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The title compound, C46H40N6O2, is a glycoluril derivative. The mol­ecule contains four fused rings, viz two nearly planar imidazole rings and two non-planar triazine rings. The triazine rings each have a chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038572/dn6280sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038572/dn6280Isup2.hkl
Contains datablock I

CCDC reference: 296554

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.064
  • wR factor = 0.190
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.95 Ratio PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C8
Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.24 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C28 - C29 .. 5.47 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C28 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C8 -C13 1.36 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 53.00 A   3
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Glycoluril derivatives have many areas of applications, such as explosives, slow-release fertilizers, cross-linkers, iodogens, stabilizers of organic compounds against photodegradation, and as reagents in combinatorial chemistry (Wu et al., 2002). As a continuation of our previous studies in this area (Wei & Wu, 2005), we present here the structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1. The molecule is built up from 4 fused rings, viz. two nearly planar imidazole five-membered rings and two non-planar triazine six-membered rings. The non-planar six-membered rings display chair conformations, as observed in the related compound dimethyl 2,6-di-tert-butyl-4,8-dioxo-1,2,5,6-tetrahydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-8 b,8c-dicarboxylate (Li et al., 2005). All distances and angles are normal within experimental error.

Experimental top

C,C-Diphenylmethylamine(1.83 g, 10 mmol) and formaldehyde (2.4 g, 40 mmol) were added to a stirred solution of 3a,6a-Diphenyl-tetrahydro-imidazo [4,5-d]imidazole-2,5-dione (1.47 g, 5 mmol) in acetonitrile (50 ml) under a nitrogen atmosphere. The mixture was stirred overnight at room temperature. The solvent was evaporated to dryness and the residue was purified by column chromatography, yielding (I) (3.18 g, 90%) as a colorless solid. Colorless block-like crystals of (I) suitable for data collection were obtained by slow evaporation of an acetic acid ethyl ester solution at 283 K.

