Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054670/hb2614sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054670/hb2614Isup2.hkl |
CCDC reference: 672848
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.059
- wR factor = 0.143
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.04 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.71 Ratio PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C18 PLAT413_ALERT_2_B Short Inter XH3 .. XHn H15A .. H7'1 .. 2.02 Ang.
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1' PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C18' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT301_ALERT_3_C Main Residue Disorder ......................... 15.00 Perc. PLAT395_ALERT_2_C Deviating X-O-Y Angle from 120 Deg for <O1' 141.20 Deg. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 5
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 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 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For a related structure, see: Cao et al. (2006). For background, see: Branda et al. (1995; Elemans et al. (1999); Isaac & Witt (2002); Cao et al. (2006); Wu et al. (2002).
The title compound was synthesized according to the procedure reported by Wu et al. (2002). Colourless blocks of (I) were obtained by slow evaporation of a dichloromethane solution at 283 K.
The methoxy and Br groups are disordered in a 0.847 (4):0.153 (4) ratio and the pendant ethoxy group is disordered over two positions in a 0.531 (14):0.469 (14) ratio. The H atoms were placed at calculated positions (C—H = 0.93–0.97 Å) and treated as riding atoms with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
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).
C21H23BrN4O8 | F(000) = 1104 |
Mr = 539.34 | Dx = 1.565 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2981 reflections |
a = 9.2246 (6) Å | θ = 2.3–19.8° |
b = 11.6031 (8) Å | µ = 1.85 mm−1 |
c = 21.4749 (15) Å | T = 292 K |
β = 95.387 (1)° | Block, colourless |
V = 2288.4 (3) Å3 | 0.15 × 0.10 × 0.10 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 4236 independent reflections |
Radiation source: fine-focus sealed tube | 2704 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
ω scans | θmax = 25.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −11→11 |
Tmin = 0.708, Tmax = 0.837 | k = −13→14 |
18458 measured reflections | l = −25→25 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0404P)2 + 3.1185P] where P = (Fo2 + 2Fc2)/3 |
4236 reflections | (Δ/σ)max < 0.001 |
