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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2142.
Published online 2008 October 18. doi:  10.1107/S1600536808033473
PMCID: PMC2959753

1,8,16,23-Tetra­kis(2-cyano­benz­yl)bis-p-xylylbis-m-xylyldiamine

Abstract

The title compound {systematic name: 2,2′,2′′,2′′′-[3,7,11,15-tetra­aza-1(1,4),5(1,3),9(1,4),13(1,3)-tetra­benzena­cyclo­hexadeca­phane-3,7,11,15-tetra­yltetra­methyl­ene]tetra­benzonitrile}, C64H56N8, is a centrosymmetric macrocycle that is consolidated into the crystal structure by C—H(...)π inter­actions.

Related literature

For synthesis, see: Chen & Martell (1991 [triangle]). For related literature, see: Vigato & Tamburini (2004 [triangle]). For related structures, see: Chen & Martell (1991 [triangle]); Comba et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2142-scheme1.jpg

Experimental

Crystal data

  • C64H56N8
  • M r = 937.17
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2142-efi1.jpg
  • a = 9.084 (5) Å
  • b = 10.999 (8) Å
  • c = 14.160 (8) Å
  • α = 73.26 (2)°
  • β = 73.012 (19)°
  • γ = 83.40 (2)°
  • V = 1295.0 (14) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 293 (2) K
  • 0.21 × 0.19 × 0.17 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.975, T max = 0.983
  • 12846 measured reflections
  • 5868 independent reflections
  • 2846 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.073
  • wR(F 2) = 0.188
  • S = 1.04
  • 5868 reflections
  • 325 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 [triangle]); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033473/tk2307sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033473/tk2307Isup2.hkl

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

Acknowledgments

We thank the Program for New Century Excellent Talents in Chinese Universities (grant No. NCET-05-0320) and the Analysis and Testing Foundation of Northeast Normal University for support.

supplementary crystallographic information

Comment

Macrocyclic compounds and their derivatives have attracted much attention recently owing to their applications in biochemistry, materials science, catalysis, encapsulation, activation, transport and separation phenomena, hydrometallurgy, etc. (Vigato & Tamburini, 2004). As an extension of our research on the macrocyclic derivatives, compound (I) was synthesized and its crystal structure determined, Fig. 1.

Bond lengths and bond angles found for (I) are within normal ranges for related crystal structures (Comba et al., 2001). The crystal structure is stabilized by C—H···π packing interactions, Table 1 and Figs 2 & 3; Cg1 and Cg2 are the centroids of the C3–C8 and C26–C31 rings, respectively.

Experimental

All chemicals were obtained from commercial sources and used without further purification except for bis-p-xylyl-bis-m-xylyldiamine which was synthesized according to the literature method (Chen & Martell, 1991). A mixture of bis-p-xylyl-bis-m-xylyldiamine (0.472 g, 1 mmol) and K2CO3 (1.00 g) in acetonitrile (30 ml) was stirred for 4 h. 2-Cyanobenzyl chloride (1 mmol) was then added and the solution refluxed for 20 h. After completion of the reaction, the reaction mixture was filtered and the filtrate was evaporated under vacuum. Colorless crystals suitable for X-ray diffraction were obtained by slow evaporation of an acetone solution of (I) after several days at room temperature.

Refinement

H atoms were treated as riding with C—H = 0.93 - 0.97 Å (CH), and with Uiso = 1.2Ueq(C).

Figures

Fig. 1.
Molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are omitted for clarity. The unlablled atoms are related by -x+1, -y+1, -z+1.
Fig. 2.
The C—H···π interactions in (I).
Fig. 3.
A view down the b-axis of the unit cell contents for (I).

