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The crystal structure of the title compound, C36H40N2O2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007136/kp6083sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007136/kp6083Isup2.hkl
Contains datablock I

CCDC reference: 605110

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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

Computing details top

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.

(1R,2R)-(+)-4,4'-Di-tert-butyl-2,2'-[1,2-diphenylethane-1,2- diylbis(nitrilomethylidyne)]diphenol top
Crystal data top
C36H40N2O2F(000) = 572
Mr = 532.70Dx = 1.171 Mg m3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2abCell parameters from 1286 reflections
a = 10.4213 (16) Åθ = 2.7–26.7°
b = 22.729 (4) ŵ = 0.07 mm1
c = 6.3769 (10) ÅT = 173 K
V = 1510.4 (4) Å3Needle, yellow
Z = 20.16 × 0.06 × 0.04 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
979 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.118
Graphite monochromatorθmax = 28.3°, θmin = 1.8°
φ and ω scansh = 1313
11737 measured reflectionsk = 2930
2142 independent reflectionsl = 88
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H 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 reflectionsΔρmax = 0.19 e Å3
202 parametersΔρmin = 0.16 e Å3
18 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/UeqOcc. (<1)
N10.9313 (2)0.55952 (12)0.8145 (4)0.0326 (7)
O10.8260 (3)0.56053 (11)0.4486 (4)0.0487 (7)
H10.890 (4)0.5494 (18)0.569 (7)0.084 (15)*
C10.7506 (3)0.60451 (15)0.5188 (6)0.0356 (9)
C20.6566 (4)0.62766 (17)0.3892 (6)0.0447 (10)
H20.64210.61120.25430.054*
C30.5847 (3)0.67433 (17)0.4567 (6)0.0452 (10)
H30.52150.68990.36480.054*
C40.5994 (3)0.70021 (18)0.6540 (6)0.0449 (10)
C50.6896 (3)0.67426 (15)0.7813 (6)0.0375 (9)
H50.70120.68980.91830.045*
C60.7645 (3)0.62671 (14)0.7212 (5)0.0310 (8)
C70.5236 (4)0.75426 (19)0.7184 (7)0.0606 (13)
C80.566 (2)0.8023 (7)0.571 (4)0.091 (4)0.621 (13)
H8A0.52170.83900.60790.137*0.621 (13)
H8B0.54430.79130.42700.137*0.621 (13)
H8C0.65870.80800.58360.137*0.621 (13)
C8A0.549 (4)0.8107 (12)0.609 (7)0.091 (4)0.379 (13)
H8A10.58040.80270.46690.137*0.379 (13)
H8A20.61370.83310.68650.137*0.379 (13)
H8A30.46940.83360.60080.137*0.379 (13)
C90.3800 (11)0.7446 (15)0.717 (3)0.115 (6)0.621 (13)
H9A0.35270.73310.57540.173*0.621 (13)
H9B0.33640.78100.75720.173*0.621 (13)
H9C0.35790.71330.81610.173*0.621 (13)
C9A0.3887 (18)0.743 (3)0.630 (6)0.115 (6)0.379 (13)
H9A10.39250.74210.47600.173*0.379 (13)
H9A20.33030.77380.67560.173*0.379 (13)
H9A30.35750.70460.68030.173*0.379 (13)
C100.5675 (14)0.7807 (5)0.9359 (14)0.101 (5)0.621 (13)
H10A0.52140.81760.96210.152*0.621 (13)
H10B0.66000.78840.93260.152*0.621 (13)
H10C0.54820.75251.04800.152*0.621 (13)
C10A0.500 (2)0.7466 (9)0.9532 (19)0.101 (5)0.379 (13)
