The main residue of the title compound, C
18H
22N
6O
6·C
2H
4Cl
2, is a derivative of glycoluril. The six-membered heterocycle adopts a chair conformation and shares two N atoms with two five-membered rings of the glycoluril unit to form the flexible sidewalls of a molecular clip. Two ethyl fragments and the solvent molecule are disordered; the site occupancy factors for the ethyl groups are 0.72/0.28 and 0.75/0.25 and for the solvent molecule 0.54/0.46. Intermolecular N—H
O and N—H
N hydrogen bonds link the cyclopenta[
cd]indene molecules into two-dimensional layers parallel to the
bc plane.
Supporting information
CCDC reference: 672816
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.072
- wR factor = 0.225
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.82 Ratio
| Author Response: This is due to disorder in main residue
|
PLAT432_ALERT_2_A Short Inter X...Y Contact C8 .. C12' .. 2.85 Ang.
| Author Response: This is due to disorder in main residue
|
Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact Cl1' .. C8' .. 3.14 Ang.
| Author Response: This is due to disorder in main residue
|
Alert level C
ABSTY03_ALERT_1_C The _exptl_absorpt_correction_type has been given as none.
However values have been given for Tmin and Tmax. Remove
these if an absorption correction has not been applied.
From the CIF: _exptl_absorpt_correction_T_min 0.938
From the CIF: _exptl_absorpt_correction_T_max 0.968
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.65 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O6
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11'
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C19
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C19'
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C20'
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C20
PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
PLAT413_ALERT_2_C Short Inter XH3 .. XHn H16 .. H12F .. 2.12 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 41.60 Deg.
C8 -C7 -H7C 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 39.50 Deg.
H7A -C7 -H7D 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 39.10 Deg.
C7 -C8 -H7C 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 15.00 Deg.
C11 -O6 -C11' 1.555 1.555 1.555
Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 26
2 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
19 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
11 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
6 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
The title compound was synthesized according to the procedure of Li et
al. (2006) in 45% isolated yield. Crystals for X-ray data collection were
obtained by slow evaporation of a 1,2-dichoroethane and methanol solution in a
ratio of 4:1 at 293 K.
C-bound H atoms were geometrically positioned (C–H= 0.93 Å (aromatic), 0.96 Å (methyl) or 0.97 Å (methylene)) and refined as riding, with
