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Acta Cryst. (2007). E63, o3861
https://doi.org/10.1107/S1600536807040639
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(R)-(+)-3,3'-(1,1'-Binaphthyl-2,2'-di­oxy)diphthalonitrile benzene solvate

X.-M. Zhang and J.-T. Lu
White single crystals of the title compound, C36H18N4O2·C6H6, were obtained by reacting (R)-(+)-1,1'-bi-2-naphthol with 3-nitro­phthalonitrile and potassium carbonate and were recrystallized from benzene. The dihedral angle between the two naphthyl rings is 79.5(5)°. The (R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl units are connected together by the intermolecular \p-\p
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040639/hg2276sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040639/hg2276Isup2.hkl
Contains datablock I

CCDC reference: 660327

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.052
  • wR factor = 0.148
  • Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C26
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C37
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C41
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C42
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C39
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C40
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       3.38
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C2     ...       1.42 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C7     -   C8     ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C33    -   C34    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C35    -   C36    ...       1.44 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            N1  -C1  -C2  -C3     18.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          2
            N1  -C1  -C2  -C7      1.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         19
            C6  -C7  -C8  -N2   -135.00 14.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         20
            C2  -C7  -C8  -N2     43.00 14.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         85
            C32 -C33 -C34 -N3    141.00 18.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         86
            C35 -C33 -C34 -N3    -38.00 19.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         95
            C29 -C35 -C36 -N4   -161.00 11.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         96
            C33 -C35 -C36 -N4     19.00 12.00   1.555   1.555   1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     1.40(2), Rep    1.400(9) ......       2.22 su-Ra
              C37  -C38     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     1.38(2), Rep    1.381(9) ......       2.22 su-Ra
              C38  -C39     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     1.39(2), Rep    1.388(8) ......       2.50 su-Ra
              C39  -C40     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     1.39(2), Rep    1.390(9) ......       2.22 su-Ra
              C40  -C41     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     1.37(2), Rep    1.375(9) ......       2.22 su-Ra
              C41  -C42     1.555   1.555


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           26.00
           From the CIF: _reflns_number_total               3821
           Count of symmetry unique reflns         3829
           Completeness (_total/calc)             99.79%
           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
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         15


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  26 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
  14 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

(R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl as well as its derivative chiral non-entrosymmetrically phthalocyanines play an important role in the molecular self-assembly and molecular recognition in chemical, physical and biological sciences, since can form metal complexes with rare earth, actinide, and some early transition metals and main-group elements. (Kobayashi et al., 1999: Buchler & Ng, 2000).

To date, a variety of chiral supramolecular architectures have been obtained based on the above mentioned multifunctional ligands (Jiang & Lin, 2006). More recently, two novel interlocked chiral nanotubes formed from Ni(acac)2 and C2-symmetric 1,1-binaphthyl-6,6'-bipyridines have been reported (Jiang & Lin, 2003). They pointed out that the twisted binding sites of chiral rigid ditopic bridging ligands based on the 1,1'-binaphthyl unit will induce the formation of helical structures when linked by a linear metal-connecting point. Herein, we report the synthesis and crystal structure of a chiral organic compound (R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl benzene solvate (I).

The molecular structure of (I) is shown in Fig. 1. The cyano group C—N bond distances in this compound range from 1.138 (5) to 1.153 (6) Å and are similar to those in inorganic coordinated complexes (Ni, Kou, Zhang et al., 2005; Ni, Kou, Zhao et al., 2005). The C18—C19 bond distance is 1.495 (4) Å. The ten carbon atoms from two naphthyl rings in the title compound, respectively, are almost coplanar with the largest deviation value of 0.0527 (5) Å and 0.0138 (5) Å from the mean plane. The dihedral angle between the two naphthyl rings is 79.5 (5)°, which are similar to that of its derivative (R)-3,3'-Dibromo-2,2'-dimethoxy-5,5',6,6',7,7',8,8'-octahydro-1,1'- binaphthalene (80.2 (3)°) (He & Ng, 2006) and significantly larger than that of (R)-3,3'-Bis(3,4,5-trifluorophenyl)-1,1'-binaphthalene-2,2'-diol (73.5 (1)°) (Kang et al., 2007) due to steric effects.

