(S,S)-N,N′-Dicyano­ethyl-1,2-(2-hydroxyphenyl)ethyl­enediamine

In the title mol­ecule {systematic name: 3,3′-[1,2-bis­(2-hydroxy­phen­yl)ethane-1,2-diyldiimino]propane­nitrile}, C₂₀H₂₂N₄O₂, there are three different types of intra­molecular hydrogen bonds, one of each of the types N—H...O [H...O = 2.51 (3) Å], N—H...N [H...N = 2.21 (3) Å] and O—H...N [H...O = 1.71 (3) Å]. In the crystal structure, mol­ecules are linked into one-dimensional chains in the a-axis direction via inter­molecular O—H...N [H...N = 1.95 (4) Å] hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.096
• Data-to-parameter ratio = 9.9

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.723     0.999
            Tmin(prime) and Tmax expected:      0.982     0.998
            RR(prime) =      0.736
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.74

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           27.51
           From the CIF: _reflns_number_total               2492
           Count of symmetry unique reflns         2509
           Completeness (_total/calc)             99.32%
           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
   2 ALERT level B = Potentially serious problem
   0 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
   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: COLLECT (Nonius, 2003); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2001); molecular graphics: SHELXTL/PC and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC.

3,3'-[1,2-bis(2-hydroxyphenyl)ethane-1,2-diyldiimino]propanenitrile

Crystal data

C20H22N4O2	F(000) = 744
Mr = 350.42	Dx = 1.226 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 16844 reflections
a = 8.4115 (3) Å	θ = 2.6–27.5°
b = 9.6525 (3) Å	µ = 0.08 mm^−1
c = 23.3886 (8) Å	T = 150 K
V = 1898.97 (11) Å^3	Plate, colourless
Z = 4	0.22 × 0.20 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer	2492 independent reflections
Radiation source: fine-focus sealed tube	1958 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 2.6°
φ scans, and ω scans with κ offsets	h = −9→10
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −11→12
Tmin = 0.723, Tmax = 0.999	l = −30→30
16844 measured reflections

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 0.1038P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2492 reflections	Δρmax = 0.14 e Å^−3
252 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXTL/PC (Sheldrick, 2001), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (3)