Refinement top

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å and Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C).

Computing details top

Data collection: SMART (Bruker,2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
2,6-Dibenzhydryl-8 b,8c-diphenyl-2,3,5,6,8 b,8c-hexahydro-2,3a,4a,6,7a,8a-hexaaza- 1H,4H-cyclopenta[def]fluorene-4,8-dione top
Crystal data top
C46H40N6O2Z = 2
Mr = 708.84F(000) = 748
Triclinic, P1Dx = 1.238 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.5691 (13) ÅCell parameters from 2204 reflections
b = 13.7434 (17) Åθ = 2.5–21.4°
c = 13.9871 (17) ŵ = 0.08 mm1
α = 78.876 (2)°T = 292 K
β = 72.706 (2)°Block, colorless
γ = 88.624 (2)°0.30 × 0.20 × 0.20 mm
V = 1902.2 (4) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3963 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 25.0°, θmin = 1.6°
ϕ and ω scansh = 1212
9562 measured reflectionsk = 1616
6617 independent reflectionsl = 816
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0818P)2 + 0.5417P]
where P = (Fo2 + 2Fc2)/3
6617 reflections(Δ/σ)max < 0.001
487 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C46H40N6O2γ = 88.624 (2)°
Mr = 708.84V = 1902.2 (4) Å3
Triclinic, P1Z = 2
a = 10.5691 (13) ÅMo Kα radiation
b = 13.7434 (17) ŵ = 0.08 mm1
c = 13.9871 (17) ÅT = 292 K
α = 78.876 (2)°0.30 × 0.20 × 0.20 mm
β = 72.706 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3963 reflections with I > 2σ(I)
9562 measured reflectionsRint = 0.018
6617 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.190H-atom parameters constrained
S = 1.03Δρmax = 0.32 e Å3
6617 reflectionsΔρmin = 0.18 e Å3
487 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
C11.0712 (5)0.9856 (3)0.1369 (4)0.1238 (17)
H10.99920.94460.17830.149*
C21.0487 (6)1.0787 (4)0.0849 (4)0.1313 (18)
H20.96271.10000.09250.158*
C31.1528 (7)1.1367 (4)0.0239 (4)0.1262 (17)
H31.13831.19780.01270.151*
C41.2760 (7)1.1088 (4)0.0147 (4)0.1230 (18)
H41.34651.15070.02780.148*
C51.3017 (5)1.0162 (4)0.0686 (3)0.1109 (14)
H51.38850.99820.06350.133*
C61.1979 (4)0.9533 (3)0.1284 (3)0.0889 (11)
C71.2254 (4)0.8491 (3)0.1795 (3)0.0947 (12)
H71.31070.85160.19340.114*
C81.2349 (5)0.7783 (3)0.1057 (3)0.0972 (13)
C91.1281 (6)0.7522 (5)0.0806 (4)0.137 (2)
H91.04510.77410.11240.164*
C101.1396 (8)0.6936 (5)0.0085 (5)0.166 (3)
H101.06490.67630.00760.200*
C111.2591 (12)0.6618 (6)0.0380 (5)0.179 (4)
H111.26780.62330.08740.215*
C121.3643 (9)0.6854 (6)0.0134 (8)0.200 (5)
H121.44640.66200.04520.240*
