Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038572/dn6280sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038572/dn6280Isup2.hkl |
CCDC reference: 296554
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (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
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.
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).
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.
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. |
C46H40N6O2 | Z = 2 |
Mr = 708.84 | F(000) = 748 |
Triclinic, P1 | Dx = 1.238 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5691 (13) Å | Cell parameters from 2204 reflections |
b = 13.7434 (17) Å | θ = 2.5–21.4° |
c = 13.9871 (17) Å | µ = 0.08 mm−1 |
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 |
Bruker SMART CCD area-detector diffractometer | 3963 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 25.0°, θmin = 1.6° |
ϕ and ω scans | h = −12→12 |
9562 measured reflections | k = −16→16 |
6617 independent reflections | l = −8→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.190 | H-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 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C46H40N6O2 | γ = 88.624 (2)° |
Mr = 708.84 | V = 1902.2 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.5691 (13) Å | Mo Kα radiation |
b = 13.7434 (17) Å | µ = 0.08 mm−1 |
c = 13.9871 (17) Å | T = 292 K |
α = 78.876 (2)° | 0.30 × 0.20 × 0.20 mm |
β = 72.706 (2)° |
Bruker SMART CCD area-detector diffractometer | 3963 reflections with I > 2σ(I) |
9562 measured reflections | Rint = 0.018 |
6617 independent reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.190 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.32 e Å−3 |
6617 reflections | Δρmin = −0.18 e Å−3 |
487 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.0712 (5) | 0.9856 (3) | 0.1369 (4) | 0.1238 (17) | |
H1 | 0.9992 | 0.9446 | 0.1783 | 0.149* | |
C2 | 1.0487 (6) | 1.0787 (4) | 0.0849 (4) | 0.1313 (18) | |
H2 | 0.9627 | 1.1000 | 0.0925 | 0.158* | |
C3 | 1.1528 (7) | 1.1367 (4) | 0.0239 (4) | 0.1262 (17) | |
H3 | 1.1383 | 1.1978 | −0.0127 | 0.151* | |
C4 | 1.2760 (7) | 1.1088 (4) | 0.0147 (4) | 0.1230 (18) | |
H4 | 1.3465 | 1.1507 | −0.0278 | 0.148* | |
C5 | 1.3017 (5) | 1.0162 (4) | 0.0686 (3) | 0.1109 (14) | |
H5 | 1.3885 | 0.9982 | 0.0635 | 0.133* | |
C6 | 1.1979 (4) | 0.9533 (3) | 0.1284 (3) | 0.0889 (11) | |
C7 | 1.2254 (4) | 0.8491 (3) | 0.1795 (3) | 0.0947 (12) | |
H7 | 1.3107 | 0.8516 | 0.1934 | 0.114* | |
C8 | 1.2349 (5) | 0.7783 (3) | 0.1057 (3) | 0.0972 (13) | |
C9 | 1.1281 (6) | 0.7522 (5) | 0.0806 (4) | 0.137 (2) | |
H9 | 1.0451 | 0.7741 | 0.1124 | 0.164* | |
C10 | 1.1396 (8) | 0.6936 (5) | 0.0085 (5) | 0.166 (3) | |
H10 | 1.0649 | 0.6763 | −0.0076 | 0.200* | |