Special details

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	0.5974 (2)	0.84380 (17)	0.28914 (6)	0.0427 (4)
H1O	0.687 (4)	0.782 (3)	0.3004 (13)	0.088 (11)*
O2	0.52324 (19)	0.47199 (19)	0.47935 (7)	0.0491 (4)
H2O	0.498 (4)	0.443 (3)	0.5164 (15)	0.096 (12)*
N1	0.7940 (2)	0.68421 (19)	0.34787 (8)	0.0335 (4)
H1N	0.827 (3)	0.597 (3)	0.3362 (10)	0.049 (7)*
N2	1.0145 (3)	0.9727 (2)	0.26327 (8)	0.0492 (5)
N3	0.6870 (2)	0.41297 (18)	0.36151 (8)	0.0335 (4)
H3N	0.700 (3)	0.393 (3)	0.3992 (11)	0.055 (8)*
N4	0.9189 (3)	0.1069 (2)	0.40783 (8)	0.0461 (5)
C1	0.6538 (2)	0.6564 (2)	0.38481 (9)	0.0326 (5)
H1A	0.6923	0.6344	0.4242	0.039*
C2	0.9237 (3)	0.7523 (2)	0.37899 (10)	0.0390 (5)
H2A	0.9586	0.6925	0.4110	0.047*
H2B	0.8853	0.8409	0.3952	0.047*
C3	1.0632 (3)	0.7798 (2)	0.33927 (10)	0.0429 (5)
H3A	1.1565	0.8067	0.3626	0.052*
H3B	1.0903	0.6927	0.3191	0.052*
C4	1.0337 (3)	0.8882 (2)	0.29673 (10)	0.0393 (5)
C5	0.5469 (3)	0.7833 (2)	0.38799 (9)	0.0351 (5)
C6	0.5218 (2)	0.8678 (2)	0.34023 (9)	0.0358 (5)
C7	0.4201 (3)	0.9813 (2)	0.34352 (11)	0.0429 (5)
H7A	0.4024	1.0373	0.3107	0.051*
C8	0.3449 (3)	1.0128 (3)	0.39441 (12)	0.0515 (7)
H8A	0.2754	1.0903	0.3965	0.062*
C9	0.3703 (3)	0.9322 (3)	0.44228 (12)	0.0527 (7)
H9A	0.3196	0.9544	0.4774	0.063*
C10	0.4704 (3)	0.8184 (2)	0.43877 (10)	0.0438 (6)
H10A	0.4873	0.7630	0.4718	0.053*
C11	0.5701 (2)	0.5272 (2)	0.36031 (9)	0.0313 (5)
H11A	0.5495	0.5474	0.3190	0.038*
C12	0.6310 (3)	0.2898 (2)	0.33134 (10)	0.0410 (5)
H12A	0.5771	0.3181	0.2956	0.049*
H12B	0.5526	0.2405	0.3554	0.049*
C13	0.7680 (3)	0.1925 (2)	0.31711 (9)	0.0379 (5)
H13A	0.7260	0.1115	0.2960	0.045*
H13B	0.8439	0.2412	0.2918	0.045*
C14	0.8523 (3)	0.1440 (2)	0.36792 (9)	0.0359 (5)
C15	0.4105 (2)	0.4900 (2)	0.38622 (9)	0.0335 (5)
C16	0.3909 (3)	0.4618 (2)	0.44463 (10)	0.0390 (5)
C17	0.2435 (3)	0.4247 (3)	0.46626 (10)	0.0467 (6)
H17A	0.2309	0.4099	0.5062	0.056*
C18	0.1148 (3)	0.4092 (3)	0.43018 (10)	0.0455 (6)
H18A	0.0141	0.3838	0.4453	0.055*
C19	0.1328 (3)	0.4306 (2)	0.37198 (10)	0.0403 (5)
H19A	0.0456	0.4175	0.3468	0.048*
