(–)-(1S,2S)-N,N′-Bis­(salicyl­idene)-1,2-di­phenyl-1,2-ethanedi­amine

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.

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

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Computing details

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

Crystal data

C28H24N2O2	F(000) = 444
Mr = 420.49	Dx = 1.231 Mg m^−3
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 6042 reflections
a = 10.1341 (13) Å	θ = 2.4–28.2°
b = 16.168 (2) Å	µ = 0.08 mm^−1
c = 6.9249 (9) Å	T = 173 K
V = 1134.6 (3) Å^3	Block, yellow
Z = 2	0.40 × 0.22 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1605 independent reflections
Radiation source: fine-focus sealed tube	1439 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick 1996)	h = −13→12
Tmin = 0.970, Tmax = 0.988	k = −20→21
7362 measured reflections	l = −9→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0645P)^2 + 0.1064P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1605 reflections	Δρmax = 0.18 e Å^−3
150 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.079 (9)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.13431 (14)	0.42496 (9)	−0.00663 (19)	0.0471 (4)
H1	−0.086 (3)	0.437 (2)	0.121 (5)	0.089 (10)*
N1	−0.06098 (14)	0.41791 (8)	0.3462 (2)	0.0340 (3)
C1	0.15636 (17)	0.43146 (10)	0.5005 (2)	0.0360 (4)
C2	0.2159 (2)	0.40430 (13)	0.3321 (3)	0.0471 (5)
H2	0.1651	0.3976	0.2179	0.057*
C3	0.3511 (2)	0.38684 (17)	0.3302 (4)	0.0634 (6)
H3	0.3918	0.3681	0.2147	0.076*
C4	0.4249 (2)	0.39666 (17)	0.4942 (4)	0.0652 (6)
H4	0.5168	0.3850	0.4921	0.078*
C5	0.3662 (2)	0.42336 (15)	0.6618 (4)	0.0571 (6)
H5	0.4175	0.4301	0.7756	0.068*
C6	0.2321 (2)	0.44054 (11)	0.6650 (3)	0.0437 (4)
H6	0.1919	0.4587	0.7815	0.052*
C7	0.01050 (17)	0.45225 (9)	0.5096 (2)	0.0335 (4)
H7	−0.0271	0.4289	0.6314	0.040*
C9	−0.22819 (17)	0.32986 (10)	0.2213 (3)	0.0361 (4)
C10	−0.22396 (18)	0.36620 (10)	0.0362 (2)	0.0381 (4)
C11	−0.3125 (2)	0.34079 (12)	−0.1047 (3)	0.0478 (5)
H11	−0.3115	0.3661	−0.2285	0.057*
C12	−0.4019 (2)	0.27880 (14)	−0.0651 (4)	0.0535 (5)
H12	−0.4622	0.2617	−0.1623	0.064*
C13	−0.4051 (2)	0.24115 (13)	0.1140 (4)	0.0564 (6)
H13	−0.4657	0.1976	0.1389	0.068*
C14	−0.3195 (2)	0.26728 (11)	0.2563 (3)	0.0475 (5)
H14	−0.3229	0.2422	0.3802	0.057*
C15	−0.14444 (17)	0.36060 (10)	0.3749 (2)	0.0349 (4)
H15	−0.1522	0.3373	0.5003	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0492 (8)	0.0537 (8)	0.0385 (7)	−0.0112 (6)	−0.0035 (6)	0.0075 (6)
N1	0.0379 (7)	0.0300 (6)	0.0340 (7)	0.0006 (6)	−0.0006 (6)	−0.0009 (5)
C1	0.0394 (8)	0.0296 (7)	0.0390 (8)	0.0039 (6)	−0.0019 (7)	0.0002 (6)
C2	0.0448 (10)	0.0538 (10)	0.0429 (9)	0.0092 (9)	−0.0009 (8)	−0.0060 (8)
C3	0.0515 (13)	0.0774 (15)	0.0613 (13)	0.0181 (12)	0.0069 (11)	−0.0096 (12)
C4	0.0397 (10)	0.0750 (14)	0.0809 (17)	0.0109 (10)	−0.0052 (12)	−0.0096 (13)
C5	0.0476 (11)	0.0596 (12)	0.0640 (13)	0.0063 (10)	−0.0162 (10)	−0.0090 (11)
C6	0.0465 (10)	0.0417 (9)	0.0429 (9)	0.0051 (8)	−0.0063 (8)	−0.0061 (7)
C7	0.0386 (8)	0.0320 (7)	0.0299 (7)	0.0016 (6)	−0.0002 (7)	0.0016 (6)
C9	0.0366 (8)	0.0292 (7)	0.0426 (8)	0.0033 (6)	0.0011 (7)	−0.0025 (6)
C10	0.0372 (9)	0.0375 (8)	0.0398 (8)	0.0021 (7)	−0.0001 (7)	−0.0022 (6)
C11	0.0448 (10)	0.0541 (11)	0.0444 (9)	0.0025 (9)	−0.0046 (9)	−0.0066 (8)
C12	0.0451 (10)	0.0513 (11)	0.0640 (13)	−0.0006 (9)	−0.0113 (9)	−0.0162 (9)
C13	0.0507 (12)	0.0411 (10)	0.0775 (14)	−0.0116 (8)	−0.0054 (12)	−0.0058 (9)
C14	0.0496 (10)	0.0361 (8)	0.0567 (11)	−0.0058 (8)	0.0006 (9)	0.0006 (8)
C15	0.0403 (8)	0.0304 (7)	0.0339 (7)	0.0033 (6)	0.0028 (7)	0.0023 (6)