369 parameters | Δρmax = 0.44 e Å−3 |
5 restraints | Δρmin = −0.29 e Å−3 |
C21H23BrN4O8 | V = 2288.4 (3) Å3 |
Mr = 539.34 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.2246 (6) Å | µ = 1.85 mm−1 |
b = 11.6031 (8) Å | T = 292 K |
c = 21.4749 (15) Å | 0.15 × 0.10 × 0.10 mm |
β = 95.387 (1)° |
Bruker SMART CCD diffractometer | 4236 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 2704 reflections with I > 2σ(I) |
Tmin = 0.708, Tmax = 0.837 | Rint = 0.056 |
18458 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 5 restraints |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.44 e Å−3 |
4236 reflections | Δρmin = −0.29 e Å−3 |
369 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 | Occ. (<1) | |
Br1 | 0.57294 (17) | 0.87084 (9) | 1.04001 (5) | 0.0952 (4) | 0.847 (4) |
Br1' | 0.8610 (16) | 0.3756 (17) | 1.0205 (8) | 0.089 (5) | 0.153 (4) |
C1 | 0.6041 (4) | 0.6566 (4) | 0.97427 (18) | 0.0435 (10) | |
C2 | 0.6485 (6) | 0.7233 (5) | 1.0268 (2) | 0.0609 (14) | |
C3 | 0.7521 (6) | 0.6827 (5) | 1.0725 (2) | 0.0666 (14) | |
H3 | 0.7813 | 0.7290 | 1.1067 | 0.080* | |
C4 | 0.8109 (5) | 0.5772 (5) | 1.0680 (2) | 0.0599 (13) | |
H4 | 0.8812 | 0.5514 | 1.0987 | 0.072* | |
C5 | 0.7665 (5) | 0.5063 (4) | 1.01703 (19) | 0.0513 (11) | |
C6 | 0.6624 (4) | 0.5463 (4) | 0.97033 (17) | 0.0442 (10) | |
C7 | 0.9300 (8) | 0.3499 (7) | 1.0566 (4) | 0.074 (3) | 0.794 (11) |
H7A | 1.0120 | 0.4011 | 1.0612 | 0.111* | 0.794 (11) |
H7B | 0.9607 | 0.2757 | 1.0431 | 0.111* | 0.794 (11) |
H7C | 0.8899 | 0.3421 | 1.0961 | 0.111* | 0.794 (11) |
O1 | 0.8177 (16) | 0.3973 (15) | 1.0096 (8) | 0.066 (4) | 0.794 (11) |
O1' | 0.575 (5) | 0.801 (4) | 1.0325 (19) | 0.084 (18) | 0.206 (11) |
C7' | 0.564 (5) | 0.904 (4) | 1.071 (2) | 0.122 (16) | 0.206 (11) |
H7'1 | 0.6253 | 0.8952 | 1.1099 | 0.183* | 0.206 (11) |
H7'2 | 0.4650 | 0.9144 | 1.0806 | 0.183* | 0.206 (11) |
H7'3 | 0.5949 | 0.9704 | 1.0494 | 0.183* | 0.206 (11) |
C8 | 0.4914 (4) | 0.7006 (4) | 0.92392 (18) | 0.0469 (10) | |
H8A | 0.4064 | 0.6511 | 0.9224 | 0.056* | |
H8B | 0.4614 | 0.7773 | 0.9352 | 0.056* | |
C9 | 0.6138 (4) | 0.4681 (3) | 0.91544 (17) | 0.0422 (10) | |
H9A | 0.6630 | 0.3945 | 0.9214 | 0.051* | |
H9B | 0.5101 | 0.4541 | 0.9152 | 0.051* | |
C10 | 0.6426 (5) | 0.7862 (4) | 0.8483 (2) | 0.0528 (11) | |
C11 | 0.7733 (5) | 0.5001 (4) | 0.83120 (18) | 0.0447 (10) | |
C12 | 0.5534 (4) | 0.6036 (3) | 0.82418 (17) | 0.0394 (9) | |
C13 | 0.4013 (4) | 0.5554 (4) | 0.80176 (18) | 0.0428 (10) | |
C14 | 0.2821 (6) | 0.3967 (5) | 0.7486 (3) | 0.0777 (16) | |