C20	0.2792 (2)	0.4714 (2)	0.35103 (10)	0.0357 (5)
H20A	0.2904	0.4872	0.3111	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0400 (9)	0.0488 (9)	0.0394 (9)	0.0022 (8)	0.0014 (7)	0.0059 (7)
O2	0.0391 (9)	0.0710 (11)	0.0373 (9)	−0.0158 (9)	−0.0060 (7)	0.0107 (9)
N1	0.0301 (9)	0.0316 (9)	0.0390 (10)	−0.0016 (7)	0.0016 (8)	−0.0024 (8)
N2	0.0554 (12)	0.0477 (11)	0.0446 (12)	0.0062 (11)	0.0088 (11)	0.0003 (10)
N3	0.0323 (9)	0.0313 (9)	0.0369 (10)	−0.0004 (7)	−0.0044 (8)	−0.0001 (8)
N4	0.0530 (12)	0.0419 (10)	0.0435 (11)	0.0072 (10)	−0.0009 (10)	0.0017 (9)
C1	0.0308 (11)	0.0340 (10)	0.0330 (10)	−0.0017 (9)	0.0019 (9)	0.0005 (9)
C2	0.0355 (11)	0.0385 (11)	0.0430 (12)	−0.0057 (10)	−0.0054 (10)	0.0022 (10)
C3	0.0307 (11)	0.0419 (12)	0.0562 (14)	−0.0039 (10)	−0.0015 (10)	0.0062 (11)
C4	0.0337 (12)	0.0398 (12)	0.0445 (13)	−0.0009 (10)	0.0067 (10)	−0.0075 (11)
C5	0.0324 (11)	0.0328 (10)	0.0401 (12)	−0.0046 (9)	0.0031 (9)	−0.0027 (9)
C6	0.0306 (10)	0.0357 (11)	0.0413 (12)	−0.0070 (9)	0.0011 (9)	−0.0021 (9)
C7	0.0329 (11)	0.0344 (11)	0.0614 (15)	−0.0032 (10)	−0.0042 (11)	0.0021 (11)
C8	0.0363 (13)	0.0368 (12)	0.0812 (19)	0.0008 (11)	0.0043 (13)	−0.0101 (13)
C9	0.0482 (14)	0.0496 (14)	0.0602 (15)	−0.0001 (12)	0.0122 (13)	−0.0147 (13)
C10	0.0444 (13)	0.0432 (13)	0.0438 (13)	−0.0017 (11)	0.0098 (11)	−0.0067 (10)
C11	0.0296 (10)	0.0314 (10)	0.0329 (10)	−0.0006 (9)	−0.0017 (9)	0.0014 (9)
C12	0.0381 (12)	0.0322 (10)	0.0527 (14)	0.0001 (10)	−0.0079 (11)	−0.0042 (10)
C13	0.0433 (13)	0.0340 (11)	0.0363 (11)	0.0016 (10)	−0.0029 (10)	0.0005 (10)
C14	0.0394 (11)	0.0304 (10)	0.0379 (12)	0.0027 (9)	0.0049 (10)	−0.0020 (9)
C15	0.0310 (11)	0.0318 (10)	0.0377 (11)	0.0000 (9)	0.0005 (9)	0.0028 (9)
C16	0.0313 (11)	0.0437 (12)	0.0420 (12)	−0.0053 (10)	−0.0050 (10)	0.0021 (10)
C17	0.0403 (13)	0.0601 (16)	0.0397 (13)	−0.0105 (12)	0.0048 (10)	0.0032 (11)
C18	0.0306 (12)	0.0503 (13)	0.0555 (15)	−0.0057 (11)	0.0037 (11)	−0.0001 (11)
C19	0.0279 (11)	0.0430 (12)	0.0500 (14)	−0.0001 (9)	−0.0075 (10)	−0.0032 (10)
C20	0.0342 (11)	0.0341 (11)	0.0389 (11)	0.0015 (9)	−0.0040 (10)	0.0010 (10)