C11 | 1.2591 (12) | 0.6618 (6) | −0.0380 (5) | 0.179 (4) | |
H11 | 1.2678 | 0.6233 | −0.0874 | 0.215* | |
C12 | 1.3643 (9) | 0.6854 (6) | −0.0134 (8) | 0.200 (5) | |
H12 | 1.4464 | 0.6620 | −0.0452 | 0.240* | |
C13 | 1.3552 (5) | 0.7452 (4) | 0.0599 (5) | 0.154 (2) | |
H13 | 1.4301 | 0.7615 | 0.0763 | 0.185* | |
C14 | 1.1496 (3) | 0.7150 (2) | 0.3242 (2) | 0.0672 (8) | |
H14A | 1.1580 | 0.6699 | 0.2773 | 0.081* | |
H14B | 1.2325 | 0.7169 | 0.3402 | 0.081* | |
C15 | 1.1169 (3) | 0.8805 (2) | 0.3491 (3) | 0.0719 (9) | |
H15A | 1.2002 | 0.8797 | 0.3650 | 0.086* | |
H15B | 1.1028 | 0.9481 | 0.3191 | 0.086* | |
C16 | 0.8844 (3) | 0.8791 (2) | 0.4481 (2) | 0.0584 (8) | |
C17 | 0.9289 (3) | 0.63908 (18) | 0.4086 (2) | 0.0522 (7) | |
C18 | 1.0127 (3) | 0.74457 (18) | 0.4915 (2) | 0.0507 (7) | |
C19 | 1.1070 (3) | 0.7317 (2) | 0.5557 (2) | 0.0532 (7) | |
C20 | 1.1341 (3) | 0.8097 (2) | 0.5968 (2) | 0.0684 (8) | |
H20 | 1.0940 | 0.8699 | 0.5849 | 0.082* | |
C21 | 1.2201 (4) | 0.7989 (3) | 0.6551 (3) | 0.0868 (11) | |
H21 | 1.2389 | 0.8520 | 0.6817 | 0.104* | |
C22 | 1.2778 (4) | 0.7095 (3) | 0.6737 (3) | 0.0892 (11) | |
H22 | 1.3359 | 0.7022 | 0.7129 | 0.107* | |
C23 | 1.2505 (4) | 0.6311 (3) | 0.6352 (3) | 0.0841 (10) | |
H23 | 1.2892 | 0.5705 | 0.6487 | 0.101* | |
C24 | 1.1654 (3) | 0.6424 (2) | 0.5762 (2) | 0.0675 (8) | |
H24 | 1.1472 | 0.5891 | 0.5498 | 0.081* | |
C25 | 0.8607 (3) | 0.71870 (18) | 0.5482 (2) | 0.0511 (7) | |
C26 | 0.8234 (3) | 0.6768 (2) | 0.6620 (2) | 0.0580 (7) | |
C27 | 0.7800 (4) | 0.7368 (3) | 0.7327 (3) | 0.0864 (11) | |
H27 | 0.7720 | 0.8045 | 0.7117 | 0.104* | |
C28 | 0.7480 (5) | 0.6946 (4) | 0.8366 (3) | 0.1191 (16) | |
H28 | 0.7165 | 0.7342 | 0.8850 | 0.143* | |
C29 | 0.7628 (5) | 0.5960 (4) | 0.8674 (3) | 0.1186 (16) | |
H29 | 0.7407 | 0.5686 | 0.9366 | 0.142* | |
C30 | 0.8088 (5) | 0.5382 (3) | 0.7985 (3) | 0.1013 (13) | |
H30 | 0.8207 | 0.4712 | 0.8200 | 0.122* | |
C31 | 0.8384 (3) | 0.5779 (2) | 0.6961 (2) | 0.0728 (9) | |
H31 | 0.8692 | 0.5370 | 0.6489 | 0.087* | |
C32 | 0.6576 (3) | 0.8045 (2) | 0.5262 (3) | 0.0671 (8) | |
H32A | 0.6031 | 0.7839 | 0.5965 | 0.081* | |
H32B | 0.6303 | 0.8696 | 0.5004 | 0.081* | |
C33 | 0.6872 (3) | 0.6404 (2) | 0.4976 (2) | 0.0620 (8) | |
H33A | 0.6784 | 0.5963 | 0.4533 | 0.074* | |
H33B | 0.6354 | 0.6111 | 0.5666 | 0.074* | |
C34 | 0.6709 (3) | 0.7710 (2) | 0.3570 (2) | 0.0634 (8) | |
H34 | 0.7676 | 0.7802 | 0.3313 | 0.076* | |
C35 | 0.6276 (3) | 0.6944 (2) | 0.3052 (2) | 0.0638 (8) | |
C36 | 0.7149 (4) | 0.6681 (2) | 0.2210 (3) | 0.0774 (9) | |
H36 | 0.8008 | 0.6954 | 0.1974 | 0.093* | |
C37 | 0.6789 (6) | 0.6025 (3) | 0.1705 (3) | 0.1030 (14) | |
H37 | 0.7396 | 0.5866 | 0.1127 | 0.124* | |
C38 | 0.5531 (6) | 0.5601 (3) | 0.2053 (4) | 0.1121 (17) | |
H38 | 0.5277 | 0.5154 | 0.1718 | 0.135* | |
C39 | 0.4645 (4) | 0.5856 (3) | 0.2916 (4) | 0.0968 (13) | |