In (I), the (R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl units are connected together by the intermolecular π–π interactions leading to chiral helical one-dimensional supramolecular structures as shown in Fig. 2.

Related literature top

For related literature, see: Buchler & Ng (2000); He & Ng (2006); Jiang & Lin (2003, 2006); Kang et al. (2007); Kobayashi (1998); Kobayashi et al. (1999); Ni, Kou, Zhang et al. (2005); Ni, Kou, Zhao et al. (2005).

Experimental top

(R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl was prepared according to the method reported in the literature (Kobayashi, 1998). A solid of (R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl (0.2 mmol) was added to the benzene solution (8 ml). The unsolved compounds was filtered and slowly evaporated to generate white single crystals suitable for X-ray diffraction analysis. Elemental analysis [found (calculated)] for C36H18N4O2: C 80.29 (80.40), H 3.37 (3.58), N 10.40% (10.62%). In the IR spectrum the cyano vibration is observed at 2238 cm-1.

Refinement top

The benzene solvate (C37–C42) was restrained to be planar regular hexagons, with target C≐C distances of 1.39 (1) Å. H atoms were placed in calculated positions and were included in the refinement in the riding-model approximation, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). The configuration of (I) was selected on the basis of the known configuration of the starting reagent, (R)-1,1'-binaphthalene-2,2'-diol, and Friedel pairs were merged.

Structure description top

(R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl as well as its derivative chiral non-entrosymmetrically phthalocyanines play an important role in the molecular self-assembly and molecular recognition in chemical, physical and biological sciences, since can form metal complexes with rare earth, actinide, and some early transition metals and main-group elements. (Kobayashi et al., 1999: Buchler & Ng, 2000).

To date, a variety of chiral supramolecular architectures have been obtained based on the above mentioned multifunctional ligands (Jiang & Lin, 2006). More recently, two novel interlocked chiral nanotubes formed from Ni(acac)2 and C2-symmetric 1,1-binaphthyl-6,6'-bipyridines have been reported (Jiang & Lin, 2003). They pointed out that the twisted binding sites of chiral rigid ditopic bridging ligands based on the 1,1'-binaphthyl unit will induce the formation of helical structures when linked by a linear metal-connecting point. Herein, we report the synthesis and crystal structure of a chiral organic compound (R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl benzene solvate (I).

The molecular structure of (I) is shown in Fig. 1. The cyano group C—N bond distances in this compound range from 1.138 (5) to 1.153 (6) Å and are similar to those in inorganic coordinated complexes (Ni, Kou, Zhang et al., 2005; Ni, Kou, Zhao et al., 2005). The C18—C19 bond distance is 1.495 (4) Å. The ten carbon atoms from two naphthyl rings in the title compound, respectively, are almost coplanar with the largest deviation value of 0.0527 (5) Å and 0.0138 (5) Å from the mean plane. The dihedral angle between the two naphthyl rings is 79.5 (5)°, which are similar to that of its derivative (R)-3,3'-Dibromo-2,2'-dimethoxy-5,5',6,6',7,7',8,8'-octahydro-1,1'- binaphthalene (80.2 (3)°) (He & Ng, 2006) and significantly larger than that of (R)-3,3'-Bis(3,4,5-trifluorophenyl)-1,1'-binaphthalene-2,2'-diol (73.5 (1)°) (Kang et al., 2007) due to steric effects.

In (I), the (R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl units are connected together by the intermolecular π–π interactions leading to chiral helical one-dimensional supramolecular structures as shown in Fig. 2.