Uiso(H) = 1.2Ueq(C), or =Ueq(C) for disordered C atoms.
N-bound H atoms were found in difference, but placed in idealized positions
(N–H= 0.86 Å), and refined as riding, with Uiso(H)=1.2Ueq(N). Two
ethyl fragments in (I) were treated as disordered between two orientations
each, with the refined occupancies 0.720 (9)/0.280 (9) and 0.754 (11)/0.246 (11),
respectively. The solvent molecule was also treated as disordered between two
positions, with the refined occupancies 0.458 (10) and 0.542 (10), respectively.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).
Diethyl
1,4-dioxo-6-(3-pyridyl)perhydro-2,3,4a,6,7a-pentaazacyclopenta[cd]indene- 2a,7
b-dicarboxylate 1,2-dichoroethane solvate
top
Crystal data top
C18H22N6O6·C2H4Cl2 | F(000) = 1080 |
Mr = 517.37 | Dx = 1.468 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2658 reflections |
a = 12.9023 (9) Å | θ = 2.3–21.1° |
b = 16.4032 (11) Å | µ = 0.33 mm−1 |
c = 12.1719 (8) Å | T = 294 K |
β = 114.657 (1)° | Block, colourless |
V = 2341.2 (3) Å3 | 0.20 × 0.10 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker SMART 4K CCD area-detector diffractometer | 2684 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.058 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
ϕ and ω scans | h = −15→12 |
13883 measured reflections | k = −19→19 |
4114 independent reflections | l = −14→14 |
Refinement top
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)] = 0.073 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.225 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.1319P)2] where P = (Fo2 + 2Fc2)/3 |
4114 reflections | (Δ/σ)max < 0.001 |
359 parameters | Δρmax = 0.35 e Å−3 |
26 restraints | Δρmin = −0.46 e Å−3 |
Crystal data top
C18H22N6O6·C2H4Cl2 | V = 2341.2 (3) Å3 |
Mr = 517.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.9023 (9) Å | µ = 0.33 mm−1 |
b = 16.4032 (11) Å | T = 294 K |
c = 12.1719 (8) Å | 0.20 × 0.10 × 0.10 mm |
β = 114.657 (1)° | |
Data collection top
Bruker SMART 4K CCD area-detector diffractometer | 2684 reflections with I > 2σ(I) |
13883 measured reflections | Rint = 0.058 |
4114 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.073 | 26 restraints |
wR(F2) = 0.225 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.35 e Å−3 |
4114 reflections | Δρmin = −0.46 e Å−3 |
359 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C19 | 0.4234 (19) | 0.4751 (19) | 0.346 (3) | 0.30 (2) | 0.458 (10) |
H19A | 0.4754 | 0.4958 | 0.4241 | 0.30* | 0.458 (10) |
H19B | 0.4679 | 0.4570 | 0.3028 | 0.30* | 0.458 (10) |
C1 | 0.5988 (3) | 0.24533 (17) | 0.1119 (3) | 0.0434 (8) | |
H1A | 0.5250 | 0.2406 | 0.0438 | 0.052* | |
H1B | 0.6482 | 0.2039 | 0.1028 | 0.052* | |
C2 | 0.6934 (3) | 0.24312 (19) | 0.3264 (3) | 0.0490 (9) | |
H2A | 0.7476 | 0.2025 | 0.3252 | 0.059* | |
H2B | 0.6830 | 0.2356 | 0.4002 | 0.059* | |
C3 | 0.5798 (3) | 0.39281 (18) | 0.0564 (3) | 0.0440 (8) | |