H39 | 0.3791 | 0.5574 | 0.3167 | 0.116* | |
C40 | 0.5033 (4) | 0.6526 (2) | 0.3399 (3) | 0.0786 (10) | |
H40 | 0.4431 | 0.6696 | 0.3973 | 0.094* | |
C41 | 0.6083 (3) | 0.8699 (2) | 0.3273 (3) | 0.0673 (8) | |
C42 | 0.4832 (3) | 0.8947 (2) | 0.3829 (3) | 0.0800 (10) | |
H42 | 0.4342 | 0.8510 | 0.4409 | 0.096* | |
C43 | 0.4322 (4) | 0.9851 (3) | 0.3513 (4) | 0.0925 (12) | |
H43 | 0.3496 | 1.0026 | 0.3893 | 0.111* | |
C44 | 0.5025 (5) | 1.0483 (3) | 0.2650 (4) | 0.1041 (15) | |
H44 | 0.4674 | 1.1087 | 0.2444 | 0.125* | |
C45 | 0.6249 (5) | 1.0237 (3) | 0.2078 (3) | 0.0979 (12) | |
H45 | 0.6717 | 1.0662 | 0.1480 | 0.117* | |
C46 | 0.6769 (4) | 0.9353 (3) | 0.2405 (3) | 0.0811 (10) | |
H46 | 0.7606 | 0.9193 | 0.2030 | 0.097* | |
N1 | 1.1222 (3) | 0.8146 (2) | 0.27600 (19) | 0.0713 (7) | |
N2 | 1.0110 (2) | 0.84708 (15) | 0.44018 (18) | 0.0575 (6) | |
N3 | 1.0429 (2) | 0.67986 (15) | 0.41668 (16) | 0.0526 (6) | |
N4 | 0.7972 (2) | 0.81214 (16) | 0.52444 (19) | 0.0565 (6) | |
N5 | 0.8272 (2) | 0.64725 (15) | 0.49379 (16) | 0.0511 (6) | |
N6 | 0.6331 (2) | 0.73545 (17) | 0.46682 (19) | 0.0628 (6) | |
O1 | 0.8544 (2) | 0.95498 (14) | 0.40072 (19) | 0.0788 (7) | |
O2 | 0.9230 (2) | 0.59828 (14) | 0.34052 (15) | 0.0674 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.103 (3) | 0.126 (4) | 0.131 (4) | −0.032 (3) | −0.062 (3) | 0.050 (3) |
C2 | 0.147 (4) | 0.116 (4) | 0.134 (4) | −0.017 (3) | −0.080 (4) | 0.032 (3) |
C3 | 0.171 (5) | 0.113 (4) | 0.082 (3) | −0.033 (4) | −0.031 (4) | 0.006 (3) |
C4 | 0.151 (5) | 0.088 (3) | 0.099 (3) | −0.047 (3) | 0.012 (4) | −0.016 (3) |
C5 | 0.099 (3) | 0.125 (4) | 0.092 (3) | −0.027 (3) | 0.006 (3) | −0.034 (3) |
C6 | 0.085 (3) | 0.109 (3) | 0.064 (2) | −0.022 (2) | −0.022 (2) | 0.007 (2) |
C7 | 0.064 (2) | 0.130 (3) | 0.076 (2) | −0.005 (2) | −0.019 (2) | 0.012 (2) |
C8 | 0.097 (3) | 0.111 (3) | 0.057 (2) | 0.021 (3) | −0.003 (2) | 0.012 (2) |
C9 | 0.136 (4) | 0.204 (6) | 0.091 (3) | 0.067 (4) | −0.052 (3) | −0.059 (4) |
C10 | 0.235 (8) | 0.194 (6) | 0.103 (4) | 0.095 (6) | −0.089 (5) | −0.060 (4) |
C11 | 0.287 (11) | 0.136 (6) | 0.061 (3) | 0.060 (8) | 0.009 (6) | 0.003 (3) |
C12 | 0.186 (8) | 0.113 (5) | 0.188 (9) | 0.038 (6) | 0.092 (7) | 0.002 (5) |
C13 | 0.102 (4) | 0.111 (4) | 0.182 (6) | 0.016 (3) | 0.036 (4) | 0.006 (4) |
C14 | 0.068 (2) | 0.072 (2) | 0.0593 (19) | 0.0074 (16) | −0.0181 (17) | −0.0107 (16) |
C15 | 0.072 (2) | 0.0594 (19) | 0.081 (2) | −0.0039 (16) | −0.0288 (19) | 0.0051 (17) |
C16 | 0.073 (2) | 0.0418 (16) | 0.074 (2) | 0.0065 (15) | −0.0377 (18) | −0.0198 (15) |
C17 | 0.076 (2) | 0.0335 (14) | 0.0521 (17) | 0.0079 (13) | −0.0255 (16) | −0.0097 (13) |
C18 | 0.0629 (18) | 0.0382 (14) | 0.0545 (16) | 0.0041 (12) | −0.0226 (14) | −0.0100 (12) |
C19 | 0.0569 (17) | 0.0513 (16) | 0.0504 (16) | −0.0045 (13) | −0.0170 (14) | −0.0053 (13) |
