 (2) |
C1 | 0.017 (3) | 0.038 (3) | 0.031 (3) | −0.003 (2) | 0.005 (2) | −0.002 (2) |
C2 | 0.026 (3) | 0.040 (3) | 0.034 (3) | 0.001 (2) | 0.007 (2) | −0.001 (2) |
C3 | 0.025 (3) | 0.039 (3) | 0.044 (3) | 0.002 (2) | 0.010 (2) | 0.002 (3) |
C4 | 0.019 (3) | 0.045 (4) | 0.040 (3) | 0.000 (2) | 0.005 (2) | 0.000 (3) |
C5 | 0.026 (3) | 0.039 (3) | 0.042 (3) | 0.002 (2) | 0.014 (2) | 0.000 (3) |
C6 | 0.022 (3) | 0.040 (3) | 0.038 (3) | 0.005 (2) | 0.005 (2) | −0.002 (2) |
C7 | 0.015 (3) | 0.035 (3) | 0.033 (3) | −0.001 (2) | 0.003 (2) | −0.004 (2) |
C8 | 0.021 (3) | 0.037 (3) | 0.028 (3) | −0.003 (2) | 0.003 (2) | −0.000 (2) |
C9 | 0.019 (3) | 0.040 (3) | 0.027 (3) | −0.005 (2) | 0.005 (2) | −0.002 (2) |
C10 | 0.023 (3) | 0.030 (3) | 0.035 (3) | 0.003 (2) | 0.008 (2) | −0.000 (2) |
C11 | 0.012 (2) | 0.032 (3) | 0.038 (3) | −0.001 (2) | 0.001 (2) | −0.005 (2) |
C12 | 0.019 (3) | 0.030 (3) | 0.043 (3) | −0.005 (2) | 0.010 (2) | −0.001 (2) |
C13 | 0.030 (3) | 0.034 (3) | 0.026 (3) | −0.001 (2) | −0.002 (2) | −0.001 (2) |
C14 | 0.028 (3) | 0.035 (3) | 0.034 (3) | 0.007 (2) | 0.006 (2) | −0.002 (2) |
C15 | 0.019 (3) | 0.043 (3) | 0.040 (3) | −0.003 (2) | 0.008 (2) | −0.003 (3) |
C16 | 0.017 (3) | 0.032 (3) | 0.032 (3) | −0.002 (2) | 0.003 (2) | −0.004 (2) |
C17 | 0.021 (3) | 0.030 (3) | 0.030 (3) | −0.002 (2) | −0.001 (2) | −0.003 (2) |
C18 | 0.019 (3) | 0.040 (3) | 0.031 (3) | 0.003 (2) | 0.005 (2) | −0.006 (2) |
Geometric parameters (Å, º) top
Cu1—N1 | 2.027 (5) | C6—H6 | 0.950 |
Cu1—N1i | 2.027 (5) | C7—C8 | 1.471 (8) |
Cu1—N2 | 2.001 (4) | C8—C9 | 1.369 (8) |
Cu1—N2i | 2.001 (4) | C9—C10 | 1.392 (8) |
N1—C1 | 1.395 (8) | C9—H9 | 0.950 |
N1—C8 | 1.373 (8) | C10—C11 | 1.451 (8) |
N2—C10 | 1.374 (8) | C11—C12 | 1.407 (8) |
N2—C17 | 1.391 (8) | C11—C16 | 1.392 (9) |
C1—C2 | 1.449 (9) | C12—C13 | 1.378 (8) |
C1—C18i | 1.383 (8) | C12—H12 | 0.950 |
C2—C3 | 1.397 (9) | C13—C14 | 1.402 (9) |
C2—C7 | 1.395 (8) | C13—H13 | 0.950 |
C3—C4 | 1.385 (9) | C14—C15 | 1.360 (9) |
C3—H3 | 0.950 | C14—H14 | 0.950 |
C4—C5 | 1.398 (8) | C15—C16 | 1.409 (8) |
C4—H4 | 0.950 | C15—H15 | 0.950 |
C5—C6 | 1.408 (9) | C16—C17 | 1.452 (8) |