Crystal data

C64H56N8V = 1295.0 (14) Å3
Mr = 937.17Z = 1
Triclinic, P1F(000) = 496
Hall symbol: -P 1Dx = 1.202 Mg m3
a = 9.084 (5) ÅMo Kα radiation, λ = 0.71069 Å
b = 10.999 (8) ŵ = 0.07 mm1
c = 14.160 (8) ÅT = 293 K
α = 73.26 (2)°Block, colorless
β = 73.012 (19)°0.21 × 0.19 × 0.17 mm
γ = 83.40 (2)°

Data collection

Rigaku R-AXIS RAPID diffractometer5868 independent reflections
Radiation source: fine-focus sealed tube2846 reflections with I > 2σ(I)
graphiteRint = 0.045
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scansh = −10→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −14→14
Tmin = 0.975, Tmax = 0.983l = −17→18
12846 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.072P)2 + 0.2406P] where P = (Fo2 + 2Fc2)/3
5868 reflections(Δ/σ)max < 0.001
325 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = −0.20 e Å3

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
C10.2541 (3)0.7033 (3)0.7026 (2)0.0587 (7)
H1A0.33500.67440.73680.070*
H1B0.18560.76110.73710.070*
C20.1184 (3)0.5227 (3)0.8221 (2)0.0580 (7)
H2A0.03460.46920.83160.070*
H2B0.07910.58230.86320.070*
C30.2436 (3)0.4416 (2)0.85999 (19)0.0514 (7)
C40.2980 (4)0.4604 (3)0.9363 (2)0.0685 (8)
H40.25930.52900.96330.082*
C50.4080 (4)0.3798 (3)0.9728 (3)0.0793 (10)
H50.44300.39421.02400.095*
C60.4666 (3)0.2779 (3)0.9339 (2)0.0648 (8)
H60.54090.22360.95920.078*
C70.4163 (3)0.2554 (3)0.85783 (19)0.0499 (6)
C80.3047 (3)0.3377 (2)0.82186 (19)0.0495 (6)
H80.26970.32300.77070.059*
C90.4840 (3)0.1459 (3)0.8133 (2)0.0548 (7)
H9A0.56840.17580.75280.066*
H9B0.52590.08200.86280.066*
C100.5508 (3)0.9901 (2)0.2845 (2)0.0554 (7)
H10A0.47591.04740.25580.066*
H10B0.62641.04120.29010.066*
C110.4700 (3)0.9112 (2)0.39063 (19)0.0497 (6)
C120.3422 (3)0.9611 (3)0.4501 (2)0.0602 (7)
H120.30261.04120.42310.072*
C130.2726 (3)0.8938 (3)0.5488 (2)0.0600 (8)
H130.18670.92990.58710.072*
C140.3260 (3)0.7751 (3)0.5925 (2)0.0502 (6)
C150.4526 (3)0.7244 (3)0.5325 (2)0.0584 (7)