C20 | 0.085 (2) | 0.0575 (18) | 0.070 (2) | −0.0059 (16) | −0.0330 (18) | −0.0113 (16) |
C21 | 0.106 (3) | 0.090 (3) | 0.077 (2) | −0.018 (2) | −0.044 (2) | −0.016 (2) |
C22 | 0.087 (3) | 0.119 (3) | 0.068 (2) | −0.011 (2) | −0.043 (2) | −0.001 (2) |
C23 | 0.092 (3) | 0.088 (3) | 0.078 (2) | 0.008 (2) | −0.043 (2) | −0.002 (2) |
C24 | 0.079 (2) | 0.0585 (19) | 0.072 (2) | 0.0064 (16) | −0.0346 (18) | −0.0099 (16) |
C25 | 0.0614 (18) | 0.0394 (14) | 0.0575 (17) | 0.0044 (12) | −0.0214 (14) | −0.0159 (13) |
C26 | 0.0608 (18) | 0.0653 (19) | 0.0520 (17) | 0.0018 (14) | −0.0162 (14) | −0.0223 (15) |
C27 | 0.105 (3) | 0.086 (2) | 0.078 (2) | 0.012 (2) | −0.028 (2) | −0.041 (2) |
C28 | 0.143 (4) | 0.152 (5) | 0.069 (3) | 0.013 (3) | −0.017 (3) | −0.061 (3) |
C29 | 0.168 (5) | 0.127 (4) | 0.058 (2) | −0.006 (3) | −0.028 (3) | −0.018 (3) |
C30 | 0.154 (4) | 0.092 (3) | 0.054 (2) | −0.011 (3) | −0.029 (2) | −0.005 (2) |
C31 | 0.098 (3) | 0.068 (2) | 0.0526 (19) | −0.0009 (18) | −0.0215 (18) | −0.0141 (16) |
C32 | 0.0617 (19) | 0.070 (2) | 0.081 (2) | 0.0140 (15) | −0.0269 (17) | −0.0333 (17) |
C33 | 0.069 (2) | 0.0576 (18) | 0.0642 (19) | −0.0055 (15) | −0.0260 (16) | −0.0138 (15) |
C34 | 0.0584 (18) | 0.0618 (18) | 0.070 (2) | 0.0036 (14) | −0.0124 (16) | −0.0237 (16) |
C35 | 0.075 (2) | 0.0555 (18) | 0.068 (2) | 0.0121 (16) | −0.0300 (18) | −0.0144 (15) |
C36 | 0.097 (3) | 0.073 (2) | 0.064 (2) | 0.0058 (18) | −0.023 (2) | −0.0192 (18) |
C37 | 0.158 (4) | 0.096 (3) | 0.075 (3) | 0.025 (3) | −0.050 (3) | −0.042 (2) |
C38 | 0.172 (5) | 0.072 (3) | 0.143 (4) | 0.026 (3) | −0.108 (4) | −0.047 (3) |
C39 | 0.097 (3) | 0.069 (2) | 0.144 (4) | 0.009 (2) | −0.068 (3) | −0.019 (3) |
C40 | 0.082 (3) | 0.071 (2) | 0.097 (3) | 0.0133 (19) | −0.040 (2) | −0.031 (2) |
C41 | 0.073 (2) | 0.0627 (19) | 0.080 (2) | 0.0156 (17) | −0.0337 (19) | −0.0294 (18) |
C42 | 0.073 (2) | 0.070 (2) | 0.112 (3) | 0.0103 (18) | −0.037 (2) | −0.040 (2) |
C43 | 0.078 (3) | 0.079 (3) | 0.147 (4) | 0.021 (2) | −0.051 (3) | −0.059 (3) |
C44 | 0.121 (4) | 0.074 (3) | 0.158 (4) | 0.035 (3) | −0.088 (4) | −0.050 (3) |
C45 | 0.128 (4) | 0.079 (3) | 0.100 (3) | 0.017 (2) | −0.056 (3) | −0.016 (2) |
C46 | 0.091 (3) | 0.076 (2) | 0.081 (2) | 0.015 (2) | −0.033 (2) | −0.015 (2) |
N1 | 0.0689 (17) | 0.0758 (17) | 0.0603 (16) | −0.0008 (13) | −0.0150 (14) | 0.0017 (14) |
N2 | 0.0631 (16) | 0.0447 (13) | 0.0653 (15) | 0.0002 (11) | −0.0240 (13) | −0.0045 (11) |
N3 | 0.0620 (15) | 0.0478 (13) | 0.0481 (13) | 0.0041 (11) | −0.0160 (12) | −0.0107 (11) |
N4 | 0.0614 (15) | 0.0460 (13) | 0.0713 (16) | 0.0072 (11) | −0.0278 (13) | −0.0214 (12) |
N5 | 0.0620 (15) | 0.0451 (12) | 0.0501 (13) | 0.0001 (10) | −0.0185 (12) | −0.0157 (10) |
N6 | 0.0678 (16) | 0.0569 (15) | 0.0702 (17) | 0.0031 (12) | −0.0258 (14) | −0.0199 (13) |