H14A | 0.2993 | 0.3142 | 0.7497 | 0.093* | |
H14B | 0.2063 | 0.4135 | 0.7756 | 0.093* | |
C15 | 0.2343 (8) | 0.4321 (7) | 0.6847 (3) | 0.128 (3) | |
H15A | 0.2148 | 0.5134 | 0.6839 | 0.192* | |
H15B | 0.1473 | 0.3910 | 0.6703 | 0.192* | |
H15C | 0.3094 | 0.4152 | 0.6580 | 0.192* | |
C16 | 0.6491 (4) | 0.6436 (3) | 0.77189 (18) | 0.0441 (10) | |
C17 | 0.5664 (5) | 0.6525 (4) | 0.7062 (2) | 0.0533 (12) | |
O6 | 0.4468 (4) | 0.6891 (3) | 0.69821 (14) | 0.0718 (10) | |
O7 | 0.6602 (12) | 0.6425 (10) | 0.6639 (4) | 0.054 (3) | 0.531 (14) |
C18 | 0.604 (2) | 0.6630 (10) | 0.5969 (6) | 0.059 (4) | 0.531 (14) |
H18A | 0.5293 | 0.7221 | 0.5941 | 0.071* | 0.531 (14) |
H18B | 0.6823 | 0.6875 | 0.5728 | 0.071* | 0.531 (14) |
C19 | 0.543 (3) | 0.5523 (17) | 0.5732 (10) | 0.160 (10) | 0.531 (14) |
H19A | 0.6145 | 0.4927 | 0.5813 | 0.240* | 0.531 (14) |
H19B | 0.5170 | 0.5581 | 0.5290 | 0.240* | 0.531 (14) |
H19C | 0.4582 | 0.5341 | 0.5939 | 0.240* | 0.531 (14) |
O7' | 0.6316 (18) | 0.5954 (13) | 0.6630 (5) | 0.074 (5) | 0.469 (14) |
C18' | 0.560 (2) | 0.615 (2) | 0.5979 (9) | 0.106 (10) | 0.469 (14) |
H18C | 0.4857 | 0.5576 | 0.5871 | 0.127* | 0.469 (14) |
H18D | 0.5145 | 0.6910 | 0.5947 | 0.127* | 0.469 (14) |
C19' | 0.6783 (18) | 0.6071 (13) | 0.5562 (5) | 0.095 (6) | 0.469 (14) |
H19D | 0.7457 | 0.6694 | 0.5650 | 0.143* | 0.469 (14) |
H19E | 0.6381 | 0.6116 | 0.5134 | 0.143* | 0.469 (14) |
H19F | 0.7282 | 0.5350 | 0.5632 | 0.143* | 0.469 (14) |
C20 | 0.8337 (5) | 0.7980 (5) | 0.7755 (3) | 0.0734 (15) | |
H20A | 0.8293 | 0.8122 | 0.7309 | 0.088* | |
H20B | 0.8584 | 0.8699 | 0.7969 | 0.088* | |
C21 | 0.9111 (5) | 0.6116 (5) | 0.7606 (2) | 0.0697 (15) | |
H21A | 0.9882 | 0.5562 | 0.7713 | 0.084* | |
H21B | 0.9062 | 0.6254 | 0.7159 | 0.084* | |
N1 | 0.5433 (3) | 0.7050 (3) | 0.86198 (14) | 0.0420 (8) | |
N2 | 0.6426 (3) | 0.5141 (3) | 0.85540 (14) | 0.0390 (8) | |
N3 | 0.6924 (4) | 0.7591 (3) | 0.79149 (16) | 0.0500 (9) | |
N4 | 0.7724 (3) | 0.5639 (3) | 0.77641 (15) | 0.0504 (9) | |
O2 | 0.2900 (3) | 0.5991 (3) | 0.81306 (14) | 0.0577 (8) | |
O3 | 0.4160 (3) | 0.4573 (3) | 0.77150 (14) | 0.0596 (9) | |
O4 | 0.6769 (4) | 0.8709 (3) | 0.87933 (17) | 0.0796 (11) | |
O5 | 0.8721 (3) | 0.4370 (3) | 0.85125 (14) | 0.0589 (8) | |
O8 | 0.9437 (3) | 0.7148 (4) | 0.79252 (18) | 0.0794 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.1399 (9) | 0.0653 (6) | 0.0747 (7) | 0.0082 (6) | −0.0197 (6) | −0.0237 (5) |
Br1' | 0.088 (10) | 0.088 (6) | 0.095 (12) | 0.012 (6) | 0.031 (9) | 0.012 (6) |
C1 | 0.040 (2) | 0.053 (3) | 0.037 (2) | −0.007 (2) | −0.0008 (18) | 0.0016 (18) |