C4 | 0.7221 (3) | 0.3900 (2) | 0.3877 (3) | 0.0496 (9) | |
C5 | 0.7473 (3) | 0.35055 (18) | 0.2168 (3) | 0.0398 (7) | |
C6 | 0.8552 (3) | 0.3164 (2) | 0.2086 (3) | 0.0502 (9) | |
C7 | 0.9642 (4) | 0.3216 (4) | 0.0915 (5) | 0.1029 (18) | |
H7A | 0.9511 | 0.2693 | 0.0508 | 0.10* | 0.720 (9) |
H7B | 1.0312 | 0.3174 | 0.1676 | 0.10* | 0.720 (9) |
H7C | 0.9487 | 0.3301 | 0.0072 | 0.10* | 0.280 (9) |
H7D | 0.9793 | 0.2641 | 0.1092 | 0.10* | 0.280 (9) |
C8 | 0.9803 (9) | 0.3879 (6) | 0.0128 (10) | 0.139 (4) | 0.720 (9) |
H8A | 0.9284 | 0.3790 | −0.0699 | 0.14* | 0.720 (9) |
H8B | 1.0572 | 0.3863 | 0.0199 | 0.14* | 0.720 (9) |
H8C | 0.9656 | 0.4402 | 0.0388 | 0.14* | 0.720 (9) |
C8' | 1.0650 (19) | 0.3728 (16) | 0.146 (3) | 0.139 (4) | 0.280 (9) |
H8'1 | 1.0879 | 0.3756 | 0.2317 | 0.14* | 0.280 (9) |
H8'2 | 1.0479 | 0.4266 | 0.1121 | 0.14* | 0.280 (9) |
H8'3 | 1.1258 | 0.3499 | 0.1299 | 0.14* | 0.280 (9) |
C9 | 0.7366 (3) | 0.44625 (18) | 0.2187 (3) | 0.0439 (8) | |
C10 | 0.8353 (3) | 0.4977 (2) | 0.2176 (3) | 0.0545 (9) | |
C11 | 1.0337 (10) | 0.5246 (6) | 0.3268 (11) | 0.103 (3) | 0.754 (11) |
H11A | 1.0406 | 0.5275 | 0.2506 | 0.10* | 0.754 (11) |
H11B | 1.1006 | 0.4970 | 0.3850 | 0.10* | 0.754 (11) |
C12 | 1.0264 (11) | 0.6081 (6) | 0.3702 (13) | 0.192 (5) | 0.754 (11) |
H12A | 0.9529 | 0.6309 | 0.3216 | 0.19* | 0.754 (11) |
H12B | 1.0847 | 0.6416 | 0.3641 | 0.19* | 0.754 (11) |
H12C | 1.0368 | 0.6056 | 0.4530 | 0.19* | 0.754 (11) |
C11' | 1.019 (4) | 0.543 (2) | 0.333 (3) | 0.103 (3) | 0.246 (11) |
H11C | 1.0947 | 0.5202 | 0.3755 | 0.10* | 0.246 (11) |
H11D | 1.0094 | 0.5860 | 0.3833 | 0.10* | 0.246 (11) |
C12' | 1.006 (3) | 0.5791 (19) | 0.211 (3) | 0.192 (5) | 0.246 (11) |
H12D | 0.9722 | 0.5391 | 0.1486 | 0.19* | 0.246 (11) |
H12E | 1.0799 | 0.5938 | 0.2157 | 0.19* | 0.246 (11) |
H12F | 0.9584 | 0.6265 | 0.1927 | 0.19* | 0.246 (11) |
C13 | 0.4906 (3) | 0.2760 (2) | 0.2311 (3) | 0.0488 (8) | |
H13A | 0.4957 | 0.3327 | 0.2112 | 0.059* | |
H13B | 0.4967 | 0.2738 | 0.3132 | 0.059* | |
C14 | 0.3768 (3) | 0.24205 (19) | 0.1459 (3) | 0.0454 (8) | |
C15 | 0.2997 (3) | 0.2838 (2) | 0.0490 (3) | 0.0596 (10) | |
H15 | 0.3170 | 0.3358 | 0.0311 | 0.072* | |
C16 | 0.1963 (3) | 0.2484 (2) | −0.0223 (4) | 0.0684 (11) | |
H16 | 0.1429 | 0.2764 | −0.0880 | 0.082* | |
C17 | 0.1738 (3) | 0.1718 (2) | 0.0053 (4) | 0.0645 (11) | |
H17 | 0.1040 | 0.1484 | −0.0432 | 0.077* | |
C18 | 0.3455 (3) | 0.1646 (2) | 0.1670 (3) | 0.0559 (9) | |
H18 | 0.3966 | 0.1359 | 0.2334 | 0.067* | |
C20 | 0.348 (2) | 0.5359 (12) | 0.281 (2) | 0.191 (10) | 0.458 (10) |
H20A | 0.3948 | 0.5781 | 0.2682 | 0.19* | 0.458 (10) |
H20B | 0.3185 | 0.5588 | 0.3352 | 0.19* | 0.458 (10) |
C19' | 0.353 (2) | 0.4923 (11) | 0.3537 (19) | 0.177 (9) | 0.542 (10) |
H19C | 0.2866 | 0.5249 | 0.3050 | 0.18* | 0.542 (10) |
H19D | 0.3791 | 0.5102 | 0.4370 | 0.18* | 0.542 (10) |