O1 | 0.0933 (16) | 0.0451 (12) | 0.1115 (18) | 0.0124 (11) | −0.0536 (15) | −0.0122 (12) |
O2 | 0.0918 (15) | 0.0592 (12) | 0.0642 (13) | 0.0125 (10) | −0.0322 (12) | −0.0302 (11) |
C1—C6 | 1.379 (6) | C23—C24 | 1.378 (4) |
C1—C2 | 1.397 (6) | C23—H23 | 0.9300 |
C1—H1 | 0.9300 | C24—H24 | 0.9300 |
C2—C3 | 1.341 (7) | C25—N5 | 1.461 (3) |
C2—H2 | 0.9300 | C25—N4 | 1.462 (3) |
C3—C4 | 1.325 (7) | C25—C26 | 1.519 (4) |
C3—H3 | 0.9300 | C26—C31 | 1.373 (4) |
C4—C5 | 1.413 (7) | C26—C27 | 1.376 (4) |
C4—H4 | 0.9300 | C27—C28 | 1.398 (6) |
C5—C6 | 1.368 (5) | C27—H27 | 0.9300 |
C5—H5 | 0.9300 | C28—C29 | 1.360 (6) |
C6—C7 | 1.534 (5) | C28—H28 | 0.9300 |
C7—N1 | 1.463 (4) | C29—C30 | 1.340 (5) |
C7—C8 | 1.530 (6) | C29—H29 | 0.9300 |
C7—H7 | 0.9800 | C30—C31 | 1.373 (5) |
C8—C9 | 1.353 (6) | C30—H30 | 0.9300 |
C8—C13 | 1.354 (6) | C31—H31 | 0.9300 |
C9—C10 | 1.384 (7) | C32—N6 | 1.450 (3) |
C9—H9 | 0.9300 | C32—N4 | 1.475 (4) |
C10—C11 | 1.343 (10) | C32—H32A | 0.9700 |
C10—H10 | 0.9300 | C32—H32B | 0.9700 |
C11—C12 | 1.322 (11) | C33—N6 | 1.454 (3) |
C11—H11 | 0.9300 | C33—N5 | 1.470 (3) |
C12—C13 | 1.415 (10) | C33—H33A | 0.9700 |
C12—H12 | 0.9300 | C33—H33B | 0.9700 |
C13—H13 | 0.9300 | C34—N6 | 1.453 (4) |
C14—N3 | 1.448 (4) | C34—C35 | 1.535 (4) |
C14—N1 | 1.467 (4) | C34—C41 | 1.537 (4) |
C14—H14A | 0.9700 | C34—H34 | 0.9800 |
C14—H14B | 0.9700 | C35—C40 | 1.357 (4) |
C15—N2 | 1.427 (4) | C35—C36 | 1.369 (4) |
C15—N1 | 1.480 (4) | C36—C37 | 1.371 (5) |
C15—H15A | 0.9700 | C36—H36 | 0.9300 |
C15—H15B | 0.9700 | C37—C38 | 1.374 (6) |
C16—O1 | 1.213 (3) | C37—H37 | 0.9300 |
C16—N2 | 1.378 (4) | C38—C39 | 1.390 (6) |
C16—N4 | 1.382 (4) | C38—H38 | 0.9300 |
C17—O2 | 1.211 (3) | C39—C40 | 1.377 (5) |
C17—N5 | 1.368 (3) | C39—H39 | 0.9300 |
C17—N3 | 1.385 (3) | C40—H40 | 0.9300 |
C18—N2 | 1.455 (3) | C41—C46 | 1.377 (5) |
C18—N3 | 1.461 (3) | C41—C42 | 1.392 (4) |
C18—C19 | 1.515 (4) | C42—C43 | 1.388 (5) |
C18—C25 | 1.580 (4) | C42—H42 | 0.9300 |
C19—C24 | 1.379 (4) | C43—C44 | 1.363 (6) |
C19—C20 | 1.382 (4) | C43—H43 | 0.9300 |
C20—C21 | 1.379 (4) | C44—C45 | 1.377 (6) |
C20—H20 | 0.9300 | C44—H44 | 0.9300 |
C21—C22 | 1.373 (5) | C45—C46 | 1.375 (5) |
C21—H21 | 0.9300 | C45—H45 | 0.9300 |
C22—C23 | 1.365 (5) | C46—H46 | 0.9300 |
C22—H22 | 0.9300 | ||
C6—C1—C2 | 121.5 (4) | C31—C26—C27 | 118.6 (3) |
C6—C1—H1 | 119.3 | C31—C26—C25 | 119.9 (2) |
C2—C1—H1 | 119.3 | C27—C26—C25 | 121.5 (3) |
C3—C2—C1 | 119.0 (5) | C26—C27—C28 | 119.2 (4) |
C3—C2—H2 | 120.5 | C26—C27—H27 | 120.4 |
C1—C2—H2 | 120.5 | C28—C27—H27 | 120.4 |
C4—C3—C2 | 121.3 (5) | C29—C28—C27 | 120.4 (4) |
C4—C3—H3 | 119.3 | C29—C28—H28 | 119.8 |
C2—C3—H3 | 119.3 | C27—C28—H28 | 119.8 |
C3—C4—C5 | 120.8 (5) | C30—C29—C28 | 120.4 (4) |
C3—C4—H4 | 119.6 | C30—C29—H29 | 119.8 |