C131.3552 (5)0.7452 (4)0.0599 (5)0.154 (2)
H131.43010.76150.07630.185*
C141.1496 (3)0.7150 (2)0.3242 (2)0.0672 (8)
H14A1.15800.66990.27730.081*
H14B1.23250.71690.34020.081*
C151.1169 (3)0.8805 (2)0.3491 (3)0.0719 (9)
H15A1.20020.87970.36500.086*
H15B1.10280.94810.31910.086*
C160.8844 (3)0.8791 (2)0.4481 (2)0.0584 (8)
C170.9289 (3)0.63908 (18)0.4086 (2)0.0522 (7)
C181.0127 (3)0.74457 (18)0.4915 (2)0.0507 (7)
C191.1070 (3)0.7317 (2)0.5557 (2)0.0532 (7)
C201.1341 (3)0.8097 (2)0.5968 (2)0.0684 (8)
H201.09400.86990.58490.082*
C211.2201 (4)0.7989 (3)0.6551 (3)0.0868 (11)
H211.23890.85200.68170.104*
C221.2778 (4)0.7095 (3)0.6737 (3)0.0892 (11)
H221.33590.70220.71290.107*
C231.2505 (4)0.6311 (3)0.6352 (3)0.0841 (10)
H231.28920.57050.64870.101*
C241.1654 (3)0.6424 (2)0.5762 (2)0.0675 (8)
H241.14720.58910.54980.081*
C250.8607 (3)0.71870 (18)0.5482 (2)0.0511 (7)
C260.8234 (3)0.6768 (2)0.6620 (2)0.0580 (7)
C270.7800 (4)0.7368 (3)0.7327 (3)0.0864 (11)
H270.77200.80450.71170.104*
C280.7480 (5)0.6946 (4)0.8366 (3)0.1191 (16)
H280.71650.73420.88500.143*
C290.7628 (5)0.5960 (4)0.8674 (3)0.1186 (16)
H290.74070.56860.93660.142*
C300.8088 (5)0.5382 (3)0.7985 (3)0.1013 (13)
H300.82070.47120.82000.122*
C310.8384 (3)0.5779 (2)0.6961 (2)0.0728 (9)
H310.86920.53700.64890.087*
C320.6576 (3)0.8045 (2)0.5262 (3)0.0671 (8)
H32A0.60310.78390.59650.081*
H32B0.63030.86960.50040.081*
C330.6872 (3)0.6404 (2)0.4976 (2)0.0620 (8)
H33A0.67840.59630.45330.074*
H33B0.63540.61110.56660.074*
C340.6709 (3)0.7710 (2)0.3570 (2)0.0634 (8)
H340.76760.78020.33130.076*
C350.6276 (3)0.6944 (2)0.3052 (2)0.0638 (8)
C360.7149 (4)0.6681 (2)0.2210 (3)0.0774 (9)
H360.80080.69540.19740.093*
C370.6789 (6)0.6025 (3)0.1705 (3)0.1030 (14)
H370.73960.58660.11270.124*
C380.5531 (6)0.5601 (3)0.2053 (4)0.1121 (17)
H380.52770.51540.17180.135*
C390.4645 (4)0.5856 (3)0.2916 (4)0.0968 (13)
H390.37910.55740.31670.116*
C400.5033 (4)0.6526 (2)0.3399 (3)0.0786 (10)
H400.44310.66960.39730.094*
C410.6083 (3)0.8699 (2)0.3273 (3)0.0673 (8)
C420.4832 (3)0.8947 (2)0.3829 (3)0.0800 (10)
H420.43420.85100.44090.096*
C430.4322 (4)0.9851 (3)0.3513 (4)0.0925 (12)
H430.34961.00260.38930.111*
C440.5025 (5)1.0483 (3)0.2650 (4)0.1041 (15)
H440.46741.10870.24440.125*
C450.6249 (5)1.0237 (3)0.2078 (3)0.0979 (12)
H450.67171.06620.14800.117*
C460.6769 (4)0.9353 (3)0.2405 (3)0.0811 (10)
H460.76060.91930.20300.097*
N11.1222 (3)0.8146 (2)0.27600 (19)0.0713 (7)
N21.0110 (2)0.84708 (15)0.44018 (18)0.0575 (6)