For related literature, see: Buchler & Ng (2000); He & Ng (2006); Jiang & Lin (2003, 2006); Kang et al. (2007); Kobayashi (1998); Kobayashi et al. (1999); Ni, Kou, Zhang et al. (2005); Ni, Kou, Zhao et al. (2005).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top
[Figure 1] Fig. 1. A view of (I) with the unique atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. All H atoms and solvate benzene were omitted for clarity.
[Figure 2] Fig. 2. The chiral helical one-dimensional supramolecular structure in (I) through intermolecular π–π interactions.
(R)-(+)-3,3'-(1,1'-Binaphthyl-2,2'-dioxy)diphthalonitrile benzene solvate top
Crystal data top
C36H18N4O2·C6H6F(000) = 1280
Mr = 616.65Dx = 1.196 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3821 reflections
a = 7.8783 (1) Åθ = 2.3–26.0°
b = 12.2854 (2) ŵ = 0.08 mm−1
c = 35.3968 (5) ÅT = 295 K
V = 3425.99 (9) Å3Block, colourless
Z = 40.28 × 0.16 × 0.12 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3821 independent reflections
Radiation source: fine-focus sealed tube2647 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		h = −9→9
Tmin = 0.979, Tmax = 0.991k = −10→15
18358 measured reflectionsl = −43→43
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.147P)2 + 0.3168P]
where P = (Fo2 + 2Fc2)/3
3821 reflections(Δ/σ)max < 0.001
433 parametersΔρmax = 0.28 e Å−3
15 restraintsΔρmin = −0.15 e Å−3
Crystal data top
C36H18N4O2·C6H6V = 3425.99 (9) Å3
Mr = 616.65Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.8783 (1) ŵ = 0.08 mm−1
b = 12.2854 (2) ÅT = 295 K
c = 35.3968 (5) Å0.28 × 0.16 × 0.12 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3821 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		2647 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.991Rint = 0.029
18358 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05215 restraints
wR(F2) = 0.149H-atom parameters constrained
S = 1.04Δρmax = 0.28 e Å−3
3821 reflectionsΔρmin = −0.15 e Å−3
433 parameters
Special details top