C5—C4—H4 | 119.6 | C28—C29—H29 | 119.8 |
C6—C5—C4 | 119.5 (5) | C29—C30—C31 | 120.0 (4) |
C6—C5—H5 | 120.2 | C29—C30—H30 | 120.0 |
C4—C5—H5 | 120.2 | C31—C30—H30 | 120.0 |
C5—C6—C1 | 117.8 (4) | C26—C31—C30 | 121.4 (3) |
C5—C6—C7 | 119.6 (4) | C26—C31—H31 | 119.3 |
C1—C6—C7 | 122.5 (3) | C30—C31—H31 | 119.3 |
N1—C7—C8 | 111.0 (3) | N6—C32—N4 | 114.0 (2) |
N1—C7—C6 | 111.1 (3) | N6—C32—H32A | 108.7 |
C8—C7—C6 | 108.8 (3) | N4—C32—H32A | 108.7 |
N1—C7—H7 | 108.6 | N6—C32—H32B | 108.7 |
C8—C7—H7 | 108.6 | N4—C32—H32B | 108.7 |
C6—C7—H7 | 108.6 | H32A—C32—H32B | 107.6 |
C9—C8—C13 | 119.0 (5) | N6—C33—N5 | 113.6 (2) |
C9—C8—C7 | 122.0 (4) | N6—C33—H33A | 108.8 |
C13—C8—C7 | 118.9 (5) | N5—C33—H33A | 108.8 |
C8—C9—C10 | 121.4 (5) | N6—C33—H33B | 108.8 |
C8—C9—H9 | 119.3 | N5—C33—H33B | 108.8 |
C10—C9—H9 | 119.3 | H33A—C33—H33B | 107.7 |
C11—C10—C9 | 119.7 (7) | N6—C34—C35 | 110.1 (2) |
C11—C10—H10 | 120.2 | N6—C34—C41 | 112.5 (2) |
C9—C10—H10 | 120.2 | C35—C34—C41 | 108.1 (2) |
C12—C11—C10 | 119.7 (9) | N6—C34—H34 | 108.7 |
C12—C11—H11 | 120.1 | C35—C34—H34 | 108.7 |
C10—C11—H11 | 120.1 | C41—C34—H34 | 108.7 |
C11—C12—C13 | 121.7 (8) | C40—C35—C36 | 118.5 (3) |
C11—C12—H12 | 119.2 | C40—C35—C34 | 121.6 (3) |
C13—C12—H12 | 119.2 | C36—C35—C34 | 119.8 (3) |
C8—C13—C12 | 118.4 (7) | C35—C36—C37 | 121.7 (4) |
C8—C13—H13 | 120.8 | C35—C36—H36 | 119.2 |
C12—C13—H13 | 120.8 | C37—C36—H36 | 119.2 |
N3—C14—N1 | 109.9 (2) | C36—C37—C38 | 119.9 (4) |
N3—C14—H14A | 109.7 | C36—C37—H37 | 120.0 |
N1—C14—H14A | 109.7 | C38—C37—H37 | 120.0 |
N3—C14—H14B | 109.7 | C37—C38—C39 | 118.7 (4) |
N1—C14—H14B | 109.7 | C37—C38—H38 | 120.7 |
H14A—C14—H14B | 108.2 | C39—C38—H38 | 120.7 |
N2—C15—N1 | 109.2 (2) | C40—C39—C38 | 120.0 (4) |
N2—C15—H15A | 109.8 | C40—C39—H39 | 120.0 |
N1—C15—H15A | 109.8 | C38—C39—H39 | 120.0 |
N2—C15—H15B | 109.8 | C35—C40—C39 | 121.2 (4) |
N1—C15—H15B | 109.8 | C35—C40—H40 | 119.4 |
H15A—C15—H15B | 108.3 | C39—C40—H40 | 119.4 |
O1—C16—N2 | 126.4 (3) | C46—C41—C42 | 118.7 (3) |
O1—C16—N4 | 125.7 (3) | C46—C41—C34 | 118.7 (3) |
N2—C16—N4 | 107.8 (2) | C42—C41—C34 | 122.6 (3) |
O2—C17—N5 | 126.4 (3) | C43—C42—C41 | 119.6 (4) |
O2—C17—N3 | 125.4 (3) | C43—C42—H42 | 120.2 |
N5—C17—N3 | 108.0 (2) | C41—C42—H42 | 120.2 |
N2—C18—N3 | 109.8 (2) | C44—C43—C42 | 120.3 (4) |
N2—C18—C19 | 112.0 (2) | C44—C43—H43 | 119.8 |
N3—C18—C19 | 112.0 (2) | C42—C43—H43 | 119.8 |
N2—C18—C25 | 102.38 (19) | C43—C44—C45 | 120.7 (4) |
N3—C18—C25 | 102.12 (19) | C43—C44—H44 | 119.7 |
C19—C18—C25 | 117.6 (2) | C45—C44—H44 | 119.7 |
C24—C19—C20 | 118.6 (3) | C46—C45—C44 | 119.0 (4) |
C24—C19—C18 | 121.3 (2) | C46—C45—H45 | 120.5 |
C20—C19—C18 | 120.1 (2) | C44—C45—H45 | 120.5 |
C21—C20—C19 | 120.6 (3) | C45—C46—C41 | 121.7 (4) |
C21—C20—H20 | 119.7 | C45—C46—H46 | 119.2 |
C19—C20—H20 | 119.7 | C41—C46—H46 | 119.2 |