H150.49070.64370.55920.070*
C160.5235 (3)0.7914 (3)0.4334 (2)0.0570 (7)
H160.60890.75510.39490.068*
C170.0341 (3)0.6353 (3)0.6741 (2)0.0650 (8)
H17A0.06400.69990.60950.078*
H17B−0.04260.67350.72200.078*
C18−0.0369 (3)0.5274 (3)0.6582 (2)0.0600 (7)
C190.0540 (4)0.4340 (3)0.6196 (2)0.0643 (8)
H190.16000.43340.60880.077*
C20−0.0083 (4)0.3423 (3)0.5969 (2)0.0792 (10)
H200.05540.28160.56910.095*
C21−0.1693 (5)0.3400 (3)0.6158 (3)0.0818 (10)
H21−0.21180.27760.60020.098*
C22−0.2617 (4)0.4274 (3)0.6561 (3)0.0772 (9)
H22−0.36790.42520.66900.093*
C23−0.1967 (3)0.5224 (3)0.6789 (2)0.0632 (8)
C24−0.2924 (4)0.6135 (3)0.7200 (3)0.0710 (9)
C250.2686 (3)0.0107 (3)0.8774 (2)0.0560 (7)
H25A0.23880.05770.92890.067*
H25B0.3237−0.06630.90420.067*
C260.1259 (3)−0.0250 (2)0.8603 (2)0.0504 (6)
C270.0631 (3)0.0487 (3)0.7840 (2)0.0677 (8)
H270.11110.12270.74090.081*
C28−0.0698 (3)0.0151 (3)0.7699 (3)0.0784 (10)
H28−0.11000.06620.71780.094*
C29−0.1422 (3)−0.0942 (3)0.8331 (3)0.0726 (9)
H29−0.2307−0.11760.82320.087*
C30−0.0843 (3)−0.1679 (3)0.9101 (2)0.0638 (8)
H30−0.1338−0.24110.95340.077*
C310.0486 (3)−0.1339 (2)0.9241 (2)0.0516 (7)
C320.1041 (3)−0.2134 (3)1.0065 (3)0.0674 (8)
N10.3723 (2)0.08726 (19)0.78530 (15)0.0472 (5)
N20.1680 (2)0.5945 (2)0.71309 (16)0.0511 (6)
N30.1478 (4)−0.2784 (3)1.0735 (3)0.0995 (10)
N4−0.3737 (4)0.6894 (4)0.7527 (3)0.1080 (11)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0600 (16)0.0602 (18)0.0538 (16)−0.0240 (14)−0.0019 (13)−0.0173 (14)
C20.0576 (17)0.0523 (17)0.0537 (16)−0.0098 (13)−0.0020 (13)−0.0086 (14)
C30.0557 (16)0.0462 (16)0.0452 (15)−0.0195 (12)−0.0032 (12)−0.0054 (12)
C40.091 (2)0.0562 (19)0.0636 (19)−0.0270 (17)−0.0185 (17)−0.0172 (16)
C50.100 (3)0.079 (2)0.076 (2)−0.035 (2)−0.042 (2)−0.017 (2)
C60.0634 (18)0.068 (2)0.0703 (19)−0.0209 (15)−0.0335 (15)−0.0071 (16)
C70.0452 (14)0.0513 (16)0.0501 (15)−0.0185 (12)−0.0111 (12)−0.0041 (13)
C80.0525 (15)0.0523 (16)0.0426 (14)−0.0136 (12)−0.0107 (12)−0.0089 (12)
