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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1757.
Published online 2008 August 16. doi:  10.1107/S160053680802552X
PMCID: PMC2960556

(E,E)-2,2′-[1,1′-(Cyclohexane-1,2-diyl­dinitrilo)diethylidyne]diphenol

Abstract

The title compound, C22H26N2O2, is chiral; the absolute configuration follows from the known chirality of the input reagents. The asymmetric unit contains two crystallographically independent mol­ecules in different orientations. The two mol­ecules are related to each other by a non-crystallographic twofold rotation axis, while each mol­ecule exhibits a further pseudo-twofold axis. Bond distances and angles are similar in the two mol­ecules. Inter­molecular C—H(...)π(ring) inter­actions and intra­molecular O—H(...)N hydrogen bonds are observed in the crystal structure.

Related literature

For examples of syntheses of non-centrosymmetric solid materials by reaction of chiral organic ligands and inorganic salts, see: Qu et al. (2004 [triangle]). For related structures, see: Figuet et al. (2001 [triangle]); Kennedy & Reglinski (2001 [triangle]); Thamotharan et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1757-scheme1.jpg

Experimental

Crystal data

  • C22H26N2O2
  • M r = 350.45
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1757-efi1.jpg
  • a = 12.608 (3) Å
  • b = 11.185 (2) Å
  • c = 14.438 (3) Å
  • β = 106.14 (3)°
  • V = 1955.8 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 (2) K
  • 0.25 × 0.15 × 0.15 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.839, T max = 1.000 (expected range = 0.829–0.989)
  • 20307 measured reflections
  • 4712 independent reflections
  • 2978 reflections with I > 2σ(I)
  • R int = 0.079

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.134
  • S = 1.04
  • 4712 reflections
  • 473 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected torsion angles (°)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802552X/ez2132sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802552X/ez2132Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by a Start-up Grant from Southeast University to HYY.

supplementary crystallographic information

Comment

The existence of a chiral centre in an organic ligand is very important for the construction of noncentrosymmetric or chiral coordination polymers that exhibit desirable physical properties such as ferroelectric behavior (Qu et al., 2004). As a part of our ongoing investigations in this field we have determined the crystal structure of the title compound, (I).

Fig. 1 shows the asymmetric unit consisting of two molecules of (I). The two crystallographically independent molecules have the same geometrical parameters within the precision of the experiments. The bond lengths and angles in (I) are comparable to the corresponding values in the related structures, tris[(5-bromosalicylidene)aminoethyl]amine (Figuet et al., 2001), N,N'-bis(salicylidene)-1,4-butanediamine (Kennedy & Reglinski, 2001) and N-(4-Butylphenyl)salicylaldimine (Thamotharan et al., 2003). The average for the N1—C1—C6—N2 and N3—C28—C23—N4 torsion angles is 67.5 (3)°, the average dihedral angle between two benzene rings within one molecule is 48.0 (1)°, and the average distance between the centers of the two benzene rings is 6.53 Å. Like other Schiff base compounds containing salicylidene (Figuet et al., 2001; Kennedy & Reglinski, 2001; Thamotharan et al., 2003) the hydroxyl groups form intramolecular hydrogen bonds with the N atoms (Table 2), thereby completing six-membered rings.

Experimental

o-Hydroxyacetophenone (0.68 g, 5.0 mmol) and (1R,2R)-(-)-diaminocyclohexane (0.30 g, 2.6 mmol) were dissolved in ethanol (30 mL), and heated to reflux for 8 h until the raw material disappeared according to TLC detection. The solution was cooled to room temperature, then solvent was removed under reduced pressure. The residue was recrystallized with iso-propanol to afford yellow crystals, some of which were suitable for X-ray analysis.

Refinement

Positional parameters of the H atoms bonded to C atoms were calculated geometrically and were allowed to ride on the C atoms with Cmethine—Hmethine = 0.97; Cmethylene—Hmethylene = 0.96; Caryl—Haryl=0.93 Å; UisoH = 1.2 UeqC. Positional parameters of the H atoms bonded to O atoms were calculated geometrically with the C—O—H angle tetrahedtral and refined in a rotating mode with O—H = 0.82 Å and UisoH = 1.5 UeqO. In the absence of significant anomalous scattering effects, 4211 Friedel pairs were merged.

