Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054438/hk2354sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054438/hk2354Isup2.hkl |
CCDC reference: 672817
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.042
- wR factor = 0.106
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.64 Ratio
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.91 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.72 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C19 PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.910 Tmax scaled 0.480 Tmin scaled 0.369 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 27.00 From the CIF: _reflns_number_total 4879 Count of symmetry unique reflns 2771 Completeness (_total/calc) 176.07% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2108 Fraction of Friedel pairs measured 0.761 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 40
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general background, see: Burnett et al. (2003); Wu et al. (2002). Fing-conformation puckering parameters, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).
The title compound was synthesized according to the procedure reported (Wu et al., 2002). Crystals appropriate for X-ray analysis were obtained by slow evaporation of the dichloromethane solution at 283 K.
When the crystal structure was solved, the atoms C15, H15A, H15B, C16, H16A, H16B and H16C were found to be disordered. During refinement, the occupancies of disordered C and H atoms were kept fixed as C15 = 0.63, C15' = 0.37, C16 = 0.63, C16' = 0.37, H15A = 0.63, H15C = 0.37, H15B = 0.63, H15D = 0.37, H16A = 0.63, H16D = 0.37, H16B = 0.63, H16E = 0.37, H16C = 0.63 and H16F = 0.37. H atoms were positioned geometrically with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.
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: SHELXTL (Bruker, 2001).
C20H20Br2N4O7 | F(000) = 1176 |
Mr = 588.22 | Dx = 1.745 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4974 reflections |
a = 10.6430 (12) Å | θ = 2.6–24.1° |
b = 11.2669 (13) Å | µ = 3.67 mm−1 |
c = 18.673 (2) Å | T = 298 K |
V = 2239.1 (4) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 4879 independent reflections |
Radiation source: fine-focus sealed tube | 3828 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ϕ andω scans | θmax = 27.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick,1996) | h = −13→7 |
Tmin = 0.406, Tmax = 0.527 | k = −14→14 |
13113 measured reflections | l = −23→23 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0534P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
