The crystal structure of the title compound, C
36H
40N
2O
2, has been determined at 173 (2) K. The molecule has
C2 symmetry and the asymmetric unit contains one half-molecule. An intramolecular O—H
N hydrogen bond is formed between the phenol OH group and the Schiff base N atom.
Supporting information
CCDC reference: 605110
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.048
- wR factor = 0.126
- Data-to-parameter ratio = 10.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.70 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.44 Ratio
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C7
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.117
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc.
PLAT213_ALERT_2_C Atom C10 has ADP max/min Ratio ............. 3.50 prolat
PLAT213_ALERT_2_C Atom C10A has ADP max/min Ratio ............. 3.50 prolat
PLAT301_ALERT_3_C Main Residue Disorder ......................... 13.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT355_ALERT_3_C Long O-H Bond (0.82A) O1 - H1 ... 1.05 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
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 28.29
From the CIF: _reflns_number_total 2142
Count of symmetry unique reflns 2184
Completeness (_total/calc) 98.08%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
9 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
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
7 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
| Author Response: We have developed an advanced undergraduate laboratory course in
inorganic chemistry, where one of the tasks is to modify known
structures of salen-based ligands, prepare their Mn(III) complexes and
then study effects of introducing substituents on enantiomeric excess
in epoxidation reactions. This course is normally taken together with
a course on Diffraction Methods in Structure Determination where
the final project is to determine a crystal structure of their newly
synthesized molecule with previously unknown crystal structure.
Here we present a result of the study.
Contribution of all authors
was crucial to success of the project. IVK - crystallographer, OVM,
SKB, MF - students who
synthesized and characterized the material and grew crystals,
SVK, TEH, EVRA - professors teaching the courses and supervising the
project.
|
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: XCIF in SHELXTL.
(1
R,2
R)-(+)-4,4'-Di-
tert-butyl-2,2'-[1,2-diphenylethane-1,2- diylbis(nitrilomethylidyne)]diphenol
top
Crystal data top
C36H40N2O2 | F(000) = 572 |