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
O10.1382 (3)0.24330 (18)0.85664 (7)0.0668 (7)
O20.3103 (4)−0.0648 (2)0.86696 (7)0.0737 (7)
N20.5117 (6)0.3449 (3)0.89188 (12)0.1093 (14)
N10.4688 (7)0.6613 (4)0.87275 (19)0.153 (2)
N30.4446 (6)−0.0563 (4)0.70672 (12)0.1135 (14)
N40.2478 (5)−0.2275 (3)0.78731 (10)0.0940 (12)
C10.3576 (7)0.6042 (4)0.86531 (16)0.0984 (15)
C20.2210 (5)0.5334 (3)0.85618 (11)0.0674 (10)
C30.0708 (5)0.5749 (3)0.84235 (12)0.0767 (11)
H30.05860.64950.83860.092*
C4−0.0598 (5)0.5060 (3)0.83415 (11)0.0744 (11)
H4−0.16250.53450.82580.089*
C5−0.0423 (5)0.3943 (3)0.83802 (10)0.0658 (9)
H5−0.13180.34820.83190.079*
C60.1085 (5)0.3523 (3)0.85096 (9)0.0576 (9)
C70.2408 (5)0.4210 (3)0.86122 (9)0.0588 (9)
C80.3917 (6)0.3773 (3)0.87786 (11)0.0729 (11)
C90.0561 (4)0.1644 (3)0.83539 (9)0.0533 (8)
C100.0262 (5)0.1796 (3)0.79661 (9)0.0630 (9)
H100.05230.24560.78520.076*
C11−0.0408 (5)0.0972 (3)0.77607 (9)0.0650 (10)
H11−0.05650.10650.75020.078*
C12−0.0872 (4)−0.0024 (3)0.79300 (9)0.0572 (9)
C13−0.1665 (5)−0.0864 (4)0.77246 (11)0.0735 (11)
H13−0.1823−0.07880.74660.088*
C14−0.2198 (5)−0.1778 (4)0.78994 (15)0.0869 (13)
H14−0.2738−0.23200.77610.104*
C15−0.1943 (5)−0.1916 (3)0.82898 (14)0.0794 (11)
H15−0.2339−0.25420.84080.095*
C16−0.1127 (5)−0.1147 (3)0.84941 (11)0.0653 (9)
H16−0.0935−0.12610.87500.078*
C17−0.0560 (4)−0.0170 (3)0.83221 (9)0.0527 (8)
C180.0245 (4)0.0673 (2)0.85308 (8)0.0490 (7)
C190.0871 (5)0.0476 (3)0.89238 (8)0.0548 (8)
C200.0049 (5)0.0909 (3)0.92492 (8)0.0609 (9)
C21−0.1454 (6)0.1520 (3)0.92207 (10)0.0766 (11)
H21−0.19300.16520.89850.092*
C22−0.2222 (7)0.1922 (4)0.95379 (12)0.1017 (15)
H22−0.32170.23240.95160.122*
C23−0.1520 (9)0.1732 (5)0.98937 (13)0.1127 (18)
H23−0.20530.20071.01080.135*
C24−0.0090 (8)0.1158 (4)0.99294 (11)0.0977 (15)
H240.03670.10461.01690.117*
C250.0740 (6)0.0717 (3)0.96123 (9)0.0737 (11)
C260.2243 (8)0.0088 (4)0.96445 (11)0.0979 (15)
H260.2711−0.00360.98820.117*
C270.3003 (6)−0.0335 (4)0.93352 (11)0.0897 (13)
H270.3980−0.07540.93600.108*
C280.2308 (5)−0.0138 (3)0.89762 (9)0.0654 (9)
C290.3806 (5)−0.0007 (3)0.83978 (10)0.0622 (9)
C300.4572 (5)0.0987 (3)0.84743 (12)0.0740 (11)
H300.46220.12410.87210.089*
C310.5255 (5)0.1595 (4)0.81873 (14)0.0855 (12)
H310.57520.22640.82410.103*
C320.5207 (5)0.1220 (4)0.78195 (14)0.0827 (12)
H320.56610.16390.76250.099*
C330.4486 (4)0.0224 (3)0.77414 (10)0.0661 (9)
C340.4460 (5)−0.0202 (4)0.73636 (12)0.0807 (12)
C350.3780 (4)−0.0403 (3)0.80310 (10)0.0586 (9)