Figures

Fig. 1.
A view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C22H26N2O2F000 = 752
Mr = 350.45Dx = 1.190 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 15855 reflections
a = 12.608 (3) Åθ = 3.1–27.5º
b = 11.185 (2) ŵ = 0.08 mm1
c = 14.438 (3) ÅT = 293 (2) K
β = 106.14 (3)ºBlock, yellow
V = 1955.8 (8) Å30.25 × 0.15 × 0.15 mm
Z = 4

Data collection

Rigaku SCXmini diffractometer4712 independent reflections
Radiation source: fine-focus sealed tube2978 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.079
Detector resolution: 13.6612 pixels mm-1θmax = 27.5º
T = 293(2) Kθmin = 3.1º
ω scansh = −16→16
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)k = −14→14
Tmin = 0.839, Tmax = 1.000l = −18→18
20307 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.134  w = 1/[σ2(Fo2) + (0.0522P)2 + 0.0566P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4712 reflectionsΔρmax = 0.15 e Å3
473 parametersΔρmin = −0.21 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

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 (Å2)

xyzUiso*/Ueq
C10.8617 (3)0.4943 (3)0.1556 (2)0.0489 (8)
H1A0.86330.40670.15630.059*
C20.7600 (3)0.5372 (4)0.0777 (2)0.0653 (10)
H2A0.76320.62340.07190.078*
H2B0.76060.50250.01630.078*
C30.6538 (3)0.5033 (5)0.1001 (3)0.0859 (14)
H3A0.64710.41690.10040.103*
H3B0.59160.53470.05050.103*
C40.6516 (3)0.5525 (5)0.1977 (3)0.0810 (13)
H4A0.65160.63920.19580.097*
H4B0.58470.52660.21240.097*
C50.7509 (3)0.5092 (4)0.2750 (2)0.0621 (10)
H5A0.74620.42300.28060.075*
H5B0.74960.54400.33620.075*
C60.8595 (3)0.5404 (3)0.2551 (2)0.0481 (8)
H6A0.86920.62740.25760.058*
C71.0699 (3)0.6613 (3)0.3580 (3)0.0662 (11)
H7A1.01170.69720.30820.099*
H7B1.13670.66070.33850.099*
H7C1.08120.70660.41640.099*
C81.0387 (3)0.5365 (3)0.3748 (2)0.0468 (8)
C91.1180 (3)0.4648 (3)0.4499 (2)0.0469 (8)
C101.2200 (3)0.5109 (4)0.5008 (3)0.0676 (11)
H10A1.23900.58740.48580.081*
C111.2940 (4)0.4480 (5)0.5724 (3)0.0806 (13)
H11A1.36150.48140.60540.097*
C121.2654 (4)0.3336 (5)0.5943 (3)0.0785 (13)
H12A1.31420.28940.64210.094*
C131.1657 (3)0.2861 (4)0.5457 (3)0.0676 (11)
H13A1.14760.20940.56100.081*
C141.0911 (3)0.3494 (3)0.4743 (2)0.0517 (9)
C151.0654 (3)0.3516 (3)0.1656 (3)0.0702 (11)
H15A1.00230.32250.18350.105*
H15B1.12980.34560.21970.105*
H15C1.07590.30460.11320.105*
C161.0473 (3)0.4797 (3)0.1349 (2)0.0478 (8)
C171.1339 (3)0.5435 (4)0.1040 (2)0.0512 (9)
C181.2338 (3)0.4887 (5)0.1053 (3)0.0716 (11)
H18A1.24570.40980.12600.086*
C191.3151 (4)0.5479 (7)0.0767 (3)0.0967 (18)
H19A1.38080.50930.07790.116*
C201.2980 (5)0.6670 (7)0.0457 (3)0.0980 (19)
H20A1.35280.70880.02770.118*
C211.2004 (5)0.7204 (5)0.0424 (3)0.0856 (14)
H21A1.18860.79850.01970.103*
C221.1184 (4)0.6632 (4)0.0713 (3)0.0643 (11)