N31.0429 (2)0.67986 (15)0.41668 (16)0.0526 (6)
N40.7972 (2)0.81214 (16)0.52444 (19)0.0565 (6)
N50.8272 (2)0.64725 (15)0.49379 (16)0.0511 (6)
N60.6331 (2)0.73545 (17)0.46682 (19)0.0628 (6)
O10.8544 (2)0.95498 (14)0.40072 (19)0.0788 (7)
O20.9230 (2)0.59828 (14)0.34052 (15)0.0674 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.103 (3)0.126 (4)0.131 (4)0.032 (3)0.062 (3)0.050 (3)
C20.147 (4)0.116 (4)0.134 (4)0.017 (3)0.080 (4)0.032 (3)
C30.171 (5)0.113 (4)0.082 (3)0.033 (4)0.031 (4)0.006 (3)
C40.151 (5)0.088 (3)0.099 (3)0.047 (3)0.012 (4)0.016 (3)
C50.099 (3)0.125 (4)0.092 (3)0.027 (3)0.006 (3)0.034 (3)
C60.085 (3)0.109 (3)0.064 (2)0.022 (2)0.022 (2)0.007 (2)
C70.064 (2)0.130 (3)0.076 (2)0.005 (2)0.019 (2)0.012 (2)
C80.097 (3)0.111 (3)0.057 (2)0.021 (3)0.003 (2)0.012 (2)
C90.136 (4)0.204 (6)0.091 (3)0.067 (4)0.052 (3)0.059 (4)
C100.235 (8)0.194 (6)0.103 (4)0.095 (6)0.089 (5)0.060 (4)
C110.287 (11)0.136 (6)0.061 (3)0.060 (8)0.009 (6)0.003 (3)
C120.186 (8)0.113 (5)0.188 (9)0.038 (6)0.092 (7)0.002 (5)
C130.102 (4)0.111 (4)0.182 (6)0.016 (3)0.036 (4)0.006 (4)
C140.068 (2)0.072 (2)0.0593 (19)0.0074 (16)0.0181 (17)0.0107 (16)
C150.072 (2)0.0594 (19)0.081 (2)0.0039 (16)0.0288 (19)0.0051 (17)
C160.073 (2)0.0418 (16)0.074 (2)0.0065 (15)0.0377 (18)0.0198 (15)
C170.076 (2)0.0335 (14)0.0521 (17)0.0079 (13)0.0255 (16)0.0097 (13)
C180.0629 (18)0.0382 (14)0.0545 (16)0.0041 (12)0.0226 (14)0.0100 (12)
C190.0569 (17)0.0513 (16)0.0504 (16)0.0045 (13)0.0170 (14)0.0053 (13)
C200.085 (2)0.0575 (18)0.070 (2)0.0059 (16)0.0330 (18)0.0113 (16)
C210.106 (3)0.090 (3)0.077 (2)0.018 (2)0.044 (2)0.016 (2)
C220.087 (3)0.119 (3)0.068 (2)0.011 (2)0.043 (2)0.001 (2)
C230.092 (3)0.088 (3)0.078 (2)0.008 (2)0.043 (2)0.002 (2)
C240.079 (2)0.0585 (19)0.072 (2)0.0064 (16)0.0346 (18)0.0099 (16)
C250.0614 (18)0.0394 (14)0.0575 (17)0.0044 (12)0.0214 (14)0.0159 (13)
C260.0608 (18)0.0653 (19)0.0520 (17)0.0018 (14)0.0162 (14)0.0223 (15)
C270.105 (3)0.086 (2)0.078 (2)0.012 (2)0.028 (2)0.041 (2)
C280.143 (4)0.152 (5)0.069 (3)0.013 (3)0.017 (3)0.061 (3)
C290.168 (5)0.127 (4)0.058 (2)0.006 (3)0.028 (3)0.018 (3)
C300.154 (4)0.092 (3)0.054 (2)0.011 (3)0.029 (2)0.005 (2)
C310.098 (3)0.068 (2)0.0526 (19)0.0009 (18)0.0215 (18)0.0141 (16)
C320.0617 (19)0.070 (2)0.081 (2)0.0140 (15)0.0269 (17)0.0333 (17)
C330.069 (2)0.0576 (18)0.0642 (19)0.0055 (15)0.0260 (16)0.0138 (15)
C340.0584 (18)0.0618 (18)0.070 (2)0.0036 (14)0.0124 (16)0.0237 (16)
C350.075 (2)0.0555 (18)0.068 (2)0.0121 (16)0.0300 (18)0.0144 (15)