4879 reflections | Δρmax = 0.87 e Å−3 |
320 parameters | Δρmin = −0.56 e Å−3 |
40 restraints | Absolute structure: Flack (1983), with 2108 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.019 (10) |
C20H20Br2N4O7 | V = 2239.1 (4) Å3 |
Mr = 588.22 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 10.6430 (12) Å | µ = 3.67 mm−1 |
b = 11.2669 (13) Å | T = 298 K |
c = 18.673 (2) Å | 0.30 × 0.20 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 4879 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick,1996) | 3828 reflections with I > 2σ(I) |
Tmin = 0.406, Tmax = 0.527 | Rint = 0.033 |
13113 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.106 | Δρmax = 0.87 e Å−3 |
S = 1.00 | Δρmin = −0.56 e Å−3 |
4879 reflections | Absolute structure: Flack (1983), with 2108 Friedel pairs |
320 parameters | Absolute structure parameter: 0.019 (10) |
40 restraints |
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 | Occ. (<1) | |
Br1 | 1.24828 (5) | 0.42440 (5) | 0.82344 (3) | 0.0778 (2) | |
Br2 | 0.83248 (6) | 0.04207 (5) | 0.93545 (3) | 0.07348 (19) | |
C1 | 1.0072 (3) | 0.3091 (3) | 0.81524 (19) | 0.0326 (8) | |
C2 | 0.9179 (4) | 0.2254 (3) | 0.83950 (17) | 0.0327 (8) | |
C3 | 0.9429 (4) | 0.1627 (4) | 0.9009 (2) | 0.0430 (9) | |
C4 | 1.1153 (4) | 0.3249 (3) | 0.8550 (2) | 0.0457 (9) | |
C5 | 1.1361 (5) | 0.2618 (4) | 0.9183 (3) | 0.0585 (13) | |
H5 | 1.2084 | 0.2754 | 0.9450 | 0.070* | |
C6 | 1.0509 (5) | 0.1809 (4) | 0.9407 (2) | 0.0580 (12) | |
H6 | 1.0648 | 0.1378 | 0.9824 | 0.070* | |
C7 | 0.7998 (3) | 0.2026 (3) | 0.7960 (2) | 0.0365 (8) | |
H7A | 0.8238 | 0.1706 | 0.7498 | 0.044* | |
H7B | 0.7500 | 0.1428 | 0.8203 | 0.044* | |
C8 | 0.9871 (3) | 0.3731 (3) | 0.7445 (2) | 0.0355 (8) | |
H8A | 1.0591 | 0.4240 | 0.7360 | 0.043* | |
H8B | 0.9855 | 0.3143 | 0.7066 | 0.043* | |
C9 | 0.6464 (3) | 0.3534 (3) | 0.83720 (18) | 0.0348 (8) | |
C10 | 0.8689 (3) | 0.5529 (3) | 0.77131 (17) | 0.0325 (8) | |
C11 | 0.5539 (4) | 0.5491 (4) | 0.8602 (2) | 0.0487 (10) | |
H11A | 0.4868 | 0.5948 | 0.8384 | 0.058* | |
H11B | 0.5211 | 0.5126 | 0.9034 | 0.058* | |
C12 | 0.6992 (5) | 0.6817 (3) | 0.8162 (2) | 0.0543 (11) | |
H12A | 0.7661 | 0.7361 | 0.8290 | 0.065* | |
H12B | 0.6320 | 0.7273 | 0.7945 | 0.065* | |
C13 | 0.7531 (3) | 0.3920 (3) | 0.72946 (16) | 0.0291 (7) | |
C14 | 0.7293 (4) | 0.3329 (3) | 0.65579 (19) | 0.0396 (9) | |
C15 | 0.8078 (10) | 0.2619 (9) | 0.5512 (4) | 0.069 (3) | 0.63 |
H15A | 0.7429 | 0.2037 | 0.5611 | 0.083* | 0.63 |
H15B | 0.7800 | 0.3106 | 0.5115 | 0.083* | 0.63 |