C20' | 0.4474 (14) | 0.5059 (9) | 0.3103 (15) | 0.145 (7) | 0.542 (10) |
H20C | 0.5008 | 0.4608 | 0.3308 | 0.145* | 0.542 (10) |
H20D | 0.4881 | 0.5567 | 0.3397 | 0.145* | 0.542 (10) |
Cl1 | 0.3467 (12) | 0.3958 (6) | 0.3638 (8) | 0.194 (5) | 0.458 (10) |
Cl2 | 0.2351 (10) | 0.5258 (4) | 0.1477 (5) | 0.204 (6) | 0.458 (10) |
Cl1' | 0.3153 (13) | 0.3950 (6) | 0.3439 (13) | 0.285 (8) | 0.542 (10) |
Cl2' | 0.3591 (9) | 0.5093 (2) | 0.1587 (5) | 0.177 (4) | 0.542 (10) |
N1 | 0.2469 (3) | 0.12886 (18) | 0.0982 (3) | 0.0627 (9) | |
N2 | 0.5853 (2) | 0.23011 (15) | 0.2236 (2) | 0.0428 (7) | |
N3 | 0.6469 (2) | 0.32622 (14) | 0.1092 (2) | 0.0380 (6) | |
N4 | 0.7410 (2) | 0.32533 (14) | 0.3273 (2) | 0.0418 (7) | |
N5 | 0.6352 (2) | 0.46129 (16) | 0.1113 (3) | 0.0544 (8) | |
H5 | 0.6118 | 0.5094 | 0.0844 | 0.065* | |
N6 | 0.7249 (2) | 0.45955 (16) | 0.3290 (2) | 0.0533 (8) | |
H6 | 0.7201 | 0.5073 | 0.3556 | 0.064* | |
O1 | 0.4855 (2) | 0.38855 (13) | −0.0294 (2) | 0.0559 (7) | |
O2 | 0.7055 (3) | 0.38493 (16) | 0.4792 (2) | 0.0753 (9) | |
O3 | 0.9188 (2) | 0.26940 (19) | 0.2803 (3) | 0.0830 (9) | |
O4 | 0.8647 (2) | 0.34583 (18) | 0.1125 (2) | 0.0712 (8) | |
O5 | 0.8239 (3) | 0.54950 (18) | 0.1454 (3) | 0.0846 (10) | |
O6 | 0.9320 (2) | 0.47937 (16) | 0.3110 (3) | 0.0705 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C19 | 0.31 (6) | 0.30 (7) | 0.29 (5) | 0.00 (4) | 0.14 (5) | −0.01 (5) |
C1 | 0.0462 (19) | 0.0367 (16) | 0.0449 (18) | −0.0002 (14) | 0.0168 (16) | −0.0029 (14) |
C2 | 0.053 (2) | 0.0409 (17) | 0.0445 (19) | −0.0002 (15) | 0.0114 (17) | 0.0092 (14) |
C3 | 0.045 (2) | 0.0413 (17) | 0.0375 (18) | 0.0022 (14) | 0.0093 (17) | 0.0071 (14) |
C4 | 0.054 (2) | 0.053 (2) | 0.0408 (19) | −0.0112 (16) | 0.0190 (18) | −0.0049 (15) |
C5 | 0.0342 (17) | 0.0398 (16) | 0.0399 (17) | 0.0013 (13) | 0.0101 (14) | 0.0041 (13) |
C6 | 0.042 (2) | 0.054 (2) | 0.052 (2) | 0.0006 (16) | 0.0157 (18) | 0.0011 (17) |
C7 | 0.076 (3) | 0.150 (5) | 0.108 (4) | 0.018 (3) | 0.063 (3) | 0.007 (3) |
C8 | 0.134 (9) | 0.160 (8) | 0.176 (9) | −0.044 (6) | 0.116 (8) | −0.033 (7) |
C8' | 0.134 (9) | 0.160 (8) | 0.176 (9) | −0.044 (6) | 0.116 (8) | −0.033 (7) |
C9 | 0.0421 (19) | 0.0399 (16) | 0.0415 (18) | −0.0001 (14) | 0.0092 (15) | 0.0056 (13) |
C10 | 0.053 (2) | 0.0460 (19) | 0.057 (2) | −0.0039 (16) | 0.0147 (19) | 0.0068 (17) |
C11 | 0.055 (4) | 0.088 (6) | 0.139 (5) | −0.020 (5) | 0.014 (3) | 0.023 (4) |
C12 | 0.157 (9) | 0.148 (8) | 0.236 (11) | −0.009 (7) | 0.048 (9) | −0.033 (8) |
C11' | 0.055 (4) | 0.088 (6) | 0.139 (5) | −0.020 (5) | 0.014 (3) | 0.023 (4) |
C12' | 0.157 (9) | 0.148 (8) | 0.236 (11) | −0.009 (7) | 0.048 (9) | −0.033 (8) |
C13 | 0.056 (2) | 0.0442 (17) | 0.049 (2) | −0.0032 (15) | 0.0244 (18) | −0.0043 (15) |
C14 | 0.047 (2) | 0.0416 (17) | 0.0496 (19) | −0.0017 (15) | 0.0218 (17) | 0.0000 (15) |
C15 | 0.059 (2) | 0.0439 (18) | 0.069 (2) | 0.0009 (17) | 0.020 (2) | 0.0131 (17) |