C90.0454 (14)0.0527 (17)0.0609 (17)−0.0097 (12)−0.0132 (13)−0.0049 (13)
C100.0556 (16)0.0425 (15)0.0572 (16)−0.0061 (12)−0.0049 (13)−0.0056 (13)
C110.0474 (14)0.0432 (15)0.0530 (16)−0.0099 (11)−0.0060 (12)−0.0090 (13)
C120.0643 (17)0.0432 (16)0.0645 (18)0.0013 (13)−0.0060 (15)−0.0142 (14)
C130.0529 (16)0.0539 (18)0.0624 (18)−0.0030 (13)0.0020 (14)−0.0168 (15)
C140.0516 (15)0.0484 (16)0.0499 (15)−0.0155 (12)−0.0068 (12)−0.0139 (13)
C150.0598 (17)0.0494 (16)0.0565 (17)−0.0009 (13)−0.0111 (14)−0.0047 (13)
C160.0537 (16)0.0557 (18)0.0501 (16)0.0009 (13)−0.0028 (13)−0.0093 (14)
C170.0586 (17)0.0560 (18)0.081 (2)−0.0091 (14)−0.0219 (15)−0.0129 (16)
C180.0638 (18)0.0516 (17)0.0633 (18)−0.0141 (14)−0.0229 (14)−0.0029 (14)
C190.0703 (19)0.0523 (18)0.077 (2)−0.0072 (15)−0.0324 (16)−0.0137 (16)
C200.105 (3)0.060 (2)0.074 (2)−0.0093 (19)−0.033 (2)−0.0090 (17)
C210.105 (3)0.061 (2)0.084 (2)−0.034 (2)−0.038 (2)−0.0013 (18)
C220.071 (2)0.064 (2)0.084 (2)−0.0225 (17)−0.0196 (18)0.0067 (18)
C230.0585 (17)0.0620 (19)0.0653 (19)−0.0165 (15)−0.0245 (15)0.0020 (15)
C240.0563 (19)0.077 (2)0.082 (2)−0.0035 (17)−0.0257 (17)−0.0179 (19)
C250.0569 (16)0.0549 (17)0.0497 (15)−0.0153 (13)−0.0077 (13)−0.0060 (13)
C260.0467 (14)0.0479 (16)0.0516 (15)−0.0080 (12)−0.0044 (12)−0.0125 (13)
C270.0641 (18)0.0572 (19)0.073 (2)−0.0102 (15)−0.0192 (16)0.0002 (16)
C280.0607 (19)0.075 (2)0.094 (3)−0.0022 (17)−0.0288 (18)−0.007 (2)
C290.0494 (17)0.075 (2)0.093 (2)−0.0097 (16)−0.0119 (17)−0.026 (2)
C300.0489 (16)0.0608 (19)0.071 (2)−0.0116 (14)−0.0001 (15)−0.0135 (16)
C310.0428 (14)0.0478 (16)0.0543 (16)−0.0078 (12)0.0019 (12)−0.0116 (13)
C320.0583 (18)0.061 (2)0.070 (2)−0.0208 (15)−0.0060 (16)−0.0015 (17)
N10.0459 (11)0.0448 (12)0.0458 (12)−0.0136 (9)−0.0057 (9)−0.0066 (10)
N20.0495 (12)0.0473 (13)0.0531 (13)−0.0104 (10)−0.0115 (10)−0.0073 (10)
N30.092 (2)0.090 (2)0.094 (2)−0.0329 (17)−0.0286 (18)0.0232 (19)
N40.080 (2)0.115 (3)0.132 (3)0.004 (2)−0.034 (2)−0.036 (2)