C16 | 0.9245 (11) | 0.2013 (11) | 0.5321 (7) | 0.106 (4) | 0.63 |
H16A | 0.9931 | 0.2565 | 0.5342 | 0.160* | 0.63 |
H16B | 0.9176 | 0.1700 | 0.4844 | 0.160* | 0.63 |
H16C | 0.9394 | 0.1375 | 0.5651 | 0.160* | 0.63 |
C15' | 0.8403 (13) | 0.3069 (15) | 0.5401 (5) | 0.059 (4) | 0.37 |
H15C | 0.8332 | 0.3781 | 0.5112 | 0.070* | 0.37 |
H15D | 0.7735 | 0.2531 | 0.5263 | 0.070* | 0.37 |
C16' | 0.9655 (12) | 0.2493 (13) | 0.5272 (8) | 0.055 (3) | 0.37 |
H16D | 1.0286 | 0.3094 | 0.5217 | 0.083* | 0.37 |
H16E | 0.9614 | 0.2020 | 0.4845 | 0.083* | 0.37 |
H16F | 0.9864 | 0.1996 | 0.5672 | 0.083* | 0.37 |
C17 | 0.6607 (3) | 0.4976 (3) | 0.74721 (17) | 0.0328 (7) | |
C18 | 0.5684 (3) | 0.5340 (4) | 0.6883 (2) | 0.0411 (8) | |
C19 | 0.5544 (5) | 0.5840 (6) | 0.5650 (2) | 0.0721 (15) | |
H19A | 0.5350 | 0.6682 | 0.5649 | 0.086* | |
H19B | 0.4759 | 0.5404 | 0.5663 | 0.086* | |
C20 | 0.6242 (5) | 0.5533 (5) | 0.4999 (2) | 0.0605 (12) | |
H20A | 0.6445 | 0.4703 | 0.5005 | 0.091* | |
H20B | 0.7003 | 0.5989 | 0.4978 | 0.091* | |
H20C | 0.5735 | 0.5705 | 0.4586 | 0.091* | |
N1 | 0.7219 (3) | 0.3072 (2) | 0.78463 (15) | 0.0307 (7) | |
N2 | 0.8741 (3) | 0.4448 (2) | 0.73897 (14) | 0.0312 (6) | |
N3 | 0.7466 (3) | 0.5948 (2) | 0.76439 (15) | 0.0361 (7) | |
N4 | 0.5948 (3) | 0.4576 (3) | 0.81106 (15) | 0.0368 (7) | |
O1 | 0.9548 (3) | 0.6058 (2) | 0.79841 (15) | 0.0480 (7) | |
O2 | 0.6257 (3) | 0.3098 (3) | 0.89449 (14) | 0.0496 (7) | |
O3 | 0.6542 (3) | 0.6257 (3) | 0.87831 (15) | 0.0538 (7) | |
O4 | 0.6307 (3) | 0.2891 (3) | 0.64205 (16) | 0.0628 (9) | |
O5 | 0.8276 (3) | 0.3372 (3) | 0.61512 (14) | 0.0626 (9) | |
O6 | 0.4591 (3) | 0.5415 (4) | 0.69709 (17) | 0.0794 (11) | |
O7 | 0.6289 (3) | 0.5551 (3) | 0.62817 (13) | 0.0467 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0410 (2) | 0.0734 (3) | 0.1189 (5) | −0.0152 (3) | −0.0261 (3) | 0.0093 (3) |
Br2 | 0.0752 (3) | 0.0742 (3) | 0.0710 (3) | 0.0035 (3) | 0.0081 (3) | 0.0415 (3) |
C1 | 0.0276 (17) | 0.0334 (18) | 0.0368 (19) | 0.0073 (14) | −0.0038 (16) | −0.0003 (15) |
C2 | 0.0355 (19) | 0.0350 (18) | 0.0278 (18) | 0.0133 (16) | 0.0007 (15) | −0.0003 (14) |
C3 | 0.054 (2) | 0.041 (2) | 0.034 (2) | 0.0088 (19) | 0.0053 (18) | 0.0040 (16) |
C4 | 0.039 (2) | 0.042 (2) | 0.057 (2) | 0.0005 (18) | −0.0129 (19) | −0.0028 (18) |
C5 | 0.049 (3) | 0.064 (3) | 0.062 (3) | 0.012 (2) | −0.027 (2) | −0.010 (2) |
C6 | 0.067 (3) | 0.066 (3) | 0.041 (2) | 0.020 (3) | −0.015 (2) | 0.007 (2) |
C7 | 0.0379 (19) | 0.0313 (17) | 0.040 (2) | −0.0056 (16) | −0.0014 (17) | 0.0063 (15) |
