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The crystal structure of the title compound, (−)-2,2′-[(1S,2S)-1,2-diphenyl-1,2-ethanediylbis(nitrilomethylidyne)]diphenol, C28H24N2O2, has been determined at 173 (2) K in the non-centrosymmetric space group P21212. The mol­ecule lies on a crystallographic twofold axis of symmetry. The asymmetric unit contains one-half of the 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/S1600536803019603/om6169sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019603/om6169Isup2.hkl
Contains datablock I

CCDC reference: 225724

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.042
  • wR factor = 0.117
  • Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.98
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT355_ALERT_3_C Long O-H Bond (0.82A) O1 - H1 = 1.03 Ang.
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 28.34 From the CIF: _reflns_number_total 1605 Count of symmetry unique reflns 1656 Completeness (_total/calc) 96.92% 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 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

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.

N,N'-Bis(salicylidene)-1,2-(1S,2S)-(-)-diphenyl-1,2-ethanediamine top
Crystal data top
C28H24N2O2F(000) = 444
Mr = 420.49Dx = 1.231 Mg m3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2abCell parameters from 6042 reflections
a = 10.1341 (13) Åθ = 2.4–28.2°
b = 16.168 (2) ŵ = 0.08 mm1
c = 6.9249 (9) ÅT = 173 K
V = 1134.6 (3) Å3Block, yellow
Z = 20.40 × 0.22 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1605 independent reflections
Radiation source: fine-focus sealed tube1439 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick 1996)
h = 1312
Tmin = 0.970, Tmax = 0.988k = 2021
7362 measured reflectionsl = 99
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)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0645P)2 + 0.1064P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
1605 reflectionsΔρmax = 0.18 e Å3
150 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.079 (9)
Special details top

Experimental. Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer equipped with an LT-2 low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber using Paratone-N oil. Data were measured using omega scans of 0.3° per frame for 30 s, such that a hemisphere was collected. A total of 1650 frames were collected with a final resolution of 0.75 Å. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. Absorption corrections were applied using SADABS based on Blessing, (1995). The structures are solved by the direct method using the SHELX90 program and refined by least squares method on F2 SHELXL93, incorporated in SHELXTL V5.1.

Carbon-bound H atoms were placed in idealized positions and refined as a riding model. The H atoms bound to the phenol O atoms were found by difference fourier and refined.