C230.8857 (2)0.5409 (3)0.6760 (2)0.0444 (7)
H23A0.87900.62680.68680.053*
C240.9936 (3)0.5162 (4)0.6505 (2)0.0539 (9)
H24A0.99590.43280.63280.065*
H24B0.99600.56440.59530.065*
C251.0939 (3)0.5445 (4)0.7343 (3)0.0656 (10)
H25A1.16040.52300.71700.079*
H25B1.09630.62970.74710.079*
C261.0910 (3)0.4776 (4)0.8245 (3)0.0653 (10)
H26A1.15300.50250.87750.078*
H26B1.09850.39260.81450.078*
C270.9838 (3)0.5003 (3)0.8508 (2)0.0536 (9)
H27A0.98080.58360.86870.064*
H27B0.98250.45170.90610.064*
C280.8828 (2)0.4711 (3)0.7670 (2)0.0442 (8)
H28A0.88170.38520.75350.053*
C290.6789 (3)0.3226 (4)0.7262 (3)0.0618 (10)
H29A0.74560.30050.71080.093*
H29B0.61980.32900.66780.093*
H29C0.66090.26270.76700.093*
C300.6950 (3)0.4407 (3)0.7775 (2)0.0460 (8)
C310.6028 (3)0.4925 (4)0.8083 (2)0.0537 (9)
C320.5077 (3)0.4256 (5)0.8044 (3)0.0759 (13)
H32A0.50430.34590.78540.091*
C330.4196 (4)0.4758 (7)0.8280 (3)0.0983 (18)
H33A0.35790.42930.82630.118*
C340.4212 (4)0.5939 (7)0.8541 (3)0.0988 (19)
H34A0.35980.62830.86720.119*
C350.5133 (4)0.6599 (5)0.8605 (3)0.0827 (14)
H35A0.51460.73960.87930.099*
C360.6064 (3)0.6113 (4)0.8396 (2)0.0608 (10)
C370.6766 (3)0.6765 (3)0.6016 (3)0.0625 (10)
H37A0.73820.70200.65340.094*
H37B0.61280.66710.62500.094*
H37C0.66160.73530.55120.094*
C380.7033 (3)0.5594 (3)0.5629 (2)0.0458 (8)
C390.6193 (3)0.5043 (3)0.4824 (2)0.0466 (8)
C400.5179 (3)0.5605 (4)0.4382 (3)0.0658 (10)
H40A0.50320.63460.46110.079*
C410.4406 (3)0.5103 (5)0.3628 (3)0.0759 (13)
H41A0.37460.55010.33520.091*
C420.4603 (3)0.4007 (4)0.3276 (3)0.0713 (12)
H42A0.40790.36650.27600.086*
C430.5573 (3)0.3421 (4)0.3689 (3)0.0624 (10)
H43A0.57010.26800.34490.075*
C440.6369 (3)0.3913 (3)0.4457 (2)0.0508 (9)
N10.9588 (2)0.5395 (3)0.13073 (17)0.0476 (7)
N20.9485 (2)0.4849 (2)0.32967 (17)0.0463 (7)
N30.7838 (2)0.5031 (2)0.79504 (17)0.0459 (6)
N40.7941 (2)0.5016 (2)0.59532 (18)0.0452 (6)
O11.0250 (3)0.7226 (2)0.0652 (2)0.0832 (9)
H10.98040.67790.07940.125*
O20.9943 (2)0.2974 (2)0.4311 (2)0.0733 (8)
H20.95890.34050.38750.110*
O30.6953 (2)0.6804 (2)0.8496 (2)0.0701 (7)
H30.74880.63840.85030.105*
O40.7305 (2)0.3302 (2)0.48161 (19)0.0667 (7)
H40.77260.36960.52420.100*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0546 (19)0.0462 (19)0.0449 (17)0.0008 (17)0.0119 (15)0.0042 (16)
C20.062 (2)0.083 (3)0.0469 (19)0.001 (2)0.0093 (17)0.008 (2)
C30.057 (2)0.120 (4)0.069 (3)−0.006 (3)−0.0028 (19)0.017 (3)
C40.055 (2)0.107 (4)0.083 (3)0.006 (3)0.023 (2)0.020 (3)
C50.061 (2)0.074 (3)0.055 (2)−0.002 (2)0.0225 (18)0.003 (2)
C60.0548 (19)0.0464 (19)0.0446 (18)−0.0062 (17)0.0161 (15)0.0042 (16)
C70.068 (2)0.048 (2)0.073 (2)−0.016 (2)0.004 (2)0.008 (2)
C80.0545 (19)0.0467 (19)0.0418 (17)−0.0036 (17)0.0178 (15)−0.0025 (15)
C90.056 (2)0.050 (2)0.0377 (17)−0.0027 (17)0.0176 (15)−0.0051 (15)