C360.3035 (5)−0.1449 (4)0.79493 (10)0.0683 (10)
C371.108 (2)0.6227 (16)0.9599 (5)0.378 (18)
H371.21310.63500.97100.454*
C381.0635 (19)0.5159 (13)0.9502 (3)0.274 (10)
H381.13830.45800.95330.329*
C390.902 (2)0.5017 (9)0.9357 (2)0.195 (4)
H390.86360.43300.92880.235*
C400.7992 (11)0.5927 (14)0.9319 (2)0.182 (5)
H400.69240.58070.92160.218*
C410.837 (2)0.6995 (12)0.9418 (3)0.305 (11)
H410.75940.75660.94040.366*
C421.002 (2)0.7105 (13)0.9537 (5)0.356 (15)
H421.04420.78020.95780.427*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0771 (16)0.0471 (14)0.0762 (14)−0.0046 (13)−0.0215 (13)0.0079 (11)
O20.0922 (19)0.0613 (15)0.0675 (14)0.0211 (15)0.0058 (14)0.0068 (12)
N10.114 (4)0.094 (3)0.253 (7)−0.037 (3)−0.053 (4)0.031 (3)
N20.102 (3)0.089 (3)0.137 (3)0.009 (2)−0.053 (3)−0.006 (2)
N30.106 (3)0.157 (4)0.077 (2)0.013 (3)0.005 (2)0.006 (3)
N40.108 (3)0.079 (3)0.095 (2)−0.011 (2)0.016 (2)−0.014 (2)
C10.090 (3)0.067 (3)0.138 (4)−0.015 (3)−0.021 (3)0.018 (3)
C20.062 (2)0.053 (2)0.088 (2)−0.009 (2)−0.003 (2)0.0094 (19)
C30.075 (3)0.052 (2)0.103 (3)0.004 (2)−0.005 (2)0.010 (2)
C40.062 (2)0.061 (3)0.100 (3)0.007 (2)−0.007 (2)0.006 (2)
C50.056 (2)0.052 (2)0.089 (2)−0.0064 (18)−0.0048 (19)0.0024 (18)
C60.063 (2)0.046 (2)0.0638 (18)−0.0059 (18)−0.0045 (17)0.0084 (15)
C70.058 (2)0.054 (2)0.0645 (19)−0.0009 (18)−0.0020 (17)0.0079 (16)
C80.068 (3)0.061 (2)0.089 (3)−0.004 (2)−0.020 (2)−0.001 (2)
C90.0576 (19)0.0480 (19)0.0544 (16)−0.0002 (17)−0.0076 (15)0.0003 (15)
C100.073 (2)0.062 (2)0.0535 (18)0.003 (2)0.0001 (17)0.0139 (17)
C110.073 (2)0.075 (3)0.0467 (16)0.020 (2)−0.0031 (17)0.0000 (18)
C120.0531 (19)0.061 (2)0.0572 (18)0.0127 (17)−0.0047 (15)−0.0109 (17)
C130.067 (2)0.071 (3)0.082 (2)0.016 (2)−0.011 (2)−0.028 (2)
C140.065 (3)0.073 (3)0.123 (4)0.007 (2)−0.014 (3)−0.040 (3)
C150.063 (2)0.054 (2)0.121 (3)−0.001 (2)0.007 (2)−0.011 (2)
C160.067 (2)0.050 (2)0.079 (2)0.0003 (19)0.0049 (19)−0.0025 (18)
C170.0512 (18)0.0486 (19)0.0582 (17)0.0077 (17)0.0021 (15)−0.0021 (15)
C180.0578 (19)0.0446 (18)0.0446 (14)0.0023 (16)−0.0006 (14)0.0032 (13)
C190.067 (2)0.0468 (19)0.0503 (16)0.0005 (17)−0.0054 (15)0.0030 (14)
C200.071 (2)0.059 (2)0.0529 (18)−0.0005 (19)0.0007 (17)0.0012 (15)
C210.083 (3)0.083 (3)0.064 (2)0.009 (2)−0.001 (2)−0.002 (2)
C220.110 (4)0.114 (4)0.081 (3)0.030 (3)0.022 (3)−0.008 (3)
C230.149 (5)0.119 (4)0.070 (3)0.014 (4)0.024 (3)−0.018 (3)
C240.134 (4)0.104 (4)0.055 (2)0.006 (4)−0.003 (3)−0.009 (2)
C250.100 (3)0.070 (2)0.0513 (19)−0.003 (2)−0.006 (2)−0.0010 (17)