C2 | 0.069 (4) | 0.059 (3) | 0.053 (3) | −0.014 (3) | −0.006 (3) | −0.003 (2) |
C3 | 0.071 (3) | 0.081 (4) | 0.045 (3) | −0.029 (3) | −0.013 (2) | −0.007 (3) |
C4 | 0.049 (3) | 0.088 (4) | 0.040 (3) | −0.016 (3) | −0.011 (2) | 0.009 (2) |
C5 | 0.046 (3) | 0.064 (3) | 0.043 (2) | −0.009 (2) | −0.001 (2) | 0.013 (2) |
C6 | 0.041 (2) | 0.055 (3) | 0.036 (2) | −0.009 (2) | −0.0036 (18) | 0.0078 (18) |
C7 | 0.064 (5) | 0.096 (6) | 0.057 (4) | 0.022 (4) | −0.028 (4) | 0.030 (4) |
O1 | 0.073 (8) | 0.076 (9) | 0.047 (4) | 0.008 (5) | −0.008 (5) | 0.005 (4) |
O1' | 0.19 (4) | 0.07 (5) | 0.09 (4) | 0.00 (4) | 0.03 (3) | −0.01 (4) |
C7' | 0.12 (3) | 0.12 (4) | 0.12 (4) | 0.00 (3) | 0.01 (3) | 0.00 (3) |
C8 | 0.043 (2) | 0.054 (3) | 0.044 (2) | 0.001 (2) | 0.0007 (19) | −0.001 (2) |
C9 | 0.038 (2) | 0.044 (2) | 0.042 (2) | −0.0020 (19) | −0.0067 (18) | 0.0040 (18) |
C10 | 0.058 (3) | 0.043 (3) | 0.054 (3) | −0.002 (2) | −0.009 (2) | 0.008 (2) |
C11 | 0.042 (3) | 0.047 (2) | 0.042 (2) | −0.001 (2) | −0.008 (2) | −0.0007 (19) |
C12 | 0.036 (2) | 0.045 (2) | 0.036 (2) | 0.0023 (18) | −0.0062 (17) | 0.0029 (17) |
C13 | 0.034 (2) | 0.050 (3) | 0.043 (2) | 0.002 (2) | −0.0029 (19) | 0.0007 (19) |
C14 | 0.059 (3) | 0.076 (4) | 0.094 (4) | −0.016 (3) | −0.010 (3) | −0.024 (3) |
C15 | 0.110 (5) | 0.171 (7) | 0.094 (5) | −0.063 (5) | −0.040 (4) | 0.001 (5) |
C16 | 0.043 (2) | 0.048 (2) | 0.041 (2) | 0.004 (2) | −0.0023 (18) | 0.0087 (18) |
C17 | 0.045 (3) | 0.071 (3) | 0.042 (2) | 0.009 (2) | −0.002 (2) | 0.004 (2) |
O6 | 0.051 (2) | 0.112 (3) | 0.0494 (19) | 0.018 (2) | −0.0089 (16) | 0.0163 (18) |
O7 | 0.062 (5) | 0.059 (7) | 0.041 (5) | 0.010 (5) | 0.000 (4) | 0.004 (4) |
C18 | 0.067 (9) | 0.064 (8) | 0.044 (6) | 0.004 (7) | 0.000 (6) | 0.006 (5) |
C19 | 0.154 (19) | 0.16 (2) | 0.16 (2) | −0.004 (16) | −0.022 (18) | −0.012 (15) |
O7' | 0.083 (9) | 0.096 (11) | 0.041 (5) | 0.027 (8) | −0.009 (5) | −0.018 (6) |
C18' | 0.12 (2) | 0.11 (2) | 0.086 (14) | 0.007 (18) | −0.001 (14) | 0.001 (15) |
C19' | 0.117 (13) | 0.107 (12) | 0.063 (8) | 0.029 (10) | 0.018 (8) | 0.018 (8) |
C20 | 0.064 (3) | 0.076 (4) | 0.080 (4) | −0.018 (3) | 0.006 (3) | 0.030 (3) |
C21 | 0.040 (3) | 0.101 (4) | 0.069 (3) | 0.008 (3) | 0.011 (2) | 0.029 (3) |
N1 | 0.042 (2) | 0.0398 (18) | 0.0427 (19) | 0.0002 (16) | −0.0017 (15) | 0.0024 (15) |
N2 | 0.0350 (19) | 0.0446 (19) | 0.0358 (17) | 0.0039 (15) | −0.0046 (14) | 0.0040 (14) |
N3 | 0.045 (2) | 0.054 (2) | 0.050 (2) | −0.0035 (17) | 0.0019 (17) | 0.0092 (17) |