C360.097 (3)0.073 (2)0.064 (2)0.0058 (18)0.023 (2)0.0192 (18)
C370.158 (4)0.096 (3)0.075 (3)0.025 (3)0.050 (3)0.042 (2)
C380.172 (5)0.072 (3)0.143 (4)0.026 (3)0.108 (4)0.047 (3)
C390.097 (3)0.069 (2)0.144 (4)0.009 (2)0.068 (3)0.019 (3)
C400.082 (3)0.071 (2)0.097 (3)0.0133 (19)0.040 (2)0.031 (2)
C410.073 (2)0.0627 (19)0.080 (2)0.0156 (17)0.0337 (19)0.0294 (18)
C420.073 (2)0.070 (2)0.112 (3)0.0103 (18)0.037 (2)0.040 (2)
C430.078 (3)0.079 (3)0.147 (4)0.021 (2)0.051 (3)0.059 (3)
C440.121 (4)0.074 (3)0.158 (4)0.035 (3)0.088 (4)0.050 (3)
C450.128 (4)0.079 (3)0.100 (3)0.017 (2)0.056 (3)0.016 (2)
C460.091 (3)0.076 (2)0.081 (2)0.015 (2)0.033 (2)0.015 (2)
N10.0689 (17)0.0758 (17)0.0603 (16)0.0008 (13)0.0150 (14)0.0017 (14)
N20.0631 (16)0.0447 (13)0.0653 (15)0.0002 (11)0.0240 (13)0.0045 (11)
N30.0620 (15)0.0478 (13)0.0481 (13)0.0041 (11)0.0160 (12)0.0107 (11)
N40.0614 (15)0.0460 (13)0.0713 (16)0.0072 (11)0.0278 (13)0.0214 (12)
N50.0620 (15)0.0451 (12)0.0501 (13)0.0001 (10)0.0185 (12)0.0157 (10)
N60.0678 (16)0.0569 (15)0.0702 (17)0.0031 (12)0.0258 (14)0.0199 (13)
O10.0933 (16)0.0451 (12)0.1115 (18)0.0124 (11)0.0536 (15)0.0122 (12)
O20.0918 (15)0.0592 (12)0.0642 (13)0.0125 (10)0.0322 (12)0.0302 (11)
Geometric parameters (Å, º) top
C1—C61.379 (6)C23—C241.378 (4)
C1—C21.397 (6)C23—H230.9300
C1—H10.9300C24—H240.9300
C2—C31.341 (7)C25—N51.461 (3)
C2—H20.9300C25—N41.462 (3)
C3—C41.325 (7)C25—C261.519 (4)
C3—H30.9300C26—C311.373 (4)
C4—C51.413 (7)C26—C271.376 (4)
C4—H40.9300C27—C281.398 (6)
C5—C61.368 (5)C27—H270.9300
C5—H50.9300C28—C291.360 (6)
C6—C71.534 (5)C28—H280.9300
C7—N11.463 (4)C29—C301.340 (5)
C7—C81.530 (6)C29—H290.9300
C7—H70.9800C30—C311.373 (5)
C8—C91.353 (6)C30—H300.9300
C8—C131.354 (6)C31—H310.9300
C9—C101.384 (7)C32—N61.450 (3)
C9—H90.9300C32—N41.475 (4)
C10—C111.343 (10)C32—H32A0.9700
C10—H100.9300C32—H32B0.9700
C11—C121.322 (11)C33—N61.454 (3)
C11—H110.9300C33—N51.470 (3)
C12—C131.415 (10)C33—H33A0.9700
C12—H120.9300C33—H33B0.9700
C13—H130.9300C34—N61.453 (4)
C14—N31.448 (4)C34—C351.535 (4)
C14—N11.467 (4)C34—C411.537 (4)
C14—H14A0.9700C34—H340.9800
C14—H14B0.9700C35—C401.357 (4)
C15—N21.427 (4)C35—C361.369 (4)
C15—N11.480 (4)C36—C371.371 (5)
C15—H15A0.9700C36—H360.9300
C15—H15B0.9700C37—C381.374 (6)
C16—O11.213 (3)C37—H370.9300
C16—N21.378 (4)C38—C391.390 (6)
C16—N41.382 (4)C38—H380.9300
C17—O21.211 (3)C39—C401.377 (5)
C17—N51.368 (3)C39—H390.9300
C17—N31.385 (3)C40—H400.9300
C18—N21.455 (3)C41—C461.377 (5)
C18—N31.461 (3)C41—C421.392 (4)