C260.128 (4)0.110 (4)0.055 (2)0.014 (3)−0.023 (2)0.007 (2)
C270.100 (3)0.100 (3)0.070 (2)0.032 (3)−0.017 (2)0.014 (2)
C280.084 (2)0.057 (2)0.0544 (18)0.012 (2)−0.0060 (18)0.0039 (16)
C290.056 (2)0.062 (2)0.069 (2)0.0143 (19)−0.0002 (17)0.0036 (18)
C300.061 (2)0.069 (3)0.092 (3)0.003 (2)−0.002 (2)−0.011 (2)
C310.061 (2)0.075 (3)0.120 (4)−0.001 (2)0.008 (2)−0.010 (3)
C320.061 (2)0.078 (3)0.110 (3)0.005 (2)0.018 (2)0.025 (3)
C330.0502 (19)0.070 (3)0.078 (2)0.010 (2)0.0092 (18)0.0082 (19)
C340.065 (2)0.104 (3)0.073 (3)0.010 (3)0.007 (2)0.018 (2)
C350.0469 (18)0.058 (2)0.071 (2)0.0127 (17)0.0007 (16)0.0024 (17)
C360.062 (2)0.072 (3)0.072 (2)0.010 (2)0.0113 (19)−0.002 (2)
C370.31 (2)0.63 (5)0.191 (13)−0.13 (3)−0.031 (15)−0.10 (2)
C380.245 (17)0.47 (3)0.105 (7)0.145 (18)0.020 (8)0.034 (10)
C390.250 (13)0.258 (13)0.079 (5)−0.030 (11)0.047 (7)0.017 (6)
C400.136 (6)0.299 (14)0.110 (5)0.025 (9)0.008 (4)0.070 (8)
C410.36 (2)0.41 (2)0.141 (8)−0.238 (19)0.027 (10)0.055 (11)
C420.33 (3)0.52 (4)0.218 (16)−0.25 (3)0.038 (17)−0.064 (19)
Geometric parameters (Å, º) top
O1—C61.374 (4)C20—C211.406 (6)
O1—C91.387 (4)C20—C251.415 (5)
O2—C291.361 (4)C21—C221.367 (6)
O2—C281.401 (4)C21—H210.9300
N1—C11.153 (6)C22—C231.395 (7)
N2—C81.140 (5)C22—H220.9300
N3—C341.139 (5)C23—C241.336 (7)
N4—C361.138 (5)C23—H230.9300
C1—C21.421 (6)C24—C251.407 (6)
C2—C31.379 (5)C24—H240.9300
C2—C71.402 (5)C25—C261.419 (7)
C3—C41.364 (6)C26—C271.352 (6)
C3—H30.9300C26—H260.9300
C4—C51.386 (5)C27—C281.404 (5)
C4—H40.9300C27—H270.9300
C5—C61.374 (5)C29—C351.386 (5)
C5—H50.9300C29—C301.389 (5)
C6—C71.390 (5)C30—C311.371 (6)
C7—C81.431 (6)C30—H300.9300
C9—C181.370 (4)C31—C321.381 (6)
C9—C101.405 (4)C31—H310.9300
C10—C111.353 (5)C32—C331.378 (6)
C10—H100.9300C32—H320.9300
C11—C121.411 (5)C33—C351.398 (5)
C11—H110.9300C33—C341.436 (6)
C12—C131.409 (5)C35—C361.442 (6)
C12—C171.421 (4)C37—C421.382 (10)
C13—C141.348 (6)C37—C381.400 (9)
C13—H130.9300C37—H370.9300
C14—C151.407 (6)C38—C391.381 (9)
C14—H140.9300C38—H380.9300
C15—C161.352 (5)C39—C401.388 (8)
C15—H150.9300C39—H390.9300
C16—C171.419 (5)C40—C411.390 (9)
C16—H160.9300C40—H400.9300
C17—C181.421 (4)C41—C421.375 (9)
C18—C191.495 (4)C41—H410.9300
C19—C281.373 (5)C42—H420.9300
C19—C201.425 (5)
C6—O1—C9121.5 (3)C20—C21—H21119.8
C29—O2—C28118.1 (3)C21—C22—C23120.4 (5)
N1—C1—C2179.7 (6)C21—C22—H22119.8
C3—C2—C7120.4 (4)C23—C22—H22119.8
C3—C2—C1120.3 (4)C24—C23—C22120.5 (4)
C7—C2—C1119.3 (4)C24—C23—H23119.7
C4—C3—C2119.6 (4)C22—C23—H23119.7
C4—C3—H3120.2C23—C24—C25121.3 (4)