N4 | 0.0330 (19) | 0.067 (2) | 0.051 (2) | 0.0159 (18) | 0.0033 (16) | 0.0132 (18) |
O2 | 0.0376 (18) | 0.073 (2) | 0.0610 (19) | 0.0082 (16) | −0.0034 (15) | −0.0094 (16) |
O3 | 0.0381 (17) | 0.064 (2) | 0.074 (2) | −0.0034 (15) | −0.0060 (15) | −0.0232 (17) |
O4 | 0.105 (3) | 0.054 (2) | 0.079 (2) | −0.024 (2) | 0.006 (2) | −0.0073 (18) |
O5 | 0.0460 (18) | 0.068 (2) | 0.0600 (19) | 0.0149 (16) | −0.0078 (15) | 0.0149 (16) |
O8 | 0.046 (2) | 0.097 (3) | 0.094 (3) | −0.015 (2) | −0.0009 (18) | 0.031 (2) |
Br1—C2 | 1.880 (6) | C13—O2 | 1.190 (5) |
Br1'—C5 | 1.748 (16) | C13—O3 | 1.324 (5) |
C1—C6 | 1.395 (6) | C14—C15 | 1.460 (8) |
C1—C2 | 1.397 (6) | C14—O3 | 1.466 (5) |
C1—C8 | 1.516 (5) | C14—H14A | 0.9700 |
C2—O1' | 1.14 (4) | C14—H14B | 0.9700 |
C2—C3 | 1.386 (7) | C15—H15A | 0.9600 |
C3—C4 | 1.347 (7) | C15—H15B | 0.9600 |
C3—H3 | 0.9300 | C15—H15C | 0.9600 |
C4—C5 | 1.399 (6) | C16—N3 | 1.449 (5) |
C4—H4 | 0.9300 | C16—N4 | 1.462 (5) |
C5—O1 | 1.365 (18) | C16—C17 | 1.544 (6) |
C5—C6 | 1.401 (5) | C17—O6 | 1.180 (5) |
C6—C9 | 1.521 (5) | C17—O7 | 1.317 (8) |
C7—O1 | 1.482 (10) | C17—O7' | 1.328 (8) |
C7—H7A | 0.9600 | O7—C18 | 1.501 (10) |
C7—H7B | 0.9600 | C18—C19 | 1.472 (16) |
C7—H7C | 0.9600 | C18—H18A | 0.9700 |
O1'—C7' | 1.474 (14) | C18—H18B | 0.9700 |
C7'—H7'1 | 0.9600 | C19—H19A | 0.9600 |
C7'—H7'2 | 0.9600 | C19—H19B | 0.9600 |
C7'—H7'3 | 0.9600 | C19—H19C | 0.9600 |
C8—N1 | 1.456 (5) | O7'—C18' | 1.509 (11) |
C8—H8A | 0.9700 | C18'—C19' | 1.481 (16) |
C8—H8B | 0.9700 | C18'—H18C | 0.9700 |
C9—N2 | 1.443 (5) | C18'—H18D | 0.9700 |
C9—H9A | 0.9700 | C19'—H19D | 0.9600 |
C9—H9B | 0.9700 | C19'—H19E | 0.9600 |
C10—O4 | 1.212 (5) | C19'—H19F | 0.9600 |
C10—N1 | 1.365 (5) | C20—O8 | 1.423 (6) |
C10—N3 | 1.380 (6) | C20—N3 | 1.451 (6) |
C11—O5 | 1.216 (5) | C20—H20A | 0.9700 |
C11—N2 | 1.367 (5) | C20—H20B | 0.9700 |
C11—N4 | 1.390 (5) | C21—O8 | 1.399 (6) |
C12—N1 | 1.437 (5) | C21—N4 | 1.463 (6) |
C12—N2 | 1.450 (5) | C21—H21A | 0.9700 |
C12—C13 | 1.545 (5) | C21—H21B | 0.9700 |
C12—C16 | 1.563 (6) | ||
C6—C1—C2 | 118.1 (4) | C14—C15—H15A | 109.5 |
C6—C1—C8 | 120.6 (3) | C14—C15—H15B | 109.5 |
C2—C1—C8 | 121.3 (4) | H15A—C15—H15B | 109.5 |
O1'—C2—C3 | 125 (2) | C14—C15—H15C | 109.5 |
O1'—C2—C1 | 113 (2) | H15A—C15—H15C | 109.5 |
C3—C2—C1 | 121.0 (5) | H15B—C15—H15C | 109.5 |
C3—C2—Br1 | 116.3 (4) | N3—C16—N4 | 112.0 (3) |
C1—C2—Br1 | 122.8 (4) | N3—C16—C17 | 107.6 (3) |
C4—C3—C2 | 120.9 (5) | N4—C16—C17 | 114.7 (3) |
C4—C3—H3 | 119.6 | N3—C16—C12 | 103.0 (3) |
C2—C3—H3 | 119.6 | N4—C16—C12 | 104.6 (3) |
C3—C4—C5 | 120.0 (4) | C17—C16—C12 | 114.4 (3) |