Mr = 532.70 | Dx = 1.171 Mg m−3 |
Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2 2ab | Cell parameters from 1286 reflections |
a = 10.4213 (16) Å | θ = 2.7–26.7° |
b = 22.729 (4) Å | µ = 0.07 mm−1 |
c = 6.3769 (10) Å | T = 173 K |
V = 1510.4 (4) Å3 | Needle, yellow |
Z = 2 | 0.16 × 0.06 × 0.04 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 979 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.118 |
Graphite monochromator | θmax = 28.3°, θmin = 1.8° |
φ and ω scans | h = −13→13 |
11737 measured reflections | k = −29→30 |
2142 independent reflections | l = −8→8 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0572P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.88 | (Δ/σ)max < 0.001 |
2142 reflections | Δρmax = 0.19 e Å−3 |
202 parameters | Δρmin = −0.16 e Å−3 |
18 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.031 (3) |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1 | 0.9313 (2) | 0.55952 (12) | 0.8145 (4) | 0.0326 (7) | |
O1 | 0.8260 (3) | 0.56053 (11) | 0.4486 (4) | 0.0487 (7) | |
H1 | 0.890 (4) | 0.5494 (18) | 0.569 (7) | 0.084 (15)* | |
C1 | 0.7506 (3) | 0.60451 (15) | 0.5188 (6) | 0.0356 (9) | |
C2 | 0.6566 (4) | 0.62766 (17) | 0.3892 (6) | 0.0447 (10) | |
H2 | 0.6421 | 0.6112 | 0.2543 | 0.054* | |
C3 | 0.5847 (3) | 0.67433 (17) | 0.4567 (6) | 0.0452 (10) | |
H3 | 0.5215 | 0.6899 | 0.3648 | 0.054* | |
C4 | 0.5994 (3) | 0.70021 (18) | 0.6540 (6) | 0.0449 (10) | |
C5 | 0.6896 (3) | 0.67426 (15) | 0.7813 (6) | 0.0375 (9) | |
H5 | 0.7012 | 0.6898 | 0.9183 | 0.045* | |
C6 | 0.7645 (3) | 0.62671 (14) | 0.7212 (5) | 0.0310 (8) | |
C7 | 0.5236 (4) | 0.75426 (19) | 0.7184 (7) | 0.0606 (13) | |
C8 | 0.566 (2) | 0.8023 (7) | 0.571 (4) | 0.091 (4) | 0.621 (13) |
H8A | 0.5217 | 0.8390 | 0.6079 | 0.137* | 0.621 (13) |
H8B | 0.5443 | 0.7913 | 0.4270 | 0.137* | 0.621 (13) |
H8C | 0.6587 | 0.8080 | 0.5836 | 0.137* | 0.621 (13) |
C8A | 0.549 (4) | 0.8107 (12) | 0.609 (7) | 0.091 (4) | 0.379 (13) |
H8A1 | 0.5804 | 0.8027 | 0.4669 | 0.137* | 0.379 (13) |
H8A2 | 0.6137 | 0.8331 | 0.6865 | 0.137* | 0.379 (13) |
H8A3 | 0.4694 | 0.8336 | 0.6008 | 0.137* | 0.379 (13) |
C9 | 0.3800 (11) | 0.7446 (15) | 0.717 (3) | 0.115 (6) | 0.621 (13) |
H9A | 0.3527 | 0.7331 | 0.5754 | 0.173* | 0.621 (13) |
H9B | 0.3364 | 0.7810 | 0.7572 | 0.173* | 0.621 (13) |
H9C | 0.3579 | 0.7133 | 0.8161 | 0.173* | 0.621 (13) |
C9A | 0.3887 (18) | 0.743 (3) | 0.630 (6) | 0.115 (6) | 0.379 (13) |
H9A1 | 0.3925 | 0.7421 | 0.4760 | 0.173* | 0.379 (13) |
H9A2 | 0.3303 | 0.7738 | 0.6756 | 0.173* | 0.379 (13) |
H9A3 | 0.3575 | 0.7046 | 0.6803 | 0.173* | 0.379 (13) |