C16 | 0.056 (3) | 0.057 (2) | 0.072 (3) | 0.0049 (19) | 0.006 (2) | 0.014 (2) |
C17 | 0.046 (2) | 0.061 (2) | 0.069 (3) | −0.0062 (18) | 0.007 (2) | 0.000 (2) |
C18 | 0.055 (2) | 0.052 (2) | 0.054 (2) | −0.0024 (17) | 0.0152 (19) | 0.0075 (16) |
C20 | 0.19 (3) | 0.19 (3) | 0.19 (3) | 0.01 (2) | 0.08 (2) | −0.003 (18) |
C19' | 0.19 (2) | 0.16 (2) | 0.180 (19) | 0.026 (17) | 0.079 (17) | −0.027 (15) |
C20' | 0.165 (15) | 0.060 (7) | 0.187 (18) | −0.044 (9) | 0.051 (14) | −0.009 (8) |
Cl1 | 0.292 (10) | 0.208 (9) | 0.166 (5) | 0.138 (8) | 0.180 (6) | 0.093 (5) |
Cl2 | 0.250 (11) | 0.163 (5) | 0.131 (4) | −0.074 (6) | 0.013 (5) | 0.025 (3) |
Cl1' | 0.368 (13) | 0.199 (9) | 0.458 (17) | 0.014 (7) | 0.342 (13) | 0.091 (8) |
Cl2' | 0.290 (10) | 0.112 (3) | 0.167 (4) | −0.010 (3) | 0.134 (6) | 0.017 (2) |
N1 | 0.058 (2) | 0.0494 (17) | 0.070 (2) | −0.0098 (15) | 0.0156 (18) | 0.0085 (15) |
N2 | 0.0431 (16) | 0.0396 (14) | 0.0403 (15) | −0.0009 (11) | 0.0119 (13) | 0.0013 (11) |
N3 | 0.0371 (14) | 0.0378 (13) | 0.0338 (13) | 0.0005 (11) | 0.0095 (12) | 0.0037 (11) |
N4 | 0.0445 (16) | 0.0393 (14) | 0.0339 (14) | −0.0030 (11) | 0.0085 (12) | 0.0045 (11) |
N5 | 0.0477 (17) | 0.0368 (14) | 0.0565 (18) | 0.0019 (12) | −0.0004 (14) | 0.0115 (13) |
N6 | 0.063 (2) | 0.0413 (15) | 0.0565 (18) | −0.0040 (13) | 0.0256 (16) | −0.0062 (13) |
O1 | 0.0483 (15) | 0.0497 (13) | 0.0466 (14) | 0.0023 (11) | −0.0032 (12) | 0.0108 (10) |
O2 | 0.105 (2) | 0.0729 (18) | 0.0578 (17) | −0.0234 (15) | 0.0442 (17) | −0.0146 (13) |
O3 | 0.0560 (18) | 0.093 (2) | 0.093 (2) | 0.0292 (15) | 0.0242 (16) | 0.0342 (17) |
O4 | 0.0566 (17) | 0.095 (2) | 0.0707 (18) | 0.0124 (14) | 0.0348 (15) | 0.0108 (15) |
O5 | 0.078 (2) | 0.0799 (19) | 0.087 (2) | −0.0123 (15) | 0.0253 (18) | 0.0347 (17) |
O6 | 0.0419 (15) | 0.0689 (17) | 0.0802 (19) | −0.0131 (12) | 0.0053 (14) | 0.0163 (14) |
Geometric parameters (Å, º) top
C19—C20 | 1.388 (18) | C10—O6 | 1.325 (4) |
C19—Cl1 | 1.70 (2) | C11—O6 | 1.449 (9) |
C19—H19A | 0.9700 | C11—C12 | 1.485 (9) |
C19—H19B | 0.9700 | C11—H11A | 0.9700 |
C1—N2 | 1.463 (4) | C11—H11B | 0.9700 |
C1—N3 | 1.471 (4) | C12—H12A | 0.9600 |
C1—H1A | 0.9700 | C12—H12B | 0.9600 |
C1—H1B | 0.9700 | C12—H12C | 0.9600 |
C2—N2 | 1.449 (4) | C11'—O6 | 1.48 (2) |
C2—N4 | 1.480 (4) | C11'—C12' | 1.542 (11) |
C2—H2A | 0.9700 | C11'—H11C | 0.9700 |
C2—H2B | 0.9700 | C11'—H11D | 0.9700 |
C3—O1 | 1.231 (4) | C12'—H12D | 0.9600 |
C3—N5 | 1.349 (4) | C12'—H12E | 0.9600 |
C3—N3 | 1.375 (4) | C12'—H12F | 0.9600 |
C4—O2 | 1.222 (4) | C13—N2 | 1.470 (4) |
C4—N6 | 1.355 (4) | C13—C14 | 1.507 (5) |
C4—N4 | 1.368 (4) | C13—H13A | 0.9700 |
C5—N4 | 1.442 (4) | C13—H13B | 0.9700 |
C5—N3 | 1.462 (4) | C14—C15 | 1.368 (5) |
C5—C6 | 1.542 (5) | C14—C18 | 1.389 (5) |
C5—C9 | 1.577 (4) | C15—C16 | 1.380 (5) |
C6—O3 | 1.197 (4) | C15—H15 | 0.9300 |
C6—O4 | 1.318 (4) | C16—C17 | 1.362 (5) |