C100.066 (2)0.073 (3)0.058 (2)−0.011 (2)0.0095 (19)0.003 (2)
C110.068 (3)0.100 (4)0.062 (3)−0.007 (3)−0.003 (2)0.001 (3)
C120.077 (3)0.096 (4)0.056 (2)0.024 (3)0.008 (2)0.009 (2)
C130.078 (3)0.060 (2)0.063 (2)0.012 (2)0.016 (2)0.011 (2)
C140.056 (2)0.054 (2)0.0447 (19)0.0023 (18)0.0143 (16)0.0006 (17)
C150.074 (3)0.055 (2)0.082 (3)0.012 (2)0.024 (2)0.013 (2)
C160.062 (2)0.047 (2)0.0317 (15)0.0017 (18)0.0088 (15)0.0032 (14)
C170.053 (2)0.065 (2)0.0331 (16)−0.0066 (19)0.0089 (15)−0.0019 (16)
C180.058 (2)0.099 (3)0.055 (2)0.001 (2)0.0117 (18)0.008 (2)
C190.061 (3)0.171 (6)0.058 (3)−0.021 (4)0.016 (2)−0.007 (3)
C200.093 (4)0.152 (6)0.055 (3)−0.064 (4)0.032 (3)−0.020 (3)
C210.116 (4)0.082 (3)0.069 (3)−0.041 (3)0.043 (3)−0.010 (2)
C220.090 (3)0.060 (2)0.051 (2)−0.017 (2)0.032 (2)−0.0024 (19)
C230.0459 (18)0.0395 (17)0.0475 (17)0.0024 (16)0.0125 (14)−0.0082 (15)
C240.0498 (19)0.056 (2)0.059 (2)0.0010 (17)0.0201 (16)−0.0061 (18)
C250.0452 (19)0.072 (3)0.079 (3)−0.003 (2)0.0167 (19)−0.011 (2)
C260.044 (2)0.068 (3)0.073 (3)0.0002 (19)−0.0009 (17)−0.009 (2)
C270.0524 (19)0.054 (2)0.0497 (19)0.0043 (18)0.0061 (15)−0.0026 (17)
C280.0467 (18)0.0364 (17)0.0477 (18)0.0043 (15)0.0101 (14)−0.0009 (15)
C290.062 (2)0.065 (2)0.058 (2)−0.011 (2)0.0145 (18)−0.008 (2)
C300.0482 (19)0.053 (2)0.0339 (16)0.0023 (17)0.0061 (14)0.0014 (15)
C310.0443 (19)0.078 (3)0.0359 (16)0.0059 (19)0.0062 (14)0.0046 (18)
C320.048 (2)0.124 (4)0.054 (2)−0.007 (2)0.0105 (18)−0.009 (2)
C330.055 (3)0.173 (6)0.071 (3)−0.008 (3)0.023 (2)−0.012 (4)
C340.062 (3)0.175 (6)0.065 (3)0.035 (4)0.026 (2)0.001 (4)
C350.083 (3)0.107 (4)0.062 (3)0.036 (3)0.026 (2)0.005 (3)
C360.062 (2)0.083 (3)0.0400 (19)0.019 (2)0.0178 (18)0.0066 (19)
C370.071 (2)0.059 (2)0.058 (2)0.025 (2)0.0190 (19)0.0029 (19)
C380.0503 (19)0.049 (2)0.0440 (17)0.0090 (17)0.0227 (15)0.0068 (16)
C390.0457 (18)0.053 (2)0.0419 (17)0.0040 (16)0.0143 (14)0.0109 (16)
C400.056 (2)0.076 (3)0.063 (2)0.008 (2)0.0127 (19)0.011 (2)
C410.050 (2)0.091 (4)0.076 (3)0.005 (2)0.000 (2)0.026 (3)
C420.058 (3)0.083 (3)0.063 (3)−0.019 (2)0.001 (2)0.019 (2)
C430.063 (2)0.065 (2)0.054 (2)−0.017 (2)0.0075 (19)0.0057 (19)
C440.051 (2)0.055 (2)0.0428 (19)−0.0020 (18)0.0078 (16)0.0073 (17)
N10.0564 (16)0.0468 (16)0.0398 (14)−0.0001 (15)0.0136 (12)0.0050 (13)
N20.0533 (16)0.0438 (16)0.0407 (14)−0.0073 (14)0.0112 (13)0.0029 (13)
N30.0463 (15)0.0470 (16)0.0439 (14)0.0026 (14)0.0117 (12)−0.0042 (13)
N40.0436 (15)0.0464 (16)0.0454 (15)0.0068 (14)0.0121 (12)−0.0005 (13)
O10.115 (3)0.0492 (17)0.101 (2)0.0006 (18)0.057 (2)0.0104 (16)
O20.0760 (18)0.0524 (16)0.0798 (19)−0.0119 (15)0.0023 (14)0.0146 (14)
O30.0811 (19)0.0616 (17)0.0761 (18)0.0126 (15)0.0362 (16)−0.0051 (15)
O40.0641 (16)0.0548 (15)0.0686 (17)0.0047 (14)−0.0023 (13)−0.0095 (13)