C10 | 0.5675 (14) | 0.7807 (5) | 0.9359 (14) | 0.101 (5) | 0.621 (13) |
H10A | 0.5214 | 0.8176 | 0.9621 | 0.152* | 0.621 (13) |
H10B | 0.6600 | 0.7884 | 0.9326 | 0.152* | 0.621 (13) |
H10C | 0.5482 | 0.7525 | 1.0480 | 0.152* | 0.621 (13) |
C10A | 0.500 (2) | 0.7466 (9) | 0.9532 (19) | 0.101 (5) | 0.379 (13) |
H10D | 0.4380 | 0.7759 | 1.0011 | 0.152* | 0.379 (13) |
H10E | 0.5814 | 0.7520 | 1.0290 | 0.152* | 0.379 (13) |
H10F | 0.4671 | 0.7070 | 0.9802 | 0.152* | 0.379 (13) |
C11 | 0.8530 (3) | 0.60006 (15) | 0.8683 (5) | 0.0337 (9) | |
H11 | 0.8529 | 0.6132 | 1.0098 | 0.040* | |
C12 | 1.0100 (3) | 0.53398 (14) | 0.9790 (5) | 0.0321 (9) | |
H12 | 0.9804 | 0.5499 | 1.1169 | 0.039* | |
C13 | 1.1488 (3) | 0.55000 (15) | 0.9503 (6) | 0.0344 (9) | |
C14 | 1.2309 (3) | 0.54526 (18) | 1.1190 (6) | 0.0519 (11) | |
H14 | 1.1981 | 0.5342 | 1.2522 | 0.062* | |
C15 | 1.3606 (4) | 0.5564 (2) | 1.0963 (8) | 0.0671 (14) | |
H15 | 1.4162 | 0.5532 | 1.2138 | 0.081* | |
C16 | 1.4090 (4) | 0.5721 (2) | 0.9042 (8) | 0.0679 (14) | |
H16 | 1.4985 | 0.5784 | 0.8869 | 0.081* | |
C17 | 1.3281 (4) | 0.57845 (19) | 0.7392 (7) | 0.0644 (13) | |
H17 | 1.3606 | 0.5911 | 0.6075 | 0.077* | |
C18 | 1.1983 (3) | 0.56663 (17) | 0.7614 (6) | 0.0481 (11) | |
H18 | 1.1432 | 0.5702 | 0.6434 | 0.058* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0334 (15) | 0.0295 (16) | 0.0348 (16) | 0.0044 (15) | −0.0010 (13) | 0.0016 (14) |
O1 | 0.0602 (17) | 0.0450 (16) | 0.0410 (16) | 0.0094 (15) | 0.0003 (14) | −0.0052 (14) |
C1 | 0.0367 (19) | 0.032 (2) | 0.039 (2) | −0.0024 (18) | 0.0031 (17) | 0.0004 (18) |
C2 | 0.045 (2) | 0.054 (3) | 0.036 (2) | −0.007 (2) | −0.0050 (19) | 0.006 (2) |
C3 | 0.0307 (19) | 0.058 (3) | 0.047 (2) | 0.005 (2) | −0.0032 (19) | 0.013 (2) |
C4 | 0.041 (2) | 0.052 (3) | 0.042 (2) | 0.0112 (19) | 0.0026 (19) | 0.012 (2) |
C5 | 0.036 (2) | 0.038 (2) | 0.039 (2) | 0.0025 (18) | 0.0018 (17) | 0.0029 (19) |
C6 | 0.0323 (19) | 0.0290 (18) | 0.032 (2) | −0.0023 (16) | −0.0022 (15) | 0.0026 (17) |
C7 | 0.054 (3) | 0.068 (3) | 0.060 (3) | 0.035 (2) | 0.007 (2) | 0.014 (3) |
C8 | 0.115 (6) | 0.040 (5) | 0.119 (9) | 0.020 (5) | 0.063 (7) | −0.010 (6) |
C8A | 0.115 (6) | 0.040 (5) | 0.119 (9) | 0.020 (5) | 0.063 (7) | −0.010 (6) |
C9 | 0.052 (4) | 0.083 (5) | 0.211 (19) | 0.029 (4) | 0.053 (7) | 0.015 (15) |
C9A | 0.052 (4) | 0.083 (5) | 0.211 (19) | 0.029 (4) | 0.053 (7) | 0.015 (15) |
C10 | 0.172 (13) | 0.069 (8) | 0.063 (4) | 0.088 (9) | −0.002 (6) | −0.004 (6) |
C10A | 0.172 (13) | 0.069 (8) | 0.063 (4) | 0.088 (9) | −0.002 (6) | −0.004 (6) |