C8 | 0.0272 (17) | 0.0390 (19) | 0.0402 (19) | 0.0005 (16) | 0.0049 (16) | 0.0027 (16) |
C9 | 0.0302 (19) | 0.0404 (19) | 0.0339 (18) | −0.0081 (16) | −0.0006 (15) | 0.0048 (15) |
C10 | 0.0343 (18) | 0.0302 (17) | 0.0329 (17) | −0.0049 (15) | 0.0014 (15) | 0.0063 (14) |
C11 | 0.046 (2) | 0.059 (3) | 0.041 (2) | 0.012 (2) | 0.0123 (18) | −0.001 (2) |
C12 | 0.062 (3) | 0.037 (2) | 0.064 (3) | 0.005 (2) | 0.010 (2) | −0.008 (2) |
C13 | 0.0270 (16) | 0.0334 (16) | 0.0270 (17) | 0.0007 (16) | −0.0017 (14) | 0.0036 (13) |
C14 | 0.049 (3) | 0.0387 (19) | 0.0315 (19) | 0.0049 (19) | −0.0007 (18) | 0.0036 (15) |
C15 | 0.081 (6) | 0.080 (5) | 0.045 (4) | −0.003 (4) | 0.004 (4) | −0.012 (4) |
C16 | 0.108 (4) | 0.106 (4) | 0.105 (4) | 0.002 (2) | 0.001 (2) | −0.002 (2) |
C15' | 0.057 (7) | 0.078 (8) | 0.040 (6) | 0.007 (7) | 0.009 (6) | −0.004 (6) |
C16' | 0.056 (4) | 0.055 (4) | 0.055 (4) | 0.001 (2) | 0.001 (2) | −0.002 (2) |
C17 | 0.0313 (18) | 0.0362 (17) | 0.0310 (16) | −0.0005 (16) | 0.0039 (16) | 0.0040 (13) |
C18 | 0.034 (2) | 0.050 (2) | 0.039 (2) | 0.0094 (18) | 0.0005 (17) | 0.0057 (17) |
C19 | 0.068 (3) | 0.106 (4) | 0.042 (2) | 0.034 (3) | −0.013 (2) | 0.017 (3) |
C20 | 0.071 (3) | 0.064 (3) | 0.046 (2) | 0.008 (3) | −0.011 (2) | 0.005 (2) |
N1 | 0.0276 (16) | 0.0320 (14) | 0.0326 (15) | 0.0005 (12) | 0.0053 (12) | 0.0059 (12) |
N2 | 0.0278 (14) | 0.0289 (15) | 0.0369 (15) | 0.0004 (12) | 0.0041 (12) | 0.0036 (12) |
N3 | 0.0369 (16) | 0.0283 (13) | 0.0432 (17) | 0.0045 (15) | 0.0015 (14) | 0.0002 (12) |
N4 | 0.0337 (15) | 0.0392 (15) | 0.0376 (16) | 0.0040 (14) | 0.0086 (14) | 0.0014 (13) |
O1 | 0.0427 (16) | 0.0432 (15) | 0.0579 (17) | −0.0130 (13) | −0.0049 (14) | −0.0044 (13) |
O2 | 0.0588 (19) | 0.0536 (16) | 0.0366 (14) | −0.0038 (15) | 0.0131 (13) | 0.0123 (12) |
O3 | 0.0584 (19) | 0.0532 (16) | 0.0499 (17) | 0.0027 (17) | 0.0067 (15) | −0.0128 (13) |
O4 | 0.069 (2) | 0.070 (2) | 0.0498 (17) | −0.0255 (19) | −0.0159 (16) | −0.0074 (15) |
O5 | 0.0555 (19) | 0.101 (3) | 0.0312 (14) | 0.020 (2) | 0.0018 (15) | −0.0157 (15) |
O6 | 0.0393 (17) | 0.135 (3) | 0.063 (2) | 0.027 (2) | −0.0009 (16) | 0.022 (2) |
O7 | 0.0426 (15) | 0.0613 (17) | 0.0363 (13) | 0.0075 (14) | −0.0027 (12) | 0.0137 (12) |
Br1—C4 | 1.899 (4) | C13—N2 | 1.430 (5) |
Br2—C3 | 1.909 (4) | C13—N1 | 1.443 (4) |
C1—C4 | 1.381 (5) | C13—C14 | 1.549 (5) |
C1—C2 | 1.413 (5) | C13—C17 | 1.579 (5) |
C1—C8 | 1.519 (5) | C14—O4 | 1.187 (5) |
C2—C3 | 1.373 (5) | C14—O5 | 1.294 (5) |
C2—C7 | 1.519 (5) | C15—C16 | 1.462 (9) |
C3—C6 | 1.384 (7) | C15—O5 | 1.479 (7) |
C4—C5 | 1.397 (6) | C15—H15A | 0.9700 |