C18—C191.515 (4)C42—C431.388 (5)
C18—C251.580 (4)C42—H420.9300
C19—C241.379 (4)C43—C441.363 (6)
C19—C201.382 (4)C43—H430.9300
C20—C211.379 (4)C44—C451.377 (6)
C20—H200.9300C44—H440.9300
C21—C221.373 (5)C45—C461.375 (5)
C21—H210.9300C45—H450.9300
C22—C231.365 (5)C46—H460.9300
C22—H220.9300
C6—C1—C2121.5 (4)C31—C26—C27118.6 (3)
C6—C1—H1119.3C31—C26—C25119.9 (2)
C2—C1—H1119.3C27—C26—C25121.5 (3)
C3—C2—C1119.0 (5)C26—C27—C28119.2 (4)
C3—C2—H2120.5C26—C27—H27120.4
C1—C2—H2120.5C28—C27—H27120.4
C4—C3—C2121.3 (5)C29—C28—C27120.4 (4)
C4—C3—H3119.3C29—C28—H28119.8
C2—C3—H3119.3C27—C28—H28119.8
C3—C4—C5120.8 (5)C30—C29—C28120.4 (4)
C3—C4—H4119.6C30—C29—H29119.8
C5—C4—H4119.6C28—C29—H29119.8
C6—C5—C4119.5 (5)C29—C30—C31120.0 (4)
C6—C5—H5120.2C29—C30—H30120.0
C4—C5—H5120.2C31—C30—H30120.0
C5—C6—C1117.8 (4)C26—C31—C30121.4 (3)
C5—C6—C7119.6 (4)C26—C31—H31119.3
C1—C6—C7122.5 (3)C30—C31—H31119.3
N1—C7—C8111.0 (3)N6—C32—N4114.0 (2)
N1—C7—C6111.1 (3)N6—C32—H32A108.7
C8—C7—C6108.8 (3)N4—C32—H32A108.7
N1—C7—H7108.6N6—C32—H32B108.7
C8—C7—H7108.6N4—C32—H32B108.7
C6—C7—H7108.6H32A—C32—H32B107.6
C9—C8—C13119.0 (5)N6—C33—N5113.6 (2)
C9—C8—C7122.0 (4)N6—C33—H33A108.8
C13—C8—C7118.9 (5)N5—C33—H33A108.8
C8—C9—C10121.4 (5)N6—C33—H33B108.8
C8—C9—H9119.3N5—C33—H33B108.8
C10—C9—H9119.3H33A—C33—H33B107.7
C11—C10—C9119.7 (7)N6—C34—C35110.1 (2)
C11—C10—H10120.2N6—C34—C41112.5 (2)
C9—C10—H10120.2C35—C34—C41108.1 (2)
C12—C11—C10119.7 (9)N6—C34—H34108.7
C12—C11—H11120.1C35—C34—H34108.7
C10—C11—H11120.1C41—C34—H34108.7
C11—C12—C13121.7 (8)C40—C35—C36118.5 (3)
C11—C12—H12119.2C40—C35—C34121.6 (3)
C13—C12—H12119.2C36—C35—C34119.8 (3)
C8—C13—C12118.4 (7)C35—C36—C37121.7 (4)
C8—C13—H13120.8C35—C36—H36119.2
C12—C13—H13120.8C37—C36—H36119.2
N3—C14—N1109.9 (2)C36—C37—C38119.9 (4)
N3—C14—H14A109.7C36—C37—H37120.0
N1—C14—H14A109.7C38—C37—H37120.0
N3—C14—H14B109.7C37—C38—C39118.7 (4)
N1—C14—H14B109.7C37—C38—H38120.7
H14A—C14—H14B108.2C39—C38—H38120.7
N2—C15—N1109.2 (2)C40—C39—C38120.0 (4)
N2—C15—H15A109.8C40—C39—H39120.0
N1—C15—H15A109.8C38—C39—H39120.0
N2—C15—H15B109.8C35—C40—C39121.2 (4)
N1—C15—H15B109.8C35—C40—H40119.4
H15A—C15—H15B108.3C39—C40—H40119.4
O1—C16—N2126.4 (3)C46—C41—C42118.7 (3)
O1—C16—N4125.7 (3)C46—C41—C34118.7 (3)
N2—C16—N4107.8 (2)C42—C41—C34122.6 (3)
O2—C17—N5126.4 (3)C43—C42—C41119.6 (4)
O2—C17—N3125.4 (3)C43—C42—H42120.2
N5—C17—N3108.0 (2)C41—C42—H42120.2
N2—C18—N3109.8 (2)C44—C43—C42120.3 (4)
N2—C18—C19112.0 (2)C44—C43—H43119.8
N3—C18—C19112.0 (2)C42—C43—H43119.8