C2—C3—H3120.2C23—C24—H24119.4
C3—C4—C5121.2 (4)C25—C24—H24119.4
C3—C4—H4119.4C24—C25—C20118.8 (4)
C5—C4—H4119.4C24—C25—C26122.2 (4)
C6—C5—C4119.4 (4)C20—C25—C26119.0 (4)
C6—C5—H5120.3C27—C26—C25120.9 (4)
C4—C5—H5120.3C27—C26—H26119.5
C5—C6—O1124.2 (3)C25—C26—H26119.5
C5—C6—C7120.5 (3)C26—C27—C28119.6 (4)
O1—C6—C7115.2 (3)C26—C27—H27120.2
C6—C7—C2118.8 (3)C28—C27—H27120.2
C6—C7—C8120.2 (3)C19—C28—O2120.6 (3)
C2—C7—C8121.0 (3)C19—C28—C27122.6 (3)
N2—C8—C7178.0 (5)O2—C28—C27116.7 (3)
C18—C9—O1116.4 (3)O2—C29—C35116.9 (3)
C18—C9—C10122.1 (3)O2—C29—C30123.2 (3)
O1—C9—C10121.0 (3)C35—C29—C30119.8 (3)
C11—C10—C9119.4 (3)C31—C30—C29120.4 (4)
C11—C10—H10120.3C31—C30—H30119.8
C9—C10—H10120.3C29—C30—H30119.8
C10—C11—C12121.4 (3)C30—C31—C32120.4 (4)
C10—C11—H11119.3C30—C31—H31119.8
C12—C11—H11119.3C32—C31—H31119.8
C13—C12—C11122.1 (3)C33—C32—C31119.8 (4)
C13—C12—C17119.2 (4)C33—C32—H32120.1
C11—C12—C17118.6 (3)C31—C32—H32120.1
C14—C13—C12120.7 (4)C32—C33—C35120.4 (4)
C14—C13—H13119.6C32—C33—C34121.1 (4)
C12—C13—H13119.6C35—C33—C34118.5 (4)
C13—C14—C15120.5 (4)N3—C34—C33178.5 (5)
C13—C14—H14119.8C29—C35—C33119.2 (4)
C15—C14—H14119.8C29—C35—C36120.4 (3)
C16—C15—C14120.6 (4)C33—C35—C36120.4 (3)
C16—C15—H15119.7N4—C36—C35177.6 (4)
C14—C15—H15119.7C42—C37—C38122.8 (12)
C15—C16—C17120.8 (4)C42—C37—H37118.6
C15—C16—H16119.6C38—C37—H37118.6
C17—C16—H16119.6C39—C38—C37116.0 (10)
C16—C17—C12118.1 (3)C39—C38—H38122.0
C16—C17—C18122.3 (3)C37—C38—H38122.0
C12—C17—C18119.6 (3)C38—C39—C40118.2 (9)
C9—C18—C17118.5 (3)C38—C39—H39120.9
C9—C18—C19120.4 (3)C40—C39—H39120.9
C17—C18—C19120.9 (3)C39—C40—C41127.8 (9)
C28—C19—C20118.1 (3)C39—C40—H40116.1
C28—C19—C18119.1 (3)C41—C40—H40116.1
C20—C19—C18122.8 (3)C42—C41—C40111.8 (10)
C21—C20—C25118.6 (3)C42—C41—H41124.1
C21—C20—C19121.6 (3)C40—C41—H41124.1
C25—C20—C19119.8 (4)C41—C42—C37122.9 (12)
C22—C21—C20120.4 (4)C41—C42—H42118.5
C22—C21—H21119.8C37—C42—H42118.5
N1—C1—C2—C3−175 (100)C18—C19—C20—C212.5 (5)
N1—C1—C2—C75 (99)C28—C19—C20—C251.2 (5)
C7—C2—C3—C41.1 (6)C18—C19—C20—C25−178.1 (3)
C1—C2—C3—C4−179.2 (4)C25—C20—C21—C220.3 (6)
C2—C3—C4—C5−2.6 (6)C19—C20—C21—C22179.7 (4)
C3—C4—C5—C61.1 (6)C20—C21—C22—C230.1 (7)
C4—C5—C6—O1178.5 (3)C21—C22—C23—C240.1 (8)
C4—C5—C6—C72.0 (6)C22—C23—C24—C25−0.8 (8)
C9—O1—C6—C529.3 (5)C23—C24—C25—C201.1 (7)
C9—O1—C6—C7−154.0 (3)C23—C24—C25—C26−178.8 (5)
C5—C6—C7—C2−3.5 (5)C21—C20—C25—C24−0.9 (6)
O1—C6—C7—C2179.7 (3)C19—C20—C25—C24179.7 (4)
C5—C6—C7—C8174.3 (3)C21—C20—C25—C26179.1 (4)
O1—C6—C7—C8−2.5 (5)C19—C20—C25—C26−0.3 (6)