C5—C6 | 1.352 (7) | C15—H15B | 0.9700 |
C5—H5 | 0.9300 | C16—H16A | 0.9600 |
C6—H6 | 0.9300 | C16—H16B | 0.9600 |
C7—N1 | 1.457 (4) | C16—H16C | 0.9600 |
C7—H7A | 0.9700 | C15'—O5 | 1.448 (9) |
C7—H7B | 0.9700 | C15'—C16' | 1.502 (9) |
C8—N2 | 1.453 (5) | C15'—H15C | 0.9700 |
C8—H8A | 0.9700 | C15'—H15D | 0.9700 |
C8—H8B | 0.9700 | C16'—H16D | 0.9600 |
C9—O2 | 1.197 (4) | C16'—H16E | 0.9600 |
C9—N1 | 1.371 (5) | C16'—H16F | 0.9600 |
C9—N4 | 1.386 (5) | C17—N4 | 1.455 (4) |
C10—O1 | 1.203 (4) | C17—N3 | 1.463 (5) |
C10—N2 | 1.360 (4) | C17—C18 | 1.530 (5) |
C10—N3 | 1.391 (5) | C18—O6 | 1.178 (4) |
C11—O3 | 1.414 (5) | C18—O7 | 1.316 (4) |
C11—N4 | 1.447 (5) | C19—O7 | 1.458 (5) |
C11—H11A | 0.9700 | C19—C20 | 1.467 (6) |
C11—H11B | 0.9700 | C19—H19A | 0.9700 |
C12—O3 | 1.404 (5) | C19—H19B | 0.9700 |
C12—N3 | 1.466 (5) | C20—H20A | 0.9600 |
C12—H12A | 0.9700 | C20—H20B | 0.9600 |
C12—H12B | 0.9700 | C20—H20C | 0.9600 |
C4—C1—C2 | 118.3 (3) | O5—C14—C13 | 111.9 (4) |
C4—C1—C8 | 121.5 (3) | C16—C15—O5 | 110.1 (9) |
C2—C1—C8 | 120.1 (3) | C16—C15—H15A | 109.6 |
C3—C2—C1 | 118.8 (4) | O5—C15—H15A | 109.6 |
C3—C2—C7 | 121.3 (4) | C16—C15—H15B | 109.6 |
C1—C2—C7 | 119.9 (3) | O5—C15—H15B | 109.6 |
C2—C3—C6 | 122.2 (4) | H15A—C15—H15B | 108.1 |
C2—C3—Br2 | 122.0 (3) | O5—C15'—C16' | 109.8 (10) |
C6—C3—Br2 | 115.8 (3) | O5—C15'—H15C | 109.7 |
C1—C4—C5 | 121.4 (4) | C16'—C15'—H15C | 109.7 |
C1—C4—Br1 | 122.0 (3) | O5—C15'—H15D | 109.7 |
C5—C4—Br1 | 116.4 (3) | C16'—C15'—H15D | 109.7 |
C6—C5—C4 | 119.9 (4) | H15C—C15'—H15D | 108.2 |
C6—C5—H5 | 120.1 | C15'—C16'—H16D | 109.5 |
C4—C5—H5 | 120.1 | C15'—C16'—H16E | 109.5 |
C5—C6—C3 | 119.4 (4) | H16D—C16'—H16E | 109.5 |
C5—C6—H6 | 120.3 | C15'—C16'—H16F | 109.5 |
C3—C6—H6 | 120.3 | H16D—C16'—H16F | 109.5 |
N1—C7—C2 | 114.3 (3) | H16E—C16'—H16F | 109.5 |
N1—C7—H7A | 108.7 | N4—C17—N3 | 110.7 (3) |
C2—C7—H7A | 108.7 | N4—C17—C18 | 111.3 (3) |
N1—C7—H7B | 108.7 | N3—C17—C18 | 111.0 (3) |
C2—C7—H7B | 108.7 | N4—C17—C13 | 103.9 (3) |
H7A—C7—H7B | 107.6 | N3—C17—C13 | 102.8 (3) |
N2—C8—C1 | 116.2 (3) | C18—C17—C13 | 116.8 (3) |
N2—C8—H8A | 108.2 | O6—C18—O7 | 126.1 (4) |
C1—C8—H8A | 108.2 | O6—C18—C17 | 123.5 (4) |
N2—C8—H8B | 108.2 | O7—C18—C17 | 110.4 (3) |
C1—C8—H8B | 108.2 | O7—C19—C20 | 110.0 (4) |
H8A—C8—H8B | 107.4 | O7—C19—H19A | 109.7 |
O2—C9—N1 | 126.3 (3) | C20—C19—H19A | 109.7 |
O2—C9—N4 | 126.1 (4) | O7—C19—H19B | 109.7 |
N1—C9—N4 | 107.6 (3) | C20—C19—H19B | 109.7 |
O1—C10—N2 | 126.8 (3) | H19A—C19—H19B | 108.2 |
O1—C10—N3 | 125.6 (3) | C19—C20—H20A | 109.5 |
N2—C10—N3 | 107.5 (3) | C19—C20—H20B | 109.5 |