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*/Ueq
O10.13431 (14)0.42496 (9)0.00663 (19)0.0471 (4)
H10.086 (3)0.437 (2)0.121 (5)0.089 (10)*
N10.06098 (14)0.41791 (8)0.3462 (2)0.0340 (3)
C10.15636 (17)0.43146 (10)0.5005 (2)0.0360 (4)
C20.2159 (2)0.40430 (13)0.3321 (3)0.0471 (5)
H20.16510.39760.21790.057*
C30.3511 (2)0.38684 (17)0.3302 (4)0.0634 (6)
H30.39180.36810.21470.076*
C40.4249 (2)0.39666 (17)0.4942 (4)0.0652 (6)
H40.51680.38500.49210.078*
C50.3662 (2)0.42336 (15)0.6618 (4)0.0571 (6)
H50.41750.43010.77560.068*
C60.2321 (2)0.44054 (11)0.6650 (3)0.0437 (4)
H60.19190.45870.78150.052*
C70.01050 (17)0.45225 (9)0.5096 (2)0.0335 (4)
H70.02710.42890.63140.040*
C90.22819 (17)0.32986 (10)0.2213 (3)0.0361 (4)
C100.22396 (18)0.36620 (10)0.0362 (2)0.0381 (4)
C110.3125 (2)0.34079 (12)0.1047 (3)0.0478 (5)
H110.31150.36610.22850.057*
C120.4019 (2)0.27880 (14)0.0651 (4)0.0535 (5)
H120.46220.26170.16230.064*
C130.4051 (2)0.24115 (13)0.1140 (4)0.0564 (6)
H130.46570.19760.13890.068*
C140.3195 (2)0.26728 (11)0.2563 (3)0.0475 (5)
H140.32290.24220.38020.057*
C150.14444 (17)0.36060 (10)0.3749 (2)0.0349 (4)
H150.15220.33730.50030.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0492 (8)0.0537 (8)0.0385 (7)0.0112 (6)0.0035 (6)0.0075 (6)
N10.0379 (7)0.0300 (6)0.0340 (7)0.0006 (6)0.0006 (6)0.0009 (5)
C10.0394 (8)0.0296 (7)0.0390 (8)0.0039 (6)0.0019 (7)0.0002 (6)
C20.0448 (10)0.0538 (10)0.0429 (9)0.0092 (9)0.0009 (8)0.0060 (8)
C30.0515 (13)0.0774 (15)0.0613 (13)0.0181 (12)0.0069 (11)0.0096 (12)
C40.0397 (10)0.0750 (14)0.0809 (17)0.0109 (10)0.0052 (12)0.0096 (13)
C50.0476 (11)0.0596 (12)0.0640 (13)0.0063 (10)0.0162 (10)0.0090 (11)
C60.0465 (10)0.0417 (9)0.0429 (9)0.0051 (8)0.0063 (8)0.0061 (7)
C70.0386 (8)0.0320 (7)0.0299 (7)0.0016 (6)0.0002 (7)0.0016 (6)
C90.0366 (8)0.0292 (7)0.0426 (8)0.0033 (6)0.0011 (7)0.0025 (6)
C100.0372 (9)0.0375 (8)0.0398 (8)0.0021 (7)0.0001 (7)0.0022 (6)
C110.0448 (10)0.0541 (11)0.0444 (9)0.0025 (9)0.0046 (9)0.0066 (8)
C120.0451 (10)0.0513 (11)0.0640 (13)0.0006 (9)0.0113 (9)0.0162 (9)
C130.0507 (12)0.0411 (10)0.0775 (14)0.0116 (8)0.0054 (12)0.0058 (9)
C140.0496 (10)0.0361 (8)0.0567 (11)0.0058 (8)0.0006 (9)0.0006 (8)
C150.0403 (8)0.0304 (7)0.0339 (7)0.0033 (6)0.0028 (7)0.0023 (6)
Geometric parameters (Å, º) top
O1—C101.348 (2)C6—H60.9500
O1—H11.03 (4)C7—C7i1.559 (3)
N1—C151.270 (2)C7—H71.0000
N1—C71.453 (2)C9—C141.393 (3)
C1—C61.381 (2)C9—C101.411 (2)
C1—C21.385 (3)C9—C151.449 (2)
C1—C71.517 (2)C10—C111.388 (3)
C2—C31.398 (3)C11—C121.379 (3)
C2—H20.9500C11—H110.9500
C3—C41.369 (4)C12—C131.382 (4)
C3—H30.9500C12—H120.9500
C4—C51.374 (3)C13—C141.378 (3)
C4—H40.9500C13—H130.9500
C5—C61.387 (3)C14—H140.9500
C5—H50.9500C15—H150.9500
C10—O1—H1105 (2)C1—C7—H7108.8
C15—N1—C7119.26 (14)C7i—C7—H7108.8
C6—C1—C2119.08 (16)C14—C9—C10118.75 (17)
C6—C1—C7118.92 (15)C14—C9—C15120.72 (16)
C2—C1—C7121.99 (15)C10—C9—C15120.44 (15)
C1—C2—C3119.9 (2)O1—C10—C11119.35 (16)
C1—C2—H2120.0O1—C10—C9120.93 (15)
C3—C2—H2120.0C11—C10—C9119.73 (16)
C4—C3—C2120.3 (2)C12—C11—C10120.02 (19)
C4—C3—H3119.9C12—C11—H11120.0
C2—C3—H3119.9C10—C11—H11120.0
C3—C4—C5120.0 (2)C11—C12—C13120.9 (2)
C3—C4—H4120.0C11—C12—H12119.5
C5—C4—H4120.0C13—C12—H12119.5
C4—C5—C6120.1 (2)C14—C13—C12119.45 (19)
C4—C5—H5120.0C14—C13—H13120.3
C6—C5—H5120.0C12—C13—H13120.3
C1—C6—C5120.64 (19)C13—C14—C9121.1 (2)
C1—C6—H6119.7C13—C14—H14119.5
C5—C6—H6119.7C9—C14—H14119.5
N1—C7—C1111.64 (13)N1—C15—C9121.70 (15)
N1—C7—C7i108.09 (11)N1—C15—H15119.2
C1—C7—C7i110.64 (17)C9—C15—H15119.2
N1—C7—H7108.8
C6—C1—C2—C30.3 (3)C14—C9—C10—O1177.70 (16)
C7—C1—C2—C3179.2 (2)C15—C9—C10—O15.9 (2)
C1—C2—C3—C40.2 (4)C14—C9—C10—C111.8 (3)
C2—C3—C4—C50.3 (4)C15—C9—C10—C11174.56 (16)
C3—C4—C5—C60.1 (4)O1—C10—C11—C12177.84 (18)
C2—C1—C6—C50.5 (3)C9—C10—C11—C121.7 (3)
C7—C1—C6—C5179.02 (18)C10—C11—C12—C130.0 (3)
C4—C5—C6—C10.3 (3)C11—C12—C13—C141.4 (4)
C15—N1—C7—C1112.74 (16)C12—C13—C14—C91.3 (3)
C15—N1—C7—C7i125.36 (16)C10—C9—C14—C130.3 (3)
C6—C1—C7—N1163.71 (14)C15—C9—C14—C13176.02 (18)
C2—C1—C7—N116.8 (2)C7—N1—C15—C9173.59 (14)
C6—C1—C7—C7i75.87 (15)C14—C9—C15—N1179.65 (17)
C2—C1—C7—C7i103.62 (16)C10—C9—C15—N13.4 (2)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N11.03 (4)1.61 (4)2.5566 (19)151 (3)
 

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