Geometric parameters (Å, º)

O1—C10	1.348 (2)	C6—H6	0.9500
O1—H1	1.03 (4)	C7—C7^i	1.559 (3)
N1—C15	1.270 (2)	C7—H7	1.0000
N1—C7	1.453 (2)	C9—C14	1.393 (3)
C1—C6	1.381 (2)	C9—C10	1.411 (2)
C1—C2	1.385 (3)	C9—C15	1.449 (2)
C1—C7	1.517 (2)	C10—C11	1.388 (3)
C2—C3	1.398 (3)	C11—C12	1.379 (3)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.369 (4)	C12—C13	1.382 (4)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.374 (3)	C13—C14	1.378 (3)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.387 (3)	C14—H14	0.9500
C5—H5	0.9500	C15—H15	0.9500
C10—O1—H1	105 (2)	C1—C7—H7	108.8
C15—N1—C7	119.26 (14)	C7^i—C7—H7	108.8
C6—C1—C2	119.08 (16)	C14—C9—C10	118.75 (17)
C6—C1—C7	118.92 (15)	C14—C9—C15	120.72 (16)
C2—C1—C7	121.99 (15)	C10—C9—C15	120.44 (15)
C1—C2—C3	119.9 (2)	O1—C10—C11	119.35 (16)
C1—C2—H2	120.0	O1—C10—C9	120.93 (15)
C3—C2—H2	120.0	C11—C10—C9	119.73 (16)
C4—C3—C2	120.3 (2)	C12—C11—C10	120.02 (19)
C4—C3—H3	119.9	C12—C11—H11	120.0
C2—C3—H3	119.9	C10—C11—H11	120.0
C3—C4—C5	120.0 (2)	C11—C12—C13	120.9 (2)
C3—C4—H4	120.0	C11—C12—H12	119.5
C5—C4—H4	120.0	C13—C12—H12	119.5
C4—C5—C6	120.1 (2)	C14—C13—C12	119.45 (19)
C4—C5—H5	120.0	C14—C13—H13	120.3
C6—C5—H5	120.0	C12—C13—H13	120.3
C1—C6—C5	120.64 (19)	C13—C14—C9	121.1 (2)
C1—C6—H6	119.7	C13—C14—H14	119.5
C5—C6—H6	119.7	C9—C14—H14	119.5
N1—C7—C1	111.64 (13)	N1—C15—C9	121.70 (15)
N1—C7—C7^i	108.09 (11)	N1—C15—H15	119.2
C1—C7—C7^i	110.64 (17)	C9—C15—H15	119.2
N1—C7—H7	108.8
C6—C1—C2—C3	−0.3 (3)	C14—C9—C10—O1	−177.70 (16)
C7—C1—C2—C3	179.2 (2)	C15—C9—C10—O1	5.9 (2)
C1—C2—C3—C4	−0.2 (4)	C14—C9—C10—C11	1.8 (3)
C2—C3—C4—C5	0.3 (4)	C15—C9—C10—C11	−174.56 (16)
C3—C4—C5—C6	−0.1 (4)	O1—C10—C11—C12	177.84 (18)
C2—C1—C6—C5	0.5 (3)	C9—C10—C11—C12	−1.7 (3)
C7—C1—C6—C5	−179.02 (18)	C10—C11—C12—C13	0.0 (3)
C4—C5—C6—C1	−0.3 (3)	C11—C12—C13—C14	1.4 (4)
C15—N1—C7—C1	112.74 (16)	C12—C13—C14—C9	−1.3 (3)
C15—N1—C7—C7^i	−125.36 (16)	C10—C9—C14—C13	−0.3 (3)
C6—C1—C7—N1	−163.71 (14)	C15—C9—C14—C13	176.02 (18)
C2—C1—C7—N1	16.8 (2)	C7—N1—C15—C9	173.59 (14)
C6—C1—C7—C7^i	75.87 (15)	C14—C9—C15—N1	−179.65 (17)
C2—C1—C7—C7^i	−103.62 (16)	C10—C9—C15—N1	−3.4 (2)

Symmetry code: (i) −x, −y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.03 (4)	1.61 (4)	2.5566 (19)	151 (3)