C3—C4—H4 | 120.0 | O6—C17—O7 | 126.7 (7) |
C5—C4—H4 | 120.0 | O6—C17—O7' | 123.9 (8) |
O1—C5—C4 | 123.8 (7) | O6—C17—C16 | 122.1 (4) |
O1—C5—C6 | 116.4 (8) | O7—C17—C16 | 108.9 (7) |
C4—C5—C6 | 119.8 (5) | O7'—C17—C16 | 112.8 (8) |
C4—C5—Br1' | 111.6 (7) | C17—O7—C18 | 117.2 (12) |
C6—C5—Br1' | 128.6 (7) | C19—C18—O7 | 106.2 (11) |
C1—C6—C5 | 120.2 (4) | C19—C18—H18A | 110.5 |
C1—C6—C9 | 120.5 (3) | O7—C18—H18A | 110.5 |
C5—C6—C9 | 119.3 (4) | C19—C18—H18B | 110.5 |
C5—O1—C7 | 119.5 (15) | O7—C18—H18B | 110.5 |
C2—O1'—C7' | 141 (5) | H18A—C18—H18B | 108.7 |
O1'—C7'—H7'1 | 109.5 | C17—O7'—C18' | 112.4 (13) |
O1'—C7'—H7'2 | 109.5 | C19'—C18'—O7' | 105.3 (12) |
H7'1—C7'—H7'2 | 108 | C19'—C18'—H18C | 110.7 |
O1'—C7'—H7'3 | 109.5 | O7'—C18'—H18C | 110.7 |
H7'1—C7'—H7'3 | 109.5 | C19'—C18'—H18D | 110.7 |
H7'2—C7'—H7'3 | 109.5 | O7'—C18'—H18D | 110.7 |
N1—C8—C1 | 113.6 (3) | H18C—C18'—H18D | 108.8 |
N1—C8—H8A | 108.8 | C18'—C19'—H19D | 109.5 |
C1—C8—H8A | 108.8 | C18'—C19'—H19E | 109.5 |
N1—C8—H8B | 108.8 | H19D—C19'—H19E | 109.5 |
C1—C8—H8B | 108.8 | C18'—C19'—H19F | 109.5 |
H8A—C8—H8B | 107.7 | H19D—C19'—H19F | 109.5 |
N2—C9—C6 | 114.0 (3) | H19E—C19'—H19F | 109.5 |
N2—C9—H9A | 108.8 | O8—C20—N3 | 111.3 (4) |
C6—C9—H9A | 108.8 | O8—C20—H20A | 109.4 |
N2—C9—H9B | 108.8 | N3—C20—H20A | 109.4 |
C6—C9—H9B | 108.8 | O8—C20—H20B | 109.4 |
H9A—C9—H9B | 107.7 | N3—C20—H20B | 109.4 |
O4—C10—N1 | 126.0 (5) | H20A—C20—H20B | 108.0 |
O4—C10—N3 | 125.4 (4) | O8—C21—N4 | 111.3 (4) |
N1—C10—N3 | 108.6 (4) | O8—C21—H21A | 109.4 |
O5—C11—N2 | 126.6 (4) | N4—C21—H21A | 109.4 |
O5—C11—N4 | 124.4 (4) | O8—C21—H21B | 109.4 |
N2—C11—N4 | 108.8 (3) | N4—C21—H21B | 109.4 |
N1—C12—N2 | 112.9 (3) | H21A—C21—H21B | 108.0 |
N1—C12—C13 | 111.5 (3) | C10—N1—C12 | 111.3 (3) |
N2—C12—C13 | 110.1 (3) | C10—N1—C8 | 120.3 (3) |
N1—C12—C16 | 103.5 (3) | C12—N1—C8 | 122.1 (3) |
N2—C12—C16 | 102.2 (3) | C11—N2—C9 | 122.6 (3) |
C13—C12—C16 | 116.2 (3) | C11—N2—C12 | 113.1 (3) |
O2—C13—O3 | 126.7 (4) | C9—N2—C12 | 122.3 (3) |
O2—C13—C12 | 123.9 (4) | C10—N3—C16 | 111.2 (3) |
O3—C13—C12 | 109.4 (3) | C10—N3—C20 | 121.3 (4) |
C15—C14—O3 | 110.5 (5) | C16—N3—C20 | 116.6 (4) |
C15—C14—H14A | 109.5 | C11—N4—C16 | 109.6 (3) |
O3—C14—H14A | 109.5 | C11—N4—C21 | 117.5 (3) |
C15—C14—H14B | 109.5 | C16—N4—C21 | 115.9 (4) |
O3—C14—H14B | 109.5 | C13—O3—C14 | 117.1 (4) |
H14A—C14—H14B | 108.1 | C21—O8—C20 | 109.8 (4) |
C6—C1—C2—O1' | −165 (3) | C16—C17—O7—C18 | −172.9 (7) |
C8—C1—C2—O1' | 13 (3) | C17—O7—C18—C19 | −86 (2) |
C6—C1—C2—C3 | 2.5 (7) | O6—C17—O7'—C18' | 18.8 (17) |