C5—H5 | 0.950 | C17—C18 | 1.383 (9) |
C6—C7 | 1.393 (9) | C18—H18 | 0.950 |
| | | |
C11···H13ii | 2.797 | H5···H12vii | 2.662 |
H18···H4iii | 2.789 | H12···H4viii | 2.466 |
H3···H3iv | 2.712 | H12···H5viii | 2.662 |
H3···H14v | 2.577 | H13···C11ix | 2.797 |
H4···H18vi | 2.789 | H14···H3x | 2.577 |
H4···H12vii | 2.466 | H14···H4x | 2.404 |
H4···H14v | 2.404 | | |
| | | |
N1—Cu1—N1i | 180.0 (2) | N1—C8—C7 | 109.9 (5) |
N1—Cu1—N2 | 90.0 (2) | N1—C8—C9 | 126.9 (5) |
N1—Cu1—N2i | 90.0 (2) | C7—C8—C9 | 123.2 (5) |
N1i—Cu1—N2 | 90.0 (2) | C8—C9—C10 | 124.2 (6) |
N1i—Cu1—N2i | 90.0 (2) | C8—C9—H9 | 117.9 |
N2—Cu1—N2i | 180.0 (2) | C10—C9—H9 | 117.9 |
Cu1—N1—C1 | 126.7 (4) | N2—C10—C9 | 126.0 (5) |
Cu1—N1—C8 | 125.9 (4) | N2—C10—C11 | 111.2 (5) |
C1—N1—C8 | 107.2 (5) | C9—C10—C11 | 122.8 (5) |
Cu1—N2—C10 | 126.9 (4) | C10—C11—C12 | 132.9 (5) |
Cu1—N2—C17 | 127.3 (4) | C10—C11—C16 | 106.2 (5) |
C10—N2—C17 | 105.8 (4) | C12—C11—C16 | 120.9 (5) |
N1—C1—C2 | 109.7 (5) | C11—C12—C13 | 117.7 (5) |
N1—C1—C18i | 124.9 (6) | C11—C12—H12 | 121.2 |
C2—C1—C18i | 125.4 (5) | C13—C12—H12 | 121.2 |
C1—C2—C3 | 132.6 (6) | C12—C13—C14 | 121.0 (5) |
C1—C2—C7 | 107.1 (5) | C12—C13—H13 | 119.5 |
C3—C2—C7 | 120.3 (6) | C14—C13—H13 | 119.5 |
C2—C3—C4 | 117.8 (6) | C13—C14—C15 | 121.8 (5) |
C2—C3—H3 | 121.1 | C13—C14—H14 | 119.1 |
C4—C3—H3 | 121.1 | C15—C14—H14 | 119.1 |
C3—C4—C5 | 122.1 (6) | C14—C15—C16 | 118.1 (6) |
C3—C4—H4 | 118.9 | C14—C15—H15 | 121.0 |
C5—C4—H4 | 118.9 | C16—C15—H15 | 121.0 |
C4—C5—C6 | 120.4 (6) | C11—C16—C15 | 120.4 (5) |
C4—C5—H5 | 119.8 | C11—C16—C17 | 106.3 (5) |
C6—C5—H5 | 119.8 | C15—C16—C17 | 133.2 (6) |
C5—C6—C7 | 116.9 (5) | N2—C17—C16 | 110.5 (5) |
C5—C6—H6 | 121.5 | N2—C17—C18 | 125.2 (5) |
C7—C6—H6 | 121.5 | C16—C17—C18 | 124.2 (5) |
C2—C7—C6 | 122.5 (5) | C1i—C18—C17 | 125.8 (5) |
C2—C7—C8 | 106.1 (5) | C1i—C18—H18 | 117.1 |
C6—C7—C8 | 131.5 (5) | C17—C18—H18 | 117.1 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x−1, y, z; (iv) −x+2, −y+1, −z+1; (v) x+1, y−1, z; (vi) x+1, y, z; (vii) −x+3/2, y−1/2, −z+1/2; (viii) −x+3/2, y+1/2, −z+1/2; (ix) −x+1/2, y+1/2, −z+1/2; (x) x−1, y+1, z. |