C11 | 0.0325 (19) | 0.032 (2) | 0.036 (2) | −0.0028 (18) | −0.0032 (17) | −0.0010 (17) |
C12 | 0.0306 (18) | 0.0306 (19) | 0.035 (2) | 0.0048 (16) | −0.0027 (15) | 0.0013 (16) |
C13 | 0.0319 (18) | 0.029 (2) | 0.042 (2) | −0.0015 (17) | 0.0001 (17) | 0.0037 (18) |
C14 | 0.044 (2) | 0.057 (3) | 0.054 (3) | −0.009 (2) | −0.012 (2) | 0.014 (2) |
C15 | 0.040 (2) | 0.080 (3) | 0.081 (4) | −0.013 (2) | −0.013 (2) | 0.018 (3) |
C16 | 0.041 (2) | 0.074 (3) | 0.089 (4) | −0.017 (2) | 0.002 (3) | 0.005 (3) |
C17 | 0.059 (3) | 0.070 (3) | 0.064 (3) | −0.018 (3) | 0.016 (2) | 0.015 (3) |
C18 | 0.043 (2) | 0.053 (3) | 0.048 (3) | −0.011 (2) | 0.0035 (18) | 0.004 (2) |
Geometric parameters (Å, º) top
N1—C11 | 1.278 (4) | C9—H9A | 0.9800 |
N1—C12 | 1.453 (4) | C9—H9B | 0.9800 |
O1—C1 | 1.348 (4) | C9—H9C | 0.9800 |
O1—H1 | 1.05 (4) | C9A—H9A1 | 0.9800 |
C1—C2 | 1.385 (5) | C9A—H9A2 | 0.9800 |
C1—C6 | 1.394 (5) | C9A—H9A3 | 0.9800 |
C2—C3 | 1.368 (5) | C10—H10A | 0.9800 |
C2—H2 | 0.9500 | C10—H10B | 0.9800 |
C3—C4 | 1.397 (5) | C10—H10C | 0.9800 |
C3—H3 | 0.9500 | C10A—H10D | 0.9800 |
C4—C5 | 1.375 (5) | C10A—H10E | 0.9800 |
C4—C7 | 1.517 (5) | C10A—H10F | 0.9800 |
C5—C6 | 1.387 (4) | C11—H11 | 0.9500 |
C5—H5 | 0.9500 | C12—C13 | 1.502 (4) |
C6—C11 | 1.448 (4) | C12—C12i | 1.559 (6) |
C7—C8A | 1.485 (13) | C12—H12 | 1.0000 |
C7—C8 | 1.505 (9) | C13—C18 | 1.364 (5) |
C7—C9 | 1.513 (10) | C13—C14 | 1.379 (5) |
C7—C10A | 1.527 (12) | C14—C15 | 1.382 (5) |
C7—C9A | 1.539 (14) | C14—H14 | 0.9500 |
C7—C10 | 1.579 (9) | C15—C16 | 1.372 (6) |
C8—H8A | 0.9800 | C15—H15 | 0.9500 |
C8—H8B | 0.9800 | C16—C17 | 1.356 (6) |
C8—H8C | 0.9800 | C16—H16 | 0.9500 |
C8A—H8A1 | 0.9800 | C17—C18 | 1.386 (5) |
C8A—H8A2 | 0.9800 | C17—H17 | 0.9500 |
C8A—H8A3 | 0.9800 | C18—H18 | 0.9500 |
| | | |
C11—N1—C12 | 117.0 (3) | H8A2—C8A—H8A3 | 109.5 |
C1—O1—H1 | 108 (2) | C7—C9—H9A | 109.5 |
O1—C1—C2 | 119.7 (3) | C7—C9—H9B | 109.5 |
O1—C1—C6 | 121.0 (3) | C7—C9—H9C | 109.5 |
C2—C1—C6 | 119.3 (3) | C7—C9A—H9A1 | 109.5 |
C3—C2—C1 | 119.6 (3) | C7—C9A—H9A2 | 109.5 |
C3—C2—H2 | 120.2 | H9A1—C9A—H9A2 | 109.5 |
C1—C2—H2 | 120.2 | C7—C9A—H9A3 | 109.5 |
C2—C3—C4 | 123.4 (4) | H9A1—C9A—H9A3 | 109.5 |
C2—C3—H3 | 118.3 | H9A2—C9A—H9A3 | 109.5 |
C4—C3—H3 | 118.3 | C7—C10—H10A | 109.5 |
C5—C4—C3 | 115.2 (4) | C7—C10—H10B | 109.5 |
C5—C4—C7 | 122.9 (4) | C7—C10—H10C | 109.5 |
C3—C4—C7 | 121.8 (4) | C7—C10A—H10D | 109.5 |
C4—C5—C6 | 123.8 (4) | C7—C10A—H10E | 109.5 |
C4—C5—H5 | 118.1 | H10D—C10A—H10E | 109.5 |
C6—C5—H5 | 118.1 | C7—C10A—H10F | 109.5 |
C5—C6—C1 | 118.6 (3) | H10D—C10A—H10F | 109.5 |