C8—C1—C2—C3 | −179.7 (4) | O7—C17—O7'—C18' | −87 (3) |
C6—C1—C2—Br1 | −177.3 (3) | C16—C17—O7'—C18' | −173.5 (11) |
C8—C1—C2—Br1 | 0.5 (6) | C17—O7'—C18'—C19' | 148.8 (19) |
O1'—C2—C3—C4 | 165 (3) | O4—C10—N1—C12 | −166.4 (4) |
C1—C2—C3—C4 | −1.0 (8) | N3—C10—N1—C12 | 16.7 (4) |
Br1—C2—C3—C4 | 178.8 (4) | O4—C10—N1—C8 | −13.7 (6) |
C2—C3—C4—C5 | −0.8 (8) | N3—C10—N1—C8 | 169.4 (3) |
C3—C4—C5—O1 | −178.3 (10) | N2—C12—N1—C10 | 95.9 (4) |
C3—C4—C5—C6 | 1.0 (7) | C13—C12—N1—C10 | −139.4 (3) |
C3—C4—C5—Br1' | 178.6 (7) | C16—C12—N1—C10 | −13.7 (4) |
C2—C1—C6—C5 | −2.3 (6) | N2—C12—N1—C8 | −56.3 (5) |
C8—C1—C6—C5 | 180.0 (4) | C13—C12—N1—C8 | 68.4 (4) |
C2—C1—C6—C9 | 177.7 (4) | C16—C12—N1—C8 | −165.9 (3) |
C8—C1—C6—C9 | −0.1 (6) | C1—C8—N1—C10 | −71.8 (5) |
O1—C5—C6—C1 | 179.9 (9) | C1—C8—N1—C12 | 77.9 (4) |
C4—C5—C6—C1 | 0.5 (6) | O5—C11—N2—C9 | 10.5 (6) |
Br1'—C5—C6—C1 | −176.6 (8) | N4—C11—N2—C9 | −173.8 (3) |
O1—C5—C6—C9 | −0.1 (10) | O5—C11—N2—C12 | 174.6 (4) |
C4—C5—C6—C9 | −179.4 (4) | N4—C11—N2—C12 | −9.7 (4) |
Br1'—C5—C6—C9 | 3.5 (9) | C6—C9—N2—C11 | 85.6 (4) |
C4—C5—O1—C7 | −2 (2) | C6—C9—N2—C12 | −77.1 (4) |
C6—C5—O1—C7 | 178.9 (11) | N1—C12—N2—C11 | −108.3 (4) |
Br1'—C5—O1—C7 | 12 (5) | C13—C12—N2—C11 | 126.3 (3) |
C3—C2—O1'—C7' | 19 (8) | C16—C12—N2—C11 | 2.2 (4) |
C1—C2—O1'—C7' | −174 (6) | N1—C12—N2—C9 | 55.9 (5) |
Br1—C2—O1'—C7' | −40 (6) | C13—C12—N2—C9 | −69.5 (4) |
C6—C1—C8—N1 | −60.5 (5) | C16—C12—N2—C9 | 166.4 (3) |
C2—C1—C8—N1 | 121.8 (4) | O4—C10—N3—C16 | 170.7 (4) |
C1—C6—C9—N2 | 60.5 (5) | N1—C10—N3—C16 | −12.4 (4) |
C5—C6—C9—N2 | −119.5 (4) | O4—C10—N3—C20 | 27.7 (7) |
N1—C12—C13—O2 | 2.0 (5) | N1—C10—N3—C20 | −155.4 (4) |
N2—C12—C13—O2 | 128.2 (4) | N4—C16—N3—C10 | −108.3 (4) |
C16—C12—C13—O2 | −116.3 (4) | C17—C16—N3—C10 | 124.8 (4) |
N1—C12—C13—O3 | −175.0 (3) | C12—C16—N3—C10 | 3.6 (4) |
N2—C12—C13—O3 | −48.8 (4) | N4—C16—N3—C20 | 36.6 (5) |
C16—C12—C13—O3 | 66.7 (4) | C17—C16—N3—C20 | −90.3 (4) |
N1—C12—C16—N3 | 5.8 (3) | C12—C16—N3—C20 | 148.5 (3) |
N2—C12—C16—N3 | −111.7 (3) | O8—C20—N3—C10 | 91.9 (5) |
C13—C12—C16—N3 | 128.4 (3) | O8—C20—N3—C16 | −49.1 (6) |
N1—C12—C16—N4 | 123.0 (3) | O5—C11—N4—C16 | −170.8 (4) |
N2—C12—C16—N4 | 5.5 (4) | N2—C11—N4—C16 | 13.4 (4) |
C13—C12—C16—N4 | −114.3 (4) | O5—C11—N4—C21 | −35.6 (6) |
N1—C12—C16—C17 | −110.7 (4) | N2—C11—N4—C21 | 148.6 (4) |
N2—C12—C16—C17 | 131.9 (3) | N3—C16—N4—C11 | 99.3 (4) |
C13—C12—C16—C17 | 12.0 (5) | C17—C16—N4—C11 | −137.7 (4) |
N3—C16—C17—O6 | −73.9 (6) | C12—C16—N4—C11 | −11.5 (4) |