H10D0.43800.77591.00110.152*0.379 (13)
H10E0.58140.75201.02900.152*0.379 (13)
H10F0.46710.70700.98020.152*0.379 (13)
C110.8530 (3)0.60006 (15)0.8683 (5)0.0337 (9)
H110.85290.61321.00980.040*
C121.0100 (3)0.53398 (14)0.9790 (5)0.0321 (9)
H120.98040.54991.11690.039*
C131.1488 (3)0.55000 (15)0.9503 (6)0.0344 (9)
C141.2309 (3)0.54526 (18)1.1190 (6)0.0519 (11)
H141.19810.53421.25220.062*
C151.3606 (4)0.5564 (2)1.0963 (8)0.0671 (14)
H151.41620.55321.21380.081*
C161.4090 (4)0.5721 (2)0.9042 (8)0.0679 (14)
H161.49850.57840.88690.081*
C171.3281 (4)0.57845 (19)0.7392 (7)0.0644 (13)
H171.36060.59110.60750.077*
C181.1983 (3)0.56663 (17)0.7614 (6)0.0481 (11)
H181.14320.57020.64340.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0334 (15)0.0295 (16)0.0348 (16)0.0044 (15)0.0010 (13)0.0016 (14)
O10.0602 (17)0.0450 (16)0.0410 (16)0.0094 (15)0.0003 (14)0.0052 (14)
C10.0367 (19)0.032 (2)0.039 (2)0.0024 (18)0.0031 (17)0.0004 (18)
C20.045 (2)0.054 (3)0.036 (2)0.007 (2)0.0050 (19)0.006 (2)
C30.0307 (19)0.058 (3)0.047 (2)0.005 (2)0.0032 (19)0.013 (2)
C40.041 (2)0.052 (3)0.042 (2)0.0112 (19)0.0026 (19)0.012 (2)
C50.036 (2)0.038 (2)0.039 (2)0.0025 (18)0.0018 (17)0.0029 (19)
C60.0323 (19)0.0290 (18)0.032 (2)0.0023 (16)0.0022 (15)0.0026 (17)
C70.054 (3)0.068 (3)0.060 (3)0.035 (2)0.007 (2)0.014 (3)
C80.115 (6)0.040 (5)0.119 (9)0.020 (5)0.063 (7)0.010 (6)
C8A0.115 (6)0.040 (5)0.119 (9)0.020 (5)0.063 (7)0.010 (6)
C90.052 (4)0.083 (5)0.211 (19)0.029 (4)0.053 (7)0.015 (15)
C9A0.052 (4)0.083 (5)0.211 (19)0.029 (4)0.053 (7)0.015 (15)
C100.172 (13)0.069 (8)0.063 (4)0.088 (9)0.002 (6)0.004 (6)
C10A0.172 (13)0.069 (8)0.063 (4)0.088 (9)0.002 (6)0.004 (6)
C110.0325 (19)0.032 (2)0.036 (2)0.0028 (18)0.0032 (17)0.0010 (17)
C120.0306 (18)0.0306 (19)0.035 (2)0.0048 (16)0.0027 (15)0.0013 (16)
C130.0319 (18)0.029 (2)0.042 (2)0.0015 (17)0.0001 (17)0.0037 (18)
C140.044 (2)0.057 (3)0.054 (3)0.009 (2)0.012 (2)0.014 (2)
C150.040 (2)0.080 (3)0.081 (4)0.013 (2)0.013 (2)0.018 (3)
C160.041 (2)0.074 (3)0.089 (4)0.017 (2)0.002 (3)0.005 (3)
C170.059 (3)0.070 (3)0.064 (3)0.018 (3)0.016 (2)0.015 (3)
C180.043 (2)0.053 (3)0.048 (3)0.011 (2)0.0035 (18)0.004 (2)
Geometric parameters (Å, º) top
N1—C111.278 (4)C9—H9A0.9800
N1—C121.453 (4)C9—H9B0.9800
O1—C11.348 (4)C9—H9C0.9800
O1—H11.05 (4)C9A—H9A10.9800
C1—C21.385 (5)C9A—H9A20.9800
C1—C61.394 (5)C9A—H9A30.9800
C2—C31.368 (5)C10—H10A0.9800
C2—H20.9500C10—H10B0.9800
C3—C41.397 (5)C10—H10C0.9800
C3—H30.9500C10A—H10D0.9800
C4—C51.375 (5)C10A—H10E0.9800
C4—C71.517 (5)C10A—H10F0.9800
C5—C61.387 (4)C11—H110.9500
C5—H50.9500C12—C131.502 (4)
C6—C111.448 (4)C12—C12i1.559 (6)
C7—C8A1.485 (13)C12—H121.0000
C7—C81.505 (9)C13—C181.364 (5)
C7—C91.513 (10)C13—C141.379 (5)
C7—C10A1.527 (12)C14—C151.382 (5)
C7—C9A1.539 (14)C14—H140.9500
C7—C101.579 (9)C15—C161.372 (6)
C8—H8A0.9800C15—H150.9500