C7—C8' | 1.455 (16) | C16—H16 | 0.9300 |
C7—O4 | 1.464 (5) | C17—N1 | 1.333 (5) |
C7—C8 | 1.519 (9) | C17—H17 | 0.9300 |
C7—H7A | 0.9700 | C18—N1 | 1.332 (4) |
C7—H7B | 0.9700 | C18—H18 | 0.9300 |
C7—H7C | 0.9700 | C20—Cl2 | 1.672 (17) |
C7—H7D | 0.9700 | C20—H20A | 0.9700 |
C8—H7C | 1.0229 | C20—H20B | 0.9700 |
C8—H8A | 0.9600 | C19'—C20' | 1.538 (17) |
C8—H8B | 0.9600 | C19'—Cl1' | 1.658 (17) |
C8—H8C | 0.9600 | C19'—H19C | 0.9700 |
C8'—H8'1 | 0.9600 | C19'—H19D | 0.9700 |
C8'—H8'2 | 0.9600 | C20'—Cl2' | 1.718 (16) |
C8'—H8'3 | 0.9600 | C20'—H20C | 0.9700 |
C9—N6 | 1.428 (4) | C20'—H20D | 0.9700 |
C9—N5 | 1.433 (4) | N5—H5 | 0.8600 |
C9—C10 | 1.532 (5) | N6—H6 | 0.8600 |
C10—O5 | 1.187 (4) | | |
| | | |
C20—C19—Cl1 | 108.4 (18) | O6—C11—H11A | 109.8 |
C20—C19—H19A | 110.0 | C12—C11—H11A | 109.8 |
Cl1—C19—H19A | 110.0 | O6—C11—H11B | 109.8 |
C20—C19—H19B | 110.0 | C12—C11—H11B | 109.8 |
Cl1—C19—H19B | 110.0 | H11A—C11—H11B | 108.3 |
H19A—C19—H19B | 108.4 | O6—C11'—C12' | 109.0 (17) |
N2—C1—N3 | 112.9 (2) | O6—C11'—H11C | 109.9 |
N2—C1—H1A | 109.0 | C12'—C11'—H11C | 109.9 |
N3—C1—H1A | 109.0 | O6—C11'—H11D | 109.9 |
N2—C1—H1B | 109.0 | C12'—C11'—H11D | 109.9 |
N3—C1—H1B | 109.0 | H11C—C11'—H11D | 108.3 |
H1A—C1—H1B | 107.8 | C11'—C12'—H12D | 109.5 |
N2—C2—N4 | 112.8 (2) | C11'—C12'—H12E | 109.5 |
N2—C2—H2A | 109.0 | H12D—C12'—H12E | 109.5 |
N4—C2—H2A | 109.0 | C11'—C12'—H12F | 109.5 |
N2—C2—H2B | 109.0 | H12D—C12'—H12F | 109.5 |
N4—C2—H2B | 109.0 | H12E—C12'—H12F | 109.5 |
H2A—C2—H2B | 107.8 | N2—C13—C14 | 111.4 (3) |
O1—C3—N5 | 126.8 (3) | N2—C13—H13A | 109.4 |
O1—C3—N3 | 123.9 (3) | C14—C13—H13A | 109.4 |
N5—C3—N3 | 109.2 (3) | N2—C13—H13B | 109.4 |
O2—C4—N6 | 126.2 (3) | C14—C13—H13B | 109.4 |
O2—C4—N4 | 125.1 (3) | H13A—C13—H13B | 108.0 |
N6—C4—N4 | 108.7 (3) | C15—C14—C18 | 117.0 (3) |
N4—C5—N3 | 112.6 (2) | C15—C14—C13 | 123.9 (3) |
N4—C5—C6 | 111.1 (3) | C18—C14—C13 | 119.1 (3) |
N3—C5—C6 | 109.2 (2) | C14—C15—C16 | 119.8 (3) |
N4—C5—C9 | 103.5 (2) | C14—C15—H15 | 120.1 |
N3—C5—C9 | 103.6 (2) | C16—C15—H15 | 120.1 |
C6—C5—C9 | 116.7 (3) | C17—C16—C15 | 118.8 (3) |
O3—C6—O4 | 126.4 (3) | C17—C16—H16 | 120.6 |
O3—C6—C5 | 123.3 (3) | C15—C16—H16 | 120.6 |
O4—C6—C5 | 110.2 (3) | N1—C17—C16 | 123.3 (4) |
C8'—C7—O4 | 116.6 (11) | N1—C17—H17 | 118.4 |
C8'—C7—C8 | 62.8 (12) | C16—C17—H17 | 118.4 |
O4—C7—C8 | 106.1 (5) | N1—C18—C14 | 124.2 (3) |
C8'—C7—H7A | 132.4 | N1—C18—H18 | 117.9 |
O4—C7—H7A | 110.5 | C14—C18—H18 | 117.9 |
C8—C7—H7A | 110.5 | C19—C20—Cl2 | 127 (2) |
C8'—C7—H7B | 48.3 | C19—C20—H20A | 105.6 |
O4—C7—H7B | 110.5 | Cl2—C20—H20A | 105.6 |
C8—C7—H7B | 110.5 | C19—C20—H20B | 105.6 |
H7A—C7—H7B | 108.7 | Cl2—C20—H20B | 105.6 |
C8'—C7—H7C | 98.6 | H20A—C20—H20B | 106.1 |
O4—C7—H7C | 109.7 | C20'—C19'—Cl1' | 111.3 (12) |
C8—C7—H7C | 41.6 | C20'—C19'—H19C | 109.4 |
H7A—C7—H7C | 70.7 | Cl1'—C19'—H19C | 109.4 |
H7B—C7—H7C | 136.7 | C20'—C19'—H19D | 109.4 |