C3—C2—C7—C61.9 (6)C24—C25—C26—C27179.3 (5)
C1—C2—C7—C6−177.8 (4)C20—C25—C26—C27−0.7 (7)
C3—C2—C7—C8−175.8 (4)C25—C26—C27—C280.8 (7)
C1—C2—C7—C84.4 (6)C20—C19—C28—O2175.5 (3)
C6—C7—C8—N2−135 (14)C18—C19—C28—O2−5.1 (5)
C2—C7—C8—N243 (14)C20—C19—C28—C27−1.1 (6)
C6—O1—C9—C18−148.6 (3)C18—C19—C28—C27178.2 (4)
C6—O1—C9—C1038.8 (5)C29—O2—C28—C1965.2 (5)
C18—C9—C10—C112.1 (5)C29—O2—C28—C27−117.9 (4)
O1—C9—C10—C11174.3 (3)C26—C27—C28—C190.2 (7)
C9—C10—C11—C122.4 (6)C26—C27—C28—O2−176.6 (4)
C10—C11—C12—C13176.1 (3)C28—O2—C29—C35−147.4 (3)
C10—C11—C12—C17−2.6 (5)C28—O2—C29—C3034.6 (5)
C11—C12—C13—C14−175.5 (4)O2—C29—C30—C31−179.9 (3)
C17—C12—C13—C143.1 (5)C35—C29—C30—C312.1 (5)
C12—C13—C14—C15−1.2 (6)C29—C30—C31—C32−0.8 (6)
C13—C14—C15—C16−1.5 (6)C30—C31—C32—C33−0.7 (6)
C14—C15—C16—C172.1 (6)C31—C32—C33—C351.0 (6)
C15—C16—C17—C12−0.1 (5)C31—C32—C33—C34−178.3 (4)
C15—C16—C17—C18177.6 (3)C32—C33—C34—N3141 (18)
C13—C12—C17—C16−2.5 (5)C35—C33—C34—N3−38 (19)
C11—C12—C17—C16176.2 (3)O2—C29—C35—C33−180.0 (3)
C13—C12—C17—C18179.8 (3)C30—C29—C35—C33−1.8 (5)
C11—C12—C17—C18−1.5 (5)O2—C29—C35—C360.0 (5)
O1—C9—C18—C17−178.6 (3)C30—C29—C35—C36178.1 (3)
C10—C9—C18—C17−6.1 (5)C32—C33—C35—C290.3 (5)
O1—C9—C18—C19−3.8 (5)C34—C33—C35—C29179.5 (3)
C10—C9—C18—C19168.7 (3)C32—C33—C35—C36−179.6 (3)
C16—C17—C18—C9−171.9 (3)C34—C33—C35—C36−0.4 (5)
C12—C17—C18—C95.7 (5)C29—C35—C36—N4−161 (11)
C16—C17—C18—C1913.3 (5)C33—C35—C36—N419 (12)
C12—C17—C18—C19−169.0 (3)C42—C37—C38—C39−3 (2)
C9—C18—C19—C28−101.1 (4)C37—C38—C39—C400.3 (10)
C17—C18—C19—C2873.6 (4)C38—C39—C40—C41−1.5 (13)
C9—C18—C19—C2078.2 (4)C39—C40—C41—C425.3 (17)
C17—C18—C19—C20−107.1 (4)C40—C41—C42—C37−8 (3)
C28—C19—C20—C21−178.2 (4)C38—C37—C42—C418 (3)

Experimental details

Crystal data
Chemical formulaC36H18N4O2·C6H6
Mr616.65
Crystal system, space groupOrthorhombic, P212121
Temperature (K)295
a, b, c (Å)7.8783 (1), 12.2854 (2), 35.3968 (5)
V (Å3)3425.99 (9)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.28 × 0.16 × 0.12
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.979, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections		18358, 3821, 2647
Rint0.029
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.149, 1.04
No. of reflections3821
No. of parameters433
No. of restraints15
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.28, −0.15

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Sheldrick, 1998), SHELXTL (Bruker, 2001).

 

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