N2—C18—C25102.38 (19)C43—C44—C45120.7 (4)
N3—C18—C25102.12 (19)C43—C44—H44119.7
C19—C18—C25117.6 (2)C45—C44—H44119.7
C24—C19—C20118.6 (3)C46—C45—C44119.0 (4)
C24—C19—C18121.3 (2)C46—C45—H45120.5
C20—C19—C18120.1 (2)C44—C45—H45120.5
C21—C20—C19120.6 (3)C45—C46—C41121.7 (4)
C21—C20—H20119.7C45—C46—H46119.2
C19—C20—H20119.7C41—C46—H46119.2
C22—C21—C20119.6 (3)C7—N1—C14110.6 (3)
C22—C21—H21120.2C7—N1—C15111.1 (3)
C20—C21—H21120.2C14—N1—C15107.0 (2)
C23—C22—C21120.6 (3)C16—N2—C15120.4 (2)
C23—C22—H22119.7C16—N2—C18112.7 (2)
C21—C22—H22119.7C15—N2—C18116.8 (2)
C22—C23—C24119.6 (3)C17—N3—C14118.5 (2)
C22—C23—H23120.2C17—N3—C18111.8 (2)
C24—C23—H23120.2C14—N3—C18115.6 (2)
C23—C24—C19121.0 (3)C16—N4—C25111.2 (2)
C23—C24—H24119.5C16—N4—C32119.9 (2)
C19—C24—H24119.5C25—N4—C32116.3 (2)
N5—C25—N4109.3 (2)C17—N5—C25111.6 (2)
N5—C25—C26110.8 (2)C17—N5—C33122.4 (2)
N4—C25—C26112.6 (2)C25—N5—C33116.1 (2)
N5—C25—C18103.5 (2)C32—N6—C34115.9 (2)
N4—C25—C18103.4 (2)C32—N6—C33109.0 (2)
C26—C25—C18116.7 (2)C34—N6—C33114.0 (2)
C6—C1—C2—C31.3 (8)N6—C34—C41—C4233.2 (4)
C1—C2—C3—C42.1 (8)C35—C34—C41—C4288.6 (3)
C2—C3—C4—C50.4 (8)C46—C41—C42—C431.5 (5)
C3—C4—C5—C62.2 (7)C34—C41—C42—C43179.5 (3)
C4—C5—C6—C13.0 (6)C41—C42—C43—C441.6 (5)
C4—C5—C6—C7174.6 (4)C42—C43—C44—C450.0 (6)
C2—C1—C6—C51.3 (7)C43—C44—C45—C461.6 (6)
C2—C1—C6—C7176.2 (4)C44—C45—C46—C411.7 (5)
C5—C6—C7—N1149.7 (3)C42—C41—C46—C450.1 (5)
C1—C6—C7—N132.8 (5)C34—C41—C46—C45178.0 (3)
C5—C6—C7—C887.8 (4)C8—C7—N1—C1458.8 (4)
C1—C6—C7—C889.6 (5)C6—C7—N1—C14180.0 (3)
N1—C7—C8—C953.9 (5)C8—C7—N1—C15177.5 (3)
C6—C7—C8—C968.7 (5)C6—C7—N1—C1561.3 (4)
N1—C7—C8—C13129.8 (4)N3—C14—N1—C7176.9 (3)
C6—C7—C8—C13107.6 (4)N3—C14—N1—C1562.0 (3)
C13—C8—C9—C100.8 (8)N2—C15—N1—C7177.2 (2)
C7—C8—C9—C10175.5 (4)N2—C15—N1—C1462.0 (3)
C8—C9—C10—C110.1 (9)O1—C16—N2—C1524.1 (4)
C9—C10—C11—C121.1 (11)N4—C16—N2—C15159.5 (2)
C10—C11—C12—C131.2 (14)O1—C16—N2—C18168.3 (3)
C9—C8—C13—C120.7 (8)N4—C16—N2—C1815.2 (3)
C7—C8—C13—C12175.7 (5)N1—C15—N2—C1687.1 (3)
C11—C12—C13—C80.2 (12)N1—C15—N2—C1855.8 (3)
N2—C18—C19—C24153.2 (3)N3—C18—N2—C16100.6 (3)
N3—C18—C19—C2429.2 (4)C19—C18—N2—C16134.3 (2)
C25—C18—C19—C2488.6 (3)C25—C18—N2—C167.3 (3)
N2—C18—C19—C2028.1 (4)N3—C18—N2—C1545.0 (3)
N3—C18—C19—C20152.0 (3)C19—C18—N2—C1580.1 (3)
C25—C18—C19—C2090.2 (3)C25—C18—N2—C15152.9 (2)
C24—C19—C20—C211.4 (5)O2—C17—N3—C1427.3 (4)
C18—C19—C20—C21179.8 (3)N5—C17—N3—C14156.7 (2)
C19—C20—C21—C220.9 (5)O2—C17—N3—C18165.6 (2)
C20—C21—C22—C230.1 (6)N5—C17—N3—C1818.4 (3)