C8—H8B0.9800C16—C171.356 (6)
C8—H8C0.9800C16—H160.9500
C8A—H8A10.9800C17—C181.386 (5)
C8A—H8A20.9800C17—H170.9500
C8A—H8A30.9800C18—H180.9500
C11—N1—C12117.0 (3)H8A2—C8A—H8A3109.5
C1—O1—H1108 (2)C7—C9—H9A109.5
O1—C1—C2119.7 (3)C7—C9—H9B109.5
O1—C1—C6121.0 (3)C7—C9—H9C109.5
C2—C1—C6119.3 (3)C7—C9A—H9A1109.5
C3—C2—C1119.6 (3)C7—C9A—H9A2109.5
C3—C2—H2120.2H9A1—C9A—H9A2109.5
C1—C2—H2120.2C7—C9A—H9A3109.5
C2—C3—C4123.4 (4)H9A1—C9A—H9A3109.5
C2—C3—H3118.3H9A2—C9A—H9A3109.5
C4—C3—H3118.3C7—C10—H10A109.5
C5—C4—C3115.2 (4)C7—C10—H10B109.5
C5—C4—C7122.9 (4)C7—C10—H10C109.5
C3—C4—C7121.8 (4)C7—C10A—H10D109.5
C4—C5—C6123.8 (4)C7—C10A—H10E109.5
C4—C5—H5118.1H10D—C10A—H10E109.5
C6—C5—H5118.1C7—C10A—H10F109.5
C5—C6—C1118.6 (3)H10D—C10A—H10F109.5
C5—C6—C11120.4 (3)H10E—C10A—H10F109.5
C1—C6—C11121.0 (3)N1—C11—C6122.3 (3)
C8A—C7—C9107.3 (19)N1—C11—H11118.9
C8—C7—C9112.9 (17)C6—C11—H11118.9
C8A—C7—C4118.7 (15)N1—C12—C13111.0 (3)
C8—C7—C4105.5 (8)N1—C12—C12i108.7 (2)
C9—C7—C4113.3 (13)C13—C12—C12i111.7 (3)
C8A—C7—C10A126 (2)N1—C12—H12108.5
C8—C7—C10A137.7 (12)C13—C12—H12108.5
C9—C7—C10A80.5 (13)C12i—C12—H12108.5
C4—C7—C10A104.8 (7)C18—C13—C14118.4 (3)
C8A—C7—C9A98 (3)C18—C13—C12122.6 (3)
C8—C7—C9A99 (2)C14—C13—C12118.9 (3)
C4—C7—C9A104 (2)C13—C14—C15120.7 (4)
C10A—C7—C9A101.4 (14)C13—C14—H14119.6
C8A—C7—C1092 (2)C15—C14—H14119.6
C8—C7—C10100.8 (12)C16—C15—C14120.0 (4)
C9—C7—C10110.4 (9)C16—C15—H15120.0
C4—C7—C10113.3 (4)C14—C15—H15120.0
C9A—C7—C10130.8 (15)C17—C16—C15119.4 (4)
C7—C8—H8A109.5C17—C16—H16120.3
C7—C8—H8B109.5C15—C16—H16120.3
C7—C8—H8C109.5C16—C17—C18120.5 (4)
C7—C8A—H8A1109.5C16—C17—H17119.8
C7—C8A—H8A2109.5C18—C17—H17119.8
H8A1—C8A—H8A2109.5C13—C18—C17120.9 (4)
C7—C8A—H8A3109.5C13—C18—H18119.6
H8A1—C8A—H8A3109.5C17—C18—H18119.6
O1—C1—C2—C3176.6 (3)C5—C4—C7—C9A141.7 (18)
C6—C1—C2—C34.2 (5)C3—C4—C7—C9A40.3 (19)
C1—C2—C3—C40.9 (5)C5—C4—C7—C105.2 (8)
C2—C3—C4—C52.0 (5)C3—C4—C7—C10172.9 (8)
C2—C3—C4—C7176.2 (4)C12—N1—C11—C6176.6 (3)
C3—C4—C5—C61.6 (5)C5—C6—C11—N1174.0 (3)
C7—C4—C5—C6176.5 (3)C1—C6—C11—N17.5 (5)
C4—C5—C6—C11.6 (5)C11—N1—C12—C13111.8 (3)
C4—C5—C6—C11177.0 (3)C11—N1—C12—C12i125.0 (3)
O1—C1—C6—C5176.3 (3)N1—C12—C13—C1822.2 (5)
C2—C1—C6—C54.5 (5)C12i—C12—C13—C1899.3 (3)
O1—C1—C6—C115.2 (5)N1—C12—C13—C14160.8 (3)
C2—C1—C6—C11174.0 (3)C12i—C12—C13—C1477.7 (3)
C5—C4—C7—C8A111 (2)C18—C13—C14—C150.8 (6)
C3—C4—C7—C8A67 (2)C12—C13—C14—C15176.3 (4)
C5—C4—C7—C8114.4 (13)C13—C14—C15—C160.3 (7)
C3—C4—C7—C863.6 (13)C14—C15—C16—C172.2 (8)
C5—C4—C7—C9121.5 (10)C15—C16—C17—C182.9 (7)
C3—C4—C7—C960.4 (11)C14—C13—C18—C170.0 (6)
C5—C4—C7—C10A35.7 (12)C12—C13—C18—C17177.0 (4)
C3—C4—C7—C10A146.2 (12)C16—C17—C18—C131.9 (7)
Symmetry code: (i) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N11.05 (4)1.64 (5)2.578 (4)147 (4)
 

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