C8'—C7—H7D | 113.7 | Cl1'—C19'—H19D | 109.4 |
O4—C7—H7D | 109.6 | H19C—C19'—H19D | 108.0 |
C8—C7—H7D | 140.2 | C19'—C20'—Cl2' | 96.2 (12) |
H7A—C7—H7D | 39.5 | C19'—C20'—H20C | 112.5 |
H7B—C7—H7D | 72.6 | Cl2'—C20'—H20C | 112.5 |
H7C—C7—H7D | 107.9 | C19'—C20'—H20D | 112.5 |
C7—C8—H7C | 39.1 | Cl2'—C20'—H20D | 112.5 |
C7—C8—H8A | 109.5 | H20C—C20'—H20D | 110.0 |
H7C—C8—H8A | 72.8 | C18—N1—C17 | 116.9 (3) |
C7—C8—H8B | 109.5 | C2—N2—C1 | 109.4 (3) |
H7C—C8—H8B | 110.5 | C2—N2—C13 | 113.4 (3) |
C7—C8—H8C | 109.5 | C1—N2—C13 | 113.2 (2) |
H7C—C8—H8C | 136.2 | C3—N3—C5 | 110.6 (2) |
C7—C8'—H8'1 | 109.5 | C3—N3—C1 | 122.5 (3) |
C7—C8'—H8'2 | 109.5 | C5—N3—C1 | 116.8 (2) |
H8'1—C8'—H8'2 | 109.5 | C4—N4—C5 | 111.7 (2) |
C7—C8'—H8'3 | 109.5 | C4—N4—C2 | 123.0 (3) |
H8'1—C8'—H8'3 | 109.5 | C5—N4—C2 | 116.0 (2) |
H8'2—C8'—H8'3 | 109.5 | C3—N5—C9 | 113.7 (2) |
N6—C9—N5 | 114.6 (3) | C3—N5—H5 | 123.2 |
N6—C9—C10 | 109.8 (3) | C9—N5—H5 | 123.2 |
N5—C9—C10 | 110.1 (3) | C4—N6—C9 | 113.8 (3) |
N6—C9—C5 | 102.1 (2) | C4—N6—H6 | 123.1 |
N5—C9—C5 | 102.1 (2) | C9—N6—H6 | 123.1 |
C10—C9—C5 | 118.0 (3) | C6—O4—C7 | 118.0 (3) |
O5—C10—O6 | 125.4 (3) | C10—O6—C11 | 118.3 (5) |
O5—C10—C9 | 123.6 (3) | C10—O6—C11' | 111.6 (16) |
O6—C10—C9 | 110.8 (3) | C11—O6—C11' | 15 (3) |
O6—C11—C12 | 109.3 (9) | | |
| | | |
N4—C5—C6—O3 | 6.1 (5) | N4—C5—N3—C3 | 107.4 (3) |
N3—C5—C6—O3 | −118.7 (4) | C6—C5—N3—C3 | −128.6 (3) |
C9—C5—C6—O3 | 124.4 (4) | C9—C5—N3—C3 | −3.7 (3) |
N4—C5—C6—O4 | −174.5 (3) | N4—C5—N3—C1 | −38.9 (3) |
N3—C5—C6—O4 | 60.7 (3) | C6—C5—N3—C1 | 85.0 (3) |
C9—C5—C6—O4 | −56.3 (4) | C9—C5—N3—C1 | −150.0 (3) |
N4—C5—C9—N6 | −0.6 (3) | N2—C1—N3—C3 | −94.8 (3) |
N3—C5—C9—N6 | 117.1 (2) | N2—C1—N3—C5 | 47.3 (3) |
C6—C5—C9—N6 | −122.9 (3) | O2—C4—N4—C5 | 174.7 (3) |
N4—C5—C9—N5 | −119.4 (3) | N6—C4—N4—C5 | −5.2 (4) |
N3—C5—C9—N5 | −1.7 (3) | O2—C4—N4—C2 | 29.4 (5) |
C6—C5—C9—N5 | 118.3 (3) | N6—C4—N4—C2 | −150.5 (3) |
N4—C5—C9—C10 | 119.8 (3) | N3—C5—N4—C4 | −107.7 (3) |
N3—C5—C9—C10 | −122.5 (3) | C6—C5—N4—C4 | 129.4 (3) |
C6—C5—C9—C10 | −2.5 (4) | C9—C5—N4—C4 | 3.5 (3) |
N6—C9—C10—O5 | −118.2 (4) | N3—C5—N4—C2 | 40.1 (3) |
N5—C9—C10—O5 | 8.9 (5) | C6—C5—N4—C2 | −82.7 (3) |
C5—C9—C10—O5 | 125.5 (4) | C9—C5—N4—C2 | 151.3 (3) |
N6—C9—C10—O6 | 58.3 (4) | N2—C2—N4—C4 | 93.3 (4) |
N5—C9—C10—O6 | −174.6 (3) | N2—C2—N4—C5 | −50.7 (4) |
C5—C9—C10—O6 | −58.0 (4) | O1—C3—N5—C9 | 172.1 (3) |
N2—C13—C14—C15 | −114.8 (4) | N3—C3—N5—C9 | −9.6 (4) |
N2—C13—C14—C18 | 66.8 (4) | N6—C9—N5—C3 | −102.7 (3) |
C18—C14—C15—C16 | 0.1 (5) | C10—C9—N5—C3 | 133.0 (3) |
C13—C14—C15—C16 | −178.3 (3) | C5—C9—N5—C3 | 6.8 (4) |
C14—C15—C16—C17 | −0.6 (6) | O2—C4—N6—C9 | −175.0 (4) |
C15—C16—C17—N1 | 0.0 (7) | N4—C4—N6—C9 | 4.9 (4) |
C15—C14—C18—N1 | 1.0 (5) | N5—C9—N6—C4 | 107.0 (3) |
C13—C14—C18—N1 | 179.6 (3) | C10—C9—N6—C4 | −128.6 (3) |
Cl1—C19—C20—Cl2 | −53 (5) | C5—C9—N6—C4 | −2.6 (3) |