C21—C22—C23—C240.7 (6)N1—C14—N3—C1781.6 (3)
C22—C23—C24—C190.2 (5)N1—C14—N3—C1855.2 (3)
C20—C19—C24—C230.8 (5)N2—C18—N3—C1795.5 (2)
C18—C19—C24—C23179.6 (3)C19—C18—N3—C17139.3 (2)
N2—C18—C25—N5111.1 (2)C25—C18—N3—C1712.6 (3)
N3—C18—C25—N52.6 (2)N2—C18—N3—C1444.0 (3)
C19—C18—C25—N5125.6 (2)C19—C18—N3—C1481.1 (3)
N2—C18—C25—N42.8 (2)C25—C18—N3—C14152.1 (2)
N3—C18—C25—N4116.5 (2)O1—C16—N4—C25166.4 (3)
C19—C18—C25—N4120.5 (2)N2—C16—N4—C2517.1 (3)
N2—C18—C25—C26126.9 (2)O1—C16—N4—C3225.9 (4)
N3—C18—C25—C26119.4 (2)N2—C16—N4—C32157.6 (2)
C19—C18—C25—C263.7 (3)N5—C25—N4—C1697.6 (2)
N5—C25—C26—C3136.8 (4)C26—C25—N4—C16138.8 (2)
N4—C25—C26—C31159.5 (3)C18—C25—N4—C1612.1 (3)
C18—C25—C26—C3181.2 (3)N5—C25—N4—C3244.5 (3)
N5—C25—C26—C27146.1 (3)C26—C25—N4—C3279.1 (3)
N4—C25—C26—C2723.4 (4)C18—C25—N4—C32154.1 (2)
C18—C25—C26—C2795.9 (3)N6—C32—N4—C1687.9 (3)
C31—C26—C27—C282.3 (5)N6—C32—N4—C2550.7 (4)
C25—C26—C27—C28179.4 (3)O2—C17—N5—C25167.6 (2)
C26—C27—C28—C291.6 (7)N3—C17—N5—C2516.4 (3)
C27—C28—C29—C300.4 (8)O2—C17—N5—C3323.2 (4)
C28—C29—C30—C311.6 (7)N3—C17—N5—C33160.9 (2)
C27—C26—C31—C301.2 (5)N4—C25—N5—C17101.4 (2)
C25—C26—C31—C30178.3 (3)C26—C25—N5—C17134.0 (2)
C29—C30—C31—C260.8 (6)C18—C25—N5—C178.2 (3)
N6—C34—C35—C4048.1 (4)N4—C25—N5—C3345.4 (3)
C41—C34—C35—C4075.1 (4)C26—C25—N5—C3379.2 (3)
N6—C34—C35—C36133.0 (3)C18—C25—N5—C33155.1 (2)
C41—C34—C35—C36103.8 (3)N6—C33—N5—C1790.4 (3)
C40—C35—C36—C371.1 (5)N6—C33—N5—C2552.6 (3)
C34—C35—C36—C37177.8 (3)N4—C32—N6—C3477.9 (3)
C35—C36—C37—C381.1 (6)N4—C32—N6—C3352.2 (3)
C36—C37—C38—C390.2 (6)C35—C34—N6—C32174.8 (2)
C37—C38—C39—C400.5 (6)C41—C34—N6—C3254.2 (3)
C36—C35—C40—C390.3 (5)C35—C34—N6—C3357.6 (3)
C34—C35—C40—C39178.6 (3)C41—C34—N6—C33178.1 (2)
C38—C39—C40—C350.5 (5)N5—C33—N6—C3253.1 (3)
N6—C34—C41—C46148.8 (3)N5—C33—N6—C3478.1 (3)
C35—C34—C41—C4689.4 (3)

Experimental details

Crystal data
Chemical formulaC46H40N6O2
Mr708.84
Crystal system, space groupTriclinic, P1
Temperature (K)292
a, b, c (Å)10.5691 (13), 13.7434 (17), 13.9871 (17)
α, β, γ (°)78.876 (2), 72.706 (2), 88.624 (2)
V3)1902.2 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9562, 6617, 3963
Rint0.018
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.190, 1.03
No. of reflections6617
No. of parameters487
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.18

Computer programs: SMART (Bruker,2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

 

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