C5—C6—C11 | 120.4 (3) | H10E—C10A—H10F | 109.5 |
C1—C6—C11 | 121.0 (3) | N1—C11—C6 | 122.3 (3) |
C8A—C7—C9 | 107.3 (19) | N1—C11—H11 | 118.9 |
C8—C7—C9 | 112.9 (17) | C6—C11—H11 | 118.9 |
C8A—C7—C4 | 118.7 (15) | N1—C12—C13 | 111.0 (3) |
C8—C7—C4 | 105.5 (8) | N1—C12—C12i | 108.7 (2) |
C9—C7—C4 | 113.3 (13) | C13—C12—C12i | 111.7 (3) |
C8A—C7—C10A | 126 (2) | N1—C12—H12 | 108.5 |
C8—C7—C10A | 137.7 (12) | C13—C12—H12 | 108.5 |
C9—C7—C10A | 80.5 (13) | C12i—C12—H12 | 108.5 |
C4—C7—C10A | 104.8 (7) | C18—C13—C14 | 118.4 (3) |
C8A—C7—C9A | 98 (3) | C18—C13—C12 | 122.6 (3) |
C8—C7—C9A | 99 (2) | C14—C13—C12 | 118.9 (3) |
C4—C7—C9A | 104 (2) | C13—C14—C15 | 120.7 (4) |
C10A—C7—C9A | 101.4 (14) | C13—C14—H14 | 119.6 |
C8A—C7—C10 | 92 (2) | C15—C14—H14 | 119.6 |
C8—C7—C10 | 100.8 (12) | C16—C15—C14 | 120.0 (4) |
C9—C7—C10 | 110.4 (9) | C16—C15—H15 | 120.0 |
C4—C7—C10 | 113.3 (4) | C14—C15—H15 | 120.0 |
C9A—C7—C10 | 130.8 (15) | C17—C16—C15 | 119.4 (4) |
C7—C8—H8A | 109.5 | C17—C16—H16 | 120.3 |
C7—C8—H8B | 109.5 | C15—C16—H16 | 120.3 |
C7—C8—H8C | 109.5 | C16—C17—C18 | 120.5 (4) |
C7—C8A—H8A1 | 109.5 | C16—C17—H17 | 119.8 |
C7—C8A—H8A2 | 109.5 | C18—C17—H17 | 119.8 |
H8A1—C8A—H8A2 | 109.5 | C13—C18—C17 | 120.9 (4) |
C7—C8A—H8A3 | 109.5 | C13—C18—H18 | 119.6 |
H8A1—C8A—H8A3 | 109.5 | C17—C18—H18 | 119.6 |
| | | |
O1—C1—C2—C3 | −176.6 (3) | C5—C4—C7—C9A | −141.7 (18) |
C6—C1—C2—C3 | 4.2 (5) | C3—C4—C7—C9A | 40.3 (19) |
C1—C2—C3—C4 | −0.9 (5) | C5—C4—C7—C10 | 5.2 (8) |
C2—C3—C4—C5 | −2.0 (5) | C3—C4—C7—C10 | −172.9 (8) |
C2—C3—C4—C7 | 176.2 (4) | C12—N1—C11—C6 | −176.6 (3) |
C3—C4—C5—C6 | 1.6 (5) | C5—C6—C11—N1 | −174.0 (3) |
C7—C4—C5—C6 | −176.5 (3) | C1—C6—C11—N1 | 7.5 (5) |
C4—C5—C6—C1 | 1.6 (5) | C11—N1—C12—C13 | −111.8 (3) |
C4—C5—C6—C11 | −177.0 (3) | C11—N1—C12—C12i | 125.0 (3) |
O1—C1—C6—C5 | 176.3 (3) | N1—C12—C13—C18 | −22.2 (5) |
C2—C1—C6—C5 | −4.5 (5) | C12i—C12—C13—C18 | 99.3 (3) |
O1—C1—C6—C11 | −5.2 (5) | N1—C12—C13—C14 | 160.8 (3) |
C2—C1—C6—C11 | 174.0 (3) | C12i—C12—C13—C14 | −77.7 (3) |
C5—C4—C7—C8A | 111 (2) | C18—C13—C14—C15 | −0.8 (6) |
C3—C4—C7—C8A | −67 (2) | C12—C13—C14—C15 | 176.3 (4) |
C5—C4—C7—C8 | 114.4 (13) | C13—C14—C15—C16 | −0.3 (7) |
C3—C4—C7—C8 | −63.6 (13) | C14—C15—C16—C17 | 2.2 (8) |
C5—C4—C7—C9 | −121.5 (10) | C15—C16—C17—C18 | −2.9 (7) |
C3—C4—C7—C9 | 60.4 (11) | C14—C13—C18—C17 | 0.0 (6) |
C5—C4—C7—C10A | −35.7 (12) | C12—C13—C18—C17 | −177.0 (4) |
C3—C4—C7—C10A | 146.2 (12) | C16—C17—C18—C13 | 1.9 (7) |
Symmetry code: (i) −x+2, −y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 1.05 (4) | 1.64 (5) | 2.578 (4) | 147 (4) |