Cl1'—C19'—C20'—Cl2' | 82.1 (15) | O3—C6—O4—C7 | −2.2 (6) |
C14—C18—N1—C17 | −1.6 (6) | C5—C6—O4—C7 | 178.5 (3) |
C16—C17—N1—C18 | 1.1 (6) | C8'—C7—O4—C6 | −89.6 (15) |
N4—C2—N2—C1 | 55.9 (3) | C8—C7—O4—C6 | −156.8 (5) |
N4—C2—N2—C13 | −71.5 (3) | O5—C10—O6—C11 | −1.3 (8) |
N3—C1—N2—C2 | −54.3 (3) | C9—C10—O6—C11 | −177.7 (6) |
N3—C1—N2—C13 | 73.2 (3) | O5—C10—O6—C11' | 14 (2) |
C14—C13—N2—C2 | −162.3 (3) | C9—C10—O6—C11' | −163 (2) |
C14—C13—N2—C1 | 72.3 (3) | C12—C11—O6—C10 | 73.4 (10) |
O1—C3—N3—C5 | −173.6 (3) | C12—C11—O6—C11' | 6 (5) |
N5—C3—N3—C5 | 8.1 (4) | C12'—C11'—O6—C10 | −35 (4) |
O1—C3—N3—C1 | −29.5 (5) | C12'—C11'—O6—C11 | 84 (6) |
N5—C3—N3—C1 | 152.1 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O1 | 0.97 | 2.56 | 2.918 (4) | 102 |
C19′—H19D···O2i | 0.97 | 2.47 | 3.166 (17) | 128 |
C1—H1B···O2ii | 0.97 | 2.42 | 3.305 (4) | 152 |
N6—H6···N1iii | 0.86 | 2.07 | 2.892 (4) | 160 |
N5—H5···O1iv | 0.86 | 2.03 | 2.862 (3) | 162 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+1, −y+1, −z. |
Experimental details
Crystal data |
Chemical formula | C18H22N6O6·C2H4Cl2 |
Mr | 517.37 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 12.9023 (9), 16.4032 (11), 12.1719 (8) |
β (°) | 114.657 (1) |
V (Å3) | 2341.2 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
|
Data collection |
Diffractometer | Bruker SMART 4K CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13883, 4114, 2684 |
Rint | 0.058 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.073, 0.225, 1.04 |
No. of reflections | 4114 |
No. of parameters | 359 |
No. of restraints | 26 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.46 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6···N1i | 0.86 | 2.07 | 2.892 (4) | 160.4 |
N5—H5···O1ii | 0.86 | 2.03 | 2.862 (3) | 162.3 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z. |
In 1905, Behrend reported that the condensation of glycoluril and formaldehyde in dilute HCl yielded an insoluble polymeric material now known as Behrend's polymer (Behrend et al., 1905). Glycoluril and its derivatives have during the past two decades established an impressive career as building blocks for supramolecular chemistry (Freeman et al., 1981; Rebek, 2005; Rowan et al., 1999; Wu et al., 2002). As a part of our ongoing investigation into glycoluril derivatives (Li et al., 2006), we report here the structure of the title compound, 1,2-dichoroethane solvate of (I) (Fig. 1).
The molecular structure of the main residue, (I), and solvent molecule are shown in Fig. 1. Molecule (I) has three fused rings, namely, two nearly planar imidazole five-membered rings that adopt envelope conformation with the C═ O groups at the flap position and one non-planar triazine six-membered ring that adopts a chair conformation.
In the crystal, the intermolecular N—H···O and N—H···N hydrogen bonds (Table 1) link the molecules of (I) into two-dimensional layers parallel to bc plane.