N4—C16—C17—O6 | 160.8 (4) | N3—C16—N4—C21 | −36.7 (5) |
C12—C16—C17—O6 | 39.9 (6) | C17—C16—N4—C21 | 86.3 (5) |
N3—C16—C17—O7 | 90.1 (7) | C12—C16—N4—C21 | −147.5 (4) |
N4—C16—C17—O7 | −35.2 (7) | O8—C21—N4—C11 | −82.3 (5) |
C12—C16—C17—O7 | −156.1 (6) | O8—C21—N4—C16 | 50.1 (5) |
N3—C16—C17—O7' | 118.2 (9) | O2—C13—O3—C14 | 1.0 (6) |
N4—C16—C17—O7' | −7.1 (10) | C12—C13—O3—C14 | 177.9 (4) |
C12—C16—C17—O7' | −128.0 (9) | C15—C14—O3—C13 | 91.6 (6) |
O6—C17—O7—C18 | −9.8 (13) | N4—C21—O8—C20 | −61.0 (5) |
O7'—C17—O7—C18 | 84 (3) | N3—C20—O8—C21 | 60.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O6i | 0.93 | 2.56 | 3.437 (5) | 159 |
C4—H4···O5ii | 0.93 | 2.43 | 3.261 (5) | 149 |
C19—H19A···O4iii | 0.96 | 2.47 | 3.41 (3) | 167 |
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+2, −y+1, −z+2; (iii) −x+3/2, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C21H23BrN4O8 |
Mr | 539.34 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 292 |
a, b, c (Å) | 9.2246 (6), 11.6031 (8), 21.4749 (15) |
β (°) | 95.387 (1) |
V (Å3) | 2288.4 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.85 |
Crystal size (mm) | 0.15 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.708, 0.837 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18458, 4236, 2704 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.143, 1.08 |
No. of reflections | 4236 |
No. of parameters | 369 |
No. of restraints | 5 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.44, −0.29 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O6i | 0.93 | 2.56 | 3.437 (5) | 159 |
C4—H4···O5ii | 0.93 | 2.43 | 3.261 (5) | 149 |
C19—H19A···O4iii | 0.96 | 2.47 | 3.41 (3) | 167 |
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+2, −y+1, −z+2; (iii) −x+3/2, y−1/2, −z+3/2. |
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Glycoluril has also become an important building block in supramolecular chemistry (Branda et al., 1995; Elemans et al., 1999; Isaac & Witt, 2002). The widespread interest in glycolurils has led to a variety of crystal structures reported for a number of its derivatives. We report here the structure of the title glycoluril derivative, (I) (Fig. 1), which is an important intermediate for the preparation glycoluril receptors (Wu et al., 2002). The bond lengths and angles in (I) present no unusual features and are similar to those found in similar compounds (Cao et al., 2006).
The C3N2O oxadiazinane six-membered ring in (I) displays a normal chair conformation. Weak intermolecular C—H···O hydrogen bonds help to establish the packing (Fig. 2).