Geometric parameters (Å, °)

C1—N21.453 (3)C16—H160.9300
C1—C141.515 (4)C17—N21.452 (3)
C1—H1A0.9700C17—C181.514 (4)
C1—H1B0.9700C17—H17A0.9700
C2—N21.477 (3)C17—H17B0.9700
C2—C31.491 (4)C18—C191.378 (4)
C2—H2A0.9700C18—C231.399 (4)
C2—H2B0.9700C19—C201.365 (4)
C3—C41.386 (4)C19—H190.9300
C3—C81.393 (4)C20—C211.411 (5)
C4—C51.373 (4)C20—H200.9300
C4—H40.9300C21—C221.343 (5)
C5—C61.375 (4)C21—H210.9300
C5—H50.9300C22—C231.412 (4)
C6—C71.378 (4)C22—H220.9300
C6—H60.9300C23—C241.392 (5)
C7—C81.390 (4)C24—N41.156 (4)
C7—C91.506 (4)C25—N11.459 (3)
C8—H80.9300C25—C261.499 (4)
C9—N11.461 (3)C25—H25A0.9700
C9—H9A0.9700C25—H25B0.9700
C9—H9B0.9700C26—C271.379 (4)
C10—N1i1.460 (3)C26—C311.394 (4)
C10—C111.517 (4)C27—C281.385 (4)
C10—H10A0.9700C27—H270.9300
C10—H10B0.9700C28—C291.377 (4)
C11—C121.380 (3)C28—H280.9300
C11—C161.381 (4)C29—C301.360 (4)
C12—C131.377 (4)C29—H290.9300
C12—H120.9300C30—C311.387 (4)
C13—C141.374 (4)C30—H300.9300
C13—H130.9300C31—C321.427 (4)
C14—C151.382 (4)C32—N31.154 (4)
C15—C161.383 (4)N1—C10i1.460 (3)
C15—H150.9300
N2—C1—C14113.9 (2)C11—C16—H16119.4
N2—C1—H1A108.8C15—C16—H16119.4
C14—C1—H1A108.8N2—C17—C18112.8 (2)
N2—C1—H1B108.8N2—C17—H17A109.0
C14—C1—H1B108.8C18—C17—H17A109.0
H1A—C1—H1B107.7N2—C17—H17B109.0
N2—C2—C3113.7 (2)C18—C17—H17B109.0
N2—C2—H2A108.8H17A—C17—H17B107.8
C3—C2—H2A108.8C19—C18—C23118.2 (3)
N2—C2—H2B108.8C19—C18—C17121.1 (3)
C3—C2—H2B108.8C23—C18—C17120.7 (3)
H2A—C2—H2B107.7C20—C19—C18121.5 (3)
C4—C3—C8117.4 (3)C20—C19—H19119.3
C4—C3—C2123.0 (3)C18—C19—H19119.3
C8—C3—C2119.5 (2)C19—C20—C21119.8 (3)
C5—C4—C3121.2 (3)C19—C20—H20120.1
C5—C4—H4119.4C21—C20—H20120.1
C3—C4—H4119.4C22—C21—C20120.3 (3)
C4—C5—C6120.3 (3)C22—C21—H21119.9
C4—C5—H5119.9C20—C21—H21119.9
C6—C5—H5119.9C21—C22—C23119.7 (3)
C5—C6—C7120.6 (3)C21—C22—H22120.1
C5—C6—H6119.7C23—C22—H22120.1
C7—C6—H6119.7C24—C23—C18119.9 (3)
C6—C7—C8118.4 (3)C24—C23—C22119.7 (3)
C6—C7—C9120.5 (3)C18—C23—C22120.4 (3)
C8—C7—C9121.1 (2)N4—C24—C23178.5 (4)
C7—C8—C3122.0 (3)N1—C25—C26114.0 (2)
C7—C8—H8119.0N1—C25—H25A108.8
C3—C8—H8119.0C26—C25—H25A108.8
N1—C9—C7113.2 (2)N1—C25—H25B108.8
N1—C9—H9A108.9C26—C25—H25B108.8
C7—C9—H9A108.9H25A—C25—H25B107.7
N1—C9—H9B108.9C27—C26—C31117.2 (3)
C7—C9—H9B108.9C27—C26—C25122.3 (2)
H9A—C9—H9B107.7C31—C26—C25120.5 (2)
N1i—C10—C11112.9 (2)C26—C27—C28121.6 (3)
N1i—C10—H10A109.0C26—C27—H27119.2
C11—C10—H10A109.0C28—C27—H27119.2
N1i—C10—H10B109.0C29—C28—C27119.9 (3)
C11—C10—H10B109.0C29—C28—H28120.1
H10A—C10—H10B107.8C27—C28—H28120.1
C12—C11—C16117.5 (2)C30—C29—C28119.9 (3)
C12—C11—C10120.0 (2)C30—C29—H29120.0
C16—C11—C10122.4 (2)C28—C29—H29120.0