Geometric parameters (Å, °)

C1—N11.459 (4)C23—C281.538 (4)
C1—C21.529 (4)C23—H23A0.9800
C1—C61.534 (4)C24—C251.521 (5)
C1—H1A0.9800C24—H24A0.9700
C2—C31.511 (5)C24—H24B0.9700
C2—H2A0.9700C25—C261.510 (5)
C2—H2B0.9700C25—H25A0.9700
C3—C41.520 (6)C25—H25B0.9700
C3—H3A0.9700C26—C271.524 (5)
C3—H3B0.9700C26—H26A0.9700
C4—C51.507 (5)C26—H26B0.9700
C4—H4A0.9700C27—C281.528 (4)
C4—H4B0.9700C27—H27A0.9700
C5—C61.516 (4)C27—H27B0.9700
C5—H5A0.9700C28—N31.460 (4)
C5—H5B0.9700C28—H28A0.9800
C6—N21.460 (4)C29—C301.501 (5)
C6—H6A0.9800C29—H29A0.9600
C7—C81.489 (5)C29—H29B0.9600
C7—H7A0.9600C29—H29C0.9600
C7—H7B0.9600C30—N31.283 (4)
C7—H7C0.9600C30—C311.474 (5)
C8—N21.281 (4)C31—C361.401 (6)
C8—C91.488 (5)C31—C321.402 (5)
C9—C101.391 (5)C32—C331.370 (6)
C9—C141.404 (5)C32—H32A0.9300
C10—C111.378 (5)C33—C341.372 (8)
C10—H10A0.9300C33—H33A0.9300
C11—C121.389 (6)C34—C351.358 (7)
C11—H11A0.9300C34—H34A0.9300
C12—C131.366 (6)C35—C361.400 (5)
C12—H12A0.9300C35—H35A0.9300
C13—C141.382 (5)C36—O31.336 (5)
C13—H13A0.9300C37—C381.498 (5)
C14—O21.339 (4)C37—H37A0.9600
C15—C161.498 (5)C37—H37B0.9600
C15—H15A0.9600C37—H37C0.9600
C15—H15B0.9600C38—N41.284 (4)
C15—H15C0.9600C38—C391.473 (5)
C16—N11.287 (4)C39—C401.408 (5)
C16—C171.474 (5)C39—C441.411 (5)
C17—C181.396 (5)C40—C411.364 (6)
C17—C221.415 (6)C40—H40A0.9300
C18—C191.377 (6)C41—C421.375 (6)
C18—H18A0.9300C41—H41A0.9300
C19—C201.403 (8)C42—C431.370 (6)
C19—H19A0.9300C42—H42A0.9300
C20—C211.356 (7)C43—C441.387 (5)
C20—H20A0.9300C43—H43A0.9300
C21—C221.377 (6)C44—O41.337 (4)
C21—H21A0.9300O1—H10.8200
C22—O11.333 (5)O2—H20.8200
C23—N41.462 (4)O3—H30.8200
C23—C241.530 (4)O4—H40.8200
N1—C1—C2107.4 (3)C24—C23—H23A109.7
N1—C1—C6110.4 (3)C28—C23—H23A109.7
C2—C1—C6110.7 (3)C25—C24—C23111.7 (3)
N1—C1—H1A109.4C25—C24—H24A109.3
C2—C1—H1A109.4C23—C24—H24A109.3
C6—C1—H1A109.4C25—C24—H24B109.3
C3—C2—C1112.0 (3)C23—C24—H24B109.3
C3—C2—H2A109.2H24A—C24—H24B107.9