O3—C11—N4 | 111.1 (3) | H20A—C20—H20B | 109.5 |
O3—C11—H11A | 109.4 | C19—C20—H20C | 109.5 |
N4—C11—H11A | 109.4 | H20A—C20—H20C | 109.5 |
O3—C11—H11B | 109.4 | H20B—C20—H20C | 109.5 |
N4—C11—H11B | 109.4 | C9—N1—C13 | 113.3 (3) |
H11A—C11—H11B | 108.0 | C9—N1—C7 | 122.4 (3) |
O3—C12—N3 | 111.3 (3) | C13—N1—C7 | 120.6 (3) |
O3—C12—H12A | 109.4 | C10—N2—C13 | 113.0 (3) |
N3—C12—H12A | 109.4 | C10—N2—C8 | 120.0 (3) |
O3—C12—H12B | 109.4 | C13—N2—C8 | 121.5 (3) |
N3—C12—H12B | 109.4 | C10—N3—C17 | 110.5 (3) |
H12A—C12—H12B | 108.0 | C10—N3—C12 | 119.2 (3) |
N2—C13—N1 | 113.2 (3) | C17—N3—C12 | 115.4 (3) |
N2—C13—C14 | 115.9 (3) | C9—N4—C11 | 120.0 (3) |
N1—C13—C14 | 108.2 (3) | C9—N4—C17 | 111.1 (3) |
N2—C13—C17 | 102.8 (3) | C11—N4—C17 | 116.4 (3) |
N1—C13—C17 | 101.9 (3) | C12—O3—C11 | 109.5 (3) |
C14—C13—C17 | 114.1 (3) | C14—O5—C15' | 129.4 (7) |
O4—C14—O5 | 127.1 (4) | C14—O5—C15 | 109.7 (5) |
O4—C14—C13 | 121.0 (4) | C18—O7—C19 | 117.7 (3) |
C4—C1—C2—C3 | −0.6 (5) | C2—C7—N1—C9 | −76.3 (4) |
C8—C1—C2—C3 | 175.3 (3) | C2—C7—N1—C13 | 80.4 (4) |
C4—C1—C2—C7 | −178.0 (3) | O1—C10—N2—C13 | 164.1 (3) |
C8—C1—C2—C7 | −2.1 (5) | N3—C10—N2—C13 | −18.8 (4) |
C1—C2—C3—C6 | 1.7 (6) | O1—C10—N2—C8 | 9.8 (5) |
C7—C2—C3—C6 | 179.0 (4) | N3—C10—N2—C8 | −173.2 (3) |
C1—C2—C3—Br2 | −176.8 (3) | N1—C13—N2—C10 | −97.6 (3) |
C7—C2—C3—Br2 | 0.5 (5) | C14—C13—N2—C10 | 136.6 (3) |
C2—C1—C4—C5 | −1.1 (6) | C17—C13—N2—C10 | 11.5 (3) |
C8—C1—C4—C5 | −177.0 (4) | N1—C13—N2—C8 | 56.3 (4) |
C2—C1—C4—Br1 | 174.4 (3) | C14—C13—N2—C8 | −69.5 (4) |
C8—C1—C4—Br1 | −1.4 (5) | C17—C13—N2—C8 | 165.4 (3) |
C1—C4—C5—C6 | 1.9 (7) | C1—C8—N2—C10 | 76.9 (4) |
Br1—C4—C5—C6 | −173.9 (4) | C1—C8—N2—C13 | −75.3 (4) |
C4—C5—C6—C3 | −0.9 (7) | O1—C10—N3—C17 | −164.6 (3) |
C2—C3—C6—C5 | −0.9 (7) | N2—C10—N3—C17 | 18.3 (4) |
Br2—C3—C6—C5 | 177.6 (3) | O1—C10—N3—C12 | −27.3 (5) |
C3—C2—C7—N1 | 124.0 (4) | N2—C10—N3—C12 | 155.5 (3) |
C1—C2—C7—N1 | −58.7 (4) | N4—C17—N3—C10 | 99.6 (3) |
C4—C1—C8—N2 | −123.9 (4) | C18—C17—N3—C10 | −136.3 (3) |
C2—C1—C8—N2 | 60.4 (4) | C13—C17—N3—C10 | −10.8 (3) |
N2—C13—C14—O4 | −178.2 (3) | N4—C17—N3—C12 | −39.4 (4) |
N1—C13—C14—O4 | 53.5 (5) | C18—C17—N3—C12 | 84.6 (4) |
C17—C13—C14—O4 | −59.1 (5) | C13—C17—N3—C12 | −149.8 (3) |
N2—C13—C14—O5 | 2.8 (4) | O3—C12—N3—C10 | −83.8 (5) |
N1—C13—C14—O5 | −125.6 (3) | O3—C12—N3—C17 | 51.5 (5) |
C17—C13—C14—O5 | 121.9 (4) | O2—C9—N4—C11 | 26.9 (6) |
N2—C13—C17—N4 | −115.6 (3) | N1—C9—N4—C11 | −155.2 (3) |
N1—C13—C17—N4 | 1.8 (3) | O2—C9—N4—C17 | 167.4 (4) |
C14—C13—C17—N4 | 118.2 (3) | N1—C9—N4—C17 | −14.7 (4) |