C13—C12—C11120.9 (3)C29—C30—C31120.0 (3)
C13—C12—H12119.6C29—C30—H30120.0
C11—C12—H12119.6C31—C30—H30120.0
C14—C13—C12122.0 (3)C30—C31—C26121.4 (3)
C14—C13—H13119.0C30—C31—C32118.1 (3)
C12—C13—H13119.0C26—C31—C32120.6 (3)
C13—C14—C15117.1 (2)N3—C32—C31179.3 (3)
C13—C14—C1122.2 (2)C25—N1—C10i110.5 (2)
C15—C14—C1120.7 (3)C25—N1—C9109.9 (2)
C14—C15—C16121.3 (3)C10i—N1—C9111.2 (2)
C14—C15—H15119.4C17—N2—C1110.6 (2)
C16—C15—H15119.4C17—N2—C2109.7 (2)
C11—C16—C15121.2 (2)C1—N2—C2109.6 (2)
N2—C2—C3—C4116.7 (3)C18—C19—C20—C21−1.9 (5)
N2—C2—C3—C8−66.8 (3)C19—C20—C21—C22−0.1 (5)
C8—C3—C4—C50.1 (4)C20—C21—C22—C230.5 (5)
C2—C3—C4—C5176.6 (3)C19—C18—C23—C24178.6 (3)
C3—C4—C5—C60.0 (5)C17—C18—C23—C24−3.6 (4)
C4—C5—C6—C70.1 (5)C19—C18—C23—C22−2.9 (4)
C5—C6—C7—C8−0.3 (4)C17—C18—C23—C22174.9 (3)
C5—C6—C7—C9178.2 (3)C21—C22—C23—C24179.5 (3)
C6—C7—C8—C30.3 (4)C21—C22—C23—C181.1 (5)
C9—C7—C8—C3−178.2 (2)N1—C25—C26—C27−27.7 (4)
C4—C3—C8—C7−0.2 (4)N1—C25—C26—C31154.1 (2)
C2—C3—C8—C7−176.9 (2)C31—C26—C27—C28−1.0 (4)
C6—C7—C9—N1145.3 (2)C25—C26—C27—C28−179.3 (3)
C8—C7—C9—N1−36.2 (3)C26—C27—C28—C290.1 (5)
N1i—C10—C11—C12−151.7 (2)C27—C28—C29—C300.9 (5)
N1i—C10—C11—C1631.4 (4)C28—C29—C30—C31−0.8 (5)
C16—C11—C12—C130.8 (4)C29—C30—C31—C26−0.3 (4)
C10—C11—C12—C13−176.3 (3)C29—C30—C31—C32179.3 (3)
C11—C12—C13—C14−0.1 (5)C27—C26—C31—C301.2 (4)
C12—C13—C14—C15−0.8 (4)C25—C26—C31—C30179.4 (2)
C12—C13—C14—C1177.2 (3)C27—C26—C31—C32−178.4 (3)
N2—C1—C14—C13109.1 (3)C25—C26—C31—C32−0.1 (4)
N2—C1—C14—C15−72.9 (3)C26—C25—N1—C10i−72.3 (3)
C13—C14—C15—C161.0 (4)C26—C25—N1—C9164.6 (2)
C1—C14—C15—C16−177.0 (3)C7—C9—N1—C25−74.6 (3)
C12—C11—C16—C15−0.6 (4)C7—C9—N1—C10i162.7 (2)
C10—C11—C16—C15176.4 (3)C18—C17—N2—C1165.5 (2)
C14—C15—C16—C11−0.3 (5)C18—C17—N2—C2−73.5 (3)
N2—C17—C18—C19−39.2 (4)C14—C1—N2—C17−65.6 (3)
N2—C17—C18—C23143.0 (3)C14—C1—N2—C2173.4 (2)
C23—C18—C19—C203.4 (4)C3—C2—N2—C17161.1 (2)
C17—C18—C19—C20−174.5 (3)C3—C2—N2—C1−77.4 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C30—H30···Cg1ii0.932.603.451 (4)152
C2—H2A···Cg2iii0.972.973.937 (4)177

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2307).

References

  • Chen, D. & Martell, A. E. (1991). Tetrahedron, 47, 6895–6902.
  • Comba, P., Jurisic, P., Lampeka, Y. D., Peters, A., Prikhod’ko, A. I. & Pritzkow, H. (2001). Inorg. Chim. Acta, 324, 99–107.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Rigaku (1998). PROCESS-AUTO Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Vigato, P. A. & Tamburini, S. (2004). Coord. Chem. Rev.248, 1717–2128.

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