Geometric parameters (Å, º)

O1—C6	1.373 (3)	C7—H7A	0.95
O1—H1O	1.00 (3)	C8—C9	1.381 (4)
O2—C16	1.382 (3)	C8—H8A	0.95
O2—H2O	0.93 (4)	C9—C10	1.387 (3)
N1—C2	1.467 (3)	C9—H9A	0.95
N1—C1	1.486 (3)	C10—H10A	0.95
N1—H1N	0.93 (3)	C11—C15	1.516 (3)
N2—C4	1.142 (3)	C11—H11A	1.00
N3—C12	1.460 (3)	C12—C13	1.523 (3)
N3—C11	1.478 (3)	C12—H12A	0.99
N3—H3N	0.91 (3)	C12—H12B	0.99
N4—C14	1.146 (3)	C13—C14	1.461 (3)
C1—C5	1.521 (3)	C13—H13A	0.99
C1—C11	1.543 (3)	C13—H13B	0.99
C1—H1A	1.00	C15—C20	1.389 (3)
C2—C3	1.520 (3)	C15—C16	1.403 (3)
C2—H2A	0.99	C16—C17	1.386 (3)
C2—H2B	0.99	C17—C18	1.380 (3)
C3—C4	1.465 (3)	C17—H17A	0.95
C3—H3A	0.99	C18—C19	1.385 (3)
C3—H3B	0.99	C18—H18A	0.95
C5—C10	1.392 (3)	C19—C20	1.383 (3)
C5—C6	1.399 (3)	C19—H19A	0.95
C6—C7	1.393 (3)	C20—H20A	0.95
C7—C8	1.382 (4)
C6—O1—H1O	102.8 (17)	C10—C9—H9A	120.2
C16—O2—H2O	110 (2)	C9—C10—C5	121.6 (2)
C2—N1—C1	112.48 (16)	C9—C10—H10A	119.2
C2—N1—H1N	109.3 (16)	C5—C10—H10A	119.2
C1—N1—H1N	104.2 (16)	N3—C11—C15	113.91 (16)
C12—N3—C11	112.53 (16)	N3—C11—C1	107.00 (15)
C12—N3—H3N	109.4 (17)	C15—C11—C1	116.55 (17)
C11—N3—H3N	105.0 (17)	N3—C11—H11A	106.2
N1—C1—C5	110.62 (16)	C15—C11—H11A	106.2
N1—C1—C11	106.98 (16)	C1—C11—H11A	106.2
C5—C1—C11	113.54 (16)	N3—C12—C13	111.31 (18)
N1—C1—H1A	108.5	N3—C12—H12A	109.4
C5—C1—H1A	108.5	C13—C12—H12A	109.4
C11—C1—H1A	108.5	N3—C12—H12B	109.4
N1—C2—C3	110.44 (18)	C13—C12—H12B	109.4
N1—C2—H2A	109.6	H12A—C12—H12B	108.0
C3—C2—H2A	109.6	C14—C13—C12	112.77 (18)
N1—C2—H2B	109.6	C14—C13—H13A	109.0
C3—C2—H2B	109.6	C12—C13—H13A	109.0
H2A—C2—H2B	108.1	C14—C13—H13B	109.0
C4—C3—C2	114.12 (19)	C12—C13—H13B	109.0
C4—C3—H3A	108.7	H13A—C13—H13B	107.8
C2—C3—H3A	108.7	N4—C14—C13	179.4 (2)
C4—C3—H3B	108.7	C20—C15—C16	117.3 (2)
C2—C3—H3B	108.7	C20—C15—C11	119.85 (18)
H3A—C3—H3B	107.6	C16—C15—C11	122.64 (19)
N2—C4—C3	178.3 (2)	O2—C16—C17	121.7 (2)
C10—C5—C6	118.0 (2)	O2—C16—C15	117.63 (19)
C10—C5—C1	120.7 (2)	C17—C16—C15	120.7 (2)
C6—C5—C1	121.29 (18)	C18—C17—C16	120.4 (2)
O1—C6—C7	117.7 (2)	C18—C17—H17A	119.8
O1—C6—C5	121.78 (19)	C16—C17—H17A	119.8
C7—C6—C5	120.5 (2)	C17—C18—C19	119.9 (2)
C8—C7—C6	120.1 (2)	C17—C18—H18A	120.0
C8—C7—H7A	119.9	C19—C18—H18A	120.0
C6—C7—H7A	119.9	C20—C19—C18	119.2 (2)
C9—C8—C7	120.2 (2)	C20—C19—H19A	120.4
C9—C8—H8A	119.9	C18—C19—H19A	120.4
C7—C8—H8A	119.9	C19—C20—C15	122.3 (2)
C8—C9—C10	119.5 (2)	C19—C20—H20A	118.8
C8—C9—H9A	120.2	C15—C20—H20A	118.8
C2—N1—C1—C5	84.7 (2)	N1—C1—C11—N3	59.2 (2)
C2—N1—C1—C11	−151.16 (17)	C5—C1—C11—N3	−178.44 (16)
C1—N1—C2—C3	−179.39 (17)	N1—C1—C11—C15	−171.97 (17)
N1—C2—C3—C4	70.5 (2)	C5—C1—C11—C15	−49.6 (2)
N1—C1—C5—C10	−142.5 (2)	C11—N3—C12—C13	162.36 (18)
C11—C1—C5—C10	97.2 (2)	N3—C12—C13—C14	60.0 (3)
N1—C1—C5—C6	37.7 (3)	N3—C11—C15—C20	−107.8 (2)
C11—C1—C5—C6	−82.6 (2)	C1—C11—C15—C20	126.8 (2)
C10—C5—C6—O1	177.4 (2)	N3—C11—C15—C16	66.8 (3)
C1—C5—C6—O1	−2.8 (3)	C1—C11—C15—C16	−58.6 (3)
C10—C5—C6—C7	−1.5 (3)	C20—C15—C16—O2	176.16 (19)
C1—C5—C6—C7	178.22 (19)	C11—C15—C16—O2	1.5 (3)
O1—C6—C7—C8	−178.0 (2)	C20—C15—C16—C17	−3.6 (3)
C5—C6—C7—C8	1.0 (3)	C11—C15—C16—C17	−178.3 (2)
C6—C7—C8—C9	0.1 (3)	O2—C16—C17—C18	−177.0 (2)
C7—C8—C9—C10	−0.7 (4)	C15—C16—C17—C18	2.7 (4)
C8—C9—C10—C5	0.2 (4)	C16—C17—C18—C19	0.1 (4)
C6—C5—C10—C9	0.9 (3)	C17—C18—C19—C20	−1.8 (4)
C1—C5—C10—C9	−178.8 (2)	C18—C19—C20—C15	0.9 (3)
C12—N3—C11—C15	58.6 (2)	C16—C15—C20—C19	1.8 (3)
C12—N3—C11—C1	−171.14 (17)	C11—C15—C20—C19	176.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	1.00 (3)	1.71 (3)	2.644 (2)	154 (3)
O2—H2O···N4^i	0.93 (4)	1.95 (4)	2.883 (3)	173 (3)
N1—H1N···N3	0.93 (3)	2.21 (3)	2.787 (3)	119 (2)
N3—H3N···O2	0.91 (3)	2.51 (3)	3.133 (3)	126 (2)
C2—H2B···N4^ii	0.99	2.60	3.489 (3)	149
C12—H12A···O1^iii	0.99	2.48	3.450 (3)	167
C17—H17A···N4^i	0.95	2.56	3.308 (3)	135

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x, y+1, z; (iii) −x+1, y−1/2, −z+1/2.