N2—C13—C17—N3 | −0.1 (3) | O3—C11—N4—C9 | 86.7 (4) |
N1—C13—C17—N3 | 117.3 (3) | O3—C11—N4—C17 | −51.8 (4) |
C14—C13—C17—N3 | −126.4 (3) | N3—C17—N4—C9 | −102.1 (3) |
N2—C13—C17—C18 | 121.5 (3) | C18—C17—N4—C9 | 134.0 (3) |
N1—C13—C17—C18 | −121.1 (3) | C13—C17—N4—C9 | 7.6 (4) |
C14—C13—C17—C18 | −4.7 (4) | N3—C17—N4—C11 | 40.0 (4) |
N4—C17—C18—O6 | 8.2 (6) | C18—C17—N4—C11 | −83.9 (4) |
N3—C17—C18—O6 | −115.5 (5) | C13—C17—N4—C11 | 149.7 (3) |
C13—C17—C18—O6 | 127.2 (5) | N3—C12—O3—C11 | −61.0 (5) |
N4—C17—C18—O7 | −171.9 (3) | N4—C11—O3—C12 | 61.0 (4) |
N3—C17—C18—O7 | 64.4 (4) | O4—C14—O5—C15' | 10.0 (11) |
C13—C17—C18—O7 | −52.9 (4) | C13—C14—O5—C15' | −171.0 (9) |
O2—C9—N1—C13 | −165.7 (4) | O4—C14—O5—C15 | −8.9 (7) |
N4—C9—N1—C13 | 16.4 (4) | C13—C14—O5—C15 | 170.0 (5) |
O2—C9—N1—C7 | −7.4 (6) | C16'—C15'—O5—C14 | −143.0 (10) |
N4—C9—N1—C7 | 174.7 (3) | C16'—C15'—O5—C15 | −98 (2) |
N2—C13—N1—C9 | 98.5 (3) | C16—C15—O5—C14 | −142.1 (9) |
C14—C13—N1—C9 | −131.6 (3) | C16—C15—O5—C15' | 73.5 (18) |
C17—C13—N1—C9 | −11.1 (4) | O6—C18—O7—C19 | −3.7 (7) |
N2—C13—N1—C7 | −60.1 (4) | C17—C18—O7—C19 | 176.4 (4) |
C14—C13—N1—C7 | 69.7 (4) | C20—C19—O7—C18 | −154.9 (4) |
C17—C13—N1—C7 | −169.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···O5 | 0.97 | 2.41 | 2.981 (5) | 117 |
C8—H8A···Br1 | 0.97 | 2.59 | 3.198 (4) | 121 |
C7—H7B···Br2 | 0.97 | 2.58 | 3.189 (3) | 121 |
C19—H19A···O2i | 0.97 | 2.46 | 3.274 (6) | 141 |
C11—H11A···O4i | 0.97 | 2.55 | 3.343 (5) | 139 |
C8—H8B···O1ii | 0.97 | 2.44 | 3.178 (5) | 133 |
C7—H7B···O6iii | 0.97 | 2.52 | 3.302 (5) | 137 |
C6—H6···O2iv | 0.93 | 2.46 | 3.182 (5) | 134 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+2, y−1/2, −z+3/2; (iii) −x+1, y−1/2, −z+3/2; (iv) x+1/2, −y+1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C20H20Br2N4O7 |
Mr | 588.22 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 298 |
a, b, c (Å) | 10.6430 (12), 11.2669 (13), 18.673 (2) |
V (Å3) | 2239.1 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.67 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick,1996) |
Tmin, Tmax | 0.406, 0.527 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13113, 4879, 3828 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.106, 1.00 |
No. of reflections | 4879 |
No. of parameters | 320 |
No. of restraints | 40 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.87, −0.56 |
Absolute structure | Flack (1983), with 2108 Friedel pairs |
Absolute structure parameter | 0.019 (10) |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Bruker, 2001).