C22—C21—C20 | 119.6 (3) | C7—N1—C14 | 110.6 (3) |
C22—C21—H21 | 120.2 | C7—N1—C15 | 111.1 (3) |
C20—C21—H21 | 120.2 | C14—N1—C15 | 107.0 (2) |
C23—C22—C21 | 120.6 (3) | C16—N2—C15 | 120.4 (2) |
C23—C22—H22 | 119.7 | C16—N2—C18 | 112.7 (2) |
C21—C22—H22 | 119.7 | C15—N2—C18 | 116.8 (2) |
C22—C23—C24 | 119.6 (3) | C17—N3—C14 | 118.5 (2) |
C22—C23—H23 | 120.2 | C17—N3—C18 | 111.8 (2) |
C24—C23—H23 | 120.2 | C14—N3—C18 | 115.6 (2) |
C23—C24—C19 | 121.0 (3) | C16—N4—C25 | 111.2 (2) |
C23—C24—H24 | 119.5 | C16—N4—C32 | 119.9 (2) |
C19—C24—H24 | 119.5 | C25—N4—C32 | 116.3 (2) |
N5—C25—N4 | 109.3 (2) | C17—N5—C25 | 111.6 (2) |
N5—C25—C26 | 110.8 (2) | C17—N5—C33 | 122.4 (2) |
N4—C25—C26 | 112.6 (2) | C25—N5—C33 | 116.1 (2) |
N5—C25—C18 | 103.5 (2) | C32—N6—C34 | 115.9 (2) |
N4—C25—C18 | 103.4 (2) | C32—N6—C33 | 109.0 (2) |
C26—C25—C18 | 116.7 (2) | C34—N6—C33 | 114.0 (2) |
C6—C1—C2—C3 | 1.3 (8) | N6—C34—C41—C42 | −33.2 (4) |
C1—C2—C3—C4 | −2.1 (8) | C35—C34—C41—C42 | 88.6 (3) |
C2—C3—C4—C5 | 0.4 (8) | C46—C41—C42—C43 | −1.5 (5) |
C3—C4—C5—C6 | 2.2 (7) | C34—C41—C42—C43 | −179.5 (3) |
C4—C5—C6—C1 | −3.0 (6) | C41—C42—C43—C44 | 1.6 (5) |
C4—C5—C6—C7 | 174.6 (4) | C42—C43—C44—C45 | 0.0 (6) |
C2—C1—C6—C5 | 1.3 (7) | C43—C44—C45—C46 | −1.6 (6) |
C2—C1—C6—C7 | −176.2 (4) | C44—C45—C46—C41 | 1.7 (5) |
C5—C6—C7—N1 | 149.7 (3) | C42—C41—C46—C45 | −0.1 (5) |
C1—C6—C7—N1 | −32.8 (5) | C34—C41—C46—C45 | 178.0 (3) |
C5—C6—C7—C8 | −87.8 (4) | C8—C7—N1—C14 | 58.8 (4) |
C1—C6—C7—C8 | 89.6 (5) | C6—C7—N1—C14 | −180.0 (3) |
N1—C7—C8—C9 | 53.9 (5) | C8—C7—N1—C15 | 177.5 (3) |
C6—C7—C8—C9 | −68.7 (5) | C6—C7—N1—C15 | −61.3 (4) |
N1—C7—C8—C13 | −129.8 (4) | N3—C14—N1—C7 | −176.9 (3) |
C6—C7—C8—C13 | 107.6 (4) | N3—C14—N1—C15 | 62.0 (3) |
C13—C8—C9—C10 | −0.8 (8) | N2—C15—N1—C7 | 177.2 (2) |
C7—C8—C9—C10 | 175.5 (4) | N2—C15—N1—C14 | −62.0 (3) |
C8—C9—C10—C11 | −0.1 (9) | O1—C16—N2—C15 | −24.1 (4) |
C9—C10—C11—C12 | 1.1 (11) | N4—C16—N2—C15 | 159.5 (2) |
C10—C11—C12—C13 | −1.2 (14) | O1—C16—N2—C18 | −168.3 (3) |
C9—C8—C13—C12 | 0.7 (8) | N4—C16—N2—C18 | 15.2 (3) |
C7—C8—C13—C12 | −175.7 (5) | N1—C15—N2—C16 | −87.1 (3) |
C11—C12—C13—C8 | 0.2 (12) | N1—C15—N2—C18 | 55.8 (3) |
N2—C18—C19—C24 | −153.2 (3) | N3—C18—N2—C16 | 100.6 (3) |
N3—C18—C19—C24 | −29.2 (4) | C19—C18—N2—C16 | −134.3 (2) |
C25—C18—C19—C24 | 88.6 (3) | C25—C18—N2—C16 | −7.3 (3) |
N2—C18—C19—C20 | 28.1 (4) | N3—C18—N2—C15 | −45.0 (3) |
N3—C18—C19—C20 | 152.0 (3) | C19—C18—N2—C15 | 80.1 (3) |
C25—C18—C19—C20 | −90.2 (3) | C25—C18—N2—C15 | −152.9 (2) |
C24—C19—C20—C21 | 1.4 (5) | O2—C17—N3—C14 | 27.3 (4) |
C18—C19—C20—C21 | −179.8 (3) | N5—C17—N3—C14 | −156.7 (2) |
C19—C20—C21—C22 | −0.9 (5) | O2—C17—N3—C18 | 165.6 (2) |
C20—C21—C22—C23 | −0.1 (6) | N5—C17—N3—C18 | −18.4 (3) |
C21—C22—C23—C24 | 0.7 (6) | N1—C14—N3—C17 | 81.6 (3) |