C1—C2—H2A109.2C26—C25—C24111.7 (3)
C3—C2—H2B109.2C26—C25—H25A109.3
C1—C2—H2B109.2C24—C25—H25A109.3
H2A—C2—H2B107.9C26—C25—H25B109.3
C2—C3—C4110.7 (4)C24—C25—H25B109.3
C2—C3—H3A109.5H25A—C25—H25B108.0
C4—C3—H3A109.5C25—C26—C27111.6 (3)
C2—C3—H3B109.5C25—C26—H26A109.3
C4—C3—H3B109.5C27—C26—H26A109.3
H3A—C3—H3B108.1C25—C26—H26B109.3
C5—C4—C3110.1 (4)C27—C26—H26B109.3
C5—C4—H4A109.6H26A—C26—H26B108.0
C3—C4—H4A109.6C26—C27—C28111.6 (3)
C5—C4—H4B109.6C26—C27—H27A109.3
C3—C4—H4B109.6C28—C27—H27A109.3
H4A—C4—H4B108.2C26—C27—H27B109.3
C4—C5—C6113.2 (3)C28—C27—H27B109.3
C4—C5—H5A108.9H27A—C27—H27B108.0
C6—C5—H5A108.9N3—C28—C27108.5 (3)
C4—C5—H5B108.9N3—C28—C23109.7 (2)
C6—C5—H5B108.9C27—C28—C23110.8 (3)
H5A—C5—H5B107.7N3—C28—H28A109.3
N2—C6—C5108.2 (3)C27—C28—H28A109.3
N2—C6—C1109.7 (3)C23—C28—H28A109.3
C5—C6—C1110.6 (3)C30—C29—H29A109.5
N2—C6—H6A109.4C30—C29—H29B109.5
C5—C6—H6A109.4H29A—C29—H29B109.5
C1—C6—H6A109.4C30—C29—H29C109.5
C8—C7—H7A109.5H29A—C29—H29C109.5
C8—C7—H7B109.5H29B—C29—H29C109.5
H7A—C7—H7B109.5N3—C30—C31116.4 (3)
C8—C7—H7C109.5N3—C30—C29124.6 (3)
H7A—C7—H7C109.5C31—C30—C29119.0 (3)
H7B—C7—H7C109.5C36—C31—C32118.0 (4)
N2—C8—C9116.7 (3)C36—C31—C30120.9 (3)
N2—C8—C7125.2 (3)C32—C31—C30121.1 (4)
C9—C8—C7118.0 (3)C33—C32—C31121.0 (5)
C10—C9—C14117.5 (3)C33—C32—H32A119.5
C10—C9—C8121.3 (3)C31—C32—H32A119.5
C14—C9—C8121.2 (3)C32—C33—C34120.8 (5)
C11—C10—C9122.7 (4)C32—C33—H33A119.6
C11—C10—H10A118.6C34—C33—H33A119.6
C9—C10—H10A118.6C35—C34—C33119.3 (5)
C10—C11—C12118.5 (4)C35—C34—H34A120.3
C10—C11—H11A120.8C33—C34—H34A120.3
C12—C11—H11A120.8C34—C35—C36121.7 (5)
C13—C12—C11120.1 (4)C34—C35—H35A119.1
C13—C12—H12A119.9C36—C35—H35A119.1
C11—C12—H12A119.9O3—C36—C35118.7 (4)
C12—C13—C14121.5 (4)O3—C36—C31122.3 (3)
C12—C13—H13A119.3C35—C36—C31119.0 (4)
C14—C13—H13A119.3C38—C37—H37A109.5
O2—C14—C13117.9 (3)C38—C37—H37B109.5
O2—C14—C9122.3 (3)H37A—C37—H37B109.5
C13—C14—C9119.7 (4)C38—C37—H37C109.5