Br1—C4 | 1.899 (4) | C9—O2 | 1.197 (4) |
C1—C4 | 1.381 (5) | C12—O3 | 1.404 (5) |
C1—C8 | 1.519 (5) | C18—O6 | 1.178 (4) |
C8—N2 | 1.453 (5) | C19—C20 | 1.467 (6) |
C4—C1—C2 | 118.3 (3) | N2—C8—C1 | 116.2 (3) |
C3—C2—C7 | 121.3 (4) | O2—C9—N1 | 126.3 (3) |
C1—C4—Br1 | 122.0 (3) | N1—C9—N4 | 107.6 (3) |
C5—C4—Br1 | 116.4 (3) | O3—C12—N3 | 111.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···O5 | 0.97 | 2.41 | 2.981 (5) | 117.2 |
C8—H8A···Br1 | 0.97 | 2.59 | 3.198 (4) | 120.7 |
C7—H7B···Br2 | 0.97 | 2.58 | 3.189 (3) | 120.6 |
C19—H19A···O2i | 0.97 | 2.46 | 3.274 (6) | 141.4 |
C11—H11A···O4i | 0.97 | 2.55 | 3.343 (5) | 139.2 |
C8—H8B···O1ii | 0.97 | 2.44 | 3.178 (5) | 133.0 |
C7—H7B···O6iii | 0.97 | 2.52 | 3.302 (5) | 137.4 |
C6—H6···O2iv | 0.93 | 2.46 | 3.182 (5) | 134.4 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+2, y−1/2, −z+3/2; (iii) −x+1, y−1/2, −z+3/2; (iv) x+1/2, −y+1/2, −z+2. |
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Diethoxycarbonyl glycoluril bearing a range of electron withdrawing functional groups on its convex face is an important building block for both molecular and supramolecular chemistry (Burnett et al., 2003). The title compound, (I), derived from diethoxycarbonyl glycoluril is an important intermediate for methylene-bridged glycoluril dimers. We report herein its crystal structure.
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987).
When the crystal structure was solved, the atoms C15, H15A, H15B, C16, H16A, H16B and H16C were found to be disordered.
Rings B (N1/N2/C1/C2/C7/C8/C13) and E (N3/N4/O3/C11/C12/C17) are not planar, having total puckering amplitudes, QT, of 2.312 (3) and 1.267 (2) Å, respectively. They adopt chair conformations [ϕ = 108.31 (2)° and θ = 4.40 (3)° (for ring E)] (Cremer & Pople, 1975). Rings C and D have envelope conformations with atoms C9 and C10 displaced by -0.207 (3) Å and -0.246 (2) Å from the planes of the other ring atoms, respectively. Ring A (C1—C6) is, of course, planar.
In the crystal structure, C—H···O and C—H···Br hydrogen bonds (Table 2, Fig. 2) result in the formation of a tape-like structure, in which they may be effective in the stabilization of the structure.