C22—C23—C24—C19 | −0.2 (5) | N1—C14—N3—C18 | −55.2 (3) |
C20—C19—C24—C23 | −0.8 (5) | N2—C18—N3—C17 | −95.5 (2) |
C18—C19—C24—C23 | −179.6 (3) | C19—C18—N3—C17 | 139.3 (2) |
N2—C18—C25—N5 | 111.1 (2) | C25—C18—N3—C17 | 12.6 (3) |
N3—C18—C25—N5 | −2.6 (2) | N2—C18—N3—C14 | 44.0 (3) |
C19—C18—C25—N5 | −125.6 (2) | C19—C18—N3—C14 | −81.1 (3) |
N2—C18—C25—N4 | −2.8 (2) | C25—C18—N3—C14 | 152.1 (2) |
N3—C18—C25—N4 | −116.5 (2) | O1—C16—N4—C25 | 166.4 (3) |
C19—C18—C25—N4 | 120.5 (2) | N2—C16—N4—C25 | −17.1 (3) |
N2—C18—C25—C26 | −126.9 (2) | O1—C16—N4—C32 | 25.9 (4) |
N3—C18—C25—C26 | 119.4 (2) | N2—C16—N4—C32 | −157.6 (2) |
C19—C18—C25—C26 | −3.7 (3) | N5—C25—N4—C16 | −97.6 (2) |
N5—C25—C26—C31 | 36.8 (4) | C26—C25—N4—C16 | 138.8 (2) |
N4—C25—C26—C31 | 159.5 (3) | C18—C25—N4—C16 | 12.1 (3) |
C18—C25—C26—C31 | −81.2 (3) | N5—C25—N4—C32 | 44.5 (3) |
N5—C25—C26—C27 | −146.1 (3) | C26—C25—N4—C32 | −79.1 (3) |
N4—C25—C26—C27 | −23.4 (4) | C18—C25—N4—C32 | 154.1 (2) |
C18—C25—C26—C27 | 95.9 (3) | N6—C32—N4—C16 | 87.9 (3) |
C31—C26—C27—C28 | −2.3 (5) | N6—C32—N4—C25 | −50.7 (4) |
C25—C26—C27—C28 | −179.4 (3) | O2—C17—N5—C25 | −167.6 (2) |
C26—C27—C28—C29 | 1.6 (7) | N3—C17—N5—C25 | 16.4 (3) |
C27—C28—C29—C30 | 0.4 (8) | O2—C17—N5—C33 | −23.2 (4) |
C28—C29—C30—C31 | −1.6 (7) | N3—C17—N5—C33 | 160.9 (2) |
C27—C26—C31—C30 | 1.2 (5) | N4—C25—N5—C17 | 101.4 (2) |
C25—C26—C31—C30 | 178.3 (3) | C26—C25—N5—C17 | −134.0 (2) |
C29—C30—C31—C26 | 0.8 (6) | C18—C25—N5—C17 | −8.2 (3) |
N6—C34—C35—C40 | 48.1 (4) | N4—C25—N5—C33 | −45.4 (3) |
C41—C34—C35—C40 | −75.1 (4) | C26—C25—N5—C33 | 79.2 (3) |
N6—C34—C35—C36 | −133.0 (3) | C18—C25—N5—C33 | −155.1 (2) |
C41—C34—C35—C36 | 103.8 (3) | N6—C33—N5—C17 | −90.4 (3) |
C40—C35—C36—C37 | 1.1 (5) | N6—C33—N5—C25 | 52.6 (3) |
C34—C35—C36—C37 | −177.8 (3) | N4—C32—N6—C34 | −77.9 (3) |
C35—C36—C37—C38 | −1.1 (6) | N4—C32—N6—C33 | 52.2 (3) |
C36—C37—C38—C39 | 0.2 (6) | C35—C34—N6—C32 | −174.8 (2) |
C37—C38—C39—C40 | 0.5 (6) | C41—C34—N6—C32 | −54.2 (3) |
C36—C35—C40—C39 | −0.3 (5) | C35—C34—N6—C33 | 57.6 (3) |
C34—C35—C40—C39 | 178.6 (3) | C41—C34—N6—C33 | 178.1 (2) |
C38—C39—C40—C35 | −0.5 (5) | N5—C33—N6—C32 | −53.1 (3) |
N6—C34—C41—C46 | 148.8 (3) | N5—C33—N6—C34 | 78.1 (3) |
C35—C34—C41—C46 | −89.4 (3) |
Experimental details
Crystal data | |
Chemical formula | C46H40N6O2 |
Mr | 708.84 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 1902.2 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9562, 6617, 3963 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.190, 1.03 |
No. of reflections | 6617 |
No. of parameters | 487 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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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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.