C16—C15—H15A109.5H37A—C37—H37C109.5
C16—C15—H15B109.5H37B—C37—H37C109.5
H15A—C15—H15B109.5N4—C38—C39116.7 (3)
C16—C15—H15C109.5N4—C38—C37125.0 (3)
H15A—C15—H15C109.5C39—C38—C37118.2 (3)
H15B—C15—H15C109.5C40—C39—C44116.6 (3)
N1—C16—C17116.1 (3)C40—C39—C38122.3 (3)
N1—C16—C15124.7 (3)C44—C39—C38121.1 (3)
C17—C16—C15119.2 (3)C41—C40—C39122.4 (4)
C18—C17—C22117.4 (4)C41—C40—H40A118.8
C18—C17—C16121.6 (4)C39—C40—H40A118.8
C22—C17—C16120.9 (3)C40—C41—C42120.0 (4)
C19—C18—C17121.9 (5)C40—C41—H41A120.0
C19—C18—H18A119.0C42—C41—H41A120.0
C17—C18—H18A119.0C43—C42—C41119.8 (4)
C18—C19—C20119.4 (5)C43—C42—H42A120.1
C18—C19—H19A120.3C41—C42—H42A120.1
C20—C19—H19A120.3C42—C43—C44121.2 (4)
C21—C20—C19119.1 (5)C42—C43—H43A119.4
C21—C20—H20A120.4C44—C43—H43A119.4
C19—C20—H20A120.4O4—C44—C43118.1 (4)
C20—C21—C22122.4 (5)O4—C44—C39121.8 (3)
C20—C21—H21A118.8C43—C44—C39120.1 (3)
C22—C21—H21A118.8C16—N1—C1125.7 (3)
O1—C22—C21118.2 (4)C8—N2—C6125.1 (3)
O1—C22—C17122.1 (3)C30—N3—C28125.3 (3)
C21—C22—C17119.7 (4)C38—N4—C23124.5 (3)
N4—C23—C24108.3 (2)C22—O1—H1109.5
N4—C23—C28109.1 (3)C14—O2—H2109.5
C24—C23—C28110.3 (3)C36—O3—H3109.5
N4—C23—H23A109.7C44—O4—H4109.5
C16—N1—C1—C6102.8 (4)C38—N4—C23—C28101.2 (3)
C8—N2—C6—C1104.3 (4)N1—C1—C6—N2−69.1 (3)
C30—N3—C28—C23100.4 (4)N3—C28—C23—N4−65.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.772.496 (4)147
O2—H2···N20.821.812.531 (4)147
O3—H3···N30.821.822.507 (4)140
O4—H4···N40.821.782.507 (4)147
C26—H26A···Cg3i0.972.963.790 (5)144
C29—H29C···Cg3ii0.962.963.721 (5)137
C37—H37C···Cg3iii0.963.003.714 (4)133

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2132).

References

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  • Qu, Z.-R., Zhao, H., Wang, Y.-P., Wang, X.-S., Ye, Q., Li, Y.-H., Xiong, R.-G., Abrahams, B. H., Liu, Z.-G., Xue, Z.-L. & You, X.-Z. (2004). Chem. Eur. J.10, 54–60. [PubMed]
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